COMPOSITION COMPRISING A (POLY)CARBODIIMIDE COMPOUND AND A COLORING AGENT

Abstract

The present invention relates to a composition (C) for the treatment of keratin fibers, comprising at least one (poly)carbodiimide compound chosen from the compounds of formula (I), and at least one coloring agent chosen from pigments, direct dyes, and mixtures thereof.

Claims

1. A composition (C) for the treatment of keratin fibers, comprising: a) at least one (poly)carbodiimide compound chosen from the compounds of formula (I) below: ##STR00029## in which formula (I): X.sub.1 and X.sub.2 independently represent an oxygen atom O, a sulfur atom S or a nitrogen atom NH; R.sub.1 and R.sub.2 independently represent a hydrocarbon-based radical optionally interrupted with one or more heteroatoms, n and z denote an integer ranging from 1 to 20, with n+z≥2 and w denotes an integer ranging from 1 to 3; L.sub.1 independently represents a C.sub.1-C.sub.18 divalent aliphatic hydrocarbon-based radical, a C.sub.3-C.sub.15 cycloalkylene radical, a C.sub.3-C.sub.12 heterocycloalkylene group or a C.sub.6-C.sub.14 arylene group, and mixtures thereof; E independently represents a group chosen from: —O—R.sub.3—O—; —S—R.sub.4—S—; —R.sub.5—N(R.sub.6)—R.sub.4—N(R.sub.6)—R.sub.5—; in which R.sub.3 and R.sub.4 independently represent a divalent hydrocarbon-based radical optionally interrupted with one or more heteroatoms; R.sub.5 independently represents a covalent bond or a saturated divalent hydrocarbon-based radical, optionally interrupted with one or more heteroatoms; R.sub.6 independently represents a hydrogen atom or a hydrocarbon-based radical, optionally interrupted with one or more heteroatoms, and b) at least one coloring agent chosen from pigments, direct dyes, and mixtures thereof.

2. The composition as claimed in claim 1, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (I) in which: X.sub.1 and X.sub.2 independently represent an oxygen atom; R.sub.1 and R.sub.2 are independently chosen from dialkylamino alcohols, alkyl esters of hydroxycarboxylic acid and monoalkyl ethers of (poly)alkylene glycol, in which a hydroxyl group has been removed, and mixtures thereof; n and z denote an integer ranging from 1 to 20, with n+z≥2 and w is equal to 1; L.sub.1 is chosen from a C.sub.1-C.sub.18 divalent aliphatic hydrocarbon-based radical, a C.sub.3-C.sub.15 cycloalkylene radical, a C.sub.3-C.sub.12 heterocycloalkylene group or a C.sub.6-C.sub.14 arylene group, and mixtures thereof; E independently represents a group chosen from: —O—R.sub.3—O—; —S—R.sub.4—S—; —R.sub.5—N(R.sub.6)—R.sub.4—N(R.sub.6)—R.sub.5—; in which R.sub.3 and R.sub.4 are independently chosen from a C.sub.6-C.sub.14 arylene radical, a C.sub.3-C.sub.12 cycloalkylene radical, a linear or branched C.sub.1-C.sub.18 alkylene radical, optionally interrupted with one or more heteroatoms, and mixtures thereof; when R.sub.5 is not a covalent bond, R.sub.5 is chosen from a C.sub.6-C.sub.14 arylene radical, a C.sub.3-C.sub.12 cycloalkylene radical, a linear or branched C.sub.1-C.sub.18 alkylene radical, optionally interrupted with one or more heteroatoms, and mixtures thereof; and R.sub.6 is chosen from a C.sub.6-C.sub.14 arylene radical, a C.sub.3-C.sub.12 cycloalkylene radical, a linear or branched C.sub.1-C.sub.18 alkylene radical, optionally interrupted with one or more heteroatoms, and mixtures thereof.

3. The composition as claimed in either one of the preceding claims, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (I) in which: X.sub.1 and X.sub.2 independently represent an oxygen atom; R.sub.1 and R.sub.2 are, independently, monoalkyl ethers of (poly)alkylene glycol, in which a hydroxyl group has been removed; n and z denote an integer ranging from 1 to 20, with n+z≥2 and w is equal to 1; L.sub.1 is a C.sub.3-C.sub.15 cycloalkylene radical; E independently represents a group chosen from: —O—R.sub.3—O—; —S—R.sub.4—S—; —R.sub.5—N(R.sub.6)—R.sub.4—N(R.sub.6)—R.sub.5—; in which R.sub.3 and R.sub.4 are independently chosen from a C.sub.6-C.sub.14 arylene radical, a C.sub.3-C.sub.12 cycloalkylene radical, a linear or branched C.sub.1-C.sub.18 alkylene radical, optionally interrupted with one or more heteroatoms, and mixtures thereof; when R.sub.5 is not a covalent bond, R.sub.5 is chosen from a C.sub.6-C.sub.14 arylene radical, a C.sub.3-C.sub.12 cycloalkylene radical, a linear or branched C.sub.1-C.sub.18 alkylene radical, optionally interrupted with one or more heteroatoms, and mixtures thereof; and R.sub.6 is chosen from a C.sub.6-C.sub.14 arylene radical, a C.sub.3-C.sub.12 cycloalkylene radical, a linear or branched C.sub.1-C.sub.18 alkylene radical, optionally interrupted with one or more heteroatoms, and mixtures thereof.

4. The composition as claimed in any one of the preceding claims, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (I) in which: X.sub.1 and X.sub.2 independently represent an oxygen atom; R.sub.1 and R.sub.2 independently represent the compound of formula (V) below:
R.sub.13—[O—CH.sub.2—C(H)(R.sub.14)].sub.q—  (V) in which R.sub.13 represents a C.sub.1-C.sub.4 alkyl group or a phenyl, preferably a C.sub.1-C.sub.4 alkyl group, more preferentially a methyl, R.sub.14 represents a hydrogen atom or a C.sub.1-C.sub.4 alkyl group, preferably a hydrogen atom and q denotes an integer ranging from 4 to 30; n and z denote an integer ranging from 2 to 20, with n+z ranging from 4 to 10 and w is equal to 1; L.sub.1 is a C.sub.3-C.sub.15 cycloalkylene radical such as cyclopentylene, cycloheptylene, cyclohexylene and 4,4-dicyclohexylenemethane, and E represents a group —O—R.sub.3—O— in which R.sub.3 is chosen from a C.sub.6-C.sub.14 arylene radical, a C.sub.3-C.sub.12 cycloalkylene radical, a linear or branched C.sub.1-C.sub.18 alkylene radical, optionally interrupted with one or more heteroatoms, and mixtures thereof.

5. The composition as claimed in any one of the preceding claims, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (I) in which: X.sub.1 and X.sub.2 independently represent an oxygen atom; R.sub.1 and R.sub.2 independently represent the compound of formula (V) below:
R.sub.13—[O—CH.sub.2—C(H)(R.sub.14)].sub.q—  (V) in which R.sub.13 represents a C.sub.1-C.sub.4 alkyl group or a phenyl, preferably a C.sub.1-C.sub.4 alkyl group, more preferentially a methyl, R.sub.14 represents a hydrogen atom or a C.sub.1-C.sub.4 alkyl group, preferably a hydrogen atom and q denotes an integer ranging from 4 to 30; n and z denote an integer ranging from 1 to 20, with n+z ranging from 4 to 10 and w is equal to 1; L.sub.1 is a C.sub.3-C.sub.15 cycloalkylene radical such as cyclopentylene, cycloheptylene, cyclohexylene and 4,4-dicyclohexylenemethane, preferably 4,4-dicyclohexylenemethane; and E represents a group- —O—R.sub.3—O— in which R.sub.3 represents a linear or branched C.sub.1-C.sub.18 alkylene radical such as methylene, propylene, butylene or ethylene, optionally interrupted with one or more heteroatoms.

6. The composition as claimed in any one of the preceding claims, characterized in that the (poly)carbodiimide compound(s) is (are) chosen from the compounds of formula (XI) below: ##STR00030## in which L.sub.i is 4,4-dicyclohexylenemethane, n and z denote an integer ranging from 1 to 20, with n+z ranging from 4 to 10, E represents a group- —O—R.sub.3—O— in which R.sub.3 represents a linear or branched C.sub.1-C.sub.18 alkylene radical such as methylene, propylene, butylene or ethylene, optionally interrupted with one or more heteroatoms, and r and s denote an integer ranging from 4 to 30.

7. The composition as claimed in any one of the preceding claims, characterized in that the total amount of the (poly)carbodiimide compound(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 composition (C).

8. The composition as claimed in any one of the preceding claims, characterized in that it comprises at least one aqueous dispersion of particles of polymer(s) chosen from polyurethanes, acrylic polymers, and mixtures thereof, preferably chosen from aqueous dispersions of acrylic polymer particles, more preferentially from aqueous dispersions of film-forming acrylic polymer particles.

9. The composition as claimed in claim 8, characterized in that the acrylic polymer(s) comprise one or more units derived from the following monomers: a) (meth)acrylic acid; and b) C.sub.1 to C.sub.30, more preferentially C.sub.1 to C.sub.20, better still C.sub.1 to C.sub.10, and even more particularly C.sub.1 to C.sub.4, alkyl (meth)acrylate.

10. The composition as claimed in either one of claims 8 and 9, characterized in that the total amount of the aqueous dispersion(s) of polymer particles present in the composition ranges from 0.1% to 40% by weight, more preferentially from 0.1% to 35% by weight and better still from 0.2% to 30% by weight, relative to the total weight of composition (C).

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

12. The composition as claimed in claim 11, characterized in that the silicone(s) are chosen from non-amino silicones, amino silicones and mixtures thereof.

13. The composition as claimed in either one of claims 11 and 12, characterized in that said silicone(s) is (are) present in a total amount ranging from 0.01% to 20% by weight relative to the total weight of the composition, preferably from 0.05% to 15% by weight, more preferentially from 0.1% to 10% by weight and even more preferentially from 0.1% to 5% by weight relative to the total weight of composition (C).

14. A process for cosmetically treating, in particular dyeing, keratin fibers such as the hair, in which composition (C) as defined in any one of claims 1 to 13 is applied to said fibers.

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

Description

EXAMPLE

Example 1: Process for Synthesizing the (Poly)Carbodiimide Compound

[0636] 50 g of 4,4′-dicyclohexylmethane diisocyanate and 0.5 g of 4,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide were placed with stirring in a 500 mL three-necked round-bottomed flask equipped with a thermometer, a stirrer and a reflux tube.

[0637] The reaction medium was heated at 140° C. under nitrogen for 4 hours, the reaction being monitored by infrared spectroscopy by means of the absorption of the isocyanate functions between 2200 and 2300 cm.sup.−1, and then cooled to 120° C.

[0638] A mixture of 5.3 g of polyethylene glycol monomer methyl ether and 1.2 g of 1,4-butanediol are introduced with stirring into the reaction medium. The temperature of 120° C. is maintained until the isocyanate functions have totally disappeared, monitored by infrared spectroscopy at 2200-2300 cm.sup.−1, and is then cooled to room temperature.

[0639] After cooling to room temperature, the reaction medium is poured dropwise with vigorous stirring into a 500 mL glass beaker containing 85 g of distilled water, to give the desired product in the form of a translucent yellow liquid.

Example 2

[0640] Composition: amounts expressed in g of active material as obtained/100 g

TABLE-US-00001 TABLES 1 Composition C1 Polycarbodiimide.sup.(1) 24 Amodimethicone (and) Trideceth-5 (and) Trideceth-10 .sup.(2)  5 Preserving agent(s), optionally neutralized thickener qs Water qs 100 .sup.(1)synthesized according to the synthetic process described in example 1 (containing 40% active material in water), .sup.(2) sold by the company Wacker under the name Belsil ADM LOG 1

TABLE-US-00002 TABLES 2 Composition C2 Acrylates copolymer.sup.(3) 40 Amodimethicone (and) Trideceth-5 (and) Trideceth-10 .sup.(2)  5 Iron oxide (CI 77491) 12 Preserving agent(s), optionally neutralized thickener qs Water qs 100 .sup.(3)sold by the company Daito Kasei Kogyo under the trade name Daitosol 3000SLPN-PE1 (aqueous dispersion containing 30% active material)

[0641] Composition C1 is mixed with composition C2 in a 50/50 ratio to obtain composition C.

[0642] Protocol:

[0643] Composition C is applied to locks of natural dry hair containing 90% white hairs, in a proportion of 0.5 g of composition per gram of lock.

[0644] The locks of hair are then dried with a hairdryer with a comb, and then combed.

[0645] The locks of hair are left at room temperature for 24 hours.

[0646] Next, the locks of hair thus dyed are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the coloring obtained with respect to shampoo washing.

[0647] Shampoo Wash Protocol:

[0648] The locks of dyed hair are combed and moistened with water at 35° C. before being passed between the fingers five times for 5 seconds. The locks of hair are then drained between two fingers.

[0649] A standard shampoo (Garnier Ultra Doux) is applied uniformly to the dyed 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.

[0650] The locks of hair are then placed in a watch glass and left to stand for 1 minute.

[0651] Next, the locks of hair are rinsed with water while passing the lock between the fingers (15 passes). The locks of hair are then drained between two fingers before the next shampoo wash.

[0652] Once the tests of several shampoo washes have been performed, the locks of hair are combed and dried with a hairdryer.

[0653] Results:

[0654] 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).

[0655] 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.

[0656] The persistence of the coloring is evaluated by the color difference ΔE between the dyed locks before shampooing, then after having undergone five shampoo washes according to the protocol described above. The lower the ΔE value, the more persistent the color with respect to shampoo washing.

[0657] The ΔE value is calculated according to the following equation:

ΔE=√{square root over ((L*−L.sub.o*).sup.2+(a*−a.sub.o*).sup.2+(b*−b.sub.o*).sup.2)}  [Math. 1]

[0658] In this equation, L*a*b* represent the values measured after dyeing the hair and after performing the shampoo washes, and L*.sub.0a.sub.0*b.sub.0* represent the values measured after dyeing the hair but before shampoo washing.

TABLE-US-00003 TABLES 3 Number of Compositions shampoo washes L* a* b* ΔE Composition C 0 36.0 29.0 22.3 0 5 37.4 27.4 20.9 2.6

[0659] The locks of hair dyed with composition an washed with five shampoo washes show goo color persistence with respect to shampoo washing.

Example 3

[0660] Composition: amounts expressed in g of active material as obtained/100 g

TABLE-US-00004 TABLES 4 Composition C′ Polycarbodiimide.sup.(1) 12 Amodimethicone (and) Trideceth-5 (and) Trideceth-10 .sup.(2)  5 Acrylates copolymer.sup.(3) 20 Iron oxide (CI 77491)  6 Preserving agent(s), optionally neutralized thickener qs Water qs 100 .sup.(1)synthesized according to the synthetic process described in example 1 (containing 40% active material in water). .sup.(2) sold by the company Wacker under the name Belsil ADM LOG 1 .sup.(3)sold by the company Daito Kasei Kogyo under the trade name Daitosol 3000SLPN-PE1 (aqueous dispersion containing 30% active material)

[0661] Protocol:

[0662] Composition C′ is applied to locks of natural dry hair containing 90% white hairs, in a proportion of 0.5 g of composition per gram of lock.

[0663] The locks of hair are then dried with a hairdryer with a comb, and then combed.

[0664] The locks of hair are left at room temperature for 24 hours.

[0665] Results:

[0666] The locks of hair treated with composition C′ show smooth, uniform, colored coating of the hair and have 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.

Example 4

[0667] Composition: amounts expressed in g of active material as obtained/100 g

TABLE-US-00005 TABLES 5 A1 B1 Composition (invention) (comparative) Polycarbodiimided.sup.(1) 24 (9.6 AM) — Carbodilite E-05 sold by the company Nisshinbo — 23.3 (9.6 AM) Chemical Inc. (containing 41.3% active material in water) Amodimethicone (and) Trideceth-5 (and) Trideceth- 5 5 10 .sup.(2) Water qs 100 qs 100 .sup.(1)synthesized according to the synthetic process described in example 1 (containing 40% active material in water), .sup.(2) sold by the company Wacker under the name Belsil ADM LOG 1

TABLE-US-00006 TABLES 6 Composition A2 Acrylates copolymer.sup.(3) 40 Amodimethicone (and) Trideceth-5 (and) Trideceth-10 .sup.(2)  5 Iron oxide (CI 77491) 12 Water qs 100 .sup.(3)sold by the company Daito Kasei Kogyo under the trade name Daitosol 3000SLPN-PE1 (aqueous dispersion containing 30% active material)

[0668] Composition A1 is mixed with composition A2 in a 50/50 ratio to obtain composition A according to the invention.

[0669] Composition B1 is mixed with composition A2 in a 50/50 ratio to obtain comparative composition B.

[0670] Protocol:

[0671] Composition A and composition B are applied to locks of natural dry hair containing 90% white hairs, in a proportion of 0.5 g of composition per gram of lock.

[0672] The locks of hair are then dried with a hairdryer with a comb, and then combed.

[0673] The locks of hair are left at room temperature for 24 hours.

[0674] Next, the locks of hair thus dyed are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the coloring obtained with respect to shampoo washing.

[0675] Shampoo wash protocol is the same as the protocol described in example 2.

[0676] Results:

[0677] 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).

[0678] 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.

[0679] The persistence of the coloring is evaluated by the color difference ΔE between the dyed locks before shampooing, then after having undergone three shampoo washes according to the protocol described in example 2. The lower the ΔE value, the more persistent the color with respect to shampoo washing.

[0680] The ΔE value is calculated according to the following equation:

ΔE=√{square root over ((L*−L.sub.0*).sup.2+(a*−a.sub.0*).sup.2+(b*−b.sub.0*).sup.2)}  [Math. 1]

[0681] In this equation, L*a*b* represent the values measured after dyeing the hair and after performing the shampoo washes, and L*.sub.0a.sub.0*b.sub.0* represent the values measured after dyeing the hair but before shampoo washing.

TABLE-US-00007 TABLES 7 Number of Compositions shampoo washes L* a* b* ΔE Composition A 0 35.95 26.62 19.47 (invention) 3 41.51 21.87 17.07 7.70 Composition B 0 37.23 28.47 20.89 — (comparative) 3 47.4 15.78 15.22 17.22

[0682] The locks of hair dyed with the composition A according to the invention and washed with three shampoo washes have ΔE values that are lower than those of the locks of hair dyed with the comparative composition B.

[0683] Thus, the colored coating of the keratin fibers obtained with the composition A according to the invention shows good persistence with respect to shampoo washing. Specifically, the locks of hair dyed with the composition A 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.