PROCESS FOR TREATING KERATIN FIBRES WITH A CATIONIC DISULFIDE COMPOUND

Abstract

The invention relates to a process for treating keratin fibres, in particular human keratin fibres such as the hair, comprising: (i) a step of applying a compound (I)

##STR00001##

and also the acid or base salts thereof, the optical or geometrical isomers thereof,
and the solvates thereof such as hydrates,
in which compound of formula (I): R.sup.1, R.sup.2, R.sup.3, R.sup.4, x, m, n, X.sup., are as defined in the description; (ii) a step of heating the keratin fibres to a temperature of at least 100 C., preferably ranging from 100 to 250 C.;
it is understood that steps (i) and (ii) may be performed at the same time or separately.

The process makes it possible to obtain good hair-conditioning cosmetic properties, with a long-lasting effect.

The invention also relates to the novel compounds and to a cosmetic composition comprising such a compound.

Claims

1-24. (canceled)

25. A method for treating keratin fibers, the method comprising: (i) applying to the keratin fibers at least one disulfide compound of formula (I): ##STR00022## an acid or base salt thereof, an optical, geometrical isomer thereof, a tautomer thereof, or a solvate thereof, wherein: R.sup.1 is chosen from a hydrocarbon-based group chosen from methyl, ethyl, i) CH.sub.2(CH.sub.2).sub.mCH.sub.3, ii) CH.sub.2(CH.sub.2).sub.m-1CH(CH.sub.3).sub.2, or iii) CH.sub.2(CH.sub.2).sub.m-1C(CH.sub.3).sub.3; R.sup.2 and R.sup.3, independently of each other, are chosen from a linear hydrocarbon-based group containing from 1 to 6 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 carbon atoms, which is saturated or unsaturated, and optionally substituted with at least one hydroxyl group; R.sup.4 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; x is an integer ranging from 1 to 20; m is an integer ranging from 1 to 20; n is an integer ranging from 1 to 20; wherein 10m+n30; X.sup., which may be identical or different, is an anionic counterion; and Y is chosen from an oxygen atom, a sulfur atom, or a N(R.sup.5) group, wherein R.sup.5 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; and (ii) heating the keratin fibers to a temperature of at least about 100 C.; wherein steps (i) and (ii) may be performed at the same time or separately.

26. The method of claim 25, wherein R.sup.1 is chosen from a hydrocarbon-based group: ethyl, and/or i) CH.sub.2(CH.sub.2).sub.mCH.sub.3, wherein m is an integer ranging from 1 to 20.

27. The method of claim 25, wherein R.sup.1 is chosen from a hydrocarbon-based group ii) CH.sub.2(CH.sub.2).sub.m-1CH(CH.sub.3).sub.2, wherein m is an integer ranging from 1 to 20.

28. The method of claim 25, wherein R.sup.1 is chosen from a hydrocarbon-based group containing from 15 to 19 carbon atoms.

29. The method of claim 25, wherein n is an integer ranging from 3 to 20.

30. The method of claim 25, wherein the sum of m+n ranges inclusively between 12 and 22, 12m+n22.

31. The method of claim 25, wherein x is an integer ranging inclusively between 1 and 4.

32. The method of claim 25, wherein R.sup.2 and R.sup.3, which may be identical or different, are chosen from a linear hydrocarbon-based group containing from 1 to 6 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 carbon atoms, which is unsubstituted.

33. The method of claim 25, wherein R.sup.2 and R.sup.3, which may be identical or different, are chosen from a linear or branched (C.sub.1-C.sub.6)alkyl group.

34. The method of claim 25, wherein X.sup. is an anionic counterion chosen from halide ions, chloride, bromide, sulfate, phosphates, RC(O)O with R denoting an optionally hydroxylated C.sub.1-C.sub.5 hydrocarbon-based radical, acetate, lactate, citrate, (C.sub.1-C.sub.4)alkyl sulfates, (C.sub.1-C.sub.4)alkylaryl-sulfonates, mesylate, tosylate, or triflate.

35. The method of claim 25, wherein the at least one disulfide compound of formula (I) is chosen from the following: ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029##

36. The method of claim 25, wherein the at least one disulfide compound is present in a cosmetic composition, and the at least one disulfide compound is present in an amount ranging from 0.5% to 20% by weight, relative to the total weight of the cosmetic composition.

37. The method of claim 25, wherein the heating step is performed at a temperature ranging from 100 C. to about 250 C.

38. The method of claim 25, further comprising drying the keratin fibers after the application step and before the heating step, wherein the drying step is performed at a temperature ranging from 20 C. to 70 C.

39. The method of claim 25, further comprising a leave-on time ranging from about 1 minute to about 60 minutes, after the application step and before the heating step.

40. The method of claim 25, wherein the heating step is performed with a straightening iron.

41. The method of claim 25, further comprising applying steam to the keratin fibers.

42. The method of claim 41, wherein the steam is applied at a flow rate of less than about 5 g/min.

43. The method of claim 40, wherein the straightening iron is applied to the hair in a continuous movement from the root to the end of the hairs, in at least one pass.

44. A compound of formula (I) below: ##STR00030## wherein: R.sup.1 is chosen from a hydrocarbon-based group chosen from methyl, ethyl, i) CH.sub.2(CH.sub.2).sub.mCH.sub.3, ii) CH.sub.2(CH.sub.2).sub.m-1CH(CH.sub.3).sub.2, or iii) CH.sub.2(CH.sub.2).sub.m-1C(CH.sub.3).sub.3; R.sup.2 and R.sup.3, independently of each other, are chosen from a linear hydrocarbon-based group containing from 1 to 6 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 carbon atoms, which is saturated or unsaturated, and optionally substituted with at least one hydroxyl group; R.sup.4 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; x is an integer ranging from 1 to 20; m is an integer ranging from 1 to 20; n is an integer ranging from 1 to 20; wherein 10m+n30; X.sup., which may be identical or different, is an anionic counterion; and Y is chosen from an oxygen atom, a sulfur atom, or a N(R.sup.5) group, wherein R.sup.5 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group, with the exclusion of: compounds wherein x is an integer inclusively between 1 and 4; n is 1 or 2; R.sup.2 and R.sup.3 are a methyl group; R.sup.1 is a C.sub.1-C.sub.20 hydrocarbon-based radical; R.sup.4 is a hydrogen atom; and X.sup. is a halide ion; ##STR00031##

45. The compound of claim 44, chosen from: ##STR00032## wherein X.sup., which may be identical or different, is an anionic counterion.

46. A cosmetic composition comprising, in a physiologically acceptable medium, a compound of formula (I): ##STR00033## wherein: R.sup.1 is chosen from a hydrocarbon-based group chosen from methyl, ethyl, i) CH.sub.2(CH.sub.2).sub.mCH.sub.3, ii) CH.sub.2(CH.sub.2).sub.m-1CH(CH.sub.3).sub.2, or iii) CH.sub.2(CH.sub.2).sub.m-1C(CH.sub.3).sub.3; R.sup.2 and R.sup.3, independently of each other, are chosen from a linear hydrocarbon-based group containing from 1 to 6 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 carbon atoms, which is saturated or unsaturated, and optionally substituted with at least one hydroxyl group; R.sup.4 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; x is an integer ranging from 1 to 20; m is an integer ranging from 1 to 20; n is an integer ranging from 1 to 20; wherein 10m+n30; X.sup., which may be identical or different, is an anionic counterion; and Y is chosen from an oxygen atom, a sulfur atom, or a N(R.sup.5) group, wherein R.sup.5 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group, wherein the compound of formula (I) is present in an amount ranging from about 0.5% to about 20% by weight, relative to the total weight of the composition.

47. A method for preparing compounds of formula (I): ##STR00034## wherein: R.sup.1 is chosen from a hydrocarbon-based group chosen from methyl, ethyl, i) CH.sub.2(CH.sub.2).sub.mCH.sub.3, ii) CH.sub.2(CH.sub.2).sub.m-1CH(CH.sub.3).sub.2, or iii) CH.sub.2(CH.sub.2).sub.m-1C(CH.sub.3).sub.3; R.sup.2 and R.sup.3, independently of each other, are chosen from a linear hydrocarbon-based group containing from 1 to 6 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 carbon atoms, which is saturated or unsaturated, and optionally substituted with at least one hydroxyl group; R.sup.4 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; x is an integer ranging from 1 to 20; m is an integer ranging from 1 to 20; n is an integer ranging from 1 to 20; wherein 10m+n30; X.sup., which may be identical or different, is an anionic counterion; and Y is chosen from an oxygen atom, a sulfur atom, or a N(R.sup.5) group, wherein R.sup.5 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group, according to scheme 1 or 2 below: ##STR00035## wherein compounds (A), (B), (C), (D) and (E): X, which may be identical or different, is an anionic counterion; Y, is chosen from an oxygen atom, a sulfur atom, or a N(R.sup.5) group, wherein R.sup.5 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; R.sup.1 is chosen from a hydrocarbon-based group chosen from methyl, ethyl, i) CH.sub.2(CH.sub.2).sub.mCH.sub.3, ii) CH.sub.2(CH.sub.2).sub.m-1CH(CH.sub.3).sub.2, or iii) CH.sub.2(CH.sub.2).sub.m-1C(CH.sub.3).sub.3; R.sup.2 and R.sup.3, independently of each other, are chosen from a linear hydrocarbon-based group containing from 1 to 6 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 carbon atoms, which is saturated or unsaturated, and optionally substituted with at least one hydroxyl group; R.sup.4 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; n is an integer ranging from 1 to 20; wherein 10m+n30; x is an integer ranging from 1 to 20; and Hal is a halogen atom; wherein Scheme 1: first, performing halogenation in the presence of a standard halogenating agent to obtain the corresponding halide (B); second, performing dicondensation (amidation, thioamidation) by adding to compound (B) the diamine disulfide (C) in the presence of a base to obtain compound (D); and third, adding at least 2 molar equivalents of the trialkylamine (E) to obtain the compounds of formula (I); ##STR00036## wherein compounds (A), (B), (C), (D), (E) and (E): X, which may be identical or different, is an anionic counterion; Y is chosen from an oxygen atom, a sulfur atom, or a N(R.sup.5) group, wherein R.sup.5 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; R.sup.1 is chosen from a hydrocarbon-based group chosen from methyl, ethyl, i) CH.sub.2(CH.sub.2).sub.mCH.sub.3, ii) CH.sub.2(CH.sub.2).sub.m-1CH(CH.sub.3).sub.2, or iii) CH.sub.2(CH.sub.2).sub.m-1C(CH.sub.3).sub.3; R.sup.2 and R.sup.3, independently of each other, are chosen from a linear hydrocarbon-based group containing from 1 to 6 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 carbon atoms, which is saturated or unsaturated, and optionally substituted with at least one hydroxyl group; R.sup.4 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; n is an integer ranging from 1 to 20; wherein 10m+n30; x is an integer ranging from 1 to 20; and R.sup.5 is chosen from a halogen atom or a (C.sub.1-C.sub.6)alkoxy group; wherein Scheme 2: first, performing condensation of the (thio)lactone (A) with the disulfide (B) in the presence of a polar solvent at a temperature close to the boiling point of the solvent, to form compound (C), which is isolated by precipitation or after evaporating off the solvent; second, placing compound (C) in a solvent, cooling the mixture to a temperature ranging from about 0 C. to about 5 C., adding a mineral base to the mixture, and then adding compound D with an amount of base in an equivalent amount relative to R.sup.5 present in (D) if R.sup.5 is a halogen atom, to obtain compound (E); and third, adding the amine (E) in an amount ranging from 2 molar equivalents to 10 molar equivalents, without a solvent or in a polar solvent, to obtain compound (I).

48. A kit comprising: a cosmetic composition comprising a packaging assembly, wherein the packaging assembly comprises a compound of formula (I): ##STR00037## an acid or base salt thereof, an optical, geometrical isomer thereof, a tautomer thereof, or a solvate thereof, wherein: R.sup.1 is chosen from a hydrocarbon-based group chosen from methyl, ethyl, i) CH.sub.2(CH.sub.2).sub.mCH.sub.3, ii) CH.sub.2(CH.sub.2).sub.m-1CH(CH.sub.3).sub.2, or iii) CH.sub.2(CH.sub.2).sub.m-1C(CH.sub.3).sub.3; R.sup.2 and R.sup.3, independently of each other, are chosen from a linear hydrocarbon-based group containing from 1 to 6 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 carbon atoms, which is saturated or unsaturated, and optionally substituted with at least one hydroxyl group; R.sup.4 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group; x is an integer ranging from 1 to 20; m is an integer ranging from 1 to 20; n is an integer ranging from 1 to 20; wherein 10m+n30; X.sup., which may be identical or different, is an anionic counterion; and Y is chosen from an oxygen atom, a sulfur atom, or a N(R.sup.5) group, wherein R.sup.5 is chosen from a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group, and a device for heating the keratin fibers to a temperature of at least about 100 C.

Description

EXAMPLE 1: PREPARATION OF COMPOUND 1

N-(17,17-dimethyl-4,13-dioxo-8,9-dithia-5,12-diaza-17-azoniatritriacont-1-yl)-N, N-dimethylhexadecan-1-ammonium dichloride

[0125] ##STR00019##

1st Step: Synthesis of N, N-(disulfanediyldiethane-2,1-diyl)bis(4-chlorobutanamide)

[0126] ##STR00020##

[0127] 107.6 g of sodium hydroxide (2.7 mol) were placed in 150 ml of water in a jacketed reactor, equipped with a condenser, an argon inlet, a temperature probe and a mechanical stirring system. The mixture was left stirring for 15 minutes at room temperature, followed by addition of 150 g of cystamine dihydrochloride (0.672 mol) and 850 ml of water. Stirring was continued for 90 minutes, setting a nominal temperature at 15 C. After 90 minutes, a temperature of 2 C. and a pH of 11.4 were reached. 1.50 ml of 4-chlorobutyryl chloride (95% tech., 1.34 mol) were added dropwise over 60-80 minutes while monitoring the addition with the temperature (<10 C.) and the pH (>9). The reaction medium was maintained at room temperature for 18 hours, while monitoring the reaction progress by TLC: 9/1 dichloromethane/methanol eluent, revelation by UV and KMnO4. The reaction medium was filtered and rinsed thoroughly with water. The precipitate was dried under vacuum at 40 C. in the presence of P.sub.2O.sub.5 to constant weight, to obtain 157 g of the expected compound in the form of a white powder.

[0128] NMR spectrum and mass spectrum compliant.

2nd Step: Synthesis of Compound 1

[0129] ##STR00021##

[0130] 5.8 g of N,N-dimethylhexadecylamine (0.01 mol) and 3.6 g (0.02156 mol) of the compound obtained in the preceding step 1 were placed in 100 ml reactor, equipped with a condenser, an argon inlet, a temperature probe and a mechanical stirring system. The reaction medium was left stirring for 15 minutes at room temperature and was then maintained at 145 C. for 6 hours. It was then allowed to cool to room temperature and the paste obtained was taken up in 50 ml of acetone. This operation was repeated three times, removing the acetone phase each time. The paste obtained was dried under vacuum at 45 C. for 6 hours. 7 g of a brown paste were obtained.

[0131] NMR spectrum and mass spectrum compliant.

EXAMPLE 2: PREPARATION OF COMPOUND 2

1st Step

[0132] 10 g (0.0779 mol) of hexadecanolide lactone, 33.3 ml of aqueous sodium hydroxide at 50% by weight (33.3 mL) in 50 ml of toluene and 0.186 g of tetrabutylammonium hydrogen sulfate were placed in a three-necked round-bottomed flask. The reaction mixture was stirred for 6 hours at 95 C. After cooling, the solid formed was filtered off, rinsed several times with ether and then placed in 400 ml of distilled water and acidified with concentrated hydrochloric acid to pH 1.5. The precipitate obtained was filtered off and then rinsed several times with distilled water, and then dried under vacuum at 60 C. 11.5 g of 16-hydroxy-hexadodecanoic acid were obtained, in the form of a white solid (97% yield).

[0133] 1H NMR and mass spectra compliant.

2nd Step

[0134] 10.62 g (0.039 mol) of 16-hydroxyhexadecanoic acid were placed in a three-necked flask under nitrogen, equipped with a condenser, a mechanical stirrer and a nitrogen inlet, followed by addition of 50 ml of hydrobromic acid at 33% by weight in acetic acid and 18.6 ml of concentrated sulfuric acid.

[0135] The assembly was then connected to three traps containing sodium hydroxide, aqueous sodium hydroxide at 25% by weight and saturated potassium carbonate solution. The reaction mixture was stirred vigorously for 15 hours at 20 C. and then refluxed for 3 hours. After cooling, the reaction mixture was poured into ice-water and the precipitate formed was extracted with dichloromethane (3100 ml). The organic phase was washed with distilled water (350 ml), dried over MgSO.sub.4 and evaporated under vacuum. 11 g of 16-bromohexadecanoic acid BrC.sub.15H.sub.30C(O)OH were recovered in the form of an off-white solid.

[0136] 1H NMR and mass spectra compliant.

3rd Step

[0137] 9.4 g (0.028 mol) of 16-bromohexadecanoic acid were placed in a round-bottomed flask under nitrogen, equipped with a condenser and a magnetic stirrer, followed by addition of 6.3 ml (2.5 equivalents) of oxalyl chloride. The reaction mixture was stirred and then heated to 40 C.

[0138] After stirring for 10 minutes at 20 C., the reaction mixture was heated slightly to allow total evolution of the gas, and was then maintained at reflux for 2 hours. After cooling, the excess oxalyl chloride was evaporated off under vacuum. 9.8 g of 16-bromohexadecanoyl chloride were obtained, in the form of a brown solid.

[0139] The product is stable if it is stored protected from light, under argon and in a refrigerator.

[0140] 1H NMR and mass spectra compliant.

4th Step

[0141] 0.9 g (0.004 mol) of cystamine hydrochloride and 40 ml of anhydrous acetonitrile were placed in a round-bottomed flask under nitrogen, equipped with a magnetic stirrer and a thermometer. The reaction mixture was stirred and cooled to 0 C., followed by dropwise addition of 4 g (0.04 mol) of triethylamine, with continued stirring at 0 C. for 3 hours. Next, 3.788 g (0.0112 mol) of 16-bromohexadecanoyl chloride in acetonitrile (5 mL) were added at 0 C. and stirring was continued at 0 C. for 1 hour and then at 20 C. for 15 hours. The solvent was evaporated off under vacuum and the residue was treated with water and then extracted with chloroform (350 ml). The organic phase was washed with 2N hydrochloric acid (215 mL) and then with distilled water (215 mL), dried over MgSO4 and finally evaporated under vacuum. The solid obtained was purified by rinsing several times with heptane/ether (5/1 vol). 4.2 g of disulfide [BrC.sub.15H30-CONHC2H4S]2- were recovered in the form of an off-white solid (82% yield).

[0142] 1H NMR and mass spectra compliant.

5th Step

[0143] 5.0 g (0.00636 mol) of dibromo disulfide obtained in step 4 and 20 ml of anhydrous tetrahydrofuran were placed in a two-necked round-bottomed flask under nitrogen, equipped with a condenser and a thermometer. The reaction mixture was heated and stirred at 40 C. until a homogeneous solution was obtained, 150 ml of triethylamine were then added dropwise and stirring was continued at 40 C. Next, the reaction mixture was refluxed for 48 hours. The excess solvent was allowed to separate out by settling, without cooling, further triethylamine (50 mL) was added and the mixture was refluxed for 30 minutes and allowed to settle again to separate out the expected product. The residue obtained, in the form of a pasty brown product, was then treated with chloroform. This treatment led to the formation of two phases: a brown phase containing the product and the colourless organic phase containing the impurities. The brown phase was separated out using a separating funnel, rinsed twice with chloroform and dried under vacuum. The brown semi-solid product was then stirred in ether until a light-beige powder was obtained. After filtration and drying under vacuum, 6 g of the expected cationic disulfide were recovered (95% yield).

[0144] 1H NMR and mass spectra compliant.

EXAMPLE 3

Compositions Prepared

[0145]

TABLE-US-00001 Compositions B A1 A2 A3 A4 (placebo) Compound 1* 0.5 5 10 20 0 Water qs 100 qs 100 qs 100 qs 100 qs 100 *amount in g per 100 g of composition

[0146] In the application examples described below, locks of hair sensitized after bleaching were used (SA 40%). The composition to be evaluated is applied at a rate of 3 g of composition per 2.7 g of tresses. Each composition evaluated was applied to two tresses.

[0147] The composition was applied to tresses of hair and then left on for 20 minutes at room temperature (25 C.).

[0148] The tresses were towel dried and then dried using a hairdryer for 10 minutes at 60 C. (blow dried).

[0149] The locks were combed before applying:

either a straightening iron at a temperature of 210 C. by performing six continuous passes through the tresses for 15 seconds,
or a steam iron at a temperature of 210 C. (Steampod LP8500 Go/7PO device by Rowenta) performing three continuous passes through the tresses for 15 seconds,
or a hairdryer at 60 C. for 10 minutes.

[0150] To evaluate the durable (persistent) nature of the cosmetic properties of the hair tresses, they were then washed with one, ten or twenty successive shampoos respectively according to the following protocol:

[0151] The treated tresses were washed with an Ultradoux camomile shampoo by Garnier, at a rate of 0.4 g of shampoo per gram of hair, at a temperature of 38 C. Moisten the lock for 5 seconds with water. Apply the shampoo, massaging the lock from the root to the end for 15 seconds. Rinse with water for 10 seconds. Wring out. Leave the locks to dry in the open air overnight.

[0152] For 10 and 20 shampoo washes, the washes were done one after the other without drying in between.

[0153] The cosmetic properties of the locks after shampooing were then evaluated after one, ten or twenty shampoo washes respectively, especially the cosmetic feel, the manageability and the ease of combing of the locks (disentangling).

[0154] The performances were recorded as follows:

for a bad result
+ for a poor result
++ for a moderate result
+++ for a good result

[0155] The following results were obtained: [0156] 1) After treating the keratin fibres with compositions A1 to A4, without a flat iron: Comparative

TABLE-US-00002 Cosmetic properties Compositions evaluated Shampoo A1 A2 A3 A4 Softness 0 shp + + + 1 shp + + Disentangling 1 shp + + Manageability 1 shp + + [0157] 2) After treating the keratin fibres with compositions A1 to A4, then with the iron: Invention

TABLE-US-00003 With iron at 210 C. - Invention Cosmetic properties Compositions evaluated Shampoos A1 A2 A3 A4 Softness 0 shp ++ ++ 1 shp + +++ ++ 10 shp +++ ++ + Disentangling 1 shp + ++ ++ +++ 10 shp ++ ++ +++ Manageability 1 shp ++ +++ ++ ++ 10 shp ++ ++ ++ ++

[0158] 3) After treating the keratin fibres with compositions A1 to A4, then with the steam iron: Invention

TABLE-US-00004 With steam iron at 210 C. - Invention Cosmetic properties Compositions evaluated Shampoos A1 A2 A3 A4 Softness 0 shp ++ ++ 1 shp + +++ ++ 10 shp +++ ++ + Disentangling 1 shp + ++ ++ +++ 10 shp ++ ++ +++ Manageability 1 shp ++ +++ +++ ++ 10 shp +++ +++ +

[0159] The locks treated via the process according to the invention, with a content of compound 1 of 5 and 10% by weight and after having been shampooed one or more ten times, have better cosmetic properties in terms of soft feel, manageability, ease of combing (disentangling). These cosmetic properties thus have good persistence on shampooing. This trend was observed with the compounds of the invention even after shampooing 20 times: see the table below.

TABLE-US-00005 With iron at 210 C. With steam iron at Cosmetic properties 210 C. evaluated Shampoos A2 A3 A2 A3 Softness 20 shp ++ ++ +++ ++ Disentangling 20 shp ++ ++ ++ ++ Manageability 20 shp ++ ++ ++ ++

EXAMPLE 4

Composition Prepared

[0160]

TABLE-US-00006 Compositions B A2 (placebo) Compound 15* 5 0 Water qs 100 qs 100 *amount in g per 100 g of composition

[0161] The evaluation and the applying conditions of compositions A2 and B above were made according to the same protocol used for example 3.

[0162] The performances were recorded as follows:

for a bad result
+ for a poor result
++ for a moderate result
+++ for a good result

[0163] The following results were obtained: [0164] 1) After treating the keratin fibres with composition A2, without iron: Comparative

TABLE-US-00007 Cosmetic properties Composition evaluated Shampoo A2 Softness 0 shp reference 1 shp + Disentangling 1 shp + Manageability 1 shp + [0165] 2) After treating the keratin fibres with composition A2, then with the iron: Invention

TABLE-US-00008 With iron at 210 C. - Invention Cosmetic properties Composition evaluated Shampoos A2 Softness 0 shp reference 1 shp ++ 10 shp ++ Disentangling 1 shp ++ 10 shp ++ Manageability 1 shp ++ 10 shp ++ [0166] 3) After treating the keratin fibres with composition A2, then with the steam iron: Invention

TABLE-US-00009 With steam iron at 210 C. - Invention Cosmetic properties Composition evaluated Shampoos A2 Softness 0 shp reference 1 shp ++ 10 shp ++ Disentangling 1 shp ++ 10 shp ++ Manageability 1 shp ++ 10 shp ++

[0167] The locks treated via the process according to the invention, with a content of compound 15 of 5% by weight and after having been shampooed one or more ten times, have better cosmetic properties in terms of soft feel, manageability, ease of combing (disentangling). These cosmetic properties thus have good persistence on shampooing.

EXAMPLE 5

Friction Test:

[0168] The surface of healthy hair is perceived as smooth, as opposed to the surface of damaged hair which is perceived as coarse and rough. Different devices have been developed to measure the friction of hair fibers or swatches, at various scales. It has been reported that damaging the hair by bleaching (Scott, Robbins, J. Soc. Cosmet. Chem., 1980, 31, 179) and permanent waving (Schwartz, Knowles, J. Soc. Cosmet. Chem., 1963, 14, 455) increases its friction coefficient. As such, restoring a lower friction coefficient is a highly desirable effect of cosmetic treatments and various chemicals have been used to this effect (Evans, Wickett. 2012, Practical Modern Hair Science. Carol Stream: Allured Business Media. 562 p.). They improve the feeling of repaired hair, and facilitate grooming practices in the wet and dry state.

[0169] We have used a simple friction measurement in this study. The 3.5-cm hair bundles are fixed on the sample holder of a Zwickiline Z2.5 materials testing machine (ZWICK, Germany). A 0.5N normal force is applied to the swatches by pinching them in a clamp covered in disposable foam bands. The foam is discarded and replaced after each measurement. A constant displacement speed of 100 mm/min is imposed by the machine. The force is recorded over time and plotted as a force/displacement curve that reaches a plateau after a few seconds. The average friction force at the plateau is recorded. The impact of a conditioning treatment on the hair friction is obtained by comparing the average friction force of untreated hair swatches and the friction force of swatches treated by the compound of interest. For measurements in the wet state (wet friction force), the hair bundles are immersed in double-distilled water for 1 minute prior to performing the friction measurement as described above. Statistical significance of the results is evaluated by Student's t-test at the 0.05% threshold.

Hair Swatches Treatment:

[0170] After the cosmetic treatments with compositions A2 and A3 described above, the swatches are divided into 150 mg swatches, by weighting using a precision balance. The swatch is subdivided into 3.5 cm-long hair bundles by cutting using sharp disposable razor blades. A disposable cable-clamp is fastened at the middle of each hair bundle to prevent the sliding of hair fibers.

Results:

[0171] We obtained the following results: [0172] 1) After treating the keratin fibres with composition A3, without iron: Comparative

TABLE-US-00010 Cosmetic properties Compositions evaluated Shampoos B (Placebo) A3 wet softness and wet 1 shp 0.56 0.32 untangling/ease of 5 shp 0.65 0.71 combing (wet friction coefficient) [0173] 2) After treating the keratin fibres with composition A3, then with the iron: Invention

TABLE-US-00011 With iron at 210 C. - Invention Cosmetic properties Compositions evaluated Shampoos B (Placebo) A3 wet softness and wet 1 shp 0.62 0.29 untangling/ease of 5 shp 0.69 0.58 combing (wet friction coefficient) [0174] 3) After treating the keratin fibres with composition A2, then with the iron: Invention

TABLE-US-00012 With iron at 210 C. - Invention Cosmetic properties Compositions evaluated Shampoos B (Placebo) A2 wet softness and wet 1 shp 0.90 0.58 untangling/ease of 5 shp 0.76 combing (wet friction coefficient) dry softness and dry 1 shp 0.68 0.56 untangling/ease of 5 shp 0.60 combing (dry friction coefficient)

[0175] With composition A2: [0176] After 1 shampoo, the composition lowers the wet and dry friction forces (improves the wet and dry conditioning) as compared with the placebo swatches. [0177] The effect still exists in the dry and wet state after 5 shampoos.

[0178] Thus, the locks treated via the process according to the invention with a content of compound 15 of 5% by weight and after having been shampooed one or five times, have better cosmetic properties in terms of wet softness, wet untangling/ease of combing, and dry softness, dry untangling/ease of combing. These cosmetic properties thus have good persistence on shampooing.

[0179] With composition A3: [0180] After 5 shampoos, the conditioning effect is completely lost when A3 was applied without the flat iron. [0181] After 5 shampoos, the conditioning effect is better than placebo when A3 was applied, and with the flat iron (wet friction force significantly different from control).

[0182] Thus, the locks treated via the process according to the invention with a content of compound 1 of 10% by weight and after having been shampooed one or five times, have better cosmetic properties in terms of wet softness and wet untangling/ease of combing. These cosmetic properties thus have good persistence on shampooing.