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

• US 20040088800A1
• Filed: 12/17/2003
• Published: 05/13/2004
• Est. Priority Date: 12/22/2000
• Status: Abandoned Application

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Cotteret, Jean
• Application Number:
  US10/451,553
• Publication Number:
  US 20040088800A1
• Time in Patent Office: Days
• US Class Current: 8/405
• CPC Class Codes: A61K 8/35 Ketones, e.g. benzophenone
• CPC Class Codes: A61K 8/362 Polycarboxylic acids
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61K 8/494 with more than one nitrogen as the only hetero atom
• CPC Class Codes: A61K 8/498 having 6-membered rings or their condensed derivatives, e.g. coumarin
• CPC Class Codes: A61K 8/60 Sugars; Derivatives thereof
• CPC Class Codes: A61Q 5/10 Preparations for permanently dyeing the hair

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.

Claims

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

R₁, R₁′

, R₂ and R₂′

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, C₁-C₄ alkoxy, amino, carboxyl, C₁-C₁₀ alkoxycarbonyl, halogen, nitro, mono- or di(C₁-C₄)alkylamino, mono- or dihydroxy(C₁-C₄)alkylamino or C₆-C₂₀ aryl groups;

a C₆-C₂₀ aryl group, which is unsubstituted or substituted with one or more groups chosen from hydroxyl, amino, nitro, halogen, carboxyl, (C₁-C₁₀)alkoxycarbonyl, C₁-C₄ alkyl, mono- or polyhydroxy(C₁-C₄)alkyl, C₁-C₄ alkoxy, mono- or di(C₁-C₄)alkylamino or mono- or dihydroxy(C₁-C₄)alkylamino groups,

x denotes 0 or 1, and, when x is equal to 0, R₁ and R₂ 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 C₁-C₁₀ alkyl, C₁-C₁₀ alkoxy, carboxyl or C₁-C₁₀ 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, C₁-C₄ alkoxy, amino, carboxyl, C₁-C₁₀ alkoxycarbonyl, halogen, nitro, mono- or di(C₁-C₄)alkylamino, mono- or dihydroxy(C₁-C₄)alkylamino or C₆-C₂₀ aryl groups;

a C₆-C₂₀ aryl group, which is unsubstituted or substituted with one or more groups chosen from hydroxyl, amino, nitro, halogen, carboxyl, (C₁-C₁₀)alkoxycarbonyl, C₁-C₄ alkyl, mono- or polyhydroxy(C₁-C₄)alkyl, C₁-C₄ alkoxy, mono- or di(C₁-C₄)alkylamino or mono- or dihydroxy(C₁-C₄)alkylamino groups,

R₃ and R₄, which may be identical or different, represent a hydrogen atom, a C₁-C₁₀ alkyl, C₁-C₁₀ monohydroxyalkyl or C₂-C₁₀ polyhydroxyalkyl radical, Na, K or NH₄.

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:

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:

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.