WO2014068795A1

WO2014068795A1 - Use of triazine derivatives for permanent deformation of keratin fibers

Info

Publication number: WO2014068795A1
Application number: PCT/JP2012/078772
Authority: WO
Inventors: Fumiko Chiba; Hiroshi Takahashi; Boni Maxime De
Original assignee: L'oreal
Priority date: 2012-10-31
Filing date: 2012-10-31
Publication date: 2014-05-08

Abstract

The present invention relates to a cosmetic composition for keratin fibers, comprising at least one specific triazine-based compound, and a process for permanent deformation of keratin fibers comprising the steps of applying the specific triazine-based compound onto the keratin fibers. The present invention makes it possible to perform a new permanent deformation of keratin fibers such as hair, without damages to the keratin fibers and malodor by using thiol-based compounds.

Description

DESCRIPTION

USE OF TRIAZINE DERIVATIVES FOR PERMANENT DEFORMATION OF

KERATIN FIBERS TECHNICAL FIELD

The present invention relates to a cosmetic composition for keratin fibers such as hair.

BACKGROUND ART

Many hair care products are marketed nowadays to easily style, texturize and add weight to hair, especially to tWnning hair, among which foams and styling gels or hair lacquers may be mentioned as examples. These products enable shaping of the hair but are removed with shampoo and thus are required to be applied on a daily basis.

The most general technique for obtaining a long-lasting deformation of hair consists, in a first step, of opening the keratin S-S disulfide bonds (cystine) with a composition comprising a suitable reducing agent (reducing step) then, once the thus treated hair has been rinsed, generally with water, reforming said disulfide bonds in a second step, by applying an oxidizing composition onto the hair which has been placed beforehand under tension, using curlers for example (oxidizing step, also called fixing step) so as to give the hair the desired form in the end.

The new shape that is imposed to the hair by means of a chemical treatment, such as explained above, is relatively long-lasting and is relatively resistant to washing operations with water or shampoo, as compared to the usual simple methods for temporarily reshaping the hair 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.

DISCLOSURE OF INVENTION

To achieve good hair shape modification performance, the composition for opening the cystine bonds contains a relatively high concentration of one or more reducing agents under the high alkaline condition. For example, thioglycolic acid, which is one of the common reducing agents, is in general used in an amount between 6 and 11 wt%, with a pH range of from 8.5 to 9.5.

Additionally, some hair deformation technologies use heating process during the reducing step in order to increase the chemical action of such reducing agents. Therefore, the hair undergoes substantial degradation that does not permit consumers to consider repeated applications nor treatment combinations (for example, perm and coloration).

In addition, thiol-based compounds which are commonly used as reducing agents for conventional hair deformation processes have malodor, and therefore, the malodor is not preferable either for consumers. An objective of the present invention is to provide a cosmetic composition for keratin fibers which can prevent or reduce the degradation of the keratin fibers by the deformation process based on conventional deformation processes for the keratin fibers, without any malodor. The above objective can be achieved by a cosmetic composition for keratin fibers comprising at least one compound represented by the following general formula (I) or a salt thereof:

wherein

each of Ri and R₂ independently represents a hydrogen atom, a CMO alkyl group, a C_2-10 alkenyl group, a Ce-io aryl group, or a C₇.₁₀ aralkyl group; these groups optionally being substituted by at least one group chosen from a hydroxyl group, an amino group, a carboxy group, and a C_2-10 acyl group; and

X represents a halogen atom, a trifluoromethanesulfonyloxy group, a piperidinyl group, a piperazinyl, an morpholinyl group, an N-alkylmo holinium group, or

where R₃, T and R₅ independently represent a C_1-10 alkyl group, a C₂.₁₀ alkenyl group, a C_6-1o aryl group, a C_7-10 aralkyl group, -CH₂-COO-C_mH_2m+i (m denotes an integer from 1 to 10), or

(n denotes an integer of from 1 to 10). When, in the above formula (I), X represents an N-alkylmorpholinium group, it is preferably an N-memylmorpholinium group.

In the above formula (I), both Ri and R₂ may represent a hydrogen atom. In the above formula (I), at least one or two of R₃, R4 and R5 may represent a C_1-10 alkyl group, preferably a methyl group.

The salt may be a salt with organic or inorganic acid or a salt with organic or inorganic base.

Particularly , if X represents an N-alkylmorpholinium group or

the compound (I) may be a salt with an anion selected from the group consisting of halide ions, triflates, nitrates, sulfates, sulfonates, boron fluorides, and perchloates.

The amount of the compound represented by the general formula (I) in the cosmetic composition according to the present invention may be from 0.1 to 50% by weight, preferably from 1 to 30% by weight, and more preferably 2 to 10% by weight, relative to the total weight of the

composition.

The pH of the cosmetic composition-according to the present invention may be from 2 to 11 , and preferably from 3 to 10, and more preferably from 4 to 9.

The cosmetic composition according to the present invention may further comprise at least one pH adjusting agent.

The cosmetic composition according to the present invention may further comprise at least one additional compound selected from the group consisting of amino acids, carboxylic acids, amines, fatty alcohols, aminosilicones, and polymers with amino, carboxylic and/or amido group(s).

The cosmetic composition according to the present invention may further comprise at least one cationic polymer. The cosmetic composition according to the present invention may further comprise a thiol-based compound, preferably at low concentration, such as up to 0.1% by weight relative to the total weight of the composition.

Another objective of the present invention is to provide a process for permanent deformation of keratin fibers which can prevent or reduce the degradation of the keratin fibers by the permanent deformation process for the keratin fibers, without any malodor.

The above objective can be achieved by a process for permanent deformation of keratin fibers comprising the steps of:

applying onto the keratin fibers the cosmetic composition according to the present invention; and keeping the keratin fibers under from a room temperature to an elevated temperature.

The process according to the present invention may further comprise the step of providing the keratin fibers with mechanical tension for the deformation before and/or after the step of applying onto the keratin fibers the cosmetic composition according to the present invention.

The process according to the present invention may further comprise the step of rinsing the keratin fibers after the step of applying onto the keratin fibers the cosmetic composition according to the present invention and/or after the step of keeping the keratin fibers from room temperature to an elevated temperature.

The elevated temperature may be from 50 to 250°C, preferably 80 to 200°C and more preferably 100 to 180°C. In the process according to the present invention, the keratin fibers may be heated to the elevated temperature by at least one heater selected from the group consisting of hot air, hot steam, high frequency induction heating, microwave heating, infra-red ray irradiation, ultrasonic wave, laser, and flash lamp irradiation. The process according to the present invention may not comprise a step of oxidizing the keratin fibers.

The present invention also relates to a use of a cosmetic composition comprising at least one compound represented by the following general formula (I) or one of their salts:

each of Ri and R₂ independently represents a hydrogen atom, a C_1-10 alkyl group, a C₂-₁₀ alkenyl group, a C_6-1o aryl group, and a C7-10 aralkyl group; these groups optionally being substituted by at least one group chosen from a hydroxyl group, an amino group, a carboxy group, and a C_2-10 acyl group,

and

X represents a halogen atom, a trifluoromethanesulfonyloxy group, a piperidinyl group, a piperazinyl, an morpholinyl group, an N-alkylmorpholinium group, or -N^RiRs where R₃, R4 and R₅ independently represent a C_1-10 alkyl group, a C_2-10 alkenyl group, a C₆.₁₀ aryl group, a

C_7-1o aralkyl group, -CH2-COO-C_mH_2m+1 (m denotes an integer from 1 to 10), or -C₆H₄-p-C_nH_2n+1 (n denotes an integer of from 1 to 10), for permanent deformation of keratin fibers.

BEST MODE FOR CARRYING OUT THE INVENTION

General permanent hair shape modification process gives a lot of damage to hair fibers due to insufficient recombination of disulfide-bonding linkage, as well as the hydrolysis of keratin protein and their extraction from hair under the high alkaline condition. Especially, repeated applications or in combination with other chemical treatments such as oxidative coloration give high levels of hair damage. Such hair damage leads to the insufficient long-lastingness of the hair shape modification effect against environmental stress such as mechanical constraints from daily shampoo, bmshing, humidity, UV and the like.

After diligent research, the inventors have discovered that it is possible to perform a new permanent deformation of keratin fibers such as hair, eyelash, eyebrow and the like, which reduces the damages to the keratin fibers and malodor by using thiol-based compounds.

The inventors have found that some specific triazine-based compounds can give good hair shape modification effect even at room temperature process without hair damage. The above triazine-based compounds form an amide bond (-CONR-) by the direct condensation of a carboxylic acid moiety and an amine moiety in the protein in the keratin fibers, in stead of forming -S-S- disulfide bond to deform or reshape the keratin fibers.

Thus, the cosmetic composition and the deformation process for the keratin fibers such as hair according to the present invention can prevent or reduce the degradation of the keratin fibers by the deformation process for the keratin fibers, because the present invention is based on a new principle of the permanent deformation of keratin fibers, and is no longer based on the

conventional permanent deformation based on the reduction-oxidation of disulfide bonds in the keratin fibers.

The cosmetic composition according to the present invention does not need to contain any reducing agent such as a thiol-based compound. Therefore, no oxidative step is required to achieve the hair shape modification effects. This means that no malodor derived from the reducing agent is present or generated; no additional hair degradation by the high alkaline condition for the reducing agent or by the oxidative step is caused; and one step process can be achieved by the sole use of the cosmetic composition according to the present invention.

Hereafter, each of the cosmetic composition for keratin fibers and the process for permanent deformation of keratin fibers according to the present invention will be described in a detailed manner.

[Cosmetic Composition]

(Triazine-Based Compound) The cosmetic composition for treating keratin fibers, in particular for deforming keratin fibers, comprises at least one compound represented by the following general formula (I) or a salt thereof:

wherein

each of Ri and R₂ independently represents a hydrogen atom, a C_1-10 alkyl group, a C₂.₁₀ alkenyl group, a C_6-io aryl group, or a C7_-10 aralkyl group, these groups optionally being substituted by at least one group chosen from a hydroxyl group, an amino group, a carboxy group, and a C_2-1o acyl group; and

X represents a halogen atom, a trifluoromethanesulfonyloxy group, a piperidinyl group, a piperazinyl, an morpholinyl group, an N-alkylmorpholinium group, or -Nrt^R-jRs where

C_7-1o aralkyl group, -CH₂-COO-C_mH_2m+1 (m denotes an integer from 1 to 10), or

(n denotes an integer of from 1 to 10),

The cosmetic composition according to the present inventions may comprise two or more of the compounds according to the above formula (I).

As the C_1-10 alkyl group, mention may be made of linear or branched C_1-10 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, and the like; and cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl- group,- and- the like. - A C_1-10 linear alkyl group is preferable. A methyl group and an ethyl group are more preferable. A methyl group is even more preferable. As the C2-10 alkenyl group, mention may be made of linear or branched C2-10 alkenyl groups such as a vinyl group, a 1-propenyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a pentenyl group, a hexenyl group, and the like; cycloalkenyl groups such as a cyclopentenyl group, a cyclohexenyl group and the like; cycloalkenylalkyl groups such as a cyclopentenylethyl group, a cyclohexenylethyl group, a cyclohexenylpropyl group and the like. A C_1-10 linear alkenyl group is preferable. A vinyl group and a 1-propenyl group are more preferable. A vinyl group is even more preferable.

As the C_6-1o aryl group, mention may be made of aryl groups such as a phenyl group, a tolyl group, a xylyl group, a mesityl group and the like. A phenyl group is preferable.

As the C7-10 aralkyl group, mention may be made of a benzyl group, a phenethyl group and the like Preferably, R and R2 may be hydrogen atoms.

It is preferable that X in the above formula (I) represent an N-alkylmoφholinium group, more preferably an N-methylmorpholinium group. It is preferable that at least one or two of R3, R4 and R₅ in the above formula (I) represent a C_1-10 alkyl group, more preferably a methyl group.

The acid may be chlorhydric acid, nitric acid, sulfuric acid, fluorhydric acid, bromhydric acid, perchloric acid, sulfonic acids, fluoroboric acid, citic acid, lactic acid, tartaric acid, or acetic acid. The base may be ammonia, soda, potash, or alcanolamine. Particularly , if X represents an N-alkylmorpholinium group or -N⁺R₃R₄R₅, the compound (I) may be a salt with an anion selected from the group consisting of halide ions, triflates, nitrates, sulfates, sulfonates, boron fluorides, and perchloates.

As the compound represented by the above formula (I),

4-(4,6-dimemoxy-l,3,5-triazin-2-yl)-4-memylmoφholinium (DMT-MM) halide is preferable, and DMT-MM chloride is more preferable. The amount of the compound represented by the above formula (I) in the cosmetic composition according to the present invention is not limited. For example, the amount of the compound represented by the formula (I) in the cosmetic composition according to the present invention may be from 0.1 to 50% by weight, preferably from 1 to 30% by weight, and more preferably 2 to 10% by weight, relative to the total weight of the cosmetic composition.

(PH)

The pH of the cosmetic composition according to the present invention is not limited. For example, the pH of the cosmetic composition according to the present invention may be from 2 to 11, and preferably from 3 to 10, and more preferably from 4 to 8.5. The cosmetic composition according to the present invention may further comprise at least one pH adjusting agent. Two or more different pH adjusting agents may be used.

As the pH adjusting agent, mention may be made of any number of acidic or alkali agents alone or in combination.

As the acidic agents, mention may be made of any inorganic or organic acids which are commonly used in cosmetic products such as citric acid, lactic acid, phosphoric acid or hydrochloric acid (HQ). HC1 is preferable.

As the alkali agents, mention may be made of any inorganic or organic basic agents which are commonly used in cosmetic products such as ammonia; alcanolamines such as mono-, di- and tri-emanolamine, isopropanolarnine; sodium and potassium hydroxides; urea, guanidine and their derivatives; basic amino acids such as lysine or arginine; and diamines such as those described in the structure below:

wherein R denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C₁-C₄ alkyl radical, and R₃, R4, R₅ and R5 independently denote a hydrogen atom, an alkyl radical or a Q-C₄ hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine and derivatives thereof. Arginine and monoethanolamine are preferred. The amount of the pH adjusting agent(s) is not limited, but may be from 0.1 to 10% by weight, preferably 1 to 5% by weight, relative to the total weight of the cosmetic composition.

(Additional Compounds) The cosmetic composition according to the present invention may further comprise at least one additional compound selected from the group consisting of amino acids, carboxylic acids, amines, fatty alcohols, aminosilicones, and polymers with amino, carboxylic and/or amido groups.

(a) Amino Acid

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 amino acid has at least one amine moiety and at least one carboxylic acid moiety, and may have two or more arnine and/or carboxylic acid moieties. Two or more amino acids may be used in combination. The acid function(s) may be carboxylic, sulfonic, phosphonic or phosphoric, and are preferably carboxylic.

As the amino acids that may be used according to the present invention, examples may include 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 include an amine function and an acid function at the same carbon atom.

The a-amino acids may be represented by the following formula:

R.— CH— COOH

I 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 CM alkyl group; a linear or branched C_1-4 hydroxyalkyl group; a linear or branched CM aminoalkyl group; a linear or branched (C_1-4 alkyl)thio(C_1-4)alkyl group; a linear or branched C₂-4 carboxyalkyl group; a linear or branched ureidoalkyl group, a linear or branched guanidinoalkyl group, a linear or branched irnidazoloalkyl group or a linear or branched indolylalkyl group, the alkyl portions of these last four groups including from one to four carbon atoms.

Preferably, the aromatic group is a C₆ aryl or C_7-1o aralkyl group, the aromatic nucleus optionally being substituted with one or more CM 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, arginine, lysine cysteine, asparagine, carnitine, glutarnine, glycine, histidine, isoleucine, leucine, methionine, N-phenylalaniiie, proline, serine, taurine, threonine, tryptophan, tyrosine, valine, hydroxyproline and mixtures thereof.

The amino acids that are particularly preferred in the present invention are arginine, lysine, cysteine, alanine, asparagine, glutarnine, glycine, isoleucine, leucine, methionine, N-phenylalanine,

(b) Carboxylic Acid As the carboxylic acids, aliphatic and aromatic carboxylic acid may be used. The aliphatic and aromatic carboxylic acid has at least one carboxylic acid moiety, and may have two or more carboxylic acid moieties. Two or more carboxylic acids may be used in combination. As the aliphatic carboxylic acid used in the present invention, there may be mentioned an aliphatic carboxylic acid containing a linear or branched hydrocarbon chain having preferably 1 to 24 carbon atoms, more preferably 2 to 22 carbon atoms and still more preferably 3 to 20 carbon atoms. Further still more preferred is an aliphatic carboxylic acid containing a linear or branched alkyl chain or alkenyl chain having the above-described carbon number. These aliphatic carboxylic acids may be either saturated or unsaturated and may be used singly or in combination of any two or more thereof.

Specific examples of the aliphatic carboxylic acid include aliphatic monocarboxylic acids such as formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid, dimethyloctanoic acid, butylheptylnonanoic acid, hexenoic acid, octenoic acid, decenoic acid, dodecenoic acid, tetradecenoic acid, hexadecenoic acid, octadecenoic acid, eicosenoic acid, docosenoic acid, linoleic acid and linolenic acid, and aliphatic dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, adipic acid, azelaic acid, sebacic acid,

decamethylenedicarboxylic acid, hexadecamethylenedicarboxylic acid and

octadecamethylenedicarboxylic acid.

As used herein, the term "aromatic carboxylic acid" means any compound including at least one entity chosen from benzene and naphthalene rings and at least one carboxylic acid function (COOH), in free or salified form, directly linked to the ring or linked to at least one substituent of the ring. In at least one embodiment, the acid function may be directly linked to the benzene or naphthalene ring.

Non-limiting examples of aromatic carboxylic acid salts include alkali metal (for example, sodium and potassium) and alkaline-earth metal (for example, calcium and magnesium) salts, organic amines, and ammonium salts.

Suitable aromatic carboxylic acids that may be used in the composition according to the present disclosure may be chosen, for example, from: benzoic acid, para-anisic acid, caffeic acid, chlorogenic acid, diphenolic acid, ferulic acid, hippuric acid, 3-hydroxybenzoic acid,

4-hydroxybenzoic acid, hydroxycinnamic acid, phenylthioglycolic acid, salicylic acid, acetylsalicylic acid, para-, meta-, or ortho-phthalic acid, the salified forms thereof, and mixtures thereof. In at least one embodiment, the at least one aromatic carboxylic acid may be benzoic acid, (c) Amine

As the amines, primary, secondary and tertiary organic amines may be used. The amine has at least one amino group, and may have two or more amino groups. Two or more amines may be used in combination.

The amine may have at least one linear or branched C_1-8 alkyl group bearing at least one hydroxyl group. Organic amines may be, in some embodiments, chosen from alkanolamines such as mono-, di- or trialkanolarnines, including one to three identical or different Ci.c₄ hydroxyalkyl radicals. Among the compounds of this type that may be mentioned, in a non-limiting manner, are monoethanolamine, diemanolamine, triethanolamine, monoisopropanolamine,

diisopropanolamine, N-dimemylammoemanolamine, 2-amino-2-methyl-l-propanol,

friiso-propanolamine, 2-amino-2-methyl- 1 ,3 -propanediol, 3 -amino- 1 ,2-propanediol,

3 -dimemylamino- 1 ,2-propanediol and tris(¾ydroxymemylamino)methane.

(d) Fatty alcohol

The term "fatty" here means the inclusion of a relatively large number of carbon atoms. Thus, alcohols which have 4 or more, preferably 6 or more, and more preferably 8 or more carbon atoms are encompassed within the scope of fatty alcohols. The fatty alcohols may be saturated or unsaturated. The fatty alcohol may be linear or branched. Two or fatty alcohols may be used in combination. The fatty alcohol may have the structure R-OH wherein R is chosen from saturated and unsaturated, linear and branched radicals containing from 8 to 40 carbon atoms, for example from 8 to 30 carbon atoms. In at least one embodiment, R is chosen from C₁₂-C₂₄ alkyl and C₁₂-C₂₄ alkenyl groups. R may be or may not be substituted with at least one hydroxyl group. Non-limiting examples of fatty alcohols that may be mentioned include lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, arachidonyl alcohol, erucyl alcohol, cetearyl alcohol, and mixtures thereof.

Examples of suitable fatty alcohols include, but are not limited to, cetyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, and mixtures thereof.

The fatty alcohol may be or may not be oxyalkylenated or glycerolated.

As used herein, the term "oxyalkylenated fatty alcohol" is understood to mean any pure fatty alcohol with the following structure:

in which:

R is chosen from saturated or unsaturated, linear or branched radicals including from 8 to 40 carbon atoms, for example, from 8 to 30 carbon atoms,

Z is an oxyethylene radical of formula (i) and/or an oxypropylene radical chosen from

oxypropylene radicals of formulas (ii)₁ and (ii)_2: C¾^~CH— O

C¾— CH?— CH?— O

m is the number of ethylene oxide groups and/or propylene oxide groups, and may range from 1 to 250, preferably from 2 to 100.

As used herein, the term "glycerolated fatty alcohol" is understood to mean any pure fatty alcohol with the following structure:

^R°-E-^{Z H}

in which:

R is chosen from saturated or unsaturated, linear or branched radicals including from 8 to 40 carbon atoms, preferably from 8 to 30 carbon atoms,

Z is a glycerol radical of formula (iii):

n is the number of glycerol groups, and may range from 1 to 30, preferably from 1 to 10.

In at least one embodiment of the present invention, the oxyalkylenated fatty alcohols used in accordance with the disclosure may be chosen from saturated or unsaturated, linear or branched fatty alcohols including from 10 to 20 carbon atoms and from 2 to 40 ethylene oxide groups.

Non-limiting examples of oxyalkylated fatty alcohols include the following commercial products: MERGITAL LM2 (Cognis) [lauryl alcohol 2 EO];

IFRALAN L12 (Ifrachem) and REWOPAL 12 (Goldschmidt) [lauryl alcohol 12 EO];

EMPILAN KA 2.5/90 FL (Albright & Wilson) and MERGITAL BL309 (Cognis) [decyl alcohol 3 EO];

EMPILAN KA 5/90 FL (Albright & Wilson) and MERGITAL BL589 (Cognis) [decyl alcohol 5 EO];

BRIJ 58 (Uniquema) and SIMULSOL 58 (Seppic) [cetyl alcohol 20 EO];

EMULGIN 05 (Cognis) [oleyl/cetyl alcohol 5 EO]:

MERGITAL OC30 (Cognis) [oleyl/cetyl alcohol 30 EO];

BRIJ 72 (Uniquema) [stearyl alcohol 2 EO];

BRIJ 76 (Uniquema) [stearyl alcohol 10 EO]; BRIJ 78P (Uniquema) [stearyl alcohol 20 EO];

BRJJ 700 (Uniquema) [stearyl alcohol 100 EO];

EMULGIN Bl (Cognis) [cetearyl alcohol 12 EO];

EMULGIN L (Cognis) [cetyl alcohol 9 EO and 2 PO]; and

WITCONOLAPM (Goldschmidt) [myristyl alcohol 3 PO].

Examples of glycerolated fatty alcohols include, but are not limited to, lauryl alcohol including 4 mol of glycerol (INCI name: polyglyceryl-4 lauryl ether), oleyl alcohol including 4 mol of glycerol (INCI name: polyglyceryl-4 oleyl ether), oleyl alcohol including 2 mol of glycerol (INCI name: polyglyceryl-2 oleyl ether), cetearyl alcohol including 2 mol of glycerol, cetearyl alcohol including 6 mol of glycerol, oleyl/cetyl alcohol including 6 mol of glycerol, and octadecanol including 6 mol of glycerol.

The fatty alcohol may represent a mixture of fatty alcohols, which means that several species of fatty alcohol may coexist, in the form of a mixture, in a commercial product.

Fatty alcohol mixtures that may be used in at least one embodiment include cetyl alcohol and cetearyl alcohol. In at least one embodiment, the non-oxyalkylenated fatty alcohol is solid or pasty at a temperature of 25°C. For the purposes of the present disclosure, the expression "fatty alcohol that is solid or pasty at 25°C" means a fatty alcohol that has a viscosity, measured with a rheometer at a shear rate of 1 s^'1, of greater than or equal to 1 Pas. According to at least one embodiment, the fatty alcohol used in the cosmetic composition according to the present invention is chosen from cetyl alcohol and cetearyl alcohol.

(e) Arninosilicone The arninosilicone may be selected from the group consisting of polydialkylsiloxanes, such as polydimethylsiloxanes (PDMS), polyalkylarylsiloxanes, and polydiarylsiloxanes which are organo-modified to include at least one amino functional group. The arninosilicone may have two or more amino groups. Two or more aminosilicones may be used in combination. Aminosilicones suitable for use according to the present invention include, but are not limited to, volatile and non- volatile, cyclic, linear, and branched aminosilicones having a viscosity ranging from 5xl0^"6 to 2.5 m²/s at 25°C, for example, from lxlO^"5 to 1 m²/s.

As the aminosilicones, mention may be made of products marketed under the trade name GP 4 Silicone Fluid and GP 7100 by GENESEE and products marketed under the trade names Q2 8220 and DOW CORMNG 929 and 939 by DOW CORNING. Substituted amine moieties may be chosen, for example, from amino C1 -C4 alkyl moieties. Aniinosiliconea may--have-additional

C!-C₄ alkoxy functional groups, such as those corresponding to the WACKER BELSIL ADM LOG 1 product. (f) Polymers with Amino, Carboxylic and/or Amido Group(s)

The term "polymer" here means a molecule having repeating units which preferably have a molecular weight of more than 5000, more preferably more than 10000, and even more preferably more than 50000. The polymers with amino carboxylic and/or amido group(s) have at least one amino, carboxylic or amido group. This polymer may have two or more amino, carboxylic and/or amido groups.

The polymers may be synthesized

by free-radical reactions (for example, polyacrylates, polymethacrylates, polyvinyls, etc.), by condensation reactions (for example, polyesters, polyethers, polyamides, polyurethanes, polydimethylsiloxanes, polypeptides, etc.), and by ring-opening reactions (for example, polyesters, etc.). The polymers may be of an origin chosen from natural, chemically modified and unmodified origins, such as polysaccharides (cellulose, dextran, chitosan, guar and the hydroxyalkyl, carboxymethyl, and amino derivatives thereof, and derivatives thereof including functional groups chosen from epoxy groups). The polymers may be in any type of topology chosen from linear, branched, starburst and hyperbranched (for example, dendrimers) chains, and block, random, and alternating chains.

The amino, carboxylic and/or amido group(s) may be naturally present on the polymer chain, for example, at the end of the polymer chain, or may be grafted along the main chain or the secondary chains, or on the branches of starburst or hyperbranched polymers.

As the polymers with amino, carboxylic and/or amido group(s), mention may be made of:

PAMAM dendrimer, for example, sold by Dendritech, DSM, Sigma-Aldrich (Starburst, PAMAM Dendrimer, G(2, O) from Dendritech);

PEI (polyethyleneimine), for example, sold by BASF under the name Lupasol;

polylysine, for example, sold by Chisso;

aminodextran, sold, for example, by Carbomer;

arninocellulose, for example, those described in WO 01/25283 from BASF;

PVA (polyvinyl acetal), for example, Airvol 540 from Air Products Chemical;

amino PVA, sold, for example, by Carbomer; and

Polyvinyl caprolactam, sold, for example, by BASF.

The amount of the additional compound(s) is not limited, but may be from 0.1 to 20% by weight, preferably 0.5 to 10% by weight, and more preferably 1.0 to 5% by weight, relative to the total weight of the cosmetic composition.

(Cationic Polymer)

The cosmetic composition according to the present invention may further comprise at least one cationic polymer. Two or more cationic polymers may be used. Thus, a single type of cationic polymer or a combination of different types of cationic polymer may be used.

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 including 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*10⁶ and preferably between approximately 10³ and approximately 3 * 10⁶.

Among the cationic polymers that may be mentioned more particularly are polymers of the polyamine, polyarnino 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 including at least one of the units of formula (I), (II), (III) or (IV) below:

in which:

R₃, which may be identical or different, denotes a hydrogen atom or a CH₃ radical;

A, which may be identical or different, represents 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;

Rt, R₅ and Re, 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;

Ri 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 memacryloyloxyethyltrimethylammonium chloride described, for example, in patent application EP-A-080 976 and sold under the name Bina Quat P 100 by the company Ciba Geigy;

- the copolymer of acrylamide and of memacryloyloxyethyltrimemylammonium

methosulfate sold under the name Reten by the company Hercules;

quaternized or non-quaternized vmylpyrrolidone/dialkylaminoalkyl acrylate 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);

dimemylaminoethyl memacrylate/vmylcaprolactam/vinylpyrrolidone terpolymers, such as the product sold under the name Gaffix VC 713 by the company ISP;

vinylpynrolidone/memacrylamidopropyldimemyla ine copolymers sold in particular under the name Styleze CC 10 by ISP, and quaternized vmylpyrrolidone/dimethylarriinopropyl methacrylamide copolymers such as the product sold under the name "Gafquat HS 100" by the company ISP; and

crosslinked memacryloyloxy(C₁-C₄)alkyltri(C₁-C₄)alkylarnmonium salt polymers such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolyrnerization of acrylamide with

dimemylaminoethyl methacrylate quaternized with methyl chloride, the homo- or copolyrnerization being followed by crosslinking with a compound containing olefinic unsaturation, in particular methylenebisacrylamide. A crosslinked

acrylamide/methacryloyloxyemyltrimethylammonium 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 Allied Colloids. A crosslinked

memacryloyloxyethyltrimemylammonium 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.

(2) Cationic polysaccharides

Cationic cellulose derivatives Cationic polymers include cellulose ether derivatives including quaternary ammonium groups, which are described in French patent 1 492 597, and in particular the polymers sold under the names "JR" (JR 400, JR 125, JR 30M) or "LR" (LR 400, LR 30M) by the company Union Carbide Corporation. These polymers are also defined in the CTFA dictionary as

hydroxyethylcellulose quaternary ammoniums that have reacted with an epoxide substituted with a trimemylammonium group.

They also include the copolymers of cellulose or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, described especially in patent US 4 131 576, such as hydroxyalkylcelluloses, for instance hydroxymethyl-, hydroxyethyl- or hydroxypropylcelluloses grafted especially with a memacryloylemyltrimemylammonium, memacrylamidopropyltrimethyl- ammonium 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 National Starch. b) Cationic guar gums The cationic guar gums described are more particularly in patents US 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-epoxypropyltrimethylarnmonium. Such products are sold especially under the trade names Jaguar C13S, Jaguar CI 5, Jaguar CI 7 and Jaguar CI 62 by the company Meyhall.

(3) Polymers consisting of piperazinyl units and of divalent alkylene or hydroxyalkylene 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.

(4) 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.

(5) The polyamino amide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents. Mention may be made, for example, of adipic acid/dialkylammohydroxyal¾yldialkylenetriamine polymers in which the alkyl radical contains from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl. Such polymers are described in particular in French patent 1 583 363.

Among these derivatives, mention may be made more particularly of the adipic

acicVdimemylammohydroxypropyl/diemylenetriamm polymers sold under the name

"Cartaretine F, F4 or F8" by the company Sandoz.

(6) The polymers obtained by reaction of a polyalkylene polyamine containing two primary amine groups and at least one secondary amine group with a dicarboxylic acid chosen from diglycolic acid and saturated aliphatic dicarboxylic acids having from 3 to 8 carbon atoms. The molar ratio between the polyalkylene polyamine and the dicarboxylic acid is between 0.8:1 and 1.4:1; the polyamino amide resulting therefrom is reacted with epichlorohydrin in a molar ratio of epicMorohydrin relative to the secondary amine group of the polyamino amide of between 0.5: 1 and 1.8:1. Such polymers are described in particular in US patents 3 227 615 and 2 961 347.

Polymers of this type are sold in particular under the name "Hercosett 57" by the company Hercules Inc. or alternatively under the name "PD 170" or "Delsette 101" by the company Hercules in the case of the adipic acid/epoxypropyl/diemylenetriamine copolymer. (7) Cyclopolymers of alkyldiallylamine or ofdialkyldiallylammoni

homopolymers or copolymers containing, as a main constituent of the chain, units corresponding to formula (V) or (VI):

in which:

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 Rg, 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 ¾ can denote, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidyl or morpholinyl; R₇ and Rg, independently of each other, preferably denote an alkyl group having from 1 to 4 carbon atoms; 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 cMorid^homopolvmer sold under the name "Merquat 100" by the company Calgon (and its homologues of low weight-average molecular mass) and the copolymers of diaUyldimemylarnmonium chloride and of acrylamide, sold under the name "Merquat 550". (8) The quaternary diammonium polymer containing repeating units corresponding to the formula:

R Ί. 0 R 1.2

— N+ -A,— N+- B,— (VII)

^R11 ^{X R}13 X

in which:

R₁₀, Rn, 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, Rn, R₁₂ and R₁₃, together or separately, constitute, with the nitrogen atoms to which they are attached, heterocycles optionally containing a second heteroatom other than nitrogen, or alternatively R₁₀, Rn, R₁₂ and R₁₃ represent a linear or branched Q-C₆ alkyl radical substituted with a nitrile, ester, acyl or amide group or a group -CO-0-R₁₄-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 Trench pjtente 2_320.3_30^2_27.0_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 preferable to use polymers that consist of repeating units corresponding to the following formula (V (CH₂)_p— (VIII)

in which:

R₁₀, Rn, Ri₂ and R₁₃, which may be identical or different, denote an aJlcyl 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. (9) Polyquaternary ammonium polymers consisting of units of formula (ΓΧ)

CH₃ ^X X^" CH₃

-N— (oy_p-NH-CO - D-NH - (CH₂)_p · N - (α¾)₂ - O - (CH₂)₂ (IX)

CH₃ CH₃ in which p denotes an integer ranging from 1 to 6 approximately, D may be nothing or may represent a group -(CH₂)_r-CO- in which r denotes a number equal to 4 or 7, and

X^" is an anion.

Such polymers may be prepared according to the processes described in patents US 4 157 388, 4 702 906 and 4 719 282. They are especially described in patent application EP-A-122 324.

Among these polymers, examples that may be mentioned include the products "Mirapol A 15", "Mirapol AD 1 ", "Mirapol AZ 1" and "Mirapol 175" sold by the company Miranol.

(10) Quaternary polymers of vinylpyrrolidone and of vinylimidazole, for instance the products sold under the names Luviquat FC 905, FC 550 and FC 370 by the company BASF. (11) Polyamines such as Polyquart H sold by Henkel, which is given under the reference name "Polyethylene glycol (15) tallow polyamine" in the CTFA dictionary.

(12) Other cationic polymers which can be used in the context of the invention are

polyalkyleneimines, in particular polyemyleneimines, polymers containing vinylpyridine or vmylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary

polyureylenes.

It is preferable that the cationic polymer be chosen f omJhej^o^ing_polymers:.

P0lyquaternium-5, such as the product Merquat 5 sold by Calgon;

Polyquaternium-6, such as the product Salcare SC 30 sold by Ciba and the product Merquat 100 sold by Calgon; Polyquaternium-7, such as the products Merquat S, Merquat 2200 and Merquat 550 sold by Calgon and the product Salcare SC 10 sold by Ciba;

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

Polyquaternium-11, 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-22, such as the product Merquat 280 sold by Calgon;

Polyquaternium-28, such as the product Styleze CC10 sold by ISP;

Polyquaternium-39, such as the product Merquat Plus 3330 sold by Calgon;

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 Calgon.

The amount of cationic polymer(s) in the cosmetic composition is not limited, but the amount of the cationic polymer(s) may be from 0.01 to 20% by weight, preferably from 0.05 to 10% by weight, and more preferably from 0.1 to 5% by weight relative to the total weight of the composition.

(Thiol-based compound)

The cosmetic composition according to the present invention does not need to contain any reducing agent such as a thiol-based compound. Therefore, malodor derived from the reducing agent can be prevented. Furthermore, degradation of the keratin fibers can be prevented, because no strong alkali is necessary.

The cosmetic composition according to the present invention may contain thiol-based compound. It is preferable, however, that the cosmetic composition according to the present invention comprise no thiol-based compound with malodor.

The "thiol-based compound" means a compound with at least one thiol. The thiol-based compound may be chosen from the group consisting of thioglycolic acid and derivatives thereof, in particular esters thereof such as glycerol or glycol monothioglycolate; dithioglycolic acid and derivatives thereof in particular esters thereof such as glycerol or glycol dithioglycolate; 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 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; 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, monoemanolamine, di-isopropanolamine or triemanolamine, respectively, may be mentioned.

However, the cosmetic composition according to the present invention may contain a small amount of at least one thiol-based compound, as long as the thiol-based compound does not hinder or reduce the effect of the present invention. For example, the cosmetic composition may contain 0.1% by weight or less, preferably 0.01% by weight or less, and more preferably 0.001% by weight or less, of a thiol-based compound, relative to the total weight of the cosmetic composition.

(Additives)

The cosmetic composition according to the present invention may also comprise one or more additives. The amount of the additive(s) is not limited, but may be from 0.1 to 10% by weight relative to the total weight of the cosmetic composition. The additive(s) may be selected from the group consisting of volatile or non volatile, linear or cyclic, silicones other than aminosilicones, anionic, nonionic or amphoteric polymers, peptides and derivatives thereof, protein hydrolyzates, synthetic or natural waxes, swelling agents and penetrating agents, as well as other active compounds, such as anionic, cationic, amphoteric or zwitterionic surfactants, non ionic surfactants other than oxyalkylenated fatty alcohols, agents for combating hair loss, anti-dandruff agents, associative-type or not, natural or synthetic thickeners, suspending agents, sequestering agents, opacifying agents, dyes, sunscreen agents, fillers, vitamins or provitamins, mineral, vegetable or synthetic oils, as well as fragrances, preserving agents, stabilizers, and mixtures thereof. The vehicle for the cosmetic 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 liquid alcohols, such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol, or polyols or polyol ethers, such as ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol or ethers thereof, such as propylene glycol monomethylether, butylene glycol, dipropylene glycol as well as diethylene glycol alkyl ethers, such as diethylene glycol monoethylether or monobutylether. The water may be present in a concentration of from 10 to 90% by weight relative to the total weight of the cosmetic composition. The organic solvent(s) may then be present in a concentration of from 0.1 to 20% by weight, and preferably from 1 to 10% by weight relative to the total weight of the composition.

The cosmetic composition according to the present invention may exist in any form such as a lotion, a gel, thickened or not, a foam, or a cream. (Permanent Deformation Process)

The process for permanent deformation of keratin fibers according to the present invention comprises, at least, the steps of:

applying onto the keratin fibers the cosmetic composition according to the present invention as explained above; and keeping the keratin fibers under room temperature or higher (i.e., an elevated temperature).

According to the process for permanent deformation of keratin fibers, such as hair, of the present invention, the keratin fibers may be subjected to mechanical tension which is typically used for permanent deformation.

The permanent deformation process for keratin fibers according to the present invention when mechanical tension is applied to keratin fibers may be performed as follows. First, keratin fibers are subjected to mechanical tension for deformation. 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 or mechanically tensioning means selected from the group consisting of a curler, a roller, a clip, a plate and an iron. 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.

Next, the cosmetic composition according to the present invention is applied to the keratin fibers. The application of the cosmetic composition according to the present invention may be performed by any means, such as a brush and a comb. It is preferable that the keratin fibers, to which the mechanical tension has been applied, be treated with the cosmetic composition according to the present invention. Lastly, the keratin fibers are maintained at room temperature or higher. If the keratin fibers are maintained at an elevated temperature, the keratin fibers are heated by applying heat energy to the keratin fibers.

Room temperature here means from 20 to 30 °C, and is typically 25 °C. The elevated

temperature is not limited as long as it is higher than room temperature. In one embodiment, the elevated temperature can be from 50 to 250°C, preferably 80 to 200°C and more preferably 100 to 180°C.

The time for heating the keratin fibers to be maintained at an elevated temperature is not limited, but preferably be from 1 second to 2 hours, and more preferably 1 minute to 1 hour.

The means to heat the keratin fibers to maintain them at an elevated temperature is not limited. One or more heating means may be used. The heating means or heater may be selected from the group consisting of hot air, hot steam, high frequency induction heating, microwave heating, infra-red ray irradiation, ultrasonic wave, laser, and flash lamp irradiation.

The reshaping or mechanically tensioning means may comprise at least one heater.-

If necessary, the cosmetic composition according to the present invention may be applied to the keratin fibers before applying mechanical tension to the keratin fibers. It is possible that the keratin fibers be left as they are for a certain amount of time, if necessary, before and/or after applying mechanical tension to the keratin fibers, before and/or after applying the cosmetic composition according to the present invention to the keratin fibers, and before and/or after mamtaining the keratin fibers under from a room temperature to a higher temperature (an elevated temperature).

The permanent deformation process for keratin fibers according to the present invention may further comprise the step of rinsing the keratin fibers after the step of applying onto the keratin fibers the cosmetic composition according to the present invention and/or after the step of keeping the keratin fibers under from at room temperature to an elevated temperature.

According to the process for deforming the keratin fibers according to the present invention, at least one amide bond is formed by the direct condensation of carboxylic acid moieties and amine moieties of the proteins in the keratin fibers. Here, the term "direct condensation" means that the compound according to the above formula (Γ) is not present in the final product with formed amide bond. Thus, the compound according to the above formula (I) acts as a catalyst.

Moreover, the shape of the keratin fibers can be deformed by the formation of the amide bond, not disulfide bond based on conventional permanent deformation technologies based on reduction and oxidation.

The process according to the present invention does not have to include a step of oxidizing the keratin fibers, because it does not reduce the disulfide bonds in the keratin fibers. Preferably, the process according to the present invention comprises no step of oxidizing the keratin fibers.

Therefore, the process according to the present invention can also prevent or reduce the degradation of the keratin fibers due to the oxidation process, typically the oxidation by an oxidizer such as hydrogen peroxide. Furthermore, the time required for the process according to the present invention can be shorter than that for a conventional process which needs an oxidizing step.

The whole time required for the process according to the present invention may be a few minutes to 2 hours, preferably 5 minutes to 1 hour, and more preferably 10 to 30 rninutes. One embodiment of the process for permanent deformation of keratin fibers such as hair according to the present invention may be a process for reshaping or permanently deforming keratin fibers, in particular hair, comprising:

a) a step of placing the keratin fibers under mechanical tension by rolling them up on at least one reshaping or mechanically tensioning means so as to form curls of the keratin fibers; b) a step of applying the cosmetic composition according to the present invention to the

keratin fibers;

c) an optional step of rinsing the keratin fibers,

d) ^" a step of heating the keratin fibers at a temperature of from a room temperature to an

elevated temperature such as a temperature between 50 and 250°C, and

e) an optional step of rinsing the keratin fibers. Another embodiment of the process for permanent deformation of keratin fibers such as hair according to the present invention may be a process for reshaping or permanently deforming keratin fibers, in particular hair, comprising:

a) a step of applying the cosmetic composition according to the present invention to the

keratin fibers;

b) an optional step of rinsing the keratin fibers,

c) a step of placing the keratin fibers under mechanical tension by rolling them up on at least one reshaping or mechanically tensioning means so as to form curls of the keratin fibers, or by pressing them by at least one reshaping or mechanically tensioning means to as to straighten the keratin fibers, followed by or while heating the keratin fibers at a temperature of from a room temperature to an elevated temperature such as a temperature between 50 and 250°C, and

d) an optional step of rinsing the keratin fibers.

According to the present invention, it is preferable that the temperature of the keratin fibers be kept constant with a fluctuation of ± 2 or 3°C over the head, if the keratin fibers are hair, of an individual. Thus, the hair style becomes uniform and homogeneous over the entirety of the hair, and a more excellent hair style can be obtained.

EXAMPLES

The present invention will be described in more detail by way of examples, which, however, should not be construed as limiting the scope of the present invention.

Examples 1 to 6 and Comparative Examples 2 to 6

[Preparations] The following compositions according to Examples 1 to 6 and Comparative Examples 2 to 6, shown in Table 1 , were prepared by mixing the components shown in Table 1. The numerical values for the amounts of the components shown in the Tables are all based on "% by weight" as active raw materials.

Behenyl ErimelhylamtBoniom chloride**: ?0wt% solution in dipropyleneglycol

[Evaluation 1]

Example 1 2 g of the composition according to Ex. 1 in Table 1 was applied at room temperature on a 1 g sample of Japanese hair swatch previously wrapped on a 1.7 cm perm-roller, and left for 30 minutes at room temperature. Then, the hair was removed from the perm-roller, rinsed with tap water, and dried at room temperature. The treated hair was curled, and presented body. These properties were maintained even after shampooing the treated hair 5 times.

Comparative Example 2 The permanent waving process according to Example 1 was repeated except that the composition according to Comp. Ex. 2 in Table 1 was used instead of the composition according to Ex. 1 in Table 1.

The treated hair was not curled. The treated hair was soft and smooth, but these properties disappeared after shampooing the treated hair only 1 time.

Example 2

The permanent waving process according to Example 1 was repeated except that the composition according to Ex. 2 in Table 1 was used instead of the composition according to Ex. 1 in Table 1.

The treated hair was curled. Furthermore, the treated hair was softer and smoother than the treated hair according to Comparative Example 2. These properties were maintained even after shampooing the treated hair 5 times.

Comparative Example 3

The permanent waving process according to Example 1 was repeated except that the composition according to Comp. Ex. 3 in Table 1 was used instead of the composition according to Ex. 1 in Table 1.

The treated hair was not curled. The treated hair presented body, but this property disappeared after shampooing the treated hair only 1 time. Example 3

The permanent waving process according to Example 1 was repeated except that the composition according to Ex. 3 in Table 1 was used instead of the composition according to Ex. 1 in Table 1. The treated hair was curled, and presented body. These properties were maintained even after shampooing the treated hair 5 times.

Comparative Example 4 The permanent waving process according to Example 1 was repeated except that the composition according to Comp. Ex. 4 in Table 1 was used instead of the composition according to Ex. 1 in Table 1.

Example 4

The permanent waving process according to Example 1 was repeated except that the composition according to Ex. 4 in Table 1 was used instead of the composition according to Ex. 1 in Table 1.

The treated hair was curled. Furthermore, the treated hair was softer and smoother than the treated hair according to Comparative Example 4. These properties were maintained even after shampooing the treated hair 5 times.

Comparative Example 5

The permanent waving process according to Example 1 was repeated except that the composition according to Comp. Ex. 5 in Table 1 was used instead of the composition according to Ex. 1 in Table 1.

The treated hair was not curled. The treated hair was soft and smooth, but these properties disappeared after shampooing the treated hair only 1 time. Example 5

The permanent waving process according to Example 1 was repeated except that the composition according to Ex. 5 in Table 1 was used instead of the composition according to Ex. 1 in Table 1. The treated hair was curled. Furthermore, the treated hair was softer and smoother than the treated hair according to Comparative Example 5. These properties were maintained even after shampooing the treated hair 5 times.

Comparative Example 6

The permanent waving process according to Example 1 was repeated except that the composition according to Comp. Ex. 6 in Table 1 was used instead of the composition according to Ex, l- in Table 1. The treated hair curled. The treated hair was soft and smooth. However, these properties disappeared after shampooing the treated hair only 1 time.

Example 6 The permanent waving process according to Example 1 was repeated except that the composition according to Ex. 6 in Table 1 was used instead of the composition according to Ex. 1 in Table 1.

The treated hair was very curled. Furthermore, the treated hair was soft and smooth. These properties were maintained even after shampooing the treated hair 5 times.

[Evaluation 2]

Comparative Example 5 2 g of the composition accordmg to Comp. Ex 5 in Table 1 was applied at room temperature on a 1 g sample of Japanese hair swatch (curly hair), and left for 30 minutes at room temperature. Then, the hair was straightened by a hair iron at 180 °C for 3 seconds. The treated hair was rinsed with tap water, and dried at room temperature. The treated hair presented body and good straightening. However, these properties disappeared after shampooing the treated hair only 1 time.

Example 5 2 g of the composition according to Ex 5 in Table 1 was applied at room temperature on a 1 g sample of Japanese hair swatch (curly hair), and left for 30 minutes at room temperature. Then, the hair was straightened by a hair iron at 180 °C for 3 seconds. The treated hair was rinsed with tap water, and dried at room temperature. The treated hair presented body and good straightening. These properties were maintained even after shampooing the treated hair 5 times.

[Evaluation 3] The odor from the hair swatches treated with the compositions according to Examples 1 to 6 and Comparative Examples 2 to 6 was checked by panelists.

The results of the above Evaluations 1 to 3 are shown in Table 2.

Claims

A cosmetic composition for treating keratin fibers, comprising at least one compound represented by the following general formula (I) or a salt thereof:

wherein

each of Ri and R₂ independently represents a hydrogen atom, a CMO alkyl group, a C2_-10 alkenyl group, a C_6-10 aryl group, or a C_7-10 aralkyl group; these groups optionally being substituted by at least one group chosen from a hydroxyl group, an amino group, a carboxy group, and a C_2-10 acyl group,

and

X represents a halogen atom, a trifluoromethanesulfonyloxy group, a piperidinyl group, a piperazinyl, an morpholinyl group, an N-alkylmorpholinium group, or

where R₃, R4 and R₅ independently represent a C_1-10 alkyl group, a C_2-1o alkenyl group, a C_6-10 aryl group, a C_7-1o aralkyl group, -CH₂-COO-C_mH_2m+1 (m denotes an integer from 1 to 10), or

(n denotes an integer of from 1 to 10).

The cosmetic composition according to Claim 1, wherein X represents an

N-alkylmoφholinium group, preferably an N-methylmorpholinium group.

The cosmetic composition according to Claim 1 or 2, wherein Ki and R₂ represent a hydrogen atom.

The cosmetic composition according to Claim 1 to 3, wherein at least one or two of R₃, R4 and R₅ represents) a C_1-10 alkyl group, preferably a methyl group.

The cosmetic composition according to any one of Claims 1 to 4, wherein the amount of the compound represented by the general formula (I) in the cosmetic composition is from 0.1 to 50% by weight, preferably from 1 to 30% by weight, and more preferably 2 to 10% by weight, relative to the total weight of the composition.

The cosmetic composition according to any one of Claims 1 to 5, wherein the pH of the cosmetic composition is from 2 to 11 , and preferably from 3 to 10, and more preferably from 4 to 8.5.

The cosmetic composition according to any one of Claims 1 to 6, further comprising at least one pH adjusting agent.

The cosmetic composition according to any one of Claims 1 to 7, further comprising at least one additional compound selected from the group consisting of amino acids, carboxylic acids, amines, fatty alcohols, aminosilicones, and polymers with amino, carboxylic and/or amido group(s).

9. The cosmetic composition according to any one of Claims 1 to 8, further comprising at least one cationic polymer

10. The cosmetic composition according to any one of Claims 1 to 9, further comprising up to 0.1% by weight of a thiol-based compound, relative to the total weight of the composition.

11. A process for permanent deformation of keratin fibers comprising the steps of:

applying onto the keratin fibers the cosmetic composition according to any one of Claims 1 to 10; and

keeping the keratin fibers under from a room temperature to an elevated temperature.

12. The process according to Claim 11 , further comprising the step of providing the keratin fibers with mechanical tension for the deformation before and/or after the step of applying onto the keratin fibers the cosmetic composition according to any one of Claims 1 to 10.

13. The process according to Claim 11 or 12, further comprising the step of rinsing the keratin fibers after the step of applying onto the keratin fibers the cosmetic composition according to any one of Claims 1 to 10 and/or after the step of keeping the keratin fibers under from room temperature to an elevated temperature.

14. The process according to any one of Claims 11 to 13, wherein the elevated temperature is from 50 to 250°C, preferably 80 to 200°C and more preferably 100 to 180°C.

15. The process according to any one of Claims 11 to 14, wherein the keratin fibers are heated to the elevated temperature by at least one heater selected from the group consisting of hot air, hot steam, high frequency induction heating, microwave heating, infra-red ray irradiation, ultrasonic wave, laser, and flash lamp irradiation.

16. The process according to any one of Claims 11 to 15, wherein a step of oxidizing the

keratin fibers is not included.

17. Use of a cosmetic composition comprising at least one compound represented by the

following general formula (I) or one of their salts:

wherein

each of Ri and R₂ independently represents a hydrogen atom,-a-C_M0 alkyl-group, a C₂.₁₀ alkenyl group, a C_6-1o aryl group, and a C_7-10 aralkyl group; these groups optionally being substituted by at least one group chosen from a hydroxyl group, an amino group, a carboxy group, and a C_2-io acyl group, and

where ₃, R4 and R5 independently represent a CMO alkyl group, a C2-10 alkenyl group, a C6-₁₀ aryl group, a C7-10 aralkyl group, -CH₂-COO-C_raH2ni+i (m denotes an integer from 1 to 10), or

- Ri-p-Cni i (n denotes an integer of from l to 10), for permanent deformation of keratin fibers