FR3058053A1 - METHOD FOR PERMANENT DEFORMATION OF HAIR USING DIAMINE AND REDUCING AGENT - Google Patents

Abstract

The present invention relates to a method of permanent deformation of keratinous fibers, in particular hair, which comprises the use of: i) one or more diamines, and ii) one or more reducing agents, said diamine (s) and / or said reducing agents being carried out in a single composition or in separate compositions applied to the fibers, it being understood that the composition (s) containing said diamine (s) does not contain (include) maleic acid or salts of maleic acid. The present invention also relates to a kit suitable for the implementation of this method.

Description

© Publication number: 3,058,053 (to be used only for reproduction orders)

©) National registration number: 16 60590 ® FRENCH REPUBLIC

NATIONAL INSTITUTE OF INDUSTRIAL PROPERTY

COURBEVOIE © Int Cl ⁸ : A 61 K8 / 41 (2017.01), A 61 Q 5/04

A1 PATENT APPLICATION

©) Date of filing: 02.11.16. (© Priority: (© Applicant (s): L'OREAL Société anonyme— FR. @ Inventor (s): SOW FATOUMATA. ©) Date of availability of the request: 04.05.18 Bulletin 18/18. ©) List of documents cited in the preliminary search report: See the end of this booklet (© References to other related national documents: ©) Holder (s): L'OREAL Société anonyme. ©) Extension request (s): (© Agent (s): CASALONGA.

PROCESS FOR PERMANENT DEFORMATION OF HAIR USING A DIAMINE AND A REDUCING AGENT.

FR 3 058 053 - A1

The present invention relates to a process for permanent deformation of keratin fibers, in particular of the hair, which comprises the implementation:

i) one or more diamines, and ii) one or more reducing agents, the said diamine (s) and the said reducing agent (s) being used in a single composition or in separate compositions applied to the fibers, it being understood that the composition (s) containing the said diamine (s) does not comprise (include) maleic acid or salts of maleic acid.

The present invention also relates to a kit suitable for implementing this method.

i

Permanent hair deformation process using a diamine and a reducing agent

The present invention relates to a process for permanent deformation of keratin fibers, in particular of the hair, which comprises the use of one or more diamines and one or more reducing agents, contained in one or more compositions applied to keratin fibers, especially the hair.

The present invention also relates to a kit comprising at least two compartments.

Many people are not satisfied with the appearance of their hair, especially people who have curly hair most often seek to get straight hair and, conversely, those who have straight hair want to have curly hair.

One of the techniques usually used to obtain permanent deformation of the hair consists, firstly, in opening the disulfide bonds -SS- of keratin (keratocystin) using a composition containing a suitable reducing agent ( reduction step) then, after rinsing the hair thus treated, generally with water, reconstituting the said disulphide bonds in a second step by applying to the hair previously tensioned (for example by curlers), an oxidizing composition ( oxidation step, also called fixing step) so as to finally give the hair the desired shape.

This technique makes it possible, for example, to straighten (straighten) hair or, on the contrary, curl hair. The new form imposed on the hair by a chemical treatment as above is permanent over time and resists in particular the action of washing with water or with shampoos, and this in contrast to the simple conventional techniques of temporary straightening, such than a styling.

The compositions which can be used for carrying out the reduction step generally contain, as reducing agents, sulphites, bisulphites, alkyl phosphines or preferably thiols. Among the latter, those commonly used are cysteine and its various derivatives, cysteamine and its derivatives, thiolactic acid or thioglycolic acid, their salts as well as their esters, in particular glycerol thioglycolate.

The oxidizing compositions necessary for the implementation of the fixing step are most often compositions based on hydrogen peroxide.

However, this technique is not entirely satisfactory. Indeed, although the latter proves to be very effective in modifying the shape of the hair, it can be aggressive for the hair fibers, which is mainly due to the different longer or shorter exposure times of the compositions used during a such process.

This technique can thus induce in the long term an alteration in the quality of the hair resulting in a decrease in their cosmetic properties, such as their shine and a degradation of their mechanical properties, more particularly of their mechanical resistance, due to swelling of the hair during rinsing between the reduction stage and the oxidation stage which can result in an increase in their porosity. These drawbacks are especially observed with thioglycolic acid which is generally used in basic medium at pH values varying from 8.5 to 9.5.

Furthermore, if the technique for permanent deformation of the hair described above is applied to hair which has been the subject of an artificial coloring beforehand, it can cause degradation or pickling of this artificial coloring.

Similarly, if a coloration is applied to permed hair according to the technique described above, the color obtained is very different from the color normally obtained on non-permed natural hair.

There is therefore a real need to find a new process for permanent deformation of keratin fibers, in particular hair which does not have all of the drawbacks described above, that is to say which does not affect the integrity and the quality of keratin fibers while providing good cosmetic properties to keratin fibers. In parallel, this process must maintain good performance in terms of permanent deformation of the keratin fibers, in particular with a residual effect with several shampoos.

It has now surprisingly been discovered that a process for permanent deformation of keratin fibers, in particular of the hair, which comprises the use of one or more diamines and one or more reducing agents applied sequentially or simultaneous on the keratin fibers made it possible to achieve the desired properties in terms of integrity, quality and cosmeticity of the keratin fibers while obtaining a good quality and lasting deformation of the keratin fibers.

The present invention therefore relates to a process for permanent deformation of keratin fibers, in particular of the hair, comprising the implementation:

i) one or more diamine (s), and ii) one or more reducing agent (s), said diamine (s) and said reducing agent (s) being used used in a single composition or in separate compositions applied to the fibers, it being understood that the composition (s) containing the said diamine (s) does not comprise (include) maleic acid nor of maleic acid salts.

The implementation of this process makes it possible to obtain a permanent deformation of the keratin fibers of good quality and remanent to several shampoos while preserving the quality and the integrity of the keratin fibers. In addition, the implementation of this process makes it possible to provide good cosmetic properties, in particular shine and softness to the touch, to keratin fibers.

Optionally, the process of the invention can also use one or more oxidizing agents.

The invention also relates to a kit suitable for implementing the method of the invention. This kit includes at least two compartments:

a first compartment comprising a reducing composition which comprises one or more reducing agents,

- a second compartment comprising an oxidizing composition which comprises one or more oxidizing agents,

one or more diamines being included in the reducing composition and / or in the oxidizing composition and / or in one or more separate composition (s) included in one or more additional compartments, it being understood that the composition (s) containing the said diamine (s) does not comprise (include) maleic acid or salts of maleic acid, and preferably does not comprise (include) monomeric compounds containing ethylenic unsaturation.

Other characteristics and advantages of the invention will appear more clearly on reading the description and the examples which follow.

As explained above, the method according to the invention comprises the implementation of one or more diamines.

Preferably, the diamine or diamines are chosen from the compounds of formula (I) below:

R \

(I) in which Ri, R ₂ , R3 and R4, independently of each other, represent a hydrogen atom or an alkyl radical, comprising from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms,

R, R ', R ”and R” ”, independently of each other, represent a hydrogen atom, an alkyl radical comprising from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, an alkoxyalkyl radical comprising from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms or an alkoxyamine radical comprising from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, n, p and q, each independently others represent a number varying from 0 to 100, preferably from 0 to 20, it being understood that for any value n, p or q greater than or equal to 2, the radicals R, R ', R ”and R” ”can be different from one CRR 'or CR ”R” ”motif to another.

In the context of the invention, the term “alkyl radical” means linear or branched alkyl radicals, which may be substituted or unsubstituted.

Preferably in formula (I), R 1, R ₂ , R 3 and R 4 represent a hydrogen atom.

Preferably in formula (I), R, R ’, R” and R ’” represent, independently of each other, a hydrogen atom or a methyl radical.

Preferably in formula (I), n, p and q, independently of each other, represent a number varying from 1 to 15.

In a particularly preferred embodiment of the process according to the invention, the diamine or diamines are chosen from the compounds of formula (I) in which:

- Ri, R ₂ , R3 and R4 are hydrogen atoms,

- R and R "are hydrogen atoms,

- R ’and R’ ”, independently of each other, are chosen from a hydrogen atom or a methyl radical,

- n and q vary from 1 to 5, preferably from 1 to 3, better are equal to 2,

- p ranges from 1 to 15, preferably ranges from 2 to 13.

Thus, the diamine or diamines are preferably chosen from polyoxyalkylenated diamines, preferably polyoxyethylenated diamines and polyoxypropylenated diamines.

As polyoxyalkylenated diamines, mention may in particular be made of the diamines sold under the brand JEFFAMINE® by the company HUNSTMAN, in particular the JEFFAMINE® of the D series, of the ED series and of the EDR series.

As JEFFAMINE® of the D series, mention may in particular be made of diamines D-230, D-400, D-2000 and D-4000.

As JEFFAMINE® of the ED series, mention may in particular be made of diamines HK-511, ED-600, ED-900 and ED-2003.

As JEFFAMINE® of the EDR series, mention may in particular be made of the EDR-148 and EDR-176 diamines.

Most preferably, the diamine or diamines used in the process according to the invention are chosen from poly (propylene glycol) bis (2-aminopropyl ether) with an average number of propylene glycol units equal to approximately 2, 5 (JEFFAMINE® D230), O, O'-bis (2-aminopropyl) polypropylene glycol-block polyethylene glycol-block-polypropylene glycol with an average number of propylene glycol units equal to approximately 3.6 and a number of units ethylene glycol equal to approximately 9 (JEFFAMINE® ED-600), or with a number of propylene glycol units equal to approximately 6 and an average number of ethylene glycol units equal to approximately 12.5 (JEFFAMINE® ED-900) and 2,2 '- (ethylenedioxy) bis (ethylamine) (JEFFAMINE® EDR-148).

Among the oxyalkylenated diamines, we can also note the

4,9-dioxa-1,12-dodecanediamine or 4,7,10-trioxa-l, 13tridecanediamine.

Preferably in the process according to the invention, the diamine or diamines represent from 1 to 50% by weight, preferably from 2 to 30% by weight, and more preferably from 5 to 15% by weight, relative to the total weight of each composition containing them.

As explained above, the method according to the invention also implements one or more reducing agents.

The reducing agent (s) are preferably chosen from sulfur-reducing agents.

Among these, there may be mentioned thioglycolic acid and its ester and amide derivatives, in particular glycerol monothioglycolate, cysteamine and its acylated derivatives (C1-C4) such as N-acetylcysteamine or N-propionyl-cysteamine, cysteine, N-acetylcysteine, thiomalic acid, panthetein, 2,3dimercaptosuccinic acid, N- (mercaptoalkyl) -o-hydroxy alkyl friend of such as those described in patent application EP354835, N- mono or N, N-dialkylmercapto-4-butyramides such as those described in patent application EP368763, aminomercaptoalkylamides such as those described in patent application EP432000, derivatives of N- (mercaptoalkyl) succinamic acids and N (mercaptoalkyl ) succinimides as described in patent application EP465342, alkylamino mercaptoalkylamides such as those described in patent application EP514282, the azeotropic mixture of 2-hydroxypropyl thioglycolate and (2-hydroxyl-methyl) thioglycolate l) ethyl described in patent application FR2679448, mercaptoalkylaminoamides such as those described in patent application FR2692481, N-mercaptoalkylalkanediamides described in patent application EP653202, derivatives of formamidine sulfinic acid, sulfites and bisulfites. If necessary, these compounds can be used in the form of salts.

In a particularly preferred manner, the reducing agent or agents are chosen from cysteine, cysteamine, thioglycolic acid and its salts or esters, sulfites, bisulfites, and mixtures of these compounds.

Very particularly preferably, the reducing agent or agents are chosen from thioglycolic acid and its salts.

The most preferred reducing agent is ammonium thioglycolate.

The reducing agent (s) preferably represent from 0.05 to 30% by weight, more preferably from 1 to 20% by weight, and very particularly from 4 to 11% by weight, relative to the total weight of the composition containing them.

As explained above, the composition (s) containing the diamine (s) does not comprise (include) maleic acid, nor of maleic acid salt.

Preferably, the composition (s) containing the diamine (s) does not comprise (comprise) monomeric compounds containing ethylenic unsaturation.

The term “ethylenically unsaturated monomeric compound” within the meaning of the present invention means a polymerizable compound consisting of a single unit and comprising at least one carbon-carbon double bond.

Mention may in particular be made, as ethylenically unsaturated monomeric compounds, of maleic acid, fumaric acid, (meth) acrylic acid and their salts, by way of example.

As explained above, in the process according to the invention, the diamine (s) and the reducing agent (s) are used in a single composition or in separate compositions.

Thus, in a first embodiment of the method according to the invention, the diamine (s) and the reducing agent (s) are present in a single composition.

In this first embodiment, the method according to the invention comprises a step of applying to the keratin fibers, preferably the hair, a composition comprising one or more diamines as defined above and one or more reducing agents as defined above.

In a second embodiment of the method according to the invention, the diamine (s) and the reducing agent (s) are used in separate compositions, the composition (s) comprising the said diamine (s) being applied before and / or after the composition comprising the said reducing agent (s).

In this second embodiment, the method according to the invention generally comprises i) a step of application to the keratin fibers, preferably the hair, of a composition comprising one or more diamines as defined above and ii ) a step of application to the keratin fibers, preferably the hair, of a composition comprising one or more reducing agents as defined above.

In a very particularly preferred variant of this second embodiment of the method according to the invention, the composition comprising the diamine (s) is applied after the composition comprising the reducing agent (s).

The method according to the invention can also comprise the use of one or more oxidizing agents present in a composition distinct from the composition comprising the reducing agent (s) and applied to the keratin fibers after the latter.

As oxidizing agents, mention may especially be made of hydrogen peroxide, urea peroxide, bromates or ferricyanides of alkali metals, peroxygenated salts such as for example persulfates, perborates and percarbonates of alkali or alkali metals - earthy like sodium, potassium, magnesium.

It is also possible to use, as oxidizing agent, one or more redox enzymes such as laccases, peroxidases and oxidoreductases with 2 electrons (such as uricase), optionally in the presence of their respective donor or cofactor.

Preferably, the oxidizing agent (s) are chosen from hydrogen peroxide, urea peroxide, bromates or ferricyanides of alkali metals, peroxygenated salts, and mixtures of these compounds.

In a particularly preferred manner, the oxidizing agent or agents are chosen from hydrogen peroxide and alkaline bromates.

Most preferably, the oxidizing agent is hydrogen peroxide.

ίο

The oxidizing agent (s) generally represent from 0.1 to 8% by weight, preferably from 0.2 to 5% by weight relative to the total weight of the composition containing them.

The oxidizing agent (s) may be in the composition comprising the diamine (s) or in a separate composition.

In one embodiment of the method according to the invention, the diamine (s), the reducing agent (s) and the oxidizing agent (s) are applied in separate compositions.

Thus, in this embodiment, the method comprises the sequential application on the keratin fibers of at least three distinct compositions:

- A first composition comprising the reducing agent (s) as defined above, then

a second composition comprising the oxidizing agent or agents as defined above, and

a third composition comprising the diamine (s) as defined above, applied before said first composition and / or simultaneously with the first composition and / or after the first composition, and before the second composition and / or simultaneously with the second composition and / or after the second composition, and preferably the third composition comprising the said diamine (s) is applied between the first composition and the second composition or simultaneously with the second composition.

Preferably, in this embodiment, the method comprises the sequential application to the keratin fibers of at least three distinct compositions:

a first composition comprising the said reducing agent (s) as defined above, then

a second composition comprising the said diamine or diamines as defined above, then

- A third composition comprising the said oxidizing agent (s) as defined above.

In another embodiment of the method according to the invention, the diamine or diamines are included in the composition comprising the said reducing agent (s) and / or in the composition comprising the said oxidizing agent (s).

In a first variant of this other embodiment, the diamine or diamines are included in the composition comprising the reducing agent (s).

Thus, in this first variant of this other embodiment of the method according to the invention, the method comprises the sequential application to the keratin fibers of at least two compositions:

i) a first composition comprising the diamine (s) and the reducing agent (s), then ii) a second composition comprising the oxidizing agent (s).

In a second variant of this other embodiment, the diamine or diamines are included in the composition comprising the oxidizing agent (s).

Thus, in this second second variant of this other embodiment of the method according to the invention, the method comprises the sequential application to the keratin fibers of at least two compositions:

i) a first composition comprising the reducing agent (s), then ii) a second composition comprising the diamine (s) and the oxidizing agent (s).

In a third variant of this other embodiment of the process according to the invention, the diamine or diamines are included in the composition comprising the reducing agent (s) and in the composition comprising the oxidizing agent (s).

Thus, in this third variant of this other embodiment of the method according to the invention, the method comprises the sequential application to the keratin fibers of at least two compositions:

i) a first composition comprising the diamine (s) and the reducing agent (s), then ii) a second composition comprising the diamine (s) and the oxidizing agent (s).

The compositions used in the process according to the invention may also comprise one or more surfactants, more particularly nonionic, anionic, cationic, or amphoteric or zwitterionic surfactants.

The nonionic surfactant (s) which can be used in the process according to the invention are described for example in "Handbook of Surfactants" by M.R. PORTER, Blackie & Son editions (Glasgow and London), 1991, pp 116-178. They are chosen in particular from alcohols, alpha-diols, (C1-C20) alkyl phenols, these compounds being polyethoxylated, polypropoxylated and / or polyglycerolated and having at least one fatty chain comprising, for example, from 8 to 18 atoms of carbon, the number of ethylene oxide and / or propylene oxide groups possibly ranging from 2 to 50 and the number of glycerol groups possibly ranging from 2 to 30.

Mention may also be made of copolymers of ethylene and propylene oxide, polyoxyalkylenated fatty acid esters, optionally oxyalkylenated alkylpolyglycosides, alkylglucoside esters, N-alkylglucamine and N-acylmethylglucamine derivatives, aldobionamides and amine oxides.

Unless stated otherwise, the term “fatty” compound (for example a fatty acid) denotes for these surfactants a compound comprising in its main chain at least one alkyl chain, saturated or unsaturated, comprising at least 6 carbon atoms, preferably 8 to 30 carbon atoms, and better still from 10 to 22 carbon atoms.

The term “anionic surfactant” is understood to mean a surfactant comprising only anionic groups as ionic or ionizable groups. These anionic groups are preferably chosen from the groups CO2H, CO2 ', SO3H, SO3', OSO3H, oso ₃ ; O2PO2H, O2PO2H-, O2PO2 ² ·.

The anionic surfactant (s) which can be used in the process of the invention are in particular chosen from alkyl sulfates, alkyl ether sulfates, alkylamidoethersulfates, alkylarylpolyethersulfates, monoglyceride sulfates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, alpha-olefin sulfonates, paraffin sulfonates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates, alkylsulfoacetates, acylsarcosinates, acylglutamates, alkylsulfosuccinamates, acylisethionates and N-acyl esters and N-acyl salts of polyglycoside-polycarboxylic acids, acyllactylates, salts of D-galactoside-uronic acids, salts of alkyl ether-carboxylic acids, salts of alkyl aryl ether-carboxylic acids, salts of alkyl amidoether acids carboxylic; or the non-salified forms of all these compounds, the alkyl and acyl groups of all these compounds containing from 6 to 24 carbon atoms and the aryl group denoting a phenyl group.

Some of these compounds can be oxyethylenated and then preferably contain from 1 to 50 ethylene oxide units.

The salts of C6-C24 alkyl monoesters and of polyglycoside-polycarboxylic acids can be chosen from C6-C24 alkyl polyglycoside-citrates, C6-C24 alkyl polyglycoside-tartrates and polyglycoside-sulfosuccinates C ₆ -C ₂ alkyl 4.

When the anionic surfactant (s) are in the form of a salt, they are not in the form of zinc salts, and they can be chosen from the alkali metal salts such as the sodium or potassium and preferably sodium salt, ammonium salts, amine salts and in particular amino alcohol salts, and alkaline earth metal salts such as the magnesium salt.

By way of example of amino alcohol salts, mention may be made in particular of the mono-, di- and tri-ethanolamine salts, the mono-, di- or tri-isopropanol-amine salts, the 2-amino- 2-methyl-13058053 propanoi, 2-amino-2-methyl-l, 3-propanediol and tri s (hydroxy methyl) ami no methane.

The alkali or alkaline earth metal salts are preferably used and in particular the sodium or magnesium salts.

Preferably used (C6-C24) alkyl sulfates, (C ₆ -C 24) alkyl ethersulfates, optionally oxyethylenated comprising from 2 to 50 ethylene oxide units, and mixtures thereof, in particular in the form of alkali metal salts or alkaline earth, ammonium, amino alcohol. More preferably, the anionic surfactant (s) are chosen from alkyl (Cio-C2o) ethersulphates, and in particular sodium laurylethersulphate containing 2.2 moles of ethylene oxide.

Preferably, the compositions used in the process according to the invention comprise one or more cationic surfactants.

The term “cationic surfactant” means a positively charged surfactant when it is contained in one of the compositions which can be used in the process according to the invention. This surfactant can carry one or more positive permanent charges or contain one or more cationizable functions within one of the compositions which can be used in the process according to the invention.

The cationic surfactant (s) are preferably chosen from primary, secondary or tertiary fatty amines, optionally polyoxyalkylenated, or their salts, quaternary ammonium salts, and mixtures thereof.

The fatty amines generally comprise at least one C8-C30 hydrocarbon chain

Mention may in particular be made, as quaternary ammonium salts, for example:

- those corresponding to the following general formula (II):

(II) in which the groups R 1 to R ₄ , which may be identical or different, represent an aliphatic group, linear or branched, comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one groups R 1 to R ₄ denoting an aliphatic radical, linear or branched, comprising from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms. The aliphatic groups can comprise heteroatoms such as in particular oxygen, nitrogen, sulfur and halogens. The aliphatic groups are for example chosen from C1-C30 alkyl, C1-C30 alkoxy, polyoxyalkylene (C2-C6), C1-C30 alkylamide, (Ci2C22) amidoalkyl (C2-C6), alkyl (Ci2- C 22) acetate, and C1-C30 hydroxyalkyl; X is an anion chosen from the group of halides, phosphates, acetates, lactates, (C ₁ -C ₄ ) alkyl sulfates, (C ₁ -C ₄ ) alkyl - or (C ₁ -C ₄ ) alkyl aryl sulfonates.

Among the quaternary ammonium salts of formula (II), tetraalkylammonium salts are preferred on the one hand, such as, for example, the dialkyldimethylammonium or alkyltrimethylammonium salts in which the alkyl group contains approximately from 12 to 22 atoms of carbon, in particular the behenyltrimethylammonium salts, distearyldimethylammonium, cetyltrimethylammonium, benzyldimethylstearylammonium or, on the other hand, the palmitylamidopropyltrimethyl ammonium salts, stearamidopropyltrimethylammonium, stearamidylethylammethyl esteraryldimethylammonium acetyl ammonium salts marketed under the name CERAPHYL® 70 by the company VAN DYK. It is particularly preferred to use the chloride salts of its compounds.

- the quaternary ammonium salts of imidazoline, such as, for example, those of formula (III) below:

R, '6

(III) in which R5 represents an alkenyl or alkyl group comprising from 8 to 30 carbon atoms, for example derived from tallow fatty acids, Re represents a hydrogen atom, a C1-C4 alkyl group or an alkenyl group or alkyl containing from 8 to 30 carbon atoms, R7 represents a C1-C4 alkyl group, Rs represents a hydrogen atom, a C1-C4 alkyl group, X is an anion chosen from the group of halides, phosphates, acetates , lactates, alkylsulfates, alkyl- or alkylaryl-sulfonates, the alkyl and aryl groups of which preferably comprise from 1 to 20 carbon atoms and from 6 to 30 carbon atoms respectively. Preferably, R5 and Re denote a mixture of alkenyl or alkyl groups containing from 12 to 21 carbon atoms, for example derived from tallow fatty acids, R7 denotes a methyl group, Rx denotes a hydrogen atom. Such a product is for example marketed under the name REWOQUAT® W 75 by the company REWO;

- the salts of quaternary di or triammonium in particular of formula (IV):

++

2X

(IV) in which R ₉ denotes an alkyl radical containing approximately from 16 to 30 carbon atoms optionally hydroxylated and / or interrupted by one or more oxygen atoms, Rio is chosen from hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms or a group (R _9a ) (Rio _a ) (Riia) N- (CH ₂ ) ₃ , R9a, Rio _a , Riia, Ru, R12, R13 and R14, identical or different, are chosen from hydrogen or an alkyl radical containing from 1 to 4 carbon atoms, and X 'is an anion chosen from the group of halides, acetates, phosphates, nitrates and methylsulfates. Such compounds are for example Finquat CT-P offered by the company FINETEX (Quaternium 89), Finquat CT offered by the company FINETEX (Quaternium 75),

- quaternary ammonium salts containing at least one ester function, such as those of formula (V) below:

θ (C _s H _2s O) _z pR ₁₈

R ₁₇ —C- (OC _r H _2r ) —N— (C _t H _2t O) -R ₁₆ χ ^Rl5 (V) in which:

Ris is selected from C 1 -C 6 alkyl groups and C 1 -C 6 hydroxyalkyl or dihydroxyalkyl groups;

Ri6 is chosen from:

O

II, R ₁₉ - c—

- the group

- the R20 groups which are C1-C22 hydrocarbon groups, linear or branched, saturated or unsaturated,

- the hydrogen atom,

Ri8 is chosen from:

O

II r ₂₁ - c—

- the group

- R22 groups which are linear or branched, saturated or unsaturated, CiC6 hydrocarbon groups,

- the hydrogen atom,

R17, R19 and R21, identical or different, are chosen from C7-C21 hydrocarbon groups, linear or branched, saturated or unsaturated;

r, s and t, identical or different, are integers ranging from 2 to 6;

y is an integer from 1 to 10;

x and z, identical or different, are integers ranging from 0 to 10;

X 'is a simple or complex, organic or inorganic anion; provided that the sum x + y + z is from 1 to 15, that when x is 0 then Ri6 is R20 and that when z is 0 then Ris is

R22

The alkyl groups R15 may be linear or branched and more particularly linear.

Preferably, R15 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.

Advantageously, the sum x + y + z is worth from 1 to 10.

When Ri6 is a hydrocarbon group R20, it can be long and have from 12 to 22 carbon atoms, or short and have from 1 to 3 carbon atoms.

When Ris is a hydrocarbon R22 group, it preferably has 1 to 3 carbon atoms.

Advantageously, R17, R19 and R21, identical or different, are chosen from C11-C21 hydrocarbon groups, linear or branched, saturated or unsaturated, and more particularly from C11-C21 alkyl and alkenyl groups, linear or branched, saturated or unsaturated.

Preferably, x and z, identical or different, are worth 0 or 1.

Advantageously, y is equal to 1.

Preferably, r, s and t, identical or different, are worth 2 or 3, and even more particularly are equal to 2.

The anion X ′ is preferably a halide (chloride, bromide or iodide) or an alkyl sulphate, more particularly methyl sulphate. It is however possible to use methanesulfonate, phosphate, nitrate, tosylate, an anion derived from organic acid such as acetate or lactate or any other anion compatible with ammonium having an ester function.

The anion X 'is even more particularly the chloride or the methyl sulphate.

Use is more particularly made, in the composition which can be used in the process according to the invention, of the ammonium salts of formula (V) in which:

Ris denotes a methyl or ethyl group, x and y are equal to 1; z is 0 or 1; r, s and t are 2;

Ri6 is chosen from:

O

II, R ₁₉ - c—

- the group

- methyl, ethyl or C14-C22 hydrocarbon groups,

- the hydrogen atom;

Ri8 is chosen from:

O

II r ₂₁ - c—

- the group

- the hydrogen atom;

R17, R19 and R21, identical or different, are chosen from C13-C17 hydrocarbon groups, linear or branched, saturated or unsaturated, and preferably from C13-C17 alkyl and alkenyl groups, linear or branched, saturated or unsaturated .

Advantageously, the hydrocarbon groups are linear.

Mention may be made, for example, of the compounds of formula (V) such as the salts (chloride or methylsulfate in particular) of diacyloxyethyldimethylammonium, of diacyloxyethyl-hydroxyethylmethylammonium, of monoacyloxyethyl-dihydroxyethyl3058053 methylammonium, of triacyloxyethyl-methylammonium, of monoacyloxyethyl-hydroxyethylmethylethyl . The acyl groups preferably have 14 to 18 carbon atoms and more particularly come from a vegetable oil such as palm or sunflower oil. When the compound contains several acyl groups, these can be the same or different.

These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, alkyldiethanolamine or alkyldiisopropanolamine optionally oxyalkylenated on C10-C30 fatty acids or on mixtures of C10-C30 fatty acids. vegetable or animal origin, or by transesterification of their methyl esters. This esterification is followed by quaternization using an alkylating agent such as an alkyl halide (preferably methyl or ethyl), dialkyl sulfate (preferably methyl or ethyl), methanesulfonate. methyl, methyl para-toluenesulfonate, glycol or glycerol hydrochloride.

Such compounds are for example sold under the names DEHYQUART® by the company HENKEL, STEPANQUAT® by the company STEPAN, NOXAMIUM® by the company CECA, REWOQUAT® WE 18 by the company REWO-WITCO.

One or more of the compositions which can be used in the process according to the invention may contain, for example, a mixture of mono-, di- and triester salts of quaternary ammonium with a majority by weight of diester salts.

It is also possible to use the ammonium salts containing at least one ester function described in patents US-A-4,874,554 and US-A-4,137,180.

Behenoylhydroxypropyltrimethylammonium chloride can be used, offered by KAO under the name Quatarmin BTC 131.

Preferably, the ammonium salts containing at least one ester function contain two ester functions.

Among the quaternary ammonium salts containing at least one ester function which can be used, it is preferred to use the salts of dip al mit oy 1 et hy lhydr oxy ethyl methylammonium.

The cationic surfactants are preferably chosen from those of formula (II) and those of formula (V), and even more preferably from those of formula (II).

The amphoteric or zwitterionic surfactant (s) which can be used in the process according to the invention can in particular be derivatives of secondary or tertiary aliphatic amines, optionally quaternized, in which the aliphatic group is a linear or branched chain containing from 8 to 22 atoms carbon, said amine derivatives containing at least one anionic group such as, for example, a carboxylate, sulfonate, sulfate, phosphate or phosphonate group. Mention may be made in particular of (C ₈ -C 20) alkyl betaines, sulfobetaines, (C ₈ alkyl C2o) amido (Cs-C6-alkyl) amido ((C8-C2o alkyl) amido (C6-C6-alkyl sulfobetaines) .

Among the derivatives of secondary or tertiary aliphatic amines, optionally quaternized which can be used, as defined above, mention may also be made of the following compounds of respective structures (B1) and (B2):

Ra-C (O) -NHCH ₂ CH2N ⁺ (Rb) (Rc) -CH ₂ C (O) O ·, M ⁺ , X '(Bl)

Formula (Bl) in which:

Ra represents a C10-C30 alkyl or alkenyl group derived from a RaCOOH acid, preferably present in hydrolyzed coconut oil, a heptyl, nonyl or undecyl group;

Rb represents a beta-hydroxyethyl group; and

Rc represents a carboxymethyl group;

M ⁺ represents a cationic counter ion derived from an alkaline, alkaline earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine, and

X 'represents an organic or inorganic anionic counter ion, preferably chosen from halides, acetates, phosphates, nitrates, (C1-C4) alkyl sulfates, (C1-C4) alkyl - or (C1-C4) aryl-sulfonates alkyl, in particular methyl sulfate and ethyl sulfate;

or else M ⁺ and X 'are absent;

Ra'-C (O) -NH-CH ₂ -CH ₂ -N (B) (B ') (B2)

Formula in which:

B represents the group -CH ₂ -CH ₂ -OX ';

B 'represents the group - (CH ₂ ) _Z Y', with z = 1 or 2;

X 'represents the group -CH ₂ -C (O) OH, -CH ₂ -C (O) OZ', -CH ₂ CH ₂ -C (O) OH, -CH ₂ -CH ₂ -C (O) OZ ', or a hydrogen atom;

Y 'represents the group -C (O) OH, -C (O) OZ', -CH ₂ -CH (OH) SO ₃ H or the group -CH ₂ -CH (OH) -SO ₃ -Z ';

Z ’represents a cationic counter ion derived from an alkali or alkaline earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;

Ra 'represents a Cio-C ₃ o alkyl or CioC ₃ o alkenyl group of a Ra'-COOH acid preferably present in coconut oil or in hydrolysed linseed oil, an alkyl group, in particular in C17 and its iso form, an unsaturated C17 group.

Compounds of this type are classified in the CTFA dictionary, ^5th edition, 1993, under the names disodium cocoamphodiacetate, disodium lauroamphodiacetate caprylamphodiacetate disodium capryloamphodiacetate, disodium cocoamphodipropionate, disodium lauroamphodipropionate, disodium caprylamphodipropionate disodium capryloamphodipropionate disodium, lauroamphodipropionic acid, cocoamphodipropionic acid.

By way of example, mention may be made of cocoamphodiacetate sold by the company RHODIA under the trade name MIRANOL® C2M concentrate

It is also possible to use compounds of formula (B’2);

Ra ”-NH-CH (Y”) - (CH ₂ ) _n -C (O) NH (CH ₂ ) _n -N (Rd) (Re) (B'2)

Formula in which:

Y ”represents the group -C (O) OH, -C (O) OZ”, -CH ₂ -CH (OH) SO ₃ H or the group -CH ₂ -CH (OH) -SO ₃ -Z ”;

Rd and Re, independently of one another, represent a C1-C4 alkyl or hydroxyalkyl radical;

Z ”represents a cationic counter ion derived from an alkali or alkaline earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;

Ra ”represents a Cio-C ₃ o alkyl or alkenyl group of an Ra” -C (O) OH acid preferably present in coconut oil or in hydrolyzed linseed oil;

n and n ’, independently of each other, denote an integer ranging from 1 to 3.

Among the compounds of formula (B’2), mention may be made of the compound classified in the CTFA dictionary under the name sodium diethylaminopropyl cocoaspartamide and marketed by the company CHIMEX under the name CHIMEXANE HB.

Among the amphoteric or zwitterionic surfactants mentioned above, use is preferably made of (C8-C ₂ o) alkyl betaines such as cocoylbetaine, (C8-C ₂ o alkyl) amido (C ₂ C ₆ cb) betaines than cocoylamidopropyl betaine, and mixtures thereof.

More preferably, the amphoteric or zwitterionic surfactant (s) are chosen from cocoylamidopropylbetaine and cocoylbetaine.

The surfactants which can be used in the process according to the invention are preferably nonionic or cationic.

Preferably when they are present, the surfactant (s) represent from 0.1 to 20% by weight, better still from 1 to 10% by weight relative to the total weight of each composition containing them.

The compositions used in the process according to the invention can also comprise one or more silicones.

The silicones which can be used in accordance with the invention can be in the form of oils, waxes, resins or gums.

Preferably, the silicone (s) are chosen from polydialkylsiloxanes, in particular polydimethylsiloxanes (PDMS), and organo-modified polysiloxanes comprising at least one functional group chosen from amino groups, aryl groups and alkoxy groups.

Organopolysiloxanes are defined in more detail in Walter NOLL's “Chemistry and Technology of Silicones” (1968), Academie Press. They can be volatile or non-volatile.

The volatile silicones are more particularly chosen from silicones having a boiling point ranging from 60 ° C. to 260 ° C., and more particularly still the silicones chosen from:

(i) cyclic polydialkylsiloxanes comprising from 3 to 7, preferably from 4 to 5 silicon atoms. It is, for example, octamethylcyclotetrasiloxane marketed in particular under the name of VOLATILE SILICONE® 7207 by UNION CARBIDE or SILBIONE® 70045 V2 by RHODIA, decamethylcyclopentasiloxane marketed under the name of VOLATILE SILICONE® 7158 by UNION CARBIDE, and SILBIONE ® 70045 V5 by RHODIA, as well as their mixtures.

Mention may also be made of cyclocopolymers of the dimethylsiloxane / methylalkylsiloxane type, such as SILICONE VOLATILE® FZ 3109 sold by the company UNION CARBIDE, of formula:

with

- Si-O -

with D 'ch ₃

CH ₃

- Si - O - C ₈ H ₁₇ I

Mention may also be made of mixtures of cyclic polydialkylsiloxanes with organic compounds derived from silicon, such as the mixture of octamethylcyclotetrasiloxane and tetratrimethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-1, l - (hexa -2,2,2 ', 2', 3,3'trimethylsilyloxy) bis-neopentane;

(ii) linear volatile polydialkylsiloxanes having 2 to 9 silicon atoms and having a viscosity less than or equal to 5.10 ' ⁶ m ² / s at 25 ° C. This is, for example, decamethyltetrasiloxane marketed in particular under the name " SH 200 "by TORAY SILICONE. Silicones included in this class are also described in the article published in Cosmetics and Toiletries, Vol. 91, Jan. 76, P. 27-32 - TODD & BYERS "Volatile Silicone fluids for cosmetics".

The non-volatile silicones which can be used according to the invention may preferably be non-volatile polydialkylsiloxanes, gums and resins of polydialkylsiloxanes, polyorganosiloxanes modified by organofunctional groups chosen from amino groups, aryl groups and alkoxy groups as well as their mixtures .

These silicones are more particularly chosen from polydialkylsiloxanes among which mention may mainly be made of polydimethylsiloxanes with trimethylsilyl end groups. The viscosity of the silicones is measured at 25 ° C. according to standard ASTM 445 Appendix C.

Among these polydialkylsiloxanes, non-limiting examples that may be mentioned include the following commercial products:

- SILBIONE® oils of series 47 and 70,047 or MIRASIL® oils sold by RHODIA such as, for example, oil 70,047 V 500,000;

- the oils of the MIRASIL® series sold by the company RHODIA;

- oils of the 200 series from the company DOW CORNING such as DC200 having a viscosity of 60,000 mm ² / s;

- VISCASIL® oils from GENERAL ELECTRIC and certain oils from the SF series (SF 96, SF 18) from GENERAL ELECTRIC.

Mention may also be made of polydimethylsiloxanes with dimethylsilanol end groups known under the name of dimethiconol (CTFA), such as oils of the 48 series from the company RHODIA.

In this class of polydialkylsiloxanes, mention may also be made of the products sold under the names "ABIL WAX® 9800 and 9801" by the company GOLDSCHMIDT which are polydialkyl (C1-C20) siloxanes.

The silicone gums which can be used in accordance with the invention are in particular polydialkylsiloxanes, preferably polydimethylsiloxanes having high number average molecular weights ranging from 200,000 to 1,000,000 used alone or as a mixture in a solvent.

The solvent can be chosen from volatile silicones, polydimethylsiloxane oils (PDMS), polyphenylmethylsiloxane oils (PPMS), isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane, tridecane or their mixtures.

Products more particularly usable in accordance with the invention are mixtures such as:

- the mixtures formed from a polydimethylsiloxane hydroxylated at the chain end, or dimethiconol (CTFA) and a cyclic polydimethylsiloxane also called cyclomethicone (CTFA) such as the product Q2 1401 sold by the company Dow Corning;

- mixtures of a polydimethylsiloxane gum and a cyclic silicone such as the product SF 1214 Silicone Fluid from the company GENERAL ELECTRIC, this product is a gum SF 30 corresponding to a dimethicone, having a number average molecular weight of 500,000 solubilized in SF 1202 Silicone Fluid oil corresponding to decamethylcyclopentasiloxane;

- mixtures of two PDMS of different viscosities, and more particularly of a PDMS gum and a PDMS oil, such as the product SF 1236 from the company GENERAL ELECTRIC. The SF product

1236 is the mixture of an SE 30 gum defined above having a viscosity of 20 m ² / s and an SF 96 oil with a viscosity of 5.10 ⁶ m ² / s. This product preferably contains 15% of SE 30 gum and 85% of an SF 96 oil.

The organopolysiloxane resins which can be used in accordance with the invention are crosslinked siloxane systems containing the units:

(R?) 2SiO2 / 2, (R?) 3SiOi / 2, R7S1O3 / 2 and S1O4 / 2 in which R7 represents an alkyl having 1 to 16 carbon atoms. Among these products, those which are particularly preferred are those in which R7 denotes a lower C1-C4 alkyl group, more particularly methyl.

Mention may be made, among these resins, of the product sold under the name "DOW CORNING 593" or those sold under the names "SILICONE FLUID SS 4230 and SS 4267" by the company GENERAL ELECTRIC and which are silicones of dimethyl / trimethyl siloxane structure.

Mention may also be made of the resins of the trimethylsiloxysilicate type sold in particular under the names X22-4914, X21-5034 and X21-5037 by the company SHINETSU.

The organomodified silicones which can be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon group.

The organomodified silicones can be polydiaryl siloxanes, in particular polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized by the organofunctional groups mentioned above.

The polyalkylarylsiloxanes are particularly chosen from polydimethyl / methylphenylsiloxanes, linear and / or branched polydimethyl / diphenylsiloxanes with a viscosity ranging from 1.10 ⁵ to 5.10 ² m ² / s at 25 ° C.

Among these polyalkylarylsiloxanes, mention may be made, by way of example, of the products sold under the following names:

- SILBIONE® oils of the 70 641 series from RHODIA;

- the oils of the RHODORSIL® 70 633 and 763 series from RHODIA;

- DOW CORNING 556 COSMETIC GRAD FLUID oil from DOW CORNING;

- BAYER PK series silicones as the product

PK20;

- the silicones of the PN and PH series from Bayer, such as the PN1000 and PH1000 products;

- certain oils from the GENERAL ELECTRIC SF series such as SF 1023, SF 1154, SF 1250, SF 1265.

Among the organomodified silicones, mention may also be made of polyorganosiloxanes comprising:

- Amino groups substituted or not, such as the products sold under the name GP 4 Silicone Fluid and GP 7100 by the company GENESEE or the products sold under the names Q2 8220 and DOW CORNING 929 or 939 by the company DOW CORNING. The substituted amino groups are in particular C1-C4 aminoalkyl groups.

- alkoxylated groups, such as the product sold under the name "SILICONE COPOLYMER F-755" by SWS SILICONES and ABIL WAX® 2428, 2434 and 2440 by the company GOLDSCHMIDT.

The silicones which can be used according to the invention generally represent from 0.1 to 30% by weight, better still from 1 to 10% by weight relative to the total weight of each composition containing them.

The compositions used in the process according to the invention can also comprise one or more non-silicone fatty substances.

By fatty substance is meant an organic compound insoluble in water at ordinary room temperature (25 ° C) and at atmospheric pressure (760 mm Hg), having a water solubility of less than 5%, preferably less at 1%, and even more preferably at 0.1%.

In addition, fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, such as, for example, chloroform, ethanol, benzene, petroleum jelly oil or decamethylcyclopentasiloxane.

The term “non-silicone fatty substance” is understood to mean a fatty substance not comprising a silicon atom.

The non-silicone fatty substance (s) which can be used in one or more of the compositions used in the process according to the invention are preferably chosen from hydrocarbons, fatty alcohols, fatty acid and / or fatty alcohol esters, unsalted fatty acids, waxes and their mixtures.

The fatty substance (s) may be liquid or non-liquid at ambient temperature and at atmospheric pressure.

The liquid fatty substances which can be used in the invention preferably have a viscosity of less than or equal to 2 Pa.s, better still less than or equal to 1 Pa.s and even better still less than or equal to 0.1 Pa.s at the temperature of 25 ° C and at a shear rate of 1 s' ¹ .

The fatty substances generally have in their structure a hydrocarbon chain comprising at least 6 carbon atoms.

By liquid hydrocarbon is meant a hydrocarbon composed only of carbon and hydrogen atoms, liquid at ordinary temperature (25 ° C) and at atmospheric pressure (760 mm Hg, or 1,013.10 ⁵ Pa).

More particularly, the liquid hydrocarbons are chosen from:

- linear or branched C6-C6 alkanes, possibly cyclic. Examples include hexane, undecane, dodecane, tridecane and isoparaffins such as isohexadecane, isododecane and isodecane.

- linear or branched hydrocarbons, of animal or synthetic mineral origin, of more than 16 carbon atoms, such as paraffin oils, and their derivatives, petroleum jelly, petroleum jelly oil, polydecenes, hydrogenated polyisobutene such than that sold under the Parléam® brand by NOF Corporation, squalane.

Preferably, the liquid hydrocarbon (s) are chosen from paraffin oils, isoparaffins, petrolatum oil, undecane, tridecane, isododecane and their mixtures.

In a very particularly preferred variant, the liquid hydrocarbon (s) are chosen from petroleum jelly oil, isoparaffins, isododecane and a mixture of undecane and tridecane.

By liquid fatty alcohol is meant a non-glycerolated and non-oxyalkylenated fatty alcohol, liquid at ordinary temperature (25 ° C) and at atmospheric pressure (760 mm Hg, or 1.013.10 ⁵ Pa). Preferably, the liquid fatty alcohols of the invention contain from 8 to 30 carbon atoms and they can be saturated or unsaturated.

The saturated liquid fatty alcohols are preferably branched. They may optionally include in their structure at least one aromatic or non-aromatic, preferably acyclic, cycle.

More particularly, the liquid saturated fatty alcohols of the invention are chosen from octyldodecanol, decyl-2tetradecanol, isostearyl alcohol, 2-hexyldecanol.

Octyldodecanol and decyl-2-tetradecanol are particularly preferred.

Unsaturated liquid fatty alcohols have in their structure at least one double or triple bond, and preferably one or more double bonds. When several double bonds are present, they are preferably 2 or 3 in number and they may or may not be conjugated.

These unsaturated fatty alcohols can be linear or branched.

They may optionally include in their structure at least one aromatic cycle or not. They are preferably acyclic.

More particularly, the liquid unsaturated fatty alcohols which can be used in the invention are chosen from oleic (or oleyl) alcohol, linoleic (or linoleyl) alcohol, linolenic (or linolenyl) alcohol and undecylenic alcohol.

pentaerythrityl, tetraisostearate

Oleic alcohol is particularly preferred.

By liquid fatty ester is meant an ester derived from a fatty acid and / or a fatty alcohol, liquid at ordinary temperature (25 ° C) and at atmospheric pressure (760 mm Hg, or 1.013.10 ⁵ Pa).

More particularly, the liquid esters are chosen from saturated or unsaturated, linear or branched, linear or branched aliphatic mono- or polyacids, in C1-C26 and linear or branched, saturated or unsaturated, aliphatic mono- or polyalcohols, in C1-C26, the total number of carbon atoms of the esters being greater than or equal to 10.

Preferably, for monoalcohol esters, at least one of the alcohol or of the acid from which the esters of the invention are derived is branched.

Among the monoesters of monoacids and monoalcohols, mention may be made of ethyl and isopropyl palmitates, alkyl myristates such as isopropyl or ethyl myristate, isocetyl stearate, isononanoate ethyl-2-hexyl, isodecyl neopentanoate, and isostearyl neopentanoate.

Esters of C4-C22 di- or tricarboxylic acids and C1-C22 alcohols and esters of mono-, di- or tricarboxylic acids and non-sugar alcohols di-, tri-, can be used. tetra- or pentahydroxylated in C4-C26 ·

Mention may in particular be made of diethyl sebacate, diisopropyl sebacate, diisopropyl adipate, di n-propyl adipate, dioctyl adipate, diisostearyl adipate, dioctyl maleate, undecylenate glyceryl, octyldodecyl stearoyl stearate, pentaerythrityl monoricinoleate, pentaerythrityl tetrapelargonate, pentaerythrityl, propylene glycol dicaprylate, propylene glycol dicaprate, tridecyl citrate triidyl citrate, triidyl acetate glyceryl trilactate, glyceryl trioctanoate, trioctyldodecyl citrate, trioleyl citrate, propylene glycol dioctanoate, neopentyl glycol diheptanoate, pentaerythryl tetraonctanoate and diethylenetarate tetraoctanoate polyethylene glycol.

Among the esters mentioned above, use is preferably made of ethyl, isopropyl, myristyl, cetyl, stearyl palmitates, ethyl-2-hexyl palmitate, 2octyldecyl palmitate, myristates of alkyls such as isopropyl, butyl, cetyl, 2-octyldodecyl myristate, hexyl stearate, propylene glycol dicaprylate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2hexyldecyl laurate, isononyl isononanate and cetyl octanoate.

Among the liquid fatty esters, it is possible to use esters and diesters of sugars and fatty acids in C6-C30, preferably in C12-C22

By "sugar" is meant oxygenated hydrocarbon compounds which have several alcohol functions, with or without aldehyde or ketone function, and which contain at least 4 carbon atoms. These sugars can be monosaccharides, oligosaccharides or polysaccharides.

Preferably, these said sugars are chosen from sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, lactose, and their derivatives, in particular alkylated, such than methylated derivatives like methylglucose.

The sugar and fatty acid esters can be chosen in particular from the group comprising the esters or mixtures of sugar esters described above and of C6-C30, preferably C12-C22 fatty acids, linear or branched, saturated or unsaturated.

If unsaturated, these compounds can have one to three carbon-carbon double bonds, conjugated or not.

The esters according to this variant can also be chosen from mono-, di-, tri- and tetraesters, polyesters and their mixtures.

These esters can be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates, arachidonates, and their mixtures such as in particular the mixed oleo-palmitate, oleo-stearate, palmitostearate esters.

More particularly, mono- and diesters are used, and in particular mono- or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates, oleostearates, sucrose, glucose or methylglucose or also methylglucose dioleate (Glucate® DO).

Among the sugar esters, it is possible to use the pentaerythrityl esters, preferably pentaerythrityl tetra-iso-stearate, pentaerythrityl tetra-octanoate, the hexaesters of caprylic and capric acids in mixture with dipentaerythritol.

Among the natural or synthetic esters of mono-, di- or triacids with glycerol, vegetable or synthetic oils can be used.

More particularly, the said vegetable or synthetic oil (s) are chosen from triglyceride oils of vegetable or synthetic origin, such as liquid triglycerides of fatty acids containing from 6 to 30 carbon atoms such as heptanoic or octanoic acid triglycerides or alternatively , for example sesame, soybean, coffee, safflower, borage, sunflower, olive, almond, apricot, camellia, bambara pea, avocado, mango, bran oils rice, cotton, rose, kiwi seeds, sea buckthorn pulp, blueberry seeds, poppy seeds, orange seeds, sweet almonds, palm, copra, vernoia, marjoram , baobab, rapeseed, ximenia, pracaxi, the triglycerides of caprylic / capric acids such as those sold by the company STEARINERIES DUBOIS or those sold under the names Miglyol® 810, 812 and 818 by the company DYNAMIT NOBEL, oil jojoba, be oil shea urea.

Preferably, as liquid esters which can be used according to the invention, plant-based triglycerides are used, in particular the oils chosen from avocado oil, olive oil, camellia oil, l apricot almond oil, and mixtures thereof and esters of C4-C22 di- or tricarboxylic acids and C1-C22 alcohols, in particular 1,3-propanediol dicaprylate.

The term “fatty acid” means an unsalified fatty acid, that is to say that the fatty acid must not be in the form of generally soluble soap, that is to say that it must not be salified by a base.

More particularly, the liquid fatty acids which can be used according to the invention are chosen from the acids of formula RCOOH, where R is a saturated or unsaturated, linear or branched radical, preferably comprising from 7 to 39 carbon atoms.

Preferably, R is a C7-C29 alkyl or C7-C29 alkenyl group, better still a C12-C24 alkyl or C12-C24 alkenyl group. R may be substituted by one or more hydroxy groups and / or one or more carboxyl groups.

Preferably, the liquid fatty acid (s) are chosen from oleic acid, linoleic acid and isostearic acid.

The fatty substance (s) which can be used in the compositions used in the process of the invention can also be chosen from non-liquid fatty substances at ambient temperature (25 ° C) and at atmospheric pressure (760 mm of Hg, ie 1,013.10 ⁵ Pa).

The term “non-liquid fatty substance” is preferably understood to mean a solid compound or a compound having a viscosity greater than 2 Pa.s at a temperature of 25 ° C. and at a shear rate of 1 s ′ ¹ .

More particularly, the non-silicone “non-liquid” fatty substances are chosen from fatty alcohols, fatty acid and / or fatty alcohol esters, non-silicone waxes, fatty amines and ethers, which are non-liquid and preferably solid.

More particularly, the non-liquid fatty alcohols which can be used according to the invention are chosen from saturated or unsaturated, linear or branched alcohols, containing from 8 to 30 carbon atoms.

Preferably, mention may be made, for example, of cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol). More particularly, cetylstearyl alcohol is used.

The fatty acid ester (s) and / or non-liquid fatty alcohols which can be used according to the invention are generally chosen from solid esters derived from C9-C26 fatty acids and from C9-C26 fatty alcohols

Preferably, examples that may be mentioned include octyldodecyl behenate, isoketyl behenate, cetyl lactate, stearyl octanoate, octyl octanoate, cetyl octanoate, oleate decyl, myristyl stearate, octyl palmitate, octyl pelargonate, octyl stearate, alkyl myristates such as cetyl, myristyl or stearyl myristate, and hexyl stearate .

The non-silicone wax (es) are chosen in particular from Carnauba wax, Candelila wax, Alfa wax, paraffin wax, ozokerite, vegetable waxes such as olive wax, rice wax, hydrogenated jojoba wax or absolute flower waxes such as essential blackcurrant flower wax sold by the company BERTIN (France), animal waxes such as beeswax, or modified beeswax (cerabellina) and ceramides or the like.

Ceramides or ceramide analogs, such as natural or synthetic glycoceramides can be chosen from the compounds corresponding to the following formula (VI):

R'CHOH — CH — CH ₂ OR

NH

C = O ^R '(VI) in which:

- R 'denotes an alkyl radical, linear or branched, saturated or unsaturated, derived from C14-C30 fatty acids, this radical possibly being substituted by a hydroxyl group in the alpha position, or a hydroxyl group in the omega position esterified by an acid C16-C30 saturated or unsaturated fat;

- R ”denotes a hydrogen atom or a (glycosyl) n, (galactosyl) m or sulfogalactosyl radical, in which n is an integer varying from 1 to 4 and m is an integer varying from 1 to 8;

- R ’” denotes a C 15 -C 26 hydrocarbon radical, saturated or unsaturated in the alpha position, this radical possibly being substituted by one or more C 1 -C 14 alkyl radicals;

it being understood that in the case of natural ceramides or glycoceramides, R ′ ”can also denote an alpha-hydroxyalkyl radical in Ci ₅ -C 26, the hydroxyl group being optionally esterified by an alpha-hydroxy acid in C16-C30 ·

The preferred ceramides in the context of the present invention are those described by DOWNING in Arch. Dermatol, Vol. 123, 13811384, 1987, or those described in French patent FR 2,673,179.

The ceramide (s) more particularly preferred according to the invention are the compounds for which R ′ denotes a saturated or unsaturated alkyl derived from C16-C22 fatty acids, R ″ denotes a hydrogen atom and R ″ ″ denotes a linear radical saturated with C15.

Preferably, the following compounds can be chosen in particular: N-linoleoyldihydrosphingosine, Noleoyldihydrosphingosine, N-palmitoyldihydrosphingosine, Nstearoyldihydrosphingosine, N-behenoyldihydrosphingosine and a mixture of these compounds.

Even more preferably, ceramides are used for which R 'denotes a saturated or unsaturated alkyl radical derived from fatty acids, R ”denotes a galactosyl or sulfogalactosyl radical and R'” denotes a group -CH = CH- (CH ₂ ) i2 -CH3.

Other waxes or waxy raw materials which can be used according to the invention are in particular marine waxes such as those sold by the company SOPHIM under the reference M82, polyethylene or polyolefin waxes in general.

The non-liquid fatty ethers which can be used according to the invention are chosen from dialkyl ethers, in particular diketyl ether and distearyl ether, alone or as a mixture.

Preferably, the non-silicone fatty substance (s) which can be used according to the invention are chosen from hydrocarbons, in particular linear or branched C6-Ci6 alkanes and linear or branched hydrocarbons, of animal or synthetic mineral origin, of more than 16 carbon atoms, such as paraffin oils, and their derivatives, petroleum jelly, petroleum jelly oil; fatty acid esters, in particular oils of vegetable origin and esters of di- or tricarboxylic acids of C4-C22 and of alcohols of C1-C22, these esters being more preferably chosen from triglycerides of vegetable origin , liquid fatty alcohols and their mixtures.

The fatty substance (s) which can be used according to the invention generally represent from 1 to 50% by weight, preferably from 2 to 30% by weight, more preferably from 5 to 15% by weight relative to the total weight of each composition containing them.

The compositions which can be used in the process according to the invention also comprise water which generally represents from 10 to 90% by weight, preferably from 10 to 80% by weight, preferably from 10 to 70% by weight, relative to the total weight of each composition.

The compositions which can be used in the process according to the invention can contain cosmetically acceptable organic solvents, including more particularly alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol, and phenylethyl alcohol, or polyols or polyol ethers such as, for example, the monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or its ethers such as, for example, propylene glycol monomethyl ether, butylene glycol, dipropylene glycol and also the alkyl ethers of diethylene glycol such as, for example, monoethyl ether or monobutyl ether of diethylene glycol.

The solvents can then represent from 0.5 to 20% by weight, preferably from 2 to 10% by weight, relative to the total weight of each composition containing them.

The pH of the compositions which can be used in the process according to the invention is generally between 2 and 11.

The reducing compositions according to the invention generally have a pH of between 7 and 11, preferably between 8 and 10.

The oxidizing compositions according to the invention generally have a pH of between 2 and 7, preferably between 2.5 and 4.

The compositions which can be used in the process according to the invention can also contain additives such as natural or synthetic polymeric thickeners, anionic, amphoteric or zwitterionic, nonionic or cationic, associative or not, nonpolymeric thickeners such as electrolytes, polymers styling, sugars, nacrants, opacifiers, sunscreens, vitamins or provitamins, perfumes, dyes, organic or mineral particles, preservatives, pH stabilizers.

A person skilled in the art will take care to choose any additives and their quantity so that they do not harm the properties of the compositions which can be used in the process of the present invention.

These additives can be present in the compositions which can be used in the process according to the invention in an amount ranging from 0 to 50% by weight relative to the total weight of each composition containing them.

The compositions used in the process according to the invention can be in the form of wax, paste, more or less fluid or thick cream, gel, foam, spray, lotion.

The compositions described above, whether or not previously mixed, are applied to the dry or wet keratin fibers, sequentially or simultaneously.

The compositions are usually left in place on the fibers for a duration ranging, in general, from 1 minute to 1 hour, preferably from 5 minutes to 30 minutes for each composition.

The method according to the invention may optionally include a step of raising the temperature, in particular using a straightening iron (flat pliers) and or a hair dryer.

The temperature during the temperature rise step can range from 50 to 230 ° C. In particular, when using a straightening iron, the temperature of the temperature raising step can range from 90 to 230 ° C, preferably from 150 to 210 ° C.

Preferably, the step of raising the temperature is carried out after the application of the composition (s) comprising the diamine (s).

The process can possibly include a step of winding the hair around curlers.

Before and after the process according to the invention, the keratin fibers can optionally be washed with a shampoo followed by rinsing with water, before being dried or left to dry.

The process according to the invention can be repeated in order to increase the effects.

Preferably, the method according to the invention is a method of straightening or straightening the hair.

The present invention also relates to a kit comprising at least two compartments:

a first compartment comprising a reducing composition which comprises one or more reducing agents as defined above,

a second compartment comprising an oxidizing composition which comprises one or more oxidizing agents as defined above,

one or more diamines as defined above included in the reducing composition and / or in the oxidizing composition and / or in one or more separate composition (s) included in one or more additional compartments, being it is understood that the composition (s) containing the said diamine (s) does not comprise (include) maleic acid or salts of maleic acid, and preferably does not include (include) monomeric ethylenically unsaturated compounds.

The following examples illustrate the present invention and should not be considered in any way as limiting the invention.

EXAMPLES:

1) Preparation of “support” compositions

Compositions A, B and C are prepared by mixing the ingredients according to Table I below.

The contents are indicated in grams of active ingredient.

Table I

Reducing composition A

Ingredients Content Ammonium thioglycolate 8.5 Dammonium dithioglycolate 2.5 Ammonium bicarbonate 2.5 Ethanolamine 1 Behentrimonium chloride 4.6 Cetrimonium chloride 4 Ceteth-2 3 Cetearyl alcohol 8 Cetyl palmitate 2 Pentasodium pentetate 0.2 Perfume 0.6 Water qs 100

Fixing composition B

Ingredients Content Hydrogen peroxide 4.8 Glycerin 1.5 Steareth-2 5 Behentrimonium chloride 1 Sodium salicylate 0.035 Tetrasodium pyrophosphate 0.04 Tetrasodium etidronate 0.2 Perfume 0.4 Phosphoric acid qs pH = 3 Water qs 100

Care composition C

Ingredients Content Cetearyl alcohol 4 Behentrimonium chloride 4 Hydrogenated starch hydrolyzate 5 Dimethicone (and) Amodimethicone 1.5 Cetyl esters 0.8 Olive oil 2 Glycerin 11.5 Propylene glycol 5 Phenoxyethanol 0.7 Citric acid Qs pH 3.5 Water Qsp 100

2) Preparation of the compositions containing one or more diamines

The compositions D, E, F and G which can be used in the process according to the invention are prepared by mixing the ingredients according to the table

II below.

Table II

Composition D

Ingredients Content 4,9-dioxa-1,12-dodecanedi amine 10 Water qs 100

Reducing composition E

Ingredients Content 4,9-dioxa-1,12-dodecanedi amine 10 Reducing composition A qs 100

Fixing composition F

Ingredients Content 4,9-dioxa-1,12-dodecanedi amine 10 Fixing composition B qs 100

Care composition G

Ingredients Content 4,9-dioxa-1,12-dodecanedi amine 10 Care composition C qs 100

3) Permanent hair deformation processes

Method 1 according to the invention

Method 1 according to the invention comprises the following successive steps:

1) a shampoo marketed under the name Optimizer Pre-Form by L'Oréal Professionnel (shampoo usually used before perms and straightenings) is applied to the hair,

2) the hair is rinsed,

3) the reducing composition A is applied,

4) 15 min exposure,

5) the hair is rinsed,

6) the composition (Composition D) is applied,

7) 5 min exposure,

8) the hair is rinsed,

9) the fixing composition B is applied,

10) 10 min exposure,

11) the hair is rinsed.

Method 1 according to the invention makes it possible to obtain good results in terms of smoothing and degradation of the fiber.

Method 2 according to the invention

Method 2 according to the invention comprises the following successive steps:

1) a shampoo marketed under the name Optimizer Pre-Form by L'Oréal Professionnel (shampoo usually used before perms and straightenings) is applied to the hair,

2) the hair is rinsed,

3) the reducing composition E is applied,

4) 15 min exposure,

5) the hair is rinsed,

6) the fixing composition B is applied,

7) 10 min exposure,

8) the hair is rinsed.

Method 2 according to the invention makes it possible to obtain good results in terms of smoothing and degradation of the fiber.

Method 3 according to the invention

Method 3 according to the invention comprises the following successive steps:

1) a shampoo marketed under the name Optimizer Pre-Form by L'Oréal Professionnel (shampoo usually used before perms and straightenings) is applied to the hair,

2) the hair is rinsed,

3) the reducing composition A is applied,

4) 15 min exposure,

5) the hair is rinsed,

6) the fixing composition F is applied,

7) 10 min exposure,

8) the hair is rinsed.

Method 3 according to the invention makes it possible to obtain good results in terms of smoothing and degradation of the fiber.

Method 4 according to the invention

Method 4 according to the invention comprises the following successive steps:

1) a shampoo marketed under the name Optimizer Pre-Form by L'Oréal Professionnel (shampoo usually used before perms and straightenings) is applied to the hair,

2) the hair is rinsed,

3) the reducing composition A is applied,

4) 15 min exposure,

5) the hair is rinsed,

6) the fixing composition B is applied,

7) 10 min exposure,

8) the hair is rinsed,

9) composition G is applied,

10) pose 10 mn,

11) the hair is rinsed.

Method 4 according to the invention makes it possible to obtain good results in terms of smoothing and degradation of the fiber.

Claims (16)

1. A process for permanent deformation of keratin fibers, in particular of the hair, comprising the implementation: i) one or more diamine (s), and ii) one or more reducing agent (s), said diamine (s) and said reducing agent (s) being used used in a single composition or in separate compositions applied to the fibers, it being understood that the composition (s) containing the said diamine (s) does not comprise (include) maleic acid nor of maleic acid salts. 2. Method according to claim 1, characterized in that the diamine or diamines are chosen from the compounds of formula (I) below: in which Ri, R2, R3 and R4, independently of one another, represent a hydrogen atom or an alkyl radical comprising from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, and more preferably represent a hydrogen atom, R, R ', R ”and R” ”, independently of each other, represent a hydrogen atom, an alkyl radical comprising from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, an alkoxyalkyl radical comprising from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms or an alkoxyamine radical comprising from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, and more preferably represent, independently of each others, a hydrogen atom or a methyl radical, n, p and q, independently of one another, represent a number varying from 0 to 100, preferably from 0 to 20, and more preferably varying from 1 to 15, being understood that for any value n, p or q greater than or equal to 2, the radicals R, R ', R ”and R” ”can be different from one motif CRR' or CR” R ”” to the other. 3. Method according to claim 2, characterized in that the diamine or diamines are chosen from the compounds of formula (I) in which: - Ri, R2, R3 and R4 are hydrogen atoms, - R and R "are hydrogen atoms, - R ’and R’ ”, independently of each other, are chosen from a hydrogen atom or a methyl radical, - n and q vary from 1 to 5, preferably from 1 to 3, better are equal to 2, - p ranges from 1 to 15, preferably ranges from 2 to 13. 4. Method according to any one of the preceding claims, characterized in that the diamine or diamines are chosen from polyoxyalkylenated diamines, preferably polyoxyethylenated diamines and polyoxypropylenated diamines. 5. Method according to any one of the preceding claims, characterized in that the diamine (s) represent from 1 to 50% by weight, preferably from 2 to 30% by weight, and more preferably from 5 to 15% by weight, relative to the total weight of each composition containing them. 6. Method according to any one of the preceding claims, characterized in that the reducing agent or agents are chosen from sulfur-reducing agents, preferably from cysteine, cysteamine, thioglycolic acid and its salts or esters, sulfites , bisulfites, and mixtures of these compounds, more preferably the reducing agent or agents are chosen from thioglycolic acid and its salts, and more preferably still the reducing agent is ammonium thioglycolate. 7. Method according to any one of the preceding claims, characterized in that the reducing agent or agents represent from 0.05 to 30% by weight, preferably from 1 to 20% by weight, and more preferably from 4 to 11% by weight, relative to the total weight of the composition containing them. 8. Method according to any one of the preceding claims, characterized in that the composition (s) containing the diamine (s) does not comprise (comprise) monomeric compounds containing ethylenic unsaturation. 9. Method according to any one of the preceding claims, characterized in that the said diamine (s) and the said reducing agent (s) are used in separate compositions, the composition (s) comprising the said diamine (s) being applied before and / or after the composition comprising the said reducing agent (s), and preferably after. 10. Method according to any one of the preceding claims, characterized in that it further comprises the use of one or more oxidizing agents, present in a composition distinct from the composition containing the said reducing agent (s) and applied to keratin fibers after this. 11. Method according to claim 10, characterized in that the oxidizing agent or agents are chosen from hydrogen peroxide, urea peroxide, bromates or ferricyanides of alkali metals, peroxygenated salts, and mixtures of these compounds , preferably are chosen from hydrogen peroxide and alkaline bromates, and more preferably, the oxidizing agent is hydrogen peroxide. 12. Method according to claim 10 or 11, characterized in that the oxidizing agent (s) represent from 0.1 to 8% by weight, preferably from 0.2 to 5% by weight, relative to the total weight of the composition containing them. 13. Method according to any one of claims 10 to 12, characterized in that the said diamine or diamines are included in the composition comprising the said reducing agent (s) and / or in the composition comprising the said oxidizing agent (s). 14. Method according to any one of claims 10 to 12, characterized in that it comprises the sequential application to the keratin fibers of at least three separate compositions: a first composition comprising the said reducing agent (s), then a second composition comprising the said oxidizing agent (s), and a third composition comprising the said diamine (s) applied before said first composition and / or, simultaneously with the first composition and / or after the first composition, and before the second composition and / or simultaneously with the second composition and / or after the second composition, and preferably the third composition comprising the said diamine (s) is applied between the first composition and the second composition or simultaneously with the second composition. 15. Method according to claim 14, characterized in that it comprises the sequential application to the keratin fibers of at least three distinct compositions: a first composition comprising the said reducing agent (s), then a second composition comprising the said diamine (s), then - A third composition comprising the said oxidizing agent (s). 16. Kit comprising at least two compartments: a first compartment comprising a reducing composition which comprises one or more reducing agents, preferably as defined in claims 6 and 7, a second compartment comprising an oxidizing composition which comprises one or more oxidizing agents, preferably as defined in claims 11 and 12, - one or more diamines, preferably as defined in claims 2 to 5, being included in the reducing composition and / or in the oxidizing composition and / or in one or more separate compositions included in one or more 5 additional compartments, it being understood that the composition (s) containing the said diamine (s) does not include (include) maleic acid or salts of maleic acid, and preferably does not include (include) monomeric compounds unsaturated 10 ethylenic.