EP1416909A2 - Einen dikationischen diazofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern - Google Patents

Einen dikationischen diazofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern

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Publication number
EP1416909A2
EP1416909A2 EP02755072A EP02755072A EP1416909A2 EP 1416909 A2 EP1416909 A2 EP 1416909A2 EP 02755072 A EP02755072 A EP 02755072A EP 02755072 A EP02755072 A EP 02755072A EP 1416909 A2 EP1416909 A2 EP 1416909A2
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EP
European Patent Office
Prior art keywords
radical
radicals
hydroxy
composition according
amino
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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Application number
EP02755072A
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English (en)
French (fr)
Inventor
Laurent Vidal
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LOreal SA
Original Assignee
LOreal SA
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Publication date
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Publication of EP1416909A2 publication Critical patent/EP1416909A2/de
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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
    • 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
    • C09B44/20—Thiazoles or hydrogenated thiazoles
    • 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
    • C09B44/12—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having one nitrogen atom as the only ring hetero atom
    • C09B44/126—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having one nitrogen atom as the only ring hetero atom in a six-membered ring, e.g. pyrridinium, quinolinium
    • 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
    • C09B44/18—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having three nitrogen atoms as the only ring hetero atoms

Definitions

  • the subject of the invention is a new dye composition for dyeing human keratin fibers, in particular hair, comprising 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 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 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 human keratin fibers and in particular the hair comprising at least one diazo dicationic dye of formula (I) below:
  • W 2 represents a carbon, pyridine or pyridazinyl aromatic group of formula (IV) below:
  • (IV) -W 3 and W 5 independently of one another represent a radical -NR 14 - or an oxygen atom -O-, or a nitrogen atom,
  • W 4 represents a linear or branched, saturated or unsaturated Cr.C 16 hydrocarbon chain, which can form one or more carbon rings comprising from 3 to 6 members, one or more carbon atoms of the carbon chain of which may be replaced by one atom of 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, W 4 not comprising a peroxide bond , nor diazo or nitroso radicals; a piperazine cycle; a group of the following formula (V):
  • - X 2 represents a nitrogen atom or a radical CR 6
  • - X 3 represents a nitrogen atom or a radical CR 17
  • - X represents a nitrogen atom or a radical CR ⁇ 8
  • - Zi represents an oxygen or sulfur atom or an NR 8 radical
  • - Z 2 represents a nitrogen atom or a CR g radical, it being understood that formula (II) does not designate an imidazolium ring, it is to say that ⁇ Z it Z 2 ) is different from (NR 8 , CR 9 ),
  • Z 3 represents a nitrogen atom or a radical CR 12 ,
  • Z represents a nitrogen atom or a CR ⁇ 3 radical, the bond a of the 5-membered cationic cycle of formula (II) is linked to the azo group of formula (I),
  • L represents a linear or branched, saturated C ⁇ -C ⁇ ⁇ hydrocarbon chain, which can form one or more carbon rings comprising from 3 to 6 members, one or more carbon atoms of the carbon chain of which can be replaced by an atom of oxygen, nitrogen or sulfur or with an SO 2 group, and the carbon atoms of which may be, independently of one another, substituted by one or more halogen atoms; L having no peroxide bond, nor diazo or nitroso radicals,
  • L represents a linear or branched, saturated or unsaturated C r C ⁇ 6 hydrocarbon chain, which can form one or more carbon rings comprising from 3 to 6 members, one or more carbon atoms of the carbon chain of which may be replaced by an atom oxygen, nitrogen or sulfur or by an SO 2 group and containing no peroxide bond, nor diazo or nitroso radicals,
  • R 3j R, R 5 , R 6 , R 7 , Rs, Rio, Ru, R12, R13, R ", R15, Rie, R ⁇ ? t R 18 represent, together or independently of one another, a hydrogen atom, a linear or branched, saturated or unsaturated C ⁇ C ⁇ 6 hydrocarbon chain, which can form one or more carbon rings comprising 3 to 6 members, one or more carbon atoms of the carbon chain of which can be replaced by an oxygen, nitrogen or sulfur atom or by an SO 2 group, and whose carbon atoms can be, independently of one another, substituted by one or more halogen atoms; R 3 , R, R5, R ⁇ , R 7 , R9, R10, Ru, R12, R13, ⁇ , R15, Rie, i7 ⁇ t R e comprising no peroxide bond, nor diazo or nitroso radicals,
  • R 3 with R, R 7 with R 9 , R TM with Rn, R ⁇ 2 st ⁇ ec R 13 and R 15 with R ⁇ 6 can form a carbonaceous aromatic ring, such as a phenyl, X is an organic or inorganic anion .
  • one or more of the carbon atoms of the hydrocarbon chain defined for the radicals L, R 3 , R 4 , R 5 , R 6 , R 7 , R 9 , R10, Ru , R ⁇ 2 , R ⁇ 3 , R ⁇ , R15, ie, R 1 7 and Ris 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: - CH, - H can become -0-H
  • 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 (CrC 6 ) 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 such as for example a methyl
  • R 3 , R 4l R 5 , R 6 , Rio, Ru, R ⁇ 2 , 13, R15, Rie, R ⁇ 7 and R 8 represent a hydrogen atom, an alkyl radical in C-, rC 4 optionally substituted by one or more radicals chosen from hydroxy, amino, (di) alkylamino in C ⁇ -C 2 ; a carboxy radical; a dC 2 alkoxy radical; an amino radical; a C r C 2 (di) alkylamino radical; a C 2 - C 4 (poly) -hydroxyalkylamino radical according to a particularly preferred embodiment, R 3 , R, R 5 , R 6 ⁇ R 10 ,
  • R1 1 , R ⁇ 2 , R13, R15, ie, R17 and Rie represent a hydrogen atom, a methyl, phenyl, 2-hydroxymethyl radical, a carboxy, a methoxy, ethoxy, 2-hydroxyethyloxy radical, an amino, methylamino radical, dimethylamino, 2-hydroxyethylamino.
  • R 7 and R 9 represent, independently of one another, a hydrogen atom; a linear or branched O 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 - C 2 , carboxy or sulfonic; an optionally substituted phenyl radical; a carboxy radical; a sulfonylamino radical.
  • R 7 and R 9 preferably represent a hydrogen atom, a phenyl radical, a CC 4 alkyl radical optionally substituted by one or more radicals chosen from hydroxy, amino, (di) alkylamino C1-C2 radicals , carboxy.
  • R 7 and R 9 preferably represent a hydrogen atom, a methyl, phenyl, 2-hydroxymethyl radical, a carboxy.
  • R ⁇ preferably represents 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 4 alkoxy, amino, (di) alkylamino CC 2 radicals, carboxy or sulfonic; an optionally substituted phenyl radical R 14 preferably represents a hydrogen atom; a linear or branched CC 4 alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, CC 2 alkoxy, amino, (di) alkylamino CC 2 radicals.
  • R ⁇ 4 preferably represents a hydrogen atom; a methyl, ethyl, 2-hydroxyethyl, 2-aminoethyl, 2-methoxyethyl, 1-carboxymethyl, 2-carboxyethyl, 2-sulfonylethyl radical.
  • R ⁇ preferably represents a hydrogen atom; a methyl, ethyl, 2-hydroxyethyl, 2-aminoethyl radical.
  • Ri, R and R 8 represent a linear or branched CC 8 alkyl radical, optionally substituted by one or more radicals chosen from hydroxy, CC 2 alkoxy, (poly) C 2 -C 4 alkoxy, amino, ( di) d-C 2 alkylamino, carboxy or sulfonic; an optionally substituted phenyl radical.
  • R 1, R 2 and R 8 preferably represent a C 1 -C 4 alkyl radical optionally substituted with one or more radicals chosen from hydroxy, CC 2 alkoxy, amino, (di) alkylamino CC 2 radicals, carboxy, sulfonic.
  • R ,, R 2 and R 8 preferably represents a methyl, ethyl, 2-hydroxyeth 'yl, 1-carboxymethyl, 2-carboxyethyl, 2-sulfonyléthyle.
  • W preferably represents a cationic group, triazolium, thiazolium, pyridinium substituted by the preferred radicals R 1f R 2 , R 7 R 10 , Ru, R ⁇ 2 , R 13 .
  • W 2 preferably represents a phenyl or pyridyl group substituted by the preferred radicals R 3 , R 4 R 5 , R e ,
  • W and W 5 represent, independently of one another, preferably a group -NR ⁇ 4 -, with the preferred meanings of R ⁇ 4 .
  • W 4 preferably represents a linear or branched C 2 -C 6 alkyl 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 -C 2 alkylamino, carboxy or sulfonic radicals; a phenyl radical optionally substituted by one or more radicals chosen from hydroxy, C ⁇ -C 2 alkoxy > (poly) hydroxy C 2 -C alkoxy, amino, (di) CC 2 alkyl, carboxy, sulfonic or an atom halogen such as chlorine, fluorine or bromine; a naphthyl radical optionally substituted by one or more radicals chosen from hydroxyl, alkoxy, C ⁇ -C 2, (poly) hydroxyalkoxy, C 2 -C, amino, (di) alkylamino, C, - C 2, carboxy, sulfonic or a
  • W preferably represents a linear or branched C 2 -C 4 alkyl radical, optionally substituted by one or more hydroxy radicals; a phenyl radical optionally substituted by one or more radicals chosen from hydroxy, CC 2 alkoxy, (poly) -C 2 -C 4 alkoxy, amino, (di) C ⁇ -C 2 , carboxy, sulfonic radicals; a naphthyl radical optionally substituted by one or more radicals chosen from, hydroxy, CC 2 alkoxy, (poly) hydroxy C 2 -C 4 alkoxy, amino, (di) alkylamino CC 2 , carboxy, sulfonic acid piperazine radical formed with the two radicals W 3 and W 5 .
  • W 4 preferably represents an ethyl, propyl, butyl, 2-hydroxypropyl radical; phenyl; naphthyl; a piperazine ring formed with the two radicals W 3 and W 6 .
  • L preferably represents a group chosen from -CO-; -CO-CH 2 - CH 2 -CO-; -CO-CO-; benzo-1, 4-dicarbonyl; ethyl; 1,4-phenyl; triazine; pyrimidine.
  • L preferably represents an ethyl or triazine group.
  • the concentration of diazo dicationic 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%.
  • 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) phenyljazo] -1 H -midazolium, -1,3-dimethyl-2- chloride [ (4-aminophenyl) azo] -1 H-lmidazolium,
  • azine dyes the following compounds may be mentioned: -Basic Blue 17 -Basic Red 2.
  • triarylmethane dyes which can be used according to the invention, mention may be made of the following compounds: -Basic Green 1 -Acid blue 9 -Basic Violet 3 -Basic Violet 14 -Basic Blue 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:
  • the additional direct dye (s) 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 from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and enzymes among which may be mentioned peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as 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, NN- bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 4-N, N-bis- ( ⁇ - hydroxyethyl) amino 2-methyl aniline, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-chloro aniline, 2- ⁇ -hydroxyethyl paraphen
  • 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-choro 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-
  • 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, 2,4-dihydrpxy 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] - ⁇ yrimidine ⁇ 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 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 (s) 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 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 alkanols at C C, 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 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 their mixtures, 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.
  • 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 as well as their derivatives, sodium or potassium hydroxides and compounds of formula (III) below: in which W is a propylene residue optionally substituted by a hydroxyl group or a CC 4 alkyl radical; R 6, R 8 and R 9, identical or different, represent a hydrogen atom, alkyl or hydroxyalkyl DC 4 DC 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 comprising 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 comprising the azo cationic dye of formula (I) can be implemented in the presence of an oxidizing agent which causes the discoloration of the fiber (direct lightening dye). This oxidizing agent can be added to the composition comprising the azo cationic 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.
  • 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 the use, to 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
  • Dye "kit” 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-2,586,913 in the name of the applicant.
  • W3 represents an oxygen atom and the other groups of formula (I) have the same designations as previously defined, or
  • - W3 represents a radical -NR 14 - and L represents an aryl or heteroaryl radical optionally substituted by one or more radicals chosen from hydroxy, CC 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 first synthetic principle consists of starting from an amino heterocycle with 5 or 6 members, such as 3-aminotriazole, 2-aminothiazoIe, 3-aminothiadiazole, 2-aminopyridine or 2-aminopyridazine, which is put in reaction with sodium nitrite in a polar protic acid solvent,. such as acetic acid or hydrochloric acid, at a temperature generally between -10 ° C and 50 ° C, in order to generate the corresponding diazonium salt.
  • a polar protic acid solvent such as acetic acid or hydrochloric acid
  • W3, W5, X1, X2 and L have the meanings previously described according to the invention.
  • the resulting condensation product then reacts with an alkylating agent such as a dialkyl sulphate 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.
  • an alkylating agent such as a dialkyl sulphate 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.
  • a second synthetic principle consists in reacting a quarternized heterocyclic azo J [_on one of the nitrogen atoms of the heterocycle in series 4-methoxyphenylazo with an aniline, phenol derivative or a heteroaromatic amine 2 in a protic solvent at a temperature between 25 ° C and 150 ° C.
  • the quarternary heterocycle can be a triazolium, thiazolium, thiadiazolium, oxazolium.
  • the same synthetic 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 from azoic V. protic solvent
  • the cationic azo derivative 3 then reacts with a di-electrophile such as an alkyl di-halide, an alkylaryl di-halide, a triazine di-halide, a pyrimidine di-halide or a bis-chloride d acid, to lead to the cationic azo compound 4.
  • a di-electrophile such as an alkyl di-halide, an alkylaryl di-halide, a triazine di-halide, a pyrimidine di-halide or a bis-chloride d acid
  • the derivative 3 can react with an aryl dihalide in the presence of a transition metal such as palladium (II) or copper (I) to yield compound 4 according to the reaction of Buchwald or Merwein well known in the literature.
  • a transition metal such as palladium (II) or copper (I)
  • the quarternary heterocycle can be a triazolium, thiazolium, thiadiazolium, oxazolium.
  • the same principle of synthesis 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 the azoic V_. .
  • Me denotes a CH3 radical.
  • the diazonium salt of 3-aminotriazole (0.5 mmol) is prepared according to the protocol described in patent GB-1186753 or US-3291788.
  • a solution of 1 mmol of bis- (N-phenylamino) -propane in 10 ml of 15% sulfuric acid is added at 0 ° C. to the diazonium salt prepared beforehand with vigorous stirring. After disappearance of the reagents, the reaction medium is poured onto ice and the precipitate is drained, then washed with water, then dried to constant weight to yield compound d.
  • Compound d (0.2 mmol) is then dissolved in 30 ml of dimethylformamide and 1 mmol of dimethylsulfate are added to this solution.
  • reaction medium is then brought to 90-100 ° C with stirring. After 6 hours, the reaction medium is poured into 100 ml of water at room temperature and the solution is concentrated to dryness until constant weight to result in 0.04 mmol of the desired compound b whose ⁇ max is 520 nm in a solution methanolic with 1% acetic acid.
  • the dye obtained dyed the hair in an iridescent red shade.

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EP02755072A 2001-06-11 2002-06-11 Einen dikationischen diazofarbstoff enthaltende farbstoffzusammensetzung zum färben von keratinischen fasern Withdrawn EP1416909A2 (de)

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FR0107615A FR2825622B1 (fr) 2001-06-11 2001-06-11 Composition pour la teinture des fibres keratiniques comprenant un colorant diazoique dicationique particulier
FR0107615 2001-06-11
PCT/FR2002/001991 WO2002100369A2 (fr) 2001-06-11 2002-06-11 Composition pour la teinture des fibres keratiniques comprenant un colorant diazoique dicationique particulier

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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.
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
EP2198832A1 (de) 2008-12-19 2010-06-23 L'oreal Verfahren zur Aufhellung der menschlichen keratinischen Fasern mit einer wasserfreien Zubereitung und kit
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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
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BR0210998A (pt) 2004-12-28
MXPA03011342A (es) 2004-03-19
FR2825622A1 (fr) 2002-12-13
CN1551756A (zh) 2004-12-01
WO2002100369A2 (fr) 2002-12-19
US20040200009A1 (en) 2004-10-14
CN1294123C (zh) 2007-01-10
FR2825622B1 (fr) 2007-06-29
KR100610541B1 (ko) 2006-08-09
US7407516B2 (en) 2008-08-05
JP2005500283A (ja) 2005-01-06
KR20040003064A (ko) 2004-01-07
WO2002100369A3 (fr) 2004-02-19

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