COMPOSITION FOR DYEING KERATIN FIBRES, COMPRISING AN OXIDATION BASE AND A PARTICULAR HETEROARYL COUPLER

Abstract

The invention relates to a composition comprising: i) at least one oxidation base, preferably of heterocyclic and/or para-phenylenediamine type; and ii) at least one heteroaryl coupler of formula (I), with R.sup.1, R.sup.2, R.sup.3, A and X as defined in the description. The invention also relates to a process for dyeing keratin fibres using ingredients i) and ii); to a kit comprising ingredients i) and ii); and to the use of ingredient i) combined with ii) for dyeing keratin fibres. The composition of the invention leads to particularly powerful, chromatic and sparingly selective colourings.

##STR00001##

Claims

1. Composition comprising: i) at least one oxidation base preferably chosen from heterocyclic bases and para-phenylenediamine bases; ii) at least one heteroaryl coupler of formula (I): ##STR00181## and also addition salts thereof with an organic or mineral acid or base, optical or geometrical isomers thereof, tautomers thereof or solvates thereof such as hydrates, in which compound of formula (I): A represents oxygen or sulfur atoms, preferably sulfur; X represents a nitrogen atom or a group CR.sup.4; R.sup.1 and R.sup.2, which may be identical or different, represent i) a linear or branched (C.sub.1-C.sub.4) alkyl group, optionally interrupted with one or more heteroatoms, and optionally hydrogenated or (C.sub.1-C.sub.4)alkylated, and/or optionally substituted, ii) optionally substituted aryl; iii) optionally substituted heteroaryl; iv) optionally substituted (hetero)cycloalkyl; or alternatively R.sup.1 and R.sup.2 form, together with the nitrogen atom that bears them, an optionally substituted heterocycloalkyl, also possibly comprising one or more heteroatoms chosen from oxygen, sulfur and nitrogen, said heterocycle preferentially being 5- or 6-membered such as morpholino, piperazino or piperidino; R.sup.3 and R.sup.4, which may be identical or different, represent i) a linear or branched (C.sub.1-C.sub.4) alkyl group, optionally interrupted with one or more heteroatoms, and optionally hydrogenated or (C.sub.1-C.sub.4)alkylated, and/or optionally substituted with one or more groups; ii) optionally substituted aryl; iii) optionally substituted heteroaryl or iv) optionally substituted (hetero)cycloalkyl.

2. Composition according to the preceding claim, in which the oxidation base(s) i) are chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases, and the addition salts thereof; preferably chosen from para-phenylenediamine bases and heterocyclic bases such as 3-aminopyrazolo[1,5-a]pyridine bases and pyrazole derivatives.

3. Composition according to either of the preceding claims, in which the oxidation base(s) i) are chosen from heterocyclic bases and more particularly from: 3-aminopyrazolo[1,5-a]pyridines preferably substituted in position 2 with: a) a (di)(C.sub.1-C.sub.6)(alkyl)amino group, the alkyl groups possibly being substituted with one or more hydroxyl, amino or imidazolium groups; b) a cationic or non-cationic 5- to 7-membered heterocycloalkyl group comprising from 1 to 3 heteroatoms, optionally substituted with one or more (C.sub.1-C.sub.6)alkyl groups such as di(C.sub.1-C.sub.4)alkylpiperazinium; c) a (C.sub.1-C.sub.6)alkoxy group optionally substituted with one or more hydroxyl groups, such as -hydroxyalkoxy, and also the addition salts thereof; pyrazole derivatives, 4,5-diamino-1-methylpyrazole, 4,5-diamino-1-(-hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4-chlorobenzyl)pyrazole, 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-(-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, 3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole, 3,5-diamino-4-(-hydroxyethyl)amino-1-methylpyrazole, and the addition salts thereof.

4. Composition according to any one of the preceding claims, in which the coupler(s) ii) are chosen from the thiazolyl couplers (I), i.e. they are such that A represents a sulfur atom and X represents a nitrogen atom: ##STR00182## and also addition salts thereof with an organic or mineral acid or base, optical or geometrical isomers thereof, tautomers thereof or solvates thereof such as hydrates, with R.sup.1, R.sup.2 and R.sup.3 as defined in the preceding claim.

5. Composition according to any one of the preceding claims, in which the coupler(s) ii) are such that, in formula (I) or (I): R.sup.1 and R.sup.2 represent i) a (C.sub.1-C.sub.6)alkyl group optionally interrupted with one or more heteroatoms chosen from oxygen, sulfur and nitrogen, preferably with at least one oxygen atom.

6. Composition according to any one of the preceding claims, in which the coupler(s) ii) are such that, in formula (I) or (I): R.sup.1 and R.sup.2 form, together with the nitrogen atom that bears them, an optionally substituted 5- or 6-membered, preferably 6-membered, heterocycloalkyl group, such as morpholino, piperazino or piperidino, particularly morpholino.

7. Composition according to any one of the preceding claims, in which the coupler(s) ii) are such that, in formula (I) or (I): R.sup.3 represents i) a (C.sub.1-C.sub.6)alkyl group which is optionally substituted, preferably with at least one hydroxyl group; ii) an optionally substituted aryl group such as phenyl; or iii) an optionally substituted 5- or 6-membered, preferably 6-membered, heterocycloalkyl, such as morpholino, piperazino or piperidino, particularly morpholino.

8. Composition according to any one of the preceding claims, in which the coupler(s) ii) are chosen from the following compounds: TABLE-US-00008 and also the optical isomers thereof, tautomers thereof, and the addition salts thereof with an acid or a base, the preferred couplers of the invention being those of formulae 1 to 3.

9. Composition according to any one of the preceding claims, in which the coupler(s) ii) are present in an amount ranging from 0.001% to 20% by weight relative to the total weight of the dye composition, preferably ranging from 0.005% to 6% by weight relative to the total weight of the dye composition.

10. Composition according to any one of the preceding claims, which comprises iii) at least one fatty substance, the content of fatty substance preferably ranging from 10% to 80% by weight, and even more particularly ranging from 20% to 80% by weight, better still from 25% to 75% by weight and most particularly from 40% to 70% by weight relative to the total weight of the dye composition, more preferentially between 50% and 60% by weight relative to the total weight of the dye composition.

11. Composition according to any one of the preceding claims, characterized in that iii) the fatty substance(s) are liquid at 25 C. and at atmospheric pressure, preferably chosen from C.sub.6-C.sub.16 hydrocarbons, hydrocarbons containing more than 16 carbon atoms, triglycerides, fatty alcohols, esters of fatty acids and/or of fatty alcohols other than triglycerides, or mixtures thereof, and preferably from liquid petrolatum, polydecenes, liquid fatty alcohols, liquid esters of fatty acids and/or of fatty alcohols, or mixtures thereof, and even more preferentially from liquid petrolatum and octyl-2-dodecanol.

12. Composition according to any one of the preceding claims, which comprises iv) one or more metal catalysts, preferably chosen from metal salts of oxidation state II, which bear two ligands derived from C.sub.2-C.sub.10 carboxylic acid or from (poly)hydroxy acid; in particular, the metal salts are complexed with two carboxylate groups such as those of formula (II):
R.sub.aC(O)O-M-OC(O)R.sub.b (II) and also the solvates thereof, such as hydrates, and enantiomers thereof, in which formula (II): M represents a metal (II) or metal.sup.2+ in oxidation state 2, R.sub.a and R.sub.b, which may be identical or different, represent a (poly)(hydroxy)(C.sub.1-C.sub.6)alkyl group; more particularly, the metal catalysts are chosen from organic acid salts of transition metals, especially of manganese, and mineral salts of rare-earth metals, especially of cerium.

13. Composition according to any one of the preceding claims, characterized in that it comprises v) one or more alkaline agents, which are preferably mineral, organic or hybrid and are chosen particularly from aqueous ammonia, alkali metal carbonates or bicarbonates such as sodium carbonate or bicarbonate, potassium carbonate or bicarbonate, sodium hydroxide or potassium hydroxide, organic amines chosen from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (III), or mixtures thereof: ##STR00351## in which formula (III) W is a divalent C.sub.1-C.sub.6 alkylene radical optionally substituted with one or more hydroxyl groups or a C.sub.1-C.sub.6 alkyl radical, and/or optionally interrupted with one or more heteroatoms such as O, or NR.sub.u; R.sub.x, R.sub.y, R.sub.z, R.sub.t and R.sub.u, which may be identical or different, represent a hydrogen atom or a C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 hydroxyalkyl or C.sub.1-C.sub.6 aminoalkyl radical; particularly e) the basifying agent(s) are chosen from alkanolamines and more particularly monoethanolamine, and amino acids in neutral or ionic form.

14. Composition according to any one of the preceding claims, which comprises vi) one or more chemical oxidizing agents, chosen in particular from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, and peracids, the chemical oxidizing agent preferably being hydrogen peroxide.

15. Process for dyeing keratin fibres, in particular human keratin fibres such as the hair, which consists in applying to said fibres the composition according to any one of the preceding claims.

16. Process according to the preceding claim, in which the composition is derived from the mixing of two compositions: a composition (A) comprising: at least one oxidation base i) as defined in any one of claims 1 to 3; at least one heteroaryl coupler ii) as defined in any one of claims 1 and 4 to 9; optionally at least one alkaline agent v) as defined in claim 13; and a composition (B) comprising: at least vi) one chemical oxidizing agent as defined in claim 14; at least one of the compositions (A) and (B) comprising: at least iii) one fatty substance as defined in claim 10 or 11, and optionally at least iv) one metal catalyst as defined in claim 12; it being understood that the content of fatty substance of the composition resulting from the mixing of compositions (A)+(B) comprises at least 10%, in particular at least 15%, more particularly at least 20% and preferably at least 25% by weight relative to the total weight of the composition.

17. Process according to claim 15, in which use is made of two aqueous compositions (B) and (C) and an anhydrous composition (A), the anhydrous composition (A) comprising at least iii) one fatty substance as defined in claim 10 or 11; composition (B) comprising: at least one oxidation base i) as defined in any one of claims 1 to 3; and at least ii) one heteroaryl coupler of formula (I) as defined in any one of claims 4 to 9; composition (C) comprising at least vi) one chemical oxidizing agent as defined in claim 14; it being understood that: at least v) one alkaline agent as defined in claim 13 is included in compositions (A) and/or (B) and preferably solely in composition (B); optionally at least iv) one metal catalyst as defined in claim 12 is included in at least one of the compositions (A), (B) or (C); these three compositions being such that the content of fatty substance of the composition resulting from the mixing of the three compositions (A)+(B)+(C) comprises at least 10%, in particular at least 15%, more particularly at least 20% and preferably at least 25% by weight relative to the total weight of the composition derived from the mixing of (A)+(B)+(C).

18. Multi-compartment device comprising a first compartment containing composition (A) as defined in claim 16 and at least a second compartment containing composition (B) as defined in claim 16, the compositions of the compartments being intended to be mixed before application to give a composition after mixing (A)+(B), the amount of fatty substance of which represents at least 10%, in particular at least 15%, more particularly at least 20% and preferably at least 25% by weight relative to the total weight of the composition resulting from the mixing of (A)+(B).

19. Use of at least one coupler ii) as defined according to any one of claims 1 and 4 to 9, for the oxidation dyeing of keratin fibres.

Description

EXAMPLES

Dye Composition

[0265] The dye composition is prepared at the time of use by mixing the three compositions below: 6.7 g of composition A+2.7 g of composition B+10 g of composition C. Each of the compositions is specified in the following tables:

Composition A

[0266]

TABLE-US-00002 Ingredients A (g %) Liquid petroleum jelly 64.5 2-Octyldodecanol 11.5 Distearyldimethylammonium-modified hectorite 3 Propylene carbonate 1 Oxyethylenated (4 OE) sorbitan monolaurate 11 Glycol distearate 8 Oxyethylenated (2 OE) lauryl alcohol 1

Composition B

[0267]

TABLE-US-00003 Ingredients B (g %) Base 1, 2 or 3* 20 10.sup.3 mol % Coupler of the invention** 1, 2, 3 or 4 20 10.sup.3 mol % Free monoethanolamine 0.14 g Sodium metabisulfite 0.7 g L-Ascorbic acid 0.25 g Propylene glycol 6.2 g Ethanol 15.1 g Hexylene glycol 3 g Dipropylene glycol 3 g Benzyl alcohol 6 g pH agent qs pH = 7 Deionized water qs 100 g Base* [00174][00175][00176]**Couplers: [00177][00178][00179][00180]

Composition C (Oxidizing Agent)

[0268]

TABLE-US-00004 Ingredients C (g %) 50% hydrogen peroxide solution 12 Liquid petroleum jelly 20 Cetylstearyl alcohol (30/70: C.sub.16/C.sub.18) 8 Oxyethylenated cetylstearyl alcohol (33 OE) 3 Tetrasodium pyrophosphate decahydrate 0.03 Crystalline sodium hexahydroxystannate 0.04 Diethylenetriaminepentaacetic acid, pentasodium salt as a 40% 0.15 aqueous solution Polydimethyldiallylammonium chloride at 40% in water, non- 0.5 stabilized Poly[(dimethyliminio)-1,3-propanediyl(dimethyliminio)-1,6- 0.25 hexanediyl dichloride] as an aqueous 60% solution Phosphoric acid qs pH Protected oxyethylenated (4 OE) rapeseed acid amides 1.3 Vitamin E 0.1 Glycerol 0.5 Deionized water qs 100

Dyeing Process

[0269] Pairs of locks of natural Caucasian hair containing 90% of grey hairs (NG) are treated with 19.4 g of dye composition mixture A+B+C, which is then left on for 35 minutes at room temperature, in comparison with a series of locks that is not treated with the composition.

[0270] After this leave-on time, the locks are washed with iNOA POST shampoo, rinsed and then dried under a hood.

[0271] The colouring obtained is measured using a Minolta CM-3600D spectrocolorimeter.

Results Obtained

Example 1

Dyeing Tests

[0272] Couplers 1 to 4 of the invention are applied in combination with bases 1 to 3.

[0273] Intense and varied colours are obtained.

[0274] The results in terms of the build-up are collated in Table 1 below.

TABLE-US-00005 TABLE 1 L* a* b* E*ab(D65) - Description (D65) (D65) (D65) build-up Colour Non-dyed control 66.68 0.4 15.05 NG lock Dyed with Base 45.19 6.04 19.81 22.72 Golden 1 + coupler 1 Dyed with Base 43.85 16.98 29.16 31.38 Coppery 1 + coupler 2 Dyed with Base 49.1 29.69 28.84 36.58 Coppery 2 + coupler 2 red Dyed with Base 39.88 9.02 3.97 29.24 Violet 3 + coupler 2 beige Dyed with Base 48.58 3.74 3.32 20.74 Beige 1 + coupler 3 Dyed with Base 45.71 21.51 17.04 29.16 Coppery 2 + coupler 3 red Dyed with Base 46.5 0.97 8.39 20.43 Grey 3 + coupler 3 Dyed with Base 51.22 5.84 6.87 17.24 Beige 1 + coupler 4 Dyed with Base 47.51 26.67 22.95 33.01 Coppery 2 + coupler 4 red Dyed with Base 47.82 0.76 8.74 19.06 Grey 3 + coupler 4

Example 2

Tests of Dyeing with Catalysis

[0275] Tests are performed this time in the presence of manganese gluconate catalyst (pretreatment composition 1) and replacing at the same molar concentration the base 2-hydroxy-3-aminopyrazolopyridine HCl of composition B with 2,5-dimethoxyaniline and this time using as coupler the heteroaryl coupler 4.

Composition 1

[0276]

TABLE-US-00006 SM Composition 1 Laureth-2 2 g Decyl glucoside 2 g Mineral oil 78.5 g PEG-150/decyl glucoside/SMDI copolymer 0.5 g Manganese gluconate (CAS No. 6485-39-8) 0.4 g Water qs 100 g

[0277] Locks of natural Caucasian hair containing 90% grey hairs (NG) are treated with: [0278] composition 1, which is left on for 10 minutes at room temperature, and then rinsed out and dried manually, [0279] the 19.4 g of dye composition mixture A+B+C, in a proportion of 6.7 g of composition A+2.7 g of composition B+10 g of composition C, which is then left on for 35 minutes at room temperature.

[0280] With the manganese gluconate pretreatment, intense blonde tints are obtained.

[0281] The results in terms of the build-up are collated in Table 2 below.

TABLE-US-00007 TABLE 2 Type of Coupling locks L* a* b* E*ab Coupler 3 + 2,5-dimethoxyaniline NG 34.52 3.89 8.97 30.81 with pretreatment with Mn.sup.2+