Process for dyeing hair comprising at least one pigment, at least one acrylate-functionalized polymer and at least one functionalized silicone chosen from silicones functionalized with at least one mercapto or thiol group

Abstract

The present invention relates to a composition intended for dyeing keratin fibres, in particular of human keratin fibres such as the hair, comprising one or more acrylate-functionalized polymers and one or more silicones chosen from silicones functionalized with one or more mercapto groups, amino silicones, and mixtures thereof, and one or more pigments.

Claims

1. A composition comprising: (i) one or more acrylate-functionalized polymers, wherein the one or more acrylate-functionalized polymer(s) is or are chosen from acrylate-functionalized silicone homopolymers and acrylate-functionalized silicone copolymers, (ii) one or more silicones functionalized with one or more mercapto groups, wherein the one or more silicone(s) functionalized with one or more mercapto groups is or are chosen from the compounds of the following formulae: ##STR00010## in which R.sub.1 denotes a saturated or unsaturated, linear or branched, optionally cyclic, hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with a heteroatom chosen from N, O, S and P, R.sub.2 denotes an alkyl group containing from 1 to 6 carbon atoms or an alkoxy group containing from 1 to 6 carbon atoms, n ranges from 0 to 132, n.sub.1 ranges from 1 to 132, and m ranges from 1 to 132, and (iii) one or more pigments.

2. The composition according to claim 1, wherein the one or more acrylate-functionalized polymer(s) is or are a polymer of formula (I) or (II) below: ##STR00011## wherein: R.sub.a denotes a saturated or unsaturated, linear or branched, optionally cyclic, hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with a heteroatom chosen from N, O, S and P, R.sub.b denotes an alkyl group containing from 1 to 6 carbon atoms or an alkoxy group containing from l to 6 carbon atoms, t ranges from 0 to 132, u ranges from 1 to 132, v ranges from 1 to 132, and X represents an acrylate-functionalized group.

3. The composition according to claim 1, wherein the one or more acrylate-functionalized polymer(s) is or are of formula (III) below: ##STR00012## in which u ranges from t to 132, and v ranges from 1 to 132.

4. The composition according to claim 1, wherein the one or more acrylate-functionalized polymer(s) is or are chosen from silicone copolymers of acrylate and of dimethylpolysiloxane.

5. The composition according to claim 1, comprising one or more acrylate-functionalized silicone homopolymers.

6. The composition according to claim 1 wherein the amount of the one or more pigments in the composition ranges from 0.5 to 30% by weight with respect to the weight of the composition.

7. A hair dye comprising the composition according to claim 1.

8. The composition according to claim 1, comprising one or more acrylate-functionalized silicone copolymers.

9. A hair dye comprising the composition according to claim 5.

10. A hair dye comprising the composition according to claim 8.

11. The composition according to claim 5, wherein the amount of the one or more pigments in the composition ranges from 0.5 to 30% by weight with respect to the weight of the composition.

12. The composition according to claim 8, wherein the amount of the one or more pigments in the composition ranges from 0.5 to 30% by weight with respect to the weight of the composition.

13. A composition comprising: one or more acrylate-functionalized polymers, wherein the one or more acrylate-functionalized polymer(s) is or are chosen from acrylate-functionalized silicone homopolymers and acrylate-functionalized silicone copolymers, one or more silicones functionalized with one or more mercapto groups, wherein the one or more silicone(s) functionalized with one or more mercapto groups is or are chosen from the compounds of the following formulae: ##STR00013## in which R.sub.1 denotes a saturated or unsaturated, linear or branched, optionally cyclic, hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with a heteroatom chosen from N, O, S and P, R.sub.2 denotes an alkyl group containing from 1 to 6 carbon atoms or an alkoxy group containing from 1 to 6 carbon atoms, n ranges from 0 to 132, n.sub.1 ranges from 1 to 132, and m ranges from 1 to 132, and one or more pigments having solubility in water at 25? C. and 760 mmHg of less than 0.05% by weight.

14. The composition according to claim 13, wherein the one or more acrylate-functionalized polymer(s) is or are a polymer of formula (I) or (II) below: ##STR00014## wherein: R.sub.a denotes a saturated or unsaturated, linear or branched, optionally cyclic, hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with a heteroatom chosen from N, O, S and P, R.sub.b denotes an alkyl group containing from 1 to 6 carbon atoms or an alkoxy group containing from 1 to 6 carbon atoms, t ranges from 0 to 132, u ranges from 1 to 132, v ranges from 1 to 132, and X represents an acrylate-functionalized group.

15. The composition according to claim 13, wherein the one or more acrylate-functionalized polymer(s) is or are of formula (III) below: ##STR00015## in which u ranges from 1 to 132, and v ranges from 1 to 132.

16. The composition according to claim 13, wherein the one or more acrylate-functionalized polymer(s) is or are chosen from silicone copolymers of acrylate and of dimethylpolysiloxane.

17. The composition according to claim 13, comprising one or more acrylate-functionalized silicone copolymers.

18. The composition according to claim 13, wherein the amount of the one or more pigments in the composition ranges from 0.5 to 30% by weight with respect to the weight of the composition.

19. A hair dye comprising the composition according to claim 13.

Description

EXAMPLES

(1) The below data were generated from natural locks of hair with 90% of white hair. On 1 gram of lock was applied 0.5 g of dyeing composition.

(2) The locks of hair were treated with the ingredients indicated in the table below:

(3) TABLE-US-00001 compositions Ingredients (weight %) 1 Composition containing Acrylate-functionalized silicone polymer.sup.(2) 0.75% (active material), pigment.sup.(3) 6% and qs 100% isododecane 2 Composition containing Silicone functionalized with mercapto groups.sup.(1) 0.5% (active material), Pigment.sup.(3) 6%, q.s. 100% isododecane 3 Composition containing Bis-Cetearyl Amodimethicone 0.25% (active material), Pigments (3) 6%, q.s. 100% isododecane 4a Composition containing silicone functionalized with mercapto groups.sup.(1) 0.5% (active material) by weight and acrylate-functionalized silicone polymer.sup.(2) 0.75% (active material) by weight, pigments.sup.(3) 6% in weight, bis-cetearyl amodimethicone 3% (active material) by weight, q.s. 100% isododecane 4b Composition containing silicone functionalized with mercapto groups.sup.(1) 6% (active material) by weight and acrylate-functionalized silicone polymer.sup.(2) 9% (active material) by weight, pigments.sup.(3) 6% in weight, bis-cetearyl amodimethicone 3% (active material) by weight, q.s. 100% isododecane .sup.(1)sold under the name KF2001 by the company Shin-Etsu (formula XXV with R1 = C.sub.3H.sub.6 and R2 = CH.sub.3) .sup.(2)sold under the name UMS 182 by the company Gelest (formula (III)) .sup.(3)IRON OXIDES (and) MICA (pearlescent pigment sold by Eckart)
Composition 5 (Comparison):

(4) TABLE-US-00002 Comparative composition 5 Conc. GLYCINE .sup.3% PHENOXYETHANOL 0.7% DIVINYLDIMETHICONE/DIMETHICONE 8.3% COPOLYMER (and) C12-13 PARETH-3 (and) C12-13 PARETH-23 (60% Active Material in an aqueous emulsion) CAPRYLYL GLYCOL .sup.1% MAGNESIUM ALUMINUM SILICATE 1.1% STYRENE/ACRYLATES/AMMONIUM METH- 21% ACRYLATE COPOLYMER (and) SODIUM LAURETH SULFATE (and) CAPRYLYL GLYCOL (40% Active material in an aqueous emulsion 40%) MICA (and) IRON OXIDES .sup.6% water q.s
I. Evaluation Procedure

(5) The compositions 1 to 4 described in the table above are applied to locks with a brush, then they were heated at 50? C. on a heating plate. After 1 hour at 50? C., the locks were treated with a straightening (10 times at 210? C.) and then left at 50? C. 1 hour more.

(6) The locks are left to stand at room temperature for a time of 48 hours before performing a first color evaluation (measurement T0).

(7) Then the locks were washed with water by soaking the locks in water for 1 hour. After 24 h a room temperature, the color was re evaluated (T1), then the color was evaluated after 2 shampoos and 24 h at room temperature (T2).

(8) For the compositions 1 to 3, the color evaluation (T2) was conducted after 1 shampoo (most of the color was removed after 1 shampoo).

(9) For composition 5, the composition was applied on a lock and left 30 min at 50? C.

(10) The color evaluation was done with a spectrophotometer in the L*a*b* system wherein According to this system, L indicates the lightness. The lowest is the value of L, the most intense is the color of the hair. The chromaticity coordinates are expressed by the parameters a* and b*, a* indicating the axis of red/green shades and b the axis of yellow/blue shades.

(11) TABLE-US-00003 L* a* b* control 63.1 0.8 16.9 T0 L* a* b* control 63.1 0.8 16.9 1 55.7 12.5 19.3 2 54.8 12.8 19.4 3 56.2 12.9 19.4 T1 L* a* b* 1 56.6 10.02 19 2 55.0 11.6 18.7 3 57.0 12.2 19.4 T2 L* a* b* 1 61.0 3.8 16.9 2 61.7 4.3 17.8 3 62.2 3.6 17.0 4a 53.1 12.2 19.7

(12) These results show that alone, these silicone did not provide a color retention after shampooing.

(13) TABLE-US-00004 L* a* b* T0 4b 53.4 13.9 20.9 5 54.8 11.2 17.7 T1 4b 52.3 14.04 21.2 5 54.4 10.71 17.9 T2 4b 54.1 12.6 21.3 5 58.7 5.5 16.7

(14) These results show that the composition of the invention exhibit an improved color fastness. Additionally, the lock treated with the composition of the invention is brighter and softer than the lock treated with the composition 5. With composition 4, there was no color transfert when rubbed with paper).

(15) Compositions with a Photoinitiator

(16) The locks of hair were treated with the ingredients indicated in the table below:

(17) TABLE-US-00005 compositions Ingredients (weight %) 1c Composition containing Acrylate-functionalized silicone polymer(2) 9% (active material), Ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate (photoinitiator) 0.9% pigment.sup.(3) 6% and qs 100% isododecane 2c Composition containing Silicone functionalized with mercapto groups.sup.(1) 6% (active material), Ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate (photoinitiator) 0.9% Pigment.sup.(3) 6%, q.s. 100% isododecane 3c Composition containing Bis-Cetearyl Amodimethicone 3% (active material), Ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate (photoinitiator) 0.9% Pigments.sup.(3) 6%, q.s. 100% isododecane 4c Composition containing silicone functionalized with mercapto groups.sup.(1) 6% (active material) and acrylate-functionalized silicone polymer.sup.(2) 9% (active material), Ethyl (2,4,6-trimethyIbenzoyl) phenylphosphinate (photoinitiator) 0.9% pigments.sup.(3) 6% , bis-cetearyl amodimethicone** 3% (active material), q.s. 100% isododecane .sup.(1)sold under the name KF2001 by the company Shin-Etsu (formula XXV with R1 = C.sub.3H.sub.6 and R2 = CH.sub.3) .sup.(2)sold under the name UMS 182 by the company Gelest (formula (III)) .sup.(3)IRON OXIDES (and) MICA (pearlescent pigment sold by Eckart).

(18) The compositions 1c to 4c described in the table above are applied to locks with a brush, then the locks were exposed to UV radiations (2?5 min).

(19) The locks are left to stand at room temperature for a time of 48 hours before performing a first color evaluation (measurement T0).

(20) Then the locks were washed with water by soaking the locks in water for 1 hour. After 24 h a room temperature, the color was re-evaluated (T1), then the color was evaluated after 2 shampoos and 24 h at room temperature (T2) and then after 5 shampoos and 24 h at room temperature for the composition of the invention.

(21) For the compositions 1 b to 3b, the color evaluation (T2) was conducted after 1 shampoo (most of the color was removed after 1 shampoo).

(22) For composition 5, the composition was applied on a lock and left 30 min at 50? C.

(23) The color evaluation was conducted as disclosed in the previous examples. The L*a*b* results are reported in the table below:

(24) TABLE-US-00006 L* a* b* control 63.1 0.8 16.9 T0 1b 53.9 14.4 19.9 2b 54.1 14.9 20.8 3b 53.07 14.13 19.7 T1 1b 55.1 12.5 18.7 2b 54.0 13.9 20.3 3b 54.9 13.5 19.3 T2 1b 58.4 3.0 14.3 2b 59.5 6.2 16.9 3b 58.5 5.0 15.7

(25) These results show that alone, these silicones did not provide a color retention. Additionally, the water in which the locks 1c to 3c were soaked was colored whereas the water for the lock 4c remains uncoloured.

(26) TABLE-US-00007 L* a* b* T0 4 53.0 13.6 20.4 5 54.8 11.2 17.7 T1 4 52.7 14.3 20.3 5 54.4 10.7 17.9 T2 4 52.1 11.7 17.9 5 58.7 5.5 16.7 T3 4 55.1 12.7 20.0

(27) These results show that the composition of the invention provide an improved color retention, still noticeable after 5 shampoo.