EP1399425A1 - Composition pour la teinture des fibres keratiniques comprenant un colorant diazo que dicationique particulier - Google Patents
Composition pour la teinture des fibres keratiniques comprenant un colorant diazo que dicationique particulierInfo
- Publication number
- EP1399425A1 EP1399425A1 EP02748945A EP02748945A EP1399425A1 EP 1399425 A1 EP1399425 A1 EP 1399425A1 EP 02748945 A EP02748945 A EP 02748945A EP 02748945 A EP02748945 A EP 02748945A EP 1399425 A1 EP1399425 A1 EP 1399425A1
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- EP
- European Patent Office
- Prior art keywords
- radical
- amino
- ium
- methyl
- composition according
- 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.)
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Classifications
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
Definitions
- the subject of the invention is a composition for dyeing keratin fibers, in particular human keratin fibers and more particularly hair, containing a particular dicationic diazo dye, as well as the process for dyeing keratin fibers using such a composition.
- Another subject of the invention is new diazo dicationic dyes.
- oxidation bases such as ortho or paraphenylenediamines, 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 belonging to the class of benzene nitrates, anthraquinones, nitropyridines, azo, indoamines, azines or triarylmethanes.
- the resulting colorings are colorations. particularly chromatic which are however temporary or semi-permanent because the nature of the interactions which bind the direct dyes to the keratinous fiber, and their desorption from the surface and or from the core of the fiber are responsible for their weak dyeing power and their bad behavior washing or sweating.
- 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 makes them generally 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 the keratin fibers with as much power as with oxidation coloring compositions.
- composition for dyeing keratin fibers in particular human keratin fibers such as the hair, comprising at least one diazo dicationic dye of formula (I) below:
- W 3 represents an oxygen atom, a radical NR 1 , a group -NR 15 -W 6 - NR 16 -, a group -NR 16 -W 6 -O-, a group -OW 6 -O-, a radical W 6 , a carbonyl radical,
- W 2 and W 4 represent, independently of one another, a carbon, pyridine or pyridazinyl aromatic group of formula (IV)
- W 6 represents a 5 or 6-membered aromatic or heteroaromatic group of formula (V):
- Xi represents a nitrogen atom or a CR 5 radical
- - X 2 represents a nitrogen atom or a CR 6 radical
- - X 3 represents a nitrogen, carbon atom or a CR 18 radical
- - 4 represents a nitrogen, carbon atom or a CR 19 radical
- - X 5 represents a nitrogen, carbon atom or a CR 20 radical
- - X 6 represents a nitrogen, carbon atom or a CR 21 radical
- Zi represents an oxygen or sulfur atom or an NR 8 radical
- Z 2 represents a nitrogen atom or a radical CR 9 ,
- - Z 3 represents a nitrogen atom or a CR12 radical
- - Z 4 represents a nitrogen atom or a CR 13 radical
- R 2 and R 8 represent, independently of one another, a linear or branched d-Cs alkyl radical , optionally substituted by one or more radicals chosen from hydroxy, CC 2 alkoxy, (poly) - C 2 -C alkoxy, amino, (di) alkylamino CC 2 , carboxy or sulfonic radicals; a phenyl radical optionally substituted by one or more radicals chosen from hydroxy, CC 2 alkoxy, (poly) - C 2 -C alkoxy, amino, (di) alkylamino CC 2 , carboxy, sulfonic or an atom halogen such as chlorine, fluorine or bromine,
- R 21 represent, independently of each other, a hydrogen atom, a linear or branched C C ⁇ 6 hydrocarbon chain, which may be saturated or unsaturated, one or more carbon atoms of the carbon chain of which may be replaced by an oxygen, nitrogen or sulfur atom 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 3 , R, R5, R ⁇ , R7, R9, R10, Ru, R12, 13, R14, R15, Rie, R 17 , Ris, R 19 , R 2 0 and R 2 ⁇ having no peroxide bond, nor diazo or nitroso radicals,
- R 7 with R 9 , R 0 with Ru and R 12 with R 13 can form a carbon aromatic ring, such as a phenyl,
- - - X is an organic or mineral anion.
- one or more of the carbon atoms of the hydrocarbon chain defined for the radicals R 3 , R 4 , R 5 , R 6 , R 7 , R 9 , R10, R11, R12 , R ⁇ 3 , R14, R15, Rie, R17, Rie, R19, R20 and R 21 may be replaced by an oxygen, nitrogen or sulfur atom or by an SO 2 group, and / or that these hydrocarbon chains are unsaturated, this means that we can, for example, make the following transformations:
- 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 being able to lead to aromatic groups.
- X is an organic or inorganic anion, for example chosen from a halide such as chloride, bromide, fluoride, iodide; a hydroxide; a sulfate; a hydrogen sulfate; an alkyl (CrC 6 ) sulphate such as for example a methyl sulphate or an ethyl sulphate; an acetate; a tartrate; an oxalate; an alkyl (CC 6 ) sulfonate such as methylsulfonate; an arylsulfonate substituted or unsubstituted by a dC 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
- R 14 , R 15 and Rie represent, preferably and independently of one another, a hydrogen atom; a linear or branched CC 6 alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, CC 2 alkoxy, (poly) hydroxy C 2 -C alkoxy, amino, (di) alkylamino CC 2 , ( poly) -hydroxya!
- kylamino, carboxy or sulfonic a phenyl radical optionally substituted by one or more radicals chosen from hydroxy, C 1 -C 2 alkoxy, (poly) -C 2 -C 4 alkoxy, amino, (di) CC 2 , carboxy, sulfonic or a d atom halogen such as chlorine, fluorine or bromine; a C ⁇ -C 4 alkylsulfonyl radical; an arylsulfonyl radical.
- R ⁇ , R 15 and R 16 represent, preferably and independently of one another, a hydrogen atom; a linear or branched CC 3 alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, C 1 -C 2 alkoxy, amino, CC 2 (di) alkylamino, carboxy or sulphonic radicals; a phenyl radical optionally substituted by one or more radicals chosen from amino, (di) alkylamino C r C 2 or (poly) -hydroxyalkylamino radicals.
- R ⁇ , R 15 and R 16 represent, preferably and independently of one another, a hydrogen atom; a linear or branched C 1 -C 3 alkyl radical which may be substituted by alkoxy, amino, carboxy, sulfonyl such as methyl, ethyl, 2-hydroxyethyl, 2-aminoethyl; 1-carboxymethyl, 2-carboxyethyl, 2-sulfonylethyl, 2-methoxyethyl; a phenyl radical optionally substituted by one or more radicals chosen from amino, (di) alkylamino CC 2 , (poly) -hydroxyalkylamino radicals.
- R ⁇ , R ⁇ 5 and R 6 are preferably chosen from a hydrogen atom; a methyl, 2-hydroxyethyl radical; a phenyl radical optionally substituted by an amino, (di) methylamino, (di) (2-hydroxyethyl) amino radical.
- R 3 , R 4 , R 5 , R 6 , Rio, Ru, R12, R13, R17, is, 1 9,
- R20 and R 21 represent, preferably and independently of one another, a hydrogen atom; a linear or branched CC 4 alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, CC 2 alkoxy, (poly) hydroxy C 2 -C 4 alkoxy, amino, (di) alkylamino C r C radicals 2 , carboxy or sulfonic; a phenyl radical optionally substituted by one or more radicals chosen from hydroxy, C r C 2 alkoxy, (poly) hydroxy C 2 -C 4 alkoxy, amino, (di) C 1 -C alkylamino C 2 , carboxy, sulfonic or a halogen atom such as chlorine, fluorine or bromine; a carboxy radical; a sulfonylamino radical; a
- R 3 , R 4 , R 5 , Re, Rio, Ru, R ⁇ 2 , R13, R17, Ris, R19, R20 and R 2 represent a hydrogen atom, a CC 4 alkyl radical optionally substituted by a or several radicals chosen from hydroxy, amino, (di) alkylamino C ⁇ -C 2 ; a carboxy radical; a CC 2 alkoxy radical; an amino radical; a CC 2 (di) alkylamino radical; a C 2 -C 4 (poly) hydroxyalkylamino radical.
- R 3 , R 4 , R 5 , R 6, R 10l R11, R12, R13, R17, Ris, R19, R20 and R 2 ⁇ represent a hydrogen atom, a methyl radical, phenyl, 2-hydroxymethyl, carboxy ,. a methoxy, ethoxy, 2-hydroxyethyloxy radical, an amino, methylamino, dimethylamino, 2-hydroxyethylamino radical.
- R 7 and R 9 represent, independently of one another, a hydrogen atom; a linear or branched C 1 -C 4 alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, C 1 -C 2 alkoxy, (poly) hydroxy C 2 -C alkoxy, amino, (di) alkylamino CC 2 , carboxy or sulfonic; a phenyl radical optionally substituted by one or more radicals chosen from hydroxy, C ⁇ -C 2 alkoxy, (poly) -hydroxy C 2 -C 4 alkoxy, amino, (di) alkylamino CC 2 , carboxy, sulfonic or a halogen atom such as chlorine, fluorine or bromine; a carboxy radical; a sulfonylamino radical.
- R 7 and R 9 preferably represent a hydrogen atom, a phenyl radical, a C r C alkyl radical optionally substituted by one or more radicals chosen from hydroxy, amino, (di) alkylamino radicals CC 2 , carboxy.
- R 7 and R 9 preferably represent a hydrogen atom, a methyl, phenyl, 2-hydroxymethyl radical, a carboxy.
- Ri, R 2 and R 8 preferably represent a CC 4 alkyl radical optionally substituted by one or more radicals, chosen from hydroxy, C r C 2 alkoxy, amino, (di) alkylamino CC 2 , carboxy, sulfonic radicals.
- R 2 and R 8 preferably represents a methyl, ethyl, 2-hydroxyethyl, 1-carboxy ethyl, 2-carboxyethyl, 2-sulfonylethyl radical.
- Wi and W 5 preferably represent, independently of one another, a cationic group imidazolium, triazolium, thiazolium, pyridinium.
- W 2 and W preferably represent, independently of one another, a phenyl or pyridyl group.
- W 6 preferably represents a phenyl, pyridyl, triazinyl, pyrimidinyl group.
- W 3 preferably represents a radical NR ⁇ , a group NR ⁇ 5 -W 6 - NR ⁇ e, a group W 6 , in which R ⁇ 4 , R ⁇ 5 , Rie and W 6 are as defined above, in particular according to the preferred modes.
- the concentration of diazo diazo dye of formula (I) can vary from 0.001 to 5% by weight approximately relative to the total weight of the dye composition, and preferably from approximately 0.05 to 2%.
- diazo dicationic dyes of formula (I) according to the present invention, mention may in particular be made of the following compounds:
- a first synthetic principle consists of starting from an amino heterocycle with 5 or 6 members, such as 2-aminoimidazole, 3-aminotriazole, 2-aminothiazole, 3-aminothiadiazole, 2-aminopyridine or 2-aminopyridazine , which is reacted with sodium nitrite in a polar protic acid solvent, such as acetic acid or hydrochloric acid, at a temperature generally between -
- aromatic derivatives are obtained by applying the conventional reactions of the literature SNAr (aromatic nucleophilic substitution), SN1 (nucleophilic substitution 1) and SN2 (nucleophilic substitution 2).
- the resulting condensation product then reacts with an alkylating agent such as a dialkyl sulfate or an alkyl halide in a polar solvent and at a temperature between 0 ° C and 150 ° C, preferably between 20 ° C and 100 ° C.
- the 5- or 6-membered heterocyclic part is thus quarternized and the azo obtained is cationic.
- a second synthesis principle consists in reacting a quarternized heterocyclic azo 2 on one of the nitrogen atoms of the heterocycle in series 4-methoxyphenylazo with an aniline derivative or a heteroaromatic amine 3 in a protic solvent at a temperature comprised between 25 ° C and 150 ° C.
- the quarternary heterocycle can be an imidazolium, triazolium, thiazolium, thiadiazolium, oxazolium.
- the same synthesis principle can be applied in a 6-membered heterocyclic series, such as pyridinium or pyridazinium, which makes it possible to obtain the compounds of formula 5 ⁇ from Pazoic.
- the cationic azo derivative 4 then reacts with a diazonium salt derived from a 5- or 6-membered heterocycle (vacuum above) at a temperature between -10 ° C and 25 ° C to yield the intermediate mono-cationic di-azo compound which reacts with an alkylating agent such as a dialkyl sulfate or an alkyl halide in a polar solvent and at a temperature between 0 ° C and 150 ° C, preferably between 20 ° C and 100 ° C to lead to the di-cationic di-azo compound 5.
- an alkylating agent such as a dialkyl sulfate or an alkyl halide in a polar solvent
- a temperature between 0 ° C and 150 ° C preferably between 20 ° C and 100 ° C to lead to the di-cationic di-azo compound 5.
- Me denotes a CH3 radical.
- 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 neutral benzenic direct dyes, acid or cationic, neutral azo direct dyes which are acidic or cationic , quinone direct dyes and in particular neutral, acidic or cationic anthraquinone dyes, azine direct dyes, methine direct dyes, triarylmethane direct dyes, indoamine direct dyes and natural direct dyes.
- direct dyes different from those of formula (I) these dyes being able in particular to be chosen from neutral benzenic direct dyes, acid or cationic, neutral azo direct dyes which are acidic or cationic , quinone direct dyes and in particular neutral, acidic or cationic anthraquinone dyes, azine direct dyes, methine direct dyes, triarylmethane direct dyes, indoamine direct dyes and natural direct dyes.
- azo direct dyes which can be used according to the invention, mention may be made of the cationic azo dyes described in patent applications WO 95/15144, WO-95/01772 and EP-714954, the content of which forms an integral part of the invention.
- the following dyes may be particularly mentioned: 1,3-dimethyl-2 chloride - [[4- (dimethylamino) phenyl] azo] -1H-lmidazolium, 1,3-dimethyl-2- chloride [(4-aminophenyl) azo] -1 H-lmidazolium, - 1-methyl-4-methyl sulfate - [(methylphenylhydrazono) methyl] -pyridinium.
- azine dyes the following compounds may be mentioned: -Basic Blue 17 -Basic Red 2.
- triarylmethane dyes which can be used according to the invention, the following compounds may be mentioned: -Basic Green 1 -Acid blue 9 -Basic Violet 3 -Basic Violet 14 -Basic Bl ⁇ e 7 -Acid Violet 49 -Basic Blue 26 -Acid Blue 7
- indoamine dyes which can be used according to the invention, mention may be made of the following compounds: -2- ⁇ -hydroxyethlyamino-5- [bis- ( ⁇ -4'-hydroxyethyl) amino] anilino-1,4-benzoquinone -2- ⁇ -hydrpxyethylamino-5- (2'-methoxy-4'-amino) anilino-1, 4-benzoquinone
- the additional direct dye (s) different from those of formula (I) of the present invention preferably represent from 0.001 to 20% by weight approximately of the total weight of the composition and even more preferably from 0.005 to 10% by weight approximately.
- 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 among hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and enzymes among which there may be mentioned peroxidases, 2-electron oxidoreductases such than uricases and 4-electron oxygenases like laccases.
- 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 there may be more particularly mentioned by way of example, 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 para-phenylenediamine, 2,6-dimethyl para-phenylenediamine, 2,6-diethyl para-phenylenediamine, 2,3-dimethyl para-phenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) para-phenylenediamine, 2-chloro para-phenylenediamine, 2- ⁇ -acetylaminoethyloxy paraphenylenediamine, and their addition salts with an acid are particularly preferred.
- N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) 1,3-diamino propanol N , N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- ( ⁇ -hydroxyethyl) N, N'-bis- (4-aminophenyl) tetramethylenediamine
- "N, N'-bis- (4-methyl-aminophenyl) tetramethylenediamine N, N'-bis- (ethyl) N, N '-bis- (4'-amino, 3'-methylphenyl) ethylenediamine, 1,8-bis- (2,
- 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 2359399; JP 88-169571; 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, the 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-dd,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 in particular be made of metaphenylenediamines, meta- aminophenols, metadiphenols, naphthalene couplers and heterocyclic couplers.
- the coupler (s) are generally present in an amount ranging from 0.001 to 10% by weight approximately of the total weight of the dye composition and more preferably from 0.005 to 6%.
- the oxidation base or bases are present in an amount preferably ranging from 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 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 CC alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
- the organic solvents may be present in proportions ranging preferably from 1 to 40% by weight approximately relative to the total weight of the dye composition, and even more preferably from 5 to 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, mineral or organic thickening agents, and in particular anionic, cationic, nonionic and amphoteric associative polymers, 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 conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic polymers, cationic, nonionic, amphoteric,
- the adjuvants mentioned above 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 and their derivatives, sodium or potassium hydroxides and the compounds of formula (III) below:
- W is a propylene residue optionally substituted by a hydroxyl group or a CC 4 alkyl radical
- R 6 , R 7 , R ⁇ and R 9 identical or different, represent a hydrogen atom, an alkyl radical in CC or hydroxyalkyl in C -C 4 .
- 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 used in the presence of an oxidizing agent which causes discoloration of the fiber (direct lightening dye).
- 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 invention also relates to an oxidation dyeing process 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.
- 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 approximately 5 to 30 minutes, 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 enabling the desired mixture to be delivered to the hair, such as the devices described in patent FR-2586 913 in the name of the applicant.
- the invention also relates to the dicationic diazo dyes of formula (I) as defined above.
- the reaction mixture was then filtered through sintered glass. The precipitate was washed with methanol. The colored solution was then concentrated, and the solid obtained chromatographed on a column of silica gel (eluent MeOH / Dichloromethane / buffer mixture: 9/1/1). The powder obtained after chromatography was taken up with a few milliliters of water and then dried. After purification, a bright dark green powder was obtained.
- the dye obtained dyed the hair in a purple shade.
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- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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FR0107613 | 2001-06-11 | ||
FR0107613A FR2825703B1 (fr) | 2001-06-11 | 2001-06-11 | Composition pour la teinture des fibres keratiniques comprenant un colorant diazoique dicationique particulier |
PCT/FR2002/001980 WO2002100834A1 (fr) | 2001-06-11 | 2002-06-10 | Composition pour la teinture des fibres keratiniques comprenant un colorant diazoïque dicationique particulier |
Publications (1)
Publication Number | Publication Date |
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EP1399425A1 true EP1399425A1 (fr) | 2004-03-24 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP02748945A Withdrawn EP1399425A1 (fr) | 2001-06-11 | 2002-06-10 | Composition pour la teinture des fibres keratiniques comprenant un colorant diazo que dicationique particulier |
Country Status (9)
Country | Link |
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US (1) | US7001436B2 (ja) |
EP (1) | EP1399425A1 (ja) |
JP (1) | JP2005501134A (ja) |
KR (1) | KR20040003063A (ja) |
CN (1) | CN100429203C (ja) |
BR (1) | BR0210995A (ja) |
FR (1) | FR2825703B1 (ja) |
MX (1) | MX247992B (ja) |
WO (1) | WO2002100834A1 (ja) |
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US11246814B2 (en) | 2015-12-18 | 2022-02-15 | L'oreal | Oxidizing composition for treating keratin materials, comprising a fatty substance and oxyalkylenated surfactants |
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FR3052969B1 (fr) | 2016-06-23 | 2020-02-21 | L'oreal | Utilisation pour la coloration des fibres keratiniques d’un compose de type azomethinique a motif derive de quinoline |
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- 2002-06-10 WO PCT/FR2002/001980 patent/WO2002100834A1/fr active Application Filing
- 2002-06-10 MX MXPA03011339 patent/MX247992B/es active IP Right Grant
- 2002-06-10 CN CNB028156846A patent/CN100429203C/zh not_active Expired - Fee Related
- 2002-06-10 EP EP02748945A patent/EP1399425A1/fr not_active Withdrawn
- 2002-06-10 BR BR0210995-6A patent/BR0210995A/pt not_active IP Right Cessation
- 2002-06-10 US US10/480,202 patent/US7001436B2/en not_active Expired - Fee Related
- 2002-06-10 KR KR10-2003-7016167A patent/KR20040003063A/ko not_active Application Discontinuation
- 2002-06-10 JP JP2003503603A patent/JP2005501134A/ja active Pending
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EP2072034A1 (fr) | 2007-12-21 | 2009-06-24 | L'Oréal | Procédé de coloration directe éclaircissante ou d'oxydation en présence d'une amine organique particulière et dispositif |
EP2072036A1 (fr) | 2007-12-21 | 2009-06-24 | L'Oréal | Procédé de coloration en présence d'un agent oxidant et d'une amine organique particulière, dispositif et composition prête à l'emploi |
EP2198838A2 (fr) | 2008-12-19 | 2010-06-23 | L'oreal | Procédé et dispositif d'éclaircissement ou de coloration directe éclaircissante ou d'oxydation des fibres kératiniques en présence d'une composition aqueuse riche en corps gras |
EP2198833A1 (fr) | 2008-12-19 | 2010-06-23 | L'oreal | Procede de coloration ou d'eclaircissement en presence d'une base inorganique et dispositif |
EP2198831A1 (fr) | 2008-12-19 | 2010-06-23 | L'Oreal | Procédé d'éclaircissement ou de coloration directe éclaircissante ou d'oxydation en présence d'une amine organique et d'une base minérale et dispositif approprié |
EP2198832A1 (fr) | 2008-12-19 | 2010-06-23 | L'oreal | Procédé d'éclaircissement de fibres kératiniques humaines mettant en oeuvre une composition anhydre et dispositif |
EP2198843A1 (fr) | 2008-12-19 | 2010-06-23 | L'oreal | Eclaircissement de fibres kératiniques humaines mettant en oeuvre une composition anhydre comprenant un melange monoethanolamine / acide amine basique et dispositif |
EP2198924A1 (fr) | 2008-12-19 | 2010-06-23 | L'oreal | Procédé de coloration des matières keratiniques mettant en oeuvre une émulsion comprenant un colorant et un agent alcalin, et une composition oxydante |
EP2198834A2 (fr) | 2008-12-19 | 2010-06-23 | L'oreal | Eclaircissement de fibres kératiniques humaines mettant en oeuvre une composition anhydre et un mélange monoéthanolamine / acide amine basique et dispositif approprié |
EP2198842A2 (fr) | 2008-12-19 | 2010-06-23 | L'oreal | Procédé de coloration éclaircissante de matières kératiniques mettant en oeuvre une composition anhydre colorante comprenant un agent alcalin et une composition oxydante |
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 (fr) | 2009-12-22 | 2011-06-29 | L'Oréal | Composition de coloration ou d'éclaircissement comprenant un corps gras et un polymere amphotère |
EP2338571A1 (fr) | 2009-12-22 | 2011-06-29 | L'Oréal | Agent de coloration et/ou de décoloration des fibres kératiniques en deux parties, comprenant un corps gras particulier et une réductone |
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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 |
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 |
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EP2338572A1 (fr) | 2009-12-22 | 2011-06-29 | L'Oréal | Agent de coloration et/ou de décoloration des fibres kératiniques en deux parties, comprenant un corps gras et un agent séquestrant |
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 |
---|---|
WO2002100834A1 (fr) | 2002-12-19 |
US20040244123A1 (en) | 2004-12-09 |
CN100429203C (zh) | 2008-10-29 |
KR20040003063A (ko) | 2004-01-07 |
US7001436B2 (en) | 2006-02-21 |
CN1541207A (zh) | 2004-10-27 |
FR2825703B1 (fr) | 2008-04-04 |
MXPA03011339A (es) | 2004-03-19 |
MX247992B (es) | 2007-08-10 |
BR0210995A (pt) | 2004-06-08 |
JP2005501134A (ja) | 2005-01-13 |
FR2825703A1 (fr) | 2002-12-13 |
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