Process for treating keratin fibres, comprising the application of a composition comprising urea or a derivative thereof, a polyol and an amino silicone

Abstract

The present invention relates to a process for treating keratin fibres, in particular human keratin fibres such as the hair, comprising: 1) a step of applying to the keratin fibres a composition comprising: a) one or more compounds chosen from urea and/or urea derivatives, b) one or more polyols, c) one or more amino silicones, 2) a step of heat treatment of the keratin fibres, the heat treatment step 2) preferably being after step 1). The present invention also relates to a composition that may be used in the process according to the invention.

Claims

1. A process for treating keratin fibres, the process comprising: 1) applying to the keratin fibres a straightening composition comprising: a) at least one compound chosen from urea and/or urea derivatives, b) at least one polyol, c) at least one amino silicone, and d) at least one hydrophilic solvent chosen from ethyl alcohol, isopropyl alcohol, or a mixture thereof; wherein the weight ratio of the at least one compound b) to the at least one compound a) is greater than or equal to 1; and 2) heat treating the keratin fibres, wherein the heat treating of the keratin fibres is performed at a temperature ranging from 90° C. to 250° C., and wherein the process does not comprise a step of applying a reducing composition before, during or after the application of said straightening composition.

2. The process according to claim 1, wherein said at least one compound a) is chosen from the compounds of formula (I) or (II), salts thereof, or hydrates thereof: ##STR00013## wherein: R1, R2, R3 and R4 are each chosen from, independently: (i) a hydrogen atom or (ii) a linear or branched, cyclic or acyclic C.sub.1-C.sub.5 lower alkyl or alkenyl radical, a C.sub.1-C.sub.5 alkoxy radical, a C.sub.6-C.sub.18 aryl radical, a 5- to 8-membered heterocyclic radical; these radicals being optionally substituted with a radical chosen from the following radicals: hydroxyl, (C.sub.1-C.sub.4)alkyl, (di)(C.sub.1-C.sub.4)(alkyl)amino, preferably dimethylamino, carboxyl, halogen, C.sub.6-C.sub.18 aryl, carboxamide, or N-methylcarboxamide; with the proviso that: when R1, R2 and R3 represent a hydrogen atom, R4 may be chosen from: carboxamide, methoxy, ethoxy, 1,2,4-triazolyl, cyclopentyl, (C.sub.1-C.sub.6)alkylcarbonyl, acetyl, (C.sub.1-C.sub.6)alkoxycarbonyl, methoxycarbonyl, ethoxycarbonyl, CO—CH═CH—COOH, phenyl optionally substituted with a chlorine atom or a hydroxyl, benzyl, or 2,5-dioxo-4-imidazolidinyl radical; when R1 and R3 represent a hydrogen atom, R2 may represent a hydrogen atom or a methyl or ethyl radical and R4 may represent an acetyl radical; when R1 and R2 represent a hydrogen atom, R3 and R4 can form, with the nitrogen atom that bears them, a 5- or 6-membered ring, piperidine, 3-methylpyrazole, 3,5-dimethylpyrazole, or maleimide ring; R1 and R2 and also R3 and R4 can form, with the nitrogen atom that bears them, an imidazole ring; R5 and R6 are chosen from, independently of each other: (iii) a hydrogen atom or (iv) a linear or branched, cyclic or acyclic C.sub.1-C.sub.5 lower alkyl, acyl or alkenyl radical, a C.sub.1-C.sub.5 alkoxy radical, a C.sub.6-C.sub.18 aryl radical, a 5- to 8-membered heterocyclic radical; these radicals being optionally substituted with a radical chosen from the following radicals: hydroxyl, amino, dimethylamino, carboxyl, halogen, C.sub.6-C.sub.18 aryl, carboxamide, or N-methylcarboxamide; A is a radical chosen from the following radicals: CH.sub.2—CH.sub.2, CH═CH, CH.sub.2—CO, CO—NH, CH═N, CO—CO, CHOH—CHOH, (HOOC)CH—CH, CHOH—CO, CH.sub.2—CH.sub.2—CH.sub.2, CH.sub.2—NH—CO, CH═C(CH.sub.3)—CO, NH—CO—NH, CH.sub.2—CH.sub.2—CO, CH.sub.2—N(CH.sub.3)—CH.sub.2, NH—CH.sub.2—NH, CO—CH(CH.sub.3)—CH.sub.2, CO—CH.sub.2—CO, CO—NH—CO, CO—CH(COOH)—CH.sub.2, CO—CH═C(COOH), CO—CH═C(CH.sub.3), CO—C(NH.sub.2)═CH, CO—C(CH.sub.3)═N, CO—CH═CH, CO—CH═N, or CO—N═CH.

3. The process according to claim 2, wherein the at least one compound a) is of formula (I) and is chosen from: urea methylurea ethylurea propylurea n-butylurea sec-butylurea isobutylurea tert-butylurea cyclopentylurea ethoxyurea hydroxyethylurea N-(2-hydroxypropyl)urea N-(3-hydroxypropyl)urea N-(2-dimethylaminopropyl)urea N-(3-dimethylaminopropyl)urea 1-(3-hydroxyphenyl)urea benzylurea N-carbamoylmaleamide N-carbamoylmaleamic acid piperidinecarboxamide 1,2,4-triazol-4-ylurea hydantoic acid methyl allophanate ethyl allophanate acetylurea hydroxyethyleneurea 2-(hydroxyethyl)ethyleneurea diallylurea chloroethylurea N,N-dimethylurea N,N-diethylurea N,N-dipropylurea cyclopentyl-1-methylurea 1,3-dimethylurea 1,3-diethylurea 1,3-bis(2-hydroxyethyl)urea 1,3-bis(2-hydroxypropyl)urea 1,3-bis(3-hydroxypropyl)urea 1,3-dipropylurea ethyl-3-propylurea sec-butyl-3-methylurea isobutyl-3-methylurea cyclopentyl-3-methylurea N-acetyl-N′-methylurea trimethylurea butyl-3,3-dimethylurea tetramethylurea, or mixtures thereof.

4. The process according to claim 2, wherein the at least one compound a) is of formula (II) and is chosen from: parabanic acid 1,2-dihydro-3H-1,2,4-triazol-2-one barbituric acid uracil 1-methyluracil 3-methyluracil 5-methyluracil 1,3-dimethyluracil 5-azauracil 6-azauracil 5-fluorouracil 6-fluorouracil 1,3-dimethyl-5-fluorouracil 5-aminouracil 6-aminouracil 6-amino-1-methyluracil 6-amino-1,3-dimethyluracil 4-chlorouracil 5-chlorouracil 5,6-dihydrouracil 5,6-dihydro-5-methyluracil 2-imidazolidone 1-methyl-2-imidazolidinone 1,3-dimethyl-2-imidazolidinone 4,5-dihydroxyimidazolidin-2-one 1-(2-hydroxyethyl)-2-imidazolidinone 1-(2-hydroxypropyl)-2-imidazolidinone 1-(3-hydroxypropyl)-2-imidazolidinone 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one 1,3-bis(2-hydroxyethyl)-2-imidazolidinone 2-imidazolidone-4-carboxylic acid 1-(2-aminoethyl)-2-imidazole 4-methyl-1,2,4-triazoline-3,5-dione 2,4-dihydroxy-6-methylpyrimidine 1-amino-4,5-dihydro-1H-tetrazol-5-one hydantoin 1-methylhydantoin 5-methylhydantoin 5,5-dimethylhydantoin 5-ethylhydantoin 5-N-propylhydantoin 5-ethyl-5-methylhydantoin 5-hydroxy-5-methylhydantoin 5-hydroxymethylhydantoin 1-allylhydantoin 1-aminohydantoin hydantoin-5-acetic acid 4-amino-1,2,4-triazolone-3,5-dione hexahydro-1,2,4,5-tetrazine-3,6-dione 5-methyl-1,3,5-triazinon-2-one 1-methyltetrahydropyrimidin-2-one 2,4-dioxohexahydro-1,3,5-triazine urazole 4-methylurazole orotic acid dihydroxyorotic acid 2,4,5-trihydroxypyrimidine 2-hydroxy-4-methylpyrimidine 4,5-diamino-2,6-dihydroxypyrimidine 1,3-dimethylbarbituric acid cyanuric acid 1-methylhexahydropyrimidine-2,4-dione 1,3-dimethyl-3,4,5,6-tetrahydro-2-(1H)-pyrimidinone 5-(hydroxymethyl-2,4-(1H, 3H)-pyrimidinedione 2,4-dihydroxypyrimidine-5-carboxylic acid 6-azathymine 5-methyl-1,3,5-triazinan-2-one N-carbamoylmaleamic acid alloxan monohydrate, or mixtures thereof.

5. The process according to claim 1, wherein the at least one compound a) is chosen from urea, hydroxyethylurea, or mixtures thereof.

6. The process according to claim 1, wherein the total amount of the at least one compound a) ranges from 1% to 15% by weight, relative to the total weight of the straightening composition.

7. The process according to claim 1, wherein the at least one compound b) is chosen from polyols comprising at least three carbon atoms, ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butylene glycol, 1,2-pentanediol, dipropylene glycol, hexylene glycol, pentylene glycol, glycerol, or a mixture thereof.

8. The process according to claim 1, wherein the total amount of the at least one compound b) ranges from 1% to 30% by weight, relative to the total weight of the straightening composition.

9. The process according to claim 1, wherein the at least one compound c) is chosen from amino silicones comprising at least 4 carbon atoms.

10. The process according to claim 1, wherein the at least one compound c) is chosen from the silicone(s) (a) to (f) below: (a) the compounds corresponding to formula (III) below:
(R.sub.1).sub.a(T).sub.3-a-Si[OSi(T).sub.2].sub.n-[(OSi(T).sub.b(R.sub.1).sub.2-b].sub.m—OSi(T).sub.3-a-(R.sub.1).sub.a  (III), wherein in formula (III): T is chosen from a hydrogen atom or a phenyl, hydroxyl (—OH), C.sub.1-C.sub.8 alkyl group, methyl, C.sub.1-C.sub.8 alkoxy, or methoxy, a is 0 or an integer from 1 to 3, b is 0 or 1, m and n are integers such that the sum (n+m) ranges from 1 to 2000, n is a number from 0 to 1999, and m is a number from 1 to 2000, R.sub.1 is a monovalent group of formula —C.sub.qH.sub.2qL in which q is an integer from 2 to 8 inclusive and L is an optionally quaternized amino group chosen from the following groups: N(R.sub.2)—CH.sub.2—CH.sub.2—N(R.sub.8).sub.2, N(R.sub.2).sub.2, N.sup.+(R.sub.2).sub.3 Q.sup.−, N.sup.+(R.sub.2) (H).sub.2.sup.−, N+(R.sub.2).sub.2HQ.sup.−, N(R.sub.2)—CH.sub.2—CH.sub.2—N+(R.sub.2)(H).sub.2 Q.sup.−, wherein:  R.sub.2 is chosen from a hydrogen atom, a phenyl group, a benzyl group, a saturated monovalent hydrocarbon-based group, or a C.sub.1-C.sub.20 alkyl group, and  Q.sup.− is chosen from an anionic counterion, a halide ion, fluoride, chloride, bromide, or iodide, (b) the compounds corresponding to formula (VI) below: ##STR00014## wherein in formula (VI): R.sup.3 is chosen from a monovalent C.sub.1-C.sub.18 hydrocarbon-based group, C.sub.1-C.sub.18 alkyl, C.sub.2-C.sub.18 alkenyl, or methyl; R.sup.4 is chosen from a divalent hydrocarbon-based group, a C.sub.1-C.sub.18 alkylene group, a divalent C.sub.1-C.sub.18, or C.sub.1-C.sub.8, alkyleneoxy group; Q.sup.− is chosen from an anionic counterion, halide ions, or chloride; r represents a mean statistical value from 2 to 20; s represents a mean statistical value from 20 to 200; (c) quaternary ammonium silicones, of formula (VII): ##STR00015## wherein in formula (VII): R.sub.6 is chosen from a divalent hydrocarbon-based group, a C.sub.1-C.sub.18 alkylene group, a divalent C.sub.1-C.sub.18, or C.sub.1-C.sub.8, alkyleneoxy group linked to the Si atom via an SiC bond; R.sub.7, which may be identical or different, is chosen from a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, a C.sub.1-C.sub.18 alkyl group, a C.sub.2-C.sub.18 alkenyl group, a ring comprising 5 or 6 carbon atoms, or methyl; R.sub.8, which may be identical or different, are each chosen from a hydrogen atom, a monovalent hydrocarbon-based group containing from 1 to 18 carbon atoms, a C.sub.1-C.sub.18 alkyl group, a C.sub.2-C.sub.18 alkenyl group, or a group —R.sub.6—N(H)—C(O)—R.sub.7 with R.sub.6 and R.sub.7 as defined previously; X.sup.−, which may be identical or different, is chosen from an anionic counterion, a halide ion, chloride, an anionic counterion derived from an organic acid, or (C.sub.1-C.sub.6)alkylcarboxylate; r represents a mean statistical value between 2 and 200 inclusive; (d) the amino silicones of formula (VIII): ##STR00016## wherein in formula (VIII): R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, are each chosen from a C.sub.1-C.sub.4 alkyl group, an aryl group, or phenyl, R.sub.5 is chosen from a C.sub.1-C.sub.4 alkyl group or a hydroxyl group, n and m, which may be identical or different, represent an integer between 1 and 5 inclusive, and x is such that the amine number is between 0.01 and 1 meq/g; (e) the amino silicones bearing polyalkoxylene groups of formula (IX): ##STR00017## wherein in formula (IX): R.sup.a, R.sup.b, R.sup.c and R.sup.d, which may be identical or different, are chosen from a hydroxyl group, a linear or branched (C.sub.1-C.sub.10)alkyl group, a (C.sub.1-C.sub.6)alkyl group, or methyl; ALK and ALK′, which may be identical or different, are chosen from a linear or branched (C.sub.1-C.sub.10)alkylene group, or propylene; A and B, which may be identical or different, are chosen from an aminopolyalkoxy group below:
R.sup.eR.sup.fN-[ALK″-O].sub.z-[ALK′″-O].sub.w-ALK.sup.a-N(R.sup.g[ALK.sup.b-O].sub.q—*, wherein: represents the point of attachment of the radical to the rest of the molecule via ALK or ALK′; R.sup.e, R.sup.f and R.sup.g, which may be identical or different, are chosen from a hydrogen atom or a linear or branched (C.sub.1-C.sub.10)alkyl group; ALK″ and ALK′″, which may be identical or different, are chosen from a linear or branched (C.sub.1-C.sub.10)alkylene, C.sub.2 or C.sub.3 alkylene group; a divalent group —CH.sub.2—CH(CH.sub.3)—, or an ethylene group; ALK.sup.a and ALK.sup.b, which may be identical or different, are chosen from a linear or branched (C.sub.1-C.sub.10)alkylene, C.sub.2 or C.sub.3 alkylene group, which is optionally substituted, ethylene, propylene group, a divalent group —CH.sub.2—CH(CH.sub.3)—, or a divalent group —CH.sub.2—CH(OH)—CH.sub.2—; q, which may be identical or different, represent 0 or 1; w, which may be identical or different, represent an integer, wherein the sum of the w values (w of A+w of B) having a mean value of between 10 and 100 inclusive; z, which may be identical or different, represent an integer, wherein the sum of the z values (z of A+z of B) having a mean value of between 1 and 20 inclusive; (f) amino silicones bearing polyalkoxylene groups constituted of polysiloxane blocks and of polyalkoxylene blocks comprising at least one amine group, chosen from: those of formula (X): ##STR00018## wherein in formula (X): R.sup.a, R.sup.b, R.sup.c and R.sup.d, which may be identical or different, are chosen from a hydroxyl group, a linear or branched (C.sub.1-C.sub.10) alkyl group, a (C.sub.1-C.sub.4)alkyl group, or methyl; R, which may be identical or different, is chosen from a linear or branched C.sub.2-C.sub.6 alkylene radical, which is optionally hydroxylated and/or optionally interrupted with an oxygen atom; a and b, which may be identical or different, each represent a number ranging from 0 to 100; R′, which may be identical or different, is chosen from a hydrogen atom, a C.sub.1-C.sub.4 alkyl radical, or a methyl radical; x denotes an integer ranging from 1 to 500 and y denotes an integer ranging from 1 to 10; those containing units of formula (XI) ##STR00019## wherein in formula (XI): R.sub.1 to R.sub.4, which may be identical or different, are chosen from a C.sub.1-C.sub.4 alkyl radical or methyl; R and R″, which may be identical or different, each represent a linear or branched C.sub.2-C.sub.6 alkylene radical, which is optionally hydroxylated and optionally interrupted with an oxygen atom; a and b, which may be identical or different, each denote an integer ranging from 0 to 100; R′ and R″, which may be identical or different, are chosen from a hydrogen atom, a C.sub.1-C.sub.4 alkyl radical, or a methyl radical; and x denotes a number ranging from 1 to 500 and y denotes a number ranging from 1 to 10; those containing units of formula (XII) or of formula (XIII) ##STR00020## wherein in formulae (XII) and (XIII): R, which may be identical or different, is chosen from a linear or branched divalent C.sub.2-C.sub.12 alkyl radical, optionally comprising one or more heteroatoms or oxygen; an ethylene radical; a linear or branched propylene radical; a linear or branched butylene radical; or a radical —CH.sub.2CH.sub.2CH.sub.2OCH(OH)CH.sub.2—; R′, which may be identical or different, is chosen from a linear or branched divalent C.sub.2-C.sub.12 alkyl radical, optionally comprising one or more heteroatoms or oxygen; an ethylene radical; a linear or branched propylene radical; a linear or branched butylene radical, a radical —CH.sub.2CH.sub.2CH.sub.2OCH(OH)CH.sub.2—, or a radical —CH(CH.sub.3)—CH.sub.2—; R″ is chosen from a hydrogen atom or a methyl radical; x denotes an integer ranging from 1 to 10 000; a denotes an integer greater than or equal to 1; b denotes an integer ranging from 0 to 200.

11. The process according to claim 10, wherein the amino silicone is chosen from the silicones of formulae (Ill), (VIII), (XI), (XII), or (XIII).

12. The process according to claim 1, wherein the total amount of the at least one amino silicone ranges from 0.1% to 4% by weight, relative to the total weight of the straightening composition.

13. The process according to claim 1, wherein the straightening composition further comprises at least one thickener.

14. The process according to claim 1, wherein the heat treating of the keratin fibres is performed at a temperature ranging from 180° C. to 230° C.

15. The process according to claim 1, wherein the heat treating step has a duration ranging from 5 seconds to 1 hour, per lock of hair.

Description

EXAMPLES

Example 1

(1) Comparative composition 1 and compositions 2 and 3 according to the invention, which may be used in the process according to the invention, were prepared on the basis of the formulations indicated in Table 1 below, in which the amounts are expressed as weight percentages relative to the total weight of the composition.

(2) TABLE-US-00001 TABLE 1 Compositions Ingredients 1 2 3 Urea 10 10 10 Ethanol 10 10 10 1,3-Propanediol 10 10 10 Amodimethicone and — — 6.67 Trideceth-5 and Trideceth-10.sup.(1) Amodimethicone and — 1.68 — Trideceth-6 and cetrimonium chloride.sup.(2) Water qs 100 qs 100 qs 100 .sup.(1)Polydimethylsiloxane bearing aminoethyl iminopropyl groups as a nonionic microemulsion containing 17% AM (Belsil AMD Log 1 from Wacker). .sup.(2)Polydimethylsiloxane bearing aminoethyl aminopropyl groups, bearing a methoxy and/or hydroxyl function and alpha-omega silanols, as a cationic 60% aqueous emulsion (Xiameter MEM-8299 from Dow Corning)

(3) The straightening process used in this example is as follows: shampooing then drying of the locks of hair studied, application of one of the compositions of Table 1 to dry hair (bath ratio=1:1) leave-on time: 5 min blow-drying: 15 passes (maximum power) straightening iron: 5 slow passes (6 sec/20 cm) per lock at 230° C. for locks of 1 to 1.5 g (on average 1.35 g).

(4) Starting locks: Natural curly type IV Caucasian

(5) The locks of hair undergo 1 and 5 shampoo washes in order to evaluate the persistence over time of the straightening processes.

(6) The curl relaxation quality and the volume control are evaluated visually after one shampoo wash and after five shampoo washes.

(7) The processes according to the invention (compositions 2 and 3) afford better curl relaxation and also better volume control than the comparative process not comprising the application of a composition comprising an amino silicone. In particular, the curl relaxation is complete from the very first shampoo wash and persistent over the following shampoo washes.

(8) Furthermore, the processes according to the invention make it possible to give the hair better cosmeticity. The locks have a smoother feel, down to the ends.

Example 2

(9) Comparative composition 4 and composition 5 according to the invention, which may be used in the process according to the invention, were prepared on the basis of the formulations indicated in Table 2 below, in which the amounts are expressed as weight percentages of active matter relative to the total weight of the composition.

(10) TABLE-US-00002 TABLE 2 Compositions Ingredients 4 5 Urea 10 10 Ethanol 10 10 1,3-Propanediol 10 10 Amodimethicone and — 1 Trideceth-5 and Trideceth- 10.sup.(1) Levulinic acid 10 10 Water qs 100 qs 100 .sup.(1)Polydimethylsiloxane bearing aminoethyl iminopropyl groups as a nonionic microemulsion containing 17% AM (Belsil AMD Log 1 from Wacker).

(11) The straightening process used in this example is as follows: shampooing then drying of the locks of hair studied, application of one of the compositions of Table 2 to dry hair (bath ratio=1:1) leave-on time: 30 min blow-drying: 15 passes with a brush (with the maximum power of the hair dryer) straightening iron: 10 slow passes (6 sec/20 cm) per lock at 210° C. for locks of 1 to 1.5 g (on average 1.35 g).

(12) Starting locks: Natural curly type IV Caucasian

(13) The locks of hair undergo 1 and 10 shampoo washes in order to evaluate the persistence over time of the straightening processes.

(14) The curl relaxation quality and the volume control are evaluated visually by comparative pictures after one shampoo wash and after ten shampoo washes. The curls are washed with a classical shampoo (DOP Camomille), rinsed, then air dried.

(15) The curls are vertically suspended then pictured.

(16) The coefficient of straightening is calculated: it corresponds to the ratio length/width of the locks of hair.

(17) Picture T corresponds to a lock of hair before the process (natural curly type IV Caucasian)

(18) Pictures D1 and D10 correspond to locks of hair treated with the composition D (comparative) after one shampoo (D1) and ten shampoos (D10).

(19) Pictures E1 and E10 correspond to locks of hair treated with the composition E (invention) after one shampoo (E1) and ten shampoos (E10).

(20) The length/width measures and the coefficient of straightening are given in the table 3 below.

(21) TABLE-US-00003 TABLE 3 D E 1 shampoo Length 18.75 19.8 Width 5.31 4.52 Coefficient of 3.53 4.38 straightening 10 Length 17.78 19.2 shampoo Width 4.52 2.8 Coefficient of 3.93 6.86 straightening

(22) The composition E according to the invention and which can be used in the process according to the invention has been able to improve the sustainability of straightening in comparison with the comparative composition D.

(23) In particular, the locks of hair treated with the composition E are straight-lined (see pictures E). The locks of hair treated with the composition D have undulations (see pictures D).

(24) This improvement is visible after one shampoo and also after ten shampoos.