Hair dyeing process using a composition comprising at least one indol(in)e compound and a polycyclic aromatic compound containing at least ten carbon atoms

Abstract

The invention relates to a process for dyeing keratin fibers by treating said fibers with i) at least one aromatic compound comprising a hydrocarbon-based polycycle comprising at least 10 carbon atoms, at least one of the rings of which is aromatic, ii) at least one indol(in)e compound; optionally iii) at least one metal salt, iv) at least hydrogen peroxide or at least one hydrogen peroxide-generating system and v) at least one basifying agent; to a dye composition comprising ingredients i) and ii), and optionally iii) to v) as defined previously and to a kit comprising ingredients i) to v) as defined previously. This hair dyeing process makes it possible to obtain better colorings which are more uniform, chromatic and long-lasting and which do not impair the cosmetic properties of the keratin fibers, and prevents changing of the color associated with the presence of indol(in)e derivatives.

Claims

1. A process for dyeing keratin fibers, comprising applying to the fibers a composition (A) comprising: i) at least one indole or indoline compound; ii) at least one aromatic compound comprising a hydrocarbon-based polycycle comprising at least 10 carbon atoms, wherein at least one ring is aromatic and substituted with at least one hydroxyl or amino group; and iii) at least one metal salt chosen from transition metal salts, rare-earth metal salts, or mixtures thereof.

2. The process according to claim 1, wherein the at least one indole or indoline compound is chosen from compounds of formula (I) below: ##STR00019## or organic or mineral acid or base salts thereof, optical isomers thereof, enantiomers or diastereoisomers, geometrical isomers or tautomers thereof, oligomers thereof, or solvates thereof, wherein: R.sub.1 is chosen from a hydrogen atom, (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.1-C.sub.6)alkylcarbonyl, (C.sub.2-C.sub.6)alkenylcarbonyl, (C.sub.1-C.sub.6)alkylthiocarbonyl, (C.sub.2-C.sub.6)alkenylthiocarbonyl radical, or a radical R.sub.gOS(O).sub.x, wherein R.sub.g is a hydrogen atom, an alkali metal or alkaline-earth metal, or a (C.sub.1-C.sub.4)alkyl and x is equal to 1 or 2, said alkyl or alkenyl groups being optionally substituted; R.sub.2 is chosen from a hydrogen atom, (C.sub.1-C.sub.6)alkyl radical, or C(Z)ZR.sub.a; wherein R.sub.a is chosen from a hydrogen atom, an alkali metal or alkaline-earth metal, or a (C.sub.1-C.sub.6)alkyl radical; Z and Z are independently chosen from an oxygen or sulfur atom, a group NR.sub.b, or N.sup.+R.sub.bR.sub.c, Q.sup.; Z may also be chosen from a covalent a bond with R.sub.b and R.sub.c, which may be identical or different, representing a hydrogen atom or a (C.sub.1-C.sub.6)alkyl radical and Q.sup. is an anionic counterion; R.sub.3 is chosen from: i) a hydrogen atom; ii) a (C.sub.1-C.sub.6)alkyl radical optionally substituted especially with a group NR.sub.bR.sub.c, N.sup.+R.sub.aR.sub.bR.sub.c, Q.sup. or C(Z)ZR.sub.a, wherein R.sub.a is chosen from a hydrogen atom, an alkali metal or alkaline-earth metal, or a (C.sub.1-C.sub.6)alkyl radical; Z and Z are independently chosen from an oxygen or sulfur atom, a group NR.sub.b, or N.sup.+R.sub.bR.sub.c, Q.sup.; Z may also be chosen from a covalent a bond with R.sub.b and R.sub.c, which may be identical or different, representing a hydrogen atom or a (C.sub.1-C.sub.6)alkyl radical and Q.sup. represents an anionic counterion; iii) a radical corresponding to formula (II) below: ##STR00020## wherein: L is chosen from a covalent a bond, or a divalent group chosen from Z, C(Z)Z, or a divalent group (C.sub.1-C.sub.6)alkylene wherein Z and Z as defined previously; R.sub.1, R.sub.2 and R.sub.4 represent the same atoms or radicals as R.sub.1, R.sub.2 and R.sub.4, respectively; ##STR00021## is the point of attachment of the radical (II) to the rest of the molecule; or alternatively R.sub.1 and R.sub.2 and/or R.sub.2 and R.sub.3 form, together with the atoms that bear them, a fused, optionally substituted heterocyclic group; or R.sub.2 and R.sub.3 form, together with the carbon atoms that bear them, a fused, optionally substituted aryl group; R.sub.4 is chosen from: i) a hydrogen atom; ii) a halogen atom; iii) a group NRR; iv) an OH group; v) a (C.sub.1-C.sub.6)alkyl radical; vi) a (C.sub.1-C.sub.6)alkoxy radical; vii) a (C.sub.1-C.sub.6)alkylthio radical; viii) an aryloxy radical; ix) an arylthio radical; x) an aryl(C.sub.1-C.sub.6)alkoxy radical; xi) an aryl(C.sub.1-C.sub.6)alkylthio radical; xii) a radical R.sub.aC(Z.sub.a)Z.sub.b wherein Z.sub.a and Z.sub.b is chosen from an oxygen or sulfur atom or NR.sub.b, R.sub.a and R.sub.b are as defined previously, or xiii) a radical corresponding to formula (III) below: ##STR00022## wherein: L is as defined previously, R.sub.1, R.sub.2 and R.sub.3 represent the same atoms or radicals as R.sub.1, R.sub.2 and R.sub.3, respectively; ##STR00023## represents the point of attachment of the radical (III) to the rest of the molecule; X and X, which may be identical or different, is a hydrogen atom or a NRR radical chosen from NH.sub.2, OR.sub.e, SR.sub.e, (C.sub.1-C.sub.6)alkyl, or R.sub.aC(Z.sub.a)Z.sub.b as defined previously, where R.sub.e is chosen from a hydrogen atom, a group (C.sub.1-C.sub.6)alkyl, aryl, or aryl(C.sub.1-C.sub.6)alkyl; Y and Y, which may be identical or different, are chosen from OR.sub.e, SR.sub.e, NRR, R.sub.fOS(O).sub.xZ.sub.d or R.sub.fOS(O).sub.x wherein R.sub.f is chosen from a hydrogen atom, an alkali metal or alkaline-earth metal, or a (C.sub.1-C.sub.4)alkyl, Z.sub.d is chosen from an oxygen atom or a group NR with R as defined previously, x as defined previously and R.sub.e representing the same atoms or radicals as R.sub.e; or the radicals R.sub.e and R.sub.e of two contiguous groups X and X and/or contiguous groups Y and Y form, together with the oxygen or sulfur atom, a heterocyclic group; the radicals X, Y, X and Y being located on any of the carbon atoms 4 to 7 and 4 to 7, respectively; particularly; R and R, which may be identical or different, are chosen from a hydrogen atom or an optionally substituted (C.sub.1-C.sub.6)alkyl group; ##STR00024## represents a single bond or a double bond; wherein n is 0 when the bond between R.sub.1 and N or R.sub.1 and N is a single bond; or n is 1 when R.sub.1 or R.sub.1 is an alkenyl group and when the end linked to the nitrogen atom is a double bond; Q.sup. is an anionic counterion; n is 0 or 1; wherein: R.sub.3 cannot represent the radical (II) when R.sub.4 represents the radical (III); and when n is 0, then n is 0; when n is 1, then n is 1; or when n is 0, a radical C(Z)ZR.sub.a is in the anionic form C(Z)Z.sup..

3. The process according to claim 2, wherein the compounds of formula (I) are monomers and R.sub.3 is chosen from a hydrogen atom or an optionally substituted (C.sub.1-C.sub.6)alkyl radical.

4. The process according to claim 2, wherein the compounds of formula (I) are indole compounds wherein the ##STR00025## bond between the carbon atoms bearing the radicals R.sub.2 and R.sub.3 is a double bond.

5. The process according to claim 2, wherein the compounds of formula (I) are chosen from the indole compounds of formula (Ia) below, or the organic or mineral acid or base salts thereof: ##STR00026## wherein: R.sub.1 and R.sub.3, which may be identical or different, are chosen from a hydrogen atom or a C.sub.1-C.sub.4 alkyl radical; R.sub.2 is chosen from a hydrogen atom or a C.sub.1-C.sub.4 or C(O)OH radical; X is chosen from a hydrogen atom, NH.sub.2, OH, a C.sub.1-C.sub.4 alkyl radical, a C.sub.1-C.sub.4 alkoxy radical, or a radical OC(O)R wherein R is chosen from H or C.sub.1-C.sub.4 alkyl; Y is chosen from OH, NH.sub.2, or a radical OC(O)R wherein R is chosen from H or C.sub.1-C.sub.4 alkyl, or the organic or mineral acid or base salts thereof.

6. The process according to claim 5, wherein the indole compounds of formula (Ia) are chosen from 5,6-dihydroxyindole, 2-methyl-5,6-dihydroxyindole, 3-methyl-5,6-dihydroxyindole, 4-hydroxyindole, 2,3-dimethyl-5,6-dihydroxyindole, 6-hydroxy 5-methoxyindole, 6-hydroxyindole, 5-hydroxyindole, 7-hydroxyindole, 7-aminoindole, 5-aminoindole, 5,6-dihydroxyindole-2-carboxylic acid, 5-aminoindole, 1-methyl-5,6-dihydroxyindole, 5-acetyloxy-6-hydroxyindole, 6-acetyl-5-hydroxyindole and 5,6-diacetyloxyindole, or the organic or mineral acid or base salts thereof.

7. The process according to claim 1, wherein the at least one indole compound is chosen from: ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## or the organic or mineral acid or base salts thereof.

8. The process according to claim 2, wherein the compounds of formula (I) are chosen from the indoline compounds of formula (Ib) below, or the enantiomers and diastereoisomers thereof or the organic or mineral acid or base salts thereof: ##STR00035## wherein: R.sub.1 and R.sub.3, which may be identical or different, are chosen from a hydrogen atom or a C.sub.1-C.sub.4 alkyl radical; R.sub.2 is chosen from a hydrogen atom or a C.sub.1-C.sub.4 or C(O)OH radical; X is chosen from a hydrogen atom, NH.sub.2, OH, a C.sub.1-C.sub.4 alkyl radical, a C.sub.1-C.sub.4 alkoxy radical, or a radical OC(O)R wherein R is chosen from H or C.sub.1-C.sub.4 alkyl; Y is chosen from OH, NH.sub.2 or a radical OC(O)R wherein R is chosen from H or C.sub.1-C.sub.4 alkyl, or the organic or mineral acid or base salts thereof.

9. The process according to claim 1, wherein composition (A) comprises at least one indole or indoline compound chosen from 5,6-dihydroxyindole or 5,6-dihydroxyindoline.

10. The process according to claim 1, wherein composition (A) comprises at least one aromatic compound comprising a hydrocarbon-based polycycle comprising at least 10 carbon atoms, wherein at least one of the rings of which is aromatic, chosen from compounds corresponding to formula (II) below: ##STR00036## or the organic or mineral acid or base salts thereof, optical isomers thereof, enantiomers or diastereoisomers, geometrical isomers or tautomers thereof, or solvates thereof; wherein: R, which may be identical or different, is chosen from a halogen atom, a (C.sub.1-C.sub.6)alkyl group, (C.sub.1-C.sub.6)alkoxy group, (C.sub.1-C.sub.6)alkylthio, (di)(C.sub.1-C.sub.6)(alkyl)amino group, hydroxyl group, thio, heterocyclic group, pyperidinyl group, or (C.sub.1-C.sub.6)(alkyl)piperazinyl group; and p is an integer chosen from 0, 1, 2, 3, 4, 5, 6 or 7.

11. The process according to claim 1, wherein composition (A) comprises at least one aromatic compound comprising a hydrocarbon-based polycycle comprising at least 10 carbon atoms, wherein at least one ring is aromatic chosen from 2,7-Naphthalenediol; 1,5-Naphthalenediol; 1-Hydroxy-naphthalene; and 2-Methyl-1-naphthol.

12. The process according to claim 1, wherein composition (A) comprises at least one metal salt chosen from iron, manganese, or zinc salts.

13. The process according to claim 1, wherein composition (A) comprises at least one metal salt chosen from metal salts in oxidation state II that bear two ligands derived from (poly)hydroxy acid.

14. The process according to claim 1, wherein composition (A) comprises at least one metal salt chosen from salts complexed with two carboxylate groups chosen from compounds of formula (VI) below:
RC(O)O-M-OC(O)R(VI) and the solvates or enantiomers thereof, wherein: M is chosen from a metal (II) or metal.sup.2+ in oxidation state 2; and R and R, which may be identical or different, are a (C.sub.1-C.sub.6)(poly)hydroxyalkyl group.

15. The process according to claim 1, wherein the at least one metal salt is chosen from organic acid salts chosen from citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates, or tartrates.

16. The process according to claim 1, further comprising at least one natural ortho-diphenol other than the indole or indoline compounds, wherein the at least one natural ortho-diphenol is chosen from extracts of tea or rose leaves, extracts of rosemary leaves, extracts of mate leaves, extracts of fruit, extracts of legumes, extracts of tree wood, extracts of quebracho wood, extracts of braziletto wood, or extracts of gall nuts.

17. The process according to claim 1, further comprising hydrogen peroxide or at least one hydrogen peroxide-generating system.

18. The process according to claim 1, further comprising a composition (B), composition (B) comprising at least one mineral basifying agent.

19. The process according to claim 18, wherein the at least one mineral basifying agent is chosen from organic amines.

20. The process according to claim 18, wherein the at least one mineral basifying agent is chosen from alkanolamines, diethanolamines, triethanolamines, 2-amino-2-methyl-1-propanol, amino acids, or mixtures thereof.

21. The process according to claim 18, wherein composition (B) is applied to the hair after composition (A).

22. The process according to claim 21, wherein between the application of composition (A) and the application of composition (B), the hair fibers are a) wiped mechanically, b) dried by heat with a heat treatment, or c) not rinsed.

23. A dyeing composition comprising i) at least one indole or indoline compound; ii) at least one aromatic compound comprising a hydrocarbon-based polycycle comprising at least 10 carbon atoms, wherein at least one ring is aromatic and substituted with at least one hydroxyl or amino group; optionally, iii) at least one metal salt chosen from transition metal salts, rare-earth metal salts, or mixtures thereof, or at least one natural ortho-diphenol; optionally iv) hydrogen peroxide or at least one hydrogen peroxide generating system; and optionally v) at least one basifying agent.

24. A kit for dyeing keratin fibers, comprising at least 2 compartments and at least 2 compositions, the compositions comprising: i) at least one indole or indoline compound; ii) at least one aromatic compound comprising a hydrocarbon-based polycycle comprising at least 10 carbon atoms, wherein at least one ring is aromatic and substituted with at least one hydroxyl or amino group; optionally iii) at least one metal salt; optionally iv) hydrogen peroxide or at least one hydrogen peroxide-generating system; and optionally v) at least one basifying agent.

Description

DYEING EXAMPLES

(1) Compositions A1, A2 and B were prepared as follows:

(2) The values given in Tables 1 and 2 are given in g per 100 g of composition:

(3) TABLE-US-00001 TABLE 1 A1 A2 Ingredients Comparative Invention 5,6-Dihydroxyindole, i) 0.5 0.5 2,7-Dihydroxynaphthalene, ii) 1 Manganese gluconate iii) 0.2 0.2 Hydrogen peroxide, iv) 2.4 2.4 Propanediol, 5 5 Caprylyl/capryl glucoside 2 2 Denatured alcohol 5 5 Demineralized water qs 100 g qs 100 g

(4) TABLE-US-00002 TABLE 2 Ingredients B Sodium bicarbonate 5 Monoethanolamine (MEA) 2 Hydroxyethylcellulose (HEC) 1.5 Demineralized water qs 100 g
For the 3 Tests:

(5) Each composition A1 and A2 is applied to locks of natural Caucasian hair containing 90% white hairs. The compositions are then left on the locks for 30 minutes at 27 C.

(6) After this leave-on time, the hair impregnated with the first composition is wiped using an absorbent paper towel. Immediately after wiping, without waiting for the hair to dry, composition B is applied; the leave-on time is 2 minutes at room temperature.

(7) Next, the lock is rinsed with tap water, shampooed with a standard shampoo (Ultra doux camomile), rinsed with tap water and dried under a hood at 40 C.

(8) Composition A2 according to the invention gives a more powerful colouring than composition A1.

(9) Colorimetric Results:

(10) The hair colouring is measured using a Minolta spectrocolorimeter (CM2600d, illuminant D65, angle 10, specular component included) in the CIELab system.

(11) 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. The higher the value of a*, the redder the shade and, the higher the value of b*, the yellower the shade.

(12) The chromaticity C* is calculated using the equation:
C*={square root over (a*.sup.2+b*.sup.2)}

(13) The colorimetric measurements were taken before exposure to light, and then after exposure to light.

(14) The locks dyed using the compositions described above were exposed to light according to the following protocol:

(15) The dyed locks are exposed to light using a Xenotest 150S machine from the company Atlas at an average lighting level (about 1250 W/m.sup.2 between 300 and 800 nm for 7 infrared filters). The humidity level is set at 60%. The exposure time is 40 hours.

(16) In this L*, a*, b* system, L* represents the intensity of the color, a* indicates the green/red color axis and b* indicates the blue/yellow color axis. The lower the value of L, the darker or more intense the color. The higher the value of a*, the redder the shade; the higher the value of b*, the yellower the shade.

(17) The variation in coloring between the colored locks which is not exposure to light (control) and after coloration and exposure to light are defined by E*, corresponding to the colour fastness to light on keratin fibers, according to the following equation:
E={square root over ((L*L.sub.o*).sup.2+(a*a.sub.o*).sup.2+(b*b.sub.o*).sup.2)}
In this equation, L*, a* and b* represent the values measured after the exposure to light of the colored hair and L.sub.0*, a.sub.0* and b.sub.0* represent the values measured before the exposure to light of the colored hair.

(18) The more important E is, the higher difference of the color before and after the light exposure of the hair, which corresponds to weaker light fastness.

(19) Results on E and C:

(20) TABLE-US-00003 TABLE 3 before Xenotest Lock before A1 + B A2 + B dyeing (Comparative) (Invention) L* 66.4 24.8 21.6 a* 0.8 0.1 0.3 b* 16.5 0.5 0.3 E 44.6 47.6

(21) TABLE-US-00004 TABLE 4 After Xenotest Lock A1 + B A2 + B before dyeing (Comparative) (Invention) L* 66.4 24.5 20.1 a* 0.8 0.9 0.6 b* 16.5 3.7 1.2 E 43.8 48.8

(22) TABLE-US-00005 TABLE 5 Results b after-before Xenotest A1 + B (Comparative) A2 + B (Invention) difference b after-before 3.2 0.9 exposure

(23) According to the results of the tables 3 and 4 it appears that composition of the invention allows to obtain a significantly higher color uptake than the comparative one. Moreover, according to the table 5, the b value after and before the xenotest treatment is significant for the dyeing process A1+B (comparative) than the dyeing process A2+B (invention).

(24) Chromaticity:

(25) The change of colour after exposure to light is reflected by the variation in the chromaticity C, and in particular the change towards yellow by the variation in b*b on the blue/yellow colour axis

(26) with C=C*C.sub.0*, C* corresponding to the chromaticity

(27) after exposure to light and C.sub.0* to the chromaticity before exposure to light,

(28) and b=b*b.sub.0*, b* corresponding to the value after exposure to light and b.sub.0* to the value before exposure to light.

(29) TABLE-US-00006 TABLE 6 Dyeing process Xenotest a* b* C* C A2 + B (invention) Before exposure 0.3 0.3 0.4 0.9 After exposure 0.6 1.2 1.3 A1 + B (comparative) Before exposure 0.1 0.5 0.5 3.3 After exposure 0.9 3.7 3.8

(30) The values of C and b are lower in the case of composition A2 than composition A1: composition A2 leads to less changing of the colour, in particular towards yellow, than composition A1.

(31) Compositions A3 to A5:

(32) The values given in Table 7 are given in g per 100 g of composition:

(33) TABLE-US-00007 TABLE 7 A3 A4 A5 Ingredients Invention Invention Invention 5,6-Dihydroxyindole, i) 0.5 0.5 0.5 1,5-Dihydroxynaphthalene, iii) 1 1-Hydroxy-naphthalene, iv) 1 2-Methyl-1-naphthol, vi) 1 Manganese gluconate vii) 0.2 0.2 0.2 Hydrogen peroxide, viii) 2.4 2.4 2.4 Propanediol, 5 5 5 Caprylyl/capryl glucoside 2 2 2 Denatured alcohol 5 5 5 Demineralized water qs 100 g qs 100 g qs 100 g

(34) Each composition A3 to A5 is applied to locks of natural Caucasian hair containing 90% white hairs. The compositions are then left on the locks for 30 minutes at 27 C.

(35) After this leave-on time, the hair impregnated with the first composition is wiped using an absorbent paper towel. Immediately after wiping, without waiting for the hair to dry, composition B is applied; the leave-on time is 2 minutes at room temperature.

(36) Next, the lock is rinsed with tap water, shampooed with a standard shampoo (Ultra doux camomile), rinsed with tap water and dried under a hood at 40 C.

(37) It has been observed that composition according to the invention containing i) 5,6-dihydroxyindole with ii) 2,7-naphtalendiol, 1,5-naphtalendiol, 1-hydroxynaphtol and 2-methy-1-naphtol and iii) metal salt in particular manganese salt allow to obtain a high level of colour uptake DE and/or intensive colour. The fastness of the colour especially vs the light is also good. On the other hand it has been observed that 2,7-naphtalendiol, 1,5-naphtalendiol, 1-hydroxynaphtol and 2-methy-1-naphtol allow to avoid the changing of the colour, in particular towards yellow.