[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

EP1377261A1 - Ein kationischer azofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern - Google Patents

Ein kationischer azofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern

Info

Publication number
EP1377261A1
EP1377261A1 EP02724397A EP02724397A EP1377261A1 EP 1377261 A1 EP1377261 A1 EP 1377261A1 EP 02724397 A EP02724397 A EP 02724397A EP 02724397 A EP02724397 A EP 02724397A EP 1377261 A1 EP1377261 A1 EP 1377261A1
Authority
EP
European Patent Office
Prior art keywords
radical
amino
composition according
composition
hydroxy
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Withdrawn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
EP02724397A
Other languages
English (en)
French (fr)
Inventor
Laurent Vidal
Madeleine Leduc
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 EP1377261A1 publication Critical patent/EP1377261A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—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
    • A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/16—1,3-Diazoles or hydrogenated 1,3-diazoles ; (Benz)imidazolium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
    • C09B62/24—Azo dyes
    • C09B62/245—Monoazo dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A61K2800/4322—Direct dyes in preparations for temporarily coloring the hair further containing an oxidizing agent

Definitions

  • the subject of the invention is a new dye composition for dyeing keratin fibers, in particular human hair, containing a particular cationic azo dye, as well as the process for dyeing keratin fibers using such a composition.
  • a subject of the invention is also new azo cationic dyes.
  • oxidation bases such as ortho or paraphenylenediami ⁇ es, ortho or paraaminophenols and heterocyclic compounds.
  • oxidation bases are colorless or weakly colored compounds which, associated with oxidizing products, give rise, through an oxidative condensation process, to colored compounds.
  • couplers or color modifiers the latter being chosen in particular from aromatic metadiamines, metaaminophenols, metadiphenols and certain heterocyclic compounds such as as indole compounds.
  • This oxidation dyeing process consists in applying to the keratin fibers, oxidation bases or a mixture of oxidation bases and couplers with an oxidizing agent, for example hydrogen peroxide, to leave on, then to rinse the fibers.
  • an oxidizing agent for example hydrogen peroxide
  • the resulting colorings are permanent, powerful, and resistant to external agents, in particular to light, bad weather, washing, perspiration and rubbing.
  • Generally applied at basic pH it makes it possible to obtain a dyeing and at the same time a lightening of the fiber which translates in practice by the possibility of obtaining a final coloration lighter than, the original color.
  • the lightening of the fiber has the advantageous effect of generating a solid color in the case of gray hair, and in the case of naturally pigmented hair, of bringing out the color, that is to say making it more visible.
  • dye keratin fibers by direct coloring.
  • the method conventionally used in direct dyeing consists in applying to the keratin fibers direct dyes which are colored and coloring molecules having an affinity for the fibers, to allow to pause, then to rinse the fibers. It is known, for example, to use direct dyes of the nitro benzene, anthraquinone, nitropyridine type, dyes of the azo, xanthene, acridine azine type or triarylmethane dyes.
  • the resulting colorings are particularly chromatic colors which are however temporary or semi-permanent because the nature of the interactions which bind the direct dyes to the keratin fiber, and their desorption from the surface and / or from the core of the fiber are responsible for their low dye power and their poor resistance to washing or perspiration.
  • These direct dyes are also generally sensitive to light due to the low resistance of the chromophore vis-à-vis photochemical attacks and lead over time to a fading of the coloring of the hair. In addition, their sensitivity to light is dependent on their uniform or aggregate distribution in the keratin fiber.
  • direct dyes are generally sensitive to the action of oxidizing agents such as hydrogen peroxide, and reducing agents such as sodium bisulfite, which generally make them difficult to use in lightening direct dye compositions based on hydrogen peroxide and based on an alkalizing agent or in oxidation dye compositions in combination with precursors of the oxidation base or coupler type.
  • oxidizing agents such as hydrogen peroxide
  • reducing agents such as sodium bisulfite
  • patent application FR 2 741 798 has described dye compositions containing direct dyes comprising at least one quaternized nitrogen atom of the azo or azomethine type, said compositions being to be mixed extemporaneously at basic pH with an oxidizing composition.
  • These compositions make it possible to obtain colorings with homogeneous, tenacious and brilliant reflections. However, they do not make it possible to dye keratin fibers with as much power as with oxidation coloring compositions.
  • - W 2 represents a divalent aromatic carbon or pyridine group of formulas (III) or (IV) below
  • Z. represents an oxygen or sulfur atom or an NR 4 radical
  • - Z 2 represents a nitrogen atom or a radical CR 3 , - R 1 and R 4 independently of one another represent a C r alkyl radical
  • C 8 optionally substituted by one or more radicals chosen from a hydroxy, a C ⁇ Ca alkoxy, a (poly) hydroxy C 2 -C 4 alkoxy radical, an amino, a (di) C ⁇ Cz alkylamino, a carboxy, a sulfonic; an optionally substituted phenyl radical, - R 2 and R 3 represent, independently of one another, a hydrogen atom; a C 1 -C 4 alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, C 1 -C 2 alkoxy, a (poly) hydroxy C 2 -C 4 alkoxy an amino, a (di) alkylamino in C, i carboxy or sulfonic; an optionally substituted phenyl radical; a carboxy radical; a sulfonylamino radical;
  • R 6 R 7 R 8 and W 4 represent, independently of one another, a hydrogen atom; a chlorine atom; a bromine atom; a linear or branched C ⁇ hydrocarbon chain which can form one or more carbon rings comprising from 3 to 6 members, and which can be saturated or unsaturated, one or more carbon atoms of the hyfrocarbon chain of which can be replaced by an atom d oxygen, nitrogen or sulfur or by an SO 2 group, and the carbon atoms of which may be, independently of one another, substituted by one or more halogen atoms; R 5 , R 6 R 7 R 8 and W 4 not comprising a peroxide bond, nor of diazo or nitroso radicals, and W being a non-aromatic substituent, - W 3 represents a thienyl, pyrazolyl, pyrrolyl, imidazolyl, furyl radical, triazolyle, thiadiazolyle, isoxazolyle, isothiazolyle,
  • alkyl means, unless otherwise indicated, an alkyl radical comprising from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, which may be linear or branched.
  • alkoxy means alkyl-O-, the term alkyl having the above meaning. According to the invention, when it is indicated that one or more of the carbon atoms of the hydrocarbon chain defined for the radicals R 5 to R 8 and W 4 can be replaced by an oxygen, nitrogen or of sulfur or by a group
  • branched hydrocarbon chain means a chain which can form one or more carbon rings comprising from 3 to 6 members.
  • unsaturated hydrocarbon chain is understood to mean a chain which can comprise one or more double bonds and / or one or more triple bonds, this hydrocarbon chain can lead to aromatic groups except for W 4 .
  • the radicals R 5 , R 6 , R 7 and R 8 are preferably chosen from a hydrogen atom, a methyl, ethyl, isopropyl, methoxymethyl, hydroxymethyl, 1-carboxymethyl, 1-aminomethyl, 1-aminoethyl, 2- radical. carboxyethyl, 2-hydroxyethyl, 3-hydroxypropyl, 1, 2-dihydroxyethyl, 1-hydroxy-2-aminoethyl, 2-hydroxy-1 aminoethyl, methoxy, ethoxy, 3-hydroxyethyloxy, 3-aminoethyloxy, amino, methylamino, dimethylamino, 2-hydroxyethylamino, 2-methoxyethylamino,.
  • R 5 , R 6 , R 7 and R 8 are chosen from a hydrogen atom, a methyl, hydroxymethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, methoxy, 2-hydroxyethoxy, amino radical. , methylamino, dimethylamino, 2-hydroxyethylamino, plus preferably a hydrogen atom, a methyl radical, a methoxy, amino radical.
  • W 4 is preferably chosen from methyl, ethyl, 2-carboxyethyl, 1-carboxymethyl, 2-hydroxyethyl, 3-hydroxypropyl, 1, 2-dihydroxyethyl, 1-hydroxy-2-aminoethyl, 2-hydroxy-1-aminoethyl radicals . According to a preferred embodiment, W4 is chosen from methyl, 2-carboxyethyl, 2-hydroxyethyl,
  • R 1 and R 4 preferably represent an alkyl radical in
  • C 1 -C 4 optionally substituted by one or more radicals chosen from a hydroxy, a C ⁇ Cz alkoxy, an amino, a (di) alkylamino C r C 2 , a carboxyl or a sulfonic, more preferably a methyl radical , ethyl, 2-hydroxyethyl, 1-carboxymethyl, 2-carboxyethyl, 2-sulfonylethyl.
  • R 2 and R 3 preferably represent a hydrogen atom, a C 1 -C 4 alkyl radical optionally substituted by one or more radicals chosen from hydroxy, amino, C (di) alkylamino r C 2 , a carboxy.
  • R 2 and R 3 represent a hydrogen atom, a methyl, ethyl, 2-hydroxyethyl, carboxy, 1-hydroxymethyl radical.
  • Z1 preferably represents NR 4 and Z 2 is preferably CR 3 .
  • W 3 is chosen from among the pyrazolyl, pyrrolyl, imidazolyl, pyridile, pyrimidyl, triazinyl, pyridazinyl, pyrazinyl rings, preferably W3 is chosen from the pyrazolyl, imidazolyl, pyridyl, pyrimidinyl, thiazolyl, triazolyl rings. .
  • W3 is a pyrimidinyl ring.
  • W3 is a ring substituted by an alkyl radical optionally substituted by a hydroxy, alkoxy, amino, mono or dialkylamino; a chlorine or fluorine atom; an amino radical, an alkylamino radical, an alkoxy radical.
  • W 3 is preferably chosen from the pyrazolyl, imidazolyl, thiazolyl, triazolyl radicals optionally substituted by one or two amino, methyl, hydroxy, and pyridyl, pyrimidinyl radicals optionally substituted by one or two methyl, methoxy, amino or chlorine radicals.
  • the mineral or organic anion X can be chosen from a halide such as chloride, bromide, fluoride, iodide; a hydroxide; a sulfate; a hydrogen sulfate; a (C 1 -C 6 ) alkyl sulphate such as for example a methyl sulphate or an ethyl sulphate; an acetate; a tartrate; an oxalate; an alkyl ⁇ CrC ⁇ sulfonate such as methylsulfonate; an arylsulfonate substituted or unsubstituted by a C 1 -C 4 alkyl radical such as for example a 4-toluylsulfonate.
  • a halide such as chloride, bromide, fluoride, iodide
  • a hydroxide such as a sulfate; a hydrogen sulfate
  • the concentration of azo cationic dye of formula (I) can vary between 0.001 and 5% by weight approximately relative to the total weight of the dye composition, and preferably between approximately 0.05 and 2%.
  • the composition of the invention may also comprise an oxidizing agent.
  • This oxidizing agent can be any oxidizing agent conventionally used for bleaching keratin fibers.
  • the oxidizing agent is preferably chosen from hydrogen peroxide, urea peroxide, bramates of alkali metals, persalts such as perborates and persulfates. The use of hydrogen peroxide is particularly preferred.
  • composition according to the invention can also comprise an oxidation base.
  • This oxidation base can be chosen from the oxidation bases conventionally used in oxidation dyeing, for example paraphenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
  • paraphenylenediamines mention may more particularly be made, for example, of paraphenylenediamine, paratoluylenediamine, 2-chloro paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine , 2,5-dimethyl paraphenylenediamine, N, N-dimethyl paraphenylenediamine, N, N-diethyl paraphenylenediamine, N, N-dipropyl paraphenylenediamine, 4-amino N, N-diethyl 3-methyl aniline, N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 4-N, N-bis- ( ⁇ - hydroxyethyl) amino 2-methyl aniline, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-chloro aniline , 2- ⁇ -hydroxyethyl
  • paraphenylenediamine paratoluylenediamine, 2-isopropyl paraphenylenediamine, 2- ⁇ -hydroxyethyl paraphenylenediamine, 2- ⁇ -hydroxyethyloxy paraphenylenediamine, 2,6-dimethyl paraphenylenediamine para-phenylenediamine, 2,3-dimethyl para-phenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) para-phenylenediamine, 2-chloro para-phenylenediamine, 2- ⁇ -acetylaminoethyloxy para-phenylenediamine, and their addition salts with an acid are particularly preferred .
  • bis-phenylalkylenediamines that may be mentioned by way of example,
  • para-aminophenol there may be mentioned by way of example, para-aminophenol, 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4- amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4- amino 2- ( ⁇ -hydroxyethyl aminomethyl) phenol, 4- amino 2-fluoro phenol, and their addition salts with an acid.
  • para-aminophenol 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4- amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4- amino 2- ( ⁇ -hydroxyethyl aminomethyl) phenol, 4- amino 2-fluoro phenol, and their addition salts with an acid.
  • ortho-aminophenols there may be mentioned by way of example, 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methyl phenol, 5-acetamido 2-amino phenol, and their addition salts with an acid.
  • heterocyclic bases for example, pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives mention may be made of the compounds described for example in patents GB 1,026,978 and GB 1,153,196, such as 2,5-diamino pyridine, 2- (4-methoxyphenyl) amino 3-amino pyridine, 2,3-diamino 6-methoxy pyridine, 2- ( ⁇ -methoxyethyl) amino 3-amino 6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid.
  • pyrimidine derivatives mention may be made of the compounds described for example in patents DE 2,359,399; JP 88-169,571; JP 05 163 124; EP 0 770 375 or patent application WO 96/15765 such as 2,4,5,6-tetra-aminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2,4-dihydroxy 5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which may be mentioned pyrazolo - [1,5-a] -pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo- [1,5-a] -pyrimidine-3,7-diamine; pyrazolo- [1,5-a] -pyrimidine-3,5
  • composition according to the invention may also contain one or more couplers conventionally used for dyeing keratin fibers.
  • couplers conventionally used for dyeing keratin fibers.
  • couplers mention may especially be made of metaphenylenediamines, meta-aminophenols, metadiphenols, naphthalene couplers and heterocyclic couplers.
  • the coupler (s) are generally present in an amount between 0.001 and 10% by weight approximately of the total weight of the dye composition and more preferably from 0.005 to 6%.
  • the oxidation base (s) are present in an amount preferably between 0.001 to 10% by weight approximately of the total weight of the dye composition, and more preferably from 0.005 to 6%.
  • the addition salts with an acid which can be used in the context of the dye compositions of the invention for the oxidation bases and the couplers are in particular chosen from hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the dye composition in accordance with the invention may also contain direct dyes different from those of formula (I), these dyes being able in particular to be chosen from nitro dyes of the benzene series, cationic direct dyes, azo direct dyes, methine direct dyes.
  • the medium suitable for dyeing also called dye support, generally consists of water or of a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water.
  • organic solvent mention may, for example, be made of lower C r C 4 alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and monomethyl ether of diethylene glycol, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • lower C r C 4 alkanols such as ethanol and isopropanol
  • polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and monomethyl ether of diethylene glycol, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the solvents may be 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 dye composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic polymers, cationic, nonionic, amphoteric, zwitterionic or mixtures thereof, inorganic or organic thickening agents, and in particular associative anionic, cationic, nonionic and amphoteric polymeric thickeners, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as for example volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents, opacifying agents.
  • 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 dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers or even using conventional buffer systems.
  • acidifying agents there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic 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, sulfonic acids.
  • basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of formula (III) below:
  • W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 4 alkyl radical
  • R 6 , R 7 , R 8 and R 9 which may be identical or different, represent a hydrogen atom, a CC 4 alkyl radical or a C r C 4 hydroxyalkyl radical.
  • the dye composition according to the invention can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair.
  • the invention also relates to a direct dyeing process which comprises the application of a dye composition containing a dye of formula (I) as defined above on keratin fibers. After a pause, the keratin fibers are rinsed leaving colored fibers to appear.
  • the application to the fibers of the dye composition containing the azo cationic dye of formula (I) can be implemented in the presence of an oxidizing agent which causes discoloration of the fiber.
  • This oxidizing agent can be added to the composition containing the cationic azo dye at the time of use or directly on the keratin fiber.
  • the composition containing the azo cationic dye of formula (I) is free from oxidation base and from coupler.
  • the invention also relates to a process for permanent oxidation dyeing which comprises applying to the fibers a dye composition which comprises a dye of formula (I), at least one oxidation base and optionally at least one coupler, in the presence of an oxidizing agent.
  • the oxidation base, the coupler and the oxidizing agent are as defined above.
  • oxidizing agent enzymes among which there may be mentioned peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases.
  • the color can be revealed at acidic, neutral or alkaline pH and the oxidizing agent can be added to the composition of the invention just at the time of use or it can be used from an oxidizing composition containing it , applied to the fibers simultaneously or sequentially to the dye composition.
  • the dye composition is mixed, preferably at the time of use, with a composition containing, in a medium suitable for dyeing, at least one oxidizing agent, this oxidizing agent being present in an amount sufficient to develop a coloration.
  • the mixture obtained is then applied to the keratin fibers. After a pause time of approximately 3 to 50 minutes, preferably 5 to 30 minutes approximately, the keratin fibers are rinsed, washed with shampoo, rinsed again and then dried.
  • the oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
  • the pH of the oxidizing composition containing the oxidizing agent is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibers preferably varies between 3 and 12 approximately, and even more preferably between 5 and 11 It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers and as defined above.
  • composition which is finally applied to the keratin fibers can be in various forms, such as in the form of liquids, creams, gels or in any other form suitable for dyeing keratin fibers, and in particular human hair.
  • Another object of the invention is a device with several compartments or "kit” for dyeing in which a first compartment contains the dye composition of the invention and a second compartment contains the oxidizing composition.
  • This device can be equipped with a means allowing the desired mixture to be delivered to the hair, such as the devices described in patent FR-2 5 ⁇ 6 913 in the name of the applicant.
  • the subject of the invention is also the cationic azo dyes of formula (I) as defined above.
  • These compounds can be obtained from the preparation methods described for example in documents EP 810824, GB 9619573, RO 106572, J. Chem. Res .., Synop. (1998), (10), 648-649, DE 19721619, US 5852179, Synth. Common 1999, 29 (13), 2271-2276

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP02724397A 2001-04-02 2002-04-02 Ein kationischer azofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern Withdrawn EP1377261A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0104468A FR2822695B1 (fr) 2001-04-02 2001-04-02 Nouvelle composition tinctiriale pour la teinture des fibres keratiniques comprenant un colorant azoique cationique particilier
FR0104468 2001-04-02
PCT/FR2002/001135 WO2002078657A1 (fr) 2001-04-02 2002-04-02 Composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant azoïque cationique

Publications (1)

Publication Number Publication Date
EP1377261A1 true EP1377261A1 (de) 2004-01-07

Family

ID=8861849

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02724397A Withdrawn EP1377261A1 (de) 2001-04-02 2002-04-02 Ein kationischer azofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern

Country Status (5)

Country Link
US (1) US6884266B2 (de)
EP (1) EP1377261A1 (de)
JP (1) JP3748854B2 (de)
FR (1) FR2822695B1 (de)
WO (1) WO2002078657A1 (de)

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2072036A1 (de) 2007-12-21 2009-06-24 L'Oréal Verfahren zum Färben in Gegenwart eines Oxidationsmittels und eines speziellen organischen Amins, Vorrichtung und gebrauchsfertige Zusammensetzung
EP2072034A1 (de) 2007-12-21 2009-06-24 L'Oréal Verfahren zum direkten aufhellenden oder oxidierenden Färben in Gegenwart eines organischen Amins und Vorrichtung hierfür
EP2198831A1 (de) 2008-12-19 2010-06-23 L'Oreal Verfahren zur Aufhellung, aufhellenden Direktfärbung oder Oxidationsfärbung in Gegenwart von organischen Aminen und Mineralbasen, sowie Kit
EP2198834A2 (de) 2008-12-19 2010-06-23 L'oreal Aufhellungsverfahren für menschliche Keratinfasern durch Einsatz einer wasserfreien Zusammensetzung und einer basischen Mischung aus Monoethanolamin und Aminsäure, sowie geeignete Vorrichtung
EP2198832A1 (de) 2008-12-19 2010-06-23 L'oreal Verfahren zur Aufhellung der menschlichen keratinischen Fasern mit einer wasserfreien Zubereitung und kit
EP2198843A1 (de) 2008-12-19 2010-06-23 L'oreal Aufhellung der menschlichen keratinischen Fasern mit einer wasserfreien Zubereitung enthaltend die Kombination aus Monoethanolamine und alkalischen Aminosäure und Kit.
EP2198842A2 (de) 2008-12-19 2010-06-23 L'oreal Verfahren zum aufhellenden Färben keratinischer Fasern mit einer wasserfreien Färbezusammensetzung enthaltend ein basisches Mittel und mit einem Oxidationsmittel
EP2198924A1 (de) 2008-12-19 2010-06-23 L'oreal Verfahren zur Färbung von Keratinmaterialien bei vorhandensein einer farbstoff und alkaliwirkstoffenthaldenden Emulsion und einer Oxidationszusammensetzung
EP2198833A1 (de) 2008-12-19 2010-06-23 L'oreal Verfahren zur Färbung oder Aufhellung der menschlichen keratinischen Haare mit einer wasserfreien Zubereitung und einer anorganischen Base und Kit
EP2198838A2 (de) 2008-12-19 2010-06-23 L'oreal Verfahren und Kit zum Aufhellen oder direkten oder oxidativen Färben keratinischer Fasern mit einer wässrigen Zusammensetzung reich an Fettkörpern
WO2010070243A1 (fr) 2008-12-19 2010-06-24 L'oreal Procédé d ' éclaircissement des cheveux mettant en oeuvre une émulsion directe comprenant un agent oxydant et une composition contenant un agent alcalin
WO2010100231A1 (en) 2009-03-04 2010-09-10 L'oreal Device for dispensing a colouring composition for keratin fibres and associated process
WO2011033236A2 (fr) 2009-09-17 2011-03-24 L'oreal Procede d'eclaircissement ou de coloration en presence d'une composition anhydre particuliere et dispositif
WO2011045526A2 (fr) 2009-10-13 2011-04-21 L'oreal Composition comprenant un corps gras et un acide organophosphonique ou l'un de ses sels, procede de coloration ou d'eclaircissementla mettant en oeuvre et dispositifs
EP2338572A1 (de) 2009-12-22 2011-06-29 L'Oréal Substanz zum Färben und/oder Entfärben von Keratinfasern bestehend aus zwei Komponenten, die einen Fettkörper und ein Sequestriermittel enthält
EP2338571A1 (de) 2009-12-22 2011-06-29 L'Oréal Substanz zum Färben und/oder Entfärben von Keratinfasern bestehend aus zwei Komponenten, die einen speziellen Fettkörper und eine Redukton enthält
EP2338463A1 (de) 2009-12-22 2011-06-29 L'Oréal Färbe- oder Aufhellungszusammensetzung, die einen Fettkörper und ein amphoteres Polymer enthält
WO2011076672A2 (en) 2009-12-22 2011-06-30 L'oreal Agent for dyeing and/or bleaching keratinous fibres in two or more parts, comprising an alkaline composition in an inverse emulsion
WO2011076647A2 (en) 2009-12-22 2011-06-30 L'oreal Inverse emulsion for treating the hair comprising a particular fatty substance and an alkaline agent
WO2011076665A1 (en) 2009-12-22 2011-06-30 L'oreal Agent in two or more parts, in emulsion form, for dyeing and/or bleaching keratin fibres
WO2011076646A2 (en) 2009-12-22 2011-06-30 L'oreal Agent for dyeing and/or bleaching keratin fibres, comprising an inverse emulsion comprising an oxidizing agent
WO2011076792A1 (en) 2009-12-22 2011-06-30 L'oreal Agent for dyeing and/or bleaching keratinous fibres in two or more parts in the form of an emulsion and of a dispersion
WO2011076790A2 (en) 2009-12-23 2011-06-30 L'oreal Method for dyeing or lightening keratinous fibres in the presence of volatile linear alkane(s) and device.
WO2011121008A1 (en) 2010-04-02 2011-10-06 L'oreal Hair treatment process using a direct emulsion comprising an oxidizing agent and a direct emulsion containing an alkaline agent
WO2011131676A2 (en) 2010-04-22 2011-10-27 L'oreal Dyeing or lightening process and inverse emulsion for treating the hair comprising a particular solvent
WO2011151203A2 (en) 2010-06-03 2011-12-08 L'oreal Cosmetic treatment process using a coating based on a copolymer containing polyamide blocks and polyether blocks
WO2015063122A1 (en) 2013-10-30 2015-05-07 L'oreal Expanded dyeing composition comprising an inert gas, an oxidation dye and an oxyalkylenated nonionic surfactant
WO2016207347A1 (en) 2015-06-25 2016-12-29 L'oreal Packaging article comprising an envelope and an anhydrous dyeing, bleaching or oxidizing composition comprising a fibrous clay, and a compound chosen from a colouring agent and/or an oxidizing agent; use and process for dyeing and/or bleaching keratin fibres
WO2018096132A1 (en) 2016-11-28 2018-05-31 L'oreal Dye composition comprising 12-hydroxystearic acid, an organic amine and a dye
WO2020260629A1 (en) 2019-06-27 2020-12-30 L'oreal Composition comprising 12-hydroxystearic acid, an organic amine and a liquid fatty substance
WO2021130088A1 (en) 2019-12-24 2021-07-01 L'oreal Cosmetic composition comprising a polymer comprising at least one cationic (meth)acrylamide unit, a particular silicone and at least one surfactant
FR3113240A1 (fr) 2020-08-10 2022-02-11 L'oreal Composition comprenant au moins un silicone particulier, au moins un alcane et au moins une teinte directe et/ou au moins un pigment

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2841901B1 (fr) * 2002-07-05 2006-02-03 Oreal Utilisation d'un compose tetraazapentamethinique en tant que colorant direct et nouveaux composes tetraazapentamethiniques
US7101406B2 (en) * 2002-12-13 2006-09-05 L'oreal Dyeing composition comprising a cationic tertiary para-phenylenediamine and a heterocyclic cationic direct dye, methods and uses
FR2848439A1 (fr) * 2002-12-13 2004-06-18 Oreal Composition tinctoriale comprenant une paraphenylenediamine tertiaire cationique et un colorant direct cationique heterocyclique, procedes et utilisations
BRPI0417719A (pt) * 2003-12-19 2007-04-03 Ciba Sc Holding Ag método de colorir com composto diazotizado tamponado e componente de acoplamento
US20050235432A1 (en) * 2004-01-28 2005-10-27 Gregory Plos Composition for dyeing keratin fibers, comprising at least one alcohol oxidase, at least one oxidation dye precursor, and at least one azo, methine or azomethine cationic direct dye, and process using this composition
JP4723874B2 (ja) * 2005-02-18 2011-07-13 花王株式会社 染毛剤組成物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2702627A1 (de) * 1977-01-22 1978-07-27 Bayer Ag Monoazofarbstoffe
FR2757387B1 (fr) * 1996-12-23 1999-01-29 Oreal Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
FR2757385B1 (fr) 1996-12-23 1999-01-29 Oreal Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02078657A1 *

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2072036A1 (de) 2007-12-21 2009-06-24 L'Oréal Verfahren zum Färben in Gegenwart eines Oxidationsmittels und eines speziellen organischen Amins, Vorrichtung und gebrauchsfertige Zusammensetzung
EP2072034A1 (de) 2007-12-21 2009-06-24 L'Oréal Verfahren zum direkten aufhellenden oder oxidierenden Färben in Gegenwart eines organischen Amins und Vorrichtung hierfür
EP2198831A1 (de) 2008-12-19 2010-06-23 L'Oreal Verfahren zur Aufhellung, aufhellenden Direktfärbung oder Oxidationsfärbung in Gegenwart von organischen Aminen und Mineralbasen, sowie Kit
EP2198834A2 (de) 2008-12-19 2010-06-23 L'oreal Aufhellungsverfahren für menschliche Keratinfasern durch Einsatz einer wasserfreien Zusammensetzung und einer basischen Mischung aus Monoethanolamin und Aminsäure, sowie geeignete Vorrichtung
EP2198832A1 (de) 2008-12-19 2010-06-23 L'oreal Verfahren zur Aufhellung der menschlichen keratinischen Fasern mit einer wasserfreien Zubereitung und kit
EP2198843A1 (de) 2008-12-19 2010-06-23 L'oreal Aufhellung der menschlichen keratinischen Fasern mit einer wasserfreien Zubereitung enthaltend die Kombination aus Monoethanolamine und alkalischen Aminosäure und Kit.
EP2198842A2 (de) 2008-12-19 2010-06-23 L'oreal Verfahren zum aufhellenden Färben keratinischer Fasern mit einer wasserfreien Färbezusammensetzung enthaltend ein basisches Mittel und mit einem Oxidationsmittel
EP2198924A1 (de) 2008-12-19 2010-06-23 L'oreal Verfahren zur Färbung von Keratinmaterialien bei vorhandensein einer farbstoff und alkaliwirkstoffenthaldenden Emulsion und einer Oxidationszusammensetzung
EP2198833A1 (de) 2008-12-19 2010-06-23 L'oreal Verfahren zur Färbung oder Aufhellung der menschlichen keratinischen Haare mit einer wasserfreien Zubereitung und einer anorganischen Base und Kit
EP2198838A2 (de) 2008-12-19 2010-06-23 L'oreal Verfahren und Kit zum Aufhellen oder direkten oder oxidativen Färben keratinischer Fasern mit einer wässrigen Zusammensetzung reich an Fettkörpern
WO2010070243A1 (fr) 2008-12-19 2010-06-24 L'oreal Procédé d ' éclaircissement des cheveux mettant en oeuvre une émulsion directe comprenant un agent oxydant et une composition contenant un agent alcalin
WO2010100231A1 (en) 2009-03-04 2010-09-10 L'oreal Device for dispensing a colouring composition for keratin fibres and associated process
WO2011033236A2 (fr) 2009-09-17 2011-03-24 L'oreal Procede d'eclaircissement ou de coloration en presence d'une composition anhydre particuliere et dispositif
WO2011045526A2 (fr) 2009-10-13 2011-04-21 L'oreal Composition comprenant un corps gras et un acide organophosphonique ou l'un de ses sels, procede de coloration ou d'eclaircissementla mettant en oeuvre et dispositifs
US8419807B2 (en) 2009-10-13 2013-04-16 L'oreal Composition including a glyceride and an organophosphonic acid or one of the salts thereof, dyeing or colour-lightening method implementing same and devices
EP2338463A1 (de) 2009-12-22 2011-06-29 L'Oréal Färbe- oder Aufhellungszusammensetzung, die einen Fettkörper und ein amphoteres Polymer enthält
EP2338572A1 (de) 2009-12-22 2011-06-29 L'Oréal Substanz zum Färben und/oder Entfärben von Keratinfasern bestehend aus zwei Komponenten, die einen Fettkörper und ein Sequestriermittel enthält
WO2011076672A2 (en) 2009-12-22 2011-06-30 L'oreal Agent for dyeing and/or bleaching keratinous fibres in two or more parts, comprising an alkaline composition in an inverse emulsion
WO2011076647A2 (en) 2009-12-22 2011-06-30 L'oreal Inverse emulsion for treating the hair comprising a particular fatty substance and an alkaline agent
WO2011076665A1 (en) 2009-12-22 2011-06-30 L'oreal Agent in two or more parts, in emulsion form, for dyeing and/or bleaching keratin fibres
WO2011076646A2 (en) 2009-12-22 2011-06-30 L'oreal Agent for dyeing and/or bleaching keratin fibres, comprising an inverse emulsion comprising an oxidizing agent
WO2011076792A1 (en) 2009-12-22 2011-06-30 L'oreal Agent for dyeing and/or bleaching keratinous fibres in two or more parts in the form of an emulsion and of a dispersion
EP2338571A1 (de) 2009-12-22 2011-06-29 L'Oréal Substanz zum Färben und/oder Entfärben von Keratinfasern bestehend aus zwei Komponenten, die einen speziellen Fettkörper und eine Redukton enthält
WO2011076790A2 (en) 2009-12-23 2011-06-30 L'oreal Method for dyeing or lightening keratinous fibres in the presence of volatile linear alkane(s) and device.
WO2011121008A1 (en) 2010-04-02 2011-10-06 L'oreal Hair treatment process using a direct emulsion comprising an oxidizing agent and a direct emulsion containing an alkaline agent
WO2011131676A2 (en) 2010-04-22 2011-10-27 L'oreal Dyeing or lightening process and inverse emulsion for treating the hair comprising a particular solvent
WO2011151203A2 (en) 2010-06-03 2011-12-08 L'oreal Cosmetic treatment process using a coating based on a copolymer containing polyamide blocks and polyether blocks
WO2015063122A1 (en) 2013-10-30 2015-05-07 L'oreal Expanded dyeing composition comprising an inert gas, an oxidation dye and an oxyalkylenated nonionic surfactant
WO2016207347A1 (en) 2015-06-25 2016-12-29 L'oreal Packaging article comprising an envelope and an anhydrous dyeing, bleaching or oxidizing composition comprising a fibrous clay, and a compound chosen from a colouring agent and/or an oxidizing agent; use and process for dyeing and/or bleaching keratin fibres
WO2018096132A1 (en) 2016-11-28 2018-05-31 L'oreal Dye composition comprising 12-hydroxystearic acid, an organic amine and a dye
US10765612B2 (en) 2016-11-28 2020-09-08 L'oreal Dye composition comprising 12-hydroxystearic acid, an organic amine and a dye
WO2020260629A1 (en) 2019-06-27 2020-12-30 L'oreal Composition comprising 12-hydroxystearic acid, an organic amine and a liquid fatty substance
FR3097761A1 (fr) 2019-06-27 2021-01-01 L'oreal Composition comprenant l’acide 12-hydroxystéarique, une amine organique et un corps gras liquide
WO2021130088A1 (en) 2019-12-24 2021-07-01 L'oreal Cosmetic composition comprising a polymer comprising at least one cationic (meth)acrylamide unit, a particular silicone and at least one surfactant
FR3113240A1 (fr) 2020-08-10 2022-02-11 L'oreal Composition comprenant au moins un silicone particulier, au moins un alcane et au moins une teinte directe et/ou au moins un pigment

Also Published As

Publication number Publication date
FR2822695B1 (fr) 2003-07-25
US20040123400A1 (en) 2004-07-01
FR2822695A1 (fr) 2002-10-04
US6884266B2 (en) 2005-04-26
JP3748854B2 (ja) 2006-02-22
WO2002078657A1 (fr) 2002-10-10
JP2004529136A (ja) 2004-09-24

Similar Documents

Publication Publication Date Title
EP1377265B1 (de) Färbezusammensetzung zum färben von keratinösen fasern mit einem kationischen azo-farbstoff
EP1377261A1 (de) Ein kationischer azofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern
WO2002078658A1 (fr) Composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant azoïque cationique
EP1377264A1 (de) Ein kationischer azofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern
EP1377263B1 (de) Ein dikationischer diazofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern
WO2002080869A2 (fr) Nouvelle composition tinctoriale pour la teinture des fibres keratiniques comprenant un colorant monoazoique dicationique particulier
FR2844269A1 (fr) Composition pour la teinture des fibres keratiniques humaines comprenant un colorant monoazoique monocationique
EP1399425A1 (de) Dikationische diazofarbstoffe enhaltende zusammensetzungen zum färben von keratinfasern
EP1399117A1 (de) Einen dikationischen diazofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern
EP1416909A2 (de) Einen dikationischen diazofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern
FR2829926A1 (fr) Composition pour la teinture des fibres keratiniques comprenant un colorant diazoique dicationique particulier
EP1413286A1 (de) Färbemittel enthaltend mindestens ein heterocyclisches Oxidationsmittel und mindestens eine substituierten 2,3-Diaminopyridin-Kupplungsmittel
WO2003028686A1 (fr) Composition tinctoriale comprenant une base d'oxydation du type diaminopyrazole et coupleur pyrazolo-azole
FR2864781A1 (fr) Composition tinctoriale comprenant au moins un colorant direct de la famille azo-pyridinio-pyridone et au moins un colorant de synthese different, procede de coloration des fibres keratiniques
EP1586302A1 (de) Färbezusammensetzung enthaltend mindestens ein Pyrazolopyrimidin als Oxidationsfarbstoffvorprodukt und mindestens ein 6-Alkoxy-2,3-diaminopyridin als Kupplerkomponente
FR2872035A1 (fr) Utilisation de composes polycationiques en teinture des fibres keratiniques
FR3030246A1 (fr) Utilisation pour la coloration des fibres keratiniques d'un compose de type azomethinique a motif pyrazolopyridine
EP1879547A1 (de) Färbemittel mit einem farbstoff und einem propylenglykolderivat
EP1586303A1 (de) Färbezusammensetzung enthaltend mindestens ein Diaminopyrazol als Entwicklerkomponente und mindestens ein 6-Alkoxy-2,3-Diaminopyridin als Kupplerkomponente
WO2002074259A2 (fr) Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement pyrrolidinyle
WO2002074269A2 (fr) Compositions pour la teinture des fibres keretiniques contenant des derives de paraphenvienediamine a groupement pyrrolidinyle
WO2003059888A1 (fr) Derives de 4,5-diaminopyrazole sous forme de dimere et leur utilisation en teinture d'oxydation de fibres keratiniques
FR2917970A1 (fr) Utilisation d'au moins un derive cationique de cyanine pour la coloration capillaire, composition le contenant, procede de traitement des fibres keratiniques mettant en oeuvre ladite composition, dispositif et utilisation

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20031103

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

17Q First examination report despatched

Effective date: 20080801

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20081212