DYE COMPOSITION BASED ON COPOLYMERS DERIVED FROM THE POLYMERIZATION OF AT LEAST ONE CROTONIC ACID MONOMER OR CROTONIC ACID DERIVATIVE AND ON SILICONE

Abstract

The subject of the present invention relates to a composition for dyeing keratin fibers, comprising: a)one or more copolymer(s) derived from the polymerization of at least one monomer of crotonic acid or crotonic acid derivative and of at least one vinyl ester monomer, b)at least one oil-in-water emulsion having a particle size D 50 of less than 350 nm and which comprises: a silicone mixture comprising (i) at least one polydialkylsiloxane comprising trialkylsilyl end groups, having a viscosity at 25 C. ranging from 40 000 to 100 000 mPa.Math.s and (ii) at least one aminosilicone having aviscosity at 25 C. ranging from 1000 to 15 000 mPa.Math.s and an amine number ranging from 2 to 10 mg of KOH per gram of aminosilicone; a surfactant mixture comprising one or more nonionic surfactants, said mixture having an HLB ranging from 10 to 16, and water and c) at least one pigment.

Claims

1. -22. (canceled)

23. A composition comprising: a) at least one copolymer derived from the polymerization of at least one monomer of crotonic acid or crotonic acid derivative and of at least one vinyl ester monomer, b) at least one oil-in-water emulsion having a particle size D.sub.50 of less than 350 nm and which comprises: a silicone mixture comprising (i) at least one polydialkylsiloxane comprising trialkylsilyl end groups, having a viscosity at 26 C. ranging from 40 000 to 100 000 mPa.Math.s and (ii) at least one aminosilicone having a viscosity at 25 C. ranging from 1000 to 15 000 mPa.Math.s and an amine number ranging from 2 to 10 mg of KOH per gram of aminosilicone; a surfactant mixture comprising one or more nonionic surfactants, said mixture having an HLB ranging from 10 to 16, and water and c) at least one pigment.

24. The composition according to claim 23, wherein the at least one copolymer is derived from the polymerization of at least one crotonic acid monomer and of at least one vinyl ester monomer.

25. The composition according to claim 23, wherein the at least one crotonic acid derivative is chosen from crotonic acid esters or amides.

26. The composition according to claim 23, wherein the at least one crotonic acid derivative is chosen from the crotonic acid esters of formula CH.sub.3CHCHCOOR1 with R1 representing a linear, branched or cyclic, saturated or unsaturated, optionally aromatic carbon-based chain, containing 1 to 30 carbon atoms, optionally comprising at least one function chosen from OH, OR with R C.sub.1-C.sub.6 alkyl, CN, or X halogen.

27. The composition according to claim 23, characterized in that the at least one crotonic acid derivative is chosen from the crotonic acid amides of formula CH.sub.3CHCHCONR2R2 with R2 and R2, which may be identical or different, representing hydrogen or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, carbon-based chain, containing 1 to 30 carbon atoms, optionally comprising at least one function chosen from OH, OR with R C.sub.1-C.sub.6 alkyl, CN, or X halogen.

28. The composition according to claim 23, wherein the at least one copolymer is derived from the polymerization of at least one monomer of crotonic acid or crotonic acid derivative and of at least two different vinyl ester monomers.

29. The composition according to claim 23, wherein the at least one vinyl ester monomer is chosen from vinyl acetate, vinyl propionate, vinyl butyrate, vinyl ethylhexanoate, vinyl neononanoate, vinyl neododecanoate, vinyl neodecanoate, vinyl pivalate, vinyl cyclohexanoate, vinyl benzoate, vinyl 4-tert-butylbenzoate, or vinyl trifluoroacetate

30. The composition according to claim 23, wherein the at least one copolymer is chosen from copolymers derived from the polymerization of crotonic acid, vinyl acetate and vinyl propionate, copolymers derived from the polymerization of crotonic acid, vinyl acetate and vinyl neodecanoate, or mixtures thereof.

31. The composition according to claim 23, wherein the copolymer is a crotonic acidivinyi acetate/vinyl neodecanoate terpolymer.

32. The composition according to claim 23, wherein the copolymers further comprise at least one monomer chosen from allylic or methallylic esters or vinyl ethers.

33. The composition according to claim 23, wherein the crotonic acid copolymer derived from the polymerization of at least one monomer of crotonic acid or crotonic acid derivative and of at least one vinyl ester monomer is present in an amount ranging from 0.05% to 15% by weight relative to the weight of the composition.

34. The composition according to claim 23, wherein the silicone mixture comprises one or more polydialkylsiloxanes comprising trialkylsilyl end groups of formula (I):
R3SiO(R2SiO)pSiR3, wherein: R, which may be identical or different, is a monovalent hydrocarbon-based radical having from 1 to 18 carbon atoms, and p is an integer ranging from 500 to 2000; having a viscosity ranging from 40 000 to 100 000 meas at 25 C.

35. The composition according to claim 23, wherein the silicone mixture comprises one or more aminosilicones of formula (11):
XR.sub.2Si(OSiAR).sub.n(OSiR.sub.2).sub.mOSiR.sub.2X, wherein: R, which may be identical or different, is a monovalent hydrocarbon-based radical having from 1 to 18 carbon atoms, X, which may be identical or different, represents R or a hydroxyl (OH) or a C.sub.1-C.sub.6 alkoxy group; A is an amino radical of formula R.sup.1[NR.sup.2R.sup.3].sub.xNR.sup.2.sub.2, or the protonated form of this amino radical, with R.sup.1 representing a C.sub.1-C.sub.6 alkylene radical, R.sup.2, which may be identical or different, being a hydrogen atom or a C.sub.1-C.sub.4 alkyl radical, R.sup.3 being a C.sub.1-C.sub.6 alkylene radical, x being 0 or 1; m and n are integers such that m+n ranges from 50 to 1000; having a viscosity at 25 C. ranging from 1000 to 15 000 mPa.Math.s.

36. The composition according to claim 23, comprising (i) at least one polydialkylsiloxane comprising trialkylsilyl end groups, having a viscosity, at 25 C., ranging from 40 000 to 100 000 mPa.Math.s, in an amount of from 70% to 90% by weight, and (ii) one or more aminosilicones having a viscosity, at 25 C., ranging from 1000 to 15 000 mPa.Math.s and an amine number ranging from 2 to 10 mg of KOH per gram of aminosilicone, in an amount of from 10% to 30% by weight relative to the total weight of the silicone mixture.

37. The composition according to claim 23, wherein the surfactant mixture comprises one or more nonionic surfactants chosen from: (i) (poly)oxyalkylenated fatty alcohols of formula: R.sub.3(OCH.sub.2CH.sub.2).sub.cOH in which: R3 represents a linear or branched alkyl or alkenyl radical comprising from 40 carbon atoms, optionally substituted with at least one hydroxyl group: and c is an integer ranging from 1 to 200; (ii) (poly)oxyalkylenated (C.sub.8-C.sub.32)alkyl phenyl ethers, comprising from 1 to 200 mol of ethylene oxide; (iii) polyoxyalkylenated esters of C.sub.8-C.sub.32 fatty acids and of sorbitan; and (iv) polyoxyethylenated esters of C.sub.8-C.sub.32 fatty acids.

38. The composition according to claim 23, wherein the oil-in-water emulsion comprises: the surfactant mixture in a total amount ranging from 5% to 15% by weight, relative to the total weight of the emulsion: and/or at least one nonionic surfactant in a total amount ranging from 5% to 15% by weight, relative to the total weight of the emulsion; the silicone mixture in a total amount ranging from 40% to 60% by weight, relative to the total weight of the emulsion; and/or the polydialkylsiloxane(s) comprising trialkylsilyl end groups, in a total amount ranging from 35% to 45% by weight, relative to the total weight of the emulsion; and/or the aminosilicone(s) in a total amount ranging from 5% to 15% by weight, relative to the total weight of the emulsion; and/or water in a total amount ranging from 25% to 50% by weight, relative to the total weight of the emulsion.

39. The composition according to claim 23, wherein the oil-in-water emulsion has a particle size D50 of between 100 and 300 nm.

40. The composition according to claim 23, wherein the composition comprises the oil-in-water emulsion in an amount ranging from 0.1% to 15% by weight, relative to the total weight of the composition.

41. The composition according to claim 23, wherein the weight ratio of the total amount of at least one copolymer of crotonic acid or crotonic acid derivative to the total amount of oil-in-water emulsion ranges from 0.1 to 10.

42. The composition according to claim 23, wherein the composition further comprises a thickener chosen from crosslinked copolymers of acrylic and/or methacrylic acid.

43. A method for dyeing keratin fibers comprising applying to the keratin fibers a composition comprising: a) at least one copolymer derived from the polymerization of at least one monomer of crotonic acid or crotonic acid derivative and of at least one vinyl ester monomer, b) at least one oil-in-water emulsion having a particle size D.sub.50 of less than 350 nm and which comprises: a silicone mixture comprising 0) at least one polydialkylsiloxane comprising trialkylsilyl end groups, having a viscosity at 25 C. ranging from 40 000 to 100 000 mPa.Math.s and (ii) at least one aminosilicone having a viscosity at 25 C. ranging from 1000 to 15 000 mPa.Math.s and an amine number ranging from 2 to 10 mg of KOH per gram of aminosilicone; a surfactant mixture comprising one or more nonionic surfactants, said mixture having an HLB ranging from 10 to 16, and water and c) at least one pigment.

Description

EXAMPLES

Example 1

Preparation of the Silicone Emulsion

[0296] 450 g of fluid aminosilicone (copolymer of dimethylsiloxane-aminoethylaminopropylmethylsiloxane comprising trimethylsilyl end groups, having an amine number of 7.2 mg of KOH/g and a viscosity of 5600 mPa.Math.s at 25 C.) are transferred into a 1st vessel; 1800 g of dimethylsiloxane comprising trimethylsilyl end groups, having a viscosity of 61 500 mPa.Math.s at 25 C., are added, with stirring, and the stirring is maintained for 2 hours at ambient temperature.

[0297] In a separate vessel, 49 g of steareth-6 and 62 g of PEG100 stearate are mixed, and the mixture is heated to 60 C. The mixture is maintained at this temperature until a liquid mixture is obtained, then 31 g of trideceth-3 and 350 g of trideceth-10 (80% of active material) are added. The surfactant mixture has an HLB=11.25. 80 g of water and 6.2 g of glacial acetic acid are added and the stirring is continued until a creamy paste is obtained.

[0298] The content of this 2nd vessel (creamy paste) is then transferred into the 1st vessel (containing the silicones), then the mixture obtained is mixed for 30 minutes at ambient temperature (20-25 C.). The mixing steps are carried out in order to obtain a homogeneous mixture; they are carried out at ambient temperature. [0299] 79.6 g of demineralized water are added and mixing is carried out for 60 minutes. [0300] 72.7 g of demineralized water are added and mixing is carried out for 50 minutes. [0301] 197.4 g of demineralized water are added and mixing is carried out for 5 minutes. [0302] 294.3 g of demineralized water are added and mixing is carried out for 5 minutes. [0303] 180 g of demineralized water are added and mixing is carried out for 5 minutes. [0304] 180 g of demineralized water are added and mixing is carried out for 5 minutes. [0305] 197.4 g of demineralized water are added and mixing is carried out for 5 minutes. [0306] 197.4 g of demineralized water are added and mixing is carried out for 3 minutes. [0307] 228.5 g of demineralized water are added and mixing is carried out for 3 minutes.

[0308] Finally, 40.5 g of 2-phenoxyethanol (preservative) are added and mixing is carried out for 3 minutes.

[0309] An oil-in-water emulsion having a particle size D.sub.50 of 170 nm is obtained.

Example 2

[0310] Compositions (g AM/100 g)

TABLE-US-00001 Composition A VA/crotonates/vinyl neodecanoate copolymer 2 Carbomer 0.75 Silicone emulsion as prepared in example 1 2 Synthetic mica and titanium dioxide 7 and Red 7 calcium lake on barium sulfate substrate Neutralizers qs Preservative, fragrance qs Ethanol 7.5 PEG-40 hydrogenated castor oil 1 Water qs 100

[0311] Protocol

[0312] Composition A is applied to locks of yak hair at a rate of 1 g of composition per gram of lock. The locks are then combed, dried with a hairdryer and then combed again.

[0313] Results: Cosmetic Feel Performance

[0314] The performance levels in terms of cosmetic feel were evaluated on dried locks by five experts, in a blind test.

[0315] In 100% of the cases, the experts judged that composition A according to the invention afforded smooth locks with clearly individualized hair strands, having a pleasant cosmetic feel, especially good softness, good suppleness and absence of tackiness.

Example 3

[0316] Compositions (g AM/100 g)

TABLE-US-00002 A1 B1 C1 Invention comparative comparative Phenoxyethanol 0.7 0.7 0.7 Silicone emulsion as prepared 2 2 2 in example 1 CI 77891 (and) synthetic 10 10 10 fluorophlogopite (and) CI 15850 VA/crotonates/vinyl 3 neodecanoate copolymer Carbomer 0.75 0.75 0.75 Polyvinylcaprolactam 3 VP/dimethylaminoethyl 3 methacrylate copolymer Ethanol 7.5 7.5 7.5 water qs 100 qs 100 qs 100 PEG-40 Hydrogenated castor oil 1 1 1

[0317] Protocol

[0318] Composition A1, B1 or C1 is applied to locks of yak hair at a rate of 1 g of composition per gram of lock.

[0319] The locks are dried with a hairdryer and then combed.

[0320] The locks are then rubbed on a white cloth.

[0321] Results: Transfer-resistance Performance

[0322] The performance levels in terms of transfer resistance were evaluated by five experts, in a blind test, who visually evaluated the amount of pigment present on the white cloth after rubbing.

[0323] In 100% of the cases, the experts judged that composition A1 according to the invention, compared with compositions B1 and C1, led to a very markedly smaller amount of pigment present on the cloth than the amount deposited by compositions B1 and C1. Composition A1 according to the invention thus has better transfer-resistance properties than the comparative compositions B1and C1.

Example 4

[0324] Compositions (g AM/100 g)

TABLE-US-00003 H I Invention Comparative VA/crotonates/vinyl neodecanoate 2 2 copolymer Carbomer 0.75 0.75 Silicone emulsion as prepared 2 in example 1 Synthetic mica and titanium 7 7 dioxide and Red 7 calcium lake on barium sulfate substrate Neutralizers qs qs Preservative, fragrance qs qs Ethanol 7.5 7.5 PEG-40 hydrogenated castor oil 1 1 Water qs 100 qs 100

[0325] Protocol

[0326] Compositions H and I are applied to locks of yak hair at a rate of 1 g of composition per gram of lock.

[0327] The locks are then combed, dried with a hairdryer and then combed again.

[0328] Results No.1: Coloring Performance Levels

[0329] The performance levels in terms of uniformity of color intensity were evaluated on dried locks by 5 experts, in a blind test.

[0330] 100% of the experts found that the lock treated with composition H according to the invention has a more intense and more uniform color result than comparative composition I.

[0331] Results No.2: Natural Feel, Suppleness and Individualization

[0332] The performance levels in terms of natural feel were evaluated on dried locks by 5 experts, in a blind test.

[0333] Action

[0334] The expert seizes the lock between the thumb and index finger and slides the fingers along the lock from the upper part to the ends. At the same time, the expert performs a slight oscillating movement with the thumb so as to get a good feeling of the possible presence of deposit or of roughness (unnatural feel).

[0335] The expert also evaluates whether the hairs separate from one another, whether they are in packets (non-individualized hair strands).

[0336] In 100% of the cases, the experts judged that composition H according to the invention afforded locks that are more individualized and have a more natural feel with, especially, good suppleness, compared with formula I according to the prior art.