Oxidation dyeing process using a composition comprising a monoaminobenzene and a metal catalyst

Abstract

The invention relates to a process for dyeing keratin fibers, comprising the use of one or more metal catalysts and of a composition (A) comprising: one or more oxidizing agents, and at least one monoaminobenzene of formula (I), or an addition salt or solvate thereof in which the radicals R1 to R5 represent, independently of each other: a hydrogen atom; a halogen atom, a C1-C6 alkyl radical, a C1-C6 alkoxy radical, a carboxylic radical (COOH), a sulfonic radical (S03 H); two of the adjacent radicals R1 to R5 possibly forming, with the carbon atoms that bear them, a saturated or unsaturated 5- to 7-membered ring, optionally comprising from 1 to 2 heteroatoms, preferably oxygen, the said ring being optionally fused with a saturated or unsaturated 5- to 6-membered ring; on condition that at least one of the radicals R1 to R5 represents an optionally substituted alkoxy radical and preferably at least one of the other radicals R1 to R5 is a hydrogen atom. ##STR00001##

Claims

1. A process for dyeing keratin fibers, the process comprising: applying to the keratin fibers a composition comprising at least one metal catalyst comprising a metal in oxidation state II, and a composition (A) comprising: at least one oxidizing agent, at least one fatty substance chosen from liquid petroleum jelly, C.sub.6-C.sub.16 alkanes, or polydecenes, present in an amount of at least about 25% by weight, relative to the total weight of composition (A), at least one coupler, and at least one oxidation base chosen from monoaminobenzenes of formula (I), or an addition salt or solvate thereof: ##STR00027## wherein the radicals R1 to R5, independently of each other, are chosen from: hydrogen atoms; halogen atoms, F, Cl, or Br; linear or branched C1-C6 or C1-C4 alkyl radicals, optionally substituted; linear or branched C1-C6 or C1-C4 alkoxy radicals, optionally substituted; or carboxylic (COOH) or sulfonic (SO3H) radicals; wherein two of the adjacent radicals R1 to R5 may form, with the carbon atoms that bear them, a saturated or unsaturated, 5- to 7-membered ring, optionally comprising from 1 to 2 heteroatoms, the ring being optionally fused with a saturated or unsaturated 5- to 6-membered ring; and with the proviso that at least one of the radicals R1 to R5 represents an optionally substituted alkoxy radical.

2. The process of claim 1, wherein the at least one metal catalyst is chosen from metal salts, metal oxides, metal complexes, transition metal salts, rare-earth metal salts, mineral salts chosen from halides, hydrated halides, anhydrous halides, carbonates, sulfates, or phosphates or mixtures thereof.

3. The process of claim 1, wherein the at least one metal catalyst is chosen from metal salts bearing a metal in oxidation state II and two (poly)hydroxy acid-based ligands.

4. The process of claim 3, wherein the metal salts are chosen from metal salts of formula (II), or hydrates thereof, solvates thereof, or enantiomers thereof:
RC(O)O-M-OC(O)R(II) wherein: M is chosen from a metal (II) or metal.sup.2+ in oxidation state 2 or manganese(II); and R and R, which may be identical or different, represent a (C1-C6)(poly)hydroxyalkyl group.

5. The process of claim 2, wherein the metal salts are organic acid salts chosen from citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates, or tartrates.

6. The process of claim 1, wherein the at least one metal catalyst is chosen from organic acid salts of transition metals, organic acid salts of manganese, mineral salts of rare-earth metals, or mineral salts of cerium.

7. The process of claim 1, wherein the composition (A) comprises at least one fatty substance in an amount ranging from about 25% to about 70%, by weight relative to the total weight of composition (A).

8. The process of claim 1, wherein the at least one fatty substance is present in an amount ranging from about 25% to about 60% by weight, relative to the total weight of composition (A).

9. The process of claim 1, wherein the cosmetic composition (A) further comprises at least one surfactant.

10. The process of claim 1, wherein the oxidation base of formula (I) is chosen from the following compounds, salts thereof, or solvates thereof: ##STR00028## ##STR00029## ##STR00030## ##STR00031## 1) para-Aminobenzene oxidation bases: ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## 2) Radical monoaminobenzene bases ##STR00039## ##STR00040## ##STR00041## ##STR00042##

11. The process of claim 1, wherein in the oxidation base of formula (I), at least one of the radicals R1 to R5 is an optionally substituted alkoxy radical, and at least one other of the radicals R1 to R5 is an alkoxy or alkyl radical or forms, with an adjacent radical and the carbon atoms to which they are attached, a ring, and the other radicals are hydrogen atoms.

12. The process of claim 1, wherein the oxidation base of formula (I) is chosen from 4-methoxy-2-methylaniline, 3-methoxy-4-methylaniline, 2,5-dimethoxyaniline, 2,6-dimethoxyaniline, or 2,4-dimethoxyaniline, or salts or solvates thereof.

13. The process of claim 1, wherein the composition comprises an additional oxidation base chosen from heterocyclic oxidation bases chosen from pyrazole or pyrazolinone oxidation bases.

14. The process of claim 1, wherein the oxidizing agent is hydrogen peroxide.

15. The process of claim 1, wherein a composition (B) comprising the said at least one metal catalyst and composition (A) are mixed together to form a mixture prior to application to the keratin fibers, and wherein the mixture is applied to wet or dry keratin fibers.

16. The process of claim 1, wherein a composition (B) comprising the said at least one metal catalyst and composition (A) are successively applied to the keratin fibers, with or without intermediate rinsing.

17. The process of claim 1, wherein composition (A) results from the mixing of two or three compositions including at least one composition (A) comprising at least one oxidation base of formula (I) and a composition (C) comprising the at least one oxidizing agent, and optionally a composition (D) comprising the at least one fatty substance.

18. A dye composition comprising: at least one oxidation base chosen from monoaminobenzenes of formula (I) or an addition salt or solvate thereof: ##STR00043## wherein the radicals R1 to R5, independently of each other, are chosen from: hydrogen atoms; halogen atoms, F, Cl, or Br; linear or branched C1-C6 or C1-C4 alkyl radicals, optionally substituted; linear or branched C1-C6 or C1-C4 alkoxy radicals, optionally substituted; or carboxylic (COOH) or sulfonic (SO3H) radicals; wherein two of the adjacent radicals R1 to R5 may form, with the carbon atoms that bear them, a saturated or unsaturated, 5- to 7-membered ring, optionally comprising from 1 to 2 heteroatoms, the ring being optionally fused with a saturated or unsaturated 5- to 6-membered ring; and with the proviso that at least one of the radicals R1 to R5 represents an optionally substituted alkoxy radical, at least one fatty substance chosen from liquid petroleum jelly, C.sub.6-C.sub.16 alkanes, or polydecenes in an amount of at least about 25%, by weight relative to the total weight of the composition; at least one coupler; and an oxidizing agent.

Description

EXAMPLE 1

1. Preparation of the Composition Based on Metal Salts

(1) Composition (B1) based on metal salts is prepared (the amounts are expressed as weight percentages).

(2) TABLE-US-00001 Composition B1 Laureth-2 2 g Decyl glucoside 2 g Liquid petroleum jelly (mineral oil) 78.5 g PEG-150/decyl alcohol/SMDI copolymer (Aculyn 0.5 g 44 sold by Rhm & Haas) Manganese gluconate (CAS No. 6485-39-8) 0.4 g Water qs 100 g

2. Preparation of a Dye Composition A1

(3) The dye composition is prepared at the time of the use by mixing: 6.7 g of composition D1 2.7 g of composition A1 or A2 10 g of composition C1
Each of the compositions is described in the following tables, the amounts being expressed as weight percentages, unless otherwise mentioned.
Composition D1

(4) TABLE-US-00002 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

(5) Composition A1 containing the monoaminobenzene of formula (I) having a pH adjusted to 7

(6) TABLE-US-00003 A1 A2 Oxidation base of formula (I) 20 10.sup.3 20 10.sup.3 mol % mol % Coupler 20 10.sup.3 mol % Free monoethanolamine 14.37 g 14.37 g Sodium metabisulfite 0.7 g 0.7 g L-Ascorbic acid 0.25 g 0.25 g EDTA 0.287 g 0.287 g Propylene glycol 6.2 g 6.2 g Ethanol 15 g 15 g Hexylene glycol 3 g 3 g Dipropylene glycol 3 g 3 g Benzyl alcohol 5 g 5 g Deionized water qs 100 g qs 100 g
Composition C1 (Oxidizing Agent)

(7) TABLE-US-00004 50% hydrogen peroxide solution 12 Liquid petroleum jelly 20 Cetylstearyl alcohol (30/70 C16/C18) 8 Oxyethylenated cetylstearyl alcohol (33 OE) 3 Tetrasodium pyrophosphate decahydrate 0.03 Sodium hexahydroxystannate 0.04 Diethylenetriaminepentaacetic acid, pentasodium 0.15 salt as a 40% aqueous solution Polydimethyldiallylammonium chloride at 40% in 0.5 water, non-stabilized Poly[(dimethyliminio)-1,3- 0.25 propanediyl(dimethyliminio)-1,6-hexanediyl dichloride] as an aqueous 60% solution Phosphoric acid qs pH = 2 Oxyethylenated (4 OE) rapeseed acid amides 1.3 Vitamin E 0.1 Glycerol 0.5 Deionized water qs 100
In composition A2, the couplers below were used:

(8) TABLE-US-00005 INCI name Resorcinol meta-Aminophenol Hydroxybenzomorpholine 2-Methyl-5-hydroxyethylaminophenol 2,4-Diaminophenoxyethanol HCl 2-Methylresorcinol 4-Amino-2-hydroxytoluene 6-Hydroxyindole 2-Amino-3-hydroxypyridine 5-Amino-6-chloro-o-cresol

(9) I. Procedure

(10) Composition (B1) based on metal salts is applied to locks of natural hair containing 90% white hairs (NG). The composition/lock bath ratio is respectively 1/1 (g/g). The leave-on time is 10 minutes at room temperature.

(11) The locks of hair are then rinsed and dried manually.

(12) Dye composition A1 is then applied by brush to each of the locks. The composition/lock bath ratio is respectively 1/1 (g/g). It is left to stand for 35 minutes at room temperature.

(13) After this leave-on time, the locks of hair are washed with iNOA POST shampoo, rinsed and then dried under a hood at a temperature of 60 C.

(14) II. Results

(15) The colour of the locks was evaluated in the CIE L*a*b* system, using a Minolta Spectrophotometer CM3600D colorimeter. In this L*a*b* system, L* represents the intensity of the colour, a* indicates the green/red colour axis and b* indicates the blue/yellow colour axis. The lower the value of L*, the darker or more intense the colour.

(16) a. Calculation of the Colour Power (DE*)

(17) In the table below, the value of DE* is calculated from the values of L*a*b* according to equation (i) below:
DE*={square root over ((L*L.sub.o*).sup.2+(a*a.sub.o*).sup.2+(b*b.sub.o*).sup.2)}(i).

(18) The dyeing power is measured from the values L*, a* and b* measured on locks of natural grey hair after dyeing or, alternatively, on locks of permanent-waved grey hair after dyeing, and L.sub.0*, a.sub.0* and b.sub.0* represent the values measured on natural undyed locks of grey hair or, respectively, on permanent-waved undyed locks of grey hair.

(19) The greater the value of DE*, the greater the dyeing power.

(20) The results in terms of the build-up are collated in the following table.

(21) TABLE-US-00006 Dyes used Colour Hair L* a* b* DE* using composition A1 4-Methoxy-2-methyl- Nacreous NG 59.58 7.02 16.92 10.1 aniline 2,5-dimethoxyaniline Golden NG 65.1 2.8 16.83 4.02

(22) Good dyeing power is obtained;

(23) TABLE-US-00007 DE* build- Dyes used Colour Hair L* a* b* up using composition A2 4-Methoxy-2-methylaniline + Mahogany NG 29.8 7.98 9.51 35.03 2,4-diaminophenoxyethanol HCl brown 4-Methoxy-2-methylaniline + Coppery NG 29.17 9.71 14.21 36.07 6-hydroxyindole brown 4-Methoxy-2-methylaniline + Coppery NG 57.94 7.32 17.2 10.97 resorcinol golden 3-Methoxy-4-methylaniline + Dark NG 29.93 6.03 9.04 34.6 2,4-diaminophenoxyethanol HCl brown 3-Methoxy-4-methylaniline + Mahogany NG 31.73 9.55 16.59 33.82 6-hydroxyindole brown 3-Methoxy-4-methylaniline + Brown NG 60.49 4.81 18.24 7.68 resorcinol 2,5-Dimethoxyaniline + Dark NG 34.24 6.29 10.47 32.22 2,4-diaminophenoxyethanol HCl brown 2,5-Dimethoxyaniline + Brown NG 32.47 7.8 15.19 34.12 6-hydroxyindole 2,5-Dimethoxyaniline + resorcinol Golden NG 58.39 6.05 19.21 10.6 2,5-Dimethoxyaniline + Golden NG 47.77 6.3 18.39 19.44 meta-aminophenol light brown 2,5-Dimethoxyaniline + Golden NG 49.6 7.38 22.29 19.49 hydroxybenzomorpholine light brown 2,5-Dimethoxyaniline + Dark NG 61.76 4.61 17.46 6.66 2-methyl-5-hydroxyethylaminophenol brown 2,5-Dimethoxyaniline + Golden NG 59.17 3.56 17.12 7.97 2-methylresorcinol 2,5-Dimethoxyaniline + Coppery NG 58.41 5.31 18.88 10.08 4-amino-2-hydroxytoluene golden 2,5-Dimethoxyaniline + Golden NG 56.74 6.66 20.97 12.99 2-amino-3-hydroxypyridine 2,5-Dimethoxyaniline + Golden NG 62.87 4.08 18.43 4.06 5-amino-6-chloro-o-cresol 2,6-Dimethoxyaniline + 2,4- Brown NG 34.47 6.31 10.93 28.74 diaminophenoxyethanol HCl 2,6-Dimethoxyaniline + Coppery NG 37.30 9.56 19.48 27.85 6-hydroxyindole brown 2,6-Dimethoxyaniline + resorcinol Coppery NG 60.89 4.15 17.10 6.75 golden 2,4-Dimethoxyaniline + Dark NG 32.39 7.61 6.96 34.68 2,4-diaminophenoxyethanol HCl brown 2,4-Dimethoxyaniline + Dark NG 31.71 9.38 12.95 34.68 6-hydroxyindole brown

(24) When the monoaminobenzene (I) is combined with a coupler, the dyeing power is improved, with a diversified range of tints depending on the combined couplers.

EXAMPLE 2

(25) A composition is prepared according to the composition A1 with 2,5-dimethoxyaniline as compound of formula (I) and 2-(2,5-diaminophenyl)ethanol sulphate (2010.sup.3 mol %). This composition was mixed as defined above with the composition C1 and D1. The resulting composition was applied on natural locks and permed locks hair according to the process previously disclosed after the application and rinsing of the composition B1 containing manganese salt. The locks were then shampooed, rinsed and dried. The resulting coloration of locks of hair was evaluated in the L*a*b* system.

(26) The selectivity of the coloration is the variation of the color between natural colored hair and permed colored hair. Natural hair is representative of the nature of the hair at the root hair and the permed hair is representative of the nature of the hair at the point.

(27) The selectivity is measured by: E, which is the color variation between a natural colored lock and a permed colored lock, is obtained from the following formula:
E={square root over ((L*L.sub.o*).sup.2+(a*a.sub.o*).sup.2+(b*b.sub.o*).sup.2)}
wherein L* indicates lightness and a* and b* are the chromaticity coordinates of the natural colored locks whereas L.sub.0* indicates the lightness and a.sub.0* et b.sub.0* are the chromaticity of the permed colored locks. The lowest is the value of E, the weakest the selective is the coloration and the best is the color of the hair.
The measured selectivity is reported in the following table:

(28) TABLE-US-00008 Color L* a* b* dE* Selectivity Natural Brown 31.2 2.5 9.9 30.8 5.9 hair Permed 25.5 3.1 8.1 38.6 hair

EXAMPLE 3

(29) The following dyeing compositions were prepared according to the above mentioned composition comprising as base and coupler the one disclosed in the table below.

(30) TABLE-US-00009 % DE after 10 shampoos Color L* a* b* dE* ** 2,5-dimethoxyaniline With IA natural permed Violet/Black 20.0 19.1 5.3 2.8 7.5 5.0 50.7 48.1 15.3 0.5 With IB natural permed violet 20.7 18.5 7.1 3.5 8.4 3.7 50.5 48.2 3.2 3.1 With IC natural permed rouge 45.15 40.85 27.4 34.9 1.3 1.4 36.3 43.1 18.9 10.7 2,4-dimethoxyaniline With IA natural Brown 32.0 5.3 2.5 35.6 6.9 permed 25.8 4.8 1.24 39.8 4.5 With IB BN red 32.1 18.1 9.2 37.3 17.5 BP 38.4 15.8 8.8 38.7 10.23 2-amino-5-chlorophenol with IA natural brown 31.9 3.5 1.4 36.3 14.5 permed 37.3 4.0 2.9 38.7 9.6 with IB natural 30.0 18.5 7.1 40.5 5.9 Permed red 26.8 18.8 6.9 42.2 1.4 **% DE after 10 shampoos: (DE after 10 shampoo DE at the time of dyeing/DE at the time of the dyeing) 100.
With these compositions, the resulting coloration is intense and with a good shampoo fastness.