COMPOSITION COMPRISING A PHOTOCROSSLINKABLE POLYMER HAVING A HYDROPHOBIC GROUP AND A COLORING AGENT

Abstract

The present invention relates to a composition (C) for the treatment of keratin fibers, comprising at least one photocrosslinkable polymer having hydrophobic groups, and at least one coloring agent chosen from pigments and mixtures thereof.

The present invention also relates to a cosmetic treatment process, in particular for dyeing keratin fibers, wherein the composition (C) is applied to said fibers.

Claims

1. A composition (C) for the treatment of keratin fibers, comprising: a. at least one photocrosslinkable polymer comprising at least one photodimerizable group and at least one hydrophobic group, and b. at least one coloring agent chosen from pigments and mixtures thereof, the hydrophobic group(s) being chosen from: a saturated or unsaturated (C.sub.1-C.sub.3W)alkyl group, optionally substituted and/or interrupted with one or more heteroatoms, an alkenyl group, a fluorinated group such as a fluorocarbon group such as CF.sub.3, CHF.sub.2, OCF.sub.3, SCF.sub.3, CF.sub.3C(O), a silicone group such as SiR.sub.aR.sub.bR.sub.c such as Si(CH.sub.3).sub.3, polydimethylsiloxane-PDMS, Si(OR).sub.3, ,-diaminopropyl PDMS, ,-dihydroxyalkyl PDMS, ,-dicarboxyalkyl PDMS, with R.sub.a, R.sub.b and R.sub.c, which may be identical or different, representing a (C.sub.1-C.sub.8)alkyl group which is optionally interrupted and/or terminated with one or more non-contiguous heteroatoms such as O or S, and R representing a (C.sub.1-C.sub.6)alkyl group.

2. The composition as claimed in claim 1, characterized in that the photodimerizable group(s) is (are) chosen from monovalent radicals having the following formulae (I) and (II): ##STR00038## and also the geometrical isomers thereof, formulae (I) and (II) wherein: Y and Z denote, independently of each other, a nitrogen atom or a C(R) group with R representing a hydrogen atom or a (C.sub.1-C.sub.4)alkyl group such as methyl; A represents a bond or a divalent group chosen from (C.sub.1-C.sub.8)alkylene, arylene, heteroarylene, cycloalkylene, heterocycloalkylene, (thio)carbonyl and (C.sub.2-C.sub.8)alkenylene radicals and combinations thereof; B represents a monovalent group chosen from (C.sub.1-C.sub.8)alkyl radicals, aryl radicals, optionally cationic heteroaryl radicals, cycloalkyl radicals, optionally cationic heterocycloalkyl radicals, (thio)carbonyl radicals and (C.sub.2-C.sub.8)alkenyl radicals and combinations thereof; X represents a divalent group chosen from (C.sub.2-C.sub.8)alkylene, arylene, heteroarylene, cycloalkylene, heterocycloalkylene, (thio)carbonyl and (C.sub.2-C.sub.8)alkenylene radicals and combinations thereof; p represents an integer between 1 and 5 inclusive, in particular between 1 and 3; preferably, p is equal to 1; ##STR00039## represents the bond that connects the part of the monovalent radical to the rest of the molecule; and it being possible for each of the cited groups to be optionally substituted with one or more halogen atoms or group(s) chosen from (C.sub.1-C.sub.6)alkyl, hydroxyl, amino, (di)(C.sub.1-C.sub.6)alkylamino, phenyl, carboxy, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxy(thio)carbonyl, hydrogeno(thio)carbonyl, sulfonato ROS(O).sub.2 or RS(O).sub.2O, amide RRNC(O) or RC(O)N(R) or acyl RC(O), or ammonium RRRN.sup.+ groups with R, R and R, which may be identical or different, representing a hydrogen atom or a (C.sub.1-C.sub.4)alkyl group.

3. The composition as claimed in either one of the preceding claims, characterized in that the photodimerizable group(s) is (are) chosen from the monovalent radicals of the following compounds: stilbene, styrylpyridinium (stilbazolium) having the formula below, and the geometric isomers thereof: ##STR00040## Where R.sup.1 and R.sup.3, which may be identical or different, represent a halogen atom or a (C.sub.1-C.sub.6)alkyl group; or alternatively two contiguous groups R.sup.1 or R.sup.3 form, together with the carbon atoms that bear them, a benzo group; R.sup.2 represents a hydrogen atom, a (C.sub.1-C.sub.6)alkyl group optionally substituted with one or more halogen atoms such as chlorine or hydroxyl; preferably, R.sup.2 represents a (C.sub.1-C.sub.6)alkyl group such as methyl, ethyl or propyl; q and r represent an integer between 0 and 4 inclusive; and Q.sup. represents an anionic counterion preferably chosen from halide ions such as chlorides, bromides, iodides, perchlorates, tetrafluoroborates, methylsulfate, phosphates, sulfates, methanesulfonates, p-toluenesulfonate; ##STR00041## represents the bond that connects the part of the monovalent radical to the rest of the molecule being understood that the pendent group A.sub.2 may be connected to the rest of the molecule via R.sup.2; preferably the ##STR00042## bond is found on the phenyl in the para position of the styryl group on A.sub.1 or connected to the rest of the molecule via R.sup.2 on A.sub.2; preferentially the styryl group of A.sub.1 and A.sub.2 is found in the position para to the pyridinium group; styrylazolium having the formula below, and the geometric isomers thereof: ##STR00043## where: A represents a sulfur atom, an oxygen atom, or a group NR.sup.2 or C(R.sup.2).sub.2; and ##STR00044## Q.sup., r, q, R.sup.1, R.sup.2, and R.sup.3 are as defined previously, preferably the ##STR00045## bond is found on the phenyl in the para position of the styryl group, styrylpyrazine, chalcone, (thio)cinnamate and (thio)cinnamamide, maleimide, (thio)coumarin, thymine, uracil, butadiene, anthracene, pyridone, pyrrolizinone, acridizinium salts, furanone, phenylbenzoxazole, and derivatives thereof.

4. The composition as claimed in any one of the preceding claims, characterized in that the hydrophobic group(s) is (are) chosen from: a (C.sub.2-C.sub.22)alkyl group, more preferentially a (C.sub.3-C.sub.16)alkyl group, preferably a (C.sub.3-C.sub.8)alkyl group.

5. The composition as claimed in any one of the preceding claims, characterized in that the photocrosslinkable polymer has a natural or synthetic backbone chosen from polysaccharides, poly(vinyl) polymers and polydiorganosiloxanes, preferably from polyvinyl alcohol and poly(vinyl acetate), which are preferably partially or totally hydrolyzed.

6. The composition as claimed in any one of the preceding claims, characterized in that the photocrosslinkable polymer(s) are chosen from the polymers comprising at least the units below: ##STR00046## with Q.sup. representing an anionic counterion preferably chosen from halide ions such as chlorides, bromides, iodides, perchlorates, tetrafluoroborates, methylsulfate, phosphates, sulfates, methanesulfonates, p-toluenesulfonate, preferably mesylate CH.sub.3OSO.sub.3.sup..

7. The composition as claimed in any one of the preceding claims, characterized in that the total amount of the photocrosslinkable polymer(s) ranges from 0.01% to 40% by weight, preferably from 0.1% to 30% by weight, better still from 0.5% to 25% by weight and even better still from 1% to 10% by weight, relative to the total weight of the composition (C).

8. The composition as claimed in any one of the preceding claims, characterized in that the total content of pigments ranges from 0.05% to 20% by weight, preferably from 0.1% to 15% by weight and better still from 0.5% to 10% by weight, relative to the total weight of the composition.

9. The composition as claimed in any one of the preceding claims, characterized in that it also comprises at least one thickener.

10. The composition as claimed in any one of the preceding claims, characterized in that it comprises at least one silicone.

11. A process for the cosmetic treatment of, in particular for dyeing, keratin fibers such as the hair, wherein the composition (C) as defined in any one of claims 1 to 10 is applied to said fibers.

12. The process as claimed in claim 11, comprising a step of irradiating the composition on the keratin materials.

13. The use of the composition (C) as defined in any one of claims 1 to 10, for the cosmetic treatment of, in particular for dyeing, keratin fibers such as the hair.

Description

EXAMPLE

Example 1

[0497] The following dye composition C1 is prepared:

[0498] Composition: amounts expressed in g of starting material as obtained/100 g

TABLE-US-00001 TABLE 1 C1 Propyl-PVA-SbQ (Polyquaternium-114 PPVA-SBQ 40.3 g from MURAMI) in an aqueous solution containing (6% am) 15% of active material Mica and iron oxide (Pearlescent Pigment 6.5 g Prestige Soft Bronze from Sudarshan Chemical) Mixture of amomethicone dimethicone in an 15 g aqueous emulsion (Belsil DADM 5050.sup.E from (7.5% AM) Wacker) Water qs 100 g

Protocol:

[0499] Composition C1 is applied to locks of dry natural hair containing 90% white hairs, at a rate of 0.5 g of composition per gram of lock.

[0500] The locks of hair are then dried with a hairdryer with a round or flat brush or a comb, and then combed.

[0501] The hair treated was irradiated under UVA at 365 nm for an energy of 8 J/cm.sup.2.

[0502] The locks of hair are left at ambient temperature for 24 hours.

[0503] Next, the locks of hair thus dyed are subsequently subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the obtained coloring with respect to shampoo washing.

Shampoo Washing Protocol:

[0504] The locks of dyed hair are combed, moistened with water at 35 C. and then passed between the fingers five times for 5 seconds. The locks of hair are then squeezed dry between two fingers.

[0505] A standard shampoo (Garnier Ultra Doux) is applied uniformly to the colored locks, in a proportion of 0.4 g of standard shampoo per gram of locks, the locks of hair being massaged gently along the length (6 passes) for 15 seconds, from the root to the end.

[0506] The locks of hair are then placed on a watch glass and left to stand for 1 minute.

[0507] Next, the locks of hair are rinsed with water while passing the lock between the fingers (15 passes). The locks of hair are then squeezed dry between two fingers before the next shampoo wash.

[0508] Once the tests of several shampoo washes have been performed, the locks of hair are combed and dried with a hairdryer.

Results:

[0509] The persistence of the color of the locks was evaluated in the CIE L*a*b* system, using a Minolta Spectrophotometer CM3600A colorimeter (illuminant D65, angle 10, specular component included).

[0510] 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.

[0511] The persistence of the coloring is evaluated by the color difference E between the colored locks before shampooing, then after having undergone five shampoo washes according to the protocol described above. The lower the E value, the more persistent the color with respect to shampoo washing.

[0512] The E value is calculated according to the following equation:

[00001]$\begin{array}{cc}E=\sqrt{{\left(L^{}-L_o^{}\right)}^2+{\left(a^{}-a_o^{}\right)}^2+{\left(b^{}-b_o^{}\right)}^2}& \left[\mathrm{Math}.1\right]\end{array}$

[0513] In this equation, L*a*b* represent the values measured after coloring the hair and after performing the shampoo washes, and L.sub.0*a.sub.0*b.sub.0* represent the values measured after coloring the hair but before shampoo washing.

TABLE-US-00002 TABLE 2 Number of shampoo washes L* a* b* E Composition 0 36.0 29.0 22.3 0 C1 5 37.4 27.4 20.9 2.6

[0514] The difference in E is small. The locks of hair dyed with the composition C and washed with five shampoo washes show good persistence of the color with respect to shampoo washing.

Example 3

[0515] The composition below was prepared:

[0516] amounts expressed in g of starting material as obtained/100 g

TABLE-US-00003 TABLE 3 C2 Propyl-PVA-SbQ 40.3 g (6% am) Mica and iron oxide (Pearlescent Pigment 4.23 Prestige Soft Bronze from Sudarshan Chemical) Black iron oxide 0.33 Yellow iron oxide 1.95 Titanium oxide-coated glass particles 1.5 Mixture of amomethicone dimethicone in an 15 g aqueous emulsion (Belsil DADM 5050.sup.E from (7.5% AM) Wacker) Water qs 100 g

[0517] Composition C2 was applied to locks of wet natural hair containing 90% white hairs, at a rate of 0.5 g of composition per gram of lock.

[0518] The locks of hair were then dried with a hairdryer, and then combed.

[0519] The hair treated was irradiated under UVA at 365 nm for an energy of 8 J/cm.sup.2.

[0520] The locks of hair are left at ambient temperature for 24 hours.

Results:

[0521] The locks of hair treated with composition C show smooth, uniform, chocolate colored coating on the hair with good cosmetic properties, notably in terms of softness, feel and good hair strand separation. The colored coating of the keratin fibers shows good persistence with respect to shampoo washing.