WO2013045702A2 - Colorant comprenant un composé iridoïde non glycosyle et un nucléophile ou un amino ou thio polymère, procédé de coloration et dispositif afférent - Google Patents

Colorant comprenant un composé iridoïde non glycosyle et un nucléophile ou un amino ou thio polymère, procédé de coloration et dispositif afférent Download PDF

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Publication number
WO2013045702A2
WO2013045702A2 PCT/EP2012/069362 EP2012069362W WO2013045702A2 WO 2013045702 A2 WO2013045702 A2 WO 2013045702A2 EP 2012069362 W EP2012069362 W EP 2012069362W WO 2013045702 A2 WO2013045702 A2 WO 2013045702A2
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radical
hydrogen atom
alkyl radical
amino
group
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PCT/EP2012/069362
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English (en)
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WO2013045702A3 (fr
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Hervé David
Gwenaëlle JEGOU
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L'oreal
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Priority claimed from FR1158745A external-priority patent/FR2980700A1/fr
Priority claimed from FR1158747A external-priority patent/FR2980701B1/fr
Priority claimed from FR1158748A external-priority patent/FR2980702B1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2013045702A2 publication Critical patent/WO2013045702A2/fr
Publication of WO2013045702A3 publication Critical patent/WO2013045702A3/fr

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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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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]
    • 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

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 nucleophilic compound or at least one amino or thio polymer, at least one particular salt, and also to a dyeing process using such a composition.
  • 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), extracted from plants such as Rubiaceae, Euphorbiaceae, Valerianaceae, Cornaceae, Gentianaceae, Caprifoliaceae, Oleaceae, Ericaceae, Loganiaceae, etc.
  • a composition comprising at least one compound of (seco)iridoid-glycoside or non-glycosyl (seco)iridoid (also known as aglycone), extracted from plants such as Rubiaceae, Euphorbiaceae, Valerianaceae, Cornaceae, Gentianaceae, Caprifoliaceae, Oleaceae, Ericaceae, Loganiaceae, etc.
  • 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 carbonyl nucleophilic compound.
  • 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 -CH 2 -glucose group;
  • 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 or a (CrC 4 )alkyloxy radical; the number of hydroxyl groups not being greater than 2;
  • R 5 represents a group -C0 2 R'6 in which R' 6 represents a hydrogen atom, a
  • R 6 represents a hydrogen atom or a group -C0 2 R'6 in which R' 6 represents a hydrogen atom, a C1-C2 alkyl radical, an alkali metal cation or an ammonium group;
  • R b represents a hydrogen atom, an acetyl group (CH 3 CO-); one of the two radicals R b representing a hydrogen atom, or alternatively two radicals R b representing a phenylmethylenyl group, the phenyl radical being optionally substituted with at least one hydroxyl or C1-C4 alkoxy radical;
  • A-i , B-i , ⁇ and ⁇ which may be identical or different, represent:
  • R-i represents a C1-C4 alkyl radical optionally substituted with a hydroxyl group, a group -Si(R 2 )(OSi(R 3 )3)3 in which R 2 and R 3 , which may be identical or different, represent a C1-C4 alkyl radical, preferably methyl;
  • R 5 an ammonium group -N + (R 5 ) 3 in which R 5 , which may be identical or different, represent a C1-C4 alkyl radical optionally bearing at least one hydroxyl group;
  • halogen atom preferably chlorine
  • an unsaturated or aromatic 5- or 6-membered heterocycle comprising at least one heteroatom, preferably oxygen; o a pyridynyl or pyridinium group; the quaternized nitrogen atom being substituted with a C1-C4 alkyl radical optionally bearing a hydroxyl group; o a C1-C4 alkyl group;
  • the groups A and B possibly forming together a 5- or 6-membered ring or heterocycle optionally comprising a heteroatom, preferably oxygen; the said ring or heterocycle being optionally fused to a phenyl radical optionally substituted with at least one acetyl (CH 3 CO-), ester -COOR 6 or -OCOR 6 group with R 6 representing a C1-C4 alkyl radical;
  • a 2 and B 2 which may be identical or different, represent:
  • o a linear or branched C1-C10 alkyl radical, possibly containing one or more unsaturations, optionally substituted with a group -SiR 3 , the radicals R, which may be identical or different, representing a C1-C4 alkyl radical; o a C 3 -C 6 alkenyl radical;
  • n is an integer from 0 to 3; the unsubstituted carbon atoms bear a hydrogen atom;
  • B represents -CR'23- or O;
  • R'23 represents a hydrogen atom or R 2 3 ;
  • R23 which may be identical or different, represent a hydroxyl group or a C1-C4 alkyl radical optionally substituted with at least one hydroxyl group;
  • two radicals R23 borne by two adjacent carbon atoms may together form a fused aromatic ring optionally substituted with at least one C1-C4 alkoxy radical or a hydroxyl group;
  • R24 which may be identical or different, represent a hydrogen atom or a linear or branched C1-C4 alkyl radical
  • the compounds of formulae (a1 ) to (d1 ) comprising, where appropriate, a cosmetically acceptable anion or mixture of anions An, ensuring the electrical neutrality of the formulations;
  • carbonyl nucleophilic oligomers or polymers chosen from polymalonic acids and esters thereof, polysuccinic acids and sulfoacetic acid polymers, or mixtures thereof.
  • nucleophile type chosen from the compounds having the following formulae, optical or geometrical isomers thereof, organic or mineral acid salts thereof, and solvates thereof:
  • * n is an integer from 0 to 4; the unsubstituted carbon atoms bear a hydrogen atom;
  • * A represents -CR- ⁇ -, -N- or -N + R i with R-n representing a CrC 4 alkyl radical;
  • R 7 which may be identical or different, represent:
  • two radicals R 7 located ortho to each other may form a 5- or 6-membered heterocycle comprising 1 or 2 heteroatoms chosen from oxygen and nitrogen or a combination thereof,
  • R 8 and Rio which may be identical or different, represent:
  • Ci-C 4 alkyl radical optionally substituted with at least one group - COOR12 or -OCOR12 with R 12 representing a C C 4 alkyl radical, a group - COR1 3 with R 13 representing a C C 4 alkyl radical,
  • R 14 representing a hydrogen atom, a Ci-C 4 alkyl radical optionally substituted with at least one C C 4 alkoxy group;
  • R1 0 is not a hydroxyl group
  • R 9 represents a hydrogen atom, a C C 4 alkyl radical, a (Ci-C 4 )alkylcarbonyl group; an acetyl radical;
  • radicals R 8 and Rg may form a 5- or 6-membered heterocycle optionally comprising another heteroatom chosen from oxygen, nitrogen and sulfur, the said heterocycle also possibly being interrupted with a CO group,
  • Rg is not a hydrogen atom or a methyl group
  • A' represents S, -(CRi 8 )2- or with R 18 representing a hydrogen atom or a Ci-C 4 alkyl radical, Ri 9 and R'i 9 , which may be identical or different, represent a hydrogen atom or a Ci-C 4 alkyl radical;
  • R 15 which may be identical or different, represent a Ci-C 4 alkyl radical, a halogen atom, preferably chlorine, or a Ci-C 4 alkoxy radical;
  • R 15 ' which may be identical or different, represent a Ci-C 2 alkyl radical
  • Ri6 represents a hydrogen atom or a C 1 -C4 alkyl radical
  • Ri6' represents a hydrogen atom or a C 1 -C4 alkyl radical
  • Ri 7 represents a C 1 -C4 alkyl radical optionally bearing a hydroxyl group
  • radicals Ri 6 and R1 7 may together form a 5- or 6-membered fused heterocycle, optionally containing one or more unsaturations, optionally substituted with at least one C 1 -C4 alkyl radical;
  • n' is an integer from 0 to 2; the unsubstituted carbon atoms bear a hydrogen atom;
  • R 2 o which may be identical or different, represent a C1-C4 alkyl radical, a halogen atom (preferably chlorine, bromine or iodine), a radical -COOR21 or - OCOR21 with R21 representing a hydrogen atom, a C1-C4 alkyl radical, an amino radical, or a C 6 aryl group (phenyl) optionally substituted with at least one hydroxyl radical;
  • X represents N, CR 22 or -CR' 22 -CO-, CR' 22 being linked to Y or to X;
  • R22, R'22 and R" 2 which may be identical or different, represent a hydrogen atom, a linear or branched C1-C4 alkyl radical optionally substituted with an amino radical, a benzyl radical, a phenyl radical, -COOR23 or -OCOR23, R23 representing a C1-C4 alkyl radical, -SOR 24 in which R 24 represents a C1-C4 alkyl radical;
  • R22 and R' 22 may together form a fused 6-membered aromatic ring
  • * t is an integer between 0 and 4.
  • R represents a hydrogen atom or a C1-C4 alkyl radical, at least one of the radicals R representing at least one hydrogen atom;
  • halogen chosen from chlorine, bromine and fluorine
  • R M 27 represents a hydrogen atom, a Ci-C 4 alkyl radical or a phenyl radical
  • R 2 8 represents a hydrogen atom or a linear Ci-C 4 alkyl radical
  • radicals R 2 7 located ortho to the radical NHR 28 and R 28 may together form a 5- or 6-membered heterocycle comprising 1 or 2 heteroatoms chosen from oxygen and nitrogen;
  • R 29 which may be identical or different, represent a linear Ci-C 4 alkyl radical, the two radicals R 29 together possibly forming a saturated 5-membered heterocycle;
  • R 30 represent, independently of each other, a hydroxyl radical, an amino radical or a pyrrolidyl radical
  • R 31 independently of each other, represent:
  • R" 27 and R31 may form a 5- or 6-membered aromatic or non-aromatic heterocycle, optionally substituted with a Ci-C 4 alkyl radical;
  • alkali metals alkaline-earth metals, transition metals such as scandium, titanium, vanadium, manganese, iron, cobalt, nickel, copper, zinc, silver or gold, or ammoniums.
  • Another subject of the present invention is represented by a process for dyeing human keratin fibres, in which such a composition is used.
  • 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 nucleophilic compound (1 ) or (2), nucleophilic oligomers or polymers, or at least one amino or thio polymer, the composition resulting from the mixing of the compartments having an amino or thio polymer(s)/compound(s) of formulae (I) and/or (II) or plant extract comprising the same] weight ratio of at least 0.01 , if it contains such amino or thio polymer(s).
  • 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.
  • the 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, an ethoxycarbonyl radical.
  • R 6 represents a hydrogen, a hydroxycarbonyl radical, a methyoxycarbonyl radical, an ethoxycarbonyl radical.
  • the compound of formula (I) and/or formula (II) 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 , a hydrogen atom) and/or genipinic acid (R 5 represents a hydroxycarbonyl radical and R 6 , a methoxycarbonyl radical).
  • the compounds of formula (I) and/or of formula (II) 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 separation of the plant parts of the plant, enrichment or concentration operations and optionally drying, starting with natural plant substances.
  • 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 preventing oxidation of the genipin or derivatives thereof, by increasing the amount of dissolved gas.
  • the juice is then stored in airtight packaging.
  • the juice recovered may then, where appropriate, undergo a step of concentration and drying.
  • the extract used is derived from Genipa americana.
  • the extract is obtained from the 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 formulae (I) and/or (II) 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 contain additional dyes other than the abovementioned compounds of formula (I) and/or 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.
  • composition according to the invention comprises at least one carbonyl nucleophilic compound (1 ) of formulae (a1 ) to (d1 ) or at least one particular carbonyl nucelophilic polymer.
  • the carbonyl nucleophilic compound (1 ) is of abovementioned formula (a1 ), isomers thereof, salts thereof or solvates thereof, this compound being alone or as a mixture.
  • carbonyl nucleophilic compounds (1 ) are of formula (b1 )
  • these compounds are preferably such that:
  • n is an integer ranging from 0 to 2;
  • * B represents -CR'23- or O;
  • R'23 represents a hydrogen atom or R 2 3 ;
  • two radicals R23 borne by two adjacent carbon atoms may together form a fused aromatic ring optionally substituted with at least one C1-C4 alkoxy radical or a hydroxyl group;
  • R 2 which may be identical or different, represent a hydrogen atom or a linear or branched C1 alkyl radical.
  • carbonyl nucleophilic compounds of formula (d1 ) examples that may be mentioned include the following compounds, isomers thereof, salts thereof or solvates thereof, these compounds being alone or as mixtures:
  • carbonyl oligomers or polymers they are chosen from polymalonic acids and esters thereof, polysuccinic acids, sulfoacetic acid polymers, and also the salts of these polymers.
  • the carbonyl nucleophilic compound(s) (1 ) are chosen from the compounds of formula (a1 ) defined previously, and also the compounds of formulae (b1 ) and (c1 ), or mixtures thereof.
  • the content of compound(s) of formulae (a1 ) to (d1 ), or of carbonyl nucleophilic oligomers or polymers is between 0.001 % and 30% by weight relative to the weight of the composition.
  • composition according to the invention comprises at least one nucleophilic compound (2) of formulae (a2) to (d'"2) or at least one particular nucleophilic polymer.
  • the nucleophilic compound (2) is of abovementioned formula (a2), isomers thereof or salts thereof, this compound being alone or as a mixture.
  • the compounds of formula (a2) are selected from those in which:
  • n is an integer from 0 to 4; the unsubstituted carbon atoms bear a hydrogen atom;
  • A represents -CRi 0 - or -N-;
  • R 7 which may be identical or different, represent:
  • two radicals R 7 located ortho to each other may form a 5- or 6-membered heterocycle comprising 1 or 2 heteroatoms chosen from oxygen and nitrogen or a combination thereof, preferably oxygen;
  • R 8 and R10 which may be identical or different, represent:
  • C1-C4 alkyl radical optionally substituted with at least one C1-C4 alkoxy group
  • R 9 represents a hydrogen atom or a C1-C4 alkyl radical
  • R 9 is not a hydrogen atom or a methyl group.
  • nucleophilic compounds(2) corresponding to formula (b2) or (b'2)
  • the compound(s) are of formulae (b2) and (b'2) such that: * n and n' are 0; the unsubstituted carbon atoms bear a hydrogen atom; * A' represents S or -(CR 18 ) 2 - with R 18 representing a hydrogen atom or a C1-C4 alkyl radical;
  • R16 represents a hydrogen atom or a C1-C4 alkyl radical
  • Ri 7 represents a C1-C4 alkyl radical optionally bearing a hydroxyl group
  • radicals Ri 6 and R1 7 may together form a 5- or 6-membered fused heterocycle, optionally containing one or more unsaturations, optionally substituted with at least one C1-C4 alkyl radical.
  • nucleophilic compound(s) (2) are of formula (c2) such that:
  • * n' is an integer ranging from 0 to 2; the unsubstituted carbon atoms bear a hydrogen atom;
  • R 2 o which may be identical or different, represent a C1-C4 alkyl radical, a chlorine atom, a radical -COOR21 or -OCOR21 with R 2 i representing a hydrogen atom, a C1-C4 alkyl radical, an amino radical, or a phenyl group;
  • X represents N, CR22 or -CR'22 which is linked to Y or to X;
  • R22, R'22 and R" 2 which may be identical or different, represent a hydrogen atom, a linear or branched C1-C4 alkyl radical optionally substituted with an amino radical, a benzyl radical, or a phenyl radical;
  • R22 and R' 22 may together form a fused 6-membered aromatic ring.
  • nucleophilic compounds of formula (c2) examples that may be mentioned include the following compounds, isomers thereof, salts thereof or solvates thereof, these compounds being alone or as mixtures:
  • nucleophilic compound(s) of formulae (d2), (d'2), (d"2) and (d'"2) examples that may be mentioned include the following compounds, isomers thereof, salts thereof or solvates thereof, these compounds being alone or as mixtures:
  • nucleophilic oligomers or polymers they are chosen from polymers of the polyallylimidazolium type, especially those prepared from 1 -allyl-3- butylimidazolium.
  • the carbonyl compound(s) (2) are chosen from the compounds of formulae (a2), (c2), (d2), (d'2), (d"2) and (d'"2), or mixtures thereof.
  • nucleophilic compound(s) (2) of formulae (a2) to (d'"2) or of nucleophilic oligomers or polymers is between 0.001 % and 30% by weight relative to the weight of the composition.
  • amino or thio polymer means macromolecules bearing at least one primary or secondary amine function or a thiol function.
  • polymer means a compound comprising at least five repeating units linked in sequence via covalent bonds.
  • the amino or thio polymer may be synthesized via radical, anionic or cationic polymerization reactions (polyacrylates, polymethacrylates, polyvinyls, etc.), via condensation reactions (polyesters, polyethers, polyamides, polyurethanes, polydimethylsiloxanes, polypeptides, etc.) or via ring-opening reactions (polyesters, etc.).
  • polysaccharides such as cellulose, dextran, chitosan, guar, starch or inulin, and amino or thio derivatives thereof.
  • the polymers may be in the form of linear, branched, star or hyperbranched chains (for instance dendrimers).
  • the chains may be in sequenced, statistical or alternating, or block form.
  • the amine or thiol chemical groups may be naturally present on the polymer chain, at the end of the chain, included in the main chain or side chains, or as a side function on the main chain or on the side chain, on the branches of the star or hyperbranched polymers or as an end group of these branches.
  • the following are most particularly preferred:
  • alkoxysilane-based polymers containing amine functions As regards the natural or modified polysaccharides containing primary or secondary amine functions, mention may be made of chitosan and derivatives thereof, polysaccharides amino-modified via standard methods known to those skilled in the art (in particular reductive amination reactions), for instance amino cellulose, and proteins such as gelatin or collagen.
  • amino silicones denote any silicone comprising at least one primary, secondary or tertiary amine or a quaternary ammonium group.
  • x' and y' are integers that are dependent on the molecular weight, generally such that the said weight-average molecular weight is between 5000 and 500 000 approximately;
  • G which may be identical or different, denote a hydrogen atom or a phenyl, OH or C1 -C8 alkyl group, for example methyl, or a C1 -C8 alkoxy, preferably methoxy,
  • a which may be identical or different, denote the number 0 or an integer from 1 to 3, in particular 0,
  • b denotes 0 or 1 , and in particular 1 ,
  • n and n are numbers such that the sum (n + m) can range especially from 1 to 2000 and in particular from 50 to 150, it being possible for n to denote a number from 0 to 1999 and in particular from 49 to 149, and for m to denote a number from 1 to 2000 and in particular from 1 to 10;
  • n and m have the meanings given above (cf. formula b3).
  • n + m and n are numbers such that the sum (n + m) may range especially from 1 to 1000, in particular from 50 to 250 and more particularly from 100 to 200,
  • n possibly denoting a number from 0 to 999, especially from 49 to 249 and more particularly from 125 to 175 and m possibly denoting a number from 1 to 1000, especially from 1 to 10 and more particularly from 1 to 5,
  • R-i, R 2 and R 3 which may be identical or different, represent a hydroxyl or Ci-C 4 alkoxy radical, at least one of the radicals Ri to R 3 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxy/alkoxy mole ratio preferably ranges from 0.2:1 to 0.4:1 , preferably from 0.25:1 to 0.35:1 and is more particularly equal to 0.3:1.
  • the weight-average molecular mass of the silicone preferably ranges from 2000 to 1 000 000 and even more particularly from 3500 to 200 000.
  • p and q are numbers such that the sum (p + q) may range especially from 1 to 1000, in particular from 50 to 350 and more particularly from 150 to 250,
  • p possibly denoting a number from 0 to 999, especially from 49 to 349 and more particularly from 159 to 239 and q possibly denoting a number from 1 to 1000, especially from 1 to 10 and more particularly from 1 to 5,
  • Ri and R 2 which may be identical or different, represent a hydroxyl or Ci-C 4 alkoxy radical, at least one of the radicals Ri or R 2 denoting an alkoxy radical.
  • the alkoxy radical is a methoxy radical.
  • the hydroxy/alkoxy mole ratio preferably ranges from 1 :0.8 to 1 :1 .1 , preferably from 1 :0.9 to 1 :1 and is more particularly equal to 1 :0.95.
  • the weight-average molecular mass of the silicone preferably ranges from 2000 to 200 000, even more particularly from 5000 to 100 000 and more particularly from 10 000 to 50 000.
  • the weight-average molecular masses of these amino silicones are measured by gel permeation chromatography (GPC) at room temperature, as polystyrene equivalents.
  • the columns used are ⁇ styragel columns.
  • the eluent is THF and the flow rate is 1 ml/minute. 200 ⁇ of a solution containing 0.5% by weight of silicone in THF are injected. Detection is performed by refractometry and UV-metry.
  • the commercial products corresponding to these silicones of structure (d3) or (e3) may include in their composition one or more other amino silicones whose structure is different from formula (d3) or (e3).
  • a product containing amino silicones of structure (d3) is sold by the company Wacker under the name Belsil® ADM 652.
  • a product containing amino silicones of structure (e3) is sold by Wacker under the name Fluid WR 1300®.
  • n and n are numbers such that the sum (n + m) can range especially from 1 to 2000 and in particular from 50 to 150, n possibly denoting a number from 0 to 1999 and especially from 49 to 149, and m possibly denoting a number from 1 to 2000 and especially from 1 to 10;
  • A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms and preferably 4 carbon atoms. This radical is preferably linear.
  • the weight-average molecular mass of the amino silicones preferably ranges from 2000 to 1 000 000 and even more particularly from 3500 to 200 000.
  • the weight-average molecular masses of these amino silicones are measured by gel permeation chromatography (GPC) at room temperature, as polystyrene equivalents.
  • the columns used are ⁇ styragel columns.
  • the eluent is THF and the flow rate is 1 ml/minute. 200 ⁇ of a solution containing 0.5% by weight of silicone in THF are injected. Detection is performed by refractometry and UV-metry.
  • Synthetic polymers that may be mentioned in particular include polyvinyls substituted with a pendent primary or secondary amine function (such as polyallylamine, polyvinylamines and copolymers thereof) and polymers prepared from the monomers below, via a radical route:
  • alkoxysilane derivatives mention may be made in particular of polymers resulting from the condensation of at least one alkoxysilane having the following formula:
  • R a , Rb and R c which may be identical or different, denote a linear or branched C C 2 o alkoxy radical, the alkyl part of which is optionally interrupted with one or more oxygen atoms, and more particularly a linear or branched C1-C20 and preferably C1-C4 alkoxy radical,
  • the compound is (3-aminopropyl)triethoxysilane.
  • Examples that may be mentioned include the following amino or thiolic polymers:
  • polysines in particular modified by reaction between an amino polymer and homocysteine thiolactone or n-acetyl-homocysteine thiolactone or gamma-thiobutyrolactone.
  • - amino-cellulose for example those described in WO 01/25283 from BASF,
  • PAMAM poly(amidoamines) sold in particular by Dendritech, DSM and Sigma-Aldrich (Starburst, PAMAM Dendrimer, G(2, O) from Dendritech)),
  • PEI polyethyleneimine
  • BASF ethyleneimine
  • Lupasol thiol derivatives thereof
  • the polymers are chosen from amino polymers.
  • amino polymers mention may be made of the polymers of classes 1/ and 21 mentioned previously.
  • the content of amino or thiolic polymer(s) is such that the weight ratio of amino or thio polymer(s)/compound(s) of formulae (I) and/or (II), in the composition, is at least 0.01 .
  • the said weight ratio is between 0.01 -4/1 .
  • the content of amino or thio polymer(s) is between 0.1 % and 10% by weight relative to the weight of the composition.
  • 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 (II I) that will be detailed below, amino polymers, purine bases, and also the addition salts thereof, and combinations thereof.
  • formula (I I I) is as follows:
  • R' 7 and R' 8 represent, independently of each other:
  • 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; phenyl, indolyl, pyrrolyl, imidazolyl, optionally substituted with one or more Ci-C 2 alkyl or hydroxyl.
  • 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(Ci-C 2 )alkylaminocarbonyl; (Ci-C 4 )alkylcarbonylamino; phenyl, indolyl, pyrrolinyl, imidazolyl optionally substituted with one or more CrC 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 C1-C4 alkyl radical or an unsubstituted phenyl radical
  • R10 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- or 6-membered heterocycle.
  • the compounds of formula (Ilia) are advantageously chosen from 2-amino-2-methylpropanoic acid; omethyl-D,L- phenylalanine; D,L-a-(hydroxymethyl)alanine; D,L-a-methyl-meta-tyrosine; omethyl- D,L-tryptophan; D,L-a-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, (CrC 4 )alkoxycarbonyl, 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 C1-C2 alkyl group; or an unsubstituted phenyl radical;
  • R" 9 represents a hydrogen, a C1-C4 alkyl radical or an unsubstituted phenyl radical
  • R10 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- or 6-membered heterocycle.
  • 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, (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;
  • R" 9 represents a hydrogen or a C1-C4 alkyl radical optionally substituted with a hydroxysulfonyl radical
  • R10 represents a hydrogen or a C1-C 4 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 Ci-C 2 alkyl group;
  • - X represents a sulfur or nitrogen atom.
  • R 9 and Ri 2 may optionally form a saturated 5-, 6- or 7-membered carbon-based ring.
  • Ri 2 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 (I lie) represents a dipeptide or an oligopeptide.
  • Ri 3 , i4, R 15 and Ri 6 represent, independently of each other:
  • X represents a nitrogen, oxygen or sulfur atom
  • Ri7 represents:
  • R18 represents:
  • 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)butyric
  • Ri3, Ri4, Ri5, Ri6 and Ri 8 have the same meaning as previously;
  • - p is an integer between 0 and 7;
  • radical Ri 8 represents a hydrogen.
  • the radicals Ri 3 and R14 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 , R15 and Ri 6 independently of each other, a hydroxyalkyl radical, a (Ci-C 4 )alkoxycarbonyl radical, a carboxaldehyde radical, a (CrC 3 )alkoxy
  • - X represents an oxygen atom, an SH or OH group, or a methylene group optionally substituted with a hydroxyl radical; - when X represents an oxygen atom, then 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 R-I8 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.
  • - o is an integer between 0 and 5
  • - v is an integer equal to 1 or 2.
  • R 18 represents a hydrogen.
  • 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.
  • R23 and R 2 4 represent, independently of each other:
  • 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 C1-C4 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 amine(s) are chosen from amino polymers, and also addition salts thereof, in particular when the composition comprises at least one nucleophilic compound (1 ) or (2).
  • 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 NH 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 composition comprises one or more amines
  • they are chosen from ammonia, the compounds of formulae (Ilia), (1Mb), (III c), (llle) and (lllg) in particular when R 20 represents a linear Ci-C 4 alkoxy group, and (UN'), or mixtures thereof.
  • 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
  • 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, silicate, phosphate, hydrogen phosphate, hydroxide, 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.
  • 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 nonvolatile, modified or unmodified silicones such as amino silicones, film-forming agents, ceramides, preserving agents, opacifiers and conductive polymers.
  • 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 and preferably between 4 and 1 1 approximately, more preferably between 6 and 1 1. It may be adjusted to the desired value by means of acidifying or basifying agents commonly used in the dyeing of keratin fibres, or alternatively using standard buffer systems.
  • acidifying agents that may be mentioned, for example, 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.
  • 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.
  • the ingredients of the abovementioned composition are advantageously 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.
  • the ready-to-use composition 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.
  • 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 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.
  • the keratin fibres may be rinsed with water, optionally washed with a shampoo, rinsed with water and dried or left to dry.
  • 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 carbonyl nucleophilic compound (1 ) of formulae (a1 ) to (d1 ), carbonyl nucleophilic oligomer or polymer, or containing at least one nucleophilic compound (2) of formulae (a2) to (d'"2), nucleophilic oligomer or polymer, or alternatively containing at least one amino or thio polymer.
  • the compound(s) of formulae (l)/(ll) or the plant extract comprising the same are stored protected from air, advantageously under an inert atmosphere.
  • the device may optionally comprise an additional compartment comprising one or more amines; or one or more salts.
  • 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 a carbonyl compound (10 "2 mol%) in a solution comprising a mixture of benzoic acid, benzyl alcohol, ethanol and water; the pH of the composition is of 9 (addition of NaOH; 0.1 M).
  • composition is applied to natural grey hair containing 90% white hairs (1 g of lock per 12 g of solution) and the said locks are placed for 30 minutes at 50°C (hotplate).
  • the extract of Genipa americana is obtained by performing the following method:
  • the fruit of unripe Genipa americana (100 g) are chopped into pieces, frozen, freeze-dried and then ground, and are then extracted in MilliQ water.
  • the suspension is stirred for one hour at room temperature.
  • the raw 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 freeze-dried.
  • HPLC analysis indicates that the extract is enriched to a proportion of 9.4% in genipin.
  • the summary table below indicates the colorations obtained as a function of the carbonyl compounds added.
  • 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 a nucleophilic compound (10 "2 mol%) in a solution comprising a mixture of benzoic acid, benzyl alcohol, ethanol and water; the pH of the composition is of 9 (addition of NaOH; 0.1 M).
  • composition is applied to natural grey hair containing 90% white hairs (1 g of lock per 12 g of solution) and the said locks are placed for 30 minutes at 50°C (hotplate).
  • the extract of Genipa americana is obtained by performing the following method:
  • the fruit of unripe Genipa americana (100 g) are chopped into pieces, frozen, freeze-dried and then ground, and are then extracted in MilliQ water.
  • the suspension is stirred for one hour at room temperature.
  • the raw 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 freeze-dried.
  • the HPLC analysis indicates that the extract is enriched to a proportion of 9.4% in genipin.
  • the summary table below indicates the colorations obtained as a function of the nucleophilic compounds added.
  • the dye compositions are obtained by dissolving with a sonicator for 20 minutes the extract of Genipa americana (3 g%; obtained according to the same method as described in example 1 ), 9.4% enriched in genipin and a carbonyl compound (0.9%) in a solution comprising a mixture water and ethanol (resp. 4/1 ), with or without adding KHC0 3 to obtain a pH of 8.
  • the carbonyl reacts with the dye to produce the orange colour.
  • the yellow colour obtained with the comparative composition corresponds to the natural colour of the carbonyl compound, without any reaction with the genipin.
  • the dye compositions are obtained by dissolving with a sonicator for 20 minutes the extract of Genipa americana (3 g%; obtained according to the same method as described in example 1 ), 9.4% enriched in genipin and a carbonyl compound (0.62%) in water at a pH of 8 (addition of KHCO 3 ).
  • Carbonyl compound 10,10-dimethyl-7,8,9,10-tetrahydro-6H-pyrido[1 ,2- a]indolium chloride.
  • composition is applied to natural grey hair containing 90% white hairs (1 g of lock per 5 g of solution) and the said locks are placed for 30 minutes at 50°C (hotplate).
  • the dye composition is obtained by dissolving with a sonicator for 20 minutes the extract of Genipa americana (3 g%; obtained according to the same method as described in example 1 ), 9.4% enriched in genipin and polylysin (0.15g%) in water at a pH of 8 (addition of KHC0 3 ).
  • composition is applied to natural grey hair containing 90% white hairs (1 g of lock per 5 g of solution) and the said locks are placed for 60 minutes at 40°C (hotplate).
  • the resulting colour is a pale green.
  • PVP polyvinylpyrrolidone
  • the PVP (300mg) is solubilised in a prior step, in an aqueous solution comprising HCI (0.1 M) at 50°C during 1 hour;
  • the dye composition is obtained by dissolving in water with a sonicator for 20 minutes the extract of Genipa americana (3 g%; obtained according to the same method as described in example 1 ), 9.4% enriched in genipin and the PVP solution (40 ⁇ ) ; the pH is 8 (addition of KHC0 3 ).
  • composition is applied to natural grey hair containing 90% white hairs (1 g of lock per 5 g of solution) and the said locks are placed for 60 minutes at 40°C (hotplate).

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Abstract

La présente invention porte sur une composition de coloration des fibres kératiniques humaines, comprenant, dans un milieu de qualité cosmétique : *un composé de formule (I) et/ou de formule (II), ou un extrait végétal le comprenant : dans lesdites formules, R1 représente hydrogène, (hydroxy)méthyle, aldéhyde; -CO2R4 et R4 : hydrogène, alkyle; -CH2- glucose; R2 : hydrogène, hydroxyle, glucose; R3 : hydrogène, hydroxyle, alkyloxy; n valant de 1 à 5; R5: -C02R'6 et R'6 : hydrogène, alkyle, cation; ** au moins un composé nucléophile particulier ou au moins un amino ou thio polymère, selon un rapport pondéral composé(s)/amino ou thio polymère de formule (I) et/ou (II) d'au moins 0,01, *** un ou plusieurs sels organiques ou minéraux. L'invention concerne également un procédé utilisant ladite composition, ainsi qu'un dispositif à compartiments multiples.
PCT/EP2012/069362 2011-09-29 2012-10-01 Colorant comprenant un composé iridoïde non glycosyle et un nucléophile ou un amino ou thio polymère, procédé de coloration et dispositif afférent WO2013045702A2 (fr)

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
FR1158745A FR2980700A1 (fr) 2011-09-29 2011-09-29 Composition de coloration comprenant un compose iridoide non glycosyle et un polymere amine ou thiole, procede de coloration, et dispositif
FR1158747A FR2980701B1 (fr) 2011-09-29 2011-09-29 Composition de coloration comprenant un compose iridoide non glycosyle et un nucleophile carbonyle particulier, procede de coloration, et dispositif
FR1158747 2011-09-29
FR1158748 2011-09-29
FR1158748A FR2980702B1 (fr) 2011-09-29 2011-09-29 Composition de coloration comprenant un compose iridoide non glycosyle et un nucleophile particulier, procede de coloration, et dipositif
FR1158745 2011-09-29
US201161548354P 2011-10-18 2011-10-18
US201161548358P 2011-10-18 2011-10-18
US201161548376P 2011-10-18 2011-10-18
US61/548,354 2011-10-18
US61/548,376 2011-10-18
US61/548,358 2011-10-18

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Publication number Priority date Publication date Assignee Title
WO2018072723A1 (fr) * 2016-10-20 2018-04-26 大连工业大学 Colorant pour colorer des fibres de coton dans du dioxyde de carbone supercritique, procédé pour sa préparation et utilisation correspondante
US10246466B2 (en) 2014-01-24 2019-04-02 Tp Therapeutics, Inc. Diaryl macrocycles as modulators of protein kinases
US10316044B2 (en) 2015-07-02 2019-06-11 Tp Therapeutics, Inc. Chiral diaryl macrocycles as modulators of protein kinases

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US4444928A (en) 1981-08-14 1984-04-24 Ciba-Geigy Corporation Polymeric malonic acid derivatives
EP0440494A2 (fr) 1990-02-02 1991-08-07 Tokiwa Kanpo Pharmaceutical Co., Ltd. Teinture de cheveux
WO2001025283A1 (fr) 1999-09-30 2001-04-12 Basf Corporation Composes d'ester de cellulose fonctionnels amines et leurs procedes de production
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

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JPH05339134A (ja) * 1992-06-05 1993-12-21 Kii Kasei Kk 染毛剤
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JP3309221B1 (ja) * 2001-04-27 2002-07-29 株式会社コスモビューティー 染毛性整髪用組成物
JP4605947B2 (ja) * 2001-07-10 2011-01-05 ホーユー株式会社 染毛剤
US7749286B2 (en) * 2006-05-01 2010-07-06 Advanced Cosmetic Technologies, Llc Composition for dyeing keratin fibers and a method of dyeing hair using same

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US4444928A (en) 1981-08-14 1984-04-24 Ciba-Geigy Corporation Polymeric malonic acid derivatives
EP0095238A2 (fr) 1982-05-20 1983-11-30 Dow Corning Corporation Compositions utiles pour le conditionnement des cheveux
EP0440494A2 (fr) 1990-02-02 1991-08-07 Tokiwa Kanpo Pharmaceutical Co., Ltd. Teinture de cheveux
WO2001025283A1 (fr) 1999-09-30 2001-04-12 Basf Corporation Composes d'ester de cellulose fonctionnels amines et leurs procedes de production
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

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10246466B2 (en) 2014-01-24 2019-04-02 Tp Therapeutics, Inc. Diaryl macrocycles as modulators of protein kinases
US10618912B2 (en) 2014-01-24 2020-04-14 Turning Point Therapeutics, Inc. Diaryl macrocycles as modulators of protein kinases
US10316044B2 (en) 2015-07-02 2019-06-11 Tp Therapeutics, Inc. Chiral diaryl macrocycles as modulators of protein kinases
WO2018072723A1 (fr) * 2016-10-20 2018-04-26 大连工业大学 Colorant pour colorer des fibres de coton dans du dioxyde de carbone supercritique, procédé pour sa préparation et utilisation correspondante
US10745564B2 (en) 2016-10-20 2020-08-18 Dalian Polytechnic University Dye for dyeing cotton fiber in supercritical carbon dioxide, preparation method and application thereof

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