WO2012113725A2 - Composition pour la coloration de fibres kératiniques comprenant un colorant direct portant une fonction disulfure/thiol, une substance grasse, un agent alcalin et un réducteur - Google Patents

Composition pour la coloration de fibres kératiniques comprenant un colorant direct portant une fonction disulfure/thiol, une substance grasse, un agent alcalin et un réducteur Download PDF

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WO2012113725A2
WO2012113725A2 PCT/EP2012/052753 EP2012052753W WO2012113725A2 WO 2012113725 A2 WO2012113725 A2 WO 2012113725A2 EP 2012052753 W EP2012052753 W EP 2012052753W WO 2012113725 A2 WO2012113725 A2 WO 2012113725A2
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group
alkyl
different
radical
optionally substituted
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PCT/EP2012/052753
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WO2012113725A3 (fr
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Frédéric Guerin
Chrystel POURILLE
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L'oreal
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the invention relates to a process for dyeing and/or lightening keratin fibres using direct dyes.
  • Direct dyeing or semi-permanent dyeing consists in introducing colour via a coloured molecule that becomes adsorbed onto the surface of the hair or that penetrates into the hair.
  • the process conventionally used in direct dyeing consists in applying to keratin fibres direct dyes, which are coloured, and colouring molecules that have affinity for the fibres, leaving the fibres in contact with the colouring molecules and then optionally rinsing the fibres.
  • this technique leads to chromatic colorations.
  • the aim of the present invention is to provide novel systems for dyeing the hair, even without the use of a chemical oxidizing agent, which make it possible to obtain improved colorations, especially in terms of fastness with respect to external agents, homogeneity of the coloration (little selectivity between the root and the end of the keratin fibres), and intensity, and/or which do not impair the cosmetic properties of the keratin fibres.
  • a cosmetic composition comprising:
  • ⁇ U represents a radical chosen from: aj - S - C' sat - (X'V - A';
  • a and A' which may be identical or different, represent a radical containing at least one quaternized cationic chromophore or at least one chromophore bearing a quaternized or quaternizable cationic group;
  • Y represents i) a hydrogen atom; or ii) a thiol-function protecting group
  • X and X' which may be identical or different, represent a linear or branched, saturated or unsaturated divalent CrC 30 hydrocarbon-based chain, optionally interrupted and/or optionally terminated at one or both of its ends with one or more divalent groups or combinations thereof chosen from:
  • R which may be identical or different, chosen from a hydrogen and a C C 4 alkyl, hydroxyalkyl or aminoalkyl radical;
  • C S at and C'sat which may be identical or different, represent an optionally substituted linear or branched, or cyclic, C Ci 8 alkylene chain;
  • Another subject of the invention is a process for dyeing and/or lightening keratin fibres, especially dark keratin fibres, by applying to the said fibres the ingredients i) to iv) as defined previously, the said ingredients being applied together or separately.
  • compositions comprising i), ii), Hi) and iv) as defined previously, for the dyeing and/or lightening of keratin fibres.
  • Another subject of the invention is a multi-compartment kit comprising i), ii), Hi) and iv) as defined previously.
  • the colorations obtained are attractive, aesthetic, intense, strong, chromatic and very fast or persistent with respect to common attacking factors or everyday assaults such as sun, sebum and especially with respect to perspiration, and other hair treatments such as successive shampooing, while at the same time respecting the keratin fibres.
  • the intensity obtained is particularly noteworthy. The same is true for the colour homogeneity or selectivity of the colour.
  • a "direct dye bearing a disulfide function" is a direct dye comprising one or more cationic chromophores that absorb light in the visible spectrum, and comprising a disulfide bond: -S-S- between two carbon atoms and is preferably indirectly bonded to the chromophore(s) of the dye, i.e. between the chromophores and the - S-S- function there is at least one methylene group;
  • a "direct dye bearing a protected-thiol function" is a direct dye comprising a chromophore, comprising a protected-thiol function -SY in which Y is a protecting group known to those skilled in the art, for instance those described in the publications Protective Groups in Organic Synthesis, T.W. Greene, John Wiley & Sons ed., NY, 1981 , pp. 193-217; Protecting Groups, P. Kocienski, Thieme, 3 rd ed.,
  • the said protected-thiol function is preferably indirectly bonded to the chromophore of the dye, i.e. between the chromophore and the function -SY there is at least one methylene group;
  • a "direct dye bearing a thiol function” is a direct dye comprising a chromophore, and comprising a thiol function -S in which Y' is i) a hydrogen atom; ii) an alkali metal; iii) an alkaline-earth metal; iv) an ammonium group: N + R R p R T R 5 or a phosphonium group: P + R a R p R T R 5 with R a , R p , R 7 and R 5 , which may be identical or different, representing a hydrogen atom or a group (C C 4 )alkyl, preferentially comprising a thiol function -SH, it being understood that the said thiol function is preferably indirectly bonded to the chromophore of the dye, i.e. between the chromophore and the function -SY there is at least one methylene group;
  • chromophore is a radical derived from a dye, i.e. a radical derived from the molecule that absorbs light in the visible radiation range that is visually perceptible by man, i.e. an absorption wavelength ab s inclusively between 400 and 800 nm; the chromophore may be fluorescent, i.e. it is capable of absorbing in the UV and visible radiation range at a wavelength ab s inclusively between 250 and 800 nm and capable of re-emitting in the visible range at an emission wavelength em inclusively between 400 and 800 nm;
  • chromophore is said to be "quaternized cationic” or "bearing a quaternized cationic group” if it comprises in its structure at least one permanent cationic charge formed from at least one quaternized nitrogen atom (ammonium) or quaternized phosphorus atom (phosphonium), preferably nitrogen;
  • a group is said to be "bearing a quaternizable cationic group" when it comprises in its structure at least one tertiary amine or tertiary phosphine at the end of a hydrocarbon-based chain, preferably C1-C10 alkyl, such as -(CR'R") p -N(R a )-Rb with R' and R", which may be identical or different, representing a hydrogen atom or a (CrC 6 )alkyl group; R a and R , which may be identical or different, representing a (CrC 6 )alkyl group, a monohydroxy(Ci-C 6 )alkyl group, a (poly)(hydroxy)(CrC 6 )alkyl group or R a and R forming, together with the nitrogen atom that bears them, a heterocycloalkyl group such as morpholino, which, once quaternized, will become morpholinium, piperidino, which,
  • the dyes according to the invention contain one or more chromophores, and these dyes are capable of absorbing light at a wavelength ab s particularly of between 400 and 700 nm inclusive;
  • the "fluorescent' dyes according to the invention are dyes containing at least one fluorescent chromophore, and these dyes are capable of absorbing in the visible range at a wavelength ab s particularly inclusively between 400 and 800 nm and of re-emitting in the visible range at a longer wavelength em than that absorbed, inclusively between 400 and 800 nm.
  • the difference between the absorption and emission wavelengths, also known as the Stoke's shift, is inclusively between 1 nm and 100 nm.
  • fluorescent dyes are dyes that are capable of absorbing at a wavelength ab s inclusively between 420 and 550 nm and of re- emitting in the visible range at a wavelength em inclusively between 470 and 600 nm;
  • chromophores are said to be "different' when they differ in their chemical structure and may be chromophores derived from different families or from the same family on condition that they have different chemical structures: for example, the chromophores may be chosen from the family of azo dyes but differ in the chemical structure of the radicals constituting them or in the respective position of these radicals;
  • an "alkylene chain” represents a divalent acyclic C C 20 hydrocarbon-based chain; particularly C C 8 and more particularly C C 2 when the chain is linear; optionally substituted with one or more groups, which may be identical or different, chosen from i) hydroxyl, ii) (CrC 2 )alkoxy, iii) (poly)hydroxy(C 2 -C 4 )alkoxy(di)(Cr C 2 )(alkyl)amino, iv) R a -Z a -C(Z b )-Z c - and v) R a -Z a -S(0) t ⁇ Z c - with Z a and Z b , which may be identical or different, representing an oxygen or sulfur atom, or a group NR a ', Z c , representing a bond, an oxygen or sulfur atom, or a group NR a ; R a , representing an alkali metal, a hydrogen
  • an "optionally substituted, saturated or unsaturated CrC 30 divalent hydrocarbon- based chain” represents a hydrocarbon-based chain, particularly of C C 8 , optionally comprising one or more conjugated or unconjugated double bonds, and in particular the hydrocarbon-based chain is saturated; the said chain is optionally substituted with one or more groups, which may be identical or different, chosen from i) hydroxyl, ii) (C C 2 )alkoxy, iii) (poly)hydroxy(C 2 -C 4 )alkoxy(di)(C C 2 )(alkyl)amino, iv) R a -Z a -C(Z b )-Z c - and v) R a -Z a -S(0) t ⁇ Z c - with Z a and Z b , which may be identical or different, representing an oxygen or sulfur atom, or a group NR a ', Z c , representing a bond, an
  • ary or heteroary radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from:
  • a C 1 -C16 and preferably d-Cs alkyl radical optionally substituted with one or more radicals chosen from hydroxyl, C C 2 alkoxy, C 2 -C 4 (poly)hydroxyalkoxy, acylamino, amino substituted with two CrC 4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, or the two radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7-membered and preferably 5- or 6-membered heterocycle optionally comprising another heteroatom identical to or different from nitrogen; a halogen atom;
  • an optionally cationic 5- or 6-membered heteroaryl radical preferentially imidazolium, optionally substituted with a (C C 4 )alkyl radical, preferentially methyl;
  • an optionally cationic 5- or 6-membered heteroaryl radical preferentially imidazolium, optionally substituted with a (C C 4 )alkyl radical, preferentially methyl;
  • an acylamino radical (-NR-C(O)-R') in which the radical R is a hydrogen atom or a C C 4 alkyl radical optionally bearing at least one hydroxyl group and the radical R' is a C C 2 alkyl radical;
  • a carbamoyl radical ((R) 2 N-C(0)-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C C 4 alkyl radical optionally bearing at least one hydroxyl group;
  • R represents a hydrogen atom or a C C 4 alkyl radical optionally bearing at least one hydroxyl group and the radical R' represents a C C 4 alkyl radical, or a phenyl radical;
  • radicals R which may be identical or different, represent a hydrogen atom or a C C 4 alkyl radical optionally bearing at least one hydroxyl group;
  • a carboxylic radical in acid or salified form preferably with an alkali metal or a substituted or unsubstituted ammonium
  • a polyhaloalkyl group preferentially trifluoromethyl
  • cyclic or heterocyclic part of a non-aromatic radical may be substituted with at least one substituent chosen from the following groups:
  • alkylcarbonylamino (R-C(O)-N(R')-) in which the radical R' is a hydrogen atom or a d-C 4 alkyl radical optionally bearing at least one hydroxyl group, and the radical R is a d-C 2 alkyl radical or an amino radical optionally substituted with one or two d-C 4 alkyl groups, which may be identical or different, themselves optionally bearing at least one hydroxyl group, the said alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7- membered heterocycle optionally comprising at least one other nitrogen or non-nitrogen heteroatom;
  • alkylcarbonyloxy (R-C(O)-O-) in which the radical R is a C C 4 alkyl radical or an amino radical substituted with one or two identical or different C C 4 alkyl groups, themselves optionally bearing at least one hydroxyl group, the said alkyl radicals possibly forming with the nitrogen atom to which it is attached a saturated or unsaturated, optionally substituted 5- to 7- membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom;
  • alkoxycarbonyl in which the radical R is a d-C 4 alkoxy radical, G is an oxygen atom or an amino group optionally substituted with a d-C 4 alkyl group optionally bearing at least one hydroxyl group, the said alkyl radical possibly forming, with the nitrogen atom to which it is attached, a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non- nitrogen heteroatom;
  • a cyclic or heterocyclic radical, or a non-aromatic portion of an aryl or heteroaryl radical may also be substituted with one or more oxo groups;
  • a hydrocarbon-based chain is unsaturated when it comprises one or more double bonds and/or one or more triple bonds;
  • an "a/yr radical represents a fused or non-fused monocyclic or polycyclic carbon- based group containing from 6 to 22 carbon atoms, and in which at least one ring is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl;
  • a heteroaryl radicar represents a fused or non-fused, optionally cationic, 5- to 22- membered monocyclic or polycyclic group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium, and at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthoxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopy
  • heterocyclic radicar or heterocycle is a fused or non-fused, 5- to 22-membered monocyclic or polycyclic non-aromatic radical, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium;
  • heterocycloalkyl radicar is a heterocyclic radical comprising at least one saturated ring
  • a "cationic heteroaryl radicar is a heteroaryl group as defined previously, which comprises a quaternized endocyclic or exocyclic cationic group,
  • the cationic charge when the cationic charge is endocyclic, it is included in the electron derealization via the mesomeric effect, for example it is a pyridinium, imidazolium or indolinium roup:
  • R and R' being a heteroaryl substituent as defined previously and particularly a (hydroxy)(d-C 8 )alkyl group such as methyl;
  • the cationic charge when exocyclic, for example, it is an ammonium or phosphonium substituent R + such as trimethylammonium, which is outside the heteroaryl such as pyridyl, indolyl, imidazolyl or naphthalimidyl in question: with R being a heteroaryl substituent as defined previously and R + an ammonium R a R b R c N + -, phosphonium R a R b R c P + - or ammonium R a R b R c N + -(Cr C 6 )alkylamino group with R a , R b and R c , which may be identical or different, representing a hydrogen atom or a (C C 8 ) alkyl group such as methyl;
  • cationic aryl bearing an exocyclic charge means an aryl ring whose quaternized cationic group is outside the said ring; it is especially an ammonium or phosphonium substituent R + such as trimethylammonium, outside the aryl such as phenyl or naphthyl:
  • an "alkyl radicaP' is a linear or branched C C 2 o and preferably C C 8 hydrocarbon- based radical
  • the term "optionally substituted' attributed to the alkyl radical means that the said alkyl radical may be substituted with one or more radicals chosen from the following radicals: i) hydroxyl, ii) C C 4 alkoxy, iii) acylamino, iv) amino optionally substituted with one or two identical or different C C 4 alkyl radicals, the said alkyl radicals possibly forming with the nitrogen atom that bears them a 5- to 7-membered heterocycle, optionally comprising another heteroatom identical to or different from nitrogen; v) or a quaternary ammonium group -N + R'R"R"', M " for which R', R" and R'", which may be identical or different, represent a hydrogen atom or a C C 4 alkyl group, or else -N + R'R"R"' forms a heteroaryl such as imidazolium optionally substituted with a C C 4 alkyl group, and M " represents the counterion of the
  • an "alkoxy" radical is an alkyloxy radical for which the alkyl radical is a linear or branched C Ci 6 and preferentially C C 8 hydrocarbon-based radical;
  • the alkoxy group when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined hereinabove;
  • ⁇ the "tone depth" is the unit known to hairstyling professionals, published in the book Science des.s capillaires [Hair treatment sciences] by Charles Zviak, 1988, published by Masson, pp. 215 and 278; the tone depths range from 1 (black) to 10 (very light blond), one unit corresponding to one tone; the higher the figure, the lighter the shade;
  • Naturally or artificially dark hair means hair whose tone depth is less than or equal to 6 (dark blond) and preferably less than or equal to 4 (chestnut-brown).
  • Artificially dyed hair is hair whose colour has been modified by a coloration treatment, for example a coloration with direct dyes or oxidation dyes;
  • thickening polymer means a polymer which, when introduced at 1 % by weight in an aqueous solution or an aqueous-alcoholic solution containing 30% ethanol, and at pH 7, or in an oil chosen from liquid petroleum jelly, isopropyl myristate or cyclopentadimethylsiloxane, makes it possible to achieve a viscosity of at least 100 cps and preferably of at least 500 cps, at 25°C and at a shear rate of 1 s ' This viscosity may be measured using a cone/plate viscometer (Haake R600 rheometer or the like).
  • the thickening polymers may thicken the aqueous phase and/or the fatty phase, preferentially the aqueous phase;
  • organic thickening polymer means a thickening polymer as defined previously, which is formed from carbon and hydrogen, and possibly nitrogen, oxygen, sulfur, halogens such as fluorine, chlorine or bromine, and also phosphorus, alkali metals such as sodium or potassium, or alkaline-earth metals such as magnesium or calcium.
  • the organic polymers according to the invention do not comprise silicon;
  • fatty substance means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1 % and even more preferentially less than 0.1 %); in addition, the fatty substances are soluble in organic solvents under the same temperature and pressure conditions, for instance in halogenated solvents such as chloroform or dichloromethane, lower alcohols such as ethanol or aromatic solvents such as benzene or toluene;
  • an "organic or mineral acid salt” is more particularly chosen from salts chosen from a salt derived from i) hydrochloric acid HCI, ii) hydrobromic acid HBr, iii) sulfuric acid H 2 S0 4 , iv) alkylsulfonic acids: Alk-S(0) 2 OH such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(0) 2 OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-0-S(0)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid;
  • an "anionic counterion” means an anion or an anionic group derived from an organic or mineral acid salt which counterbalances the cationic charge of the dye; more particularly, the anionic counterion is chosen from: i) halides such as chloride or bromide; ii) nitrates; iii) sulfonates, including C C 6 alkylsulfonates: Alk-S(0) 2 0 " such as methanesulfonate or mesylate and ethanesulfonate; iv) arylsulfonates: Ar- S(0) 2 0 " such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfates: Alk-0-S(0)0 " such as methyl sulfate and ethyl sulfate;
  • addition salts that may be used in the context of the invention are especially chosen from addition salts with a cosmetically acceptable base such as basifying agents as defined below, for instance alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines;
  • a cosmetically acceptable base such as basifying agents as defined below, for instance alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines;
  • composition according to the invention is cosmetic, i.e. it is in a cosmetic medium and comprises:
  • the cosmetic medium means a medium that is suitable for dyeing keratin fibres, also known as a dye support, which is a cosmetic medium generally formed from water or a mixture of water and one or more organic solvents or a mixture of organic solvents.
  • the composition comprises water in a content especially inclusively between 5% and 95% relative to the total weight of the composition.
  • organic solvent means an organic substance that is capable of dissolving another substance without chemically modifying it.
  • Organic solvents examples include C C 4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • C C 4 lower alkanols such as ethanol and isopropanol
  • polyols and polyol ethers for instance 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether
  • aromatic alcohols for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the organic solvents are preferably present in proportions preferably inclusively between 0.1 % and 40% by weight approximately relative to the total weight of the dye composition, more preferentially between 1 % and 30% by weight approximately and even more particularly inclusively between 5% and 25% by weight relative to the total weight of the composition.
  • the direct dye(s) bearing a disulfide, thiol or protected-thiol function used in the invention are of formula (I) as defined previously.
  • the dyes of formula (I) bearing a thiol function are as defined previously, i.e. U representing the radical b) Y.
  • the direct dye of formula (I) is a thiol dye, i.e. Y represents i) a hydrogen atom.
  • Y is a protecting group known to those skilled in the art, for instance those described in the publications "Protective Groups in Organic Synthesis", T. W. Greene, published by John Wiley & Sons, NY, 1981 , pp. 193-217; "Protecting Groups”, P. Kocienski, Thieme, 3rd edition, 2005, chapter 5, and Ullmann's Encyclopedia, "Peptide Synthesis", pp. 4-5, 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007.a19 157;
  • Y represents a thiol-function protecting group chosen from the following radicals:
  • arylcarbonyl for instance phenylcarbonyl
  • aryl such as phenyl, dibenzosuberyl or 1 ,3,5- cycloheptatrienyl
  • heteroaryl especially including the following cationic or non-cationic heteroaryl radicals comprising from 1 to 4 heteroatoms: i) 5-, 6- or 7-membered monocyclic radicals such as furanyl or furyl, pyrrolyl or pyrryl, thiophenyl or thienyl, pyrazolyl, oxazolyl, oxazolium, isoxazolyl, isoxazolium, thiazolyl, thiazolium, isothiazolyl, isothiazolium, 1 ,2,4-triazolyl, 1 ,2,4-triazolium, 1 ,2,3-triazolyl, 1 ,2,3-triazolium, 1 ,2,4-oxazolyl, 1 ,2,4- oxazolium, 1 ,2,4-thiadiazolyl, 1 ,2,4-thiadiazolium, pyrylium, thiopyridyl, pyri
  • the two rings A and C optionally comprise a heteroatom
  • ring B is a 5-, 6- or 7-membered ring, particularly a 6-membered ring, and contains at least one heteroatom, for instance piperidyl or pyranyl
  • the heterocycloalkyl group especially represents a saturated or partially saturated 5-, 6- or 7-membered monocyclic group comprising from 1 to 4 heteroatoms chosen from oxygen, sulfur and nitrogen, such as di/tetrahydrofuryl, di/tetrahydrothiophenyl, di/tetrahydropyrrolyl, di/tetrahydropyranyl, di/tetra/hexahydrothiopyranyl, dihydropyridyl, piperazinyl, piperidinyl, tetramethylpiperidyl, morpholinyl, di/tetra/hexahydroazepinyl, di/tetrahydropyr
  • R' c , R' d , R' e , R' f , R' 9 and R' h which may be identical or different, represent a hydrogen atom or a (C C 4 ) alkyl group, or alternatively two groups R' 9 with R' h , and/or R' e with R' f , form an oxo or thioxo group, or alternatively R' 9 with R' e together form a cycloalkyl; and v represents an integer between 1 and 3 inclusive; preferentially, R' c to R' h represent a hydrogen atom; and An'" " represents a counterion;
  • R' c , R' d , R' e and R' f which may be identical or different, representing a hydrogen atom or a (C C 4 )alkyl group; preferentially, R' c to R' f represent a hydrogen atom; and An'" " represents a counterion;
  • (di)aryl(C C 4 )alkyl such as 9-anthracenyl methyl, phenylmethyl or diphenylmethyl optionally substituted with one or more groups especially chosen from (C C 4 ) alkyl, (C C 4 ) alkoxy such as methoxy, hydroxyl, alkylcarbonyl or (di)(C C 4 )(alkyl)amino such as dimethylamino;
  • the heteroaryl group especially being a cationic or noncationic, 5- or 6-membered monocyclic radical comprising from 1 to 4 heteroatoms chosen from nitrogen, oxygen and sulfur, such as pyrrolyl, furanyl, thiophenyl, pyridyl, pyridyl N-oxide such as 4-pyridyl or 2-pyridyl-N-oxide, pyrylium, pyridinium or triazinyl groups, optionally substituted with one or more groups such as alkyl, particularly methyl; advantageously, the (di)heteroaryl(C C 4 )alkyl is (di)heteroarylmethyl or (di)heteroarylethyl;
  • R 1 , R 2 and R 3 which may be identical or different, representing a halogen atom or a group chosen from:
  • aryl such as phenyl optionally substituted with one or more groups, for instance (C C 4 )alkyl, (C C 4 )alkoxy or hydroxyl;
  • heteroaryl such as thiophenyl, furanyl, pyrrolyl, pyranyl or pyridyl, optionally substituted with a (C C 4 )alkyl group;
  • R' 1 and R' 2 which may be identical or different, representing a hydroxyl, (C C 4 )alkoxy or alkyl group, R' 3 representing a hydroxyl or (C C 4 )alkoxy group, and Z 1 representing an oxygen or sulfur atom;
  • alkoxyalkyi such as methoxymethyl (MOM), ethoxyethyl (EOM) and isobutoxymethyl.
  • the thiol-protected dyes of formula (I) comprise a group Y chosen from i) aromatic cationic 5- or 6-membered monocyclic heteroaryl comprising from 1 to 4 heteroatoms chosen from oxygen, sulfur and nitrogen, such as oxazolium, isoxazolium, thiazolium, isothiazolium, 1 ,2,4-triazolium, 1 ,2,3-triazolium, 1 ,2,4- oxazolium, 1 ,2,4-thiadiazolium, pyrylium, pyridinium, pyrimidinium, pyrazinyl, pyrazinium, pyridazinium, triazinium, tetrazinium, oxazepinium, thiepinyl, thiepinium, imidazolium; ii) cationic 8- to 11-membered bicyclic heteroaryl such as indolinium, benzimidazolium,
  • R' c and R' d which may be identical or different, represent a hydrogen atom or a group (Ci-C 4 )alkyl; preferentially R' c to R' d represent a group (C C 4 )alkyl such as methyl; and An'" " represents a counterion.
  • Y represents a group chosen from oxazolium, isoxazolium, thiazolium, isothiazolium, 1 ,2,4-triazolium, 1 ,2,3-triazolium, 1 ,2,4-oxazolium, 1 ,2,4-thiadiazolium, pyrylium, pyridinium, pyrimidinium, pyrazinium, pyridazinium, triazinium and imidazolium, benzimidazolium, benzoxazolium, benzothiazolium, these groups being optionally substituted with one or more (C C 4 )alkyl groups, especially methyl.
  • Y represents a protecting group such as:
  • cationic 5- or 6-membered monocyclic heteroaryl such as pyrylium, pyridinium, pyrimidinium, pyrazinium, pyridazinium, triazinium, imidazolium; these groups being optionally substituted with one or more identical or different (C C 4 )alkyl groups such as methyl; cationic 8- to 1 1-membered bicyclic heteroaryl such as benzimidazolium or benzoxazolium; these groups being optionally substituted with one or more identical or different (C C 4 )alkyl groups such as methyl;
  • M + with M + representing an alkali metal such as sodium or potassium.
  • C sa t and C' sa t independently of each other, represent a linear or branched or cyclic, optionally substituted C Ci 8 alkylene chain.
  • C sa t and C' sa t represent a chain -(CH 2 ) k - with k being an integer between 1 and 8 inclusive.
  • X and X' represent a chain -(CH 2 ) k - with k being an integer between 1 and 8 inclusive.
  • T and T' which may be identical or different, represent one or more radicals or combinations thereof chosen from: -0-; -S-; -N(R)-; -N + (R)(R°)-; -S(O)-; -S(0) 2 -; - C(O)-; with R, R°, which may be identical or different, representing a hydrogen atom, a C C 4 alkyl radical, C C 4 hydroxyalkyl radical or an aryl(C C 4 )alkyl radical; and a cationic or non-cationic, preferentially monocyclic heterocycloalkyl or heteroaryl radical, preferentially containing two heteroatoms (more preferentially two nitrogen atoms) and preferentially being 5- to 7-membered, more preferentially imidazolium;
  • indices t and t' which may be identical or different, are equal to 0 or 1 ;
  • an aryl, alkylaryl or arylalkyl radical in which the alkyl radical is C C 4 and the aryl radical is preferably C 6 , being optionally substituted with at least one group S0 3 M with M representing a hydrogen atom, an alkali metal or an ammonium group substituted with one or more identical or different, linear or branched C Ci 8 alkyl radicals optionally bearing at least one hydroxyl;
  • Z represents:
  • M represents a hydrogen atom, an alkali metal or an ammonium group or an ammonium group substituted with one or more identical or different, linear or branched C Ci 0 alkyl radicals optionally bearing at least one hydroxyl; 0-4 represents an integer between 0 and 4 inclusive, and q represents an integer inclusively between 1 and 6. i).4).
  • a and A ' :
  • radicals A and/or A' of formula (I) contain at least one quaternized cationic chromophore or at least one chromophore bearing a quaternized or quaternizable cationic group.
  • the dyes (I) according to the invention are disulfides and comprise identical quaternized cationic chromophores A and ⁇ '.
  • the dyes of formula (I) according to the invention are symmetrical disulfides, i.e. they contain a C 2 axis of symmetry, i.e. formula (I) is such that:
  • chromophores that are useful, mention may be made of those derived from the following dyes: acridines; acridones; anthranthrones; anthrapyrimidines; anthraquinones; azines; (poly)azos, hydrazono or hydrazones, in particular arylhydrazones; azomethines; benzanthrones; benzimidazoles; benzimidazolones; benzindoles; benzoxazoles; benzopyrans; benzothiazoles; benzoquinones; bisazines; bis-isoindolines; carboxanilides; coumarins; cyanins such as azacarbocyanins, diazacarbocyanins, diazahemicyanins, hemicyanin, or tetraazacarbocyanins; diazines; diketopyrrolopyrroles; dioxazines; diphenylamines; di
  • cationic azo chromophores mention may be made particularly of those derived from the cationic dyes described in the Kirk Othmer Encyclopedia of Chemical
  • azo chromophores A and/or A' that may be used according to the invention, mention may be made of the cationic azo dyes described in patent applications WO 95/15144, WO 95/01772 and EP-714954.
  • the coloured chromophore A and/or A' is chosen from cationic chromophores, preferentially those derived from dyes known as "basic dyes".
  • cationic quinone chromophores A and/or A' those mentioned in the abovementioned Colour Index International are suitable for use, and among those, mention may be made, inter alia, of the radicals derived from the following dyes:
  • cationic azine chromophores A and/or A' those listed in the Colour Index International are suitable for use, and among those, for example the radicals derived from the following dyes:
  • the chromophores A and/or A' are chosen from those derived from dyes of the type such as azo and hydrazono.
  • the cationic radicals A and/or A' in formula (I) comprise at least one cationic azo chromophore derived from a dye described in EP 850 636, FR 2 788 433, EP 920 856, WO 99/48465, FR 2 757 385, EP 85/0637, EP 91/8053, WO 97/44004, FR 2 570 946, FR 2 285 851 , DE 2 538 363, FR 2 189 006, FR 1 560 664, FR 1 540 423, FR 1 567 219, FR 1 516 943, FR 1 221 122, DE 4 220 388, DE 4 137 005, WO 01/66646, US 5 708 151 , WO 95/01772, WO 515 144, GB 1 195 386, US 3 524 842, US 5 879 413, EP 1 062 940, EP 1 133 976, GB 738 5
  • a and/or A' of formula (I) contain at least one cationic radical borne by, or included in, at least one of the chromophores.
  • the cationic radical is a quaternary ammonium; more preferentially, the cationic charge is endocyclic.
  • cationic radicals are, for example, a cationic radical:
  • an endocyclic charge such as the following cationic heteroaryl groups: acridinium, benzimidazolium, benzobistriazolium, benzopyrazolium, benzopyridazinium, benzoquinolium, benzothiazolium, benzotriazolium, benzoxazolium, bipyridinium, bis- tetrazolium, dihydrothiazolium, imidazopyridinium, imidazolium, indolium, isoquinolium, naphthoimidazolium, naphthoxazolium, naphthopyrazolium, oxadiazolium, oxazolium, oxazolopyridinium, oxonium, phenazinium, phenoxazolium, pyrazinium, pyrazolium, pyrazoyltriazolium, pyridinium, pyridinoimidazolium, pyrrolium, pyrylium
  • Ar + represents an aralkyl radical, such as phenyl or naphthyl, bearing an exocyclic cationic charge, particularly tri(CrC 8 )alkylammonium such as trimethylammonium;
  • Ar represents an aryl group, especially phenyl, optionally substituted, preferentially with one or more electron-donating groups such as i) optionally substituted (C C 8 )alkyl, ii) optionally substituted (C C 8 )alkoxy, iii) (di)(CrC 8 )(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group, iv) aryl(CrC 8 )alkylamino, v) optionally substituted A/-(Ci-C 8 )alkyl-A/-aryl(CrC 8 )alkylamino or alternatively Ar represents a julolidine group;
  • - Ar is an optionally substituted divalent (hetero)alkylene group such as phenylene, particularly para-phenylene, or naphthalene, which are optionally substituted, preferentially with one or more groups (CrC 8 )alkyl, hydroxyl or (CrC 8 )alkoxy;
  • - Ar" is an optionally substituted (hetero)aryl group such as phenyl or pyrazolyl, which is optionally substituted, preferentially with one or more groups (CrC 8 )alkyl, hydroxyl, (di)(CrC 8 )(alkyl)amino, (CrC 8 )alkoxy or phenyl;
  • R a and R b which may be identical or different, represent a hydrogen atom or a group (d-Cs)alkyl, which is optionally substituted, preferentially with a hydroxyl group;
  • R a with a substituent of Het + and/or R b with a substituent of Ar form, together with the atoms that bear them, a (hetero)cycloalkyl; particularly, R a and R b represent a hydrogen atom or a group (CrC 4 )alkyl, which is optionally substituted with a hydroxyl group;
  • Q " represents an organic or mineral anionic counterion such as a halide or an alkyl sulfate
  • R 1 representing a group (C C 4 )alkyl such as methyl
  • R 2 and R 3 which may be identical or different, representing a hydrogen atom or a group (Ci-C 4 )alkyl such as methyl;
  • R 4 representing a hydrogen atom or an electron-donating group such as optionally substituted (CrC 8 )alkyl, optionally substituted (C C 8 )alkoxy, or (di)(CrC 8 )(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group; particularly, R 4 is a hydrogen atom,
  • - Z represents a group CH or a nitrogen atom, preferentially CH,
  • the chromophores (11-1 ) and (IV-1 ) are derived from Basic Red 51 , Basic
  • the dyes of formula (I) are fluorescent, i.e. they contain at least one fluorescent chromophore as defined previously.
  • fluorescent chromophores A and/or A' that are useful in the present invention, mention may be made of radicals derived from the following dyes: acridines, acridones, benzanthrones, benzimidazoles, benzimidazolones, benzindoles, benzoxazoles, benzopyrans, benzothiazoles, coumarins, difluoro ⁇ 2-[(2H-pyrrol-2-ylidene-kN)methyl]-1 H- pyrrolato-kN ⁇ bores (BODIPY ®), diketopyrrolopyrroles, fluorindines, (poly)methines (especially cyanins and styryls/hemicyanins), naphthalimides, naphthanilides, naphthylamine (such as dans
  • the fluorescent chromophore A and/or A' is cationic and comprises at least one quaternary ammonium radical such as those derived from the polymethine dyes of formulae (VI) and (VI') below:
  • W + representing a cationic heterocyclic or heteroaryl group, particularly comprising a quaternary ammonium optionally substituted with one or more groups (d-C 8 )alkyl optionally substituted especially with one or more hydroxyl groups;
  • W' + representing a divalent heterocyclic or heteroaryl radical as defined for W + ;
  • Ar representing an aryl group such as phenyl or naphthyl, optionally substituted preferentially with i) one or more halogen atoms such as chlorine or fluorine; ii) one or more groups (CrC 8 )alkyl, preferably of C C 4 such as methyl; iii) one or more hydroxyl groups; iv) one or more (C C 8 )alkoxy groups such as methoxy; v) one or more hydroxy(CrC 8 )alkyl groups such as hydroxyethyl, vi) one or more amino groups or (di)(CrC 8 )alkylamino, preferably with the C C 4 alkyl part optionally substituted with one or more hydroxyl groups, such as (di)hydroxyethylamino, vii) with one or more acylamino groups; viii) one or more heterocycloalkyl groups such as piperazinyl, piperidyl or 5- or 6-membered heteroary
  • Ar' is a divalent aryl radical as defined for Ar
  • n' represents an integer between 1 and 4 inclusive, and in particular m is 1 or 2; more preferentially 1 ;
  • R c and R d which may be identical or different, represent a hydrogen atom or an optionally substituted group (d-C 8 )alkyl, preferentially of C C 4 , or alternatively R c contiguous with W + or W' + and/or R d contiguous with Ar or Ar' form, with the atoms that bear them, a (hetero)cycloalkyl, particularly R c is contiguous with W + or W' + and forms a (hetero)cycloalkyl such as cyclohexyl;
  • Q " is an organic or mineral anionic counterion as defined previously;
  • the disulfide, thiol or protected-thiol dye is a quaternized or quaternizable fluorescent dye such that, in formula (I) with p and p' equal to 1 and A and/or A' representing a naphthalimidyl radical optionally bearing an exocyclic cationic charge of formula (VII) or (VII'):
  • W + or W' + is an imidazolium, pyridinium, benzimidazolium, pyrazolium, benzothiazolium or quinolinium optionally substituted with one or more identical or different C1-C4 alkyl radicals.
  • dyes of the invention mention may be made of the disulfide dyes chosen from formulae (VIII) to (XIV) and the thiol or protected-thiol dyes chosen from
  • G and G' which may be identical or different, represent a group -NR c R d , -NR' c R' d or Ci-C 6 alkoxy which is optionally substituted, preferentially unsubstituted; preferentially, G and G' represent a group -NR c R d or -NR' c R'd, respectively;
  • R 1 , R 2 , R 3 and R 4 which may be identical or different, represent a hydrogen atom or a d-C-e alkyl group; preferentially a hydrogen atom;
  • R a and R' a which may be identical or different, represent an aryl(C C 4 )alkyl group or a Ci-C 6 alkyl group optionally substituted with a hydroxyl or amino, C C 4 alkylamino or C C 4 dialkyi amino group, the said alkyl radicals possibly forming, with the nitrogen atom that bears them, a 5- to 7-membered heterocycle, optionally comprising another nitrogen or non-nitrogen heteroatom; preferentially, R a and R' a represent a C C 3 alkyl group optionally substituted with a hydroxyl group, or a benzyl group;
  • R and R' which may be identical or different, represent a hydrogen atom, an aryl(CrC 4 )alkyl group or a C C 6 alkyl group that is optionally substituted; preferentially, R and R' b represent a hydrogen atom or a C C 3 alkyl or benzyl group;
  • R c , R'c, Rd and R' d which may be identical or different, represent a hydrogen atom, an aryl(Ci-C 4 )alkyl or C C 6 alkoxy group or a C C 6 alkyl group that is optionally substituted;
  • R c , R' c , Rd and R' d preferentially represent a hydrogen atom, a hydroxyl, C C 3 alkoxy, amino or C C 3 (di)alkylamino group, or a C C 3 alkyl group that is optionally substituted with i) a hydroxyl group, ii) amino, iii) C C 3 (di)alkylamino, or iv) quaternary ammonium (R")(R"')(R"")N + -;
  • heterocyclic or heteroaryl group or alternatively two adjacent radicals R c and R d , R' c and R' d borne by the same nitrogen atom together form a heterocyclic or heteroaryl group; preferentially, the heterocycle or heteroaryl is monocyclic and 5- to 7-membered; more preferentially, the groups are chosen from imidazolyl and pyrrolidinyl;
  • R e and R' e which may be identical or different, represent a linear or branched C C 6 alkylene or C 2 -C 6 alkenylene hydrocarbon-based chain;
  • R f and R' f which may be identical or different, represent a group di(C C 4 )alkylamino, (R")(R"')N- or a quaternary ammonium group (R")(R"')(R"")N + - in which R", R'" and R"", which may be identical or different, represent a hydrogen atom or a C C 4 alkyl group or alternatively (R")(R"')(R"")N + - represents an optionally substituted cationic heteroaryl group, preferentially an imidazolinium group optionally substituted with a C C 3 alkyl group;
  • R g , R'g, R" g , R"'g, Rh, R'h, R"h, and R"' h represent a hydrogen atom, a halogen atom, an amino, C C 4 alkylamino, C C 4 dialkylamino, cyano, carboxyl, hydroxyl or trifluoromethyl group, an acylamino, C C 4 alkoxy, (poly)hydroxy(C 2 -C 4 )alkoxy, alkylcarbonyloxy, alkoxycarbonyl or alkylcarbonylamino radical, an acylamino, carbamoyl or alkylsulfonylamino radical, an aminosulfonyl radical, or a C Ci 6 alkyl radical optionally substituted with a group chosen from C Ci 2 alkoxy, hydroxyl, cyano, carboxyl, amino, C C 4 alkylamino and Ci-C 4 dialkylamino, or alternative
  • R, and R g ; R'" and R"' g ; R', and R' h ; and/or R" and R" h together form a fused (hetero)cycloalkyl, preferentially cycloalkyl such as cyclohexyl;
  • G represents -NR c R d
  • G' represents -NR' c R' d
  • two groups R c and R' g ; R' c and R" g ; R d and R g ; R' d and R"' g together form a saturated heteroaryl or heterocycle, optionally substituted with one or more groups (d-C 6 )alkyl, preferentially a 5- to 7-membered heterocycle containing one or two heteroatoms chosen from nitrogen and oxygen; more preferentially the heterocycle is chosen from morpholinyl, piperazinyl, piperidyl and pyrrolidinyl groups;
  • Ri, R'i, R"i, and R'" which may be identical or different, represent a hydrogen atom or a Ci-C 4 alkyl group
  • Ri , R2, R3, R 4 , R'i , R'2, R'3, and R' 4 which may be identical or different, represent a hydrogen atom or a C C 4 alkyl, C1-C12 alkoxy, hydroxyl, cyano, carboxyl, amino, Ci-C 4 alkylamino or C C 4 dialkylamino group, the said alkyl radicals possibly forming with the nitrogen that bears them a 5- to 7-membered heterocycle optionally comprising another nitrogen or non-nitrogen heteroatom;
  • Ri , R2, R3, R 4 , R'i , R'2, R'3, and R' 4 are hydrogen atoms or an amino group; more preferentially, R ⁇ R 2 , R3, R 4 , R'i , R'2, R'3, and R' 4 represent a hydrogen atom;
  • T a T , which may be identical or different, represent i) either a covalent ⁇ bond, ii) or one or more radicals or combinations thereof chosen from -S0 2 -, -0-, -S-, -N(R)-, -N + (R)(R°)-, -CO-, with R, R°, which may be identical or different, representing a hydrogen atom, a C C 4 alkyl or C C 4 hydroxyalkyl radical, or an aryl(C C 4 )alkyl;
  • T a is identical to T and they represent a covalent ⁇ bond or a group chosen from -N(R)-, -C(0)-N(R)-, -N(R)-C(0)-, -O-C(O)-, -C(0)-0- and -N + (R)(R°)-, with R, R°, which may be identical or different, representing a hydrogen atom or a C1-C4 al
  • the heterocycles are identical, monocyclic, saturated and 5- to 8-membered and comprise in total two nitrogen atoms; • represents an aryl or heteroaryl group fused to the imidazolium or phenyl ring; or alternatively is absent from the imidazolium or phenyl ring; preferentially, when the ring is present, the ring is a benzo;
  • Y is as defined previously; in particular, Y represents a hydrogen atom or a protecting group such as:
  • cationic 5- or 6-membered monocyclic heteroaryl such as pyrylium, pyridinium, pyrimidinium, pyrazinium, pyridazinium, triazinium, imidazolium; these groups being optionally substituted with one or more identical or different (C C 4 )alkyl groups such as methyl;
  • M + with M + representing an alkali metal such as sodium or potassium
  • M' representing an anionic counterion, derived from a salt of an organic or mineral acid, or from an organic or mineral base that ensures the electrical neutrality of the molecule.
  • the dyes of formula (I) are chosen from dyes with a naphthalimidyl disulfide, thiol or protected-thiol chromophore, chosen from formulae (XIII), ( ⁇ ), (XIV) and (XIV) as defined previously.
  • the dyes of formula (I) are chosen from disulfide, thiol or protected-thiol dyes chosen from formulae (XV) to (XV) below:
  • R and R' which may be identical or different, represent a hydroxyl group, an amino group (NR a R b ) or an ammonium group (N + R a R b R c ), An " ; preferentially hydroxyl; with R a , R b and R c , which may be identical or different, representing a hydrogen atom or a (CrC 4 )alkyl group;
  • R a and R of the amino or ammonium group form a 5- to 7-membered heterocycle optionally comprising another nitrogen or non- nitrogen heteroatom, such as morpholinyl, piperazinyl, piperidyl, pyrrolyl, morpholinium, piperazinium, piperidinium or pyrrolinium, and An " representing an anionic counterion;
  • R' and R which may be identical or different, represent a hydrogen atom or a group as defined for R and R'", respectively;
  • R g , R' g , R" g , R"' g , R h , R' h , R" h and R'" h represent a hydrogen or halogen atom, an amino, (di)(C C 4 )alkylamino, cyano, carboxyl, hydroxyl, trifluoromethyl, acylamino, C C 4 alkoxy, C 2 -C 4 (poly)hydroxyalkoxy, (C C 4 )alkylcarbonyloxy, (C C 4 )alkoxycarbonyl, (C C 4 )alkylcarbonylamino, acylamino, carbamoyl or (Ci-C 4 )alkylsulfonylamino group, an aminosulfonyl radical or a radical (CrCi 6 )alkyl optionally substituted with a group chosen from (CrCi 2 )alkoxy, hydroxyl
  • R'i, R"i, R"'i and R" which may be identical or different, represent a hydrogen atom or a (C C 4 )alkyl group; in particular R',, R" , R'",, and R"", represent a hydrogen atom;
  • m' which may be identical or different, represent an integer between 1 and 10 inclusive; in particular an integer between 2 and 4 inclusive; preferentially, m and m' are equal to 2;
  • the dyes of the invention belong to formula (XVa) or (XVa) which bear an ethylene group connecting the pyridinium part to the phenyl ortho or para to the pyridinium, i.e. 2-4', 4-2', 4-4':
  • R h and R" h are ortho to the pyridinium group and R' h and R" h represent a hydrogen atom.
  • Another aspect of the invention concerns the dyes of formula (XVa) or (XV'a) bearing groups R g , R" g in position 3' and R' g /R" g which represent a hydrogen atom.
  • the dyes of formulae (XVa) and (XV'a) bear their ethylene group para to the phenyl bearing the amino group: R'(CH2)p-N-(CH 2 )q-R and/or R"(CH2)p-N-(CH 2 )q-R'", i.e. in position 4', preferentially bear an ethylene or styryl group linking the pyridinium part to the phenyl ortho to the pyridinium, i.e. 2-4'.
  • the dyes of the invention belong to formul
  • Ri represents a C C 6 alkyl group substituted with one or more hydroxyl groups or - C(0)OR' with R' representing a hydrogen atom, a C C 4 alkyl group or a group - C(0)-0 " and, in the latter case, an anionic counterion An " is absent; in particular represents a C C 6 alkyl group substituted with one or more hydroxyl groups and more specifically with only one hydroxyl group;
  • R 2 represents a C C 6 alkyl group optionally substituted with one or more hydroxyl groups; • or alternatively the groups R- ⁇ and R 2 form, together with the nitrogen atom that bears them, a saturated heterocyclic radical substituted with at least one hydroxyl, (poly)hydroxy(CrC 4 )alkyl and/or -C(0)OR' group with R' representing a hydrogen atom, a C C 4 alkyl group or a group -C(0)-0 " and, in the latter case, an anionic counterion An " is absent; such as pyrrolidinyl and piperidyl;
  • R 3 represents a hydrogen atom or a group -C(0)OR" with R" representing a hydrogen atom, an alkali metal or a C C 6 alkyl group or alternatively R 3 represents a group -C(0)-0 " and, in the latter case, an anionic counterion An " is absent;
  • the dyes of the invention belong to:
  • R'i represents a C C 4 alkyl group substituted with one or more hydroxyl groups, particularly with only one hydroxyl group, or -C(0)OR' with R' representing a hydrogen atom, a C C 4 alkyl group or a group -C(0)-0 " and, in the latter case, an anionic counterion An " is absent; preferentially, R represents a C C 4 alkyl group substituted with a hydroxyl group;
  • R' 2 represents a C C 4 alkyl group optionally substituted with one or more hydroxyl groups, particularly with only one hydroxyl group;
  • R and R' 2 are identical;
  • n and m which may be identical or different, represent an integer between 1 and 4 inclusive; preferentially, n is equal to 3 and m is equal to 2;
  • the bond between the pyridinium ring and the double bond of the ethylene or styryl group is located in position 2 or 4 of the pyridinium, preferentially at 4.
  • the dyes i) as defined previously are chosen from compounds 44, 49, 49a and 55, especially 44, 49 and 55.
  • the dye i) is a dye comprising a "permanent" cationic charge, i.e. containing in its structure at least one quaternized nitrogen atom (ammonium) or quaternized phosphorus atom (phosphonium); preferentially quaternized nitrogen.
  • a "permanent" cationic charge i.e. containing in its structure at least one quaternized nitrogen atom (ammonium) or quaternized phosphorus atom (phosphonium); preferentially quaternized nitrogen.
  • composition according to the invention contains, in a cosmetic medium, an amount of dyes bearing a disulfide, thiol or protected-thiol function as defined previously, especially of formula (I) as defined previously, generally inclusively between 0.001 % and 30% relative to the total weight of the composition.
  • the amount of dyes bearing a disulfide, thiol or protected-thiol function as defined previously, especially of formula (I), is inclusively between 0.01 % and 5% by weight relative to the total weight of the composition.
  • the dye(s) are in an amount of between 0.01 % and 2%. i) .5).
  • the cosmetically acceptable organic or mineral acid salt and counterion of the dyes of the invention is inclusively between 0.01 % and 5% by weight relative to the total weight of the composition.
  • the dye(s) are in an amount of between 0.01 % and 2%. i) .5).
  • addition salts that may be used in the context of the invention may be chosen from addition salts with a cosmetically acceptable base such as basifying agents as defined below, for instance alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
  • a cosmetically acceptable base such as basifying agents as defined below, for instance alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
  • composition of the invention comprises one or more fatty substances.
  • the fatty substances of the invention are not oxyalkylenated.
  • the fatty substances of the invention are chosen from hydrocarbons, fatty alcohols, fatty esters, silicones and fatty ethers, or mixtures thereof.
  • the fatty substances of the invention may be liquid or non-liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013* 10 5 Pa).
  • the liquid fatty substances of the invention preferably have a viscosity of less than or equal to 2 Pa.s, better still less than or equal to 1 Pa.s and even better still less than or equal to 0.1 Pa.s at a temperature of 25°C and at a shear rate of 1 s '
  • liquid hydrocarbon means a hydrocarbon composed solely of carbon and hydrogen atoms, which is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013*10 5 Pa).
  • liquid hydrocarbons are chosen from:
  • C6"Ci6 lower alkanes examples include hexane, undecane, dodecane, tridecane, and isoparaffins, for instance isohexadecane, isododecane and isodecane.
  • liquid hydrocarbon(s) are chosen from liquid paraffins and liquid petroleum jelly.
  • liquid fatty alcohol means a non-glycerolated and non-oxyalkylenated fatty alcohol that is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1 .013x 10 5 Pa).
  • the liquid fatty alcohols of the invention comprise from 8 to 30 carbon atoms.
  • liquid fatty alcohols of the invention may be saturated or unsaturated.
  • the saturated liquid fatty alcohols are preferably branched. They may optionally comprise in their structure at least one aromatic or non-aromatic ring. They are preferably acyclic.
  • liquid saturated fatty alcohols of the invention are chosen from octyldodecanol, isostearyl alcohol and 2-hexyldecanol.
  • Octyldodecanol is most particularly preferred.
  • These unsaturated liquid fatty alcohols exhibit, in their structures, at least one double or triple bond.
  • the fatty alcohols of the invention bear in their structure one or more double bonds. When several double bonds are present, there are preferably 2 or 3 of them, and they may be conjugated or unconjugated.
  • These unsaturated fatty alcohols may be linear or branched.
  • They may optionally comprise in their structure at least one aromatic or non-aromatic ring. They are preferably acyclic.
  • liquid unsaturated fatty alcohols of the invention are chosen from oleyl alcohol, linoleyl alcohol, linolenyl alcohol and undecylenyl alcohol.
  • Oleyl alcohol is most particularly preferred.
  • liquid fatty ester means an ester derived from a fatty acid and/or from a fatty alcohol and that is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1 .013x 10 5 Pa).
  • the esters are preferably liquid esters of saturated or unsaturated, linear or branched Ci-C 2 6 aliphatic monoacids or polyacids and of saturated or unsaturated, linear or branched C C 2 6 aliphatic monoalcohols or polyalcohols, the total number of carbon atoms of the esters being greater than or equal to 10.
  • At least one from among the alcohol and the acid from which the esters of the invention are derived is branched.
  • ethyl palmitate isopropyl palmitate
  • alkyl myristates such as isopropyl myristate or ethyl myristate
  • isocetyl stearate 2-ethylhexyl isononanoate
  • isodecyl neopentanoate isostearyl neopentanoate.
  • Esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1-C22 alcohols and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and of non-sugar C 4 -C 2 6 dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols may also be used.
  • composition may also comprise, as liquid fatty ester, sugar esters and diesters of C 6 -C 30 and preferably C12-C22 fatty acids.
  • sugar esters and diesters of C 6 -C 30 and preferably C12-C22 fatty acids.
  • sugar esters oxygen-bearing hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms.
  • sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars include sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may be chosen especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C 6 -C 30 and preferably C12-C22 fatty acids. If they are unsaturated, these compounds may have one to three conjugated or non-conjugated carbon-carbon double bonds.
  • esters according to this variant may also be selected from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleopalmitate, oleostearate and palmitostearate mixed esters.
  • monoesters and diesters and especially sucrose, glucose or methylglucose monooleates or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates.
  • esters of mono-, di- or triacids with glycerol may also be used.
  • oils of plant origin or synthetic triglycerides that may be used in the composition of the invention as liquid fatty esters, examples that may be mentioned include:
  • oils of plant or synthetic origin such as liquid fatty acid triglycerides comprising from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, maize oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, sunflower oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil.
  • Liquid fatty esters derived from monoalcohols will preferably be used as esters according to the invention.
  • Isopropyl myristate and isopropyl palmitate are particularly preferred.
  • liquid silicone means an organopolysiloxane that is liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013* 10 5 Pa).
  • the silicone is chosen from liquid polydialkylsiloxanes, especially liquid polydimethylsiloxanes (PDMS) and liquid polyorganosiloxanes comprising at least one aryl group.
  • PDMS liquid polydimethylsiloxanes
  • silicones may also be organomodified.
  • organomodified silicones that can be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon-based group.
  • Organopolysiloxanes are defined in greater detail in Walter Noll's Chemistry and Technology of Silicones (1968), Academic Press. They may be volatile or non-volatile.
  • the silicones are more particularly chosen from those having a boiling point of between 60°C and 260°C, and even more particularly from:
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably 4 to 5 silicon atoms.
  • cyclocopolymers of the type such as dimethylsiloxane/methylalkylsiloxane, such as Silicone Volatile® FZ 3109 sold by the company Union Carbide, of formula:
  • Non-volatile polydialkylsiloxanes may also be used.
  • non-volatile silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes containing trimethylsilyl end groups.
  • oils of the 200 series from the company Dow Corning such as DC200 with a viscosity of 60 000 mm 2 /s;
  • CTFA dimethiconol
  • silicones containing aryl groups are polydiarylsiloxanes, especially polydiphenylsiloxanes and polyalkylarylsiloxanes. Examples that may be mentioned include the products sold under the following names:
  • oils of the SF series from General Electric such as SF 1023, SF 1154, SF 1250 and SF 1265.
  • the organomodified liquid silicones may especially contain polyethyleneoxy and/or polypropyleneoxy groups. Mention may thus be made of the silicone KF-6017 proposed by Shin-Etsu, and the oils Silwet® L722 and L77 from the company Union Carbide.
  • the liquid fatty acids are preferably unsaturated and/or branched fatty acids. Mention may be made in particular of oleic acid.
  • the liquid fatty ethers are chosen from liquid dialkyl ethers such as dicaprylyl ether.
  • the fatty substances may be non-liquid at room temperature and at atmospheric pressure.
  • non-liquid preferably means a solid compound or a compound that has a viscosity of greater than 2 Pa.s at a temperature of 25°C and at a shear rate of 1 s '
  • non-liquid fatty substances are chosen from fatty alcohols, fatty acid and/or fatty alcohol esters, nonsilicone waxes, silicones or fatty ethers which are non- liquid and preferably solid.
  • non-liquid fatty alcohols that are suitable for use in the invention are more particularly chosen from saturated or unsaturated, linear or branched alcohols comprising from 8 to 30 carbon atoms. Mention may be made, for example, of cetyl alcohol, stearyl alcohol and a mixture thereof (cetylstearyl alcohol).
  • non-liquid esters of fatty acids and/or of fatty alcohols mention may be made especially of solid esters derived from C 9 -C 2 6 fatty acids and from C 9 -C 2 6 fatty alcohols.
  • esters mention may be made of octyldodecyl behenate; isocetyl behenate; cetyl lactate; stearyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; myristyl stearate; octyl palmitate; octyl pelargonate; octyl stearate; alkyl myristates such as cetyl, myristyl or stearyl myristate; hexyl stearate.
  • esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1-C22 alcohols and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and of C 2 -C 2 6 dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols may also be used.
  • myristyl cetyl or stearyl palmitates
  • alkyl myristates such as cetyl myristate, and stearyl myristyl myristate.
  • the (non-silicone) wax(es) are selected in particular from carnauba wax, candelilla wax, esparto grass wax, paraffin wax, ozokerite, plant waxes such as olive wax, rice wax, hydrogenated jojoba wax or the absolute waxes of flowers such as the essential wax of blackcurrant blossom sold by the company Bertin (France), animal waxes, for instance beeswaxes or modified beeswaxes (cerabellina); other waxes or waxy starting materials that may be used according to the invention are especially marine waxes such as the product sold by the company Sophim under the reference M82, and polyethylene waxes or polyolefin waxes in general.
  • the non-liquid silicones in accordance with the invention may be present in the form of waxes, resins or gums.
  • the non-liquid silicone is chosen from polydialkylsiloxanes, especially polydimethylsiloxanes (PDMS), and organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • PDMS polydimethylsiloxanes
  • organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • the silicone gums that can be used in accordance with the invention are especially polydialkylsiloxanes and preferably polydimethylsiloxanes with high number-average molecular weights of between 200 000 and 1 000 000, used alone or as a mixture in a solvent.
  • This solvent can be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane and tridecane, or mixtures thereof.
  • Products that can be used more particularly in accordance with the invention are mixtures such as:
  • CTFA dimethiconol
  • CFA cyclic polydimethylsiloxane also known as cyclomethicone
  • a polydimethylsiloxane gum with a cyclic silicone such as the product SF 1214 Silicone Fluid from the company General Electric; this product is an SF 30 gum corresponding to a dimethicone, having a number-average molecular weight of 500 000, dissolved in the oil SF 1202 Silicone Fluid corresponding to decamethylcyclopentasiloxane;
  • the product SF 1236 is a mixture of a gum SE 30 defined above with a viscosity of 20 m 2 /s and of an oil SF 96 with a viscosity of 5x10 "6 m 2 /s. This product preferably comprises 15% of gum SE 30 and 85% of an oil SF 96.
  • organopolysiloxane resins that may be used in accordance with the invention are crosslinked siloxane systems containing the following units:
  • R represents an alkyl containing 1 to 16 carbon atoms.
  • these products the ones that are particularly preferred are those in which R denotes a C C 4 lower alkyl group, more particularly methyl.
  • resins of the type such as the trimethyl siloxysilicate sold in particular under the names X22-4914, X21-5034 and X21-5037 by the company Shin-Etsu.
  • the additional organomodified silicones include the polyorganosiloxanes containing:
  • substituted or unsubstituted amine groups for instance the products sold under the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning.
  • the substituted amine groups are, in particular, C C 4 aminoalkyl groups;
  • the non-liquid fatty ethers are chosen from dialkyl ethers and especially dicetyl ether and distearyl ether, alone or as a mixture.
  • compositions of the invention contain one or more fatty substances that are liquid at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013*10 5 Pa), optionally combined with one or more fatty substances that are non-liquid under the same conditions.
  • the fatty substance is chosen from liquid petroleum jelly, polydecenes and liquid esters, or mixtures thereof.
  • the fatty substance(s) used in the composition according to the present invention may be present in the composition in an amount ranging from 25% to 90%, preferably in an amount ranging from 30% to 80% and even more preferentially in an amount ranging from 35% to 70% by weight relative to the total weight of the composition.
  • composition according to the invention comprises one or more alkaline agents.
  • This agent may be chosen from mineral or organic or hybrid alkaline agents, or mixtures thereof.
  • the mineral alkaline agent(s) are preferably chosen from aqueous ammonia, alkali carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates, sodium hydroxide or potassium hydroxide, or mixtures thereof.
  • the alkaline agent(s) are organic amines, i.e. they contain at least one substituted or unsubstituted amino group.
  • the organic alkaline agent(s) are preferentially chosen from organic amines with a pK at 25°C of less than 12, preferably less than 10 and even more advantageously less than 6. It should be noted that it is the pK corresponding to the function of highest basicity.
  • Hybrid compounds that may be mentioned include the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid.
  • organic alkaline agent(s) are chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (XVII) below:
  • W is a divalent C C 6 alkylene radical optionally substituted with a hydroxyl group or a Ci-C 6 alkyl radical, and/or optionally interrupted with one or more heteroatoms such as oxygen or NR U ;
  • R x , R y , R z R l and R u which may be identical or different, represent a hydrogen atom or a C C 6 alkyl, C C 6 hydroxyalkyl or C C 6 aminoalkyl radical.
  • Examples of such amines that may be mentioned include 1 ,3-diaminopropane, 1 ,3- diamino-2-propanol, spermine and spermidine.
  • alkanolamine means an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched C C 8 alkyl groups bearing one or more hydroxyl radicals.
  • Alkanolamines such as monoalkanolamines, dialkanolamines or trialkanolamines comprising from one to three identical or different C C 4 hydroxyalkyl radicals are in particular suitable for performing the invention.
  • amino acids that may be used are of natural or synthetic origin, in their L, D or racemic form, and comprise at least one acid function chosen more particularly from carboxylic acid, sulfonic acid, phosphonic acid or phosphoric acid functions.
  • the amino acids may be in neutral or ionic form.
  • amino acids that may be used in the present invention, mention may be made especially of aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N- phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.
  • the amino acids are basic amino acids comprising an additional amine function optionally included in a ring or in a ureido function.
  • Such basic amino acids are preferably chosen from those corresponding to formula (XVIII) below:
  • the compounds corresponding to formula (XVIII) are histidine, lysine, arginine, ornithine and citrulline.
  • the organic amine may also be chosen from organic amines of heterocyclic type.
  • histidine that has already been mentioned in the amino acids, mention may be made in particular of pyridine, piperidine, imidazole, triazole, tetrazole and benzimidazole.
  • the organic amine may also be chosen from amino acid dipeptides.
  • amino acid dipeptides that may be used in the present invention, mention may be made especially of carnosine, anserine and baleine.
  • the organic amine is chosen from compounds comprising a guanidine function.
  • amines of this type that may be used in the present invention, besides arginine, which has already been mentioned as an amino acid, mention may be made especially of creatine, creatinine, 1 , 1-dimethylguanidine, 1 , 1-diethylguanidine, glycocyamine, metformin, agmatine, N-amidinoalanine, 3-guanidinopropionic acid, 4-guanidinobutyric acid and 2-
  • composition of the invention preferably contains one or more alkanolamines and/or one or more basic amino acids, more advantageously one or more alkanolamines. More preferentially still, the organic amine is monoethanolamine.
  • the composition of the invention comprises, as alkaline agent, one or more alkanolamines.
  • the alkanolamine is ethanolamine (or monoethanolamine).
  • the composition comprises, as alkaline agent, one or more alkanolamines (preferably ethanolamine) and aqueous ammonia.
  • alkanolamines preferably ethanolamine
  • the alkanolamine(s) are present in a predominant amount relative to the aqueous ammonia.
  • the composition according to the invention has a content of alkaline agent(s) ranging from 0.01 % to 30% by weight, preferably from 0.1 % to 20% by weight and better still from 1 % to 10% by weight relative to the weight of the said composition. iv) at least one reducing agent.
  • composition of the invention comprises one or more reducing agents.
  • the reducing agent(s) are chosen from thiols such as thioglycolic acid, thiolactic acid, 3-mercaptopropionic acid, thiomalic acid, 2,3-dimercaptosuccinic acid, cysteine, N-glycyl-L-cysteine, L-cysteinylglycine and also esters and salts thereof, thioglycerol, cysteamine and C C 4 acyl derivatives thereof, N-mesylcysteamine, N- acetylcysteine, N-mercaptoalkylamides of sugars such as N-(mercapto-2-ethyl) gluconamide, pantetheine, N-(mercaptoalkyl)-a hydroxyalkylamides, for example those described in patent application EP-A-354 835, N-mono- or N,N-dialkylmercapto-4- butyramides, for example those described in patent application EP-A
  • the reducing agent may alternatively be chosen from hydrides such as sodium or potassium borohydride or alkali metal or alkaline-earth metal sulfites or bisulfites; or alternatively from phosphorus derivatives such as phosphines or phosphites.
  • the reducing agent(s) are preferably chosen from thiols.
  • the preferred reducing agents are thioglycolic acid and cysteine, or salts thereof.
  • the reducing agent is preferably used as an aqueous solution.
  • the concentration of reducing agent(s) is inclusively between 0.01 % and
  • composition according to the invention may also comprise one or more chemical oxidizing agent(s).
  • chemical oxidizing agent means an oxidizing agent other than atmospheric oxygen.
  • the chemical oxidizing agents are for example chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof and percarbonates of alkali metals or alkaline-earth metals.
  • the oxidizing agent is hydrogen peroxide.
  • the content of oxidizing agent(s) more particularly represents from 0.1 % to 20% by weight and preferably from 0.5% to 10% by weight relative to the weight of the composition containing them. vi) optionally at least one thickening organic polymer;
  • composition according to the invention may also contain vi) one or more thickening organic polymers.
  • thickening polymer means a polymer which, when introduced at 1 % by weight in an aqueous solution or an aqueous-alcoholic solution containing 30% ethanol, and at pH 7, or in an oil chosen from liquid petroleum jelly, isopropyl myristate or cyclopentadimethylsiloxane, makes it possible to achieve a viscosity of at least 100 cps and preferably of at least 500 cps, at 25°C and at a shear rate of 1 s ' This viscosity may be measured using a cone/plate viscometer (Haake R600 rheometer or the like).
  • the thickening polymers may thicken the aqueous phase and/or the fatty phase, preferentially the aqueous phase.
  • organic thickening polymer means a thickening polymer as defined previously, which is formed from carbon and hydrogen, and possibly nitrogen, oxygen, sulfur, halogens such as fluorine, chlorine or bromine, and also phosphorus, alkali metals such as sodium or potassium, or alkaline-earth metals such as magnesium or calcium.
  • the organic polymers according to the invention do not comprise silicon.
  • the organic thickening polymers according to the invention may be of natural or synthetic origin.
  • the thickening polymers may be anionic, cationic, amphoteric or nonionic associative or non-associative polymers.
  • They may be thickeners for the aqueous or oily phases.
  • Aqueous-phase-thickening polymers that may be mentioned include non-associative thickening polymers bearing sugar units.
  • sucgar unit means a unit derived from a carbohydrate of formula C n (H 2 0) n -i or (CH 2 0) n , which may be optionally modified by substitution and/or by oxidation and/or by dehydration.
  • sugar units that may be included in the composition of the thickening polymers of the invention are preferably derived from the following sugars:
  • Thickening polymers of the invention include native gums such as:
  • a) tree or shrub exudates including:
  • gum arabic branched polymer of galactose, arabinose, rhamnose and glucuronic acid
  • ⁇ ghatti gum polymer derived from arabinose, galactose, mannose, xylose and glucuronic acid
  • ⁇ karaya gum (polymer derived from galacturonic acid, galactose, rhamnose and glucuronic acid);
  • gum tragacanth (or tragacanth) (polymer of galacturonic acid, galactose, fucose, xylose and arabinose);
  • gums derived from algae including:
  • ⁇ agar (polymer derived from galactose and anhydrogalactose);
  • ⁇ alginates polymers of mannuronic acid and of glucuronic acid
  • gums derived from seeds or tubers including:
  • ⁇ guar gum (polymer of mannose and galactose);
  • locust bean gum polymer of mannose and galactose
  • ⁇ fenugreek gum polymer of mannose and galactose
  • ⁇ tamarind gum polymer of galactose, xylose and glucose
  • ⁇ konjac gum polymer of glucose and mannose
  • microbial gums including:
  • ⁇ xanthan gum polymer of glucose, mannose acetate, mannose/pyruvic acid and glucuronic acid
  • ⁇ gellan gum polymer of partially acylated glucose, rhamnose and glucuronic acid
  • ⁇ scleroglucan gum glucose polymer
  • e) plant extracts including:
  • These polymers may be physically or chemically modified.
  • a physical treatment that may especially be mentioned is the temperature.
  • Chemical treatments that may be mentioned include esterification, etherification, amidation and oxidation reactions. These treatments can lead to polymers that may especially be nonionic, anionic or amphoteric.
  • these chemical or physical treatments are applied to guar gums, locust bean gums, starches and celluloses.
  • nonionic guar gums that may be used according to the invention may be modified with C C 6 (poly)hydroxyalkyl groups.
  • C C 6 (poly)hydroxyalkyl groups that may be mentioned, for example, are hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups.
  • guar gums are well known in the prior art and can be prepared, for example, by reacting the corresponding alkene oxides such as, for example, propylene oxides, with the guar gum so as to obtain a guar gum modified with hydroxypropyl groups.
  • the degree of hydroxyalkylation preferably ranges from 0.4 to 1.2, and corresponds to the number of alkylene oxide molecules consumed by the number of free hydroxyl functions present on the guar gum.
  • nonionic guar gums optionally modified with hydroxyalkyl groups are sold, for example, under the trade names Jaguar HP8, Jaguar HP60 and Jaguar HP120 by the company Rhodia Chimie.
  • the botanical origin of the starch molecules used in the present invention may be cereals or tubers.
  • the starches are chosen, for example, from corn starch, rice starch, cassava starch, barley starch, potato starch, wheat starch, sorghum starch and pea starch.
  • the starches may be chemically or physically modified especially by one or more of the following reactions: pregelatinization, oxidation, crosslinking, esterification, etherification, amidation, heat treatments.
  • Distarch phosphates or compounds rich in distarch phosphate will preferentially be used, for instance the products sold under the references Prejel VA-70-T AGGL (gelatinized hydroxypropyl cassava distarch phosphate), Prejel TK1 (gelatinized cassava distarch phosphate) and Prejel 200 (gelatinized acetyl cassava distarch phosphate) by the company Avebe, or Structure Zea from National Starch (gelatinized corn distarch phosphate).
  • amphoteric starches may also be used, these amphoteric starches comprising one or more anionic groups and one or more cationic groups.
  • the anionic and cationic groups may be linked to the same reactive site of the starch molecule or to different reactive sites; they are preferably linked to the same reactive site.
  • the anionic groups may be of carboxylic, phosphate or sulfate type, preferably carboxylic.
  • the cationic groups may be of primary, secondary, tertiary or quaternary amine type.
  • the starch molecules may be derived from any plant source of starch, especially such as corn, potato, oat, rice, tapioca, sorghum, barley or wheat. It is also possible to use the starch hydrolysates mentioned above.
  • the starch is preferably derived from potato.
  • the non-associative thickening polymers of the invention may be cellulose-based polymers not comprising any Ci 0 -C 30 fatty chains in their structure.
  • cellulose-based polymer means any polysaccharide compound bearing in its structure sequences of glucose residues connected via ⁇ -1 ,4 bonds; besides unsubstituted celluloses, the cellulose derivatives may be anionic, cationic, amphoteric or nonionic.
  • the cellulose-based polymers of the invention may be chosen from unsubstituted celluloses, including those in a monocrystalline form, and cellulose ethers.
  • cellulose ethers cellulose esters and cellulose ester ethers are distinguished.
  • cellulose esters are inorganic esters of cellulose (cellulose nitrates, sulfates, phosphates, etc.), organic cellulose esters (cellulose monoacetates, triacetates, amidopropionates, acetatebutyrates, acetatepropionates and acetatetrimellitates, etc.), and mixed organic/inorganic esters of cellulose, such as cellulose acetatebutyrate sulfates and cellulose acetatepropionate sulfates.
  • cellulose ester ethers mention may be made of hydroxypropylmethylcellulose phthalates and ethylcellulose sulfates.
  • nonionic cellulose ethers not containing a Ci 0 -C 30 fatty chain i.e. "non- associative”
  • anionic cellulose ethers not containing a fatty chain mention may be made of (poly)carboxy(CrC 4 )alkylcelluloses, and salts thereof. Examples that may be mentioned include carboxymethylcelluloses, carboxymethylmethylcelluloses (for example Blanose 7M from the company Aqualon) and carboxymethylhydroxyethylcelluloses, and the sodium salts thereof.
  • cationic cellulose ethers not containing a fatty chain
  • the commercial products corresponding to this definition are more particularly the products sold under the names Celquat® L 200 and Celquat® H 100 by the company National Starch.
  • nonassociative thickening polymers not bearing sugar units that may be used, mention may be made of crosslinked acrylic or methacrylic acid homopolymers or copolymers, crosslinked 2-acrylamido-2-methylpropanesulfonic acid homopolymers and crosslinked acrylamide copolymers thereof, ammonium acrylate homopolymers, or copolymers of ammonium acrylate and of acrylamide, alone or mixtures thereof.
  • a first family of nonassociative thickening polymers that is suitable for use is represented by crosslinked acrylic acid homopolymers.
  • homopolymers of this type mention may be made of those crosslinked with an allyl alcohol ether of the sugar series, such as, for example, the products sold under the names Carbopol 980, 981 , 954, 2984 and 5984 by the company Noveon or the products sold under the names Synthalen M and Synthalen K by the company 3 VSA.
  • the nonassociative thickening polymers may also be crosslinked (meth)acrylic acid copolymers, such as the polymer sold under the name Aqua SF1 by the company Noveon.
  • the nonassociative thickening polymers may be chosen from crosslinked 2- acrylamido-2-methylpropanesulfonic acid homopolymers and the crosslinked acrylamide copolymers thereof.
  • composition may similarly comprise, as nonassociative thickening polymers, ammonium acrylate homopolymers or copolymers of ammonium acrylate and of acrylamide.
  • ammonium acrylate homopolymers that may be mentioned is the product sold under the name Microsap PAS 5193 by the company Hoechst.
  • copolymers of ammonium acrylate and of acrylamide that may be mentioned is the product sold under the name Bozepol C Wunsch or the product PAS 5193 sold by the company Hoechst.
  • aqueous-phase thickening polymers mention may also be made of the non-cellulose-based associative polymers that are well known to those skilled in the art and especially of nonionic, anionic, cationic or amphoteric nature.
  • sociative polymers are polymers that are capable, in an aqueous medium, of reversibly associating with each other or with other molecules.
  • Their chemical structure more particularly comprises at least one hydrophilic region and at least one hydrophobic region.
  • hydrophobic group means a radical or polymer with a saturated or unsaturated, linear or branched hydrocarbon-based chain, comprising at least 10 carbon atoms, preferably from 10 to 30 carbon atoms, in particular from 12 to 30 carbon atoms and more preferentially from 18 to 30 carbon atoms.
  • the hydrocarbon-based group is derived from a monofunctional compound.
  • the hydrophobic group may be derived from a fatty alcohol such as stearyl alcohol, dodecyl alcohol or decyl alcohol. It may also denote a hydrocarbon-based polymer, for instance polybutadiene.
  • anionic associative polymers those that are particularly preferred according to the invention are polymers formed from 20% to 60% by weight of acrylic acid and/or of methacrylic acid, from 5% to 60% by weight of lower alkyl (meth)acrylates, from 2% to 50% by weight of fatty-chain allyl ether, and from 0 to 1 % by weight of a crosslinking agent which is a well-known copolymerizable unsaturated polyethylenic monomer, for instance diallyl phthalate, allyl (meth)acrylate, divinylbenzene, (poly)ethylene glycol dimethacrylate or methylenebisacrylamide.
  • a crosslinking agent which is a well-known copolymerizable unsaturated polyethylenic monomer, for instance diallyl phthalate, allyl (meth)acrylate, divinylbenzene, (poly)ethylene glycol dimethacrylate or methylenebisacrylamide.
  • crosslinked terpolymers of methacrylic acid, of ethyl acrylate and of polyethylene glycol (10 EO) stearyl alcohol ether (Steareth-10), in particular those sold by the company Ciba under the names Salcare SC 80® and Salcare SC 90®, which are aqueous 30% emulsions of a crosslinked terpolymer of methacrylic acid, of ethyl acrylate and of steareth-10 allyl ether (40/50/10).
  • polymers comprising i) at least one hydrophilic unit of unsaturated olefinic carboxylic acid type, and ii) at least one hydrophobic unit of the type such as a (Ci 0 -C 30 ) alkyl ester of an unsaturated carboxylic acid.
  • (Cio-C 30 )alkyl esters of unsaturated carboxylic acids that are useful in the invention comprise, for example, lauryl acrylate, stearyl acrylate, decyl acrylate, isodecyl acrylate and dodecyl acrylate, and the corresponding methacrylates, lauryl methacrylate, stearyl methacrylate, decyl methacrylate, isodecyl methacrylate and dodecyl methacrylate.
  • anionic associative polymers of this type use will be made more particularly of those formed from 95% to 60% by weight of acrylic acid (hydrophilic unit), 4% to 40% by weight of Ci 0 -C 30 alkyl acrylate (hydrophobic unit) and 0 to 6% by weight of crosslinking polymenzable monomer, or alternatively those formed from 98% to 96% by weight of acrylic acid (hydrophilic unit), 1 % to 4% by weight of Ci 0 -C 30 alkyl acrylate (hydrophobic unit) and 0.1 % to 0.6% by weight of crosslinking polymenzable monomer such as those described previously.
  • those most particularly preferred according to the present invention are the products sold by the company Goodrich under the trade names Pemulen TR1 ®, Pemulen TR2® and Carbopol 1382®, and even more preferentially Pemulen TR1 ®, and the product sold by the company SEPPIC under the name Coatex SX®.
  • a nonionic monourethane which is the product of reaction of a monohydric surfactant with a monoisocyanate containing monoethylenic unsaturation
  • Example 3 such as those described in patent application EP-A-0 173 109 and more particularly the terpolymer described in Example 3, namely a methacrylic acid/methyl acrylate/behenyl alcohol dimethyl-meta-isopropenylbenzylisocyanate ethoxylated (40 EO) terpolymer, as an aqueous 25% dispersion.
  • a methacrylic acid/methyl acrylate/behenyl alcohol dimethyl-meta-isopropenylbenzylisocyanate ethoxylated (40 EO) terpolymer as an aqueous 25% dispersion.
  • amphiphilic polymers comprising at least one ethylenically unsaturated monomer bearing a sulfonic group, in free or partially or totally neutralized form and comprising at least one hydrophobic part. These polymers may be crosslinked or noncrosslinked. They are preferably crosslinked.
  • the ethylenically unsaturated monomers bearing a sulfonic group are especially chosen from vinylsulfonic acid, styrenesulfonic acid, (meth)acrylamido(Cr C 2 2)alkylsulfonic acids, N-(Ci-C22)alkyl(meth)acrylamido(CrC 2 2)alkylsulfonic acids such as undecylacrylamidomethanesulfonic acid, and also partially or totally neutralized forms thereof.
  • Use will more preferably be made of (meth)acrylamido(Ci-C 2 2)alkylsulfonic acids, such as, for example, acrylamidomethanesulfonic acid, acrylamidoethanesulfonic acid, acrylamidopropanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, methacrylamido-2-methylpropanesulfonic acid, 2-acrylamido-n-butanesulfonic acid, 2- acrylamido-2,4,4-trimethylpentanesulfonic acid, 2-methacrylamidododecylsulfonic acid, 2-acrylamido-2,6-dimethyl-3-heptanesulfonic acid, and also partially or totally neutralized forms thereof.
  • (meth)acrylamido(Ci-C 2 2)alkylsulfonic acids such as, for example, acrylamidomethanesulfonic acid, acrylamidoethanes
  • APMS 2-Acrylamido-2-methylpropanesulfonic acid
  • amphiphilic polymers in accordance with the invention may be chosen especially from random amphiphilic AMPS polymers modified by reaction with a C6-C22 n- monoalkylamine or di-n-alkylamine, and such as those described in Patent Application WO 00/31154. These polymers may also contain other ethylenically unsaturated hydrophilic monomers selected, for example, from (meth)acrylic acids, ⁇ -substituted alkyl derivatives thereof or esters thereof obtained with monoalcohols or mono- or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, maleic anhydride, itaconic acid or maleic acid, or mixtures of these compounds.
  • the preferred polymers of this family are chosen from amphiphilic copolymers of AMPS and of at least one ethylenically unsaturated hydrophobic monomer.
  • copolymers may also contain one or more ethylenically unsaturated monomers not comprising a fatty chain, such as (meth)acrylic acids, ⁇ -substituted alkyl derivatives thereof or esters thereof obtained with monoalcohols or mono- or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, maleic anhydride, itaconic acid or maleic acid, or mixtures of these compounds.
  • monomers not comprising a fatty chain such as (meth)acrylic acids, ⁇ -substituted alkyl derivatives thereof or esters thereof obtained with monoalcohols or mono- or polyalkylene glycols, (meth)acrylamides, vinylpyrrolidone, maleic anhydride, itaconic acid or maleic acid, or mixtures of these compounds.
  • copolymers which may or may not be crosslinked and which may or may not be neutralized, comprising from 15% to 60% by weight of AMPS units and from 40% to 85% by weight of (C 8 -Ci 6 )alkyl(meth)acrylamide units or of (C 8 -
  • Ci 6 )alkyl(meth)acrylate units with respect to the polymer, such as those described in Application EP-A-750 899;
  • terpolymers comprising from 10 mol% to 90 mol% of acrylamide units, from 0.1 mol% to 10 mol% of AMPS units and from 5 mol% to 80 mol% of n-(C 6 - Ci 8 )alkylacrylamide units, such as those described in Patent US-5 089 578.
  • copolymers of totally neutralized AMPS and of dodecyl methacrylate and also crosslinked and non-crosslinked copolymers of AMPS and of n- dodecylmethacrylamide, such as those described in the Morishima articles mentioned above.
  • cationic associative polymers that may be mentioned are:
  • Polyacrylate-1 Crosspolymer is the product of polymerization of a monomer mixture comprising:
  • Ci-C 30 alkyl esters of (meth)acrylic acid o one or more Ci-C 30 alkyl esters of (meth)acrylic acid
  • - (Ill) quaternized (poly)hydroxyethylcelluloses modified with groups comprising at least one fatty chain, such as alkyl, arylalkyl or alkylaryl groups comprising at least 8 carbon atoms, or mixtures thereof.
  • the alkyl radicals borne by the above quaternized celluloses or hydroxyethylcelluloses preferably comprise from 8 to 30 carbon atoms.
  • the aryl radicals preferably denote phenyl, benzyl, naphthyl or anthryl groups.
  • Examples of quaternized alkylhydroxyethylcelluloses containing C 8 -C 30 fatty chains that may be mentioned include the products Quatrisoft LM 200®, Quatrisoft LM-X 529-18-A®, Quatrisoft LM-X 529-18B® (Ci2 alkyl) and Quatrisoft LM-X 529-8® (Ci 8 alkyl) sold by the company Aqualon, and the products Crodacel QM®, Crodacel QL® (C12 alkyl) and Crodacel QS® (Ci 8 alkyl) sold by the company Croda, and the product Softcat SL 100® sold by the company Aqualon.
  • Such polymers are described, for example, in patent application WO-00/68282.
  • cationic poly(vinyllactam) polymers according to the invention vinylpyrrolidone/dimethylaminopropylmethacrylamide/dodecyldimethylmethacrylamido- propylammonium tosylate terpolymers, vinylpyrrolidone/dimethylaminopropylmethacrylamide/cocoyldimethylmethacrylamido- propylammonium tosylate terpolymers, vinylpyrrolidone/dimethylaminopropylmethacrylamide/lauryldimethylmethacrylamido- propylammonium tosylate or chloride terpolymers are used in particular.
  • amphoteric associative polymers are preferably chosen from those comprising at least one non-cyclic cationic unit. Even more particularly, the ones that are preferred are those prepared from or comprising 1 mol% to 20 mol%, preferably 1.5 mol% to 15 mol% and even more particularly 1.5 mol% to 6 mol% of fatty-chain monomer relative to the total number of moles of monomers.
  • Amphoteric associative polymers according to the invention are described and prepared, for example, in patent application WO 98/44012.
  • amphoteric associative polymers the ones that are preferred are acrylic acid/(meth)acrylamidopropyltrimethylammonium chloride/stearyl methacrylate terpolymers.
  • the associative polymers of nonionic type that may be used according to the invention are preferably chosen from:
  • polyurethane polyethers comprising in their chain both hydrophilic blocks usually of polyoxyethylenated nature and hydrophobic blocks, which may be aliphatic sequences alone and/or cycloaliphatic and/or aromatic sequences.
  • celluloses or derivatives thereof modified with groups comprising at least one fatty chain, such as alkyl, arylalkyl or alkylaryl groups or mixtures thereof in which the alkyl groups are of C 8 , and in particular:
  • nonionic alkylhydroxyethylcelluloses such as the products Natrosol Plus Grade 330
  • nonionic nonoxynylhydroxyethylcelluloses such as the product Amercell HM-1500 sold by the company Amerchol;
  • nonionic alkylcelluloses such as the product Bermocoll EHM 100 sold by the company Berol Nobel;
  • associative guar derivatives for instance hydroxypropyl guars modified with a fatty chain, such as the product Esaflor HM 22 (modified with a C 2 2 alkyl chain) sold by the company Lamberti; the product Miracare XC 95-3 (modified with a d 4 alkyl chain) and the product RE 205-146 (modified with a C 2 o alkyl chain) sold by Rhodia Chimie.
  • the polyurethane polyethers comprise at least two hydrocarbon-based lipophilic chains containing from 6 to 30 carbon atoms, separated by a hydrophilic block, the hydrocarbon-based chains possibly being pendent chains or chains at the end of the hydrophilic block. In particular, it is possible for one or more pendent chains to be included.
  • the polymer may comprise a hydrocarbon-based chain at one end or at both ends of a hydrophilic block.
  • the polyurethane polyethers may be multiblock, in particular in triblock form.
  • the hydrophobic blocks may be at each end of the chain (for example: triblock copolymer containing a hydrophilic central block) or distributed both at the ends and in the chain (for example multiblock copolymer).
  • These same polymers may also be graft polymers or star polymers.
  • the nonionic fatty-chain polyurethane polyethers may be triblock copolymers in which the hydrophilic block is a polyoxyethylenated chain comprising from 50 to 1000 oxyethylene groups.
  • the nonionic polyurethane polyethers comprise a urethane bond between the hydrophilic blocks, whence arises the name.
  • By extension, also included among the nonionic fatty-chain polyurethane polyethers are those in which the hydrophilic blocks are linked to the lipophilic blocks via other chemical bonds.
  • nonionic fatty-chain polyurethane polyethers that may be used in the invention, it is also possible to use Rheolate 205® containing a urea function, sold by the company Rheox, or Rheolate® 208, 204 or 212, and also Acrysol RM 184®.
  • the product DW 1206B® from Rohm & Haas containing a C 2 o alkyl chain and a urethane bond, sold at a solids content of 20% in water, may also be used.
  • solutions or dispersions of these polymers especially in water or in aqueous-alcoholic medium.
  • examples of such polymers that may be mentioned are Rheolate® 255, Rheolate® 278 and Rheolate® 244 sold by the company Rheox.
  • the products DW 1206F and DW 1206J sold by the company Rohm & Haas may also be used.
  • polyurethane polyethers that may be used according to the invention are in particular those described in the article by G. Fonnum, J. Bakke and Fk. Hansen - Colloid Polym. Sci. 271 , 380.389 (1993).
  • a polyurethane polyether that may be obtained by polycondensation of at least three compounds comprising (i) at least one polyethylene glycol comprising from 150 to 180 mol of ethylene oxide, (ii) stearyl alcohol or decyl alcohol, and (iii) at least one diisocyanate.
  • Aculyn 46® is a polycondensate of polyethylene glycol containing 150 or 180 mol of ethylene oxide, of stearyl alcohol and of methylenebis(4-cyclohexyl isocyanate) (SMDI), at 15% by weight in a matrix of maltodextrin (4%) and water (81 %);
  • Aculyn 44® is a polycondensate of polyethylene glycol containing 150 or 180 mol of ethylene oxide, of decyl alcohol and of methylenebis(4- cyclohexyl isocyanate) (SMDI), at 35% by weight in a mixture of propylene glycol (39%) and water (26%)].
  • Use may also be made of fatty-phase-thickening polymers.
  • the polymers for structuring the oily phase via physical interactions are chosen from polyamides, silicone polyamides, saccharide or polysaccharide mono- or polyalkyl esters, N-acylamino acid amide derivatives, and copolymers comprising an alkylene or styrene block, these copolymers possibly being diblock, triblock, multiblock or radial-block polymers, also known as star copolymers, or alternatively comb polymers.
  • polymers that are soluble or dispersible in the oil or fatty phase by heating above their melting point m.p.
  • These polymers are especially block copolymers consisting of at least two blocks of different chemical nature, one of which is crystallizable.
  • block copolymers of olefin or of cycloolefin containing a crystallizable chain for instance those derived from the block polymerization of:
  • block copolymers may be in particular (ethylene/norbornene) block copolymers and (ethylene/propylene/ethylidenenorbornene) block terpolymers.
  • oc-olefins such as those mentioned above and in particular block bipolymers of ethylene and of 1 -octene may also be used.
  • the preferred copolymers are those that simultaneously contain at room temperature a crystallizable block and an amorphous block that are both hydrophobic and lipophilic, sequentially distributed; mention may be made, for example, of polymers containing one of the crystallizable blocks and one of the amorphous blocks below:
  • polyester type for instance poly(alkylene terephthalate)
  • polyolefin type for instance polyethylenes or polypropylenes.
  • amorphous and lipophilic block for instance: amorphous polyolefins or copoly(olefin)s such as poly(isobutylene), hydrogenated polybutadiene or hydrogenated poly(isoprene).
  • poly(6-caprolactone)-b-poly(butadiene) block copolymers preferably used hydrogenated, such as those described in the article Melting behaviour of poly(h- caprolactone)-block-polybutadiene copolymers from S. Nojima, Macromolecules, 32, 3727- 3734 (1999).
  • the semi-crystalline polymers that may be used in the context of the invention may be non-crosslinked or partially crosslinked, provided that the degree of crosslinking does not impede their dissolution or dispersion in the liquid oily phase by heating above their melting point. It may then be a case of chemical crosslinking, by reaction with a multifunctional monomer during the polymerization. It may also be a case of physical crosslinking, which may then be due either to the establishment of bonds of hydrogen or dipolar type between groups borne by the polymer, for instance dipolar interactions between carboxylate ionomers, these interactions being in small amount and borne by the polymer backbone; or due to a phase separation between the crystallizable blocks and the amorphous blocks borne by the polymer.
  • the semi-crystalline polymers that are suitable for the invention are non- crosslinked.
  • semi-crystalline polymers that may be used in the composition according to the invention, mention may be made of the Intelimer® products from the company Landec described in the brochure "Intelimer® polymers”. These polymers are in solid form at room temperature (25°C). They bear crystallizable side chains and contain the monomer. Mention may be made especially of Landec IP22®, with a melting point m.p. of 56°C, which is a viscous, impermeable, non-tacky product at room temperature.
  • polymer Structure O sold by the company National Starch, such as the product described in document US-A-5 736 125, of m.p. 44°C, and also semi-crystalline polymers containing crystallizable side chains comprising fluoro groups as described in Examples 1 , 4, 6, 7 and 8 of document WO-A-01/19333.
  • the semi-crystalline polymers that are suitable for use in the present invention are especially alkyl acrylates, among which mention may be made of the Landec copolymers:
  • IPA 13-1® polystearyl acrylate, m.p. of 49°C and MW of 145 000;
  • IPA 13-3® polyacrylate/methacrylic acid, m.p. of 65°C and MW of 114 000;
  • IPA 13-4® polyacrylate/vinylpyrrolidone, m.p. of 44°C and MW of 387 000;
  • polyamides used in the composition according to the invention are preferably those described in document US-A-5 783 657 from the company Union Camp.
  • ⁇ n denotes a whole number of amide units such that the number of ester groups represents from 10% to 50% of the total number of ester and amide groups;
  • R 1 is independently in each case an alkyl or alkenyl group containing at least 4 carbon atoms and especially from 4 to 24 carbon atoms;
  • ⁇ R 2 represents independently in each case a C 4 to C 55 hydrocarbon-based group, on condition that 50% of the groups R 2 represent a C 30 to C 55 hydrocarbon-based group;
  • ⁇ R 3 represents independently in each case an organic group bearing at least two carbon atoms, hydrogen atoms and optionally one or more oxygen or nitrogen atoms;
  • R 4 represents independently in each case a hydrogen atom, a Ci to Cio alkyl group or a direct bond to R 3 or to another R 4 such that the nitrogen atom to which are attached both R 3 and R 4 forms part of a heterocyclic structure defined by R 4 -N-R 3 , with at least 50% of the groups R 4 representing a hydrogen atom.
  • ester groups of this polyamide represent from 15% to 40% and at best from 20% to 35% of the total number of ester and amide groups.
  • n advantageously represents an integer ranging from 1 to 10 and better still from 1 to 5, limits inclusive.
  • R 1 is a C 12 to C 22 and preferably Ci 6 to C 22 alkyl group.
  • R 2 may be a Cio to C 42 hydrocarbon-based (alkylene) group.
  • at least 50% and better still at least 75% of the groups R 2 are groups containing from 30 to 42 carbon atoms.
  • the other groups R 2 are C 4 to C19 and better still C 4 to C12 hydrogen-containing groups.
  • R 3 represents a C 2 to C 36 hydrocarbon-based group or a polyoxyalkylene group and R 4 represents a hydrogen atom.
  • R 3 represents a C 2 to C12 hydrocarbon- based group.
  • the hydrocarbon-based groups may be linear, cyclic or branched, and saturated or unsaturated groups.
  • the alkyl and alkylene groups may be linear or branched, and saturated or unsaturated groups.
  • the thickening of the oily phase may be obtained by means of one or more polyamides defined above.
  • these polyamides are in the form of mixtures, these mixtures also possibly containing a synthetic product corresponding to a polyamide as defined above with n being 0, i.e. a diester.
  • polyamide resins resulting from the condensation of an aliphatic dicarboxylic acid and a diamine (including compounds containing, respectively, more than two carboxyl groups and more than two amine groups), the carboxyl and amine groups of adjacent individual units being condensed in the form of an amide bond.
  • These polyamide resins are especially the products sold under the brand name Versamid® by the companies General Mills, Inc. and Henkel Corp., under the brand name Onamid®, especially Onamid S or C. These resins have a weight-average molecular mass ranging from 6000 to 9000.
  • US-A-3 645 705 and US-A-3 148 125 Use is made more especially of Versamid® 30 or 744.
  • structuring polyamides that may be used in the composition according to the invention, mention may also be made of the commercial products sold or manufactured by the company Arizona Chemical under the names Uniclear 80 and Uniclear 100. They are sold, respectively, in the form of an 80% (active material) gel and a 100% (active material) gel in a mineral oil. They have a softening point of from 88 to 105°C. These commercial products are a mixture of copolymers of a C36 diacid coupled with ethylenediamine, having an average molecular mass of about 6000. The terminal ester groups result from the esterification of the remaining acid end groups with cetyl alcohol, stearyl alcohol or mixtures thereof (also known as cetylstearyl alcohol).
  • dextrin or inulin alkyl or polyalkyl esters that are suitable for use in the invention, mention may be made of dextrin or inulin alkyl or polyalkyl esters. It may especially be a dextrin mono- or polyester of at least one fatty acid corresponding especially to formula XX) below:
  • n is an integer ranging from 3 to 200, especially ranging from 20 to 150 and in particular ranging from 25 to 50,
  • Ri, R 2 and R 3 which may be identical or different, are chosen from hydrogen and an acyl group (R-C(O)-) in which the radical R is a linear or branched, saturated or unsaturated hydrocarbon-based group containing from 7 to 29, in particular from 7 to 21 , especially from 1 1 to 19, more particularly from 13 to 17, or even 15, carbon atoms, with the proviso that at least one of the said radicals R-i, R 2 or R 3 is other than hydrogen.
  • R ⁇ R 2 and R 3 may represent hydrogen or an acyl group (R-C(O)-) in which R is a hydrocarbon-based radical as defined above, with the proviso that at least two of the said radicals R ⁇ R 2 and R 3 are identical and other than hydrogen.
  • radicals R ⁇ R 2 and R 3 may all contain an acyl group (R-C(O)), which is identical or different and especially identical.
  • n mentioned above advantageously ranges from 25 to 50 and is especially equal to 38 in the general formula of the saccharide ester that may be used in the present invention.
  • radicals R ⁇ R 2 and/or R 3 which may be identical or different, contain an acyl group (R-C(O))
  • these radicals may be chosen especially from caprylic, capric, lauric, myristic, palmitic, stearic, arachic, behenic, isobutyric, isovaleric, 2-ethylbutyric, ethylmethylacetic, isoheptanoic, 2-ethylhexanoic, isononanoic, isodecanoic, isotridecanoic, isomyristic, isopalmitic, isostearic, isoarachic, isohexanoic, decenoic, dodecenoic, tetradecenoic, myristoleic, hexadecenoic, palmitoleic, oleic, elaidic, asclepinic, gondoleic, eicosenoic, sorbic, lino
  • At least one dextrin palmitate is used as fatty acid ester of dextrin.
  • This ester may be used alone or as a mixture with other esters.
  • the fatty acid ester of dextrin has a degree of substitution of less than or equal to 2.5, especially ranging from 1.5 to 2.5 and preferably from 2 to 2.5 on the basis of one glucose unit.
  • the weight-average molecular weight of the dextrin ester may in particular be from 10 000 to 150 000, especially from 12 000 to 100 000 and even from 15 000 to 80 000.
  • Dextrin esters in particular dextrin palmitates, are commercially available under the name Rheopearl TL or Rheopearl KL by the company Chiba Flour.
  • the N-acylamino acid amides that may be used are, for example, diamides from the combination of an N-acylamino acid with amines comprising from 1 to 22 carbon atoms, such as those described in document FR 2 281 162. They are, for example, alkylglutamic acid amide derivatives such as the laurylglutamic acid dibutylamide sold by the company Ajinomoto under the name Gelling Agent GP-1 , or alternatively the 2-ethylhexylglutamic acid dibutylamide sold by the company Ajinomoto under the name Gelling Agent GA-01. 4) Copolymers comprising an alkylene or styrene block
  • the copolymers may have a comb or the block structure of diblock, triblock, multiblock and/or radial or star type and may comprise at least two thermodynamically incompatible segments.
  • the structuring agent may comprise, for example, a styrene segment as described in patent applications EP 0 497 144, WO 98/42298, US 6 225 690, US 6 174 968 and US 6 225 390, an ethylene/butylene segment or an ethylene/propylene segment as described in patent applications US 6 225 690, US 6 174 968 and US 6 225 390, a butadiene segment, an isoprene segment, a polyvinyl segment, for instance polyalkyl (meth)acrylate or polyvinyl alcohol or polyvinyl acetate, a silicone segment as described in patent applications US 5 468 477 and US 5 725 882, or a combination of these segments.
  • a styrene segment as described in patent applications EP 0 497 144, WO 98/42298, US 6 225 690, US 6 174 968 and US 6 225 390
  • a diblock copolymer is usually defined as being of A-B type in which a hard segment (A) is followed by a soft segment (B).
  • a triblock copolymer is usually defined as being of A-B-A type or as a ratio of a hard segment, a soft segment and a hard segment.
  • a multiblock, radial or star copolymer may comprise any type of combination of hard segments and soft segments, with the proviso that the characteristics of the hard segments and of the soft segments are conserved.
  • hard segments of block copolymers that may be mentioned is styrene
  • soft segments of block copolymers that may be mentioned include ethylene, propylene and butylene, and a combination thereof.
  • the triblock copolymers and especially those of polystyrene/polyisoprene or polystyrene/polybutadiene type, which are suitable for use in the invention may be those sold under the reference Luvitol HSB by the company BASF. Mention may also be made of triblock copolymers of polystyrene/copoly(ethylene-propylene) or polystyrene/copoly(ethylene-butylene) type, such as those sold under the reference Kraton by the company Shell Chemical Co., or under the reference Gelled Permethyl 99 A by the company Penreco. Such triblock copolymers are particularly preferred according to the invention.
  • polymers bearing in the backbone at least one crystallizable block are preferred.
  • aqueous-phase or fatty-phase thickening polymers may be used alone or as mixtures in all proportions.
  • the thickeners are aqueous-phase thickeners.
  • the polymers in the cosmetic compositions in accordance with the present invention advantageously have in solution or in dispersion, at 1 % active material in water, a viscosity, measured using a Rheomat RM 180 rheometer at 25°C, of greater than 0.1 ps and even more advantageously greater than 0.2 cp, at a shear rate of 200 s '
  • the organic thickening polymer(s) are chosen from cellulose-based polymers.
  • the organic thickening polymer(s) are present in the composition according to the invention in a content ranging from 0.01 % to 10% by weight and preferably from 0.1 % to 5% by weight relative to the total weight of the composition.
  • the composition of the invention contains at least one surfactant.
  • the surfactant(s) may be nonionic, anionic, cationic, amphoteric or zwitterionic.
  • the composition of the invention contains at least one nonionic surfactant.
  • nonionic surfactants according to the invention, mention may be made, alone or as mixtures, of fatty alcohols, a-diols and alkylphenols, these three types of compound being polyethoxylated, polypropoxylated and/or polyglycerolated and containing a fatty chain comprising, for example, 8 to 40 carbon atoms, the number of ethylene oxide or propylene oxide groups possibly ranging especially from 2 to 50 and the number of glycerol groups possibly ranging especially from 2 to 30.
  • polyethoxylated fatty amides preferably having from 2 to 30 ethylene oxide units, polyglycerolated fatty amides containing on average 1 to 5, and in particular 1.5 to 4, glycerol
  • nonionic surfactant is chosen from:
  • fatty chain means a linear or branched, saturated or unsaturated hydrocarbon-based chain comprising from 6 to 30 carbon atoms and preferably from 8 to 30 carbon atoms.
  • alkylpolyglycosides As regards the alkylpolyglycosides, they are well known and may be represented more particularly by the following general formula:
  • Ri represents a linear or branched alkyl and/or alkenyl radical comprising from about 8 to 24 carbon atoms, or an alkylphenyl radical whose linear or branched alkyl radical comprises from 8 to 24 carbon atoms;
  • R 2 represents an alkylene radical comprising from about 2 to 4 carbon atoms
  • G represents a sugar unit comprising from 5 to 6 carbon atoms
  • t is an integer between 0 and 10, preferably between 0 and 4 and in particular between 0 and 4;
  • v denotes an integer between 1 and 15 inclusive.
  • Preferred alkylpolyglycosides according to the present invention are compounds of formula (V) in which R-i more particularly denotes a linear or branched, saturated or unsaturated alkyl radical comprising from 8 to 18 carbon atoms, t denotes a value ranging from 0 to 3 and more particularly equal to 0, and G may denote glucose, fructose or galactose, preferably glucose.
  • the degree of polymerization i.e. the value of v in formula (XXI), may range from 1 to 15 and preferably from 1 to 4.
  • the average degree of polymerization is more particularly between 1 and 2 and even more preferentially from 1 .1 to 1.5.
  • glycoside bonds between the sugar units are of 1 -6 or 1 -4 type and preferably of 1 -4 type.
  • Compounds of formula (XXI) are especially represented by the products sold by the company Cognis under the names Plantaren® (600 CS/U, 1200 and 2000) or Plantacare® (818, 1200 and 2000). It is also possible to use the products sold by the company SEPPIC under the names Triton CG 1 10 (or Oramix CG 1 10) and Triton CG 312 (or Oramix® NS 10), the products sold by the company BASF under the name Lutensol GD 70 or those sold by the company Chem Y under the name AG10 LK.
  • the mono- or polyglycerolated surfactants preferably comprise on average from 1 to 30 glycerol groups, more particularly from 1 to 10 and in particular from 1.5 to 5 glycerol groups.
  • the monoglycerolated or polyglycerolated surfactants are preferably chosen from the compounds of the following formulae:
  • R represents a saturated or unsaturated, linear or branched hydrocarbon-based radical comprising from 8 to 40 carbon atoms and preferably from 10 to 30 carbon atoms; m is an integer between 1 and 30, preferably between 1 and 10 and more particularly from 1.5 to 6; R may optionally comprise heteroatoms, for instance oxygen and nitrogen. In particular, R may optionally comprise one or more hydroxyl and/or ether and/or amide groups. R preferably denotes optionally mono- or polyhydroxylated Ci 0 -C 2 o alkyl and/or alkenyl radicals.
  • Use may be made, for example, of the polyglycerolated (3.5 mol) hydroxylauryl ether sold under the name Chimexane® NF from Chimex.
  • the (poly)ethoxylated fatty alcohols that are suitable for performing the invention are chosen more particularly from alcohols containing from 8 to 30 carbon atoms, and preferably from 12 to 22 carbon atoms.
  • the (poly)ethoxylated fatty alcohols more particularly contain one or more linear or branched, saturated or unsaturated hydrocarbon-based groups, comprising 8 to 30 carbon atoms, which are optionally substituted, in particular with one or more (in particular 1 to 4) hydroxyl groups. If they are unsaturated, these compounds may have one to three conjugated or non-conjugated carbon-carbon double bonds.
  • the (poly)ethoxylated fatty alcohol(s) preferably have the following formula:
  • R a representing a linear or branched C 8 -C 40 alkyl or linear or branched C 8 -C 30 alkenyl (preferentially C 8 -C 30 alkyl) group
  • - n is an integer between 1 and 200 inclusive, preferentially between 2 and 50 and more particularly between 2 and 30, such as 20.
  • the (poly)ethoxylated fatty alcohols are more particularly fatty alcohols comprising from 8 to 22 carbon atoms, oxyethylenated with 1 to 30 mol of ethylene oxide (1 to 30 EO).
  • fatty alcohols comprising from 8 to 22 carbon atoms, oxyethylenated with 1 to 30 mol of ethylene oxide (1 to 30 EO).
  • nonionic surfactants use is preferably made of C6-C24 alkyl polyglucosides and (poly)ethoxylated fatty alcohols, and C 8 -Ci 6 alkyl polyglucosides are more particularly used.
  • the amount of nonionic surfactant preferably ranges from 0.5% to 25% by weight, in particular from 1 % to 20% by weight and more particularly from 2% to 10% by weight relative to the total weight of the composition of the invention.
  • composition according to the invention may contain one or more amphoteric surfactants.
  • amphoteric or zwitterionic surfactant(s) that may be used in the present invention may especially be optionally quaternized secondary or tertiary aliphatic amine derivatives containing at least one anionic group, for instance a carboxylate, sulfonate, sulfate, phosphate or phosphonate group, and in which the aliphatic group or at least one of the aliphatic groups is a linear or branched chain comprising from 8 to 22 carbon atoms.
  • R a represents a Ci 0 -C 30 alkyl or alkenyl group derived from an acid R a -C(0)-OH preferably present in hydrolysed coconut oil, or a heptyl, nonyl or undecyl group;
  • R b represents a ⁇ -hydroxyethyl group
  • R c represents a carboxymethyl group
  • X represents the group -CH 2 -C(0)-OH, -CH 2 -C(0)-OZ', -CH 2 CH 2 -C(0)-OH, -CH 2 - CH 2 -C(0)-OZ', or a hydrogen atom;
  • ⁇ Y" represents -C(0)-OH, -C(0)-OZ' or the group -CH 2 -CH(OH)-S0 3 H or -CH 2 -CH(OH)-S0 3 Z';
  • Z' represents an ion derived from an alkali or alkaline-earth metal, such as sodium, potassium or magnesium; an ammonium ion; or an ion derived from an organic amine and in particular from an aminoalcohol, such as mono-, di- and triethanolamine, mono-, di- or triisopropanolamine, 2-amino-2-methyl-1 -propanol, 2- amino-2-methyl-1 ,3-propanediol and tris(hydroxymethyl)aminomethane; • R a ' represents a Ci 0 -C 30 alkyl or alkenyl group of an acid R a C(0)-OH preferably present in coconut oil or in hydrolysed linseed oil, an alkyl group, especially of C17 and its iso form, or an unsaturated C17 group.
  • an alkali or alkaline-earth metal such as sodium, potassium or magnesium
  • an ammonium ion or an ion derived from an organic amine and
  • the compounds corresponding to formula (XXIII) are preferred. These compounds are also classified in the CTFA dictionary, 5th edition, 1993, under the names disodium cocoamphodiacetate, disodium lauroampho-diacetate, disodium caprylamphodiacetate, disodium caprylampho-diacetate, disodium cocoamphodipropionate, disodium lauroamphodipropionate, disodium caprylampho-dipropionate, disodium caprylamphodipropionate, lauroamphodipropionic acid, cocoampho-dipropionic acid.
  • N-cocoylamidocarboxymethyl glycinate of an alkali metal such as sodium, or cocoamphodiacetate sold by the company Rhodia under the trade name Miranol ® C2M Concentrate.
  • amphoteric or zwitterionic surfactants use is preferably made of cocoylamidopropylbetaine, cocoylbetaine and the N- cocoylamidocarboxymethyl glycinate of an alkali metal such as sodium.
  • composition according to the invention preferably comprises from 0.01 % to 20% by weight, in particular from 0.5% to 10% by weight and better still from 1 % to 5% by weight of amphoteric or zwitterionic surfactant(s), relative to the total weight of the composition.
  • the composition of the invention contains at least one nonionic surfactant.
  • surfactants according to the invention use is made more particularly of C 6 -C 2 4 alkyl polyglucosides and more particularly C 8 -Ci 6 alkyl polyglucosides.
  • the surfactant(s) are preferably present in the composition in an amount ranging from 0.01 % to 40% by weight, preferably from 0.05% to 30% by weight, better still from 0.1 % to 20% and even better still from 0.2% to 10% by weight, relative to the total weight of the composition.
  • composition comprising the ingredients i) to iv) as defined previously and optionally the ingredients v) to viii) may also contain various adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic polymers, or mixtures thereof, mineral thickeners, penetrants, sequestrants, fragrances, buffers, dispersants, film-forming agents, preserving agents and opacifiers.
  • adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic polymers, or mixtures thereof, mineral thickeners, penetrants, sequestrants, fragrances, buffers, dispersants, film-forming agents, preserving agents and opacifiers.
  • the above adjuvants are generally present in an amount, for each of them, inclusively between 0.01 % and 20% by weight relative to the weight of the composition.
  • composition comprising the dye(s) bearing a disulfide, thiol or protected-thiol function especially of formula (I) as defined previously of the process of the invention may also contain one or more additional direct dyes other than the disulfide, thiol or protected- thiol direct dyes of formula (I) according to the invention.
  • direct dyes are chosen, for example, from those conventionally used in direct dyeing, and among which mention may be made of any commonly used aromatic and/or non-aromatic dye such as neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, natural direct dyes, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes, azine, triarylmethane, indoamine, methine, styryl, porphyrin, metalloporphyrin, phthalocyanine, cyanine and methine direct dyes, and fluorescent dyes, other than the dyes of formula (I).
  • aromatic and/or non-aromatic dye such as neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, natural direct dyes, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes, azine,
  • composition comprising the dye(s) bearing a disulfide, thiol or protected-thiol function especially of formula (I) as defined previously of the process of the invention may also contain one or more oxidation bases and/or one or more couplers conventionally used for the dyeing of keratin fibres.
  • oxidation bases mention may be made of para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, bis-para-aminophenols, ortho- aminophenols and heterocyclic bases, and the addition salts thereof.
  • couplers mention may be made especially of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and the addition salts thereof.
  • the coupler(s) are each generally present in an amount inclusively between 0.001 % and 10% by weight and preferably between 0.005% and 6% by weight relative to the total weight of the dye composition.
  • the oxidation base(s) present in the dye composition are each generally present in an amount inclusively between 0.001 % and 10% by weight and preferably between 0.005% and 6% by weight relative to the total weight of the dye composition.
  • the addition salts of the oxidation bases and couplers used in the context of the invention are especially chosen from the salts of addition with an acid, such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates, and the salts of addition with a base, such as alkali metal hydroxides, for instance sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines.
  • an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates
  • a base such as alkali metal hydroxides, for instance sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines.
  • composition of the process of the invention contains at least one oxidation base and optionally at least one coupler as defined above.
  • This embodiment may be implemented in the presence of one or more chemical oxidizing agents.
  • chemical oxidizing agent means chemical oxidizing agents other than atmospheric oxygen, such as those described previously.
  • the content of oxidizing agent(s) is generally inclusively between 1 % and 40% by weight relative to the weight of the composition and preferably between 1 % and 20% by weight relative to the weight of the composition containing them.
  • the pH of the composition according to the invention is generally inclusively between 2 and 12 approximately and preferably between 3 and 1 1 approximately. It may be adjusted to the desired value by means of acidifying or basifying agents usually used in the dyeing of keratin fibres, or alternatively using standard buffer systems.
  • the pH of the composition is preferentially inclusively between 6 and 9, particularly between 7 and 9, and more particularly between 7.5 and 9.
  • acidifying agents that may be mentioned, for example, are mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid or sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid and lactic acid, and sulfonic acids.
  • alkaline agents that may be mentioned, for example, are aqueous ammonia, alkali metal carbonates, alkanolamines such as monoethanolamine, diethanolamine and triethanolamine, and other alkaline agents iv) as defined previously.
  • the dye composition comprising i) the dye(s) bearing a disulfide, thiol or protected-thiol function especially of formula (I) as defined previously and the ingredients ii), Hi), iv) and optionally the ingredients v) to ix) as defined previously may be in various galenical forms, such as in the form of liquids, lotions, creams or gels, or in any other form that is suitable for dyeing keratin fibres. They may also be conditioned under pressure in an aerosol can in the presence of a propellant or in a non-aerosol can, and form a mousse.
  • the process for dyeing keratin fibres, especially dark keratin fibres, according to the invention comprises the step of applying to the keratin fibres:
  • ingredients i) to ⁇ v), vi) and vii) possibly being applied either together onto the said fibres or separately.
  • an ingredient i) that is fluorescent is used in the dye composition or the dyeing process.
  • the fluorescent dyes of formula (I) are chosen from the dyes of formulae (XIII), ( ⁇ '), (XIV), (XIV), (XVa), (XV'a), (XV) to (XV), (XVI), (XVI'), (XVIa) and (XVI'a) as defined previously.
  • the fluorescent dyes i) as defined previously used for lightening keratin fibres are chosen from compounds 44, 49, 49a and 55.
  • the dyeing process according to the invention may be performed in one step by applying to the keratin fibres the composition according to the invention comprising the ingredients i) to v) and vi) to vii) as defined previously, in one or more steps.
  • the reducing agent iv) as defined previously may be applied as a pretreatment before the application of the dye composition containing the ingredients i) to Hi) and vi) to vii) as defined previously.
  • the reducing composition comprising the reducing agent iv) and the ingredients Hi) and optionally vii) as defined previously is applied to the keratin fibres as a pretreatment before the application of the dye composition comprising the ingredients i) and ii) as defined previously and optionally the ingredients v) and vii) as defined previously.
  • the reducing composition comprising the reducing agent iv) and the ingredients Hi) and vii) as defined previously is applied to the keratin fibres as a pretreatment before the application of the dye composition comprising the ingredients i) and ii) as defined previously and the ingredients v) and vii) as defined previously.
  • the reducing composition comprising the reducing agent iv) and the ingredient Hi) as defined previously is applied to the keratin fibres as a pretreatment before the application of the dye composition comprising the ingredients i), ii) and vi) as defined previously.
  • the reducing composition comprising the reducing agent iv) and the ingredient Hi) as defined previously is applied to the keratin fibres as a pretreatment before the application of the dye composition comprising the ingredients i), ii) and vii) as defined previously.
  • the process of the invention comprises a first step of reducing pretreatment with a reducing composition that is applied to the keratin fibres, comprising the ingredients iv) and Hi) as defined previously, followed, in a second step, by the application of a dye composition comprising the ingredients i) and ii) as defined previously.
  • the process of the invention comprises a first step of reducing pretreatment with a reducing composition that is applied to the keratin fibres, comprising the ingredients iv) and optionally vii) as defined previously, followed, in a second step, by the application of a dye composition comprising the ingredients i), ii) and Hi) as defined previously, and possibly the ingredients v) and vii) as defined previously.
  • the reducing pretreatment may be of short duration, especially from 1 second to 30 minutes and preferably from 1 minute to 15 minutes, with one or more reducing agents as mentioned previously.
  • the keratin fibres are preferentially rinsed with water.
  • the leave-on time of the dye composition i.e. comprising the ingredient i) as defined previously, is inclusively between 5 minutes and 1 hour and preferably between 10 minutes and 40 minutes.
  • the dye composition i.e. the composition comprising the ingredient i
  • the dye composition is generally applied at room temperature. However, it may be applied at temperatures ranging from 20 to 180°C.
  • the reducing agent instead of using the reducing agent as a pretreatment, it is used as a post-treatment, after the application of the dye composition.
  • the dyeing process does not comprise any reducing pretreatment or post-treatment step.
  • the dyeing process comprises the step of applying the composition according to the invention, which comprises the ingredients i) to iv) and optionally vi) to vii) as defined previously.
  • the process of the invention may be preceded by a deprotection step for restoring the SH function in situ.
  • the deprotection step may also be performed during a step of pretreatment of the hair, for instance the hair reducing pretreatment.
  • a treatment with one or more chemical oxidizing agents may optionally be performed after the application of ingredients i) to Hi) and optionally vi) to vii) as defined previously to the keratin fibres.
  • a fixing composition comprising at least one cosmetic chemical oxidizing agent such as the ingredient v) as defined previously and optionally the ingredient vi) as defined previously may be used.
  • a cosmetic chemical oxidizing agent such as the ingredient v) as defined previously and optionally the ingredient vi) as defined previously
  • it may be chosen especially from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, and also enzymes, among which mention may be made of peroxidases, 2- electron oxidoreductases such as uricases, and 4-electron oxygenases such as laccases.
  • the use of hydrogen peroxide is particularly preferred.
  • the leave-on time of the oxidizing (fixing) composition is inclusively between 1 second and 40 minutes and preferably between 15 seconds and 15 minutes.
  • the application of the oxidizing composition takes place after the application of the dye composition, i.e. the composition comprising the ingredient i) as defined previously and optionally the ingredient vi) as defined previously.
  • the keratin fibres are preferentially rinsed with water.
  • the pH of the composition that contains i) is preferentially inclusively between 4 and 10 and particularly between 5 and 7; and the pH of the composition that contains iv) is preferentially inclusively between 4 and 10 and particularly between 7 and 10.
  • the dyeing and/or lightening process according to the invention may be followed by shampooing with a standard shampoo and/or drying of the keratin fibres.
  • compositions A, B and C in which:
  • At least one fluorescent disulfide dye in a concentration inclusively between 0.01 g% and 5 g% and preferably between 0.05 g% and 2 g%;
  • a fatty substance preferably chosen from mineral oils such as liquid petroleum jelly, in a concentration preferably inclusively between 30 g% and 80 g%; and optionally
  • composition A preferably being inclusively between 4 and 10, and more particularly between 5 and 7; > the reducing composition B comprises:
  • At least one alkaline agent preferably comprising an amine group, in a concentration preferably inclusively between 0.1 g% and 30 g% and more particularly between 0.5 g% and 5 g%;
  • composition B preferably being inclusively between 5 and 12, and more particularly inclusively between 7 and 10;
  • the fixing composition C comprises: v) at least one oxidizing agent in a concentration preferably inclusively between 0.01 g% and 30 g% and more particularly between 0.5 g% and 5 g%, the pH of composition C preferably being inclusively between 1.5 and
  • the fixing composition may also comprise a thickening organic polymer vi) as defined previously; just like compositions A and/or B.
  • the dye composition A is mixed with the reducing composition B in the following proportions: Mixing of 9 volumes of composition A with 1 volume of composition B in a bowl. The mixture is applied to the hair with a leave-on time preferably inclusively between 5 minutes and 1 hour and preferably between 10 minutes and 40 minutes. The hair is rinsed and is then optionally shampooed, shampooing preferably being performed, and the hair is then dried.
  • the dyeing formula A is mixed with the reducing composition B in the following proportions: Mixing of 9 volumes of composition A with 1 volume of composition B in a bowl. The mixture is applied to the hair with a leave-on time preferably inclusively between 5 minutes and 1 hour and more particularly inclusively between 10 minutes and 40 minutes.
  • the hair is optionally rinsed, preferably rinsed.
  • the fixing composition C is then applied to the hair with a leave-on time preferably inclusively between 1 minute and 30 minutes and more particularly inclusively between 3 minutes and 10 minutes.
  • the hair is rinsed and is then optionally shampooed, shampooing preferably being performed, and the hair is then dried.
  • the reducing formula is applied to the hair with a leave-on time preferably inclusively between 5 minutes and 1 hour and more particularly inclusively between 10 minutes and 40 minutes.
  • the hair is optionally rinsed, preferably rinsed.
  • the dye formula is applied to the hair with a leave-on time preferably inclusively between 5 minutes and 1 hour and more particularly inclusively between 10 minutes and 40 minutes.
  • the hair is optionally rinsed, preferably rinsed.
  • the fixing composition C is then applied to the hair with a leave-on time preferably inclusively between 1 minute and 30 minutes and more particularly between 3 minutes and 10 minutes.
  • the hair is rinsed and is then optionally shampooed, shampooing preferably being performed, and the hair is then dried.
  • Dyeing kit of the invention A subject of the invention is also a multi-compartment dyeing device or "kit” comprising a first compartment containing a dye composition comprising the composition containing the ingredient i), a second compartment which contains a reducing agent iv) as defined previously; the ingredients ii) to Hi) and optionally the ingredients v) to vii) as defined previously being divided among the first two compartments, and optionally a third compartment comprising at least one oxidizing agent as defined previously.
  • the device comprises a first compartment which contains a dye composition comprising the composition containing the ingredients i), ii) and optionally the ingredients vi) to vii) as defined previously; a second compartment which contains at least one reducing agent iv) as defined previously and Hi), and optionally the ingredients vi) as defined previously, and optionally a third compartment comprising at least one oxidizing agent v) as defined previously.
  • the dyeing device contains a first compartment containing a dye composition that comprises at least i) a protected-thiol dye, and the ingredients ii) and optionally the ingredients vii) as defined previously, a second compartment containing an agent capable of deprotecting the protected thiol to liberate the thiol, a third compartment that contains at least one reducing agent iv) as defined previously, and optionally the ingredients vii) as defined previously, and optionally a fourth compartment comprising an oxidizing agent v) as defined previously.
  • the first compartment contains i) and ii) as defined previously and optionally the ingredients vii) and vii) as defined previously, and the second compartment comprises the ingredients iv) and Hi) as defined previously;
  • the first compartment contains ingredients i) and ii) as defined previously and the second compartment comprises the ingredients iv) and Hi) and optionally the ingredients vii) as defined previously.
  • a third compartment may be present, which contains an oxidizing agent v) as defined previously, and optionally a fourth compartment containing an agent that is capable of deprotecting the protected thiol to liberate the thiol if the ingredient i) of the first compartment is a protected thiol.
  • Each of the devices mentioned above may be equipped with a means for applying the desired mixture to the hair, for instance the devices described in patent FR 2 586 913.
  • the examples that follow serve to illustrate the invention without, however, being limiting in nature.
  • the direct thiol, protected thiol or disulfide dyes of formula (I) that are useful in the present invention are known compounds and may be prepared according to methods known to those skilled in the art, especially from the methods described in patent applications EP 1 647 580, EP 2 004 759, WO 2007/1 10 541 , WO 2007/1 10 540, WO 2007/110 539, WO 2007/110 538, WO 2007/110 537, WO 2007/1 10 536, WO 2007/110 535, WO 2007/1 10 534, WO 2007/110 533, WO 2007/1 10 532, WO 2007/110 531 , EP 2 070 988 and WO 2009/040 354.
  • composition A 9 volumes of composition A are mixed with 1 volume of composition B in a bowl.
  • the mixture is applied to brown hair (dark hair having a tone height of 4 (TH4)), with a leave-on time of 20 minutes.
  • the hair is rinsed.
  • the fixing formula C is applied to the hair, with a leave-on time of 5 minutes.
  • the hair is rinsed and is then shampooed, and the hair is then dried.
  • the color of the locks was evaluated in the L*a*b* system by means of a M INOLTA ® CM 3600D spectrocolorimeter (llluminant D65).
  • L* represents the lightness
  • a* indicates the green/red color axis
  • b* the blue/yellow color axis.
  • L*, a* and b* represent the values after treatement
  • L 0 *, a 0 * and b 0 * represent the values measured before treatment
  • compositions A+B+C A mahogany colouration is obtained which is intense and persistent (even after several washing operations).

Abstract

L'invention concerne un procédé de coloration et/ou d'éclaircissement de fibres kératiniques telles que les cheveux, qui utilise i) au moins un colorant direct portant une fonction disulfure, thiol ou thiol protégé et ii) au moins 25 % d'une ou de plusieurs substances grasses, iii) au moins un agent alcalin et iv) au moins un réducteur. L'invention concerne également une composition comprenant les ingrédients i) à iv), l'utilisation de la combinaison de i), ii), iii) et iv) pour la coloration et/ou l'éclaircissement de fibres kératiniques, et un kit à compartiments multiples comprenant les ingrédients i) à iv). Le procédé de coloration et la composition selon l'invention permettent notamment une coloration durable de fibres kératiniques, qui est forte, chromatique et/ou homogène, avec ou sans l'utilisation d'un oxydant.
PCT/EP2012/052753 2011-02-25 2012-02-17 Composition pour la coloration de fibres kératiniques comprenant un colorant direct portant une fonction disulfure/thiol, une substance grasse, un agent alcalin et un réducteur WO2012113725A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR1151560A FR2971939B1 (fr) 2011-02-25 2011-02-25 Composition pour colorer les fibres keratiniques comprenant un colorant direct a fonction disulfure/thiol, un corps gras, un agent alcalin, et un agent reducteur
FR1151560 2011-02-25
US201161450366P 2011-03-08 2011-03-08
US61/450,366 2011-03-08

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WO2012113725A2 true WO2012113725A2 (fr) 2012-08-30
WO2012113725A3 WO2012113725A3 (fr) 2012-12-20

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US9383644B2 (en) 2014-09-18 2016-07-05 Heraeus Precious Metals North America Daychem LLC Sulfonic acid derivative compounds as photoacid generators in resist applications
WO2016146813A1 (fr) * 2015-03-19 2016-09-22 Basf Se Colorants directs cationiques
JP2016531987A (ja) * 2013-09-02 2016-10-13 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ スチリルスルフィド染料
US9477150B2 (en) 2015-03-13 2016-10-25 Heraeus Precious Metals North America Daychem LLC Sulfonic acid derivative compounds as photoacid generators in resist applications

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