WO2013045703A1 - Composition de colorant comprenant un composé iridoïde non glycosylé et un aldéhyde ou une imine particulier, procédé de coloration et dispositif associé - Google Patents

Composition de colorant comprenant un composé iridoïde non glycosylé et un aldéhyde ou une imine particulier, procédé de coloration et dispositif associé Download PDF

Info

Publication number
WO2013045703A1
WO2013045703A1 PCT/EP2012/069365 EP2012069365W WO2013045703A1 WO 2013045703 A1 WO2013045703 A1 WO 2013045703A1 EP 2012069365 W EP2012069365 W EP 2012069365W WO 2013045703 A1 WO2013045703 A1 WO 2013045703A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
radical
alkyl radical
optionally substituted
alkyl
Prior art date
Application number
PCT/EP2012/069365
Other languages
English (en)
Inventor
Hervé David
Gwenaëlle JEGOU
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L'oreal filed Critical L'oreal
Priority to KR1020147011554A priority Critical patent/KR102065332B1/ko
Priority to JP2014532432A priority patent/JP6612026B2/ja
Publication of WO2013045703A1 publication Critical patent/WO2013045703A1/fr

Links

Classifications

    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from 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
    • A61Q5/10—Preparations for permanently dyeing the hair
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]

Definitions

  • the present invention relates to a dye composition
  • a dye composition comprising, in a cosmetically acceptable medium, at least one compound from the non-glycosyl iridoid family extracted from plants, and at least one particular aldehyde or imine compound, and also to a dyeing process using such a composition.
  • a cosmetically acceptable medium at least one compound from the non-glycosyl iridoid family extracted from plants, and at least one particular aldehyde or imine compound
  • patent application EP 440 494 discloses a hair dyeing process using a composition comprising at least one compound of (seco)iridoid-glycoside or non-glycosyl
  • (seco)iridoid also known as aglycone
  • plants such as Rubiaceae, Euphorbiaceae, Valerianaceae, Cornaceae, Gentianaceae, Caprifoliaceae, Oleaceae,
  • the aim of the present invention is thus to overcome the drawbacks described above.
  • the colour build-up can be substantially improved using compounds of non-glycosyl iridoid type and derivatives thereof, and, in general, any natural extract containing the same, by combining this compound with a particular aldehyde or imine compound.
  • composition for dyeing human keratin fibres comprising, in a cosmetically acceptable medium:
  • Ri represents a hydrogen atom, a methyl radical, a hydroxymethyl radical, an aldehyde group; a group -CO2R4 in which R 4 represents a hydrogen atom or a C1-C2 alkyl radical; a group -CH 2 -glucose;
  • R 2 represents a hydrogen atom, a hydroxyl radical or a glucose radical
  • R 3 which may be identical or different, represent a hydrogen atom, a hydroxyl radical, a (CrC 4 )alkyloxy radical; the number of hydroxyl groups not being greater than 2;
  • n is an integer between 1 and 5;
  • R 5 represents a group -C0 2 R'6 in which R' 6 represents a hydrogen atom or a C C 2 alkyl radical; an alkali metal cation, an ammonium group;
  • R 6 represents a hydrogen, a group -C0 2 R' 6 in which R' 6 represents a hydrogen atom, a C C 2 alkyl radical, an alkali metal cation, an ammonium group;
  • n is an integer equal to 0 or 1 ,
  • X represents an oxygen atom, NR"-i with R"-i representing a hydrogen atom or a C1-C10 alkyl radical;
  • the compounds may also be:
  • R' 3 OH additional primary monoalcohol
  • R' 3 represents a a C1-C5 alkyl radical or a symmetrical 1 ,2- or 1 ,3-diol containing a C 2 -C 3 alkyl chain
  • n is equal to 0;
  • radicals R'i and R' 2 independently of each other, represents a hydrogen atom or an unsubstituted linear Ci-C 6 alkyl radical
  • the monovalent radical A and divalent radical A-i represent a group chosen from:
  • aryl-ethylenyl radical an aryl-ethylenyl radical, the aryl group being C 6 and optionally substituted with at least one C1-C2 alkyl or C1-C2 alkoxy radical,
  • R' 4 represents a C1-C2 alkyl radical or a phenyl group
  • R' 5 represents a Ci-C 8 alkyl radical optionally substituted with at least one hydroxyl group, an ammonium group -N + R" 6 with R" 6 , which may be identical or different, representing a C C 2 alkyl radical, a group -SiR' 7 with R' 7 , which may be identical or different, representing a C C 2 alkyl radical; a benzyl radical (-CH 2 -C 6 H 6 ),
  • two radicals -OR' 5 located ortho to the C 6 aryl group may form a 5- or 6-membered heterocycle by means of the two radicals R' 5 ,
  • R' 8 which may be identical or different, represent a Ci-C 6 alkyl radical optionally substituted with a hydroxyl group, a carboxylic group (-COOH) in acid or salified form, or a sulfonic group (-S0 3 H) in acid or salified form; the radicals R' 8 possibly forming a saturated or unsaturated 5- or 6- membered heterocycle with the nitrogen atom that bears them, optionally comprising another heteroatom chosen from O, N and NR' 9 in which R' 9 represents a Ci-C 2 alkyl radical; the heterocycle being optionally substituted with a hydroxyl group,
  • R' 10 represents a C 6 aryl group fused to a 6-membered hydrocarbon-based ring optionally substituted with at least one C C 2 alkyl radical
  • R'n represents a C C 2 alkyl radical, a halogen atom preferably chosen from chlorine and bromine, a group -0-S0 2 -C 6 H 6 ,
  • an unsaturated cationic or non-cationic 5- or 6-membered heterocycle comprising one or two heteroatoms chosen from O, N and NR' 12 in which R' 12 represents a C C 2 alkyl group optionally fused to a saturated or unsaturated, aromatic or non-aromatic 5- or 6-membered ring, one of the heteroatoms possibly being included in the two rings; the heterocycle or the fused ring possibly being substituted with at least one Ci-C 2 alkoxy radical,
  • the said aryl group being optionally fused to a 5- or 6-membered heterocyclic group, comprising one or two heteroatoms chosen from O, N and NR' 13 in which R' 13 represents a CrC 4 alkyl radical, the heterocycle being optionally fused to a C 6 aryl group,
  • the said aryl group being optionally fused to a C 6 aryl group optionally substituted with at least one Ci-C 2 alkoxy group;
  • a cationic or non-cationic, saturated or unsaturated, aromatic or non- aromatic 5- or 6-membered heterocyclic group comprising one or two identical or different heteroatoms preferably chosen from O, N and NR' 14 with R' 14 representing a hydrogen atom, a Ci-C 6 alkyl radical or a C 6 aryl radical optionally substituted with a group (R'i 5 ) 2 NCO- or (R' 15 )CO-NH- in which R' 15 , which may be identical or different, represent a Ci-C 2 alkyl radical;
  • the said heterocyclic group being optionally fused to a 6-membered aryl group which is itself optionally substituted with at least one C C 2 alkyl, d-C 4 alkoxy or phenoxy group;
  • the said heterocyclic group being optionally substituted with at least: o a hydroxyl group,
  • Ci-C 2 alkyl radical optionally substituted with a hydroxyl radical
  • an amino radical -N(R' 16 )2 in which R' 16 which may be identical or different, represent a C C 4 alkyl radical optionally substituted with a hydroxyl group, the radicals R'i 6 possibly forming a saturated or unsaturated 5- or 6- membered heterocycle with the nitrogen atom that bears them, optionally comprising another heteroatom chosen from O, N and NR' 17 in which R' 17 represents a C C 2 alkyl radical,
  • the divalent radical A 2 represents a linear C-I-C-IO alkylene chain connecting two radicals A-i via a carbon, oxygen or nitrogen atom;
  • a final subject of the invention consists of a multi-compartment device comprising a first compartment containing at least one compound of formula (I) and/or (II) or the plant extract comprising the same, and a second compartment containing at least one compound of formula (i) or (ii), an oxidized oligo- or polysaccharides comprising at least one aldehyde or imine function.
  • composition according to the invention makes it possible to obtain varied, shampoo-fast colorations, which do not degrade the hair.
  • the human keratin fibres treated via the process according to the invention are preferably the hair.
  • the mineral acid salts are more particularly hydrochlorides, hydrobromides, sulfates and phosphates; the organic acid salts are more particularly citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates and acetates.
  • solvates are more particularly hydrates.
  • the composition comprises, in a cosmetically acceptable medium, at least one compound of the abovementioned formula (I) and/or formula (II), or a plant extract comprising the same.
  • Ri represents a hydrogen atom, a methyl radical, a hydroxymethyl radical, an aldehyde group; a hydroxycarbonyl radical, a methoxycarbonyl group or an ethoxycarbonyl group.
  • R 2 represents a hydrogen atom or a hydroxyl radical.
  • R 3 which may be identical or different, represent a hydrogen atom, a hydroxyl group, a methoxy group, an ethoxy group or an n-butyloxy group.
  • R 5 represents a hydroxycarbonyl radical, a methoxycarbonyl radical or an ethoxycarbonyl radical.
  • R 6 represents a hydrogen, a hydroxycarbonyl radical, a methoxycarbonyl radical or an ethoxycarbonyl radical.
  • the compound of formula (I) and/or of formula (I I) is genipin (R-i represents a methoxycarbonyl group) and/or geniposic acid or a salt thereof (Ri represents a carboxylic group in acid or salified form) and/or genipic acid (R 5 represents a hydroxycarbonyl radical and R 6 represents a hydrogen atom) and/or genipinic acid (R 5 represents a hydroxycarbonyl radical and R 6 represents a methoxycarbonyl radical).
  • the compounds of formula (I) and/or of formula (I I) are generally found in plant extracts originating from the following plants: Veronica persica; Genipa americana; Apodytes dimidiata; Randia canthioides; Tarenna attenuata and preferably Genipa americana.
  • extract denotes juices or powders obtained via one or more operations of separation of the vegetal parts of the plant, of enrichment or concentration and optionally of drying, starting with natural plant substances.
  • the aerial parts are washed, if necessary, either ground, optionally in a frozen form, or chopped at room temperature, and then macerated in a suitable solvent, in particular ethanol or water, and then filtered, concentrated and optionally dried.
  • a suitable solvent in particular ethanol or water
  • fruit In the more particular case of fruit, it is optionally frozen, and washed with water to remove the impurities present. They may optionally be sterilized, in particular with a solution comprising ethanol and chlorine.
  • the fruit is thawed, if necessary, and pressed, for example using a specially adapted hydraulic press.
  • the juice thus recovered is filtered and degassed in the presence of nitrogen, this operation avoiding the oxidation of genipin or derivatives thereof by increasing the amount of dissolved gas.
  • the juice is then stored in airtight hermetic packaging.
  • the juice recovered may then, where appropriate, undergo a step of concentration and drying.
  • the extract used is obtained from Genipa americana.
  • the extract is obtained from unripe fruit of Genipa americana.
  • the first step in the preparation of the extract consists in first freezing the fruit and in performing a cryomilling step, for example at a temperature of between -20°C and -200°C on the frozen fruit. A fine, homogeneous powder is thus collected.
  • the active agent(s) of formula (I) and/or (I I) are extracted, for example with water.
  • the extract is then concentrated and then optionally dried.
  • the content of compound of formula (I) and/or of formula (II) in the dry extract ranges from 0.01 % to 30% by weight.
  • the content of compound of formula (I) and/or of formula (II) in the composition is between 0.001 % and 20% by weight relative to the weight of the composition.
  • the dye composition may also comprise additional dyes other than the abovementioned compounds of formula (I) and/or of formula (II).
  • direct dyes may be 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, indoamine direct dyes and natural direct dyes.
  • oxidation bases mention may be made of para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, bis-para-aminophenols, ortho- aminophenols and heterocyclic bases, and the addition salts thereof.
  • couplers mention may be made especially of meta- phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene couplers and heterocyclic couplers, and the addition salts thereof.
  • the oxidation base(s) present in the dye composition are each generally present in an amount of between 0.001 % and 10% by weight and preferably between 0.005% and 6% by weight relative to the total weight of the dye composition.
  • the coupler(s) are each generally present in an amount of between 0.001 % and 10% by weight and preferably between 0.005% and 6% by weight relative to the total weight of the dye composition.
  • addition salts of the oxidation bases and couplers that can be used within the context of the invention are especially chosen from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the composition also comprises at least one aldehyde or imine compound chosen from the abovementioned formulae (i) and (ii), and also oxidized oligo- or polysaccharide comprising at least one aldehyde or imine function.
  • the compounds of formulae (i) and (ii) are such that X represents an oxygen atom.
  • Compounds (i) and (ii) may also be in the form of a 5- or 6-membered cyclic or acyclic acetal resulting from the condensation of an additional primary monoalcohol (R' 3 OH) in which R' 3 represents a CrC 5 alkyl radical or a symmetrical 1 ,2- or 1 ,3-diol containing a C 2 -C 3 alkyl chain,
  • R' 3 represents a CrC 5 alkyl radical or a symmetrical 1 ,2- or 1 ,3-diol containing a C 2 -C 3 alkyl chain
  • These compounds may also be in the form of a hemiacetal resulting from the condensation of a hydroxyl group present on A or A-i when A or A-i represents an alkyl radical and when n is equal to 0.
  • an organic or mineral anion or mixture of anions that can equilibrate the charge(s) of the said compounds, selected, for example, from a halide such as chloride, bromide, fluoride or iodide; a hydroxide; a sulfate; a hydrogen sulfate; an alkyl sulfate in which the linear or branched alkyl moiety is Ci-C 6 , such as the methyl sulfate or ethyl sulfate ion; carbonates and hydrogen carbonates; salts of carboxylic acids, such as formate, acetate, citrate, tartrate and oxalate
  • the nonionic or anionic oxidized polysaccharide comprise one or more aldehyde groups and optionally one or more anionic groups. These anionic groups are preferably carboxylic or carboxylate groups.
  • nonionic or anionic oxidized polysaccharide used may be represented by formula (I) below:
  • P represents a polysaccharide chain consisting of monosaccharides comprising 5 carbon atoms or more than 5 carbon atoms, preferably 6 or more than 6 carbon atoms and more particularly 6 carbon atoms.
  • X is chosen from a hydrogen atom, the ions derived from an alkali metal or an alkaline- earth metal such as sodium or potassium, ammonia, organic amines such as monoethanolamine, diethanolamine, triethanolamine and 3-amino-1 ,2-propanediol and basic amino acids such as lysine, arginine, sarcosine, ornithine and citrulline,
  • M is such that the degree of substitution of the polysaccharide with one or more aldehyde groups (DS(CHO)) is within the range from 0.001 to 2 and preferably from 0.005 to 1 .
  • n is such that the degree of substitution of the polysaccharide with one or more carboxylic groups (DS(COOX)) is within the range from 0 to 2 and preferably from 0.001 to 1 .5.
  • degree of substitution DS(CHO) or DS (COOX) of the polysaccharides according to the invention means the ratio between the number of carbons oxidized as an aldehyde or carboxylic group for all the repeating units and the number of elemental monosaccharides (even opened by preoxidation) constituting the polysaccharide.
  • the groups CHO and COOX may be obtained during the oxidation of certain carbon atoms, for example in position C2, C3 or C6, of a saccharide unit containing 6 carbon atoms.
  • the oxidation may take place at C2 and at C3, more particularly from 0.01 % to 75% by number and preferably from 0.1 % to 50% by number of the rings having possibly been opened.
  • the polysaccharide chain, represented by P is preferably chosen from inulins, celluloses, starches, pectins, guar gums, xanthan gums, pullulan gums, alginate gums, agar-agar gums, carrageenan gums, gellan gums, gum arables, xyloses and tragacanth gums, and derivatives thereof.
  • derivative means the compounds obtained by chemical modification of the mentioned compounds. They may be esters, amides or ethers of the said compounds.
  • the oxidation may take place according to a process known in the art, for example according to the process described in FR 2 842 200, in document FR 2 854 161 or in the article "Hydrophobic films from maize bran hemicelluloses" by E. Fredon et al., Carbohydrate Polymers 49, 2002, pages 1 to 12.
  • Another oxidation process is described in the article “water soluble oxidized starches by peroxide reaction extrusion” Industrial Crops and Products 75 (1997) 45-52 - R. E. Wing, J. L. Willet.
  • These oxidation processes are simple to perform, are efficient and do not generate any toxic by-products or byproducts that are difficult to remove.
  • the peroxide may be an alkali metal or alkaline-earth metal percarbonate or perborate, an alkyl peroxide, peracetic acid or hydrogen peroxide.
  • the amount of peroxide in the reaction medium is generally between 0.05 and 1 molar equivalent per glucose unit of the polysaccharide.
  • a single phthalocyanin or a mixture of phthalocyanins may be used as catalyst.
  • the amount of catalyst depends on the desired degree of substitution. In general, a small amount, for example an amount corresponding to 0.003 to 0.016 molar equivalent per 100 glucose units of polysaccharide, is suitable for use.
  • the process may also be performed by placing the polysaccharide in pulverulent form in contact with the catalyst dissolved in a small volume of water and with the peroxide. This process is referred to as a "semi-dry" process.
  • the polysaccharide is obtained by oxidation of inulin, cellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, methylcellulose, starch, starch acetate, hydroxyethyl starch, hydroxypropyl starch, guar gum, carboxymethyl guar gum, carboxymethylhydroxypropyl guar gum, hydroxyethyl guar gum, hydroxypropyl guar gum, xylose, xanthan gum or carrageenan gum, or mixtures thereof.
  • polysaccharides that are the most particularly preferred in the invention are those corresponding to formula (I) in which P represents a polymer chain derived from inulin and from starch; m is such that the degree of substitution of the polysaccharide with one or more aldehyde groups (DS(CHO)) is within the range from 0.005 to 2.5; n is such that the degree of substitution of the polysaccharide with one or more carboxylic groups (DS(COOX)) is within the range from 0.001 to 2.
  • oxidized oligo- and polysaccharide comprising at least one aldehyde or imine function
  • the composition comprises at least one compound of formula (i).
  • formula (i) is such that:
  • radicals R'i and R' 2 independently of each other, represent a hydrogen atom or an unsubstituted linear Ci-C 6 alkyl radical
  • A represents:
  • R' 5 represents a Ci-C 6 alkyl radical, o an aryl-ethylenyl radical, the aryl group being C 6 and optionally substituted with at least one C1-C2 alkyl or d-C 2 alkoxy radical, o an unsaturated cationic or non-cationic 5- or 6-membered heterocycle comprising one or two heteroatoms chosen from O, N and N R' 12 in which R'i2 represents a Ci-C 2 alkyl group optionally fused to a saturated or unsaturated, aromatic or non-aromatic 5- or 6-membered ring, one of the heteroatoms possibly being included in the two rings; the heterocycle or the fused ring possibly being substituted with at least one Ci-C 2 alkoxy radical,
  • aryl group being optionally fused to a 5- or 6-membered heterocyclic group, comprising one or two heteroatoms chosen from O, N and N R' 13 in which R' 13 represents a Ci-C 4 alkyl radical;
  • 6-membered heterocyclic group comprising one or two identical or different heteroatoms preferably chosen from O, N and N R' 14 with R' 14 representing a hydrogen atom, a CrC 6 alkyl radical or a C 6 aryl radical optionally substituted with a group (R' ⁇ NCO- or (R'i 5 )CO-N H- in which R' 15 represent a CrC 2 alkyl radical;
  • heterocyclic group being optionally fused to a 6-membered aryl group which is itself optionally substituted with at least one Ci-C 2 alkyl or C1-C4 alkoxy group;
  • Ci-C 2 alkyl radical optionally substituted with a hydroxyl radical
  • R' 16 an amino radical -N(R' 16 )2 in which R' 16 , which may be identical or different, represent a Ci-C 4 alkyl radical optionally substituted with a hydroxyl group
  • the radicals R'i 6 possibly forming a saturated or unsaturated 5- or 6-membered heterocycle with the nitrogen atom that bears them, optionally comprising another heteroatom chosen from O, N and N R' 17 in which R' 17 represents a C C 2 alkyl radical
  • the content of compound(s) of formula (i) or (ii), or of oxidized oligo- or polysaccharide comprising at least one aldehyde or imine function is between 0.001 % and 30% by weight relative to the weight of the composition.
  • - oxidized cellulose (Rn 9032-52-4) known under the names 2,3-Dialdehyde cellulose; 2,3-Dialdehydocellulose; Aldehydocellulose; Cellulose 2,3-dialdehyde; Cellulose dialdehyde; Dialdehyde cellulose;
  • the composition may comprise at least one primary or secondary amine or addition salts thereof, ammonia or hydroxylamine, or mixtures thereof.
  • addition salts of these amine compounds that may be used in the context of the invention are especially chosen from addition salts with an acid, such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, dodecylbenzenesulfonat.es, phosphates and acetates, and preferably the hydrochlorides, citrates, succinates, tartrates, phosphates and lactates.
  • an acid such as hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, dodecylbenzenesulfonat.es, phosphates and acetates
  • hydrochlorides, citrates, succinates, tartrates, phosphates and lactates such as hydrochlorides, hydrobromides
  • the primary or secondary amine(s) that may be used in the context of the invention are chosen from the amines of formula (III) that will be detailed below, amino polymers, purine bases, and also the addition salts thereof, and combinations thereof.
  • R' 7 and R' 8 represent, independently of each other:
  • the compounds of formula (III) are advantageously not oxidation bases or oxidation couplers employed in the dyeing of keratin fibres.
  • ureido N(R) 2 -CO-NR'-) in which the radicals R and R', independently of each other, represent a hydrogen atom or a C C 4 alkyl or (Ci-C 4 )alkylsulfonylamino radical;
  • the groups present as substituents are chosen from the following groups: carboxylic in acid or salified form; hydroxyl; C C 4 alkoxy; (CrC 8 )alkoxy carbonyl; thiol; (CrC 4 )alkylthio; amino; mono- and di(Ci-C 4 )alkylamino; aminocarbonyl; mono- and di(C C 2 )alkylaminocarbonyl; (Ci-C 4 )alkylcarbonylamino; phenyl, indolyl, pyrrolinyl, imidazolyl optionally substituted with one or more C C 2 alkyl or hydroxyl.
  • the amine(s) of formula (III) which may be identical or different, comprise from 1 to 5 primary and/or secondary amine functions; the amine(s) not comprising any N-N bonds. Also, the amine(s) of formula (III) do not comprise more than two heteroatoms bonded together.
  • the amine(s) are compounds of formula (III), more particularly chosen from the compounds of formulae (Ilia) to (llli), (llli') below, and also the addition salts thereof.
  • R 9 represents a hydrogen atom, a linear or branched Ci-C 6 alkyl radical, preferably substituted with one or more hydroxyl, hydroxycarbonyl, thiol, (CrC 4 )alkylthio, amido, amino or guanidine groups, a phenyl radical, optionally substituted with one or more hydroxyl, an indolyl radical optionally substituted with one or more hydroxyl, an imidazolyl radical, a pyrrolinyl radical optionally substituted with a Ci-C 2 alkyl group; or an unsubstituted phenyl radical;
  • R" 9 denotes a hydrogen, a C C 4 alkyl radical or an unsubstituted phenyl radical
  • - Rio represents a hydrogen or a C C 4 alkyl radical
  • R" 9 and R 9 possibly forming, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered heterocycle.
  • the compounds of formula (Ilia) are advantageously chosen from 2-amino-2-methylpropanoic acid; omethyl-D,L-phenylalanine; D,L-o (hydroxymethyl)alanine; D,L-a-methyl-meta-tyrosine; a-methyl-D,L-tryptophan; D,L-o methylhistidine dihydrochloride; L-2-methylserine; (S)-2-methylcysteine dihydrochloride; (S)-2-methyl-2-pyrrolidinecarboxylic acid.
  • R 9 represents a hydrogen atom, a linear or branched Ci-C 6 alkyl radical, preferably substituted with one or more hydroxyl, hydroxycarbonyl, (Ci-C 4 )alkoxycarbonyl, thiol, (C C 4 )alkylthio, amido, amino or guanidine groups, a phenyl radical, optionally substituted with one or more hydroxyl, an indolyl radical optionally substituted with one or more hydroxyl, an imidazolyl radical, a pyrrolinyl radical optionally substituted with a Ci-C 2 alkyl group; or an unsubstituted phenyl radical;
  • R" 9 represents a hydrogen, a C C 4 alkyl radical or an unsubstituted phenyl radical
  • - Rio represents a hydrogen or a C C 4 alkyl radical
  • R 9 and Rn may optionally form a saturated 5- membered carbon-based ring.
  • Rn represents a linear or branched, optionally substituted C1-C10 alkyl radical; a benzyl radical; and even more preferably a linear or branched C1-C4 alkyl radical optionally substituted with at least one hydroxyl group, preferably from 1 to 2 hydroxyl groups; a benzyl radical.
  • - R 9 represents a hydrogen atom, a linear or branched Ci-C 6 alkyl radical, preferably substituted with one or more hydroxyl, (CrC 4 )alkoxycarbonyl, hydroxycarbonyl, thiol, (C C 4 )alkylthio, amido, amino or guanidine groups, a phenyl radical, optionally substituted with one or more hydroxyl, an indolyl radical optionally substituted with one or more hydroxyl, an imidazolyl radical, a pyrrolinyl radical optionally substituted with a C1-C2 alkyl group; - R" 9 represents a hydrogen or a C1-C4 alkyl radical optionally substituted with a hydroxysulfonyl radical;
  • R1 0 represents a hydrogen or a C1-C4 alkyl radical
  • R" 9 and R 9 possibly forming, together with the nitrogen atom to which they are attached, a saturated 5-membered heterocycle
  • Ci-C 6 alkyl radical preferably substituted with one or more hydroxyl, thiol, (C C 4 )alkylthio, amido or amino, a phenyl radical, optionally substituted with one or more hydroxyl, an indolyl radical optionally substituted with one or more hydroxyl, an imidazolyl radical, a pyrrolinyl radical optionally substituted with a C1-C2 alkyl group;
  • - X represents a sulfur or nitrogen atom.
  • R 9 and R12 may optionally form a saturated 5-, 6- or 7-membered carbon-based ring.
  • R12 represents an alkyl radical defined as previously and most particularly an amino acid residue and/or the corresponding methyl or ethyl ester thereof chosen from alanine, arginine, asparagine, aspartate, cysteine, glutamate, glutamine, glycine, histidine, lysine, methionine, phenylalanine, proline, pyrrolysine, serine, threonine, tryptophan, tyrosine, valine, leucine or isoleucine
  • the compound of formula (III c) represents a dipeptide or an oligopeptide.
  • Ri3, Ri4 > Ri5 and Ri 6 represent, independently of each other:
  • X represents a nitrogen, oxygen or sulfur atom
  • Ri7 represents:
  • R18 represents:
  • - o is an integer between 0 and 5.
  • the radicals Ri 6 and Ri 7 may optionally form, with the carbon atom for R 16 and the atom X for the radical Ri 7 to which each is attached, a saturated or unsaturated 5- or 6-membered heterocycle, optionally substituted as indicated previously, optionally aromatic, optionally comprising another nitrogen or non- nitrogen heteroatom.
  • the radicals Ri 8 and Ri 5 may optionally form, with the nitrogen atom for R 18 and the carbon atom for the radical Ri 5 to which each is attached, a saturated or unsaturated 5- or 6-membered heterocycle, optionally substituted as indicated previously, optionally aromatic, optionally comprising another nitrogen or non-nitrogen heteroatom.
  • L-2- aminohexanoic acid amide hydrochloride L-phenylalanine amide; (S)-(+)-aminosuccinic acid; (R)-2-(methylamino)succinic acid; ethyl nipecotate; 3-piperidine carboxylic acid; 3- phenyl-3-alanine; ethyl 3-aminobutyrate; 2-carboethylamine; D,L-3-aminoadipic acid; ⁇ - alanine ethyl ester hydrochloride; ethyl 3-amino-3-ureido-N-butyrate; dimethyl (S)- aminosuccinate hydrochloride; ⁇ -L-alanine methyl ester hydrochloride; 4- carboxyethoxypiperidine; 4-aminobutyric acid; D,L-3-aminoadipic acid; 4- (methylamino
  • Ri3, Ri4, Ri5, Ri6 and Ri 8 have the same meaning as previously;
  • - p is an integer between 0 and 7; - u is an integer equal to 1 or 2.
  • the radical Ri 8 represents a hydrogen.
  • radicals Ri 3 and Ri 4 may optionally form, with the carbon for R 13 and Ri 4 to which these substituents are attached, a saturated 5- or 6-membered heterocycle.
  • Ri 3 , Ri 4 , Ri 5 and Ri 6 independently of each other, a hydroxyalkyl radical, a (d- C 4 )alkoxycarbonyl radical, a carboxaldehyde radical, a (CrC 3 )alkoxy
  • - q is an integer between 1 and 18;
  • - X represents an oxygen atom, an SH or OH group, or a methylene group optionally substituted with a hydroxyl radical;
  • R 18 forms a 5- or 6-membered rings optionally substituted with one or more hydroxy(methyl), preferably from 1 to 4 hydroxy(methyl) groups.
  • the radicals Ri 6 and Ri 8 or R 13 and Ri 8 may optionally form, with the carbon atom for R 16 (or for R 13 ) and the nitrogen atom for the radical Ri 8 to which each is attached, a saturated or unsaturated 5- or 6-membered heterocycle, optionally substituted as indicated previously, optionally aromatic, optionally comprising another nitrogen or non-nitrogen heteroatom.
  • the amine of formula (lllf) may be a ⁇ - amino alcohol originating from the reduction of the acid or ester function to an alcohol of one of the 20 esterified or non-esterified amino acids.
  • Ri3, Ri4 > Ri5 have the same meaning as previously;
  • - o is an integer between 0 and 5
  • - v is an integer equal to 1 or 2.
  • R 18 represents a hydrogen.
  • radicals Ri 3 , Ri4, Ri 5 and Ri 6 independently of each other, may also represent a hydroxyl radical, a (CrC 4 )alkoxycarbonyl radical, a carboxaldehyde radical, a (CrC 3 )alkoxy;
  • R21 and R22 possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated 5- or 7-membered heterocycle, optionally substituted as indicated previously, optionally aromatic, optionally comprising another nitrogen or non- nitrogen heteroatom; the alkyl radical not comprising any nitro, nitroso, peroxo or diazo functions,
  • - w is an integer between 1 and 10.
  • the alkyl radicals Ri 6 and R21 may optionally form, with the carbon atom for R 16 and the nitrogen atom for the radical R21 to which each is attached, a saturated or unsaturated 5- or 6-membered heterocycle, optionally substituted as indicated previously, optionally aromatic, optionally comprising another nitrogen or non-nitrogen heteroatom.
  • the alkyl radicals Ri 8 and R 2 i may optionally form, with the first nitrogen atom for R 18 and the last nitrogen atom for the radical R 2 i to which each is attached, a saturated or unsaturated 5- to 14-membered heterocycle, optionally substituted as indicated previously, optionally aromatic, optionally comprising another nitrogen or non-nitrogen heteroatom.
  • R 2 3 and R 24 represent, independently of each other:
  • Ci-C 6 alkyl radical optionally interrupted with one or more heteroatoms and/or with one or more groups comprising at least one heteroatom, preferably chosen from oxygen, nitrogen, sulfur, CO, SO and S0 2 or combinations thereof; the alkyl radical not comprising any nitro, nitroso, peroxo or diazo functions;
  • R-CO- an alkylcarbonyl radical in which R represents a C C 4 alkyl radical
  • halogen atom preferably chosen from bromine, chlorine and fluorine
  • RO-CO- an alkoxycarbonyl group in which R represents a C1-C4 alkyl radical
  • RCO-NR'- an alkylcarbonylamino group in which the radical R represents a C C 4 alkyl radical and the radical R' represents a hydrogen atom or a C1-C4 alkyl radical;
  • - Y represents a carbon or nitrogen atom
  • - z, z' and z" represent, independently of each other, a carbon atom, a nitrogen atom or a nitrogen atom substituted with a hydrogen;
  • - x is an integer between 0 and 2; when x is less than 2, the unsubstituted carbon atom(s) bear a hydrogen atom;
  • - x' is an integer equal to 0 or 1 ; when x' is less than 1 , the unsubstituted carbon atom(s) bear a hydrogen atom.
  • amines which may or may not be in salt form: lauroylethylenediamine, octopamine, oleamine, palmitamine, 2-(2- aminoethoxy)ethanol, 2-amino-4,5-dimethylthiazole, hexetidine, mecamylamine, tranylcypromine, triamterene, methyl[2-(3-trimethoxysilylpropylamino)ethylamine], bis(triethoxysilylpropyl)amine, N 1 -(3-(trimethoxysilyl)propyl)hexane-1 ,6-diamine, diethylenetriaminopropyltrimethoxysilane, N-(3-triethoxysilylpropyl)ethylenediamine, N-(3- trimethoxysilylethyl)ethylenediamine.
  • the amines are chosen from amino polymers, and also the addition salts thereof.
  • amino polymers means macromolecules of more or less high molecular weight containing one or more primary or secondary amine functions.
  • polymer means a compound comprising at least five repeating units linked in sequence via covalent bonds.
  • the amino polymer may be synthesized:
  • polysaccharides cellulose, dextran, chitosan, guar
  • amino or thiol derivatives thereof may be of natural origin, optionally chemically modified, for instance polysaccharides (cellulose, dextran, chitosan, guar) and amino or thiol derivatives thereof.
  • the polymers may be in any type of topology: linear, branched, star or hyperbranched chain (for instance dendrimers), block, random or alternating chains.
  • the chemical groups may be naturally present on the polymer chain, at the end of the chain, grafted along the main chain or side chains, or on the branches of star or hyperbranched polymers.
  • polyamino acids containing free OH or N H 2 or SH or COOH groups for example polylysine
  • polylysine and in particular from polylysine; chitosan; polyethoxylated amines such as carboxyPEG-8 amine, carboxyPEG-12 amine or carboxyPEG-24 amine; or combinations thereof.
  • the amine(s) are chosen from purine bases, in particular chosen from adenine, adenosine, guanine, guanosine G, thymine, thymidine T, uracil, uridine U, cytosine, cytidine C, addition salts thereof, and combinations thereof.
  • the composition comprises one or more amines, they are chosen from ammonia, the compounds of formulae (I l ia), (1 Mb), (I I I c), (ll le) and (l l lg) in particular when R 2 o represents a linear C1-C4 alkoxy group, and (U N'), or mixtures thereof.
  • the composition comprises one or more primary or secondary amines, ammonia or hydroxylamine, their content represents in the composition between 0.001 % and 65% by weight and preferably between 0.001 % and 30% by weight relative to the weight of the composition.
  • composition according to the invention may optionally comprise at least one enzyme, chosen, for example, from isolase, ⁇ -glucosidase derived, for example, from sweet almond (EC 3.2.1.21 ), alcohol oxidase (EC 1 .1.3.13), alcohol dehydrogenases EC 1 .1 .1.1 , alcohol dehydrogenases EC 1.1 .1 .2, alcohol dehydrogenases EC 1 .1.1.71 , aromatic alcohol dehydrogenases EC 1.1.1 .90, also known as aryl alcohol dehydrogenases, aromatic alcohol dehydrogenases EC 1.1.1 .97, 3-hydroxybenzyl alcohol dehydrogenases EC 1 .1.1 .97, coniferyl alcohol dehydrogenases EC 1.1 .1 .194, cinnamyl alcohol dehydrogenases EC 1 .1.1.195, methanol dehydrogenases EC 1.1.1 .244, aromatic alcohol oxidases EC 1.1 .3.7, also known as
  • the concentration of the enzyme used in the dye composition is between 0.005% and 40% by weight relative to the total weight of the said composition and preferably between 0.05% and 10% by weight relative to the weight of this composition.
  • composition comprising the compound(s) of formulae (I) and/or (II) may optionally comprise one or more salts.
  • these salts are generally chosen from organic solvents and/or mineral salts, and also combinations thereof.
  • the anions composing these salts may be either inorganic (chloride, carbonate, hydrogen carbonate, sulfate, hydrogen sulfate, hydroxide, silicate, phosphate, hydrogen phosphate, etc.) or organic (aspartate, formate, acetate, lactate, citrate, gluconate, succinate, malate, fumarate, orotate, etc.).
  • the cations composing these salts, associated with the above anions may be derived either from alkali metals (preferably lithium, sodium or potassium), from alkaline- earth metals (preferably magnesium or calcium) or from transition metals (scandium, titanium, vanadium, manganese, molybdenum, iron, cobalt, nickel, copper, zinc, silver or gold). Other cations may also form salts, for instance ammoniums.
  • the cations will be chosen from alkali metals (lithium, sodium or potassium), alkaline-earth metals (magnesium or calcium), ammoniums, and also the following transition metals: manganese, molybdenum, iron, copper, zinc, silver and gold.
  • the cosmetically acceptable medium generally comprises at least water or a mixture of water and of at least one organic solvent.
  • organic solvents include Ci-C 4 lower alkanols, such as ethanol and isopropanol; polyols such as 1 ,3-propanediol or 1 ,6-hexanediol and polyol ethers, for instance 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the solvents are preferably present in proportions preferably of between 1 % and 99% by weight relative to the weight of the composition and even more preferentially between 5% and 95% by weight relative to the weight of the composition.
  • composition used in the process according to the invention may also contain various adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, mineral or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents, for instance volatile or non-volatile, modified or unmodified silicones such as amino silicones, film-forming agents, ceramides, preserving agents, opacifiers and conductive polymers.
  • adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric
  • the above adjuvants are generally present in an amount for each of them of between 0.01 % and 20% by weight relative to the weight of the composition.
  • the pH of the composition is generally between 3 and 14 approximately, preferably between 4 and 1 1 approximately and more preferentially between 6 and 1 1 .
  • lt may be adjusted to the desired value by means of acidifying or basifying agents customarily used in the dyeing of keratin fibres, or alternatively using standard buffer systems.
  • acidifying agents are mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
  • basifying agents examples that may be mentioned include aqueous ammonia, alkali metal carbonates and the amines mentioned previously.
  • the composition may be in various forms, such as in the form of a liquid, a cream or gel, powders to be mixed before use to obtain poultices, infusions, or in any other form that is suitable for dyeing keratin fibres, and especially the hair.
  • ingredients of the abovementioned composition are advantageously stored separately.
  • the compound of formula (I) or (II) or plant extract comprising the same and the aldehyde or imine compound(s) or the oxidized oligo- or polysaccharide containing an aldehyde or imine function are stored separately.
  • composition used in the process according to the invention may also comprise one or more oxidizing agents. In this case, it is referred to as a ready-to-use composition.
  • Oxidizing agent oxidizing agent
  • the ready-to-use composition is advantageously obtained by the extemporaneous mixing, before application, of a composition described previously with at least one composition comprising one or more oxidizing agents.
  • the oxidizing agent is preferably chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates and percarbonates of alkali metals or alkaline-earth metals, such as sodium, potassium and magnesium.
  • Oxidizing agents that are also suitable for use include those of enzymatic type, for instance 4-electron oxidoreductases (such as laccases), 2-electron oxidoreductases (such as uricase), where appropriate in the presence of the respective donor or cofactor thereof, and peroxidases.
  • 4-electron oxidoreductases such as laccases
  • 2-electron oxidoreductases such as uricase
  • This oxidizing agent is advantageously formed by hydrogen peroxide in aqueous solution (aqueous hydrogen peroxide solution), the titer of which may range more particularly from 1 to 40 volumes and even more preferentially from 5 to 40 volumes.
  • composition used in the invention may result from the extemporaneous mixing of several compositions.
  • composition that has just been described is thus applied to human keratin fibres, in particular the hair.
  • the applied composition does not comprise any oxidizing agent.
  • composition does not comprise an oxidation dye (bases or couplers).
  • the ready-to-use composition that has just been detailed and that is obtained by extemporaneous mixing, before application, of the composition described previously free of oxidizing agent with an oxidizing composition, is applied to the fibres.
  • composition comprises one or more oxidation dyes (bases or couplers) or when it is desired to obtain a lightening effect.
  • the composition free of oxidizing agent and an oxidizing composition are applied successively and without intermediate rinsing.
  • the oxidizing composition used comprises one or more oxidizing agents as defined above.
  • the pH of the oxidizing composition is less than 7.
  • the oxidizing composition may take the form of a solution, an emulsion or a gel. It may optionally comprise one or more additives conventionally used in the field of dyeing human keratin fibres, as a function of the desired galenical form. Once again, reference may be made to the list of additives given above.
  • the mixture applied to the fibres is left in place for a time generally from about 1 minute to 5 hours and preferably from 10 minutes to 3 hours.
  • the temperature at which the composition(s) are applied it is generally between 20 and 200°C and advantageously between 20°C and 55°C.
  • This operation may thus be performed using, for example, a heating hood, an infrared lamp or a straightening or curling iron.
  • the process according to the invention may advantageously be performed in the presence of a light stimulus.
  • UVA radiation in particular an irradiance of between 0.01 and 0.40 milliwatt/cm 2 and preferably between 0.1 and 0.2 milliwatt/cm 2 , delivered by continuous-spectrum lamps or line- spectrum lamps
  • UVB radiation in particular an irradiance of between 0.01 and 0.20 milliwatt/cm 2 and preferably between 0.01 and 0.1 milliwatt/cm 2 delivered by continuous-spectrum lamps or by line-spectrum lamps.
  • these compounds are alkali metal, alkaline-earth metal or ammonium, carbonate, hydrogen carbonate, chloride, sulfate, silicate, monobasic phosphate or acetate salts.
  • this stimulus is performed by using a composition
  • a composition comprising, in a cosmetically acceptable medium, at least one salt chosen from lithium, sodium, potassium, calcium or ammonium carbonate; sodium or potassium hydrogen carbonate; calcium, lithium or sodium chloride; ammonium, sodium or magnesium sulfate; sodium silicate; monobasic sodium or potassium phosphate; sodium acetate.
  • the composition advantageously has a salt content ranging from 0.001 % to 40% by weight relative to the weight of the composition, and even more preferentially between 0.001 % and 20% by weight relative to the weight of the composition.
  • a final subject of the invention consists of a multi-compartment device comprising a first compartment containing at least one compound of formula (I) and/or (II) or the plant extract comprising the same, and a second compartment containing at least one compound of formula (i) or (ii), an oxidized oligo- or polysaccharide comprising at least one aldehyde or imine function.
  • the compound(s) of formula (l)/(ll) or the plant extract comprising the same are stored protected from air, advantageously under an inert atmosphere.
  • the device may optionally comprise a third compartment comprising one or more amines, or one or more salts.
  • a third compartment comprising one or more amines, or one or more salts.
  • the dye compositions are obtained by dissolving with a sonicator for 30 minutes the extract of Genipa americana (10 g%), 9.4% enriched in genipin and vanillin (1 .5 g%) in an aqueous solution.
  • the extract is obtained by performing the following method:
  • Unripe Genipa americana fruit 100 g is chopped into pieces, frozen, lyophilized and then ground, before being extracted with milliQ water.
  • the suspension is stirred for 1 hour at room temperature.
  • the starting material is then separated from the solvent by centrifugation at 7500 rpm for 15 minutes, and the supernatant is then filtered through a Whatman GF/C filter.
  • This filtered extract is then frozen, and then lyophilized.
  • HPLC analysis indicates that the extract is enriched in genipin to an amount of
  • the organic and/or inorganic salts are added to the compositions.
  • the composition is again ultrasonicated for 15 minutes.
  • composition is applied to grey hair containing 90% white hairs (1 g of lock per 5 g of solution) and the said locks are placed for 2 hours at 40°C (hotplate).
  • the dye compositions are obtained by dissolving with a sonicator for 20 minutes the extract of Genipa americana (5x10 "3 mol%), 9.4% enriched in genipin and the ingredient (10 "2 mol%) in a mixture of benzoic acid, benzyl alcohol, ethanol and water; the pH of the composition being of 9.5 (addition of NaOH ; 0.1 M)
  • composition is applied to natural and/or permanent-waved grey hair containing 90% white hairs (1 g of lock per 10 g of solution) and the said locks are placed for 30 minutes at 50°C (hotplate).
  • the dye compositions are obtained by dissolving with a sonicator for 20 minutes the extract of Genipa americana (3g%), 9.4% enriched in genipin and vanillin (0.4g%) if present, in water; the pH of the composition being of 8 (addition of KHC0 3 ).
  • composition is applied to natural grey hair containing 90% white hair (1 g of lock per 5 g of solution) and the said locks are placed for 60 minutes at 30°C (hotplate).
  • the imine is prepared by reacting vanillin (0.4g%) in a mixture of water (5ml) / ethanol (1 ml), with 3-aminopropanol (0.2g%) in the presence of acetic acid, during 30 minutes at ambient temperature.
  • the resulting imine is then added to the extract of Genipa americana (3g%), 9.4% enriched in genipin.
  • the pH of the composition is then adjusted to 8 by addition of KHC0 3 and then put in a sonicator during 20 minutes.
  • composition is applied to natural grey hair containing 90% white hair (1 g of lock per 6 g of solution) and the said locks are placed for 60 minutes at 40°C (hotplate).
  • the colour of hair is dark blue.
  • the dye composition is obtained by dissolving with a sonicator for 20 minutes the extract of Genipa americana (3g%), 9.4% enriched in genipin and oxidized inulin (0.3g%) in an aqueous solution at a pH of 8 (addition of KHC0 3 ).
  • composition is applied to natural grey hair containing 90% white hair (1 g of lock per 5 g of solution) and the said locks are placed for 60 minutes at 40°C (hotplate).
  • the hair is coloured in golden yellow.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une composition pour colorer des fibres de kératine humaine, comprenant dans un milieu acceptable au plan cosmétique : un composé de formule (I) et/ou de formule (II) ci-dessous, ou un extrait végétal le comprenant : avec R1 : hydrogène, (hydroxy)méthyle, aldéhyde, -CO2R4 et R4 : hydrogène, alkyle, - CH2-glucose; R2 : hydrogène, hydroxyle, glucose; R3 : hydrogène, hydroxyle, alkyloxy; n compris entre 1 et 5; R5 : -C02R'6 et R'6 : hydrogène, alkyle, cation; au moins un composé aldéhyde ou imine de formules (i) et (ii), et également un oligo- ou polysaccharide oxydé comprenant au moins une fonction aldéhyde ou imine : avec n égal à 0 ou 1; X : O, NR'-1 ; A : COOH, aryle éventuellement substitué, hétérocycle à 5 ou 6 chaînons saturé ou insaturé cationique ou non cationique comprenant un ou deux hétéroatomes, alkyle, alcényle éventuellement substitué; A2 alkylène divalent; les composés étant éventuellement, dans le cas des aldéhydes, sous forme acétal ou hémiacétal. L'invention concerne également un procédé employant une telle composition et un dispositif multicompartiment comprenant un premier compartiment contenant au moins un composé de formule (I) et/ou (II) ou un extrait végétal le comprenant, et un deuxième compartiment contenant au moins un composé de formule (i) ou (ii), un oligo- ou polysaccharide oxydé comprenant au moins une fonction aldéhyde ou imine.
PCT/EP2012/069365 2011-09-29 2012-10-01 Composition de colorant comprenant un composé iridoïde non glycosylé et un aldéhyde ou une imine particulier, procédé de coloration et dispositif associé WO2013045703A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020147011554A KR102065332B1 (ko) 2011-09-29 2012-10-01 비글리코실 이리도이드 화합물 및 특정한 알데히드 또는 이민을 포함하는 염료 조성물, 이를 사용하는 염색 방법 및 이를 위한 장치
JP2014532432A JP6612026B2 (ja) 2011-09-29 2012-10-01 非グリコシルイリドイド化合物及び特定のアルデヒド又はイミンを含む染料組成物、染色方法、並びにそのための装置

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR1158743A FR2980699B1 (fr) 2011-09-29 2011-09-29 Composition de coloration comprenant un compose iridoide non glycosyle et un aldehyde ou imine particulier, procede de coloration, et dispositif
FR1158743 2011-09-29
US201161548362P 2011-10-18 2011-10-18
US61/548,362 2011-10-18

Publications (1)

Publication Number Publication Date
WO2013045703A1 true WO2013045703A1 (fr) 2013-04-04

Family

ID=45524688

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/069365 WO2013045703A1 (fr) 2011-09-29 2012-10-01 Composition de colorant comprenant un composé iridoïde non glycosylé et un aldéhyde ou une imine particulier, procédé de coloration et dispositif associé

Country Status (4)

Country Link
JP (1) JP6612026B2 (fr)
KR (1) KR102065332B1 (fr)
FR (1) FR2980699B1 (fr)
WO (1) WO2013045703A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3111814B1 (fr) * 2020-06-30 2023-10-20 Oreal Procédé de coloration des fibres kératiniques à partir de poudre et/ou extrait colorant de plantes indigofères et de composés comportant au moins un groupement carbonyle

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0440494A2 (fr) 1990-02-02 1991-08-07 Tokiwa Kanpo Pharmaceutical Co., Ltd. Teinture de cheveux
JPH05339134A (ja) * 1992-06-05 1993-12-21 Kii Kasei Kk 染毛剤
FR2842200A1 (fr) 2002-07-12 2004-01-16 Centre Nat Rech Scient Procede pour l'obtention de polysaccharides modifies
FR2854161A1 (fr) 2003-04-28 2004-10-29 Centre Nat Rech Scient Derives de polysaccharides cristallins, procedes pour leur obtention et leurs applications
WO2005105020A2 (fr) 2004-05-04 2005-11-10 Vedic Hindus-Indústria, Comércio, Importação E Exportação Ltda. Procede d'elaboration de compose pour le dessin de tatouage non permanent, et procede d'utilisation du compose
US20090246343A1 (en) * 2008-03-28 2009-10-01 Wild Flavors, Inc. Stable Natural Color Process, Products and Use Thereof
WO2010076545A1 (fr) * 2008-12-31 2010-07-08 Lvmh Recherche Matieres colorantes et leur utilisation dans des compositions, en particulier des compositions cosmetiques

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53134824A (en) * 1977-04-28 1978-11-24 Taito Kk Novel nitrogenncontaining monoterpene derivative
JPH0660089B2 (ja) * 1990-01-23 1994-08-10 六郎 清原 染毛化粧料
JPH0425723A (ja) * 1990-05-21 1992-01-29 Shiseido Co Ltd 紫外線強度測定素子
JP2873518B2 (ja) * 1991-09-03 1999-03-24 台糖株式会社 クチナシ赤色系色素の製造方法
DE19618595A1 (de) * 1996-05-09 1997-11-13 Wella Ag Färbemittel
FR2870731B1 (fr) * 2004-05-28 2006-07-28 Oreal Composition pour la coloration des fibres keratiniques comprenant un pigment et des polymeres aptes a reagir l'un avec l'autre pour former des liaisons covalentes
KR101191005B1 (ko) * 2009-12-31 2012-10-16 배영애 파마겸 염모 키트 및 그를 이용한 파마겸 염모방법

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0440494A2 (fr) 1990-02-02 1991-08-07 Tokiwa Kanpo Pharmaceutical Co., Ltd. Teinture de cheveux
JPH05339134A (ja) * 1992-06-05 1993-12-21 Kii Kasei Kk 染毛剤
FR2842200A1 (fr) 2002-07-12 2004-01-16 Centre Nat Rech Scient Procede pour l'obtention de polysaccharides modifies
FR2854161A1 (fr) 2003-04-28 2004-10-29 Centre Nat Rech Scient Derives de polysaccharides cristallins, procedes pour leur obtention et leurs applications
WO2005105020A2 (fr) 2004-05-04 2005-11-10 Vedic Hindus-Indústria, Comércio, Importação E Exportação Ltda. Procede d'elaboration de compose pour le dessin de tatouage non permanent, et procede d'utilisation du compose
US20090246343A1 (en) * 2008-03-28 2009-10-01 Wild Flavors, Inc. Stable Natural Color Process, Products and Use Thereof
WO2010076545A1 (fr) * 2008-12-31 2010-07-08 Lvmh Recherche Matieres colorantes et leur utilisation dans des compositions, en particulier des compositions cosmetiques

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
E. FREDON ET AL.: "Hydrophobic films from maize bran hemicelluloses", CARBOHYDRATE POLYMERS, vol. 49, 2002, pages 1 - 12
R. E. WING; J. L. WILLET: "water soluble oxidized starches by peroxide reaction extrusion", INDUSTRIAL CROPS AND PRODUCTS, vol. 75, 1997, pages 45 - 52
TALLENT W H: "Two New Antibiotic cyclopentanoid Monoterpenes of Plant origin", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 20, no. 7, 1 January 1964 (1964-01-01), pages 1781 - 1787, XP002627316, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(01)99179-3 *

Also Published As

Publication number Publication date
KR102065332B1 (ko) 2020-01-13
FR2980699A1 (fr) 2013-04-05
JP2014528400A (ja) 2014-10-27
JP6612026B2 (ja) 2019-11-27
FR2980699B1 (fr) 2013-09-13
KR20140084093A (ko) 2014-07-04

Similar Documents

Publication Publication Date Title
FR2957795A1 (fr) Procede de coloration mettant en jeu un derive d'iridoide glycosyle
WO2013045701A2 (fr) Procédé de coloration utilisant une composition comprenant un composé iridoïde glycosylique et un nucléophile ou un polymère aminé ou thiolé et composition et dispositifs s'y rapportant
WO2014154871A1 (fr) Procédé de teinture au moyen d'un composé iridoïde et dispositifs pour celui-ci
KR102071728B1 (ko) 글리코실 이리도이드 화합물 및 특정한 알데히드 또는 이민을 포함하는 염료 조성물, 염색 방법 및 이를 위한 장치
EP2978749A1 (fr) Composes derives d'iridoides proteges ou non, composition les comprenant, utilisation comme colorant des fibres keratiniques et dispositifs
KR102222530B1 (ko) 이리도이드로부터 수득된 모발 염색 전구체를 이용하는 염색 방법, 조성물, 전구체 및 이를 포함하는 장치
FR2957794A1 (fr) Procede de coloration mettant en jeu des colorants iridoides non glycosyles, composition tinctoriales et utilisation
WO2013045702A2 (fr) Colorant comprenant un composé iridoïde non glycosyle et un nucléophile ou un amino ou thio polymère, procédé de coloration et dispositif afférent
WO2013045703A1 (fr) Composition de colorant comprenant un composé iridoïde non glycosylé et un aldéhyde ou une imine particulier, procédé de coloration et dispositif associé
FR3003760A1 (fr) Procede de coloration utilisant un compose iridoide et dispositifs
JP4279592B2 (ja) 光活性化可能ジアジリン活性剤化合物、これを含む組成物、及びその使用
US8668745B2 (en) Brightening agent comprising acylpyridinium compounds and defined alkalizing agents
FR3059233B1 (fr) Composition tinctoriale comprenant l'acide 12-hydroxystearique, une amine organique et un colorant
FR2980700A1 (fr) Composition de coloration comprenant un compose iridoide non glycosyle et un polymere amine ou thiole, procede de coloration, et dispositif
FR2980704A1 (fr) Composition de coloration comprenant un compose iridoide glycosyle et un polymere amine ou thiole, procede de coloration et dispositifs
FR2957797A1 (fr) Procede de coloration mettant en jeu un colorant a base d'iridoide glycosyle en presence d'une base
FR2957796A1 (fr) Procede de coloration mettant en jeu un colorant a base d'iridoide non glycosyle en presence d'une base
FR2980701A1 (fr) Composition de coloration comprenant un compose iridoide non glycosyle et un nucleophile carbonyle particulier, procede de coloration, et dispositif
FR2980703A1 (fr) Composition de coloration comprenant un compose iridoide glycosyle et un nucleophile carbonyle, procede de coloration et dispositifs
US8597371B2 (en) Lightening agent comprising acyl pyridinium compounds and cationic polysaccharides
FR2980706A1 (fr) Composition de coloration comprenant un compose iridoide glycosyle et un nucleophileparticulier, procede de coloration et dispositifs
FR2980702A1 (fr) Composition de coloration comprenant un compose iridoide non glycosyle et un nucleophile particulier, procede de coloration, et dipositif

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12770104

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2014532432

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20147011554

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 12770104

Country of ref document: EP

Kind code of ref document: A1