HAIR DYEING PROCESS USING AT LEAST ONE SILICONE COMPRISING AT LEAST ONE CARBOXYLIC ACID ANHYDRIDE GROUP, AT LEAST ONE AMINO SILICONE AND AT LEAST ONE PIGMENT AND/OR DIRECT DYE

Abstract

The subject of the present invention is a process for treating keratin fibers using a) at least one silicone comprising at least one carboxylic acid anhydride group, b) at least one amino silicone, and c) at least one coloring agent chosen from pigments, direct dyes and mixtures thereof, the compounds a), b) and c) being applied together or separately, in one or more compositions.

Claims

1.-15. (canceled)

16. A process for treating keratin fibers, comprising: applying to the keratin fibers: a) at least one silicone comprising at least one carboxylic acid anhydride group, b) at least one amino silicone; and c) at least one coloring agent chosen from pigments, direct dyes and mixtures thereof, wherein the a) at least one silicone, b) at least one amino silicone, and c) at least one coloring agent are applied to the keratin fibers, together or separately, in one or more compositions.

17. The process of claim 16, wherein the at least one silicone comprising at least one carboxylic acid anhydride group chosen from organosiloxanes of formula (I): ##STR00026## wherein: R.sub.1 is independently chosen from an alkyl group containing from 1 to 20 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH); a cycloalkyl group containing from 3 to 20 carbon atoms; an alkoxy group containing from 1 to 2 carbon atoms; an aryl group containing from 6 to 12 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH) or a group of formula (II): ##STR00027## wherein R.sub.3 represents an alkyl group containing from 1 to 4 carbon atoms; p denotes an integer ranging from 0 to 4; R.sub.2 is independently chosen from an alkyl group containing from 1 to 20 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH); a cycloalkyl group containing from 3 to 20 carbon atoms; an alkoxy group containing from 1 to 2 carbon atoms; an aryl group containing from 6 to 12 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH); m denotes an integer ranging from 1 to 10; and n denotes an integer ranging from 1 to 50; wherein at least one of the radicals R1 represents a group of formula (II).

18. The process of claim 16, wherein the at least one silicone comprising at least one carboxylic acid anhydride group is chosen from organosiloxanes of formula (III): ##STR00028## wherein: R.sub.1 is independently chosen from an alkyl group containing from 1 to 20 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH); a cycloalkyl group containing from 3 to 20 carbon atoms; an alkoxy group containing from 1 to 2 carbon atoms; an aryl group containing from 6 to 12 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH) or a group of formula (II): ##STR00029## wherein R.sub.3 represents an alkyl group containing from 1 to 4 carbon atoms; p denotes an integer ranging from 0 to 4; R.sub.2 is independently chosen from an alkyl group containing from 1 to 20 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH); a cycloalkyl group containing from 3 to 20 carbon atoms; an alkoxy group containing from 1 to 2 carbon atoms; an aryl group containing from 6 to 12 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH); R.sub.4 represents an alkyl group containing from 1 to 4 carbon atoms; A represents an alkylene group containing from 1 to 4 carbon atoms; m denotes an integer ranging from 1 to 10; and n denotes an integer ranging from 1 to 50.

19. The process of claim 16, wherein the at least one silicone comprising at least one carboxylic acid anhydride group is chosen from organosiloxanes of formula (IV): ##STR00030## wherein: R.sub.2 is independently chosen from an alkyl group containing from 1 to 20 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH); a cycloalkyl group containing from 3 to 20 carbon atoms; an alkoxy group containing from 1 to 2 carbon atoms; an aryl group containing from 6 to 12 carbon atoms, optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH); A represents an alkylene group containing from 1 to 4 carbon atoms; m denotes an integer ranging from 1 to 10; and n denotes an integer ranging from 1 to 50.

20. The process of claim 16, wherein the one or more compositions used in the process comprise the at least one silicone comprising at least one carboxylic acid anhydride group in a total amount ranging from 0.1% to 40% by weight, relative to the total weight of the composition.

21. The process of claim 16, wherein the at least one amino silicone is chosen from amino silicones corresponding to formula (B): ##STR00031## wherein: R.sub.1 is independently chosen from a hydrogen atom, a phenyl group, a hydroxyl group, a C.sub.1-C.sub.8 alkyl group; R.sub.2 represents a monovalent radical of formula —C.sub.qH.sub.2qL wherein q is a number ranging from 2 to 8 and L is an optionally quaternized amino group chosen from: —N(R″).sub.2; —N.sup.+(R″).sub.3A.sup.−; —NR″-Q-N(R″).sub.2 and —NR″-Q-N.sup.+(R″).sub.3A.sup.−, wherein R″ is independently chosen from a hydrogen atom, a phenyl group, a benzyl group or a saturated monovalent hydrocarbon-based radical; Q denotes a linear or branched group of formula C.sub.rH.sub.2r, r being an integer ranging from 2 to 6; and A.sup.− represents a cosmetically acceptable anion comprising a halide; R.sub.3 is independently chosen from a C.sub.1-C.sub.8 alkyl group, or a monovalent radical of formula —C.sub.qH.sub.2qL wherein q is a number ranging from 2 to 8 and L is an optionally quaternized amine group chosen from: —N(R″).sub.2; —N.sup.+(R″).sub.3A.sup.−; —NR″-Q-N(R″).sub.2 and —NR″-Q-N.sup.+(R″).sub.3A.sup.−, wherein R″ is independently chosen from a hydrogen atom, a phenyl group, a benzyl group or a saturated monovalent hydrocarbon-based radical, for example a C.sub.1-C.sub.20 alkyl group; Q denotes a linear or branched group of formula C.sub.rH.sub.2r, r being an integer ranging from 2 to 6; and A.sup.− represents a cosmetically acceptable anion comprising a halide; and m and n are numbers such that the sum (n+m) ranges from 1 to 2000, wherein m denotes a number from 0 to 1999, and n denotes a number from 1 to 2000.

22. The process of claim 21, wherein the at least one amino silicone is chosen from amino silicones corresponding to formula (C): ##STR00032## wherein m and n are numbers such that the sum (n+m) ranges from 1 to 2000.

23. The process of claim 16, wherein the at least one amino silicone is present in a total amount ranging from 0.01% to 20% by weight, relative to the total weight of the one or more compositions.

24. The process of claim 16, wherein at least one of the one or more compositions comprises one or more oils.

25. The process of claim 24, wherein the one or more oils are chosen from C.sub.8-C.sub.16 alkanes.

26. The process of claim 16, wherein the at least one coloring agent is present in a total amount ranging from 0.05% to 30% by weight, relative to the total weight of the one or more compositions.

27. A process for cosmetically treating keratin fibers, comprising: applying to the keratin fibers a composition (A) comprising at least one amino silicone; optionally washing, rinsing, drying and/or wringing out the keratin fibers; and applying to the keratin fibers a composition (B) comprising at least one silicone comprising at least one carboxylic acid anhydride group; wherein at least one of the composition (A) or the composition (B) comprises at least one coloring agent chosen from pigments, direct dyes and mixtures thereof, wherein the at least one amino silicone, the at least one silicone, and the at least one coloring agent are applied to the keratin fibers, together or separately, in one or more compositions.

28. The process of claim 16, further comprising applying to the keratin fibers a makeup-removing composition comprising at least one hydrocarbon-based oil.

29. The process as claimed in claim 28, wherein the application of the one or more compositions to the keratin fibers is carried out before the application of the makeup-removing composition.

30. A multi-compartment device comprising: a first compartment containing a composition (A) comprising at least one amino silicone; a second compartment containing a composition (B) comprising at least one silicone comprising at least one carboxylic acid anhydride group; and optionally a third compartment containing a makeup-removing composition (D) comprising at least one hydrocarbon-based oil; wherein at least one of the composition (A) or the composition (B) comprises at least one coloring agent chosen from pigments, direct dyes and mixtures thereof.

Description

EXAMPLE

Example 1

[0490] Composition Base Coat: Compositions (g/100 g)

TABLE-US-00001 TABLE 1 Compositions A B Amodimethicone (KF-8004 5 5 sold by the company Shin Etsu) Pigment (red iron oxide) 5 5 Cetyl PEG/PPG-10/1 — 1 dimethicone (Abil EM 90 sold by the company Evonik Goldschmidt) Isododecane qs 100 10 Water — qs 100

[0491] Composition Top Coat: Compositions (g/100 g)

TABLE-US-00002 TABLE 2 Compositions C D Silicone comprising at least 5 5 one carboxylic acid anhydride group (X-22-168A sold by the company Shin Etsu) Cetyl PEG/PPG-10/1 — 1 dimethicone (Abil EM 90 sold by the company Evonik Goldschmidt) Isododecane qs 100 6 Water — qs 100

[0492] Protocol:

[0493] Compositions A and B according to the invention (base coat compositions) are applied respectively to locks of natural dry hair containing 90% gray hairs, in a proportion of 0.5 g of composition per gram of lock.

[0494] The locks of hair are then combed and dried with a hairdryer.

[0495] Compositions C and D according to the invention (top coat compositions) are then applied respectively to said locks of dry hair, in a proportion of 0.5 g of composition per gram of lock.

[0496] The locks of hair are then combed and dried with a hairdryer. The locks of hair are left at ambient temperature for 24 hours.

[0497] The locks of hair have a natural feel and can be separated with the fingers or by using a comb and/or a brush.

[0498] The locks of hair thus dyed are then subjected to a test of several repeated shampoo washes so as to evaluate the resistance (persistence) of the coloring obtained with respect to shampoo washing.

[0499] Shampoo wash protocol:

[0500] The locks are washed with a standard shampoo (Gamier Ultra Doux) respectively at T=24 h.

[0501] The locks of hair are then rinsed, combed and dried with a hairdryer.

[0502] The next shampoo wash is then performed on the locks thus dried.

[0503] Results:

[0504] The persistence of the color of the locks was evaluated in the CIE L*a*b* system, using a Minolta Spectrophotometer CM3600D colorimeter (illuminant D65, angle 10°, specular component included).

[0505] In this L*a*b* system, L* represents the intensity of the color, a* indicates the green/red color axis and b* the blue/yellow color axis.

[0506] The persistence of the coloring is evaluated by the color difference ΔE between the dyed locks before shampooing, then after having undergone 2, 5, 10 and 20 shampoo washes according to the protocol described above. The lower the ΔE value, the more persistent the color with respect to shampoo washing.

[0507] The ΔE value is calculated according to the following equation:

[00001]$\begin{array}{cc}\Delta E=\sqrt{{\left(L^{\star }-L_0^{\star }\right)}^2+{\left(a^{\star }-a_0^{\star }\right)}^2+{\left(b^{\star }-b_0^{\star }\right)}^2}& \left[\mathrm{Math}.1\right]\end{array}$

[0508] In this equation, L*a*b* represent the values measured after dyeing the hair and after performing the shampoo washes, and L.sub.0*a.sub.0*b.sub.0* represent the values measured after dyeing the hair but before shampoo washing.

TABLE-US-00003 TABLE 3 Number of shampoo Compositions washes L* a* b* ΔE Compositions 0 39.49 22.48 18.41 — A + C 2 38.52 25.07 21.51 4.15 5 42.79 18.73 16.92 5.21 10 48.04 17.13 18.15 10.09 20 54.96 10.69 16.79 19.52 Compositions 0 37.54 32.81 28.53 — B + D 2 40.38 32.56 28.82 2.87 5 38.69 31.38 27.03 2.37 10 43.35 29.1 25.25 7.63 20 47.92 23.1 21.47 15.87

[0509] The locks of hair dyed with the compositions A+C or with the compositions B+D according to the invention and washed with two, five, ten or twenty shampoo washes have low ΔE values.

[0510] Thus, the colored coating of the keratin fibers obtained with compositions A+C or with compositions B+D according to the invention shows good persistence with respect to shampoo washing. Indeed, the locks of hair dyed with the compositions A+C or with the compositions B+D according to the invention and washed with two, five, ten or twenty shampoo washes have good color persistence.

Example 2

[0511] Composition Base Coat: Compositions (g/100 g)

TABLE-US-00004 TABLE 4 Compositions B Amodimethicone (KF-8004 5 sold by the company Shin Etsu) Pigment (red iron oxide) 5 Cetyl PEG/PPG-10/1 1 dimethicone (Abil EM 90 sold by the company Evonik Goldschmidt) Isododecane 10 Water qs 100

[0512] Composition Top Coat: Compositions (g/100 g) AM: Active Material

TABLE-US-00005 TABLE 5 D1 D2 Compositions (invention) (comparative) Silicone comprising at least 5 am — one carboxylic acid anhydride group (X-22-168A sold by the company Shin Etsu) Dimethicone PEG-7 — 5 am phosphate (Silsense PE-200L Silicone sold by the company Lubrizol) Cetyl PEG/PPG-10/1 1 1 dimethicone (Abil EM 90 sold by the company Evonik Goldschmidt) Isododecane 6 6 Water qs 100 qs 100

[0513] Protocol:

[0514] Composition B (base coat composition) is applied respectively to locks of natural dry hair containing 90% gray hairs, in a proportion of 0.5 g of composition per gram of lock.

[0515] The locks of hair are then combed and dried with a hairdryer.

[0516] Composition D1 according to the invention and comparative composition D2 (top coat compositions) are then applied respectively to said locks of dry hair, in a proportion of 0.5 g of composition per gram of lock.

[0517] The locks of hair are then combed and dried with a hairdryer. The locks of hair are left at ambient temperature for 24 hours.

[0518] The locks of hair have a natural feel and can be separated with the fingers or by using a comb and/or a brush.

[0519] The locks of hair thus dyed are then subjected to a test of several repeated shampoo washes so as to evaluate the resistance (persistence) of the coloring obtained with respect to shampoo washing.

[0520] The Shampoo wash protocol is the same as the one described in example 1.

[0521] Results:

[0522] The persistence of the color of the locks was evaluated in the CIE L*a*b* system, using a Minolta Spectrophotometer CM3600D colorimeter (illuminant D65, angle 10°, specular component included).

[0523] In this L*a*b* system, L* represents the intensity of the color, a* indicates the green/red color axis and b* the blue/yellow color axis.

[0524] The persistence of the coloring is evaluated by the color difference ΔE between the dyed locks before shampooing, then after having undergone 3 shampoo washes according to the protocol described in example 1. The lower the ΔE value, the more persistent the color with respect to shampoo washing.

[0525] The ΔE value is calculated according to the following equation:

[00002]$\begin{array}{cc}\Delta E=\sqrt{{\left(L^{\star }-L_0^{\star }\right)}^2+{\left(a^{\star }-a_0^{\star }\right)}^2+{\left(b^{\star }-b_0^{\star }\right)}^2}& \left[\mathrm{Math}.2\right]\end{array}$

[0526] In this equation, L*a*b* represent the values measured after dyeing the hair and after performing the shampoo washes, and L.sub.0*a.sub.0*b.sub.0* represent the values measured after dyeing the hair but before shampoo washing.

TABLE-US-00006 TABLE 3 Number of shampoo Compositions washes L* a* b* ΔE Compositions 0 37.26 31 25.48 — B + D1 (invention) 3 38.53 28.88 23.22  3.35 Compositions 0 36.69 29.02 23.56 — B + D2 (comparative) 3 63.6 3.97 17.06 37.33

[0527] The locks of hair dyed with the compositions B+D1 according to the invention and washed with three shampoo washes have lower ΔE values than the locks of hair dyed with the comparative composition B+D2.

[0528] Thus, the colored coating of the keratin fibers obtained with compositions B+D1 according to the invention shows good persistence with respect to shampoo washing. Indeed, the locks of hair dyed with compositions B+D1 according to the invention and washed with three shampoo washes have better persistence of the color than the locks of hair dyed with the comparative composition B+D2.