WO2002080863A2 - Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using - Google Patents

Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using Download PDF

Info

Publication number
WO2002080863A2
WO2002080863A2 PCT/US2001/047459 US0147459W WO02080863A2 WO 2002080863 A2 WO2002080863 A2 WO 2002080863A2 US 0147459 W US0147459 W US 0147459W WO 02080863 A2 WO02080863 A2 WO 02080863A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
chosen
composition
polymer
film
Prior art date
Application number
PCT/US2001/047459
Other languages
French (fr)
Other versions
WO2002080863A3 (en
Inventor
Mohamed Kanji
Carl Orr
Carlos O. Pinzon
Original Assignee
L'oreal Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L'oreal Sa filed Critical L'oreal Sa
Priority to CA002399467A priority Critical patent/CA2399467A1/en
Priority to JP2002578902A priority patent/JP2004519548A/en
Priority to AU2001297750A priority patent/AU2001297750A1/en
Priority to BR0108238-8A priority patent/BR0108238A/en
Priority to EP01273639A priority patent/EP1353626A2/en
Publication of WO2002080863A2 publication Critical patent/WO2002080863A2/en
Publication of WO2002080863A3 publication Critical patent/WO2002080863A3/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90Block copolymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8123Compositions of homopolymers or copolymers of compounds having one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers, e.g. PVC, PTFE
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88Polyamides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/10Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara

Definitions

  • the present invention relates to compositions and methods for caring for, treating, and making up at least one keratinous material, for example at least one human keratinous material, such as skin, including the scalp, lips, superficial body growths, including the nails, and/or at least one keratinous fiber, which includes the hair, eyelashes, and eyebrows.
  • the compositions are transfer resistant cosmetic compositions.
  • the compositions are pliable and/or comfortable to wear upon application.
  • the compositions in one embodiment, comprise at least one structuring polymer and at least one film-forming silicone resin.
  • the invention in one embodiment, relates to cosmetic, dermatological, and pharmaceutical products containing this composition. Due to the good stability of the compositions of the invention, it is possible to add at least one UV blocker to the composition.
  • the expression "at least one" means one or more and thus, includes individual components as well as mixtures/combinations.
  • compositions including pigmented cosmetics such as foundations, concealers, lipsticks, mascaras, and other cosmetic and sunscreen compositions, have been developed for longer wear and non- transfer properties. This is accomplished by the use of compositions that form a film after application.
  • Such compositions generally contain volatile solvents which evaporate on contact with the skin or other keratinous materials, leaving behind a layer comprising waxes and/or resins, pigments, fillers, and actives.
  • these compositions tend to be uncomfortable for the wearer as the compositions remain on the skin or other keratinous materials as a brittle or non-flexible film.
  • Such compositions may not be either pliable or soft, and they may not be comfortable to wear. There may also be a tendency for such compositions to flake off because of poor adherence to the skin or other keratinous materials.
  • compositions may have a tendency to be tacky, resulting in poor application and spreadability characteristics.
  • a composition which is transfer resistant may deposit a film onto keratinous materials which may not transfer when the keratinous materials comes into contact with, for example, other keratinous materials, such as skin, or with a cup, paper, a cigarette, or a handkerchief.
  • the transfer resistance of a composition may be evaluated by an art recognized transfer resistance test.
  • a composition is applied to the clean, bare skin of a group of subjects as a smooth, thin layer, such as a 1" x 1" square in size.
  • the composition is allowed to air dry for 5 minutes, and using a facial tissue or other cloth or sponge and medium pressure, the area is wiped as if attempting to wipe the product off of the skin.
  • the subjects are then asked to evaluate the results. Positive results are described as the presence of a makeup film that could not be easily removed without soap and water. For example, the results may be rated on a scale of 1 to 5 with 5 being the best and 1 being the worst.
  • the present invention in one embodiment, provides compositions comprising at least one structuring polymer, e.g., a polyamide polymer, comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom.
  • the compositions also comprise at least one liquid fatty phase comprising at least one film-forming silicone resin.
  • the present invention also relates to methods for making such compositions.
  • compositions comprising combinations of at least one structuring polymer, e.g., a polyamide polymer, and at least one film-forming silicone resin.
  • at least one structuring polymer e.g., a polyamide polymer
  • the at least one film-forming silicone resin are present in an amount effective to provide transfer resistant properties, and may also provide at least one of the following properties: pliability, softness, and wearing comfort.
  • compositions which are useful for the care, make-up and/or treating of at least one keratinous material, which compositions may be of suitable hardness to allow their preparation in the form of a stick or other structured form, which may be stable.
  • stability can be tested by placing the composition in a controlled environment chamber for 8 weeks at 25°C.
  • the physical condition of the sample is inspected as it is placed in the chamber.
  • the sample is then inspected again at 24 hours, 3 days, 1 week, 2 weeks, 4 weeks and 8 weeks.
  • the sample is examined for abnormalities in the composition such as bending or leaning if the composition is in stick form, phase separation, melting, or syneresis.
  • syneresis is the appearance of droplets on the surface of a composition that are visible to the naked eye.
  • the stability is further tested by repeating the 8 week test at 4°C, 37°C, 45°C, 50°C, and under freeze-thaw conditions.
  • a composition is considered to lack stability if in any of these tests an abnormality that impedes functioning of the composition is observed. The skilled artisan will readily recognize an abnormality that impedes functioning of a composition based on the intended application.
  • Structured liquid fatty phases in cosmetic or dermatological products are known in the art. Structured liquid fatty phases may be found, for example, in solid compositions such as deodorants, balms, lip compositions, concealer products, and cast foundations.
  • the compositions of the invention may comprise at least one liquid fatty phase.
  • liquid fatty phase means a fatty phase which is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg, i.e., 101 kPa) and which is composed of at least one fatty substance, such as an oil, which is liquid at room temperature and not soluble in water. If the at least one liquid fatty phase comprises two or more fatty substances, they should be mutually compatible, i.e., forming a homogenous phase macroscopically.
  • Structured liquid fatty phases may make it possible to control the exudation of the liquid fatty phase from the solid compositions of which they are components, including exudation in a wet or hot atmosphere or environment. Structuring of the liquid fatty phase may also limit bleeding of this phase outside of the intended area of application and especially into wrinkles and fine lines after it has been deposited, for example, on keratinous materials.
  • keratinous material is meant to comprise hair, lips, skin, scalp and superficial body growths such as eyelashes, eyebrows, and nails.
  • the invention applies not only to make-up products for at least one keratinous material such as lip compositions, lip pencils, foundations, including foundations which may be cast in the form of a stick or a dish, concealer products, temporary tattoo products, eyeliners, and mascara bars, but also to body hygiene products such as deodorant sticks, and to care products and products for treating at least one keratinous material such as sunscreen and after-sun products which may be in stick form.
  • keratinous material such as lip compositions, lip pencils, foundations, including foundations which may be cast in the form of a stick or a dish, concealer products, temporary tattoo products, eyeliners, and mascara bars, but also to body hygiene products such as deodorant sticks, and to care products and products for treating at least one keratinous material such as sunscreen and after-sun products which may be in stick form.
  • the present invention may be in the form of a mascara product including mascara bars, an eyeliner product, a foundation product, a lipstick product, a blush for cheeks or eyelids, a deodorant product, a make-up product for the body, a make-up- removing product, an eyeshadow product, a face powder product, a concealer product, a treating shampoo product, a hair conditioning product, a sunscreen (antisun) product, a colorant for the skin or hair, or a skin care formula such as, for example, anti-pimple or shaving cut formulas.
  • a deodorant product is a body hygiene product and does not relate to care, make-up, or treatment of keratinous materials, including keratinous fibers, skin, or lips.
  • the composition of the present invention may be in a form chosen from a paste, a solid, a gel, and a cream. It may also be an emulsion, such as an oil-in-water or water-in-oil emulsion, a multiple emulsion, such as an oil-in-water-in-oil emulsion or a water-in-oil-in-water emulsion, or a solid, rigid or supple gel, including anhydrous gels. In one embodiment, the composition of the invention is anhydrous.
  • the composition of the invention may, for example, comprise an external or continuous liquid fatty phase. By "external or continuous" phase, it is meant, by way of example, the water phase in a water-in-oil emulsion, wherein the oil droplets are dispersed throughout the external or continuous water phase.
  • the composition of the invention is transparent or clear, including for example, a composition without pigments.
  • the composition can also be in a form chosen from a translucent anhydrous gel and a transparent anhydrous gel.
  • the composition can also be a molded composition or cast as a stick or a dish.
  • the composition in one embodiment is a solid such as a molded stick or a poured stick. Structuring polymer
  • the at least one structuring polymer in the composition of the invention is a solid that is not deformable at room temperature (25°C) and atmospheric pressure (760 mmHg, i.e., 101 kPa).
  • the at least one structuring polymer is capable of structuring the composition without opacifying it. This may be due to the fact that the polymer does not crystallize.
  • the structuring of the liquid fatty phase comprising the at least one structuring polymer may be due to the hydrogen interactions between two molecules of the polymer and/or between the molecules of the polymer and the liquid fatty phase.
  • the at least one structuring polymer of the present invention comprises a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom.
  • the at least one structuring polymer further comprises at least one terminal fatty chain chosen from alkyl and alkenyl chains, such as of at least 4 carbon atoms, and further such as comprising from 8 to 120 carbon atoms, bonded to the polymer skeleton via at least one linking group.
  • the terminal fatty chain may, for example, be functionalized.
  • the at least one structuring polymer may also further comprise at least one pendant fatty chain chosen from alkyl and alkenyl chains, such as of at least 4 carbon atoms, and further such as comprising from 8 to 120 carbon atoms, bonded to any carbon or heteroatom of the polymer skeleton via at least one linking group.
  • the pendant fatty chain may, for example, be functionalized.
  • the at least one structuring polymer may comprise at least one pendant fatty chain as defined above, at least one terminal fatty chain as defined above, or both, and one or both types of chains can be functionalized.
  • the at least one structuring polymer comprises at least two hydrocarbon-based repeating units.
  • the at least one structuring polymer comprises at least three hydrocarbon-based repeating units and as an even further example, the at least three repeating units are identical.
  • “functionalized” means comprising at least one functional (reactive) group.
  • functional groups include hydroxyl groups, ether groups, oxyalkylene groups, polyoxyalkylene groups, carboxylic acid groups, amine groups, amide groups, halogen containing groups, including fluoro and perfluoro groups, halogen atoms, ester groups, siloxane groups, and polysiloxane groups.
  • the expression "functionalized chain” means, for example, an alkyl chain comprising at least one functional group chosen, for example, from those recited above.
  • the hydrogen atoms of at least one alkyl chain may be substituted at least partially with fluorine atoms.
  • these chains may be linked directly to the polymer skeleton or via an ester function or a perfluoro group.
  • polymer means a compound containing at least 2 repeating units, such as, for example, a compound containing at least 3 repeating units, which may be identical.
  • hydrocarbon-based repeating unit includes a repeating unit comprising from 2 to 80 carbon atoms, such as, for example, from 2 to 60 carbon atoms.
  • the at least one hydrocarbon-based repeating unit may also comprise oxygen atoms.
  • the hydrocarbon-based repeating unit may be chosen from saturated and unsaturated hydrocarbon-based repeating units which in turn may be chosen from linear hydrocarbon-based repeating units, branched hydrocarbon-based repeating units, and cyclic hydrocarbon-based repeating units.
  • the at least one hydrocarbon-based repeating unit may comprise, for example, at least one heteroatom that is part of the polymer skeleton, i.e., not pendant.
  • the at least one heteroatom may be chosen, for example, from nitrogen, sulphur, and phosphorus.
  • the at least one heteroatom may be a nitrogen atom, such as a non-pendant nitrogen atom.
  • the at least one hydrocarbon-based repeating unit may comprise at least one heteroatom, with the proviso that the at least one heteroatom is not nitrogen.
  • the at least one heteroatom is combined with at least one atom chosen from oxygen and carbon to form a heteroatom group.
  • the heteroatom group comprises a carbonyl group.
  • the at least one repeating unit comprising at least one heteroatom may be chosen, for example, from amide groups, carbamate groups, and urea groups.
  • the at least one repeating unit comprises amide groups forming a polyamide skeleton.
  • the at least one repeating unit comprises carbamate groups and/or urea groups forming a polyurethane skeleton, a polyurea skeleton, and/or a polyurethane- polyurea skeleton.
  • the pendant chains for example, can be linked directly to at least one of the heteroatoms of the polymer skeleton.
  • the at least one hydrocarbon-based repeating unit may comprise at least one heteroatom group, with the proviso that the at least one heteroatom group is not an amide group.
  • the polymer skeleton comprises at least one repeating unit chosen from silicone units and oxyalkylene units, and wherein the at least one repeating unit may be located between the hydrocarbon-based repeating units.
  • compositions of the invention comprise at least one structuring polymer with nitrogen atoms, such as amide, urea, or carbamate units, such as amide units, and at least one polar oil.
  • the percentage of the total number of fatty chains ranges from 40% to 98% relative to the total number of repeating units and fatty chains, and as a further example, from 50% to 95%.
  • the polymer skeleton is a polyamide skeleton
  • the percentage of the total number of fatty chains ranges from 40% to 98% relative to the total number of all amide units and fatty chains, and as a further example, from 50% to 95%.
  • the nature and proportion of the at least one hydrocarbon-based repeating unit comprising at least one heteroatom depends on the nature of a liquid fatty phase of the composition and is, for example, similar to the nature of the liquid fatty phase.
  • the at least one structuring polymer e.g., a polyamide polymer
  • the invention is drawn to a structured composition containing at least one liquid fatty phase structured with at least one structuring polymer, wherein the at least one structuring polymer is a polyamide polymer comprising a polymer skeleton comprising at least one amide repeating unit and optionally at least one pendant fatty chain and/or at least one terminal chain that are optionally functionalized and comprise from 8 to 120 carbon atoms, bonded to at least one of the amide repeating units via at least one linking group.
  • the liquid fatty phase further may contain at least one organogellator for gelling the liquid fatty phase.
  • the pendant fatty chains may be linked to at least one of the nitrogen atoms in the amide repeating units.
  • the at least one structuring polymer e.g., a polyamide polymer
  • the weight-average molecular mass may range from 1000 to 30,000, such as from 2000 to 20,000, further such as from 2000 to 10,000.
  • the at least one structuring polymer e.g., a polyamide polymer
  • the at least one structuring polymer is not soluble in water or in an aqueous phase.
  • the at least one structuring polymer e.g., a polyamide polymer
  • the at least one structuring polymer e.g., a polyamide polymer
  • the at least one structuring polymer may, for example, be chosen from polyamide polymers.
  • a polyamide polymer may comprise, for example, a polymer skeleton which comprises at least one amide repeating unit, i.e., a polyamide skeleton.
  • the polyamide skeleton may further comprise at least one terminal fatty chain chosen from alkyl chains, for example, alkyl chains comprising at least four carbon atoms, and alkenyl chains, for example, alkenyl chains comprising at least four carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group, and/or at least one pendant fatty chain chosen from alkyl chains, for example, alkyl chains comprising at least four carbon atoms, and alkenyl chains, for example, alkenyl chains comprising at least four carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group.
  • the polyamide skeleton may comprise at least one terminal fatty chain chosen from fatty chains comprising from 8 to 120 carbon atoms, such as, for example, from 12 to 68 carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group and/or at least one pendant fatty chain chosen from fatty chains comprising from 8 to 120 carbon atoms, such as, for example, from 12 to 68 carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group, such as bonded to any carbon or nitrogen of the polyamide skeleton via the at least one linking group.
  • the at least one linking group is chosen from single bonds and urea, urethane, thiourea, thiourethane, thioether, thioester, ester, ether and amine groups.
  • the at least one linking group is chosen from ureas, esters, and amines, and as a further example, is chosen from esters and amines.
  • the bond is, for example, an ester bond.
  • these polymers comprise a fatty chain at each end of the polymer skeleton, such as the polyamide skeleton.
  • the at least one structuring polymer e.g., a polyamide polymer
  • the at least one structuring polymer may be readily soluble in oils (i.e., water-immiscible liquid compounds) and thus may give macroscopically homogeneous compositions even with a high content (at least 25%) of the polyamide polymers, unlike certain polymers of the prior art that do not contain such alkyl or alkenyl chains at the end of the polyamide skeleton.
  • oils i.e., water-immiscible liquid compounds
  • a composition is soluble if it has a solubility of greater than 0.01 g per 100 ml of solution at 25°C.
  • the polyamide polymers can be chosen from polymers resulting from at least one polycondensation reaction between at least one acid chosen from at least one dicarboxylic acid comprising at least 32 carbon atoms, such as from 32 to 44 carbon atoms, and at least one amine chosen from diamines comprising at least 2 carbon atoms, such as from 2 to 36 carbon atoms, and triamines comprising at least 2 carbon atoms, such as from 2 to 36 carbon atoms.
  • the at least one dicarboxylic acid can, for example, be chosen from dimers of at least one fatty acid comprising at least 16 carbon atoms, such as oleic acid, linoleic acid, and linolenic acid.
  • the at least one amine can, for example, be chosen from diamines, such as ethylenediamine, hexylenediamine, hexamethylenediamine, phenylenediamine, and triamines.
  • the at least one amine can be ethylenetriamine.
  • the polyamide polymers may also be chosen from polymers comprising at least one terminal carboxylic acid group.
  • the at least one terminal carboxylic acid group can, for example, be esterified with at least one alcohol chosen from monoalcohols comprising at least 4 carbon atoms.
  • the at least one alcohol can be chosen from monoalcohols comprising from 10 to 36 carbon atoms.
  • the monoalcohols can comprise from 12 to 24 carbon atoms, such as from 16 to 24 carbon atoms, and, for example, 18 carbon atoms.
  • the at least one polyamide polymer may be chosen from those described in U.S. Patent No. 5,783,657, which are polymers of formula (I):
  • - n is an integer which represents the number of amide units such that the number of ester groups present in said at least one polyamide polymer ranges from 10% to 50% of the total number of all said ester groups and all said amide groups comprised in said at least one polyamide polymer;
  • R 1 which are identical or different, are each chosen from alkyl groups comprising at least 4 carbon atoms and alkenyl groups comprising at least 4 carbon atoms.
  • the alkyl group comprises from 4 to 24 carbon atoms and the alkenyl group comprises from 4 to 24 carbon atoms;
  • R 2 which are identical or different, are each chosen from C 4 to C 42 hydrocarbon-based groups, with the proviso that at least 50% of all R 2 are chosen from C 30 to C 2 hydrocarbon-based groups;
  • R 3 which are identical or different, are each chosen from organic groups comprising atoms chosen from carbon atoms, hydrogen atoms, oxygen atoms, and nitrogen atoms, with the proviso that R 3 comprises at least 2 carbon atoms;
  • R 4 which are identical or different, are each chosen from hydrogen atoms, C- ⁇ to C10 alkyl groups and a direct bond to at least one group chosen from R 3 and another R 4 such that when said at least one group is chosen from another R 4 , the nitrogen atom to which both R 3 and R 4 are bonded forms part of a heterocyclic structure defined in part by R 4 -N-R 3 , with the proviso that at least 50% of all R 4 are chosen from hydrogen atoms.
  • the at least one terminal fatty chain of formula (I) is linked to the last heteroatom, in this case nitrogen, of the polyamide skeleton.
  • the terminal chains are functionalized.
  • the ester groups of formula (I) which form part of the terminal and/or pendant fatty chains for purposes of the invention are present in amounts ranging from 15% to 40% of the total number of ester and amide groups (i.e., heteroatom groups), such as, for example, from 20% to 35%.
  • n may be an integer ranging from 1 to 10, for example an integer ranging from 1 to 5, and as a further example, an integer ranging from 3 to 5.
  • R 1 which are identical or different, can, for example, each be chosen from C-I2 to C22 alkyl groups, such as from C ⁇ 6 to C22 alkyl groups.
  • R 2 which are identical or different, can, for example, each be chosen from C 10 to C 42 alkyl groups. At least 50% of all R 2 , for example, at least 75% of all R 2 , which are identical or different, can, for example, each be chosen from groups comprising from 30 to 42 carbon atoms. In these embodiments, the remaining R 2 , which are identical or different, can, for example, each be chosen from C 4 to C 18 groups, such as from C 4 to C 12 groups.
  • R 3 which can be identical or different, can, for example, each be chosen from C 2 to C 36 hydrocarbon- based groups and polyoxyalkylene groups. In another embodiment, R 3 , which can be identical or different, can each, for example, be chosen from C 2 to C-12 hydrocarbon-based groups.
  • R 4 which can be identical or different, can each be chosen from hydrogen atoms.
  • hydrocarbon-based groups may be chosen from linear, cyclic, and branched, saturated and unsaturated groups.
  • the hydrocarbon-based groups can be chosen from aliphatic and aromatic groups. In one example, the hydrocarbon-based groups are chosen from aliphatic groups.
  • the alkyl and alkylene groups may be chosen from linear, cyclic, and branched, saturated and unsaturated groups.
  • the pendant and terminal fatty chains of the at least one structuring polymer may be chosen from linear, cyclic, and branched, saturated and unsaturated groups.
  • the pendant and terminal fatty chains can be chosen from aliphatic and aromatic groups. In one example, the pendant and terminal fatty chains are chosen from aliphatic groups.
  • the structuring of the liquid fatty phase is obtained with the aid of at least one structuring polymer, such as the at least one polyamide polymer of formula (I).
  • the at least one polyamide polymer of formula (I) may, for example, be in the form of a mixture of polymers, and this mixture may also comprise a compound of formula (I) wherein n is equal to zero, i.e., a diester.
  • Non-limiting examples of at least one polyamide polymer which may be used in the composition according to the present invention include the commercial products made or sold by Arizona Chemical under the names Uniclear 80 and Uniclear 100. These are sold, respectively, in the form of an 80% (in terms of active material) gel in a mineral oil and a 100% (in terms of active material) gel. These polymers have a softening point ranging from 88 °C to 94 °C, and may be mixtures of copolymers derived from monomers of (i) C 3 6 diacids and (ii) ethylenediamine, and have a weight-average molecular mass of about 6000. Terminal ester groups result from esterification of the remaining acid end groups with at least one alcohol chosen from cetyl alcohol and stearyl alcohol. A mixture of cetyl and stearyl alcohols is sometimes called cetylstearyl alcohol.
  • polyamide polymers are those made or sold under the brand name Versamid by the companies General Mills Inc. and Henkel Corp. (Versamid 930, 744 or 1655) or by the company Olin Mathieson Chemical Corp. under the brand name Onamid, for example, Onamid S or C.
  • These resins have a weight- average molecular mass ranging from 6000 to 9000.
  • polyamides useful in the compositions of the invention include those made or sold by the company Arizona Chemical under the references Uni-Rez (2658, 2931 , 2970, 2621 , 2613, 2624, 2665, 1554, 2623, and 2662) and the product made or sold under the reference Macromelt 6212 by the company Henkel.
  • Uni-Rez 2658, 2931 , 2970, 2621 , 2613, 2624, 2665, 1554, 2623, and 2662
  • Macromelt 6212 by the company Henkel.
  • U.S. Patent No. 5,500,209 Such polyamides display high melt viscosity characteristics.
  • MACROMELT 6212 for example, has a high melt viscosity at 190°C of 30-40 poise (as measured by a Brookfield Viscometer, Model RVF #3 spindle, 20 RPM).
  • the at least one polyamide polymer may be chosen from polyamide resins from vegetable sources.
  • Polyamide resins from vegetable sources may be chosen from, for example, the polyamide resins of U.S. Patent Nos. 5,783,657 and 5,998,570.
  • the structuring polymers of the invention may be non-waxy polymers.
  • the at least one structuring polymer e.g., a polyamide polymer
  • the at least one structuring polymer may be present in the composition in an amount ranging, for example, from 0.5% to 80%, such as from 2% to 60%, and further such as from 5% to 40%, by weight, relative to the total weight of the composition.
  • the at least one structuring polymer, e.g., a polyamide polymer may be present in the composition in an amount ranging, for example, from 5% to 25% by weight, relative to the total weight of the composition.
  • the at least one structuring polymer in the composition according to the invention corresponds to the polyamide polymers of formula (I). Due to fatty chain(s), these polymers may be readily soluble in oils and thus lead to compositions that are macroscopically homogeneous even with a high content (at least 25%) of at least one structuring polymer.
  • the at least one structuring polymer, e.g., a polyamide polymer, in the compositions of the invention may have a softening point greater than 50°C, such as from 65°C to 190°C, further such as from 65°C to less than 150°C, and further such as from 70°C to less than 130°C, and even further such as from 80°C to 105°C.
  • This softening point may be lower than that of structuring polymers used in the art which may facilitate the use of the at least one structuring polymer of the present invention and may limit the degradation of the liquid fatty phase.
  • the softening point can be measured by the well-known art-recognized method of Differential Scanning Calorimetry ("DSC"), with a temperature rise ranging from 5 °C to 10 °C per minute.
  • DSC Differential Scanning Calorimetry
  • the at least one film-forming silicone resin useful in the compositions of the invention may be chosen from any silicone resin that has film forming properties.
  • the at least one film-forming silicone resin is chosen from silsesquioxanes and siloxysilicates.
  • silicone polymers or derivatives as film-forming agents in cosmetic compositions. See, e.g., U.S. Patent Nos. 5,965,112, 5,800,816, 5,911 ,974, and 5,959,009.
  • Silicone resin nomenclature is known in the art as "MDTQ” nomenclature, whereby a silicone resin is described according to the various monomeric siloxane repeating units which make up the polymer.
  • MDTQ denotes a different type of unit.
  • the symbol M denotes the monofunctional unit (CH3)3SiOi/2. This unit is considered monofunctional because the silicone atom only shares one oxygen for the formation of the chain.
  • the "M” unit can be represented as:
  • At least one of the methyl groups can be replaced, such as, for example, to give a unit with formula [R(CH 3 ) 2 ]SiO ⁇ / , as represented in the following structure:
  • R is other than a methyl group.
  • the symbol “D” denotes the difunctional unit (CH )2SiO 2 /2, where two of the available bonds from the silicone atom are used for binding to oxygen for the formation of the polymeric chain.
  • the “D” unit which is the major building block of dimethicone oils, can be represented as:
  • T denotes the trifunctional unit, (CH 3 )SiO 3/2 , where three of the available bonds from the silicone atom are used for binding to oxygen for the formation of the polymeric chain.
  • the "T” unit can be represented as:
  • any methyl group could be replaced in “D” or “T” with a group R which is other than methyl.
  • the symbol “Q” denotes a quadrifunctional unit SiO / 2 , where all four of the available bonds from the silicone atom are used for binding to oxygen for the formation of the polymeric chain.
  • the "Q" unit can be represented as:
  • each of the silicones will vary depending on the type of monomer, the type of substitution, the size of the polymeric chain, and the degree of cross linking or size of the side chain. Different properties are attained depending on whether the backbone is a silicone chain with carbon-based side chains or whether the backbone is carbon-based with silicone side chains.
  • the at least one film-forming silicone resin may, in one embodiment, be chosen from siloxysilicates and silsesquioxanes. Any siloxysilicates or silsesquioxanes that functions as a film-former is within the practice of the invention.
  • the at least one film-forming silicone resin is chosen from substituted siloxysilicates and silsesquioxanes.
  • a substituted siloxysilicate or a substituted silsesquioxane may be, for example, a siloxysilicate or a silsesquioxane where a methyl group has been substituted with a longer carbon chain such as an ethane, propane, or butane chain. The carbon chain may be saturated or unsaturated.
  • the at least one film-forming silicone resin is chosen from siloxysilicates such as trimethylsiloxysilicat.es, which are represented by the following formula: [(CH 3 ) 3 -Si-O] x -(SiO 4/2 ) y (MQ units), where x and y can have values ranging from 50 to 80.
  • a siloxysilicate may be chosen from any combination of M and Q units, such as, for example, [(R)3-Si-O] x -(SiO /2 )y, where R is chosen from methyl groups and longer carbon chains.
  • the film-forming silicone resin is chosen from silsesquioxanes that are represented by the following formula: (CH 3 SiO 3/2 ) x (T units), where x has a value of up to several thousand and the CH 3 may be replaced by an R, as described above for T units.
  • the silsesquioxane is chosen from polymethylsilsesquioxanes, which are silsesquioxanes that do not have a substituent replacing the methyl group.
  • the polymethylsilsesquioxanes useful in the present invention are film- formers and can, for example, have about 500 or less T units, such as, for example, from about 50 to about 500 T units.
  • the film forming silicone resins have a melting point ranging from about 40°C to about 80°C. These silicone resins are soluble or dispersible in volatile silicones or other organic liquids.
  • the at least one film-forming silicone resins may be solid at about 25°C.
  • the at least one film-forming silicone resins may have a molecular weight ranging from 1000 to 10,000 grams/mole.
  • the at least one film-forming silicone resin is present in the composition in an amount ranging from 0.5% to 20% by weight, relative to the total weight of the composition, such as, for example, ranging from1% to 10%.
  • polymethylsilsesquioxanes are film-formers.
  • T Resins such as TospearlTM from Toshiba or KMP590 from Shin-Etsu are highly insoluble, and therefore are not effective film-formers.
  • the molecular weight of these polymethylsilsesquioxanes is difficult to determine, and they generally contain a thousand or more T units.
  • a polymethylsilsesquioxane useful in accordance with the present invention is Belsil PMS MK, also referred to as Resin MK, available from Wacker Chemie.
  • This polymethylsilsesquioxane is a polymer primarily formed of polymerized repeating units of CH3SiO 3/ 2 (T units), and which can also contain up to about 1 % (by weight or by mole) of (CHs) 2 SiO 2/2 (D units). It is believed that the polymers are in a "cage” and “ladder” configuration, as exemplified in the figure below. The weight-average molecular weight of the "cage" unit has been calculated to be 536.
  • the majority of the polymer is in the "ladder" configuration, where the ends are capped with ethoxy (CH 3 CH 2 O) groups.
  • the weight percent of ethoxy present is about 4.5%, and the mole percent is about 7% (silicone units). Since this functionality can react with water, a small and variable amount of SiOH can also be present.
  • the weight-average molecular weight can be, for example, from about 500 to about 50,000, such as about 10,000.
  • Polymethylsilsesquioxanes suitable for use in the present invention also include KR-220L available from SHIN-ETSU.
  • the structure of KR-220L is made up of mostly silicone T-units (CH 3 Si ⁇ 3 2), with Si-OH or silanol end units. There are no D units.
  • Other polymethylsilsesquioxanes that can be useful in the practice of the invention include KR-242A, which has a structure of about 98% methyl T units and about 2% dimethyl D units, with Si-OH or silanol end units, and KR-251 , which has a structure of about 88% methyl T units and about 12% dimethyl D units, with Si-OH or silanol end units, both of which are available from SHIN-ETSU.
  • the at least one film-forming silicone resin is chosen from combinations of M, D, T, and Q units comprising at least two units chosen from M, D, T, and Q, which satisfy the relationship R n SiO( 4 -n) /2 wherein n is a value ranging from 1.0 to 1.50.
  • R may be a methyl group or any carbon chain as long as the silicone resin retains its film-forming properties. Up to 5% of silanol or alkoxy functionality may also be present in the resin structure as a result of processing.
  • the at least one film-forming silicone resin comprises repeating M units and Q units.
  • the ratio of M units to Q units may be, for example, about 0.7:1.
  • the at least one film-forming silicone resin may be chosen, for example, from Wacker 803 and 804, available from Wacker Silicones Corporation and G.E. 1170-002 from General Electric.
  • the at least one film-forming silicone resin is a copolymer, wherein at least one unit of the copolymer is chosen from M, D, T, and Q silicone units, and wherein at least one additional unit of the copolymer is chosen from an ester.
  • the at least one film-forming silicone resin may be chosen from, for example, diisostearoyl trimethylolpropane siloxysilicates, such as SF 1318, available from GE Silicones.
  • compositions according to the present invention can additionally comprise at least one additional film-former.
  • the at least one additional film- former may improve, for example, smoothness or spreadability, water- resistance, transfer resistance properties, or other cosmetic or pharmaceutical properties desired by one of skill in the art.
  • the at least one additional film former may be chosen from, for example, polyethylene, vinylpyrrolidone/vinyl acetate (PVP VA) copolymers such as the Luviskol® VA grades (all ranges) from BASF ® Corporation and the PVP/VA series from ISP, acrylic fluorinated emulsion film formers including Foraperle® film formers such as Foraperle® 303 D from Elf Atochem (although Foraperle® may not be appropriate for some cosmetic formulations) GANEX ® copolymers such as butylated PVP, PVP/Hexadecene copolymer, PVP/Eicosene copolymer or tricontanyl, Poly(vinylpyrrolidone/
  • the at least one additional film former which also may be used within the framework of the invention includes film formers having any film former chemistry known in the art such as, for example, PVP, acrylates, urethane, synthetic polymers of the polycondensate type, free-radical type, or ionic type, polymers of natural origin, and mixtures thereof, as well as any other film former known within the practice of the cosmetic and pharmaceutical arts which one skilled in the art may determine to be compatible.
  • film formers having any film former chemistry known in the art such as, for example, PVP, acrylates, urethane, synthetic polymers of the polycondensate type, free-radical type, or ionic type, polymers of natural origin, and mixtures thereof, as well as any other film former known within the practice of the cosmetic and pharmaceutical arts which one skilled in the art may determine to be compatible.
  • the at least one additional film-former may be determined by one of skill in the art, and can vary considerably based on the application.
  • the at least one additional film-former may be used in an amount ranging from 0.1% to 20%, such as, for example, ranging from 1 % to 10%, by weight, relative to the total weight of the composition.
  • the amounts of the at least one film-forming silicone resin and of the at least one structuring polymer, e.g., a polyamide polymer, may be chosen according to the desired hardness and desired stability of the compositions, and according to the specific application envisaged.
  • the respective amounts of the at least one structuring polymer, e.g., a polyamide polymer, and of the at least one film-forming silicone resin can be such that a disintegrable solid which does not flow under its own weight is obtained.
  • hardness of the composition may be considered.
  • the hardness of a composition may, for example, be expressed in gram force (gf).
  • compositions of the present invention may, for example, have a hardness ranging from 20 gf to 2000 gf, for example, ranging from 20 gf to 900 gf, and further, such as, for example ranging from 20 gf to 600 gf.
  • a first test for hardness is according to a method of penetrating a probe into the composition and in particular using a texture analyzer (for example TA-XT2i from Rheo) equipped with an ebonite cylinder of height 25 mm and diameter 8 mm.
  • the hardness measurement is carried out at 20 °C at the center of 5 samples of the composition.
  • the cylinder is introduced into each sample of composition at a pre-speed of 2 mm/s, and then at a speed of 0.5 mm/s, and finally at a post-speed of 2 mm/s, the total displacement being 1 mm.
  • the recorded hardness value is that of the maximum peak observed.
  • the measurement error is ⁇ 50gf.
  • a second test for hardness is the "cheese wire” method, which involves cutting an 8.1 mm or 12.7 mm stick of composition and measuring its hardness at 20°C using a DFGHS 2 tensile testing machine from Indelco- Chatillon Co. at a speed of 100 mm/minute.
  • the hardness value from this method is expressed in gram force as the shear force required to cut a stick under the above conditions.
  • the hardness of compositions according to the present invention which may be in stick form may, for example, range from 30 gf to 300 gf, such as from 30 gf to 250 gf, and further, such as from 30 gf to 200 gf.
  • the hardness of the composition of the present invention may be such that the compositions are self-supporting and can easily disintegrate to form a satisfactory deposit on keratinous materials.
  • this hardness may impart good impact strength to the inventive compositions which may be molded or cast, for example, in stick or dish form.
  • the skilled artisan may choose to evaluate a composition using at least one of the tests for hardness outlined above based on the application envisaged and the hardness desired. If one obtains an acceptable hardness value, in view of the intended application, from at least one of these hardness tests, the composition falls within the scope of the invention.
  • compositions in stick form may also possess the properties of deformable, flexible elastic solids and may also have noteworthy elastic softness upon application to keratinous materials.
  • the compositions in stick form of the prior art do not have this elasticity and flexibility.
  • the at least one liquid fatty phase may comprise at least one oil.
  • the at least one oil may have an affinity with the at least one structuring polymer, e.g., a polyamide polymer,.
  • the at least one oil may, for example, be chosen from polar oils and apolar oils, including hydrocarbon-based liquid oils and oily liquids at room temperature.
  • the compositions of the invention comprise at least one structuring polymer, e.g., a polyamide polymer, and at least one polar oil.
  • the polar oils of the invention may, for example, be added to the apolar oils, the apolar oils may act as co-solvent for the polar oils.
  • the structuring of the at least one liquid fatty phase may, for example, be obtained with the aid of at least one structuring polymer, such as the polyamide polymer of formula (I).
  • the polymers of formula (I) may be in the form of mixtures of polymers, these mixtures also possibly containing a synthetic product corresponding to a compound of formula (I) in which n is 0, i.e., a diester.
  • the liquid fatty phase of the composition may contain more than 30%, for example, more than 40%, of liquid oil(s) having a chemical nature similar to that of the skeleton of the at least one structuring polymer, and, for example, from 50% to 99.4%.
  • the liquid fatty phase structured with a polyamide-type skeleton contains a high quantity, i.e., greater than 30%, for example greater than 40%, relative to the total weight of the liquid fatty phase, or, for example, from 50% to 99.4%, of at least one apolar, such as hydrocarbon-based, oil.
  • hydrocarbon-based oil means an oil comprising carbon and hydrogen atoms, optionally with at least one group chosen from hydroxyl, ester, carboxyl, and ether groups.
  • this fatty phase may contain more than 30%, for example, more than 40%, relative to the total weight of the liquid fatty phase and, for example, from 50% to 99.4%, of at least one silicone- based liquid oil, relative to the total weight of the liquid fatty phase.
  • this fatty phase may contain more than 30%, for example more than 40% by weight, or, for example, from 50% to 99.4% by weight, of at least one liquid apolar, such as hydrocarbon-based, oil, relative to the total weight of the liquid fatty phase.
  • the at least one polar oil useful in the invention may be chosen from:
  • oils with a high content of triglycerides comprising fatty acid esters of glycerol in which the fatty acids may have varied chain lengths from C 4 to C 24 , these chains possibly being chosen from linear and branched, and saturated and unsaturated chains; these oils are chosen from, for example, wheat germ oil, corn oil, sunflower oil, karite butter, castor oil, sweet almond oil, macadamia oil, apricot oil, soybean oil, cotton oil, alfalfa oil, poppy oil, pumpkin oil, sesame oil, marrow oil, rapeseed oil, avocado oil, hazelnut oil, grape seed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, olive oil, rye oil, safflower oil, candlenut oil, passion flower oil and musk rose oil; or alternatively caprylic/capric acid triglycerides such as those made or sold by Stearineries Dubois, or those
  • R 5 COOR 6 in which R 5 is chosen from cyclic, linear, and branched fatty acid residues containing from 1 to 40 carbon atoms, and Re is chosen from, for example, a hydrocarbon-based chain containing from 1 to 40 carbon atoms, for example, 1-4 carbon atoms, on condition that R 5 + R 6 > 10, such as, for example, purcellin oil (cetostearyl octanoate), isononyl isononanoate, C ⁇ 2 -C-
  • - Cs to C 26 fatty acids such as oleic acid, linolenic acid or linoleic acid.
  • the at least one apolar oil according to the invention may be chosen from, for example, silicone oils chosen from volatile and non-volatile, linear, branched, and cyclic polydimethylsiloxanes (PDMSs) that are liquid at room temperature; polydimethylsiloxanes comprising alkyl or alkoxy groups which are pendant and/or at the end of the silicone chain, the groups each containing from 2 to 24 carbon atoms; phenylsilicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes and 2- phenylethyl trimethylsiloxysilicates; hydrocarbons chosen from cyclic, linear and branched, volatile and non-volatile hydrocarbons of synthetic and mineral origin, such as volatile liquid paraffins (such as isoparaffins and isod
  • the structured oils for example those structured with polyamides such as those of formula (I), or the polyurethanes, polyureas, or polyurea-urethanes, may be, in one embodiment, apolar oils, such as an oil or a mixture of hydrocarbon oils chosen from those of mineral and synthetic origin, chosen from hydrocarbons such as alkanes such as Parieam® oil, isoparaffins including isododecane, and squalane, and mixtures thereof. These oils may, in one embodiment, be combined with at least one phenylsilicone oil.
  • apolar oils such as an oil or a mixture of hydrocarbon oils chosen from those of mineral and synthetic origin, chosen from hydrocarbons such as alkanes such as Parieam® oil, isoparaffins including isododecane, and squalane, and mixtures thereof.
  • the liquid fatty phase in one embodiment, contains at least one non-volatile oil chosen from, for example, hydrocarbon-based oils of mineral, plant and synthetic origin, synthetic esters or ethers, silicone oils and mixtures thereof.
  • the total liquid fatty phase may be present, for example, in an amount ranging from 1% to 99.4% by weight, relative to the total weight of the composition, for example, ranging from 5% to 99.4%, such as ranging from 5% to 95.5%, ranging from 10% to 80%, and further ranging from 20% to 75%.
  • volatile solvent or oil means any non-aqueous medium capable of evaporating on contact with the skin or the lips in less than one hour at room temperature and atmospheric pressure.
  • the volatile solvent(s) of the invention is(are) organic solvents, such as volatile cosmetic oils that are liquid at room temperature, having a non-zero vapor pressure at room temperature and atmospheric pressure, ranging, for example, from 10 "2 to 300 mmHg (1.33 Pa to 10,000 Pa) and, as a further example, greater than 0.3 mmHg (4Pa).
  • non-volatile oil means an oil which remains on the skin or the lips at room temperature and atmospheric pressure for at least several hours, such as those having a vapor pressure of less than 10 "2 mmHg (1.33Pa).
  • these volatile solvents or oils may facilitate the staying power or long wearing properties of the composition on the keratinous materials.
  • the solvents can be chosen from hydrocarbon-based solvents, silicone solvents optionally comprising alkyl or alkoxy groups that are pendant or at the end of a silicone chain, and a mixture of these solvents.
  • the volatile oil(s), in one embodiment, may be present in an amount ranging up to and including 95.5%, relative to the total weight of the composition, such as, for example, from 2% to 75% or, as a further example, from 10% to 45%. This amount will be adapted by a person skilled in the art according to the desired staying power or long wearing properties.
  • the at least one liquid fatty phase of the compositions of the invention may further comprises a dispersion of lipid vesicles.
  • the compositions of the invention may also, for example, be in the form of a fluid anhydrous gel, a rigid anhydrous gel, a fluid simple emulsion, a fluid multiple emulsion, a rigid simple emulsion or a rigid multiple emulsion.
  • the simple emulsion or multiple emulsion may comprise a continuous phase chosen from an aqueous phase optionally containing dispersed lipid vesicles, or a fatty phase optionally containing dispersed lipid vesicles.
  • the composition has a continuous oily phase or fatty phase and is an anhydrous composition, for example, in stick or dish form.
  • An anhydrous composition is one that has less than 10% water by weight, such as, for example, less than 5% by weight. Additional Components
  • compositions of the invention may further comprise at least one additional fatty material.
  • the at least one additional fatty material may, for example, be chosen from gums, fatty materials that are pasty or viscous at ambient temperature, and resins.
  • compositions of the invention should be cosmetically and/or dermatologically acceptable, i.e., they should contain a non-toxic physiologically acceptable medium and should be able to be applied to human keratinous materials.
  • the composition of the present invention in one embodiment, may comprise a physiologically acceptable medium, e.g., a physiologically acceptable oil or solvent.
  • a physiologically acceptable medium e.g., a physiologically acceptable oil or solvent.
  • cosmetically and/or dermatologically acceptable means that compositions of the invention have a pleasant appearance, odor, and taste.
  • compositions of the present invention may also further comprise at least one suitable additive commonly used in the field concerned chosen from coloring agents, antioxidants, essential oils, preserving agents, fragrances, fillers, pasty fatty substances, waxy fatty substances, neutralizing agents, liposoluble or lipodispersible gelling agents, liposoluble polymers, and cosmetically active agents and dermatological active agents, i.e., an agent having a beneficial effect on keratinous materials, such as, for example, emollients, moisturizers, vitamins, essential fatty acids, and sunscreens.
  • the compositions of the invention may also further comprise water, optionally thickened with an aqueous-phase thickener or gelled with a hydrophilic gelling agent and/or containing ingredients soluble in water.
  • the at least one additive may be present in an amount ranging from 0.01 % to 20%, such as, for example, from 0.01% to 10%, by weight, relative to the total weight of the composition.
  • the at least one suitable additive is chosen from at least one wax.
  • a "wax" may be any lipophilic fatty compound which is soluble in the liquid fatty phase, unlike most fillers of pigments.
  • Non- limiting examples of such waxes include waxes of natural origin, such as beeswax, camauba wax, candelilla wax, ouricury wax, Japan wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite wax, microcrystalline waxes, lanolin wax, montan wax and ozokerites, hydrogenated oils such as hydrogenated jojoba oil, jojoba esters, waxes of synthetic origin, such as polyethylene waxes derived from polymerization of ethylene, waxes obtained by Fischer-Tropsch synthesis, fatty acid esters and glycerides, and silicone waxes such as derivatives of poly(di)methylsiloxane.
  • the at least one wax may be present in the composition in an amount up to 3%, and in another embodiment, in an amount of at least 3%, such as up to 30% or up to 50%. In one embodiment, th e wax may be present in an amount ranging from 0.05% to 15% relative to the total weight of the composition, such as from 0.1% to 10%.
  • the at least one wax may, for example, have a melting point greater then about 45°C, such as, for example, greater than about 55°C.
  • compositions of the invention may also comprise at least one coloring agent chosen from pigments, dyes, nacreous pigments (i.e., nacres), and pearling agents.
  • the at least one coloring agent may be chosen, for example, in order to obtain make-up compositions which give good coverage, that is, which do not leave a significant amount of the at least one keratinous material to which it is applied showing through.
  • the pigments may also reduce the sticky feel of the compositions, unlike soluble dyes.
  • the coloring agents are pigments (nacreous or non-nacreous).
  • liposoluble dyes which may be used according to the present invention include Sudan red, DC Red 17, DC Green 6, ⁇ -carotene, soybean oil, Sudan brown, DC Yellow 11 , DC Violet 2, DC Orange 5, quinoline yellow, and annatto.
  • the liposoluble dyes when present, may be present in an amount ranging up to 20% by weight of the total weight of the composition, such as from 0.1% to 6%.
  • the pigments which may be used according to the present invention may be chosen from white, colored, mineral, organic, coated and uncoated pigments.
  • mineral pigments include titanium dioxide, optionally surface-treated, zirconium oxide, zinc oxide, cerium oxide, iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • organic pigments include carbon black, pigments of D & C type, and lakes based on cochineal carmine, barium, strontium, calcium and aluminum. If present, the pigments may have an amount ranging up to 40% by weight of the total weight of the composition, such as from 1% to 35%, and further such as from 2% to 25%.
  • the nacreous pigments (or nacres) which may be used according to the present invention may be chosen from white nacreous pigments such as mica coated with titanium or with bismuth oxychloride, colored nacreous pigments such as titanium mica with iron oxides, titanium mica with ferric blue or chromium oxide, titanium mica with an organic pigment chosen from those mentioned above, and nacreous pigments based on bismuth oxychloride.
  • the nacres, if present, may have an amount ranging up to 30% by weight of the total weight of the composition, such as from 0.1 % to 20%.
  • the coloring agents are pigments.
  • An embodiment of the invention relates to a keratinous material care, make-up, or treatment composition
  • a structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer, e.g., a polyamide polymer, comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, and at least one film-forming silicone resin.
  • structuring polymer e.g., a polyamide polymer, comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, and at least one film-forming silicone resin.
  • an embodiment of the invention relates to a keratinous material care make-up, or treatment composition
  • a structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer comprising a polymer skeleton, e.g., a polyamide polymer, comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, at least one film-forming silicone resin, and at least one coloring agent.
  • an embodiment of the invention relates to a method of caring for, treating, or making up at least one keratinous material comprising applying to the at least one keratinous material a structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer, e.g., a polyamide polymer, comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, and at least one film-forming silicone resin.
  • a structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer, e.g., a polyamide polymer, comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, and at least one film-forming silicone resin.
  • One embodiment of the present invention is a cosmetic process for caring for, making up, or treating at least one keratinous material, such as that of a human being, comprising the application to the at least one keratinous material a cosmetic composition comprising at least one polyamide polymer comprising a polyamide skeleton and at least one film- forming silicone resin.
  • the polyamide skeleton comprises at least one end group with at least one chain chosen from alkyl chains comprising at least four carbon atoms and alkenyl chains comprising at least four carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group.
  • the polyamide skeleton may further comprise at least one pendant group with at least one chain chosen from alkyl chains comprising at least four carbon atoms and alkenyl chains comprising at least four carbon atoms, bonded to any carbon or nitrogen of the polyamide skeleton via at least one linking group.
  • the present invention is directed to a process of making a cosmetic composition in the form of a physiologically acceptable composition, comprising including in the composition at least one structuring polymer, e.g., a polyamide polymer, comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom.
  • the polymer skeleton comprises at least one end group with at least one chain chosen from alkyl chains comprising at least four carbon atoms and alkenyl chains comprising at least four carbon atoms, bonded to the at least one polymer skeleton via at least one linking group.
  • the polymer skeleton may further comprise at least one pendant group with at least one chain chosen from alkyl chains comprising at least four carbon atoms and alkenyl chains comprising at least four carbon atoms, bonded to any carbon or heteroatom of the polymer skeleton via at least one linking group.
  • the composition also comprises at least one film-forming silicone resin.
  • Another embodiment of the invention relates to a lip composition in stick form comprising at least one continuous liquid fatty phase, at least one film-forming silicone resin and at least one non-waxy structuring polymer having a weight-average molecular mass of less than 100,000.
  • the packaging and application device for any subject of the invention may be chosen and manufactured by persons skilled in the art on the basis of their general knowledge, and adapted according to the nature of the composition to be packaged. Indeed, the type of device to be used can be, for example, linked to the consistency of the composition,, for example, to its viscosity; it can also depend on the nature of the constituents present in the composition, such as the presence of volatile compounds.
  • a transfer resistant mascara was prepared by mixing the following ingredients. PHASE INCI NAME w/w%
  • Phases A, B, and C were each prepared separately by mixing together the ingredients of each phase. The three phases were then combined and the resulting mascara was found to have transfer resistant properties upon application to eye lashes.
  • a transfer resistant mascara was prepared from the following ingredients. PHASE INCI NAME w/w%
  • Phase A was mixed with a homogenizer for 20 minutes at room temperature and then heated to 65°C for 15 minutes. In a separate beaker, phase C was combined with propeller mixing and heated to 85-90°C. Once phase A and phase C reached their respective temperatures, phase C was added to phase A. The batch was homogenized for 5 minutes while maintaining the heat at 80-85°C and phase B was added. The mixture was homogenized for 30 minutes at 80-85°C and then removed from the homogenizer and cooled to 30-35°C using sweep mixing. The ingredients were combined and the resulting mascara was found to have transfer resistant properties upon application to eye lashes.

Abstract

Compositions, in one embodiment a transfer resistant cosmetic composition, which may also be pliable and comfortable to wear upon application to a substrate. The compositions comprise at least one structuring polymer and at least one film-forming silicone resin. The at least one structuring polymer may be a polyamide polymer. The invention, in one embodiment, relates to cosmetic, dermatological, and pharmaceutical products containing this composition.

Description

COSMETIC COMPOSITIONS CONTAINING AT LEAST ONE
HETERO POLYMER AND AT LEAST ONE FILM-FORMING
SILICONE RESIN AND METHODS OF USING
The present invention relates to compositions and methods for caring for, treating, and making up at least one keratinous material, for example at least one human keratinous material, such as skin, including the scalp, lips, superficial body growths, including the nails, and/or at least one keratinous fiber, which includes the hair, eyelashes, and eyebrows. In one embodiment of the invention, the compositions are transfer resistant cosmetic compositions. In another embodiment of the invention, the compositions are pliable and/or comfortable to wear upon application. The compositions, in one embodiment, comprise at least one structuring polymer and at least one film-forming silicone resin. The invention, in one embodiment, relates to cosmetic, dermatological, and pharmaceutical products containing this composition. Due to the good stability of the compositions of the invention, it is possible to add at least one UV blocker to the composition. As used herein, the expression "at least one" means one or more and thus, includes individual components as well as mixtures/combinations.
Many cosmetic compositions, including pigmented cosmetics such as foundations, concealers, lipsticks, mascaras, and other cosmetic and sunscreen compositions, have been developed for longer wear and non- transfer properties. This is accomplished by the use of compositions that form a film after application. Such compositions generally contain volatile solvents which evaporate on contact with the skin or other keratinous materials, leaving behind a layer comprising waxes and/or resins, pigments, fillers, and actives. However, these compositions tend to be uncomfortable for the wearer as the compositions remain on the skin or other keratinous materials as a brittle or non-flexible film. Such compositions may not be either pliable or soft, and they may not be comfortable to wear. There may also be a tendency for such compositions to flake off because of poor adherence to the skin or other keratinous materials. Furthermore, compositions may have a tendency to be tacky, resulting in poor application and spreadability characteristics.
The need therefore still remains for improved long-wearing cosmetic compositions which transfer little or not at all, i.e., "transfer-free" or transfer resistant compositions, which also possess good cosmetic properties such as pliability and comfort. For example, a composition which is transfer resistant may deposit a film onto keratinous materials which may not transfer when the keratinous materials comes into contact with, for example, other keratinous materials, such as skin, or with a cup, paper, a cigarette, or a handkerchief.
The transfer resistance of a composition may be evaluated by an art recognized transfer resistance test. In one such test, a composition is applied to the clean, bare skin of a group of subjects as a smooth, thin layer, such as a 1" x 1" square in size. The composition is allowed to air dry for 5 minutes, and using a facial tissue or other cloth or sponge and medium pressure, the area is wiped as if attempting to wipe the product off of the skin. The subjects are then asked to evaluate the results. Positive results are described as the presence of a makeup film that could not be easily removed without soap and water. For example, the results may be rated on a scale of 1 to 5 with 5 being the best and 1 being the worst.
To achieve at least one of the foregoing advantages, the present invention, in one embodiment, provides compositions comprising at least one structuring polymer, e.g., a polyamide polymer, comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom. The compositions also comprise at least one liquid fatty phase comprising at least one film-forming silicone resin. The present invention also relates to methods for making such compositions.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only, and are not restrictive of the invention. The invention, in one embodiment, provides compositions comprising combinations of at least one structuring polymer, e.g., a polyamide polymer, and at least one film-forming silicone resin. In one embodiment, the at least one structuring polymer, e.g., a polyamide polymer, and the at least one film- forming silicone resin are present in an amount effective to provide transfer resistant properties, and may also provide at least one of the following properties: pliability, softness, and wearing comfort.
One subject of the invention is cosmetic and/or dermatological compositions which are useful for the care, make-up and/or treating of at least one keratinous material, which compositions may be of suitable hardness to allow their preparation in the form of a stick or other structured form, which may be stable.
As defined herein, stability can be tested by placing the composition in a controlled environment chamber for 8 weeks at 25°C. In this test, the physical condition of the sample is inspected as it is placed in the chamber. The sample is then inspected again at 24 hours, 3 days, 1 week, 2 weeks, 4 weeks and 8 weeks. At each inspection, the sample is examined for abnormalities in the composition such as bending or leaning if the composition is in stick form, phase separation, melting, or syneresis. As used herein, syneresis is the appearance of droplets on the surface of a composition that are visible to the naked eye. The stability is further tested by repeating the 8 week test at 4°C, 37°C, 45°C, 50°C, and under freeze-thaw conditions. A composition is considered to lack stability if in any of these tests an abnormality that impedes functioning of the composition is observed. The skilled artisan will readily recognize an abnormality that impedes functioning of a composition based on the intended application.
Structured liquid fatty phases in cosmetic or dermatological products are known in the art. Structured liquid fatty phases may be found, for example, in solid compositions such as deodorants, balms, lip compositions, concealer products, and cast foundations. The compositions of the invention, in one embodiment, may comprise at least one liquid fatty phase. As used herein, "liquid fatty phase" means a fatty phase which is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg, i.e., 101 kPa) and which is composed of at least one fatty substance, such as an oil, which is liquid at room temperature and not soluble in water. If the at least one liquid fatty phase comprises two or more fatty substances, they should be mutually compatible, i.e., forming a homogenous phase macroscopically.
Structured liquid fatty phases may make it possible to control the exudation of the liquid fatty phase from the solid compositions of which they are components, including exudation in a wet or hot atmosphere or environment. Structuring of the liquid fatty phase may also limit bleeding of this phase outside of the intended area of application and especially into wrinkles and fine lines after it has been deposited, for example, on keratinous materials. As used herein, "keratinous material" is meant to comprise hair, lips, skin, scalp and superficial body growths such as eyelashes, eyebrows, and nails.
The invention applies not only to make-up products for at least one keratinous material such as lip compositions, lip pencils, foundations, including foundations which may be cast in the form of a stick or a dish, concealer products, temporary tattoo products, eyeliners, and mascara bars, but also to body hygiene products such as deodorant sticks, and to care products and products for treating at least one keratinous material such as sunscreen and after-sun products which may be in stick form. The present invention may be in the form of a mascara product including mascara bars, an eyeliner product, a foundation product, a lipstick product, a blush for cheeks or eyelids, a deodorant product, a make-up product for the body, a make-up- removing product, an eyeshadow product, a face powder product, a concealer product, a treating shampoo product, a hair conditioning product, a sunscreen (antisun) product, a colorant for the skin or hair, or a skin care formula such as, for example, anti-pimple or shaving cut formulas. As defined herein, a deodorant product is a body hygiene product and does not relate to care, make-up, or treatment of keratinous materials, including keratinous fibers, skin, or lips.
For example, the composition of the present invention may be in a form chosen from a paste, a solid, a gel, and a cream. It may also be an emulsion, such as an oil-in-water or water-in-oil emulsion, a multiple emulsion, such as an oil-in-water-in-oil emulsion or a water-in-oil-in-water emulsion, or a solid, rigid or supple gel, including anhydrous gels. In one embodiment, the composition of the invention is anhydrous. The composition of the invention may, for example, comprise an external or continuous liquid fatty phase. By "external or continuous" phase, it is meant, by way of example, the water phase in a water-in-oil emulsion, wherein the oil droplets are dispersed throughout the external or continuous water phase.
In another embodiment, the composition of the invention is transparent or clear, including for example, a composition without pigments. The composition can also be in a form chosen from a translucent anhydrous gel and a transparent anhydrous gel. The composition can also be a molded composition or cast as a stick or a dish. The composition in one embodiment is a solid such as a molded stick or a poured stick. Structuring polymer
In one embodiment, the at least one structuring polymer in the composition of the invention is a solid that is not deformable at room temperature (25°C) and atmospheric pressure (760 mmHg, i.e., 101 kPa). In a further embodiment, the at least one structuring polymer is capable of structuring the composition without opacifying it. This may be due to the fact that the polymer does not crystallize. Moreover, the structuring of the liquid fatty phase comprising the at least one structuring polymer may be due to the hydrogen interactions between two molecules of the polymer and/or between the molecules of the polymer and the liquid fatty phase. As defined above, the at least one structuring polymer of the present invention comprises a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom. In one embodiment, the at least one structuring polymer further comprises at least one terminal fatty chain chosen from alkyl and alkenyl chains, such as of at least 4 carbon atoms, and further such as comprising from 8 to 120 carbon atoms, bonded to the polymer skeleton via at least one linking group. The terminal fatty chain may, for example, be functionalized. The at least one structuring polymer may also further comprise at least one pendant fatty chain chosen from alkyl and alkenyl chains, such as of at least 4 carbon atoms, and further such as comprising from 8 to 120 carbon atoms, bonded to any carbon or heteroatom of the polymer skeleton via at least one linking group. The pendant fatty chain may, for example, be functionalized. The at least one structuring polymer may comprise at least one pendant fatty chain as defined above, at least one terminal fatty chain as defined above, or both, and one or both types of chains can be functionalized.
In one embodiment, the at least one structuring polymer comprises at least two hydrocarbon-based repeating units. As a further example, the at least one structuring polymer comprises at least three hydrocarbon-based repeating units and as an even further example, the at least three repeating units are identical.
As used herein, "functionalized" means comprising at least one functional (reactive) group. Non-limiting examples of functional groups include hydroxyl groups, ether groups, oxyalkylene groups, polyoxyalkylene groups, carboxylic acid groups, amine groups, amide groups, halogen containing groups, including fluoro and perfluoro groups, halogen atoms, ester groups, siloxane groups, and polysiloxane groups.
For purposes of the invention, the expression "functionalized chain" means, for example, an alkyl chain comprising at least one functional group chosen, for example, from those recited above. For example, in one embodiment, the hydrogen atoms of at least one alkyl chain may be substituted at least partially with fluorine atoms.
According to the invention, these chains may be linked directly to the polymer skeleton or via an ester function or a perfluoro group.
For the purposes of the invention, the term "polymer" means a compound containing at least 2 repeating units, such as, for example, a compound containing at least 3 repeating units, which may be identical.
As used herein to describe the structuring polymers, the expression "hydrocarbon-based repeating unit" includes a repeating unit comprising from 2 to 80 carbon atoms, such as, for example, from 2 to 60 carbon atoms. The at least one hydrocarbon-based repeating unit may also comprise oxygen atoms. The hydrocarbon-based repeating unit may be chosen from saturated and unsaturated hydrocarbon-based repeating units which in turn may be chosen from linear hydrocarbon-based repeating units, branched hydrocarbon-based repeating units, and cyclic hydrocarbon-based repeating units. The at least one hydrocarbon-based repeating unit may comprise, for example, at least one heteroatom that is part of the polymer skeleton, i.e., not pendant. The at least one heteroatom may be chosen, for example, from nitrogen, sulphur, and phosphorus. For example, the at least one heteroatom may be a nitrogen atom, such as a non-pendant nitrogen atom. In another embodiment, the at least one hydrocarbon-based repeating unit may comprise at least one heteroatom, with the proviso that the at least one heteroatom is not nitrogen. In another embodiment, the at least one heteroatom is combined with at least one atom chosen from oxygen and carbon to form a heteroatom group. In one embodiment, the heteroatom group comprises a carbonyl group.
The at least one repeating unit comprising at least one heteroatom may be chosen, for example, from amide groups, carbamate groups, and urea groups. In one embodiment, the at least one repeating unit comprises amide groups forming a polyamide skeleton. In another embodiment, the at least one repeating unit comprises carbamate groups and/or urea groups forming a polyurethane skeleton, a polyurea skeleton, and/or a polyurethane- polyurea skeleton. The pendant chains, for example, can be linked directly to at least one of the heteroatoms of the polymer skeleton. In yet another embodiment, the at least one hydrocarbon-based repeating unit may comprise at least one heteroatom group, with the proviso that the at least one heteroatom group is not an amide group. In one embodiment, the polymer skeleton comprises at least one repeating unit chosen from silicone units and oxyalkylene units, and wherein the at least one repeating unit may be located between the hydrocarbon-based repeating units.
In one embodiment, the compositions of the invention comprise at least one structuring polymer with nitrogen atoms, such as amide, urea, or carbamate units, such as amide units, and at least one polar oil.
In one embodiment, in the at least one structuring polymer, the percentage of the total number of fatty chains ranges from 40% to 98% relative to the total number of repeating units and fatty chains, and as a further example, from 50% to 95%. In a further embodiment wherein the polymer skeleton is a polyamide skeleton, in the at least one structuring polymer, the percentage of the total number of fatty chains ranges from 40% to 98% relative to the total number of all amide units and fatty chains, and as a further example, from 50% to 95%.
In a further embodiment, the nature and proportion of the at least one hydrocarbon-based repeating unit comprising at least one heteroatom depends on the nature of a liquid fatty phase of the composition and is, for example, similar to the nature of the liquid fatty phase. For example, and not to be limited as to theory, the at least one structuring polymer, e.g., a polyamide polymer, may have an affinity with the liquid fatty phase, and, for example, with a chemical portion of one of the oils forming the liquid fatty phase of the composition, so that physical links with the oils, such as hydrogen bonds, are formed. The more polar the hydrocarbon-based repeating units containing a heteroatom, and in high proportion, which corresponds to the presence of several heteroatoms, the greater the affinity the at least one structuring polymer may have for polar oils. Conversely, the more non-polar, or even apolar, and lesser in proportion the hydrocarbon- based repeating units containing a heteroatom, the greater the affinity the at least one structuring polymer may have for apolar oils.
In another embodiment, the invention is drawn to a structured composition containing at least one liquid fatty phase structured with at least one structuring polymer, wherein the at least one structuring polymer is a polyamide polymer comprising a polymer skeleton comprising at least one amide repeating unit and optionally at least one pendant fatty chain and/or at least one terminal chain that are optionally functionalized and comprise from 8 to 120 carbon atoms, bonded to at least one of the amide repeating units via at least one linking group. The liquid fatty phase further may contain at least one organogellator for gelling the liquid fatty phase. The at least one liquid fatty phase, the at least one structuring polymer, e.g., a polyamide polymer, and optionally the at least one organogellator, together form a physiologically acceptable medium.
When the at least one structuring polymer has amide repeating units, the pendant fatty chains may be linked to at least one of the nitrogen atoms in the amide repeating units.
In one embodiment, the at least one structuring polymer, e.g., a polyamide polymer, may have a weight-average molecular mass up to and including 1 ,000,000, such as, for example, up to and including 500,000, and as a further example, up to and including 100,000, and as a further example, up to and including 50,000. For example,the weight-average molecular mass may range from 1000 to 30,000, such as from 2000 to 20,000, further such as from 2000 to 10,000.
The at least one structuring polymer, e.g., a polyamide polymer, is not soluble in water or in an aqueous phase. In one embodiment of the invention, the at least one structuring polymer, e.g., a polyamide polymer, has no ionic groups or functions, i.e., is nonionic. In another embodiment, the at least one structuring polymer, e.g., a polyamide polymer, can have one ionizable function.
As discussed, the at least one structuring polymer may, for example, be chosen from polyamide polymers. A polyamide polymer may comprise, for example, a polymer skeleton which comprises at least one amide repeating unit, i.e., a polyamide skeleton. In one embodiment, the polyamide skeleton may further comprise at least one terminal fatty chain chosen from alkyl chains, for example, alkyl chains comprising at least four carbon atoms, and alkenyl chains, for example, alkenyl chains comprising at least four carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group, and/or at least one pendant fatty chain chosen from alkyl chains, for example, alkyl chains comprising at least four carbon atoms, and alkenyl chains, for example, alkenyl chains comprising at least four carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group. In one embodiment, the polyamide skeleton may comprise at least one terminal fatty chain chosen from fatty chains comprising from 8 to 120 carbon atoms, such as, for example, from 12 to 68 carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group and/or at least one pendant fatty chain chosen from fatty chains comprising from 8 to 120 carbon atoms, such as, for example, from 12 to 68 carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group, such as bonded to any carbon or nitrogen of the polyamide skeleton via the at least one linking group. In one embodiment, the at least one linking group is chosen from single bonds and urea, urethane, thiourea, thiourethane, thioether, thioester, ester, ether and amine groups. For example, the at least one linking group is chosen from ureas, esters, and amines, and as a further example, is chosen from esters and amines. The bond is, for example, an ester bond. In one embodiment, these polymers comprise a fatty chain at each end of the polymer skeleton, such as the polyamide skeleton.
In one embodiment, due to the presence of at least one chain, the at least one structuring polymer, e.g., a polyamide polymer, may be readily soluble in oils (i.e., water-immiscible liquid compounds) and thus may give macroscopically homogeneous compositions even with a high content (at least 25%) of the polyamide polymers, unlike certain polymers of the prior art that do not contain such alkyl or alkenyl chains at the end of the polyamide skeleton. As defined herein, a composition is soluble if it has a solubility of greater than 0.01 g per 100 ml of solution at 25°C.
In a further embodiment, the polyamide polymers can be chosen from polymers resulting from at least one polycondensation reaction between at least one acid chosen from at least one dicarboxylic acid comprising at least 32 carbon atoms, such as from 32 to 44 carbon atoms, and at least one amine chosen from diamines comprising at least 2 carbon atoms, such as from 2 to 36 carbon atoms, and triamines comprising at least 2 carbon atoms, such as from 2 to 36 carbon atoms. The at least one dicarboxylic acid can, for example, be chosen from dimers of at least one fatty acid comprising at least 16 carbon atoms, such as oleic acid, linoleic acid, and linolenic acid. The at least one amine can, for example, be chosen from diamines, such as ethylenediamine, hexylenediamine, hexamethylenediamine, phenylenediamine, and triamines. In one embodiment, the at least one amine can be ethylenetriamine.
The polyamide polymers may also be chosen from polymers comprising at least one terminal carboxylic acid group. The at least one terminal carboxylic acid group can, for example, be esterified with at least one alcohol chosen from monoalcohols comprising at least 4 carbon atoms. For example, the at least one alcohol can be chosen from monoalcohols comprising from 10 to 36 carbon atoms. In a further embodiment, the monoalcohols can comprise from 12 to 24 carbon atoms, such as from 16 to 24 carbon atoms, and, for example, 18 carbon atoms.
In one embodiment, the at least one polyamide polymer may be chosen from those described in U.S. Patent No. 5,783,657, which are polymers of formula (I):
R*
R'- -O-l-C — R2 C — N — R3— N- C — R2 — C — O — R1
O O O II O II in which:
- n is an integer which represents the number of amide units such that the number of ester groups present in said at least one polyamide polymer ranges from 10% to 50% of the total number of all said ester groups and all said amide groups comprised in said at least one polyamide polymer;
- R1, which are identical or different, are each chosen from alkyl groups comprising at least 4 carbon atoms and alkenyl groups comprising at least 4 carbon atoms. In one embodiment, the alkyl group comprises from 4 to 24 carbon atoms and the alkenyl group comprises from 4 to 24 carbon atoms;
- R2, which are identical or different, are each chosen from C4 to C42 hydrocarbon-based groups, with the proviso that at least 50% of all R2 are chosen from C30 to C 2 hydrocarbon-based groups;
- R3 , which are identical or different, are each chosen from organic groups comprising atoms chosen from carbon atoms, hydrogen atoms, oxygen atoms, and nitrogen atoms, with the proviso that R3 comprises at least 2 carbon atoms; and
- R4, which are identical or different, are each chosen from hydrogen atoms, C-\ to C10 alkyl groups and a direct bond to at least one group chosen from R3 and another R4 such that when said at least one group is chosen from another R4, the nitrogen atom to which both R3 and R4 are bonded forms part of a heterocyclic structure defined in part by R4-N-R3, with the proviso that at least 50% of all R4 are chosen from hydrogen atoms.
In one embodiment, the at least one terminal fatty chain of formula (I) is linked to the last heteroatom, in this case nitrogen, of the polyamide skeleton. In a further embodiment, the terminal chains are functionalized. In another embodiment, the ester groups of formula (I) which form part of the terminal and/or pendant fatty chains for purposes of the invention, are present in amounts ranging from 15% to 40% of the total number of ester and amide groups (i.e., heteroatom groups), such as, for example, from 20% to 35%.
In formula (I), in one embodiment, n may be an integer ranging from 1 to 10, for example an integer ranging from 1 to 5, and as a further example, an integer ranging from 3 to 5. In one embodiment of the present invention, R1, which are identical or different, can, for example, each be chosen from C-I2 to C22 alkyl groups, such as from Cι6 to C22 alkyl groups.
In one embodiment of the present invention, R2, which are identical or different, can, for example, each be chosen from C10 to C42 alkyl groups. At least 50% of all R2, for example, at least 75% of all R2, which are identical or different, can, for example, each be chosen from groups comprising from 30 to 42 carbon atoms. In these embodiments, the remaining R2, which are identical or different, can, for example, each be chosen from C4 to C18 groups, such as from C4 to C12 groups.
In one embodiment of the invention, R3, which can be identical or different, can, for example, each be chosen from C2 to C36 hydrocarbon- based groups and polyoxyalkylene groups. In another embodiment, R3, which can be identical or different, can each, for example, be chosen from C2 to C-12 hydrocarbon-based groups.
In one embodiment, R4, which can be identical or different, can each be chosen from hydrogen atoms.
As used herein, hydrocarbon-based groups may be chosen from linear, cyclic, and branched, saturated and unsaturated groups. The hydrocarbon-based groups can be chosen from aliphatic and aromatic groups. In one example, the hydrocarbon-based groups are chosen from aliphatic groups. The alkyl and alkylene groups may be chosen from linear, cyclic, and branched, saturated and unsaturated groups.
In general, the pendant and terminal fatty chains of the at least one structuring polymer may be chosen from linear, cyclic, and branched, saturated and unsaturated groups. The pendant and terminal fatty chains can be chosen from aliphatic and aromatic groups. In one example, the pendant and terminal fatty chains are chosen from aliphatic groups.
According to the invention, the structuring of the liquid fatty phase is obtained with the aid of at least one structuring polymer, such as the at least one polyamide polymer of formula (I). The at least one polyamide polymer of formula (I) may, for example, be in the form of a mixture of polymers, and this mixture may also comprise a compound of formula (I) wherein n is equal to zero, i.e., a diester.
Non-limiting examples of at least one polyamide polymer which may be used in the composition according to the present invention include the commercial products made or sold by Arizona Chemical under the names Uniclear 80 and Uniclear 100. These are sold, respectively, in the form of an 80% (in terms of active material) gel in a mineral oil and a 100% (in terms of active material) gel. These polymers have a softening point ranging from 88 °C to 94 °C, and may be mixtures of copolymers derived from monomers of (i) C36 diacids and (ii) ethylenediamine, and have a weight-average molecular mass of about 6000. Terminal ester groups result from esterification of the remaining acid end groups with at least one alcohol chosen from cetyl alcohol and stearyl alcohol. A mixture of cetyl and stearyl alcohols is sometimes called cetylstearyl alcohol.
Other non-limiting examples of at least one polyamide polymer which may be used in the composition according to the present invention include polyamide polymers or polyamide resins resulting from the condensation of at least one aliphatic dicarboxylic acid and at least one diamine, the carbonyl and amine groups being condensed via an amide bond. Examples of these polyamide polymers are those made or sold under the brand name Versamid by the companies General Mills Inc. and Henkel Corp. (Versamid 930, 744 or 1655) or by the company Olin Mathieson Chemical Corp. under the brand name Onamid, for example, Onamid S or C. These resins have a weight- average molecular mass ranging from 6000 to 9000. For further information regarding these polyamides, reference may be made to U.S. Patent Nos. 3,645,705 and 3,148,125.
Other examples of polyamides useful in the compositions of the invention include those made or sold by the company Arizona Chemical under the references Uni-Rez (2658, 2931 , 2970, 2621 , 2613, 2624, 2665, 1554, 2623, and 2662) and the product made or sold under the reference Macromelt 6212 by the company Henkel. For further information regarding these polyamides, reference may be made to U.S. Patent No. 5,500,209. Such polyamides display high melt viscosity characteristics. MACROMELT 6212, for example, has a high melt viscosity at 190°C of 30-40 poise (as measured by a Brookfield Viscometer, Model RVF #3 spindle, 20 RPM).
In a further embodiment, the at least one polyamide polymer may be chosen from polyamide resins from vegetable sources. Polyamide resins from vegetable sources may be chosen from, for example, the polyamide resins of U.S. Patent Nos. 5,783,657 and 5,998,570.
The structuring polymers of the invention may be non-waxy polymers.
In one embodiment, the at least one structuring polymer, e.g., a polyamide polymer, may be present in the composition in an amount ranging, for example, from 0.5% to 80%, such as from 2% to 60%, and further such as from 5% to 40%, by weight, relative to the total weight of the composition. In a further embodiment, the at least one structuring polymer, e.g., a polyamide polymer may be present in the composition in an amount ranging, for example, from 5% to 25% by weight, relative to the total weight of the composition.
In one embodiment, the at least one structuring polymer in the composition according to the invention corresponds to the polyamide polymers of formula (I). Due to fatty chain(s), these polymers may be readily soluble in oils and thus lead to compositions that are macroscopically homogeneous even with a high content (at least 25%) of at least one structuring polymer.
The at least one structuring polymer, e.g., a polyamide polymer, in the compositions of the invention may have a softening point greater than 50°C, such as from 65°C to 190°C, further such as from 65°C to less than 150°C, and further such as from 70°C to less than 130°C, and even further such as from 80°C to 105°C. This softening point may be lower than that of structuring polymers used in the art which may facilitate the use of the at least one structuring polymer of the present invention and may limit the degradation of the liquid fatty phase. The softening point can be measured by the well-known art-recognized method of Differential Scanning Calorimetry ("DSC"), with a temperature rise ranging from 5 °C to 10 °C per minute. Film-Forming Silicone Resin
The at least one film-forming silicone resin useful in the compositions of the invention may be chosen from any silicone resin that has film forming properties. In one embodiment, the at least one film-forming silicone resin is chosen from silsesquioxanes and siloxysilicates.
The use of silicone polymers or derivatives as film-forming agents in cosmetic compositions is known in the art. See, e.g., U.S. Patent Nos. 5,965,112, 5,800,816, 5,911 ,974, and 5,959,009. Silicone resin nomenclature is known in the art as "MDTQ" nomenclature, whereby a silicone resin is described according to the various monomeric siloxane repeating units which make up the polymer. Each letter of "MDTQ" denotes a different type of unit. The symbol M denotes the monofunctional unit (CH3)3SiOi/2. This unit is considered monofunctional because the silicone atom only shares one oxygen for the formation of the chain. The "M" unit can be represented as:
Si-O-,/2 H3C^ |
CH3 At least one of the methyl groups can be replaced, such as, for example, to give a unit with formula [R(CH3)2]SiOι/ , as represented in the following structure:
Figure imgf000018_0001
where R is other than a methyl group.
The symbol "D" denotes the difunctional unit (CH )2SiO2/2, where two of the available bonds from the silicone atom are used for binding to oxygen for the formation of the polymeric chain. The "D" unit, which is the major building block of dimethicone oils, can be represented as:
Figure imgf000018_0002
The symbol "T" denotes the trifunctional unit, (CH3)SiO3/2, where three of the available bonds from the silicone atom are used for binding to oxygen for the formation of the polymeric chain. The "T" unit can be represented as:
Figure imgf000018_0003
As in the "M" unit, any methyl group could be replaced in "D" or "T" with a group R which is other than methyl. Finally, the symbol "Q" denotes a quadrifunctional unit SiO /2, where all four of the available bonds from the silicone atom are used for binding to oxygen for the formation of the polymeric chain. The "Q" unit can be represented as:
Figure imgf000019_0001
The number of different silicones which can be manufactured is staggering. It would be clear to one skilled in the art that the properties of each of the silicones will vary depending on the type of monomer, the type of substitution, the size of the polymeric chain, and the degree of cross linking or size of the side chain. Different properties are attained depending on whether the backbone is a silicone chain with carbon-based side chains or whether the backbone is carbon-based with silicone side chains.
As described above, the at least one film-forming silicone resin may, in one embodiment, be chosen from siloxysilicates and silsesquioxanes. Any siloxysilicates or silsesquioxanes that functions as a film-former is within the practice of the invention. In one embodiment, the at least one film-forming silicone resin is chosen from substituted siloxysilicates and silsesquioxanes. A substituted siloxysilicate or a substituted silsesquioxane may be, for example, a siloxysilicate or a silsesquioxane where a methyl group has been substituted with a longer carbon chain such as an ethane, propane, or butane chain. The carbon chain may be saturated or unsaturated.
In one embodiment, the at least one film-forming silicone resin is chosen from siloxysilicates such as trimethylsiloxysilicat.es, which are represented by the following formula: [(CH3)3-Si-O]x-(SiO4/2)y (MQ units), where x and y can have values ranging from 50 to 80. In a further embodiment, a siloxysilicate may be chosen from any combination of M and Q units, such as, for example, [(R)3-Si-O]x-(SiO /2)y, where R is chosen from methyl groups and longer carbon chains.
In a further embodiment, the film-forming silicone resin is chosen from silsesquioxanes that are represented by the following formula: (CH3SiO3/2)x (T units), where x has a value of up to several thousand and the CH3 may be replaced by an R, as described above for T units. In one embodiment, the silsesquioxane is chosen from polymethylsilsesquioxanes, which are silsesquioxanes that do not have a substituent replacing the methyl group. The polymethylsilsesquioxanes useful in the present invention are film- formers and can, for example, have about 500 or less T units, such as, for example, from about 50 to about 500 T units.
In one embodiment of the invention, the film forming silicone resins have a melting point ranging from about 40°C to about 80°C. These silicone resins are soluble or dispersible in volatile silicones or other organic liquids. In one embodiment, the at least one film-forming silicone resins may be solid at about 25°C. In one embodiement, the at least one film-forming silicone resins may have a molecular weight ranging from 1000 to 10,000 grams/mole. In one embodiment, the at least one film-forming silicone resin is present in the composition in an amount ranging from 0.5% to 20% by weight, relative to the total weight of the composition, such as, for example, ranging from1% to 10%.
Not all polymethylsilsesquioxanes are film-formers. For example, the highly polymerized polymethylsilsesquioxanes (T Resins), such as Tospearl™ from Toshiba or KMP590 from Shin-Etsu are highly insoluble, and therefore are not effective film-formers. The molecular weight of these polymethylsilsesquioxanes is difficult to determine, and they generally contain a thousand or more T units.
An example of a polymethylsilsesquioxane useful in accordance with the present invention is Belsil PMS MK, also referred to as Resin MK, available from Wacker Chemie. This polymethylsilsesquioxane is a polymer primarily formed of polymerized repeating units of CH3SiO3/2 (T units), and which can also contain up to about 1 % (by weight or by mole) of (CHs)2SiO2/2 (D units). It is believed that the polymers are in a "cage" and "ladder" configuration, as exemplified in the figure below. The weight-average molecular weight of the "cage" unit has been calculated to be 536. The majority of the polymer is in the "ladder" configuration, where the ends are capped with ethoxy (CH3CH2O) groups. The weight percent of ethoxy present is about 4.5%, and the mole percent is about 7% (silicone units). Since this functionality can react with water, a small and variable amount of SiOH can also be present. The weight-average molecular weight can be, for example, from about 500 to about 50,000, such as about 10,000.
Figure imgf000021_0001
Cage Ladder
Polymethylsilsesquioxanes suitable for use in the present invention also include KR-220L available from SHIN-ETSU. The structure of KR-220L is made up of mostly silicone T-units (CH3Siθ32), with Si-OH or silanol end units. There are no D units. Other polymethylsilsesquioxanes that can be useful in the practice of the invention include KR-242A, which has a structure of about 98% methyl T units and about 2% dimethyl D units, with Si-OH or silanol end units, and KR-251 , which has a structure of about 88% methyl T units and about 12% dimethyl D units, with Si-OH or silanol end units, both of which are available from SHIN-ETSU.
In one embodiment of the invention, the at least one film-forming silicone resin is chosen from combinations of M, D, T, and Q units comprising at least two units chosen from M, D, T, and Q, which satisfy the relationship RnSiO(4-n)/2 wherein n is a value ranging from 1.0 to 1.50. Some resins of this type are disclosed in U.S. Patent No. 6,074,654. R may be a methyl group or any carbon chain as long as the silicone resin retains its film-forming properties. Up to 5% of silanol or alkoxy functionality may also be present in the resin structure as a result of processing.
In a further embodiment, the at least one film-forming silicone resin comprises repeating M units and Q units. The ratio of M units to Q units may be, for example, about 0.7:1. The at least one film-forming silicone resin may be chosen, for example, from Wacker 803 and 804, available from Wacker Silicones Corporation and G.E. 1170-002 from General Electric.
In a further embodiment, the at least one film-forming silicone resin is a copolymer, wherein at least one unit of the copolymer is chosen from M, D, T, and Q silicone units, and wherein at least one additional unit of the copolymer is chosen from an ester. The at least one film-forming silicone resin may be chosen from, for example, diisostearoyl trimethylolpropane siloxysilicates, such as SF 1318, available from GE Silicones.
The compositions according to the present invention can additionally comprise at least one additional film-former. The at least one additional film- former may improve, for example, smoothness or spreadability, water- resistance, transfer resistance properties, or other cosmetic or pharmaceutical properties desired by one of skill in the art. The at least one additional film former may be chosen from, for example, polyethylene, vinylpyrrolidone/vinyl acetate (PVP VA) copolymers such as the Luviskol® VA grades (all ranges) from BASF® Corporation and the PVP/VA series from ISP, acrylic fluorinated emulsion film formers including Foraperle® film formers such as Foraperle® 303 D from Elf Atochem (although Foraperle® may not be appropriate for some cosmetic formulations) GANEX® copolymers such as butylated PVP, PVP/Hexadecene copolymer, PVP/Eicosene copolymer or tricontanyl, Poly(vinylpyrrolidone/diethylaminoethyl methacrylate) or PVP/Dimethylaminoethylmethacrylate copolymers such as Copolymer 845, Resin ACO-5014 (Imidized IB/MA copolymer), other PVP based polymers and copolymers, alkyl cycloalkylacrylate copolymers (See, e.g., WO 98/42298), Mexomere® film formers and other allyl stearate/vinyl acetate copolymers (allyl stearate/VA copolymers), polyolprepolymers such as PPG-12/SMDI copolymer, polyolprepolymers such as PPG-1 2/SM Dl copolymer, Poly(oxy- 1 ,2-ethanediyl), α-hydro-ω-hydroxy-polymer with 1 ,1'-methylene-bis-(4- isocyanatocyclohexane) available from Barnet, Avalure™ AC Polymers (Acrylates Copolymer) and Avalure™ UR polymers (Polyurethane Dispersions), available from BFGoodrich.
The at least one additional film former which also may be used within the framework of the invention includes film formers having any film former chemistry known in the art such as, for example, PVP, acrylates, urethane, synthetic polymers of the polycondensate type, free-radical type, or ionic type, polymers of natural origin, and mixtures thereof, as well as any other film former known within the practice of the cosmetic and pharmaceutical arts which one skilled in the art may determine to be compatible.
An appropriate amount of the at least one additional film-former may be determined by one of skill in the art, and can vary considerably based on the application. For example, in one embodiment, the at least one additional film-former may be used in an amount ranging from 0.1% to 20%, such as, for example, ranging from 1 % to 10%, by weight, relative to the total weight of the composition.
The amounts of the at least one film-forming silicone resin and of the at least one structuring polymer, e.g., a polyamide polymer, may be chosen according to the desired hardness and desired stability of the compositions, and according to the specific application envisaged. The respective amounts of the at least one structuring polymer, e.g., a polyamide polymer, and of the at least one film-forming silicone resin can be such that a disintegrable solid which does not flow under its own weight is obtained. Depending on the intended application, such as, for example, a stick, hardness of the composition may be considered. The hardness of a composition may, for example, be expressed in gram force (gf). The compositions of the present invention may, for example, have a hardness ranging from 20 gf to 2000 gf, for example, ranging from 20 gf to 900 gf, and further, such as, for example ranging from 20 gf to 600 gf.
This hardness can be measured in one of two ways. A first test for hardness is according to a method of penetrating a probe into the composition and in particular using a texture analyzer (for example TA-XT2i from Rheo) equipped with an ebonite cylinder of height 25 mm and diameter 8 mm. The hardness measurement is carried out at 20 °C at the center of 5 samples of the composition. The cylinder is introduced into each sample of composition at a pre-speed of 2 mm/s, and then at a speed of 0.5 mm/s, and finally at a post-speed of 2 mm/s, the total displacement being 1 mm. The recorded hardness value is that of the maximum peak observed. The measurement error is ± 50gf.
A second test for hardness is the "cheese wire" method, which involves cutting an 8.1 mm or 12.7 mm stick of composition and measuring its hardness at 20°C using a DFGHS 2 tensile testing machine from Indelco- Chatillon Co. at a speed of 100 mm/minute. The hardness value from this method is expressed in gram force as the shear force required to cut a stick under the above conditions. According to this method, the hardness of compositions according to the present invention which may be in stick form may, for example, range from 30 gf to 300 gf, such as from 30 gf to 250 gf, and further, such as from 30 gf to 200 gf.
The hardness of the composition of the present invention may be such that the compositions are self-supporting and can easily disintegrate to form a satisfactory deposit on keratinous materials. In addition, this hardness may impart good impact strength to the inventive compositions which may be molded or cast, for example, in stick or dish form. The skilled artisan may choose to evaluate a composition using at least one of the tests for hardness outlined above based on the application envisaged and the hardness desired. If one obtains an acceptable hardness value, in view of the intended application, from at least one of these hardness tests, the composition falls within the scope of the invention.
According to the present invention, the compositions in stick form may also possess the properties of deformable, flexible elastic solids and may also have noteworthy elastic softness upon application to keratinous materials. The compositions in stick form of the prior art do not have this elasticity and flexibility. Liquid fatty phase
The at least one liquid fatty phase, in one embodiment, may comprise at least one oil. In one embodiment, the at least one oil may have an affinity with the at least one structuring polymer, e.g., a polyamide polymer,. The at least one oil may, for example, be chosen from polar oils and apolar oils, including hydrocarbon-based liquid oils and oily liquids at room temperature. In one embodiment, the compositions of the invention comprise at least one structuring polymer, e.g., a polyamide polymer, and at least one polar oil. The polar oils of the invention may, for example, be added to the apolar oils, the apolar oils may act as co-solvent for the polar oils.
According to the invention, the structuring of the at least one liquid fatty phase may, for example, be obtained with the aid of at least one structuring polymer, such as the polyamide polymer of formula (I). In general, the polymers of formula (I) may be in the form of mixtures of polymers, these mixtures also possibly containing a synthetic product corresponding to a compound of formula (I) in which n is 0, i.e., a diester.
In one embodiment, the liquid fatty phase of the composition may contain more than 30%, for example, more than 40%, of liquid oil(s) having a chemical nature similar to that of the skeleton of the at least one structuring polymer, and, for example, from 50% to 99.4%. In one embodiment, the liquid fatty phase structured with a polyamide-type skeleton contains a high quantity, i.e., greater than 30%, for example greater than 40%, relative to the total weight of the liquid fatty phase, or, for example, from 50% to 99.4%, of at least one apolar, such as hydrocarbon-based, oil. For the purposes of the invention, the expression "hydrocarbon-based oil" means an oil comprising carbon and hydrogen atoms, optionally with at least one group chosen from hydroxyl, ester, carboxyl, and ether groups.
For a liquid fatty phase structured with at least one polymer containing a partially silicone-based skeleton, this fatty phase may contain more than 30%, for example, more than 40%, relative to the total weight of the liquid fatty phase and, for example, from 50% to 99.4%, of at least one silicone- based liquid oil, relative to the total weight of the liquid fatty phase.
For a liquid fatty phase structured with at least one polymer of the hydrocarbon-based type, this fatty phase may contain more than 30%, for example more than 40% by weight, or, for example, from 50% to 99.4% by weight, of at least one liquid apolar, such as hydrocarbon-based, oil, relative to the total weight of the liquid fatty phase.
For example, the at least one polar oil useful in the invention may be chosen from:
- hydrocarbon-based plant oils with a high content of triglycerides comprising fatty acid esters of glycerol in which the fatty acids may have varied chain lengths from C4 to C24, these chains possibly being chosen from linear and branched, and saturated and unsaturated chains; these oils are chosen from, for example, wheat germ oil, corn oil, sunflower oil, karite butter, castor oil, sweet almond oil, macadamia oil, apricot oil, soybean oil, cotton oil, alfalfa oil, poppy oil, pumpkin oil, sesame oil, marrow oil, rapeseed oil, avocado oil, hazelnut oil, grape seed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, olive oil, rye oil, safflower oil, candlenut oil, passion flower oil and musk rose oil; or alternatively caprylic/capric acid triglycerides such as those made or sold by Stearineries Dubois, or those made or sold under the names Miglyol 810, 812 and 818 by Dynamit Nobel;
- synthetic oils or esters of formula R5COOR6 in which R5 is chosen from cyclic, linear, and branched fatty acid residues containing from 1 to 40 carbon atoms, and Re is chosen from, for example, a hydrocarbon-based chain containing from 1 to 40 carbon atoms, for example, 1-4 carbon atoms, on condition that R5 + R6 > 10, such as, for example, purcellin oil (cetostearyl octanoate), isononyl isononanoate, Cι2-C-|5 alkyl benzoates, isopropyl myristate, 2-ethylhexyl palmitate, isostearyl isostearate and alkyl or polyalkyl octanoates, decanoates or ricinoleates; hydroxylated esters such as isostearyl lactate and diisostearyl malate; and pentaerythritol esters;
- synthetic ethers containing from 10 to 40 carbon atoms;
- Cs to C26 fatty alcohols such as oleyl alcohol; and
- Cs to C26 fatty acids such as oleic acid, linolenic acid or linoleic acid.
The at least one apolar oil according to the invention may be chosen from, for example, silicone oils chosen from volatile and non-volatile, linear, branched, and cyclic polydimethylsiloxanes (PDMSs) that are liquid at room temperature; polydimethylsiloxanes comprising alkyl or alkoxy groups which are pendant and/or at the end of the silicone chain, the groups each containing from 2 to 24 carbon atoms; phenylsilicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes and 2- phenylethyl trimethylsiloxysilicates; hydrocarbons chosen from cyclic, linear and branched, volatile and non-volatile hydrocarbons of synthetic and mineral origin, such as volatile liquid paraffins (such as isoparaffins and isododecane) or non-volatile liquid paraffins and derivatives thereof, liquid petrolatum, liquid lanolin, polydecenes, hydrogenated polyisobutene such as hydrogenated polybutene, for example, Parieam®, from Nippon Oils and Fats, and squalane; and mixtures thereof. The structured oils, for example those structured with polyamides such as those of formula (I), or the polyurethanes, polyureas, or polyurea-urethanes, may be, in one embodiment, apolar oils, such as an oil or a mixture of hydrocarbon oils chosen from those of mineral and synthetic origin, chosen from hydrocarbons such as alkanes such as Parieam® oil, isoparaffins including isododecane, and squalane, and mixtures thereof. These oils may, in one embodiment, be combined with at least one phenylsilicone oil.
The liquid fatty phase, in one embodiment, contains at least one non-volatile oil chosen from, for example, hydrocarbon-based oils of mineral, plant and synthetic origin, synthetic esters or ethers, silicone oils and mixtures thereof.
In another embodiment, the total liquid fatty phase may be present, for example, in an amount ranging from 1% to 99.4% by weight, relative to the total weight of the composition, for example, ranging from 5% to 99.4%, such as ranging from 5% to 95.5%, ranging from 10% to 80%, and further ranging from 20% to 75%.
For the purposes of the invention, the expression "volatile solvent or oil" means any non-aqueous medium capable of evaporating on contact with the skin or the lips in less than one hour at room temperature and atmospheric pressure. The volatile solvent(s) of the invention is(are) organic solvents, such as volatile cosmetic oils that are liquid at room temperature, having a non-zero vapor pressure at room temperature and atmospheric pressure, ranging, for example, from 10"2 to 300 mmHg (1.33 Pa to 10,000 Pa) and, as a further example, greater than 0.3 mmHg (4Pa). The expression "non-volatile oil" means an oil which remains on the skin or the lips at room temperature and atmospheric pressure for at least several hours, such as those having a vapor pressure of less than 10"2 mmHg (1.33Pa).
According to the invention, these volatile solvents or oils may facilitate the staying power or long wearing properties of the composition on the keratinous materials. The solvents can be chosen from hydrocarbon-based solvents, silicone solvents optionally comprising alkyl or alkoxy groups that are pendant or at the end of a silicone chain, and a mixture of these solvents.
The volatile oil(s), in one embodiment, may be present in an amount ranging up to and including 95.5%, relative to the total weight of the composition, such as, for example, from 2% to 75% or, as a further example, from 10% to 45%. This amount will be adapted by a person skilled in the art according to the desired staying power or long wearing properties.
The at least one liquid fatty phase of the compositions of the invention may further comprises a dispersion of lipid vesicles. The compositions of the invention may also, for example, be in the form of a fluid anhydrous gel, a rigid anhydrous gel, a fluid simple emulsion, a fluid multiple emulsion, a rigid simple emulsion or a rigid multiple emulsion. The simple emulsion or multiple emulsion may comprise a continuous phase chosen from an aqueous phase optionally containing dispersed lipid vesicles, or a fatty phase optionally containing dispersed lipid vesicles. In one embodiment, the composition has a continuous oily phase or fatty phase and is an anhydrous composition, for example, in stick or dish form. An anhydrous composition is one that has less than 10% water by weight, such as, for example, less than 5% by weight. Additional Components
The compositions of the invention may further comprise at least one additional fatty material. The at least one additional fatty material may, for example, be chosen from gums, fatty materials that are pasty or viscous at ambient temperature, and resins.
Needless to say, the compositions of the invention should be cosmetically and/or dermatologically acceptable, i.e., they should contain a non-toxic physiologically acceptable medium and should be able to be applied to human keratinous materials. Thus, the composition of the present invention, in one embodiment, may comprise a physiologically acceptable medium, e.g., a physiologically acceptable oil or solvent. For purposes of the invention, "cosmetically and/or dermatologically acceptable" means that compositions of the invention have a pleasant appearance, odor, and taste.
The compositions of the present invention may also further comprise at least one suitable additive commonly used in the field concerned chosen from coloring agents, antioxidants, essential oils, preserving agents, fragrances, fillers, pasty fatty substances, waxy fatty substances, neutralizing agents, liposoluble or lipodispersible gelling agents, liposoluble polymers, and cosmetically active agents and dermatological active agents, i.e., an agent having a beneficial effect on keratinous materials, such as, for example, emollients, moisturizers, vitamins, essential fatty acids, and sunscreens. The compositions of the invention may also further comprise water, optionally thickened with an aqueous-phase thickener or gelled with a hydrophilic gelling agent and/or containing ingredients soluble in water. The at least one additive may be present in an amount ranging from 0.01 % to 20%, such as, for example, from 0.01% to 10%, by weight, relative to the total weight of the composition.
In one embodiment, the at least one suitable additive is chosen from at least one wax. As used herein, a "wax" may be any lipophilic fatty compound which is soluble in the liquid fatty phase, unlike most fillers of pigments. Non- limiting examples of such waxes include waxes of natural origin, such as beeswax, camauba wax, candelilla wax, ouricury wax, Japan wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite wax, microcrystalline waxes, lanolin wax, montan wax and ozokerites, hydrogenated oils such as hydrogenated jojoba oil, jojoba esters, waxes of synthetic origin, such as polyethylene waxes derived from polymerization of ethylene, waxes obtained by Fischer-Tropsch synthesis, fatty acid esters and glycerides, and silicone waxes such as derivatives of poly(di)methylsiloxane.
In one embodiment, the at least one wax may be present in the composition in an amount up to 3%, and in another embodiment, in an amount of at least 3%, such as up to 30% or up to 50%. In one embodiment, th e wax may be present in an amount ranging from 0.05% to 15% relative to the total weight of the composition, such as from 0.1% to 10%. The at least one wax may, for example, have a melting point greater then about 45°C, such as, for example, greater than about 55°C.
Needless to say, the person skilled in the art will take care to select the optional additional additives and the amounts thereof such that not all of the possible advantageous properties of the composition according to the invention are, or are substantially, adversely affected by the addition(s) envisaged.
The compositions of the invention may also comprise at least one coloring agent chosen from pigments, dyes, nacreous pigments (i.e., nacres), and pearling agents. The at least one coloring agent may be chosen, for example, in order to obtain make-up compositions which give good coverage, that is, which do not leave a significant amount of the at least one keratinous material to which it is applied showing through. The pigments may also reduce the sticky feel of the compositions, unlike soluble dyes. In one embodiment, the coloring agents are pigments (nacreous or non-nacreous).
Representative liposoluble dyes which may be used according to the present invention include Sudan red, DC Red 17, DC Green 6, β-carotene, soybean oil, Sudan brown, DC Yellow 11 , DC Violet 2, DC Orange 5, quinoline yellow, and annatto. The liposoluble dyes, when present, may be present in an amount ranging up to 20% by weight of the total weight of the composition, such as from 0.1% to 6%.
The pigments which may be used according to the present invention may be chosen from white, colored, mineral, organic, coated and uncoated pigments. Representative examples of mineral pigments include titanium dioxide, optionally surface-treated, zirconium oxide, zinc oxide, cerium oxide, iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate and ferric blue. Representative examples of organic pigments include carbon black, pigments of D & C type, and lakes based on cochineal carmine, barium, strontium, calcium and aluminum. If present, the pigments may have an amount ranging up to 40% by weight of the total weight of the composition, such as from 1% to 35%, and further such as from 2% to 25%.
The nacreous pigments (or nacres) which may be used according to the present invention may be chosen from white nacreous pigments such as mica coated with titanium or with bismuth oxychloride, colored nacreous pigments such as titanium mica with iron oxides, titanium mica with ferric blue or chromium oxide, titanium mica with an organic pigment chosen from those mentioned above, and nacreous pigments based on bismuth oxychloride. The nacres, if present, may have an amount ranging up to 30% by weight of the total weight of the composition, such as from 0.1 % to 20%. In one embodiment, the coloring agents are pigments.
An embodiment of the invention relates to a keratinous material care, make-up, or treatment composition comprising a structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer, e.g., a polyamide polymer, comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, and at least one film-forming silicone resin.
Additionally, an embodiment of the invention relates to a keratinous material care make-up, or treatment composition comprising a structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer comprising a polymer skeleton, e.g., a polyamide polymer, comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, at least one film-forming silicone resin, and at least one coloring agent.
Additionally, an embodiment of the invention relates to a method of caring for, treating, or making up at least one keratinous material comprising applying to the at least one keratinous material a structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer, e.g., a polyamide polymer, comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, and at least one film-forming silicone resin.
One embodiment of the present invention is a cosmetic process for caring for, making up, or treating at least one keratinous material, such as that of a human being, comprising the application to the at least one keratinous material a cosmetic composition comprising at least one polyamide polymer comprising a polyamide skeleton and at least one film- forming silicone resin. The polyamide skeleton comprises at least one end group with at least one chain chosen from alkyl chains comprising at least four carbon atoms and alkenyl chains comprising at least four carbon atoms, bonded to the at least one polyamide skeleton via at least one linking group. The polyamide skeleton may further comprise at least one pendant group with at least one chain chosen from alkyl chains comprising at least four carbon atoms and alkenyl chains comprising at least four carbon atoms, bonded to any carbon or nitrogen of the polyamide skeleton via at least one linking group.
In another embodiment, the present invention is directed to a process of making a cosmetic composition in the form of a physiologically acceptable composition, comprising including in the composition at least one structuring polymer, e.g., a polyamide polymer, comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom. The polymer skeleton comprises at least one end group with at least one chain chosen from alkyl chains comprising at least four carbon atoms and alkenyl chains comprising at least four carbon atoms, bonded to the at least one polymer skeleton via at least one linking group. The polymer skeleton may further comprise at least one pendant group with at least one chain chosen from alkyl chains comprising at least four carbon atoms and alkenyl chains comprising at least four carbon atoms, bonded to any carbon or heteroatom of the polymer skeleton via at least one linking group. The composition also comprises at least one film-forming silicone resin.
Another embodiment of the invention relates to a lip composition in stick form comprising at least one continuous liquid fatty phase, at least one film-forming silicone resin and at least one non-waxy structuring polymer having a weight-average molecular mass of less than 100,000.
The packaging and application device for any subject of the invention may be chosen and manufactured by persons skilled in the art on the basis of their general knowledge, and adapted according to the nature of the composition to be packaged. Indeed, the type of device to be used can be, for example, linked to the consistency of the composition,, for example, to its viscosity; it can also depend on the nature of the constituents present in the composition, such as the presence of volatile compounds.
The invention will be illustrated by, but is not intended to be limited to, the following examples. The present invention may be embodied in other specific forms without departing from its spirit or essential characteristics. The described embodiments are to be considered in all respects as illustrative only and not restrictive. The scope of the invention is, therefore, indicated by the appended claims, rather than by the foregoing description. All changes which come within the meaning and range of equivalency of the claims are to be embraced within their scope. Example 1. Transfer Resistant Mascara
A transfer resistant mascara was prepared by mixing the following ingredients. PHASE INCI NAME w/w%
A Isododecane 41.97
Alkyl Silicone Resin 7.00 with Alkyl Groups (MK Resin)
Isododecane Gel 16.50
(Versagel MD 870)
Quatemium 18 Hectorite 4.00
Black Iron Oxide 5.00
B Propylene Carbonate 1.32
C Paraffin 3.00
Carnauba Wax 5.20
Beeswax 7.00
Synthetic Beeswax 4.00
Uniclear 100 5.00
Phenoxyethanol 0.01
Phases A, B, and C were each prepared separately by mixing together the ingredients of each phase. The three phases were then combined and the resulting mascara was found to have transfer resistant properties upon application to eye lashes. Example 2. Transfer Resistant Mascara
A transfer resistant mascara was prepared from the following ingredients. PHASE INCI NAME w/w%
Isododecane 40.4
Trimethylsiloxysilicate 7.0
Isododecane with 14.0 a) styrene-ethylene/butylene-styrene triblock copolymer, and 1.2 b) styrene-ethylene/propylene radial copolymer 1.2
Disteardimonium Hectorite 5.5 Iron Oxides 5.0
B Propylene Carbonate 1.8
C Allyl stearate/VA copolymer 5.0
Waxes 16.8
Preservatives 0.01
Uniclear 100 5.00
Phase A was mixed with a homogenizer for 20 minutes at room temperature and then heated to 65°C for 15 minutes. In a separate beaker, phase C was combined with propeller mixing and heated to 85-90°C. Once phase A and phase C reached their respective temperatures, phase C was added to phase A. The batch was homogenized for 5 minutes while maintaining the heat at 80-85°C and phase B was added. The mixture was homogenized for 30 minutes at 80-85°C and then removed from the homogenizer and cooled to 30-35°C using sweep mixing. The ingredients were combined and the resulting mascara was found to have transfer resistant properties upon application to eye lashes.

Claims

WHAT IS CLAIMED IS:
1. A composition comprising at least one liquid fatty phase which comprises:
(i) at least one structuring polymer comprising: a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom; and (ii) at least one film-forming silicone resin.
2. The composition according to claim 1 , wherein the composition is in a form chosen from a fluid anhydrous gel, rigid anhydrous gel, fluid simple emulsion, rigid simple emulsion, fluid multiple emulsion, and rigid multiple emulsion.
3. A structured anhydrous composition comprising at least one liquid fatty phase structured with at least one structuring polymer comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom and at least one film-forming silicone resin.
4. An anhydrous composition comprising at least one liquid fatty phase which comprises:
(i) at least one structuring polymer comprising: a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom; and (ii) at least one film-forming silicone resin.
5. An anhydrous composition comprising at least one liquid fatty phase which comprises:
(i) at least one structuring polymer comprising: a polymer skeleton which comprises at least three hydrocarbon-based repeating units comprising at least one heteroatom; and (ii) at least one film-forming silicone resin.
6. An anhydrous composition according to claim 5, wherein said at least three hydrocarbon-based repeating units are identical.
7. The composition according to one of claims 1-6, wherein said at least one structuring polymer further comprises at least one of: at least one terminal fatty chain chosen from alkyl chains and alkenyl chains, wherein said at least one terminal fatty chain is bonded to said polymer skeleton via at least one linking group; and at least one pendant fatty chain chosen from alkyl chains and alkenyl chains, wherein said at least one pendant fatty chain is bonded to said polymer skeleton via at least one linking group.
8. The composition according to claim 7, wherein said alkyl chains and said alkenyl chains each comprise at least four carbon atoms.
9. The composition according to one of claims 7 or 8, wherein said alkyl chains and said alkenyl chains each comprise from 8 to 120 carbon atoms.
10. The composition according to one of claims 7-9, wherein said alkyl chains and said alkenyl chains each comprise from 12 to 68 carbon atoms.
11. The composition according to one of claims 7-10, wherein said at least one linking group is chosen from single bonds and urea, urethane, thiourea, thiourethane, thioether, thioester, ester, ether and amine groups.
12. The composition according to one of claims 7-11 , wherein said at least one linking group is chosen from urea, ester, and amine groups.
13. The composition according to one of claims 7-12, wherein said at least one linking group is chosen from ester and amine groups.
14. The composition according to one of claims 7-13, wherein said at least one linking group is an ester group present in a proportion ranging from 15% to 40% of the total number of all ester and heteroatom groups in the at least one structuring polymer.
15. The composition according to one of claims 7-14, wherein said at least one linking group is an ester group present in a proportion ranging from 20% to 35% of the total number of all ester and heteroatom groups in the at least one structuring polymer.
16. The composition according to one of claims 7-15, wherein said at least one terminal fatty chain is functionalized.
17. The composition according to one of claims 7-16, wherein said at least one pendant fatty chain is functionalized.
18. The composition according to one of claims 7-17, wherein in said at least one structuring polymer, the percentage of the total number of fatty chains ranges from 40% to 98%, relative to the total number of all repeating units and fatty chains in the at least one structuring polymer.
19. The composition according to one of claims 7-18, wherein in said at least one structuring polymer, the percentage of the total number of fatty chains ranges from 50% to 95%, relative to the total number of all repeating units and fatty chains in the at least one structuring polymer.
20. The composition according to one of claims 1-19, wherein said at least one structuring polymer has a weight-average molecular mass of less than 100,000.
21. The composition according to one of claims 1-20, wherein said at least one structuring polymer has a weight-average molecular mass of less than 50,000.
22. The composition according to one of claims 1-21 , wherein said at least one structuring polymer has a weight-average molecular mass ranging from 1000 to 30,000.
23. The composition according to one of claims 1-22, wherein said at least one hydrocarbon based repeating unit comprises from 2 to 80 carbon atoms.
24. The composition according to one of claims 1-23, wherein said at least one heteroatom of said at least one hydrocarbon-based repeating unit is chosen from nitrogen, sulphur, and phosphorus.
25. The composition according to claim 24, wherein said at least one heteroatom is a nitrogen atom.
26. The composition according to one of claims 1-25, wherein said at least one heteroatom is combined with at least one atom chosen from oxygen and carbon to form a heteroatom group.
27. The composition according to claim 26, wherein said at least one heteroatom group is chosen from amide groups, carbamate groups, and urea groups.
28. The composition according to one of claims 26 or 27, wherein said at least one heteroatom group is an amide group and said polymer skeleton is a polyamide skeleton.
29. The composition according to one of claims 26-28, wherein said at least one heteroatom group is chosen from carbamate groups and urea groups and said polymer skeleton is chosen from a polyurethane skeleton, a polyurea skeleton and a polyurethane-polyurea skeleton.
30. The composition according to one of claims 1-29, wherein said at least one structuring polymer is chosen from polyamide polymers of formula (I):
Rq
R' O- C — R2 C — N — R3— N- C R2 C — O — R1
O O O II O II in which:
- n is an integer which represents the number of amide units such that the number of ester groups present in said at least one polyamide polymer ranges from 10% to 50% of the total number of all ester groups and all amide groups comprised in said at least one polyamide polymer; - R1, which are identical or different, are each chosen from alkyl groups comprising at least 4 carbon atoms and alkenyl groups comprising at least 4 carbon atoms;
- R2, which are identical or different, are each chosen from C4 to C42 hydrocarbon-based groups, with the proviso that at least 50% of all R2 are chosen from C30 to C42 hydrocarbon-based groups;
- R3, which are identical or different, are each chosen from organic groups comprising atoms chosen from carbon atoms, hydrogen atoms, oxygen atoms and nitrogen atoms, with the proviso that R3 comprises at least 2 carbon atoms; and
- R4, which are identical or different, are each chosen from hydrogen atoms, C-i to C10 alkyl groups and a direct bond to at least one group chosen from R3 and another R4 such that when said at least one group is chosen from another R4, the nitrogen atom to which both R3 and R4 are bonded forms part of a heterocyclic structure defined in part by R4-N-R3, with the proviso that at least 50% of all R4 are chosen from hydrogen atoms.
31. The composition according to claim 30, wherein in said formula (I), n is an integer ranging from 1 to 5.
32. The composition according to one of claims 30 or 31 , wherein in said formula (I), said alkyl groups of R1 and said alkenyl groups of R1 each independently comprise from 4 to 24 carbon atoms.
33. The composition according to one of claims 30-32, wherein in said formula (I), R1, which are identical or different, are each chosen from C12 to C22 alkyl groups.
34. The composition according to one of claims 30-33, wherein in said formula (I), R1, which are identical or different, are each chosen from C-iβ to C22 alkyl groups.
35. The composition according to one of claims 30-34, wherein in said formula (I), R2, which are identical or different, are each chosen from C10 to C-42 hydrocarbon based groups, with the proviso that at least 50% of all R2 are chosen from C3o to C42 hydrocarbon based groups.
36. The composition according to one of claims 30-35, wherein in said formula (I), R3, which can be identical or different, are each chosen from C2 to C36 hydrocarbon-based groups and polyoxyalkylene groups.
37. The composition according to one of claims 30-36, wherein R3, which can be identical or different, are each chosen from C2 to C12 hydrocarbon-based groups.
38. The composition according to one of claims 30-37, wherein in said formula (I), R4, which can be identical or different, are each chosen from hydrogen atoms.
39. The composition according to one of claims 30-38, wherein said at least one polymer of formula (I) is in the form of a mixture of polymers, wherein said mixture optionally also comprises a polymer of formula (I) wherein n is equal to zero.
40. The composition according to one of claims 1-39, wherein said at least one structuring polymer has a softening point greater than 50°C.
41. The composition according to one of claims 1 -40, wherein said at least one structuring polymer has a softening point ranging from 65°C to less than 150°C.
42. The composition according to one of claims 1-41 , wherein said at least one structuring polymer has a softening point ranging from 70°C to less than 130°C.
43. The composition according to one of claims 1-42, wherein said at least one structuring polymer is present in the composition in an amount ranging from 0.5% to 80% by weight, relative to the total weight of the composition.
44. The composition according to one of claims 1-43, wherein said at least one structuring polymer is present in the composition in an amount ranging from 2% to 60% by weight, relative to the total weight of the composition.
45. The composition according to one of claims 1-44, wherein said composition has a hardness ranging from 20 gf to 2000 gf.
46. The composition according to one of claims 1-45, wherein said composition has a hardness ranging from 30 gf to 250 gf.
47. The composition according to one of claims 1 -46, wherein said at least one liquid fatty phase of the composition comprises at least one oil, wherein said at least one oil is chosen from at least one polar oil and at least one apolar oil, each having an affinity with said at least one structuring polymer.
48. The composition according to claim 47, wherein said at least one polar oil is chosen from:
- hydrocarbon-based plant oils with a high content of triglycerides comprising fatty acid esters of glycerol in which the fatty acids comprise chains having from 40 to 24 carbon atoms, said chains optionally being chosen from cyclic, linear and branched, saturated and unsaturated chains;
- synthetic oils or esters of formula R5COOR6 in which R5 is chosen from cyclic, linear and branched fatty acid residues comprising from 1 to 40 carbon atoms and Re is chosen from hydrocarbon-based chains comprising from 1 to 40 carbon atoms, with the proviso that R5 + R6 > 10;
- synthetic ethers containing from 10 to 40 carbon atoms;
- Cs to C-26 fatty alcohols; and
- C8 to C26 fatty acids.
49. The composition according to claim 47, wherein said at least one apolar oil is chosen from:
- silicone oils chosen from volatile and non-volatile, linear and cyclic polydimethylsiloxanes that are liquid at room temperature; - polydimethylsiloxanes comprising alkyl or alkoxy groups which are pendant and/or at the end of the silicone chain, the groups each containing from 2 to 24 carbon atoms;
- phenylsilicones; and
- hydrocarbons chosen from linear and branched, volatile and nonvolatile hydrocarbons of synthetic and mineral origin.
50. The composition according to one of claims 1-49, wherein said at least one liquid fatty phase comprises at least one non-volatile oil.
51. The composition according to claim 50, wherein said at least one non-volatile oil is chosen from hydrocarbon-based oils of mineral, plant and synthetic origin, synthetic esters and ethers, and silicone oils.
52. The composition according to one of claims 1-51 , wherein said at least one liquid fatty phase is present in an amount ranging from 1 % to 99.4% by weight, relative to the total weight of the composition.
53. The composition according to one of claims 1-52, wherein said at least one liquid fatty phase is present in an amount ranging from 10% to 80% by weight, relative to the total weight of the composition.
54. The composition according to one of claims 1-53, wherein said at least one liquid fatty phase comprises at least one volatile solvent chosen from hydrocarbon-based solvents and silicone solvents optionally comprising alkyl or alkoxy groups that are pendant or at the end of a silicone chain.
55. The composition according to claim 54, wherein said at least one volatile solvent is present in an amount up to 95.5% by weight, relative to the total weight of the composition.
56. The composition according to one of claims 54 or 55, wherein said at least one volatile solvent is present in an amount ranging from 10% to 45% by weight, relative to the total weight of the composition.
57. The composition according to one of claims 1-56, wherein said composition further comprises at least one additional fatty material.
58. The composition according to claim 57, wherein said at least one additional fatty material is chosen from gums, fatty materials pasty or viscous at ambient temperature, and resins.
59. The composition according to one of claims 1-58, wherein said at least one film-forming silicone resin is chosen from silsesquioxanes and siloxysilicates.
60. The composition according to claim 59, wherein said silsesquioxanes comprise repeating units of (RSiO3/2)χ, where X is less than 2000.
61. The composition according to claim 60, wherein x is 500 or less.
62. The composition according to claim 59, wherein said silsesquioxanes are chosen from polymethylsilsesquioxanes comprising repeating units of formula (CH3SiO3/2).
63. The composition according to claim 59, wherein said siloxysilicates are chosen from trimethylsiloxysilicates.
64. The composition according to claim 63, wherein said trimethylsiloxysilicates comprise repeating units of [(CH3)3-Si-O]χ-(SiO4/2)y, where x ranges from 50 to 80 and y ranges from 50 to 80.
65. The composition according to claim 62, wherein said polymethylsilsesquioxanes comprising repeating units of formula (CH3SiO3/2) further comprise up to 1% of polymerized repeating units of formula
Figure imgf000045_0001
66. The composition according to one of claims 1-65, wherein the at least one film-forming silicone resin comprises at least two units chosen from M, D, T, and Q and said at least two units satisfy the relationship RnSiO(4-n)/2, wherein n is a value ranging from 1.0 to 1.50.
67. The composition according to claim 66, wherein said at least one film-forming silicone resin is a solid at 25°C.
68. The composition according to claim 66, wherein said at least one film-forming silicone resin has a weight average molecular weight ranging from 1000 to 10,000 grams/mole.
69. The composition according to one of claims 1-68, wherein said at least one film-forming silicone resin comprises repeating M units and repeating Q units.
70. The composition according to claim 69, wherein the ratio of M units to Q units is 0.7:1.
71. The composition according to one of claims 1 -70, wherein said at least one film-forming silicone resin is present in the composition in an amount ranging from 1% to 10% by weight, relative to the total weight of the composition.
72. The composition according to one of claims 1-71 , wherein said composition further comprises at least one additional film-former.
73. The composition according to one of claims 1-72, wherein said composition is a solid.
74. The composition according to one of claims 1-73, wherein said composition is a solid chosen from molded and poured sticks.
75. The composition according to one of claims 1-74, further comprising at least one fatty alcohol.
76. The composition according to claim 75, wherein said at least one fatty alcohol is chosen from C8 to C26 fatty alcohols.
77. The composition according to one of claims 75 or 76, wherein said at least one fatty alcohol is chosen from C12 to C2o fatty alcohols.
78. The composition according to one of claims 75-77, wherein said C12 to C2o fatty alcohols are chosen from myristyl alcohol, cetyl alcohol, stearyl alcohol and behenyl alcohol.
79. The composition according to one of claims 75-78, wherein said at least one fatty alcohol is present in an amount ranging from 0.1% to 15.0% by weight, relative to the weight of the composition.
80. The composition according to one of claims 75-79 wherein said at least one fatty alcohol is present in an amount ranging from 0.5% to 8.0% by weight, relative to the weight of the composition.
81. The composition according to one of claims 1-80, further comprising at least one oil-soluble polymer.
82. The composition according to claim 81 , wherein said at least oil- soluble polymer is chosen from alkylated guar gums and alkyl celluloses.
83. The composition according to one of claims 81 or 82, wherein- said at least one oil-soluble polymer is present in an amount ranging from 0.05% to 10% by weight, relative to the weight of the composition.
84. The composition according to one of claims 81-83, wherein said at least one oil-soluble polymer is present in an amount ranging from 0.1 % to 3% by weight, relative to the weight of the composition.
85. The composition according to one of claims 1-84, further comprising at least one oil-soluble cationic surfactant.
86. The composition according to claim 85, wherein said at least one oil-soluble cationic surfactant is chosen from quaternary ammonium compounds, fatty amines, and salts of fatty amines.
87. The composition according to one of claims 85 or 86, wherein said at least one oil-soluble cationic surfactant is present in an amount ranging from 0.1 % to 10% by weight, relative to the weight of the composition.
88. The composition according to one of claims 85-87, wherein said at least one oil-soluble cationic surfactant is present in an amount ranging from 0.5% to 2% by weight, relative to the weight of the composition.
89. The composition according to one of claims 1-88, further comprising at least one wax.
90. The composition according to claim 89, wherein said at least one wax is chosen from carnauba wax, candelilla wax, ouricury wax, Japan wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite wax, microcrystalline waxes, lanolin wax, montan wax, polyethylene waxes, waxes obtained by Fischer-Tropsch synthesis, silicone waxes, ozokerites, hydrogenated jojoba oil, fatty acid esters, and fatty acid ester glycerides.
91. The composition according to one of claims 89 or 90, wherein said at least one wax is present in an amount ranging from 0.5% to 15 %, relative to the total weight of said composition.
92. A composition comprising at least one liquid fatty phase which comprises:
(i) at least one structuring polymer, wherein said at least one structuring polymer is at least one polyamide polymer comprising: a polymer skeleton which comprises at least one amide repeating unit; and
(ii) at least one film-forming silicone resin.
93. The composition according to claim 92, wherein said at least one polyamide polymer is chosen from polymers resulting from at least one polycondensation reaction between at least one dicarboxylic acid comprising at least 32 carbon atoms and at least one amine chosen from diamines comprising at least 2 carbon atoms and triamines comprising at least 2 carbon atoms.
94. The composition according to claim 93, wherein said at least one dicarboxylic acid comprises from 32 to 44 carbon atoms and said at least one amine comprises from 2 to 36 carbon atoms.
95. The composition according to one of claims 93 or 94, wherein said at least one dicarboxylic acid is chosen from dimers of at least one fatty acid comprising at least 16 carbon atoms.
96. The composition according to one of claims 93-95, wherein said at least one fatty acid is chosen from oleic acid, linoleic acid and linolenic acid.
97. The composition according to one of claims 93-96, wherein said at least one amine is chosen from ethylenediamine, hexylenediamine, hexamethylenediamine, phenylenediamine and ethylenetriamine.
98. The composition according to one of claims 93-97, wherein said at least one polyamide polymer is chosen from polymers comprising at least one terminal carboxylic acid group.
99. The composition according to claim 98, wherein said at least one terminal carboxylic acid group is esterified with at least one alcohol chosen from monoalcohols comprising at least 4 carbon atoms.
100. The composition according to one of claims 92-99, wherein said at least one film-forming silicone resin is chosen from silsesquioxanes and siloxysilicates.
101. The composition according to claim 100, wherein said silsesquioxanes comprise repeating units of (RSiO3/2)x, where X is less than 2000.
102. The composition according to claim 101 , wherein x is 500 or less.
103. The composition according to claim 100, wherein said silsesquioxanes are chosen from polymethylsilsesquioxanes comprising repeating units of formula (CH3SiO3/2).
104. The composition according to claim 100, wherein said siloxysilicates are chosen from trimethylsiloxysilicates.
105. The composition according to claim 104, wherein said trimethylsiloxysilicates comprise repeating units of [(CH3)3-Si-O]x-(SiO4/2)y, where x ranges from 50 to 80 and y ranges from 50 to 80.
106. The composition according to claim 103, wherein said polymethylsilsesquioxanes comprising repeating units of formula (CH3SiO3/2) further comprise up to 1% of polymerized repeating units of formula
Figure imgf000049_0001
107. The composition according to one of claims 92-106, wherein the at least one film-forming silicone resin comprises at least two units chosen from M, D, T, and Q and said at least two units satisfy the relationship RnSiO(4-n) 2, wherein n is a value ranging from 1.0 to 1.50.
108. The composition according to claim 107, wherein said at least one film-forming silicone resin is a solid at 25°C.
109. The composition according to claim 107, wherein said at least one film-forming silicone resin has a weight average molecular weight ranging from 1000 to 10,000 grams/mole.
110. The composition according to one of claims 92-109, wherein said at least one film-forming silicone resin comprises repeating M units and repeating Q units.
111. The composition according to claim 110, wherein the ratio of M units to Q units is 0.7:1.
112. The composition according to one of claims 92-111 , wherein said at least one film-forming silicone resin is present in the composition in an amount ranging from 1 % to 10% by weight, relative to the total weight of the composition.
113. The composition according to one of claims 92-112, wherein said composition further comprises at least one additional film-former.
114. The composition according to one of claims 92-113, wherein the composition is in a form chosen from a fluid anhydrous gel, rigid anhydrous gel, fluid simple emulsion, rigid simple emulsion, fluid multiple emulsion, and rigid multiple emulsion.
115. The composition according to one of claims 92-114, wherein said composition is a solid.
116. The composition according to one of claims 92-115, further comprising at least one wax.
117. A foundation, mascara, eye liner, concealer, lipstick, blush for cheeks or eyelids, body makeup, sun screen, colorant for skin or hair, skin care formula, shampoo, after shampoo treatment, or makeup removing product comprising: at least one liquid fatty phase in said foundation, mascara, eye liner, concealer, lipstick, blush for cheeks or eyelids, body makeup, sun screen, colorant for skin or hair, skin care formula, shampoo, after shampoo treatment, or makeup removing product which comprises:
(i) at least one structuring polymer comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom; and
(ii) at least one film-forming silicone resin.
118. An anhydrous deodorant comprising: at least one liquid fatty phase in said deodorant which comprises: (i) at least one structuring polymer comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom; and
(ii) at least one film-forming silicone resin.
119. A make-up and/or care and/or treatment composition for at least one keratinous material comprising: at least one liquid fatty phase in said composition which comprises: (i) at least one structuring polymer comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom; and
(ii) at least one film-forming silicone resin.
120. A lip composition in stick form comprising at least one continuous liquid fatty phase, at least one film-forming silicone resin, and at least one non-waxy structuring polymer having a weight-average molecular mass of less than 100,000 in said lip composition.
121. A make up, care, or treatment composition for the skin or lips comprising a structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom, at least one film-forming silicone resin, and at least one coloring agent.
122. A treatment, care or make-up composition for at least one keratinous material comprising a structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, at least one film-forming silicone resin, and at least one coloring agent.
123. A structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, wherein the at least one structuring polymer further comprises at least one terminal fatty chain, optionally functionalized, chosen from alkyl chains and alkenyl chains, wherein said at least one terminal fatty chain is bonded to said polymer skeleton via at least one linking group chosen from amides, ureas, and esters, wherein when said at least one linking group is chosen from esters, said at least one terminal fatty chain is chosen from branched alkyl groups and at least one film-forming silicone resin.
124. A structured composition comprising at least one liquid fatty phase structured with at least one structuring polymer comprising a polymer skeleton comprising at least one hydrocarbon-based repeating unit comprising at least one heteroatom, wherein the at least one structuring polymer further comprises at least one pendant fatty chain, optionally functionalized, chosen from alkyl chains and alkenyl chains, wherein said at least one pendant fatty chain is bonded to said polymer skeleton via at least one linking group chosen from amides, ureas, and esters, wherein when said at least one linking group is chosen from esters, said at least one pendant fatty chain is chosen from branched alkyl groups and at least one film-forming silicone resin.
125. A method for care, make up, or treatment of at least one keratinous material, comprising applying to said at least one keratinous material a cosmetic composition comprising: at least one liquid fatty phase which comprises:
(i) at least one structuring polymer comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom, and
(ii) at least one film-forming silicone resin.
126. A method for making a cosmetic composition in the form of a physiologically acceptable composition comprising including in said composition at least one liquid fatty phase which comprises:
(i) at least one structuring polymer comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom; and
(ii) at least one film-forming silicone resin.
127. A composition comprising at least one liquid fatty phase which comprises:
(i) at least one structuring polymer comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom, and at least one terminal fatty chain chosen from alkyl chains and alkenyl chains, wherein said at least one terminal fatty chain is bonded to said polymer skeleton via at least one linking group; and
(ii) at least one film-forming silicone resin.
128. A method for providing at least one property of resistance to shear and stability to a cosmetic composition, comprising including in said cosmetic composition a cosmetic composition at least one liquid fatty phase which comprises: (i) at least one structuring polymer comprising a polymer skeleton which comprises at least one hydrocarbon-based repeating unit comprising at least one heteroatom; and
(ii) at least one film-forming silicone resin, and further wherein said at least one structuring polymer and said at least one film-forming silicone resin are present in a combined amount effective to provide at least one property chosen from resistance to shear and stability to said composition.
129. A composition comprising at least one liquid fatty phase which comprises:
(i) at least one structuring polymer comprising: a polymer skeleton which comprises a) at least one hydrocarbon-based repeating unit comprising at least one heteroatom and b) at least one of:
- at least one terminal fatty chain, optionally functionalized, chosen from alkyl chains and alkenyl chains, wherein said at least one terminal fatty chain is bonded to said polymer skeleton via at least one linking group; and
- at least one pendant fatty chain, optionally functionalized, chosen from alkyl chains and alkenyl chains, wherein said at least one pendant fatty chain is bonded to said polymer skeleton via at least one linking group; and
(ii) at least one film-forming silicone resin.
PCT/US2001/047459 2000-12-12 2001-12-12 Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using WO2002080863A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA002399467A CA2399467A1 (en) 2000-12-12 2001-12-12 Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using
JP2002578902A JP2004519548A (en) 2000-12-12 2001-12-12 Cosmetic composition comprising at least one heteropolymer and at least one film-forming silicone resin and method of using the same
AU2001297750A AU2001297750A1 (en) 2000-12-12 2001-12-12 Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using
BR0108238-8A BR0108238A (en) 2000-12-12 2001-12-12 Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of employing them
EP01273639A EP1353626A2 (en) 2000-12-12 2001-12-12 Cosmetic compositions containing at least one polyamide and at least one film-forming silicone resin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/733,899 2000-12-12
US09/733,899 US8080257B2 (en) 2000-12-12 2000-12-12 Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using

Publications (2)

Publication Number Publication Date
WO2002080863A2 true WO2002080863A2 (en) 2002-10-17
WO2002080863A3 WO2002080863A3 (en) 2003-05-01

Family

ID=24949563

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/047459 WO2002080863A2 (en) 2000-12-12 2001-12-12 Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using

Country Status (8)

Country Link
US (1) US8080257B2 (en)
EP (1) EP1353626A2 (en)
JP (1) JP2004519548A (en)
CN (1) CN100413488C (en)
AU (1) AU2001297750A1 (en)
BR (1) BR0108238A (en)
CA (1) CA2399467A1 (en)
WO (1) WO2002080863A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8025869B2 (en) 2005-06-28 2011-09-27 L'oréal Cosmetic compositions having enhanced wear properties

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8080257B2 (en) 2000-12-12 2011-12-20 L'oreal S.A. Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using
US6726900B2 (en) * 2001-05-18 2004-04-27 Revlon Consumer Products Corporation Long wearing composition for making up eyes, skin, and lips
US20050008598A1 (en) 2003-07-11 2005-01-13 Shaoxiang Lu Cosmetic compositions comprising a structuring agent, silicone powder and swelling agent
WO2004066918A2 (en) 2003-01-17 2004-08-12 L'oreal Long wear cosmetic composition
US20040156806A1 (en) * 2003-02-11 2004-08-12 Patil Anjali Abhimanyu Cosmetic compositions containing siloxane resins
US20040161395A1 (en) * 2003-02-14 2004-08-19 Patil Anjali Abhimanyu Cosmetic compositions containing composite siloxane polymers
WO2004082611A2 (en) * 2003-03-14 2004-09-30 L'oreal Poss and eposs containing cosmetics and personal care products
US8604151B2 (en) 2004-02-02 2013-12-10 Dow Corning Corporation Bodied siloxane resin including M, Q, and T-propyl units and capped with additional M units
CN1914251B (en) 2004-02-02 2012-03-28 陶氏康宁公司 MQ-T propyl siloxane resins
ATE405612T1 (en) * 2004-02-02 2008-09-15 Dow Corning MQ AND T-PROPYL SILOXANE RESIN COMPOSITIONS
ATE448264T1 (en) * 2004-03-16 2009-11-15 Dow Corning COMPOSITIONS CONTAINING ALKYL-PHENYL-SILSESQUIOXANE RESINS
US8394394B2 (en) 2004-05-26 2013-03-12 L'oréal Mousse formulations
US7611726B2 (en) * 2004-07-15 2009-11-03 L'oréal Shine-enhancing film formers
US20080081022A1 (en) * 2004-09-13 2008-04-03 L'oreal Poss Containing Cosmetic Compositions Having Improved Wear And/Or Pliability And Methods Of Making Improved Cosmetic Compositions
FR2881343B1 (en) * 2005-01-31 2007-04-20 Oreal SOLID COSMETIC COMPOSITION FOR MAKE-UP AND / OR CARE
US20060193801A1 (en) * 2005-01-31 2006-08-31 L'oreal Solid cosmetic composition textured with an organic copolymer
US8241617B2 (en) * 2005-08-01 2012-08-14 L'oréal Methods for removing make-up compositions from keratin materials
US8388940B2 (en) * 2006-03-13 2013-03-05 L'oreal Mascara compositions
US8758739B2 (en) * 2006-05-03 2014-06-24 L'oreal Cosmetic compositions containing block copolymers, tackifiers and gelling agents
US8673282B2 (en) * 2006-05-03 2014-03-18 L'oreal Cosmetic compositions containing block copolymers, tackifiers and a selective solvent for soft blocks
US8673283B2 (en) * 2006-05-03 2014-03-18 L'oreal Cosmetic compositions containing block copolymers, tackifiers and a solvent mixture
US8673284B2 (en) * 2006-05-03 2014-03-18 L'oreal Cosmetic compositions containing block copolymers, tackifiers and a selective solvent for hard blocks
US8778323B2 (en) * 2006-05-03 2014-07-15 L'oréal Cosmetic compositions containing block copolymers, tackifiers and modified silicones
US8557230B2 (en) * 2006-05-03 2013-10-15 L'oreal Cosmetic compositions containing block copolymers, tackifiers and shine enhancing agents
US8715634B2 (en) * 2006-10-24 2014-05-06 L'oreal Volumizing compositions
US8658141B2 (en) * 2007-01-12 2014-02-25 L'oreal Cosmetic composition containing a block copolymer, a tackifier, a silsesquioxane wax and/or resin
US8603444B2 (en) * 2007-01-12 2013-12-10 L'oréal Cosmetic compositions containing a block copolymer, a tackifier and a high viscosity ester
US20080171008A1 (en) * 2007-01-17 2008-07-17 L'oreal S.A. Composition containing a polyorganosiloxane polymer, a tackifier, a wax and a block copolymer
WO2009080953A2 (en) * 2007-12-05 2009-07-02 L'oreal Cosmetic make-up and/or care method using a siloxane resin and a phenyl silicone oil
US20120219516A1 (en) 2011-02-25 2012-08-30 L'oreal S.A. Cosmetic compositions having long lasting shine
US10532020B2 (en) 2012-08-22 2020-01-14 Revlon Consumer Products Corporation Nail coatings having enhanced adhesion
AU2014257171B2 (en) 2013-04-22 2019-05-16 Creative Nail Design, Inc. Nail coatings having enhanced adhesion
WO2015105931A1 (en) 2014-01-08 2015-07-16 Dow Corning Corporation Method for capping mq-type silicone resins
AU2017229125B2 (en) 2016-03-08 2021-07-29 Living Proof, Inc. Long lasting cosmetic compositions
FR3061432B1 (en) * 2016-12-30 2020-05-29 Lvmh Recherche COMPOSITION OF MASCARA AND PACKAGING
WO2019055440A1 (en) 2017-09-13 2019-03-21 Living Proof, Inc. Long lasting cosmetic compositions
EP3681921A2 (en) 2017-09-13 2020-07-22 Living Proof, Inc. Color protectant compositions
US20190262257A1 (en) 2018-02-28 2019-08-29 L'oreal Matte lip compositions

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5500209A (en) * 1994-03-17 1996-03-19 The Mennen Company Deodorant and antiperspirant compositions containing polyamide gelling agent
US5783657A (en) * 1996-10-18 1998-07-21 Union Camp Corporation Ester-terminated polyamides of polymerized fatty acids useful in formulating transparent gels in low polarity liquids
US5911974A (en) * 1994-10-25 1999-06-15 Revlon Consumer Products Corporation Cosmetic compositions
US6074654A (en) * 1995-11-07 2000-06-13 The Procter & Gamble Company Transfer resistant cosmetic compositions
EP1031342A1 (en) * 1999-02-24 2000-08-30 L'oreal Mascara composition containing wax, film forming polymer and silicone
WO2001052799A1 (en) * 2000-01-24 2001-07-26 L'oreal Transfer-resistant composition structured in rigid form by a polymer

Family Cites Families (383)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2379413A (en) 1940-06-28 1945-07-03 American Cyanamid Co Amides of high molecular weight carboxylic acids
US2463264A (en) 1942-12-23 1949-03-01 Ciba Ltd Derivatives of cyclic amidines and process of making same
US2450940A (en) 1944-04-20 1948-10-12 John C Cowan Polyamides from polymeric fat acids
US2662068A (en) 1951-03-16 1953-12-08 Gen Mills Inc Organic solvent gels
US2663649A (en) 1952-07-01 1953-12-22 T F Washburn Co Ester modified polyamide resins
US2962461A (en) 1956-11-30 1960-11-29 T F Washburn Company Method for determining end point of polyamide modified vehicle cooks
US2890097A (en) 1958-05-12 1959-06-09 Thompson J Coe Shrinkproofing textiles with polyamides and volatile polyepoxides
US3086914A (en) 1959-06-23 1963-04-23 Faberge Inc Lip-coloring compositions
NL254088A (en) 1959-07-29
US3148125A (en) 1961-03-22 1964-09-08 Yardley Of London Inc Clear lipstick
US3156572A (en) 1961-10-18 1964-11-10 Interchonical Corp Printing inks
US3255082A (en) 1962-04-16 1966-06-07 Procter & Gamble Method of preparing stable aluminum chlorhydrate-alkali metal- and alkaline earth metal salt complex antiperspirant stick
US3157681A (en) 1962-06-28 1964-11-17 Gen Mills Inc Polymeric fat acids
US3324041A (en) * 1964-01-17 1967-06-06 Shell Oil Co Oil-in-water settable aqueous emulsions
US3412115A (en) 1964-11-02 1968-11-19 Gen Mills Inc Polyamide resin
US3341465A (en) 1965-01-14 1967-09-12 Drew Chem Corp Novel gel emulsions
GB1117129A (en) 1965-09-18 1968-06-19 Yardley And Company Ltd A cosmetic preparation
GB1194901A (en) 1965-09-18 1970-06-17 Yardley And Company Ltd Polyamide Compositions
DE1617947C3 (en) 1966-02-23 1974-10-31 Yardley & Co. Ltd., London Hair cleansers and fixatives
GB1220069A (en) 1966-12-13 1971-01-20 Harold Samuel Akronglod Improvements in or relating to a hydrophilic gel
FR1529329A (en) 1967-06-28 1968-06-14 Max Factor & Co Composition and method for restoring broken nails
JPS5010282B1 (en) 1968-06-25 1975-04-19
US3615289A (en) 1969-03-26 1971-10-26 Avon Prod Inc Candle composition
US3645705A (en) 1970-03-03 1972-02-29 Kolar Lab Inc Transparent combustible material suitable for candle bodies
US3819342A (en) * 1971-03-26 1974-06-25 Avon Prod Inc Transparent candle
US3778394A (en) 1972-08-24 1973-12-11 Gen Mills Chem Inc Polymeric fatty acid polyamide modified with a rosin adduct
US3857960A (en) 1972-12-29 1974-12-31 Bristol Myers Co Toilet oil bar
US3926655A (en) 1973-01-31 1975-12-16 Hercules Inc Clear perfumed polyamide resin and method of making it
CA1022288A (en) 1973-01-31 1977-12-06 Jeffrey M. Miles Clear perfumed polyamide resin and method of preparing it
US4137306A (en) 1973-06-05 1979-01-30 Armour Pharmaceutical Company Anhydrous antiperspirant stick compositions
LU67772A1 (en) 1973-06-08 1975-03-06
USRE29871E (en) 1973-06-08 1978-12-26 L'oreal Fatty compositions for use in cosmetic makeup compositions and said cosmetic makeup compositions
US4049792A (en) 1973-06-26 1977-09-20 The Procter & Gamble Company Antiperspirant stick
GB1506701A (en) * 1973-12-06 1978-04-12 Scotus Marine Ltd Pressure sensing device
US4128436A (en) 1974-05-29 1978-12-05 Coats Brothers & Company Ltd. Rheological agents
US3969087A (en) 1974-08-07 1976-07-13 Ajinomoto Co., Ltd. Gels of nonpolar liquids with N-acyl amino acids and derivatives thereof as gelling agents
FR2315991A1 (en) 1975-06-30 1977-01-28 Oreal METHOD OF MANUFACTURING AQUEOUS DISPERSIONS OF LIPID SPHERULES AND CORRESPONDING NEW COMPOSITIONS
US4087555A (en) 1975-09-08 1978-05-02 Helena Rubinstein, Inc. Skin cream containing milk protein
US4051159A (en) 1976-01-12 1977-09-27 Avon Products, Inc. Transparent fragrance releasing composition and method of making same
US4062819A (en) 1976-09-07 1977-12-13 Emery Industries, Inc. Polyamide blends having improved processing characteristics
JPS584777B2 (en) 1976-09-30 1983-01-27 三菱電機株式会社 average temperature detection tube
LU76035A1 (en) * 1976-10-20 1978-05-16
NL185519C (en) 1976-12-23 1990-05-01 Schering Ag METHOD FOR PREPARING MELTING ADHESIVES FOR TEXTILE AND FORMED PRODUCTS.
JPS5437837A (en) 1977-08-26 1979-03-20 Shiseido Co Ltd Makeup cosmetics
FR2416008A1 (en) 1978-02-02 1979-08-31 Oreal LIPOSOME LYOPHILISATES
JPS54113445A (en) 1978-02-23 1979-09-05 Kanebo Ltd Lipstick having sheath-core structure
IT1163973B (en) 1978-03-17 1987-04-08 Shiseido Co Ltd COMPOSITION OF GEL INCLUDING A CLAY MINERAL AND A LIQUID CRYSTAL, AND COSMETIC PREPARATION THAT CONTAINS IT
US4279658A (en) * 1978-08-16 1981-07-21 Grain Processing Corporation Chemical-mechanical starch conversion
US4275055A (en) 1979-06-22 1981-06-23 Conair Corporation Hair conditioner having a stabilized, pearlescent effect
DE2942680C2 (en) 1979-10-23 1986-02-27 Schering AG, 1000 Berlin und 4709 Bergkamen Hot melt adhesives based on polyester amides and their use for bonding organic and inorganic substrates
US4376194A (en) 1979-12-21 1983-03-08 Toray Industries, Inc. Polyester amide and process for producing the same
JPS56123909A (en) 1980-03-06 1981-09-29 Isehan:Kk Nail reinforcing agent
US4387090A (en) 1980-12-22 1983-06-07 The Procter & Gamble Company Hair conditioning compositions
JPS56166276A (en) 1980-05-27 1981-12-21 Kao Corp Printing ink
US4337298A (en) 1980-11-19 1982-06-29 Gulf Oil Corporation Polymer compositions and laminates produced by bonding or coextrusion
US4466936A (en) 1981-02-03 1984-08-21 Bayer Aktiengesellschaft Production of molds using gel compositions with depot action based on a polyurethane matrix and relatively high molecular weight polyols
DE3206398A1 (en) * 1982-02-23 1983-09-01 Basf Ag, 6700 Ludwigshafen S-TRIAZINE DERIVATIVES AND THEIR USE AS LIGHT PROTECTION AGENTS
JPS58206628A (en) 1982-05-27 1983-12-01 Toray Ind Inc Preparation of polyether ester amide
LU84210A1 (en) 1982-06-17 1984-03-07 Oreal COMPOSITION BASED ON CATIONIC POLYMERS, ANIONIC POLYMERS AND WAXES FOR USE IN COSMETICS
DE3243794A1 (en) 1982-11-26 1984-05-30 Schering AG, 1000 Berlin und 4709 Bergkamen ALCOHOL SOLE PRINTING INKS
GB8302683D0 (en) 1983-02-01 1983-03-02 Unilever Plc Skin treatment composition
DE3411920A1 (en) 1983-03-30 1984-10-25 Estee Lauder Inc., New York, N.Y. Airtightly sealable container
US4552693A (en) 1983-03-30 1985-11-12 Avon Products, Inc. Transparent fragrance emitting articles
US5102656A (en) 1983-07-29 1992-04-07 The Mennen Company Antiperspirant creams
JPS6055021A (en) 1983-09-05 1985-03-29 Daiseru Hiyurusu Kk Production of polyamide/polysiloxane block copolymer
WO1985002852A1 (en) 1983-12-27 1985-07-04 Daicel Chemical Industries, Ltd. Polyesteramides
DE3420009A1 (en) 1984-05-29 1985-12-05 Schering AG, 1000 Berlin und 4709 Bergkamen METHOD FOR PRODUCING ANTI-SLIP SLAGS
US4712571A (en) 1984-06-29 1987-12-15 Chesebrough-Pond's, Inc. Nail polish compositions and means for applying same
EP0169997B1 (en) 1984-07-28 1991-09-18 Kernforschungszentrum Karlsruhe Gmbh Process for purifying smoke
JPH0615452B2 (en) 1984-09-06 1994-03-02 株式会社資生堂 Makeup cosmetics
US5268029A (en) 1985-02-12 1993-12-07 Elf France Cationic emulsions of bituminous binders of the type bitumen/polymer and cationic emulsifying system preferably utilizable for obtaining said emulsions
US4806338A (en) 1985-05-30 1989-02-21 The Procter & Gamble Company Antiperspirant aerosol compositions
US4769285A (en) 1985-07-23 1988-09-06 Minnesota Mining And Manufacturing Company Polyamide-acrylate blends
US4937069A (en) 1985-11-15 1990-06-26 Bristol-Myers Squibb Company Anhydrous semi-solid antiperspirant suspension
US4806345C1 (en) 1985-11-21 2001-02-06 Johnson & Son Inc C Cross-linked cationic polymers for use in personal care products
US4820765A (en) 1985-12-20 1989-04-11 Henkel Corporation Polyamide from diamine and excess aromatic dicarboxylic acid
US4699779A (en) 1986-02-18 1987-10-13 Victor Palinczar Waterproof sunscreen compositions
GB2196978B (en) 1986-09-25 1990-04-18 Plough Cosmetic nail strengthening compositions and method of using same
US4822601A (en) * 1987-03-13 1989-04-18 R.I.T.A. Corporation Cosmetic base composition with therapeutic properties
JPS63313710A (en) 1987-06-16 1988-12-21 Toray Silicone Co Ltd Face cleaning cosmetic
JP2691729B2 (en) 1987-06-23 1997-12-17 株式会社資生堂 Solid water-in-oil emulsified cosmetic
US5069897A (en) 1987-10-16 1991-12-03 The Proctor & Gamble Company Antiperspirant creams
JPH02127568A (en) 1988-07-08 1990-05-16 Kuraray Co Ltd High-strength and high-modulus fiber having improved abrasion resistance
JPH0234669A (en) 1988-07-22 1990-02-05 Kao Corp Dye-containing nacreous pigment and cosmetic containing same
US5126136A (en) * 1988-08-05 1992-06-30 Merat Pierre H Skin protection lotion
JP2641271B2 (en) 1988-10-17 1997-08-13 帝人株式会社 Surface-modified wholly aromatic polyamide fiber
US5196260A (en) 1988-11-19 1993-03-23 Ciba-Geigy Corporation Process for the treatment of fibrous materials with modified organopolysiloxanes and the materials
DE3839136A1 (en) 1988-11-19 1990-05-23 Pfersee Chem Fab METHOD FOR THE TREATMENT OF FIBROUS MATERIALS WITH MODIFIED ORGANOPOLYSILOXANS AND THE MATERIALS TREATED THEREFORE
CA2003346C (en) 1988-11-23 2000-02-15 Luis C. Calvo Fluorescent cosmetic compositions
DE3843892A1 (en) 1988-12-24 1990-06-28 Wella Ag OXIDATION HAIR AGENTS CONTAINING DIAMINOPYRAZOL DERIVATIVES AND NEW DIAMINOPYRAZOLE DERIVATIVES
US5034219A (en) 1989-03-13 1991-07-23 Sterling Drug Inc. Pre-perm hair conditioner
JP2664481B2 (en) 1989-06-09 1997-10-15 松本油脂製薬株式会社 Treatment agent for fiber modification
EP0412710B1 (en) 1989-08-07 1995-07-19 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
US5290555A (en) * 1989-09-14 1994-03-01 Revlon Consumer Products Corporation Cosmetic compositions with structural color
CA2033642A1 (en) 1990-01-11 1991-07-12 Dilip R. Abayasekara Graft polymers of epsilon-caprolactam
JP3044048B2 (en) 1990-02-28 2000-05-22 東レ・ダウコーニング・シリコーン株式会社 Organopolysiloxane-based elastomer powder and method for producing the same
US5925337A (en) * 1990-03-01 1999-07-20 L'oreal Waterproof composition for covering the eyelashes, and process for the preparation thereof
FR2659011B1 (en) 1990-03-01 1994-09-30 Oreal WATER RESISTANT COMPOSITION FOR COATING EYELASHES, AND PREPARATION METHOD THEREOF.
US5472686A (en) 1990-12-28 1995-12-05 Nippon Unicar Company Limited Cosmetic formulations
US5073364A (en) 1990-06-19 1991-12-17 Revlon, Inc. Pressed powder cosmetic product
ATE132736T1 (en) 1990-06-21 1996-01-15 Revlon Consumer Prod Corp COSMETIC PREPARATIONS
US5075103A (en) 1990-07-06 1991-12-24 Dow Corning Corporation Hair fixatives comprising nonpolar silsesquioxanes
US5085859A (en) * 1990-07-06 1992-02-04 Dow Corning Corporation Hair fixatives
FR2666014B1 (en) * 1990-08-23 1994-10-28 Oreal COSMETIC COMPOSITION FOR HAIR CONTAINING A FILM - FORMING POLYMER AND A SILICONE INCORPORATED IN A WAX MICRODISPERSION, AND COSMETIC TREATMENT METHOD.
US5237071A (en) 1991-01-22 1993-08-17 Fairmount Chemical Company, Inc. Process for preparing 2,2'-methylene-bis(6-(2H-benzotriazol-2-yl)-4-hydrocarbyl phenols)
US5166355A (en) 1991-02-04 1992-11-24 Fairmount Chemical Co., Inc. Process for preparing substituted 2,2'-methylene-bis-[6-(2H-benzotriazol-2-yl)-4-hydrocarbyl-phenols]
FR2673179B1 (en) 1991-02-21 1993-06-11 Oreal CERAMIDES, THEIR PREPARATION PROCESS AND THEIR APPLICATIONS IN COSMETICS AND DERMOPHARMACY.
FR2673372B1 (en) 1991-02-28 1993-10-01 Oreal COSMETIC COMPOSITION CAPABLE OF REDUCING SKIN DEFECTS.
FR2674126B1 (en) 1991-03-19 1995-03-10 Secma USE OF RED LIME ALGAE FOR THE PREPARATION OF COSMETIC COMPOSITIONS.
DE4110506A1 (en) * 1991-03-30 1992-10-01 Huels Chemische Werke Ag EMULSIFIERS FOR THE PRODUCTION OF OIL-IN-WATER EMULSIONS OF ETHERIC OILS USED IN COSMETICS OR MEDICINE
FR2674851B1 (en) 1991-04-04 1995-02-10 Oreal S-TRIAZINIC DERIVATIVES CARRYING BENZYLIDENE CAMPHOR SUBSTITUENTS, FILTERING COSMETIC COMPOSITIONS AND THEIR USE FOR PROTECTING THE SKIN AND HAIR FROM ULTRAVIOLET RADIATION.
IT1245889B (en) * 1991-04-12 1994-10-25 Alfa Wassermann Spa PHARMACEUTICAL FORMULATIONS FOR ORAL USE GAS RESISTANT CONTAINING SALTS OF BILE ACIDS.
IT1247973B (en) 1991-06-04 1995-01-05 Sigma Prod Chim 1,3,5-TRIAZINE DERIVATIVES, THEIR PREPARATION AND USE AS SOLAR FILTERS
FR2677543B1 (en) 1991-06-13 1993-09-24 Oreal COSMETIC FILTERING COMPOSITION BASED ON BENZENE 1,4-DI ACID (3-METHYLIDENE-10-CAMPHOSULFONIC) AND NANOPIGMENTS OF METAL OXIDES.
FR2677544B1 (en) 1991-06-14 1993-09-24 Oreal COSMETIC COMPOSITION CONTAINING A MIXTURE OF NANOPIGMENTS OF METAL OXIDES AND MELANIC PIGMENTS.
US5679357A (en) 1991-08-01 1997-10-21 L'oreal Cationic dispersions based on ceramides and/or glycoceramides
DE4128748A1 (en) * 1991-08-29 1993-03-04 Beiersdorf Ag COSMETIC PENS
FR2687569B1 (en) 1992-02-21 1995-06-09 Oreal COSMETIC COMPOSITION FOR EYE MAKE-UP, COMPRISING A MICRODISPERSION OF WAX.
DE4208297A1 (en) 1992-03-16 1993-09-23 Henkel Kgaa COLORING KERATINIC FIBERS WITH INDOLINES UNDER METAL CATALYSIS
IT1255729B (en) 1992-05-19 1995-11-15 Giuseppe Raspanti s-triazine derivatives as photostabilising agents
JP3442101B2 (en) * 1992-07-27 2003-09-02 日清オイリオ株式会社 Lanolin-like synthetic oils and cosmetics and external preparations containing them
US5272241A (en) 1992-08-21 1993-12-21 General Electric Company Amino acid functionalized silicones and method for preparation
DE4234886A1 (en) 1992-10-16 1994-04-21 Wella Ag New N-phenylaminopyrazole derivatives and agents and processes for coloring hair
US5372852A (en) 1992-11-25 1994-12-13 Tektronix, Inc. Indirect printing process for applying selective phase change ink compositions to substrates
JP3393903B2 (en) 1992-11-30 2003-04-07 株式会社資生堂 Makeup cosmetics
CA2107253C (en) * 1992-12-15 1998-04-21 Anthony Castrogiovanni Cosmetic compositions with improved transfer resistance
US5683817A (en) 1992-12-28 1997-11-04 E. I. Du Pont De Nemours And Company Polyamide composition and method of producing goods
FR2700690B1 (en) 1993-01-25 1995-03-24 Oreal Anhydrous solid dispersion containing organofluorinated hydrocarbon compounds and its use in cosmetics.
US5302379A (en) 1993-03-05 1994-04-12 Dow Corning Corporation Nail lacquer primary film forming resin
FR2702676B1 (en) 1993-03-18 1995-05-19 Oreal Oil-in-water emulsion containing a perfluoropolyether, composition comprising it, process for preparation and use in cosmetics and dermatology.
US5534247A (en) * 1993-03-25 1996-07-09 Maybelline Intermediate Co. Mascara composition
US5389363A (en) * 1993-04-23 1995-02-14 Revlon Consumer Products Corporation Cosmetic compositions for lengthening, coloring and curling eyelashes
SK53294A3 (en) 1993-05-07 1995-04-12 Albright & Wilson Concentrated aqueous mixture containing surface active matter and its use
US5299979A (en) * 1993-05-11 1994-04-05 Moore Business Forms, Inc. Shipping form with label
US5574083A (en) 1993-06-11 1996-11-12 Rohm And Haas Company Aromatic polycarbodiimide crosslinkers
FR2712805B1 (en) * 1993-11-24 1996-01-19 Oreal Cosmetic composition for make-up in the form of a mascara containing at least one wax and one pseudo-latex.
US5866149A (en) 1993-12-10 1999-02-02 L'oreal Composition for making up the eyelashes and the eyebrows stabilized oxyethylenated derivatives
JPH07179795A (en) 1993-12-24 1995-07-18 Nippon Oil & Fats Co Ltd Resin composition for cationic electrodeposition coating
JP2832143B2 (en) * 1993-12-28 1998-12-02 信越化学工業株式会社 Silicone fine particles and method for producing the same
FR2715843B1 (en) 1994-02-09 1996-04-12 Oreal Sunscreen cosmetic compositions, preparation process and use.
DE4405510A1 (en) 1994-02-22 1995-08-24 Henkel Kgaa Emulsions
EP0669323B2 (en) 1994-02-24 2004-04-07 Haarmann & Reimer Gmbh Cosmetic and dermatological preparations, containing phenylene-1,4-bisbenzimidazole sulfonic acids
US5486431A (en) 1994-03-02 1996-01-23 Micron Communications, Inc. Method of producing button-type batteries and spring-biased concave button-type battery
WO1995024439A2 (en) 1994-03-11 1995-09-14 Henkel Kommanditgesellschaft Auf Aktien Dimer fatty acid-based polyamide
US5610199A (en) 1994-03-22 1997-03-11 Estee Lauder Inc. Solid lipophilic composition and process for its preparation
JP3405588B2 (en) 1994-03-31 2003-05-12 株式会社資生堂 Oil-in-water type eyelash cosmetic
AU701587B2 (en) * 1994-05-13 1999-02-04 Unilever Plc Detergent composition
US6180117B1 (en) * 1994-05-27 2001-01-30 General Electric Company Method of preparing microemulsions of amino silicone fluids and MQ resin mixtures
JP3422434B2 (en) 1994-05-31 2003-06-30 新日鐵化学株式会社 Silicate group-containing polyimide
FR2720641B1 (en) 1994-06-03 1996-07-26 Oreal Sunscreen cosmetic compositions comprising 2,4,6-tris [p- (2'-ethylhexyl-1'-oxycarbonyl) anilino] -1,3,5-triazine and dioctyl malate and uses.
US5510452A (en) 1994-07-11 1996-04-23 Rheox, Inc. Pourable liquid polyesteramide rheological additives and the use thererof
FR2725369B1 (en) 1994-10-07 1997-01-03 Oreal COSMETIC OR DERMATOLOGICAL COMPOSITION CONSISTING OF AN OIL IN WATER EMULSION BASED ON OIL CELLS PROVIDED WITH A LAMELLAR LIQUID CRYSTAL COATING
FR2725366B1 (en) * 1994-10-10 1996-11-22 Oreal COSMETIC COMPOSITION COMPRISING SILICONE OILS
US5872246A (en) 1994-10-17 1999-02-16 Aqualon Company Ethyl guar
US5540853A (en) 1994-10-20 1996-07-30 The Procter & Gamble Company Personal treatment compositions and/or cosmetic compositions containing enduring perfume
JPH08180654A (en) * 1994-12-22 1996-07-12 Pioneer Electron Corp Information reproducing device
US5628029A (en) * 1995-02-03 1997-05-06 Vlsi Technology, Inc. Apparatus for monitoring distributed I/O device by providing a monitor in each I/O device control for generating signals based upon the device status
JPH08225316A (en) 1995-02-21 1996-09-03 Kao Corp Spherical inorganic powder
US5849333A (en) 1995-04-04 1998-12-15 American Westmin, Inc. Delaminated transparent talc
US5603925A (en) 1995-04-21 1997-02-18 The Mennen Company Clear or translucent tack-free antiperspirant stick or gel composition and manufacturing method
FR2734716B1 (en) 1995-06-01 1997-08-14 Oreal COSMETIC COMPOSITION IN THE FORM OF FLEXIBLE PASTE AND PROCESS FOR PREPARING THE SAME
JP3027008B2 (en) 1995-06-21 2000-03-27 ロレアル Cosmetic composition containing polymer particle dispersion
FR2735685B1 (en) 1995-06-21 1997-08-01 Oreal COMPOSITIONS FOR DYEING KERATIN FIBERS COMPRISING AN ORTHO-DIAMINO PYRAZOLE AND A MANGANESE SALT DYEING PROCESS USING THESE COMPOSITIONS
FR2735689B1 (en) 1995-06-21 1997-08-01 Oreal COMPOSITION COMPRISING A DISPERSION OF POLYMER PARTICLES IN A NON-AQUEOUS MEDIUM
CA2225996A1 (en) 1995-06-26 1997-01-16 Revlon Consumer Products Corporation Glossy transfer resistant cosmetic compositions
ZA966814B (en) 1995-08-18 1998-02-12 Colgate Palmolive Co Clear cosmetic gel composition.
JP3242561B2 (en) 1995-09-14 2001-12-25 メルク・ジヤパン株式会社 Flaky aluminum oxide, pearlescent pigment and method for producing the same
US6063398A (en) 1995-09-20 2000-05-16 L'oreal Cosmetic or dermopharmaceutical patch containing, in an anhydrous polymeric matrix, at least one active compound which is, in particular, unstable in oxidizing mediums, and at least one water-absorbing agent
FR2740330B1 (en) 1995-10-27 1997-12-05 Oreal COMPOSITION CONSISTING OF A POLYMERIC SYSTEM AND USE OF THE SAID SYSTEM
US5725845A (en) * 1995-11-03 1998-03-10 Revlon Consumer Products Corporation Transfer resistant cosmetic stick compositions with semi-matte finish
CN1098064C (en) * 1995-11-07 2003-01-08 普罗克特和甘保尔公司 Compositions and methods for improving performance of long-wearing cosmetic products
US6019962A (en) * 1995-11-07 2000-02-01 The Procter & Gamble Co. Compositions and methods for improving cosmetic products
US5972095A (en) 1995-11-17 1999-10-26 Maybelline Cosmetics Corporation Fast drying nail enamel composition and method
DE19543730A1 (en) 1995-11-23 1997-05-28 Ciba Geigy Ag Until resorcinyl-triazines
DE19543988A1 (en) 1995-11-25 1997-05-28 Wella Ag Oxidative hair dye composition
DE19603018C2 (en) 1996-01-17 1998-02-26 Lancaster Group Gmbh Cosmetic self-tanning agent with light protection effect
FR2744721B1 (en) 1996-02-12 1999-06-18 Oreal NOVEL INSOLUBLE S-TRIAZINE DERIVATIVES, PROCESS FOR THEIR PREPARATION, COMPOSITIONS CONTAINING THEM AND USES THEREOF
US5645632A (en) 1996-02-14 1997-07-08 Union Camp Corporation Diesters of polymerized fatty acids useful in formulating hot-melt inks
US5825543A (en) 1996-02-29 1998-10-20 Minnesota Mining And Manufacturing Company Diffusely reflecting polarizing element including a first birefringent phase and a second phase
US5871764A (en) 1996-02-29 1999-02-16 Johnson & Johnson Consumer Products, Inc. Skin toning formulation
US5750121A (en) * 1996-03-15 1998-05-12 Elizabeth Arden, A Division Of Conopco, Inc. Color cosmetic composition containing alcohol modified wax
FR2746302B1 (en) 1996-03-20 1998-12-24 Oreal COSMETIC COMPOSITIONS COMPRISING NANOPIGMENTS
IT1283295B1 (en) 1996-03-22 1998-04-16 3V Sigma Spa SOLAR FILTERS
US5667770A (en) 1996-03-25 1997-09-16 Elizabeth Arden Company, Division Of Conopco, Inc. Long wearing lipstick
US5919441A (en) 1996-04-01 1999-07-06 Colgate-Palmolive Company Cosmetic composition containing thickening agent of siloxane polymer with hydrogen-bonding groups
US5874069A (en) 1997-01-24 1999-02-23 Colgate-Palmolive Company Cosmetic composition containing silicon-modified amides as thickening agents and method of forming same
US5807968A (en) 1996-04-04 1998-09-15 Henkel Corporation Polyamide compositions and related methods
JPH09295922A (en) 1996-04-30 1997-11-18 Japan Synthetic Rubber Co Ltd Polymer particle and hair cosmetic
US5750125A (en) * 1996-06-19 1998-05-12 Estee Lauder, Inc. Clear cosmetic sticks and process for its preparation
FR2751533B1 (en) * 1996-07-23 2003-08-15 Oreal COMPOSITION OF OXIDIZING DYE FOR KERATINIC FIBERS CONTAINING A NON-IONIC AMPHIPHILIC POLYMER
FR2751543B1 (en) 1996-07-24 1998-09-11 Oreal COMPOSITION COMPRISING A POLYMERIC SYSTEM AND USE OF SAID SYSTEM IN PARTICULAR IN COSMETICS
TR199900236T2 (en) 1996-08-06 1999-04-21 Braun Aktiengesellschaft Rotary roller for epilator.
US5837223A (en) 1996-08-12 1998-11-17 Revlon Consumer Products Corporation Transfer resistant high lustre cosmetic stick compositions
US5830447A (en) 1996-09-04 1998-11-03 The Procter & Gamble Company Personal care compositions
US5993787A (en) 1996-09-13 1999-11-30 Johnson & Johnson Consumer Products, Inc. Composition base for topical therapeutic and cosmetic preparations
US6045823A (en) * 1996-09-19 2000-04-04 Dragoco Gerberding & Co. Ag Process for producing solid anhydrous composition, and pharmaceutical and cosmetic products comprising same
DE69735435T2 (en) 1996-10-18 2006-09-14 Arizona Chemical Co., Jacksonville ESTER-TERMINATED POLYAMIDE GEL
US5891425A (en) 1996-10-29 1999-04-06 Procter & Gamble Company Antiperspirant cream composition having improved rheology
EP0889719B1 (en) 1996-11-16 2003-04-02 Wella Aktiengesellschaft Agents for dying and decolorizing fibers
FR2756176B1 (en) 1996-11-26 1998-12-18 Oreal COSMETIC COMPOSITION COMPRISING A FLUORINATED COMPOUND AND HAVING IMPROVED COMFORT
CA2220033A1 (en) 1996-11-26 1998-05-26 L'oreal Non-transfer topical composition containing a fluorinated or silicone compound and offering improved comfort, its use
US5871758A (en) * 1996-12-11 1999-02-16 E-L Management Corp. Dual phase cosmetic composition
US6361764B2 (en) * 1996-12-13 2002-03-26 Societe L'oreal S.A. Insoluble s-triazine derivatives and their use as UV filters
JPH10175816A (en) * 1996-12-18 1998-06-30 Toray Dow Corning Silicone Co Ltd Cosmetic raw material, cosmetic and production of cosmetic
US6190673B1 (en) 1996-12-20 2001-02-20 The Procter & Gamble Company Gel compositions containing gellants in the form of alkyl amides of tri-carboxylic acids
CN1224343A (en) 1997-01-20 1999-07-28 莱雅公司 Cosmetic composition contg. as coating agent for keratinous fibre a film-forming mixture consisting of polymer particles capable of being film-forming and particles not capable of being film-formed
DE19707309B4 (en) 1997-02-11 2004-08-12 Lancaster Group Gmbh Solid cosmetic compositions based on solidified oils
US5908631A (en) * 1997-02-27 1999-06-01 L'oreal S.A. Monohydric alcohol-free composition for topical use comprising solubilized ethylcellulose
CN1249740A (en) * 1997-02-28 2000-04-05 新日本理化株式会社 p-hydroxybenzoic esters, plasticizer contg. same, polyamide resin composition, and molded objects
EP0863145B1 (en) 1997-03-03 2003-10-01 F. Hoffmann-La Roche Ag Sunscreen compositions
US5976512A (en) 1997-03-03 1999-11-02 Roche Vitamins Inc. Symetrical hydroxyphenyl-s-triazine compositions
US5785960A (en) 1997-03-19 1998-07-28 Elizabeth Arden Co., Division Of Conopco, Inc. Method and system for customizing dermatological foundation products
JPH10259344A (en) 1997-03-19 1998-09-29 Kao Corp Ink-form protective film forming agent
DE19716070C2 (en) 1997-04-17 2000-08-24 Cognis Deutschland Gmbh Sunscreen
JP3564259B2 (en) 1997-05-09 2004-09-08 楠本化成株式会社 Anti-settling agent for water-based paint
US6165457A (en) 1997-05-12 2000-12-26 The Procter & Gamble Company Personal care compositions containing toughened grafted polymers
TW432055B (en) 1997-05-16 2001-05-01 Ciba Sc Holding Ag Resorcinyl-triazines, their preparation process and a cosmetic composition containing them
EP0878469B1 (en) 1997-05-16 2004-10-27 Ciba SC Holding AG Resorcinyl-triazines
US5972359A (en) 1997-05-23 1999-10-26 The Procter & Gamble Company Skin care compositions and method of improving skin appearance
US6015574A (en) * 1997-06-09 2000-01-18 L'oreal Lipophilic carrier systems
US5945085A (en) * 1997-06-19 1999-08-31 Church & Dwight Co., Inc. Aerosol deodorant-antiperspirant product
DE19726184A1 (en) 1997-06-20 1998-12-24 Beiersdorf Ag Oil-in-water or multiple emulsion with high concentration of suspended UVB filter
FR2765103B1 (en) 1997-06-26 2001-02-02 Oreal COSMETIC OR DERMATOLOGICAL COMPOSITION CONTAINING AT LEAST ONE FLUORINATED SILICONE WITH AN ALKYL CHAIN
FR2765799B1 (en) 1997-07-08 1999-08-27 Oreal GLOSSY COMPOSITION CONTAINING AROMATIC OILS THICKENED BY A POLYSACCHARIDE ALKYLETHER
GB9715751D0 (en) 1997-07-26 1997-10-01 Ciba Geigy Ag Formulations
ATE269894T1 (en) * 1997-07-29 2004-07-15 Procter & Gamble AQUEOUS GEL DETERGENT COMPOSITIONS FOR LAUNDRY
US6051216A (en) 1997-08-01 2000-04-18 Colgate-Palmolive Company Cosmetic composition containing siloxane based polyamides as thickening agents
EP0916335B1 (en) * 1997-08-13 2004-11-03 Basf Aktiengesellschaft Cosmetic and parmaceutical compositions containing a photostable UV filter
US6001980A (en) 1997-09-03 1999-12-14 Hoechst Celanese Corporation Polyester toner composition for electrophotographic imaging systems
US6165454A (en) 1997-09-18 2000-12-26 Colgate-Palmolive Company Stabilized hair care products
JPH11106216A (en) 1997-10-01 1999-04-20 Kao Corp Zinc oxide dispersion and cosmetic formulated therewith
US5959009A (en) 1997-10-31 1999-09-28 E-L Management Corp Mascara waterproofing composition
US6251409B1 (en) 1997-11-11 2001-06-26 Clarigen, Inc. Use of particles in the composition of cosmetic products
DE19750246A1 (en) 1997-11-13 1999-05-20 Huels Chemische Werke Ag Use of carboxamide gemini surfactant(s)
FR2772602B1 (en) 1997-12-22 2000-01-28 Oreal NON-TRANSFER COSMETIC COMPOSITION COMPRISING A DISPERSION OF POLYMER PARTICLES IN A LIQUID FAT PHASE AND A LIPOSOLUBLE POLYMER
FR2772601B1 (en) 1997-12-22 2000-01-28 Oreal NON-TRANSFER COSMETIC COMPOSITION COMPRISING A DISPERSION OF NON-FILMIFIABLE POLYMER PARTICLES IN A PARTIALLY NON-VOLATILE LIQUID FAT PHASE
FR2772600B1 (en) 1997-12-22 2000-03-17 Oreal NON-TRANSFER COSMETIC COMPOSITION COMPRISING A DISPERSION OF POLYMER PARTICLES IN A FATTY LIQUID PHASE
TWI225793B (en) 1997-12-25 2005-01-01 Ajinomoto Kk Cosmetic composition
FR2773064B1 (en) 1997-12-29 2000-05-05 Oreal USE OF A VOLATILE FLUORINATED SOLVENT AS A DRYING ACCELERATOR IN COSMETIC PRODUCTS
FR2773066B1 (en) 1997-12-29 2000-06-09 Oreal USE OF A VOLATILE FLUORINATED SOLVENT AS AN ANTI-TRANSFER AGENT IN COSMETIC PRODUCTS
EP0933376B1 (en) 1998-01-02 2003-08-20 F. Hoffmann-La Roche Ag Silanyl-triazines as light screening compositions
TW587943B (en) * 1998-01-13 2004-05-21 Kose Corp Powder composition, a powder dispersion in oil and a cosmetic composition containing said powder composition and a powder dispersion in oil
FR2774587B1 (en) 1998-02-09 2000-03-10 Oreal USE OF A WAX MICRODISPERSION IN A COSMETIC OR DERMATOLOGICAL COMPOSITION
DE19812152A1 (en) 1998-03-20 1999-09-23 Basf Ag Use of polymerized fatty acid derivatives and fatty alcohol derivatives as solubilizers
FR2777456B1 (en) 1998-04-15 2001-04-27 Oreal FLUORINATED ANHYDROUS COMPOSITION AND COSMETIC MAKE-UP OR CARE PRODUCTS CONTAINING THE SAME
EP0951897B1 (en) * 1998-04-21 2003-09-03 L'oreal Topical composition containing an olefinic copolymer with controlled crystallisation
JP4251685B2 (en) 1998-04-22 2009-04-08 メルク株式会社 UV absorber
US6183760B1 (en) 1998-04-29 2001-02-06 Avon Products, Inc. Cosmetic stick
US5882363A (en) * 1998-05-07 1999-03-16 The Noville Corporation Clear compositions for use in solid transparent candles
JP2000038321A (en) 1998-05-20 2000-02-08 Shin Etsu Chem Co Ltd Hair cosmetic
JP2000038316A (en) 1998-05-20 2000-02-08 Shin Etsu Chem Co Ltd Make-up cosmetic
JP2000038314A (en) 1998-05-20 2000-02-08 Shin Etsu Chem Co Ltd Oily cosmetic
EP0958805A3 (en) 1998-05-20 2003-07-09 Shin-Etsu Chemical Co., Ltd. Makeup cosmetic composition
DE19822599C2 (en) 1998-05-20 2003-02-06 Goldschmidt Ag Th Copolymers hydrophobically modified polyaspartic esters and their use
DE19822601A1 (en) 1998-05-20 1999-11-25 Goldschmidt Ag Th Hydrophobically modified polyaspartic acid derivatives in O / W emulsions
DE19822791A1 (en) 1998-05-20 1999-11-25 Basf Ag Use of amides of polymerized fatty acids as thickeners
JP2000038317A (en) 1998-05-20 2000-02-08 Shin Etsu Chem Co Ltd Make-up cosmetic
EP0958804A2 (en) 1998-05-20 1999-11-24 Shin-Etsu Chemical Co., Ltd. Hair-care treatment composition
FR2779640B1 (en) * 1998-06-15 2000-08-04 Oreal COSMETIC COMPOSITION CONTAINING A CATIONIC POLYMER AND AN ACRYLIC TERPOLYMER AND USE OF THIS COMPOSITION FOR THE TREATMENT OF KERATINIC MATERIALS
DE19828463A1 (en) 1998-06-26 1999-12-30 Basf Ag 4,4-Diarylbutadienes as water-soluble, photostable UV filters for cosmetic and pharmaceutical preparations
US6054517A (en) 1998-07-10 2000-04-25 Noville Corporation Clear compositions for use in solid transparent candles
US5981680A (en) 1998-07-13 1999-11-09 Dow Corning Corporation Method of making siloxane-based polyamides
FR2781666B1 (en) 1998-07-30 2000-09-08 Oreal SOLID COSMETIC COMPOSITION AND USES THEREOF
GB2340838B (en) 1998-08-21 2002-02-13 Cray Valley Ltd Resins and composites containing them
JP2000086429A (en) 1998-09-14 2000-03-28 Kose Corp Cosmetic
JP3672003B2 (en) 1998-09-14 2005-07-13 株式会社コーセー Cosmetics
JP3671327B2 (en) 1998-09-14 2005-07-13 株式会社コーセー Water-in-oil cosmetics
US6156325A (en) 1998-09-16 2000-12-05 L'oreal Nail enamel composition containing a urea-modified thixotropic agent
FR2783417B1 (en) 1998-09-17 2002-06-28 Oreal TOPICAL COSMETIC OR DERMATOLOGICAL COMPOSITIONS COMPRISING DENDRITIC POLYESTERS
US6042815A (en) * 1998-10-21 2000-03-28 Revlon Consumer Products Corporation Water and oil emulsion solid cosmetic composition
FR2785179A1 (en) 1998-10-30 2000-05-05 Oreal Cosmetic composition for use in make-up, comprises aqueous dispersion of particles of film-forming polymer and polyorganosiloxane polyester
FR2785528B1 (en) 1998-11-10 2002-08-30 Oreal COSMETIC COMPOSITION WITH CONTINUOUS LIPOPHILIC PHASE CONTAINING A NEW PIGMENT
US5976514A (en) * 1998-11-20 1999-11-02 Procter & Gamble Company Low-irritation antiperspirant and deodorant compositions containing a volatile, nonpolar hydrocarbon liquid
DE19855649A1 (en) 1998-12-03 2000-06-08 Basf Ag Dimeric alpha-alkyl-styrene derivatives as photostable UV filters in cosmetic and pharmaceutical preparations
US6197100B1 (en) * 1998-12-04 2001-03-06 Hercules Incorporated Dispersible water soluble polymers
US6150022A (en) * 1998-12-07 2000-11-21 Flex Products, Inc. Bright metal flake based pigments
FR2787318B1 (en) 1998-12-21 2002-10-11 Oreal COMPOSITION FOR COATING KERATIN FIBERS
US6268466B1 (en) 1999-01-04 2001-07-31 Arizona Chemical Company Tertiary amide terminated polyamides and uses thereof
FR2787998B1 (en) 1999-01-06 2001-02-09 Oreal COSMETIC COMPOSITION COMPRISING A STYRENE / ACRYLATE COPOLYMER AND A FATTY PHASE
JP4043680B2 (en) * 1999-02-17 2008-02-06 信越化学工業株式会社 Organic silicone resin powder
US6423306B2 (en) * 1999-02-26 2002-07-23 L'oreal Sa Cosmetic compositions containing di-block, tri-block, multi-block and radial block copolymers
DE19911748A1 (en) 1999-03-16 2000-09-21 Schwan Stabilo Cosmetics Gmbh Process for increasing the tensile strength, breaking strength and flexural strength of colored leads and colored pencils containing such leads
DK1162943T3 (en) * 1999-03-25 2007-01-15 3M Innovative Properties Co Non-firming coating composition
FR2791558B1 (en) 1999-03-30 2001-08-10 Oreal HYPOALLERGENIC MAKEUP OR CARE COMPOSITION CONTAINING A CROSSLINKED OXYALKYLENE ORGANOPOLYSILOXANE, USES THEREOF
JP3802288B2 (en) 1999-04-16 2006-07-26 味の素株式会社 Oily raw material composition
FR2792829B1 (en) 1999-04-28 2004-02-13 Oreal COSMETIC COMPOSITION COMPRISING A WAX MICRODISPERSION AND A COLORING POLYMER
FR2793683B1 (en) 1999-05-20 2003-07-25 Oreal CARE AND MAKEUP ANHYDROUS COMPOSITION CONTAINING FIBERS AND POLYOLS
JP3932155B2 (en) * 1999-06-03 2007-06-20 信越化学工業株式会社 Spherical silicone resin fine particles
US6214329B1 (en) * 1999-06-07 2001-04-10 Revlon Consumer Products Corporation Mascara compositions and method for curling lashes
JP3850202B2 (en) 1999-06-11 2006-11-29 信越化学工業株式会社 Cosmetics
US6231498B1 (en) 1999-06-23 2001-05-15 Pulsion Medical Systems Ag Combined catheter system for IABP and determination of thermodilution cardiac output
FR2795634A1 (en) 1999-06-30 2001-01-05 Oreal MASCARA COMPRISING FILM-FORMING POLYMERS
FR2795635B1 (en) 1999-06-30 2006-09-15 Oreal MASCARA COMPRISING FILMOGENIC POLYMERS
FR2795640B1 (en) * 1999-07-01 2001-08-31 Oreal CARE OR MAKE-UP COMPOSITION CONTAINING FIBERS AND A HYDROPHILIC ORGANOPOLYSILOXANE
US6103250A (en) 1999-07-06 2000-08-15 Revlon Consumer Products Corporation Anhydrous cosmetic compositions containing emulsifying siloxane elastomer
FR2795950B1 (en) 1999-07-08 2003-05-09 Oreal MASCARA COMPRISING A POLYURETHANE AND FIBERS
US6177523B1 (en) 1999-07-14 2001-01-23 Cardiotech International, Inc. Functionalized polyurethanes
FR2796271B1 (en) 1999-07-15 2002-01-11 Oreal COMPOSITION WITHOUT WAX STRUCTURED IN A RIGID FORM BY A POLYMER
FR2796270B1 (en) 1999-07-15 2002-01-11 Oreal A LIQUID FAT PHASE COMPOSITION GELLED BY A POLYAMIDE WITH TERMINAL ESTER GROUPS
FR2796272B1 (en) 1999-07-15 2003-09-19 Oreal COMPOSITION WITHOUT WAX STRUCTURED IN A RIGID FORM BY A POLYMER
FR2796276B1 (en) 1999-07-15 2003-05-16 Oreal SOLID COMPOSITION COMPRISING AN OIL AND A PARTICULAR GELLING COMPOUND, COSMETIC PROCESSING METHOD AND USE OF THE SAME
FR2796273B1 (en) * 1999-07-15 2003-09-12 Oreal COMPOSITION WITH A LIQUID FATTY PHASE GELIFIED BY A POLYAMIDE WITH TERMINAL ESTER GROUPS
FR2796550B1 (en) 1999-07-21 2003-05-09 Asepta Lab PREPARATIONS AND APPLICATIONS OF N-ACYLAMINOACID ESTERS
FR2798655B1 (en) 1999-09-21 2001-11-16 Oreal COMPOSITION COMPRISING A COMPOUND DERIVED FROM CYCLOHEXANE, COMPOUND AND USE OF SAID COMPOUND FOR STRUCTURING A COMPOSITION
FR2799366B1 (en) 1999-10-07 2001-12-07 Oreal COMPOSITION IN THE FORM OF AN OIL-IN-WATER EMULSION CONTAINING FIBERS, AND ITS IN PARTICULAR COSMETIC USES
FR2799367A1 (en) 1999-10-07 2001-04-13 Oreal COMPOSITION IN THE FORM OF AN OIL-IN-WATER EMULSION CONTAINING FIBERS, AND ITS IN PARTICULAR COSMETIC USES
FR2799646B1 (en) 1999-10-15 2001-12-07 Oreal COMPOSITION IN THE FORM OF A WATER-IN-OIL EMULSION, CONTAINING FIBERS, AND ITS USE IN THE COSMETIC FIELD
DE19951010A1 (en) 1999-10-22 2001-04-26 Henkel Kgaa Composition for dyeing keratin-containing fibers, especially human hair, contains combination of 1,4-diaza-cycloheptane and diamino-pyrazole derivatives as developer
JP4164209B2 (en) 1999-10-28 2008-10-15 信越化学工業株式会社 Cosmetics
US6299979B1 (en) 1999-12-17 2001-10-09 Ppg Industries Ohio, Inc. Color effect coating compositions having reflective organic pigments
FR2804017B1 (en) 2000-01-25 2002-07-26 Oreal LONG COMPOSITION HELD STRUCTURED BY A POLYMER AND A PASTY FATTY BODY
FR2802806B1 (en) 1999-12-28 2002-02-08 Oreal LONG COMPOSITION HELD STRUCTURED BY A POLYMER AND A PASTY FATTY BODY
DE60019541T2 (en) 1999-12-28 2006-03-09 L'oreal Structured long-lasting preparation containing a polymer and pasty fatty substances
US6428773B1 (en) 2000-01-13 2002-08-06 Color Access, Inc. Shadow-effect cosmetic composition
FR2804014B1 (en) 2000-01-21 2002-10-18 Oreal NANOEMULSION BASED ON AMPHIPHILIC LIPIDS AND CATIONIC POLYMERS AND USES
FR2804286B1 (en) * 2000-01-28 2002-09-06 Oreal USE OF POLYAMINOACID DERIVATIVES AS PRESERVATIVES, COMPOSITIONS COMPRISING THE SAME AND STORAGE METHOD USING THE SAME
JP4104264B2 (en) 2000-02-01 2008-06-18 信越化学工業株式会社 Novel silicone compound and cosmetics using the same
US6423324B1 (en) 2000-06-20 2002-07-23 Cosmolab, Inc. Temperature-stable polyamide resin-based composition, and products
FR2810562B1 (en) 2000-06-23 2003-04-18 Oreal SOLID EMULSION WITH LIQUID FAT PHASE STRUCTURED BY A POLYMER
US6432391B1 (en) * 2000-07-07 2002-08-13 L'ORéAL S.A. Transparent scented solid cosmetic composition
FR2811225B1 (en) 2000-07-07 2004-04-16 Oreal TRANSPARENT SCENTED SOLID COMPOSITION
US6475500B2 (en) 2000-07-10 2002-11-05 The Procter & Gamble Company Anhydrous cosmetic compositions
US6696049B2 (en) 2000-07-10 2004-02-24 The Procter & Gamble Company Cosmetic compositions
US6524598B2 (en) * 2000-07-10 2003-02-25 The Procter & Gamble Company Cosmetic compositions
US20020018790A1 (en) 2000-07-10 2002-02-14 Vatter Michael Lee Cosmetic compositions
FR2811552B1 (en) 2000-07-17 2002-12-27 Oreal COMPOSITION, IN PARTICULAR COSMETIC OR PHARMACEUTICAL, IN SOLID FORM
GB0019231D0 (en) * 2000-08-04 2000-09-27 Unilever Plc Antiperspirant compositions
FR2816506B1 (en) 2000-11-16 2003-01-10 Thierry Bernoud COSMETIC COMPOSITION THICKENED BY POLYAMIDE RESIN
US6503521B1 (en) * 2000-11-22 2003-01-07 L'ORéAL S.A. Fiber-containing base composition for use with mascara
DE10060467B4 (en) 2000-12-05 2007-02-22 Wella Ag Powdered bleaching agent or hair dye and process for its preparation
FR2817476B1 (en) 2000-12-05 2003-01-03 Oreal MAKE-UP CARE COMPOSITION CONTAINING FIBERS AND A DISPERSING COPOLYMER
JP3976226B2 (en) 2000-12-08 2007-09-12 信越化学工業株式会社 Polyhydric alcohol-modified silicone and cosmetics containing the same
JP4949550B2 (en) 2000-12-11 2012-06-13 信越化学工業株式会社 Cosmetics
AU2001220877A1 (en) 2000-12-12 2002-06-24 L'oreal S.A. Cosmetic composition comprising heteropolymers and a solid substance and method of using same
US7276547B2 (en) 2000-12-12 2007-10-02 L'oreal S.A. Compositions comprising heteropolymers and at least one oil-soluble polymers chosen from alkyl celluloses and alkylated guar gums
FR2817742B1 (en) 2000-12-12 2004-12-24 Oreal TRANSPARENT OR TRANSLUCENT COSMETIC COMPOSITIONS COLORED BY PIGMENTS
US20020168335A1 (en) 2000-12-12 2002-11-14 Nathalie Collin Cosmetic composition comprising a wax and a polymer
EP1343458B1 (en) 2000-12-12 2008-02-13 L'oreal Cosmetic composition comprising a mixture of polymers
US6835399B2 (en) * 2000-12-12 2004-12-28 L'ORéAL S.A. Cosmetic composition comprising a polymer blend
EP1343454B1 (en) 2000-12-12 2009-12-09 L'oreal S.A. Cosmetic composition comprising a polymer and fibres
FR2817743B1 (en) 2000-12-12 2003-01-10 Oreal USE OF A POLYMER FOR OBTAINING FAST MAKEUP OF KERATINIC MATERIALS
US6881400B2 (en) * 2000-12-12 2005-04-19 L'oreal S.A. Use of at least one polyamide polymer in a mascara composition for increasing the adhesion of and/or expressly loading make-up deposited on eyelashes
US20030082126A9 (en) 2000-12-12 2003-05-01 Pinzon Carlos O. Cosmetic compositions containing heteropolymers and oil-soluble cationic surfactants and methods of using same
AU2002256544A1 (en) 2000-12-12 2002-06-24 L'oreal Sa Cosmetic compositions containing at least one heteropolymer and at least one gelling agent and methods of using the same
FR2817739B1 (en) 2000-12-12 2005-01-07 Oreal TRANSPARENT OR TRANSLUCENT COLORED COSMETIC COMPOSITION
US20020111330A1 (en) 2000-12-12 2002-08-15 Carlos Pinzon Compositions containing heteropolymers and methods of using same
US8080257B2 (en) 2000-12-12 2011-12-20 L'oreal S.A. Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using
FR2817740B1 (en) * 2000-12-12 2006-08-04 Oreal METHOD FOR MANUFACTURING A COLORED COSMETIC COMPOSITION OF CONTROLLED TRANSMITTANCE MAKE-UP
AU2001225389A1 (en) 2000-12-12 2002-06-24 L'oreal S.A. Composition comprising at least one heteropolymer and at least one inert filler and methods for use
CN1256937C (en) 2000-12-12 2006-05-24 莱雅公司 Cosmetic composition comprising wax and polymer
US20020107314A1 (en) 2000-12-12 2002-08-08 Carlos Pinzon Compositions containing heteropolymers and oil-soluble esters and methods of using same
WO2002047628A1 (en) 2000-12-13 2002-06-20 L'oréal Composition structured with a polymer containing a heteroatom and an organogelator
FR2818148B1 (en) * 2000-12-15 2005-06-24 Oreal COMPOSITION, ESPECIALLY COSMETIC, CONTAINING 7-HYDROXY DHEA AND / OR 7-KETO DHEA AND AT LEAST ONE ISOFLAVONOID
US6726917B2 (en) 2000-12-18 2004-04-27 L'oreal Sa Fiber-containing cosmetic composition
AU2001220204A1 (en) 2000-12-21 2002-07-01 L'oreal S.A. Cosmetic composition comprising a polymer and fibres
FR2819400B1 (en) 2001-01-15 2004-12-03 Oreal COSMETIC COMPOSITION FOR MAKE-UP OR CARE OF KERATINIC MATERIALS INCLUDING A MIXTURE OF POLYMERS
FR2819402B1 (en) 2001-01-17 2003-02-21 Oreal NAIL POLISH CONTAINING A POLYMER
WO2002056847A1 (en) 2001-01-17 2002-07-25 L'oreal Cosmetic composition comprising a polymer and a fluorinated oil
FR2819398A1 (en) 2001-01-17 2002-07-19 Oreal Composition useful in cosmetics, especially foundation sticks, comprises lipophilic liquid and low molecular weight polymer
FR2819399B1 (en) * 2001-01-17 2003-02-21 Oreal COSMETIC COMPOSITION CONTAINING POLYMER AND FLUORINATED OIL
US7025953B2 (en) * 2001-01-17 2006-04-11 L'oreal S.A. Nail polish composition comprising a polymer
ITMI20010162A1 (en) 2001-01-30 2002-07-30 Intercos Italiana LIGHT AND HANDLABLE SOLID COSMETIC PRODUCT
CN1507342A (en) 2001-05-10 2004-06-23 宝洁公司 Cosmetic composition conprising silicone elastomer
US6552160B2 (en) * 2001-05-14 2003-04-22 Arizona Chemical Company Ester-terminated poly(ester-amides) useful for formulating transparent gels in low polarity fluids
US6497861B1 (en) 2001-06-21 2002-12-24 Color Access, Inc. Stable cosmetic emulsion with polyamide gelling agent
AU2002345721B2 (en) 2001-06-19 2005-06-16 Color Access, Inc. Stable cosmetic emulsion with polyamide gelling agent
US6716420B2 (en) * 2001-10-05 2004-04-06 L′Oreal Methods of use and of making a mascara comprising at least one coloring agent and at least one heteropolymer
US20050008598A1 (en) 2003-07-11 2005-01-13 Shaoxiang Lu Cosmetic compositions comprising a structuring agent, silicone powder and swelling agent
US20040247549A1 (en) 2002-06-12 2004-12-09 L'oreal S.A. Cosmetic emulsions containing at least one hetero polymer and at least one sunscreen and methods of using the same
US20040042980A1 (en) 2002-06-12 2004-03-04 L'oreal Cosmetic emulsions containing at least one hetero polymer and at least one sunscreen, and methods of using same
FR2842416B1 (en) * 2002-07-19 2004-12-17 Oreal COSMETIC COMPOSITION
US7008629B2 (en) * 2002-07-22 2006-03-07 L'ORéAL S.A. Compositions comprising at least one heteropolymer and fibers, and methods of using the same
US6749173B2 (en) 2002-09-27 2004-06-15 The Hartfiel Company Valve arrangement and method of directing fluid flow
FR2848822B1 (en) 2002-12-24 2006-01-13 Oreal COSMETIC COMPOSITION OF FOUNDATION TYPE FOR MAKE-UP OF DARK SKIN
US20040166133A1 (en) 2003-01-21 2004-08-26 L'oreal Method of making a mascara composition comprising polyamide polymer and at least one solid substance having a melting point of 45oC or greater
FR2854795B1 (en) 2003-05-16 2006-08-11 Oreal COSMETIC COMPOSITION FOR CREATING A COLOR VARIATION WITH THE OBSERVATION ANGLE
US20050008595A1 (en) * 2003-05-16 2005-01-13 Duffournier Franck Girier Cosmetic compositions with optical variability
US7011523B2 (en) * 2003-10-22 2006-03-14 Ultradent Products, Inc. Bleaching compositions and devices having a solid adhesive layer and bleaching gel adjacent thereto
JP4230312B2 (en) 2003-08-21 2009-02-25 富士重工業株式会社 VEHICLE PATH ESTIMATION DEVICE AND TRAVEL CONTROL DEVICE EQUIPPED WITH THE PATH ESTIMATION DEVICE
US7022398B2 (en) * 2003-09-18 2006-04-04 Amcol International Corporation Moisture-impervious water-swellable clay-containing “water-stop” composition containing a water-penetrable coating
US20050089541A1 (en) * 2003-10-23 2005-04-28 L'oreal Chlorhexidine-containing O/W emulsion
US20050191327A1 (en) 2003-12-24 2005-09-01 Wei Yu Cosmetic composition comprising two different hetero polymers and method of using same
US20060257336A1 (en) 2004-04-19 2006-11-16 Veronique Ferrari Cosmetic composition comprising silica particles, reflecting particles, and at least one polymer, preparative processes, and uses thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5500209A (en) * 1994-03-17 1996-03-19 The Mennen Company Deodorant and antiperspirant compositions containing polyamide gelling agent
US5911974A (en) * 1994-10-25 1999-06-15 Revlon Consumer Products Corporation Cosmetic compositions
US6074654A (en) * 1995-11-07 2000-06-13 The Procter & Gamble Company Transfer resistant cosmetic compositions
US5783657A (en) * 1996-10-18 1998-07-21 Union Camp Corporation Ester-terminated polyamides of polymerized fatty acids useful in formulating transparent gels in low polarity liquids
EP1031342A1 (en) * 1999-02-24 2000-08-30 L'oreal Mascara composition containing wax, film forming polymer and silicone
WO2001052799A1 (en) * 2000-01-24 2001-07-26 L'oreal Transfer-resistant composition structured in rigid form by a polymer

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8025869B2 (en) 2005-06-28 2011-09-27 L'oréal Cosmetic compositions having enhanced wear properties

Also Published As

Publication number Publication date
WO2002080863A3 (en) 2003-05-01
US8080257B2 (en) 2011-12-20
US20020114773A1 (en) 2002-08-22
AU2001297750A1 (en) 2002-10-21
BR0108238A (en) 2003-03-11
CN1466446A (en) 2004-01-07
EP1353626A2 (en) 2003-10-22
JP2004519548A (en) 2004-07-02
CA2399467A1 (en) 2002-06-12
CN100413488C (en) 2008-08-27

Similar Documents

Publication Publication Date Title
US8080257B2 (en) Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using
US7011823B2 (en) Method of making a mascara composition comprising a polyamide polymer and at least one inert filler
US20040120912A1 (en) Compositions containing at least one oil structured with at least one silicone-polyamide polymer, and at least one crystalline silicone compound and methods of using the same
US20040115154A1 (en) Compositions containing at least one oil structured with at least one silicone-polyamide polymer, and at least one short chain ester and methods of using the same
US20040042980A1 (en) Cosmetic emulsions containing at least one hetero polymer and at least one sunscreen, and methods of using same
EP1343457B1 (en) Cosmetic composition comprising hetero polymers and a solid substance and method of using same
US20040115153A1 (en) Compositions containing at least one oil structured with at least one silicone-polyamide polymer, and at least one silicone gum and methods of using the same
US20010031280A1 (en) Composition comprising at least one hetero polymer and at least one pasty fatty substance and methods for use
US20040247549A1 (en) Cosmetic emulsions containing at least one hetero polymer and at least one sunscreen and methods of using the same
JP4227075B2 (en) Solid emulsion containing a liquid fatty phase structured with a polymer
JP2004515608A (en) Cosmetic composition containing heteropolymer and oil-soluble cationic surfactant and method of using the composition
US20020172696A1 (en) Cosmetic composition containing a polymer and a fluoro oil
US20040166133A1 (en) Method of making a mascara composition comprising polyamide polymer and at least one solid substance having a melting point of 45oC or greater
WO2002049602A1 (en) Structured composition comrpising a heteroatome polymer and fibers
US20030235600A1 (en) Cosmetic compositions comprising at least one polyester and at least one polyheteroatom

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 2399467

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 018049168

Country of ref document: CN

AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2001273639

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2001273639

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642