FR3043549A1 - PROCESS FOR TREATING KERATIN FIBERS WITH A COMPOSITION COMPRISING A RETICULATING AGENT AND A STEAM IRON - Google Patents

Abstract

The present invention relates to a process for treating keratinous fibers, especially human keratinous fibers such as the hair, implementing i) a step of applying at least one crosslinking agent which contains at least one (thio) carbonyl group and ii) a smoothing / straightening step by means of a steam iron, in particular a steam smoothing iron, in particular i) is applied first and secondly ii) the steam smoothing iron is applied without an intermediate rinsing step especially to water.

Description

PROCESS FOR TREATING KERATIN FIBERS WITH A COMPOSITION COMPRISING A RETICULATING AGENT AND A STEAM IRON

The present invention relates to a process for treating keratinous fibers, especially human keratinous fibers such as the hair, implementing i) a step of applying at least one crosslinking agent which contains at least one (thio) carbonyl group and ii) a smoothing / straightening step by means of a steam iron, in particular a steam smoothing iron, in particular i) is applied first and secondly ii) the steam smoothing iron is applied without an intermediate rinsing step especially to water.

In the hair field, consumers want to have compositions to make a temporary change to their hair, and aiming for a good performance of the effect achieved. In general, it is desired that the change persists shampoos for at least 15 days, or more depending on the nature of the change.

Heat treatments are generally used to change the shape of the hair, in a sustainable way. These treatments allow a visual modification of the appearance of the hairstyle, associating a decrease of the degree of crimp, a reduction of the overall volume of the hair, a decrease of the frizzotis, a gain in discipline, a smoother visual aspect, a substantial gain shine, resistance to moisture and heat for maintaining the hairstyle all day long.

Moreover, this type of treatment has the advantage of facilitating the daily care of the hair, with the use of less care products, including rinsed care such as conditioners or masks, or care rinsed such as serums, skincare creams or balms, disciplinary foams. Hair drying is facilitated, with a greatly shortened brushing time and a reduction in the daily use of flat tongs, in both time and intensity. This thus makes it possible to limit the risks of damage to the hair by combined factors of mechanical and thermal stress. To these heat treatments, we associate several technologies. A first technology relies on the use of compositions based on thiol reducers. These technologies require a rigorous respect of the conditions of application recommended by the suppliers, in particular in terms of quantity and time of break. In addition, they may be contraindicated on hair too sensitized and not be compatible with the same day application of other treatments such as staining or discoloration. They are otherwise smelly.

Another technology relies on the use of formalin (or formaldehyde) based compositions and its derivatives. These treatments have the particularity to be robust, perfectly compatible with all other conventional hair treatments, such as thiol smoothing mentioned above, alkaline straightening, coloring or discoloration of all types, made before or after.

They give the hair an excellent discipline, a very strong shine and an ease of care in everyday life. The movement of hair in "snake" is also also characteristic. However, in case of repetition of applications, new hair damage appears that can lead to hair breakage. In addition, for toxicological reasons, the use of some of these compounds is now prohibited and / or regulated. So we are looking more and more to avoid the use of such substances, which can be aggressive for the hair and other keratin materials.

Another technology relies on the use of acid-based compositions, and particularly on the use of glyoxylic acid. It has thus been proposed, by the application WO2011 / 104282, a new method for semi-permanently smoothing the hair, which consists in applying a solution of α-ketoacid or α-keto acid to the hair for 15 to 120 minutes, then drying. and finally smooth iron, at a temperature of about 200 ° C, the hair. The α-keto acid employed is preferably glyoxylic acid.

However, it has been found that glyoxylic acid may not be well tolerated, particularly when the scalp is sensitive and / or irritated. Its volatility, amplified by the use of iron heat, can also be a problem. Moreover, the compositions of the prior art can alter the hair and / or alter the color.

It has also been proposed treatments using a composition comprising a base associated with a heat treatment to smooth the hair. Such treatments make it possible to obtain a good relaxation of the loops but can lead to alterations of the hair fiber. The document EP1837010 notably describes a smoothing / straightening process using a composition comprising sodium hydroxide and a heat treatment. WO2007 / 144707 discloses a smoothing / straightening process using a composition comprising a non-hydroxylated base such as monoethanolamine (MEA), ethylene diamine, associated with a heat treatment. WO2009 / 117344 also describes a smoothing / straightening method using a composition comprising a non-hydroxylated base and a protein denaturant associated with a heat treatment.

To limit the alterations of the hair fibers, it has also been proposed to use compositions comprising weak acids at alkaline pH associated with a heat treatment. Document WO2010 / 049434 for example describes a smoothing / straightening process in which a composition comprising a dicarboxylic acid such as maleic acid and a heat treatment is applied.

There is still a need to develop a method of hair treatment, including a smoothing / straightening method that allows smoothing / straightening and / or reducing hair curling effectively and sustainably by limiting hair degradation. In particular, a method is sought which makes it possible to obtain good relaxation of loops and, if possible, durable over time.

This (these) technical problem (s) has (have) been solved (s) by a process for treating keratinous fibers, especially human keratinous fibers such as the hair, implementing: i) a step of applying at least one crosslinking agent which contains at least one (thio) carbonyl group; and ii) a step of smoothing / straightening by means of a steam iron, in particular a steam smoothing iron at a temperature greater than or equal to 100 ° C; in particular i) is applied first and then second ii) the steam smoothing iron is applied without intermediate rinsing step including water.

The method of the invention makes it possible in particular to obtain a good relaxation of loops, which is durable, while limiting the degradation of the keratinous fibers. In addition, this process makes it possible to obtain bright, disciplined keratinous fibers with a very pleasant feel or repair of keratinous fibers. The "snake" movement of the keratinous fibers after treatment with the process of the invention is characteristic of Brazilian smoothing without using a product such as formalin. In addition, the process of the invention allows a significant reduction in the volume of keratinous fibers after treatment, smoothing and straightening. Other characteristics and advantages of the invention will emerge more clearly on reading the description and examples which follow.

For the purposes of the present invention, and unless a different indication is given, the following terms mean: a "hydrocarbon chain" is "unsaturated" when it comprises one or more unsaturations ie double bonds and / or one or more triple bonds ; the "aryl" or "heteroaryl" radicals or the aryl or heteroaryl part of a radical may be substituted by at least one substituent carried by a carbon atom, chosen from: a C 1 -C 8 alkyl radical, optionally substituted with one or more radicals chosen from hydroxyl, C 1 -C 2 alkoxy, (C 2 -C 4) (poly) hydroxyalkoxy, acylamino, amino radicals substituted by two identical or different C 1 -C 4 alkyl radicals; carriers having at least one hydroxyl group, or both radicals being able to form, with the nitrogen atom to which they are attached, a 5- to 7-membered, preferably 5 or 6-membered, optionally substituted saturated or unsaturated heterocyclic ring comprising optionally another heteroatom identical or different from the nitrogen; . a halogen atom such as chlorine, fluorine or bromine; . a hydroxyl group; . a C 1 -C 2 alkoxy radical; . a C2-C4 (poly) -hydroxyalkoxy radical; . an amino radical; . nitro or nitroso; . a 5- or 6-membered heterocycloalkyl radical; . a 5- or 6-membered optionally cationic heteroaryl radical, preferentially imidazolium, and optionally substituted with a (Cr C4) alkyl radical, preferably methyl; An amino radical substituted with one or two identical or different C 1 -C 6 alkyl radicals optionally carrying at least: i) a hydroxyl group, ii) an amino group optionally substituted by one or two optionally substituted C 1 -C 3 alkyl radicals said alkyl radicals being able to form, with the nitrogen atom to which they are attached, a 5- to 7-membered optionally substituted saturated or unsaturated heterocycle optionally comprising at least one other non-nitrogen heteroatom; An acylamino radical (-N (R) -C (O) -R ') in which the radical R is a hydrogen atom, a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group and the R' radical; is a C1-C2 alkyl radical; A carbamoyl radical ((R) 2 N-C (O) -) in which the R radicals, which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical optionally carrying at least one hydroxyl group; A carboxylic acid or ester radical, (-OC (O) R ') or (-C (O) OR'), in which the radical R 'is a hydrogen atom or a C4-C4 alkyl radical optionally bearing a at least one hydroxyl group and the radical R 'is a C1-C2 alkyl radical; ♦ the carboxylic radical may be in acid or salified form (preferably with an alkali metal or ammonium, substituted or not); An alkylsulphonylamino radical (R'S (O) 2 -N (R) -) in which the radical R represents a hydrogen atom, a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group and the radical R 'represents a C1-C4 alkyl radical, a phenyl radical; An aminosulphonyl radical ((R) 2 N -S (O) 2 -) in which the R radicals, which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group; ; . a cyano group (CN); . a (poly) haloalkyl group, preferentially trifluoromethyl (CF3); the cyclic or heterocyclic part of a non-aromatic heterocycloalkyl radical may be substituted by at least one substituent carried by a carbon atom chosen from the groups: hydroxyl; . C1-C4 alkoxy, (poly) hydroxyalkoxy C2-C4; . alkylcarbonylamino ((RC (O) -NR'-) in which the radical R 'is a hydrogen atom, a C1-C4 alkyl radical optionally bearing at least one hydroxyl group and the radical R is an alkyl radical; C1-C2, amino substituted with two identical or different C1-C4 alkyl groups optionally bearing at least one hydroxyl group, said alkyl radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7-membered ring, saturated or unsaturated optionally substituted optionally comprising at least one other heteroatom different or different from nitrogen; alkylcarbonyloxy ((RC (O) -O-) in which the radical R is a C1-C4 alkyl, amino radical; substituted with two identical or different C4-C4 alkyl groups optionally bearing at least one hydroxyl group, said alkyl radicals being able to form, with the nitrogen atom to which they are attached, a heterocycle comprising from 5 to 7 members ns, optionally substituted saturated or unsaturated optionally comprising at least one other heteroatom different or different from nitrogen; . alkoxycarbonyl ((RO-C (O) -) in which the radical R is a C 1 -C 4 alkyl radical, amino substituted with two identical or different C 4 -C 4 alkyl groups optionally carrying at least one hydroxyl group, said alkyl radicals; capable of forming, with the nitrogen atom to which they are attached, an optionally substituted 5 to 7-membered saturated or unsaturated heterocycle optionally comprising at least one other heteroatom which may or may not be different from nitrogen; or a nonaromatic part of an aryl or heteroaryl radical may also be substituted by one or more oxo groups; an "aryl" radical represents a mono or polycyclic group, condensed or not, comprising from 6 to 22 carbon atoms, and wherein at least one ring is aromatic, particularly the aryl radical is phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl and more preferably is a phenyl or tetrahydronaphthyl radical; a "heteroaryl" radical represents a mono or polycyclic group, condensed or not, comprising from 5 to 22 ring members, from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium, and at least one of which is aromatic; preferably heteroaryl is selected from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyle, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyle, naphthooxazolyle, naphthopyrazolyle, oxadiazolyl, oxazolyl, oxazolopyridyl phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridinyl, thiazoylimidazolyl, thiopyryl, triazolyl, xanthyl and its ammonium salt; - a "cyclic" radical is a "cycloalkyl" radical i.e. a non-aromatic radical, mono- or polycyclic, condensed or not, containing from 5 to 22 carbon atoms, which may comprise from one to more unsaturations such as cyclohexyl or cyclopentyl; a "heterocyclic" or "heterocycloalkyl" radical is a saturated or unsaturated, non-aromatic mono or polycyclic radical, condensed or otherwise, containing from 5 to 22 ring members, comprising from 1 to 6 heteroatoms chosen from the nitrogen atom, d oxygen, sulfur and selenium morpholinyl, thiomoropholinye, piperidinyl, piperazinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothophenyl, azepanyl, thioazepanyl; preferentially pirrolidinyl and morpholino; an "alkyl" radical is a C 18 hydrocarbon radical; particularly C 4 -C 4 such as methyl or ethyl; an "alkenyl" radical is a C2-C10 hydrocarbon radical, linear or branched, comprising one or more double bonds, conjugated or otherwise, in particular comprising a two or three double bonds, preferably a single double bond; the expression "optionally substituted" assigned to the alkyl or alkenyl radical implies that said alkyl radical may be substituted by one or more radicals chosen from the radicals i) hydroxyl, ii) alkoxy C1-C4, iii) acylamino, iv ) amino optionally substituted with one or two identical or different C 1 -C 4 alkyl radicals, said alkyl radicals being able to form, with the nitrogen atom carrying them, a 5- to 7-membered heterocycle, optionally comprising another heteroatom different or not nitrogen, v) phenyl, vi) (Cr C6) alkoxycarbonyl, vii) (CrC6) alkylcarbonyloxy, viii) HC (O) -O-; an "alkoxy" radical is an alkyl-oxy or alkyl-O- radical for which the alkyl radical is a linear or branched C 1 -C 8 hydrocarbon-based radical; especially when C 1 -C 4 is methoxy or ethoxy, and when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above; a "(poly) haloalkyl" radical is an "alkyl" radical as defined above in which one or more hydrogen atoms are substituted or replaced by one or more halogen atoms such as the fluorine, chlorine or bromine, as polyhaloalkyl there may be mentioned trifluoromethyl group; an "alkylthio" radical is an alkyl-S- radical for which the alkyl radical is a hydrocarbon radical, linear or branched, in CrC8; especially when the alkylthio group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above; an anionic counterion is organic or mineral preferentially chosen from halide anions such as CI ', Br', Γ, and organic anions such as mesylates; when the expression "at least one" is used, it implies "one or more"; the bounds defining the range of a range of values are within this range of values. i) the crosslinking agent with (thio) carbonyl group (s)

The method for treating the keratinous fibers of the invention implements i) a step of applying at least one crosslinking agent which comprises one or more group (s) (thio) carbonyl (s) ie one or more selected groups among carbonyl C = O and thiocarbonyl C = S.

By "crosslinking agent" or "polymer network" is meant a chemical agent which is used in polymer chemistry to form three-dimensional polymer networks also called crosslinking. The crosslinking reactions are carried out using a crosslinking agent chemically or physically (light, heat), creating macromolecular networks between the polymers.

According to one embodiment of the invention, the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen (s) among this (them) of formula (I) ):

Formulas (I) in which:

W represents: i) an optionally substituted (hetero) aryl or optionally substituted (hetero) cycloalkyl group, preferably represents a 5- or 6-membered phenyl or heteroaryl such as pyridinyl or heterocycloalkyl comprising at least one oxygen atom; 5 to 8 members such as tetrahydrofuryl, piperazynyl or hexahydrofuro [3,2-b] furanyl,

ii) a group * -A- (CR2R3) xA * when w is 2, with R2 and R3, identical or different, representing a hydrogen atom or a group (CrC6) alkyl such as methyl, x represents an integer inclusive between 0 and 10, preferably x is 1, * represents the point of attachment to the groups -X1-C (X2) -C (= CH2) -R1 and A represents an optionally substituted (hetero) aryl group or (hetero) optionally substituted cycloalkyl, preferably A

represents a phenyl; iii) a hydrocarbon chain, linear or branched, polyvalent, preferably di or trivalent, saturated or unsaturated, preferably saturated, optionally substituted, preferably with a hydroxyl group or with a phenyl group, and comprising from 1 to 20 atoms of carbon; • n represents an integer inclusive between 0 and 5; more particularly between 0 and 3, such that n = 0 or 1; U and w represent an integer inclusive between 2 and 10, more particularly between 2 and 5, such that u = 2 and w = 2 or 3.

In particular, W represents a divalent C 1 -C 6 alkyl or trivalent C 1 -C 10 alkyl group.

According to another embodiment of the invention, the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen (s) among this (them) of formula ( II) or (III):

(II) (NI)

As well as their salts of acids or bases, organic or mineral, their tautomers and their solvates such as hydrates;

Formulas (II) and (III) in which: • X and X ', identical or different, preferably identical, represent an oxygen or sulfur atom, preferably oxygen; ALK represents a linear or branched hydrocarbon chain comprising from 1 to 10 carbon atoms, saturated or unsaturated, in particular by 1 to 3 unsaturations, conjugated or otherwise, said chain is optionally substituted by one or more groups chosen from: a) a hydroxy group; b) a -C (X) -ORb group with X as defined above, and Rb representing a hydrogen atom, an alkali metal, or alkaline earth metal, and c) a heterocyclic lactone group comprising from 4 to 8 members, saturated or unsaturated, nonaromatic, which may be optionally substituted in particular with one or more hydroxyl groups; • ALK 'represents a divalent hydrocarbon chain, linear or branched, comprising from 1 to 10 carbon atoms, saturated or unsaturated, in particular by 1 to 3 unsaturations, conjugated or not; R represents i) a hydrogen atom or ii) a group ORa with Ra representing a hydrogen atom, an alkali metal, alkaline earth metal, or a (C 1 -C 6) alkyl, (C 2 -C 6) alkenyl group, or C2-C6) alkynyl, preferably R represents a hydrogen atom or a group ORa with Ra representing a hydrogen atom, an alkaline metal, alkaline earth metal;

• R 'and R ", which are identical or different, represent a group chosen from: - ALK" -O- with ALK "representing a linear or branched hydrocarbon-based chain comprising from 1 to 10 carbon atoms, and optionally from 1 to 3 unsaturations conjugated or unconjugated, preferably ALK "represents a (CrC6) alkyl, (C2-C6) alkenyl or (C2-C6) alkynyl group; -C (O) -ORb with and Rb representing a hydrogen atom, an alkali metal, or alkaline earth metal; - an NRcRd amino group with Rc and Rd, identical or different, representing a hydrogen atom or a (CrC6) alkyl, (C2-C6) alkenyl, or (C2-C6) alkynyl, preferably NH2; it being understood that ALK ', R' or R "contains at least one group comprising at least one unsaturation.

According to a particular embodiment of the invention, the at least one crosslinking agent (s) containing a (thio) carbonyl group (s) is (are) chosen from among them of formula (II). )

According to a particular embodiment of the invention, the at least one crosslinking agent (s) with a (thio) carbonyl group (s) of formula (II) is (are) such that R represents i) a hydrogen atom.

According to another particular variant of the invention, the agent (s) with (group) (thio) carbonyl (s) of formula (II) is (are) such that R represents (ii) an ORa group with Ra representing a hydrogen atom, an alkali metal, alkaline earth metal, or a (CrC4) alkyl group, preferably R represents a hydrogen atom or an ORa group with Ra representing a hydrogen atom, an alkali metal, or alkaline earth.

According to a preferred embodiment of the invention, the agent (s) with (group) (thio) carbonyl (s) of formula (II) is (are) such that ALK represents a (Cr C6) alkyl group optionally substituted with one or more groups selected from: a) hydroxy; b) -C (O) -ORb with and Rb representing a hydrogen atom, an alkali metal or alkaline earth metal, and c) a heterocycle lactone comprising from 4 to 6 members, which may be optionally substituted with from one to three hydroxy groups.

In particular ALK is substituted by one or more groups selected from a) and c) as defined above.

According to one particular embodiment of the invention, the agent (s) with (group) (thio) carbonyl (s) of formula (II) is (are) such that X represents an oxygen atom.

According to a particular embodiment of the invention the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) of formula (III).

According to one particular embodiment of the invention, the agent (s) with (group) (thio) carbonyl (s) of formula (III) is (are) such that R 'and R ", which are identical or different , represent ALK "-O- with ALK" as defined above, preferably ALK "are identical and represent a group (CrC6) alkyl, or (C2-C6) alkenyl.

According to another particular embodiment of the invention the agent (s) with (group) (thio) carbonyl (s) of formula (III) is (are) such that R 'and R ", identical or different, represent: -C (O) -ORb with and Rb representing a hydrogen atom, an alkali metal, or alkaline earth metal; an NRcRd amino group with Rc and Rd, identical or different, representing a hydrogen atom or a (CrC6) alkyl, (C2-C6) alkenyl or (C2-Ce) alkynyl group, preferably an NH2 amino group.

According to one particular embodiment of the invention, the agent (s) with (group) (thio) carbonyl (s) of formula (III) is (are) such that ALK 'represents a linear divalent hydrocarbon chain or branched, comprising from 1 to 6 unsaturated carbon atoms by 1 to 3 unsaturations, conjugated or not.

Preferably ALK 'represents a (C2-C6) alkenylene or (C2-C6) alkynylene group, more preferably (C2-C6) alkenylene, even more preferably (C2-C4) alkenylene such as ethylene -CH = CH-,

According to one particular embodiment of the invention, the agent (s) with (group) (thio) carbonyl (s) of formula (III) is (are) such that X and X 'represent an atom of oxygen.

According to a preferred variant of the invention, the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen from among the compounds of formula (I) and in 1 to 16 of the following table, as well as their optical and geometric isomers, their tautomers and acid or base salts, mineral or organic:

According to a preferred variant of the invention, the at least one crosslinking agent (s) containing (thio) carbonyl group (s) is (are) chosen from compounds of formula (II) or ( III) and in particular 17 to 26 of the following table, as well as their optical isomers, geometric, their tautomers and acid or base salts, mineral or organic:

According to a particular embodiment of the invention, the at least one crosslinking agent (s) with a (thio) carbonyl group (s) as defined above is (are) in a cosmetic composition in an amount of between 1% and 80% by weight of the composition which comprises them, more particularly in a quantity of between 3% and 50% by weight, preferably between 5% and 30% by weight, more preferably between 7% and 20% by weight such as 10% by weight relative to the total weight of the composition (s) comprising.

Cosmetic composition

The composition used in the process of the invention may be aqueous or anhydrous. It is preferably aqueous and then comprises water at a concentration ranging from 10 to 99%, more preferably from 30 to 99%, more preferably from 50 to 98% by weight relative to the total weight of the composition. In particular the composition is aqueous when it comprises one or more agent (s) crosslinking (s) group (s) (thio) carbonyl (s) of formula (II) as defined above.

The composition may especially comprise one or more water-soluble organic solvents such as C 1 -C 7 alcohols; mention may be made in particular of C 1 -C 7 aliphatic monoalcohols, for example ethanol, or alcoolβ-C7 aromatic alcohols such as benzyl alcohol, which may be used alone or as a mixture with water.

According to a particular embodiment of the invention, the agent (s) or agent (s) crosslinking (s) group (s) (thio) carbonyl (s), in particular of formula (III), are in a composition hydroalcoholic or even alcoholic ie which mainly comprises solvent aliphatic monoalcohols such as ethanol.

According to one variant, the cosmetic composition comprises at least one organic solvent which is liquid at room temperature (25 ° C.) and at atmospheric pressure, which is aprotic and / or apolar lipophilic, in particular an oil such as isododecane.

The composition used in the process of the invention may further comprise at least one usual cosmetic ingredient, especially chosen from propellants; solid fatty substances and especially C8-C40 esters, C8-C40 acids; C8-C40 aliphatic alcohols, sunscreens; moisturizing agents; antidandruff agents; antioxidants; chelating agents; pearlescent and opacifying agents; plasticizing or coalescing agents; the charges; thickeners or gelling agents, polymeric or not other than the cellulosic polymers already mentioned; emulsifiers; polymers in particular conditioning or styling; the perfumes; silanes; crosslinking agents. The composition may of course include several cosmetic ingredients listed above.

Depending on their nature and the purpose of the composition, the usual cosmetic ingredients may be present in customary amounts, easily determinable by those skilled in the art, and which may be included, for each ingredient, between 0.01 to 80% by weight . Those skilled in the art will take care to choose the ingredients in the composition, as well as their amounts, so that they do not adversely affect the properties of the compositions of the present invention.

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

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

The agent (s) or agent (s) crosslinking (s) group (s) (thio) carbonyl (s) as (s) previously defined (s) can be applied (s) on dry or wet hair, preferably on dry hair.

The bath ratio of the composition which comprises the agent (s) or the agent (s) crosslinking (s) to group (s) (thio) carbonyl (s) as (s) defined (s) previously applied may vary from 0.1 to 10, more particularly from 0.2 to 5, and preferably from 0.5 to 3. Relative bath, means the ratio between the total weight of the applied composition and the total weight of keratinous fibers to be treated. ii) Steam iron step

The method for treating keratinous fibers according to the invention comprises a step of smoothing / straightening the keratinous fibers with a steam iron, ie an "iron" which comprises a device that emits water vapor and that applies this water vapor before, during or after the smoothing / straightening, preferably before the smoothing / straightening step and more preferably just before the smoothing / straightening step (0.5 to 10 seconds before).

By "iron" is meant, in the sense of the present invention, a device for heating the keratinous fibers contacting said fibers and the heating device. The end of the iron coming into contact with the keratin fibers generally has two flat surfaces. These two surfaces can be metallic or ceramic. In particular, these two surfaces can be smooth or notched or curved.

According to a particular embodiment, the iron of the steam iron is at a temperature of between 65 ° C. and 250 ° C., particularly between 80 ° C. and 230 ° C., more particularly greater than or equal to 100 ° C. and preferably between 100 ° C. and 190 ° C. Preferably, step ii) of the keratinous fiber treatment process is carried out at a temperature ranging from 150 to 220 ° C., preferably ranging from 160 ° C. to 220 ° C., preferably ranging from 160 ° C. to 210 ° C. , in particular ranging from 180 ° C. to 200 ° C. As examples of irons used in the smoothing process according to the invention, mention may be made of all types of flat iron with steam, and in particular, but not limited to, those described in US Pat. The application of steam iron can be carried out by successive separate keys of a few seconds, or by progressive displacement or sliding along wicks of keratin fibers, especially hair.

Preferably, the application of steam iron in the process according to the invention is in continuous movement from the root to the tip of the hair, in one or more passages, in particular in two to twenty passages. The duration of each steam iron passage can range from 2 seconds to 1 minute.

Advantageously, the keratinous fibers, in particular the hair, are applied with steam at a flow rate of less than 5 g / min. in particular between 1 and 4 g / min. The application of the steam can be implemented using any known apparatus to generate the amount of steam useful in the method of the invention. According to a particular embodiment, this apparatus is portable, that is to say that the reservoir for generating the steam is in contact with the part of the device comprising the steam distribution orifices. The step of applying the water vapor can be performed before, during or after the heating step, and preferably before and more preferably just before the smoothing / straightening step (0.5 to 10 seconds before).

Preferably, the step of smoothing / straightening the keratinous fibers is carried out for a duration ranging from 2 seconds to 30 minutes, and preferably from 2 seconds to 20 minutes, better from 2 seconds to 10 minutes, better from 2 seconds to 5 minutes. minutes, and even better from 2 seconds to 2 minutes.

Preferably step ii) is carried out with a vapor straightener.

The method according to the invention may also comprise an additional step of drying the keratinous fibers after step i) and before step ii). The drying step can be performed by means of a hairdryer, a helmet or by free drying. The drying step is advantageously carried out at a temperature ranging from 20 to 70 ° C.

After the step of smoothing / straightening with steam iron, the keratinous fibers may optionally be rinsed with water or washed with a shampoo. The keratinous fibers are then optionally dried by means of a hairdryer or a helmet or in the open air.

According to one embodiment, the method according to the invention is implemented on natural keratinous fibers, in particular natural hair.

According to another embodiment, the method according to the invention is implemented on keratinous fibers, in particular damaged hair. Damaged hair is defined as dry or coarse or brittle or split or soft hair.

The treatment method according to the invention is particularly used on human keratinous fibers, especially sensitized hair, such as discolored, defrosted or permed fibers.

The method according to the invention can be implemented on keratinous fibers, especially hair, dry or wet. Preferably, the method is implemented on natural keratin fibers.

After step i) of the process of the invention, and before carrying out step ii), it is possible to leave the crosslinking agent (s) containing at least one group (thio) the carbonyl or the composition (s) containing (s) applied for a period of from 1 to 60 minutes, preferably from 2 to 50 minutes, preferably from 5 to 45 minutes. The exposure time can be carried out at a temperature ranging from 15 ° C to 45 ° C, preferably at room temperature (25 ° C).

The cosmetic composition which contains at least one crosslinking agent which comprises at least one (thio) carbonyl group as described above is advantageously applied to the keratinous fibers in an amount ranging from 0.1 to 10 grams, preferably from 0.2 to 5 grams of composition per gram of keratin fibers.

After application of the cosmetic composition containing at least one crosslinking agent which contains at least one (thio) carbonyl group on the keratinous fibers, the latter may be dewatered to remove the excess of composition or washed with water or with a shampoo .

The treatment method according to the invention can be implemented before, during and / or after an additional cosmetic treatment process for keratinous fibers, such as a temporary shaping process (shaping with curlers, curling iron , hair straightener) or a method of shaping durable (permanent, straightening) keratin fibers.

The following examples are illustrative of the present invention.

The amounts indicated in the examples are expressed as percentage by weight. at) . Protocol for the Preparation of the Compositions of the Process of the Invention: Malic acid 17, lyxose 19, erythrose 21, ribose 23, D-glucoronolactone 25, tartaric acid 18, and glycolic acid are tested in solution at 10% by weight in water at spontaneous pH. Maleeamic acid 24 and diethyl maleate 26 are tested at 10% by weight in ethanol, and diallyl maleate 22 is tested at 10% in isododecane. b). Protocol for evaluating the technical effect (stability, performance during / after application, texture)

Each composition produced in the preceding preparation protocol a) was tested on 4 DARK BROWN 936 type IV wicks: 2 natural wicks and 2 wicks discolored according to smoothing treatment protocols.

To quantify the contribution of steam, for each crosslinker and each type of wick (natural or discolored): a wick was smoothed with a Rowenta steampod LP8500 GB / 7PO steamer, and the other was smoothed with this same apparatus used in conventional straightening iron (without steam = Comparative 1) under the same experimental conditions.

We placed ourselves at equivalent smoothing either: 1 passage steam iron = 3 passages of iron and not with number of equivalent passages.

The operating conditions that were followed are as follows:

Classic straightening iron (Comparative 2): 10 passes at 210 ° C.

- Steam iron: 3 slow passages at 210 ° C B1) Conventional iron straightener (Comparative 1)

The locks were wetted by 5 passes under water at 37 ° C. and then placed in a glass chute.

In an 8 mL flask was added 0.054 g of crosslinking agent to be tested with 5.4 g of solvent (water, ethanol, or isododecane) i.e. 5.454 g of compositions which were prepared according to a) above.

The compositions were then applied to each wick and allowed to stand for 15 minutes at room temperature. The treated locks were then dewatered. B2) Protocol for Brazilian smoothing with conventional iron:

The locks of keratinous fibers were combed and then underwent 5 successive blow-offs in position 2 (80 ° C) of the hair dryer with a medium-diameter round brush. Each of the locks were then separated into 2. Each part underwent 10 smooth iron strokes with a comb on each half and then 2/3 passes on the set.

The locks were then washed with a shampoo such as Ultra-Sweet Chamomile and Flower Honey

Each wick was then pressed in different places so as not to touch the loop and then dried flat. B3) Protocol with iron and water vapor

The locks were wetted by 5 passes under water at 37 ° C and then placed in a glass chute. In

In an 8 mL flask was added 0.054 g of crosslinking agent to be tested with 5.4 g of solvent (water, ethanol, or isododecane) i.e. 5.454 g of compositions which were prepared according to a) above.

The compositions were then applied to each wick and allowed to stand for 15 minutes at room temperature. The treated locks were then dewatered. B4) Brazilian smoothing protocol with steam iron:

The locks of keratinous fibers were combed and then underwent 5 successive blow-offs in position 2 (80 ° C) of the hair dryer with a medium-diameter round brush. Each of the wicks were then separated into 2. Each part underwent 3 passages of 15 seconds (wick of 27 cm long) with steam on each half then 2/3 passages on the whole.

The locks were then washed with a shampoo such as Ultra-Sweet Chamomile and Flower Honey

Each wick was then pressed in different places so as not to touch the loop and then dried flat. vs). Results of the evaluation

The in vitro orientation tests were evaluated on the following 5 criteria: loop relaxation, touch, discipline, and durability

The average performance of the crosslinkers with iron vapor (invention) and with conventional iron have been compiled in the tables below:

Glossary of the notation: 1- no effect (-) 2- light effect (+) 3- marked effect (++) 4- good effect (+++)

The process according to the invention which implements the steam iron step has made it possible to obtain a significant superiority in the cosmetic performances obtained on all the evaluation criteria compared with the conventional iron-free straightener without steam.

It has been found that all the parameters are significantly higher with the process of the invention which implements a step of steam vs. iron. the comparative process, which represents a very important performance gain.

The relaxation of the loops is much better, the care given to the hair with the keratinous fiber treatment method of the invention that the method without steam iron. In addition the smoothing time was found to be much lower which allowed a level of keratin fiber treatment process to save time professional hairdressers and avoids additional gestures for said professionals. The method according to the invention has made it possible to obtain good relaxation of loops, which is durable over time.

The smoothing time was decreased by an average of three compared with a conventional steamless process.

Claims (18)

1. A method for treating keratinous fibers, especially human keratinous fibers such as the hair, using: i) a step of applying at least one crosslinking agent which contains at least one (thio) carbonyl group; and ii) a smoothing / straightening step using a steam iron; in particular i) is applied first and then second ii) the steam smoothing iron is applied without intermediate rinsing step. 2. Method according to the preceding claim wherein the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen (s) of (their) formula (I) Formulas (I) wherein: • W represents: i) either an optionally substituted (hetero) aryl or optionally substituted (hetero) cycloalkyl group, preferably represents a 5- or 6-membered phenyl or heteroaryl such as pyridinyl or heterocycloalkyl comprising at least at least one 5 to 8-membered oxygen atom such as tetrahydrofuryl, piperazynyl or hexahydrofuro [3,2-b] furanyl, ii) is a group -A- (CR 2 R 3) x A * when w is 2, with R 2 and R3, identical or different, representing a hydrogen atom or a (CrC6) alkyl group such as methyl, x represents an integer between 0 and 10, preferably x is 1, * represents the point of attachment to the groups -X1 -C (X2) -C (= CH2) -R1 and A represents an optionally substituted (hetero) aryl group o optionally substituted u (hetero) cycloalkyl, preferably A represents phenyl; iii) a hydrocarbon chain, linear or branched, polyvalent, preferably di or trivalent, saturated or unsaturated, preferably saturated, optionally substituted, preferably with a hydroxyl group or with a phenyl group, and comprising from 1 to 20 atoms of carbon; • n represents an integer inclusive between 0 and 5; more particularly between 0 and 3, such that n = 0 or 1; U and w represent an integer inclusive between 2 and 10, more particularly between 2 and 5, such that u = 2etw = 2 or 3; in particular, W represents a divalent C 1 -C 10 alkyl or trivalent C 1 -C 10 alkyl group. 3. Method according to any one of the preceding claims wherein the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen (s) from (their) formula ( II) or (III): (II) (III) as well as their salts of organic or inorganic acids or bases, their tautomers and their solvates such as hydrates; Formulas (II) and (III) in which: • X and X ', identical or different, preferably identical, represent an oxygen or sulfur atom, preferably oxygen; ALK represents a linear or branched hydrocarbon chain comprising from 1 to 10 carbon atoms, saturated or unsaturated, in particular by 1 to 3 unsaturations, conjugated or otherwise, said chain is optionally substituted by one or more groups chosen from: a) a hydroxy group; b) a -C (X) -ORb group with X as defined above, and Rb representing a hydrogen atom, an alkali metal, or alkaline earth metal, and c) a heterocyclic lactone group comprising from 4 to 8 members, saturated or unsaturated, nonaromatic, which may be optionally substituted in particular with one or more hydroxyl groups; • ALK 'represents a divalent hydrocarbon chain, linear or branched, comprising from 1 to 10 carbon atoms, saturated or unsaturated, in particular by 1 to 3 unsaturations, conjugated or not; R represents i) a hydrogen atom or ii) a group ORa with Ra representing a hydrogen atom, an alkali metal, alkaline earth metal, or a (C 1 -C 6) alkyl, (C 2 -C 6) alkenyl group, or C2-C6) alkynyl, preferably R represents a hydrogen atom or a group ORa with Ra representing a hydrogen atom, an alkaline metal, alkaline earth metal; • R 'and R ", which are identical or different, represent a group chosen from: - ALK" -O- with ALK "representing a linear or branched hydrocarbon-based chain comprising from 1 to 10 carbon atoms, and optionally from 1 to 3 unsaturations conjugated or unconjugated, preferably ALK "represents a (CrC6) alkyl, (C2-C6) alkenyl or (C2-C6) alkynyl group; -C (O) -ORb with and Rb representing a hydrogen atom, an alkali metal, or alkaline earth metal; an NRcRd amino group with Rc and Rd, identical or different, representing a hydrogen atom or a (CrC6) alkyl, (C2-C6) alkenyl, or (C2-C6) alkynyl group, preferably NH2; it being understood that ALK ', R' or R "contains at least one group comprising at least one unsaturation. 4. Method according to any one of the preceding claims wherein the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen (s) from (their) formula ( II) as defined in the preceding claim. 5. Method according to any one of the preceding claims wherein the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen (s) from (their) formula ( II) as defined in the preceding claim with R representing i) a hydrogen atom. 6. Method according to any one of claims 1 to 4 wherein the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen (s) from (their) formula (II) as defined in claim 3 with R representing ii) a group ORa with Ra representing a hydrogen atom, an alkali metal, alkaline earth metal, or a group (Ci-C4) alkyl, preferably R represents a group ORa with Ra representing a hydrogen atom, an alkali metal, or alkaline earth metal. 7. Method according to any one of the preceding claims wherein the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen (s) from (their) formula ( II) as defined in claim 3, with ALK representing a (C 1 -C 6) alkyl group optionally substituted by one or more groups selected from: a) hydroxy; b) -C (O) -ORb with and Rb representing a hydrogen atom, an alkali metal or alkaline earth metal, and c) a heterocycle lactone comprising from 4 to 6 members, which may be optionally substituted with from one to three hydroxy groups; in particular ALK is substituted by one or more groups chosen from a) and c) as defined above. 8. Method according to any one of the preceding claims wherein the agent (s) crosslinking (s) group (s) (thio) carbonyl (s) is (are) chosen (s) among them (them) of formula ( II) as defined in claim 3, with X representing an oxygen atom. 9. Method according to any one of claims 1 to 3 wherein the agent (s) crosslinking (s) is (are) of formula (III), as (s) defined (s) in claim 3. 10. Process according to any one of claims 1 to 3 and 9 wherein the agent (s) crosslinking (s) is (are) of formula (III), as (s) that defined (s) in claim 3, with R 'and R ", identical or different, representing ALK" -O- with ALK "as defined above, preferably ALK" are identical and represent a group (CrC6) alkyl, or (C2-C6) alkenyl. 11. Process according to any one of claims 1 to 3 and 9 wherein the agent (s) crosslinking (s) is (are) of formula (III), as (s) that defined (s) in claim 3, with R 'and R ", identical or different, representing: - -C (O) -ORb with and Rb representing a hydrogen atom, an alkali metal or alkaline earth metal; an NRcRd amino group with Rc and Rd, identical or different, representing a hydrogen atom or a (CrC6) alkyl, (C2-C6) alkenyl or (C2-C6) alkynyl group, preferably an NH2 amino group. 12. Process according to any one of claims 1 to 3 and 9 to 11 wherein the agent (s) crosslinking (s) is (are) of formula (III), as (s) that defined (s) in the claim 3, with ALK 'representing a divalent hydrocarbon chain, linear or branched, comprising from 1 to 6 unsaturated carbon atoms by 1 to 3 unsaturations, conjugated or otherwise; preferably ALK 'represents a (C2-C6) alkenylene or (C2-C6) alkynylene group, more preferably (C2-C6) alkenylene, even more preferably (C2-C4) alkenylene such as ethylene -CH = CH-, 13. Process according to any one of claims 1 to 3 and 9 to 12 wherein the agent (s) crosslinking (s) is (are) of formula (III), as (s) defined (s) in claim 3, with X and X 'represents an oxygen atom. 14. Process according to any one of the preceding claims, in which the crosslinking agent (s) is (are) of the following formula as well as their optical isomers, and geometric, their tautomers and acid or base salts, mineral. or organic: 15. The process as claimed in any one of the preceding claims, in which the crosslinking agent (s) is (are) in the group (s) (thio) carbonyl (s) as defined in any one of of the preceding claims is (are) in a cosmetic composition, preferably in an amount of between 1% and 80% by weight of the composition which they comprise, more particularly in a quantity of between 3% and 50% by weight. weight, preferably between 5% and 30% by weight, more preferably between 7% and 20% by weight such as 10% by weight relative to the total weight of the composition (s) comprising. 16. A method according to any one of the preceding claims wherein the step ii) smoothing / straightening by means of a steam iron said iron being at a temperature between 65 ° C and 250 ° C, particularly between 80 ° C and 230 ° C ° C, more preferably greater than or equal to 100 ° C and preferably between 100 ° C and 190 ° C; preferably, step ii) of the process for treating keratinous fibers is carried out at a temperature ranging from 150 to 220 ° C., preferably ranging from 160 ° C. to 220 ° C., preferably ranging from 160 ° C. to 210 ° C. , in particular ranging from 180 ° C. to 200 ° C. 17. A method according to any one of the preceding claims wherein the step ii) straightening / straightening by means of a steam iron said iron being applied in continuous movement from the root to the tip of said fibers, in particular fibers human keratin such as the hair, in one or more passages, in particular in two to twenty passages, the duration of each passage of the iron can range from 2 seconds to 1 minute. 18. A method according to any one of the preceding claims wherein the step ii) smoothing / straightening by means of a steam iron, the steam having a flow rate of less than 5 g / min. in particular between 1 and 4 g / min, preferably step ii) is carried out with a vapor straightener.