WO2020002521A1 - Procédé de coloration de fibres de kératine par l'utilisation d'un monosaccharide, d'un polysaccharide portant des groupes amine et d'un colorant - Google Patents

Procédé de coloration de fibres de kératine par l'utilisation d'un monosaccharide, d'un polysaccharide portant des groupes amine et d'un colorant Download PDF

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Publication number
WO2020002521A1
WO2020002521A1 PCT/EP2019/067199 EP2019067199W WO2020002521A1 WO 2020002521 A1 WO2020002521 A1 WO 2020002521A1 EP 2019067199 W EP2019067199 W EP 2019067199W WO 2020002521 A1 WO2020002521 A1 WO 2020002521A1
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group
acid
preferentially
chosen
formula
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Andrew Greaves
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LOreal SA
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LOreal SA
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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
    • A61K8/60—Sugars; Derivatives thereof
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/882—Mixing prior to application
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • the present invention relates to a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, comprising the application to said keratin fibres a) of at least one monosaccharide, b) of at least one particular polysaccharide, in salified or non-salified form, and c) of at least one dyestuff, followed by a heat treatment of the keratin fibres.
  • the present invention also relates to a composition at acidic pH (C) comprising a) at least one monosaccharide, b) at least one polysaccharide bearing amine groups, in salified or non-salified form, and c) at least one dyestuff.
  • C composition at acidic pH
  • the present invention also relates to a kit comprising a multi-compartment device containing a) at least one monosaccharide, b) at least one polysaccharide bearing amine groups, and c) at least one dyestuff, and to a device for heating keratin fibres.
  • Two types of dyeing have essentially been developed for dyeing keratin materials, and in particular human keratin fibres.
  • the first type of dyeing is“permanent” or oxidation dyeing, which uses dyeing compositions containing oxidation dye precursors, generally referred to as oxidation bases.
  • oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
  • the second type of dyeing is "semi-permanent” dyeing or direct dyeing, which consists in applying, to the keratin fibres, direct dyes, which are coloured and colouring molecules that have affinity for said fibres, in leaving them on for a time, and then in rinsing them off.
  • This type of process does not require the use of an oxidizing agent to develop the colouring. However, it is possible to use such an agent in order to obtain, along with the colouring, a lightening effect. This is then referred to as direct dyeing or semi-permanent dyeing under lightening conditions.
  • Permanent or semi-permanent dyeing processes under lightening conditions therefore need to use, with the dye composition, an aqueous composition comprising at least one oxidizing agent, under alkaline pH conditions in the vast majority of cases.
  • the colourings thus obtained are only short-lasting. Specifically, given the low interaction between the colouring agents and the fibres, the colourings have a tendency to fade out, or even to disappear, rapidly, with respect to external agents, such as light, sweat, mechanical actions (brushing, styling) and notably after a few shampoo washes.
  • the dyeing power of these compositions may not be entirely satisfactory, or even may be poor, and lead to a restricted range of colours.
  • the colourings may also be too selective, i.e. the difference in colouring is too great along the same keratin fibre that is differently sensitized between its end and its root.
  • a subject of the present patent application is thus a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, comprising:
  • steps (i), (ii) and (iii) may be performed simultaneously or sequentially, before being followed by
  • composition (C) Another subject of the invention is an aqueous composition having an acid pH (pH ⁇ 7), also referred to as composition (C), comprising:
  • Another subject of the invention relates to a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, comprising a step of applying to said keratin fibres an aqueous composition (C), as described previously, followed by a step of heat treatment of said keratin fibres at a temperature greater than or equal to 80°C, preferably with an iron.
  • a process for dyeing keratin fibres in particular human keratin fibres such as the hair, comprising a step of applying to said keratin fibres an aqueous composition (C), as described previously, followed by a step of heat treatment of said keratin fibres at a temperature greater than or equal to 80°C, preferably with an iron.
  • the combination of the particular monosaccharide and of the amino polysaccharide makes it possible to form a protective film around the fibres containing the dyestuff.
  • the colourings obtained are more resistant to external agents, and are notably persistent with respect to shampoo washing.
  • the colourings and the treated keratin fibres are also resistant to rubbing and other forms of mechanical attack such as brushing and combing. It should also be noted that the treated keratin fibres do not transfer the colour to tissues and do not stain the scalp.
  • Fibres dyed with the combination of the particular monosaccharide(s), of the amine polysaccharide(s) and of the dyestuff(s) according to the invention make it possible to dye and in addition to improve the cosmetic nature of damaged keratin fibres intrinsically, while at the same time maintaining or even improving the manageability (taming), the frizziness control and/or the persistence of styling of said fibres.
  • This combination also makes it possible to prevent the breakage of natural keratin fibres, while maintaining or even improving the manageability (taming), the frizziness control and/or the persistence of the styling of said fibres.
  • the colourings also have improved colouring properties, notably in terms of intensity, uniformity and persistence, notably with respect to shampoo washing.
  • the present invention relates to a kit comprising:
  • a multi-compartment device comprising a first compartment containing a cosmetic composition (ca) comprising a) one or more monosaccharides; a second compartment containing a cosmetic composition (cb) comprising b) one or more polysaccharides bearing amine group(s) and optionally d) one or more organic or mineral acids; and a third compartment containing a dye composition (cc) comprising c) one or more dyestuffs chosen from pigments and direct dyes, and mixtures thereof; and
  • polysaccharides refers to a polysaccharide sugar which is a polymer constituted of several saccharides bonded together via O-oside bonds, said polymers being constituted of monosaccharide units as defined previously, said monosaccharide units comprising at least 5 carbon atoms, preferably 6; in particular, the monosaccharide units are linked together via a 1,4 or 1,6 bond as a (alpha) or b (beta) anomer, it being possible for each oside unit to be of L or D configuration, and also the salts thereof and the solvates thereof such as the hydrates of said monosaccharides; more particularly, they are polymers formed from a certain number of saccharides (or monosaccharides) having the general formula: -[C x (H 2 0) y )] n - where x is an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive and preferably
  • the term“bearing amine group(s)” means that the monosaccharide(s) a) or polysaccharide(s) b) are substituted with one or more amino group(s) NR I R 2 i.e. at least one of the hydroxyl groups of at least one saccharide unit is replaced with a group NR I R 2 with Ri and R 2 , which may be identical or different, representing i) a hydrogen atom, ii) a (Ci-C 6 )alkyl group that is optionally substituted, preferably with one or more hydroxyl or NH 2 groups, iii) an aryl group such as phenyl, iv) an aryl(Ci-C 4 )alkyl group such as benzyl, v) a (hetero)cyclo(C5-C 7 )alkyl group such as cyclohexyl, morpholinyl, piperazinyl, piperidyl, vi) a (
  • low molecular weight means that the polysaccharide bearing an amine group has an average molecular weight of less than 400 000 Da;
  • organic or mineral acid salt more particularly means organic or mineral acid salts in particular chosen from a salt derived from i) hydrochloric acid HC1, ii) hydrobromic acid HBr, iii) sulfuric acid H 2 S0 4 , iv) alkylsulfonic acids: Alk-S(0) 2 OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S(0) 2 OH such as benzenesulfonic acid and toluenesulfonic acid; vi) alkoxysulfinic acids: Alk-0-S(0)0H such as methoxysulfinic acid and ethoxysulfinic acid; vii) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; viii) phosphoric acid H 3 P0 4 ; ix) triflic acid CF3SO3H and
  • alkyl group or unsaturated C 2 -C 3 o radical being optionally interrupted and/or optionally substituted preferably with one or more hydroxyl groups and not substituted with one or more amino radicals
  • R preferably denoting a (Ci-C 6 )alkyl group optionally interrupted and/or optionally substituted with 1, 2 or 3 hydroxyl groups; preferentially, R represents a (Ci- C 4 )alkyl group such as methyl or ethyl
  • the organic monocarboxylic acids (I) are chosen from acetic acid, glycolic acid and lactic acid, and mixtures thereof, and more particularly from acetic acid and lactic acid;
  • A represents a saturated or unsaturated, cyclic or non-cyclic, aromatic or non aromatic polyvalent hydrocarbon-based group comprising from 1 to 30 carbon atoms, optionally interrupted with one or more heteroatoms such as oxygen and/or optionally substituted notably with one or more hydroxyl groups and t represents an integer between 1 and 5 inclusive; preferably, A represents a divalent (Ci-C 6 )alkylene group optionally substituted notably with one or more hydroxyl groups and not substituted with at least one amino radical, and t is equal to 1, 2 or 3, the polycarboxylic acids of formula (II) are preferably chosen from tartaric acid, succinic acid, fumaric acid and citric acid, and mixtures thereof; and
  • amino acids including more carboxylic acid radicals than amino groups, such as gamma-carboxyglutamic acid, aspartic acid, glutamic acid, in particular gamma-carboxyglutamic acid; in particular, salts of monocarboxylic acids other than pyrrolidonecarboxylic acid, 100 OE and 500 OE ethoxylated stearic acids, and linoleic acid;
  • an“alkyl radical” is a linear or branched Ci-Cio, preferably Ci-C 6 and in particular Ci-C 4 hydrocarbon-based radical, such as methyl or ethyl, unless otherwise indicated;
  • a (Cx-Cy)alkyl radical is a linear or branched Cx-Cy hydrocarbon-based radical; the expression“optionally interrupted” attributed to the alkyl radical or to the polyvalent hydrocarbon-based group A as defined previously means that said radical may be interrupted with one or more groups or heteroatoms chosen from O, S, CO or combinations thereof such as -CO-O- or -O-CO-, preferably interrupted with one or more non- adjacent oxygen atoms;
  • the expression“optionally substituted” attributed to the alkyl radical or to the polyvalent hydrocarbon-based group A as defined previously means that said radical may be substituted with one or more radicals chosen from the following radicals: i) hydroxyl, ii) Ci-C 4 alkoxy, iii) carboxyl, iv) acylamino, v) amino optionally substituted with one or two identical or different Ci-C 4 alkyl radicals, 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;
  • an“alkoxy radical” is an alkyl-oxy radical for which the alkyl radical is a linear or branched C 1 -C 10 , preferentially Ci-C 6 and more particularly C 1 -C 4 hydrocarbon-based radical such as methoxy or ethoxy;
  • aryl or heteroaryl 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 one of the following atoms or groups:
  • Ci-C 6 preferably Ci-C 4 , alkyl
  • radical R is a hydrogen atom or a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group and the radical R' is a Ci-C 2 alkyl radical;
  • R represents a hydrogen atom or a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group and the radical R' represents a C 1 -C 4 alkyl radical, or a phenyl radical;
  • radicals R which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group; - cyano;
  • cyclic or heterocyclic part of a non-aromatic group may be substituted with at least one substituent chosen from the following groups:
  • R-C(O)-N(R’)- - alkylcarbonylamino
  • R-C(O)-N(R’)- a radical atom or a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group
  • the radical R is a Ci-C 2 alkyl group or an amino optionally substituted with one or two identical or different C 1 -C 4 alkyl groups which themselves optionally bear at least one hydroxyl group;
  • R-C(O)-O- - alkylcarbonyloxy
  • R-C(O)-O- the radical R is a C 1 -C 4 alkyl radical or an amino group optionally substituted with one or two identical or different C 1 -C 4 alkyl groups which themselves optionally bear at least one hydroxyl group;
  • R-G-C(O)- - alkoxycarbonyl
  • R-G-C(O)- the radical R is a C 1 -C 4 alkoxy radical and G is an oxygen atom, or an amino group optionally substituted with a C 1 -C 4 alkyl group which itself optionally bears at least one hydroxyl group;
  • a cyclic or heterocyclic radical, or a non-aromatic part of an aryl or heteroaryl radical may also be substituted with one or more oxo groups;
  • an "aryl” radical represents a monocyclic or fused or non-fused polycyclic carbon-based group, comprising from 6 to 22 carbon atoms, at least one ring of which is aromatic; such as phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl, preferentially phenyl;
  • a“heteroaryl radical” represents an optionally cationic, 5- to 22-membered, monocyclic or fused or non-fused polycyclic group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, (benz)imidazolyl, (benzo)bistriazolyl, (benzo)pyrazolyl, (benzo)pyridazinyl, (benzo)quinolyl, (benzo)thiazolyl, (benzo)triazolyl, (benz)oxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthoxazolyl, naphthopyrazolyl, oxadiazolyl, ox
  • heterocyclic radical is a fused or non-fused, 5- to 22-membered monocyclic or polycyclic but non-aromatic radical that may contain one or two unsaturations, including from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium;
  • a“heterocycloalkyl radical” is a heterocyclic radical comprising at least one saturated ring
  • fibres or hair are elastic, have no body, do not hold shape, and the head of hair is flat without volume;
  • the dyeing process according to the present invention comprises a step consisting in applying to keratin fibres a) one or more monosaccharides, and also the a or b anomers thereof, the optical isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof, also referred to as ingredients a).
  • the monosaccharide(s) a) that may be used according to the present invention may or may not contain amine groups, i.e. they may be chosen from monosaccharides not comprising any amine groups, monosaccharides comprising at least one amine group, and mixtures thereof.
  • the monosaccharide(s) a) are chosen from monosaccharides not comprising any amine groups, and also the a or b anomers thereof, the isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof.
  • the monosaccharide(s) a) denote a mixture of monosaccharides, one of which is xylose or the a or b anomers thereof, the isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof.
  • the monosaccharide(s) a) denote a single monosaccharide, in particular xylose or the a or b anomers thereof, the isomers thereof of L or D configuration and the solvates thereof such as hydrates.
  • the monosaccharide(s) a) are chosen from C 7 monosaccharides: heptoses, such as aldoheptoses and keto heptoses, and also the a or b anomers thereof, the isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof.
  • the monosaccharide(s) a) are C 6 monosaccharides: hexoses, and also the a or b anomers thereof, the isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof.
  • the monosaccharide(s) a) are chosen from hexoses of formula (Al), and also the a or b anomers thereof, the isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof:
  • R a , R b , R d , R e and R f which may be identical or different, represent i) a hydroxyl group, ii) a (Ci-C 4 )alkoxy group, the alkyl chain of which may be optionally substituted, notably with one or more hydroxyl groups, or iii) a carboxyl group; more preferentially, R a , R b , R d , R e and R f represent a hydroxyl group.
  • the monosaccharide(s) a) are chosen from the hexoses of formula (Al) of D configuration, also known as D-glucopyrans, and better still from the hexoses of formula (Al) of b (beta) anomeric configuration.
  • the monosaccharide(s) a) are chosen from hexoses of formula (AG) below, and also the a or b anomers thereof, the optical isomers thereof of L or D configuration, preferably D configuration, and the solvates thereof such as hydrates, and mixtures thereof:
  • the monosaccharide(s) a) are advantageously chosen from aldohexoses and ketohexoses, preferably from glucose, galactose, allose, altrose, mannose, gulose, idose and talose, and also the alpha or beta anomers thereof, the optical isomers thereof of L or D configuration, the solvates thereof such as hydrates, and mixtures thereof, more preferentially from glucose and galactose, better still glucose, and even better still glucose of D configuration.
  • aldohexoses and ketohexoses preferably from glucose, galactose, allose, altrose, mannose, gulose, idose and talose, and also the alpha or beta anomers thereof, the optical isomers thereof of L or D configuration, the solvates thereof such as hydrates, and mixtures thereof, more preferentially from glucose and galactose, better still glucose, and even better still glucose of D configuration.
  • the monosaccharide(s) a) are C5 monosaccharides: pentoses, and also the a or b anomers thereof, the optical isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof.
  • the monosaccharide(s) a) are chosen from the pentoses of formula (A2), and also the a or b anomers thereof, the isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof:
  • formula (A2), Rg, Rh, Ri and Rj which may be identical or different, represent i) a hydroxyl group, or ii) a (Ci-C 4 )alkoxy group, the alkyl chain of which may be optionally substituted, notably with one or more hydroxyl groups.
  • the monosaccharide(s) a) are chosen from the pentoses of formula (A2) of D configuration, and better still from the pentoses of formula (A2) of b (beta) anomeric configuration.
  • the monosaccharide(s) a) are chosen from aldopentoses and ketopentoses, and mixtures thereof, and more preferentially xylose, arabinose, lyxose, ribose, ribulose and xylulose, and also the a or b anomers thereof, the optical isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof.
  • the monosaccharide(s) a) are advantageously chosen from monosaccharides not comprising any amine groups, and preferably from xylose and glucose, and mixtures thereof.
  • the monosaccharide(s) a) are chosen from monosaccharides bearing an amine group, i.e. monosaccharides comprising at least one amine group, and also the a or b anomers thereof, the optical isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof.
  • the monosaccharide(s) a) are chosen from monosaccharides bearing amine group(s), they are preferably salified with a mineral acid such as hydrochloric acid.
  • the monosaccharide(s) a) bear amine group(s) and denote a mixture of monosaccharide(s) bearing amine group(s), one of which is glucosamine or the salts thereof with an organic or mineral acid such as hydrochloric acid, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the monosaccharide(s) a) bear amine group(s) and denote a single monosaccharide bearing amine group(s), in particular glucosamine or the salts thereof with an organic or mineral acid or more particularly the mineral acid salts thereof such as the hydrochloric acid salt thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the monosaccharide(s) a) are C 5 monosaccharides bearing amine group(s): pentosamines, and also the a or b anomers thereof, the optical isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof.
  • the pentosamines are chosen from aldopentosamines and ketopentosamines such as xylosamine, arabinosamine, lyxosamine, ribosamine, ribulosamine and xylulosamine and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the monosaccharide(s) a) are chosen from C 7 monosaccharides bearing amine group(s): heptosamines such as aldoheptosamines and ketoheptosamines and also the organic or mineral acid salts thereof, and also the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the monosaccharide(s) a) are chosen from C 6 monosaccharides: hexosamines and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the monosaccharide(s) a) of the invention are chosen from the hexosamines of formula (A3) below and also the salts thereof with an organic or mineral acid such as hydrochloric acid, and also the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates:
  • R a , R b , R d , R e and R f which may be identical or different, represent (1) a hydroxyl group, (2) a (Ci-C 4 )alkoxy group, the alkyl chain of which may be optionally substituted notably with one or more hydroxyl groups, (3) a carboxyl group, or (4) a group NR I R 2 with Ri and R 2 , which may be identical or different, representing i) a hydrogen atom, ii) a (Ci-C 6 )alkyl group that is optionally substituted, preferably with one or more hydroxyl or NH 2 groups, iii) an aryl group such as phenyl, iv) an aryl(Ci-C 4 )alkyl group such as benzyl, v) a (hetero)cyclo(C5-C 7 )alkyl group such as cyclohexyl, morpholinyl, piperazinyl,
  • At least one of the radicals R a , R b , R d , R e and R f represents a group NR I R 2 and preferably at least one of the radicals R a , R b , R d , R e and R f represents a group NR I R 2 and the radicals other than NR I R 2 denote a hydroxyl group.
  • Ri and R 2 are chosen from hydrogen and -C(0)-R’i in which R’i is as defined previously; and more preferentially Ri and R 2 represent i) a hydrogen atom or ii) -C(0)-R’ i, with R’ i representing a (Ci-C 4 )alkyl group such as methyl.
  • R b represents a group NR I R 2 such as NH 2 or -N(H)-C(0)-R’ i with R’i representing a (Ci-C 4 )alkyl group such as methyl, and more preferentially NH 2 , and R a , R d , R e and R f , represent a hydroxyl group.
  • the monosaccharide(s) a) are chosen from the hexosamines of formula (A3) of D configuration, also known as D-glucopyrans, and more preferentially from the hexosamines of formula (A3) of b (beta) anomeric configuration.
  • the monosaccharide(s) a) of the invention are chosen from the hexosamines of formula (A3’) below and also the salts thereof with an organic or mineral acid such as hydrochloric acid, and also the a or b anomers thereof, the optical isomers thereof of L or D, preferably D, configuration, and the solvates thereof such as hydrates, and mixtures thereof:
  • R a , R b , R d , R e and R f are as defined previously for (A3).
  • the monosaccharide(s) a) are advantageously chosen from hexosamines, preferably from aldohexosamines and ketohexosamines, and mixtures thereof, more preferentially from glucosamine, galactosamine, allosamine, altrosamine, mannosamine, gulosamine, idosamine and talosamine, and mixtures thereof.
  • the monosaccharide(s) a) are chosen from glucosamine and galactosamine, and also the salts thereof with an organic or mineral acid such as hydrochloric acid, the a or b anomers thereof, the optical isomers thereof of L or D configuration and the solvates thereof such as hydrates, and mixtures thereof; more preferentially, the monosaccharide a) is glucosamine, better still glucosamine of D configuration, and even better still glucosamine salified with a mineral acid such as hydrochloric acid.
  • the dyeing process according to the present invention also comprises a step consisting in applying to keratin fibres b) one or more polysaccharides bearing amine group(s), and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration and the solvates thereof such as hydrates, also referred to as ingredients b).
  • the polysaccharide(s) bearing amine group(s) b) have an average molecular weight (MW) of less than or equal to 400 kDa and more preferentially less than 200 kDa.
  • MW average molecular weight
  • the polysaccharide(s) bearing amine group(s) b) have a low average molecular weight MW, i.e. they have a molecular weight of less than 100 kDa, preferably less than 40 kDa; more preferentially, they have an average MW of between 1 kDa and 30 kDa and better still between 3 kDa and 28 kDa.
  • the polysaccharide(s) bearing amine group(s) b) are preferably of natural animal or plant origin, or else are derived from synthesis, semisynthesis or biosynthesis.
  • the polysaccharide(s) bearing amine group(s) b) are chosen from polysaccharides bearing C5-C7 saccharide units bearing amine group(s), and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates, and mixtures thereof. More particularly, the polysaccharide(s) bearing amine group(s) b) bear C 6 saccharide unit bearing amine group(s), these polysaccharides bearing amine group(s) are then referred to as polyhexosamines.
  • the saccharide units of the polysaccharide bearing amine group(s) b) are of b (beta) anomeric configuration and/or D configuration.
  • the saccharide units of the polysaccharide bearing amine group(s) b) are connected together between the atoms of carbon 1 of one saccharide unit and of carbon 4 of the other saccharide unit, denoted (l 4).
  • the polysaccharide(s) bearing amine group(s) are preferably chosen from polysaccharides bearing a saccharide unit of formula (B) below, and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates, and mixtures thereof.
  • - n is an integer greater than or equal to 2, preferably between 3 and 3000, more preferentially between 5 and 2500, and better still between 10 and 2300;
  • R a , R b and R c which may be identical or different for each saccharide unit, represent (1) a hydroxyl group, (2) a (Ci-C 4 )alkoxy group, the alkyl chain of which may be optionally substituted notably with one or more hydroxyl and/or carboxyl groups, (3) a carboxyl group, or (4) a group NR I R 2 with Ri and R 2 , which may be identical or different, representing i) a hydrogen atom, ii) a (Ci-C 6 )alkyl group that is optionally substituted, preferably with one or more hydroxyl or NH 2 groups, iii) an aryl group such as phenyl, iv) an aryl(Ci-C 4 )alkyl group such as benzyl, v) a (hetero)cyclo(C5-C 7 )alkyl group such as cyclohexyl, morpholinyl, piperaziny
  • At least one of the radicals R a , R b or R c of at least one saccharide unit represents a group NR I R 2 and that at least one of the groups NR I R 2 of at least one saccharide unit represents an NH 2 group.
  • Ri and R 2 are chosen from a hydrogen atom and -C(0)-R’i in which R’i is as defined previously; and more preferentially Ri and R 2 represent i) a hydrogen atom or ii) -C(0)-R’ i, with R’ i representing a (Ci-C 4 )alkyl group such as methyl.
  • R a of at least one saccharide unit represents a group NR I R 2 with Ri which represents a hydrogen atom and R 2 is chosen from i) a hydrogen atom or ii) a group -C(0)-R’ i , and R b and R c represent a hydroxyl group, it being understood that at least one of the groups NR I R 2 of at least one saccharide unit represents an NH 2 group.
  • polysaccharide(s) bearing amine group(s) b) are chosen from polysaccharides bearing saccharide units of formula (Bl) below, and also the organic or mineral acid salts thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates, and mixtures thereof:
  • - R’ represents a hydrogen atom or a (Ci-C 4 )alkylcarbonyl group such as acetyl
  • - R represents a hydrogen atom or a (Ci-C 4 )alkyl group optionally substituted with a carboxyl group such as -CH(C0 2 H)-CH 3 ;
  • - n is an integer greater than or equal to 2, preferably between 3 and 3000, more preferentially between 5 and 2500, and better still between 10 and 2300;
  • At least one saccharide unit bears an NH 2 amino group and at least one other saccharide unit bears at least one N(H)-R' group with R' representing a (Ci-C 4 )alkylcarbonyl group such as acetyl CH 3 -C(0)-.
  • the saccharide units of formula (B) or (Bl) are of D configuration, also referred to as D-glucopyran.
  • saccharide units of formula (B) or (Bl) are of b (beta) anomeric configuration.
  • the polysaccharides b) are chosen from the polysaccharides bearing a saccharide unit of formula (B2) below and also the organic or mineral acid salts thereof, and the solvates thereof such as hydrates, and mixtures thereof:
  • R a , R b and R c are as defined for (B) previously; and the radicals R a , R b and R c of each saccharide unit may be identical or different; and
  • - n is an integer greater than or equal to 2, preferably between 3 and 3000, more preferentially between 5 and 2500, and better still between 10 and 2300;
  • At least one of the radicals R a , R b or R c of at least one saccharide unit represents a group NR I R 2 , with Ri and R 2 as defined previously for (B), and that at least one of the groups NR I R 2 of at least one saccharide unit represents an NH 2 group; preferably, at least one saccharide unit bears a group R a representing a group -N(H)-R' with R' representing a (Ci-C 4 )alkylcarbonyl group such as acetyl CH 3 -C(0)-.
  • the polysaccharide(s) bearing amine group(s) b) are chosen from chitin and chitosan, and derivatives thereof, and more preferentially chitosan. More particularly, the polysaccharide(s) bearing amine group(s) b) are chosen from polysaccharides bearing a saccharide unit of formula (B3) below, and also the organic or mineral acid salts thereof, and the solvates thereof such as hydrates, and mixtures thereof:
  • - n is an integer greater than or equal to 2, preferably between 3 and 3000, more preferentially between 5 and 2500, and better still between 10 and 2300;
  • At least one saccharide unit bears an NH 2 amino group and at least one other saccharide unit bears a group N(H)-R' with R' representing a (Ci- C 4 )alkylcarbonyl group such as acetyl CH 3 -C(0)-.
  • polysaccharide(s) bearing amine group(s) b) are chosen from the chitosans of formula (B4) below, and also the organic or mineral acid salts thereof, and the solvates thereof such as hydrates, and mixtures thereof:
  • - n is an integer greater than or equal to 2, preferably between 3 and 3000, more preferentially between 5 and 2500, and better still between 10 and 2300;
  • - p is greater than 0 and ranges up to 0.5, preferably from 0.05 to 0.3, and better still from 0.1 to 0.20 such as 0.15 with m+p being equal to 1;
  • At least one saccharide unit bears an amino group NH 2 and at least one other saccharide unit bears a group N(H)-R'i with R'i representing a (Ci-C 4 )alkylcarbonyl group such as acetyl CH 3 -C(0)-.
  • the polysaccharide(s) bearing amine group(s) b) are salified, or in salified form, using one or more organic or mineral acids, and preferably using one or more organic acids.
  • organic or mineral acid(s) that may be used correspond to the mineral and organic acids described previously in the section "organic or mineral acid salt”.
  • the polysaccharide(s) bearing amine group(s) b) are salified using one or more organic acid(s) chosen from:
  • R represents a (hetero)aryl radical such as phenyl, a (hetero)aryl(Ci-C 4 )alkyl radical such as benzyl, a (Ci-C3o)alkyl radical or an unsaturated C2-C30 radical (i.e.
  • alkyl or unsaturated C2-C30 radicals being optionally interrupted and/or optionally substituted preferably with one or more hydroxyl groups and not substituted with one or more amino radicals;
  • R preferably denoting a (Ci-C6)alkyl group optionally interrupted and/or optionally substituted with 1, 2 or 3 hydroxyl groups; preferably, R represents a (Ci-C 4 )alkyl group such as methyl or ethyl;
  • A represents a saturated or unsaturated, cyclic or non-cyclic, aromatic or non-aromatic polyvalent hydrocarbon-based group comprising from 1 to 30 carbon atoms, optionally interrupted with one or more heteroatoms such as oxygen and/or optionally substituted notably with one or more hydroxyl groups and t represents an integer between 1 and 5 inclusive; preferably, A represents a divalent (Ci-C6)alkylene group optionally substituted notably with one or more hydroxyl groups and not substituted with at least t amino radicals, and t is equal to 1, 2 or 3; and
  • the monocarboxylic organic acids of formula (I) are chosen from acetic acid, glycolic acid, lactic acid, and mixtures thereof, and more preferentially from acetic acid, lactic acid, and mixtures thereof.
  • polycarboxylic acids of formula (II) are chosen from tartaric acid, succinic acid, fumaric acid, maleic acid, citric acid, and mixtures thereof.
  • the amino acids including more carboxylic acid radicals than amino groups are chosen from gamma-carboxyglutamic acid, aspartic acid, glutamic acid, and mixtures thereof, and more preferentially gamma-carboxyglutamic acid.
  • the organic acid(s) that may be used are chosen from acetic acid, glycolic acid, lactic acid, tartaric acid, succinic acid, fumaric acid, maleic acid, citric acid, gamma-carboxyglutamic acid, aspartic acid, glutamic acid, and mixtures thereof, and preferably, the organic acid is lactic acid.
  • the polysaccharide(s) bearing amine group(s) b) are chosen from chitosans, salified using organic acid, preferentially using monocarboxylic acid of formula (I) as defined previously or polycarboxylic acid of formula (II) as defined previously, even more preferentially salified using carboxylic acid of formula (I) such as lactic acid.
  • the polysaccharide(s) bearing amine group(s) b) denote a mixture of polysaccharide(s) bearing amine group(s), one of which is a chitosan or the organic or mineral acid salts thereof, preferably the salts thereof with an organic acid such as lactic acid, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the polysaccharide(s) bearing amine group(s) b) denote a single polysaccharide bearing amine group(s), in particular a mixture of chitosan or the organic or mineral acid salts thereof or more particularly the organic acid salts thereof such as the lactic acid salt thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the polysaccharide(s) bearing amine group(s) b) denote a single polysaccharide bearing amine group(s), in particular a chitosan or the organic or mineral acid salts thereof or more particularly the organic acid salts thereof such as the lactic acid salt thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the dyestuffs in particular a chitosan or the organic or mineral acid salts thereof or more particularly the organic acid salts thereof such as the lactic acid salt thereof, the a or b anomers thereof, the optical isomers thereof of L or D configuration, and the solvates thereof such as hydrates.
  • the dyeing process according to the present invention also comprises a step consisting in applying to the keratin fibres c) one or more dyestuffs chosen from pigments and direct dyes, and mixtures thereof, also referred to as ingredients c).
  • the dyestuff(s) are chosen from pigments.
  • pigment is understood to denote a white or coloured solid particle which is naturally insoluble in the hydrophilic and lipophilic liquid phases usually employed in cosmetics or which is rendered insoluble by formulation in the form of a lake, where appropriate. More particularly, the pigment has little or no solubility in aqueous-alcoholic media.
  • Pigments that may be mentioned include organic and inorganic pigments such as those defined and described in Ullmann's Encyclopedia of Industrial Chemistry "Pigment organics", 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007. a20 371 and ibid, "Pigments, Inorganic, 1. General” 2009 Wiley-VCH Verlag GmbH & Co. KGaA,
  • They may in particular be monoazo pigments, including b-naphthols, monoazopyrrolone pigments or benzimidazolone pigments; diazo pigments, such as diazodiarylide pigments and bis(N-acetoacetarylide) pigments, or triazo or tetraazo pigments.
  • azo metal complex pigments Mention may also be made of azo metal complex pigments.
  • pigments are also advantageous, namely isoindolinone and isoindoline pigments, phthalocyanine pigments; quinacridone pigments; perinone pigments; perylene pigments; anthraquinone pigments such as hydroxyanthraquinone pigments; aminoanthraquinone pigments including acylaminoanthraquinones and azo anthraquinone pigments; heterocyclic anthraquinones; polycarboxylic anthraquinone pigments, pyranthrone pigments; anthranthrone pigments; diketopyrrolopyrrole (DPP) pigments; thioindigo pigments; dioxazine pigments; triphenylmethane pigments; quinophthalone pigments; and fluorescent pigments.
  • isoindolinone and isoindoline pigments phthalocyanine pigments
  • quinacridone pigments such as hydroxyanthraquinone pigments;
  • the dyes comprise one or more solubilizing groups such as -SO 3 H or -COOH
  • these dyes are made insoluble and consequently pigments by formation of a lake, i.e. by salification (e.g. Na, Ca, St, Ba, etc.) and divided mainly into b-naphthol and 2-hydroxy-3-naphthoic acid pigments "(BON) pigment lakes”.
  • the pigment may be at least partly organic.
  • the pigment is an organic pigment. According to another embodiment of the invention, the pigment is a mineral pigment.
  • the microcapsules according to the invention comprise not more than 80% by weight of pigment relative to the weight of the polymer matrix.
  • they may comprise from 0.5% to 75% by weight, for example from 1% to 70% by weight, notably from 20% to 65% by weight or even from 30% to 60% by weight of pigment relative to the weight of the polymer matrix.
  • the degree of encapsulation depends on the desired modification of the shade and may thus vary significantly according to the effect that it is desired to obtain.
  • pigments that may be used in the present invention, mention may be made of carbon black, titanium oxide, chromium oxide, pigments of D&C or FD&C type and lakes thereof, and especially those known under the names D&C Blue No. 4, D&C Brown No. 1, FD&C Green No. 3, D&C Green No. 5, D&C Green No. 6, FD&C Green No. 8, 20 D&C Orange No. 4, D&C Orange No. 5, D&C Orange No. 10, D&C Orange No. 11, FD&C Red No. 4, D&C Red No. 6, D&C Red No. 7, D&C Red No. 17, D&C Red No. 21, D&C Red No. 22, D&C Red No. 27, D&C Red No. 28, D&C Red No.
  • lakes examples include lakes based on barium, strontium, calcium or aluminium, or alternatively diketopyrrolopyrroles.
  • pigments with an optical effect such as particles including a natural or synthetic organic or mineral substrate, for example glass, acrylic resins, polyester, polyurethane, polyethylene terephthalate, ceramics or aluminas, said substrate being optionally covered with metal substances, for instance aluminium, gold, silver, platinum, copper or bronze, or with metal oxides, for instance titanium dioxide, iron oxide or chromium oxide.
  • a natural or synthetic organic or mineral substrate for example glass, acrylic resins, polyester, polyurethane, polyethylene terephthalate, ceramics or aluminas
  • metal substances for instance aluminium, gold, silver, platinum, copper or bronze, or with metal oxides, for instance titanium dioxide, iron oxide or chromium oxide.
  • They may also be nacres.
  • nacres means iridescent particles, which are notably produced by certain molluscs in their shell, or alternatively which are synthesized.
  • the nacreous pigments may be chosen from mica coated with titanium or with bismuth oxychloride, titanium mica coated with iron oxides, titanium mica coated notably with ferric blue or with chromium oxide, titanium mica coated with an organic pigment of the abovementioned type, and also nacreous pigments based on bismuth oxychloride. Use may also be made of interference pigments, notably liquid- crystal or multilayer pigments.
  • pigments having a structure may be, for example, of sericite/brown iron oxide/titanium dioxide/silica type.
  • pigments having a structure may be, for example, of silica microsphere type containing iron oxide.
  • the pigments in accordance with the invention may be in the form of pigment powder or paste. They may be coated or uncoated.
  • the pigments in accordance with the invention may be chosen, for example, from white or coloured pigments, lakes, pigments with special effects such as nacres or flakes, and mixtures thereof.
  • white or coloured mineral pigments examples include zirconium oxide or cerium oxide, chromium oxides, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • white or coloured organic pigments examples include nitroso, nitro, azo, xanthene, quinoline, anthraquinone and phthalocyanine compounds, compounds of metallic complex type, and isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds.
  • the white or coloured organic pigments may be chosen from carmine, carbon blacks such as Black 2, aniline black, azo yellow, quinacridone, phthalocyanine blue, sorghum red, the blue pigments codified in the Color Index under the references Cl 42090, 69800, 69825, 73000, 74100, 74160, the yellow pigments codified in the Color Index under the references Cl 11680, 11710, 15985, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references Cl 61565, 61570, 74260, the orange pigments codified in the Color Index under the references Cl 11725, 15510, 45370, 71105, the red pigments codified in the Color Index under the references Cl 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880,
  • carbon blacks such as Black 2 or lakes such as D&C Red 7.
  • pigment pastes of organic pigments such as the products sold by the company Hoechst under the names:
  • the pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1 184 426. These composite pigments may be composed notably of particles including:
  • the term “lake” refers to dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.
  • the inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate, calcium aluminium borosilicate and aluminium.
  • pigments with special effects refers to pigments that generally create a coloured appearance (characterized by a certain shade, a certain vivacity and a certain level of luminance) that is non-uniform and that changes as a function of the conditions of observation (light, temperature, angles of observation, etc.). They thus contrast with white or coloured pigments that afford a standard uniform opaque, semi-transparent or transparent shade.
  • pigments with special effects include white nacreous pigments such as mica coated with titanium or with bismuth oxychloride, coloured nacreous pigments such as mica coated with titanium and with iron oxides, mica coated with titanium and especially with ferric blue or with chromium oxide, mica coated with titanium and with an organic pigment as defined above, and also nacreous pigments based on bismuth oxychloride.
  • Pigments with an interference effect which are not attached to a substrate, such as liquid crystals (Helicones HC from Wacker) or interference holographic glitter flakes (Geometric Pigments or Spectra f/x from Spectratek).
  • Pigments with special effects also comprise fluorescent pigments, whether these are substances that are fluorescent in daylight or that produce an ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, sold, for example, by the company Quantum Dots Corporation.
  • Quantum dots are luminescent semiconductive nanoparticles that are capable of emitting, under light excitation, radiation with a wavelength of between 400 nm and 700 nm. These nanoparticles are known from the literature. In particular, they may be manufactured according to the processes described, for example, in US 6 225 198 or US 5 990 479, in the publications cited therein and also in the following publications: Dabboussi B.O. et a ,“(CdSe)ZnS core-shell quantum dots: synthesis and characterisation of a size series of highly luminescent nanocrystallites”, Journal of Physical Chemistry B, vol.
  • the pigments in accordance with the invention are preferably coloured pigments.
  • the size of a pigment other than the nacres in solution is generally between
  • 10 nm and 10 pm preferably between 50 nm and 5 pm and even more preferentially between 100 nm and 3 pm.
  • the size of a nacre in solution is generally between 1 and 200 pm, preferably between 1 and 80 pm and even more preferentially between 1 and 50 pm.
  • mineral pigments examples that may be mentioned include titanium dioxide (rutile or anatase) optionally surface-treated and codified in the Color Index under the reference Cl 77891; black, yellow, red and brown iron oxides, codified under the references Cl 77499, 77492 and 77491; manganese violet (Cl 77742); ultramarine blue (Cl 77007); hydrated chromium oxide (Cl 77289); ferric blue (077510).
  • organic pigments that may be mentioned, for example, are the pigment Yellow 3 sold notably under the trade name Jaune Covanor W 1603 by the company Wackherr (Cl 17710), D & C Red No. 19 (Cl 45170), D & C Red No. 9 (Cl 15585), D & C Red No. 21 (Cl 45380), D & C Orange No. 4 (Cl 15510), D & C Orange No. 5 (Cl 45370), D & C Red No. 27 (Cl 45410), D & C Red No. 13 (Cl 15630), D & C Red No. 7 (Cl 15850-1), D & C Red No. 6 (Cl 15850-2), D & C Yellow No.
  • nacreous pigments which may be chosen notably from white nacreous pigments such as mica coated with titanium oxide or bismuth oxide; coloured nacreous pigments such as titanium mica with iron oxides, titanium mica with ferric blue or with chromium oxide, titanium mica with an organic pigment of the abovementioned type, and also those based on bismuth oxychloride.
  • Pigment pastes of organic pigment are used more particularly, such as the products sold by the company Hoechst under the names:
  • the dyestuff(s) are advantageously chosen from pigments, preferably from white organic pigments, coloured organic pigments, and mixtures thereof, and more preferentially carbon blacks, such as Black 2, lakes, such as D&C Red 7, and mixtures thereof.
  • the dyestuff(s) are chosen from direct dyes.
  • direct dye means natural and/or synthetic dyes, other than oxidation dyes. These are dyes that will spread superficially on the fibre.
  • They may be ionic or nonionic, preferably cationic or nonionic, either as sole dyes.
  • direct dyes are chosen, for example, from neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, tetraazapentamethine dyes, neutral, acidic or cationic quinone and in particular anthraquinone dyes, azine direct dyes, triarylmethane direct dyes, azomethine direct dyes and natural direct dyes.
  • Suitable direct dyes include azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryl dyes; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes, and natural direct dyes, alone or as mixtures.
  • the direct dye(s) contain at least one quaternized cationic chromophore or at least one chromophore bearing a quaternized or quaternizable cationic group.
  • the direct dyes comprise at least one quatemized cationic chromophore.
  • acridines such as azacarbocyanines, diazacarbocyanines, diazahemicyanines, hemicyanines or tetraazacarbocyanines; diazines; diketopyrrolopyrroles; dioxazines; diphenylamines; diphenylmethanes; di
  • cationic azo dyes mention may be made particularly of those resulting from the cationic dyes described in Kirk-Othmer’s Encyclopedia of Chemical Technology,“Dyes, Azo”, J. Wiley & Sons, updated on 19 April 2010.
  • the direct dye(s) are chosen from cationic dyes known as "basic dyes".
  • cationic quinone dyes those mentioned in the abovementioned Colour Index International are suitable and, among these, mention may be made, inter alia, of the following dyes:
  • azine dyes that are suitable for use, mention may be made of those listed in the Colour Index International, for example the following dyes:
  • the cationic direct dyes are chosen from those resulting from dyes of azo and hydrazono type.
  • the direct dyes are cationic azo dyes, described in EP 850 636, FR 2 788 433, EP 920 856, WO 99/48465, FR 2 757 385, EP 850 637, EP 918 053, 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 738 585, DE 2 527 638, FR 2 275 462, GB 1974-27645, Acta Histochem
  • the cationic direct dye(s) comprise(s) a quaternary ammonium group; more preferentially, the cationic charge is endocyclic.
  • cationic radicals are, for example, a cationic radical:
  • an endocyclic charge such as comprising a cationic heteroaryl group chosen from: acridinium, benzimidazolium, benzobistriazolium, benzopyrazolium, benzopyridazinium, benzoquinolium, benzothiazolium, benzotriazolium, benzoxazolium, bipyridinium, bistetrazolium, dihydrothiazolium, imidazopyridinium, imidazolium, indolium, isoquinolium, naphthoimidazolium, naphthoxazolium, naphthopyrazolium, oxadiazolium, oxazolium, oxazolopyridinium, oxonium, phenazinium, phenooxazolium, pyrazinium, pyrazolium, pyrazoyltriazolium, pyridinium, pyridinoimidazolium, pyrrolium, pyry
  • Het + represents a cationic heteroaryl radical, preferentially bearing an endocyclic cationic charge, such as imidazolium, indolium or pyridinium, optionally substituted, preferentially with at least one (Ci-C 8 ) alkyl group such as methyl;
  • Ar + represents an aryl radical, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferentially ammonium, particularly tri(Ci- Cg)alkyl ammonium, such as trimethylammonium;
  • Ar represents an aryl group, notably phenyl, which is optionally substituted, preferentially with one or more electron-donating groups such as i) optionally substituted (Ci-Cg)alkyl, ii) optionally substituted (Ci-Cg)alkoxy, iii) (di)(Ci- Cg)(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group, iv) aryl(Ci-Cg)alkylamino, v) optionally substituted N-(Ci-Cg)alkyl-N- aryl(Ci-Cg)alkylamino or alternatively Ar represents a julolidine group;
  • Ar represents an optionally substituted (hetero)aryl group, such as phenyl or pyrazolyl, which are optionally substituted, preferentially by one or more (Ci- Cg)alkyl, hydroxyl, (di)(Ci-Cg)(alkyl)amino, (Ci-Cg)alkoxy or phenyl groups;
  • R a and R b which may be identical or different, represent a hydrogen atom or a (Ci-Cg)alkyl group, which is optionally substituted, preferentially with a hydroxyl group;
  • R a substituent with a substituent of Het + and/or R b with a substituent of Ar form, together with the atoms that bear them, a (hetero)cyclo alkyl; in particular, R a and R b represent a hydrogen atom or a (Ci-C 4 )alkyl group optionally substituted with a hydroxyl group;
  • Q represents an organic or mineral anionic counterion, such as a halide or an alkyl sulfate.
  • R 1 represents a (Ci-C 4 )alkyl group such as methyl
  • R and R which may be identical or different, represent a hydrogen atom or a (Ci-C 4 )alkyl group, such as methyl;
  • R 4 represents a hydrogen atom or an electron-donating group such as optionally substituted (Ci-Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, or (di)(Ci- C 8 )(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group; particularly, R 4 is a hydrogen atom,
  • - Z represents a CH group or a nitrogen atom, preferentially CH
  • - Q is an anionic counterion as defined previously, in particular a halide, such as chloride, or an alkyl sulfate, such as methyl sulfate or mesityl.
  • the dyes of formulae (III- 1 ) and (V-l) are chosen from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or derivatives thereof:
  • a halide such as chloride
  • an alkyl sulfate such as methyl sulfate or mesityl.
  • the direct dyes are fluorescent, i.e. they contain at least one fluorescent chromophore as defined previously.
  • Fluorescent dyes that may be mentioned include the radicals resulting from the following dyes: acridines, acridones, benzanthrones, benzimidazoles, benzimidazolones, benzindoles, benzoxazoles, benzopyrans, benzothiazoles, coumarins, difluoro ⁇ 2-[(2H-pyrrol-2-ylidene-kN)methyl]-lH-pyrrolato-kN ⁇ borons (BODIPY ® ), diketopyrrolopyrroles, fluorindines, (poly)methines (in particular cyanines and styryls/hemicyanines), naphthalimides, naphthanilides, naphthylamines (such as dansyls), oxadiazoles, oxa
  • the fluorescent dye(s) are cationic and comprise at least one quaternary ammonium radical, such as those of formula (VII) below:
  • W + represents a cationic heterocyclic or heteroaryl group, particularly comprising a quaternary ammonium optionally substituted with one or more (Ci- Cg)alkyl groups, optionally substituted notably with one or more hydroxyl groups;
  • ⁇ 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 (Ci-Cg)alkyl, preferably of Ci-C 4 such as methyl; iii) one or more hydroxyl groups; iv) one or more (Ci-Cg)alkoxy groups such as methoxy; v) one or more hydroxy(Ci-Cg)alkyl groups such as hydroxyethyl, vi) one or more amino groups or (di)(C i -Cgjalkylamino, preferably with the C 1 -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 heterocyclo alkyl groups such as piperazinyl, piperidyl
  • m represents an integer between 1 and 4 inclusive, and in particular m has the value 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 (Ci-Cg)alkyl group, preferentially of Ci-C 4 , or alternatively R c contiguous with W + and/or R contiguous with Ar form, with the atoms that bear them, a (hetero)cycloalkyl; particularly, R c is contiguous with W + and they form a (hetero)cycloalkyl such as cyclohexyl;
  • Q is an organic or mineral anionic counterion as defined previously.
  • a subject of the present invention is also an aqueous composition (C) at acidic pH comprising:
  • ingredients a), b) and c) as defined previously are applied sequentially and are preferably included in three separate compositions (ca), (cb) and (cc).
  • composition (ca) comprises a) one or more monosaccharides as defined previously
  • composition (cb) comprises b) one or more polysaccharide(s) bearing amine group(s), in salified or non-salified form, as defined previously, and optionally c) one more mineral or organic acid(s)
  • composition (cc) comprises one or more dyestuffs as defined previously.
  • compositions (C) and (C) are examples of The mineral or organic acid(s) that may be used in compositions (C) and
  • the content of the monosaccharide(s), present in compositions (C) and (ca), preferably ranges from 0.01% to 20% by weight, more preferentially from 0.05% to 10% by weight and better still from 0.1% to 5% by weight, relative to the total weight of the composition comprising same.
  • compositions (C) and (cb) preferably ranges from 0.01% to 20% by weight, more preferentially from 0.05% to 10% by weight and even better still from 0.1% to 5% by weight, relative to the total weight of the composition comprising same.
  • the weight ratio of the content of monosaccharide(s) and the amount of polysaccharide(s) bearing amine group(s), present in composition (C) of the invention preferably ranges from 0.5 to 10.
  • compositions (C) and composition(s) (ca), (cb) and/or (cc) are cosmetic compositions, i.e. they contain a physiologically acceptable medium, i.e. a medium that is compatible with human keratin materials such as the skin (of the body, face, area around the eyes, or the scalp), the hair, the eyelashes, the eyebrows, bodily hair, the nails or the lips.
  • a physiologically acceptable medium i.e. a medium that is compatible with human keratin materials such as the skin (of the body, face, area around the eyes, or the scalp), the hair, the eyelashes, the eyebrows, bodily hair, the nails or the lips.
  • (cc) is advantageously an aqueous medium. It may be constituted, for example, of water or of a mixture of water and of at least one cosmetically acceptable organic solvent.
  • organic solvents examples include C 2 -C 4 lower alcohols, such as ethanol and isopropanol; polyols, notably those containing from 2 to 6 carbon atoms, for instance glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol; polyol ethers, for instance 2-butoxyethanol, propylene glycol monomethyl ether and diethylene glycol monomethyl ether or monoethyl ether; and mixtures thereof.
  • C 2 -C 4 lower alcohols such as ethanol and isopropanol
  • polyols notably those containing from 2 to 6 carbon atoms, for instance glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol
  • polyol ethers for instance 2-butoxyethanol, propylene glycol monomethyl ether and diethylene
  • the cosmetic composition(s) (C), (ca), (cb) and/or (cc) each comprise from 50% to 99.8% by weight of water, relative to the weight of each composition.
  • composition(s) (C), (ca), (cb) and/or (cc) of the invention may be adjusted with an organic or mineral acid, or with an alkaline agent chosen from mineral, organic or hybrid alkaline agents or mixtures thereof.
  • the pH values may be adjusted with d) one or more organic or mineral acids as defined previously in the section“Organic or mineral acid salt”.
  • composition (ca) which comprises a) one or more monosaccharides as defined previously, and notably glucose or xylose, is at an acidic pH, i.e. less than 7, in particular less than or equal to 6. More particularly, the pH of composition (ca) is between 2 and 6, preferentially between 2.5 and 5.5 and more preferentially between 3.5 and 5, such as 4.5.
  • the monosaccharide(s) a), present in composition (ca) are in the presence of one or more mineral acid(s), more particularly hydrochloric acid.
  • composition (cb) which comprises b) one or more polysaccharide(s) bearing amine group (s) as defined previously, and in particular a polysaccharide bearing saccharide units of formula (B), (Bl), (B2), (B3) or (B4) as defined previously, such as chitosan, is at an acidic pH, i.e. less than 7, and in particular less than or equal to 6. More particularly, the pH of composition (cb) is between 2 and 6, preferentially between 2.5 and 5.5 and more preferentially between 3.5 and 5, such as 4.5.
  • the polysaccharide(s) bearing amine group(s) b), present in composition (cb), are in the presence of one or more organic acid(s), preferentially chosen from the monocarboxylic acids of formula (I) or the polycarboxylic acids of formula (II) as defined previously, and even more preferentially from the carboxylic acids of formula (I), such as lactic acid.
  • organic acid(s) preferentially chosen from the monocarboxylic acids of formula (I) or the polycarboxylic acids of formula (II) as defined previously, and even more preferentially from the carboxylic acids of formula (I), such as lactic acid.
  • composition (C) comprises:
  • the pH of said composition (C) is acidic, i.e. less than 7, preferably less than or equal to 6, more preferentially between 2 and 6, even better still between 2.5 and 5.5 and even more preferentially between 3.5 and 5, such as 4.5.
  • composition (C) comprises:
  • polysaccharide(s) bearing amine group(s) as defined previously, preferably a polysaccharide bearing saccharide units of formula (B), (Bl), (B2), (B3) or (B4) as defined previously, more preferentially chitosan, in the presence of one or more mineral acid(s), preferably lactic acid,
  • the pH of said composition (C) is acidic, i.e. less than 7, preferably less than or equal to 6, more preferentially between 2 and 6, even better still between 2.5 and 5.5 and even more preferentially between 3.5 and 5, such as 4.5.
  • composition (C) comprises:
  • composition (C) optionally one or more mineral or organic acids;
  • the pH of said composition (C) is acidic, i.e. less than 7, preferably less than or equal to 6, more preferentially between 2 and 6, even better still between 2.5 and 5.5 and even more preferentially between 3.5 and 5, such as 4.5.
  • composition (C) comprises:
  • polysaccharide(s) bearing amine group(s) as defined previously, preferably a polysaccharide bearing saccharide units of formula (B), (Bl), (B2), (B3) or (B4) as defined previously, more preferentially chitosan, and even better still chitosan with an average molecular weight of less than or equal to 400 kDa, in the absence of organic or mineral acid(s), and
  • one or more mineral or organic acids said acid c) preferably being chosen from hydrochloric acid, the organic monocarboxylic acids of formula (I) as defined previously, the polycarboxylic acids of formula (II) as defined previously, and more preferentially from hydrochloric acid, lactic acid, citric acid, fumaric and maleic acid, and mixtures thereof;
  • the pH of said composition (C) is acidic, i.e. less than 7, preferably less than or equal to 6, more preferentially between 2 and 6, even better still between 2.5 and 5.5 and even more preferentially between 3.5 and 5, such as 4.5.
  • composition (C) comprises one or more monosaccharides a) chosen from monosaccharides bearing an amine group as defined previously.
  • compositions (C), (ca), (cb) and/or (cc) may be adjusted with one or more mineral alkaline agents which are preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates, sodium hydroxide or potassium hydroxide, or mixtures thereof.
  • mineral alkaline agents which are preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates, sodium hydroxide or potassium hydroxide, or mixtures thereof.
  • the pH values may also be adjusted with one or more organic alkaline agents which are organic amines, i.e. they contain at least one substituted or unsubstituted amino group.
  • organic alkaline agent(s) are more preferentially chosen from organic amines with a pK b at 25°C of less than 12, preferably of less than 10 and even more advantageously of less than 6. It should be noted that it is the pK b corresponding to the function of highest basicity.
  • the pH values may also be adjusted with one or more hybrid compounds.
  • 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 (VIII) below:
  • Ci-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 1 and R u which may be identical or different, represent a hydrogen atom, a Ci-C 6 alkyl radical, a Ci-C 6 hydroxyalkyl radical or a Ci-C 6 aminoalkyl radical.
  • composition (C) of the invention may be salified or non-salified.
  • composition (C) corresponds to composition (C) at acidic pH and comprises:
  • composition (C) corresponds to composition (C”) at acidic pH and comprises:
  • compositions (C) and/or (cc) may optionally also comprise one or more additional direct dyes other than the direct dyes mentioned previously.
  • 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 other than pigments and/or one or more direct dyes that are sparingly soluble or insoluble in aqueous-alcoholic solvents, 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.
  • 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 other than pigments and/or one or
  • Compositions (C), (ca), (cb) and/or (cc) may also optionally comprise one or more additives other than the compounds of the invention and among which mention may be made of cationic, anionic, nonionic, amphoteric or zwitterionic surfactants, cationic, anionic, nonionic or amphoteric polymers, or mixtures thereof, other than the polysaccharides of the invention, antidandruff agents, anti-seborrhoea agents, agents for preventing hair loss and/or for promoting hair regrowth, vitamins and provitamins including panthenol, sunscreens, sequestrants, plasticizers, solubilizers, silicones, oils, mineral or organic thickeners, notably polymeric thickeners, antioxidants, hydroxy acids, fragrances, preserving agents and ceramides.
  • additives other than the compounds of the invention and among which mention may be made of cationic, anionic, nonionic, amphoteric or zwitterionic surfactants
  • compositions according to the invention are not, or are not substantially, adversely affected by the envisaged addition(s).
  • the above additives may generally be present in an amount, for each of them, of between 0 and 20% by weight relative to the total weight of the composition comprising same.
  • the process for dyeing keratin fibres, in particular human keratin fibres such as the hair, according to the present invention comprises:
  • steps (i), (ii) and (iii) may be performed simultaneously or sequentially, before being followed by
  • the dyeing process according to the present invention may optionally also comprise a step of drying the keratin fibres.
  • this step of drying the keratin fibres follows steps (i), (ii) and (iii) and precedes the heat treatment step (iv).
  • steps (i), (ii) and (iii) are performed simultaneously, i.e. together.
  • a) the monosaccharide(s) as defined previously, b) the polysaccharide(s) bearing amine group(s), in salified or non-salified form, as defined previously, and c) the dyestuff(s) chosen from pigments, direct dyes, and mixtures thereof, as defined previously, are applied together or else the process of the invention comprises a first step of applying to the keratin fibres an aqueous composition (C) as defined previously.
  • the process of the invention comprises a first step consisting in applying to the keratin fibres composition (C) as defined previously, optionally followed by a step of drying said keratin fibres, followed by a step of heat treatment of said keratin fibres at a temperature of greater than 80°C, preferably of between l00°C and 250°C, and preferably with an iron.
  • composition (C) is composition (C) as defined previously.
  • composition (C) represents a composition (C") as defined previously.
  • the process of the invention comprises:
  • a step consisting in simultaneously applying to the keratin fibres a) the monosaccharide(s) as defined previously, b) the polysaccharide(s) bearing amine group(s) as defined previously, and c) the dyestuff(s) chosen from pigments, direct dyes, and mixtures thereof, as defined previously, followed by a leave-on time of between 1 and 60 minutes,
  • the process of the invention comprises:
  • steps (i) and (ii) may be performed simultaneously, before or after step (iii).
  • the process may comprise:
  • a step consisting in applying to said keratin fibres a) one or more monosaccharides as defined previously, and b) one or more polysaccharides bearing amine group(s), in salified or non-salified form, as defined previously,
  • the process may comprise: - a step consisting in applying to said keratin fibres the mixture of compositions (ca) and (cb) as defined previously, followed by a leave-on time of between 1 and 30 minutes,
  • the process may comprise:
  • the process may comprise:
  • the process of the invention does not use oxidized polysaccharide, more generally the process of the invention does not use a compound comprising at least one aldehyde group.
  • composition (cb), (C), (C) or (C") as defined previously does not contain oxidized polysaccharide and more generally composition (cb), (C), (C) or (C") does not contain a compound comprising at least one aldehyde group.
  • the process according to invention may also comprise an additional step of drying the keratin fibres after the application a) of the monosaccharide(s) as defined previously, b) of the polysaccharide(s) bearing amine group(s) as defined previously and/or c) of the dyestuff(s) as defined previously or after application of compositions (C), (C’), (C”), (ca), (cb) and/or (cc) containing same and before the step of heat treatment (iv) of the keratin fibres performed at a temperature of at least 80°C.
  • the process of the invention involves a step of drying the keratin fibres, in particular human keratin fibres such as the hair, before the heat treatment step (iv).
  • the drying step is notably performed using a hairdryer, a hood, or else with a towel, an absorbent or by drying naturally.
  • This drying step is advantageously performed at a temperature ranging from 20 to 70°C.
  • the keratin fibre heat treatment step (iv) of the process of the invention is preferably performed at a temperature of between 80°C and 250°C, it being understood that the temperature is that of the heating means, in particular of the iron, and not the temperature of the keratin fibres.
  • the heat treatment step (iv) is performed on dry keratin fibres.
  • the keratin fibre heat treatment step (iv) is performed at a temperature of at least l00°C, in particular at a temperature of between l00°C and 250°C, inclusive.
  • the keratin fibre heat treatment step (iv) is performed at a temperature ranging from l50°C to 220°C, preferably ranging from l60°C to 220°C, more preferentially ranging from l60°C to 200°C, and even better still ranging from l30°C to l90°C.
  • the heat treatment temperatures correspond to the temperatures of the heating means, in particular of the iron when an iron is used, and not the temperature of the keratin fibres.
  • This heat treatment step (iv) is advantageously performed using an iron.
  • iron means a device for heating keratin fibres by placing said fibres in contact with the heating device.
  • the iron is other than a heating comb.
  • the end of the iron which comes into contact with the keratin fibres generally has two surfaces. These two surfaces may be made of metal or of ceramic. In particular, these two surfaces may be smooth or crimped or curved.
  • the heat treatment step may be performed by means of a straightening iron, a curling iron, a crimping iron or a steam iron such as a Steampod.
  • the heat treatment step is performed by means of a straightening iron.
  • steam irons refers to irons which comprise a device which emits steam and which applies this steam before, during or after the straightening/relaxing.
  • irons that may be used in the process according to the invention, mention may be made of any type of flat hair iron, and in particular, in a non-limiting manner, those described in patents US 5 957 140 and US 5 046 516.
  • the iron may be applied by successive separate strokes lasting a few seconds or by gradual movement or sliding along the keratin fibres, in particular along human keratin fibres such as the hair.
  • the iron is applied in the process according to the invention by a continuous movement from the root to the end of the keratin fibres, notably human keratin fibres such as the hair, in one or more strokes, in particular in one to twenty strokes.
  • Each stroke of the hair iron may last from 2 seconds to 1 minute for a length of the treated keratin fibres of 30 cm ⁇ 3 cm.
  • Step (iv) of heat treatment of the keratin fibres is performed for a time that may range advantageously from 100 milliseconds to 30 minutes, preferably from 1 second to 15 minutes, more preferentially from 2 seconds to 10 minutes, even better still from 3 seconds to 5 minutes and even better still from 4 seconds to 1 minute.
  • the bath ratio of the composition(s) applied before the heat treatment step of the process preferably ranges from 0.1 to 10, and more preferentially from 0.2 to 5.
  • the term "bath ratio" means the ratio between the total weight of the applied composition and the total weight of keratin fibres to be treated.
  • the keratin fibres may be optionally rinsed with water or washed with a shampoo.
  • the keratin fibres are then optionally dried using a hairdryer or a hood or left to dry naturally.
  • the dyeing process is performed one or more times, optionally spaced by one or more cosmetic treatments, preferably spaced by one or more shampoo washes, to treat keratin fibres that have regrown or that have undergone other treatments liable to cause changes in the colouring, or to obtain the desired colour intensity.
  • the process is performed on keratin fibres, in particular human keratin fibres such as the hair, which are notably natural, notably natural hair.
  • a subject of the invention is also a kit comprising:
  • a multi-compartment device comprising a first compartment containing a cosmetic composition (ca) comprising one or more monosaccharides as defined previously; a second compartment containing a cosmetic composition (cb) comprising one or more polysaccharides bearing amine group(s) as defined previously and optionally one or more organic or mineral acids as defined previously; and a third compartment containing a dye composition (cc) comprising one or more dyestuffs as defined previously; and
  • each compartment of the kit may be released either sequentially or simultaneously.
  • composition packaging assembly i.e. the multi-compartment device
  • the composition packaging assembly is, in a known manner, any packaging that is suitable for storing cosmetic compositions (notably a bottle, tube, spray bottle or aerosol bottle).
  • Such a kit allows the process for dyeing keratin fibres according to the invention to be performed.
  • composition (A) and the dye composition (B) according to the present invention were prepared from the ingredients mentioned in the tables below, the contents of which are expressed as weight percentages relative to the total weight of the composition comprising same.
  • composition (A) and the dye composition (B) obtained below are applied according to processes 1 to 9 below:
  • the dye composition (B) is diluted to 10% in water.
  • the solution thus obtained is applied to two locks of sensitized hair at a rate of 0.5 g of composition per gram of hair. After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7- second strokes with a straightening iron at a temperature of l90°C.
  • the dye composition (B) is diluted to 10% in composition
  • the mixture thus obtained is applied to two locks of sensitized hair at a rate of 0.5 g of composition per gram of hair. After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7- second strokes with a straightening iron at a temperature of l90°C.
  • the dye composition (B) is diluted to 10% in water.
  • the solution thus obtained is applied to two locks of sensitized hair at a rate of 0.5 g of composition per gram of hair. After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood.
  • Composition (A) is then applied to the two locks of hair at a rate of 0.5 g of composition per gram of hair. After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • the dye composition (B) is diluted to 10% in water.
  • the solution thus obtained is applied to two locks of sensitized hair at a rate of 0.5 g of composition per gram of hair. After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood.
  • Composition (A) is then applied to the two locks of hair at a rate of 0.5 g of composition per gram of hair. After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • composition (A) followed by the leave-on time, drying under a hood and five successive strokes with a straightening iron were repeated three times.
  • the locks of hair of processes 2, 4, 6 and 8 are washed with a shampoo according to the following protocol:
  • the locks are rinsed thoroughly with water at 37°C for 15 seconds.
  • the locks are then washed with a DOP shampoo, in a proportion of 0.4 g of shampoo per gram of hair.
  • the locks are then rinsed with water for 15 seconds, followed by being drained dry, combed and then dried.
  • the colouring obtained by means of the process of the invention does not transfer onto the user’s fingers.
  • the colour of the locks is then evaluated by colorimetry in the CIE L* a* b* system, using a Minolta CM 3600 spectrocolorimeter (illuminant D65, angle 10°, specular component included).
  • L* represents the intensity of the colour
  • a* indicates the green/red colour axis
  • b* the blue/yellow colour axis. The smaller the value of L*, the darker and more powerful the colouring.
  • L*, a* and b* represent the values measured on locks of hair after shampoo washing, namely the locks of hair of processes 2, 4, 6, 8 and 9 mentioned above
  • L0*, aO* and bO* represent the values measured on the respective locks of hair not washed with the shampoo, namely the locks of hair of processes 1, 3, 5 and 7 mentioned above.
  • the value of DE* for process 2 was calculated with L*, a* and b* representing the values obtained for process 2, and L 0 *, a 0 * and b 0 * representing the values obtained for process 1.
  • the colouring obtained by means of the process of the invention is also persistent with respect to shampoo washing at least five times (process 9).
  • compositions Compositions (A’) and (A") and the dye composition (B’) according to the present invention were prepared from the ingredients mentioned in the tables below, the contents of which are expressed as weight percentages relative to the total weight of the composition comprising same.
  • composition (A’) and the dye composition (B’) obtained above are applied according to processes 11 and 13 below.
  • the comparatives were prepared by replacing composition (A') with water according to processes 10 and 12 below.
  • composition (A') and the dye composition (B') obtained above are applied according to processes 15 and 17 below and the comparatives are prepared by replacing composition (A") with water according to processes 14 and 16 below.
  • the dye composition (B') is applied to two locks of natural grey hair at a rate of 1 g of composition per gram of hair. After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood. Water, adjusted to pH 3.5 with lactic acid, is then applied to the two locks of hair at a rate of 3 g of composition per gram of hair.
  • the locks After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • the dye composition (B') is applied to two locks of natural grey hair at a rate of 1 g of composition per gram of hair.
  • composition (A’) is then applied to the two locks of hair at a rate of 3 g of composition per gram of hair.
  • the locks After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • the dye composition (B') is applied to two locks of natural grey hair at a rate of 2 g of composition per gram of hair.
  • the locks are dried under a hood. Water, adjusted to pH 3.5 with lactic acid, is then applied to the two locks of hair at a rate of 10 g of composition per gram of hair.
  • the locks After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • the dye composition (B') is applied to two locks of natural grey hair at a rate of 2 g of composition per gram of hair.
  • composition (A’) is then applied to the two locks of hair at a rate of lOg of composition per gram of hair.
  • the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • dye composition (B') are diluted in 50 g of water, adjusted to pH 3.5 with lactic acid.
  • the mixture thus obtained is applied to two locks of natural grey hair at a rate of 5 g of mixture per gram of hair.
  • the locks After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • the mixture thus obtained is applied to two locks of natural grey hair at a rate of 5 g of mixture per gram of hair.
  • the locks After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • the mixture thus obtained is applied to two locks of natural grey hair at a rate of 3g of mixture per gram of hair.
  • the locks After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • the locks After a leave-on time of 5 minutes at 33°C, the locks are dried under a hood, and are then each subjected to five successive 7-second strokes with a straightening iron at a temperature of l90°C.
  • the locks are rinsed thoroughly with water at 37°C for 15 seconds.
  • the locks are then washed with a DOP shampoo, in a proportion of 0.4 g of shampoo per gram of hair.
  • the locks are then rinsed with water for 15 seconds, followed by being drained dry, combed and then dried.
  • the colour of the locks and the colour transfer onto a cotton fabric are evaluated visually.
  • the fabric is dragged over the length of the lock using a constant finger pressure and the final colour of the fabric is evaluated.

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Abstract

La présente invention concerne un procédé de coloration de fibres de kératine, en particulier des fibres de kératine humaines telles que les cheveux, comprenant l'application sur lesdites fibres de kératine a) d'au moins un monosaccharide, b) d'au moins un polysaccharide particulier, sous forme salifiée ou non, et c) d'au moins un colorant, suivie d'un traitement thermique des fibres de kératine. La présente invention concerne également une composition à pH acide (C) comprenant a) au moins un monosaccharide, b) au moins un polysaccharide portant un ou des groupes amine, sous forme salifiée ou non, et c) au moins un colorant. La présente invention concerne également un kit comprenant un dispositif à plusieurs compartiments contenant a) au moins un monosaccharide, b) au moins un polysaccharide portant un ou des groupes amine, et c) au moins un colorant, et un dispositif de chauffage des fibres de kératine.
PCT/EP2019/067199 2018-06-29 2019-06-27 Procédé de coloration de fibres de kératine par l'utilisation d'un monosaccharide, d'un polysaccharide portant des groupes amine et d'un colorant Ceased WO2020002521A1 (fr)

Applications Claiming Priority (2)

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FR1856006A FR3083106B1 (fr) 2018-06-29 2018-06-29 Procede de coloration des fibres keratiniques mettant en oeuvre un monosaccharide, un polysaccharide a groupes amines et une matiere colorante
FR1856006 2018-06-29

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WO2020002521A1 true WO2020002521A1 (fr) 2020-01-02

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WO2024223198A1 (fr) * 2023-04-26 2024-10-31 Henkel Ag & Co. Kgaa Procédé de coloration sans rinçage pour fibres kératiniques comprenant l'application d'un agent colorant contenant du chitosane, un pigment, de l'acide et de l'eau et le chauffage ultérieur
WO2025021351A1 (fr) * 2023-07-27 2025-01-30 Henkel Ag & Co. Kgaa Amélioration de la solidité au lavage de fibres de kératine teintes avec des colorants directs au moyen d'un procédé d'étanchéité utilisant du chitosane
WO2025257372A1 (fr) * 2024-06-13 2025-12-18 L'oreal Procédé de coloration de fibres kératiniques à l'aide d'un composé contenant des fonctions acétoacétate, d'un composé (poly)amine et d'un colorant direct
WO2026002418A1 (fr) * 2024-06-27 2026-01-02 Henkel Ag & Co. Kgaa Procédé de coloration de fibres de kératine, comprenant l'utilisation d'un colorant ayant un polymère filmogène et un composé de coloration, et utilisation d'un agent post-traitement ayant un polymère filmogène

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Publication number Priority date Publication date Assignee Title
DE102023203838A1 (de) * 2023-04-26 2024-10-31 Henkel Ag & Co. Kgaa Verfahren zur Färbung von Keratinfasern, umfassend die Anwendung eines Färbemittels mit Chitosan und farbgebender Verbindung und die Anwendung eines Nachbehandlungsmittels mit Proteinhydrolysat und/oder Aminosäure
DE102023203837A1 (de) * 2023-04-26 2024-10-31 Henkel Ag & Co. Kgaa Verfahren zur Färbung von Keratinfasern, umfassend die Anwendung eines Färbemittels mit Chitosan und farbgebender Verbindung und die Anwendung eines Shampoos
DE102023203839A1 (de) * 2023-04-26 2024-10-31 Henkel Ag & Co. Kgaa Verfahren zum Färben von Keratinfasern umfassend die Anwendung eines alkalischen Vorbehandlungsmittels und die Anwendung eines Färbemittels mit Chitosan und farbgebender Verbindung

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WO2024223198A1 (fr) * 2023-04-26 2024-10-31 Henkel Ag & Co. Kgaa Procédé de coloration sans rinçage pour fibres kératiniques comprenant l'application d'un agent colorant contenant du chitosane, un pigment, de l'acide et de l'eau et le chauffage ultérieur
DE102023203833A1 (de) 2023-04-26 2024-10-31 Henkel Ag & Co. Kgaa Leave-on Färbeverfahren für Keratinfasern umfassend die Anwendung eines Färbemittels mit Chitosan, Pigment, Säure und Wasser und eine nachfolgende Erwärmung
WO2025021351A1 (fr) * 2023-07-27 2025-01-30 Henkel Ag & Co. Kgaa Amélioration de la solidité au lavage de fibres de kératine teintes avec des colorants directs au moyen d'un procédé d'étanchéité utilisant du chitosane
WO2025257372A1 (fr) * 2024-06-13 2025-12-18 L'oreal Procédé de coloration de fibres kératiniques à l'aide d'un composé contenant des fonctions acétoacétate, d'un composé (poly)amine et d'un colorant direct
FR3163260A1 (fr) * 2024-06-13 2025-12-19 L'oreal Procédé de coloration des fibres kératiniques mettant en œuvre un composé à fonctions acétoacétates, un composé (poly)aminé et un colorant direct
WO2026002418A1 (fr) * 2024-06-27 2026-01-02 Henkel Ag & Co. Kgaa Procédé de coloration de fibres de kératine, comprenant l'utilisation d'un colorant ayant un polymère filmogène et un composé de coloration, et utilisation d'un agent post-traitement ayant un polymère filmogène

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