DE20110356U1 - m-Dihydroxybenzene derivatives as well as colorants for keratin fibers containing these compounds - Google Patents

m-Dihydroxybenzene derivatives as well as colorants for keratin fibers containing these compounds

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Publication number
DE20110356U1
DE20110356U1 DE20110356U DE20110356U DE20110356U1 DE 20110356 U1 DE20110356 U1 DE 20110356U1 DE 20110356 U DE20110356 U DE 20110356U DE 20110356 U DE20110356 U DE 20110356U DE 20110356 U1 DE20110356 U1 DE 20110356U1
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benzene
amino
dihydroxy
group
diamino
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Procter and Gamble Deutschland GmbH
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Wella GmbH
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
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    • A61K8/00—Cosmetics or similar toiletry preparations
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    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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    • A61Q5/10—Preparations for permanently dyeing the hair
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/50—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/12—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
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    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C07D317/66—Nitrogen atoms not forming part of a nitro radical

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Description

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Claims (12)

1. 1,3-Dihydroxy-benzol-Derivat der allgemeinen Formel (I) oder dessen physiologisch verträgliche, wasserlösliche Salze,
worin
R1 und R2 unabhänging voneinander gleich Wasserstoff, einer C1-C2-Alkoxygruppe, einer C1-C6-Alkylgruppe, einer C3-C6-Alkenylgruppe, einer C2-C4-Hydroxyalkylgruppe, einer C3-C4-Dihydroxyalkylgruppe, einer C2-C4-Aminoalkylgruppe, einer C2-C4-Dimethylaminoalkylgruppe, einer C2-C4-Acetylaminoalkylgruppe einer C2-C4-Methoxyalkylgruppe, einer C2-C4-Ethoxyalkylgruppe, einer C1-C4-Cyanalkylgruppe, einer C1-C4-Carboxyalkylgruppe, einer C1-C4-Aminocarbonylalkylgruppe, einer Pyridylmethylgruppe, einer Furfurylgruppe, einer Thienylmethylgruppe, einer substituierten Pyridylgruppe oder einem Rest der Formel (II) sind
oder R1 und R2 gemeinsam mit dem Sickstoffatom einen Ring der Formel
bilden;
R3 gleich Wasserstoff oder einer C1-C4-Alkylgruppe ist;
R4, R5, R6, R7 und R8 unabhängig voneinander Wasserstoff, ein Halogenatom, eine Cyanogruppe, eine Hydroxygruppe, eine C1-C4-Alkoxygruppe, eine C1-C4-Hydroxyalkoxygruppe, eine C1-C6-Alkyl­ gruppe, eine C1-C4-Alkylthioethergruppe, eine Mercaptogruppe, eine Nitrogruppe, eine C1-C6-Alkylaminogruppe, eine Di(C1-C6-alkyl)amino­ gruppe, eine (Dihydroxy(C3-C4)alkyl)aminogruppe, eine Di(C1-C4- hydroxyalkyl)aminogruppe, eine (C2-C4-Hydroxyalkyl)-(C1-C6-alkyl)- aminogruppe, eine Trifluormethangruppe eine -C(O)H-Gruppe, eine -C(O)CH3-Gruppe, eine -C(O)CF3-Gruppe, eine -Si(CH3)3-Gruppe, eine C1-C4-Hydroxyalkylgruppe, eine C2-C4-Dihydroxyalkylgruppe, eine Carboxygruppe oder eine Pyrrolidingruppe darstellen, oder zwei nebeneinanderliegende Reste R6 bis R10 eine -O-CH2-O-Brücke bilden;
R9 gleich Wasserstoff, einer Hydroxygruppe, einer Carboxygruppe, einer Aminocarbonylgruppe oder einer Hydroxymethylgruppe ist;
R10 gleich Wasserstoff oder einer C1-C6-Alkylgruppe ist; und n gleich 0 oder 1 ist;
wobei mindestens einer der Reste R1 und R2 nicht gleich Wasserstoff ist.1. 1,3-dihydroxy-benzene derivative of the general formula (I) or its physiologically compatible, water-soluble salts,
wherein
R1 and R2 independently of one another are hydrogen, a C 1 -C 2 alkoxy group, a C 1 -C 6 alkyl group, a C 3 -C 6 alkenyl group, a C 2 -C 4 hydroxyalkyl group, a C 3 -C 4 Dihydroxyalkyl group, a C 2 -C 4 aminoalkyl group, a C 2 -C 4 dimethylaminoalkyl group, a C 2 -C 4 acetylaminoalkyl group, a C 2 -C 4 methoxyalkyl group, a C 2 -C 4 ethoxyalkyl group, a C 1 Are -C 4 cyanalkyl group, a C 1 -C 4 carboxyalkyl group, a C 1 -C 4 aminocarbonylalkyl group, a pyridylmethyl group, a furfuryl group, a thienylmethyl group, a substituted pyridyl group or a radical of the formula (II)
or R1 and R2 together with the nitrogen atom form a ring of the formula
form;
R3 is hydrogen or a C 1 -C 4 alkyl group;
R4, R5, R6, R7 and R8 independently of one another are hydrogen, a halogen atom, a cyano group, a hydroxy group, a C 1 -C 4 alkoxy group, a C 1 -C 4 hydroxyalkoxy group, a C 1 -C 6 alkyl group, a C 1 -C 4 alkylthioether group, a mercapto group, a nitro group, a C 1 -C 6 alkylamino group, a di (C 1 -C 6 alkyl) amino group, a (dihydroxy (C 3 -C 4 ) alkyl) amino group, a di (C 1 -C 4 hydroxyalkyl) amino group, a (C 2 -C 4 hydroxyalkyl) - (C 1 -C 6 alkyl) amino group, a trifluoromethane group a -C (O) H group, a -C (O) CH 3 group, a -C (O) CF 3 group, a -Si (CH 3 ) 3 group, a C 1 -C 4 hydroxyalkyl group, a C 2 -C 4 dihydroxyalkyl group represent a carboxy group or a pyrrolidine group, or two adjacent radicals R6 to R10 form an -O-CH2-O bridge;
R9 is hydrogen, a hydroxy group, a carboxy group, an aminocarbonyl group or a hydroxymethyl group;
R10 is hydrogen or a C 1 -C 6 alkyl group; and n is 0 or 1;
wherein at least one of R1 and R2 is not hydrogen. 2. 1,3-Dihydroxy-benzol-Derivat nach Anspruch 1, dadurch gekennzeichnet, dass es ausgewählt ist aus Verbindungen der Formel (I) bei denen (i) R3 gleich Wasserstoff ist und/oder (ii) eine der Restgruppen R1 oder R2 gleich einer C2-C4-Hydroxyalkylgruppe, einer 3,4-Methylen­ dioxyphenylgruppe oder einer Phenylgruppe ist. 2. 1,3-dihydroxy-benzene derivative according to claim 1, characterized in that it is selected from compounds of formula (I) in which (i) R3 is hydrogen and / or (ii) one of the residual groups R1 or R2 is a C 2 -C 4 hydroxyalkyl group, a 3,4-methylene dioxyphenyl group or a phenyl group. 3. 1,3-Dihydroxy-benzol-Derivat der Formel (I) nach Anspruch 1, dadurch gekennzeichnet, dass es ausgewählt ist aus der Gruppe bestehend aus 1,3-Dihydroxy-4-(methylaminomethyl)-benzol, 1,3-Dihydroxy-4-(allylaminomethyl)-benzol, 2-(2,4-Dihydroxybenzyl­ amino)-ethanol, 1,3-Dihydroxy-4-(pyrrolidin-1-yl-methyl)-benzol, 1-(2,4-Dihydroxybenzyl)-pyrrolidin-3-ol, [1-(2,4-Dihydroxybenzyl)- pyrrolidin-2-yl]-methanol, 1,3-Dihydroxy-4-[(2-aminoethylamino)-methyl]- benzol, 1,3-Dihydroxy-4-morpholin-4-ylmethyl-benzol, 1-(2,4-Dihydroxy­ benzyl)-piperidin-4-ol, 1-(2,4-Dihydroxybenzyl)-piperidin-3-ol, N-[2-(2,4-Dihydroxybenzylamino)-ethyl]-acetamid, 3-[2-(2,4-Dihydroxy­ benzylamino)-1-hydroxyethyl]-phenol, 1,3-Dihydroxy-4-[(2-methoxyethyl­ amino)-methyl]-benzol, 2-(2,4-Dihydroxybenzylamino)-propan-1-ol, 1,3-Dihydroxy-4-{[(tetrahydrofuran-2-ylmethyl)-amino]-methyl}-benzol, 1,3-Dihydroxy-4-((2-aminophenylamino)-methyl)-benzol, 1,3-Dihydroxy-4- ((3-aminophenyl-amino)-methyl)-benzol, 1,3-Dihydroxy-4-((2-hydroxy­ phenylamino)-methyl)-benzol, 1,3-Dihydroxy-4-((3-hydroxyphenylamino)- methyl)-benzol, 1,3-Dihydroxy-4-((2-hydroxyphenylamino)-methyl)-benzol, 1,3-Dihydroxy-4-((4-hydroxy-phenylamino)-methyl)-benzol, 1,3-Dihydroxy- 4-((4-methyl-phenyl-amino)-methyl)-benzol, 1,3-Dihydroxy-5-(methyl­ aminomethyl)-benzol, 1,3-Dihydroxy-5-(allylaminomethyl)-benzol, 2-(3,5-Dihydroxybenzylamino)-ethanol, 1,3-Dihydroxy-5-(pyrrolidin-1-yl­ methyl)-benzol, 1-(3,5-Dihydroxybenzyl)-pyrrolidin-3-ol, [1-(3,5-Dihydroxy­ benzyl)-pyrrolidin-2-yl]-methanol, 1,3-Dihydroxy-5-[(2-aminoethylamino)- methyl]-benzol, 1,3-Dihydroxy-5-morpholin-5-yl-methyl-benzol, 1-(3,5-Dihydroxy-benzyl)-piperidin-5-ol, 1-(3,5-Dihydroxybenzyl)-piperidin- 3-ol, N-[2-(3,5-Dihydroxybenzylamino)-ethyl]-acetamid, 3-[2-(3,5-Dihydroxybenzylamino)-1-hydroxyethyl]-phenol, 1,3-Dihydroxy- 5-[(2-methoxyethylamino)-methyl]-benzol, 2-(3,5-Dihydroxybenzylamino)- propan-1-ol, 1,3-Dihydroxy-5-{[(tetrahydrofuran-2-yl-methyl)-amino]- methyl}-benzol, 1,3-Dihydroxy-5-((2-aminophenylamino)-methyl)-benzol, 1,3-Dihydroxy-5-((3-aminophenyl-amino)-methyl)-benzol, 1,3-Dihydroxy-5- ((2-hydroxy-phenylamino)-methyl)-benzol, 1,3-Dihydroxy-5-((3-hydroxy­ phenylamino)-methyl)-benzol, 1,3-Dihydroxy-5-((2-hydroxyphenylamino)- methyl)-benzol, 1,3-Dihydroxy-5-((4-hydroxyphenylamino)-methyl)-benzol und 1,3-Dihydroxy-5-((4-methyl-phenylamino)-methyl)-benzol, sowie deren physiologisch verträglichen Salzen.3. 1,3-dihydroxy-benzene derivative of the formula (I) according to claim 1, characterized in that it is selected from the group consisting of 1,3-dihydroxy-4- (methylaminomethyl) benzene, 1,3-dihydroxy-4- (allylaminomethyl) benzene, 2- (2,4-dihydroxybenzyl amino) ethanol, 1,3-dihydroxy-4- (pyrrolidin-1-ylmethyl) benzene, 1- (2,4-dihydroxybenzyl) pyrrolidin-3-ol, [1- (2,4-dihydroxybenzyl) - pyrrolidin-2-yl] methanol, 1,3-dihydroxy-4 - [(2-aminoethylamino) methyl] - benzene, 1,3-dihydroxy-4-morpholin-4-ylmethyl-benzene, 1- (2,4-dihydroxy benzyl) piperidin-4-ol, 1- (2,4-dihydroxybenzyl) piperidin-3-ol, N- [2- (2,4-dihydroxybenzylamino) ethyl] acetamide, 3- [2- (2,4-dihydroxy benzylamino) -1-hydroxyethyl] phenol, 1,3-dihydroxy-4 - [(2-methoxyethyl amino) methyl] benzene, 2- (2,4-dihydroxybenzylamino) propan-1-ol, 1,3-dihydroxy-4 - {[(tetrahydrofuran-2-ylmethyl) amino] methyl} benzene, 1,3-dihydroxy-4 - ((2-aminophenylamino) methyl) benzene, 1,3-dihydroxy-4- ((3-aminophenylamino) methyl) benzene, 1,3-dihydroxy-4 - ((2-hydroxy phenylamino) methyl) benzene, 1,3-dihydroxy-4 - ((3-hydroxyphenylamino) - methyl) benzene, 1,3-dihydroxy-4 - ((2-hydroxyphenylamino) methyl) benzene, 1,3-dihydroxy-4 - ((4-hydroxyphenylamino) methyl) benzene, 1,3-dihydroxy- 4 - ((4-methylphenylamino) methyl) benzene, 1,3-dihydroxy-5- (methyl aminomethyl) benzene, 1,3-dihydroxy-5- (allylaminomethyl) benzene, 2- (3,5-dihydroxybenzylamino) ethanol, 1,3-dihydroxy-5- (pyrrolidin-1-yl methyl) benzene, 1- (3,5-dihydroxybenzyl) pyrrolidin-3-ol, [1- (3,5-dihydroxy benzyl) pyrrolidin-2-yl] methanol, 1,3-dihydroxy-5 - [(2-aminoethylamino) - methyl] benzene, 1,3-dihydroxy-5-morpholin-5-yl-methyl-benzene, 1- (3,5-dihydroxybenzyl) piperidin-5-ol, 1- (3,5-dihydroxybenzyl) piperidine- 3-ol, N- [2- (3,5-dihydroxybenzylamino) ethyl] acetamide,  3- [2- (3,5-dihydroxybenzylamino) -1-hydroxyethyl] phenol, 1,3-dihydroxy- 5 - [(2-methoxyethylamino) methyl] benzene, 2- (3,5-dihydroxybenzylamino) - propan-1-ol, 1,3-dihydroxy-5 - {[(tetrahydrofuran-2-ylmethyl) amino] - methyl} benzene, 1,3-dihydroxy-5 - ((2-aminophenylamino) methyl) benzene, 1,3-dihydroxy-5 - ((3-aminophenylamino) methyl) benzene, 1,3-dihydroxy-5- ((2-hydroxyphenylamino) methyl) benzene, 1,3-dihydroxy-5 - ((3-hydroxy phenylamino) methyl) benzene, 1,3-dihydroxy-5 - ((2-hydroxyphenylamino) - methyl) benzene, 1,3-dihydroxy-5 - ((4-hydroxyphenylamino) methyl) benzene and 1,3-dihydroxy-5 - ((4-methylphenylamino) methyl) benzene, and their physiologically acceptable salts. 4. Mittel zum oxidativen Färben von Keratinfasern auf der Basis einer Entwicklersubstanz-Kupplersubstanz-Kombination, dadurch gekenn­ zeichnet, dass es in einem geeigneten kosmetischen Träger mindestens ein 1,3-Dihydroxy-benzol-Derivat der Formel (I) nach einem der Ansprüche 1 bis 3 enthält.4. Agent for the oxidative dyeing of keratin fibers on the basis of a Developer substance-coupler substance combination, characterized thereby records that it is in a suitable cosmetic carrier at least a 1,3-dihydroxy-benzene derivative of the formula (I) according to one of the Claims 1 to 3 contains. 5. Mittel nach Anspruch 4, dadurch gekennzeichnet, dass das 1,3-Dihydroxy-benzol-Derivat der Formel (I) in einer Menge von 0,005 bis 20 Gewichtsprozent enthalten ist.5. Means according to claim 4, characterized in that the 1,3-dihydroxy-benzene derivative of the formula (I) in an amount of 0.005 to 20 percent by weight is included. 6. Mittel nach Anspruch 4 oder 5, dadurch gekennzeichnet, dass die Entwicklersubstanz ausgewählt ist aus der Gruppe bestehend aus 1,4-Diamino-benzol, 1,4-Diamino-2-methyl-benzol, 1,4-Diamino-2,6- dimethyl-benzol, 1,4-Diamino-3,5-diethyl-benzol, 1,4-Diamino-2,5- dimethyl-benzol, 1,4-Diamino-2,3-dimethyl-benzol, 2-Chlor-1,4-diamino­ benzol, 1,4-Diamino-2-(thiophen-2-yl)benzol, 1,4-Diamino-2-(thiophen-3- yl)benzol, 1,4-Diamino-2-(pyridin-3-yl)benzol, 2,5-Diaminobiphenyl, 1,4-Diamino-2-methoxymethyl-benzol, 1,4-Diamino-2-aminomethyl­ benzol, 1,4-Diamino-2-hydroxymethyl-benzol, 1,4-Diamino-2-(2-hydroxy­ ethoxy)-benzol, 2-(2-(Acetylamino)ethoxy)-1,4-diamino-benzol, 4-Phenylamino-anilin, 4-Dimethylamino-anilin, 4-Diethylamino-anilin, 4-Dipropylamino-anilin, 4-[Ethyl(2-hydroxyethyl)-amino]-anilin, 4-[Di(2- hydroxyethyl)amino]-anilin, 4-[Di(2-hydroxyethyl)-amino]-2-methyl-anilin, 4-[(2-Methoxyethyl)amino]-anilin, 4-[(3-Hydroxypropyl)amino]-anilin, 4-[(2,3-Dihydroxypropyl)amino]-anilin, 1,4-Diamino-2-(1-hydroxyethyl)- benzol, 1,4-Diamino-2-(2-hydroxyethyl)-benzol, 1,4-Diamino-2-(1 - methylethyl)-benzol, 1,3-Bis[(4-aminophenyl)-(2-hydroxyethyl)amino]-2- propanol, 1,4-Bis[(4-aminophenyl)amino]-butan, 1,8-Bis(2,5-diamino­ phenoxy)-3,6-dioxaoctan, 4-Amino-phenol, 4-Amino-3-methyl-phenol, 4-Amino-3-(hydroxymethyl)-phenol, 4-Amino-3-fluor-phenol, 4-Methyl­ amino-phenol, 4-Amino-2-(aminomethyl)-phenol, 4-Amino-2- (hydroxymethyl)-phenol, 4-Amino-2-fluor-phenol, 4-Amino-2-[(2- hydroxyethyl)-amino]methyl-phenol, 4-Amino-2-methyl-phenol, 4-Amino-2-(methoxymethyl)-phenol, 4-Amino-2-(2-hydroxyethyl)-phenol, 5-Amino-salicylsäure, 2,5-Diamino-pyridin, 2,4,5,6-Tetraamino-pyrimidin, 2,5,6-Triamino-4-(1H)-pyrimidon, 4,5-Diamino-1-(2-hydroxyethyl)-1H­ pyrazol, 4,5-Diamino-1-(1-methylethyl)-1 H-pyrazol, 4,5-Diamino-1-[(4- methylphenyl)methyl]-1H-pyrazol, 1-[(4-Chlorphenyl)methyl]-4,5-diamino- 1H-pyrazol, 4,5-Diamino-1-methyl-1H-pyrazol, 2-Amino-phenol, 2-Amino- 6-methyl-phenol, 2-Amino-5-methyl-phenol und 1,2,4-Trihydroxybenzol.6. Composition according to claim 4 or 5, characterized in that the Developer substance is selected from the group consisting of 1,4-diamino-benzene, 1,4-diamino-2-methyl-benzene, 1,4-diamino-2,6- dimethyl-benzene, 1,4-diamino-3,5-diethyl-benzene, 1,4-diamino-2,5- dimethyl benzene, 1,4-diamino-2,3-dimethyl benzene, 2-chloro-1,4-diamino benzene, 1,4-diamino-2- (thiophene-2-yl) benzene, 1,4-diamino-2- (thiophene-3- yl) benzene, 1,4-diamino-2- (pyridin-3-yl) benzene, 2,5-diaminobiphenyl,  1,4-diamino-2-methoxymethyl-benzene, 1,4-diamino-2-aminomethyl benzene, 1,4-diamino-2-hydroxymethyl-benzene, 1,4-diamino-2- (2-hydroxy ethoxy) benzene, 2- (2- (acetylamino) ethoxy) -1,4-diamino-benzene, 4-phenylamino-aniline, 4-dimethylamino-aniline, 4-diethylamino-aniline, 4-dipropylamino-aniline, 4- [ethyl (2-hydroxyethyl) amino] aniline, 4- [di (2- hydroxyethyl) amino] aniline, 4- [di (2-hydroxyethyl) amino] -2-methylaniline, 4 - [(2-methoxyethyl) amino] aniline, 4 - [(3-hydroxypropyl) amino] aniline, 4 - [(2,3-dihydroxypropyl) amino] aniline, 1,4-diamino-2- (1-hydroxyethyl) - benzene, 1,4-diamino-2- (2-hydroxyethyl) benzene, 1,4-diamino-2- (1 - methylethyl) benzene, 1,3-bis [(4-aminophenyl) - (2-hydroxyethyl) amino] -2- propanol, 1,4-bis [(4-aminophenyl) amino] butane, 1,8-bis (2,5-diamino phenoxy) -3,6-dioxaoctane, 4-amino-phenol, 4-amino-3-methyl-phenol, 4-amino-3- (hydroxymethyl) phenol, 4-amino-3-fluorophenol, 4-methyl aminophenol, 4-amino-2- (aminomethyl) phenol, 4-amino-2- (hydroxymethyl) phenol, 4-amino-2-fluoro-phenol, 4-amino-2 - [(2- hydroxyethyl) amino] methylphenol, 4-amino-2-methylphenol, 4-amino-2- (methoxymethyl) phenol, 4-amino-2- (2-hydroxyethyl) phenol, 5-amino-salicylic acid, 2,5-diamino-pyridine, 2,4,5,6-tetraamino-pyrimidine, 2,5,6-triamino-4- (1H) pyrimidone, 4,5-diamino-1- (2-hydroxyethyl) -1H pyrazole, 4,5-diamino-1- (1-methylethyl) -1 H-pyrazole, 4,5-diamino-1 - [(4- methylphenyl) methyl] -1H-pyrazole, 1 - [(4-chlorophenyl) methyl] -4,5-diamino- 1H-pyrazole, 4,5-diamino-1-methyl-1H-pyrazole, 2-amino-phenol, 2-amino- 6-methylphenol, 2-amino-5-methylphenol and 1,2,4-trihydroxybenzene. 7. Mittel nach einem der Ansprüche 4 bis 6, dadurch gekennzeichnet, dass es zusätzlich zu den Verbindungen der Formel (I) noch weitere bekannte Kupplersubstanzen, welche ausgewählt sind aus der Gruppe bestehend aus N-(3-Dimethylamino-phenyl)-harnstoff, 2,6-Diaminopyridin, 2-Amino-4-[(2-hydroxyethyl)amino]-anisol, 2,4-Diamino-1-fluor-5- methyl-benzol, 2,4-Diamino-1-methoxy-5-methyl-benzol, 2,4-Diamino-1- ethoxy-5-methyl-benzol, 2,4-Diamino-1-(2-hydroxyethoxy)-5-methyl­ benzol, 2,4-Di[(2-hydroxyethyl)amino]-1,5-dimethoxy-benzol, 2,3-Diamino- 6-methoxy-pyridin, 3-Amino-6-methoxy-2-(methylamino)-pyridin, 2,6-Diamino-3,5-dimethoxy-pyridin, 3,5-Diamino-2,6-dimethoxy-pyridin, 1,3-Diamino-benzol, 2,4-Diamino-1-(2-hydroxyethoxy)-benzol, 1,3-Diamino-4-(2,3-dihydroxypropoxy)-benzol, 1,3-Diamino-4-(3- hydroxypropoxy)-benzol, 1,3-Diamino-4-(2-methoxyethoxy)-benzol, 2,4-Diamino-1,5-di(2-hydroxyethoxy)-benzol, 1-Aminoethoxy)-2,4- diamino-benzol, 2-Amino-1-(2-hydroxyethoxy)-4-rriethylamino-benzol, 2,4-Diaminophenoxy-essigsäure, 3-[Di(2-hydroxyethyl)amino]-anilin, 4-Amino-2-di[(2-hydroxyethyl)amino]-1-ethoxy-benzol, 5-Methyl-2-(1- methylethyl)-phenol, 3-[(2-Hydroxyethyl)amino]-anilin, 3-[(2-Aminoethyl)- amino]-anilin, 1,3-Di(2,4-diaminophenoxy)-propan, Di(2,4-diamino­ phenoxy)-methan, 1,3-Diamino-2,4-dimethoxy-benzol, 2,6-Bis(2-hydroxy­ ethyl)amino-toluol, 4-Hydroxyindol, 3-Dimethylamino-phenol, 3-Diethyl­ amino-phenol, 5-Amino-2-methyl-phenol, 5-Amino-4-fluor-2-methyl­ phenol, 5-Amino-4-methoxy-2-methyl-phenol, 5-Amino-4-ethoxy-2-methyl­ phenol, 3-Amino-2,4-dichlor-phenol, 5-Amino-2,4-dichlor-phenol, 3-Amino- 2-methyl-phenol, 3-Amino-2-chlor-6-methyl-phenol, 3-Amino-phenol, 2-[(3-Hydroxyphenyl)amino]-acetamid, 5-[(2-Hydroxyethyl)amino]-4- methoxy-2-methyl-phenol, 5-[(2-Hydroxyethyl)amino]-2-methyl-phenol, 3-[(2-Hydroxyethyl)amino]-phenol, 3-[(2-Methoxyethyl)amino]-phenol, 5-Amino-2-ethyl-phenol, 5-Amino-2-methoxy-phenol, 2-(4-Amino-2- hydroxy-phenoxy)-ethanol, 5-[(3-Hydroxypropyl)amino]-2-methyl-phenol, 3-[(2,3-Dihydroxypropyl)amino]-2-methyl-phenol, 3-[(2-Hydroxyethyl)- amino]-2-methyl-phenol, 2-Amino-3-hydroxy-pyridin, 2,6-Dihydroxy-3,4- dimethylpyridin, 5-Amino-4-chlor-2-methyl-phenol, 1-Naphthol, 2-Methyl-1- naphthol, 1,5-Dihydroxy-naphthalin, 1,7-Dihydroxy-naphthalin, 2,3-Dihydroxy-naphthalin, 2,7-Dihydroxy-naphthalin, 2-Methyl-1-naphthol­ acetat, (m-Dihydroxy-phenyl)-acrylamid, 1-Chlor-2,4-dihydroxy-benzol, 2-Chlor-(m-Dihydroxy-phenyl)-acrylamid, 1,2-Dichlor-3,5-dihydroxy-4- methyl-benzol, 1,5-Dichlor-2,4-dihydroxy-benzol, 1,3-Dihydroxy-2-methyl­ benzol, 3,4-Methylendioxy-phenol, 3,4-Methylendioxy-anilin, 5-[(2-Hydroxyethyl)amino]-1, 3-benzodioxol, 6-Brom-1-hydroxy-3,4- methylendioxy-benzol, 3,4-Diamino-benzoesäure, 3,4-Dihydro-6-hydroxy- 1,4(2H)-benzoxazin, 6-Amino-3,4-dihydro-1,4(2H)-benzoxazin, 3-Methyl- 1-phenyl-5-pyrazolon, 5,6-Dihydroxy-indol, 5,6-Dihydroxy-indolin, 5-Hydroxy-indol, 6-Hydroxy-indol, 7-Hydroxy-indol und 2,3-Indolindion, enthält.7. Composition according to one of claims 4 to 6, characterized in that in addition to the compounds of formula (I) there are still others known coupler substances which are selected from the group consisting of N- (3-dimethylaminophenyl) urea, 2,6-diaminopyridine,  2-amino-4 - [(2-hydroxyethyl) amino] anisole, 2,4-diamino-1-fluoro-5- methyl-benzene, 2,4-diamino-1-methoxy-5-methyl-benzene, 2,4-diamino-1- ethoxy-5-methyl-benzene, 2,4-diamino-1- (2-hydroxyethoxy) -5-methyl benzene, 2,4-di [(2-hydroxyethyl) amino] -1,5-dimethoxy-benzene, 2,3-diamino- 6-methoxy-pyridine, 3-amino-6-methoxy-2- (methylamino) -pyridine, 2,6-diamino-3,5-dimethoxypyridine, 3,5-diamino-2,6-dimethoxypyridine, 1,3-diamino-benzene, 2,4-diamino-1- (2-hydroxyethoxy) benzene, 1,3-diamino-4- (2,3-dihydroxypropoxy) benzene, 1,3-diamino-4- (3- hydroxypropoxy) benzene, 1,3-diamino-4- (2-methoxyethoxy) benzene, 2,4-diamino-1,5-di (2-hydroxyethoxy) benzene, 1-aminoethoxy) -2,4- diamino-benzene, 2-amino-1- (2-hydroxyethoxy) -4-rriethylamino-benzene, 2,4-diaminophenoxyacetic acid, 3- [di (2-hydroxyethyl) amino] aniline, 4-amino-2-di [(2-hydroxyethyl) amino] -1-ethoxy-benzene, 5-methyl-2- (1- methylethyl) phenol, 3 - [(2-hydroxyethyl) amino] aniline, 3 - [(2-aminoethyl) - amino] aniline, 1,3-di (2,4-diaminophenoxy) propane, di (2,4-diamino phenoxy) methane, 1,3-diamino-2,4-dimethoxy-benzene, 2,6-bis (2-hydroxy ethyl) aminotoluene, 4-hydroxyindole, 3-dimethylaminophenol, 3-diethyl aminophenol, 5-amino-2-methylphenol, 5-amino-4-fluoro-2-methyl phenol, 5-amino-4-methoxy-2-methylphenol, 5-amino-4-ethoxy-2-methyl phenol, 3-amino-2,4-dichlorophenol, 5-amino-2,4-dichlorophenol, 3-amino 2-methylphenol, 3-amino-2-chloro-6-methylphenol, 3-aminophenol, 2 - [(3-hydroxyphenyl) amino] acetamide, 5 - [(2-hydroxyethyl) amino] -4- methoxy-2-methylphenol, 5 - [(2-hydroxyethyl) amino] -2-methylphenol, 3 - [(2-hydroxyethyl) amino] phenol, 3 - [(2-methoxyethyl) amino] phenol, 5-amino-2-ethylphenol, 5-amino-2-methoxyphenol, 2- (4-amino-2- hydroxyphenoxy) ethanol, 5 - [(3-hydroxypropyl) amino] -2-methylphenol, 3 - [(2,3-dihydroxypropyl) amino] -2-methylphenol, 3 - [(2-hydroxyethyl) - amino] -2-methylphenol, 2-amino-3-hydroxy-pyridine, 2,6-dihydroxy-3,4-  dimethylpyridine, 5-amino-4-chloro-2-methylphenol, 1-naphthol, 2-methyl-1- naphthol, 1,5-dihydroxy-naphthalene, 1,7-dihydroxy-naphthalene, 2,3-dihydroxy-naphthalene, 2,7-dihydroxy-naphthalene, 2-methyl-1-naphthol acetate, (m-dihydroxyphenyl) acrylamide, 1-chloro-2,4-dihydroxybenzene, 2-chloro (m-dihydroxyphenyl) acrylamide, 1,2-dichloro-3,5-dihydroxy-4- methyl benzene, 1,5-dichloro-2,4-dihydroxy-benzene, 1,3-dihydroxy-2-methyl benzene, 3,4-methylenedioxy-phenol, 3,4-methylenedioxy-aniline, 5 - [(2-hydroxyethyl) amino] -1, 3-benzodioxole, 6-bromo-1-hydroxy-3,4- methylenedioxy-benzene, 3,4-diamino-benzoic acid, 3,4-dihydro-6-hydroxy- 1,4 (2H) -benzoxazine, 6-amino-3,4-dihydro-1,4 (2H) -benzoxazine, 3-methyl- 1-phenyl-5-pyrazolone, 5,6-dihydroxy-indole, 5,6-dihydroxy-indoline, 5-hydroxy-indole, 6-hydroxy-indole, 7-hydroxy-indole and 2,3-indolinedione, contains. 8. Mittel nach einem der Ansprüche 4 bis 7, dadurch gekennzeichnet, dass die Entwicklersubstanzen und Kupplersubstanzen, bezogen auf die Gesamtmenge des Färbemittels, jeweils in einer Gesamtmenge von 0,005 bis 20 Gewichtsprozent enthalten sind.8. Agent according to one of claims 4 to 7, characterized in that the developer substances and coupler substances, based on the Total amount of the colorant, each in a total amount of 0.005 up to 20 percent by weight are included. 9. Mittel nach einem der Ansprüche 4 bis 8, dadurch gekennzeichnet, dass es zusätzlich mindestens einen direktziehenden Farbstoff enthält.9. Composition according to one of claims 4 to 8, characterized in that it also contains at least one substantive dye. 10. Mittel nach einem der Ansprüche 4 bis 9, dadurch gekennzeichnet, dass es einen pH-Wert von 6,5 bis 11,5 aufweist.10. Agent according to one of claims 4 to 9, characterized in that it has a pH of 6.5 to 11.5. 11. Mittel nach einem der Ansprüche 4 bis 10, dadurch gekennzeichnet, dass es ein Haarfärbemittel ist. 11. Agent according to one of claims 4 to 10, characterized characterized that it is a hair dye.   12. Gebrauchsfertiges Mittel zum oxidativen Färben von Haaren, dadurch gekennzeichnet, dass es mindestens ein 1,3-Dihydroxy-benzol- Derivat der Formel (I) gemäß einem der Ansprüche 1 bis 3 sowie ein Oxidationsmittel enthält.12. Ready-to-use agent for oxidative coloring of hair, characterized in that there is at least one 1,3-dihydroxy-benzene Derivative of formula (I) according to one of claims 1 to 3 and a Contains oxidizing agents.
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002096901A2 (en) * 2001-05-25 2002-12-05 Wella Aktiengesellschaft 1,3-dihydroxybenzene derivatives and colorants containing said compounds
WO2006097224A1 (en) * 2005-03-18 2006-09-21 Unilever Plc Novel resorcinol derivatives for skin
WO2006097223A1 (en) * 2005-03-18 2006-09-21 Unilever Plc Novel resorcinol derivatives
WO2012013418A2 (en) 2010-07-29 2012-02-02 Unilever Plc Skin care compositions comprising substituted monoamines
WO2012013417A2 (en) 2010-07-29 2012-02-02 Unilever Plc Skin care compositions comprising substituted diamines
JP2013545770A (en) * 2010-12-16 2013-12-26 ロレアル Method for removing pigments of keratin components using resorcinol derivatives

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002096901A2 (en) * 2001-05-25 2002-12-05 Wella Aktiengesellschaft 1,3-dihydroxybenzene derivatives and colorants containing said compounds
WO2002096901A3 (en) * 2001-05-25 2003-03-13 Wella Ag 1,3-dihydroxybenzene derivatives and colorants containing said compounds
US7125428B2 (en) 2001-05-25 2006-10-24 Wella Ag 1,3-Dihydroxybenzene derivatives and colorants containing said compounds
WO2006097224A1 (en) * 2005-03-18 2006-09-21 Unilever Plc Novel resorcinol derivatives for skin
WO2006097223A1 (en) * 2005-03-18 2006-09-21 Unilever Plc Novel resorcinol derivatives
US7468464B2 (en) 2005-03-18 2008-12-23 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Resorcinol derivatives for skin
WO2012013418A2 (en) 2010-07-29 2012-02-02 Unilever Plc Skin care compositions comprising substituted monoamines
WO2012013417A2 (en) 2010-07-29 2012-02-02 Unilever Plc Skin care compositions comprising substituted diamines
US8476251B2 (en) 2010-07-29 2013-07-02 Conopco, Inc. Skin care compositions comprising substituted diamines
JP2013545770A (en) * 2010-12-16 2013-12-26 ロレアル Method for removing pigments of keratin components using resorcinol derivatives

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