WO2001062217A2 - Oil-based cosmetics containing water-soluble actives - Google Patents
Oil-based cosmetics containing water-soluble actives Download PDFInfo
- Publication number
- WO2001062217A2 WO2001062217A2 PCT/US2001/005636 US0105636W WO0162217A2 WO 2001062217 A2 WO2001062217 A2 WO 2001062217A2 US 0105636 W US0105636 W US 0105636W WO 0162217 A2 WO0162217 A2 WO 0162217A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- complex
- oil
- fatty acid
- water
- polyglycerol
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/676—Ascorbic acid, i.e. vitamin C
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9794—Liliopsida [monocotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
Definitions
- the invention relates to cosmetic compositions. More specifically, the invention relates to cosmetic compositions containing water-soluble active ingredients.
- the actives In addition to the benefit obtained from the standard cosmetic components, such as emollients and moisturizers, the actives generally provide an added measure of utility in their biological activity, for example, antioxidant or free-radical scavenging activity, keratolytic activity, or antiirritant or antiinflammatory activity. Active components come in many forms, however, and a compound having a desired activity may not be compatible with the vehicle of choice.
- Lipsticks, lip glosses and the like are, to a large extent, almost exclusively based on anhydrous formulas.
- the combination of waxes, oils and pigments used in these products results in a product that is easy to apply, gives good color coverage, and feels moist on the lips both during and after application.
- these constituents are normally highly hydrophobic.
- the formula cannot ordinarily readily accommodate elements that are not oil soluble.
- Water soluble components such as water-soluble actives, as well as other water soluble components such as flavorings, are incompatible with this type of system, and thus, the typical lip formulation is very limited in the variety of components that can be added.
- the ability to incorporate water soluble ingredients into anhydrous formulas would provide a great advantage.
- the present invention now makes this possible, by providing a means for rendering water-soluble components compatible with an oil-based vehicle.
- the invention relates to anhydrous cosmetic and pharmaceutical compositions comprising an oil phase, the composition containing a least one water-soluble component rendered compatible with the oil phase.
- the water soluble component is rendered compatible with the oil phase by being complexed with a polyhydric alcohol and a polyglycerol fatty acid ester.
- the invention also relates to a method for making an anhydrous cosmetic composition containing a water soluble active comprising dissolving the water soluble active in a polyhydric alcohol to form a solution, mixing the solution with a polyglycerol fatty acid ester to form an oil-compatible complex, and adding the complex to an anhydrous cosmetically acceptable vehicle.
- the complexes so formed are useful in a variety of different types of oil- based cosmetics.
- the present invention is based on the observation that it is possible to render a water soluble active component compatible with an oil base by first dissolving the active in a polyhydric alcohol, and then complexing the solution with a polyglycerol fatty acid ester.
- the active component in the complex then behaves substantially as an oil soluble component, with virtually no incompatibility problems in an anhydrous base.
- the first step to accomplishing this oil compatible complex is the dissolution of the water-soluble active in the polyhydric alcohol.
- the alcohol chosen can be any polyhydric alcohol that is capable of solubilizing a water soluble active.
- the preferred polyhydric alcohol is a C2-C6 alcohol, containing from 2-6 hydroxyl groups.
- Examples of such alcohols include, but are not limited to, propylene glycol, dipropylene glycol, butylene glycol, or glycerol. Particularly preferred for use in the invention is glycerol.
- the amounts used of each of the polyhydric alcohol and active are not absolute, but will be determined routinely on a case- by-case basis depending upon the active chosen and the solubility of the active in the chosen polyhydric alcohol. The overall goal is to get as much active dissolved into the alcohol as possible, so as to permit flexibility in incorporation of adequate amounts of the active in the final solution. It is preferred to have at least about 50% active in the alcohol solution, and more preferred to have at least about 70% and most preferred to have about 90% active in the alcohol solution. Dissolution of the active material in the alcohol ordinarily will be conducted at a temperature of about 50°-100°C, taking into account the temperature sensitivity of the active, with stirring until uniform.
- the solution is then combined with the polyglycerol fatty acid ester.
- the preferred polyglycerol is a hexaglycerol, an octaglycerol or a decaglycerol .
- the fatty acid ester is prepared by reaction of the polymeric glycerol with either a saturated or unsaturated fatty acid, resulting in the substitution of the fatty acid moiety on one or more, preferably two or more, more preferably four or more, of the hydroxyl sites on the glycerol molecule.
- useful fatty acids are C12-C22 fatty acids, e.g., oleic acid, linoleic acid, stearic acid, palmitic acid, myristic acid or lauric acid. Particularly preferred is an ester formed between a polyglycerol and an unsaturated fatty acid, particularly oleic acid.
- polyglycerol fatty acid esters are commercially available; just two examples are Caprol 10G40 from Abitec (Ohio) , and Net-DGPO from Barnet (Ohio) .
- the complex is formed by adding the active/polyhydric alcohol solution to the polyglycerol fatty acid ester at the same temperature as was used to prepare the solution, under continuous agitation until the mixture is clear.
- the relative amounts of active-containing solution and ester are not critical, and can range from about 10:90 to 50:50 solution: ester .
- water-soluble active ingredients examples include alpha and beta hydroxy acids, and water-soluble derivatives thereof, ascorbic acid (Vitamin C) and its water-soluble derivatives, shikonin(a moisturizer), caffeine, glucuronic acid, whitening agents such as kojic acid and phenyldithiazolyl-thiourea, water-soluble collagen, whey protein, water-soluble plant extracts, such as algal extracts, aloe, and green tea.
- water-soluble materials include alpha and beta hydroxy acids, and water-soluble derivatives thereof, ascorbic acid (Vitamin C) and its water-soluble derivatives, shikonin(a moisturizer), caffeine, glucuronic acid, whitening agents such as kojic acid and phenyldithiazolyl-thiourea, water-soluble collagen, whey protein, water-soluble plant extracts, such as algal extracts, aloe, and green tea.
- the complex of the invention can of course be applied to any anhydrous makeup, for example, a foundation, concealer, blush, or eyeshadow, as well as to an anhydrous skin care product, such as an SPF/sunscreen product, in liquid, powder, petrolatum-type gel, or solid/stick form.
- an anhydrous skin care product such as an SPF/sunscreen product
- a particularly preferred use of the complex of the invention is in a lip product, such as a lipstick, lip balm or gloss; as noted above, products of this type comprise extremely hydrophobic materials, and therefore, it is very difficult to incorporate into them any hydrophilic materials.
- the complex of the present invention incorporation of water soluble actives is a relatively simple matter.
- the lipstick or gloss may be a typical wax-based formulation.
- wax-based in the present context is intended a product comprising at least about 5% by weight or more of wax, more preferably at least about 10%, most preferably about 10% to about 30% by weight of the total wax-based product.
- the term “wax” will be understood to encompass any organic component that is solid at room temperature, which component can be used to solidify the liquid components of the product when all are heated together, then cooled to room temperature.
- This definition includes waxes in the traditional sense, i.e., those plant, animal or mineral waxes containing primarily esters of higher fatty acids and alcohols, free higher acids and alcohols, and saturated hydrocarbons; examples of such traditional waxes include, but are not limited to, carnauba wax, candelilla wax, beeswax, synthetic wax, shellac wax, spermaceti, lanolin wax, ozokerite, bran wax, ceresin wax, bayberry wax, paraffin, rice wax and jojoba wax.
- wax-like materials including, but not limited to, various fatty alcohols, fatty acids, fatty esters, polyethylenes, polyethylene glycols, and sterols as well as synthetic resinous products having a wax-like, i.e., hard, brittle, relatively non-greasy, texture, such as silicone waxes.
- the complex is used in the preparation of oil-based, gelled, substantially clear solid or semi-solid products, particularly lip products, with or without waxes.
- the clear appearance of such products is highly desirable, but the addition to the gels of other materials risks the development of cloudiness in the otherwise clear product. Retention of clarity can be difficult even with the addition of materials that are compatible with the base, and normally, clarity is retained by the matching of refractive indices of the materials to be incorporated, and/or with the addition of clarity enhancing compounds.
- the complex of the present invention no such additional steps are required: the complex containing the water-soluble ingredient is added directly to the anhydrous vehicle components, and because of the compatibility of the novel complex with the oil base, the resulting product remains clear.
- the complex can be used with any clear gelled oil-based system.
- Clear gelled systems, and methods for making same are well known in the art, and include, but are not limited to, oil bases gelled with dextrin fatty acid esters (e.g., JP US Patent No. 5106625, JP 9235210), dibenzyl monosorbitol acetal (DBMSA; e.g., US Patent No. 5,610,199), or lanosterol and derivatives thereof (e.g. , JP 281887; JP 9188604).
- DBMSA dibenzyl monosorbitol acetal
- lanosterol and derivatives thereof e.g. , JP 281887; JP 9188604
- a complex containing the water-soluble saccharin is prepared as follows: Material Weight percent
- the saccharin is sprinkled into glycerin and mixed by propeller mixer at a temperature of 85°-95°C.
- the polyglyceryl-10 pentaoleate is added to it, and mixed until the mixture is clear.
- This example illustrates the preparation of an oil-based gelled lip gloss containing a complex of the invention.
- Phase I components are sprinkled together and mixed by propeller mixer at room temperature. When Phase I is uniform the temperature is raised to 80°-100°C until the mixture becomes clear. Phase II materials are added into Phase I, at the same temperature, until the mixture is clear.
- Phase III materials are added to the mixture, and combined under the same conditions of mixing and temperature, until the colors and sweetener are evenly dispersed.
- Phase IV and Phase V ingredients are then added and mixed at the same temperature until clear.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001561284A JP2003523374A (en) | 2000-02-23 | 2001-02-22 | Oily cosmetics containing water-soluble active ingredients |
AU43212/01A AU4321201A (en) | 2000-02-23 | 2001-02-22 | Oil-based cosmetics containing water-soluble actives |
CA002368665A CA2368665A1 (en) | 2000-02-23 | 2001-02-22 | Oil-based cosmetics containing water-soluble actives |
EP01916155A EP1202703A2 (en) | 2000-02-23 | 2001-02-22 | Oil-based cosmetics containing water-soluble actives |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US51120800A | 2000-02-23 | 2000-02-23 | |
US09/511,208 | 2000-02-23 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2001062217A2 true WO2001062217A2 (en) | 2001-08-30 |
WO2001062217A3 WO2001062217A3 (en) | 2002-02-28 |
Family
ID=24033906
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2001/005636 WO2001062217A2 (en) | 2000-02-23 | 2001-02-22 | Oil-based cosmetics containing water-soluble actives |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1202703A2 (en) |
JP (1) | JP2003523374A (en) |
AU (1) | AU4321201A (en) |
CA (1) | CA2368665A1 (en) |
WO (1) | WO2001062217A2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007102125A3 (en) * | 2006-03-06 | 2008-01-03 | Procter & Gamble | Lipophilic personal care composition |
US9931294B2 (en) | 2015-12-29 | 2018-04-03 | L'oreal | Stable skin care composition having cosmetically acceptable oils |
WO2023118357A1 (en) * | 2021-12-21 | 2023-06-29 | Chanel Parfums Beaute | Long wear liquid anhydrous composition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5995453B2 (en) * | 2012-01-31 | 2016-09-21 | アサヌマ コーポレーション株式会社 | Cosmetics and method for producing the same |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3677691A (en) * | 1968-09-24 | 1972-07-18 | Kohnstamm & Co Inc H | Nontoxic dyes in polyglycerol fatty acid ester and glycol or glycerine and its mixture therein |
WO1997042944A1 (en) * | 1996-05-13 | 1997-11-20 | Novartis Consumer Health S.A. | Topical composition |
EP0895808A2 (en) * | 1997-08-08 | 1999-02-10 | Mitsubishi Chemical Corporation | Solubilizing agent and hydrosol composition obtained by using the same |
US6193986B1 (en) * | 1997-02-25 | 2001-02-27 | The Nisshin Oil Mills, Ltd. | Oily composition with increased stability and process for producing the same |
-
2001
- 2001-02-22 WO PCT/US2001/005636 patent/WO2001062217A2/en not_active Application Discontinuation
- 2001-02-22 CA CA002368665A patent/CA2368665A1/en not_active Abandoned
- 2001-02-22 AU AU43212/01A patent/AU4321201A/en not_active Abandoned
- 2001-02-22 EP EP01916155A patent/EP1202703A2/en not_active Withdrawn
- 2001-02-22 JP JP2001561284A patent/JP2003523374A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3677691A (en) * | 1968-09-24 | 1972-07-18 | Kohnstamm & Co Inc H | Nontoxic dyes in polyglycerol fatty acid ester and glycol or glycerine and its mixture therein |
WO1997042944A1 (en) * | 1996-05-13 | 1997-11-20 | Novartis Consumer Health S.A. | Topical composition |
US6193986B1 (en) * | 1997-02-25 | 2001-02-27 | The Nisshin Oil Mills, Ltd. | Oily composition with increased stability and process for producing the same |
EP0895808A2 (en) * | 1997-08-08 | 1999-02-10 | Mitsubishi Chemical Corporation | Solubilizing agent and hydrosol composition obtained by using the same |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007102125A3 (en) * | 2006-03-06 | 2008-01-03 | Procter & Gamble | Lipophilic personal care composition |
US9931294B2 (en) | 2015-12-29 | 2018-04-03 | L'oreal | Stable skin care composition having cosmetically acceptable oils |
WO2023118357A1 (en) * | 2021-12-21 | 2023-06-29 | Chanel Parfums Beaute | Long wear liquid anhydrous composition |
Also Published As
Publication number | Publication date |
---|---|
JP2003523374A (en) | 2003-08-05 |
AU4321201A (en) | 2001-09-03 |
EP1202703A2 (en) | 2002-05-08 |
WO2001062217A3 (en) | 2002-02-28 |
CA2368665A1 (en) | 2001-08-30 |
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