US20040194232A1 - Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibers - Google Patents

Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibers Download PDF

Info

Publication number
US20040194232A1
US20040194232A1 US10/832,254 US83225404A US2004194232A1 US 20040194232 A1 US20040194232 A1 US 20040194232A1 US 83225404 A US83225404 A US 83225404A US 2004194232 A1 US2004194232 A1 US 2004194232A1
Authority
US
United States
Prior art keywords
amino
para
phenylenediamine
diamino
pyrazole
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
US10/832,254
Inventor
Roland de la Mettrie
Jean Cotteret
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal 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 LOreal SA filed Critical LOreal SA
Priority to US10/832,254 priority Critical patent/US20040194232A1/en
Publication of US20040194232A1 publication Critical patent/US20040194232A1/en
Abandoned legal-status Critical Current

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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/411Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/66Enzymes
    • 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
    • A61K8/73Polysaccharides
    • A61K8/737Galactomannans, e.g. guar; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/08Preparations for bleaching the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5422Polymers characterized by specific structures/properties characterized by the charge nonionic

Definitions

  • the present invention relates to an oxidizing composition intended for treating keratin fibres, comprising at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme and at least one nonionic guar gum, as well as to its uses for dyeing, for permanently reshaping or for bleaching keratin fibres, in particular human hair.
  • Oxidation dye precursors in particular para-phenylenediamines, ortho- or para-aminophenols and heterocyclic bases which are generally referred to as oxidation bases.
  • Oxidation dye precursors, or oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise to coloured compounds and dyes by a process of oxidative condensation.
  • the dyes must also be able to cover white hair and, lastly, they must be as unselective as possible, i.e. they must give the smallest possible colour differences along the same length of keratin fibre, which may in fact be differently sensitized (i.e. damaged) between its tip and its root.
  • the oxidation dyeing of keratin fibres is generally carried out in alkaline medium, in the presence of hydrogen peroxide.
  • alkaline media in the presence of hydrogen peroxide has the drawback of causing appreciable degradation of the fibres, as well as considerable bleaching of the keratin fibres, which is not always desirable.
  • the oxidation dyeing of keratin fibres can also be carried out using oxidizing systems other than hydrogen peroxide, such as enzymatic sytems.
  • oxidizing systems other than hydrogen peroxide, such as enzymatic sytems.
  • compositions comprising an oxidation dye precursor in combination with enzymes such as pyranose oxidase, glucose oxidase or uricase, in the presence of a donor for the said enzymes.
  • the reducing compositions which may be used in order to carry out the first step of a permanent-waving operation generally contain, as reducing agents, sulphites, bisulphites, alkylphosphines or, preferably, thiols.
  • thiols those commonly used are cysteine and the various derivatives thereof, cysteamine and the derivatives thereof, thiolactic acid or thioglycolic acid, the salts thereof and the esters thereof, in particular glyceryl thioglycolate.
  • compositions based on aqueous hydrogen peroxide, sodium bromate or persalts such as sodium perborate which have the drawback of being liable to damage the hair.
  • the problem of the technique of the permanent-waving operations known to date is that their application to the hair induces long-term adverse changes in the quality of the hair.
  • the essential causes of these adverse changes in the quality of the hair are a reduction in its cosmetic properties, such as its sheen and its feel, and degradation of its mechanical properties, more particularly degradation of its mechanical strength due to swelling of the keratin fibres during the rinsing between the reduction step and the oxidation step, which can also be reflected by an increase in its porosity.
  • the hair is weakened and can become brittle during subsequent treatments such as blow-drying.
  • the aim of the present invention is to solve the problems mentioned above.
  • compositions containing, as oxidizing system, at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme and at least one nonionic guar gum which can constitute, in the presence of oxidation dye precursors (oxidation bases) and optionally couplers, ready-to-use dye formulations which lead to more homogeneous, more intense and more chromatic colorations without giving rise to any significant degradation, these colorations being relatively unselective and showing good resistance to the various aggressive factors to which the hair may be subjected.
  • oxidizing composition containing, as oxidizing system, at least one enzyme of 2-electron oxidoreductase typein the presence of at least one donor for the said enzyme and at least one nonionic guar gum, makes it possible to solve the technical problems mentioned above.
  • this type of oxidizing composition improves the curl hold obtained over time, substantially reduces the porosity of permanent-waved hair and improves the compatibility of permanent-waved hair with respect to subsequent treatments.
  • the Applicant has also discovered, surprisingly, that the use, in a process for bleaching keratin fibres, of an oxidizing composition containing, as oxidizing system, at least one enzyme of 2-electron oxidoreductase typein the presence of at least one donor for the said enzyme and at, least one nonionic guar gum makes it possible to solve the technical problems mentioned above, in particular to improve the compatibility of bleached hair with respect to subsequent treatments.
  • This type of oxidizing composition gives a more uniform bleaching effect on the hair and improves the cosmetic properties, such as the feel.
  • the subject of the present invention is thus, firstly, a cosmetic and/or dermatological composition intended for treating keratin fibres, in particular human keratin fibres and more particularly human hair, comprising, in a support which is suitable for keratin fibres:
  • the 2-electron oxidoreductase(s) used in the oxidizing compositions in accordance with the invention can be chosen in particular from pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases and uricases.
  • the 2-electron oxidoreductase is preferably chosen from uricases of animal, microbiological or biotechnological origin.
  • uricase extracted from boar liver uricase from Arthrobacter globiformis, as well as uricase from Aspergillus flavus.
  • the 2-electron oxidoreductase(s) can be used in pure crystalline form or in a form diluted in a diluent which is inert with respect to the said 2-electron oxidoreductase.
  • the 2-electron oxidoreductase(s) in accordance with the invention preferably represent(s) from 0.01 to 20% by weight approximately relative to the total weight of the composition, and even more preferably from 0.1 to 5% by weight approximately relative to this weight.
  • the term donor is understood to refer to the various substrates also necessary for the functioning of the said 2-electron oxidoreductase(s).
  • the nature of the donor (or substrate) for the said enzyme varies depending on the nature of the 2-electron oxidoreductase used.
  • donors for the pyranose oxidases mention may be made of D-glucose, L-sorbose and D-xylose
  • a donor for the glucose oxidases mention may be made of D-glucose
  • donors for the glycerol oxidases mention may be made of glycerol and dihydroxyacetone
  • donors for the lactate oxidases mention may be made of lactic acid and its salts
  • donors for the pyruvate oxidases mention may be made of pyruvic acid and its salts
  • uric acid and its salts mention may be made.
  • the donor(s) (or substrate(s)) used in accordance with the invention preferably represent from 0.01 to 20% by weight approximately relative to the total weight of the composition in accordance with the invention, and even more preferably from 0.1 to 5% approximately relative to this weight.
  • unmodified or. chemically modified nonionic guar gums can be used.
  • the unmodified nonionic guar gums are, for example, the products sold under the name Vidogum GH 175 by the company Unipectine and under the name Jaguar C by the company Meyhall.
  • nonionic guar gums which can be used according to the invention are preferably modified with C 1 -C 6 hydroxyalkyl groups.
  • hydroxyalkyl groups mention may be made, for example, of hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups.
  • guar gums are well known in the state of the art and can be prepared, for example, by reacting corresponding alkene oxides, such as, for example, propylene oxides, with the guar gum, so as to obtain a guar gum modified with hydroxypropyl groups.
  • alkene oxides such as, for example, propylene oxides
  • the degree of hydroxyalkylation which corresponds to the number of alkylene oxide molecules consumed by the number of free hydroxyl functions present on the guar gum, preferably ranges from 0.4 to 1.2.
  • nonionic guar gums optionally modified with hydroxyalkyl groups are sold, for example, under the trade names Jaguar HP8, Jaguar HP60 and Jaguar HP120, Jaguar DC 293 and Jaguar HP 105 by the company Rhône-Poulenc (Meyhall) or under the name Galactasol 4H4FD2 by the company Aqualon.
  • the concentration of nonionic guar gum can range from 0.01 to 10% by weight approximately relative to the total weight of the composition, and preferably between 0.1 and 5% approximately.
  • a subject of the present invention is also a ready-to-use composition for the oxidation dyeing of keratin fibres, and in particular human keratin fibres such as the hair, of the type comprising, in a medium which is suitable for dyeing, at least one oxidation base and, where appropriate, one or more couplers, which is characterized in that it contains:
  • oxidation base(s) used in the ready-to-use dye composition is not a critical factor. They can be chosen, in particular, from para-phenylenediamines, double bases, para-aminophenols, ortho-aminophenols and heterocyclic oxidation bases.
  • R 1 represents a hydrogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a (C 1 -C 4 )alkoxy (C 1 -C 4 )alkyl radical, a C 1 -C 4 alkyl radical substituted with a nitrogenous group, a phenyl radical or a 4′-aminophenyl radical;
  • R 2 represents a hydrogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a (C 1 -C 4 )alkoxy (C 1 -C 4 )alkyl radical or a C 1 -C 4 alkyl radical substituted with a nitrogenous group;
  • R 3 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 1 -C 4 hydroxyalkoxy radical, an acetylamino (C 1 -C 4 )alkoxy radical, a C 1 -C 4 mesylaminoalkoxy radical or a carbamoylamino (C 1 -C 4 ) alkoxy radical,
  • a halogen atom such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 -C 4 alkyl radical such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 -C 4 alkyl radical such as a chlorine, bromine, iodine or fluorine atom
  • R 4 represents a hydrogen or halogen atom or a C 1 -C 4 alkyl radical.
  • nitrogenous groups of formula (I) above mention may be made in particular of amino, mono (C 1 -C 4 ) alkylamino, di(C 1 -C 4 )alkylamino, tri(C 1 -C 4 )alkylamino, monohydroxy (C 1 -C 4 )alkylamino, imidazolinium and ammonium radicals.
  • para-phenylenediamines of formula (I) above mention may be made more particularly of para-phenylenediamine, para-toluylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis( ⁇ -hydroxyethyl)-para-phenylenediamine, 4-amino-N,N-bis( ⁇ -hydroxyethyl)-2-methylaniline, 4-amino
  • para-phenylenediamine para-toluylenediamine, 2-isopropyl-para-phenylenediamine, 2- ⁇ -hydroxyethyl-para-phenylenediamine, 2- ⁇ -hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N,N-bis ( ⁇ -hydroxyethyl)-para-phenylenediamine, 2-chloro-para-phenylenediamine and 2- ⁇ -acetylaminoethyloxy-para-phenylenediamine and the addition salts thereof with an acid are most particularly preferred.
  • double bases is understood to refer to the compounds containing at least two aromatic rings bearing amino and/or hydroxyl groups.
  • Z 1 and Z 2 which may be identical or different, represent a hydroxyl or —NH 2 radical which may be substituted with a C 1 -C 4 alkyl radical or with a linker arm Y;
  • the linker arm Y represents a linear or branched alkylene chain containing from 1 to 14 carbon atoms, which may be interrupted by or terminated with one or more nitrogenous groups and/or one or more hetero atoms such as oxygen, sulphur or nitrogen atoms, and optionally substituted with one or more hydroxyl or C 1 -C 4 alkoxy radicals;
  • R 5 and R 6 represent a hydrogen or halogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a C 1 -C 4 aminoalkyl radical or a linker arm Y;
  • R 7 , R 8 , R 9 , R 10 , R 11 and R 12 which may be identical or different, represent a hydrogen atom, a linker arm Y or a C 1 -C 4 alkyl radical;
  • nitrogenous groups of formula (II) above mention may be made in particular of amino, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, tri(C 1 -C 4 )alkylamino, monohydroxy(C 1 -C 4 )alkylamino, imidazo-linium and ammonium radicals.
  • N,N′-bis( ⁇ -hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-di-aminopropanol and 1,8-bis (2,5-diaminophenoxy)-3,5-dioxaoctane, or one of the addition salts thereof with an acid, are particularly preferred.
  • R 13 represents a hydrogen or halogen atom or a C 1 -C 4 alkyl, C 1 -C 4 monohydroxyalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, C 1 -C 4 aminoalkyl or hydroxy (C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkyl radical,
  • R 14 represents a hydrogen or halogen atom or a C 1 -C 4 -alkyl, C 1 -C 4 monohydroxyalkyl, C 2 -C 4 polyhydroxyalkyl, C 1 -C 4 aminoalkyl, C 1 -C 4 cyanoalkyl or (C 1 -C 4 ) alkoxy-(C 1 -C 4 ) alkyl radical,
  • para-aminophenols of formula (III) above mention may be made more particularly of para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-( ⁇ -hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
  • para-aminophenol 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-( ⁇ -hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and
  • ortho-aminophenols which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made more particularly of 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid.
  • heterocyclic bases which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made more particularly of pyridine derivatives, pyrimidine derivatives, pyrazole derivatives and pyrazolopyrimidine derivatives, and the addition salts thereof with an acid.
  • pyridine derivatives mention may be made more particularly of the compounds described, for example, in patents GB 1,026,978 and GB 1,153,196, such as 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-( ⁇ -methoxyethyl)amino-3-amino-6-methoxypyridine and 3,4-diaminopyridine, and the addition salts thereof with an acid.
  • pyrimidine derivatives mention may be made more particularly of the compounds described, for example, in German patent DE 2,359,399 or Japanese patent JP 88-169,571 or patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine, and the addition salts thereof with an acid.
  • 2,4,5,6-tetraaminopyrimidine 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine, and the addition salts thereof with an acid.
  • R 15 , R 16 , R 17 and R 18 which may be identical or different, denote a hydrogen atom, a C 1 -C 4 alkyl radical, an aryl radial, a C 1 -C 4 hydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl radical, a C 1 -C 4 aminoalkyl radical (it being possible for the amine to be protected with an acetyl, ureido or sulphonyl radical), a (C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkyl radical, a di[(C 1 -C 4 )alkyl]amino (C 1 -C 4 )alkyl radical (it being possible for the dialkyl radicals to form a 5- or 6-membered carbon-based ring or a heterocycle),
  • the radicals X which may be identical or different, denote a hydrogen atom, a C 1 -C 4 alkyl radical, an aryl radical, a C 1 -C 4 hydroxyalkyl radical, a C 2 -C 4 polyhydroxyalkyl radical, a C 1 -C 4 aminoalkyl radical, a (C 1 -C 4 )alkylamino (C 1 -C 4 )alkyl radical, a di[(C 1 -C 4 )alkyl]amino (C 1 -C 4 )alkyl radical (it being possible for the dialkyls to form a 5- or 6-membered carbon-based ring or a heterocycle), a hydroxy (C 1 -C 4 )alkyl- or di-[hydroxy(C 1 -C 4 )alkyl]amino (C 1 -C 4 )alkyl radical, an amino radical, a (C 1 -C 4 )alkyl- or di
  • i is equal to 0, 1, 2 or 3;
  • p is equal to 0 or 1;
  • q is equal to 0 or 1;
  • n is equal to 0 or 1;
  • n is equal to 0 and the groups NR 15 R 16 and NR 17 R 18 occupy the (2,3); (5,6); (6,7); (3,5) or (3,7) positions;
  • n is equal to 1 and the group NR 15 R 16 (or NR 17 R 18 ) and the OH group occupy the (2,3); (5,6); (6,7); (3,5) or (3,7) positions.
  • pyrazolo[1,5-a]pyrimidines of formula (IV) above can be prepared by cyclization starting with an aminopyrazole, according to the syntheses described in the following references:
  • the oxidation base(s) in accordance with the invention preferably represent(s) from 0.0005 to 12% by weight approximately relative to the total weight of the ready-to-use dye composition, and even more preferably from 0.005 to 6% by weight approximately relative to this weight.
  • the couplers which can be used are those used conventionally in oxidation dye compositions, i.e. meta-phenylenediamines, meta-aminophenols and meta-diphenols, mono- or polyhydroxylated naphthalene derivatives, sesamol and its derivatives and heterocyclic compounds such as, for example, indole derivatives, indoline derivatives, benzimidazole derivatives, benzomorpholine derivatives, sesamol derivatives, pyrazoloazole derivatives, pyrroloazole derivatives, imidazoloazole derivatives, pyrazolo-pyrimidine derivatives, pyrazoline-3,5-dione derivatives, pyrrolo[3,2-d]oxazole derivatives, pyrazolo [3,4-d]thiazole derivatives, thiazoloazole S-oxide derivatives and thiazoloazole S,S-dioxide. derivatives, and the addition salts thereof with an
  • couplers can be chosen in particular from 2-methyl-5-aminophenol, 5-N-( ⁇ -hydroxyethyl) amino-2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxy-benzene, 2,4-diamino-1-( ⁇ -hydroxyethyloxy)benzene, 2-amino-4-( ⁇ -hydroxyethylamino) -1-methoxybenzene, 1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol, ⁇ -naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine, 1H-3-methylpyrazol-5-one and 1-phenyl-3-'methylpyrazol-5-one, and
  • these couplers preferably represent from 0.0001 to 10% by weight approximately relative to the total weight of the ready-to-use dye composition, and even more preferably from 0.005 to 5% by weight approximately relative to this weight.
  • addition salts with an acid which can be used in the context of the dye compositions of the invention are chosen in particular from the hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
  • the dye composition of the invention can also contain, in addition to the oxidation bases defined above and the optional combined couplers, direct dyes to enrich the shades with glints.
  • direct dyes can be chosen in particular from nitro dyes, azo dyes or anthraquinone dyes.
  • the subject of the invention is also a process for dyeing keratin fibres, and in particular human. keratin fibres such as the hair, using the ready-to-use dye composition as defined above.
  • At least one ready-to-use dye composition as defined above is placed on the fibres, for a period which is sufficient to develop the desired coloration, after which the fibres are rinsed, optionally washed with shampoo, rinsed again and dried.
  • the time required to develop the coloration on the keratin fibres is generally beteen 3 and 60 minutes and even more precisely between 5 and 40 minutes.
  • the process includes a first step which consists in separately storing, on the one hand, a composition (A) comprising, in a medium which is suitable for dyeing, at least one oxidation base and optionally at least one coupler as defined above, and, on the other hand, a composition (B) containing, in a medium which is suitable for dyeing, at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme and at least one nonionic guar gum containing at least one hydrophilic unit and at least one fatty chain, and then in mixing them together at the time of use, before applying this mixture to the keratin fibres.
  • a composition (A) comprising, in a medium which is suitable for dyeing, at least one oxidation base and optionally at least one coupler as defined above
  • a composition (B) containing, in a medium which is suitable for dyeing, at least one enzyme of 2-electron oxidoreductase type in the presence of at
  • the nonionic guar gum is incorporated into composition (A).
  • Another subject of the invention is a multi-compartment dyeing device or “kit” or any other multi-compartment packaging system, a first compartment of which contains composition (A) as defined above and a second compartment of which contains composition (B) as defined above.
  • kit a multi-compartment dyeing device or “kit” or any other multi-compartment packaging system, a first compartment of which contains composition (A) as defined above and a second compartment of which contains composition (B) as defined above.
  • These devices can be equipped with means for applying the desired mixture to the hair, such as the devices described in patent FR-2,586,913 in the name of the Applicant.
  • a subject of the present invention is also a, novel process for treating keratin substances, in particular the hair, in order to obtain a permanent reshaping of this hair, in particular in the form of permanent-waved hair, this process comprising the following steps: (i) a reducing composition is applied to the keratin substance to be treated, the keratin substance being placed under mechanical tension before, during or after the said application, (ii) the keratin substance is optionally rinsed, (iii) an oxidizing composition as defined above is applied to the optionally rinsed keratin substance, (iv) the keratin substance is optionally rinsed again.
  • the first step (i) of this process consists in applying a reducing composition to the hair. This application is carried out lock by lock or all at once.
  • the reducing composition comprises, for example, at least one reducing agent, which can be chosen in particular from thioglycolic acid, cysteine, cysteamine, glyceryl thioglycolate, thiolactic acid or thiolactic or thioglycolic acid salts.
  • the usual step for placing the hair under tension in a shape corresponding to the desired final shape for this hair can be carried out by any suitable means, in particular mechanical means, known per se for maintaining the hair under tension, such as, for example, rollers, curlers and the like.
  • the hair can also be shaped without the aid of external means, simply with the fingers.
  • the hair onto which the reducing composition has been applied should, conventionally, be left to stand for a few minutes, generally between 5 minutes and one hour, preferably between 10 and 30 minutes, so as to give the reducing agent enough time to act correctly on the hair.
  • This waiting phase preferably takes place at a temperature ranging from 35° C. to 45° C., while preferably also protecting the hair with a hood.
  • step (ii) the hair impregnated with the reducing composition is then rinsed thoroughly with an aqueous composition.
  • step (iii)) the oxidizing composition of the invention is applied to the hair thus rinsed, with the aim of fixing the new shape given to the hair.
  • the hair onto which the oxidizing composition has been applied is then conventionally, left for a standing or waiting phase lasting a few minutes, generally between 3 and 30 minutes, preferably between 5 and 15 minutes.
  • step (iv) the hair impregnated with the oxidizing composition is rinsed thoroughly, generally with water.
  • the oxidizing composition according to the invention can also be used in a process for bleaching keratin fibres, and in particular the hair.
  • the bleaching process according to the invention comprises a step of applying an oxidizing composition according to the invention to the keratin fibres in the presence or absence of an auxiliary oxidizing agent.
  • a second step of the bleaching process according to the invention is a step of rinsing the keratin fibres.
  • the medium which is suitable for the keratin fibres (or the support) for the ready-to-use dye compositions and for the oxidation compositions used for the permanent reshaping or bleaching of keratin- fibres in accordance with the invention generally consists of water or of a mixture of water and at least one organic solvent in order to dissolve the compounds which would not be sufficiently soluble in water.
  • organic solvent By way of organic solvent, mention may be made, for example, of C 1 -C 4 alkanols such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and aromatic alcohols such as benzyl alcohol or phenoxyethanol, similar products and mixtures thereof.
  • C 1 -C 4 alkanols such as ethanol and isopropanol
  • glycerol glycols and glycol ethers
  • glycols and glycol ethers such as 2-butoxyethanol
  • propylene glycol propylene glycol monomethyl ether
  • aromatic alcohols such as benzyl alcohol or phenoxyethanol
  • the solvents can be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.
  • the pH of the ready-to-use dye compositions and of the oxidizing compositions used for the permanent reshaping or bleaching of the keratin fibres in accordance with the invention is chosen such that the enzymatic activity of the 2-electron oxidoreductase is not adversely affected. It is generally between 5 and 11 approximately, and preferably between 6.5 and 10 approximately. It can be adjusted to the desired value using acidifying or basifying agents usually used for dyeing keratin fibres.
  • inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
  • basifying agents mention may be made, by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines, 2-methyl-2-aminopropanol and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (V) below:
  • W is a propylene residue optionally substituted with a hydroxyl group or a C 1 -C 4 alkyl radical
  • R 13 , R 14 , R 15 and R 16 which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl radical.
  • the ready-to-use dye compositions and the oxidizing compositions for the permanent reshaping or bleaching of keratin fibres in accordance with the invention can also contain various adjuvants used conventionally in compositions for dyeing, permanently reshaping or bleaching the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickeners, antioxidants, enzymes other than the 2-electron oxidoreductases used in accordance with the invention, such as, for example, peroxidases, penetration agents, sequestering agents, fragrances, buffers, dispersing agents, conditioners such as, for example, silicones, film-forming agents, preserving agents and opacifiers.
  • adjuvants used conventionally in compositions for dyeing, permanently reshaping or bleaching the hair
  • the ready-to-use dye compositions and the oxidizing compositions used for the permanent reshaping or bleaching of keratin fibres in accordance with the invention can be in various forms, such as in the form of liquids, creams or gels, which are optionally pressurized, or in any other form which is suitable for dyeing, permanently reshaping or bleaching keratin fibres, and in particular human hair.
  • the oxidation dyes(s) and the 2-electron oxido-reductase(s) are present in the said composition, which must be free of oxygen gas, so as to avoid any premature oxidation of the oxidation dye(s).
  • the ready-to-use dye composition below was prepared (contents in grams): Uricase from Arthrobacter globiformis at a 1.5 g concentration of 20 International Units (I.U.)/mg, sold by the company Sigma Uric acid 1.5 g (C 8 -C 10 )alkyl polyglucoside as an aqueous 8.0 g solution containing 60% active material (A.M.), sold under the name Oramix CG110 by the company SEPPIC Para-phenylenediamine 0.324 g Resorcinol 0.32 g Hydroxypropyl guar gum sold under the name 1.6 g Jaguar HP 60 by the company Mayhall Ethanol 20.0 g Monoethanolamine qs pH 9.5 Demineralized waterqs 100 g
  • This ready-to-use dye composition was applied to locks of natural grey hair containing 90% white hairs for 30 minutes. The hair was then rinsed, washed with a standard shampoo and then dried.

Abstract

The present application relates to a cosmetic composition intended for treating keratin fibres, comprising, in a support which is suitable for keratin fibres: (a) at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme; (b) at least one nonionic guar gum; as well as to processes for treating keratin fibres, in particular processes for dyeing, permanently reshaping or bleaching the hair, using this composition.

Description

  • The present invention relates to an oxidizing composition intended for treating keratin fibres, comprising at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme and at least one nonionic guar gum, as well as to its uses for dyeing, for permanently reshaping or for bleaching keratin fibres, in particular human hair. [0001]
  • It is known to dye keratin fibres, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular para-phenylenediamines, ortho- or para-aminophenols and heterocyclic bases which are generally referred to as oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise to coloured compounds and dyes by a process of oxidative condensation. [0002]
  • It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or colour modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds. [0003]
  • The variety of compounds used as regards the oxidation bases and the couplers allows a wide range of colours to be obtained. [0004]
  • The so-called “permanent” coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus it must have no toxicological drawbacks, it must be able to give shades of the desired intensity and it must be able to withstand external agents (light, bad weather, washing, permanent-waving, perspiration, rubbing). [0005]
  • The dyes must also be able to cover white hair and, lastly, they must be as unselective as possible, i.e. they must give the smallest possible colour differences along the same length of keratin fibre, which may in fact be differently sensitized (i.e. damaged) between its tip and its root. [0006]
  • The oxidation dyeing of keratin fibres is generally carried out in alkaline medium, in the presence of hydrogen peroxide. However, the use of alkaline media in the presence of hydrogen peroxide has the drawback of causing appreciable degradation of the fibres, as well as considerable bleaching of the keratin fibres, which is not always desirable. [0007]
  • The oxidation dyeing of keratin fibres can also be carried out using oxidizing systems other than hydrogen peroxide, such as enzymatic sytems. Thus, it has already been proposed to dye keratin fibres, in particular in patent application EP-A-0,310,675, with compositions comprising an oxidation dye precursor in combination with enzymes such as pyranose oxidase, glucose oxidase or uricase, in the presence of a donor for the said enzymes. Although being used under conditions which do not result in degradation of the keratin fibres which is comparable to that caused by the dyes used in the presence of hydrogen peroxide, these dye formulations nevertheless lead to colorations which are still insufficient, both as regards the homogeneity of the colour distributed along the fibre (“unison”) and as regards the chromaticity (luminosity), the dyeing power and the resistance to the various aggressive factors to which the hair may be subjected. [0008]
  • It is known that the most common technique for obtaining a permanent reshaping of the hair consists, in a first stage, in opening the keratin -S-S-disulphide (cysteine) bonds using a composition containing a suitable reducing agent (reduction step) followed, after having rinsed the head of hair thus treated, by reconstituting, in a second stage, the said disulphide bonds by applying to the hair, which has been placed under tension beforehand (rollers and the like), an oxidizing composition (oxidation step, also known as the fixing step) so as finally to give to the hair the desired shape. This technique thus makes it equally possible either to make the hair wavy or to straighten it or to remove its curliness. The new shape given to the hair by a chemical treatment such as above is remarkably long-lasting and in particular resists the action of washing with water or shampoos, as opposed to simple standard techniques for temporary reshaping, such as hairsetting. [0009]
  • The reducing compositions which may be used in order to carry out the first step of a permanent-waving operation generally contain, as reducing agents, sulphites, bisulphites, alkylphosphines or, preferably, thiols. Among the thiols, those commonly used are cysteine and the various derivatives thereof, cysteamine and the derivatives thereof, thiolactic acid or thioglycolic acid, the salts thereof and the esters thereof, in particular glyceryl thioglycolate. [0010]
  • As regards the oxidizing compositions needed to carry out the fixing step, use is usually made in practice of compositions based on aqueous hydrogen peroxide, sodium bromate or persalts such as sodium perborate, which have the drawback of being liable to damage the hair. [0011]
  • The problem of the technique of the permanent-waving operations known to date is that their application to the hair induces long-term adverse changes in the quality of the hair. The essential causes of these adverse changes in the quality of the hair are a reduction in its cosmetic properties, such as its sheen and its feel, and degradation of its mechanical properties, more particularly degradation of its mechanical strength due to swelling of the keratin fibres during the rinsing between the reduction step and the oxidation step, which can also be reflected by an increase in its porosity. The hair is weakened and can become brittle during subsequent treatments such as blow-drying. [0012]
  • The same problem of adverse changes in keratin fibres is encountered during processes for bleaching the hair. [0013]
  • It is known that the permanent reshaping or bleaching of keratin fibres can also be carried out under milder conditions using oxidizing systems other than hydrogen peroxide, such as enzymatic systems. Thus, processes for the permanent reshaping or bleaching of keratin fibres have already been proposed, in particular in patent application EP-A-0,310,675, with compositions comprising an enzyme such as pyranose oxidase, glucose oxidase or uricase, in the presence of a donor for the said enzyme. Although being used under conditions which do not result in degradation of the keratin fibres which is comparable to that caused by conventional permanent-waving or bleaching processes, these oxidizing formulations nevertheless lead to results which are still insufficient, as regards the curl hold over time, as regards the compatibility of permanent-waved or bleached hair with subsequent treatments, as regards the reduction of the mechanical properties of the permanent-waved hair, in particular the reduction of the porosity of the hair, and as regards the reduction of the cosmetic properties such as the feel, or alternatively as regards the uniformity of the bleaching along the keratin fibres. [0014]
  • The aim of the present invention is to solve the problems mentioned above. [0015]
  • The Applicant has discovered, surprisingly, novel compositions containing, as oxidizing system, at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme and at least one nonionic guar gum, which can constitute, in the presence of oxidation dye precursors (oxidation bases) and optionally couplers, ready-to-use dye formulations which lead to more homogeneous, more intense and more chromatic colorations without giving rise to any significant degradation, these colorations being relatively unselective and showing good resistance to the various aggressive factors to which the hair may be subjected. [0016]
  • The Applicant has also discovered, unexpectedly, that the use, in a process for the permanent reshaping of keratin fibres, of an oxidizing composition containing, as oxidizing system, at least one enzyme of 2-electron oxidoreductase typein the presence of at least one donor for the said enzyme and at least one nonionic guar gum, makes it possible to solve the technical problems mentioned above. In particular, this type of oxidizing composition improves the curl hold obtained over time, substantially reduces the porosity of permanent-waved hair and improves the compatibility of permanent-waved hair with respect to subsequent treatments. [0017]
  • The Applicant has also discovered, surprisingly, that the use, in a process for bleaching keratin fibres, of an oxidizing composition containing, as oxidizing system, at least one enzyme of 2-electron oxidoreductase typein the presence of at least one donor for the said enzyme and at, least one nonionic guar gum makes it possible to solve the technical problems mentioned above, in particular to improve the compatibility of bleached hair with respect to subsequent treatments. This type of oxidizing composition gives a more uniform bleaching effect on the hair and improves the cosmetic properties, such as the feel. [0018]
  • These discoveries form the basis of the present invention. [0019]
  • The subject of the present invention is thus, firstly, a cosmetic and/or dermatological composition intended for treating keratin fibres, in particular human keratin fibres and more particularly human hair, comprising, in a support which is suitable for keratin fibres: [0020]
  • (a) at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme, [0021]
  • (b) at least one nonionic guar gum. [0022]
  • The 2-electron oxidoreductase(s) used in the oxidizing compositions in accordance with the invention can be chosen in particular from pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases and uricases. [0023]
  • According to the invention, the 2-electron oxidoreductase is preferably chosen from uricases of animal, microbiological or biotechnological origin. [0024]
  • By way of example, mention may be made of uricase extracted from boar liver, uricase from [0025] Arthrobacter globiformis, as well as uricase from Aspergillus flavus.
  • The 2-electron oxidoreductase(s) can be used in pure crystalline form or in a form diluted in a diluent which is inert with respect to the said 2-electron oxidoreductase. [0026]
  • The 2-electron oxidoreductase(s) in accordance with the invention preferably represent(s) from 0.01 to 20% by weight approximately relative to the total weight of the composition, and even more preferably from 0.1 to 5% by weight approximately relative to this weight. [0027]
  • According to the invention, the term donor is understood to refer to the various substrates also necessary for the functioning of the said 2-electron oxidoreductase(s). [0028]
  • The nature of the donor (or substrate) for the said enzyme varies depending on the nature of the 2-electron oxidoreductase used. For example, as donors for the pyranose oxidases, mention may be made of D-glucose, L-sorbose and D-xylose; as a donor for the glucose oxidases, mention may be made of D-glucose; as donors for the glycerol oxidases, mention may be made of glycerol and dihydroxyacetone; as donors for the lactate oxidases, mention may be made of lactic acid and its salts; as donors for the pyruvate oxidases, mention may be made of pyruvic acid and its salts; and lastly, as donors for the uricases, mention may be made of uric acid and its salts. [0029]
  • The donor(s) (or substrate(s)) used in accordance with the invention preferably represent from 0.01 to 20% by weight approximately relative to the total weight of the composition in accordance with the invention, and even more preferably from 0.1 to 5% approximately relative to this weight. [0030]
  • According to the invention, unmodified or. chemically modified nonionic guar gums can be used. [0031]
  • The unmodified nonionic guar gums are, for example, the products sold under the name Vidogum GH 175 by the company Unipectine and under the name Jaguar C by the company Meyhall. [0032]
  • The nonionic guar gums which can be used according to the invention are preferably modified with C[0033] 1-C6 hydroxyalkyl groups.
  • Among the hydroxyalkyl groups, mention may be made, for example, of hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups. [0034]
  • These guar gums are well known in the state of the art and can be prepared, for example, by reacting corresponding alkene oxides, such as, for example, propylene oxides, with the guar gum, so as to obtain a guar gum modified with hydroxypropyl groups. [0035]
  • The degree of hydroxyalkylation, which corresponds to the number of alkylene oxide molecules consumed by the number of free hydroxyl functions present on the guar gum, preferably ranges from 0.4 to 1.2. [0036]
  • Such nonionic guar gums optionally modified with hydroxyalkyl groups are sold, for example, under the trade names Jaguar HP8, Jaguar HP60 and Jaguar HP120, Jaguar DC 293 and Jaguar HP 105 by the company Rhône-Poulenc (Meyhall) or under the name Galactasol 4H4FD2 by the company Aqualon. [0037]
  • The concentration of nonionic guar gum can range from 0.01 to 10% by weight approximately relative to the total weight of the composition, and preferably between 0.1 and 5% approximately. [0038]
  • A subject of the present invention is also a ready-to-use composition for the oxidation dyeing of keratin fibres, and in particular human keratin fibres such as the hair, of the type comprising, in a medium which is suitable for dyeing, at least one oxidation base and, where appropriate, one or more couplers, which is characterized in that it contains: [0039]
  • (a) at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme, [0040]
  • (b) at least one nonionic guar gum. [0041]
  • The nature of the oxidation base(s) used in the ready-to-use dye composition is not a critical factor. They can be chosen, in particular, from para-phenylenediamines, double bases, para-aminophenols, ortho-aminophenols and heterocyclic oxidation bases. [0042]
  • Among the para-phenylenediamines which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made in particular of the compounds of formula (I) below, and the addition salts thereof with an acid: [0043]
    Figure US20040194232A1-20041007-C00001
  • in which: [0044]
  • R[0045] 1 represents a hydrogen atom, a C1-C4 alkyl radical, a C1-C4 monohydroxyalkyl radical, a C2-C4 polyhydroxyalkyl radical, a (C1-C4)alkoxy (C1-C4)alkyl radical, a C1-C4 alkyl radical substituted with a nitrogenous group, a phenyl radical or a 4′-aminophenyl radical;
  • R[0046] 2 represents a hydrogen atom, a C1-C4 alkyl radical, a C1-C4 monohydroxyalkyl radical, a C2-C4 polyhydroxyalkyl radical, a (C1-C4)alkoxy (C1-C4)alkyl radical or a C1-C4 alkyl radical substituted with a nitrogenous group;
  • R[0047] 3 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a C1-C4 alkyl radical, a C1-C4 monohydroxyalkyl radical, a C1-C4 hydroxyalkoxy radical, an acetylamino (C1-C4)alkoxy radical, a C1-C4 mesylaminoalkoxy radical or a carbamoylamino (C1-C4) alkoxy radical,
  • R[0048] 4 represents a hydrogen or halogen atom or a C1-C4 alkyl radical.
  • Among the nitrogenous groups of formula (I) above, mention may be made in particular of amino, mono (C[0049] 1-C4) alkylamino, di(C1-C4)alkylamino, tri(C1-C4)alkylamino, monohydroxy (C1-C4)alkylamino, imidazolinium and ammonium radicals.
  • Among the para-phenylenediamines of formula (I) above, mention may be made more particularly of para-phenylenediamine, para-toluylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(β-hydroxyethyl)-para-phenylenediamine, 4-amino-N,N-bis(β-hydroxyethyl)-2-methylaniline, 4-amino-2-chloro-N,N-bis(β-hydroxyethyl)aniline, 2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(β-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N,N-(ethyl-β-hydroxyethyl)-para-phenylenediamine, N-(β,γ-dihydroxypropyl)-para-phenylenediamine, N-(4′-aminophenyl)-para-phenylene-diamine, N-phenyl-para-phenylenediamine, 2-β-hydroxy-ethyloxy-para-phenylenediamine, 2-β-acetylamino-ethyloxy-para-phenylenediamine and N-(β-methoxyethyl)-para-phenylenediamine, and the addition salts thereof with an acid. [0050]
  • Among the para-phenylenediamines of formula (I) above, para-phenylenediamine, para-toluylenediamine, 2-isopropyl-para-phenylenediamine, 2-β-hydroxyethyl-para-phenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N,N-bis (β-hydroxyethyl)-para-phenylenediamine, 2-chloro-para-phenylenediamine and 2-β-acetylaminoethyloxy-para-phenylenediamine and the addition salts thereof with an acid are most particularly preferred. [0051]
  • According to the invention, the term double bases is understood to refer to the compounds containing at least two aromatic rings bearing amino and/or hydroxyl groups. [0052]
  • Among the double bases which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made in particular of the compounds corresponding to formula (II) below, and the addition salts thereof with an acid: [0053]
    Figure US20040194232A1-20041007-C00002
  • in which: [0054]
  • Z[0055] 1 and Z2, which may be identical or different, represent a hydroxyl or —NH2 radical which may be substituted with a C1-C4 alkyl radical or with a linker arm Y;
  • the linker arm Y represents a linear or branched alkylene chain containing from 1 to 14 carbon atoms, which may be interrupted by or terminated with one or more nitrogenous groups and/or one or more hetero atoms such as oxygen, sulphur or nitrogen atoms, and optionally substituted with one or more hydroxyl or C[0056] 1-C4 alkoxy radicals;
  • R[0057] 5 and R6 represent a hydrogen or halogen atom, a C1-C4 alkyl radical, a C1-C4 monohydroxyalkyl radical, a C2-C4 polyhydroxyalkyl radical, a C1-C4 aminoalkyl radical or a linker arm Y;
  • R[0058] 7, R8, R9, R10, R11 and R12, which may be identical or different, represent a hydrogen atom, a linker arm Y or a C1-C4 alkyl radical;
  • it being understood that the compounds of formula (II) contain only one linker arm Y per molecule. [0059]
  • Among the nitrogenous groups of formula (II) above, mention may be made in particular of amino, mono(C[0060] 1-C4)alkylamino, di(C1-C4)alkylamino, tri(C1-C4)alkylamino, monohydroxy(C1-C4)alkylamino, imidazo-linium and ammonium radicals.
  • Among the double bases of formula (II) above, mention may be made more particularly of N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-amino-phenyl)ethylenediamine, N,N′-bis(4-aminophenyl)-tetramethylenediamine, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(4-methylaminophenyl)tetramethylenediamine, N,N′-bis-(ethyl) -N,N′-bis(4′-amino-3′-methylphenyl)ethylenediamine and 1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and the addition salts thereof with an acid. [0061]
  • Among these double bases of formula (II), N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-di-aminopropanol and 1,8-bis (2,5-diaminophenoxy)-3,5-dioxaoctane, or one of the addition salts thereof with an acid, are particularly preferred. [0062]
  • Among the para-aminophenols which can be used as oxidation bases. in the dye compositions in accordance with the invention, mention may be made in particular of the compounds corresponding to formula (III) below, and the addition salts thereof with an acid: [0063]
    Figure US20040194232A1-20041007-C00003
  • in which: [0064]
  • R[0065] 13 represents a hydrogen or halogen atom or a C1-C4 alkyl, C1-C4 monohydroxyalkyl, (C1-C4) alkoxy (C1-C4) alkyl, C1-C4 aminoalkyl or hydroxy (C1-C4) alkylamino (C1-C4) alkyl radical,
  • R[0066] 14 represents a hydrogen or halogen atom or a C1-C4-alkyl, C1-C4 monohydroxyalkyl, C2-C4 polyhydroxyalkyl, C1-C4 aminoalkyl, C1-C4 cyanoalkyl or (C1-C4) alkoxy-(C1-C4) alkyl radical,
  • it being understood that at least one of the radicals R[0067] 13 or R14 represents a hydrogen atom.
  • Among the para-aminophenols of formula (III) above, mention may be made more particularly of para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(β-hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid. [0068]
  • Among the ortho-aminophenols which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made more particularly of 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid. [0069]
  • Among the heterocyclic bases which can be used as oxidation bases in the dye compositions in accordance with the invention, mention may be made more particularly of pyridine derivatives, pyrimidine derivatives, pyrazole derivatives and pyrazolopyrimidine derivatives, and the addition salts thereof with an acid. [0070]
  • Among the pyridine derivatives, mention may be made more particularly of the compounds described, for example, in patents GB 1,026,978 and GB 1,153,196, such as 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-(β-methoxyethyl)amino-3-amino-6-methoxypyridine and 3,4-diaminopyridine, and the addition salts thereof with an acid. [0071]
  • Among the pyrimidine derivatives, mention may be made more particularly of the compounds described, for example, in German patent DE 2,359,399 or Japanese patent JP 88-169,571 or patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine, and the addition salts thereof with an acid. [0072]
  • Among the pyrazole derivatives, mention may be made more particularly of the compounds described in patents DE 3,843,892, DE 4,133,957 and patent. applications WO 94/08969, WO 94/08970, FR-A-2,733,749 and DE 195 43 988, such as 4,5-diamino-1-methyl-pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4′-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethyl-pyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-1-methyl-pyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole, 4,5-diamino-l-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-iso-propylpyrazole, 4,5-diamino-3-methyl-1-isopropyl-pyrazole, 4-amino-5-(2′-aminoethyl) amino-1,3-dimethylpyrazole, 3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3,5-diamino-4-(β-hydroxyethyl)amino-1-methylpyrazole, and the addition salts thereof with an acid. [0073]
  • Among the pyrazolopyrimidine derivatives, mention may be made more particularly of the. pyrazolo[1,5-a]pyrimidines of formula (IV) below, and the addition salts thereof with an acid or with a base and the tautomeric forms thereof, when a tautomeric equilibrium exists: in which: [0074]
    Figure US20040194232A1-20041007-C00004
  • in which: [0075]
  • R[0076] 15, R16, R17 and R18, which may be identical or different, denote a hydrogen atom, a C1-C4 alkyl radical, an aryl radial, a C1-C4 hydroxyalkyl radical, a C2-C4 polyhydroxyalkyl radical, a (C1-C4) alkoxy (C1-C4) alkyl radical, a C1-C4 aminoalkyl radical (it being possible for the amine to be protected with an acetyl, ureido or sulphonyl radical), a (C1-C4) alkylamino (C1-C4) alkyl radical, a di[(C1-C4)alkyl]amino (C1-C4)alkyl radical (it being possible for the dialkyl radicals to form a 5- or 6-membered carbon-based ring or a heterocycle), a hydroxy (C1-C4)alkyl- or di[hydroxy-(C1-C4)alkyl]amino (C1-C4)alkyl radical;
  • the radicals X, which may be identical or different, denote a hydrogen atom, a C[0077] 1-C4 alkyl radical, an aryl radical, a C1-C4 hydroxyalkyl radical, a C2-C4 polyhydroxyalkyl radical, a C1-C4 aminoalkyl radical, a (C1-C4)alkylamino (C1-C4)alkyl radical, a di[(C1-C4)alkyl]amino (C1-C4)alkyl radical (it being possible for the dialkyls to form a 5- or 6-membered carbon-based ring or a heterocycle), a hydroxy (C1-C4)alkyl- or di-[hydroxy(C1-C4)alkyl]amino (C1-C4)alkyl radical, an amino radical, a (C1-C4)alkyl- or di[(C1-C4)alkyl]amino radical; a halogen atom, a carboxylic acid group or a sulphonic acid group;
  • i is equal to 0, 1, 2 or 3; [0078]
  • p is equal to 0 or 1; [0079]
  • q is equal to 0 or 1; [0080]
  • n is equal to 0 or 1; [0081]
  • with the proviso that: [0082]
  • the sum p+q is other than 0; [0083]
  • when p+q is equal to 2, then n is equal to 0 and the groups NR[0084] 15R16 and NR17R18 occupy the (2,3); (5,6); (6,7); (3,5) or (3,7) positions;
  • when p+q is equal to 1, then n is equal to 1 and the group NR[0085] 15R16 (or NR17R18) and the OH group occupy the (2,3); (5,6); (6,7); (3,5) or (3,7) positions.
  • When the pyrazolo[1,5-a]pyrimidines of formula (IV) above are such that they contain a hydroxyl group on one of the positions 2, 5 or 7 a to a nitrogen atom, a tautomeric equilibrium exists represented, for example, by the following scheme: [0086]
    Figure US20040194232A1-20041007-C00005
  • Among the pyrazolo[1,5-a]pyrimidines of formula (IV) above, mention may be made in particular of: [0087]
  • pyrazolo[1,5-a]pyrimidine-3,7-diamine; [0088]
  • 2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; [0089]
  • pyrazolo[1,5-a]pyrimidine-3,5-diamine; [0090]
  • 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine; [0091]
  • 3-aminopyrazolo[1,5-a]pyrimidin-7-ol; [0092]
  • 3-aminopyrazolo[1,5-a]pyrimidin-5-ol; [0093]
  • 2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol; [0094]
  • 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol; [0095]
  • 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)-(2-hydroxy-ethyl)amino]ethanol; [0096]
  • 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)-(2-hydroxy-ethyl)amino]ethanol; [0097]
  • 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; [0098]
  • 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; [0099]
  • 2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; and the addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists. [0100]
  • The pyrazolo[1,5-a]pyrimidines of formula (IV) above can be prepared by cyclization starting with an aminopyrazole, according to the syntheses described in the following references: [0101]
  • EP 628559 Beiersdorf-Lilly. [0102]
  • R. Vishdu, H. Navedul, Indian J. Chem., 34b (6), 514, 1995. [0103]
  • N. S. Ibrahim, K. U. Sadek, F. A. Abdel-Al, Arch. Pharm., 320, 240, 1987. [0104]
  • R. H. Springer, M. B. Scholten, D. E. O'Brien, T. Novinson, J. P. Miller, R. K. Robins, J. Med. Chem., 25, 235, 1982. [0105]
  • T. Novinson, R. K. Robins, T. R. Matthews, J. Med. Chem., 20, 296, 1977. [0106]
  • U.S. Pat. No. 3,907,799 ICN Pharmaceuticals. [0107]
  • The pyrazolo[1,5-a]pyrimidines of formula (IV) above can also be prepared by cyclization starting from hydrazine, according to the syntheses described in the following references: [0108]
  • A. McKillop and R. J. Kobilecki, Heterocycles, 6(9), 1355, 1977. [0109]
  • E. Alcade, J. De Mendoza, J. M. Marcia-Marquina, C. Almera, J. Elguero, J. Heterocyclic Chem., 11(3), 423, 1974. [0110]
  • K. Saito, I. Hori, M. Higarashi, H. Midorikawa, Bull. Chem. Soc. Japan, 47(2), 476, 1974. [0111]
  • The oxidation base(s) in accordance with the invention preferably represent(s) from 0.0005 to 12% by weight approximately relative to the total weight of the ready-to-use dye composition, and even more preferably from 0.005 to 6% by weight approximately relative to this weight. [0112]
  • The couplers which can be used are those used conventionally in oxidation dye compositions, i.e. meta-phenylenediamines, meta-aminophenols and meta-diphenols, mono- or polyhydroxylated naphthalene derivatives, sesamol and its derivatives and heterocyclic compounds such as, for example, indole derivatives, indoline derivatives, benzimidazole derivatives, benzomorpholine derivatives, sesamol derivatives, pyrazoloazole derivatives, pyrroloazole derivatives, imidazoloazole derivatives, pyrazolo-pyrimidine derivatives, pyrazoline-3,5-dione derivatives, pyrrolo[3,2-d]oxazole derivatives, pyrazolo [3,4-d]thiazole derivatives, thiazoloazole S-oxide derivatives and thiazoloazole S,S-dioxide. derivatives, and the addition salts thereof with an acid. [0113]
  • These couplers can be chosen in particular from 2-methyl-5-aminophenol, 5-N-(β-hydroxyethyl) amino-2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxy-benzene, 2,4-diamino-1-(β-hydroxyethyloxy)benzene, 2-amino-4-(β-hydroxyethylamino) -1-methoxybenzene, 1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol, α-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine, 1H-3-methylpyrazol-5-one and 1-phenyl-3-'methylpyrazol-5-one, and the addition salts thereof with an acid. [0114]
  • When they are present, these couplers preferably represent from 0.0001 to 10% by weight approximately relative to the total weight of the ready-to-use dye composition, and even more preferably from 0.005 to 5% by weight approximately relative to this weight. [0115]
  • In general, the addition salts with an acid which can be used in the context of the dye compositions of the invention (oxidation bases and couplers) are chosen in particular from the hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates. [0116]
  • The dye composition of the invention can also contain, in addition to the oxidation bases defined above and the optional combined couplers, direct dyes to enrich the shades with glints. These direct dyes can be chosen in particular from nitro dyes, azo dyes or anthraquinone dyes. [0117]
  • The subject of the invention is also a process for dyeing keratin fibres, and in particular human. keratin fibres such as the hair, using the ready-to-use dye composition as defined above. [0118]
  • According to this process, at least one ready-to-use dye composition as defined above is placed on the fibres, for a period which is sufficient to develop the desired coloration, after which the fibres are rinsed, optionally washed with shampoo, rinsed again and dried. [0119]
  • The time required to develop the coloration on the keratin fibres is generally beteen 3 and 60 minutes and even more precisely between 5 and 40 minutes. [0120]
  • According to a first specific embodiment of the invention, the process includes a first step which consists in separately storing, on the one hand, a composition (A) comprising, in a medium which is suitable for dyeing, at least one oxidation base and optionally at least one coupler as defined above, and, on the other hand, a composition (B) containing, in a medium which is suitable for dyeing, at least one enzyme of 2-electron oxidoreductase type in the presence of at least one donor for the said enzyme and at least one nonionic guar gum containing at least one hydrophilic unit and at least one fatty chain, and then in mixing them together at the time of use, before applying this mixture to the keratin fibres. [0121]
  • According to another specific embodiment of the invention, the nonionic guar gum is incorporated into composition (A). [0122]
  • Another subject of the invention is a multi-compartment dyeing device or “kit” or any other multi-compartment packaging system, a first compartment of which contains composition (A) as defined above and a second compartment of which contains composition (B) as defined above. These devices can be equipped with means for applying the desired mixture to the hair, such as the devices described in patent FR-2,586,913 in the name of the Applicant. [0123]
  • A subject of the present invention is also a, novel process for treating keratin substances, in particular the hair, in order to obtain a permanent reshaping of this hair, in particular in the form of permanent-waved hair, this process comprising the following steps: (i) a reducing composition is applied to the keratin substance to be treated, the keratin substance being placed under mechanical tension before, during or after the said application, (ii) the keratin substance is optionally rinsed, (iii) an oxidizing composition as defined above is applied to the optionally rinsed keratin substance, (iv) the keratin substance is optionally rinsed again. [0124]
  • The first step (i) of this process consists in applying a reducing composition to the hair. This application is carried out lock by lock or all at once. [0125]
  • The reducing composition comprises, for example, at least one reducing agent, which can be chosen in particular from thioglycolic acid, cysteine, cysteamine, glyceryl thioglycolate, thiolactic acid or thiolactic or thioglycolic acid salts. [0126]
  • The usual step for placing the hair under tension in a shape corresponding to the desired final shape for this hair (for example curls) can be carried out by any suitable means, in particular mechanical means, known per se for maintaining the hair under tension, such as, for example, rollers, curlers and the like. [0127]
  • The hair can also be shaped without the aid of external means, simply with the fingers. [0128]
  • Before carrying out the following optional rinsing step (ii), the hair onto which the reducing composition has been applied should, conventionally, be left to stand for a few minutes, generally between 5 minutes and one hour, preferably between 10 and 30 minutes, so as to give the reducing agent enough time to act correctly on the hair. This waiting phase preferably takes place at a temperature ranging from 35° C. to 45° C., while preferably also protecting the hair with a hood. [0129]
  • In the optional second step of the process (step (ii)), the hair impregnated with the reducing composition is then rinsed thoroughly with an aqueous composition. [0130]
  • Next, in a third step (step (iii)), the oxidizing composition of the invention is applied to the hair thus rinsed, with the aim of fixing the new shape given to the hair. [0131]
  • As in the case of the application of the reducing composition, the hair onto which the oxidizing composition has been applied is then conventionally, left for a standing or waiting phase lasting a few minutes, generally between 3 and 30 minutes, preferably between 5 and 15 minutes. [0132]
  • If the hair was maintained under tension by external means, these means (rollers, curlers or the like) can be removed from the hair before or after the fixing step. [0133]
  • Lastly, in the final step of the process according to the invention (step (iv)), which is also optional, the hair impregnated with the oxidizing composition is rinsed thoroughly, generally with water. [0134]
  • Hair which is soft and easy to disentangle is finally obtained. The hair is wavy. [0135]
  • The oxidizing composition according to the invention can also be used in a process for bleaching keratin fibres, and in particular the hair. [0136]
  • The bleaching process according to the invention comprises a step of applying an oxidizing composition according to the invention to the keratin fibres in the presence or absence of an auxiliary oxidizing agent. Conventionally, a second step of the bleaching process according to the invention is a step of rinsing the keratin fibres. [0137]
  • The medium which is suitable for the keratin fibres (or the support) for the ready-to-use dye compositions and for the oxidation compositions used for the permanent reshaping or bleaching of keratin- fibres in accordance with the invention generally consists of water or of a mixture of water and at least one organic solvent in order to dissolve the compounds which would not be sufficiently soluble in water. By way of organic solvent, mention may be made, for example, of C[0138] 1-C4 alkanols such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and aromatic alcohols such as benzyl alcohol or phenoxyethanol, similar products and mixtures thereof.
  • The solvents can be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately. [0139]
  • The pH of the ready-to-use dye compositions and of the oxidizing compositions used for the permanent reshaping or bleaching of the keratin fibres in accordance with the invention is chosen such that the enzymatic activity of the 2-electron oxidoreductase is not adversely affected. It is generally between 5 and 11 approximately, and preferably between 6.5 and 10 approximately. It can be adjusted to the desired value using acidifying or basifying agents usually used for dyeing keratin fibres. [0140]
  • Among the acidifying agents, mention may be made, by way of example, of inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids. [0141]
  • Among the basifying agents, mention may be made, by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines, 2-methyl-2-aminopropanol and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (V) below: [0142]
    Figure US20040194232A1-20041007-C00006
  • in which W is a propylene residue optionally substituted with a hydroxyl group or a C[0143] 1-C4 alkyl radical; R13, R14, R15 and R16, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl or C1-C4 hydroxyalkyl radical.
  • The ready-to-use dye compositions and the oxidizing compositions for the permanent reshaping or bleaching of keratin fibres in accordance with the invention can also contain various adjuvants used conventionally in compositions for dyeing, permanently reshaping or bleaching the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickeners, antioxidants, enzymes other than the 2-electron oxidoreductases used in accordance with the invention, such as, for example, peroxidases, penetration agents, sequestering agents, fragrances, buffers, dispersing agents, conditioners such as, for example, silicones, film-forming agents, preserving agents and opacifiers. [0144]
  • Needless to say, a person skilled in the art will take care to select this or these optional complementary compound(s) such that the advantageous properties intrinsically associated with the compositions in accordance with the invention are not, or are not substantially, adversely affected by the addition or additions envisaged. [0145]
  • The ready-to-use dye compositions and the oxidizing compositions used for the permanent reshaping or bleaching of keratin fibres in accordance with the invention can be in various forms, such as in the form of liquids, creams or gels, which are optionally pressurized, or in any other form which is suitable for dyeing, permanently reshaping or bleaching keratin fibres, and in particular human hair. [0146]
  • In the case of a ready-to-use dye composition, the oxidation dyes(s) and the 2-electron oxido-reductase(s) are present in the said composition, which must be free of oxygen gas, so as to avoid any premature oxidation of the oxidation dye(s). [0147]
  • Concrete examples illustrating the invention will now be given. [0148]
  • In the text hereinabove and hereinbelow, except where otherwise mentioned, the percentages are expressed on a weight basis. [0149]
  • The examples which follow illustrate the invention without being limiting in nature.[0150]
  • EXAMPLE 1 Dye Composition
  • The ready-to-use dye composition below was prepared (contents in grams): [0151]
    Uricase from Arthrobacter globiformis at a  1.5 g
    concentration of 20 International Units
    (I.U.)/mg, sold by the company Sigma
    Uric acid  1.5 g
    (C8-C10)alkyl polyglucoside as an aqueous  8.0 g
    solution containing 60% active material
    (A.M.), sold under the name Oramix CG110
    by the company SEPPIC
    Para-phenylenediamine 0.324 g
    Resorcinol  0.32 g
    Hydroxypropyl guar gum sold under the name  1.6 g
    Jaguar HP 60 by the company Mayhall
    Ethanol  20.0 g
    Monoethanolamine qs pH 9.5
    Demineralized waterqs   100 g
  • This ready-to-use dye composition was applied to locks of natural grey hair containing 90% white hairs for 30 minutes. The hair was then rinsed, washed with a standard shampoo and then dried. [0152]
  • Locks of hair dyed a matt dark-blond colour were obtained. [0153]
  • EXAMPLE 2 Oxidizing Composition for Permanent-Waving or Bleaching
  • [0154]
    Uricase from Arthrobacter globiformis at a  1.8 g
    concentration of 20 International Units
    (I.U.)/mg, sold by the company Sigma
    Uric acid 1.65 g
    Ethanol 20.0 g
    (C8-C10)alkyl polyglucoside as an aqueous  8.0 g
    solution containing 60% active material
    (A.M.), sold under the name Oramix CG110
    by the company SEPPIC
    Hydroxypropyl guar gum sold under the name 0.25 g
    Jaguar HP 60 by the company Mayhall
    2-Methyl-2-amino-1-propanol qs pH 9.5
    Demineralized water qs  100 g

Claims (30)

1-27 (Canceled)
28. A ready-to-use composition for the oxidation dyeing of keratin fibers comprising:
at least one enzyme chosen from 2-electron oxidoreductases;
at least one donor for said at least one enzyme;
at least one nonionic guar gum; and
at least one oxidation base.
29. The ready-to-use composition of claim 28, wherein said at least one oxidation base is chosen from para-phenylenediamines, double bases, ortho- and para-aminophenols, heterocyclic bases, and acid addition salts thereof.
30. The ready-to-use composition of claim 28, wherein said at least one oxidation base is present in an amount ranging from 0.0005 to 12% by weight relative to the total weight of the composition.
31. The ready-to-use composition of claim 29, wherein said acid addition salts are chosen from hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
32. The ready-to-use composition of claim 28, further comprising at least one coupler.
33. The ready-to-use composition of claim 32, wherein said at least one coupler is a meta-aminophenol coupler chosen from meta-aminophenol, 5-amino-2-methoxyphenol, 5-amino-2-(β-hydroxyethyloxy)phenol, 5-amino-2-methylphenol, 5-N-(β-hydroxyethyl)amino-2-methyl phenol, 5-N-(β-hydroxyethyl)amino-4-methoxy-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-2,4-dimethoxyphenol, 5-(γ-hydroxypropylamino)-2methylphenol and acid-addition salts thereof.
34. The ready-to-use composition of claim 33, wherein said at least one meta-aminophenol coupler is present in an amount ranging from 0.0001 to 10% by weight relative to the total weight of the composition.
35. The ready-to-use composition of claim 33, wherein the acid addition salts are chosen from hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
36. The ready-to-use composition of claim 28, further comprising at least one direct dye.
37. The ready-to-use composition of claim 29, further comprising water or a mixture of water and at least one organic solvent.
38. A ready-to-use composition for the oxidation dyeing of keratin fibers comprising:
at least one 2-electron oxidoreductase enzyme chosen from pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases and uricases;
at least one donor for said at least one enzyme chosen from D-glucose, L-sorbose, D-xylose, glycerol, dihydroxyacetone, pyruvic acid and its salts, lactic acid and its salts, and uric acid and its salts;
at least one nonionic guar gum chosen from unmodified guar gums and chemically modified guar gums, wherein said chemically modified guar gums are modified with C1-C6 hydroxyalkyl groups chosen from hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups, where in said C1-C6 hydroxyalkyl groups have a degree of hydroxyalkylation ranging from 0.4 to 1.2;
at least one oxidation base chosen from para-phenylenediamine compounds chosen from: para-phenylenediamine, para-toluylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N, N-dimethyl-para phenylenediamine, N,N-diethyl-para-phenylenediamine, N, N-dipropyl-para-phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(β-hydroxyethyl)para-phenylenediamine, 4-amino-N,N-bis(β-hydroxyethyl)-2-methylaniline, 4-amino-2-chloro-N,N-bis(β-hydroxyethyl)aniline, 2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(β-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-paraphenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N,N-(ethyl-β-phydroxyethyl)-para-phenylenediamine, N-(β,γ-dihydroxypropyl)-para-phenylene-diamine, N-(4′-aminophenyl)-para-phenylenediamine, N-phenyl-paraphenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2-β-acetylaminoethyloxy-para-phenylenediamine, N-(β-methoxyethyl)-para-phenylenediamine, and acid-addition salts thereof;
double bases chosen from: N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-amino-phenyl)ethylenediamine, N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(4methylaminophenyl)tetramethylenediamine, N,N′-bis(ethyl)-N,N′-bis(4′-amino-3′-methylphenyl)ethylenediamine, 1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and acid-addition salts thereof;
ortho-aminophenols chosen from: 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, and acid-addition salts thereof;
pyridine compounds chosen from: 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-amino-pyridine, 2,3-diamino-6-methoxypyridine, 2-(ÿ-methoxy-ethyl)amino-3-amino-6-methoxypyridine, 3,4-diaminopyridine, and acid-addition salts thereof;
pyrimidine compounds chosen from: 2,4,5,6-tetraamino-pyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triamino-pyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-tri-amino-pyrimidine, and acid-addition salts thereof;
pyrazole compounds chosen from: 4,5-diamino-1-methyl-pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4′-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethyl-pyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5 diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-di-methyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methyl-pyrazole, 4,5-diamino-3-tert-butyl-1-methyl-pyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methyl-pyrazole, 4,5-diamino-3 hydroxymethyl-1-iso-propyl-pyrazole, 4,5-diamino-3-methyl-1-isopropyl-pyrazole, 4-amino-5-(2′-amino-ethyl)amino-1,3-dimethyl-pyrazole, 3,4,5-triamino-pyrazole, 1-methyl-3,4,5-tri-amino-pyrazole, 3,5-diamino-1-methyl-4-methylamino-pyrazole, 3,5-diamino-4-(β-hydroxyethyl)amino-1-methyl-pyrazole, and acid-addition salts thereof,
pyrazolopyrimidine compounds chosen from: pyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, pyrazolo[1,5-a]pyrimidine-3,5-diamine, 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine, 3-aminopyrazolo[1,5-a]pyrimidin-7-ol, 3-aminopyrazolo[1,5-a]pyrimidin-5-ol, 2-(3-aminopyrazolo[1,5-alpyrimidin-7-ylamino)ethanol, 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol, 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)-(2-hydroxy-ethyl)amino]ethanol, 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)-(2-hydroxy-ethyl)amino]ethanol, 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; and addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists; and
at least one meta-aminophenol coupler chosen from meta-aminophenol, 5-amino-2-methoxyphenol, 5-amino-2-(β-hydroxyethyloxy)phenol, 5-amino-2-methylphenol, 5-N-(β-hydroxyethyl)amino-2-methylphenol, 5-N-(β-hydroxyethyl)amino-4-methoxy-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-2,4-dimethoxyphenol, 5-(γ-hydroxypropylamino)-2-methylphenol and acid-addition salts thereof.
39. A ready-to-use composition for the oxidation dyeing of keratin fibers comprising uricase from Arthrobacter globiformis, uric acid, C8-C10 alkyl polyglucoside, para-phenylenediamine, resorcinol, and hydroxylpropyl guar gum.
40. A ready-to-use composition for the oxidation dyeing of keratin fibers comprising uricase from Arthrobacter globiformis, uric acid, C8-C10 alkyl polyglucoside, and hydroxylpropyl guar gum.
41. A method for dyeing keratin fibers comprising applying to said keratin fibers a composition, and then developing for a period of time sufficient to achieve a desired coloration, wherein said composition comprises:
at least one enzyme chosen from 2-electron oxidoreductases;
at least one donor for said at least one enzyme; and
at least one nonionic guar gum.
42. The method of claim 41, wherein said time sufficient ranges from 3 to 60 minutes.
43. The method of claim 42, wherein said time sufficient ranges from 5 to 40 minutes.
44. The method of claim 41, wherein said composition further comprises at least one oxidation base.
45. The method of claim 44, wherein said composition further comprises at least one coupler.
46. A method for dyeing keratin fibers comprising applying to said keratin fibers a composition, and then developing for a period of time sufficient to achieve a desired coloration, wherein said composition comprises:
at least one 2-electron oxidoreductase enzyme chosen from pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases and uricases;
at least one donor for said at least one enzyme chosen from D-glucose, L-sorbose, D-xylose, glycerol, dihydroxyacetone, pyruvic acid and its salts, lactic acid and its salts, and uric acid and its salts;
at least one nonionic guar gum chosen from unmodified guar gums and chemically modified guar gums, wherein said chemically modified guar gums are modified with C1-C6 hydroxyalkyl groups chosen from hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups, wherein said C1-C6 hydroxyalkyl groups have a degree of hydroxyalkylation ranging from 0.4 to 1.2;
at least one oxidation base chosen from
para-phenylenediamine compounds chosen from: para-phenylenediamine, para-toluylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-paraphenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-paraphenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-paraphenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(β-hydroxyethyl)para-phenylenediamine, 4-amino-N,N-bis(β-hydroxyethyl)-2-methylaniline, 4-amino2-chloro-N,N-bis(β-hydroxyethyl)aniline, 2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(β-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N,N-(ethyl-β-hydroxyethyl)-para-phenylenediamine, N-(β,γ-dihydroxypropyl)-para-phenylene-diamine, N-(4′-aminophenyl)-para-phenylenediamine, N-phenyl-paraphenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2-β-acetylaminoethyloxy-para-phenylenediamine, N-(β-methoxyethyl)-para-phenylenediamine, and acid-addition salts thereof;
double bases chosen from: N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-amino-phenyl)ethylenediamine, N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(4methylaminophenyl)tetramethylenediamine, N,N′-bis(ethyl)-N,N′-bis(4′-amino-3′-methylphenyl)ethylenediamine, 1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and acid-addition salts thereof;
ortho-aminophenols chosen from: 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, and acid-addition salts thereof;
pyridine compounds chosen from: 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-amino-pyridine, 2,3-diamino-6-methoxypyridine, 2-(ÿ-methoxy-ethyl)amino-3-amino-6-methoxypyridine, 3,4-diaminopyridine, and acid-addition salts thereof;
pyrimidine compounds chosen from: 2,4,5,6-tetraamino-pyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triamino-pyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-tri-amino-pyrimidine, and acid-addition salts thereof;
pyrazole compounds chosen from: 4,5-diamino-1-methyl-pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4′-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethyl-pyrazole, 4,5-diamino-3-methyl-l-phenylpyrazole, 4,5diamino-l-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methyl-pyrazole, 4,5-diamino-3-tert-butyl-1-methyl-pyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole, 4,5diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methyl-pyrazole, 4,5-diamino-3-hydroxymethyl-1-iso-propyl-pyrazole, 4,5-diamino-3-methyl-1-isopropyl-pyrazole, 4-amino-5-(2′-amino-ethyl)amino-1,3-dimethyl-pyrazole, 3,4,5-triamino-pyrazole, 1-methyl-3,4,5-tri-aminopyrazole, 3,5-diamino-1-methyl-4-methylamino-pyrazole, 3,5-diamino-4-(β-hydroxyethyl)amino-1-methyl-pyrazole, and acid-addition salts thereof,
pyrazolopyrimidine compounds chosen from: pyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, pyrazolo[1,5-a]pyrimidine-3,5-diamine, 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine, 3-aminopyrazolo[1,5-a]pyrimidin-7-ol, 3-aminopyrazolo[1,5-a]pyrimidin-5-ol, 2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol, 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol, 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)-(2-hydroxy-ethyl)amino]ethanol, 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)-(2-hydroxy-ethyl)amino]ethanol, 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; and addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists; and
at least one meta-aminophenol coupler chosen from meta-aminophenol, 5-amino-2-methoxyphenol, 5-amino-2-(β-hydroxyethyloxy)phenol, 5-amino-2-methylphenol, 5-N-(β-hydroxyethyl)amino-2-methylphenol, 5-N-(βhydroxyethyl)amino-4-methoxy-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-2,4-dimethoxyphenol, 5-(y-hydroxypropylamino)-2-methylphenol and acid-addition salts thereof.
47. A method for dyeing keratin fibers comprising:
separately storing a first composition;
separately storing a second composition;
thereafter mixing said first composition with said second composition;
applying said mixture to said fibers, and then developing for a period of time sufficient to achieve a desired coloration;
wherein said first composition comprises at least one oxidation base chosen from para-phenylenediamine compounds chosen from: para-phenylenediamine, para-toluylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-paraphenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-paraphenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-paraphenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(β-hydroxyethyl)para-phenylenediamine, 4-amino-N,N-bis(β-hydroxyethyl)-2-methylaniline, 4-amino2-chloro-N,N-bis(β-hydroxyethyl)aniline, 2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(β-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-paraphenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N,N-(ethyl-β-hydroxyethyl)-para-phenylenediamine, N-(β,γ-dihydroxypropyl)-para-phenylene-diamine, N-(4′-aminophenyl)-para-phenylenediamine, N-phenyl-paraphenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2-β-acetylaminoethyloxy-para-phenylenediamine, N-(β-methoxyethyl)-para-phenylenediamine, and acid-addition salts thereof;
double bases chosen from: N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-amino-phenyl)ethylenediamine, N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(4-methylaminophenyl)tetramethylenediamine, N,N′-bis(ethyl)-N,N′-bis(4′-amino-3′-methylphenyl)ethylenediamine, 1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and acid-addition salts thereof;
ortho-aminophenols chosen from: 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, and acid-addition salts thereof;
pyridine compounds chosen from: 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-amino-pyridine, 2,3-diamino-6-methoxypyridine, 2-(ÿ-methoxy-ethyl)amino-3-amino-6-methoxypyridine, 3,4-diaminopyridine, and acid addition salts thereof;
pyrimidine compounds chosen from: 2,4,5,6-tetraamino-pyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triamino-pyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-tri-amino-pyrimidine, and acid-addition salts thereof;
pyrazole compounds chosen from: 4,5-diamino-1-methyl-pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4′-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethyl-pyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1 -methyl-3-phenylpyrazole, 4-amino-1,3-di-methyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methyl-pyrazole, 4,5-diamino-3-tert-butyl-1-methyl-pyrazole, 4,5-diamino-i-tert-butyl-3-methylpyrazole, 4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole, 4,5 diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methyl-pyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropyl-pyrazole, 4,5-diamino-3-methyl-1-isopropyl-pyrazole, 4-amino-5-(2′-amino-ethyl)amino-1,3-dimethyl-pyrazole, 3,4,5-triamino-pyrazole, 1-methyl-3,4,5-tri-amino-pyrazole, 3,5-diamino-1-methyl-4-methylamino-pyrazole, 3,5-diamino-4-(,-hydroxyethyl)amino-1-methyl-pyrazole, and acid-addition salts thereof,
pyrazolopyrimidine compounds chosen from: pyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5-dimethylpyrazolo(1, 5-a]pyrimidine-3,7-diamine, pyrazolo[1, 5-a]pyrimidine-3,5-diamine, 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine, 3-aminopyrazolo[1,5-a]pyrimidin-7-ol, 3-aminopyrazolo[1,5-a]pyrimidin-5-ol, 2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol, 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol, 2-[(3-aminopyrazolo[1, 5-a]pyrimidin-7-yl)-(2-hydroxy-ethyl)amino]ethanol, 2-[(7-aminopyrazolo[1, 5-a]pyrimidin-3-yl)-(2-hydroxy-ethyl)amino]ethanol, 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; and addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists;
wherein said second composition comprises at least one enzyme chosen from 2-electron oxidoreductases and at least one donor for said at least one enzyme; and
wherein at least one of said first and said second compositions further comprises at least one nonionic guar gum.
48. The method of claim 47, wherein said first composition further comprises at least one meta-aminophenol coupler chosen from meta-aminophenol, 5-amino-2-methoxyphenol, 5-amino-2-(β-hydroxyethyloxy)phenol, 5-amino-2-methylphenol, 5N-(β-hydroxyethyl)amino-2-methylphenol, 5-N-(β-hydroxyethyl)amino-4-methoxy-2-methylphenol, 5-amino4-methoxy-2-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-2,4-dimethoxyphenol, 5-(γ-hydroxypropylamino)-2-methylphenol and acid-addition salts thereof.
49. A multi-compartment kit for dyeing keratin fibers comprising at least two separate compartments wherein:
a first compartment contains a first composition; and
a second compartment contains a second composition;
wherein said first composition comprises at least one oxidation base;
wherein said second composition comprises at least one enzyme chosen from 2-electron oxidoreductases and at least one donor for said at least one enzyme;
wherein at least one of said first compartment and said second compartment further comprises at least one nonionic guar gum.
50. The multi-compartment kit of claim 49, wherein said first compartment further comprises at least one coupler.
51. A method for treating keratin fibers to obtain a permanent reshaping of said keratin fibers comprising:
applying a reducing composition to said keratin fibers, said fibres being placed under tension before, after, or during said application of said reducing composition; and
applying an oxidizing composition to said fibers;
wherein said oxidizing composition comprises at least one enzyme chosen from 2-electron oxidoreductases, at least one donor for said at least one enzyme, and at least one nonionic guar gum.
52. The method of claim 51, further comprising a rinsing step after the application of said reducing composition to said keratin fibers.
53. The method of claim 51, further comprising a rinsing step after the application of said oxidizing composition to said keratin fibers.
54. The method of claim 51, wherein said reducing composition is a reducing agent chosen from thioglycolic acid, cysteine, cysteamine, glycerol thioglycolic acid, thiolactic acid and thiolactic and thioglycolic acid salts.
55. A method for bleaching keratin fibers comprising:
applying an effective amount of an oxidizing composition to said fibers;
thereafter rinsing said fibers;
wherein said oxidizing composition comprises at least one enzyme chosen from 2-electron oxidoreductases, at least one donor for said at least one enzyme; and at least one nonionic guar gum.
56. The method of claim 55, wherein said oxidizing composition further comprises an auxiliary oxidizing agent.
US10/832,254 1997-10-03 2004-04-27 Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibers Abandoned US20040194232A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US10/832,254 US20040194232A1 (en) 1997-10-03 2004-04-27 Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibers

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR9712356A FR2769216B1 (en) 1997-10-03 1997-10-03 OXIDIZING COMPOSITION AND USES FOR DYEING, PERMANENT DEFORMATION OR DECOLORATION OF KERATINIC FIBERS
FR97/12356 1997-10-03
US09/319,163 US6241784B1 (en) 1997-10-03 1998-09-22 Oxidizing composition and uses for dyeing, for permanently setting or bleaching keratin fibres
US09/832,876 US20030000025A9 (en) 1997-10-03 2001-04-12 Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres
US10/832,254 US20040194232A1 (en) 1997-10-03 2004-04-27 Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibers

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US09/832,876 Continuation US20030000025A9 (en) 1997-10-03 2001-04-12 Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres

Publications (1)

Publication Number Publication Date
US20040194232A1 true US20040194232A1 (en) 2004-10-07

Family

ID=9511802

Family Applications (3)

Application Number Title Priority Date Filing Date
US09/319,163 Expired - Fee Related US6241784B1 (en) 1997-10-03 1998-09-22 Oxidizing composition and uses for dyeing, for permanently setting or bleaching keratin fibres
US09/832,876 Abandoned US20030000025A9 (en) 1997-10-03 2001-04-12 Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres
US10/832,254 Abandoned US20040194232A1 (en) 1997-10-03 2004-04-27 Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibers

Family Applications Before (2)

Application Number Title Priority Date Filing Date
US09/319,163 Expired - Fee Related US6241784B1 (en) 1997-10-03 1998-09-22 Oxidizing composition and uses for dyeing, for permanently setting or bleaching keratin fibres
US09/832,876 Abandoned US20030000025A9 (en) 1997-10-03 2001-04-12 Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres

Country Status (18)

Country Link
US (3) US6241784B1 (en)
EP (1) EP0966247B1 (en)
JP (1) JP3630373B2 (en)
KR (1) KR100322397B1 (en)
CN (1) CN1250196C (en)
AR (1) AR016945A1 (en)
AT (1) ATE295145T1 (en)
AU (1) AU718348B2 (en)
BR (1) BR9806171A (en)
CA (1) CA2271984A1 (en)
CZ (1) CZ205899A3 (en)
DE (1) DE69830152T8 (en)
ES (1) ES2245040T3 (en)
FR (1) FR2769216B1 (en)
HU (1) HUP0001212A3 (en)
RU (1) RU2179435C2 (en)
WO (1) WO1999017721A1 (en)
ZA (1) ZA989000B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090226386A1 (en) * 2005-11-28 2009-09-10 Anne Sophie Brillouet Self-tanning composition

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2769219B1 (en) * 1997-10-03 2000-03-10 Oreal OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS
US20020170123A9 (en) * 1997-10-03 2002-11-21 L'oreal S.A. Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres
FR2769217B1 (en) * 1997-10-03 2000-03-17 Oreal OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS
FR2769211B1 (en) * 1997-10-03 1999-12-24 Oreal KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME
FR2769221B1 (en) * 1997-10-03 2000-01-14 Oreal OXIDIZING COMPOSITION AND USES FOR DYEING, PERMANENT DEFORMATION OR DECOLORATION OF KERATINIC FIBERS
FR2769216B1 (en) * 1997-10-03 1999-12-31 Oreal OXIDIZING COMPOSITION AND USES FOR DYEING, PERMANENT DEFORMATION OR DECOLORATION OF KERATINIC FIBERS
FR2788520B1 (en) * 1999-01-19 2003-02-28 Oreal NOVEL CATIONIC MONO-BENZENIC DYES, THEIR USE FOR OXIDATION DYEING OF KERATINIC FIBERS, TINCTORIAL COMPOSITIONS AND DYEING METHODS
FR2789576B1 (en) * 1999-02-16 2002-04-26 Oreal KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME
CN1202804C (en) 1999-12-24 2005-05-25 汉高狮王化妆品有限公司 One-pack type post-foamable oxidation hair-dye composition
US6599330B2 (en) 2000-03-10 2003-07-29 Revlon Consumer Products Corporation Method for coloring hair with removable hair color
JP3414353B2 (en) 2000-03-15 2003-06-09 日本電気株式会社 CDMA demodulator and method
US20020163109A1 (en) * 2001-04-03 2002-11-07 Raytheon Company Conformal firing of ceramic radomes
FR2831804B1 (en) * 2001-11-08 2004-07-30 Oreal PROCESS FOR PERMANENT DEFORMATION OF HAIR USING PARTICULAR AMINO SILICONES
US20050188478A1 (en) * 2004-01-28 2005-09-01 Gregory Plos Composition for dyeing keratin fibers, comprising at least one alcohol oxidase and at least one sugar-based nonionic surfactant, and a process using this composition
FR2865393B1 (en) * 2004-01-28 2006-05-26 Oreal KERATIN FIBER DYEING COMPOSITION CONTAINING ALCOHOL OXIDASE AND SUGAR DERIVED NONIONIC SURFACTANT, PROCESS USING THE SAME
FR2994093B1 (en) * 2012-08-02 2014-10-24 Oreal COLORING COMPOSITION COMPRISING COLOR PRECURSOR, ANIONIC SURFACTANT, ALKYLPOLYGLUCOSIDE SURFACTANT, FATTY BODY AND NONIONIC GUAR GUM

Citations (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3893803A (en) * 1972-10-10 1975-07-08 Procter & Gamble Hair dyeing premixes containing peroxidase enzymes stabilized with heme complexing agents
US3907799A (en) * 1971-08-16 1975-09-23 Icn Pharmaceuticals Xanthine oxidase inhibitors
US4003699A (en) * 1974-11-22 1977-01-18 Henkel & Cie G.M.B.H. Oxidation hair dyes based upon tetraaminopyrimidine developers
US4157388A (en) * 1977-06-23 1979-06-05 The Miranol Chemical Company, Inc. Hair and fabric conditioning compositions containing polymeric ionenes
US4185087A (en) * 1977-12-28 1980-01-22 Union Carbide Corporation Hair conditioning compositions containing dialkylamino hydroxy organosilicon compounds and their derivatives
USRE30199E (en) * 1973-11-29 1980-01-29 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Oxidation hair dyes based upon tetraaminopyrimidine developers
US4390689A (en) * 1979-12-21 1983-06-28 Societe Anonyme Dite: L'oreal Polycationic polymers and their preparation
US4523985A (en) * 1983-12-22 1985-06-18 Sputtered Films, Inc. Wafer processing machine
US4702906A (en) * 1979-12-21 1987-10-27 Societe Anonyme Dite: L'oreal Cosmetic agents based on polycationic polymers, and their use in cosmetic compositions
US4719282A (en) * 1986-04-22 1988-01-12 Miranol Inc. Polycationic block copolymer
US4823985A (en) * 1985-09-10 1989-04-25 L'oreal Forming in situ a composition consisting of two separately packaged constituents and dispensing assembly for carrying out this process
US4961925A (en) * 1987-03-31 1990-10-09 Kyowa Hakko Kogyo Co., Ltd. Hair preparation composition
US4997641A (en) * 1990-04-09 1991-03-05 Colgate-Palmolive Company Hair conditioning shampoo containing C6 -C10 alkyl sulfate or alkyl alkoxy sulfate
US5192332A (en) * 1983-10-14 1993-03-09 L'oreal Cosmetic temporary coloring compositions containing protein derivatives
US5348736A (en) * 1989-06-21 1994-09-20 Colgate-Palmolive Company Stabilized hair-treating compositions
US5415857A (en) * 1989-06-21 1995-05-16 Colgate-Palmolive Company Hair conditioning shampoos containing aminosilicone conditioning agent
US5580357A (en) * 1993-06-16 1996-12-03 L'oreal Composition for the oxidation dyeing of keratinous fibres comprising a para-aminophenol, a meta-aminophenol and an ortho-aminophenol, and dyeing process using such a composition
US5679328A (en) * 1993-02-23 1997-10-21 L'oreal Thickening combination based on guar gum or on nonionic cellulose gum and on a crosslinked polymer and cosmetic or dermatological hair or skin treatment composition containing such a combination
US5685882A (en) * 1994-07-22 1997-11-11 L'oreal Use of guar gum in non-rinsed compositions for the dyeing of keratin fibers
US5849041A (en) * 1996-03-16 1998-12-15 Wella Aktiengesellschaft Oxidation hair dye composition and method of dyeing hair using same
US5965114A (en) * 1996-11-20 1999-10-12 Wella Ag Dye-containing mass, composition containing it and method for dyeing keratin fibers, especially human hair
US5976195A (en) * 1996-09-06 1999-11-02 L'oreal Oxidation dye composition for keratin fibers containing an oxidation dye precursor and amphiphilic polymer
US6027719A (en) * 1997-04-28 2000-02-22 Yamahatsu Sangyo Kaisha, Ltd. Aqueous cosmetic composition containing stably solubilized uric acid and water-soluble polymer and method for stably solubilizing uric acid in aqueous cosmetic composition
US6074631A (en) * 1997-08-14 2000-06-13 Novo Nordisk A/S Reduction of malodour
US6080391A (en) * 1997-08-14 2000-06-27 Novo Nordisk A/S Reduction of malodour
US6129770A (en) * 1995-06-26 2000-10-10 Henkel Kommanditgesellschaft Auf Aktien (Kgaa) Hair dye agents with at least one conditioner
US6241784B1 (en) * 1997-10-03 2001-06-05 L'oreal S.A. Oxidizing composition and uses for dyeing, for permanently setting or bleaching keratin fibres
US6251145B1 (en) * 1997-10-03 2001-06-26 L'oreal S.A. Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6254646B1 (en) * 1997-10-03 2001-07-03 L'oreal S.A. Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6270534B1 (en) * 1997-10-03 2001-08-07 L'oreal S.A. Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6273920B1 (en) * 1997-10-03 2001-08-14 L'oreal S.A. Oxidizing composition and uses for treating keratin fibres

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE626050A (en) 1962-03-30
DE1492175A1 (en) 1965-07-07 1970-02-12 Schwarzkopf Gmbh Hans Method for coloring living hair
IT1013014B (en) * 1970-11-09 1977-03-30 Procter & Gamble SOLUTION FOR DYING HAIR AND COMPOSITION USED IN IT
DE2359399C3 (en) 1973-11-29 1979-01-25 Henkel Kgaa, 4000 Duesseldorf Hair dye
JPS63169571A (en) 1987-01-06 1988-07-13 Nec Corp Tone detector
DE3843892A1 (en) 1988-12-24 1990-06-28 Wella Ag OXIDATION HAIR AGENTS CONTAINING DIAMINOPYRAZOL DERIVATIVES AND NEW DIAMINOPYRAZOLE DERIVATIVES
WO1992005764A1 (en) 1990-09-28 1992-04-16 The Procter & Gamble Company Improved shampoo compositions
DE4133957A1 (en) 1991-10-14 1993-04-15 Wella Ag HAIR DYE CONTAINING AMINOPYRAZOLE DERIVATIVES AND NEW PYRAZOLE DERIVATIVES
US5296588A (en) 1991-12-31 1994-03-22 Lever Brothers Company, Division Of Conopco, Inc. Process of preparing N-substituted aldonamides
FR2692782B1 (en) * 1992-06-25 1995-06-23 Oreal PROCESS FOR DYEING KERATINIC FIBERS WITH INDOLIC OR INDOLINIC DERIVATIVES, HYDROGEN PEROXIDE AND PEROXYDASE.
DE4234885A1 (en) 1992-10-16 1994-04-21 Wella Ag Process for the preparation of 4,5-diaminopyrazole derivatives, their use for dyeing hair and new pyrazole derivatives
DE4234887A1 (en) 1992-10-16 1994-04-21 Wella Ag Oxidation hair dye containing 4,5-diaminopyrazole derivatives as well as new 4,5-diaminopyrazole derivatives and process for their preparation
ES2107788T3 (en) 1992-11-25 1997-12-01 Unilever Nv ALDONAMIDES AND THEIR USE AS SURFACTANTS.
EP0628559B1 (en) 1993-06-10 2002-04-03 Beiersdorf-Lilly GmbH Pyrimidine compounds and their use as pharmaceuticals
DE4440957A1 (en) 1994-11-17 1996-05-23 Henkel Kgaa Oxidation dye
CA2150596A1 (en) * 1994-12-16 1996-06-17 Yoshio Tsujino Oxidation hair dye composition
FR2733749B1 (en) 1995-05-05 1997-06-13 Oreal COMPOSITIONS FOR DYEING KERATINIC FIBERS CONTAINING DIAMINO PYRAZOLES, DYEING PROCESS, NOVEL DIAMINO PYRAZOLES, AND PREPARATION METHOD THEREOF
DE19543988A1 (en) 1995-11-25 1997-05-28 Wella Ag Oxidative hair dye composition
DE19547991A1 (en) * 1995-12-21 1997-06-26 Beiersdorf Ag Use of combinations of uricase and uric acid

Patent Citations (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3907799A (en) * 1971-08-16 1975-09-23 Icn Pharmaceuticals Xanthine oxidase inhibitors
US3893803A (en) * 1972-10-10 1975-07-08 Procter & Gamble Hair dyeing premixes containing peroxidase enzymes stabilized with heme complexing agents
USRE30199E (en) * 1973-11-29 1980-01-29 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Oxidation hair dyes based upon tetraaminopyrimidine developers
US4003699A (en) * 1974-11-22 1977-01-18 Henkel & Cie G.M.B.H. Oxidation hair dyes based upon tetraaminopyrimidine developers
US4157388A (en) * 1977-06-23 1979-06-05 The Miranol Chemical Company, Inc. Hair and fabric conditioning compositions containing polymeric ionenes
US4185087A (en) * 1977-12-28 1980-01-22 Union Carbide Corporation Hair conditioning compositions containing dialkylamino hydroxy organosilicon compounds and their derivatives
US4390689A (en) * 1979-12-21 1983-06-28 Societe Anonyme Dite: L'oreal Polycationic polymers and their preparation
US4702906A (en) * 1979-12-21 1987-10-27 Societe Anonyme Dite: L'oreal Cosmetic agents based on polycationic polymers, and their use in cosmetic compositions
US5192332A (en) * 1983-10-14 1993-03-09 L'oreal Cosmetic temporary coloring compositions containing protein derivatives
US4523985A (en) * 1983-12-22 1985-06-18 Sputtered Films, Inc. Wafer processing machine
US4823985A (en) * 1985-09-10 1989-04-25 L'oreal Forming in situ a composition consisting of two separately packaged constituents and dispensing assembly for carrying out this process
US4719282A (en) * 1986-04-22 1988-01-12 Miranol Inc. Polycationic block copolymer
US4961925A (en) * 1987-03-31 1990-10-09 Kyowa Hakko Kogyo Co., Ltd. Hair preparation composition
US5348736A (en) * 1989-06-21 1994-09-20 Colgate-Palmolive Company Stabilized hair-treating compositions
US5415857A (en) * 1989-06-21 1995-05-16 Colgate-Palmolive Company Hair conditioning shampoos containing aminosilicone conditioning agent
US4997641A (en) * 1990-04-09 1991-03-05 Colgate-Palmolive Company Hair conditioning shampoo containing C6 -C10 alkyl sulfate or alkyl alkoxy sulfate
US5679328A (en) * 1993-02-23 1997-10-21 L'oreal Thickening combination based on guar gum or on nonionic cellulose gum and on a crosslinked polymer and cosmetic or dermatological hair or skin treatment composition containing such a combination
US5580357A (en) * 1993-06-16 1996-12-03 L'oreal Composition for the oxidation dyeing of keratinous fibres comprising a para-aminophenol, a meta-aminophenol and an ortho-aminophenol, and dyeing process using such a composition
US5685882A (en) * 1994-07-22 1997-11-11 L'oreal Use of guar gum in non-rinsed compositions for the dyeing of keratin fibers
US6129770A (en) * 1995-06-26 2000-10-10 Henkel Kommanditgesellschaft Auf Aktien (Kgaa) Hair dye agents with at least one conditioner
US5849041A (en) * 1996-03-16 1998-12-15 Wella Aktiengesellschaft Oxidation hair dye composition and method of dyeing hair using same
US5976195A (en) * 1996-09-06 1999-11-02 L'oreal Oxidation dye composition for keratin fibers containing an oxidation dye precursor and amphiphilic polymer
US5965114A (en) * 1996-11-20 1999-10-12 Wella Ag Dye-containing mass, composition containing it and method for dyeing keratin fibers, especially human hair
US6027719A (en) * 1997-04-28 2000-02-22 Yamahatsu Sangyo Kaisha, Ltd. Aqueous cosmetic composition containing stably solubilized uric acid and water-soluble polymer and method for stably solubilizing uric acid in aqueous cosmetic composition
US6080391A (en) * 1997-08-14 2000-06-27 Novo Nordisk A/S Reduction of malodour
US6074631A (en) * 1997-08-14 2000-06-13 Novo Nordisk A/S Reduction of malodour
US6241784B1 (en) * 1997-10-03 2001-06-05 L'oreal S.A. Oxidizing composition and uses for dyeing, for permanently setting or bleaching keratin fibres
US6251145B1 (en) * 1997-10-03 2001-06-26 L'oreal S.A. Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6254646B1 (en) * 1997-10-03 2001-07-03 L'oreal S.A. Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6270534B1 (en) * 1997-10-03 2001-08-07 L'oreal S.A. Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6273920B1 (en) * 1997-10-03 2001-08-14 L'oreal S.A. Oxidizing composition and uses for treating keratin fibres

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090226386A1 (en) * 2005-11-28 2009-09-10 Anne Sophie Brillouet Self-tanning composition

Also Published As

Publication number Publication date
AU9269398A (en) 1999-04-27
DE69830152T8 (en) 2006-08-24
DE69830152T2 (en) 2006-01-26
HUP0001212A3 (en) 2001-12-28
US6241784B1 (en) 2001-06-05
AR016945A1 (en) 2001-08-01
CN1250196C (en) 2006-04-12
FR2769216A1 (en) 1999-04-09
JP3630373B2 (en) 2005-03-16
US20030000025A9 (en) 2003-01-02
ES2245040T3 (en) 2005-12-16
EP0966247B1 (en) 2005-05-11
CA2271984A1 (en) 1999-04-15
KR20000068945A (en) 2000-11-25
KR100322397B1 (en) 2002-03-18
CN1241134A (en) 2000-01-12
BR9806171A (en) 2001-01-09
WO1999017721A1 (en) 1999-04-15
CZ205899A3 (en) 1999-09-15
EP0966247A1 (en) 1999-12-29
US20020026674A1 (en) 2002-03-07
FR2769216B1 (en) 1999-12-31
ATE295145T1 (en) 2005-05-15
DE69830152D1 (en) 2005-06-16
AU718348B2 (en) 2000-04-13
HUP0001212A2 (en) 2000-09-28
RU2179435C2 (en) 2002-02-20
ZA989000B (en) 1999-04-12
JP2000507981A (en) 2000-06-27

Similar Documents

Publication Publication Date Title
US6254646B1 (en) Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6270534B1 (en) Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US20020004959A1 (en) Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres
US6241784B1 (en) Oxidizing composition and uses for dyeing, for permanently setting or bleaching keratin fibres
US6261325B1 (en) Oxidizing composition for treating keratin fibres
US6273920B1 (en) Oxidizing composition and uses for treating keratin fibres
US6342078B1 (en) Oxidation dyeing composition for keratin fibres and dyeing method using said composition
US6783559B2 (en) Composition for the oxidation dyeing of keratin fibres and dyeing process using this composition
US6312477B1 (en) Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres
US6692537B1 (en) Oxidizing composition and use for dyeing, permanently setting or bleaching keratin fibres
US6312479B1 (en) Oxidation dyeing composition for keratin fibres and dyeing method using said composition
US6682572B2 (en) Oxidation dyeing composition for keratin fibres
US20060080789A2 (en) Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres

Legal Events

Date Code Title Description
STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION