WO2015021516A1

WO2015021516A1 - Method for the treatment of hair from a composition comprising an organic mono acid and an aminosilicone

Info

Publication number: WO2015021516A1
Application number: PCT/BR2013/000304
Authority: WO
Inventors: Camila BIATO
Original assignee: L'oreal
Priority date: 2013-08-13
Filing date: 2013-08-13
Publication date: 2015-02-19
Also published as: BR112016002831A2

Abstract

The object of the present invention is a method for the treatment of hair, comprising the application to the hair of a composition comprising at least one organic monoacid and at least one aminosilicone, and a step of heating the hair at a temperature higher than 100°C. The method according to the invention makes it possible to obtain a solution for treatment of the hair in a way which is lasting and compatible with any type of past or future hair treatment and provides a volume reduction.

Description

"METHOD FOR THE TREATMENT OF HAIR FROM A COMPOSITION COMPRISING AN ORGANIC MONO ACID AND AN AMINOSILICONE"

The present invention relates to a process for treating hair with a composition comprising an organic mono acid and an aminosilicone.

In the hair field, consumers wish to have available compositions which make it possible to introduce a temporary change to their hair and to do this while targeting a good wear property for the effect produced. In general, it is desirable for the change to withstand shampooing operations for a minimum of 15 days, indeed even more, depending on the nature of the said change.

Treatments already exist for modifying the colour or the shape of the hair and also, to some extent, the texture of the hair. One of the known treatments for modifying the texture of the hair consists of the combination of heat and of a formaldehyde-comprising composition. This treatment is especially effective in conferring a better appearance on damaged hair and/or in treating long hair and curly hair.

The heat use can be that of the iron (flat tongs or crimping iron), the temperature of which can generally reach 200°C or more.

However, there is an increasing desire to avoid the use of such substances, which can prove to be aggressive to the hair and other keratinous substances.

Application WO2011/104282 has thus provided a novel method for semi-permanently smoothing the hair which consists in applying an a-aceto acid solution to the hair for from 15 to 120 minutes, in then drying and, finally, in smoothing the hair with an iron at a temperature of approximately 200°C. The a-aceto acid employed is preferably glyoxylic acid.

However, it has been found that glyoxylic acid may not always be well tolerated, in particular when the scalp is sensitive and/or irritated. Its volatility combined with a hot process may cause problems. Furthermore, cosmetic formulations of prior art can detrimentally affect the hair and/or detrimentally affect the colour thereof. In point of fact, the desired treatment is very particularly intended to repair artificially dyed hair. It is therefore preferable to avoid the use of active agents capable of introducing a reinforcing effect but while contributing to detrimentally affecting the hair and/or its artificial colour.

The object of the invention is to develop a method for changing the aspect of the hair, such as smoothing and/or straightening hair without detrimental effect on the integrity and/or color of the hair fibres. Another object of the invention is to develop a method for changing the aspect of the hair and resistant to water.

Thus, a subject-matter of the present invention is a method for the treatment of hair, comprising the application to the hair of a composition comprising at least one organic monoacid and at least one aminosilicone, and a step of heating the hair at a temperature higher than 100°C.

It has been found that the method according to the invention makes it possible to obtain a solution for treatment of the hair in a way which is lasting and compatible with any type of past or future hair treatment.

In particular, the method according to the invention will not detrimentally affect the integrity of the fibre. In addition, it will improve qualities of use and the mechanical properties of the hair, such as the resistance to moisture, and the sheen, and will reduce volume and frizz. It will also reduce colour modification of hair.

In that which follows, the expression "at least one" is equivalent to the expression "one or more".

The method of the present invention is carried out with a composition comprising at least one organic mono acid. According to the present invention, a mono acid is an organic compound comprising a unique acid group. According to one embodiment, the monoacid is chosen from compounds of formula (I), their stereoisomers, their organic or mineral salts or their corresponding solvates:

O

I I

R OH

(I)

wherein X represents a carbon atom (carboxylic acids), a group P-OH (phosphonic acids ), a group P-H (phosphinic acids) or a group S=0 (sulfonic acids), et R represents an alkyle, alcenyle , aryle or aralkyle group with a linear, branched or cyclic alkyle group comprising from 1 to 20 carbon atoms, a linear, branched or cyclic alcenyle group comprising from 2 to 20 carbon atoms, an aryle ou aralkyle group comprising from 6 to 20 carbon atoms, these groups being eventually substituted by one or more groups selected from halogen atoms and from the groups hydroxyl, trifluoromethyl, alcoxy C1-C4.

Among the monoacid of formula (I), mention can be made of glycolic acid (also called hydroxyacetic acid), lactic acid, 1-hydroxy-1- cyclopropanecarboxylic acid, 2-hydroxy-3-butenoic acid, 2-hydroxyisobutyric acid, 2-hydroxy-n-butyric acid, glyceric acid, 2-hydroxy-3-methylbutyric acid, 2- hydroxy-2-methylbutyric acid, 2-hydroxyvaleric acid, 1- hydroxycyclohexanecarboxylic acid, mandelic acid, 2-hydroxy-3-methylvaleric acid, 2-trifluoromethyl-2-hydroxypropionic acid, hexahydromandelic acid, 2- hydroxyoctanoic acid, 3-phenylactic acid, 3-hydroxymandelic acid, 4- hydroxymandelic acid, 2-hydroxynonanoic acid, 3-methoxymandelic acid, 4- methoxymandelic acid, 3-(4-hydroxyphenyl)lactic acid, D-chlorolactic acid, 1- cyclopentanol-1 -carboxylic acid, 1 ,2-dihydroxycyclobutanecarboxylic acid, 2- ethyl-2-hydroxybutyric acid, D-hydroxyisocaproic acid, D-hydroxycaproic acid, 2-hydroxy-3,3-dimethylbutyric acid, gluconic acid, salicylic acid, 2- hydroxyhexanoic, 3-hydroxyhexanoic, 4-hydroxyhexanoic, 5-hydroxyhexanoic, 6-hydroxyhexanoic, hydroxypropyl sulfonic acid,, methane sulfonic acid, methane phosphonic acid, methyl phosphinic acid and the stereoisomers, organic or mineral salts and solvates thereof.

Particularly preferred monoacid of formula (I) are selected from : glycolic acid, lactic acid, glyceric acid, gluconic acid, salicylic acid, 2- hydroxyisobutyric acid , 3-hydroxybutyric acid , 4-hydroxybutyric acid , 2- hydroxy-n-butyric acid , 2-hydroxyhexanoic acid, 3-hydroxyhexanoic acid, 4- hydroxyhexanoic acid, 5-hydroxyhexanoic acid, 6-hydroxyhexanoic acid, 2- hydroxypentanoic acid, 3-hydroxypentanoic acid, 4-hydroxypentanoic acid, hydroxypropylsulfonic acid , their stereoisomers, their organic or mineral salts or their corresponding solvates.

In a preferred embodiment, the monoacid is a monocarboxylic acid.

In this embodiment monocarboxylic acids are preferably substituted on R radical by at least one hydroxyle group. According to this preference R radical is particularly an alkyle, alcenyle , aryle or aralkyle group with a linear, branched or cyclic alkyle group comprising from 1 to 20 carbon atoms, a linear, branched or cyclic alcenyle group comprising from 2 to 20 carbon atoms, an aryle or aralkyle group comprising from 6 to 20 carbon atoms, these groups being substituted by at least one hydroxyle group being preferably located in position alpha or beta from the carboy group and these groups being eventually substituted by one or more other groups selected from halogen atoms and from the groups trifluoromethyl, alcoxy C1-C4.

According to this preferred embodiment, monoacids of formula (I) are selected from glycolic acid, lactic acid, glyceric acid, gluconic acid, salicylic acid, 2-hydroxyisobutyric acid, 2-hydroxy-n-butyric acid, 2-hydroxyhexanoic acid, 2-hydroxypentanoic acid their stereoisomers, their organic or mineral salts or their corresponding solvates. More preferably monoacids of formula (I) are selected from glycolic acid , lactic acid, glyceric acid, gluconic acid, salicylic acid, their stereoisomers, their organic or mineral salts or their corresponding solvates.

According to a specific embodiment, the method of the invention is carried out with a composition comprising at least glycolic acid with preferably at least one additional monocarboxylic acid of formula (I). Preferably, the composition contains glycolic acid and salicylic acid.

The amount of monoacids, their stereoisomers, their organic or mineral salts or their corresponding solvates in the composition useful in the method of the present invention varies largely. However, monoacids, their stereoisomers, their organic or mineral salts or their corresponding solvates are preferably present in the composition at a concentration ranging from 0.01 % to 50% by weight, in particular from 0.1 % to 20% by weight and preferably from 1 % to 5% by weight, with respect to the total weight of the composition.

The composition useful in the method of the invention contains an aminosilicone

"Aminosilicone" means any polysiloxane having at least one primary, secondary, tertiary amine function or a quaternary ammonium group. Preferably, the aminosilicones useful in the present invention are selected from:

(a) the compounds corresponding to the following formula (II):

(R¹)a(T)₃-a-Si[OSi(T)₂]_n-[OSi(T)_b(R¹)_2-b]_m-OSi(T)_3-a-(R¹)_a (II) wherein:

T is a hydrogen atom, or a phenyl, hydroxyl (-OH), or C C₈ alkyl radical, and preferably methyl or C-i-Cs alkoxy, preferably methoxy,

a denotes the number 0 or an integer from 1 to 3, and preferably 0,

b denotes 0 or 1 , and in particular 1 ,

m and n are numbers such that the sum (n + m) can vary notably from 1 to 2000 and in particular from 50 to 150, with n denoting a number from 0 to 1999 and notably from 49 to 149 and m denoting a number from 1 to 2000, and notably from 1 to 10;

R¹ is a monovalent radical of formula -C_qH_2qL in which q is a number from 2 to 8 and L is an amino group optionally quaternized selected from the groups:

-N(R²)-CH₂-CH₂-N(R²)₂;

-N(R²)₂; -N⁺(R²)₃ Q-;

-N⁺(R²) (H)₂ Q-;

-N⁺(R²)₂HQ-;

-N(R²)-CH₂-CH₂-N⁺(R²)(H)₂ Q^",

in which R² denotes a hydrogen atom, a phenyl, a benzyl, or a saturated monovalent hydrocarbon radical, for example a Ci-C₂o alkyl radical, and Q^" represents a halide ion such as for example fluoride, chloride, bromide or iodide.

In particular, the aminosilicones corresponding to the definition of formula (II) are selected from the compounds having the following formula (lla):

in which R, R', R", which may be identical or different, denote a Ci-C alkyl radical, preferably CH₃; a C-i-C₄ alkoxy radical, preferably methoxy; or OH; A represents a linear or branched, C3-C_6> preferably C₃-C₆, alkylene radical; m and n are integers that depend on the molecular weight and whose sum is preferably between 1 and 2000.

According to a first embodiment, R, R', R", which may be identical or different, represent a Ci-C₄ alkyl radical or hydroxyl radical, A represents a C₃ alkylene radical, and m and n are such that the weight-average molecular weight of the compound is between about 5000 and 500 000. Compounds of this type are called "amodimethicone" in the CTFA dictionary. According to a second embodiment, R, R', R", which may be identical or different, represent a Ci-C₄ alkoxy radical or hydroxyl radical, at least one of the radicals R or R" is an alkoxy radical and A represents a C₃-C₄ alkylene radical. The hydroxy/alkoxy molar ratio is preferably between 0.2/1 and 0.4/1 and advantageously equal to 0.3/1. Moreover, m and n are such that the weight-average molecular weight of the compound is between 2000 and 10⁶. More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000.

In this category of compounds, we may mention, among others, the product Belsil®ADM 652, marketed by Wacker.

According to a third embodiment, R, R", which are different, represent a Ci-C₄ alkoxy radical or hydroxyl radical, at least one of the radicals R, R" is an alkoxy radical, R' represents a methyl radical and A represents a C₃- C₄ alkylene radical. The hydroxy/alkoxy molar ratio is preferably between 1/0.8 and 1/1.1 , and advantageously is equal to 1/0.95. Moreover, m and n are such that the weight-average molecular weight of the compound is between 2000 and 200000. More particularly, n is between 0 and 999 and m is between 1 and 1000, the sum of n and m being between 1 and 1000.

More particularly, we may mention the product FluidWR® 1300, marketed by Wacker.

According to a fourth embodiment, R, R" represent a hydroxyl radical, R' represents a methyl radical and A is a C₄-C₈, preferably C₃-C₄ alkylene radical. Moreover, m and n are such that the weight-average molecular weight of the compound is between 2000 and 10⁶. More particularly, n is between 0 and 1999 and m is between 1 and 2000, the sum of n and m being between 1 and 2000.

A product of this type is notably marketed under the name DC28299 by Dow Corning. The molecular weight of these silicones is determined by gel permeation chromatography (room temperature, polystyrene standard; columns μ styragem; eluent THF; flow of 1 mm/m; inject 200 μΙ of a 0.5 wt.% solution of silicone in THF and use detection by refractometry and with a UV- meter).

An aminosilicone corresponding to the definition of formula (II) can also be polymer called "tnmethylsilylamodimethicone" in the CTFA dictionary (7th edition 1997), and having the following formula (lib):

wherein n and m have the meanings given above according to formula (II) or (lla).

Such compounds are described for example in EP0095238; a compound of formula (lib) is for example sold under the name Q2-8220 by the company OSI.

(b) Aminosilicones having the following formula (III):

wherein:

R³ represents a monovalent C-i-C-ia hydrocarbon radical, and preferably a Cr

C ₈ alkyl radical or C2-C18 alkenyl radical, for example methyl ;

R⁴ represents a divalent hydrocarbon radical, notably a C^ds alkylene radical or a divalent C1-C18, for example C-i-Cs, alkyleneoxy radical;

Q^" is a halide ion, for example chloride;

r represents an average random value from 2 to 20 and in particular from 2 to 8; s represents an average random value from 20 to 200 and in particular from 20 to 50.

Such compounds are described more particularly in patent US

4185087.

A compound included in this class is that sold by the company Union Carbide under the name "Ucar Silicone ALE 56".

(c) Quaternary ammonium silicones of formula (IV):

2X

R₇ OH R₇ R₇ i ; I I 1

R₈ - N - CH₂-CH-CH₂- R₆ ^■Si - O - - Si— R₆ - CH₂ - CHOH - CH₂ - N 1- R₈

i

R₇ R₇ R₇

r (XII)

wherein :

R₇, which may be identical or different, represent a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, and in particular a Ci-Ci₈ alkyl radical, a C₂-Ci₈ alkenyl radical or a ring comprising 5 or 6 carbon atoms, for example methyl;

F*6 represents a divalent hydrocarbon radical, notably a C Cis alkylene radical or a divalent CrCis, for example Ci-C₈, alkyleneoxy radical joined to the Si by an SiC bond;

Re, which may be identical or different, represent a hydrogen atom, a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, and in particular a Ci-C₁₈ alkyl radical, a C₂-Ci₈ alkenyl radical, a radical -R₆-NHCOR₇; X^" is an anion such as a halide ion, for example chloride or a salt of an organic acid (acetate etc.);

r represents an average random value from 2 to 200 and in particular from 5 to 100.

These silicones are for example described in application EP-A-0530974.

As a compound of formula (IV), mention may be made of the product referred to in the CTFA dictionary (1997 Edition) under the name Quaternium 80 such as that offered by the company EVONIK GOLDSCHMIDT under the names ABIL QUAT 3272 or 3474.

d) Aminosilicones of the following formula (V) :

wherein :

- Ri , R2, R3 and R₄, which may be identical or different, denote a C C₄ alkyl radical or a phenyl group,

- R₅ denotes a C C₄ alkyl radical or a hydroxyl group,

- n is an integer in the range from 1 to 5,

- m is an integer in the range from 1 to 5,

and in which x is selected in such a way that the amine index is between 0.01 and 1 meq/g.

Aminosilicones useful in the present invention are preferably aminosilicones of formula (II), (lla) or (lib).

Aminosilicones are present in the composition useful for the invention in an amount that can largely vary. According to one embodiment, the aminosilicone(s) are present in an amount of at least 0.01 wt.% by weight , preferably in an amount in the range from 0.1 to 20 wt.%, more particularly in an amount in the range from 0.1 to 10 wt.%, relative to the total weight of the composition.

The composition used in the method of the invention preferably does not contain a colouring agent or reducing agent.

The term "colouring agents" is understood to mean, according to the present invention, agents for colouring keratinous fibres, such as direct dyes, pigments or oxidation dye precursors (bases and couplers). If they are present, their content does not exceed 0.001% by weight, with respect to the total weight of the composition. This is because, at such content, only the composition would be dyed, that is to say that an effect of dyeing the keratinous fibres would not be observed.

It should be remembered that oxidation dye precursors, oxidation bases and couplers are colourless or only slightly coloured compounds which, by a condensation reaction in the presence of an oxidizing agent, give a coloured entity. With regard to direct dyes, these compounds are coloured and exhibit a degree of affinity for the keratinous fibres.

The term "reducing agent" is understood to mean, according to the present invention, an agent capable of reducing the disulfide bonds of the hair, such as the compounds chosen from thiols, alkali metal sulfites, hydrides or phosphines.

The compositions used according to the invention can be provided in any formulation form conventionally used and in particular in the form of an aqueous, alcoholic or aqueous/alcoholic solution or suspension or oily solution or suspension; of a solution or a dispersion of the lotion or serum type; of an emulsion, in particular having a liquid or semi-liquid consistency, of the O/W, W/O or multiple type; of a suspension or emulsion having a soft consistency of (O/W) or (W/O) cream type; of an aqueous or anhydrous gel, or of any other cosmetic form.

The composition can comprise one or more organic solvents, for example water-soluble solvents such as C1-C7 alcohols; mention may be made of aliphatic C1-C7 monoalcohols, aromatic C6-C7 monoalcohols, C3-C7 polyols or C3-C7 polyol ethers, which can be employed alone or as a mixture with water.

The compositions of the invention can be aqueous or anhydrous. Advantageously, the composition comprises from 20 to 95% of water based on the total weight of the composition. More preferably the composition is a hydro alcoholic composition.

The composition used in the method of the invention can additionally comprise at least one additional ingredient for example chosen from oils; solid fatty substances such as fatty alcohol, fatty ester ; non-ionic surfactants, surfactants ; sunscreens ; moisturizing agents; antidandruff agents; antioxidants; chelating agents; pearlescent and opacifying agents; plasticizing or coalescing agents; fillers; silicones other than aminosilicones; thickeners and particularly polymeric thickeners ; gelling agents ; emulsifiers ; conditioning or styling polymers; fragrances; basifying or acidifying agents; silanes; or crosslinking agents.

Depending on their nature and the purpose of the composition, the additional ingredients can be present in an amount which can be easily determined by a person skilled in the art.

In the method of the invention, the composition exhibits preferably an acidic pH, more preferably less than 4. In a preferred embodiment the pH can vary from 1 to 3, preferably from 1 ,5 to 3, better from 1 ,7 to 3.

pH can be adjusted with acidic agents other than organic monoacids of the invention such as mineral acids as chlorhydric acid or phosphoric acid, or with basic agents such as mineral basic agents as ammonia, carbonates, bicarbonates, hydroxides or organic basic agents such as alkanolamines.

The composition useful in the method of the invention can contain a cellulose polymer.

The cellulose polymers may be anionic, cationic, amphoteric or non-ionic polymers.

The term "cellulose" polymer means, according to the invention, any polysaccharide compound having in its structure sequences of glucose residues linked together via β-1 ,4 linkages; in addition to unsubstituted celluloses, the cellulose derivatives may be anionic, cationic, amphoteric or non-ionic. Thus, the cellulose polymers of the invention can be chosen from unsubstituted celluloses, including in a microcrystalline form, and cellulose ethers. Among these cellulose polymers, cellulose ethers, cellulose esters and cellulose ester ethers are distinguished. Among the cellulose esters are inorganic esters of cellulose (cellulose nitrates, sulfates, phosphates, etc.), organic cellulose esters (cellulose monoacetates, triacetates, amidopropionates, acetatebutyrates, acetatepropionates and acetatetrimellitates, etc.), and mixed organic/inorganic esters of cellulose, such as cellulose acetatebutyrate sulfates and cellulose acetatepropionate sulfates. Among the cellulose ester ethers, mention may be made of hydroxypropylmethylcellulose phthalates and ethylcellulose sulfates.

According to one particular embodiment of the invention, the cellulose polymer(s) are associative or non-associative.

The "non-associative" cellulose polymers of the invention are cellulose polymers which do not comprise a fatty chain, i.e. which preferably do not comprise a Ci₀-C₃₀ chain in their structure. Associative polymers contain such a fatty chain.

According to a first variant, the cellulose polymer(s) are non- associative, non-ionic. Mention may be made of (Ci-C₄)alkylcelluloses such as methylcelluloses and ethylcelluloses for example Ethocel standard 100 Premium from Dow Chemical ; (poly)hydroxy(C-i-C4)alkylcelluloses such as hydroxymethylcelluloses, hydroxyethylcelluloses for example Natrosol 250 HHR provided by Aqualon and hydroxypropylcelluloses for example Klucel EF from Aqualon ; mixed (poly)hydroxy(Ci-C₄)alkyl-(Ci-C4)alkylcelluloses such as hydroxypropylmethylcelluloses for example Methocel E4M from Dow Chemical ; hydroxyethylmethylcelluloses, hydroxyethylethylcelluloses for example Bermocoll E 481 FQ from Akzo Noble and hydroxybutylmethylcelluloses. According to a second variant, the cellulose polymer(s) are anionic. Among the anionic cellulose ethers, mention may be made of (poly)carboxy(CrC₄)alkylcelluloses and salts thereof. Examples that may be mentioned include carboxymethylcelluloses, carboxymethylmethylcelluloses for example Blanose 7M from the company Aqualon and carboxymethylhydroxyethylcelluloses, and the sodium salts thereof.

According to a third variant, the cellulose polymer(s) are cationic. Among the cationic cellulose, mention may be made of cationic cellulose derivatives such as cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, and described in particular in patent US 4 131 576, such as (poly)hydroxy(Ci-C₄)alkyl celluloses, for instance hydroxymethyl-, hydroxyethyl- or hydroxypropylcelluloses grafted in particular with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt. The commercial products corresponding to this definition are more particularly the products sold under the names Celquat® L 200 and Celquat® H 100 by the company National Starch.

The cellulose polymers are preferably non-ionic and free of fatty chain (non associative non ionic alkylcellulose polymer). Preferably, the cellulose polymer(s) useful in the invention are chosen from non ionic cellulose ethers such as (C C_^ alkylcelluloses, (poly)hydroxy(CrC₄)alkylcelluloses ; (poly)hydroxy(Ci-C₄)alkyl-(C C₄)alkylcelluloses such as hydroxypropylmethylcelluloses ; hydroxyethylmethylcelluloses ; hydroxyethylethylcelluloses ; hydroxybutylmethylcelluloses ; hydroxymethylcelluloses ; hydroxyethylcelluloses and hydroxypropylcelluloses.

The cellulose polymer(s) may be present in the composition useful in the invention in an amount ranging from 0.05% to 10% by weight, in particular from 0.1 % to 5% by weight and preferably from 0.2% to 3% by weight relative to the total weight of the composition.

These compositions can be packaged in pump-action sprays or in aerosol containers, in order to provide for application of the composition in the vaporized (lacquer) form or in the form of a mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray or a mousse, for the treatment of the hair. In these cases, the composition preferably comprises at least one propellant.

The method according to the invention can be provided in the form of a hair product, in particular a hair care, styling or shaping product. The method especially finds advantageous applications for the retention of the hairstyle or the shaping of the hair, or the volume and frizz reduction. Additional advantages are for the conditioning, shaping, reinforcing and/or repairing of the hair, in particular for improving the disentangling, smoothing, combability, manageability and softness of the hair.

The method of the invention comprises a heating step at a temperature higher than 150°C, preferably ranging from 150 to 250°C. The heating step can be carried out with irons such as flat irons, flat tongs or a crimping iron capable of raising the temperature to a value ranging from 150°C to 250°C.

According to a specific embodiment, the composition is applied on dried hair. After a posing time, usually of at least 10 min, preferably between 15 and 45 min, more preferably around 30 min, the hair are brushed and then straightened with a flat iron at a temperature of at least 150°C, preferably ranging from 200 to 250°C. Then the hair are rinsed with water and dried.

Before the application of the composition, the hair can be shampooed and dried.

The method of the invention is preferably used without a deformation step using reducing agent or a composition with pH over 10. The following examples serve to illustrate the invention without, however, exhibiting a limiting nature.

EXAMPLES

The following compositions were prepared at the time of use (given in weight %), pH of the composition being adjusted to 2.2 ± 0.2 :

COMPOSITION 1

The above composition with pH equal to 2.2 was applied on shampooed and blow-dried naturally curled hair. After having left the composition on hair for 30 min, the hair was brushed and then heated with a flat iron at a temperature from 200-250°C. Then the hair was rinsed.

By using the method of the invention, the hair thus treated exhibit a substantial reduction of volume.

The following compositions were prepared at the time of use (given in weight %):

COMPOSITION 2

COMPOSITION 3

(3-hydroxy-2-pentylcyclopentyl)acetic acid 10%

AMODIMETHICONE (and) TRIDECETH-5 (and) 2%

TRIDECETH-10 sold under the name DC(R)2-2899 by

DOW CORNING

AMODIMETHICONE (and) TRIDECETH-6 (and) 2%

CETRIMONIUM CHLORIDE sold under the name Belsil

ADM by Wacker

WATER QSP COMPOSITION 4

The above compositions were applied on shampooed and wet sensibilized or natural curly hair swatches. After having left the composition on hair for 15 min, the hair were brushed and then heated with a flat iron at a temperature from 200-250°C. Then the hair were rinsed and shampooed.

By using the method of the invention, the hair swatches thus treated exhibit a reduction of the curl, a strong soft touch, an increase of discipline.

Claims

1. METHOD FOR THE TREATMENT OF HAIR COMPRISING THE^ APPLICATION TO THE HAIR OF A COMPOSITION, comprising at least one organic monoacid and at least one aminosilicone, and a step of heating the hair at a temperature higher than 100°C.

2. METHOD, according to claim 1 wherein the monoacids are selected from compounds having the following formula (I) their stereoisomers, their organic or mineral salts or their corresponding solvates:

O

I I

R OH

(I)

wherein X represents a carbon atom, a group P-OH, a group P-H or a group S=O et R represents an alkyle, alcenyle , aryle or aralkyle group with a linear, branched or cyclic alkyle group comprising from 1 to 20 carbon atoms , a linear, branched or cyclic alcenyle group comprising from 2 to 20 carbon atoms, an aryle ou aralkyle group comprising from 6 to 20 carbon atoms, these groups being eventually substituted by one or more groups selected from halogen atoms and from the groups hydroxyle, trifluoromethyle, alcoxy C1-C4.

3. METHOD, according to claim 1 or 2 wherein organic monoacids are carboxylic acids.

4. METHOD, according to any of claims 1 to 3 wherein the monoacids are selected from compounds having the following formula (I) wherein X is a carbon atom and R radical is an alkyle, alcenyle , aryle or aralkyle group with a linear, branched or cyclic alkyle group comprising from 1 to 20 carbon atoms, a linear, branched or cyclic alcenyle group comprising from 2 to 20 carbon atoms, an aryle ou aralkyle group comprising from 6 to 20 carbon atoms, these groups being sustituted by at least one hydroxyle group being preferably located in position alpha or beta from the carboy group and these groups being eventually substituted by one or more other groups selected from halogen atoms and from the groups trifluoromethyle, alcoxy C1- C4.

5. METHOD, according to any of claims 1 to 4 wherein the monoacids are selected from glycolic acid, lactic acid, glyceric acid, gluconic acid, salicylic acid, 2-hydroxyisobutyric acid, 2-hydroxy-n-butyric acid, 2- hydroxyhexanoic acid, 2-hydroxypentanoic acid their stereoisomers, their organic or mineral salts or their corresponding solvates and more preferably are selected from glycolic acid, lactic acid, glyceric acid, gluconic acid, salicylic acid, their stereoisomers, their organic or mineral salts or their corresponding solvates.

6. METHOD, according to claims 1 to 5 wherein the composition comprises at least glycolic acid with at least one additional monocarboxylic acid of formula (I), preferably glycolic acid and salicylic acid.

7. METHOD, according to one of the preceding claims wherein the monoacids their stereoisomers, their organic or mineral salts or their corresponding solvates are present in the composition in an amount from 0.1 to 50% by weight, in particular from 0.1 % to 20% by weight and preferably from 1 % to 5% by weight, with respect to the total weight of the composition.

8. METHOD, according to one of the preceding claims, wherein the composition contains an aminosilicone of formula (II)

(R¹)a(T)_3-a-Si[OSi(T)₂]_n-[OSi(T)_b(R¹)₂._b]_m-OSi(T)_3-a-(R¹)a (II)

wherein:

T is a hydrogen atom, or a phenyl, hydroxyl (-OH), or CrC₈ alkyl radical, and preferably methyl or C-i-Cs alkoxy, preferably methoxy,

a denotes the number 0 or an integer from 1 to 3, and preferably 0,

b denotes 0 or 1 , and in particular 1 ,

-N(R²)-CH₂-CH₂-N(R²)₂;

-N(R²)₂; -N⁺(R²)₃ Q-;

-N⁺(R²) (H)₂ Q-;

-N⁺(R²)₂HQ^";

-N(R²)-CH₂-CH₂-N⁺(R²)(H)₂ Cf,

9. METHOD, according to one of the preceding claims, wherein the composition contains an aminosilicone of formula (lla):

a) in which R, R', R", which may be identical or different, denote a C-1-C4 alkyl radical, preferably CH₃; a C1-C4 alkoxy radical, preferably methoxy; or OH; A represents a linear or branched, C3-C8, preferably C₃-C₆, alkylene radical; m and n are integers that depend on the molecular weight and whose sum is preferably between 1 and 2000.

10. METHOD, according to one of the preceding claims, wherein the composition contains an aminosilicone of formula (lib): (CH₃)₃

wherein n and m have the meanings according to formula (II) or (lla).

11. METHOD, according to one of the preceding claims, wherein aminosilicones are present in an amount of at least 0.01 wt.% by weight , preferably in an amount in the range from 0.1 to 20 wt.%, more particularly in an amount in the range from 0.1 to 10 wt.%, relative to the total weight of the composition.

12. METHOD, according to one of Claims 1 to 11 wherein the composition is hydro alcoholic.

13. METHOD, according to any of the preceding claims wherein the composition exhibits an acidic pH, preferably less than 4., preferably varying from 1 to 3, more preferably from 1 ,5 to 3, better from 1 ,7 to 3.

14. METHOD, according to one of the preceding claims, wherein the heating step is carried out at a temperature from 150 to 250°C, preferably with flat irons in order to straight the hair.

15. METHOD according to any one of the preceding claims wherein the composition is applied on dried hair, and after a posing time of at least 10 min, preferably from 15 to 45 min, the hair are brushed and then straightened with a flat iron at a temperature of at least 150°C, preferably ranging from 200 to 250°C.

16. USE OF A COMPOSITION, comprising at least one organic monoacid preferably substituted with at least one hydroxyl radical and at least one aminosilicone for style retention and/or volume reduction and/or frizz reduction.