Composition for the oxidation dyeing of keratinous fibres comprising a diamino pyrazole and a carbonyl compound

Abstract

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.

1 . 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,    at least one carbonyl compound selected from the compounds of formulae (I), (II) and (III) and the polyimides                          in which    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, C 1 -C 4  alkyl, mono- or polyhydroxy(C 1 -C 4 )alkyl, C 1 -C 4  alkoxy, mono- or di(C 1 -C 4 )alkylamino or mono- or dihydroxy(C 1 -C 4 )alkylamino groups,    x denotes 0 or 1, and, when x is equal to 0, 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,                          in which:    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 )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, C 1 -C 4  alkyl, mono- or polyhydroxy(C 1 -C 4 )alkyl, C 1 -C 4  alkoxy, mono- or di(C 1 -C 4 )alkylamino or mono- or dihydroxy(C 1 -C 4 )alkylamino groups,    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 .    
     
     
         2 . Composition according to  claim 1 , characterized in that the compounds of formula (I) are chosen from urea, aliphatic aldehydes or ketones, aromatic aldehydes or ketones, β-dicarbonyl compounds, γ-pyrones, chromones, aldoses and ketoses.  
     
     
         3 . Composition according to  claim 1 , characterized in that the compound of formula (II) is maleic acid.  
     
     
         4 . Composition according to  claim 1 , characterized in that the compound of formula (III) is maleic anhydride.  
     
     
         5 . Composition according to  claim 1 , characterized in that the polyimide is an aromatic polyimide.  
     
     
         6 . Composition according to  claim 5 , characterized in that the polyimide is obtained from pyromellitic dianhydride or benzophenone dianhydride.  
     
     
         7 . Composition according to any one of  claims 1  to  6 , characterized in that the carbonyl compound(s) preferably represent(s) from 0.00001% to 10% by weight approximately relative to the total weight of the dye composition, even more preferably from 0.001% to 5% and even more preferentially from 0.001% to 3% by weight approximately relative to this weight.  
     
     
         8 . Composition according to any one of  claims 1  to  7 , characterized in that the 4,5- or 3,4-diaminopyrazoles are chosen from the 4,5- or 3,4-diaminopyrazoles of formula (IV) or (V) below, and/or the addition salts thereof with an acid:  
       
         
           
           
               
               
           
         
       
       in which: 
 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 -C 4  alkoxy, nitro, trifluoromethyl, amino or C 1 -C 4  alkylamino radical; a benzyl radical; a benzyl radical substituted with a halogen atom or with a C 1 -C 4  alkyl, C 1 -C 4  alkoxy, methylenedioxy or amino radical; a radical  
                     
 in which m and 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, and 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 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 heterocycle chosen from thiophene, furan and pyridine, or a radical —(CH 2 ) p —O—(CH 2 ) q —OR″, in which p and q are integers, which may be identical or different, between 1 and 3 inclusive and R″ is as defined above, it being understood that: 
 at least one of the radicals R 5 , R 6 , R 7  and R 8  represents a hydrogen atom.  
 
 
     
     
         9 . Composition according to any one of  claims 1  to  7 , characterized in that the triaminopyrazoles are chosen from the compounds of formula (VI) below, and the addition salts thereof with an acid:  
       
         
           
           
               
               
           
         
       
       in which: 
 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.  
 
     
     
         10 . Composition according to  claim 8 , characterized in that the 4,5- or 3,4-diaminopyrazoles of formula (IV) are chosen from 4,5-diamino-1-(4′-methoxybenzyl)pyrazole, 4,5-diamino-1-(4′-methyl-benzyl)pyrazole, 4,5-diamino-1-(4′-chlorobenzyl)-pyrazole, 4,5-diamino-1-(3′-methoxybenzyl)pyrazole, 4-amino-1-(4′-methoxybenzyl)-5-methylaminopyrazole, 4-amino-5-(β-hydroxyethyl)amino-1-(4′-methoxybenzyl)-pyrazole, 4-amino-5-(β-hydroxyethyl)amino-1-methyl-pyrazole, 4-amino-(3)-5-methylaminopyrazole, 3-(5),4-diaminopyrazole, 4,5-diamino-1-methylpyrazole, 4,5-diamino-1-ethylpyrazole, 4,5-diamino-1-isopropyl-pyrazole, 4,5-diamino-1-hydroxyethylpyrazole, 4,5-diamino-1-benzylpyrazole, 4-diamino-5-hydroxyethyl-amino-1-hydroxyethylpyrazole, 4-diamino-5-methylamino-1-hydroxyethylpyrazole, 3-amino-4,5,7,8-tetrahydro-pyrazolo[1,5-a]pyrimidine, 7-amino-2,3-dihydro-1H-imidazole[1,2-b]pyrazole, 3-amino-8-methyl-4,5,7,8-tetrahydropyrazolo[1,5-a]pyrimidine, 2-(4,5-diamino-1-pyrazolyl)-1-ethanesulphonic acid, 2-(4,5-diamino-1-pyrazolyl)acetamide, 2-(4,5-diamino-1-pyrazolyl)acetic acid, 2-(2-dimethylaminoethyl)-2H-pyrazole-3,4-diamine and 2-(2-methoxyethyl)-2H-pyrazole-3,4-diamine, and the addition salts thereof with an acid.  
     
     
         11 . Composition according to  claim 10 , characterized in that the 4,5- or 3,4-diaminopyrazoles of formula (IV) are chosen from: 
 4,5-diamino-1-benzylpyrazole,    4,5-diamino-1-(4′-chlorobenzyl)pyrazole,    4,5-diamino-1-methylpyrazole,    4,5-diamino-1-hydroxyethylpyrazole,    2-(2-methoxyethyl)-2H-pyrazole-3,4-diamine, and the addition salts thereof with an acid.    
     
     
         12 . Composition according to  claim 8 , characterized in that the 4,5-diaminopyrazoles of formula (V) are chosen from: 
 1-benzyl-4,5-diamino-3-methylpyrazole,    4,5-diamino-1-(β-hydroxyethyl)-3-(4′-methoxyphenyl)-pyrazole,    4,5-diamino-1-(β-hydroxyethyl)-3-(4′-methylphenyl)-pyrazole,    4,5-diamino-1-(β-hydroxyethyl)-3-(3′-methylphenyl)-pyrazole,    4,5-diamino-3-methyl-1-isopropylpyrazole,    4,5-diamino-3-(4′-methoxyphenyl)-1-isopropylpyrazole,    4,5-diamino-1-ethyl-3-methylpyrazole,    4,5-diamino-1-ethyl-3-(4′-methoxyphenyl)pyrazole,    4,5-diamino-3-hydroxymethyl-1-methylpyrazole,    4,5-diamino-1-ethyl-3-hydroxymethylpyrazole,    4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole,    4,5-diamino-3-hydroxymethyl-1-tert-butylpyrazole,    4,5-diamino-3-hydroxymethyl-1-phenylpyrazole,    4,5-diamino-3-hydroxymethyl-1-(2′-methoxyphenyl)-pyrazole,    4,5-diamino-3-hydroxymethyl-1-(3′-methoxyphenyl)-pyrazole,    4,5-diamino-3-hydroxymethyl-1-(4′-methoxyphenyl)-pyrazole,    1-benzyl-4,5-diamino-3-hydroxymethylpyrazole,    4,5-diamino-3-methyl-1-(2′-methoxyphenyl)pyrazole,    4,5-diamino-3-methyl-1-(3′-methoxyphenyl)pyrazole,    4,5-diamino-3-methyl-1-(4′-methoxyphenyl)pyrazole,    3-aminomethyl-4,5-diamino-1-methylpyrazole,    3-aminomethyl-4,5-diamino-1-ethylpyrazole,    3-aminomethyl-4,5-diamino-1-isopropylpyrazole,    3-aminomethyl-4,5-diamino-1-tert-butylpyrazole,    4,5-diamino-3-dimethylaminomethyl-1-methylpyrazole,    4,5-diamino-3-dimethylaminomethyl-1-ethylpyrazole,    4,5-diamino-3-dimethylaminomethyl-1-isopropyl-pyrazole,    4,5-diamino-3-dimethylaminomethyl-1-tert-butyl-pyrazole,    4,5-diamino-3-ethylaminomethyl-1-methylpyrazole,    4,5-diamino-3-ethylaminomethyl-1-ethylpyrazole,    4,5-diamino-3-ethylaminomethyl-1-isopropylpyrazole,    4,5-diamino-3-ethylaminomethyl-1-tert-butylpyrazole,    4,5-diamino-3-methylaminomethyl-1-methylpyrazole,    4,5-diamino-3-methylaminomethyl-1-isopropylpyrazole,    4,5-diamino-1-ethyl-3-methylaminomethylpyrazole,    1-tert-butyl-4,5-diamino-3-methylaminomethylpyrazole,    4,5-diamino-3-[(β-hydroxyethyl)aminomethyl]-1-methyl-pyrazole,    4,5-diamino-3-[(β-hydroxyethyl)aminomethyl]-1-iso-propylpyrazole,    4,5-diamino-1-ethyl-3-[(β-hydroxyethyl)aminomethyl]-pyrazole,    1-tert-butyl-4,5-diamino-3-[(β-hydroxyethyl)amino-methyl]pyrazole,    4-amino-5-(β-hydroxyethyl)amino-1,3-dimethylpyrazole,    4-amino-5-(β-hydroxyethyl)amino-1-isopropyl-3-methyl-pyrazole,      4 -amino-5-(β-hydroxyethyl)amino-1-ethyl-3-methyl-pyrazole,    4-amino-5-(β-hydroxyethyl)amino-1-tert-butyl-3-methylpyrazole,    4-amino-5-(β-hydroxyethyl)amino-1-phenyl-3-methyl-pyrazole,    4-amino-5-(β-hydroxyethyl)amino-1-(2-methoxyphenyl)-3-methylpyrazole,    4-amino-5-(β-hydroxyethyl)amino-1-(3-methoxyphenyl)-3-methylpyrazole,    4-amino-5-(β-hydroxyethyl)amino-1-(4-methoxyphenyl)-3-methylpyrazole,    4-amino-5-(β-hydroxyethyl)amino-1-benzyl-3-methyl-pyrazole,    4-amino-1-ethyl-3-methyl-5-methylaminopyrazole,    4-amino-1-tert-butyl-3-methyl-5-methylaminopyrazole,    4,5-diamino-1,3-dimethylpyrazole,    4,5-diamino-3-tert-butyl-1-methylpyrazole,    4,5-diamino-1-tert-butyl-3-methylpyrazole,    4,5-diamino-1-methyl-3-phenylpyrazole,    4,5-diamino-1-(β-hydroxyethyl)-3-methylpyrazole,    4,5-diamino-1-(β-hydroxyethyl)-3-phenylpyrazole,    4,5-diamino-1-methyl-3-(2′-chlorophenyl)pyrazole,    4,5-diamino-1-methyl-3-(4′-chlorophenyl)pyrazole,    4,5-diamino-1-methyl-3-(3′-trifluoromethylphenyl)-pyrazole,    4,5-diamino-1,3-diphenylpyrazole,    4,5-diamino-3-methyl-1-phenylpyrazole,    4-amino-1,3-dimethyl-5-phenylaminopyrazole,    4-amino-1-ethyl-3-methyl-5-phenylaminopyrazole,    4-amino-1,3-dimethyl-5-methylaminopyrazole,    4-amino-3-methyl-1-isopropyl-5-methylaminopyrazole,    4-amino-3-isobutoxymethyl-1-methyl-5-methylamino-pyrazole,    4-amino-3-methoxyethoxymethyl-1-methyl-5-methylamino-pyrazole,    4-amino-3-hydroxymethyl-1-methyl-5-methylamino-pyrazole,    4-amino-1,3-diphenyl-5-phenylaminopyrazole,    4-amino-3-methyl-5-methylamino-1-phenylpyrazole,    4-amino-1,3-dimethyl-5-hydrazinopyrazole,    5-amino-3-methyl-4-methylamino-1-phenylpyrazole,    5-amino-1-methyl-4-(N,N-methylphenyl)amino-3-(4′-chlorophenyl)pyrazole,    5-amino-3-ethyl-1-methyl-4-(N,N-methylphenyl)amino-pyrazole,    5-amino-1-methyl-4-(N,N-methylphenyl)amino-3-phenyl-pyrazole,    5-amino-3-ethyl-4-(N,N-methylphenyl)aminopyrazole,    5-amino-4-(N,N-methylphenyl)amino-3-phenylpyrazole,    5-amino-4-(N,N-methylphenyl)amino-3-(4′-methylphenyl)-pyrazole,    5-amino-3-(4′-chlorophenyl)-4-(N,N-methylphenyl)-aminopyrazole,    5-amino-3-(4′-methoxyphenyl)-4-(N,N-methylphenyl)-aminopyrazole,    4-amino-5-methylamino-3-phenylpyrazole,    4-amino-5-ethylamino-3-phenylpyrazole,    4-amino-5-ethylamino-3-(4′-methylphenyl)pyrazole,    4-amino-3-phenyl-5-propylaminopyrazole,    4-amino-5-butylamino-3-phenylpyrazole,    4-amino-3-phenyl-5-phenylaminopyrazole,    4-amino-5-benzylamino-3-phenylpyrazole,    4-amino-5-(4′-chlorophenyl)amino-3-phenylpyrazole,    4-amino-3-(4′-chlorophenyl)-5-phenylaminopyrazole,    4-amino-3-(4′-methoxyphenyl)-5-phenylaminopyrazole,    1-(4′-chlorobenzyl)-4,5-diamino-3-methylpyrazole,    4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole,      4 -amino-1-ethyl-3-methyl-5-methylaminopyrazole,    4-amino-5-(2′-aminoethyl)amino-1,3-dimethylpyrazole, and the addition salts thereof with an acid.    
     
     
         13 . Composition according to  claim 12 , characterized in that the 4,5-diaminopyrazoles of formula (V) are chosen from: 
 4,5-diamino-1,3-dimethylpyrazole,    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-methylpyrazole,    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-methylpyrazole,    4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole,    4,5-diamino-3-methyl-1-isopropylpyrazole,    4-amino-5-(2′-aminoethyl)amino-1,3-dimethylpyrazole, and the addition salts thereof with an acid.    
     
     
         14 . Composition according to  claim 9 , characterized in that the triaminopyrazoles of formula (VI) are chosen from 3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methyl-aminopyrazole and 3,5-diamino-4-(β-hydroxyethyl)amino-1-methylpyrazole, and the addition salts thereof with an acid.  
     
     
         15 . Composition according to any one of the preceding  claims 1  to  14 , characterized in that the 4,5- or 3,4-diaminopyrazole(s) and/or the triaminopyrazole(s) and/or the corresponding addition salt(s) with an acid represent from 0.0005% to 12% by weight relative to the total weight of the dye composition.  
     
     
         16 . Composition according to  claim 15 , characterized in that the 4,5- or 3,4-diamino-pyrazole(s) and/or the triaminopyrazole(s) and/or the corresponding addition salt(s) with an acid represent from 0.005% to 6% by weight relative to the total weight of the dye composition.  
     
     
         17 . Composition according to any one of the preceding  claims 1  to  16 , characterized in that 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 preferably between 0.01 and 10.  
     
     
         18 . Composition according to any one of the preceding  claims 1  to  17 , characterized in that the addition salts with an acid are chosen from the hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.  
     
     
         19 . Composition according to any one of the preceding  claims 1  to  18 , characterized in that it contains at least one coupler.  
     
     
         20 . Composition according to  claim 19 , characterized in that the coupler(s) 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.  
     
     
         21 . Composition according to any one of the preceding  claims 1  to  20 , characterized in that it contains at least one additional oxidation base other than the pyrazoles defined in  claims 1  to  14 .  
     
     
         22 . Composition according to  claim 21 , characterized in that the additional oxidation base(s) represent(s) from 0.0005% to 12% by weight approximately relative to the total weight of the dye composition.  
     
     
         23 . Composition according to any one of the preceding  claims 1  to  22 , characterized in that it has a pH of between 3 and 12.  
     
     
         24 . Composition according to any one of the preceding  claims 1  to  23 , characterized in that it is in the form of liquids, creams or gels or in any other form that is suitable for dyeing keratin fibres, and especially human hair.  
     
     
         25 . Process for dyeing keratin fibres, and in particular human keratin fibres such as the hair, characterized in that at least one dye composition as defined in any one of  claims 1  to  24  is applied to these fibres, and the colour is revealed at acidic, neutral or alkaline pH using an oxidizing agent.  
     
     
         26 . Process according to  claim 25 , characterized in that the oxidizing agent present in the oxidizing composition is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates, percarbonates and persulphates, and peracids.  
     
     
         27 . Process for dyeing keratin fibres, and in particular human keratin fibres such as the hair, characterized in that a composition containing at least one carbonyl compound as defined in any one of  claims 1  to  24  is applied to these fibres in a first stage, a composition containing at least one diaminopyrazole as defined in any one of  claims 1  to  24  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.  
     
     
         28 . Multi-compartment device comprising a first compartment containing a dye composition as defined in any one of  claims 1  to  24  and a second compartment containing an oxidizing composition.  
     
     
         29 . Multi-compartment device comprising a first compartment containing a carbonyl compound as defined in any one of  claims 1  to  24 , a second compartment containing a diaminopyrazole as defined in any one of  claims 1  to  24 , and a third compartment containing an oxidizing composition.