FR3058054B1 - PROCESS FOR PERMANENT DEFORMATION OF HAIR USING DIAMINE AND ALKALINE OR ALKALINE-EARTH HYDROXIDE - Google Patents

Abstract

The present invention relates to a method of permanent deformation of keratinous fibers, in particular hair, which comprises the application to the fibers of: i) one or more diamines, and ii) one or more alkaline hydroxide (s) (s) or alkaline earth, said diamine (s) and the alkali or alkaline earth hydroxide (s) being applied in one and the same composition, or in separate compositions, it being understood that the composition (s) containing said diamine (s) does not comprise maleic acid or salts of maleic acid. The present invention also relates to kits suitable for carrying out this method.

Description

Method of permanent hair deformation using a diamine and an alkaline or alkaline-earth hydroxide

The present invention relates to a method of permanent deformation of keratinous fibers, in particular hair, which comprises the use of one or more diamines and one or more alkaline or alkaline-earth hydroxides, contained in one or more compositions applied to said fibers.

The present invention also relates to kits comprising at least two compartments, suitable for the implementation of this method.

Many people are unhappy with the appearance of their hair, especially those with curly hair are more likely to get straight hair and, conversely, those with straight hair want to have curly hair.

The first of the techniques usually used to obtain a permanent deformation of the hair consists, first of all, in opening the disulfide bonds -SS- of keratin (keratocystin) using a composition containing a suitable reducing agent. (reduction step) then, after having rinsed the hair thus treated, generally with water, to reconstitute in a second time said disulfide bonds by applying to the hair previously put under tension (for example by hair curlers), an oxidizing composition (Oxidation step, also called fixation) so as finally to give the hair the desired shape.

This technique allows indifferently to achieve, either the waving of the hair, their straightening, their curing or smoothing.

The second technique for obtaining a permanent deformation of hair consists in performing an operation called lanthionization, using a composition containing a base belonging to the family of hydroxides. It leads to replace disulfide bonds (-CH2-S-S-CH2-) by lanthionine bonds (-CEE-S-CEE-).

The compositions generally used for the lanthionization contain as a base a hydroxide such as an alkali or alkaline earth metal hydroxide. Compared with the first technique described above using a reducing agent, this lanthionization technique does not require a fixation step, since the formation of lanthionine bridges is irreversible. It is therefore done in one step. However, it is usual to perform a neutralizing shampoo after this type of process to lower the pH of the fiber.

The straightening products may be in the form of ready-to-use compositions or in the form of kits of at least two compositions to be mixed at the time of use, one of which comprises hydroxides in high concentration.

These two techniques make it possible to perform either the waving of the hair, or their straightening, curing or smoothing. However, the lanthionization technique is mainly used for shaping naturally frizzy hair.

These techniques used for smoothing are generally implemented on curly or bulky hair in order to obtain more or less pronounced smoothing and a reduction in the volume and the apparent mass of the hair.

However, such a technique is not entirely satisfactory. Indeed, although the latter is very effective in changing the shape of the hair, it is often degrading for hair fibers, which is mainly due to high levels of hydroxides and / or very alkaline pH and different more or less long exposure times of these compositions.

This technique can thus induce in the long term an alteration of the quality and integrity of the fibers, in particular capillaries, resulting in a reduction of their cosmetic properties, such as their gloss, their softness, their ease of disentangling and a degradation of their mechanical properties. , more particularly their mechanical strength.

Furthermore, it has also been found that the use of these alkaline agents can cause discomfort of the scalp (irritation, itching, etc.).

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

It has now been discovered, surprisingly, that a method of permanent deformation of keratinous fibers, in particular straightening fibers, in particular hair, which comprises the use of one or more diamines and one or more alkaline hydroxides or alkaline earth applied sequentially or simultaneously on the keratinous fibers allowed to achieve the desired properties in terms of integrity, quality and cosmetics keratin fibers while obtaining a good quality deformation and durable keratin fibers.

The subject of the present invention is therefore a process for the permanent deformation of keratinous fibers, in particular hair straightening fibers, in particular hair comprising the application to the fibers of: i) one or more diamines, and ii) a or more alkali or alkaline earth hydroxide (s), wherein said diamine (s) and said alkaline or alkaline earth hydroxide (s) are applied in a single composition, or in separate compositions, it being understood that the composition (s) containing said diamine (s) does not comprise (include) maleic acid or maleic acid salts.

The implementation of this method makes it possible to obtain a permanent deformation of the keratinous fibers, in particular a straightening, of good quality and remaining after several shampoos while preserving the quality and the integrity of the keratinous fibers. In addition, the implementation of this method makes it possible to provide good cosmetic properties, in particular gloss and softness to the touch, to keratinous fibers.

Optionally, the method of the invention can also implement one or more acids not containing ethylenic unsaturation. The invention also relates to kits suitable for implementing the method of the invention.

A first kit comprises at least two compartments: a first compartment comprising a first composition which comprises one or more alkaline or alkaline-earth hydroxides, a second compartment comprising a second composition which comprises one or more acids which do not contain ethylenic unsaturation, one or more diamines being included in the first composition and / or in the second composition and / or in one or more separate compositions included in one or more additional compartments, it being understood that the composition (s) containing the or said diamines comprise (include) no maleic acid or maleic acid salts, and preferably do not include (include) ethylenically unsaturated monomeric compounds.

A second kit comprises at least two compartments: a first compartment comprising a first composition which comprises one or more alkaline or alkaline earth hydroxides, a second compartment comprising a second composition which comprises one or more diamines, optionally one or a plurality of acids not containing ethylenic unsaturation, included in the second composition and / or in one or more separate compositions included in one or more additional compartments, it being understood that the composition (s) containing said diamine (s) does not include maleic acid or maleic acid salts, and preferably does not include any monomeric ethylenically unsaturated compounds.

The composition comprising the alkali or alkaline-earth hydroxyl or hydroxides applied to the keratin fibers may result from the mixing, at the time of use, of at least one composition comprising the alkali or alkaline-earth metal hydroxide or hydroxides and at least one other composition. Other characteristics and advantages of the invention will emerge more clearly on reading the description and examples which follow.

As explained above, the process according to the invention comprises the use of one or more diamines.

In a preferred manner, the diamine or diamines are chosen from the following compounds of formula (I):

in which R 1, R 2, R 3 and R 4, 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, R, R ', R "and R'", independently of each other, represent a hydrogen atom, an alkyl radical comprising from 1 to with 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, independently of each other, represent a number ranging from 0 to 100, preferably from 0 to 20, it being understood that for any higher value n, p or q or equal to 2, the radicals R, R ', R "and R'" may be different from one CRR 'or CR "R'" to the other.

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

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

Preferably in the formula (I), R, R ', R "and R'" represent, independently of one another, a hydrogen atom or a methyl radical.

Preferably in the 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: R 1, R 2, R 3 and R 4 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 2, p varies 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. Examples of polyoxyalkylenated diamines that may be mentioned are the diamines sold under the trade name 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 especially 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 diamines EDR-148 and EDR-176.

In a very particularly preferred manner, 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 about 2, (JEFFAMINE® D-230), O, O'-bis (2-aminopropyl) polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol with an average number of propylene glycol units equal to about 3.6 and one number of ethylene glycol units equal to about 9 (JEFFAMINE® ED-600), or with a number of propylene glycol units equal to about 6 and an average number of ethylene glycol units equal to about 12.5 (JEFFAMINE® ED -900) and 2,2 '- (ethylenedioxy) bis (ethylamine) (JEFFAMINE® EDR-148).

Among the oxyalkylenated diamines, there may also be mentioned 4,9-dioxa-1,12-dodecanediamine or 4,7,10-trioxa-1,3-tridecanediamine.

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 composition (s) containing the diamine (s) does not include maleic acid or maleic acid salt.

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

Monomeric compound with ethylenic unsaturation 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. As ethylenically unsaturated monomeric compounds, there may be mentioned maleic acid, fumaric acid, (meth) acrylic acid and their salts.

As explained above, the process according to the invention also uses one or more alkali or alkaline earth hydroxides.

Alkali or alkaline earth hydroxide means a compound of the following formula:

M (OH) X with M being a metal selected from alkali metals (group 1 of the periodic table of elements) or alkaline earth metals (group 2 of the periodic table of elements), where x is a number equal to 1 or 2.

Preferably, the alkali or alkaline earth metal hydroxide (s) are chosen from sodium hydroxide, lithium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide and a mixture of these. compounds, more preferably from sodium hydroxide, lithium hydroxide, calcium hydroxide and a mixture of these compounds.

The alkali or alkaline earth metal hydroxide or hydroxides generally represent from 0.5 to 60% by weight, preferably from 1 to 55% by weight, better still from 2 to 50% by weight relative to the total weight of the composition containing them.

The composition comprising the alkali or alkaline earth metal or hydroxides may further comprise guanidine carbonate.

In this particular embodiment, the composition comprising the alkali or alkaline earth metal hydroxide (s) and the guanidine carbonate may result from the mixture of at least one composition comprising the alkali or alkaline earth metal hydroxide (s) and at least one composition comprising guanidine carbonate. The concentration of guanidine carbonate in the composition further comprising the alkali or alkaline earth metal hydroxide (s) can vary from 0.1 to 60% by weight, preferably from 1 to 50% by weight, better still from 2 to 40% by weight. weight relative to the total weight of the composition.

As explained above, in the process according to the invention, the diamine (s) and the alkali or alkaline-earth metal (s) hydroxide (s) are used in one and the same composition or in separate compositions.

Thus, in a first mode of implementation of the process according to the invention, the diamine (s) and the alkali or alkaline earth hydroxyl (s) are present in one and the same composition.

In a second embodiment of the process according to the invention, the diamine (s) and the alkali or alkaline earth hydroxide (s) are used in separate compositions, the composition (s) comprising said diamine (s). (s) being applied before and / or after the composition comprising the alkali or alkaline earth metal hydroxide (s).

In this second embodiment, the method according to the invention generally comprises i) a step of application to the keratinous fibers, preferably the hair of a composition comprising one or more diamines as defined above and ii ) an application step on the keratinous fibers, preferably the hair of a composition comprising one or more alkali or alkaline earth hydroxides as defined above.

In a variant of this second embodiment of the process according to the invention, the composition comprising the diamine or diamines is applied before the composition comprising the alkali or alkaline-earth metal hydroxide (s).

In a variant of this second embodiment of the process according to the invention, the composition comprising the diamine or diamines is applied after the composition comprising the alkali or alkaline-earth metal hydroxide (s).

Preferably, the composition (s) comprising said diamine (s) is (are) applied (s) after the composition comprising the alkali or alkaline earth metal hydroxide (s).

The process according to the invention may also comprise the application to the fibers of one or more acids which do not contain ethylenic unsaturation, in a composition distinct from the composition containing the alkali or alkaline earth metal hydroxide (s) and applied to the fibers after it.

An acid which does not contain ethylenic unsaturation means an acid, preferably a carboxylic acid, not comprising a carbon-carbon double bond. The acid which does not contain ethylenic unsaturation is preferably citric acid.

The acid or acids not containing ethylenic unsaturation generally represent from 0.01 to 15% by weight, preferably from 0.05 to 10% by weight, relative to the total weight of the composition containing them.

The acid or acids not containing ethylenic unsaturation can be in the composition comprising the diamine (s) or in a separate composition.

In one embodiment of the process according to the invention, the diamine or diamines, the alkali or alkaline earth hydroxide (s) and the acid (s) not containing ethylenic unsaturation are applied in separate compositions.

Thus, in one variant of this embodiment, the method comprises the sequential application on the keratinous fibers of at least three distinct compositions: a first composition comprising the alkali or alkaline earth hydroxyl or hydroxides as defined herein; above, then - a second composition comprising the acid (s) not containing ethylenic unsaturation as defined above, and - a third composition comprising the diamine or diamines applied before the 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 said diamine or diamines is applied between the first composition and the second composition or simultaneously with the second composition.

Preferably, in the variant of this embodiment, the process comprises the sequential application on the keratinous fibers of at least three distinct compositions: a first composition comprising the alkali or alkaline earth hydroxyl or hydroxides as defined above, then - a second composition comprising the diamine (s) as defined above, then - a third composition comprising the acid (s) not containing ethylenic unsaturation as defined above.

In another embodiment of the process according to the invention, the diamine or diamines are included in the composition comprising the alkali metal or alkaline earth metal hydroxide (s) and / or in the composition comprising the acid (s) containing no such acid (s). ethylenic unsaturation.

In a first variant of this other embodiment, the diamine or diamines are included in the composition comprising the alkali or alkaline earth hydroxyl or said hydroxides.

Thus, in this first variant of this alternative embodiment of the process according to the invention, the process comprises the sequential application on the keratinous fibers of at least two compositions: i) a first composition comprising the diamine (s) and the alkali or alkaline earth metal hydroxide or hydroxides, and then ii) a second composition comprising the acid or acids which do not contain ethylenic unsaturation.

In a second variant of this alternative embodiment, the diamine or diamines are included in the composition comprising the acid or acids not containing ethylenic unsaturation.

Thus, in this second variant of this alternative embodiment of the process according to the invention, the process comprises the sequential application on the keratin fibers of at least two compositions: i) a first composition comprising the hydroxide (s) alkali or alkaline earth, and ii) a second composition comprising the diamine (s) and the acid (s) not containing ethylenic unsaturation.

In a third variant of this alternative embodiment of the process according to the invention, the diamine or diamines are included in the composition comprising the alkali or alkaline-earth metal hydroxide (s) and in the composition comprising the acid (s) not containing ethylenic unsaturation.

Thus, in this third variant of this alternative embodiment of the process according to the invention, the process comprises the sequential application on the keratin fibers of at least two compositions: i) a first composition comprising the diamine (s) and the alkali or alkaline earth metal hydroxide or hydroxides and then ii) a second composition comprising the diamine (s) and the acid (s) not containing ethylenic unsaturation.

For this alternative embodiment, an additional composition containing the diamine or diamines may be applied before and / or after the composition containing the alkali or alkaline-earth metal hydroxide (s) and / or after the composition containing the acid (s) not comprising no ethylenic unsaturation.

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

The nonionic surfactant (s) that can be used in the process according to the invention are described for example in "Handbook of Surfactants" by M. R. PORTER, Blackie & Son (Glasgow and London), 1991, pp 116-178. They are chosen in particular from alcohols, alpha-diols, (C 1 -C 20) alkylphenols, these compounds being polyethoxylated, polypropoxylated and / or polyglycerolated and having at least one fatty chain comprising, for example, from 8 to 18 carbon atoms. carbon, the number of ethylene oxide groups and / or propylene oxide may range from 2 to 50 and the number of glycerol groups may range from 2 to 30.

Mention may also be made of copolymers of ethylene oxide and propylene oxide, esters of polyoxyalkylenated fatty acids, alkylpolyglycosides, optionally oxyalkylenated, esters of alkylglucosides, derivatives of N-alkylglucamine and N-acyl-methylglucamine, aldobionamides and amine oxides.

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

The term "anionic surfactant" is understood to mean a surfactant comprising as ionic or ionizable groups only anionic groups. These anionic groups are preferably chosen from the groups CO2H, CO2 ', SO3H, SO3', OSO3H, oso3; O2PO2H, O2PO2H-, O2PO22 ·.

The anionic surfactant (s) that may be used in the process of the invention are chosen from alkyl sulphates, alkyl ether sulphates, alkyl amido ether sulphates, alkylaryl polyether sulphates, monoglyceride sulphates, alkyl sulphonates, alkyl amide sulphonates, alkyl aryl sulphonates, alpha-olefin-sulfonates, paraffin-sulfonates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamide-sulfosuccinates, alkylsulfoacetates, acylsarcosinates, acylglutamates, alkylsulfosuccinamates, acylisethionates and N-acyltaurates, monoesters salts of alkyl and polyglycoside-polycarboxylic acids, acyllactylates, D-galactoside-uronic acid salts, alkyl ether-carboxylic acid salts, alkyl aryl ether carboxylic acid salts, alkyl acid salts amidoether carboxylic acids; or the non-salified forms of all these compounds, the alkyl and acyl groups of all these compounds having from 6 to 24 carbon atoms and the aryl group denoting a phenyl group.

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

The salts of C 6 -C 24 alkyl monoesters and of polyglycoside-polycarboxylic acids may be chosen from C 6 -C 24 alkyl polyglycoside-citrates, C 6 -C 24 alkyl polyglycoside-tartrates and polyglycoside-sulphosuccinates. C6-C24 alkyl.

When the anionic surfactant (s) are in salt form, they are not in the form of zinc salts, and they may be chosen from alkali metal salts such as the sodium or potassium salt and preferably sodium salt, ammonium salts, amine and especially aminoalcohol salts, and alkaline earth metal salts such as magnesium salt. By way of example of aminoalcohol salts, mention may be made in particular of the salts of mono-, di- and tri-ethanolamine, the salts of mono-, di- or tri-isopropanolamine, the salts of 2-amino- 2-methyl-1-propanol, 2-amino-2-methyl-1,3-propanediol and tris (hydroxymethyl) amino methane.

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

Alkyl (C6-C24) sulphates, alkyl (C6-C24) ether sulphates, optionally oxyethylenated, comprising from 2 to 50 ethylene oxide units, and mixtures thereof, in particular in the form of alkali metal salts, are preferably used. alkaline earth, ammonium, aminoalcohol. More preferably, the anionic surfactant (s) are chosen from (C 10 -C 20) alkyl ether sulphates, and in particular sodium lauryl ether sulphate 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 that 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 in one of the compositions that 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. As quaternary ammonium salts, there may be mentioned, for example: those corresponding to the following general formula (II):

in which the groups R 1 to R 4, which may be identical or different, represent a linear or branched aliphatic group containing from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the groups R 1 to R4 denotes a linear or branched aliphatic radical containing 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-C30alkyl, C1-C30alkoxy, polyoxyalkylene (C2-C6), C1-C30alkylamide, (C2-C22) alkylamido (C2-C6) alkyl, ( C12-C22) acetate, and hydroxyalkyl C1-C30; X "is an anion selected from the group of halides, phosphates, acetates, lactates, (C 1 -C 4) alkyl sulfates, (C 1 -C 4) alkyl or (C 1 -C 4) alkylarylsulfonates.

Of the quaternary ammonium salts of formula (II), tetraalkylammonium salts are preferred, for example dialkyl dimethyl ammonium or alkyl trimethyl ammonium salts in which the alkyl group contains from about 12 to 22 carbon atoms. carbon, in particular the salts of behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, benzyldimethylstearylammonium or, on the other hand, the salts of palmitylamidopropyltrimethylammonium, of stearamidopropyltrimethylammonium, the salts of stearamidopropyldimethylcétéaryl ammonium, or the salts of stearamidopropyldimethyl- (myristylacetate) ammonium. sold under the name CERAPHYL® 70 by VAN DYK. It is particularly preferred to use the chloride salts of its compounds. the quaternary ammonium salts of imidazoline, for example those of formula (III) below:

wherein R5 is alkenyl or alkyl having 8 to 30 carbon atoms, for example fatty acid derivatives of tallow, Re represents a hydrogen atom, a C1-C4 alkyl group or an alkenyl or alkyl group having 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 and lactates. alkylsulfates, alkyl- or alkylarylsulfonates, the alkyl and aryl groups of which preferably comprise from 1 to 20 carbon atoms and from 6 to 30 carbon atoms, preferably R.sup.5 and R.sub.1 denote a mixture of alkenyl or alkyl groups comprising from 12 to 21 carbon atoms, for example fatty acid derivatives of tallow, R 7 denotes a methyl group, R x denotes a hydrogen atom, such a product is for example marketed under the name REWOQUAT® W 75 by the N REWO - quaternary di or triammonium salts in particular of formula (IV):

in which R 9 denotes an alkyl radical containing about 16 to 30 carbon atoms, optionally hydroxylated and / or interrupted by one or more oxygen atoms, R 10 is chosen from hydrogen or an alkyl radical containing from 1 to 4 carbon atoms.

carbon or a group (R9a) (R10a) (Riia) N- (CH2) 3, Rga, Rio, Riia, Ru, R12, R13 and R14, which are identical or different, are chosen from hydrogen or an alkyl radical containing 1 to 4 carbon atoms, and X 'is an anion selected from the group of halides, acetates, phosphates, nitrates and methylsulfates. Such compounds are, for example, the Finquat CT-P proposed by Finetex (Quaternium 89), the Finquat CT proposed by Finetex (Quaternium 75), the quaternary ammonium salts containing at least one ester function, such as those of formula (V) below:

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: - the group

the groups R2o which are linear or branched, saturated or unsaturated C1-C22 hydrocarbon groups, - the hydrogen atom,

Ri8 is chosen from: - the group

the groups R22 which are linear or branched, saturated or unsaturated C 1 -C 6 hydrocarbon-based groups, R 17, R 19 and R 21, which are identical or different, are chosen from C 7 -C 21 hydrocarbon-based 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, which are identical or different, are integers ranging from 0 to 10; X 'is a simple or complex anion, organic or inorganic; with the proviso that the sum x + y + z is from 1 to 15, that when x is 0 then R 6 is R 20 and that when z is 0 then Ris is R 22

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 from 1 to 10.

When Ri6 is a hydrocarbon R20 group, it may be long and have 12 to 22 carbon atoms, or short and have 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, which are identical or different, are chosen from linear or branched, saturated or unsaturated C11-C21 hydrocarbon groups, and more particularly from linear or branched, saturated or saturated C11-C21 alkyl and alkenyl groups. or unsaturated.

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

Advantageously, y is 1.

Preferably, r, s and t, identical or different, are 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 . However, it is possible to use methanesulphonate, phosphate, nitrate, tosylate, an anion derived from an organic acid such as acetate or lactate or any other anion compatible with ammonium with an ester function. The anion X 'is even more particularly chloride or methylsulfate.

In the composition that can be used in the process according to the invention, the ammonium salts of formula (V) in which:

R a is methyl or ethyl, x and y are 1; z is 0 or 1; r, s and t are 2;

Ri6 is chosen from: - the group

- methyl, ethyl or C14-C22 hydrocarbon groups, - the hydrogen atom;

Ris is chosen from: - the group

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

Advantageously, the hydrocarbon groups are linear.

There may be mentioned, for example, the compounds of formula (V) such as the salts (in particular chloride or methylsulfate) of diacyloxyethyl-dimethylammonium, diacyloxyethyl-hydroxyethyl-methylammonium, monoacyloxyethyl-dihydroxyethyl-methylammonium, triacyloxyethyl-methylammonium, monoacyloxyethyl-hydroxyethyl dimethylammonium and mixtures thereof. The acyl groups preferably have from 14 to 18 carbon atoms and come more particularly from a vegetable oil

like palm oil or sunflower oil. When the compound contains more than one acyl group, the latter groups may be identical or different.

These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, alkyldiethanolamine or alkyldiisopropanolamine, optionally oxyalkylenated, with C10-C30 fatty acids or with mixtures of C10-C30 fatty acids. plant 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), a dialkyl sulphate (preferably methyl or ethyl), methanesulfonate. methyl, para-toluenesulfonate methyl, chlorohydrin glycol or glycerol.

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 that can be used in the process according to the invention may contain, for example, a mixture of quaternary ammonium mono-, di- and triester salts 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 US-A-4874554 and US-A-4137180.

The behenoylhydroxypropyltrimethylammonium chloride proposed by KAO can be used 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 that can be used, it is preferred to use dipalmethylethyl hydroxyethyl methyl ammonium salts.

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) that may be used in the process according to the invention may be in particular derivatives of secondary or tertiary aliphatic amines, optionally quaternized, in which the aliphatic group is a linear or branched chain comprising from 8 to 22 atoms. carbon, said amine derivatives containing at least one anionic group such as, for example, a carboxylate group, sulfonate, sulfate, phosphate or phosphonate. Mention may in particular be made of (C 8 -C 20) betaines, sulfobetaines, (C 8 -C 20) alkylamido (C 8 -C 20) alkyl or C 8 -C 20 alkylamido (C 6 -C 18) alkylsulfobetaines. .

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

Ra-C (O) -NHCH2CH2N + (Rb) (Rc) -CH2C (O) O ·, M +, X '(B1)

Formula (B1) in which:

Ra represents a C10-C30 alkyl or alkenyl group derived from an 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 counterion derived from an alkali metal, 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 counterion, preferably chosen from halides, acetates, phosphates, nitrates, (C 1 -C 4) alkyl sulphates, (C 1 -C 4) alkyl or (C 1 -C 4) alkylarylsulfonates, in particular methylsulphate and ethylsulphate; or else M + and X 'are absent;

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

Wherein B is -CH2-CH2-O-X '; B 'represents the group - (CH2) ZY', with z = 1 or 2; X 'represents the group -CH2-C (O) OH, -CH2-C (O) OZ', -CH2-CH2-C (O) OH, -CH2-CH2-C (O) OZ ', or an atom hydrogen; Y 'represents the group -C (O) OH, -C (O) OZ', -CH2-CH (OH) -SO3H or the group -CH2-CH (OH) -SO3-Z '; Z 'represents a cationic counterion derived from an alkaline or alkaline earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;

Ra 'represents a C10-C30 alkyl or C10-C30 alkenyl group of a Ra'-COOH acid, preferably present in coconut oil or in hydrolyzed linseed oil, an alkyl group, in particular a C17 group, and its iso form, an unsaturated C17 group.

Compounds of this type are classified in the CTFA dictionary, 5th edition, 1993, under the names cocoamphodiacétate disodium, lauroamphodiacétate disodium, caprylamphodiacétate disodium, capryloamphodiacétate disodium, cocoamphodipropionate disodium, lauroamphodipropionate disodium, caprylamphodipropionate disodium, capryloamphodipropionate disodium, lauroamphodipropionic acid, cocoamphodipropionic acid. By way of example, mention may be made of cocoamphodiacetate marketed by RHODIA under the trade name MIRANOL® C2M concentrate

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

Ra "-NH-CH (Y") - (CH2) n-C (O) NH (CH2) n -N (Rd) (Re) (B'2)

Wherein Y "is -C (O) OH, -C (O) OZ", -CH2-CH (OH) -SO3H or -CH2-CH (OH) -SO3-Z ";

Rd and Re, independently of one another, represent a C1-C4 alkyl or hydroxyalkyl radical; Z "represents a cationic counterion derived from an alkaline or alkaline earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;

Ra "represents a C10-C30 alkyl or alkenyl group of an acid Ra" -C (O) OH preferably present in coconut oil or in hydrolysed 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 Chimex under the name CHIMEXANE HB.

Among the amphoteric or zwitterionic surfactants mentioned above, use is preferably made of (C 8 -C 20) alkyl betaines such as cocoylbetaine, (C 8 -C 20) alkylamido (C 2 -C 8) alkylbetaines, such as cocoylamidopropylbetaine, and their mixtures.

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

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

Preferably, when they are present, the surfactant or surfactants 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 may further comprise one or more silicones.

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

Preferably, the silicone or silicones are chosen from polydialkylsiloxanes, in particular polydimethylsiloxanes (PDMS), and organomodified polysiloxanes comprising at least one functional group chosen from amino groups, aryl groups and alkoxy groups.

Organopolysiloxanes are further defined in Walter NOLL's "Chemistry and Technology of Silicones" (1968), Academie Press. They can be volatile or nonvolatile.

The volatile silicones are more particularly chosen from silicones having a boiling point ranging from 60 ° C. to 260 ° C., and more particularly still silicones chosen from: (i) cyclic polydialkylsiloxanes containing from 3 to 7, preferably from 4 to 5 silicon atoms. It is, for example, octamethylcyclotetrasiloxane sold in particular under the name VOLATILE SILICONE® 7207 by UNION CARBIDE or SILBIONE® 70045 V2 by RHODIA, decamethylcyclopentasiloxane marketed under the name 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 the VOLATILE® SILICONE FZ 3109 marketed by UNION CARBIDE, of formula:

Cyclic polydialkylsiloxane mixtures with organic compounds derived from silicon may also be mentioned, such as the mixture of octamethylcyclotetrasiloxane and tetramethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-1,1 '- (hexa). -2,2,2 ', 2', 3,3'-trimethylsilyloxy) bis-neopentane;

(ii) linear volatile polydialkylsiloxanes having 2 to 9 silicon atoms and having a viscosity of less than or equal to 5 × 10 -6 m 2 / s at 25 ° C. It is, for example, decamethyltetrasiloxane marketed in particular under the name "SH 200 By the company 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 that may be used according to the invention may preferably be non-volatile polydialkylsiloxanes, polydialkylsiloxane gums and resins, polyorganosiloxanes modified with organofunctional groups chosen from amino groups, aryl groups and alkoxy groups, and mixtures thereof. .

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

Among these polydialkylsiloxanes, mention may be made, without limitation, of the following commercial products: SILBIONE® oils of the 47 and 70 047 series or the MIRASIL® oils marketed by RHODIA, such as, for example, the 70 047 V 500 000 oil; the oils of the MIRASIL® series marketed by RHODIA; the oils of the 200 series of Dow Corning, such as DC200 having a viscosity of 60,000 mm 2 / s; - VISCASIL® oils from GENERAL ELECTRIC and some oils from 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 the 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 GOLDSCHMIDT, which are polydialkyl (C1-C20) siloxanes.

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

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

More particularly useful products according to the invention are mixtures such as: - mixtures formed from an end-hydroxylated polydimethylsiloxane, or dimethiconol (CTFA) and a cyclic polydimethylsiloxane also called cyclomethicone (CTFA) such that the product Q2 1401 marketed 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 an SF 30 gum corresponding to a dimethicone, having a number average molecular weight of 500,000 solubilized in oil SF 1202 Silicone Fluid corresponding to decamethylcyclopentasiloxane; mixtures of two PDMSs 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 product SF 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 comprises 15% of SE 30 gum and 85% of an SF 96 oil.

The organopolysiloxane resins used in accordance with the invention are crosslinked siloxane systems containing the units: (R7) 2SiO2 / 2, (R3) 3SiOi / 2, R7S1O3 / 2 and S104 / 2 in which R7 represents an alkyl having 1 to 16 carbon atoms. Among these products, those that are particularly preferred are those in which R 7 denotes a lower C 1 -C 4 alkyl group, more particularly methyl.

Among these resins may be mentioned the product marketed 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 trimethylsiloxysilicate type resins sold in particular under the names X22-4914, X21-5034 and X21-5037 by the company Shin-Etsu.

The organomodified silicones that may 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-based group.

The organomodified silicones may be polydiaryl siloxanes, especially polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized with the organofunctional groups mentioned above.

The polyalkylarylsiloxanes are especially chosen from polydimethyl / methylphenylsiloxanes and 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: SITBIONE® oils of the 70 641 series from RHODIA; - the RHODORSIL® 70 633 and 763 RHODIA series of oils; - DOW CORNING 556 COSMETIC GRAD FLUID oil from Dow Corning; the silicones of the PK series of BAYER, such as the product PK20; the silicones of the PN, PH series of BAYER, such as the PN1000 and PH1000 products; - some oils of the SF series of GENERAL ELECTRIC such as SF 1023, SF 1154, SF 1250, SF 1265.

Among the organomodified silicones, mention may also be made of polyorganosiloxanes comprising: substituted or unsubstituted amino groups, for instance 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 marketed under the name "Silicone Copolymer F-755" by SWS Silicones and Abil Wax® 2428, 2434 and 2440 by the company GOLDSCHMIDT.

The silicones that 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 may further comprise one or more non-silicone fatty substances.

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

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

Non-silicone fatty substance is understood to mean a fatty substance that does not comprise a silicon atom.

The non-silicone fatty substance (s) that 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 esters and / or fatty alcohol esters, unsalified fatty acids, waxes and mixtures thereof.

The fatty substance or bodies may be liquid or non-liquid at room temperature and at atmospheric pressure.

The liquid fatty substances that may 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 more preferably less than or equal to 0.1 Pa.s at the temperature of 25 Pa. ° 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 solely of carbon and hydrogen atoms, liquid at ordinary temperature (25 ° C.) and at atmospheric pressure (760 mmHg, ie 1.013 × 10 5 Pa).

More particularly, the liquid hydrocarbons are chosen from: - linear or branched, optionally cyclic C6-C10 alkanes. As examples, mention may be made of 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 liquid paraffins, and derivatives thereof, petroleum jelly, liquid petroleum jelly, polydecenes, hydrogenated polyisobutene, that sold under the Parléam® brand by NOF Corporation, the squalane.

Preferably, the liquid hydrocarbon or hydrocarbons are chosen from paraffin oils, isoparaffins, liquid petroleum jelly, tundecane, tridecane, isododecane and mixtures thereof.

In a very particularly preferred variant, the liquid hydrocarbon or hydrocarbons are chosen from liquid petroleum jelly, 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 mmHg, ie 1.013 × 10 5 Pa). Preferably, the liquid fatty alcohols of the invention have from 8 to 30 carbon atoms and they can be saturated or unsaturated.

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

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

The unsaturated liquid fatty alcohols have in their structure at least one double or triple bond, and preferably one or more double bonds. When more than one double bond is present, it is preferably 2 or 3 and may or may not be conjugated.

These unsaturated fatty alcohols can be linear or branched.

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

More particularly, the liquid unsaturated fatty alcohols that can be used in the invention are chosen from oleic (or oleyl) alcohol, linoleic (or linoleyl) alcohol, linolenic (or linolenyl) alcohol and undecylenic alcohol. Oleyl 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 mmHg, ie 1.013 × 10 5 Pa).

More particularly, the liquid esters are chosen from linear or branched C 1 -C 26 saturated or unsaturated aliphatic mono- or polyacids and linear or branched C 1 -C 26 saturated or unsaturated aliphatic mono- or polyalcohols, the total number of carbon atoms of the esters being greater than or equal to 10.

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

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

It is possible to use esters of C 4 -C 22 di- or tricarboxylic acids and of C 1 -C 22 alcohols and esters of mono-, di- or tricarboxylic acids and di-, tri-, non-sugar alcohols. tetra- or pentahydroxylated C4-C26 ·

Mention may especially be made of diethyl sebacate, diisopropyl sebacate, diisopropyl adipate, di-n-propyl adipate, dioctyl adipate, diisostearyl adipate, dioctyl maleate, dioctyl maleate and the like. glyceryl, octyldodecyl stearoyl stearate, pentaerythrityl monoricinoleate, pentaerythrityl tetraisonanoate, pentaerythrityl tetrapelargonate, pentaerythrityl tetraisostearate, pentaerythrityl tetraoctanoate, propylene glycol dicaprylate, propylene glycol dicaprate, tridecyl, triisopropyl citrate, triisotearyl citrate, glyceryl trilactate, glyceryl trioctanoate, trioctyldodecyl citrate, trioleyl citrate, propylene glycol dioctanoate, neopentyl glycol diheptanoate, diethylene glycol diisanonate, and polyethylene glycol distearates.

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

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

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

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

The esters of sugars and fatty acids may be chosen in particular from the group comprising the esters or mixtures of esters of sugars described above and of C 6 -C 30, preferably C 12 -C 22 fatty acids, linear or branched, saturated or unsaturated. If unsaturated, these compounds may comprise one to three carbon-carbon double bonds, conjugated or otherwise.

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

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

More particularly, mono- and di-esters, and especially mono- or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates, oleostearates, sucrose, glucose or methylglucose, or else methylglucose dioleate (Glucate® OD) are used.

Among the sugar esters, pentaerythrityl esters, preferably pentaerythrityl tetraisisostea, pentaerythrityl tetraoctanoate, caprylic and capric acid hexaesters mixed with dipentaerythritol can be used.

Among the natural or synthetic esters of mono-, di- or triacids with glycerol, it is possible to use vegetable or synthetic oils.

More particularly, said one or more vegetable or synthetic oils 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 triglycerides of heptanoic or octanoic acids or else such as sesame, soy, coffee, safflower, borage, sunflower, olive, apricot kernel, camellia, bambara pea, avocado, mango, rice, cotton, rose, kiwifruit seed, sea buckthorn pulp, blueberry seed, poppy, orange peel, sweet almond, palm, copra, vernoia, marjoram , baobab, rapeseed, ximenia, pracaxi, 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, the oil of jojoba, the oil of be urea of shea.

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

By fatty acid is meant a non-salified 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 that may be used according to the invention are chosen from acids of formula RCOOH, where R is a saturated or unsaturated radical, linear or branched, preferably containing from 7 to 39 carbon atoms.

Preferably, R is a C7-C29 alkyl or C7-C29 alkenyl group, more preferably 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 or acids are chosen from oleic acid, linoleic acid and isostearic acid.

The fatty substance (s) that may be used in the compositions used in the process of the invention may also be chosen from non-liquid fatty substances at room temperature (25 ° C.) and at atmospheric pressure (760 mmHg, ie 1.013 × 10 5 Pa). ).

By non-liquid fats, is preferably meant a solid compound or a compound having a viscosity greater than 2 Pa.s at a temperature of 25 ° C and a shear rate of 1 s'1.

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

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

For example, cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol) may be mentioned. More particularly, cetylstearyl alcohol is used.

The fatty acid ester (s) and / or non-liquid fatty alcohol (s) that can be used according to the invention are generally chosen from solid esters derived from C 9 -C 26 fatty acids and from C 9 -C 26 fatty alcohols.

By way of example, octyldodecyl behenate, isoketyl behenate, cetyl lactate, stearyl octanoate, octyl octanoate, cetyl octanoate and oleate may be mentioned as examples. decyl alcohol, myristyl stearate, octyl palmitate, octyl pelargonate, octyl stearate, alkyl myristates such as cetyl, myristyl or stearyl myristate, and hexyl stearate .

The non-silicone wax or waxes 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 waxes of flowers such as the essential wax of blackcurrant sold by the company BERTIN (France), animal waxes such as beeswax, or modified beeswaxes (cerabellina) and ceramides or the like.

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

in which: R 'denotes a linear or branched, saturated or unsaturated, alkyl radical 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 esterified position; saturated or unsaturated C16-C30 fatty acid; - R "denotes a hydrogen atom or a (glycosyl) n, (galactosyl) m or sulfogalactosyl radical, in which n is an integer ranging from 1 to 4 and m is an integer ranging from 1 to 8;

- R '"denotes a hydrocarbon radical C15-C26, saturated or unsaturated in the alpha position, this radical may be substituted by one or more C1-C14 alkyl radicals; it being understood that in the case of natural ceramides or glycoceramides, R '' may also designate a C15-C26 alpha-hydroxyalkyl radical, the hydroxyl group optionally being esterified with a C16-C30 alpha-hydroxy acid.

Preferred ceramides in the context of the present invention are those described by DOWNING in Arch. Dermatol, Vol. 123, 1381-1384, 1987, or those described in French patent FR 2 673 179.

The most preferred ceramides or ceramides 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 in C15.

Preferably, the following compounds may be chosen: N-linoleoyldihydrosphingosine, N-oleoyldihydrosphingosine, N-palmitoyldihydrosphingosine, N-stearoyldihydrosphingosine, N-behenoyldihydrosphingosine and a mixture of these compounds.

Even more preferably, the ceramides for which R 'denotes a saturated or unsaturated alkyl radical derived from fatty acids, R "denotes a galactosyl or sulphogalactosyl radical and R'" denotes a group -CH = CH- (CH2) i2- CH3. Other waxes or waxy raw materials that can be used according to the invention are in particular marine waxes, such as those sold by SOPHIM under the reference M82, and polyethylene or polyolefin waxes in general.

The non-liquid fatty ethers that 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) that can be used according to the invention are chosen from hydrocarbons, in particular linear or branched C6-C10 alkanes and linear or branched hydrocarbons, of animal or synthetic mineral origin, of more than 16 carbon atoms, such as paraffin oils, and derivatives thereof, petroleum jelly, vaseline oil; esters of fatty acids, in particular vegetable oils and esters of C4-C22 di- or tricarboxylic acids and of C1-C22 alcohols, these esters being more preferably chosen from triglycerides of vegetable origin. , liquid fatty alcohols and mixtures thereof.

The fatty substance (s) that 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 that can be used in the process according to the invention also comprise water, which generally represent from 10 to 90% by weight, preferably from 10 to 80% by weight, preferably from 10 to 70% by weight, relative to total weight of each composition.

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

The solvents may 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 that can be used in the process according to the invention is generally between 2 and 14.

The composition comprising one or more alkali or alkaline earth hydroxides according to the invention generally has a pH of between 7 and 14, preferably between 8 and 13.8.

The composition comprising one or more acids not containing ethylenic unsaturation, when it is present, generally has a pH of between 2 and 7, preferably between 2.5 and 6.

The compositions that may be used in the process according to the invention may also contain additives such as natural or synthetic polymeric thickeners, anionic, amphoteric or zwitterionic, nonionic or cationic, associative or non-associative, non-polymeric thickeners such as electrolytes, polymers and the like. styling, sugars, pearlescent agents, opacifiers, sunscreens, vitamins or provitamins, perfumes, colorants, organic or inorganic particles, preservatives, pH stabilizers. Those skilled in the art will take care to choose the possible additives and their quantity so that they do not adversely affect the properties of the process of the present invention.

These additives may be present in the compositions that 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 may be in any form compatible with an application on keratinous fibers, for example in the form of wax, paste, more or less fluid or thick cream, gel, foam, spray, lotion.

The compositions described above are applied to the dry or wet keratin fibers, sequentially or simultaneously.

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

The process according to the invention may optionally comprise a step of raising the temperature, in particular by means of a straightening iron (flat tongs) 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) and / or after the application of the composition (s) comprising the one or more acids not containing ethylenic unsaturation. At the end of the process according to the invention, the keratinous fibers may optionally be washed with a shampoo followed by rinsing with water, before being dried or allowed 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 smoothing or straightening the hair. The invention also relates to kits suitable for implementing the method of the invention.

A first kit according to the invention comprises at least two compartments: a first compartment comprising a first composition which comprises one or more alkaline or alkaline-earth hydroxides as defined above, a second compartment comprising a second composition which comprises one or more a plurality of acids not containing ethylenic unsaturation as defined above, one or more diamines as defined above being included in the first composition and / or in the second composition and / or in one or more separate compositions, (s) in one or more additional compartments, it being understood that the composition (s) containing said diamine (s) does not comprise (include) maleic acid or salts of maleic acid, and preferably does not include ( include) no monomeric ethylenically unsaturated compounds.

Thus, in a first preferred embodiment, the first kit according to the invention comprises two compartments: a first compartment comprising a first composition which comprises one or more alkaline or alkaline-earth hydroxides as defined above and one or more diamines such as defined above, - a second compartment comprising a second composition which comprises one or more acids not containing ethylenic unsaturation as defined above.

In a second preferred embodiment, the first kit comprises at least two compartments: a first compartment comprising a first composition which comprises one or more alkaline or alkaline-earth hydroxides as defined above, a second compartment comprising a second composition which comprises one or more acids not containing ethylenic unsaturation as defined above, one or more diamines as defined above included in the second composition and / or in one or more separate compositions included in one or more several additional compartments.

A second kit according to the invention comprises at least two compartments: a first compartment comprising a first composition which comprises one or more alkaline or alkaline-earth hydroxides as defined above, a second compartment comprising a second composition which comprises comprises one or more diamines as defined above, - optionally one or more acids not containing ethylenic unsaturation as defined above, included in the second composition and / or in one or more separate compositions included in one or more additional compartments, it being understood that the composition (s) containing said diamine (s) does not comprise (include) maleic acid or maleic acid salts, and preferably does not include (include) monomeric compounds with ethylenic unsaturation.

The following examples illustrate the present invention and should not be construed in any way as limiting the invention. EXAMPLES: 1) Preparation of the "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

Basic Cream A

"Activator" composition B

Neutralizing composition C

2) Preparation of compositions containing one or more diamines

The compositions D, E, F and G that can be used in the process according to the invention are prepared by mixing the ingredients according to Table II below.

Table II

Composition D

Basic composition E

Activating composition F

Neutralizing composition G

3) Methods of permanent hair deformation

Comparative process

The comparative method comprises the following successive steps: 1) the base cream A and the activator composition B are mixed, 2) the mixture is applied, 3) 15 minutes laying, 4) the hair is rinsed, 5) the composition " neutralizing "C is applied, 6) the hair is rinsed.

Process 1 according to the invention

The process according to the invention comprises the following successive steps: 1) the base cream A and the activator composition B are mixed, 2) the mixture is applied, 3) 15 minutes laying, 4) the hair is rinsed, 5) the "neutralizing" composition C is applied, 6) the hair is rinsed, 7) the composition D is applied, 8) 5 minutes laying, 9) the hair is rinsed.

The method 1 according to the invention makes it possible to obtain better results in terms of smoothing and degradation of the fiber compared to the comparative method.

Method 2 according to the invention

Process 2 according to the invention comprises the following successive steps: 1) the base cream A and the activating composition B are mixed, 2) the mixture is applied, 3) 15 minutes laying, 4) the hair is rinsed, 5 ) the composition D is applied, 6) laying 5 minutes, 7) the hair is rinsed, 8) the "neutralizing" composition C is applied, 9) the hair is rinsed.

The method 2 according to the invention makes it possible to obtain better results in terms of smoothing and degradation of the fiber compared with the comparative method.

Claims (19)

1. Process for the permanent deformation of keratinous fibers, in particular hair, comprising the application to the fibers of: i) one or more diamine (s) chosen from the compounds of formula (I) below: in which R 1, R 2, R 3 and R 4, independently of one another, represent a hydrogen atom or an alkyl radical comprising from 1 to 10 carbon atoms, R, R ', R "and R'" independently each other represents a hydrogen atom, an alkyl radical comprising from 1 to 10 carbon atoms, an alkoxyalkyl radical comprising from 1 to 10 carbon atoms or an alkoxyamine radical comprising from 1 to 10 carbon atoms, n, p and q, independently of each other, represent a number ranging from 1 to 100, it being understood that for any value n, p or q greater than or equal to 2, the radicals R, R ', R "and R5" may be different from one CRR 'or CR "R5" unit to another, and ii) one or more alkaline or alkaline earth hydroxide (s), said amine (s) and said hydroxide (s) (s) alkaline (s) or alkaline-earth being applied within a single composition, it is in separate compositions, eta It is understood that the composition (s) containing said diamine (s) does not include (include) maleic acid or maleic acid salts. 2. Process according to claim 1, characterized in that the diamines are chosen from the compounds of formula (I) in which: R 1, R 2, R 3 and R 4, independently of each other, represent a hydrogen atom or a alkyl radical comprising 1 to 4 carbon atoms, and more preferably represent a hydrogen atom, R, R 5, R "and R" ', independently of each other, represent a hydrogen atom, an alkyl radical comprising from 1 to 4 carbon atoms, an alkoxyalkyl radical comprising 1 to 4 carbon atoms or an alkoxyamine radical comprising 1 to 4 carbon atoms, and more preferentially represent, independently of one another, a hydrogen atom or a radical methyl, n, p and q, independently of each other, represent a number varying from 1 to 20, and more preferably ranging from 1 to 15. 3. Process according to claim 1 or 2, characterized in that the diamine or diamines are chosen from compounds of formula (I) in which: R 1, R 2, R 3 and R 4 are hydrogen atoms, - R and R "Are hydrogen atoms, - R 'and R'", independently of one another, are chosen from a hydrogen atom or a methyl radical, - n and q vary from 1 to 5, preferably from 1 to 3, more preferably 2, p varies from 1 to 15, preferably from 2 to 13. 4. Process according to any one of the preceding claims, characterized in that the diamine or diamines are chosen from polyoxyalkylenated diamines, preferably polyoxyethylene diamines and polyoxypropylene diamines. 5. Method according to any one of the preceding claims, characterized in that 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. 6. Process according to any one of the preceding claims, characterized in that the composition (s) containing the diamine (s) does not comprise (include) monomeric compounds with ethylenic unsaturation. 7. Process according to any one of the preceding claims, characterized in that the diamine (s) and the alkali or alkaline-earth metal (s) are used in one and the same composition. 8. Process according to any one of claims 1 to 6, characterized in that the diamine (s) and the alkali or alkaline-earth metal (s) are used in separate compositions, the composition (s) comprising the or said diamine (s) being applied before and / or after the composition comprising the alkali or alkaline earth metal hydroxide (s), and preferably after, 9. Process according to any one of the preceding claims, characterized in that the alkali or alkaline-earth hydroxide or hydroxides are chosen from sodium hydroxide, lithium hydroxide, potassium hydroxide, hydroxide and sodium hydroxide. calcium, magnesium hydroxide, and a mixture of these compounds, preferably from sodium hydroxide, lithium hydroxide, calcium hydroxide, and a mixture of these compounds. 10. Process according to any one of the preceding claims, characterized in that the alkaline or alkaline earth hydroxyl or alkanes represent from 0.5 to 60% by weight, preferably from 1 to 55% by weight, better still from 2 to 50% by weight, relative to the total weight of the composition containing them, 11. Process according to any one of the preceding claims, characterized in that the composition comprising the alkali or alkaline earth hydroxide or hydroxides also comprises guanidine carbonate. 12. Method according to any one of the preceding claims, characterized in that it further comprises the application to the fibers of one or more acids not containing ethylenic unsaturation. in a composition distinct from the composition containing the alkali or alkaline earth metal hydroxide (s) and applied to the fibers thereafter. 13. The method of claim 12, characterized in that the acid or acids not containing ethylenic unsaturation are carboxylic acids, preferably the acid not containing ethylenic unsaturation is citric acid. 14. The method of claim 12 or 13, characterized in that the acid or acids not containing ethylenic unsaturation represent from 0.01 to 15% by weight, preferably from 0.05 to 10% by weight, relative to to the total weight of the composition containing them. 15. Process according to any one of Claims 12 to 14, characterized in that the diamine or diamines are included in the composition containing the alkali or alkaline-earth metal hydroxide (s) and / or in the composition comprising the acid (s) not comprising no ethylenic unsaturation, ΐ 16. Method according to any one of claims 12 to 15, characterized in that it comprises the sequential application on the keratinous fibers of at least three distinct compositions: a first composition comprising the alkali or alkaline hydroxide or alkali and then - a second composition comprising the one or more acids having no ethylenic unsaturation, and - a third composition comprising said diamine or diamines applied before the 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 one or more diamines is applied between the first composition and the second composition or simultaneously with the second composition. 17. The method of claim 16, characterized in that it comprises the sequential application on the keratin fibers of at least three distinct compositions: a first composition comprising the alkali or alkaline earth hydroxide (s), then ~ a second composition comprising said diamine (s), followed by a third composition comprising said acid (s) not containing ethylenic unsaturation. 18. Kit comprising at least two compartments: a first compartment comprising a first composition which comprises one or more alkaline or alkaline-earth hydroxides, preferably as defined in claims 9 and 10, a second compartment comprising a second composition which comprises one or more acids not containing ethylenic unsaturation, preferably as defined in claims 13 and 14, - one or more diamines of formula (I) as defined in claim 1, preferably as defined in the claims 2 to 5, being included in the first composition and / or in the second composition and / or in one or more separate compositions included in one or more additional compartments. it being understood that the composition (s) containing said diamine (s) does not comprise (include) maleic acid or maleic acid salts, and preferably does not include (include) monomeric ethylenically unsaturated compounds. 19. Kit comprising at least two compartments: a first compartment comprising a first composition which comprises one or more alkaline or alkaline earth hydroxides, preferably as defined in claims 9 and 9. 10, - a second compartment comprising a second composition which comprises one or more diamines of formula (I) as defined in claim 1, preferably as defined in claims 2 to 5, - optionally one or more acids not comprising ethylenically unsaturated, preferably as defined in claims 13 and 14, included in the second composition and / or in one or more separate compositions included in one or more additional compartments, it being understood that the composition or compositions ( s) containing said diamine (s) does not include (include) maleic acid or maleic acid salts, and preferably does not include (include) ethylenically unsaturated monomeric compounds.