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WO2008037778A2 - Composition servant à teindre des fibres de kératine comprenant un dérivé de diamino-n,n-dihydropyrazolone et un stabilisant - Google Patents

Composition servant à teindre des fibres de kératine comprenant un dérivé de diamino-n,n-dihydropyrazolone et un stabilisant Download PDF

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Publication number
WO2008037778A2
WO2008037778A2 PCT/EP2007/060280 EP2007060280W WO2008037778A2 WO 2008037778 A2 WO2008037778 A2 WO 2008037778A2 EP 2007060280 W EP2007060280 W EP 2007060280W WO 2008037778 A2 WO2008037778 A2 WO 2008037778A2
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amino
radical
optionally substituted
composition according
radicals
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WO2008037778A3 (fr
Inventor
Alain Baudry
François Cottard
Florence Laurent
Aziz Fadli
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LOreal SA
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LOreal SA
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Priority claimed from FR0654020A external-priority patent/FR2906460B1/fr
Priority claimed from FR0654023A external-priority patent/FR2906462B1/fr
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Publication of WO2008037778A3 publication Critical patent/WO2008037778A3/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/678—Tocopherol, i.e. vitamin E
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the invention relates to a composition for dyeing keratin fibres, and in particular human keratin fibres such as the hair, comprising at least one diamino-N,N- dihydropyrazolone derivative or an addition salt thereof, as oxidation base, and at least one particular stabilizer.
  • Oxidation dye precursors in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds such as diaminopyrazole derivatives, pyrazolo [ 1, 5-a] - pyrimidine derivatives, pyrimidine derivatives, pyridine derivatives, indole derivatives and indoline derivatives, which are generally known as oxidation bases.
  • Oxidation dye precursors, or oxidation bases are colourless or weakly coloured compounds that, when combined with oxidizing products, can give rise to coloured compounds and dyes via a process of oxidative condensation. Permanent colorations are thus obtained.
  • couplers or coloration modifiers the latter being chosen especially from meta-phenylenediamines, meta- aminophenols, meta-hydroxyphenols and certain hetero ⁇ cyclic compounds.
  • the "permanent" coloration obtained by means of these oxidation dyes should moreover satisfy a certain number of requirements. Thus, it should have no toxicological drawbacks, it should be able to produce shades in the desired intensity, and it should show good resistance to external agents such as light, bad weather, washing, permanent waving, perspiration and rubbing.
  • the dyes should also be able to cover grey hair, and, finally, they should be as unselective as possible, i.e. they should produce the smallest possible coloration differences along the same keratin fibre, which may indeed be differently sensitized (i.e. damaged) between its end and its root. They should also show good chemical stability in formulations. They should have a good toxicological profile.
  • oxidation bases such as para- phenylenediamine and para-aminophenol derivatives makes it possible to obtain a relatively broad range of colours at basic pH without, however, producing shades of good chromaticity, while at the same time giving the hair excellent properties in terms of colour intensity, colour uniformity and fastness to external agents.
  • oxidation dyes are sensitive to oxidizing agents.
  • a decrease and a deterioration of the dyeing power of the dyes are observed, which may lead to a modification of the expected shade. Browning of the dye solutions, which lose their aesthetic clear original appearance, may also be observed.
  • This modification of the dyeing power and this browning of the dye solutions are usually due to oxidation on contact with air, which may take place either during the dissolution of the dyes with stirring, or during the storage of the dye composition in containers that are hermetically sealed but that contain a certain volume of air.
  • the degradation of the dye composition may be very substantial if the bottle is restoppered after a partial use of the amount of dye composition and if the remaining part is not used until several days after the first opening.
  • oxidation bases in particular diamino-N, N-dihydropyrazolone derivatives and addition salts thereof as described in document FR 2 866 338, optionally combined with couplers, are not very stable when they are formulated in liquid medium, despite the presence of reducing agents or antioxidants.
  • the aim of the present invention is to provide novel compositions for colouring keratin fibres, which are stable while at the same time having good dyeing properties .
  • composition for dyeing keratin fibres comprising, in a suitable medium: • at least one oxidation base chosen from diamino-N,N- dihydropyrazolone derivatives of formula (I), and the addition salts thereof:
  • Ri, R 2 , R 3 and R 4 which may be identical or different, represent:
  • R 3 and R 4 may also represent a hydrogen atom
  • R 5 , R 6 and R 7 which may be identical or different, represent : - a hydrogen atom
  • Ci-C 4 alkyl radical optionally substituted with one or more radicals chosen from a hydroxyl, Ci-C 2 alkoxy, carboxamido CONR 8 R 9 , sulfonyl SO 2 R 8 or aryl radical optionally substituted with a (Ci-C 4 ) alkyl, hydroxyl, C x -C 2 alkoxy, amino or (di) (Ci-C 2 ) alkylamino radical; aryl optionally substituted with a (Ci-C 4 ) alkyl, hydroxyl, C x -C 2 alkoxy, amino or (di) (Ci-C 2 ) alkylamino radical;
  • R 6 and R 7 which may be identical or different, may also represent a carboxamido radical CONR 8 R 9 ; a sulfonyl radical SO 2 R 8 ;
  • R 8 and R 9 which may be identical or different, represent a hydrogen atom; a linear or branched Ci-C 4 alkyl radical optionally substituted with one or more hydroxyl or C x -C 2 alkoxy radicals;
  • Ri and R 2 on the one hand, and R 3 and R 4 , on the other hand, may form, with the nitrogen atom(s) to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle optionally substituted with one or more radicals chosen from the group consisting of halogen atoms, amino, (di) (Ci-C 4 ) alkylamino, hydroxyl, carboxyl, carboxamido or (Ci-C 2 ) alkoxy radicals, or Ci-C 4 alkyl radicals optionally substituted with one or more hydroxyl, amino, (di) alkylamino, alkoxy, carboxyl or sulfonyl radicals;
  • R 3 and R 4 may also form, together with the nitrogen atom to which they are attached, a 5- or 7-membered heterocycle, the carbon atoms of which may be replaced with an optionally substituted oxygen or nitrogen atom;
  • At least one stabilizer chosen from vitamin E, vitamin E esters and a dithionite • at least one stabilizer chosen from vitamin E, vitamin E esters and a dithionite.
  • the diamino-N, N-dihydropyrazolone derivatives and the addition salts thereof show better stability in the presence of these stabilizers than in the presence of other reducing agents or antioxidants such as ammonium thiolactate or erythorbic acid, while at the same time maintaining good dyeing properties.
  • the present invention makes it possible to obtain a strong, chromatic, aesthetic, sparingly selective coloration in varied shades, which shows good resistance to the various attacking factors to which the hair may be subjected, such as shampooing, light, sweat and permanent reshaping.
  • Another subject of the invention is a process for dyeing keratin fibres using the composition of the present invention, and also the use of this composition for dyeing keratin fibres.
  • a subject of the invention is a dyeing kit comprising, on the one hand, a dye composition containing an oxidation base of formula (I), as oxidation base, and a stabilizer chosen from vitamin E, vitamin E esters and a dithionite, and, on the other hand, a composition containing an oxidizing agent.
  • alkyl radical means linear or branched alkyl radicals which are Ci-Ci 0 unless otherwise indicated, preferentially Ci-C 6 and even more preferentially C x -C 4 , such as the methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, pentyl or hexyl radical.
  • R 2 which may be identical or different, are chosen from:
  • Ci-C 6 alkyl radical optionally substituted with a hydroxyl, (Ci-C 2 ) alkoxy, amino or (di) (Ci-C 2 ) alkylamino radical;
  • radicals Ri and R 2 which may be identical or different, are chosen from methyl, ethyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl and phenyl radicals.
  • radicals Ri and R 2 form, together with the nitrogen atoms to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered ring.
  • the radicals Ri and R 2 form, together with the nitrogen atoms to which they are attached, a pyrazolidine or pyridazolidine ring, optionally substituted with one or more C x -C 4 alkyl, hydroxyl, (Ci-C 2 ) alkoxy, carboxyl, carboxamido, amino or (di) (Ci-C 2 ) alkylamino radicals.
  • radicals Ri and R 2 form, together with the nitrogen atoms to which they are attached, a pyrazolidine or pyridazolidine ring.
  • radicals R 3 and R 4 which may be identical or different, they are more particularly chosen from a hydrogen atom; a linear or branched Ci-C 6 alkyl radical optionally substituted with one or more hydroxyl, (Ci-C 2 ) alkoxy, amino or
  • the radicals R 3 and R 4 which may be identical or different, are chosen from a hydrogen atom and a methyl, ethyl, isopropyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl or 2-carboxyethyl radical.
  • the radicals R 3 and R 4 represent a hydrogen atom.
  • the radicals R 3 and R 4 form, together with the nitrogen atom to which they are attached, a 5- or 7-membered ring chosen from pyrrolidine, piperidine, homopiperidine, piperazine and homopiperazine heterocycles; the said rings possibly being substituted with one or more hydroxyl, amino, (di) (Ci-C 2 ) alkylamino, carboxyl, carboxamido or
  • Ci-C 4 alkyl radicals optionally substituted with one or more hydroxyl, amino or C x -C 2 (di) alkylamino radicals.
  • radicals R 3 and R 4 form, together with the nitrogen atom to which they are attached, a 5- or 7-membered ring chosen from pyrrolidine, 2,5-di- methylpyrrolidine, pyrrolidine-2-carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, 4-hydroxypyr- rolidine-2-carboxylic acid, 2, 4-dicarboxypyrrolidine, 3-hydroxy-2-hydroxymethylpyrrolidine, 2-carboxamidopyr- rolidine, 3-hydroxy-2-carboxamidopyrrolidine,
  • 2- (diethylcarboxamido) pyrrolidine 2-hydroxymethyl- pyrrolidine, 3, 4-dihydroxy-2-hydroxymethylpyrrolidine, 3-hydroxypyrrolidine, 3, 4-dihydroxypyrrolidine, 3-amino- pyrrolidine, 3-methylaminopyrrolidine, 3-dimethylamino- pyrrolidine, 4-amino-3-hydroxypyrrolidine, 3-hydroxy- 4- (2-hydroxyethyl) aminopyrrolidine, piperidine, 2, 6-dimethylpiperidine, 2-carboxypiperidine, 2-carbox- amidopiperidine, 2-hydroxymethylpiperidine, 3-hydroxy- 2-hydroxymethylpiperidine, 3-hydroxypiperidine,
  • the radicals R 3 and R 4 form, together with the nitrogen atom to which they are attached, a 5- or 7-membered ring chosen from pyrrolidine, 3-hydroxy ⁇ pyrrolidine, 3-aminopyrrolidine, 3-dimethylamino- pyrrolidine, pyrrolidine-2-carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, piperidine, hydroxypiperidine, homopiperidine, diazepane, N-methylhomopiperazine and N- ⁇ -hydroxyethyl- homopiperazine .
  • a 5- or 7-membered ring chosen from pyrrolidine, 3-hydroxy ⁇ pyrrolidine, 3-aminopyrrolidine, 3-dimethylamino- pyrrolidine, pyrrolidine-2-carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, piperidine, hydroxypiperidine, homopiperidine, diazepane, N-methylhomopiperazine and N- ⁇ -hydroxyethy
  • the radicals R 3 and R 4 form, together with the nitrogen atom to which they are attached, a 5-membered ring such as pyrrolidine, 3-hydroxy- pyrrolidine, 3-aminopyrrolidine or 3-dimethylamino- pyrrolidine .
  • the compounds of formula (I) may be optionally salified with strong mineral acids, for instance HCl, HBr, HI,
  • H 2 SO 4 or H 3 PO 4 or organic acids, for instance acetic acid, lactic acid, tartaric acid, citric acid or succinic acid, benzenesulfonic acid, para- toluenesulfonic acid, formic acid or methanesulfonic acid.
  • organic acids for instance acetic acid, lactic acid, tartaric acid, citric acid or succinic acid, benzenesulfonic acid, para- toluenesulfonic acid, formic acid or methanesulfonic acid.
  • solvates for example a hydrate or a solvate of a linear or branched alcohol such as ethanol or isopropanol.
  • diamino-N, N-dihydro- pyrazolone derivatives of formula (I), or the addition salts thereof, which are particularly preferred are the following:
  • the oxidation base(s) chosen from the diamino-N,N- dihydropyrazolone derivatives of formula (I) and the addition salts thereof are each generally present in an amount of between 0.001% and 10% and preferably between 0.005% and 6% by weight approximately relative to the total weight of the dye composition.
  • the dithionite (s) may be chosen from dithionites of alkali metals or alkaline-earth metals, of transition metals, of zinc, of aluminium, of ammonium, and of hydroxylated or non-hydroxylated amines. They may or may not be hydrated.
  • the dithionites are alkali metal dithionites. Even more preferentially, it is sodium dithionite (Na 2 S 2 O 4 ) .
  • the dithionite (s) is (are) each generally present in an amount of between 0.001% and 10%, preferably between 0.01% and 5% and even more preferentially between 0.1% and 1.5% by weight relative to the total weight of the dye composition.
  • the vitamin E esters may be chosen from vitamin E acetate, vitamin E palmitate and vitamin E succinate.
  • the compound (s) chosen from vitamin E and vitamin E esters is (are) each generally present in an amount of between 0.001% and 10%, preferably between 0.01% and 5% and even more preferentially between 0.05% and 1% by weight relative to the total weight of the dye composition .
  • the dye composition of the invention may contain one or more couplers conventionally used for dyeing keratin fibres.
  • couplers conventionally used for dyeing keratin fibres.
  • couplers mention may be made especially of meta-phenylenediamines, meta- aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and the addition salts thereof.
  • Examples that may be mentioned include 2-methyl-5- aminophenol, 5-N- ( ⁇ -hydroxyethyl) amino-2-methylphenol, 6-chloro-2-methyl-5-aminophenol, 3-aminophenol, 1,3-di- hydroxybenzene, 1, 3-dihydroxy-2-methylbenzene, 4-chloro- 1, 3-dihydroxybenzene, 2, 4-diamino-l- ( ⁇ -hydroxyethyloxy) - benzene, 2-amino-4- ( ⁇ -hydroxyethylamino) -1-methoxy- benzene, 1, 3-diaminobenzene, l,3-bis(2,4- diaminophenoxy) propane, 3-ureidoaniline, 3-ureido-l- dimethylaminobenzene, sesamol, 1- ⁇ -hydroxyethylamino- 3, 4-methylenedioxybenzene, ⁇ -naphthol, 2-methyl-l- naphthol, 6-hydroxyindole, 4-hydroxy
  • the coupler (s) present in the composition of the invention is (are) each generally present in an amount of between 0.001% and 10% and preferably between 0.005% and 6% by weight approximately relative to the total weight of the dye composition.
  • the dye composition of the invention may contain oxidation bases other than those that are useful in the present invention and conventionally used for the dyeing of keratin fibres.
  • composition of the present invention may also comprise additional oxidation bases chosen from para- phenylenediamines, bis (phenyl) alkylenediamines, para- aminophenols, bis-para-aminophenols, ortho-amino- phenols, ortho-phenylenediamines and heterocyclic bases other than the derivatives of formula (I) as defined above, and the addition salts thereof.
  • additional oxidation bases chosen from para- phenylenediamines, bis (phenyl) alkylenediamines, para- aminophenols, bis-para-aminophenols, ortho-amino- phenols, ortho-phenylenediamines and heterocyclic bases other than the derivatives of formula (I) as defined above, and the addition salts thereof.
  • para-phenylenediamines that may be mentioned, for example, are para-phenylenediamine, para- tolylenediamine, 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-N,N-bis ( ⁇ -hydroxyethyl) amino- 2-methylaniline, 4-N,N-bis ( ⁇ -hydroxyethyl) amino- 2-methylani
  • para-phenylenediamine para-tolylenediamine, 2-isopropyl- para-phenylenediamine, 2- ⁇ -hydroxyethyl-para-phenylene- diamine, 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- ⁇ -acetylamino- ethyloxy-para-phenylenediamine, and the addition salts thereof with an acid are particularly preferred.
  • the bis (phenyl) alkylenediamines that may be mentioned, for example, are N, N'-bis ( ⁇ -hydroxyethyl) - N, N' -bis (4'-aminophenyl) -1, 3-diaminopropanol, N, N'-bis- ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylene- diamine, N, N' -bis (4-aminophenyl) tetramethylenediamine, N, N' -bis ( ⁇ -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 l,8
  • para-aminophenols that may be mentioned, for example, are para-aminophenol, 4-amino-3-methylphenol,
  • ortho-aminophenols that may be mentioned, for example, are 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 mention may be made, for example, of pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives which may be mentioned are the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino- pyridine, 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.
  • pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo-
  • pyrimidine derivatives which may be mentioned are the compounds described, for example, in patent DE 2 359 399 or patents JP 88-169 571; JP 05 63 124; EP 0 770 375 or patent application WO 96/15765, such as 2,4,5, 6-tetraaminopyrimidine, 4-hydroxy-2, 5, 6-triamino- pyrimidine, 2-hydroxy-4, 5, 6-triaminopyrimidine, 2,4- dihydroxy-5, 6-diaminopyrimidine and 2, 5, 6-triamino ⁇ pyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which mention may be made of 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
  • pyrazole derivatives which may be mentioned are the compounds described in patents DE 3 843 892 and 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-l-methylpyrazole, 4, 5-diamino-l- ( ⁇ -hydroxy- ethyl) pyrazole, 3, 4-diaminopyrazole, 4, 5-diamino-l- (4' - chlorobenzyl) pyrazole, 4, 5-diamino-l, 3-dimethyl- pyrazole, 4, 5-diamino-3-methyl-l-phenylpyrazole, 4,5- diamino-l-methyl-3-phenylpyrazole, 4-amino-l, 3- dimethyl-5-hydrazinopyrazole, l-benzyl-4, 5-diamino- 3-methylpyrazole, 4, 5-diamin
  • the oxidation base(s) present in the composition of the invention is (are) each generally present in an amount of between 0.001% and 10% by weight approximately relative to the total weight of the dye composition, and preferably between 0.005% and 6%.
  • the addition salts of the oxidation bases and of the couplers that may be used in the context of the invention are chosen especially from the addition salts with an acid, such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, (Ci-C 4 ) alkylsulfonates, tosylates, benzenesulfonates, phosphates and acetates, and the addition salts with a base, such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines .
  • an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, (Ci-C 4 ) alkylsulfonates, tosylates, benzenesulfonates, phosphates and acetates
  • a base such as sodium hydroxide, potassium hydroxide, ammoni
  • the dye composition in accordance with the invention may also contain one or more direct dyes, which may be chosen especially from dyes of the nitrobenzene series, azo direct dyes and methine direct dyes. These direct dyes may be of nonionic, anionic or cationic nature.
  • the medium that is suitable for dyeing is a cosmetic medium that generally consists of water or a mixture of water and at least one organic solvent to dissolve the compounds which would not be sufficiently soluble in water.
  • organic solvent mention may be made, for example, of Ci-C 4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the solvents are 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 dye composition in accordance with the invention can also contain various adjuvants conventionally used in compositions for dyeing 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, and in particular anionic, cationic, nonionic or amphoteric associative polymeric thickeners, reducing agents or antioxidants other than those that are useful in the present invention, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents, for instance silicones, which may be volatile or non ⁇ volatile, and modified or unmodified, film-forming agents, ceramides, preserving agents and opacifiers.
  • adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof
  • the above adjuvants are generally present in an amount for each of them of between 0.01% and 20% by weight relative to the weight of the dye composition.
  • the pH of the dye composition in accordance with the invention is generally between about 3 and 12 and preferably between about 5 and 11. It may be adjusted to the desired value using acidifying or basifying agents usually used in the dyeing of keratin fibres, or alternatively using standard buffer systems.
  • acidifying agents that may be mentioned, for example, are inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid and lactic acid, and sulfonic acids.
  • inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid and lactic acid, and sulfonic acids.
  • basifying agents that may be mentioned, for example, are aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamine and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (II) below:
  • W is a propylene residue which is unsubstituted or substituted with a hydroxyl group or a Ci-C 4 alkyl radical
  • R a , R b , R c and R d which may be identical or different, represent a hydrogen atom, a Ci-C 4 alkyl radical or a C x -C 4 hydroxyalkyl radical.
  • the dye composition according to the invention may be in various forms, such as in the form of liquids, creams or gels, or in any other form that is suitable for dyeing keratin fibres, and especially human hair.
  • the process of the present invention is a process in which the composition according to the present invention as described above is applied to the fibres, and the colour is developed using an oxidizing agent.
  • the colour may be developed at acidic, neutral or alkaline pH and the oxidizing agent may be added to the composition of the invention just at the time of use, or it may be used starting with an oxidizing composition containing it, which is applied simultaneously or sequentially to the composition of the invention.
  • the composition according to the present invention is mixed, preferably at the time of use, with a composition containing, in a medium that is suitable for dyeing, at least one oxidizing agent, this oxidizing agent being present in an amount that is sufficient to develop a coloration.
  • the mixture obtained is then applied to the keratin fibres. After an action time of 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, the keratin fibres are rinsed, washed with shampoo, rinsed again and then dried.
  • the oxidizing agents conventionally used for the oxidation dyeing of keratin fibres are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and oxidase enzymes, among which mention may be made of peroxidases, 2-electron oxidoreductases such as uricases, and 4-electron oxygenases, for instance laccases. Hydrogen peroxide is particularly preferred.
  • the oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
  • the pH of the oxidizing composition containing the oxidizing agent is such that, after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibres ranges preferably between 3 and 12 approximately and even more preferably between 5 and 11. It may be adjusted to the desired value by means of acidifying or basifying agents usually used in the dyeing of keratin fibres and as defined above.
  • the ready-to-use composition that is finally applied to the keratin fibres may be in various forms, such as in the form of liquids, creams or gels or any other form that is suitable for dyeing keratin fibres, and especially human hair.
  • Another subject of the invention is a multi-compartment dyeing device or "kit", in which a first compartment contains the dye composition of the present invention defined above with the exception of the oxidizing agent and a second compartment contains an oxidizing composition.
  • This device may be equipped with a 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 the use for the oxidation dyeing of keratin fibres, and in particular of human keratin fibres such as the hair, of a composition as defined above.
  • the mixture obtained is applied to locks of natural grey hair containing 90% white hairs. After a leave-in time of 30 minutes at 25°C ⁇ 3°C, the locks are rinsed, washed with a standard shampoo, rinsed again and then dried.
  • the hair coloration is evaluated visually. A coppery blonde shade is obtained.
  • the mixture obtained is applied to locks of natural grey hair containing 90% white hairs. After a leave-in time of 30 minutes at 25°C ⁇ 3°C, the locks are rinsed, washed with a standard shampoo, rinsed again and then dried .
  • the hair coloration is evaluated visually. A coppery blonde shade is obtained.

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Abstract

L'invention concerne une composition servant à teindre des fibres de kératine, comprenant au moins un dérivé de diamino-N,N-dihydropyrazolone ou un sel d'addition de celui-ci, en tant qu'agent oxydant, et au moins un stabilisant choisi parmi un dithionite, la vitamine E et un ester de la vitamine E. L'invention concerne également le procédé de teinture utilisant une telle composition. La composition selon l'invention est stable et permet d'obtenir une coloration dans différents tons qui est intense, chromatique, esthétique, modérément sélective et présente une bonne résistance aux différents facteurs agressifs auxquels les cheveux peuvent être soumis, tels que les shampooings, la lumière, la transpiration et la mise en forme permanente.
PCT/EP2007/060280 2006-09-29 2007-09-27 Composition servant à teindre des fibres de kératine comprenant un dérivé de diamino-n,n-dihydropyrazolone et un stabilisant Ceased WO2008037778A2 (fr)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
FR0654020A FR2906460B1 (fr) 2006-09-29 2006-09-29 Composition de coloration des fibres keratiniques comprenant un derive de diamino-n,n-dihydro-pyrazolone et un dithionite.
FR0654023A FR2906462B1 (fr) 2006-09-29 2006-09-29 Composition de coloration des fibres keratiniques comprenant un derive de diamino-n,n-dihydro-pyrazolone et la vitame e ou l'un de ses esters.
FR0654020 2006-09-29
FR0654023 2006-09-29
US84900306P 2006-10-04 2006-10-04
US84900506P 2006-10-04 2006-10-04
US60/849,005 2006-10-04
US60/849,003 2006-10-04

Publications (2)

Publication Number Publication Date
WO2008037778A2 true WO2008037778A2 (fr) 2008-04-03
WO2008037778A3 WO2008037778A3 (fr) 2008-05-22

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PCT/EP2007/060280 Ceased WO2008037778A2 (fr) 2006-09-29 2007-09-27 Composition servant à teindre des fibres de kératine comprenant un dérivé de diamino-n,n-dihydropyrazolone et un stabilisant

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2277881A4 (fr) * 2008-04-18 2011-09-07 Shionogi & Co Composé hétérocyclique présentant une activité inhibitrice sur p13k
FR2971708A1 (fr) * 2011-02-18 2012-08-24 Oreal Composition de coloration d'oxydation comprenant de la carnitine ou derive, procede de coloration capillaire et utilisation de carnitine comme stabilisant de ces compositions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU77994A1 (fr) * 1977-08-19 1979-05-23 Oreal Compositions tinctoriales a base de colorants d'oxydation comprenant un acide(2,5-dihydroxyphenyl)alcanoique ou l'un de ses sels a titre d'anti-oxydant et procede de preparation
FR2866338B1 (fr) * 2004-02-18 2006-06-02 Oreal Composition pour la teinture des fibres keratiniques comprenant au moins un derive de diamino-n,n-dihydro-pyrazolone

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2277881A4 (fr) * 2008-04-18 2011-09-07 Shionogi & Co Composé hétérocyclique présentant une activité inhibitrice sur p13k
FR2971708A1 (fr) * 2011-02-18 2012-08-24 Oreal Composition de coloration d'oxydation comprenant de la carnitine ou derive, procede de coloration capillaire et utilisation de carnitine comme stabilisant de ces compositions

Also Published As

Publication number Publication date
WO2008037778A3 (fr) 2008-05-22

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