Classifications

• • 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
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/362—Polycarboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/42—Amides
• • 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
  • A61K8/30—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
  • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
  • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
• • 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
  • A61K8/60—Sugars; Derivatives thereof

Definitions

• the present invention relates to a composition for the oxidation dyeing of keratin fibres, in particular of human keratin fibres such as the hair, comprising at least one oxidation base chosen from 4,5- or 3,4-diaminopyrazoles and triaminopyrazoles, in combination with at least one selected carbonyl compound, and also to the dyeing process using this composition with an oxidizing agent.
• Oxidation dye precursors in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols or heterocyclic compounds such as pyrazole derivatives 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 end and its root.
• compositions for the oxidation dyeing of keratin fibres containing pyrazole derivatives such as 4,5-diaminopyrazoles, 3,4-diaminopyrazoles or 3,4,5-triaminopyrazoles as oxidation base have already been proposed, especially in German patent applications DE 3 843 892, DE 4 234 887, DE 4 234 886, DE 4 234 885 or DE 195 43 988,.
• pyrazole derivatives such as 4,5-diaminopyrazoles, 3,4-diaminopyrazoles or 3,4,5-triaminopyrazoles as oxidation base
• German patent applications DE 3 843 892, DE 4 234 887, DE 4 234 886, DE 4 234 885 or DE 195 43 988 are not entirely satisfactory since, during the dyeing processes, side reactions take place that can have adverse effects in terms of the harmlessness and of the dyeing properties obtained, and especially the strength and resistance of the colorations with respect to the various attacking factors to which the
• the invention is aimed at developing novel dye compositions that do not have the drawbacks of the dyes of the prior art, in particular strong dyes that are particularly resistant to the various attacking factors to which the hair may be subjected, and which show good harmlessness.
• one subject of the invention is a composition for the oxidation dyeing of human keratin fibres, and in particular of human keratin fibres such as the hair, comprising, in a medium that is suitable for dyeing:
• At least one oxidation base chosen from 4,5- or 3,4-diaminopyrazoles and triaminopyrazoles,
• R 1 , R 1 ′, R 2 and R 2 ′ denote, independently of each other, a hydrogen atom; a saturated or unsaturated aliphatic hydrocarbon-based chain containing from 1 to 30 carbon atoms, which may be interrupted with one or more hetero atoms or with one or more carbonyl groups, which is unsubstituted or substituted with one or more groups chosen from hydroxyl, C 1 -C 4 alkoxy, amino, carboxyl, C 1 -C 10 alkoxycarbonyl, halogen, nitro, mono- or di(C 1 -C 4 )alkylamino, mono- or dihydroxy(C 1 -C 4 )alkylamino or C 6 -C 20 aryl groups; a C 6 -C 20 aryl group, which is unsubstituted or substituted with one or more groups chosen from hydroxyl, amino, nitro, halogen, carboxyl, (C 1 -C 10 )alkoxycarbonyl,
• x denotes 0 or 1
• R 1 and R 2 can form, together with the C ⁇ O group, a saturated ring optionally fused to one or more benzene nuclei that may be substituted with one or more C 1 -C 10 alkyl, C 1 -C 10 alkoxy, carboxyl or C 1 -C 10 alkoxycarbonyl radicals,
• B denotes a saturated or unsaturated aliphatic hydrocarbon-based chain containing from 1 to 30 carbon atoms, which may be interrupted with one or more hetero atoms or with one or more carbonyl groups, which is unsubstituted or substituted with one or more groups chosen from hydroxyl, C 1 -C 4 alkoxy, amino, carboxyl, C 1 -C 10 alkoxycarbonyl, halogen, nitro, mono- or di(C 1 -C 4 )alkylamino, mono- or dihydroxy(C 1 -C 4 )alkyl-amino or C 6 -C 20 aryl groups; a C 6 -C 20 aryl group, which is unsubstituted or substituted with one or more groups chosen from hydroxyl, amino, nitro, halogen, carboxyl, (C 1 -C 10 )alkoxy-carbonyl, C 1 -C 4 alkyl, mono- or polyhydroxy(C 1 -C 4 .
• R 3 and R 4 which may be identical or different, represent a hydrogen atom, a C 1 -C 10 alkyl, C 1 -C 10 monohydroxyalkyl or C 2 -C 10 polyhydroxyalkyl radical, Na, K or NH 4 .
• the oxidation dye composition of the invention makes it possible to obtain, with good harmlessness, strong, relatively unselective colorations in varied shades, which show excellent resistance properties both with respect to atmospheric agents such as light and bad weather and with respect to perspiration and various treatments to which the hair may be subjected (shampooing or permanent reshaping).
• urea aliphatic aldehydes or ketones, for instance acetone, aromatic aldehydes or ketones, for instance p-dimethylaminobenzaldehyde or 5-nitrosalicylaldehyde
• ⁇ -dicarbonyl compounds for instance ⁇ , ⁇ -dimethylacetylacetone
• ⁇ -pyrones such as 2,6-dimethylpyrone, 2,6-di(ethoxycarbonyl)pyrone and 2-hydroxy-6-methylpyrone
• chromones for instance 2-methylchromone
• aldoses or ketoses such as glyceraldehyde, dihydroxyacetone, D-glucose, D-fructose, D-erythrose, D-ribose, D-xylose, D-threose, D-erythrulose and D-sorbose.
• the polyimides are polycondensates derived from tetraacids (or from dianhydrides) and from diamines. Preferably, among these, aromatic polyimides are used.
• aromatic polyimides are used.
• An example that may be mentioned is the polyimides obtained from pyromellitic dianhydride or benzophenone dianhydride. Mention may be made most particularly of the products derived from pyromellitic dianhydride and from 4,4′-diaminodiphenyl ether (Kapton H from the company DuPont).
• carbonyl compounds of the invention that are preferably used are urea, aliphatic or aromatic ketones, maleic acid, ketoses or aldoses.
• the carbonyl compound(s) in accordance with the invention preferably represent(s) from 0.00001% to 10% by weight and even more preferably from 0.001% to 5% by weight approximately relative to the total weight of the dye composition, and even more preferentially from 0.001% to 3% by weight approximately relative to this weight.
• 4,5- or 3,4-diaminopyrazoles that are useful in the dye compositions of the invention, mention may be made particularly of the diamino-pyrazoles chosen from the 4,5- or 3,4-diaminopyrazoles of formula (IV) or (V) below, and/or the addition salts thereof with an acid:
• R 5 , R 6 , R 7 , R 8 and R 9 which may be identical or different, represent a hydrogen atom; a C 1 -C 6 alkyl radical which is unsubstituted or substituted with at least one substituent chosen from OR, NHR, NRR′, SR, SOR, SO 2 R, COR, COOH, CONH 2 , CONHR, CONRR′, PO(OH) 2 , SH and SO 3 X, a non-cationic heterocycle, Cl, Br or I, X denoting a hydrogen atom, Na, K or NH 4 , and R and R′, which may be identical or different, representing a C 1 -C 4 alkyl or alkenyl; a C 2 -C 4 hydroxyalkyl radical; a C 2 -C 4 aminoalkyl radical; a phenyl radical; a phenyl radical substituted with a halogen atom or a C 1 -C 4 alkyl, C 1
• n are integers, which may be identical or different, between 0 and 3 inclusive
• X represents an oxygen atom or an NH group
• Y represents a hydrogen atom or a C 1 -C 4 alkyl radical
• Z represents a methyl radical when n is equal to 0, or Z represents a C 1 -C 4 alkyl radical, a group OR or NR′′R′′′ when n is greater than or equal to 1, R′′ and R′′′, which may be identical or different, denoting a hydrogen atom or a C 1 -C 4 alkyl radical; or
• R 9 forms with the nitrogen atom of the group NR 7 R 8 in position 5 an at least 4-membered heterocycle
• R 10 represents a C 1 -C 6 alkyl radical; a C 1 -C 4 hydroxy-alkyl 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 )alkylamino-(C 1 -C 4 )alkyl radical; a hydroxy(C 1 -C 4 )alkylamino(C 1 -C 4 )-alkyl radical; a (C 1 -C 4 )alkoxymethyl radical; a phenyl radical; a phenyl radical substituted with a halogen atom or with a C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, amino or C 1 -C 4 alkylamino radical; a benzyl radical; a benzyl radical substituted with
• At least one of the radicals R 5 , R 6 , R 7 and R 8 represents a hydrogen atom.
• R 11 and R 12 which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl or C 2 -C 4 hydroxyalkyl radical.
• 4,5- or 3,4-diaminopyrazoles of formula (IV) above that may be mentioned more particularly are 4,5-diamino-1-(4′-methoxybenzyl)-pyrazole, 4,5-diamino-1-(4′-methylbenzyl)pyrazole, 4,5-diamino-1-(4′-chlorobenzyl)pyrazole, 4,5-diamino-1-(3′-methoxybenzyl)pyrazole, 4-amino-1-(4′-methoxy-benzyl)-5-methylaminopyrazole, 4-amino-5-( ⁇ -hydroxy-ethyl)amino-1-(4′-methoxybenzyl)pyrazole, 4-amino-5-( ⁇ -hydroxyethyl)amino-1-methylpyrazole, 4-amino-(3)-5-methylaminopyrazole, 3-(5),4-diaminopyrazole, 4,5
• diaminopyrazoles that are useful in the present invention may be obtained via synthetic processes that are well known to those skilled in the art.
• the 4,5-diaminopyrazoles of formula (V) may be prepared according to the synthetic process as described, for example, in French patent application FR-A-2 733 749.
• triaminopyrazoles of formula (VI) above that may be mentioned more particularly are 3,4,5-triaminopyrazole, 1-methyl-3,4,5-triamino-pyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3,5-diamino-4-( ⁇ -hydroxyethyl)amino-1-methyl-pyrazole, and the additions salts thereof with an acid.
• the 4,5- or 3,4-diaminopyrazole(s) and/or the triaminopyrazole(s) in accordance with the invention and/or the corresponding addition salt(s) with an acid preferably represent from 0.0005% to 12% by weight approximately relative to the total weight of the dye composition and more preferably from 0.005% to 6% by weight approximately relative to this weight.
• the weight ratio of the carbonyl compound(s) to the 4,5- or 3,4-diaminopyrazole(s) and/or the triaminopyrazole(s) and/or the addition salt(s) with an acid is between 0.001 and 100 and even more preferably between 0.01 and 10.
• the dye compositions in accordance with the invention preferably contain at least one coupler.
• the couplers that may be used are those conventionally used for oxidation dyeing, and especially meta-phenylene-diamines, meta-aminophenols, meta-diphenols, naphthol derivatives and heterocyclic couplers.
• meta-phenylenediamines, meta-aminophenols and meta-diphenols which may be used as additional couplers in the dye composition in accordance with the invention are preferably chosen from the compounds corresponding to formula (1) below, and the addition salts thereof with an acid:
• a and B which may be identical or different, represent a hydroxyl, amino or —NHR 22 radical in which R 22 represents a C 1 -C 4 alkyl, C 1 -C 4 monohydroxy-alkyl or C 2 -C 4 polyhydroxyalkyl radical,
• R 19 , R 20 and R 21 which may be identical or different, represent a hydrogen atom or a halogen atom such as a bromine, chlorine, iodine or fluorine atom, or a C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 monohydroxyalkyl, C 2 -C 4 polyhydroxyalkyl, C 1 -C 4 monohydroxyalkoxy or C 2 -C 4 polyhydroxyalkoxy radical.
• a halogen atom such as a bromine, chlorine, iodine or fluorine atom
• heterocyclic coupler(s) which may be used as additional couplers in the dye composition in accordance with the invention can be chosen in particular from indole derivatives, indoline derivatives, pyridine derivatives, pyrimidine derivatives and pyrazolones, and the addition salts thereof with an acid.
• heterocyclic couplers mention may be made in particular, for example, of sesamol, 1-N-( ⁇ -hydroxyethyl)amino-3′,4-methylenedioxybenzene, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methyl-indole, 6-hydroxyindoline, 6-hydroxybenzomorpholine, 2,6-dihydroxy-4-methylpyridine, 3,5-diamino-2,6-di-methoxypyridine, 2-amino-3-hydroxypyridine, 1-H-3-methylpyrazol-5-one and 1-phenyl-3-methylpyrazol-5-one, and the addition salts thereof with an acid.
• naphthol derivatives that may be mentioned are ⁇ -naphthol and 2-methyl-1-naphthol.
• the additional coupler(s) preferably represent(s) from 0.0001% to 10% by weight approximately relative to the total weight of the dye composition, and even more preferably from 0.005% to 5% by weight approximately relative to this weight.
• the dye compositions in accordance with the invention may also contain other oxidation bases conventionally used for oxidation dyeing, other than a diaminopyrazole and a triaminopyrazole and/or direct dyes, especially to modify the shades or to enrich them with glints.
• the additional oxidation bases that may be used in the context of the present invention are chosen from those conventionally known in oxidation dyeing, and among which mention may be made especially of ortho- and para-phenylenediamines, double bases, ortho- and para-aminophenols, and heterocyclic bases other than the pyrazoles of the invention, and also the addition salts thereof with an acid, and especially:
• R a represents a hydrogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxy-alkyl 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 b represents a hydrogen atom, a C 1 -C 4 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical, a C 2 -C 4 polyhydroxy-alkyl 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 c represents a hydrogen atom, a halogen atom such as a chlorine atom, a C 1 -C 4 alkyl radical, a sulfo radical, a carboxyl 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 atom, a C 1 -C 4 alkyl radical, a sulfo radical, a carboxyl 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 -
• R d represents a hydrogen or halogen atom or a C 1 -C 4 alkyl radical
• R a and R b may also form with the nitrogen atom that bears them a 5- or 6-membered nitrogenous heterocycle optionally substituted with one or more alkyl, hydroxyl or ureido groups.
• para-phenylenediamines of formula (2) above mention may be made more particularly of para-phenylenediamine, para-tolylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylene-diamine, 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)-3-methylaniline, 4-amino-3-ch
• para-phenylenediamine para-tolylenediamine, 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 and 2-chloro-para-phenylenediamine, and the addition salts thereof with an acid are most particularly preferred.
• the double bases are compounds comprising at least two aromatic nuclei 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 6 alkoxy radicals;
• R e and R f 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 g , R h , R i , R j , R k and R l which may be identical or different, represent a hydrogen atom, a linker arm Y or a C 1 -C 4 alkyl radical;
• N,N′-bis( ⁇ -hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diamino-propanol and 1,8-bis(2,5-diaminophenoxy)-3,6-dioxa-octane, or one of the addition salts thereof with an acid, are particularly preferred.
• R m represents a hydrogen or halogen atom such as fluorine 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 n represents a hydrogen or halogen atom such as fluorine 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.
• halogen atom such as fluorine 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 (4) mention may be made more particularly of para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluoro-phenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol and 4-amino-2-( ⁇ -hydroxyethylaminomethyl)phenol, and the addition salts thereof with an acid.
• the ortho-aminophenols that may be used as oxidation bases in the context of the present invention are chosen especially from 2-aminophenol, 2-amino-1-hydroxy-5-methylbenzene, 2-amino-1-hydroxy-6-methyl-benzene and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid.
• (V) 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 and pyrazole 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 patents DE 2 359 399; JP 88-169 571; JP 91-10659 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-tri-aminopyrimidine, 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-dimethyl-pyrazolo[1,5-a]pyrimidine-3,7-diamine, pyrazolo[1,5-a]-pyrimidine-3,5-diamine, 2,7-d
• the additional oxidation bases may preferably represent from 0.0005% to 12% by weight approximately relative to the total weight of the dye composition.
• 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 hydro-chlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
• the medium that is suitable for the dyeing (or the support) generally consists of water or of a mixture of water and at least one organic solvent in order to dissolve the compounds that would not be sufficiently soluble in water.
• organic solvent mention may be made, for example, of C 1 -C 4 lower 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.
• the pH of the dye composition in accordance with the invention is generally between 3 and 12 approximately and preferably between 5 and 11 approximately. It may be adjusted to the desired value with the aid of acidifying or basifying agents commonly used in the dyeing of keratin fibres.
• inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as tartaric acid, citric acid or lactic acid, and sulphonic acids.
• basifying agents are aqueous ammonia, alkaline carbonates, alkanolamines such as monoethanolamine, diethanolamine and triethanolamine and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (5) below:
• R is a propylene residue optionally substituted with a hydroxyl group or a C 1 -C 4 alkyl radical
• R 17 , R 18 , R 19 and R 20 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 dye composition in accordance with the invention can also contain various adjuvants used conventionally 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, antioxidants, penetration agents, sequestering agents, fragrances, buffers, dispersing agents, conditioners, such as, for example, volatile or non-volatile silicones, which are modified or unmodified, film-forming agents, ceramides, preserving agents and opacifiers.
• adjuvants used conventionally 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, antioxidant
• the dye composition in accordance with the invention can 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.
• a subject of the invention is also a process for dyeing keratin fibres, and in particular human keratin fibres such as the hair, using the dye composition as defined above.
• the dye composition as defined above is applied to the fibres, the colour being developed at acidic, neutral or alkaline pH using an oxidizing agent, this oxidizing agent possibly being added just at the time of use to the dye composition or by means of an oxidizing composition applied simultaneously or sequentially.
• the dye composition described above is mixed, at the time of use, with an oxidizing composition containing, in a medium which is suitable for dyeing, at least one oxidizing agent present in an amount which is sufficient to develop a coloration.
• the mixture obtained is then applied to the keratin fibres and is left to stand on them for about 3 to 60 minutes, preferably about 5 to 40 minutes, after which the fibres are rinsed, washed with shampoo, rinsed again and dried.
• the oxidizing agent present in the oxidizing composition as defined above may be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratin fibres, and among which mention may be made of hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates, percarbonates and persulphates, and peracids. Hydrogen peroxide is particularly preferred.
• the pH of the oxidizing composition containing the oxidizing agent as defined above is such that, after mixing it with the dye composition, the pH of the resulting composition applied to the keratin fibres preferably ranges between about 3 and 12 and even more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or basifying agents usually used for the dyeing of keratin fibres and as defined above.
• the oxidizing composition as defined above can also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
• the dye composition that is applied to the keratin fibres can 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 in particular human hair.
• a composition containing at least the carbonyl compound is applied to these fibres in a first stage, and a composition containing at least one diaminopyrazole is applied in a second stage, the application of the composition containing the carbonyl compound(s) possibly being followed by a rinsing step, the colour being developed using an oxidizing agent.
• Another subject of the invention is a multi-compartment device or dyeing “kit” or any other multi-compartment packaging system, a first compartment of which contains the dye composition as defined above and a second compartment of which contains the oxidizing composition as defined above.
• These devices 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.
• the device comprises at least three compartments, a first compartment that contains the carbonyl compound that is useful for the invention, a second compartment that contains a diaminopyrazole, and a third compartment that contains an oxidizing composition.
• AM denotes Active Material EXAMPLES 1 2 3 4 5 6 7 8 9 10 4,5-Diamino-1- ⁇ - 0.645 0.645 0.645 0.645 0.645 0.645 0.645 0.645 0.645 0.645 0.645 0.645 hydroxyethyl- pyrazole dihydrochloride (oxidation base) 3-Amino-6-methyl- 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 0.369 phenol (coupler) Urea (carbonyl 0.1 — — — — — — — — — — compound according to the invention) p-Dimethylamino-
• each dye composition above was mixed with an equal amount by weight of an oxidizing composition consisting of a 20-volumes aqueous hydrogen peroxide solution (6% by weight).
• each dye composition above was mixed with an equal amount by weight of an oxidizing composition consisting of a 20-volumes aqueous hydrogen peroxide solution (6% by weight).

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• 2000
  • 2000-12-22 FR FR0016952A patent/FR2818538B1/fr not_active Expired - Fee Related
• 2001
  • 2001-11-26 WO PCT/FR2001/003729 patent/WO2002051373A1/fr active IP Right Grant
  • 2001-11-26 ES ES01272054T patent/ES2266103T3/es not_active Expired - Lifetime
  • 2001-11-26 DE DE60120477T patent/DE60120477T2/de not_active Expired - Lifetime
  • 2001-11-26 JP JP2002552520A patent/JP2004519446A/ja not_active Withdrawn
  • 2001-11-26 US US10/451,553 patent/US20040088800A1/en not_active Abandoned
  • 2001-11-26 AT AT01272054T patent/ATE328647T1/de not_active IP Right Cessation
  • 2001-11-26 EP EP01272054A patent/EP1345580B9/fr not_active Revoked
• 2007
  • 2007-10-23 US US11/975,995 patent/US7951209B2/en not_active Expired - Fee Related

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