WO2017018498A1

WO2017018498A1 - Composition, process, method and use for keratin fibers

Info

Publication number: WO2017018498A1
Application number: PCT/JP2016/072243
Authority: WO
Inventors: Qinghua Li; Tomotaka Michitsuji; Hayato Nishimura; Daisuke Ishii
Original assignee: L'oreal
Priority date: 2015-07-28
Filing date: 2016-07-22
Publication date: 2017-02-02
Also published as: JP2017025051A

Abstract

The present invention relates to a composition for keratin fibers, such as hair, comprising: (a) at least one reducing agent; (b) at least one polyol with 4 or more carbon atoms, wherein the amount of the polyol in the composition is less than 1.0% by weight relative to the total weight of the composition. The present invention can be used to deform or reshape keratin fibers, preferably hair, and can provide the keratin fibers with sufficient reshaping efficiency such as strong wave intensity, distinct wave deepness and good regularity of curl, as well as less damage to the keratin fibers which results in excellent hair conditioning effects such as good elasticity and suppleness of the keratin fibers.

Description

DESCRIPTION

COMPOSITION, PROCESS, METHOD AND USE FOR KERATIN FIBERS TECHNICAL FIELD

The present invention relates to a composition, in particular a cosmetic composition, and a reshaping process, in particular waving, as well as a method and a use, for keratin fibers such as hair.

BACKGROUND ART

In long-lasting deformation of keratin fibers such as hair, first the disulphide bonds -S-S- of the keratin (cystine) are opened using a composition containing a suitable reducing agent (reduction stage), then the hair thus treated is optionally rinsed, secondly the disulphide bonds are reconstituted by applying, on the keratin fibers previously put under tension (curlers etc.), an oxidizing composition (oxidation stage, also called fixation) so as to finally give the keratin fibers the desired form. This technique thus makes it possible to carry out either waving or straightening of the keratin fibers. For example, JP-B-S62-9566 or USP 4459284 discloses a standard process for permanent waving or straightening of keratin fibers such as hair in line with the above steps.

The new shape imposed on the keratin fibers by chemical treatment as described above is relatively long-lasting and notably withstands the action of washing with water or shampoo, in contrast to the simple conventional techniques of temporary styling by using foams, styling gels, or lacquers.

Many compositions and processes for the above chemical treatment have been proposed. Generally, they offer good performance on the day of treatment.

However, there are various drawbacks such as follows in the above chemical treatment process that may not be suitable from the viewpoint of consumer's or hair-dresser's expectations:

Insufficient long-lastingness against environmental stress (mechanical constraints from brushing, frequent shampoos, light exposure, high humidity and the like);

Insufficient reshaping efficiency;

High levels of keratin fiber degradation or damage due to the deformation of the keratin fibers, especially in repeated applications or in combination with other chemical treatments such as oxidative coloration;

- Long processing time; and

Malodor of ammonia or sulfur-containing compounds during and after the deformation process.

In particular, sufficient reshaping efficiency and less damage to the keratin fibers are important. There is indeed a need to improve a composition for deforming keratin fibers to provide sufficient reshaping efficiency, such as strong wave intensity of the curled keratin fibers, deepness of the curl, and regularity of the curl, as well as less damage to the keratin fibers which results in excellent hair conditioning effects such as good elasticity and suppleness of the keratin fibers. DISCLOSURE OF INVENTION

An objective of the present invention is to provide a composition, preferably a cosmetic composition, for keratin fibers, such as hair, which can be used to deform or reshape the keratin fibers, and can provide the keratin fibers with sufficient reshaping efficiency such as strong wave intensity, distinct wave deepness and good regularity of curl, as well as less damage to the keratin fibers which results in excellent hair conditioning effects such as good elasticity and suppleness of the keratin fibers. The above objective of the present invention can be achieved by a composition, in particular a cosmetic composition, for keratin fibers, such as hair, comprising:

(a) at least one reducing agent;

(b) at least one polyol with 4 or more carbon atoms,

wherein

the amount of the polyol in the composition is less than 1.0% by weight relative to the total weight of the composition.

The (b) polyol may be selected from glycols. The (b) polyol may be selected from the group consisting of butylene glycol, pentylene glycol, hexylene glycol, and mixtures thereof.

The amount of the (b) polyol(s) in the composition may be from 0.001 to less than 1.0% by weight, preferably from 0.01 to less than 0.5% by weight, and more preferably from 0.1 to 0.3% by weight, relative to the total weight of the composition.

The (a) reducing agent may be selected from the group consisting of thioglycolic acid, thiolactic acid, cysteine, N-acetylcysteine, cysteamine, lactonethiol compounds such as butyrolactonethiol, glyceryl monothioglycolate, sulfite or bisulfite compounds, thioglycerine, their derivatives, and their salts.

The amount of the (a) reducing agent(s) in the composition may be from 0.01 to 25% by weight, preferably from 0.1 to 20% by weight, and more preferably from 1.0 to 15% by weight, relative to the total weight of the composition.

The composition according to the present invention may further comprise (c) at least one alkaline agent.

The composition according to the present invention may have a pH of 9.0 or less, preferably 8.5 or less, and more preferably 8.0 or less.

The composition according to the present invention may further comprise (d) at least one surfactant. The composition according to the present invention may be free of dicarboxylic acid, preferably α,ω-dicarboxylic acid with 5 to 10 carbon atoms, and more preferably adipic acid.

The composition according to the present invention is preferably intended for reshaping, in particular permanent waving, of keratin fibers, preferably the hair. The composition according to the present invention can be used to deform or reshape keratin fibers, preferably the hair, and can provide the keratin fibers with sufficient reshaping efficiency such as strong wave intensity, distinct wave deepness and good regularity of curl, as well as excellent hair conditioning effects due to less damage to the keratin fibers, such as good elasticity and suppleness of the keratin fibers.

The present invention also relates to a reshaping process, in particular permanent waving, for keratin fibers, preferably the hair, comprising the steps of:

applying onto the keratin fibers a composition;

optionally rinsing the keratin fibers;

applying onto the keratin fibers an oxidizing composition comprising at least one oxidizing agent; and

optionally rinsing and/or drying the keratin fibers,

wherein

the composition comprises

(a) at least one reducing agent;

(b) at least one polyol with 4 or more carbon atoms,

wherein

The present invention also relates to a method for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by a reducing composition comprising at least one reducing agent in combination with an oxidizing composition comprising at least one oxidizing agent, characterized by adding at least one polyol with 4 or more carbon atoms to the reducing composition in an amount of less than 1.0% by weight relative to the total weight of the reducing composition.

The present invention also relates to a use of at least one polyol with 4 or more carbon atoms in a reducing composition comprising at least one reducing agent wherein the amount of the polyol in the reducing composition is less than 1.0% by weight relative to the total weight of the reducing composition, for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by the reducing composition in combination with an oxidizing composition comprising at least one oxidizing agent.

The process, method and use according to the present invention can be used to deform or reshape keratin fibers, preferably hair, and can provide the keratin fibers with sufficient reshaping efficiency such as strong wave intensity, distinct wave deepness and good regularity of curl, as well as excellent hair conditioning effects due to less damage to the keratin fibers, such as good elasticity and suppleness of the keratin fibers.

BEST MODE FOR CARRYING OUT THE INVENTION

After diligent research, the inventors have found that the use of a polyol with 4 or more carbon atoms in a reducing composition which is used in combination with an oxidizing composition for reshaping keratin fibers, in particular hair, can enhance the reshaping efficiency, such as strong wave intensity, distinct wave deepness, good regularity of curl, as well excellent hair conditioning effects due to less damage to the keratin fibers, such as good elasticity and suppleness of the keratin fibers. Thus, one aspect of the present invention is a composition, in particular a cosmetic composition, for keratin fibers, such as hair, comprising:

(a) at least one reducing agent;

(b) at least one polyol with 4 or more carbon atoms,

wherein

Another aspect of the present invention is a reshaping process, in particular permanent waving, for keratin fibers, preferably the hair, comprising the steps of:

applying onto the keratin fibers a composition;

optionally rinsing the keratin fibers;

optionally rinsing and/or drying the keratin fibers,

wherein

the composition comprises

(a) at least one reducing agent;

(b) at least one polyol with 4 or more carbon atoms,

wherein

Another aspect of the present invention is a method for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by a reducing composition comprising at least one reducing agent in combination with an oxidizing composition comprising at least one oxidizing agent, characterized by adding at least one polyol with 4 or more carbon atoms to the reducing composition in an amount of less than 1.0% by weight relative to the total weight of the reducing composition.

Another aspect of the present invention is a use of at least one polyol with 4 or more carbon atoms in a reducing composition comprising at least one reducing agent wherein the amount of the polyol in the reducing composition is less than 1.0% by weight relative to the total weight of the reducing composition, for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by the reducing composition in a combination of an oxidizing composition comprising at least one oxidizing agent.

Hereafter, the composition, process, method and use according to the present invention will each be described in a detailed manner.

[Composition] (Reducing Agent) The composition according to the present invention comprises at least one (a) reducing agent. Two or more reducing agents may be used in combination. Thus, a single type of reducing agent or a combination of different types of reducing agents may be used.

The (a) reducing agent(s) may be present in the composition according to the present invention, in an amount of, for example, from 0.01 to 25% by weight, preferably from 0.1 to 20% by weight, and more preferably from 1.0 to 15% by weight, relative to the total weight of the composition.

The (a) reducing agent may be selected from thiol reducing agents and non-thiol reducing agents.

(i) Thiol Reducing Agent

The "thiol reducing agent" here means a reducing agent with at least one thiol group.

The thiol reducing agent may preferably be chosen from the group consisting of thioglycolic acid and derivatives thereof, in particular esters thereof such as glycerol or glycol

monothioglycolate; thiolactic acid and derivatives thereof, in particular esters thereof such as glycerol monothiolactate; 3-mercaptopropionic acid and derivatives thereof, in particular esters thereof such as glycerol 3-mercaptopropionate and ethyleneglycol

3-mercaptopropionate; cysteamine and derivatives thereof, in particular Q-Q acyl derivatives thereof such as N-acetylcysteamine and N-propionylcysteamine; mono-thioglycerol and derivatives thereof, in particular esters; cysteine and derivatives thereof, in particular esters such as N-acetylcysteine, N-alkanoylcysteine and cysteine alkyl esters; thioglycerine and derivatives thereof, in particular s-alkyl derivatives, and salts thereof.

As the above salts, mention may be made of, for example, ammonium salts; primary-, secondary- or tertiary-amine salts; alkaline metal salts; and alkaline earth metal salts. As the primary-, secondary- or tertiary-amine, for example, monoethanolamine, di-isopropanolamine or triethanolamine, respectively, may be mentioned.

As the thiol reducing agent, it is preferable to use mercapto carboxylic acid or amine. The mercapto carboxylic acid or amine here means a compound with at least one mercapto group and at least one carboxyl group or at least one amino group. It is preferable that the mercapto carboxylic acid or amine have one mercapto group and one carboxyl group or one amino group. The mercapto carboxylic acid or amine here does not encompass a compound with both carboxyl and amino groups such as cysteine and homocysteine.

As examples of the mercapto carboxylic acid, mention may be made of thioglycolic acid, thiolactic acid, 3-mercapto propionic acid, thiotartaric acid, mercapto succinic acid (thiomalic acid), and dimercapto adipic acid. It is preferable that the mercapto carboxylic acid be selected from the group consisting of thioglycolic acid, thiolactic acid, and

3-mercaptopropionic acid. The mercapto carboxylic acid may be in the form of a derivative thereof. The mercapto carboxylic acid derivative here means a compound in which the OH moiety of the mercapto carboxylic acid has been replaced with another group such as alkoxy group and amino group. Thus, the mercaptocarboxylic acid derivative can be prepared by the reaction between the mercapto carboxylic acid and, for example, alcohols or amines.

As examples of the mercapto carboxylic acid derivatives, mention may be made of mercapto caboxylates such as methylthioglycolate, ethylthioglycolate, glycolmonothioglycolate, 1 ,2-propyleneglycolmonothioglycolate, glycerolmonothioglycolate, glycolmonothiolactate, glycerolmonothiolactate, and glycerolmono-3-mercaptopropionate; and mercaptocarboxylic acid amides such as thioglycolamide, N-hydroxyethylthioglycolamide, 3 -mercaptopropionamide, and N-hydroxyethyl-3 -mercaptopropionamide.

As examples of the mercapto amine, mention may be made of cysteamine and cysteamine derivatives. As examples of the cysteamine derivatives, mention may be made of

N-acylcysteamines. As the acyl group of the N-acylcysteamines, mention may be made of an alkanoyl group such as acetyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, isostearoyl, and the like. As the cysteamine derivative, N-acetylcysteamine is preferable.

It may be preferable to use mercapto carboxylic acid or amine, in combination with cysteine or a derivative thereof as mentioned above.

Other suitable examples of the thiol reducing agent that may be used in the cosmetic composition for the present invention include, but are not limited to, sugar N-mercapto alkyl amides such as N-(mercapto-2-ethyl)gluconamide, β-mercaptopropionic acid and derivatives thereof; thiomalic acid; pantheteine; N-(mercaptoalkyl)co-hydroxyalkyl amides such as those described in European Patent Application No. 0 354 835 and N-mono- or

Ν,Ν-dialkylmercapto 4-butyramides such as those described in European Patent Application No. 0 368 763; aminomercaptoalkyl amides such as those described in European Patent Application No. 0 432 000 and alkylaminomercaptoalkylamides such as those described in European Patent Application No. 0 514 282; (2/3) hydroxy-2 propyl thioglycolate; and the hydroxy-2 methyl- 1 ethyl thioglycolate-based mixture (67/33) described in French Patent Application No. 2 679 448.

It is preferable that the thiol reducing agent be selected from the group consisting of thioglycolic acid, thiolactic acid, cysteine, N-acetylcysteine, cysteamine, lactonethiol compound such as butyrolactonethiol, glyceryl monothioglycolate, sulfite or bisulfite compounds, thioglycerine, their derivatives, and their salts such as ethanolamine thioglycolate, ammonium thioglycolate and cysteamine HC1. (ii) Non-Thiol Reducing Agent

The "non-thiol reducing agent" here means a reducing agent with no thiol group.

The non-thiol reducing agent may preferably be chosen from the group consisting of sulfites, bisulfites, sulfinates, phosphines, sugars, reductones and hydrides. More preferably, the non-thiol reducing agent may be selected from ammonium sulfites and bisulfites as well as metal sulfites and bisulfites, more preferably alkali metal or alkali earth metal sulfites and bisulfites, and more preferably sodium sulfites and bisulfites. As the sulfinates, mention may be made of sulfmic acid salts, and benzenesulfmic acid salts such as sodium salts thereof. The sulfinic acid derivatives as described in FR-A-2814948 can also be used. A preferred sulfinate compound is 2-hydroxy-2-sulfinatoacetic acid, disodium salt. As the phosphines, mention may be made of monophosphine and diphosphines as described in FR-A-2870119. According to one particular embodiment of the present invention, the phosphine(s) can be chosen from the compounds of formula (I) below:

in which:

L is a linker that represents a covalent bond or a divalent hydrocarbon-based radical optionally comprising one or more hetero atoms chosen from an oxygen atom, a sulfur atom, a nitrogen atom and a silicon atom;

m is an integer equal to 0 or 1 ;

q is an integer equal to 1 or 2;

p is an integer equal to 0 or 1 ;

R^J1, R^J and R , which may be identical or different, represent:

a hydrogen atom;

a halogen atom;

a hydroxy 1 radical;

a carboxyl radical;

a monovalent hydrocarbon-based radical optionally comprising one or more hetero atoms chosen from a sulfur atom, an oxygen atom, a nitrogen atom, a phosphorus atom and a silicon atom, optionally substituted with one or more radicals chosen from:

a halogen atom,

a hydroxyl radical,

an alkoxy radical,

a haloalkyl radical,

an amino radical,

a carboxyl radical,

an alkoxycarbonyl radical,

an amido radical,

an alkylaminocarbonyl radical,

an acylamino radical,

a mono- or di(alkyl)amino radical,

a mono- or di(hydroxyalkyl)amino radical,

an N-aryl-N-alkylamino radical,

an aromatic or heteroaromatic ring, which is unsubstituted or substituted with one or more radicals chosen from a halogen atom, a hydroxyl radical, an alkoxy radical and a mono- or di(alkyl)amino radical,

a cyano radical,

a radical that increases the solubility of the phosphine in water, such as sulfonate, sulfinate, phosphonate or carboxylate radicals,

a substituted or unsubstituted, aromatic or non-aromatic heterocyclic radical;

a substituted or unsubstituted aryl radical;

a substituted or unsubstituted arylalkyl radical;

an arylalkyloxy radical;

a substituted or unsubstituted, aromatic or non-aromatic heterocyclic radical;

a silyl radical;

it being understood that:

when q=l , m=0 and p=l ;

when q=2, m=l and p=0 or 1, with: when p=0, the linker L is attached to the phosphorus atom; and

when p=l , the linker L is attached to one of the radicals R , R and R ,

and acid-addition salts thereof. In all the above definitions, when a radical is substituted, the substituents are chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, mono- or dialkylamino, mono- or

dihydroxyalkylamino and carboxyl. For example, the radical p-methoxyphenyl is a substituted aryl radical. Preferably, the radicals R , R and R do not simultaneously represent a hydrogen atom.

Advantageously, but optionally, at least one of the radicals R , R and R denotes, as a hydrocarbon-based radical, an optionally substituted alkyl radical. According to one particular embodiment of the present invention, R , R and R are chosen from a hydrogen atom; an alkyl radical; a cycloalkyl radical optionally substituted with one or more alkyl radicals; an alkoxy radical; an alkoxyalkyl radical; a haloalkyl radical; a cyanoalkyl radical; a hydroxyalkyl radical; a carboxyalkyl radical; a halogen atom; a hydroxyl radical; a carboxyl radical; an alkenyl radical; a mono- or dialkylamino radical; an

N-aryl-N-alkylaminoalkyl radical; an aryl radical optionally substituted with one or more radicals chosen from an alkyl radical, an alkoxy radical, a mono- or dialkylamino radical, a mono- or dialkylaminoalkyl radical, a haloalkyl radical, a hydroxyl radical, a carboxyl radical, a halogen atom, and an aryl radical substituted with a mono- or dialkylaminoalkyl radical; an arylalkyl radical; an arylalkyloxy radical; a pyrrolidino radical; a furyl radical; a morpholino radical; a thienyl radical; a pyridyl radical; a trialkylsilyl radical; and an alkyl radical substituted with a pyrrolidino radical, a furyl radical, a morpholino radical or a thienyl radical.

By way of example, R , R and R may be chosen from a hydrogen atom; a methyl radical; an ethyl radical; a propyl radical; an isopropyl radical; an n-butyl radical; an isobutyl radical; a tert-butyl radical; an octyl radical; a cyclohexyl radical; a cyclopentyl radical; a methoxy radical; an ethoxy radical; a methoxypropyl radical; a chloroethyl radical; a cyanoethyl radical; a hydroxymethyl radical; a hydroxypropyl radical; a carboxyethyl radical; a chlorine atom; a hydroxyl radical; a carboxyl radical; a trifluoromethyl radical; a chloromethyl radical; an allyl radical; a vinyl radical; a dimethylamino radical; a diethylamino radical; a

di(isopropyl)amino radical; a phenyl radical; an o-tolyl radical; an m-tolyl radical; a p-tolyl radical; a dimethylphenyl radical; a trimethylphenyl radical; an o-methoxyphenyl radical; an m-methoxyphenyl radical; a p-methoxyphenyl radical; a dimethoxyphenyl radical; a trimethoxyphenyl radical; an o-(dimethylamino)phenyl radical; an m-(dimethylamino)phenyl radical; a p-(dimethylamino)phenyl radical; a di(tert-butyl)phenyl radical; a

tri(tert-butyl)phenyl radical; a trifluoromethylphenyl radical; a bis(trifluoromethyl)phenyl radical; an o-fluorophenyl radical; an m-fiuorophenyl radical; a p-fluorophenyl radical; an o-chlorophenyl radical; an m-chlorophenyl radical; a p-chlorophenyl radical; an

o-hydroxyphenyl radical; an m-hydroxyphenyl radical; a p-hydroxyphenyl radical; a

4-(diethylaminomethyl)phenyl radical; a 3,5-dimethyl-4-methoxyphenyl radical; a

2-methylbiphenyl radical; a benzyl radical; a benzyloxy radical; a naphthyl radical; a morpholino radical; a morpholinomethyl radical; a pyrrolidino radical; a furyl radical; a pyridyl radical; a thienyl radical; a trimethylsilyl radical; a

2-(4-diethylaminomethyl-phenyl)phenyl radical; a 5-methyl-2-isopropylcyclohexyl radical; an N-methyl-N-phenylaminomethyl radical; and a carboxyphenyl radical. The phosphines that are useful in the context of the present invention may be optionally salified with strong mineral acids, for instance HCl, HBr, H₂S0₄ or HBF₄ or organic acids, for instance acetic acid, lactic acid, tartaric acid, citric acid or succinic acid.

According to one particular embodiment of the present invention, the phosphine(s) that is (are) useful in the context of the present invention is (are) chosen from monophosphines. For example, when the phosphine(s) is (are) of formula (I), q is then preferably equal to 1.

Examples of monophosphines that may be mentioned include tri(hydroxymethyl)phosphine; tri(hydroxypropyl)phosphine; bis(hydroxymethyl)(phenyl)phosphine; allyldiphenylphosphine; benzyldiphenylphosphine; bis(3,4,5-trimethoxyphenyl)chlorophosphine;

bis(3,4,5-trimethoxyphenyl)phosphine; benzyloxy(diisopropylamino)methylphosphine;

bis(diisopropylamino)chlorophosphine; bis(2-cyanoethyl)phosphine;

bis(3 , 5 -di-tert-butylphenyl)chlorophosphine; bis(3 , 5 -di-tert-butyl-phenyl)phosphine ;

bis(diethylamino)methylphosphine; bis(diethylamino)chlorophosphine;

bis(diethylamino)phenylphosphine; bis(3,5-dimethyl-4-methoxyphenyl)chlorophosphine; bis(3,5-dimethyl-4-methoxyphenyl)phosphine; bis(3,5-dimethylphenyl)chlorophosphine; bis(3,5-dimethylphenyl)diethylaminophosphine; bis(3,5-dimethylphenyl)phosphine;

bis(3,5-ditrifluoromethylphenyl)chlorophosphine; bis(3,5-ditrifluoromethylphenyl)phosphine; bis(4-fluorophenyl)chlorophosphine; bis(2-furyl)chlorophosphine; bis(2-furyl)phosphine; bis(hydroxymethyl)phenylphosphine; bis(4-methoxyphenyl)phenylphosphine;

bis(3,5-dimethylphenyl)phosphine; bis(3,5-di-tert-butylphenyl)chlorophosphine;

bis(3,5-di-tert-butylphenyl)phosphine; bis(3,5-ditrifluoromethylphenyl)chlorophosphine; bis(3,5-ditrifluoromethylphenyl)phosphine; bis(4-fluorophenyl)chlorophosphine;

bis(4-methoxyphenyl)chlorophosphine; bis(4-methoxyphenyl)phenylphosphine;

bis(4-methylphenyl)chlorophosphine; bis(4-methylphenyl)phosphine;

bis(4-trifluoromethylphenyl)chlorophosphine; bis(4-trifluoromethylphenyl)phosphine;

bis(diethylamino)methylphosphine; bis(diethylamino)phenylphosphine;

bis(hydroxymethyl)phenylphosphine; bis(o-tolyl)chlorophosphine; bis(o-tolyl)phosphine; bis(pyrrolidino)methylphosphine; butyldichlorophosphine; butyldiphenylphosphine;

tert-butyldiphenylphosphine; cyclohexyl(diethylamino)chlorophosphine;

cyclohexyl(dimethyl-amino)chlorophosphine; cyclohexyldichlorophosphine;

cyclohexyldiphenylphosphine; 2-chloroethyldiphenylphosphine;

2-(dicyclohexylphosphino)biphenyl;

2-dicyclo-hexylphosphino-2'-(N,N-dimethylamino)biphenyl; diethyl-aminodiethylphosphine; dimethylaminodichlorophosphine; (4-dimethylaminophenyl)diphenylphosphine;

N-[(diphenyl-phosphinyl)methyl]-N-methylaniline; o-diphenylphosphinobenzoic acid;

2-methoxy(dichlorophosphino)benzene; 4-methoxyphenyl(diethylamino)chlorophosphine; 4-methoxyphenyl(dimethylamino)chlorophosphine;

(2-methoxyphenyl)methylphenylphosphine; 2-methoxyphosphinobenzene;

(5-methyl-2-isopropylcyclohexyl)diphenylphosphine; triphenylphosphine;

diallylphenylphosphine; dibenzylphosphine; dibutylphenylphosphine; dibutylphosphine;

dicyclohexylchlorophosphine; dicyclohexylphenylphosphine; dicyclohexylphosphine;

diethylchlorophosphine; diethylphenylphosphine; diethylphosphine; diisobutylphosphine; diisopropylchlorophosphine; diisopropylphosphine; dimethyl(phenyl)phosphine;

dimethyl(trimethylsilyl)phosphine; dimethylchlorophosphine; diphenyl(o-tolyl)phosphine; diphenyl(p-tolyl)phosphine; diphenyl(trimethylsilyl)phosphine; diphenylchlorophosphine; diphenylphosphine; diphenylpropylphosphine; diphenylvinylphosphine;

di-tert-butylchlorophosphine; di-tert-butylhydroxyphosphine; di-tert-butylmethylphosphine; di-tert-butylphenylphosphine; di-tert-butylphosphine; divinylphenylphosphine; ethyl-dichlorophosphine; ethyldiphenylphosphine; isopropyl-dichlorophosphine; methoxydiethoxyphosphine; methyl-dichlorophosphine; methyldiphenylphosphine;

methyl-phenylchlorophosphine; phenylphosphine; propyldichlorophosphine;

tert-butylbis(trimethylsilyl)phosphine; tert-butyldichlorophosphine;

tert-butyldiethylphosphine; tert-butyldiphenylphosphine; tert-butylphosphine;

tri(m-tolyl)phosphine; tri(o-tolyl)phosphine; tri(p-tolyl)phosphine; tricyclohexylphosphine; tricyclopentylphosphine; triethylphosphine; triisobutylphosphine; triisopropylphosphine; trimethylphosphine; tri-n-butylphosphine; tri-n-octylphosphine; tripropylphosphine;

tris( 1 -naphthyl)phosphine; tris(2,4,6-trimethylphenyl)phosphine;

tris(2,6-dimethoxyphenyl)phosphine; tris(2-carboxyethyl)phosphine;

tris(2-cyanoethyl)phosphine; tris(2-furyl)phosphine; tris(2-methoxyphenyl)phosphine;

tris(2-thienyl)phosphine; tris(3,5-dimethyl-4-methoxy)phosphine;

tris(3 -chlorophenyl)phosphine; tris(3 -fluoro-phenyl)phosphine;

tris(3-methoxyphenyl)phosphine; tris(3-methoxypropyl)phosphine;

tris(4-chlorophenyl)phosphine; tri

tris(4-methoxyphenyl)phosphine;

tris(hydroxymethyl)phosphine; tris(trimethylsilyl)phosphine;

tris [3 , 5 -bis(trifluoromethyl)pheny l]phosphine ; tri-tert-butylphosphine ;

2-cyanoethyldiphenylphosphine; 2-dicyclohexylphosphino-2'-methylbiphenyl;

bis(2,4,6-trimethylphenyl)phosphine; and 2-(di-tert-butyl-phosphino)biphenyl.

Preferably, the monophosphines are chosen from trihydroxymethylphosphine;

trihydroxypropylphosphine; and bis(hydroxymethyl)phenylphosphine.

According to another particular embodiment of the present invention, the phosphine(s) that is (are) useful in the context of the present invention is (are) diphosphines. When the phosphine(s) is (are) of formula (I), q is then preferably equal to 2.

Preferably, p is equal to 0 and the linker L is a covalent bond or a divalent radical chosen from a binaphthylene radical; a methylene radical; an ethylene radical; a propylene radical; a butylene radical; a pentylene radical; a hexylene radical; a phenylene radical; a

meta-dimethylenebenzene radical; an N-methyl-N'-methylhydrazo radical; a vinylene radical; and a diethyleneoxy radical.

As examples of diphosphines that are useful in the context of the present invention, mention may be made of 2,2'-bis(dicyclohexyiphosphino)- 1 , 1 '-binaphthyl;

2,2'-bis[bis(3 ,5-dimethylphenylphosphino)]- 1 , 1 '-binaphthyl;

1.4- bis[bis(3,5-dimethylphenyl)phosphino]butane;

1.2- bis[bis(3,5-dimethylphenyl)phosphino]ethane;

bis[bis(3,5-dimethylphenyl)phosphino]methane;

1.5- bis[bis(3,5-dimethylphenyl)phosphino]pentane;

1.3- bis[bis(3,5-dimethylphenyl)phosphino]propane;

2,2'-bis[bis(3,5-ditrifluoromethylphenyl)phosphino]-l,r-binaphthyl;

1.4- bis[bis(3,5-ditrifluoromethylphenyl)phosphino]butane;

1.2- bis[bis(3,5-ditrifluoromethylphenyl)phosphino]ethane;

bis[bis(3,5-ditrifiuoromethylphenyl)phosphino]methane;

1.5- bis-[bis(3,5-ditrifluoromethylphenyl)phosphino]pentane;

1.3- bis[bis(3,5-ditrifluoromethylphenyl)phosphino]-propane;

1 ,2-bis(di-tert-butylphosphino)benzene; 1 ,4-bis(di-tert-butylphosphino)butane;

1 ,2-bis(di-tert-butylphosphino)ethane; 1 ,3 -bis(di-tert-butylphosphinomethyl)benzene; 1 ,3 -bis(di-tert-butylphosphino)propane; 1 ,2-bis(dichlorophosphino)benzene;

1 ,3 -bis(dichlorophosphino)benzene; 1 ,4-bis(dichlorophosphino)benzene;

1 ,4-bis(dichlorophosphino)butane; 1 ,2-bis(dichlorophosphino)- 1 ,2-dimethylhydrazine;

1.2- bis(dichlorophosphino)ethane; bis(dichlorophosphino)methane;

1.3- bis(dichlorophosphino)propane; 1 ,2-bis(dicyclohexyl-phosphino)benzene;

2,2'-bis(dicyclohexylphosphino)- 1 , 1 '-binaphthyl; 1 ,4-bis(dicyclohexylphosphino)butane; (2R,3R)bis(dicyclohexylphosphino)butane; (2S,3S)-bis(dicyclohexylphosphino)butane;

l,2-bis(dicyclohexylphosphino)ethane; bis(dicyclohexylphosphino)methane;

1 ,3 -bis(dicyclohexylphosphino)propane;

bis[2-(4-diethylan inoniethylphenyl)phenylphosphino]ethylether;

1 ,2-bis(diethylphosphino)ethane; 1 ,2-bis(dimethyl-phosphino)benzene;

1.4- bis(dimethylphosphino)butane; 1 ,2-bis(dimethylphosphino)ethane;

bis(dimethylphosphino)methane; 1 ,3-bis(dimethylphosphino)propane;

1.2- bis(diphenylphosphino)benzene; 1 ,3 -bis(diphenylphosphino)benzene;

1 ,4-bis(diphenylphosphino)benzene; 2,2'-bis(diphenylphosphino)- 1 , 1 '-binaphthyl;

1 ,4-bis(di-phenylphosphino)butane; 1 ,2-bis(diphenylphosphino)ethane;

cis- 1 ,2-bis(diphenylphosphino)ethylene; trans- 1 ,2-bis(diphenylphosphino)ethylene;

bis(2-diphenylphosphino)ethyl ether; 1 ,6-bis(diphenylphosphinO)hexane;

bis(diphenylphosphino)methane; l,5-bis(diphenylphosphino)pentane;

1.3- bis(diphenylphosphino)propane; 1 ,2-bis(ditrifluoromethylphosphino)ethane;

1.2- bis[(2-methoxyphenyl)phenylphosphino]ethane; 1 ,2-bis-(phenylphosphino)ethane;

1.3- bis(phenylphosphino)propane; bis-2-[(phenyl)(3-pyridyl)phosphinoethyl] ether;

1 ,2-bis(phosphino)benzene; 1 ,2-bis(phosphino)ethane; bis(phosphino)methane;

1 ,2-bis(trifluoro-methyl)phosphino)ethane; bis(di-tert-butylphosphino)pentane; and tetraphenylbiphosphine.

According to one particular embodiment of the present invention, the phosphine(s) that is (are) useful in the context of the present invention is (are) soluble in a cosmetically acceptable medium. Preferably, the phosphine(s) that is (are) useful in the context of the present invention is (are) water-soluble.

In the context of the present invention, the term "water-soluble" means any phosphine whose solubility in water is greater than 0.01%, preferably greater than 1%, and even preferably greater than 2 or 5% by weight at 20°C and at atmospheric pressure (760 mm Hg, i.e.

1,013.105 Pa). Preferably, the phosphine is trihydroxymethylphosphine.

As the sugars, mention may be made of ribose, glucose, maltose, galactose, lactose, and xylose.

As the reductones, mention may be made of ascorbic acid and erythorbic acid.

As the hydrides, mention may be made of boron hydrides such as sodium borohydride, lithium hydride, and phosphorous hydride. Precursors of hydrides and especially of boron hydrides such as diborane, tetraborane, pentaborane, decaborane and dodecaborane can be used.

Preferred non-thiol-based reducing agents are chosen from sulfites, bisulfites and phosphines.

In one embodiment, it may be preferable to use non-thiol reducing agent(s) because the malodor derived from sulfur atom(s) can be reduced or avoided. (Polyol)

The composition according to the present invention also comprises at least one (b) polyol with 4 or more carbon atoms. Two or more polyols may be used in combination. Thus, a single type of polyol or a combination of different types of polyols may be used.

The term "polyol" here means an alcohol having two or more hydroxy groups, and does not encompass a saccharide or a derivative thereof. The derivative of a saccharide includes a sugar alcohol which is obtained by reducing one or more carbonyl groups of a saccharide, as well as a saccharide or a sugar alcohol in which the hydrogen atom or atoms in one or more hydroxy groups thereof has or have been replaced with at least one substituent such as an alkyl group, a hydroxyalkyl group, an alkoxy group, an acyl group or a carbonyl group. The (b) polyol can promote the penetration of the (a) reducing agent(s) into the keratin fibers, and can reduce or cancel hydrophobic interactions that are non-reactive bonds in the keratin fibers. Due to the use of the (b) polyol with the (a) reducing agent(s), cancellation of the internal bonds in the keratin fibers can be performed even with a small amount of the (a) reducing agent(s). Therefore, the deformation of keratin fibers is possible with reduced damage due to the use of a small amount of the (a) reducing agent(s).

The (b) polyol may be a C₄-C₁₂ polyol, preferably a C₄-C₉ polyol, and more preferably a C₄-C₆ polyol, comprising at least 2 hydroxy groups, and preferably 2 to 5 hydroxy groups. The (b) polyol with 4 or more carbon atoms may be a natural or synthetic polyol. The polyol may have a linear, branched or cyclic molecular structure.

The (b) polyol may be selected from glycerins and glycols. The (b) polyol may be selected from the group consisting of diglycerin, polyglycerin, diethyleneglycol, dipropyleneglycol, polyethyleneglycol (5 to 50 ethyleneoxide groups), polypropyleneglycol(5 to 50

propyleneoxide groups), butyleneglycol, pentyleneglycol, hexyleneglycol, and a combination thereof.

It is preferable that the (b) polyol be selected from glycols, preferably a C₄-C ₁₂ glycol, more preferably a C₄-C₉ glycol, and even more preferably a C₄-C₆ glycol, comprising at least 2 hydroxy groups.

It is preferable that the (b) polyol be selected from the group consisting of butylene glycol, pentylene glycol, hexylene glycol, and mixtures thereof.

The amount of the (b) polyol(s) in the composition may be from 0.001 to less than 1.0% by weight, preferably from 0.01 to 0.5% by weight, and more preferably from 0.1 to 0.3% by weight, relative to the total weight of the composition. The use of the (b) polyol in an amount of 1.0% by weight or more, preferably 1.5% by weight or more, and more preferably 2.0% by weight or more, relative to the total weight of the composition is not preferable, because the reshaping efficiency of the keratin fibers can be deteriorated.

(Alkaline Agent) The composition according to the present invention may comprise (c) at least one alkaline agent. Two or more (c) alkaline agents may be used in combination. Thus, a single type of alkaline agent or a combination of different types of alkaline agents may be used. The (c) alkaline agent may be an inorganic alkaline agent. It is preferable that the inorganic alkaline agent be selected from the group consisting of ammonia; alkaline metal hydroxides; alkaline earth metal hydroxides; alkaline metal phosphates and monohydrogenophosphates such as sodium phosphate or sodium monohydrogenophosphate. It is also preferable that the inorganic alkaline agent be selected from inorganic ammonium salts such as ammonium carbonate and ammonium bicarbonate; and alkylammonium hydroxides such as

tetramethylammonium hydroxide.

As examples of the inorganic alkaline metal hydroxides, mention may be made of sodium hydroxide and potassium hydroxide. As examples of the alkaline earth metal hydroxides, mention may be made of calcium hydroxide and magnesium hydroxide. As the inorganic alkaline agent, sodium hydroxide is preferable.

The alkaline agent may be an organic alkaline agent. It is preferable that the organic alkaline agent be selected from the group consisting of monoamines and derivatives thereof; diamines and derivatives thereof; polyamines and derivatives thereof; basic amino acids and derivatives thereof; oligomers of basic amino acids and derivatives thereof; polymers of basic amino acids and derivatives thereof; urea and derivatives thereof; and guanidine and derivatives thereof. As examples of the organic alkaline agents, mention may be made of alkanolamines such as mono-, di- and tri-ethanolamine, and isopropanolamine; urea, guanidine and their derivatives; basic amino acids such as lysine, ornithine or arginine; and diamines such as those described in the structure below:

R1 R3

N-R-N

R2 R4

wherein R denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C C₄ alkyl radical, and R_1; R₂, R₃ and R4 independently denote a hydrogen atom, an alkyl radical or a C₁-C₄ hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine and derivatives thereof. Arginine, urea and monoethanolamine are preferable. The amount of the (c) alkaline agent in the composition may be from 0.01 to 15% by weight, preferably from 0.05 to 10% by weight, and more preferably from 0.1 to 8% by weight, relative to the total weight of the composition.

(pH)

The pH of the composition according to the present invention may be 9.0 or less, preferably 8.9 or less, and more preferably 8.8 or less.

If the pH of a composition comprising reducing agent(s) is relatively milder (lower) than that of conventional compositions for reshaping keratin fibers, the reshaping efficiency provided by the reducing agent(s) may be deteriorated. However, in the composition according to the present invention, the use of the (b) polyol can compensate for the deterioration of reshaping efficiency. Thus, the composition according to the present invention can exert excellent reshaping efficiency even if the pH thereof is relatively milder.

Further, due to the relatively milder pH, the composition according to the present invention can further reduce the damage to keratin fibers.

Furthermore, if the pH of the composition according to the present invention is 9.0 or less, preferably 8.9 or less, and more preferably 8.8 or less, the malodor caused by the reducing agent(s) and the like can be reduced. The composition according to the present invention may have a pH of 7.0 or more. It is preferable that the pH of the composition according to the present invention be 7.2 or more, and more preferably 7.4 or more.

The pH of the composition according to the present invention may be from 7.0 to 9.0, preferably from 7.0 to 8.9, and more preferably from 7.0 to 8.8.

Thus, the composition according to the present invention comprises water.

The amount of the water in the composition may be from 50 to 99% by weight, preferably from 60 to 95% by weight, and more preferably from 70 to 90% by weight, relative to the total weight of the composition.

(Surfactant) The composition according to the present invention may comprise (d) at least one surfactant. Two or more (d) surfactants may be used. Thus, a single type of surfactant or a combination of different types of surfactants may be used.

Any surfactant may be used for the present invention. The (d) surfactant may be selected from the group consisting of anionic surfactants, amphoteric surfactants, cationic surfactants and nonionic surfactants. Two or more surfactants may be used in combination. Thus, a single type of surfactant or a combination of different types of surfactants may be used.

According to one embodiment of the present invention, the amount of the (d) surfactant(s) may range from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight, and more preferably from 0.1 to 1% by weight, relative to the total weight of the composition used in the process according to the present invention.

(i) Anionic Surfactants

The composition may comprise at least one anionic surfactant. Two or more anionic surfactants may be used in combination.

It is preferable that the anionic surfactant be selected from the group consisting of

(C₆-C₃₀)alkyl sulfates, (C₆-C3o)alkyl ether sulfates, (C₆-C₃₀)alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates; (C₆-C3₀)alkylsulfonates,

(C₆-C₃o)alkylamide sulfonates, (C₆-C3o)alkylaryl sulfonates, α-olefin sulfonates, paraffin sulfonates; (C₆-C₃o)alkyl phosphates; (C₆-C₃₀)alkyl sulfosuccinates, (C₆-C₃₀)alkyl ether sulfosuccinates, (C₆-C₃₀)alkylamide sulfosuccinates; (C₆-C₃₀)alkyl sulfoacetates; (C₆-C₂₄)acyl sarcosinates; (C₆-C₂₄)acyl glutamates; (C₆-C₃₀)alkylpolyglycoside carboxylic ethers; (C₆-C₃₀)alkylpolyglycoside sulfosuccinates; (C₆-C₃₀)alkyl sulfosuccinamates; (C₆-C₂₄)acyl isethionates; N-(C₆-C₂₄)acyl taurates; C₆-C₃o fatty acid salts; coconut oil acid salts or hydrogenated coconut oil acid salts; (C₈-C₂o)acyl lactylates; (C₆-C₃₀)alkyl-D-galactoside uronic acid salts; polyoxyalkylenated (C₆-C₃₀)alkyl ether carboxylic acid salts;

polyoxyalkylenated (C₆-C₃o)alkylaryl ether carboxylic acid salts; and polyoxyalkylenated (C₆-C₃₀)alkylamido ether carboxylic acid salts; and corresponding acid forms.

In at least one embodiment, the anionic surfactants are in the form of salts such as salts of alkali metals, for instance sodium; salts of alkaline-earth metals, for instance magnesium; ammonium salts; amine salts; and amino alcohol salts. Depending on the conditions, they may also be in acid form.

It is more preferable that the anionic surfactant be selected from salts of (C -C₃₀)alkyl sulfate, (C₆-C₃₀)alkyl ether sulfates or polyoxyalkylenated (C₆-C₃₀)alkyl ether carboxylic acid salified or not.

(ii) Amphoteric Surfactants

The composition may comprise at least one amphoteric surfactant. Two or more amphoteric surfactants may be used in combination.

The amphoteric or zwitterionic surfactants can be, for example (non-limiting list), amine derivatives such as aliphatic secondary or tertiary amine, and optionally quaternized amine derivatives, in which the aliphatic radical is a linear or branched chain including 8 to 22 carbon atoms and containing at least one water-solubilizing anionic group (for example, carboxylate, sulphonate, sulphate, phosphate or phosphonate).

The amphoteric surfactant may preferably be selected from the group consisting of betaines and amidoaminecarboxylated derivatives.

It is preferable that the amphoteric surfactant be selected from betaine-type surfactants.

The betaine-type amphoteric surfactant is preferably selected from the group consisting of alkylbetaines, alkylamidoalkylbetaines, sulfobetaines, phosphobetaines, and

alkylamidoalkylsulfobetaines, in particular, (C₈-C₂₄)alkylbetaines,

(C₈-C₂₄)alkylamido(CrC₈)alkylbetaines, sulphobetaines, and

(C₈-C₂₄)alkylamido(C₁-C₈)alkylsulphobetaines. In one embodiment, the amphoteric surfactants of betaine type are chosen from (C₈-C₂₄)alkylbetaines,

(C₈-C₂₄)alkylamido(C₁-C₈)alkylsulphobetaines, sulphobetaines, and phosphobetaines.

Non-limiting examples that may be mentioned include the compounds classified in the CTFA International Cosmetic Ingredient Dictionary & Handbook, 15th Edition, 2014, under the names cocobetaine, laurylbetaine, cetylbetaine, coco/oleamidopropylbetaine,

cocamidopropylbetaine, palmitamidopropylbetaine, stearamidopropylbetaine,

cocamidoethylbetaine, cocamidopropylhydroxysultaine, oleamidopropylhydroxysultaine, cocohydroxysultaine, laurylhydroxysultaine, and cocosultaine, alone or as mixtures.

The betaine-type amphoteric surfactant is preferably an alkylbetaine and an

alkylamidoalkylbetaine, in particular cocobetaine and cocamidopropylbetaine. Among the amidoaminecarboxylated derivatives, mention may be made of the products sold under the name Miranol, as described in U.S. Pat. Nos. 2,528,378 and 2,781,354 and classified in the CTFA dictionary, 3rd edition, 1982 (the disclosures of which are incorporated herein by reference), under the names Amphocarboxyglycinates and

Amphocarboxypropionates, with the respective structures:

R₁-CONHCH₂CH2-N⁺(R2)(R₃)(CH₂COO^") M⁺ X- (Bl) in which:

Ri denotes an alkyl radical of an acid Ri-COOH present in hydrolysed coconut oil, a heptyl, nonyl or undecyl radical,

R₂ denotes a beta-hydroxyethyl group,

R₃ denotes a carboxymethyl group,

M⁺ denotes a cationic ion derived from alkaline metals such as sodium; ammonium ion; or an ion derived from an organic amine;

X^" denotes an organic or inorganic anionic ion such as halides, acetates, phosphates, nitrates, alkyl(C₁-C4)sulfates, alkyl(C₁-C₄)- or alkyl(C₁-C₄)aryl-sulfonates, particularly methylsulfate and ethylsulfate; or M⁺ and X^" are not present; R₁'-CONHCH₂CH₂-N(B)(C) (B2) in which:

R denotes an alkyl radical of an acid Ri'-COOH present in coconut oil or in hydrolysed linseed oil, an alkyl radical, such as a C₇, C₉, C or C₁₃ alkyl radical, a C₁₇ alkyl radical and its iso-form, or an unsaturated C₁₇ radical,

B represents -CH₂CH₂OX,

C represents -(CH₂)_Z-Y', with z=l or 2,

X' denotes a -CH₂-COOH group, -CH₂-COOZ', -CH₂CH₂-COOH, -CH₂CH₂-COOZ' or a hydrogen atom, and

Y' denotes -COOH, -COOZ', -CH₂-CHOH-S0₃Z\ -CH₂-CHOH-S0₃H radical or a

-CH₂-CH(OH)-S0₃-Z' radical,

wherein Z' represents an ion of an alkaline or alkaline earth metal such as sodium, an ion derived from an organic amine or an ammonium ion;

and

R_a"-NH-CH(Y")-(CH₂)_n-C(0)-NH-(CH₂)_n-N(Rd)(Re) (B'2) in which:

Y" denotes -C(0)OH, -C(0)OZ", -CH₂-CH(OH)-S0₃H or -CH₂-CH(OH)-S0₃-Z", wherein Z" denotes a cationic ion derived from alkaline metal or alkaline-earth metals such as sodium, an ion derived from organic amine or an ammonium ion;

Rd and Re denote a C₁-C₄ alkyl or C C₄ hydroxyalkyl radical;

R_a" denotes a C_!o-C₃₀ group alkyl or alkenyl group from an acid, and

n and n' independently denote an integer from 1 to 3.

It is preferable that the amphoteric surfactant with formula Bl and B2 be selected from (Cg-C₂₄)-alkyl amphomonoacetates, (C₈-C₂₄)alkyl amphodiacetates, (C₈-C₂₄)alkyl

amphomonopropionates, and (C₈-C₂₄)alkyl amphodipropionates

These compounds are classified in the CTFA dictionary, 5th edition, 1993, under the names Disodium Cocoamphodiacetate, Disodium Lauroamphodiacetate, Disodium

Caprylamphodiacetate, Disodium Capryloamphodiacetate, Disodium Cocoamphodipropionate, Disodium Lauroamphopropionate, Disodium Caprylamphodipropionate, Disodium

Caprylamphodipropionate, Lauroamphodipropionic acid and Cocoamphodipropionic acid.

By way of example, mention may be made of the cocoamphodiacetate sold under the trade name Miranol® C2M concentrate by the company Rhodia Chimie.

Among compounds of formula (B'2) mention may be made of sodium diethylaminopropyl cocoaspartamide (CTFA) marketed by CHIMEX under the denomination CHIMEXANE HB.

(iii) Cationic Surfactants

The composition may comprise at least one cationic surfactant, Two or more cationic surfactants may be used in combination.

The cationic surfactant may be selected from the group consisting of optionally

polyoxyalkylenated, primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.

Examples of quaternary ammonium salts that may be mentioned include, but are not limited to:

those of general formula (B3) below:

R i R_¾

\ /

N

¾ / \ R4

(B3)

wherein

R_ls R₂, R₃, and R , which may be identical or different, are chosen from linear and branched aliphatic radicals including from 1 to 30 carbon atoms and optionally including heteroatoms such as oxygen, nitrogen, sulfur and halogens. The aliphatic radicals may be chosen, for example, from alkyl, alkoxy, C₂-C₆ polyoxyalkylene, alkylamide,

(C₁₂-C₂₂)alkylamido(C₂-C₆)alkyl, (C₁₂-C₂₂)alkylacetate and hydroxyalkyl radicals; and aromatic radicals such as aryl and alkylaryl; and X^" is chosen from halides, phosphates, acetates, lactates, (C₂-C₆) alkyl sulfates and alkyl- or alkylaryl-sulfonates;

quaternary ammonium salts of imidazoline, for instance those of formula (B4) below:

(B4)

wherein:

R₅ is chosen from alkenyl and alkyl radicals including from 8 to 30 carbon atoms, for example fatty acid derivatives of tallow or of coconut;

R6 is chosen from hydrogen, Ci-C₄ alkyl radicals, and alkenyl and alkyl radicals including from 8 to 30 carbon atoms; R₇ is chosen from C1-C4 alkyl radicals;

R is chosen from hydrogen and Q-C4 alkyl radicals; and

X^" is chosen from halides, phosphates, acetates, lactates, alkyl sulfates, alkyl sulfonates, and alkylaryl sulfonates. In one embodiment, R₅ and are, for example, a mixture of radicals chosen from alkenyl and alkyl radicals including from 12 to 21 carbon atoms, such as fatty acid derivatives of tallow, R₇ is methyl and R₈ is hydrogen. Examples of such products include, but are not limited to, Quaternium-27 (CTFA 1997) and Quaternium-83 (CTFA 1997), which are sold under the names "Rewoquat®" W75, W90, W75PG and W75HPG by the company Witco;

Di or tri quaternary ammonium salts of formula (B5):

R w R. 12

2X-

R 11 ¾3

(B5)

wherein:

R₉ is chosen from aliphatic radicals including from 16 to 30 carbon atoms;

R₁₀ is chosen from hydrogen or alkyl radicals including from 1 to 4 carbon atoms or a group

-(CH₂)₃ (R_16a)(R_17a)(R_18a)N⁺X--;

Rn, R₁₂, R₁₃, R₁₄, R_16a, R_17a, and R_18a, which may be identical or different, are chosen from hydrogen and alkyl radicals including from 1 to 4 carbon atoms; and

X^" is chosen from halides, acetates, phosphates, nitrates, ethyl sulfates, and methyl sulfates.

An example of one such diquaternary ammonium salt is FINQUAT CT-P of FINETEX

(Quaternium-89) or FINQUAT CT (Quaternium-75);

and

a

wherein:

R₂₂ is chosen from Ci-C₆ alkyl radicals and Cj-C₆ hydroxyalkyl and dihydroxyalkyl radicals; R₂₃ is chosen from:

the radical below:

O

R.

26

linear and branched, saturated and unsaturated CrC₂₂ hydrocarbon-based radicals R₂₇, and hydrogen,

R₂₅ is chosen from:

the radical below:

O

R.

28 linear and branched, saturated and unsaturated C_\-Ce hydrocarbon-based radicals R₂₉, and hydrogen,

R24, R26, and R₂8, which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C₇-C₂₁, hydrocarbon-based radicals;

r, s, and t, which may be identical or different, are chosen from integers ranging from 2 to 6; each of rl and tl , which may be identical or different, is 0 or 1 , and r2+rl=2r and tl+2t=2t; y is chosen from integers ranging from 1 to 10;

x and z, which may be identical or different, are chosen from integers ranging from 0 to 10; X^" is chosen from simple and complex, organic and inorganic anions; with the proviso that the sum x+y+z ranges from 1 to 15, that when x is 0, R₂₃ denotes R₂₇, and that when z is 0, R₂₅ denotes R₂₉. R22 may be chosen from linear and branched alkyl radicals. In one embodiment, R₂₂ is chosen from linear alkyl radicals. In another embodiment, R₂₂ is chosen from methyl, ethyl, hydroxyethyl, and dihydroxypropyl radicals, for example methyl and ethyl radicals. In one embodiment, the sum x+y+z ranges from 1 to 10. When R₂₃ is a hydrocarbon-based radical R₂ , it may be long and include from 12 to 22 carbon atoms, or short and include from 1 to 3 carbon atoms. When R₂₅ is a hydrocarbon-based radical R₂₉, it may include, for example, from 1 to 3 carbon atoms. By way of a non-limiting example, in one embodiment, R₂₄, R₂₆, and R₂₈, which may be identical or different, are chosen from linear and branched, saturated and unsaturated, Cn-C₂₁ hydrocarbon-based radicals, for example from linear and branched, saturated and unsaturated Cu-C₂₁ alkyl and alkenyl radicals. In another embodiment, x and z, which may be identical or different, are 0 or 1. In one embodiment, y is equal to 1. In another embodiment, r, s and t, which may be identical or different, are equal to 2 or 3, for example equal to 2. The anion X^" may be chosen from, for example, halides, such as chloride, bromide, and iodide; and C C₄ alkyl sulfates, such as methyl sulfate. However, methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate and lactate, and any other anion that is compatible with the ammonium including an ester function, are other non-limiting examples of anions that may be used according to the present invention. In one embodiment, the anion X^" is chosen from chloride and methyl sulfate.

In another embodiment, the ammonium salts of formula (B6) may be used, wherein:

R₂₂ is chosen from methyl and ethyl radicals,

x and y are equal to 1 ;

z is equal to 0 or 1 ;

r, s and t are equal to 2;

R23 is chosen from:

the radical below:

O x26 ^

methyl, ethyl, and C₁₄-C₂₂ hydrocarbon-based radicals, hydi

R₂₅ is chosen from:

the radical below:

O

R 28

and hydrogen;

R24, R26, and R₂₈, which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C₁₃-C₁₇ hydrocarbon-based radicals, for example from linear and branched, saturated and unsaturated, C₁₃-C₁₇ alkyl and alkenyl radicals.

In one embodiment, the hydrocarbon-based radicals are linear. Non-limiting examples of compounds of formula (B6) that may be mentioned include salts, for example chloride and methyl sulfate, of diacyloxyethyl-dimethylammonium, of

diacyloxyethyl-hydroxyethyl-methylammonium, of

monoacyloxyethyl-dihydroxyethyl-methylammonium, of triacyloxyethyl-methylammonium, of monoacyloxyethyl-hydroxyethyl-dimethyl-ammonium, and mixtures thereof. In one embodiment, the acyl radicals may include from 14 to 18 carbon atoms, and may be derived, for example, from a plant oil, for instance palm oil and sunflower oil. When the compound includes several acyl radicals, these radicals may be identical or different.

These products may be obtained, for example, by direct esterification of optionally

oxyalkylenated triethanolamine, triisopropanolamine, alkyldiethanolamine or

alkyldiisopropanolamine onto fatty acids or onto mixtures of fatty acids of plant or animal origin, or by transesterification of the methyl esters thereof. This esterification may be followed by a quatemization using an alkylating agent chosen from alkyl halides, for example methyl and ethyl halides; dialkyl sulfates, for example dimethyl and diethyl sulfates; methyl methanesulfonate; methyl para-toluenesulfonate; glycol chlorohydrin; and glycerol

chlorohydrin.

Such compounds are sold, for example, under the names Dehyquart® by the company Cognis, Stepanquat® by the company Stepan, Noxamium® by the company Ceca, and "Rewoquat® WE 18" by the company Rewo-Goldschmidt.

Other non-limiting examples of ammonium salts that may be used in the composition according to the present invention include the ammonium salts including at least one ester function described in U.S. Pat. Nos. 4,874,554 and 4,137,180.

Among the quaternary ammonium salts mentioned above that may be used in the composition according to the present invention include, but are not limited to, those corresponding to formula (I), for example tetraalkylammonium chlorides, for instance

dialkyldimethylammonium and alkyltrimethylammonium chlorides in which the alkyl radical includes from about 12 to 22 carbon atoms, such as behenyltrimethylammonium,

distearyldimethylammonium, cetyltrimethylammonium and benzyldimethylstearylammomum chloride; palmitylamidopropyltrimethylammonium chloride; and

stearamidopropyldimethyl(myristyl acetate)ammonium chloride, sold under the name

"Ceraphyl® 70" by the company Van Dyk.

According to one embodiment, the cationic surfactant that may be used in the composition according to the present invention is chosen from behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, Quaternium-83, Quaternium-87, Quaternium-22, behenylamidopropyl-2,3-dihydroxypropyldimethylammonium chloride,

palmitylamidopropyltrimethylammonium chloride, and stearamidopropyldimethylamine.

(iv) Nonionic Surfactants

The composition comprises at least one nonionic surfactant. Two or more nonionic surfactants may be used in combination. The nonionic surfactants are compounds well known in themselves (see, e.g., in this regard, "Handbook of Surfactants" by M. R. Porter, Blackie & Son publishers (Glasgow and London), 1991, pp. 116-178). Thus, they can, for example, be chosen from alcohols, alpha-diols, alkylphenols and esters of fatty acids, these compounds being ethoxylated, propoxylated or glycerolated and having at least one fatty chain comprising, for example, from 8 to 30 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range from 2 to 50, and for the number of glycerol groups to range from 1 to 30. Maltose derivatives may also be mentioned. Non-limiting mention may also be made of copolymers of ethylene oxide and/or of propylene oxide; condensates of ethylene oxide and/or of propylene oxide with fatty alcohols; polyethoxylated fatty amides comprising, for example, from 2 to 30 mol of ethylene oxide; polyglycerolated fatty amides comprising, for example, from 1.5 to 5 glycerol groups, such as from 1.5 to 4; ethoxylated fatty acid esters of sorbitan comprising from 2 to 30 mol of ethylene oxide; ethoxylated oils of plant origin; fatty acid esters of sucrose; fatty acid esters of polyethylene glycol; polyethoxylated fatty acid mono or diesters of glycerol (C₆-C₂₄)alkylpolyglycosides; N-(C6-C₂₄)alkylglucamine derivatives;

amine oxides such as (C₁o-C₁₄)alkylamine oxides or N-(C₁₀-C₁₄)acylaminopropylmorpholine oxides; silicone surfactants; and mixtures thereof. The nonionic surfactants may preferably be chosen from monooxyalkylenated,

polyoxyalkylenated, monoglycerolated or polyglycerolated nonionic surfactants. The oxyalkylene units are more particularly oxyethylene or oxypropylene units, or a combination thereof, and are preferably oxyethylene units. Examples of monooxyalkylenated or polyoxyalkylenated nonionic surfactants that may be mentioned include:

monooxyalkylenated or polyoxyalkylenated (C₈-C₂₄)alkylphenols,

saturated or unsaturated, linear or branched, monooxyalkylenated or polyoxyalkylenated

C₈-C₃o alcohols,

saturated or unsaturated, linear or branched, monooxyalkylenated or polyoxyalkylenated C₈-C₃₀ amides,

esters of saturated or unsaturated, linear or branched, C₈-C₃₀ acids and of polyalkylene glycols,

monooxyalkylenated or polyoxyalkylenated esters of saturated or unsaturated, linear or branched, C₈-C₃₀ acids and of sorbitol,

saturated or unsaturated, monooxyalkylenated or polyoxyalkylenated plant oils,

condensates of ethylene oxide and/or of propylene oxide, inter alia, alone or as mixtures.

The surfactants preferably contain a number of moles of ethylene oxide and/or of propylene oxide of between 1 and 100 and most preferably between 2 and 50. According to one of the embodiments of the present invention, the polyoxyalkylenated nonionic surfactants are chosen from polyoxyethylenated fatty alcohol (polyethylene glycol ether of fatty alcohol) and polyoxyethylenated fatty ester (polyethylene glycol ester of fatty acid). Examples of polyoxyethylenated saturated fatty alcohol (or C₈-C₃₀ alcohols) that may be mentioned include the adducts of ethylene oxide with lauryl alcohol, especially those containing from 9 to 50 oxyethylene units and more particularly those containing from 10 to 12 oxyethylene units (Laureth-10 to Laureth-12, as the CTFA names); the adducts of ethylene oxide with behenyl alcohol, especially those containing from 9 to 50 oxyethylene units (Beheneth-9 to Beheneth-50, as the CTFA names); the adducts of ethylene oxide with cetearyl alcohol (mixture of cetyl alcohol and stearyl alcohol), especially those containing from 10 to 30 oxyethylene units (Ceteareth-10 to Ceteareth-30, as the CTFA names); the adducts of ethylene oxide with cetyl alcohol, especially those containing from 10 to 30 oxyethylene units (Ceteth-10 to Ceteth-30, as the CTFA names); the adducts of ethylene oxide with stearyl alcohol, especially those containing from 10 to 30 oxyethylene units (Steareth-10 to

Steareth-30, as the CTFA names); the adducts of ethylene oxide with isostearyl alcohol, especially those containing from 10 to 50 oxyethylene units (Isosteareth-10 to Isosteareth-50, as the CTFA names); and mixtures thereof. Examples of polyoxyethylenated unsaturated fatty alcohol (or C₈-C₃₀ alcohols) that may be mentioned include the adducts of ethylene oxide with oleyl alcohol, especially those containing from 2 to 50 oxyethylene units and more particularly those containing from 10 to 40 oxyethylene units (Oleth-10 to Oleth-40, as the CTFA names); and mixture thereof. As examples of monoglycerolated or polyglycerolated nonionic surfactants,

monoglycerolated or polyglycerolated C -C₄₀ alcohols are preferably used.

In particular, the monoglycerolated or polyglycerolated C -C₄o alcohols correspond to the following formula:

RO-[CH₂-CH(CH₂OH)-0]_m-H or RO-[CH(CH₂OH)-CH₂0]_m-H in which R represents a linear or branched C₈-C₄₀ and preferably C₈-C₃₀ alkyl or alkenyl radical, and m represents a number ranging from 1 to 30 and preferably from 1.5 to 10.

As examples of compounds that are suitable in the context of the present invention, mention may be made of lauryl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Lauryl Ether), lauryl alcohol containing 1.5 mol of glycerol, oleyl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Oleyl Ether), oleyl alcohol containing 2 mol of glycerol (INCI name: Polyglyceryl-2 Oleyl Ether), cetearyl alcohol containing 2 mol of glycerol, cetearyl alcohol containing 6 mol of glycerol, oleocetyl alcohol containing 6 mol of glycerol, and octadecanol containing 6 mol of glycerol.

The alcohol may represent a mixture of alcohols in the same way that the value of m represents a statistical value, which means that, in a commercial product, several species of polyglycerolated fatty alcohol may coexist in the form of a mixture.

Among the monoglycerolated or polyglycerolated alcohols, it is preferable to use the C /C₁₀ alcohol containing 1 mol of glycerol, the C₁₀/C₁₂ alcohol containing 1 mol of glycerol and the C₁₂ alcohol containing 1.5 mol of glycerol.

The monoglycerolated or polyglycerolated C -C₄₀ fatty esters may correspond to the following formula: R'0-[CH₂-CH(CH₂OR'")-0]_m-R" or R'0-[CH(CH₂OR'")-CH₂0]_m-R" in which each of R', R" and R"' independently represents a hydrogen atom, or a linear or branched C₈-C₄₀ and preferably C -C₃o alkyl-CO- or alkenyl-CO-radical, with the proviso that at least one of R', R" and R'" is not a hydrogen atom, and m represents a number ranging from 1 to 30 and preferably from 1.5 to 10. Examples of polyoxyethylenated fatty esters that may be mentioned include the adducts of ethylene oxide with esters of lauric acid, palmitic acid, stearic acid or behenic acid, and mixtures thereof, especially those containing from 9 to 100 oxyethylene units, such as PEG-9 to PEG-50 laurate (CTFA names: PEG-9 laurate to PEG-50 laurate); PEG-9 to PEG-50 palmitate (CTFA names: PEG-9 palmitate to PEG-50 palmitate); PEG-9 to PEG-50 stearate (CTFA names: PEG-9 stearate to PEG-50 stearate); PEG-9 to PEG-50 palmitostearate; PEG-9 to PEG-50 behenate (CTFA names: PEG-9 behenate to PEG-50 behenate); polyethylene glycol 100 EO monostearate (CTFA name: PEG- 100 stearate); and mixtures thereof.

According to one of the embodiments of the present invention, the nonionic surfactant may be selected from esters of polyols with fatty acids with a saturated or unsaturated chain containing for example from 8 to 24 carbon atoms, preferably 12 to 22 carbon atoms, and polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, and more preferably from 10 to 100 oxyalkylene units, such as glyceryl esters of a C -C₂₄, preferably C₁₂-C₂₂, fatty acid or acids and polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, and more preferably from 10 to 100 oxyalkylene units; sorbitol esters of a C₈-C₂4, preferably C₁₂-C₂₂, fatty acid or acids and polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, and more preferably from 10 to 100 oxyalkylene units; sugar (sucrose, maltose, glucose, fructose, and/or alkylglycose) esters of a C -C₂₄, preferably C₁₂-C₂₂, fatty acid or acids and polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, and more preferably from 10 to 100 oxyalkylene units; ethers of fatty alcohols; ethers of sugar and a C₈-C₂₄, preferably C₁₂-C₂₂, fatty alcohol or alcohols; and mixtures thereof.

As glyceryl esters of fatty acids, glyceryl stearate (glyceryl mono-, di- and/or tristearate) (CTFA name: glyceryl stearate), glyceryl laurate or glyceryl ricinoleate and mixtures thereof can be cited, and as polyoxyalkylenated derivatives thereof, mono-, di- or triester of fatty acids with a polyoxyalkylenated glycerol (mono-, di- or triester of fatty acids with a polyalkylene glycol ether of glycerol), preferably polyoxyethylenated glyceryl stearate

(mono-, di- and/or tristearate), such as PEG-20 glyceryl stearate (mono-, di- and/or tristearate) can be cited.

Mixtures of these surfactants, such as for example the product containing glyceryl stearate and PEG- 100 stearate, marketed under the name ARLACEL 165 by Uniqema, and the product containing glyceryl stearate (glyceryl mono- and distearate) and potassium stearate marketed under the name TEGIN by Goldschmidt (CTFA name: glyceryl stearate SE), can also be used.

The sorbitol esters of C₈-C₂₄ fatty acids and polyoxyalkylenated derivatives thereof can be selected from sorbitan palmitate, sorbitan isostearate, sorbitan trioleate and esters of fatty acids and alkoxylated sorbitan containing for example from 20 to 100 EO, such as for example sorbitan monostearate (CTFA name: sorbitan stearate), sold by the company ICI under the name Span 60, sorbitan monopalmitate (CTFA name: sorbitan palmitate), sold by the company ICI under the name Span 40, and sorbitan tristearate 20 EO (CTFA name:

polysorbate 65), sold by the company ICI under the name Tween 65, polyethylene sorbitan trioleate (polysorbate 85) or the compounds marketed under the trade names Tween 20 or Tween 60 by Uniqema.

As esters of fatty acids and glucose or alkylglucose, glucose palmitate, alkylglucose sesquistearates such as methylglucose sesquistearate, alkylglucose palmitates such as methylglucose or ethylglucose palmitate, methylglucoside fatty esters, the diester of methylglucoside and oleic acid (CTFA name: Methyl glucose dioleate), the mixed ester of methylglucoside and the mixture of oleic acid/hydroxystearic acid (CTFA name: Methyl glucose dioleate/hydroxystearate), the ester of methylglucoside and isostearic acid (CTFA name: Methyl glucose isostearate), the ester of methylglucoside and lauric acid (CTFA name: Methyl glucose laurate), the mixture of monoester and diester of methylglucoside and isostearic acid (CTFA name: Methyl glucose sesqui-isostearate), the mixture of monoester and diester of methylglucoside and stearic acid (CTFA name: Methyl glucose sesquistearate) and in particular the product marketed under the name Glucate SS by AMERCHOL, and mixtures thereof can be cited.

As ethoxylated ethers of fatty acids and glucose or alkylglucose, ethoxylated ethers of fatty acids and methylglucose, and in particular the polyethylene glycol ether of the diester of methylglucose and stearic acid with about 20 moles of ethylene oxide (CTFA name: PEG-20 methyl glucose distearate) such as the product marketed under the name Glucam E-20 distearate by AMERCHOL, the polyethylene glycol ether of the mixture of monoester and diester of methyl-glucose and stearic acid with about 20 moles of ethylene oxide (CTFA name: PEG-20 methyl glucose sesquistearate) and in particular the product marketed under the name Glucamate SSE-20 by AMERCHOL and that marketed under the name Grillocose PSE-20 by GOLDSCHMIDT, and mixtures thereof, can for example be cited.

As sucrose esters, saccharose palmito-stearate, saccharose stearate and saccharose

monolaurate can for example be cited. As sugar ethers, alkylpolyglucosides can be used, and for example decylglucoside such as the product marketed under the name MYDOL 10 by Kao Chemicals, the product marketed under the name PLANTAREN 2000 by Henkel, and the product marketed under the name

ORAMIX NS 10 by Seppic, caprylyl/capryl glucoside such as the product marketed under the name ORAMIX CG 110 by Seppic or under the name LUTENSOL GD 70 by BASF, laurylglucoside such as the products marketed under the names PLANTAREN 1200 N and PLANTACARE 1200 by Henkel, coco-glucoside such as the product marketed under the name PLANTACARE 818 UP by Henkel, cetostearyl glucoside possibly mixed with cetostearyl alcohol, marketed for example under the name MONTANOV 68 by Seppic, under the name TEGO-CARE CG90 by Goldschmidt and under the name EMULGADE KE3302 by Henkel, arachidyl glucoside, for example in the form of the mixture of arachidyl and behenyl alcohols and arachidyl glucoside marketed under the name MONTANOV 202 by Seppic, cocoylethylglucoside, for example in the form of the mixture (35/65) with cetyl and stearyl alcohols, marketed under the name MONTANOV 82 by Seppic, and mixtures thereof can in particular be cited.

Mixtures of glycerides of alkoxylated plant oils such as mixtures of ethoxylated (200 EO) palm and copra (7 EO) glycerides can also be cited.

The nonionic surfactant according to the present invention preferably contains alkenyl or a branched C₁₂-C₂₂ acyl chain such as an oleyl or isostearyl group. More preferably, the nonionic surfactant according to the present invention is PEG-20 glyceryl triisostearate.

According to one of the embodiments of the present invention, the nonionic surfactant may be selected from copolymers of ethylene oxide and of propylene oxide, in particular copolymers of the following formula: HO(C₂H₄0)_a(C₃H₆0)_b(C₂H₄0)_cH in which a, b and c are integers such that a+c ranges from 2 to 100 and b ranges from 14 to 60, and mixtures thereof.

According to one of the embodiments of the present invention, the nonionic surfactant may be selected from silicone surfactants. Non-limiting mention may be made of those disclosed in documents US-A-5364633 and US-A-5411744.

The silicone surfactant ma preferably be a compound of formula (I):

in which:

R_l3 R₂ and R₃, independently of each other, represent a Ci-C^ alkyl radical or a radical

-(CH₂)_x-(OCH₂CH₂)y-(OCH₂CH₂CH₂)_z-OR₄, at least one radical R R₂ or R₃ not being an alkyl radical; R4 being a hydrogen, an alkyl radical or an acyl radical;

A is an integer ranging from 0 to 200;

B is an integer ranging from 0 to 50; with the proviso that A and B are not simultaneously equal to zero;

x is an integer ranging from 1 to 6;

y is an integer ranging from 1 to 30;

z is an integer ranging from 0 to 5.

According to one preferred embodiment of the present invention, in the compound of formula (I), the alkyl radical is a methyl radical, x is an integer ranging from 2 to 6 and y is an integer ranging from 4 to 30.

As examples of silicone surfactants of formula (I), mention may be made of the compounds of formula (II):

(CH₃)₃SiO - [(CH₃)₂SiO]_A - (CH₃SiO)_B - Si(CH₃)₃

I (ID

(CH₂)₂-(OCH₂CH₂)_y-OH

in which A is an integer ranging from 20 to 105, B is an integer ranging from 2 to 10 and y is an integer ranging from 10 to 20.

As examples of silicone surfactants of formula (I), mention may also be made of the compounds of formula (III):

H-(OCH₂CH₂)_y-(CH₂)₃-[(CH₃)₂SiO]_A'-(CH₂)₃-(OCH₂CH₂)_y-OH (III) in which A' and y are integers ranging from 10 to 20.

Compounds of the present invention which may be used are those sold by the company Dow Corning under the names DC 5329, DC 7439-146, DC 2-5695 and Q4-3667. The compounds DC 5329, DC 7439-146 and DC 2-5695 are compounds of formula (II) in which, respectively, A is 22, B is 2 and y is 12; A is 103, B is 10 and y is 12; A is 27, B is 3 and y is 12.

The compound Q4-3667 is a compound of formula (III) in which A is 15 and y is 13. (Acid) The composition according to the present invention may comprise at least one acid. Two or more acids may be used in combination. Thus, a single type of acid or a combination of different types of acids may be used.

The acid may be used to adjust the pH of the composition according to the present invention.

It is preferable that the composition according to the present invention include acid(s), if necessary, to control the pH of the composition to be 9.0 or less, preferably 8.9 or less, and more preferably 8.8 or less. As the acid, mention may be made of any inorganic or organic acids which are commonly used in cosmetic products such as citric acid, lactic acid, sulfuric acid, phosphoric acid or hydrochloric acid (HC1). HC1 is preferable.

The acid(s) may be used in a total amount of from 0.1 to 15% by weight, preferably from 0.2 to 10% by weight, more preferably from 0.3 to 5% by weight, relative to the total weight of the composition, depending on their solubility.

(Amino Acid) The composition according to the present invention may comprise at least one amino acid other than the above reducing agent, alkaline agent or acid. Two or more amino acids may be used in combination. Thus, a single type of amino acid or a combination of different types of amino acids may be used. The term "amino acid" here means a compound which is not obtained by polycondensation of identical or different amino acids. In addition, the term "amino acid" here encompasses not only an amino acid itself but also an amino acid in the form of a salt thereof. As the salt, mention may be made of sodium salt, magnesium salt, potassium salt, calcium salt, and the like.

The amino acids that may be used according to the present invention comprise at least one amine function and at least one acid function.

The acid function(s) may be carboxylic, sulfonic, phosphonic or phosphoric, and are preferably carboxylic.

The amino acids that may be used according to the present invention may be a-amino acids, β-amino acids, or γ-amino acids. Preferably, the amino acids used in the present invention are a-amino acids, i.e., they comprise an amine function and an acid function at the same carbon atom. The α-amino acids may be represented by the following formula:

in which:

when p=2, R represents a hydrogen atom, an aliphatic group optionally containing one or several nitrogen atoms, a heterocyclic portion, or an aromatic group, or

when p=l, R can form a heterocycle with the nitrogen atom of -N(H)_P. This heterocycle is preferably a saturated 5-membered ring, optionally substituted with one or more C_1-4 alkyl or hydroxyl groups.

Preferably, the aliphatic group is a linear or branched C_1-4 alkyl group; a linear or branched C_1-4 hydroxyalkyl group; a linear or branched C_1-4 aminoalkyl group; a linear or branched (C_1-4 alkyl)thio(C_1-4)alkyl group; a linear or branched C_2-4 carboxyalkyl group; a linear or branched ureidoalkyl group, a linear or branched guanidinoalkyl group, a linear or branched imidazoloalkyl group or a linear or branched indolylalkyl group, the alkyl portions of these last four groups comprising from one to four carbon atoms.

Preferably, the aromatic group is a C₆ aryl or C_7-10 aralkyl group, the aromatic nucleus optionally being substituted with one or more C_1-4 alkyl or hydroxyl groups.

As amino acids that may be used in the present invention, mention may be made especially of aspartic acid, glutamic acid, alanine, asparagine, carnitine, glutamine, glycine, histidine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine, valine, hydroxyproline and mixtures thereof.

Preferably, the amino acids comprise only one amine function, which may or may not be engaged in a ring, and only one acid function. The amino acids that are particularly preferred in the present invention are alanine, asparagine, glutamine, glycine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, threonine, tyrosine and valine.

The aminoacid(s) may be used in a total amount of from 0.001 to 10% by weight, preferably from 0.05 to 5% by weight, more preferably from 0.01 to 1% by weight, relative to the total weight of the composition. (Conditioning Agent)

The composition according to the present invention may comprise at least one conditioning agent. Two or more conditioning agents may be used in combination. Thus, a single type of conditioning agent or a combination of different types of conditioning agents may be used.

The conditioning agent can provide keratin fibers such as hair with conditioning effects.

It is preferable that the conditioning agent be selected from cationic polymers. The composition according to the present invention may comprise at least one cationic polymer. A single type of cationic polymer may be used, but two or more different types of cationic polymers may be used in combination. It should be noted that, for the purposes of the present invention, the term "cationic polymer" denotes any polymer containing cationic groups and/or groups that may be ionized into cationic groups.

Such polymers may be chosen from those already known per se as improving the cosmetic properties of the hair, i.e., especially those described in patent application EP-A-337 354 and in French patents FR-2 270 846, 2 383 660, 2 598 611 , 2 470 596 and 2 519 863. The cationic polymers that are preferred are chosen from those containing units comprising primary, secondary, tertiary and/or quaternary amine groups, which may either form part of the main polymer chain or may be borne by a side substituent directly attached thereto.

The cationic polymers used generally have a number-average molecular mass of between approximately 500 and approximately 5^χ 10⁶ and preferably between approximately 10³ and approximately 3 ^χ 10⁶.

Among the cationic polymers that may be mentioned more particularly are polymers of the polyamine, polyamino amide and polyquaternary ammonium type.

These are known products. They are described in particular in French patents 2 505 348 and 2 542 997. Among the said polymers, mention may be made of the following.

(1) homopolymers or copolymers derived from acrylic or methacrylic esters or amides and comprising at least one of the units of formula (I), (II), (III) or (IV) below:

in which

R-3, which may be identical or different, denote a hydrogen atom or a CH₃ radical;

A, which may be identical or different, represent a linear or branched alkyl group of 1 to

6 carbon atoms, preferably 2 or 3 carbon atoms, or a hydroxyalkyl group of 1 to 4 carbon atoms;

R4, R₅ and R^, which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl radical and preferably an alkyl group containing from 1 to 6 carbon atoms;

R_\ and R₂, which may be identical or different, represent hydrogen or an alkyl group containing from 1 to 6 carbon atoms, and preferably methyl or ethyl; and

X denotes an anion derived from an inorganic or organic acid, such as a methosulfate anion or a halide such as chloride or bromide.

The polymers of family (1) can also contain one or more units derived from comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetone

acrylamides, acrylamides and methacrylamides substituted on the nitrogen with lower (C₁-C₄) alkyls, acrylic or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinyl-caprolactam, and vinyl esters.

Thus, among these polymers of family (1), mention may be made of:

- copolymers of acrylamide and of dimethylaminoethyl methacrylate quaternized with dimethyl sulfate or with a dimethyl halide, such as the product sold under the name Hercofloc by the company Hercules,

- the copolymers of acrylamide and of methacryloyloxyethyltrimethylammonium chloride described, for example, in patent application EP-A-080 976 and sold under the name Bina Quat P 100 by the company BASF,

- the copolymer of acrylamide and of methacryloyloxyethyltrimethylammonium methosulfate sold under the name Reten by the company Hercules,

- quaternized or non-quaternized vinylpyrrolidone/dialkylaminoalkyl aery late or methacrylate copolymers, such as the products sold under the name "Gafquat" by the company ISP, for instance "Gafquat 734" or "Gafquat 755", or alternatively the products known as

"Copolymer 845, 958 and 937". These polymers are described in detail in French patents 2 077 143 and 2 393 573,

- dimethylaminoethyl methacrylate/vinylcaprolactam/vinylpyrrolidone terpolymers, such as the product sold under the name Gaffix VC 713 by the company ISP, and

- vinylpyrrolidone/methacrylamidopropyldimethylamine copolymers sold in particular under the name Styleze CC 10 by ISP, and quaternized vinylpyrrolidone/dimethylaminopropyl methacrylamide copolymers such as the product sold under the name "Gafquat HS 100" by the company ISP. (2) The cellulose ether derivatives comprising quaternary ammonium groups, which are described in French patent 1 492 597, and in particular the polymers sold under the names "JPv" (JR 400, JR 125, JR 30M) or "LR" (LR 400, LR 30M) by the company Amerchol. These polymers are also defined in the CTFA dictionary as hydroxyethylcellulose quaternary ammoniums that have reacted with an epoxide substituted with a trimethylammonium group.

(3) Cationic cellulose derivatives such as the copolymers of cellulose or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, described especially in US patent 4 131 576, such as hydroxyalkylcelluloses, for instance hydroxymethyl-,

hydroxyethyl- or hydroxypropylcelluloses grafted especially with a methacryloylethyl- trimethylammonium, methacrylamidopropyltrimethylammonium or

dimethyldiallylammonium salt.

The commercial products corresponding to this definition are more particularly the products sold under the name Celquat L 200 and Celquat H 100 by the company Akzo Nobel.

(4) The cationic guar gums described more particularly in US patents 3 589 578 and

4 031 307, such as guar gums containing trialkylammonium cationic groups. Use is made, for example, of guar gums modified with a salt (e.g., chloride) of

2,3-epoxypropyltrimethylammonium. Mention may be made of guar

hydroxypropyltrimonium chloride and hydroxypropyl guar hydroxypropyl trimonium chloride, such as those sold especially under the trade names Jaguar C13S, Jaguar CMS, Jaguar C 17 and Jaguar C 162 by the company Solvay.

(5) Polymers consisting of piperazinyl units and of divalent alkylene or hydroxy alkylene radicals containing straight or branched chains, optionally interrupted by oxygen, sulfur or nitrogen atoms or by aromatic or heterocyclic rings, and also the oxidation and/or quaternization products of these polymers. Such polymers are described, in particular, in French patents 2 162 025 and 2 280 361. (6) Water-soluble polyamino amides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyamino amides can be crosslinked with an

epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bis-unsaturated derivative, a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide or alternatively with an oligomer resulting from the reaction of a difunctional compound which is reactive with a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide, an epihalohydrin, a diepoxide or a bis-unsaturated derivative; the crosslinking agent being used in proportions ranging from 0.025 to 0.35 mol per amine group of the polyamino amide; these polyamino amides can be alkylated or, if they contain one or more tertiary amine functions, they can be quaternized. Such polymers are described, in particular, in French patents 2 252 840 and 2 368 508.

(7) Cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium, such as the homopolymers or copolymers containing, as a main constituent of the chain, units

corresponding to formula (V) or (VI):

in which formulae

k and t are equal to 0 or 1 , the sum k + 1 being equal to 1 ; R₉ denotes a hydrogen atom or a methyl radical; R₇ and R₈, independently of each other, denote an alkyl group having from 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably has 1 to 5 carbon atoms, a lower (C₁-C₄) amidoalkyl group, or R₇ and R₈ can denote, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidyl or morpholinyl; R₇ and R₈, independently of each other, preferably denote an alkyl group having from 1 to 4 carbon atoms; and Y^" is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate. These polymers are described in particular in French patent 2 080 759 and in its Certificate of Addition 2 190 406.

Among the polymers defined above, mention may be made more particularly of the dimethyldiallylammonium chloride homopolymer sold under the name "Merquat 100" by the company Nalco (and its homologues of low weight-average molecular mass) and the copolymers of diallyldimethylammonium chloride and of acrylamide, sold under the name "Merquat 550".

(8) The quaternary diammonium polymer containing repeating units corresponding to the formula:

in which formula (VII):

R₁₀, n, R₁₂ and R₁₃, which may be identical or different, represent aliphatic, alicyclic or arylaliphatic radicals containing from 1 to 20 carbon atoms or lower hydroxyalkylaliphatic radicals, or alternatively R₁₀, R_11; R₁₂ and R₁₃, together or separately, constitute, with the nitrogen atoms to which they are attached, heterocycles optionally containing a second hetero atom other than nitrogen, or alternatively R₁₀, Ru, R₁₂ and R₁₃ represent a linear or branched C C₆ alkyl radical substituted with a nitrile, ester, acyl or amide group or a group

-CO-0-R₁ -D or -CO-NH-R₁₄-D where R₁₄ is an alkylene and D is a quaternary ammonium group;

Ai and Bi represent polymethylene groups containing from 2 to 20 carbon atoms which may be linear or branched, saturated or unsaturated, and which may contain, linked to or intercalated in the main chain, one or more aromatic rings or one or more oxygen or sulfur atoms or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and

X^" denotes an anion derived from an inorganic or organic acid;

Ai, R₁₀ and R₁₂ can form, with the two nitrogen atoms to which they are attached, a piperazine ring; in addition, if Ai denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, Bi can also denote a group -(CH₂)_n-CO-D-OC-(CH₂)_n- in which D denotes:

i) a glycol residue of formula: -0-Z-0-, where Z denotes a linear or branched

hydrocarbon-based radical or a group corresponding to one of the following formulae:

-(CH₂-CH₂-0)_x-CH₂-CH₂-; and

-[CH₂-CH(CH₃)-0]_y-CH₂-CH(CH₃)- where x and y denote an integer from 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing an average degree of polymerization; ii) a bis-secondary diamine residue such as a piperazine derivative;

iii) a bis-primary diamine residue of formula -NH-Y-NH-, where Y denotes a linear or branched hydrocarbon-based radical, or alternatively the divalent radical

-CH₂-CH₂-S-S-CH₂-CH₂-; or

iv) a ureylene group of formula -NH-CO-NH-.

Preferably, X^" is an anion such as chloride or bromide.

These polymers generally have a number-average molecular mass of between 1000 and 100 000.

Polymers of this type are described in particular in French patents 2 320 330, 2 270 846, 2 316 271 , 2 336 434 and 2 413 907 and US patents 2 273 780, 2 375 853, 2 388 614, 2 454 547, 3 206 462, 2 261 002, 2 271 378, 3 874 870, 4 001 432, 3 929 990, 3 966 904, 4 005 193, 4 025 617, 4 025 627, 4 025 653, 4 026 945 and 4 027 020.

It is more particularly possible to use polymers that consist of repeating units corresponding to the following formula (

- _p— (VIII)

in which

Rio, Rn, Ri2 and R₁₃, which may be identical or different, denote an alkyl or hydroxyalkyl radical containing from 1 to 4 carbon atoms approximately, n and p are integers ranging from 2 to 20 approximately, and X^" is an anion derived from a mineral or organic acid.

One particularly preferred compound of formula (VIII) is that for which R₁₀, Ru R₁₂ and R₁₃ represent a methyl group, n=3, p=6 and X=C1, which is called Hexadimethrine chloride according to the INCI(CTFA) nomenclature.

(9) Polyamines such as Polyquart H sold by Cognis, which is given under the reference name "Polyethylene glycol (15) tallow polyamine" in the CTFA dictionary.

(10) Crosslinked methacryloyloxy(Ci-C4)alkyltri(C₁-C₄)alkylammonium salt polymers such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with

dimethylaminoethyl methacrylate quaternized with methyl chloride, the homo- or

copolymerization being followed by crosslinking with a compound containing olefinic unsaturation, in particular methylenebisacrylamide. A crosslinked

acrylamide/methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion containing 50% by weight of the said copolymer in mineral oil can be used more particularly. This dispersion is sold under the name "Salcare® SC 92" by the company BASF. A crosslinked methacryloyloxyethyltrimethylammonium chloride homopolymer containing about 50% by weight of the homopolymer in mineral oil or in a liquid ester can also be used. These dispersions are sold under the names "Salcare® SC 95" and "Salcare® SC 96" by the company Allied Colloids. (11) Other cationic polymers which can be used in the context of the present invention are polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes and chitin derivatives. It is preferable that the cationic polymer be a polyquaternium polymer or a polymeric quaternary ammonium salt.

Polymeric quaternary ammonium salts are cationic polymers comprising at least one quaternized nitrogen atom. Mention may in particular be made, as polymeric quaternary ammonium salts, of the Polyquaternium products (CTFA name), which contribute mainly to the quality of foam and feeling of the skin after use, in particular the feeling of the skin after use. These polymers can preferably be chosen from the following polymers:

Polyquaternium-5, such as the product Merquat 5 sold by Nalco;

Polyquaternium-6, such as the product Salcare SC 30 sold by BASF and the product Merquat 100 sold by Nalco;

Polyquaternium-7, such as the products Merquat S, Merquat 2200, Merquat 7SPR, and

Merquat 550 sold by Nalco and the product Salcare SC 10 sold by BASF;

Polyquaternium- 10, such as the product Polymer JR400 sold by Amerchol;

Polyquaternium-ll, such as the products Gafquat 755, Gafquat 755N and Gafquat 734 sold by ISP;

Polyquaternium- 15, such as the product Rohagit KF 720 F sold by Rohm;

Polyquaternium- 16, such as the products Luviquat FC905, Luviquat FC370, Luviquat HM552 and Luviquat FC550 sold by BASF;

Polyquaternium-28, such as the product Styleze CC 10 sold by ISP;

Polyquaternium-44, such as the product Luviquat Care sold by BASF; Polyquaternium-46, such as the product Luviquat Hold sold by BASF; and

Polyquaternium-47, such as the product Merquat 2001 sold by Nalco.

Preferably, the cationic polymer is chosen from, Polyquaternium-10, Polyquaternium-47, hydroxypropyl guar hydroxypropyl trimonium chloride and their mixtures.

The amount of the cationic polymer(s) is not limited, but the amount of the cationic polymer may be from 0.01 to 10% by weight, preferably 0.05 to 5% by weight, and more preferably 0.1 to 1% by weight, relative to the total weight of the composition.

(Dicarboxylic Acid)

The composition according to the present invention may be free of dicarboxylic acid which is present as it is (i.e., dicarboxylic acid itself or a salt thereof). The meaning of "free of is as explained above. As the dicarboxylic acid, mention may be made of α,ω-dicarboxylic acid with 5 to 10 carbon atoms, and preferably adipic acid.

Due to the very small amount or the absence of dicarboxylic acid, malodor caused by the dicarboxylic acid during the use of the composition according to the present invention may be reduced or prevented.

(Other Ingredients)

The composition according to the present invention may also comprise at least one additional ingredient.

The amount of the additional ingredient(s) is not limited, but may be from 0.1 to 10% by weight relative to the total weight of the composition according to the present invention. The additional ingredient(s) may be selected from the group consisting of thickeners; anionic, nonionic or amphoteric polymers; peptides and derivatives thereof; protein hydrolyzates; swelling agents and penetrating agents; agents for combating hair loss; anti-dandruff agents; associative-type or not, natural or synthetic thickeners for oils; suspending agents;

sequestering agents; opacifying agents; dyes; sunscreen agents; vitamins or provitamins; fragrances; preserving agents, stabilizers; and mixtures thereof.

The vehicle for the composition according to the present invention is preferably an aqueous medium consisting of water and may advantageously contain one or several cosmetically acceptable organic solvents, which particularly include monohydric alcohols, such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol, as well as ethylene glycol alkyl ethers such as ethylene glycol monomethyl, monoethyl and monobutyl ethers; propylene glycol alkyl ethers such as propylene glycol monomethyl, monoethyl and monomutyl ethers; diethylene glycol alkyl ethers such as diethylene glycol monomethyl, monoethyl and monobutyl ethers. [Process]

The present invention also relates to a reshaping process, in particular permanent waving, for keratin fibers, preferably the hair.

The reshaping process according to the present invention can be performed by: (i) applying onto keratin fibers the composition described above;

(ii) optionally rinsing the keratin fibers;

(iii) applying onto the keratin fibers an oxidizing composition comprising at least one oxidizing agent; and

(iv) optionally rinsing and/or drying the keratin fibers.

The step (i) is for reducing the disulfide bonds in keratin fibers.

The composition used in the step (i) for reducing the disulfide bonds in keratin fibers, can be used as a permanent waving composition for the keratin fibers.

In the step (i), the above-described composition is applied to the keratin fibers. The application of the composition may be performed by any means, such as a brush and a comb. It may be possible that the keratin fibers after the application of the composition be left as they are for a certain amount of time typically from 1 minute to 1 hour, preferably from 10 to 40 minutes, if necessary, in order to let the composition penetrate into the keratin fibers.

In the step (ii), the keratin fibers may be rinsed preferably with water. According to the present invention, keratin fibers such as hair may be subjected to mechanical tension which is typically used for permanent deformation of the keratin fibers before and/or after the step (i), preferably before the step (iii).

The mechanical tension can be applied to the keratin fibers by any means to deform the keratin fibers to an intended shape. For example, the mechanical tension may be provided by at least one reshaping means selected from the group consisting of a curler, a roller, and a clip. The reshaping means may comprise at least one heater. If the keratin fibers are rolled around a curler, this rolling-up may be performed on the entire length of the keratin fibers or, for example, on half the length of the keratin fibers. Depending on, for example, the desired hairstyle shape and amount of curls, the rolling-up may be performed with more or less thick locks.

If necessary, the keratin fibers may be provided with heat, for deforming or reshaping the keratin fibers, preferably after the step (i) or the step (ii) if present, or before the step (iii). For example, the keratin fibers which may or may not be under mechanical tension are heated with a heating means such as a heating iron (when straightening) or a heating rod (when waving) at typically from 50 to 150°C, preferably 70 to 100°C for typically 5 minutes to 2 hours, preferably 10 minutes to 1 hour. In step (iii), the keratin fibers are oxidized by an oxidizing composition. The oxidizing composition comprises at least one oxidizing agent. Preferably, the oxidizing agent(s) is (are) chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, and peroxygenated salts, for instance alkali metal or alkaline-earth metal persulfates, perborates and percarbonates, and peracids and precursors thereof It is preferable that the oxidizing composition comprise sodium bromate, especially as an aqueous solution thereof (aqueous sodium bromate solution). The concentration of the sodium bromate in the oxidizing composition may range from 0.1 to 20% by weight, preferably 1 to 10% by weight, relative to the total weight of the oxidizing composition. In one embodiment, the oxidizing composition comprises hydrogen peroxide, especially as an aqueous solution thereof (aqueous hydrogen peroxide solution). The concentration of the hydrogen peroxide in the oxidizing composition may range from 0.1 to 20% by weight, preferably 1 to 10% by weight, relative to the total weight of the oxidizing composition.

The oxidizing composition may be aqueous or nonaqueous. The term "aqueous" means that the developer comprises more than 5% by weight of water, preferably more than 10% by weight of water and even more advantageously more than 20% by weight of water.

Usually, the pH of the oxidizing composition, when it is aqueous, is less than 8. The oxidizing composition may also contain at least one additional ingredient explained in detail previously in the context of the composition according to the present invention.

The oxidizing composition may be in various forms, for instance a shampoo, a gel, a mousse, a thickened lotion and a cream.

According to the present invention, it is preferable that the step (iii) perform mild oxidation by applying an oxidizing composition with a short, or with no, standing time on the keratin fibers. As the standing time, mention may be made of 3 minutes to 40 minutes, preferably 5 minutes to 30 minutes.

In step (iv), the keratin fibers may be rinsed preferably with water, and/or may be dried. The drying of the keratin fibers can be performed with a conventional drying means such as a hair drier. [Method and Use]

The present invention also relates to a use of at least one polyol with 4 or more carbon atoms in a reducing composition comprising at least one reducing agent wherein the amount of the polyol in the reducing composition is less than 1.0% by weight relative to the total weight of the reducing composition, for enhancing reshaping efficiency for keratin fibers with less damage to the keratin fibers provided by the reducing composition in combination with an oxidizing composition comprising at least one oxidizing agent.

The polyol can promote the penetration of the reducing agent(s) into keratin fibers, and can reduce or cancel hydrophobic interactions that are non-reactive bonds in the keratin fibers. Due to the use of the polyol with the reducing agent(s), cancellation of the internal bonds in the keratin fibers can be performed even with a small amount of the reducing agent(s).

Therefore, the deformation of keratin fibers is possible with reduced damage due to the use of a small amount of the reducing agent(s).

The polyol used in the present invention is not intended for conditioning keratin fibers. Thus, the amount of polyol used in the present invention is limited such that it is less than 1.0% by weight relative to the total weight of the composition. The use of the polyol in an amount of 1.0% by weight or more, preferably 1.5% by weight or more, and more preferably 2.0% by weight or more, relative to the total weight of the composition is not preferable, because the reshaping efficiency of the keratin fibers can be deteriorated.

EXAMPLES

The present invention will be described in a more detailed manner by way of examples. However, these examples should not be construed as limiting the scope of the present invention.

[Examples 1-11 and Comparative Examples 1-7]

The following compositions according to Examples 1-11 and Comparative Examples 1-7, shown in Tables 1 and 2 were prepared by mixing the ingredients shown in Tables 1 and 2. The numerical values for the amounts of the ingredients shown in Tables 1 and 2 are all based on "% by weight" as active raw materials. The pH of the compositions according to Examples 1-11 and Comparative Examples 1-7 were 8.8.

Table 1

Table 2

[Evaluation]

The compositions according to Examples 1-11 and Comparative Examples 1-7 were used for permanent waving of the hair.

Each of the compositions according to Example 1-11 and Comparative Examples 1-7 in an amount of 40 g was applied to the hair on half of the head of each of 4 panelists, the hair was wound around a rod, and the hair was left for 30 min. Then, the hair was rinsed off with water. Next, an oxidizing lotion (neutralizer) which has the composition shown in Table 3 below was applied onto the hair, and the hair was left for 20 min. Then, the rod was removed, and the hair was rinsed off with water and dried.

Table 3: Oxidizing Lotion

The panelists evaluated the cosmetic properties, such as wave intensity, deepness, regularity of curl, wave elasticity and suppleness, provided by the compositions according to Examples 1-11 and Comparative Examples 1-7 in accordance with the criteria shown below. (Wave Intensity) Wave intensity: the greater the number of curls formed, the stronger the wave intensity is.

The criteria of the evaluation were as follows.

++: significantly stronger wave intensity

+: stronger wave intensity

0: benchmark

-: less wave intensity

— : significantly less wave intensity

(Deepness)

Deepness (defined waves): the shorter the hair length becomes after the permanent waving process, the more deepness it has.

The criteria of the evaluation were as follows.

++: significantly better defined waves

+: better defined waves

0: benchmark

-: less defined waves

— : significantly less defined waves

(Regularity of Curl)

Regularity of curl: the more each curl size and curl shape from the root to the tip of the hair are similar to each other, the more regularity of curl.

The criteria of the evaluation were as follows.

++: significantly better regularity of curl

+: better regularity of curl

0: benchmark

-: less regularity of curl

— : significantly less regularity of curl

(Wave Elasticity) Wave elasticity: when the wet waved hair is pulled to the same length and then released, the longer the bounce lasts, the more wave elasticity.

The criteria of the evaluation were as follows.

++: significantly better wave elasticity

+: better wave elasticity

0: benchmark

-: less wave elasticity

— : significantly less wave elasticity

(Suppleness) Suppleness: the property of being pliant and flexible

The criteria of the evaluation were as follows.

++: significantly more feeling of suppleness, 4 panelists said better suppleness than

benchmark

+: more feeling of suppleness, 3 panelists said better suppleness than benchmark 0: benchmark

-: less feeling of suppleness, 3 panelists said less suppleness than benchmark — : significantly less feeling of suppleness, 4 panelists said less suppleness than

benchmark

The results of the evaluations are shown in Tables 1 and 2. The compositions according to Comparative Examples 1-6 do not comprise a polyol with 4 or more carbon atoms in an amount of less than 1.0% by weight relative to the total weight of the composition, and therefore, the cosmetic properties provided by the compositions according to Comparative Examples 1-6 are inferior to those provided by the compositions according to Examples 1-9.

Specifically, the composition according to Example 1 includes a combination of ethanolamine thioglycolate and cysteine (ingredients (a)), and 0.1% by weight of pentyleneglycol

(ingredient (b)). Thus, the composition according to Example 1 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 1 including 2.5% by weight of pentyleneglcol or Comparative Example 6, as a control, including no polyol.

The composition according to Example 2 includes a combination of ethanolamine

thioglycolate and cysteine (ingredients (a)), and 0.1% by weight of pentyleneglycol and 0.1 % by weight of hexyleneglycol (ingredients (b)). Thus, the composition according to Example 2 can also provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 6.

The composition according to Example 3 includes a combination of ethanolamine

thioglycolate and cysteine (ingredients (a)), and 0.1% by weight of hexyleneglycol

(ingredients (b)). Thus, the composition according to Example 3 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 2 including 2.5% by weight of hexyelne glycol or Comparative Example 6, as a control, including no polyol.

The composition according to Example 4 includes a combination of ethanolamine

thioglycolate and cysteine (ingredients (a)), and 0.1% by weight of hexyleneglycol and 0.1% by weight of butyleneglycol (ingredients (b)). Thus, the composition according to Example 4 can also provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 6.

The composition according to Example 5 includes a combination of ethanolamine

thioglycolate and cysteine (ingredients (a)), and 0.1% by weight of butyleneglycol

(ingredients (b)). Thus, the composition according to Example 5 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 3 including 2.5% by weight of butyleneglycol or Comparative Example 6, as a control, including no polyol.

The composition according to Example 6 includes a combination of ethanolamine

thioglycolate and cysteine (ingredients (a)), and 0.1% by weight of pentyleneglycol, 0.1% by weight of hexyleneglycol and 0.1% by weight of butyleneglycol (ingredients (b)). Thus, the composition according to Example 6 can also provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 6.

The composition according to Example 7 includes a combination of ethanolamine

thioglycolate and cysteine (ingredients (a)), and 0.5% by weight of pentyleneglycol

(ingredient (b)). Thus, the composition according to Example 7 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 1 including 2.5% by weight of pentyleneglcol or Comparative Example 6, as a control, including no polyol. These cosmetic effects provided by Example 7 are inferior to those provided by Example 1.

However, the cosmetic effects provided by Example 7 are sufficient to realize the purpose of the present invention.

The composition according to Example 8 includes a combination of ethanolamine

thioglycolate and cysteine (ingredients (a)), and 0.5% by weight of hexyleneglycol (ingredient (b)). Thus, the composition according to Example 8 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 2 including 2.5% by weight of hexyelne glycol or

Comparative Example 6, as a control, including no polyol. These cosmetic effects provided by Example 8 are inferior to those provided by Example 2. However, the cosmetic effects provided by Example 8 are sufficient to realize the purpose of the present invention. The composition according to Example 9 includes a combination of ethanolamine

thioglycolate and cysteine (ingredients (a)), and 0.5% by weight of butyleneglycol (ingredient (b)). Thus, the composition according to Example 9 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 3 including 2.5% by weight of butyleneglycol or Comparative Example 6, as a control, including no polyol. These cosmetic effects provided by Example 9 are inferior to those provided by Example 3. However, the cosmetic effects provided by Example 9 are sufficient to realize the purpose of the present invention.

The composition according to Comparative Example 4 including 0.1% by weight of propylene cannot exert better cosmetic effects than Comparative Example 6 which is a control including no polyol. Rather, the composition according to Comparative Example 5 including 2.5% by weight of propylene exert inferior cosmetic effects to Comparative

Example 6 which is a control including no polyol. It should be noted that the addition of a relatively large amount of polyol does not contribute to enhance cosmetic effects.

The composition according to Comparative Example 7 does not comprise a polyol with 4 or more carbon atoms in an amount of less than 1.0% by weight relative to the total weight of the composition, and therefore, the cosmetic properties provided by the composition according to Comparative Example 7 are inferior to those provided by the compositions according to Examples 10 and 11. Specifically, the composition according to Example 10 includes a combination of cysteamine HC1 and ammonium thioglycolate (ingredients (a)), and 0.1% by weight of pentyleneglycol (ingredient (b)). Thus, the composition according to Example 10 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 7 including no pentyleneglcol.

The composition according to Example 11 includes a combination of cysteamine HC1 and ammonium thioglycolate (ingredients (a)), and 0.1% by weight of hexyleneglycol (ingredient (b)). Thus, the composition according to Example 11 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 7 including no hexyleneglycol.

The evaluation results for Examples 1-11 show that the use of a combination of a reducing agent and a polyol with 4 or more carbon atoms in an amount of less than 1.0% by weight relative to the total weight of the composition can provide superior cosmetic effects such as good wave intensity, good deepness, good regularity of curl, good wave elasticity and good suppleness.

Claims

A composition for keratin fibers, comprising:

(a) at least one reducing agent;

(b) at least one polyol with 4 or more carbon atoms,

wherein

The composition according to Claim 1 , wherein the (b) polyol is selected from glycols.

The composition according to Claims 1 or 2, wherein the (b) polyol is selected from the group consisting of butylene glycol, pentylene glycol, hexylene glycol, and mixtures thereof.

The composition according to any one of Claims 1 to 3, wherein the amount of the (b) polyol(s) in the composition is from 0.001 to less than 1.0% by weight, preferably from 0.01 to less than 0.5% by weight, and more preferably from 0.1 to 0.3% by weight, relative to the total weight of the composition.

The composition according to any one of Claims 1 to 4, wherein the (a) reducing agent is selected from the group consisting of thioglycolic acid, thiolactic acid, cysteine, N-acetylcysteine, cysteamine, lactonethiol compounds such as

butyrolactonethiol, glyceryl monothioglycolate, sulfite or bisulfite compounds, thioglycerine, their derivatives, and their salts.

The composition according to any one of Claims 1 to 5, wherein the amount of the (a) reducing agent(s) in the composition is from 0.01 to 25% by weight, preferably from 0.1 to 20% by weight, and more preferably from 1.0 to 15% by weight, relative to the total weight of the composition.

The composition according to any one of Claims 1 to 6, further comprising (c) at least one alkaline agent.

The composition according to any one of Claims 1 to 7, wherein the pH of the composition is 9.0 or less, preferably 8.

9 or less, and more preferably 8.8 or less.

The composition according to any one of Claims 1 to 8, wherein the composition further comprises (d) at least one surfactant.

10. The composition according to any one of Claims 1 to 7, wherein the composition is free of dicarboxylic acid, preferably α,ω-dicarboxylic acid with 5 to 10 carbon atoms, and more preferably adipic acid.

11. The composition according to any one of Claims 1 to 8, wherein the composition is intended for reshaping, in particular permanent waving, of keratin fibers, preferably the hair.

12. A reshaping process, in particular permanent waving, for keratin fibers, preferably the hair, comprising the steps of:

applying onto the keratin fibers a composition;

optionally rinsing the keratin fibers;

optionally rinsing and/or drying the keratin fibers,

wherein

the composition comprises:

(a) at least one reducing agent;

(b) at least one polyol with 4 or more carbon atoms,

wherein

13. A method for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by a reducing composition comprising at least one reducing agent in combination with an oxidizing composition comprising at least one oxidizing agent, characterized by adding at least one polyol with 4 or more carbon atoms to the reducing composition in an amount of less than 1.0% by weight relative to the total weight of the reducing composition.

14. A use of at least one polyol with 4 or more carbon atoms in a reducing composition comprising at least one reducing agent wherein the amount of the polyol in the reducing composition is less than 1.0% by weight relative to the total weight of the reducing composition, for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by the reducing composition in combination with an oxidizing composition comprising at least one oxidizing agent.