EP2083791A2 - Zusammenstzung zur färbung von keratinmaterial mit einem supramolekularen färbesystem - Google Patents

Zusammenstzung zur färbung von keratinmaterial mit einem supramolekularen färbesystem

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Publication number
EP2083791A2
EP2083791A2 EP07866440A EP07866440A EP2083791A2 EP 2083791 A2 EP2083791 A2 EP 2083791A2 EP 07866440 A EP07866440 A EP 07866440A EP 07866440 A EP07866440 A EP 07866440A EP 2083791 A2 EP2083791 A2 EP 2083791A2
Authority
EP
European Patent Office
Prior art keywords
substituted
group
unsubstituted
sau
hydrogen atom
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP07866440A
Other languages
English (en)
French (fr)
Inventor
Nicolas Daubresse
Timo Luukas
Sandrine Chodorowski-Kimmes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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 LOreal SA filed Critical LOreal SA
Publication of EP2083791A2 publication Critical patent/EP2083791A2/de
Withdrawn legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966Triazines or their condensed derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair

Definitions

  • the subject of the present invention is a cosmetic dyeing composition for keratin materials, comprising, in a suitable medium, at least one supramolecular dyeing system, in particular a cosmetic composition for dyeing human keratin fibers such as the hair or a makeup composition for the materials.
  • keratin such as lips, eyelashes, skin and nails.
  • This staining technique consists in applying to the keratinous fibers a composition containing dye precursors such as oxidation bases and couplers. These precursors under the action of an oxidizing agent will form in the hair one or more colored species.
  • oxidation bases and couplers allow to obtain a rich palette of colors.
  • the resulting colorations are permanent, strong, and resistant to external agents, including light, weather, washing, perspiration and friction.
  • the coloring is carried out using oxidizing products such as hydrogen peroxide in basic medium. These oxidizing agents attack hair keratin, the cosmetic and mechanical properties of which can deteriorate greatly in the case of repeated staining, which can lead to difficult styling or shaping.
  • oxidizing agents attack hair keratin, the cosmetic and mechanical properties of which can deteriorate greatly in the case of repeated staining, which can lead to difficult styling or shaping.
  • the standard dyes that are used are in particular nitrobenzene, anthraquinone, nitropyridine, azo, azo, xanthene, acridine, azine or triarylmethane dyes or natural dyes. These dyes may be nonionic, anionic, cationic or amphoteric. These dyes are colored molecules and dyes having an affinity for keratinous fibers.
  • the colorations that result are particularly chromatic colorations that are however temporary or semi-permanent because the nature of the interactions that bind the direct dyes to the keratinous fiber, and their desorption of the surface and / or the core of the fiber are responsible for poor resistance to washing or perspiration.
  • coloring compositions which make it possible to obtain colorations having a toughness close to the oxidation coloring without the disadvantages associated with the presence of an oxidizing agent.
  • a cosmetic composition for coloring keratin materials comprising in a suitable medium, a supramolecular dye system, the dye system comprising either
  • (COLOR) is any chromophore with a maximum absorption of between 300 nm and 1200 nm, covalently bonded to (SAU),
  • SAU represents an acceptor / donor radical capable of forming at least three hydrogen bonds, and capable of associating under appropriate conditions, ie
  • radicals (COLORANT) or (COLORANT') may be the same or different.
  • m or m 'or p is greater than 1, the radicals (SAU), (SAU') or (SAU '') may be identical or different.
  • a composition which makes it possible to obtain a coloration of the keratinous materials having good dyeing properties while respecting these keratin materials such as the hair, the eyelashes, lips, nails and skin.
  • a composition makes it possible to obtain a tenacious but easily erasable coloring by the cancellation of the non-covalent interactions connecting the various dyes of formulas (I) and / or (I ').
  • the composition of the invention makes it possible to obtain better properties such as stability to light, water, perspiration and washes, as well as an ease of erasing the color due to the reversibility of the existing interactions in such a molecular system.
  • the dyes of formula (I) and / or (I ') and the compounds of formula (II) useful in the composition of the invention are for example described in patent application EP 1 310 533 and EP 1 486 539.
  • the self-assembly process can take place between the dyes (I) and / or (I ') but also between the dyes of formula (I) and / or (I') and compounds of formula (II) having no dye moiety.
  • chromophores useful in the present invention mention may be made of the radicals derived from acridine dyes, acridones, anthranthrones, anthrapyrimidines, anthraquinones, azines, azo, azomethines, benzanthrones, benzimidazoles, benzimidazolones, benzindoles, benzoxazoles, benzopyrans, benzothiazoles, benzoquinones, bisazines, bis isoindolines, carboxanilides, coumarins, cyanines (azacarbocyanine, diazacarbocyanine, diazahemicyanine, hemicyanine, tetraazacarbocyanine, diazines, diketopyrrolopyrroles, dioxazines, diphenylamines, diphenylmethanes, dithiazines, flavonoids such as flavanthrones and flavones, fluorindines,
  • nitro chromophores that may be used according to the invention, mention may be made, in a nonlimiting manner, of the radicals derived from the following dyes: -1,4-diamino-2-nitrobenzene
  • azo chromophores the following compounds, described in the Color Index International 3rd edition: Disperse Red 17 Yellow -Acid 9 -Acid Black 1 -Acid 36 -Acid Yellow Orange Red -Acid 7 33 35 Red -Acid Acid Yellow 23 -Acid Orange 24 -Disperse Black 9. Mention may also be made of 1- (4'-aminodiphenylazo) -2-methyl-4bis- ( ⁇ -hydroxyethyl) aminobenzene and 4-hydroxy-3- acid ( 2-methoxyphenylazo) -1-naphthalene sulfonic acid. Among the quinonic chromophores, mention may be made of the radicals resulting from the following dyes: -Disperse Red 15
  • indoamine chromophores that can be used according to the invention, mention may be made of the radicals derived from the following dyes:
  • Preferred chromophores are those absorbing light between 380 nm and 850 nm.
  • radical "SAU” or “SAU” or “SAU” is an acceptor / donor radical which can form at least three hydrogen bonds, preferably 3 or 4 hydrogen bonds.
  • radicals "SAU” or "SAU” can be found, without limitation, in the publications: Chem. Soc. Rev., 2001, 30, pp. 83-93; Tetrahedron, 57 (2001), pages 1139-1159; J. Am. Chem. Soc., 2001, 123, pages 409 to 416; Adv. Mater., 2000, 12, No. 12, pages 874-878; Chem. Eur. J., 2001, 7, No. 10, pages 2059-2065; J. Am. Chem. Soc., 2000, 122, 5006-5007; Chem.
  • the radical (SAU) or (SAU ') or (SAU' ') comprises rings with 5 or 6 atoms, these rings being (hetero) aromatic or unsaturated heterocycles.
  • these rings consist of C and / or atomes atoms and with conjugated double bonds to stabilize and direct the H interactions.
  • the radical is N-(2-aminoethyl)-2-aminoethyl radical
  • (SAU) or (SAU ') or (SAU' ') have 6-atom rings comprising C and / or ⁇ and with conjugated double bonds to stabilize and direct the H interactions.
  • the radical (SAU) or (SAU ') or (SAU' ') is preferably chosen from the radicals derived from the compounds
  • aminopyrimidones aminopyrimidones, ureidopyrimidones, trimellitic acid,
  • acylaminopyridines ureidopyridines, carbamoylpyridines, acylaminotriazines, ureidotriazines, and especially ureidoaminotriazines, acylaminoaminotriazines,
  • phthalhydrazides 2-aminopyrimidine-4,6 (1H, 5H) -diones, and / or 4,6-diaminopyrimidin-2 (1H) -ones substituted on their position, respectively, with a carbon radical, in particular alkylene radical; , linear, branched or cyclic, C 1 -C 20 saturated or unsaturated, optionally aromatic, which may contain one or more heteroatoms; and derivatives of these compounds as well as tautomeric forms.
  • ureidopyrimidones ureidopyrimidones
  • ureidopyridines carbamoylpyridines
  • phthalhydrazides 2-aminopyrimidine-4,6 (1H, 5H) -diones, and / or 4, ⁇ -diaminopyrimidin-2 (1H) -ones; and their derivatives.
  • radicals (SAU) or (SAU ') or (SAU' ') when they are different and present in the same dyeing composition are chosen from the following combinations
  • Radicals (SAU) or (SAU ') or (SAU), COLORANT or COLORANT X may comprise one or more linking arms L depending on the values of n, n', m, m ', p , q) such as alkylene radicals, linear or branched, optionally substituted; optionally substituted cycloalkylene radicals; the arylenes radicals, optionally substituted;
  • amino radicals (-NH- or -NR-) or -O-, -SO-, -SO 2 - or -C (O) -; as well as their combinations of the same category and / or of different categories, leading in particular to cycloalkylene alkylenes, biscycloalkylenes, biscycloalkylenesalkylenes, arylenealkylenes, bisphenylenesalkylenes, oxyalkylenes and aminoalkylenes.
  • radicals may optionally be substituted, in particular with one or more alkyl groups in optionally comprising heteroatoms selected from O, N, S, F and P, and combinations thereof.
  • alkylene radicals there may be mentioned, for example, C 1 -C 30 alkylene radicals, for example the methylene radical -
  • (CH 2 ) n - (n> 2) such as the ethylene, butylene, especially 1,4-butylene and 1,6-hexylene radicals and the C 3 -C 10 branched alkylene radicals, such as the radicals 1, 4- (4-methylpentylene), 1, 6- (2,2,4-trimethylhexylene), 1,5-5- (5-methylhexylene), 1,6- (6-methylheptylene), 1,5- (2,2,5-trimethyl hexylene), 1,7- (3,7-dimethyl octylene), 2,2-dimethylpropylene and 1,6- (2,4,4-trimethyl hexylene).
  • cycloalkylene radicals there may be mentioned for example the cyclopentylene and cyclohexylene radicals, optionally substituted in particular with alkyl groups.
  • cycloalkylenesalkylenes mention may be made, for example, of the isophorone radical of formula:
  • n is an integer of 0 to 4; and R4, which may be identical or different, represents H or a C1-C12 alkyl radical, especially a methyl radical; 4, 4'-methylene biscyclohexylene may be mentioned in particular.
  • arylene radicals there may be mentioned, for example, the phenylene radical, the tolylene radicals, in particular the 2,4- and 2,3-tolylene radicals, and the naphthylene radicals, in particular 2,4-naphthylene or 2,6-naphthylene radicals. naphthylene.
  • arylenealkylene radicals such as the benzylene radical:
  • p is an integer of 0 to 5.
  • n an integer of 0 to 4
  • R a identical or different, represent H or a C 1 -C 4 alkyl radical, preferably a methyl radical.
  • oxyalkylene radicals optionally substituted include for example alkylene oxide radicals of the formula -O- (R 'O) y - wherein R' identical or different, represents an alkylene radical, linear or branched C2-C 4 , especially ethylene or propylene; and y is an integer of 1 to 500, preferably 1 to 200 and more preferably 5 to 100.
  • linking arms By way of example of linking arms, mention may be made of methylene, ethylene, linear or branched propylene, linear or branched butylene, linear or branched pentylene or linear or branched hexylene radicals, optionally substituted and / or interrupted as indicated above. .
  • saturated or unsaturated aromatic or non-aromatic ring or heterocycle interrupting the alkyl radical of the linking arm mention may be made of phenylene or naphthylene, phenanthrylene, triazinyl, pyrimidinyl, pyridinyl, pyridazinyl and quinoxalinyl radicals, cyclohexyl.
  • link arms mention may be made of:
  • R ' represents: an alkyl radical C ⁇ -Cl 6, optionally substituted, optionally interrupted by one or more heteroatoms or by one or more groups comprising at least one heteroatom, preferably selected from oxygen, nitrogen sulfur, such as -CO, -SO 2 or combinations thereof, a hydroxyl group, a C 1 -C 4 alkoxy group. • a (poly) hydroxyalkoxy, C 2 -C 4;
  • R represents a C 1 -C 4 alkyl radical.
  • RCO-O- alkylcarbonyloxy radical
  • R-CO- alkylcarbonyl radical in which R represents a C 1 -C 4 alkyl radical; An amino group;
  • RCO-NR'- an alkylcarbonylamino group in which the radical R represents an alkyl radical Ci-C 4 and the radical R 'represents a hydrogen atom or an alkyl radical in C 1 -C 4 alkyl;
  • An aminocarbonyl group ((R) 2 N-CO-) in which the radicals R independently of one another represent a hydrogen atom or a C 1 -C 4 alkyl radical; a ureido group (N (R) 2 -CO-NR'-) in which the radicals R and R ', independently of each other, represent a hydrogen atom or a C 1 -C 4 alkyl radical;
  • An aminosulphonyl group ((R) 2 N-SO-) in which the radicals R independently of one another represent a hydrogen atom or a C 1 -C 4 alkyl radical;
  • An alkylsulphonylamino group (RSO 2 -NR'-) in which the radicals R, R ', independently of one another, represent a hydrogen atom, a C 1 -C 4 alkyl radical;
  • R-SO- An alkylsulfinyl group (R-SO-) in which R represents a C 1 -C 4 alkyl radical; • an alkylsulfonyl group (R-SO2-) wherein R represents an alkyl radical C 4 -C;
  • a halogen atom preferably chlorine or fluorine
  • R '' are identical, represent a hydrogen, an alkyl radical Ci-C 4.
  • Rs and R 9 represent, independently of one another, a hydrogen atom, a C 1 -C 6 alkyl radical optionally substituted with one or more identical or different radicals chosen from hydroxyl and C 1 -C 2 alkoxy, ( poly) hydroxyalkoxy, C 2 - C 4, amino, (di) alkylamino-C 2 or optionally substituted aryl.
  • COLORANT Preferably, “COLORANT”, “COLORANT”, “SAU”, “SAU” and “SAU” include one to three linking arms.
  • the acid addition salts of the supramolecular dyes of the invention of formula (I) or (I ') may be by way of example the addition salts with an organic or inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid or (alkyl- or phenyl) sulfonic acids such as p-toluenesulphonic acid or methylsulphonic acid, or salts of carboxylic acids as for example acetates, lactates, benzoates, salicylates, citrates.
  • an organic or inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid or (alkyl- or phenyl) sulfonic acids such as p-toluenesulphonic acid or methylsulphonic acid
  • carboxylic acids as for example acetates, lactates, benzoates, salicylates, citrates.
  • solvates of the supramolecular dyeing systems of the invention are for example the hydrates of such systems or the combination of a compound of formula (I), (I ') or (II) (II') with a linear or branched alcohol C 3 -C 4 such as methanol, ethanol, isopropanol, n-propanol.
  • Coloranti and Colorant2 groups are as defined for "COLORANT", and R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted acyl group, substituted or unsubstituted sulfonyl group, substituted or unsubstituted phosphoryl group or group heterocyclic, L represents a linker as defined above.
  • n 2 and O 2 are the same or different and greater than or equal to 1; m 2 can be greater than or equal to 0,
  • R1 and R2 are the same or different and represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted sulfoxy group, a substituted sulfone group or unsubstituted, substituted or unsubstituted amino group, nitrile group, saturated or unsaturated, substituted or unsubstituted alkyl group, substituted or unsubstituted acyl group, substituted or unsubstituted sulfonyl group, substituted or unsubstituted aryl group a substituted or unsubstituted aralkyl group, a heterocyclic group or a "COLORING" group, or R1 and R2 represent the atoms necessary to form a ring system; Y represents a divalent COLORING group;
  • R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a heterocyclic group, a dye, OR1 or NR2R3;
  • R1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a group heterocyclic, a group Coloranti or Colorant2;
  • R2 and R3 are the same or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a heterocyclic group, a substituted or unsubstituted acyl group a substituted or unsubstituted sulfonyl group, a Coloranti or Colorant 2 group , or R2 and R3 represent the atoms necessary to form a ring with the nitrogen atom; the groups Coloranti and Colorant2 are as defined for COLORANT.
  • the groups Coloranti and Dye 2 are as defined for COLORANT.
  • Li, L 2 and L 3 are identical or different and represent a linker as defined above.
  • R represents a hydrogen atom, a substituted or unsubstituted alkyl group, an aryl group substituted or unsubstituted, an aralkyl group substituted or unsubstituted heterocyclic group, or a group Coloranti Dye 2, ENT or NR2R3;
  • R1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group or a heterocyclic group;
  • R2 and R3 are the same or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a heterocyclic group or R2 and R3 represent the atoms necessary to form a ring with the nitrogen atom; the groups Coloranti and Colorant2 are as defined for COLORANT.
  • R1 and R2 are the same or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a heterocyclic group, OR3 or NR4R5;
  • R3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group or a heterocyclic group;
  • R4 and R5 are the same or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a heterocyclic group or R4 and R5 represent the necessary atoms to form a cycle with nitrogen; the groups Coloranti and Colorant2 are as defined for COLORANT.
  • R3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group;
  • the COLORING group is as defined above and comprises a link arm;
  • L represents a link arm
  • X is 0, NR3, (CH2) n where n is at least 1;
  • R1 and R2 are the same or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted acyl group, a sulfonyl group substituted or unsubstituted, a heterocyclic group or R1 and R2 represent the atoms necessary to form with the nitrogen atom a ring;
  • R3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group;
  • the COLORING group is as defined previously
  • R 1 and R 2 are the same or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted acyl group, substituted or unsubstituted sulfonyl group, substituted or unsubstituted cycloalkyl group or heterocyclic group;
  • X is NR3 or CR4R5;
  • R3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted cycloalkyl group or a heterocyclic group;
  • R4 and R5 are the same or different and represent a hydrogen atom, a substituted or unsubsti
  • L represents a linker as defined above.
  • R1 and R2 are identical or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group; substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted heterocyclic group;
  • X is NR3 or CR4R5;
  • R3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted cycloalkyl group or a heterocyclic group;
  • R4 and R5 are the same or different and represent a hydrogen atom, a substituted or unsubstituted alkyl group
  • the coloring compositions contain at least one dye
  • the coloring compositions contain only at least one dye
  • COLOR may be the same or different.
  • compositions are formulated which contain dyes according to formula (I) and / or
  • the coloring compositions of the invention generally contain from 0.01% to 40%, preferably from 0.05% to 15%, and in particular from 0.5% to 5% by weight of the supramolecular dye system relative to the total weight of the composition
  • the medium suitable for coloring generally consists of water or comprises water and at least one organic solvent to solubilize compounds that are not sufficiently soluble in water.
  • organic solvent there may be mentioned for example lower alkanols Ci-C 4, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the solvents are preferably present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.
  • the dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in hair dyeing compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, or mixtures thereof, anionic polymers, cationic, nonionic, amphoteric, zwitterionic or their mixtures, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as as for example, volatile or nonvolatile silicones, modified or unmodified, film formers, ceramides, preservatives, opacifying agents ", oils, waxes.
  • adjuvants are generally present in an amount ranging from them between 0.01 and 20% by weight relative to the weight of the composition.
  • the pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 9 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents usually used for coloring keratin materials, especially the hair, or else using conventional buffer systems.
  • acidifying agents mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids.
  • mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids.
  • alkalinizing agents that may be mentioned, by way of example, are ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, sodium or potassium hydroxides and following formula (III):
  • W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 4 alkyl radical;
  • R a , Rb, Rc and R d identical or different, represent a hydrogen atom, an alkyl radical in C 1 -C 4 hydroxyalkyl or Ci-C 4.
  • hydrophobic dyes For more hydrophobic dyes, mention may especially be made of tripropylene glycol monomethyl ether, propylene glycol n-propyl ether, tri or dipropylene glycol mono or di alkyl ether derivatives, propylene glycol methyl ether acetate and propylene phenyl ether. glycol.
  • the dyeing composition according to the invention may be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin materials, and in particular human hair.
  • the dyeing process is such that the composition according to the present invention as defined above is applied to the fibers for a time sufficient to obtain the desired effect.
  • the materials on which the composition is applied may be dry or wet.
  • the coloration of the keratin materials is obtained during the formation of supramolecular systems by formation of hydrogen bonds.
  • the formation of the supramolecular dye system can be obtained spontaneously by evaporation, for example from the water contained in the dyeing medium. This formation of the supramolecular dye system can be promoted by the presence of particular compounds in the staining medium, for example volatile compounds, or by rinsing, washing or heating.
  • the keratinous materials thus colored can then be rinsed, washed and dried.
  • Such an application can be carried out in the presence of an oxidizing agent, this oxidizing agent can be applied simultaneously or prior to the application of the composition of the invention in order to obtain a preliminary or simultaneous lightening of the keratinous fiber.
  • the oxidizing agent is present in the composition of the invention.
  • the oxidizing agents conventionally used for the oxidation dyeing of keratinous fibers are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and oxidase enzymes. among which there may be mentioned peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred.
  • the invention also relates to a kit which contains at least a first composition comprising one or more compounds of formula (I), (I ') or (II) or (II') and a second composition comprising an oxidizing agent.
  • the kit further comprises a composition comprising the alkaline agent.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
EP07866440A 2006-10-25 2007-10-25 Zusammenstzung zur färbung von keratinmaterial mit einem supramolekularen färbesystem Withdrawn EP2083791A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0654515A FR2907674B1 (fr) 2006-10-25 2006-10-25 Composition de coloration des matieres keratiniques a partir d'un systeme colorant supramoleculaire.
US86103806P 2006-11-27 2006-11-27
PCT/FR2007/001767 WO2008059125A2 (fr) 2006-10-25 2007-10-25 Composition de coloration des matieres keratiniques a partir d'un systeme colorant supramoleculaire

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Publication Number Publication Date
EP2083791A2 true EP2083791A2 (de) 2009-08-05

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EP07866440A Withdrawn EP2083791A2 (de) 2006-10-25 2007-10-25 Zusammenstzung zur färbung von keratinmaterial mit einem supramolekularen färbesystem

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US (1) US20100242188A1 (de)
EP (1) EP2083791A2 (de)
FR (1) FR2907674B1 (de)
WO (1) WO2008059125A2 (de)

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WO2013004982A2 (fr) 2011-07-07 2013-01-10 L'oreal Procédés de traitement cosmétique et kit

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Publication number Priority date Publication date Assignee Title
WO2011083243A1 (fr) 2010-01-05 2011-07-14 L'oreal Procédés de traitement cosmétique et kit
WO2013004982A2 (fr) 2011-07-07 2013-01-10 L'oreal Procédés de traitement cosmétique et kit

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FR2907674A1 (fr) 2008-05-02
FR2907674B1 (fr) 2014-10-24
US20100242188A1 (en) 2010-09-30
WO2008059125A2 (fr) 2008-05-22
WO2008059125A3 (fr) 2008-07-24

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