FR2961208A1 - Use of pyrrolidin-2-one compounds as a dispersing agent for the care, makeup and coloring of keratin fibers and useful for conditioning keratin materials - Google Patents

Abstract

Use of pyrrolidin-2-one compounds (I) and their organic or inorganic acid or base salts, optical isomers, stereoisomers or enantiomers and diastereomers, geometric isomers, tautomers, and solvates such as hydrates, as a dispersing agent for the care, makeup and coloring of keratin fibers, is claimed. Use of pyrrolidin-2-one compounds of formula (I) and their organic or inorganic acid or base salts, optical isomers, stereoisomers or enantiomers and diastereomers, geometric isomers, tautomers, and solvates such as hydrates, as a dispersing agent for the care, makeup and coloring of keratin fibers, is claimed. X : O or a divalent amino group of formula (-N(R5)-); R5 : H, 1-30C alkyl, preferably 1-6C alkyl, optionally substituted by one or more -OH, -SH, -NH 2, tri(1-6C) alkyl ammonium, or cationic heteroaryl, such as pyridinium, imidazolium, and/or guanidinium; R1, R2 : saturated linear 1-30C, branched 3-30C or cyclic 3-7C hydrocarbon chain (optionally substituted and interrupted by (i) one or more heteroatoms of O-, -N (R6) or -S-, and/or (ii) one or more -S(O)-, -S(O) 2-, -C(O)-, -N +>(R6)(R7)-, preferably -N(R6)-C(O)-, -C(O)-N(R6)-, -N(R6)-C(O)-N(R7)- or -S-S- and/or optionally (iii) optionally saturated 3-6 membered ring optionally substituted by one or more groups of OH or -NRR1a), divalent chain of formula (-cycl-Alk-cycl1-), or unsaturated linear 2-30C, branched 3-30C or cyclic 3-7C hydrocarbon chain (optionally substituted and interrupted by (i) one or more heteroatoms of O-, -N(R6) or -S-, and/or (ii) one or more -S(O)-, -S(O) 2-, -C(O)-, -N +>(R6)(R7)-, preferably -N(R6)-C(O)-, -C(O)-NR6-, -NR6-C(O)-NR7- or -S-S- and/or optionally (iii) optionally saturated 3-6 membered ring optionally substituted by one or more groups of OH or -NRR1a). Or R2 represents a sigma bond. cycl, cycl1 : cyclic hydrocarbon chain, preferably 5-6C cycloalkylene such as cyclohexylene or cyclopentylene; Alk : optionally substituted 1-6C alkylene chain, preferably unsubstituted; A1, A2 : H, OH, SH, ONR7R8, -O-P(O)(OH) 2, -O-S(OH) 2OH, SO 2OH, COOH, or 3-8 membered (hetero)cycle (optionally saturated and optionally substituted by one or more OH-1-6C alkyl, OH or -NRR1a, and the (hetero)cycle can be cationic, (i) ammonium group of formula (-N +>(R7)(R8)(R9)), (ii) guanidine group of formula (RR1aN-C(=NR2a)-N(R4a)-), preferably H 2N-C(=NH)-NH-, (iii) guanidinium group of formula (RR1aN-C(=N +>R2aR3a)-N(R4a)-), or (iv) pyrrolidin-2-one group of formula (G) or (H)); Xaa : -O- or -N(R5)-; R1aa, R2aa : R1; A1aa, A2aa : A1, where A1a and A2a cannot simultaneously represent (G) or (H); R3, R4, R3aa, R4aa : H, 1-12C linear alkyl chain or 3-12C branched alkyl chain; R6 : H, 1-20C linear alkyl or 3-20C branched alkyl, optionally substituted by group (G) or (H) and preferably terminated by (G) or (H); R7-R9 : H or 1-6C alkyl optionally substituted by one or more OH; or NR7R8, NR8R9, NR7R9 : cationic or non cationic 4-7 membered heterocycle, preferably cationic heteroaryl optionally substituted by one or more 1-6C alkyl optionally substituted by one or more OH; and R, R1a, R2a, R3a : H or 1-18C alkyl optionally substituted by one or more OH, provided that when A1, A2, R1, R2, and/or R5 contain or designate a cationic group, then the electroneutrality of (I) is provided by an anionic counter ion or its mixture. Independent claims are included for: (1) cosmetic composition comprising (I); and (2) the pyrrolidin-2-one compounds (I) comprising at least two 2-pyrrolidinone groups functionalized in position 4 by an ester, an acid or an amide, preferably two or three pyrrolidones groups , provided that R can represent an ethylene group and that these compounds are different compounds (Q) comprising e.g. 1-[2-[2-(4-carboxy-2-oxo-pyrrolidin-1-yl)ethylamino]ethyl]-5-oxo-pyrrolidine-3-carboxylic acid (A1), 1-[2-[2-[2-(4-carboxy-2-oxo-pyrrolidin-1-yl)ethylamino]ethylamino]ethyl]-5-oxo-pyrrolidine-3-carboxylic acid (A2), and 1-[2-[2-[2-[2-[2-(4-carboxy-2-oxo-pyrrolidin-1-yl)ethylamino]ethylamino]ethylamino]ethylamino]ethyl]-5-oxo-pyrrolidine-3-carboxylic acid (A3). [Image] [Image].

Description

The invention relates to the use of compounds derived from poly-2-pyrrolidone functionalized in the 4-position by an ester radical, carboxylic acid, or amide as a dispersing agent for cosmetic active agents for the treatment of keratin materials, in particular for the makeup, the dyeing of keratinous fibers, as an active ingredient in the care of said fibers. It also relates to novel polypyrrolidone derivatives and a cosmetic composition comprising them.

It is known in the field of the skin, makeup compositions of keratin materials generally contain a proportion of dyestuffs in particulate form greater than or equal to 5% by weight relative to the total weight of the composition. The formulation of makeup compositions must take into account the dispersion of these dyestuffs and the stability of said compositions. Moreover, it is also sought to optimize the spreading properties on the skin and its integuments of these coloring matters, the behavior of the color after application and / or non-transfer properties.

Moreover, in the hair care field, it is well known that hair which has been sensitized, in particular damaged and / or embrittled, to varying degrees under the action of atmospheric agents or under the action of mechanical treatments and / or chemical, such as stains, discolourations and perms, are often difficult to disentangle and comb, and also lack softness. It has already been proposed for the treatment of keratin materials and in particular hair, cosmetic compositions containing conditioning cationic surfactants, such as those described in US 2006/0078529. However, such compositions do not yet have the desired cosmetic qualities, in particular in terms of sensory properties, in particular to touch the hair after treatment. The treatment of keratinous fibers with cosmetic compositions, for example by shampoos, or by dyeing compositions in particular involving chemical oxidizing agents, or the alteration of the fibers by external agents such as light, requires the use of conditioning agent to regain flexibility of keratin fibers. Moreover, on wet hair, and often after rinsing, the fibers remain too stiff after the cosmetic treatment or treatments. It is therefore of great interest to find a way to soften keratin fibers. In addition to flexibility, there is also a need to improve the disentanglement, smoothness, combability and manageability of the hair; to facilitate the shaping of the hair, and to make more pleasant and fluid the touch of keratinous fibers.

In the field of hair dyeing, it is known to obtain so-called "permanent" dyes with dye compositions containing oxidation dye precursors, generally known as oxidation bases, such as ortho or para-phenylenediamines, ortho or para-aminophenols and heterocyclic compounds. These oxidation bases are colorless or weakly colored compounds which, when combined with oxidizing products, can give rise to colored compounds by a process of oxidative condensation. It is also known that the shades obtained can be varied by combining these oxidation bases with couplers or color modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds. This oxidation dyeing process consists in applying bases or a mixture of bases and couplers to the keratinous fibers with hydrogen peroxide (H2O2 or hydrogen peroxide) as an oxidizing agent, to be allowed to diffuse, then to rinse the fibers. The resulting colorations are permanent, strong, and resistant to external agents, including light, weather, washing, perspiration and friction. It is also known to dye keratinous fibers, especially human fibers, by direct dyeing. The method conventionally used in direct dyeing consists in directly applying to the keratin fibers "direct" dyes which are colored and dyestuff molecules having an affinity for said fibers. The compositions comprising these dyes are then left to diffuse on the fibers, and then the fibers are rinsed. The resulting colorations are temporary or semipermanent colorations because they tend to fade quickly after successive washing with shampoos. Indeed, most of the dyes used in direct dyeing are soluble in water and are desorbed from the fiber during shampoos.

For permanent coloring or direct dyeing, it can be observed a problem of dispersion of dyes or precursors staining in conventional media which has the effect of reducing the coloring power of dyes. The colors are notably less intense and less chromatic.

The 2-pyrrolidone derivatives functionalized with esters in the 4-position are known in the field of inks (see, for example, EP 1 342 759, WO 2008/131396); to improve the transdermal passage of drugs (1nt J. Pharmaceutics, 44 (1-3), 15-24 (1988)) and as natural gas inhibitors (EP 2,028,247 and EP 2,022,781). Other amide functionalized 2-pyrrolidones have been used in ink jet printing formulas (EP 2 142 610); as antiepileptic (J. Med Chem 47 (3), 530-549 (2004)); anticonvulsant (WO 2001/062726) or as a lubricating oil additive (FR 2,243,959) or a gel additive (WO 2010/039509).

The technical problems mentioned above have been solved by using, as a dispersing agent for the makeup, the coloration of the keratinous fibers, as a care active agent for said fibers one or more compounds of formula (I): ## STR1 ## cl) 1 as well as their organic or inorganic acid or base salts, optical isomers: stereoisomers or enantiomers and diastereoisomers, geometric isomers, tautomers, and solvates such as hydrates; formula (I) wherein: X represents an oxygen atom or a divalent amino group -N (R5) -; with R5 representing a hydrogen atom, a linear or branched (C1-C30) alkyl group especially (C1-C6) alkyl, optionally substituted with one or more -OH, -SH, -NH2, tri (C1-C6) groups; ) alkylammonium, cationic heteroaryl such as pyridinium, imidazolium, and / or guanidinium; R and R 2, which are identical or different, represent: a hydrocarbon chain optionally substituted, in particular by - N + (R 1) (R 8) (R 9), said chain is linear saturated in C 1 -C 30 or branched in C 3 -C 30 or cyclic in C 3 -C7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more -S (O) -, -S (O) 2 groups -, -C (O) -, -N + (R6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N (R6) -, -N (R6) -C (O) -N (R7) - or -SS- and / or optionally iii) a saturated or unsaturated carbon ring of 3 to 6 members optionally substituted with one or more identical radicals or different, especially chosen from hydroxyl OH or amino-NRR '; a divalent -Cycl-Alk-Cycl'- chain with: 15 Cycl, and Cycl ', identical or different, preferably identical, representing a cyclic hydrocarbon chain, especially a C 5 -C 6 cycloalkylene, such as cyclohexylene or cyclopentylene and representing an optionally substituted (C 1 -C 6) alkylene chain; preferentially unsubstituted; A hydrocarbon chain optionally substituted, in particular by - N + (R 1) (R 8) (R 9), said chain is linear unsaturated C 2 -C 30 or branched C 3 -C 30 or cyclic C 3 -C 7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more -S (O) -, -S (O) 2 groups -, -C (O) -, -N + (R6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N (R6) -, - N (R6) -C (O) -N (R7) - or -SS- and / or optionally iii) a saturated or unsaturated carbon ring of 3 to 6 members optionally substituted in particular by one or more radicals identical or different selected from hydroxyl OH or amino - NRR '; or R2 and / or R'2 represent (s) a bond 6; o A, and A2, which are identical or different, representing: a hydrogen atom, or a group chosen from a) -OH, b) -SH, c) -NR, R8; d) -O-P (O) (OH) 2; E) -O-S (O) 20H; f) -S (O) 20H; g) -C (O) OH; h) (hetero) saturated or unsaturated 3 to 6-membered ring optionally substituted with one or more identical or different radicals chosen from (hydroxy) (C 1 -C 6) alkyl, hydroxyl, and -NRR ', said (hetero) ring being to be cationic; i) ammonium -N + (R,) (R8) (R9): j) guanidine RR'N-C (= NR ") - N (R" ") -,

H2NN particularly NH; k) guanidinium RR'NC (= N + R "R" ') - N (R "") - and I) a radical of formula (G) or (H): or 0 R "2 X' ~ NA ,, 2 ONR "4 (G) ONR" 4 A "/ 1 (H) R" 3 R "formulas (G) and (H) in which: X X" represents an oxygen atom -O- or -N ( R5) - with R5 as defined above; R "1 and R" 2, which may be identical or different, are as defined for R'1 and R'2 above, for example 1 and 2, which are identical or different, are as defined for A1 and A2 with A "1 and A" 2 can not simultaneously represent a radical (G) or (H); - representing the point of attachment of the radicals (G) and (H) to the remainder R 3, R 4, R "3 and R" 4, which may be identical or different, represent a hydrogen atom or a linear C 1 -C 12 or branched C 3 -C 12 alkyl chain; hydrogen atom, or a linear (C 1 -C 29) alkyl or branched (C 3 -C 29) alkyl group, optionally substituted with a radical (G) or (H), preferably terminated by a radical (G) or (H) o R7, R8, and R9, which may be identical or different, representing a hydrogen atom or a (C 1 -C 6) alkyl group optionally substituted by one or more hydroxyl groups; or else R, with R8, or R8 with R9, or R, together with R9 together with the nitrogen atom carrying them, a cationic or non-cationic heterocycle, comprising from 4 to 7 chain members, preferably cationic heteroaryl, optionally substituted, in particular by one or more identical or different radicals, (C 1 -C 6) alkyl optionally substituted with one or more hydroxyls; R, R ', R "and R"', which may be identical or different, represent a hydrogen atom or a (C 1 -C 18) alkyl group optionally substituted by one or more hydroxyl groups; it being understood that when A, and / or A2 and / or R, and / or R2 and / or R5 contain or designate a cationic group, the electroneutrality of the compounds of formula (I) is ensured by an anionic counterion or a mixture of anionic counterions such as cosmetically acceptable organic or inorganic anions, especially acetate, lactate, tartrate, citrate, halide (Cl-, Br), SO42-, McSO4, EtSO4, ethosulphate, hydrogen sulfate, paratoluene sulphonate, mesylate.

Another subject of the invention is a method for treating keratin materials using the compound of formula (I), as defined above (II) or (III) as defined below.

Another subject of the invention is the compounds of formula (I) comprising at least two 2-pyrrolidinone groups functionalized at the 4-position by an ester, an acid or an amide, preferably two or three pyrrolidone groups, it being understood that R, may represent an ethylene group and that said compounds are different from the following Ln- compounds: OH o with m = 1, 2 and 4 OH OH LL 0 CH 2 -OH 0 IC-O-CH 2 -IC-CH 2 -0- ## STR1 ## N 0 - CH 2 - L \ 0- IC \ / Ô / 0 Me N Q1 SH i-Bu b 0 L2 I0 1V ~ L 0-CH2-bH-0-IC N / Bu-i MeO C-OMe -O LG OMe ON OMe

Unexpectedly, the compounds of formula (I) have proved to be highly effective dispersing agents and skincare active agents for keratin fibers such as the hair. It has been furthermore found that the derivatives of formula (I) are dispersing / emulsifying agents which improve the formulation of said makeup compositions and / or their cosmetic properties of texture, spreading, holding and non-transfer.

For the purposes of the present invention, and unless a different indication is given:

"Saturated carbon rings" are cycloalkyls such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; preferentially cyclohexyl; The "unsaturated carbon rings" are C3-C6 rings, and having 1 to 3 double bonds, conjugated or otherwise, particularly of the cycloalkylene type such as hexylenyl, or aryl such as phenyl;

"Heterocycles" are hydrocarbon rings of which one or more of the carbon atoms have been substituted with one or more heteroatoms such as oxygen, sulfur or nitrogen, said heterocycle may be saturated; it is heterocycloalkyls preferably comprising from 3 to 6 members such as morpholinyl thiomoropholinye, piperidinyl, piperazinyl, pyrrolidinyl, tetrahydrofuranyl azepanyl preferentially pirrolidinyl and morpholino; or else said heterocycle is unsaturated and comprises from 1 to 3 double bonds, conjugated or otherwise, particularly of heterocycloalkenyl or heteroaryl type, as defined below

An "aryl" radical represents a mono or polycyclic group, condensed or not, comprising from 6 to 22 carbon atoms, and of which at least one ring is aromatic; preferably the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl;

A "heteroaryl radical" represents a mono- or polycyclic group, fused or non-fused, optionally cationic, comprising from 5 to 22 members, from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium, and of which at least one ring is aromatic; preferably heteroaryl is selected from acridinyl, benzimidazolyl, 35 benzobistriazolyl, benzopyrazolyl, benzopyridazinyle, benzoquinolyl, 10 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, thiopyrylyl, triazolyl, xanthyl and its ammonium salt;

The "(hetero) rings" are either heterocycles or saturated or unsaturated carbon rings as defined above;

The "cyclic hydrocarbon chain" is a divalent chain comprising from 3 to 7 chain members, which may be saturated or unsaturated with from 1 to 3 unsaturations, in particular that cycloalkylene or arylene such as those chosen from: C - The aromatic part of a radical (hetero) cyclic may be substituted by a substituent carried by a carbon atom, chosen from: a C1-C16 alkyl radical, preferably C1-C8, optionally substituted with one or more radicals chosen from hydroxyl and alkoxy radicals; C1-C2, (poly) -hydroxyalkoxy C2-C4, acylamino, amino substituted with two identical or different C1-C4 alkyl radicals, optionally bearing at least one hydroxyl group or, the two 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 heterocycle optionally comprising another heteroatom identical or different from nitrogen; a halogen atom such as chlorine, fluorine or bromine; a hydroxyl group; a C1-C2 alkoxy radical; a C2-C4 (poly) -hydroxyalkoxy radical; an amino radical; nitro; a 5- or 6-membered heterocycloalkyl radical; a 5- or 6-membered optionally cationic heteroaryl radical, preferentially imidazolium, and optionally substituted by a (C1-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 with one or two C 1 -C 3 alkyl radicals optionally substituted, said alkyl radicals being able to form, with the nitrogen atom to which they are attached, an optionally substituted 5 to 7-membered heterocyclic ring, saturated or unsaturated, optionally comprising at least one other heteroatom which is different from or different from nitrogen, iii ) a quaternary ammonium group -N + R'R "R" ', M- for which R', R ", R" ', which may be identical or different, represent a hydrogen atom, or a C1-C4 alkyl group; and M- represents the inorganic organic counterion such as the halide, iv) or a 5- or 6-membered optionally cationic heteroaryl radical, preferably imidazolium, and optionally substituted with a (C 1 -C 4) alkyl radical, preferably methyl; an acylamino radical (-NR-C (O) R ') 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 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 bearing 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, an optionally substituted C1-C4 alkyl radical; carrier of at least one hydroxyl group and the radical R 'is a C1-C2 alkyl radical; the carboxylic radical which may be in acidic or salified form (preferably with an alkali metal or an ammonium, substituted or unsubstituted); An alkylsulphonylamino radical (R'S (O) 2-NR-) 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 R 'radical; 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 polyhaloalkyl group, preferentially trifluoromethyl (CF3);

the non-aromatic part of a cyclic or heterocyclic radical may be substituted by at least one substituent carried by a carbon atom chosen from the groups: hydroxyl, C 1 -C 4 alkoxy and C 2 -C 4 poly (hydroxy) alkoxy - alkylcarbonylamino ((RC (O) -NR'-) in which the radical R 'is a hydrogen atom, a C1-C4 alkyl radical optionally carrying at least one hydroxyl group and the radical R is a radical; C 1 -C 2 alkyl, amino substituted with two identical or different C 1 -C 4 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 5 to 7-membered, optionally substituted saturated or unsaturated compound optionally comprising at least one other non-nitrogen heteroatom or otherwise; alkylcarbonyloxy ((RC (O) -O-) in which the radical R is a C 1 -C 4 alkyl radical; , amino substituted by two gro identical or different alkyl groups C1-C4 optionally carrying at least one hydroxyl group, said alkyl radicals being able to form, with the nitrogen atom to which they are attached, a 5- to 7-membered heterocycle, saturated or unsaturated, optionally substituted, optionally comprising at least one other heteroatom different or different from nitrogen; - alkoxycarbonyl ((RO-C (O) -) wherein the radical R is a C1-C4 alkyl, amino substituted by two identical or different C1-C4 alkyl groups optionally bearing at least one hydroxyl group, said alkyl radicals which can form, 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 is different from or different from nitrogen; a compound containing one or more cationic groups which implies that said compound comprises at least one cationic group other than an acid salt, particularly said compound comprises at least one group chosen from tri (C 1 -C 6) alkylammonium, guanidinium -N + (R 6) (R 1) -; (hetero) ring or cationic heteroaryl; -N + (R 1) (R 8) (R 9) and guanidinium RR'NC (= N + R "R" ') - N (R) "") - as defined above;

a cyclic, heterocyclic radical or a non-aromatic part of an aryl or heteroaryl radical may also be substituted with one or more oxo groups;

a hydrocarbon chain is unsaturated when it comprises one or more double bonds and / or one or more triple bonds which may or may not be conjugated; preferentially it comprises from 1 to 3 double bonds;

an "organic or inorganic acid salt" is, for example, chosen from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H 2 SO 4, iv) alkyl sulphonic acids: Alk-S (O) 2OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S (O) 2OH such as benzene sulfonic acid and toluene sulfonic acid; (vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid, x) alkoxysulfinic acids: Alk-O-S (O) OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid P (O) (OH) 3; xiii) acetic acid CH3C (O) OH; xiv) triflic acid CF3S (O) 2OH and xv) tetrafluoroboric acid HBF4;

an "organic or inorganic base salt" is, for example, chosen from a salt derived from mineral bases such as i) NaOH sodium hydroxide, ii) potassium hydroxide KOH, or organic bases such as iii) ammonia; iv) amines and hydroxyamines such as (tri) (C 1 -C 6) alkylamine (tri) hydroxy (C 1 -C 6) alkylamine; salts derived from alkali or alkaline earth metals; or "alkalinizing agents" as defined below; an "anionic counterion" is an anion or an anionic group associated with the cationic charge of the dye; more particularly the anionic counterion is selected from i) halides such as chloride, bromide; ii) nitrates; iii) sulfonates, including C1-C6 alkylsulfonates: Alk-S (O) 20- such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfonates: Ar-S (O) 2O- such as benzenesulphonate and toluenesulphonate or tosylate; v) citrate; vi) succinate; (vii) tartrate; viii) lactate; ix) alkyl sulphates Alk-O-S (O) O- such as methysulphate and ethylsulphate; x) Ar-O-S (O) O- aryl sulphates, such as benzenesulphate and toluenesulphate; xi) alkoxysulfates: Alk-O-S (O) 2O- such as methoxy sulfate and ethoxysulfate; xii) aryloxysulfates: Ar-O-S (O) 2 O-, xiii) phosphate; (xiv) acetate; xv) triflate and xvi) borates such as tetrafluoroborate;

an "alkyl" radical is a hydrocarbon radical, linear or branched, saturated, comprising from 1 to 30, particularly from 10 to 20, preferably from 1 to 6 carbon atoms, more preferably from 1 to 3 carbon atoms, such as the radical; methyl or ethyl;

an "alkenyl" radical is a linear or branched, unsaturated hydrocarbon-based radical comprising from 2 to 30 carbon atoms, particularly from 10 to 20 carbon atoms and comprising from 1 to 5 conjugated or non-conjugated double bonds, particularly 1 to 2 double bonds, preferably 1 single double bond

an "alkoxy" radical is an "alkyl-oxy" alkyl-O- radical in which the alkyl part is as defined previously;

the alkyl, alkoxy or (hetero) cycloalkyl radical followed by "optionally substituted with ..." means that the radicals may have one or more hydrogen atoms substituted with one or more substituents in question, particularly one or two substituents in question; the expression "optionally substituted" attributed to the alkyl radical, the hydrocarbon-based chain or the alkylene chain, meaning that said alkyl radicals or hydrocarbon-based chain 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 C1-C4 alkyl radicals, said alkyl radicals being able to form with the nitrogen atom which carries them a heterocyle comprising from 5 to 10 carbon atoms; 7-membered ring, optionally comprising another heteroatom different or different from nitrogen; v) or a quaternary ammonium group -N R'R "R" ', M for which R', R ", R" ', identical

or different represent a hydrogen atom, or a C1-C4 alkyl group, or else -N R'R "R" 'forms a heteroaryl heterocycle such that

imidazolium optionally substituted with a Cl-C4 alkyl group, and M represents the counterion of the corresponding organic acid, mineral or halide; and vi) -N + (R6) (R1) (R8) I as defined above. Compounds of formula (I), (II) or (III) According to one preferred embodiment of the invention, the compound of formula contains at least two radicals, preferably two or three radicals, 2-pyrrolidinones functionalized in position 4 by an ester, a acid or an amide preferentially radical (G). More particularly, R, represents a divalent chain -alk-T-alk 'with - T representing: - either a covalent bond 6, - or a heteroatom such as O,

or a group -N (R '6) - with R' 6 representing a hydrogen atom or a (C 1 -C 6) alkyl group, or -alk "- (G);

- or a divalent group -X.-alk "-Xb- with Xa and Xb, identical or different, representing a heteroatom such as O or a group NH; - alk, alk ', and alk", identical or different, representing a (C 1 -C 6) alkylene group, preferably alk, alk 'and alk "are identical and represent an ethylene or propylene chain, and - A represents a radical (G) as defined above.

According to another preferred embodiment of the invention, the compound of formula contains at least two radicals, preferably two or three radicals, 2-pyrrolidinones functionalized in the 4-position by an ester, an acid or an amide preferably radical (H). More particularly, R2 represents a divalent chain -alk-T-alk'- with -T representing: - either a covalent bond 6, - or a heteroatom such as O, - or a group -N (R'6) - with R ' 6 representing a hydrogen atom or a (C 1 -C 6) alkyl group, or -alk "- (H); - a divalent group -X.-alk" -Xb- with Xa and Xb, identical or different , representing a heteroatom such as O or an NH group; - alk, alk ', and alk ", identical or different, representing a (C 1 -C 6) alkylene group, preferably alk, alk' and alk" are identical and represent an ethylene chain, or propylene; and - A2 represents a radical (H) as defined above.

According to a particularly preferred embodiment of the invention, the compounds of formula (I) containing one or more cationic groups.

According to one particular embodiment of the invention, the compounds of formula (I) are such that X and X "represent an oxygen atom or an amino group -N (R5) -particularly R5 = H or a group (C According to another particular embodiment of the invention, in the compounds of formula (I), the radicals R 3, R 4, R "3 and R" 4 represent a hydrogen atom.

According to one variant, the compounds of formula (I) are such that R 1 and / or R 2, which are identical or different, represent: a hydrocarbon chain optionally substituted, in particular by -N + (R 1) (R 5) (R 9), said chain is saturated or unsaturated, linear C1-C3o or branched C3-C30 or cyclic C3-C, preferably cycloalkyl; said hydrocarbon chain is optionally interrupted by: one or more heteroatoms such as -O-, -N (R6) - or -S-, one or more -S (O) -, -S (O) 2- groups, -C (O) -, -N + (R6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N (R6 ) -, -N (R6) -C (O) -N (R) - or -SS- and / or optionally - a 3 to 6-membered saturated or unsaturated carbon ring optionally substituted by one or more identical or different radicals especially chosen from hydroxyl (OH) or amino (-NRR '). According to another advantageous variant of the invention, the compounds of formula (I) are such that R2 and / or R'2 represent a bond 6. A particularly advantageous variant of the invention relates to the compounds of formula (I) in which R, denotes a linear saturated C 1 -C 20 or branched C 3 -C 20 hydrocarbon-based chain optionally interrupted by one or more heteroatoms such as O, S or -N (R 6) -, -N + (R 6) (R 1) - groups, -N (R6) -C (O) -, -C (O) -N (R6) -, -N (R6) -C (O) -N (R) - or -SS- and / or optionally substituted by one or more identical or different radicals chosen from hydroxyl OH or -NR'R. Preferentially, the hydrocarbon chain is not interrupted or substituted. In particular, the compound of formula (I) is such that the radical R 6 represents a (C 1 -C 6) alkyl group which is optionally substituted, preferably terminated, with a radical (G) or (H) as defined above and R represents an atom hydrogen or a (C 1 -C 6) alkyl group. Preferably, R "2 represents a (C 1 -C 4) alkylene group According to another advantageous variant of the invention, the compound of formula (I) is such that R 2 denotes a linear saturated C 1 -C 12 or branched hydrocarbon chain. C3-C12 optionally interrupted by one or more heteroatoms such as O, S or -N (R6) -, -N + (R6) (R1) -, -N (R6) -C (O) -, -C ( 0) -N (R6) -, -N (R6) -C (O) -N (R7) - or -SS- and / or optionally substituted with one or more identical or different radicals chosen from hydroxyl OH or NRR 'with R, and R 'preferably representing a (C 1 -C 6) alkyl group, preferably the hydrocarbon chain is not interrupted or substituted, According to a particularly preferred embodiment of the invention, the compounds of formula (I) are such that X = X ', R = R', and R2 = R'2 and have the following formula (II) or (III): R ~ R4- N ~ O ONR4 ON ~ R4 R '/ 1 A'1 R4NO R 1 X -R 2 OR R 3 X 2A, A'2 R "X Compounds of formula (II) and (III) with c: X represents an oxygen atom or a group -N (R5) -; with R 5 representing a hydrogen atom, a linear C 1 -C 30 or branched C 3 -C 30 alkyl chain optionally substituted by one or more groups chosen from -OH, -SH, -NH 2 -R, and R 2, which are identical or different, represent a hydrocarbon chain optionally substituted in particular by -N + (R7) (R5) (R9) said chain is saturated, linear C1-C20 or branched C3-C20 or cyclic C3-C7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more -S (O) -, -S (O) 2 groups -, -C (O) -, -N + (R6) (R7) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N ( R6) -, -N (R6) -C (O) -N (R7) - or -SS- and / or optionally 2 R3 O iii) a saturated or unsaturated 3 to 6-membered carbon ring optionally substituted by one or more identical or different radicals chosen in particular from hydroxyl OH or amino-NRR '; a divalent chain -Cycl-Alk-Cycl'- with: Cycl, and Cycl ', identical or different, preferably identical, representing a cyclic hydrocarbon chain especially a C5-C6 cycloalkylene, such as cyclohexylene or cyclopentylene and ^ AIk representing a optionally substituted (C1-C6) alkylene chain; preferentially unsubstituted; a hydrocarbon chain optionally substituted, in particular by -N + (R 1) (R 6) (R 9), said chain is linear unsaturated C 2 -C 20 or branched C 3 -C 20 or cyclic C 3 -C 7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more -S (O) -, -S (O) 2 groups -, -C (O) -, -N + (R6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N (R6) -, -N (R6) -C (O) -N (R7) - or -SS- and / or optionally iii) a saturated or unsaturated carbon ring of 3 to 6 members optionally substituted in particular by one or more radicals identical or different selected from hydroxyl OH or amino-NRR '; with R, R ', independently selected from a hydrogen atom or a (hydroxy) (C1-C16) alkyl group; - R6 represents a hydrogen atom or a linear (C 1 -C 26) alkyl or branched (C 3 -C 26) alkyl radical, optionally terminated by a radical of structure (G) or (H), O R "2 X '~ NA "2 ONR" 4 ONR "4 R" (G) A "/ 1 (H) or 1 formulas (G) and (H) in which: R" 3 \ X "has the same meaning as X, ie represents an oxygen atom -O- or -N (R5) - with R5 as defined above; R "q and R" 2, which are identical or different, are as defined for R 'and R'2 above; - A ,, A'2, and A "2, identical or different, represent a hydrogen atom, or a group selected from NRR ', N + (R) (R8) (R9), -OH, -SH , -OPO3H2, -OSO3H, -SO3H, and -CO2H .- R ', and R'2, respectively R "q and R" 2 have the same meaning as R, and R2; R'2 and R "2 may besides designating a covalent bond.

Preferably A'2 and A "2, respectively A ', and A" 1, are identical. In particular, R 7, R 8, and R 9 independently represent a (C 1 -C 19) -alkyl (hydroxy) -alkyl radical. According to another preferred embodiment of the invention, the radicals R3, R4, R'3; R'4; R "3 and R" 4 represent, independently of one another, a hydrogen atom, a linear (C 1 -C 12) alkyl or branched (C 3 -C 12) alkyl chain. Even more particularly, R3 = R4 = R "3 = R" 4 = H; X is O or -NR5; R5 represents a hydrogen atom, a C1-C6 or branched C3-C6 linear alkyl chain.

According to a particular embodiment of the invention, R, R 'are independently selected from H or C 1 -C 6 alkyl. R 6 preferably denotes a hydrogen atom or a C 3 -C 20 linear or branched C 1 -C 20 alkyl radical, optionally terminated by a radical of structure (G) 0 R "2 R" 3 ~ X "2 ONR" 4 (G) formula (G) in which: - R "q and R" 2, identical or different, represent: ^ a chain hydrocarbon optionally substituted, in particular with N + (R 1) (R 8) (R 9), said chain is saturated, linear C 1 -C 29 or branched C 3 -C 20 or cyclic C 3 -C 7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more -S (O) -, -S (O) 2 groups -, -C (O) -, -N + (R'6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N (R6) -, - N (R6) -C (O) -N (R,) - or -SS- and / or optionally iii) a saturated or unsaturated carbon ring of 3 to 6 members optionally substituted with one or several identical or different radicals chosen in particular from hydroxyl OH or amino-NRR '; particularly R and R ', which are identical or different, are chosen from H and C 1 -C 6 alkyl. a hydrocarbon chain optionally substituted, in particular with -N + (R 1) (R 6) (R 9), said chain is saturated, linear in C 1 -C 20 or branched in C 3 -C 20 or cyclic in C 3 -C 7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R'6) - or -S-, ii) one or more -S (O) -, -S groups ( 0) 2-, -C (O) -, -N + (R6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (0) ) -N (R6) -, - N (R6) -C (O) -N (R1) - or -SS- and / or optionally iii) a 3 to 6-membered saturated or unsaturated carbon ring optionally substituted with one or more identical or different radicals in particular chosen from hydroxyl OH or amino-NRR '; R '6 denotes more particularly a hydrogen atom or a linear or branched C1-C20 alkyl radical C3-C20, optionally terminated by a radical of structure (H) R "4 A" / 1 (H) Formula (H in which: R "A ', A' 2, and A" 2 independently represent a hydrogen atom, a radical -NRR ', a radical -N + (R7) (R8) (R9), An- and An-represents anionic counterion. Preferably A ', and A "1, respectively A'2 and A" 2 are identical R7, R8, R9 independently represent a radical (hydroxy) C1-C18 alkyl; R3, R4, R'3; R'4; R "3; R" 4 represent, independently of one another, a hydrogen atom, a linear C, -C12 or branched C3-C12-X "alkyl chain has the same meaning as X; R ', and R 2, respectively, R "q and R" 2 have the same meaning as R, and R2, R'2 and R "2 may further designate a covalent bond. Even more preferably, the compounds of formula (I), (II) or (III) are such that: R 3 = R 4 = R "3 = R" 4 = H hydrogen atom; X represents O or -NH 2 R 2 denotes: a divalent radical - (CH 2) '- T- (CH 2) n - a radical chosen from Q, net iii: CH, CH 3 O with n integer inclusive between 1 and 10; m integer inclusively between 6 and 20; and p = 0 or 1 -T- denotes a covalent bond or an oxygen or sulfur atom, a radical -SO2- or -NH-CO-NH- or -SS- or -NH- or -N [(C, -C16) alkyl] -, or a radical selected from: H3 ~ CN or N- (CH2) y X and NR 1 \ \\ O With y designating an integer inclusive between 2 and 10, X has the same definition (O or NH) R ', and R "q denote a linear saturated C, -C, O or branched C 3 -C 10 hydrocarbon chain, and R' and R" are preferably identical.

A ', and are identical and chosen from a hydrogen atom, a radical NRR', a radical N + (R7) (R8) (R9), An- with R, R 'independently denoting a hydrogen atom or a radical C1-C4 alkyl and R7, R8, R9 independently denoting a C1-C18 alkyl radical R, denotes: a divalent radical - (CH2) '- T- (CH2) n, a radical chosen from Q, net iii such as defined above for R2, with -T- denoting a covalent bond or an oxygen or sulfur atom, a radical -SO2- or -NH-CO-NH- or -SS- or -NH- or -N [ (C, - C16) alkyl] -, or a radical chosen from: XA "~ R" ~ zz and N- (CH2) yXII NO ^^ r0 An- - (CH2) XIINO XN, A "R7 R 2 and R 2 are as defined above for R 2, R '2 and R "2 denote a C 3 -C 10 linear or C 3 -C 10 branched linear or saturated hydrocarbon chain. Preferably, R'2 and R "2 are identical, A'2 and A" 2 are identical and chosen from a hydrogen atom, a radical NRR ', a radical N + (R7) (R5) (R9), An -, preferably H and R, R 'independently denote a hydrogen atom or a C1-C4 alkyl radical

When the compounds of formula (II) or (III) contain or designate a cationic group, the electroneutrality of these compounds is provided by an anion or a mixture of cosmetically acceptable organic or inorganic anions, such as acetate, lactate, tartrate, citrate, Cl-, Br, SO42-, McSO4, EtSO4, ethosulfate, hydrogen sulfate, paratoluene sulfonate, mesylate.

As mentioned above, the subject of the present invention is also new compounds comprising at least two 2-pyrrolidinone groups functionalized at the 4-position by an ester, an acid or an amide, preferably two or three pyrrolidone groups, it being understood that R, can not represent an ethylene group and that said compounds are different from LuL compounds as described above.

According to one particular embodiment of the invention, the compounds of formula (I) contain three 2-pyrrolidinone groups functionalized at the 4-position by an ester, an acid or an amide with: X representing O or -NR 5; R 5 represents a hydrogen atom, a linear C 1 -C 30 or branched C 3 -C 30 alkyl chain optionally substituted with one or more -OH, -SH, -NH 2, trialkyl (C 1 -C 6) ammonium, pyridinium or imidazolium radicals; guanidinium; R 1 and R 2 independently denote: a saturated linear C 1 -C 20 or branched C 3 -C 20 saturated hydrocarbon chain interrupted by a NR 10 or N + (R 6) (R 7) radical, and optionally substituted by one or more heteroatoms such as O, NR 6; , S, S = O, O = S = O, or CO or N + (R6) (R7) groups or combinations thereof such as -NR6-CO- or -NHCONH- or -SS- and / or optionally containing one or more saturated or unsaturated 3- to 6-membered carbon rings and / or optionally substituted with one or more identical or different radicals selected from OH hydroxyl or -NRR 'amino; a linear unsaturated C2-C20 or branched C3-C20 hydrocarbon chain, interrupted by an NR16 or N + (R6) (R3) radical, optionally containing one or more heteroatoms such as O, NR6, S, S = O, 0 = S = O or CO or N + (R6) (R) An-groups or combinations thereof such as -NR6-CO- or -NHCONH- or -SS- and / or optionally containing one or more saturated or unsaturated carbon rings from 3 to 6 members and / or optionally substituted by one or more identical or different radicals chosen from hydroxyl (OH) or -NRR '; R and R ', which may be identical or different, represent a hydrogen atom or (hydroxy) C 1 -C 16 alkyl; R 6 denotes a hydrogen atom or a C 3 -C 20 linear or branched C 1 -C 20 alkyl radical; - Rio denotes a linear (C 1 -C 20) alkyl radical or (C 3 -C 20) branched alkyl terminated by a radical of structure, (G) or (H) as defined above;

R, denotes a (C 1 -C 16) -hydroxyalkyl radical; A, and A2 represent: a hydrogen atom, a radical NRR ', a radical N + (R) (R6) (R9), An- a radical of formula (G) or (H) as defined above and A , 25 and A2 can not simultaneously denote a radical (G) and / or (H); A 'and A'2, respectively A "q and A" 2, represent: - a hydrogen atom - a radical NRR' - a radical N + (R,) (R6) (R9), An- an OH radical, an SH radical, an OPO3H2 radical, an OSO3H radical, an SO3H radical or a CO2H radical; R8 and R9 independently denote a C1-C19 (hydroxy) alkyl radical; - R3, R4, R'3, R'4 independently denote a hydrogen atom or a linear C1-C2 or branched C3-C12 alkyl radical; - R ', and R'2, respectively R "q and R" 2, have the same meaning as R, and R2, R "2 may further designate a covalent bond, and - X' and X" have the same meaning X. According to a preferred embodiment, the compounds of formula (I) contain three 2-pyrrolidinone groups functionalized at the 4-position by an ester, an acid or an amide and X representing O; and the compound of formula (I) comprises three groups (G). Another variant corresponds to the compounds of formula (I) which comprises three groups (H) and X representing NR5; Another variant corresponds to the compounds of formula (I) which comprises three groups (G) and X represents O; and another variant corresponds to compounds of formula (I) which comprises three groups (G) and X represents NR5.

According to one particular embodiment of the invention, the compounds of formula (I) contain two 2-pyrrolidinone groups functionalized at the 4-position by an ester, acid or amide group which are: Those of formula (I) for which A denotes a radical (G) and for which X = NR5: Compounds of structure (I) such that Al denotes a radical of structure (G) and A2 denotes a hydrogen atom, a radical NRR ', a radical N + (R) ( R9) (R9) An-, an OH radical, an SH radical, an OPO3H2 radical, a OSO3H, SO3H, or CO2H radical; R6 being limited to a hydrogen atom or a linear or branched C1-C20 alkyl C3-C20 radical, the other substituents being as defined above; - Those of formula (I) for which A, denotes a radical (G) and for which X = O: 28 Compounds of structure (I) such that Al denotes a radical of structure (G) and A2 denotes a hydrogen atom a radical NRR ', a radical N + (R) (R6) (R9) An-, an OH radical, a radical SH, a radical OPO3H2, a radical OSO3H, SO3H, or CO2H; R6 being limited to a hydrogen atom or a linear or branched C1-C20 alkyl C3-C20 radical, the other substituents being as defined above; - Those of formula (I) for which Al denotes a radical (H) and for which X = NR5: Compounds of structure (I) such that Al denotes a radical of structure (H) and A2 denotes a hydrogen atom, a NRR 'radical, an N + radical (R,) (R6) (R9) An-, an OH radical, an SH radical, an OPO3H2 radical, an OSO3H, SO3H, or CO2H radical; R6 being limited to a hydrogen atom or a linear or branched C1-C20 alkyl C3-C20 radical, the other substituents being as defined above; - Those of formula (I) for which Al denotes a radical (H) and for which X = O: Compounds of structure (I) such that Al denotes a radical of structure (H) and A2 denotes a hydrogen atom, a NRR 'radical, an N + radical (R,) (R6) (R9) An-, an OH radical, an SH radical, an OPO3H2 radical, an OSO3H, SO3H, or CO2H radical; R6 being limited to a hydrogen atom or a linear or branched C1-C20 alkyl C3-C20 radical, the other substituents being as defined above; Derivatives having 2 or 3 2-carboxy pyrrolidinone-carboxy groups of formula (I), (II), (III): Compounds of formula (II) NOO ~, O ~ / OOO o O ~~ OOOOONO / O OOO NOO 0 0 0 0 OONONN \ ~ {po 000 0 0 o 0 opo /// o 0 /// o VVV NN ~ OO \ OOO ~~ OOOO l ~~ p O iN NO ~ ^ 7 / OIJ \ IO Ooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo ,,. / \ oo / -, s / S ~ - .. OO o N Off / NOOONOOONO OSO OSNOON o NNO \ O ~ SIS / OO ° ONOON (\ / O + AN- N ~ O o ~ Î o oo N ~ O o SNO \ ôl - \ OON ~ / ONOOO SO OHONOO ~ Off \ ~ NHO / OO ~ OON \ / OOONNOHONOO - \ N ~ OONN \ OO 0 ~ 0 = OOOOO // OONNON \ N ~ NOO ~ OO 0 N \ / - II O- / YO Inl OO JI O NT NONNNO ~ N \ \ OO OO, Nr OONO ^ ~ SO ONON -N IOI 0 OO NH OJNO / NNN NH HON ~ N. ONON p ~ N ~ \ NO --NO It / O ~ \ NO O ///// O, N O - \ / ^ IY ~ HN ^ 7O ~ \ N --- `NJ OHN Io OHNO ~ N IfOI ~ iN O = __, ~ 7 ~ O ^ ~~~ ~ NO N ~ II {o ^ / ~ HO ~ J7 NO Q_ NO H0 ~ \ NN 0 iN H o N d- -z xz xz -z zx xz zx o xz -z xz xz oooo OI ~ NNHNOO Hui NHHONNOO O- Hui NHHONNN ^ ~ HHONNO ^ / iN N / v \ N ~ O ° H II NOONONNO ~ OH HN O NfH NO OH oz ~ ° xz o ~ x ~ z xz o zx oo zx z ~ ozoz ~ zo ~ zx po ~ ~ z I ° I ° O z \) ° o xz xz xz o ~ ozx zo ° 0 xz z O oo oo zozzzoozz xz ~ xz 0 O zx zx z xz z \ ^ oo zz z 0 0 ozoozzo xz ozo 0 \ ) OZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZZ OZ OO 0 OO 0N OHNON NH OO / \ NO, ~ ~ YN H = ~ JY HN o HH, NOONNOO HN N HO - o ^ i ~ N,, N oo NI ~ JT o ~ - oII} ~ ~ / -O oH, N ~ ox H,, N v ~ N o ~ Y 'NOJ ~ 1) O ~ 7 HN ~ ONOH ~ o N r ~ o \ Ili` / ~ \ H \ I7 / I ~ / JONNN HN NH ~ OO o - NHO ~ \ ~ NH ONO ~ N ~ NH N iN OHO ~ / \ HOO NH NH O ## EQU1 ## where ## STR2 ## where ## STR2 ## where ## STR2 ## NO o NH IN `1 NH / HN pf OON ~} II ~ + ~ N ^ / i ~ \ N ~ HONO An- (/ \ J An- O \ An- \ NN ^ iN ~~ NO HNO -N / Compounds of formula (III) oo ~ oo ~ O o N N o n ~ n ~ p I -O HO O ~ OO -pH OO ed HN N o O ~ ~ o o o o o o o o o N o o o N o o o o o o o o o o o / o) HO N (NNOO \ ~ O p HO 1 JN HN SNO ~ (\ `~~; \ HN O - NN7 \ k 1 An- AN- O O NH O / / N - NNO \ - \ _ HN s O) rcN ON An- // ## EQU1 ## OS t OO ~ - o ~ -SNN ~ \ I + / ~ / NO o \ \ o o O O O HO \ o N ~ / SS ~ / NO o OWX 0 NH SN HN \ 0 O p O py ZO OH O In this case, we have the following information: ## EQU1 ## ## STR1 ## ## EQU1 ## ## STR1 ## ## STR1 ## ## STR1 ## ## STR2 ## oo / ~ nn \\ o \ / o o o o o o o o ~ ~ o o o o o o o o o o o o o o o o o o o o NO // OON Name with An-representative anionic counterion such as acetate, lactate, tartrate, citrate, halides such as Cl-, Br, SO42-, McSO4, EtSO4, ethosulfate, hydrogen sulfate, paratoluene sulfonate, and (C 1 -C 6) alkoxysulfate such as mesylate; above compounds, as well as their organic or inorganic acid or base salts, optical isomers: stereoisomers or enantiomers and diastereoisomers, and solvates such as hydrates.

The compounds of formula (I) of the invention are prepared according to the following general synthetic routes: Derivatives of formula I with A, re-resent a radical G and with X = NR .. or O The diamine is applied solution in an alcohol such as, for example, ethanol, isopropanol, butanol and then is added to the itaconic acid ester dissolved in the same alcohol. The mixture is then brought to reflux by eliminating the methanol formed. The derivative is thus obtained and isolated. The derivative B is obtained by saponification of the derivative (A) under standard conditions, such as, for example, in a methanol / water mixture in the presence of an excess of sodium hydroxide and then after evaporation of the alcohol, addition of a solution of acid such as for example hydrochloric acid by cooling at low temperature (0 to 5 ° C) to obtain a pH of the order of 1 to 3. The derivative (B) is thus obtained either by precipitation followed by filtration, either by extraction with an organic solvent such as, for example, dichloromethane, ethyl acetate and then dry evaporation of the organic phase. The derivative (B) can be reacted under conditions of peptide type condensation (Dicyclohexylcarbodiimide / low temperature / dimethylformamide then addition of N-hydroxysuccinimide) to yield derivative (C) which can be isolated or not. The derivative (D) is then obtained by adding the amine (or alcohol) dissolved in a solvent, such as for example dichloromethane, on the derivative (C) dissolved in the same solvent. The derivative (B) can also be converted into acid chloride by an agent such as, for example, thionyl chloride, oxalyl chloride and then the acid chloride obtained is reacted with the amine (or alcohol) to lead to the compound (D). The quaternized goat compound (I) is obtained by reacting the compound (D) and an alkylating agent such as, for example, methyl iodide, dimethyl sulphate, ethyl iodide, diethyl sulphate, or a halide. The derivative (E) is isolated either by filtration or by dry evaporation followed by washing with an organic solvent such as, for example, acetone or ethyl acetate. An ion exchange can be carried out if necessary at the end of the reaction, by contact with an ion exchange resin selected according to the desired exchanges. These resins are, for example, IRA 402 (alkyl sulphate exchange in chlorides), IRA 400 (iodide exchange in chloride).

Derivatives of formula I with A, re-resent an H radical with X = NR5 or O The amine is dissolved in an alcohol such as for example ethanol, isopropanol, butanol and is then added to the ester of itaconic acid dissolved in the same alcohol. The mixture is then refluxed to remove the methanol formed.

The derivative is thus obtained and isolated. The derivative (L) is obtained by saponification of the derivative (K) under standard conditions, such as, for example, in a methanol / water mixture in the presence of an excess of sodium hydroxide and then after evaporation of the alcohol, addition of a solution of acid such as for example hydrochloric acid by cooling at low temperature (0 to 5 ° C) to obtain a pH of about 1 to 3. The derivative (L) is thus obtained either by precipitation followed filtration, or by extraction with an organic solvent such as for example dichloromethane, ethyl acetate, and then dry evaporation of the organic phase. The derivative (L) can be reacted under conditions of peptide type condensation (Dicyclohexylcarbodiimide / low temperature / dimethylformamide then addition of N-hydroxysuccinimide) to yield the derivative (M) which can be isolated or not. The N derivative is then obtained by adding the amine (or alcohol) dissolved in a solvent, such as for example dichloromethane, on the derivative (M) dissolved in the same solvent. The derivative (L) can also be converted into acid chloride by an agent such as, for example, thionyl chloride, oxalyl chloride and then the acid chloride obtained is reacted with the amine (or alcohol) to lead to the compound (N). The quaternized goat compound (I) is obtained by reacting the compound (N) and an alkylating agent such as, for example, methyl iodide, dimethylsulfate, ethyl iodide, diethylsulfate, or a halide. The derivative (E) is isolated either by filtration or by dry evaporation followed by washing with an organic solvent such as, for example, acetone or ethyl acetate. An ion exchange can be carried out if necessary at the end of the reaction, by contact with an ion exchange resin selected according to the desired exchanges. These resins are, for example, IRA 402 (alkyl sulphate exchange in chlorides), IRA 400 (iodide exchange in chloride).

General scheme of synthesis of the compounds of formula (I) such that A, represents a radical (G) with X = NR5 or O: O 2 ~ p u 0 ~ + H2N-R. NH 2 EtOH O reflux (A) quaternizing agent General synthetic scheme of the compounds of formula (I) such that A, represents a radical (H) with X = NR5 or O: _RZ ~ A2] + An- + f Ad-R2 , X0 An- (1) C + Al R NH2 EtOH (K) reflux CH3OH / NaOH reflux + H HO CH2Cl2 2 HX-R2 CH2Cl2 NHS / DCC DMF 0-5 ° CO HX-R ~ XH CI O tertiary base ( ## STR2 ## Si quaternization quaternizing agent Y (I) X \ R2 Cosmetic composition: The compounds of formula (I), (II) or (III) may be in a cosmetic composition. In addition, an object of the invention relates to a cosmetically acceptable composition which contains which contains one or more cationic or non-cationic compound of formula (I) as defined above, comprising one or more pyrrolidone radicals. The composition according to the invention is cosmetically acceptable for the conditioning of keratin materials i.e. it generally comprises water or a mixture of water and one or more organic solvents or a mixture of organic solvents. Preferably, the cosmetic composition of the invention contains water. In particular, it contains at least 50% by weight relative to the total weight of the composition, of water. More particularly, it comprises more than 70% by weight of water relative to the total weight of the composition. By organic solvent is meant an organic substance capable of dissolving or dispersing another substance without chemically modifying it.

Organic Solvents: As an organic solvent, there may be mentioned, for example, C1-C4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, hexylene glycol, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol.

The organic solvents are present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately. According to a particular embodiment of the invention, the composition contains as support only water and no organic solvents other than those of formula (I) as defined above. Adjuvants: The composition or compositions of the dyeing method according to the invention may also contain various adjuvants conventionally used in hair dyeing compositions, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants. or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, mineral or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents, agents clouding.

Said adjuvants are preferably chosen from surfactants such as anionic, nonionic surfactants or mixtures thereof and inorganic or organic thickening agents other than those of formula (I). The adjuvants above are generally present in an amount for each of them between 0.01 and 40% by weight relative to the weight of the composition, preferably between 0.1 and 20% by weight relative to the weight of the composition. Of course, one skilled in the art will take care to choose this or these optional additional compounds in such a way that the advantageous properties intrinsically attached to the composition according to the invention is not, or not substantially, impaired by the addition or additions considered.

Dyes: The composition may comprise one or more pigments and / or one or more direct dyes. These direct dyes are, for example, chosen from those conventionally used in direct dyeing, and among which may be mentioned all the aromatic and / or nonaromatic dyes of current use such as neutral, benzene neutral, acidic or cationic direct dyes, direct dyes neutral azo, acidic or cationic, natural direct dyes other than pigments and / or one or more direct dyes not or not soluble in hydro-alcoholic solvents, quinone direct dyes and in particular neutral, acidic or cationic anthraquinone dyes, dyes direct azine, triarylmethane, indoamine, methines, styryl, porphyrins, metalloporphyrins, phthalocyanines, methine cyanines, and fluorescent dyes.

Among the natural direct dyes that may be mentioned are lawsone, juglone, indigo, isatin, curcumin, spinulosin, apigenidine, orceins. It is also possible to use the extracts or decoctions containing these natural dyes, and in particular poultices or extracts made from henna. The additional direct dye (s) used in the composition preferably represents from 0.001% to 10% by weight approximately of the total weight of the composition (s) containing them and even more preferentially from 0.05% to 5% by weight approximately. The cosmetic composition according to the invention comprising one or more pigments and / or one or more direct dyes which are poorly or not soluble in hydro-alcoholic solvents as defined above may also use or comprise one or more oxidation bases and / or or one or more couplers conventionally used for dyeing keratinous fibers. Among the oxidation bases that may be mentioned are para-phenylenediamines, bisphenylalkylenediamines, para-aminophenols, bis-para-aminophenols, ortho-aminophenols, heterocyclic bases and their addition salts. Among these couplers, it is possible to mention in particular, meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalenic couplers, heterocyclic couplers and their addition salts. The oxidation base (s) present in the composition (s) are in general present each in an amount of between 0.001% and 10% by weight relative to the total weight of the corresponding composition (s).

According to another particular embodiment of the invention, the composition according to the invention does not contain an oxidation base.

According to yet another embodiment, the composition does not contain a coupler. Preferably, the composition according to the invention does not contain an oxidation base or aromatic amine type couplers. The cosmetic composition of the invention may be in various galenical forms, such as a powder, a lotion, a mousse, a cream, a gel or in any other form suitable for dyeing keratinous fibers. They can also be packaged in a pump bottle without propellant or under pressure in an aerosol bottle in the presence of a propellant and form a foam.

The pH of the composition According to one particular embodiment of the invention, the pH of the conditioning composition is less than 7, preferably between 6 and 2 and particularly between 3 and 5. The pH of the composition according to the invention can be adjusted. to the desired value by means of acidifying or basifying agents usually used for dyeing keratin fibers or else using conventional buffer systems. Among the acidifying agents of the compositions used in the invention, mention may be made, for example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid and carboxylic acids, such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids.

Alkalizing Agents The composition according to the invention may contain one or more basifying agent (s). The amount of alkalinizing agent (s) is preferably such that the pH of the composition is between 8 and 12. More particularly between 9 and 11. The basifying agent is preferably chosen from ammonia, alkanolamines. such as mono-, di- and triethanolamines, alkali metal carbonate salts, guanidine, imidazole, sodium, potassium or calcium hydroxides and arginine and the compounds of formula (IV) below: Wherein: - W is a propylene residue optionally substituted by a hydroxyl group or a C1-C4 alkyl radical; Ra, Rb, Rd and Rd, which are identical or different, represent a hydrogen atom, a C1-C4 alkyl radical or a C1-C4 hydroxyalkyl radical. More particularly, the alkalinizing agent (s) is (are) chosen from ethanolamine, carbonate salts, guanidine, imidazole, calcium hydroxide and arginine. The keratinous substances The compounds of formula (I) are effective on keratin materials, in particular keratinous fibers such as human keratin fibers such as the hair.

Process for treating keratinous substances

An object of the invention relates to the process of dyeing by treatment or application to keratinous materials of one or more compounds of formula (I) as defined above that can be applied to the materials either directly or in a cosmetic composition comprising the compounds of formula (I). The exposure time for the coloration to be carried out is between 3 and 120 minutes. Preferably, after application of the composition containing the direct dye (s) and / or the pigment (s) which are little or not soluble in hydroalcoholic solvents; the composition is left to act for 10 to 60 minutes. Whatever the mode of application, the application temperature is generally between room temperature and 80 ° C and more particularly between 15 ° C and 45 ° C. Thus, it is advantageous, after application of the compounds of formula (I) as defined above, to subject the hair to heat treatment by heating at a temperature of between 30 and 60 ° C. In practice, this operation can be carried out by means of a hairdressing helmet, a hair dryer, an infrared dispenser and other conventional heating devices. Both heating and smoothing of the hair can be used as a heating iron at a temperature of between 60 and 220 ° C and preferably between 120 and 200 ° C. A particular embodiment of the invention relates to a process for conditioning keratin materials, in particular keratin fibers such as the hair, which is produced at ambient temperature (25 ° C.). After the application of the compounds of formula (I) as defined above to the keratinous fibers, said locks are preferably rinsed with water, washed with conventional shampoo and dried by means such as we have previously described. According to a particular dyeing process of the invention, the compounds of formula (I) are found in a cosmetic composition which is applied in one step to the keratinous fibers, particularly the hair, and then left for between 15 and 60 minutes, preferably minutes, then said fibers are rinsed with water, washed with conventional shampoo and dried. The following non-limiting examples illustrate the invention without limiting its scope.

EXAMPLES OF SYNTHESIS: Example 1: Synthesis of dimethyl 1,1'-fethane-1,2-diylbis (oxyethane-2,1-diylylbis (5-oxopyrrolidine-3-carboxylate) (compound 1) o To a solution of 31.6 g of methyl diester of itaconic acid (0.2 mole), a solution of 14.8 g of 2,2 '- (ethylene) dioxydiethylamine dissolved in 200 ml of ethanol was added dropwise at room temperature. After stirring for 24 h at room temperature, the solvents were evaporated under reduced pressure to give 39.5 g of the expected product in the form of an orange oil in almost quantitative yield.1H and 13C NMR spectra are consistent with the structure of the product. compound 1.

Example 2: Synthesis of 1,1'-fethan-1,2-diylbis (oxyethane-2,1-diyl) (5-oxopyrrolidine-3-carboxylic acid) to a solution of 10.4 g of compound 1 ( 0.026 mole) in 100 ml of water and 100 ml of methanol, 5 grams of sodium hydroxide (0.125 mole - 4eq) in pellets were added and the reaction mixture was refluxed for 5 h, then allowed to warm to room temperature. The mixture was then ice-cold at 0.degree.-5.degree. C. At this temperature, a solution of 6N hydrochloric acid was added dropwise until a pH of 2. After saturation of the medium with chloride. of sodium, the expected compound was extracted with 3 x 100 ml of dichloromethane.After drying over sodium sulphate, filtration and evaporation under reduced pressure, 10 g of a light yellow oil were thus obtained with an almost quantitative yield. 1H NMR and 13C are consistent with the structure of the expected compound.

Example 3 Synthesis of methyl 5-oxo-1-propylpyrrolidine-3-carboxylate To a solution of 8.90 ml of dimethyl itaconate (63.2 mmol) in 200 ml of ethanol was added dropwise a solution of 3.75 g of 1-aminopropane (63.2 mmol) in 50 ml of ethanol and then, after addition, the reaction medium was stirred for 24 h. The solvents were then evaporated under reduced pressure to give 11 g of the expected product in the form of a pale yellow oil with an almost quantitative yield The 1 H and 13 C NMR spectra are in accordance with the structure of the expected compound.

Example 4: Synthesis of 5-oxo-1-propylpyrrolidine-3-carboxylic acid

To a solution of 9.7 g of the compound of Example 3 (52.56 mmol) in 100 ml of water and 100 ml of methanol, 10 g of sodium hydroxide (0.252 mole - 4.8 eq) are added in pellets and the reaction mixture is then heated to reflux for 5H. It was then allowed to come to room temperature and then the medium was ice-cold at T = 0-5 ° C. At this temperature, a solution of 6N hydrochloric acid was added dropwise until a pH of 3 was obtained. After evaporation to dryness, the residue was taken up in 200 ml of methanol, the salts were filtered and then evaporated to dryness. the filtrate. 8.5 g of the expected product were thus obtained in the form of a beige powder with an almost quantitative yield. The 1H and 13C NMR spectra are consistent with the structure of the expected compound. EXAMPLE 5 Synthesis of 5-oxo-1-propylpyrrolidine-3-carbonyl chloride To a suspension of 4 g of Example 4 (23.3 mmol) in 50 ml of dichloromethane, 6 g of chloride were added under argon. of oxalyl (0.0472 mol) and then the medium was stirred at room temperature for 72 H. The supernatant was then removed and the gel obtained, maintained under argon, was taken up twice with 50 ml of dichloromethane. After evaporation of the organic phase to dryness, 4.2 g of the expected product were obtained in the form of a yellow viscous liquid with a quantitative yield.

The 1H and 13C NMR spectra are consistent with the structure of the expected compound.

Example 6 Synthesis of N, N'-hexane-1,6-diylbis (5-oxo-1-propylpyrrolidine-3-carboxamide) A solution of 0.85 g of hexanemethylenediamine (7.5 mmol) and 2 g of N, N-diisopropylethylamine (15 mmol) in 50 ml of dichloromethane was prepared. This solution was cooled to 5 ° C and a solution of 2.8 g of the compound of Example 5 (15 mmol) dissolved in 20 ml of N, N-dimethylformamide was added dropwise so as to maintain a temperature. close to 5 ° C,. After the addition, the reaction mixture was kept overnight at room temperature. The reaction medium was then poured into 10 ml of water and then the organic phase was dried over sodium sulfate. After filtration and evaporation to dryness, 1.6 g of the expected product were obtained in the form of an orange gum with a yield of 50%. The 1H and 13C NMR spectra are in accordance with the structure of the expected compound. c1 - / '7115

Claims (5)

CLAIMS1- Use of a compound of formula (I) as a dispersing agent for the makeup, the coloring of keratinous fibers, or as a care asset of said fibers; compounds of formula (I): O) LX / R2N A 2 as well as its organic or inorganic acid or base salts, optical isomers: stereoisomers or enantiomers and diastereoisomers, geometrical isomers, tautomers, and solvates such as hydrates; formula (I) wherein: X represents an oxygen atom or a divalent amino group -N (R5) -; with R5 representing a hydrogen atom, a linear or branched (C1-C3o) alkyl group especially (C1-C6) alkyl, optionally substituted with one or more -OH, -SH, -NH2, tri (C1-) groups; C6) alkylammonium, cationic heteroaryl such as pyridinium, imidazolium, and / or guanidinium; R 1 and R 2, which are identical or different, represent: an optionally substituted hydrocarbon chain, said chain is saturated linear in C 1 -C 30 or branched in C 3 -C 30 or cyclic in C 3 -C 7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more -S (O) -, -S (O) 2 groups -, -C (O) -, -N + (R6) (R7) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N ( R6) -, -N (R6) -C (O) -N (R7) - or -SS- and / or optionally iii) a saturated or unsaturated carbon ring of 3 to 6 members optionally substituted with one or more identical radicals or different, especially chosen from hydroxyl OH or amino-NRR '; a divalent -Cycl-Alk-Cycl'- chain with: R 3, Cycl and Cycl ', identical or different, preferably identical, representing a cyclic hydrocarbon chain, especially a C 5 -C 6 cycloalkylene, such as cyclohexylene or cyclopentylene and Alk representing an optionally substituted (C 1 -C 6) alkylene chain; preferentially unsubstituted; an optionally substituted hydrocarbon chain, said chain is linear unsaturated C2-C30 or branched C3-C30 or cyclic C3-C7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more -S (O) -, -S (O) 2 groups -, -C (O) -, -N + (R6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N (R6) -, - N (R6) -C (O) -N (R) - or -SS- and / or optionally iii) a saturated or unsaturated carbon ring of 3 to 6 members, optionally substituted in particular by one or more identical or different radicals selected from hydroxyl OH or amino - NRR '; or alternatively R 2 and / or R '2 represents a bond 6: A, and A 2, which may be identical or different, representing: a hydrogen atom, or a group chosen from a) -OH, b) -SH c) -NR, R8; d) -O-P (O) (OH) 2; E) -O-S (O) 2OH; f) -S (O) 2OH; g) -C (O) OH; h) (hetero) saturated or unsaturated 3 to 6-membered ring optionally substituted with one or more identical or different radicals chosen from (hydroxy) (C 1 -C 6) alkyl, hydroxyl, and -NRR ', said (hetero) ring being to be cationic; i) ammonium -N + (R,) (R8) (R9): j) guanidine RR'NC (= NR ") - N (R" ") -, H2NN particularly NH; k) guanidinium RR'NC (= N + R "R" ') - N (R "") - and I) a radical of formula (G) or (H): ## STR2 ## Wherein: X "represents an oxygen atom -O- or -N (R5) - with R5 as defined above; And R "1 and R" 2, which are identical or different, are as defined for R'1 and R'2 above; 1 to 1 and A "2, identical or different, are as defined for A1 and A2 with A" 1 and A "2 can not simultaneously represent a radical (G) or (H); representing the point of attachment of the radicals (G) and (H) to the rest of the molecule; R 3, R 4, R "3 and R" 4, which may be identical or different, represent a hydrogen atom or a linear C 1 -C 12 or branched C 3 -C 12 alkyl chain; R 6 represents a hydrogen atom, or a linear (C 1 -C 29) alkyl or branched (C 3 -C 29) alkyl group, optionally substituted with a radical (G) or (H); preferably terminated with a radical (G) or (H); R7, R8 and R9, which may be identical or different, representing a hydrogen atom or a (C 1 -C 6) alkyl group optionally substituted by one or more hydroxyl groups; or else R, with R8, or R8 with R9, or R, together with R9 together with the nitrogen atom carrying them, a cationic or non-cationic heterocycle, comprising from 4 to 7 chain members, preferably cationic heteroaryl, optionally substituted, in particular by one or more identical or different radicals, (C 1 -C 6) alkyl optionally substituted with one or more hydroxyls; R, R ', R "and R"', which may be identical or different, represent a hydrogen atom or a (C 1 -C 18) alkyl group optionally substituted by one or more hydroxyl groups, it being understood that when A, and / or A2 and / or R, and / or R2 and / or R5 contain or designate a cationic group, the electroneutrality of the compounds of formula (I) is provided by an anionic counterion or a mixture of anionic counterions. 2. Use according to the preceding claim wherein the compound or compounds of formula (I) are such that X, and X "represent an oxygen atom or an amino group -N (R5) - particularly R5 = H or a group ( C, -C6) alkyl. 3. Use according to any one of the preceding claims wherein the compound or compounds of formula (I) are such that the radicals R3, R4, R'3, R'4, R "3, R" 4 represent a hydrogen atom . 4. Use according to any one of the preceding claims wherein the compound or compounds of formula (I) are such that they contain at least two radicals, preferably two or three radicals, 2-pyrrolidinones functionalized in position 4 by an ester, an acid or an amide; radical (G), in particular R, represents a divalent chain -alk-T-alk'- with: - T representing: - either a covalent bond 6, - or a heteroatom such as O, - or a group -N (R 6) - with R '6 representing a hydrogen atom or a (C 1 -C 6) alkyl group, or -alk "- (G) - a divalent group -X.-alk" -Xb- with ) (a and Xb, identical or different, representing a heteroatom such as O or a group NH; - alk, alk ', and alk ", identical or different, representing a (C 1 -C 6) alkylene group, preferentially alk, alk and alk "are identical and represent an ethylene chain, or propylene, and - A, represents a radical (G). 5. Use according to any one of claims 3 in which the compound or compounds of formula (I) are such that they contain at least two radicals, preferably two or three radicals, 2-pyrrolidinones functionalized in position 4 by an ester, a acid or a radical amide (H), especially R2 represents a divalent chain -alk-T-alk'- with: - T representing: - either a covalent bond a, - a heteroatom such as 0, - or a group - N (R '6) - with R' 6 representing a hydrogen atom or a (C 1 -C 6) alkyl group, or -alk "- (H); - a divalent group -Xa-alk" -Xb with Xa and Xb, identical or different, representing a heteroatom such as O or an NH group; - alk, alk ', and alk ", identical or different, representing a (C 1 -C 6) alkylene group, preferentially alk, alk' and alk" are identical and represent an ethylene chain, or propylene; and A2 represents a radical (H). Use according to any one of the preceding claims, in which the compound (s) of formula (I) are such that R 1 and / or R 2 denote a saturated linear C, -C 30 or branched C 3 -C 30 hydrocarbon chain optionally interrupted by one or several heteroatoms such as O, S or -N (R6) -, N + (R6) (R7) -, -N (R6) -C (O) -, C (O) -N (R6) -, -N (R6) -C (O) -N (R7) - or -SS- and / or optionally substituted with one or more identical or different radicals selected from hydroxyl (OH) or -NRR '. The use as claimed in any one of the preceding claims, wherein the compound or compounds of formula (I) are such that the radical R 6 represents a (C 1 -C 6) alkyl group optionally terminated by a radical (G) or (H) and R, represents a hydrogen atom or a (C 1 -C 6) alkyl group. Use according to any one of the preceding claims wherein the compound (s) of formula (I) are such that radical A represents: - a hydrogen atom, - a radical -OH, - a radical -S (0) 2OH a radical NRR ', a radical -OP (O) (OH) 2 - a radical -OS (O) 2OH- a radical -C (O) OH - a (hetero) ring saturated or unsaturated 4 to 6 members this (hetero) ring may be cationic, - a radical of formula: -N + (R7) (R8) (R9) or (G). 9. Use according to any one of the preceding claims wherein the one or more compounds of formula (I) contain one or more cationic groups. 10. Use according to any one of the preceding claims wherein the compound (s) of formula (I) are such that: A2 represents: - a hydrogen atom, - a hydroxyl radical, - a (hetero) saturated or unsaturated ring from 4 to 6 members, this (hetero) ring being cationic, - a radical of formula: -N + (R7) (R8) (R9). 11. Use according to any one of the preceding claims wherein the compound (s) of formula (I) are such that R2 represents a saturated C1-C10 hydrocarbon chain optionally interrupted by one or more oxygen atoms, in particular saturated hydrocarbon chain. interrupted by several oxygens - [O-CH2-CH2] '- O-, with n being an integer of 1 to 4. 12. Use according to any one of the preceding claims wherein the compound (s) of formula (I) one or more long aliphatic chains, ie a C10-C30 alkyl or alkenyl group, more particularly C14-C22, preferentially C16-C20, such as C16. 13.. Use according to any one of the preceding claims wherein the compound (s) of formula (I) are such that: X = X ', R = R', and R2 = R'2 and are of formula (II) or (III ) R 3 R 4 R 4 R 4 R 4 R 1 R 4 R 1 R 1 R 1 R 1 R 1 R 1 R 2 R 2 R 2 R 2 R 2 III) with: - X represents an oxygen atom or a group -N (R5) -; with R5 representing a hydrogen atom, a linear C1-C30 or branched C3-C30 alkyl chain optionally substituted with one or several groups chosen from -OH, -SH, -NH2 -R, and R2 identical or different, represent: a hydrocarbon chain optionally substituted in particular by -N + (R7) (R5) (R9) said chain is saturated, linear C1- C2o or branched C3-C20 or cyclic C3-C7, said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more groups -S (O) -, -S (O) 2-, -C (O) -, -N + (R6) (R7) -, or combinations of i) and ii), especially -N (R6) -C (O) -, -C (O) -N (R6) -, -N (R6) -C (O) -N ( R7) - or -SS- and / or optionally 2 R3 Oiii) a saturated or unsaturated 3 to 6-membered carbon ring optionally substituted by one or more identical or different radicals, in particular chosen from hydroxyl OH or amino -NRR '; a divalent chain -Cycl-Alk-Cycl'- with: Cycl, and Cycl ', identical or different, preferably identical, representing a cyclic hydrocarbon chain especially a C5-C6 cycloalkylene, such as cyclohexylene or cyclopentylene and ^ AIk representing a optionally substituted (C1-C6) alkylene chain; preferentially unsubstituted; a hydrocarbon chain optionally substituted, in particular by -N + (R 1) (R 6) (R 9), said chain is linear unsaturated C 2 -C 20 or branched C 3 -C 20 or cyclic C 3 -C 7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more -S (O) -, -S (O) 2 groups -, -C (O) -, -N + (R6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N (R6) -, -N (R6) -C (O) -N (R7) - or -SS- and / or optionally iii) a saturated or unsaturated carbon ring of 3 to 6 members optionally substituted in particular by one or more radicals identical or different selected from hydroxyl OH or amino-NRR '; with R, R ', independently selected from a hydrogen atom or a (hydroxy) (C1-C16) alkyl group; - R6 represents a hydrogen atom or a linear (C 1 -C 26) alkyl or branched (C 3 -C 26) alkyl radical, optionally terminated by a radical of structure (G) or (H), O R "2 X '~ NA "2 ONR" 4 ONR "4 R" (G) A "/ 1 (H) or 1 formulas (G) and (H) in which: R" 3 \ X "has the same meaning as X, ie represents an oxygen atom -O- or -N (R5) - with R5 as defined above; R "q and R" 2, which are identical or different, are as defined for R 'and R'2 above; - A ,, A'2, and A "2, identical or different, represent a hydrogen atom, or a group selected from NRR ', N + (R7) (R3) (R9), -OH, -SH, -OP03H2, -OSO3H, -SO3H, and -CO2H-R ', and R'2, respectively R "q and R" 2 have the same meaning as R, and R2; R'2 and R "2 further designate a covalent bond; and preferably A'2 and A "2, respectively A ', and A" 1, are identical. 14.. Use according to any one of the preceding claims wherein the compound (s) of formula (I) are such that R3 = R4 = R "3 = R" 4 = H; X is O or -NR5; R5 represents a hydrogen atom, a C1-C6 or branched C3-C6 linear alkyl chain. 15.. Use according to any one of the preceding claims, in which the compound or compounds of formula (I) are such that R6 preferably denotes a hydrogen atom or a linear or branched C1-C20 alkyl radical C3-C20, optionally terminated by a radical of structure (G) OR "2 R" 3 \ X "2 ONR" 4 (G) formula (G) in which: - R "q and R" 2, identical or different, represent: a hydrocarbon chain optionally substituted, in particular with - N + (R7) (R3) (R9) said chain is saturated, linear C1-C20 or branched C3-C20 or cyclic C3-C7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R6) - or -S-, ii) one or more -S (O) -, -S (O) 2 groups -, -C (O) -, -N + (R'6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N (R6) -, - N (R6) -C (O) -N (R7) - or -SS- and / or optionally iii) a 3 to 6-membered saturated or unsaturated carbon ring optionally substituted by one or more identical or different radicals chosen in particular from hydroxyl OH or amino-NRR '; particularly R and R ', which are identical or different, are chosen from H and C 1 -C 6 alkyl. a hydrocarbon chain optionally substituted, in particular with -N + (R 1) (R 8) (R 9), said chain is saturated, linear in C 1 -C 20 or branched in C 3 -C 20 or cyclic in C 3 -C 7; said hydrocarbon chain is optionally interrupted by: i) one or more heteroatoms such as -O-, -N (R'6) - or -S-, ii) one or more -S (O) -, -S (0 groups ) 2-, -C (O) -, -N + (R6) (R,) -, or the combinations of i) and ii), particularly -N (R6) -C (O) -, -C (O) -N (R6) -, - N (R6) -C (O) -N (R,) - or -SS- and / or optionally iii) a saturated or unsaturated carbon ring of 3 to 6 members optionally substituted with one or several identical or different radicals chosen in particular from hydroxyl OH or amino-NRR '; R '6 denotes more particularly a hydrogen atom or a linear or branched C1-C20 alkyl radical C3-C20, optionally terminated by a radical of structure (H) R "4 A" / 1 (H) Formula (H) in which: A'1, A'2, A "1 and A" 2 independently represent a hydrogen atom, a radical -NRR ', a radical -N + (R,) (R8) (R9), An- and An-represents anionic counterion. Preferably A'1 and A "1, respectively A'2 and A" 2 are identical R "R7, R8, R9 independently represent a radical (hydroxy) C1-C18 alkyl; R3, R4, R'3; R ' 4; R "3; R "4 represent independently of each other a hydrogen atom, a linear C, -C12 or branched C3-C12 alkyl chain X" has the same meaning as X; R ', and R'2, respectively, R "q and R" 2 have the same meaning as R, and R2, R'2 and R "2 may further denote a covalent bond 16. Use according to any of the claims wherein the one or more compounds of formula (I) are such that R 3 = R 4 = R 3 = R 4 = H hydrogen atom; X represents O or -NH 2 R 2 represents: a divalent radical - ( CH2) '- T- (CH2) n - a radical chosen from Q, net iii: CH, CH3O H3 with n integer inclusively between 1 and 10; m integer inclusively between 6 and 20; and 20 p = 0 or 1 -T- denotes a covalent bond or an oxygen or sulfur atom, a radical -SO2- or -NH-CO-NH- or -SS- or -NH- or -N [(C, -C16 ), or a radical chosen from: ## STR2 ## where y denotes an integer between 2 and 10 inclusively, X is as defined above, in particular O or NH R '; , and R "q denote a C, -C, O or branched C3-C10 linear saturated hydrocarbon chain. Preferably, R 'and R "are identical to A' and are identical and chosen from a hydrogen atom, a radical NRR ', a radical N + (R7) (R8) (R9), An- with R, R 'independently denoting a hydrogen atom or a C1-C4 alkyl radical and R7, R8, R9 independently denoting a C1-C18 alkyl radical R, denotes: a divalent radical - (CH2)' - T- (CH2) ), a radical chosen from Q, net iii as defined above for R2, with -T- denoting a covalent bond or an oxygen or sulfur atom, a radical -SO2- or -NH-CO-NH- or -SS- or -NH- or -N [(C 1 -C 16) alkyl] -, or a radical selected from: ## STR5 ## and X and y are as defined previously for R 2, R '2 and R "2 denote a linear or C 3 -C 10 branched Covalent or linear hydrocarbon chain. Preferably, R '2 and R "2 are identical, An-N 1 - (CH 2) XIINOXN, A" R 7 R 2 OA 2 and A "2 are identical and chosen from a hydrogen atom, a radical NRR ', a radical N + (R,) (R8) (R9), An-, preferably H and R, R' independently denote a hydrogen atom or a C1-C4 alkyl radical 17. Use according to a any one of the preceding claims wherein the compound (s) of formula (I) are selected from the following compounds: NO OOO OOO OOO OOO OO O OO OO OO // O o // OO o o o o o oOONNNOO ~ ONN o ~ 7 0 ~~ o IOoO OO OO NOO NOO OO O OO OII OO OO OO OO OOO O OO OO O OO OFF OO NOOONOOO OO OSNOO o NNO \ O ~ SIS / OO ° ONOON (\ / O + AN- N ~ O o ~ o o N o o o SNO \ o l - \ OON ~ / ONOOO SO OHONOO ~ Off \ ~ NHO / OO ~ OON \ / OOONNOHONOO - \ N ~ O ON 0 0 0 0 = OOOOO // OONNON \ N ~ NOO ~ OO 0 N \ / - II O- / YO Inl OO JI O NT NONNNO ~ N \ \ O OO O, Nr OONO ^ ~ SO ONON -NIoI OIO NH OJNO / NNN NH HON ~ N. ONON p ~ N ~ \ NO --NO It / O ~ \ NO O //// / O, N O - \ / ^ IY ~ HN ^ 7O ~ \ N --- `NJ OHN Io OHNO ~ N IfOI ~ iN O = __, ~ 7 ~ O ^ ~~~~ NO N ~ II {o ^ / `HO ~ J7 NO Q_ NO H0 ~ \ NN 0 iN Ho O) -z xz xz -z zx xz zx o xz -z xz ooo OO I ~ NNHNOO Hui NHHONNOO O- Hui NHHONNN ^ ~ HHON NO ^ / IN N / v \ N ~ O ° H II NOONONNO ~ OH HN O NfH NON OHo z ~ ° xz o ~ x ~ z xz o zx oo zx z ~ ozoz ~ zo ~ zx po ~ ~ z I ° I ° O z \ ) O xz xz xz o ~ ozx zo ° 0 xz z O o o o o oo oo zozzzoozz xz ~ xz 0 O zx zx z xz z \ ^ oo zz z 0 0 ozoozzo xz ozo 0 \) xz zz -z-zz 6 ## EQU1 ## i ~ N,, N oo NI ~ JT o ~ - 2961208 104 oII N ~ ox H} ~ / -O oH o ~ Y 'N,, N v ~ N, JO yYY / / .. It A ° ~. / / O o HN r ~ o O \ Ili` / N \ O \ H \ I7 / I ~ / JON HN NNNHON / --- 5 O o HO \ N ~~ NH OO N5 NH 2961208 106 N iN OHO ~ ## STR1 ## wherein: ## STR1 ## ## STR5 ## abo NO 0 O o -O ~ IO HO O ed HN ON 0 ~ ooo / o ~ o oo ef -NO o NN ,, N o N o o HN VA OHO gh \ OO \ HO ~ ~ N HO O - OO ^ / \) O p 1 J 2961208 109 i NN HN SNO ~ (\ `~~; \ HN O - NN7 \ k 1 An- An- 0 NH O / / NO NO ~ HN s ON __ An- O An- N / A N / N N / O 1 OI 1 () NNONOOO \ O -N op 0 o \ X7 O ~ OH N \ / An- OOO \ ~~ N o N + ~~ N OH qr 2961208 110 O HN o M ~ O An NO ~ N \ NS OS t OO ~ - O o ~~ SNON \ I + / ~ / N ~ o UV HO OH O, Name / N% o O \ 0 O // \ 7 O o WX ## EQU2 ## ad OO 0 0 NIA NO p NO ae OO OOJOJNNO HO ~ N p NOO `/ \) ag ah 2961208 112 NINONONOOOON ai aj OH N / ONO HO O \ OO ak al O o A \ ON \ / j \ NO \ N o N \ an an an OH a a a a a a a a a ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar ar NON NON NON NON NON NON NON NON NON with An-representative anionic counterion; above compounds, as well as their organic or inorganic acid or base salts, optical isomers: stereoisomers or enantiomers and diastereoisomers, and solvates such as hydrates. 18.. Compound of formula (I) as defined in any preceding claim comprising at least two 2-pyrrolidinone radicals functionalized at the 4-position with an ester, an acid or an amide, preferably two or three pyrrolidone groups, it being understood that R, can represent an ethylene group and that said compounds are different from the compounds of the formula ## STR2 ## with m = 1, 2 and 44 OH OH OO 0-CH 2 -IC-CH 2 -O-CH 2 -OH Me Me 0 CH 2 -OH 0 i-Bu -O-CH 2 -t -CH 2 -O -H 2 -OH Bu-i LUI O -o L`G 116HO O ## STR2 ## ## STR2 ## ## STR2 ## ## STR2 ## Wherein a cosmetic composition comprising one or more compounds of formula (I) is provided. as defined in any one of the preceding claims 2961208 118 20. Process for conditioning keratin materials, by treatment or applicati on said keratin materials of one or more compounds of formula (I) as defined in any one of claims 1 to 18 or by application of the cosmetic composition as defined in the preceding claim.