DE10114970C2 - 1,2-Diaminobenzol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 1,2-Diaminobenzol-Derivate - Google Patents

1,2-Diaminobenzol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 1,2-Diaminobenzol-Derivate

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Publication number
DE10114970C2
DE10114970C2 DE2001114970 DE10114970A DE10114970C2 DE 10114970 C2 DE10114970 C2 DE 10114970C2 DE 2001114970 DE2001114970 DE 2001114970 DE 10114970 A DE10114970 A DE 10114970A DE 10114970 C2 DE10114970 C2 DE 10114970C2
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Germany
Prior art keywords
benzene
diamino
thienyl
phenyl
methyl
Prior art date
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Expired - Fee Related
Application number
DE2001114970
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English (en)
Other versions
DE10114970A1 (de
Inventor
Cecile Pasquier
Veronique Charriere
Hans-Juergen Braun
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Procter and Gamble Deutschland GmbH
Original Assignee
Wella GmbH
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Priority to DE2001114970 priority Critical patent/DE10114970C2/de
Publication of DE10114970A1 publication Critical patent/DE10114970A1/de
Application granted granted Critical
Publication of DE10114970C2 publication Critical patent/DE10114970C2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
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    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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    • 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
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Description

Die Erfindung betrifft neue 1,2-Diaminobenzol-Derivate sowie Mittel zum oxidativen Färbung von Keratinfasern, insbesondere menschlichen Haaren, welche 1,2-Diaminobenzol-Derivate enthalten.
Auf dem Gebiet der Färbung von Keratinfasern, insbesondere der Haarfärbung, haben Oxidationsfarbstoffe eine wesentliche Bedeutung erlangt. Die Färbung entsteht hierbei durch Reaktion bestimmter Entwicklersubstanzen mit bestimmten Kupplersubstanzen in Gegenwart eines geeigneten Oxidationsmittels. Als Entwicklersubstanzen werden hierbei insbesondere 1,4-Diaminobenzol, 2,5-Diaminotoluol, 2-(2,5-Diaminophenyl)ethanol, 3-Methyl-4-aminophenol und 4,5-Diamino-1- (2-hydroxyethyl)-1H-Pyrazol eingesetzt, während als Kupplersubstanzen beispielsweise Resorcin, 2-Methylresorcin, 4-Chlorresorcin, 1-Naphthol, 3-Aminophenol, 5-Amino-2-methylphenol und Derivate des m-Phenylen­ diamins zu nennen sind.
An Oxidationsfarbstoffe, die zur Färbung menschlicher Haare verwendet werden, werden neben der Färbung in der gewünschten Intensität zahlreiche zusätzliche Anforderungen gestellt. So müssen die Farbstoffe in toxikologischer und dermatologischer Hinsicht unbedenklich sein und die erzielten Haarfärbungen eine gute Lichtechtheit, Dauerwellechtheit, Säureechtheit und Reibeechtheit aufweisen. Auf jeden Fall aber müssen solche Färbungen ohne Einwirkung von Licht, Reibung und chemischen Mitteln über einen Zeitraum von mindestens 4 bis 6 Wochen stabil bleiben. Außerdem ist es erforderlich, daß durch Kombination geeigneter Entwicklersubstanzen und Kupplersubstanzen eine breite Palette verschiedener Farbnuancen erzeugt werden kann.
Die Verwendung von 1,4-Diaminobenzolen als Entwicklersubstanz in Oxidationshaarfärbemitteln ist aus dem Stand der Technik, beispielsweise der EP 0634163 A1 bekannt. Ebenfalls ist die Verwendung von mit einem aromatischen oder heteroaromatischen Rest substituierten 1,4-Diamino­ benzolen in Oxidationshaarfärbemitteln aus dem Stand der Technik, beispielsweise der DE 199 22 392 C1, DE 198 22 041 A1, DE 198 12 058 C1 und DE 198 12 059, bekannt.
Mit den derzeit eingesetzten Färbemitteln auf der Basis von 1,4-Diamino­ benzolen ist es jedoch nicht möglich, die vorgenannten Anforderungen in allen Punkten zu erfüllen.
Es bestand daher weiterhin ein Bedürfnis nach neuen Oxidationsfarbstoff­ vorstufen, welche die vorgenannten Anforderung in besonderem Masse erfüllen.
Hierzu wurde nun überraschenderweise gefunden, daß bestimmte 1,2-Diaminobenzol-Derivate die gestellten Anforderungen in besonders hohem Masse erfüllen. So werden bei Verwendung dieser Substanzen mit den meisten bekannten Kuppler- oder Entwicklersubstanzen farbstarke Farbnuancen erhalten, die außerordentlich lichtecht und waschecht sind.
Gegenstand der vorliegende Erfindung sind daher Mittel zur oxidativen Färbung von Keratinfasern, insbesondere menschlichen Haaren, auf der Basis einer Entwicklersubstanz-Kupplersubstanz-Kombination, welche mindestens ein 1,2-Diaminobenzol-Derivat aus der Gruppe bestehend aus 1,2-Diamino-4-(2-thienyl)benzol; 1,2-Diamino-4-(3-thienyl)benzol; 1,2-Diamino-4-(3-furyl)benzol; 1,2-Diamino-4-(pyrrol-3-yl)benzol; 1,2-Diamino-4-(1-methyl-1H-pyrrol-3-yl)benzol; 1,2-Diamino-4-(3-methyl- 2-thienyl)benzol; 1,2-Diamino-4-(5-methyl-2-thienyl)benzol; 1,2-Diamino- 4-(3-brom-2-thienyl)benzol; 1,2-Diamino-4-(5-chlor-2-thienyl)benzol; 1,2-Diamino-4-(5-acetyl-2-thienyl)benzol; 1,2-Diamino-4-(5-nitro-2- thienyl)benzol; 1,2-Diamino-4-(3,4-dinitro-2-thienyl)benzol; 1,2-Diamino-4- (5-formyl-2-thienyl)benzol; 1,2-Diamino-4-(2-methyl-3-thienyl)benzol; 1,2-Diamino-4-(2-methyl-3-furyl)benzol; 1,2-Diamino-4-(4-methyl-3- thienyl)benzol; 1,2-Diamino-4-(4-methyl-3-furyl)benzol; 1,2-Diamino-4-(5- methyl-3-thienyl)benzol; 1,2-Diamino-4-(5-methyl-3-furyl)benzol; 1,2-Diamino-4-(2-ethyl-3-thienyl)benzol; 1,2-Diamino-4-(2-ethyl-3- furyl)benzol; 1,2-Diamino-4-(4-ethyl-3-thienyl)benzol; 1,2-Diamino-4-(4- ethyl-3-furyl)benzol; 1,2-Diamino-4-(5-ethyl-3-thienyl)benzol; 1,2-Diamino- 4-(5-ethyl-3-furyl)benzol; 1,2-Diamino-4-(2-chlor-3-thienyl)benzol; 1,2-Diamino-4-(2-chlor-3-furyl)benzol; 1,2-Diamino-4-(4-chlor-3-thienyl)­ benzol; 1,2-Diamino-4-(4-chlor-3-furyl)benzol; 1,2-Diamino-4-(5-chlor-3- thienyl)benzol; 1,2-Diamino-4-(5-chlor-3-furyl)benzol; 1,2-Diamino-4-(2- dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(2-dimethylamino-3- furyl)benzol; 1,2-Diamino-4-(4-dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(4-dimethylamino-3-furyl)benzol; 1,2-Diamino-4-(5- dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(5-dimethylamino-3- furyl)benzol; 1,2-Diamino-4-(2-formyl-3-thienyl)benzol; 1,2-Diamino-4-(2- formyl-3-furyl)benzol; 1,2-Diamino-4-(4-formyl-3-thienyl)benzol; 1,2-Diamino-4-(4-formyl-3-furyl)benzol; 1,2-Diamino-4-(5-formyl-3- thienyl)benzol; 1,2-Diamino-4-(5-formyl-3-furyl)benzol; 1,2-Diamino-4-(2- acetyl-3-thienyl)benzol; 1,2-Diamino-4-(2-acetyl-3-furyl)benzol; 1,2-Diamino-4-(4-acetyl-3-thienyl)benzol; 1,2-Diamino-4-(4-acetyl-3- furyl)benzol; 1,2-Diamino-4-(5-acetyl-3-thienyl)benzol; 1,2-Diamino-4-(5- acetyl-3-furyl)benzol; 1,2-Diamino-4-(2-cyano-3-thienyl)benzol; 1,2-Diamino-4-(1,3-thiazol-2-yl)benzol; 1,2-Diamino-4-(5-nitro-1,3-thiazol- 2-yl)benzol; 1,2-Diamino-4-(1H-pyrazol-4-yl)benzol; 1,2-Diamino-4-(3- methyl-1H-pyrazol-4-yl)benzol; 1,2-Diamino-4-(3,5-dimethyl-1H-pyrazol-4- yl)benzol; 1,2-Diamino-4-phenyl-benzol; 1,2-Diamino-4-(4-methylphenyl)- benzol; 1,2-Diamino-4-(3-methylphenyl)-benzol; 1,2-Diamino-4-(2-methyl­ phenyl)-benzol; 1,2-Diamino-4-(2,3-dimethylphenyl)benzol; 1,2-Diamino- 4-(2,4-dimethylphenyl)benzol; 1,2-Diamino-4-(2,5-dimethylphenyl)benzol; 1,2-Diamino-4-(2,6-dimethylphenyl)benzol; 1,2-Diamino-4-(3,4-dimethyl­ phenyl)benzol; 1,2-Diamino-4-(3,5-dimethylphenyl)benzol; 1,2-Diamino-4- (2,4,5-trimethylphenyl)benzol; 1,2-Diamino-4-(2,4,6- trimethylphenyl)benzol; 1,2-Diamino-4-(4-chlor-phenyl)benzol; 1,2- Diamino-4-(3-chlorphenyl)-benzol; 1,2-Diamino-4-(2-chlorphenyl)benzol; 1,2-Diamino-4-(4-fluor-phenyl)benzol; 1,2-Diamino-4-(3- fluorphenyl)benzol; 1,2-Diamino-4-(2-fluorphenyl)benzol; 1,2-Diamino-4- (4-bromphenyl)benzol; 1,2-Diamino-4-(3-bromphenyl)benzol; 1,2- Diamino-4-(2-bromphenyl)benzol; 1,2-Diamino-4-(4-jodphenyl)benzol; 1,2- Diamino-4-(3-jodphenyl)benzol; 1,2-Diamino-4-(2-jodphenyl)benzol; 1,2- Diamino-4-(3,5-dichlorphenyl)benzol; 1,2-Diamino-4-(2,3- dichlorphenyl)benzol; 1,2-Diamino-4-(3,4-dichlorphenyl)benzol; 1,2-Diamino-4-(4-(trifluormethyl-phenyl)benzol; 1,2-Diamino-4-(3-(trifluor­ methylphenyl)benzol; 1,2-Diamino-4-(2-(trifluormethylphenyl)benzol; 1,2-Diamino-4-(4-chlor-3-trifluoromethyl-phenyl)benzol; 1,2-Diamino-4-(4- methoxyphenyl)benzol; 1,2-Diamino-4-(3-methoxyphenyl)benzol; 1,2-Diamino-4-(2-methoxyphenyl)benzol; 1,2-Diamino-4-(4-ethoxy­ phenyl)benzol; 1,2-Diamino-4-(3-ethoxyphenyl)-benzol; 1,2-Diamino-4-(2- ethoxyphenyl)benzol; 1,2-Diamino-4-(2,4-dimethoxyphenyl)benzol; 1,2-Diamino-4-(2,5-dimethoxyphenyl)benzol; 1,2-Diamino-4-(3,4- dimethoxyphenyl)benzol; 1,2-Diamino-4-(1,3-benzodioxol-5-yl)benzol; 1,2-Diamino-4-(4-methylthiophenyl)benzol; 1,2-Diamino-4-(3-methylthio­ phenyl)benzol; 1,2-Diamino-4-(2-methylthio-phenyl)benzol; 1,2-Diamino- 4-(4-methoxy-2-methylphenyl)benzol; 1,2-Diamino-4-(4- cyanophenyl)benzol; 1,2-Diamino-4-(3-cyanophenyl)-benzol; 1,2-Diamino- 4-(2-cyanophenyl)-benzol; 1,2-Diamino-4-(4-hydroxy-phenyl)benzol; 1,2-Diamino-4-(3-hydroxyphenyl)-benzol; 1,2-Diamino-4-(2-hydroxy­ phenyl)benzol; 1,2-Diamino-4-(4-hydroxy-2-methylphenyl)benzol; 1,2-Diamino-4-(4-nitrophenyl)benzol; 1,2-Diamino-4-(3-nitrophenyl)benzol; 1,2-Diamino-4-(2-nitrophenyl)benzol; 1,2-Diamino-4-(2-methyl-4-nitro­ phenyl)benzol; 1,2-Diamino-4-(4-methyl-3-nitro-phenyl)-benzol; 1,2-Diamino-4-(4-methyl-2-nitro-phenyl)benzol; 1,2-Diamino-4-(4- methoxy-2-nitro-phenyl)benzol; 1,2-Diamino-4-(4-aminophenyl)benzol; 1,2-Diamino-4-(3-aminophenyl)-benzol; 1,2-Diamino-4-(4-amino-3-methyl­ phenyl)benzol; 1,2-Diamino-4-(4-dimethylamino-phenyl)benzol; 1,2-Diamino-4-(3-dimethyl-aminophenyl)-benzol; 1,2-Diamino-4-(4-di(2- hydroxyethyl)amino-phenyl)benzol; 1,2-Diamino-4-(3-di(2-hydroxyethyl)- amino-phenyl)benzol; 1,2-Diamino-4-(2,4-diaminophenyl)benzol; 1,2-Diamino-4-(2,4-dimethyl-aminophenyl)-benzol; 1,2-Diamino-4-(2,4- di(2-hydroxyethyl)amino-phenyl)benzol; 1,2-Diamino-4-(4-formyl­ phenyl)benzol; 1,2-Diamino-4-(3-formylphenyl)-benzol; 1,2-Diamino-4-(2- formylphenyl)-benzol; 1,2-Diamino-4-(4-acetylphenyl)benzol; 1,2-Diamino- 4-(3-acetylphenyl)benzol; 1,2-Diamino-4-(2-acetylphenyl)benzol; 1,2-Diamino-4-(4-(trimethylsilyl)-phenyl)benzol; 1,2-Diamino-4-(3- (trimethylsilyl)-phenyl)benzol; 1,2-Diamino-4-(2-(trimethylsilyl)-phenyl)­ benzol; 1,2-Diamino-4-(4-hydroxycarbonylphenyl)-benzol; 1,2-Diamino-4- (3-hydroxycarbonylphenyl)benzol; 1,2-Diamino-4-(2-hydroxycarbonyl­ phenyl)benzol; 1,2-Diamino-4-(4-ethoxycarbonylphenyl)-benzol; 1,2-Diamino-4-(3-ethoxycarbonylphenyl)benzol; 1,2-Diamino-4-(2- ethoxycarbonylphenyl)benzol; 1,2-Diamino-4-(4-methoxy-carbonylphenyl)­ benzol; 1,2-Diamino-4-(3-methoxycarbonylphenyl)benzol; 1,2-Diamino-4- (2-methoxycarbonylphenyl)benzol; 1,2-Diamino-4-(4-carboxamidophenyl)­ benzol; 1,2-Diamino-4-(3-carboxamidophenyl)benzol; 1,2-Diamino-4-(2- carboxamidophenyl)benzol; 1,2-Diamino-4-(4-benzophenon)benzol; 1,2-Diamino-4-(4-cyanomethyl-phenyl)benzol; 1,2-Diamino-4-(3-cyano­ methyl-phenyl)benzol; 1,2-Diamino-4-(2-cyanomethyl-phenyl)benzol; 1,2-Diamino-4-(2-pyridinyl)-benzol; 1,2-Diamino-4-(3-pyridinyl)benzol; 1,2-Diamino-4-(4-pyridinyl)-benzol; 1,2-Diamino-4-(3-methyl-2-pyridinyl)- benzol; 1,2-Diamino-4-(4-methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(5- methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(6-methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(5-nitro-2-pyridinyl)benzol und 1,2-Diamino-4-(5- pyrimidinyl)-benzol oder deren physiologisch verträgliche Salze enthalten.
Die vorgenannten 1,2-Diaminobenzol-Derivate können sowohl als freie Basen als auch in Form ihrer physiologisch verträglichen Salze mit anorganischen oder organischen Säuren, wie zum Beispiel Salzsäure, Schwefelsäure, Phosphorsäure, Essigsäure, Propionsäure, Milchsäure oder Zitronensäure, eingesetzt werden.
Bevorzugte 1,2-Diaminobenzol-Derivate sind hierbei das 1,2-Diamino-4-(2-thienyl)benzol; 1,2-Diamino-4-(3-thienyl)benzol; 1,2-Diamino-4-(3-furyl)benzol; 1,2-Diamino-4-(4-methyl-3-thienyl)benzol; 1,2-Diamino-4-phenyl-benzol; 1,2-Diamino-4-(4-methylphenyl)benzol; 1,2-Diamino-4-(3-methylphenyl)benzol; 1,2-Diamino-4-(3,4-dimethyl­ phenyl)benzol; 1,2-Diamino-4-(4-methoxyphenyl)benzol; 1,2-Diamino-4- (3-methoxyphenyl)benzol; 1,2-Diamino-4-(2,4-dimethoxyphenyl)benzol; 1,2-Diamino-4-(3,4-dimethoxyphenyl)benzol; 1,2-Diamino-4-(1,3-benzo­ dioxol-5-yl)benzol; 1,2-Diamino-4-(4-methylthiophenyl)benzol; 1,2-Diamino-4-(4-cyanophenyl)benzol; 1,2-Diamino-4-(4-hydroxyphenyl)­ benzol; 1,2-Diamino-4-(3-hydroxyphenyl)benzol; 1,2-Diamino-4-(4- hydroxy-2-methylphenyl)benzol; 1,2-Diamino-4-(4-cyanomethyl­ phenyl)benzol; 1,2-Diamino-4-(3-cyanomethyl-phenyl)benzol; 1,2-Diamino-4-(2-cyano-methyl-phenyl)benzol; 1,2-Diamino-4-(2- pyridinyl)benzol; 1,2-Diamino-4-(3-pyridinyl)benzol; 1,2-Diamino-4-(5- methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(6-methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(5-pyrimidinyl)benzol oder deren physiologisch verträgliche Salze.
Die erfindungsgemäßen 1,2-Diaminobenzol-Derivate sind in dem erfindungsgemäßen Färbemittel in einer Gesamtmenge von etwa 0,005 bis 20 Gewichtsprozent enthalten, wobei eine Menge von etwa 0,01 bis 5 Gewichtsprozent und insbesondere von 0,1 bis 2,5 Gewichtsprozent bevorzugt ist.
Die hier beschriebenen 1,2-Diaminobenzol-Derivate können sowohl alleine als auch in Kombination mit weiteren Entwicklersubstanzen und/oder Kupplersubstanzen verwendet werden.
Als Kupplersubstanzen können beispielsweise N-(3-Dimethylamino­ phenyl)-harnstoff, 2,6-Diamino-pyridin, 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-hydroxy­ ethyl)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-dihydroxy­ propoxy)-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-(2-Aminoethoxy)-2,4-diamino-benzol, 2-Amino-1-(2-hydroxyethoxy)-4- methylamino-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-diaminophenoxy)- methan, 1,3-Diamino-2,4-dimethoxy-benzol, 2,6-Bis(2-hydroxyethyl)amino­ toluol, 4-Hydroxyindol, 3-Dimethylamino-phenol, 3-Diethylamino-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-Hydroxy-ethyl)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-hydroxyphenoxy)-ethanol, 5-[(3-Hydroxy-propyl)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, 1,3-Dihydroxy- benzol, 1-Chlor-2,4-dihydroxy-benzol, 2-Chlor-1,3-dihydroxy-benzol, 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 eingesetzt werden.
Als Entwicklersubstanzen können beispielsweise 1,4-Diaminobenzol, 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-diaminobenzot, 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-hydroxyethoxy)-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-Hydroxy­ propyl)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-hydroxy­ ethyl)amino]-2-propanol, 1,4-Bis[(4-Aminophenyl)-amino]-butan, 1,8-Bis­ (2,5-diaminophenoxy)-3,6-dioxaoctan, 4-Amino-phenol, 4-Amino-3-methyl- phenol, 4-Amino-3-(hydroxymethyl)-phenol, 4-Amino-3-fluor-phenol, 4-Methylamino-phenol, 4-Amino-2-(aminomethyl)-phenol, 4-Amino-2- (hydroxymethyl)-phenol, 4-Amino-2-fluor-phenol, 4-Amino-2-[(2-hydroxy­ ethyl)-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)-1H-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-Trihydroxy-phenol eingesetzt werden.
Die Kupplersubstanzen und Entwicklersubstanzen können in dem erfindungsgemäßen Färbemittel jeweils einzeln oder im Gemisch miteinander enthalten sein, wobei die Gesamtmenge an Kuppler­ substanzen und Entwicklersubstanzen in dem erfindungsgemäßen Färbemittel (bezogen auf die Gesamtmenge des Färbemittels) jeweils etwa 0,005 bis 20 Gewichtsprozent, vorzugsweise etwa 0,01 bis 5 Gewichts­ prozent und insbesondere 0,1 bis 2,5 Gewichtsprozent, beträgt.
Die Gesamtmenge der in dem hier beschriebenen Färbemittel enthaltenen Entwicklersubstanz-Kupplersubstanz-Kombination beträgt vorzugsweise etwa 0,01 bis 20 Gewichtsprozent, wobei eine Menge von etwa 0,02 bis 10 Gewichtsprozent und insbesondere 0,2 bis 6 Gewichtsprozent besonders bevorzugt ist. Die Entwicklersubstanzen und Kupplersubstanzen werden im allgemeinen in etwa äquimolaren Mengen eingesetzt; es ist jedoch nicht nachteilig, wenn die Entwicklersubstanzen diesbezüglich in einem gewissen Uberschuß oder Unterschuß vorhanden sind.
Weiterhin kann das erfindungsgemäße Färbemittel zusätzlich andere Farbkomponenten, beispielsweise 6-Amino-2-methylphenol und 2-Amino-5- methylphenol, sowie ferner übliche direktziehende Farbstoffe, zum Beispiel Triphenylmethanfarbstoffe wie 4-[(4'-aminophenyl)-(4'-imino-2",5"- cyclohexadien-1"-yliden)-methyl]-2-methylaminobenzol-monohydrochlorid (C.I. 42 510) und 4-[(4'amino-3'-methyl-phenyl)-(4"-imino-3"-methyl- 2",5"cyclohexadien-1"-yliden)-methyl]-2-methyl-aminobenzol­ monohydrochlorid (C.I. 42 520), aromatische Nitrofarbstoffe wie 4-(2'-hydroxyethyl)amino-nitrotoluol, 2-Amino-4,6-dinitrophenol, 2-Amino-5- (2'-hydroxyethyl)amino-nitrobenzol, 2-Chlor-6-(ethylamino)-4-nitro-phenol, 4-Chlor-N-(2-hydroxyethyl)-2-nitroanilin, 5-Chlor-2-hydroxy-4-nitroanilin, 2-Amino-4-chlor-6-nitrophenol und 1-[(2'-Ureidoethyl)amino-4-nitrobenzol, Azofarbstoffe wie 6-[(4'-Aminophenyl)azo]-5hydroxy-naphthalin-1-sulfon­ säure-Natriumsalz (C.I. 14 805) und Dispersionsfarbstoffe wie beispiels­ weise 1,4-Diaminoanthrachinon und 1,4,5,8-Tetraaminoantrachinon, enthalten. Die Färbemittel können diese Farbkomponenten in einer Menge von etwa 0,1 bis 4 Gewichtsprozent enthalten.
Selbstverständlich können die Kupplersubstanzen und Entwickler­ substanzen sowie die anderen Farbkomponenten, sofern es Basen sind, auch in Form der physiologisch verträglichen Salze mit organischen oder anorganischen Säuren, wie beispielsweise Salzsäure oder Schwefelsäure, beziehungsweise - sofern sie aromatische OH-Gruppen besitzen - in Form der Salze mit Basen, zum Beispiel als Alkaliphenolate, eingesetzt werden.
Darüber hinaus können in den Färbemitteln, falls diese zur Färbung von Haaren verwendet werden sollen, noch weitere übliche kosmetische Zusätze, beispielsweise Antioxidantien wie Ascorbinsäure, Thioglykolsäure oder Natriumsulfit, sowie Parfümöle, Komplexbildner, Netzmittel, Emulgatoren, Verdicker und Pflegestoffe enthalten sein.
Die Zubereitungsform des erfindungsgemäßen Färbemittels kann beispielsweise eine Lösung, insbesondere eine wässrige oder wässrig- alkoholische Lösung sein. Die besonders bevorzugten Zubereitungsformen sind jedoch eine Creme, ein Gel oder eine Emulsion. Ihre Zusammen­ setzung stellt eine Mischung der Farbstoffkomponenten mit den für solche Zubereitungen üblichen Zusätzen dar.
Übliche Zusätze in Lösungen, Cremes, Emulsionen oder Gelen sind zum Beispiel Lösungsmittel wie Wasser, niedere aliphatische Alkohole, beispielsweise Ethanol, Propanol oder Isopropanol, Glycerin oder Glykole wie 1,2-Propylenglykol, weiterhin Netzmittel oder Emulgatoren aus den Klassen der anionischen, kationischen, amphoteren oder nichtionogenen oberflächenaktiven Substanzen wie zum Beispiel Fettalkoholsulfate, oxethylierte Fettalkoholsulfate, Alkylsulfonate, Alkylbenzolsulfonate, Alkyltrimethylammoniumsalze, Alkylbetaine, oxethylierte Fettalkohole, oxethylierte Nonylphenole, Fettsäurealkanolamide und oxethylierte Fettsäureester ferner Verdicker wie höhere Fettalkohole, Stärke, Cellulosederivate, Petrolatum, Paraffinöl und Fettsäuren, sowie außerdem Pflegestoffe wie kationische Harze, Lanolinderivate, Cholesterin, Pantothensäure und Betain. Die erwähnten Bestandteile werden in den für solche Zwecke üblichen Mengen verwendet, zum Beispiel die Netzmittel und Emulgatoren in Konzentrationen von etwa 0,5 bis 30 Gewichts-prozent, die Verdicker in einer Menge von etwa 0,1 bis 25 Gewichts-prozent und die Pflegestoffe in einer Konzentration von etwa 0,1 bis 5 Gewichtsprozent.
Je nach Zusammensetzung kann das erfindungsgemäße Färbemittel schwach sauer, neutral oder alkalisch reagieren. Vorzugsweise weist das erfindungsgemäße Färbemittel einen pH-Wert von 5 bis 11,5 auf, wobei ein pH-Wert von etwa 6,8 bis 10,5 besonders bevorzugt ist. Die basische Einstellung erfolgt vorzugsweise mit Ammoniak, es können aber auch organische Amine, zum Beispiel Monoethanolamin und Triethanolamin, oder auch anorganische Basen wie Natriumhydroxid und Kaliumhydroxid verwendet werden. Für eine pH-Einstellung im sauren Bereich kommen anorganische oder organische Säuren, zum Beispiel Phosphorsäure, Essigsäure Zitronensäure oder Weinsäure, in Betracht.
Für die Anwendung zur oxidativen Färbung von Haaren vermischt man das vorstehend beschriebene Färbemittel unmittelbar vor dem Gebrauch mit einem Oxidationsmittel und trägt eine für die Haarfärbebehandlung ausreichende Menge, je nach Haarfülle, im allgemeinen etwa 60 bis 200 Gramm, dieses Gemisches auf das Haar auf.
Als Oxidationsmittel zur Entwicklung der Haarfärbung kommen haupt­ sächlich Wasserstoffperoxid oder dessen Additionsverbindungen an Harnstoff, Melamin, Natriumborat oder Natriumcarbonat in Form einer 3- bis 12prozentigen, vorzugsweise 6prozentigen, wässrigen Lösung, aber auch Luftsauerstoff in Betracht. Wird eine 6prozentige Wasserstoffperoxidlösung als Oxidationsmittel verwendet, so beträgt das Gewichtsverhältnis zwischen Haarfärbemittel und Oxidationsmittel 5 : 1 bis 1 : 2, vorzugsweise jedoch 1 : 1. Grössere Mengen an Oxidationsmittel werden vor allem bei höheren Farbstoffkonzentrationen im Haarfärbemittel, oder wenn gleichzeitig eine stärkere Bleichung des Haares beabsichtigt ist, verwendet. Man läßt das Gemisch bei 15 bis 50 Grad Celsius etwa 10 bis 45 Minuten lang, vorzugsweise 30 Minuten lang, auf das Haar einwirken, spült sodann das Haar mit Wasser aus und trocknet es. Gegebenenfalls wird im Anschluß an diese Spülung mit einem Shampoo gewaschen und eventuell mit einer schwachen organischen Säure, wie zum Beispiel Zitronensäure oder Weinsäure, nachgespült. Anschliessend wird das Haar getrocknet.
Die Haarfärbemittel mit einem Gehalt an den erfindungsgemäßen 1,2-Diaminobenzol-Derivaten im oxidativen System ermöglichen Haarfärbungen mit ausgezeichneter Farbechtheit, insbesondere was die Lichtechtheit, Waschechtheit und Reibeechtheit anbetrifft. Hinsichtlich der färberischen Eigenschaften bieten die erfindungsgemäßen Haarfärbemittel je nach Art und Zusammensetzung der Farbkomponenten eine breite Palette verschiedener Farbnuancen, welche sich von blonden über braune, purpure, violette bis hin zu blauen und schwarzen Farbtönen erstreckt. Hierbei zeichnen sich die Farbtöne durch ihre besondere Farbintensität aus. Die sehr guten färberischen Eigenschaften der Haarfärbemittel gemäß der vorliegenden Anmeldung zeigen sich weiterhin darin, daß diese Mittel eine Anfärbung von ergrauten, chemisch nicht vorgeschädigten Haaren problemlos und mit guter Deckkraft ermöglichen.
Die Herstellung der erfindungsgemäßen 1,2-Diaminobenzol-Derivate kann unter Verwendung von bekannten Syntheseverfahren erfolgen, beispielsweise durch eine Tetrakis(triphenylphospin)palladium (0) katalysierte Kupplung eines geeigneten substituierten 1,2-Diamino- Benzolborsäurederivates der Formel (I)
mit einer geeigneten halogensubstituierten zyklischen Verbindung und anschliessende Abspaltung der für die Kupplungsreaktion erforderlichen Schutzgruppen.
Die in der Formel (I) verwendeten Restgruppen haben hierbei die folgende Bedeutung:
Ra stellt eine Schutzgruppe dar, wie sie zum Beispiel in dem Kapitel "Protective Groups" in Organic Synthesis, Kapitel 7, Wiley Interscience, 1991 beschrieben wird;
Rb ist gleich Wasserstoff oder Ra;
Rc ist gleich Wasserstoff oder einer substituierten C2-C3-Brücke.
Die erfindungsgemäßen 1,2-Diaminobenzol-Derivate sind in Wasser gut löslich und ermöglichen allein oder in Kombination mit Entwicklern oder Kupplern Färbungen mit hoher Farbintensität und ausgezeichneter Farbechtheit, insbesondere was die Lichtechtheit, Waschechtheit und Reibeechtheit anbetrifft. Die Verbindungen der Formeln (I) weisen weiterhin eine ausgezeichnete Lagerstabilität, insbesondere als Bestandteil der vorstehend beschriebenen Färbemittel, auf.
Ein weiterer Gegenstand der vorliegenden Erfindung sind die neuen 1,2-Diaminobenzol-Derivate, welche ausgewählt sind aus der Gruppe bestehend aus 1,2-Diamino-4-(2-thienyl)benzol; 1,2-Diamino-4-(3- thienyl)benzol; 1,2-Diamino-4-(3-furyl)benzol; 1,2-Diamino-4-(pyrrol-3- yl)benzol; 1,2-Diamino-4-(1-methyl-1H-pyrrol-3-yl)benzol; 1,2-Diamino-4- (3-methyl-2-thienyl)benzol; 1,2-Diamino-4-(5-methyl-2-thienyl)benzol; 1,2-Diamino-4-(3-brom-2-thienyl)benzol; 1,2-Diamino-4-(5-chlor-2-thienyl)­ benzol; 1,2-Diamino-4-(5-acetyl-2-thienyl)benzol; 1,2-Diamino-4-(5-nitro- 2-thienyl)benzol; 1,2-Diamino-4-(3,4-dinitro-2-thienyl)benzol; 1,2-Diamino- 4-(5-formyl-2-thienyl)benzol; 1,2-Diamino-4-(2-methyl-3-thienyl)benzol; 1,2-Diamino-4-(2-methyl-3-furyl)benzol; 1,2-Diamino-4-(4-methyl-3- thienyl)benzol; 1,2-Diamino-4-(4-methyl-3-furyl)benzol; 1,2-Diamino-4-(5- methyl-3-thienyl)benzol; 1,2-Diamino-4-(5-methyl-3-furyl)benzol; 1,2-Diamino-4-(2-ethyl-3-thienyl)benzol; 1,2-Diamino-4-(2-ethyl-3- furyl)benzol; 1,2-Diamino-4-(4-ethyl-3-thienyl)benzol; 1,2-Diamino-4-(4- ethyl-3-furyl)benzol; 1,2-Diamino-4-(5-ethyl-3-thienyl)benzol; 1,2-Diamino- 4-(5-ethyl-3-furyl)benzol; 1,2-Diamino-4-(2-chlor-3-thienyl)benzol; 1,2-Diamino-4-(2-chlor-3-furyl)benzol; 1,2-Diamino-4-(4-chlor-3-thienyl)­ benzol; 1,2-Diamino-4-(4-chlor-3-furyl)benzol; 1,2-Diamino-4-(5-chlor-3- thienyl)benzol; 1,2-Diamino-4-(5-chlor-3-furyl)benzol; 1,2-Diamino-4-(2- dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(2-dimethylamino-3- furyl)benzol; 1,2-Diamino-4-(4-dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(4-dimethylamino-3-furyl)benzol; 1,2-Diamino-4-(5- dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(5-dimethylamino-3- furyl)benzol; 1,2-Diamino-4-(2-formyl-3-thienyl)benzol; 1,2-Diamino-4-(2- formyl-3-furyl)benzol; 1,2-Diamino-4-(4-formyl-3-thienyl)benzol; 1,2-Diamino-4-(4-formyl-3-furyl)benzol; 1,2-Diamino-4-(5-formyl-3- thienyl)benzol; 1,2-Diamino-4-(5-formyl-3-furyl)benzol; 1,2-Diamino-4-(2- acetyl-3-thienyl)benzol; 1,2-Diamino-4-(2-acetyl-3-furyl)benzol; 1,2-Diamino-4-(4-acetyl-3-thienyl)benzol; 1,2-Diamino-4-(4-acetyl-3- furyl)benzol; 1,2-Diamino-4-(5-acetyl-3-thienyl)benzol; 1,2-Diamino-4-(5- acetyl-3-furyl)benzol; 1,2-Diamino-4-(2-cyano-3-thienyl)benzol; 1,2-Diamino-4-(1,3-thiazol-2-yl)benzol; 1,2-Diamino-4-(5-nitro-1,3-thiazol- 2-yl)benzol; 1,2-Diamino-4-(1H-pyrazol-4-yl)benzol; 1,2-Diamino-4-(3- methyl-1H-pyrazol-4-yl)benzol; 1,2-Diamino-4-(3,5-dimethyl-1H-pyrazol-4- yl)benzol; 1,2-Diamino-4-(4-methylphenyl)-benzol; 1,2-Diamino-4-(3- methylphenyl)-benzol; 1,2-Diamino-4-(2-methyl-phenyl)-benzol; 1,2-Diamino-4-(2,3-dimethylphenyl)benzol; 1,2-Diamino-4-(2,4- dimethylphenyl)benzol; 1,2-Diamino-4-(2,5-dimethylphenyl)benzol; 1,2-Diamino-4-(2,6-dimethylphenyl)benzol; 1,2-Diamino-4-(3,4-dimethyl­ phenyl)benzol; 1,2-Diamino-4-(3,5-dimethylphenyl)benzol; 1,2-Diamino-4- (2,4,5-trimethylphenyl)benzol; 1,2-Diamino-4-(2,4,6-trimethylphenyl)­ benzol; 1,2-Diamino-4-(3-chlorphenyl)-benzol; 1,2-Diamino-4-(2- chlorphenyl)-benzol; 1,2-Diamino-4-(4-fluor-phenyl)benzol; 1,2-Diamino-4- (3-fluor-phenyl)benzol; 1,2-Diamino-4-(2-fluorphenyl)benzol; 1,2-Diamino- 4-(4-bromphenyl)benzol; 1,2-Diamino-4-(3-bromphenyl)benzol; 1,2-Diamino-4-(2-bromphenyl)benzol; 1,2-Diamino-4-(4-jodphenyl)benzol; 1,2-Diamino-4-(3-jodphenyl)benzol; 1,2-Diamino-4-(2-jodphenyl)benzol; 1,2-Diamino-4-(3,5-dichlorphenyl)benzol; 1,2-Diamino-4-(2,3-dichlor­ phenyl)benzol; 1,2-Diamino-4-(3,4-dichlorphenyl)benzol; 1,2-Diamino-4- (4-(trifluormethyl-phenyl)benzol; 1,2-Diamino-4-(3-(trifluor-methylphenyl)­ benzol; 1,2-Diamino-4-(2-(trifluormethylphenyl)benzol; 1,2-Diamino-4-(4- chlor-3-trifluoromethyl-phenyl)benzol; 1,2-Diamino-4-(4-methoxyphenyl)­ benzol; 1,2-Diamino-4-(3-methoxyphenyl)benzol; 1,2-Diamino-4-(2- methoxy-phenyl)benzol; 1,2-Diamino-4-(4-ethoxy-phenyl)benzol; 1,2-Diamino-4-(3-ethoxyphenyl)-benzol; 1,2-Diamino-4-(2-ethoxyphenyl)­ benzol; 1,2-Diamino-4-(2,4-dimethoxyphenyl)benzol; 1,2-Diamino-4-(2,5- dimethoxyphenyl)-benzol; 1,2-Diamino-4-(3,4-dimethoxy-phenyl)benzol; 1,2-Diamino-4-(1,3-benzodioxol-5-yl)benzol; 1,2-Diamino-4-(4-methyl­ thiophenyl)benzol; 1,2-Diamino-4-(3-methylthio-phenyl)benzol; 1,2-Diamino-4-(2-methylthio-phenyl)benzol; 1,2-Diamino-4-(4-methoxy-2- methylphenyl)benzol; 1,2-Diamino-4-(4-cyanophenyl)benzol; 1,2-Diamino- 4-(3-cyanophenyl)-benzol; 1,2-Diamino-4-(4-hydroxy-phenyl)benzol; 1,2-Diamino-4-(3-hydroxyphenyl)-benzol; 1,2-Diamino-4-(2-hydroxy­ phenyl)-benzol; 1,2-Diamino-4-(4-hydroxy-2-methylphenyl)benzol; 1,2-Diamino-4-(4-nitrophenyl)benzol; 1,2-Diamino-4-(3-nitrophenyl)benzol; 1,2-Diamino-4-(2-nitrophenyl)benzol; 1,2-Diamino-4-(2-methyl-4-nitro­ phenyl)benzol; 1,2-Diamino-4-(4-methyl-3-nitro-phenyl)-benzol; 1,2-Diamino-4-(4-methyl-2-nitro-phenyl)benzol; 1,2-Diamino-4-(4- methoxy-2-nitro-phenyl)benzol; 1,2-Diamino-4-(4-aminophenyl)-benzol; 1,2-Diamino-4-(3-aminophenyl)-benzol; 1,2-Diamino-4-(4-amino-3-methyl­ phenyl)benzol; 1,2-Diamino-4-(4-dimethylamino-phenyl)benzol; 1,2-Diamino-4-(3-dimethyl-aminophenyl)-benzol; 1,2-Diamino-4-(4-di(2- hydroxyethyl)amino-phenyl)benzol; 1,2-Diamino-4-(3-di(2-hydroxyethyl)­ amino-phenyl)benzol; 1,2-Diamino-4-(2,4-dimethyl-aminophenyl)-benzol; 1,2-Diamino-4-(2,4-di(2-hydroxyethyl)amino-phenyl)benzol; 1,2-Diamino- 4-(4-formylphenyl)benzol; 1,2-Diamino-4-(3-formylphenyl)-benzol; 1,2-Diamino-4-(2-formylphenyl)-benzol; 1,2-Diamino-4-(4-acetylphenyl)­ benzol; 1,2-Diamino-4-(3-acetylphenyl)benzol; 1,2-Diamino-4-(2-acetyl­ phenyl)-benzol; 1,2-Diamino-4-(4-(trimethylsilyl)-phenyl)benzol; 1,2-Diamino-4-(3-(trimethylsilyl)-phenyl)benzol; 1,2-Diamino-4-(2- (trimethylsilyl)-phenyl)-benzol; 1,2-Diamino-4-(4-hydroxycarbonylphenyl)­ benzol; 1,2-Diamino-4-(3-hydroxycarbonylphenyl)benzol; 1,2-Diamino-4- (2-hydroxycarbonyl-phenyl)benzol; 1,2-Diamino-4-(4-ethoxycarbonyl­ phenyl)-benzol; 1,2-Diamino-4-(3-ethoxycarbonylphenyl)benzol; 1,2- Diamino-4-(2-ethoxycarbonylphenyl)benzol; 1,2-Diamino-4-(4-methoxy­ carbonylphenyl)benzol; 1,2-Diamino-4-(3-methoxycarbonylphenyl)benzol; 1,2-Diamino-4-(2-methoxycarbonylphenyl)benzol; 1,2-Diamino-4-(4- carboxamidophenyl)benzol; 1,2-Diamino-4-(3-carboxamidophenyl)benzol; 1,2-Diamino-4-(2-carboxamidophenyl)benzol; 1,2-Diamino-4-(4- benzophenon)benzol; 1,2-Diamino-4-(4-cyanomethyl-phenyl)benzol; 1,2-Diamino-4-(3-cyano-methyl-phenyl)benzol; 1,2-Diamino-4-(2- cyanomethyl-phenyl)benzol; 1,2-Diamino-4-(2-pyridinyl)-benzol; 1,2-Diamino-4-(3-pyridinyl)benzol; 1,2-Diamino-4-(3-methyl-2-pyridinyl)- benzol; 1,2-Diamino-4-(4-methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(5- methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(6-methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(5-nitro-2-pyridinyl)benzol und 1,2-Diamino-4-(5- pyrimidinyl)-benzol sowie deren physiologisch verträglichen Salzen.
Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn darauf zu beschränken.
Beispiele 1. Herstellungsbeispiele Beispiel 1 bis 66 Synthese von 1,2-Diamino-benzol-Derivaten (Allgemeine Synthesevorschrift) A. Synthese von 1,2-di(tert.-Butyloxycarbonylamino)benzol
10,8 g (0,1 mol) o-Phenylendiamin und 52,4 g (0,24 mol) Di-tert.-butyl­ dicarbonat werden in einer Mischung von 125 ml 2 N Natriumhydroxid und 180 ml Dichlormethan gelöst und 24 Stunden lang bei Raumtemperatur gerührt. Anschliessend wird die organische Phase abgetrennt, mit einer gesättigten wässrigen Kochsalzlösung bis zu einem neutralem pH-Wert gewaschen, über MgSO4 getrocknet, filtriert und eingeengt.
Der erhaltene Rückstand wird in 200 ml Hexan aufgenommen. Der Niederschlag wird sodann abfiltriert und mit 50 ml Hexan nachgewaschen, und getrocknet.
Es werden 29,2 g (95% der Theorie) 1,2-di(tert.-Butyloxycarbonylamino) benzol mit einem Schmelzpunkt von 125-126°C erhalten.
1H-NMR (300 MHz, DMSO): δ = 8,49 (s, 2H, NH); 7,47 (m, 2H, H4 und H5); 7,07 (m, 2H, H3 und H6); 1,48 (s, 18H).
CHN-Analyse
B. Synthese von 1,2-di(tert.-Butyloxycarbonylamino)-4-brombenzol
10 g (32 mmol) 1,2-di(tert.-Butyloxycarbonylamino)benzol aus Stufe A und 6,3 g (35,2 mmol) N-Bromsuccinimid werden unter Stickstoff in 120 ml 1,2-Dimethoxyethan gelöst und 6 Stunden lang bei Raumtemperatur gerührt. Anschliessend wird die Reaktionsmischung in 600 ml Eis/Wasser unter kräftiger Rührung gegossen. Der Niederschlag wird abfiltriert und mit Wasser nachgewaschen, und getrocknet.
Es werden 12,2 g (98% der Theorie) 1,2-di(tert.-Butyloxycarbonylamino)-4- brombenzol mit einem Schmelzpunkt von 162-164°C erhalten.
1H-NMR (300 MHz, DMSO): δ = 8,67 (s, 1H, NH); 8,62 (s, 1H, NH); 7,75 (d, J = 2,2, 1H, H3); 7,46 (d, J = 8,7, 1H, H6); 7,24 (dd, J = 2,2, J = 8,7, 1H, H5); 1,48 (s, 18H).
CHN-Analyse
C. Synthese von 1,2-di(tert.-Butyloxycarbonylamino)-4-(5,5-dimethyl- [1,3,2]dioxaborinan-2-yl)benzol
6 g (15,4 mmol) 1,2-di(tert.-Butyloxycarbonylamino)-4-brombenzol aus Stufe B und 5,2 g (23,1 mmol) 5,5,5',5'-Tetramethyl-2,2'-Bi-[1,3,2-dioxa­ borinan] werden unter Argon in 120 ml Dioxan gelöst. Anschliessend werden 0,34 g (0,0046 mmol) [1,1'-Bis(diphenylphosphino)ferrocen]- dichlor-Palladium(II) und 4,6 g Kaliumacetat zugegeben und die Reaktionsmischung 6 Stunden lang auf 80°C erwärmt. Nach Beendigung der Reaktion wird die Reaktionsmischung in 600 ml Eis/Wasser gegossen, der Niederschlag abfiltriert, mit Wasser nachgewaschen und getrocknet. Das rohe Produkt wird aus Ethanol umkristallisiert.
Es werden 4,3 g (67% der Theorie) 1,2-di(tert.-Butyloxycarbonylamino)-4- (5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzol mit einem Schmelzpunkt von 180-182°C erhalten.
1H-NMR (300 MHz, DMSO): δ = 8,54 (s, 1H, NH); 8,48 (s, 1H, NH); 7,8 (s, 1H, H3); 7,54 (d, J = 8,1, 1H, H6); 7,39 (d, J = 8,1, 1H, H5); 3,74 (s, 4H, OCH2); 1,48 (s, 18H, CH3), 0,95 (s, 6H, CH3).
CHN-Analyse
D. Synthese der Hydrochloride der 1,2-Diamino-benzol-Derivate (allgemeine Synthese-Vorschrift)
0,25 g (0,6 mmol) 1,2-di(tert.-Butyloxycarbonylamino)-4-(5,5-dimethyl- [1,3,2]dioxaborinan-2-yl)benzol aus Stufe C und 0,78 mmol der entsprechenden Bromaryl oder Bromheteroaryl werden unter Argon in 4 ml 1,2-Dimethoxyethan gelöst. Anschliessend werden 0,02 g Tetrakis- (triphenylphosphin)-palladium (0,018 mmol) und 0,8 ml 2 N Kaliumcarbonat­ lösung zugegeben und die Reaktionsmischung auf 80°C erwärmt. Nach Beendigung der Reaktion wird die Reaktionsmischung in 15 ml Essigsäureethylester gegossen. Anschliessend wird die organische Phase abgetrennt, mit einer 1 N Natriumhydroxid Lösung gewaschen, über MgSO4 getrocknet, filtriert und eingeengt. Der Rückstand wird abschliessend an Kieselgel mit Hexan/Diethylether gereinigt.
Das so erhaltene Produkt wird in 2 ml Ethanol gelöst und mit 1,8 ml einer 2,9 molaren ethanolischen Salzsäurelösung versetzt. Die Reaktions­ mischung wird anschliessend auf 55°C erwärmt. Nach Beendigung der Reaktion wird der Niederschlag abfiltriert, mit Ethanol gewaschen und sodann getrocknet.
1. 1,2-Diamino-4-(2-thienyl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-thiophen
Ausbeute: 0,081 g (51% der Theorie)
ESI-MS: 191 [M + H]+
(100)
2. 1,2-Diamino-4-(3-thienyl)benzol dihydrochlorid
Verwendetes Bromderivat: 3-Brom-thiophen
Ausbeute: 0,06 g (38% der Theorie)
ESI-MS: 191 [M + H]+
(100)
3. 1,2-Diamino-4-(3-furyl)benzol dihydrochlorid
Verwendetes Bromderivat: 3-Brom-furan
Ausbeute: 0,031 g (21% der Theorie)
ESI-MS: 175 [M + H]+
(100)
4. 1,2-Diamino-4-(5-chlor-2-thienyl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-5-chlor-thiophen
Ausbeute: 0,065 g (25% der Theorie)
ESI-MS: 223 [M - H]+
(100)
5. 1,2-Diamino-4-(5-acetyl-2-thienyl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-5-acetyl-thiophen
Ausbeute: 0,063 g (35% der Theorie)
ESI-MS: 255 [M + Na]+
(100)
6. 1,2-Diamino-4-(2-chlor-3-thienyl)benzol dihydrochlorid
Verwendetes Bromderivat: 3-Brom-2-chlor-thiophen
Ausbeute: 0,034 g (20% der Theorie)
ESI-MS: 225 [M + Na]+
(100)
7. 1,2-Diamino-4-(5-methyl-3-thienyl)benzol dihydrochlorid
Verwendetes Bromderivat: 3-Brom-4-methyl-thiophen
Ausbeute: 0,064 g (39% der Theorie)
ESI-MS: 205 [M + H]+
(100)
8. 1,2-Diamino-4-(1,3-thiazol-2-yl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-thiazol
Ausbeute: 0,056 g (36% der Theorie)
ESI-MS: 192 [M + H]+
(100)
9. 1,2-Diamino-4-phenyl-benzol dihydrochlorid
Verwendetes Bromderivat: Brombenzol
Ausbeute: 0,05 g (41% der Theorie)
ESI-MS: 185 [M + H]+
(100)
1
H-NMR (300 MHz, DMSO): δ = 7,53 (d, J = 7,2, 2H, H2' und H6'); 7,42 (t, J = 7,2, 2H, H3' und H5'); 7,31 (m, 2H, H3 und H4'); 7,20 (d, J = 8,1, 1H, H5); 7,08 (d, J = 8,1, 1H, H6); 4,30 (br s, NH3+).
CHN-Analyse
10. 1,2-Diamino-4-(4-methylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 4-Brom-toluol
Ausbeute: 0,059 g (36% der Theorie)
ESI-MS: 199 [M + H]+
(100)
11. 1,2-Diamino-4-(3-methylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 3-Brom-toluol
Ausbeute: 0,065 g (40% der Theorie)
ESI-MS: 199 [M + H]+
(100)
12. 1,2-Diamino-4-(2,3-dimethylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2,3-dimethyl-benzol
Ausbeute: 0,038 g (22% der Theorie)
ESI-MS: 213 [M + H]+
(100)
13. 1,2-Diamino-4-(2,5-dimethylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2,5-dimethyl-benzol
Ausbeute: 0,055 g (32% der Theorie)
ESI-MS: 213 [M + H]+
(100)
14. 1,2-Diamino-4-(2,4-dimethylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2,4-dimethyl-benzol
Ausbeute: 0,078 g (43% der Theorie)
ESI-MS: 213 [M + H]+
(100)
15. 1,2-Diamino-4-(3,4-dimethylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-3,4-dimethyl-benzol
Ausbeute: 0,087 g (51% der Theorie)
ESI-MS: 213 [M + H]+
(100)
16. 1,2-Diamino-4-(3,5-dimethylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-3,5-dimethyl-benzol
Ausbeute: 0,063 g (37% der Theorie)
ESI-MS: 213 [M + H]+
(100)
17. 1,2-Diamino-4-(2,4,5-trimethylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2,4,5-trimethyl-benzol
Ausbeute: 0,054 g (31% der Theorie)
ESI-MS: 227 [M + H]+
(100)
18. 1,2-Diamino-4-(4-chlorphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-chlor-benzol
Ausbeute: 0,084 g (48% der Theorie)
ESI-MS: 219 [M + H]+
(100)
19. 1,2-Diamino-4-(3-chlorphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-3-chlor-benzol
Ausbeute: 0,090 g (51% der Theorie)
ESI-MS: 219 [M + H]+
(100)
20. 1,2-Diamino-4-(2-chlorphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2-chlor-benzol
Ausbeute: 0,089 g (51% der Theorie)
ESI-MS: 219 [M + H]+
(100)
21. 1,2-Diamino-4-(4-fluorphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-fluor-benzol
Ausbeute: 0,085 g (52% der Theorie)
ESI-MS: 203 [M + H]+
(100)
22. 1,2-Diamino-4-(3,5-dichlorphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-3,5-dichlor-benzol
Ausbeute: 0,100 g (51% der Theorie)
ESI-MS: 253 [M + H]+
(100)
23. 1,2-Diamino-4-(4-(trifluormethylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-trifluormethyl-benzol
Ausbeute: 0,101 g (52% der Theorie)
ESI-MS: 253 [M + H]+
(100)
24. 1,2-Diamino-4-(3-(trifluormethylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-3-trifluormethyl-benzol
Ausbeute: 0,100 g (52% der Theorie)
ESI-MS: 253 [M + H]+
(100)
25. 1,2-Diamino-4-(4-chlor-3-trifluoromethyl-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-chlor-3-trifluormethyl-benzol
Ausbeute: 0,082 g (38% der Theorie)
ESI-MS: 287 [M + H]+
(100)
26. 1,2-Diamino-4-(4-methoxyphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-methoxy-benzol
Ausbeute: 0,063 g (34% der Theorie)
ESI-MS: 215 [M + H]+
(100)
27. 1,2-Diamino-4-(3-methoxyphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-3-methoxy-benzol
Ausbeute: 0,069 g (40% der Theorie)
ESI-MS: 215 [M + H]+
(100)
28. 1,2-Diamino-4-(2-methoxyphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2-methoxy-benzol
Ausbeute: 0,061 g (35% der Theorie)
ESI-MS: 237 [M + Na]+
(100)
29. 1,2-Diamino-4-(3,4-dimethoxyphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2,4-dimethoxy-benzol
Ausbeute: 0,032 g (15% der Theorie)
ESI-MS: 267 [M + Na]+
(100)
30. 1,2-Diamino-4-(2,4-dimethoxyphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-3,4-dimethoxy-benzol
Ausbeute: 0,095 g (50% der Theorie)
ESI-MS: 245 [M + H]+
(100)
31. 1,2-Diamino-4-(2,5-dimethoxyphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2,5-dimethoxy-benzol
Ausbeute: 0,020 g (20% der Theorie)
ESI-MS: 267 [M + Na]+
(100)
32. 1,2-Diamino-4-(1,3-benzodioxol-5-yl)benzol dihydrochlorid
Verwendetes Bromderivat: 5-Brom-1,3-benzodioxol
Ausbeute: 0,082 g (45% der Theorie)
ESI-MS: 229 [M + H]+
(100)
33. 1,2-Diamino-4-(4-methylthio-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-methylthio-benzol
Ausbeute: 0,088 g (48% der Theorie)
ESI-MS: 231 [M + H]+
(100)
34. 1,2-Diamino-4-(4-methoxy-2-methyl-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-methoxy-2-methyl-benzol
Ausbeute: 0,085 g (47% der Theorie)
ESI-MS: 229 [M + H]+
(100)
35. 1,2-Diamino-4-(4-cyano-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 4-Brom-benzonitril
Ausbeute: 0,100 g (61% der Theorie)
ESI-MS: 232 [M + Na]+
(100)
36. 1,2-Diamino-4-(3-cyano-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 3-Brom-benzonitril
Ausbeute: 0,079 g (50% der Theorie)
ESI-MS: 232 [M + Na]+
(100)
37. 1,2-Diamino-4-(4-hydroxyphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 4-Brom-phenol
Ausbeute: 0,079 g (48% der Theorie)
ESI-MS: 201 [M + H]+
(100)
38. 1,2-Diamino-4-(3-hydroxyphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 3-Brom-phenol
Ausbeute: 0,081 g (50% der Theorie)
ESI-MS: 201 [M + H]+
(100)
39. 1,2-Diamino-4-(4-hydroxy-2-methylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 4-Brom-3-methyl-phenol
Ausbeute: 0,027 g (16% der Theorie)
ESI-MS: 215 [M + H]+
(100)
40. 1,2-Diamino-4-(4-nitrophenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-nitro-benzol
Ausbeute: 0,067 g (37% der Theorie)
ESI-MS: 252 [M + Na]+
(100)
41. 1,2-Diamino-4-(3-nitrophenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-3-nitro-benzol
Ausbeute: 0,063 g (35% der Theorie)
ESI-MS: 252 [M + Na]+
(100)
42. 1,2-Diamino-4-(2-nitrophenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2-nitro-benzol
Ausbeute: 0,089 g (49% der Theorie)
ESI-MS: 252 [M + Na]+
(100)
43. 1,2-Diamino-4-(2-methyl-4-nitro-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2-methyl-4-nitro-benzol
Ausbeute: 0,041 g (22% der Theorie)
ESI-MS: 266 [M + Na]+
(100)
44. 1,2-Diamino-4-(4-methyl-3-nitro-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-methyl-3-nitro-benzol
Ausbeute: 0,096 g (51% der Theorie)
ESI-MS: 266 [M + Na]+
(100)
45. 1,2-Diamino-4-(4-methyl-2-nitro-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-methyl-2-nitro-benzol
Ausbeute: 0,087 g (46% der Theorie)
ESI-MS: 266 [M + Na]+
(100)
46. 1,2-Diamino-4-(4-methoxy-2-nitro-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-methoxy-2-nitro-benzol
Ausbeute: 0,060 g (16% der Theorie)
ESI-MS: 282 [M + Na]+
(100)
47. 1,2-Diamino-4-(4-aminophenyl)benzol trihydrochlorid
Verwendetes Bromderivat: 4-Brom-anilin
Ausbeute: 0,023 g (13% der Theorie)
ESI-MS: 200 [M + H]+
(100)
48. 1,2-Diamino-4-(3-aminophenyl)benzol trihydrochlorid
Verwendetes Bromderivat: 3-Brom-anilin
Ausbeute: 0,074 g (40% der Theorie)
ESI-MS: 200 [M + H]+
(100)
49. 1,2-Diamino-4-(4-amino-3-methyl-phenyl)benzol trihydrochlorid
Verwendetes Bromderivat: 4-Brom-2-methyl-anilin
Ausbeute: 0,052 g (27% der Theorie)
ESI-MS: 214 [M + H]+
(100)
50. 1,2-Diamino-4-(4-acetylphenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 4-Brom-acetophenon
Ausbeute: 0,078 g (44% der Theorie)
ESI-MS: 249 [M + Na]+
(100)
51. 1,2-Diamino-4-(4-benzophenon)benzol dihydrochlorid
Verwendetes Bromderivat: 4-Brom-benzophenon
Ausbeute: 0,100 g (46% der Theorie)
ESI-MS: 311 [M + Na]+
(100)
52. 1,2-Diamino-4-(4-ethoxycarbonyl-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 4-Brom-benzosäure ethylester
Ausbeute: 0,106 g (54% der Theorie)
ESI-MS: 279 [M + Na]+
(100)
53. 1,2-Diamino-4-(3-ethoxycarbonyl-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 3-Brom-benzosäure ethylester
Ausbeute: 0,068 g (35% der Theorie)
ESI-MS: 279 [M + Na]+
(100)
54. 1,2-Diamino-4-(4-carboxamid)benzol dihydrochlorid
Verwendetes Bromderivat: 4-Brom-benzamid
Ausbeute: 0,065 g (36% der Theorie)
ESI-MS: 250 [M + Na]+
(100)
55. 1,2-Diamino-4-(4-cyanomethyl-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-4-cyanomethyl-benzol
Ausbeute: 0,095 g (54% der Theorie)
ESI-MS: 246 [M + Na]+
(100)
56. 1,2-Diamino-4-(3-cyanomethyl-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-3-cyanomethyl-benzol
Ausbeute: 0,074 g (41% der Theorie)
ESI-MS: 246 [M + Na]+
(100)
57. 1,2-Diamino-4-(2-cyanomethyl-phenyl)benzol dihydrochlorid
Verwendetes Bromderivat: 1-Brom-2-cyanomethyl-benzol
Ausbeute: 0,017 g (10% der Theorie)
ESI-MS: 246 [M + Na]+
(100)
58. 1,2-Diamino-4-(2-pyridinyl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-pyridin
Ausbeute: 0,070 g (46% der Theorie)
ESI-MS: 208 [M + Na]+
(100)
59. 1,2-Diamino-4-(3-pyridinyl)benzol dihydrochlorid
Verwendetes Bromderivat: 3-Brom-pyridin
Ausbeute: 0,054 g (35% der Theorie)
ESI-MS: 184 [M - H]+
(100)
60. 1,2-Diamino-4-(5-methyl-2-pyridinyl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-5-methyl-pyridin
Ausbeute: 0,063 g (39% der Theorie)
ESI-MS: 222 [M + Na]+
(100)
61. 1,2-Diamino-4-(6-methyl-2-pyridinyl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-6-methyl-pyridin
Ausbeute: 0,095 g (57% der Theorie)
ESI-MS: 222 [M + Na]+
(100)
62. 1,2-Diamino-4-(4-methyl-2-pyridinyl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-4-methyl-pyridin
Ausbeute: 0,054 g (33% der Theorie)
ESI-MS: 222 [M + Na]+
(100)
63. 1,2-Diamino-4-(3-methyl-2-pyridinyl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-3-methyl-pyridin
Ausbeute: 0,036 g (22% der Theorie)
ESI-MS: 222 [M + Na]+
(100)
64. 1,2-Diamino-4-(5-nitro-2-pyridinyl)benzol dihydrochlorid
Verwendetes Bromderivat: 2-Brom-5-nitro-pyridin
Ausbeute: 0,106 g (58% der Theorie)
ESI-MS: 253 [M + Na]+
(100)
65. 1,2-Diamino-4-(5-pyrimidinyl)benzol dihydrochlorid
Verwendetes Bromderivat: 5-Brom-pyrimidin
Ausbeute: 0,055 g (58% der Theorie)
ESI-MS: 185 [M - H]+
(100)
II. Beispiele für Haarfärbemittel Beispiele 66 bis 130 Haarfärbemittel
Es werden Haarfärbelösungen der folgenden Zusammensetzung hergestellt:
1,25 mmol 1,2-Diaminobenzol-Derivat gemäß Tabelle 1
1,25 mmol Entwicklersubstanz/Kupplersubstanz gemäß Tabelle 1
10,0 g Laurylethersulfat (28prozentige wässrige Lösung)
9,0 g Ammoniak (22prozentige wässrige Lösung)
7,8 g Ethanol
0,3 g Ascorbinsäure
0,3 g Ethylendiaminotetraessigsäure-Dinatriumsalz-Hydrat
ad 100,0 g Wasser, vollentsalzt
30 g der vorstehenden Färbelösung werden unmittelbar vor der Anwendung mit 30 g einer 6prozentigen Wasserstoffperoxidlösung vermischt. Anschliessend wird das Gemisch auf gebleichte Haare aufgetragen. Nach einer Einwirkungszeit von 30 Minuten bei 40°C wird das Haar mit Wasser gespült, mit einem handelsüblichen Shampoo gewaschen und getrocknet. Die resultierenden Färbungen sind in Tabelle 1 zusammengefasst.
Tabelle 1
Alle Gewichtsangaben stellen, soweit nicht anders angegeben, Gewichts­ prozente dar.

Claims (10)

1. Mittel zur oxidativen Färbung von Keratinfasern, auf der Basis einer Entwicklersubstanz-Kupplersubstanz-Kombination, dadurch gekenn­ zeichnet, dass es mindestens ein 1,2-Diaminobenzol-Derivat aus der Gruppe bestehend aus 1,2-Diamino-4-(2-thienyl)benzol; 1,2-Diamino-4-(3- thienyl)benzol; 1,2-Diamino-4-(3-furyl)benzol; 1,2-Diamino-4-(pyrrol-3- yl)benzol; 1,2-Diamino-4-(1-methyl-1H-pyrrol-3-yl)benzol; 1,2-Diamino-4- (3-methyl-2-thienyl)benzol; 1,2-Diamino-4-(5-methyl-2-thienyl)benzol; 1,2-Diamino-4-(3-brom-2-thienyl)benzol; 1,2-Diamino-4-(5-chlor-2- thienyl)benzol; 1,2-Diamino-4-(5-acetyl-2-thienyl)benzol; 1,2-Diamino-4- (5-nitro-2-thienyl)benzol; 1,2-Diamino-4-(3,4-dinitro-2-thienyl)benzol; 1,2-Diamino-4-(5-formyl-2-thienyl)benzol; 1,2-Diamino-4-(2-methyl-3- thienyl)benzol; 1,2-Diamino-4-(2-methyl-3-furyl)benzol; 1,2-Diamino-4-(4- methyl-3-thienyl)benzol; 1,2-Diamino-4-(4-methyl-3-furyl)benzol; 1,2-Diamino-4-(5-methyl-3-thienyl)benzol; 1,2-Diamino-4-(5-methyl-3- furyl)benzol; 1,2-Diamino-4-(2-ethyl-3-thienyl)benzol; 1,2-Diamino-4-(2- ethyl-3-furyl)benzol; 1,2-Diamino-4-(4-ethyl-3-thienyl)benzol; 1,2-Diamino- 4-(4-ethyl-3-furyl)benzol; 1,2-Diamino-4-(5-ethyl-3-thienyl)benzol; 1,2-Diamino-4-(5-ethyl-3-furyl)-benzol; 1,2-Diamino-4-(2-chlor-3- thienyl)benzol; 1,2-Diamino-4-(2-chlor-3-furyl)benzol; 1,2-Diamino-4-(4- chlor-3-thienyl)-benzol; 1,2-Diamino-4-(4-chlor-3-furyl)benzol; 1,2-Diamino-4-(5-chlor-3-thienyl)benzol; 1,2-Diamino-4-(5-chlor-3- furyl)benzol; 1,2-Diamino-4-(2-dimethylamino-3-thienyl)-benzol; 1,2-Diamino-4-(2-dimethylamino-3-furyl)benzol; 1,2-Diamino-4-(4- dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(4-dimethylamino-3- furyl)benzol; 1,2-Diamino-4-(5-dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(5-dimethylamino-3-furyl)benzol; 1,2-Diamino-4-(2-formyl- 3-thienyl)benzol; 1,2-Diamino-4-(2-formyl-3-furyl)benzol; 1,2-Diamino-4- (4-formyl-3-thienyl)benzol; 1,2-Diamino-4-(4-formyl-3-furyl)benzol; 1,2-Diamino-4-(5-formyl-3-thienyl)benzol; 1,2-Diamino-4-(5-formyl-3-furyl)­ benzol; 1,2-Diamino-4-(2-acetyl-3-thienyl)benzol; 1,2-Diamino-4-(2-acetyl- 3-furyl)benzol; 1,2-Diamino-4-(4-acetyl-3-thienyl)benzol; 1,2-Diamino-4-(4- acetyl-3-furyl)benzol; 1,2-Diamino-4-(5-acetyl-3-thienyl)benzol; 1,2-Diamino-4-(5-acetyl-3-furyl)benzol; 1,2-Diamino-4-(2-cyano-3-thienyl)­ benzol; 1,2-Diamino-4-(1,3-thiazol-2-yl)benzol; 1,2-Diamino-4-(5-nitro-1,3- thiazol-2-yl)benzol; 1,2-Diamino-4-(1H-pyrazol-4-yl)benzol; 1,2-Diamino-4- (3-methyl-1H-pyrazol-4-yl)benzol; 1,2-Diamino-4-(3,5-dimethyl-1H- pyrazol-4-yl)benzol; 1,2-Diamino-4-phenyl-benzol; 1,2-Diamino-4-(4- methylphenyl)-benzol; 1,2-Diamino-4-(3-methylphenyl)-benzol; 1,2-Diamino-4-(2-methyl-phenyl)-benzol; 1,2-Diamino-4-(2,3-dimethyl­ phenyl)benzol; 1,2-Diamino-4-(2,4-dimethylphenyl)benzol; 1,2-Diamino-4- (2,5-dimethylphenyl)benzol; 1,2-Diamino-4-(2,6-dimethylphenyl)benzol; 1,2-Diamino-4-(3,4-dimethyl-phenyl)benzol; 1,2-Diamino-4-(3,5-dimethyl­ phenyl)benzol; 1,2-Diamino-4-(2,4,5-trimethylphenyl)benzol; 1,2-Diamino- 4-(2,4,6-trimethylphenyl)benzol; 1,2-Diamino-4-(4-chlor-phenyl)benzol; 1,2-Diamino-4-(3-chlorphenyl)-benzol; 1,2-Diamino-4-(2-chlorphenyl)­ benzol; 1,2-Diamino-4-(4-fluor-phenyl)benzol; 1,2-Diamino-4-(3-fluor­ phenyl)benzol; 1,2-Diamino-4-(2-fluorphenyl)benzol; 1,2-Diamino-4-(4- bromphenyl)benzol; 1,2-Diamino-4-(3-bromphenyl)benzol; 1,2-Diamino-4- (2-bromphenyl)benzol; 1,2-Diamino-4-(4-jodphenyl)benzol; 1,2-Diamino-4- (3-jodphenyl)benzol; 1,2-Diamino-4-(2-jodphenyl)benzol; 1,2-Diamino-4- (3,5-dichlorphenyl)benzol; 1,2-Diamino-4-(2,3-dichlorphenyl)benzol; 1,2-Diamino-4-(3,4-dichlorphenyl)benzol; 1,2-Diamino-4-(4-(trifluormethyl­ phenyl)benzol; 1,2-Diamino-4-(3-(trifluor-methylphenyl)benzol; 1,2-Diamino-4-(2-(trifluormethylphenyl)benzol; 1,2-Diamino-4-(4-chlor-3- trifluoromethyl-phenyl)benzol; 1,2-Diamino-4-(4-methoxyphenyl)benzol; 1,2-Diamino-4-(3-methoxyphenyl)benzol; 1,2-Diamino-4-(2-methoxy­ phenyl)benzol; 1,2-Diamino-4-(4-ethoxy-phenyl)benzol; 1,2-Diamino-4-(3- ethoxyphenyl)-benzol; 1,2-Diamino-4-(2-ethoxyphenyl)benzol; 1,2-Diamino-4-(2,4-dimethoxyphenyl)benzol; 1,2-Diamino-4-(2,5- dimethoxyphenyl)benzol; 1,2-Diamino-4-(3,4-dimethoxyphenyl)benzol; 1,2-Diamino-4-(1,3-benzodioxol-5-yl)benzol; 1,2-Diamino-4-(4-methyl­ thiophenyl)benzol; 1,2-Diamino-4-(3-methylthio-phenyl)benzol; 1,2-Diamino-4-(2-methylthio-phenyl)benzol; 1,2-Diamino-4-(4-methoxy-2- methylphenyl)benzol; 1,2-Diamino-4-(4-cyanophenyl)benzol; 1,2-Diamino- 4-(3-cyanophenyl)-benzol; 1,2-Diamino-4-(2-cyanophenyl)-benzol; 1,2-Diamino-4-(4-hydroxyphenyl)benzol; 1,2-Diamino-4-(3-hydroxy­ phenyl)-benzol; 1,2-Diamino-4-(2-hydroxyphenyl)benzol; 1,2-Diamino-4- (4-hydroxy-2-methylphenyl)benzol; 1,2-Diamino-4-(4-nitrophenyl)benzol; 1,2-Diamino-4-(3-nitrophenyl)benzol; 1,2-Diamino-4-(2-nitrophenyl)benzol; 1,2-Diamino-4-(2-methyl-4-nitro-phenyl)benzol; 1,2-Diamino-4-(4-methyl- 3-nitro-phenyl)-benzol; 1,2-Diamino-4-(4-methyl-2-nitro-phenyl)benzol; 1,2-Diamino-4-(4-methoxy-2-nitro-phenyl)benzol; 1,2-Diamino-4-(4-amino­ phenyl)benzol; 1,2-Diamino-4-(3-aminophenyl)-benzol; 1,2-Diamino-4-(4- amino-3-methyl-phenyl)benzol; 1,2-Diamino-4-(4-dimethylaminophenyl)- benzol; 1,2-Diamino-4-(3-dimethylaminophenyl)-benzol; 1,2-Diamino-4-(4- di(2-hydroxyethyl)aminophenyl)benzol; 1,2-Diamino-4-(3-di(2-hydroxy­ ethyl)amino-phenyl)benzol; 1,2-Diamino-4-(2,4-diaminophenyl)benzol; 1,2-Diamino-4-(2,4-dimethyl-aminophenyl)-benzol; 1,2-Diamino-4-(2,4- di(2-hydroxyethyl)amino-phenyl)benzol; 1,2-Diamino-4-(4-formylphenyl)- benzol; 1,2-Diamino-4-(3-formylphenyl)-benzol; 1,2-Diamino-4-(2-formyl­ phenyl)-benzol; 1,2-Diamino-4-(4-acetylphenyl)benzol; 1,2-Diamino-4-(3- acetylphenyl)benzol; 1,2-Diamino-4-(2-acetylphenyl)benzol; 1,2-Diamino- 4-(4-(trimethylsilyl)-phenyl)benzol; 1,2-Diamino-4-(3-(trimethylsilyl)- phenyl)benzol; 1,2-Diamino-4-(2-(trimethylsilyl)-phenyl)benzol; 1,2-Diamino-4-(4-hydroxycarbonylphenyl)-benzol; 1,2-Diamino-4-(3- hydroxycarbonylphenyl)benzol; 1,2-Diamino-4-(2-hydroxycarbonylphenyl)­ benzol; 1,2-Diamino-4-(4-ethoxycarbonylphenyl)-benzol; 1,2-Diamino-4- (3-ethoxycarbonylphenyl)benzol; 1,2-Diamino-4-(2-ethoxycarbonyl­ phenyl)benzol; 1,2-Diamino-4-(4-methoxy-carbonylphenyl)-benzol; 1,2-Diamino-4-(3-methoxycarbonylphenyl)benzol; 1,2-Diamino-4-(2- methoxycarbonylphenyl)benzol; 1,2-Diamino-4-(4-carboxamidophenyl)­ benzol; 1,2-Diamino-4-(3-carboxamidophenyl)benzol; 1,2-Diamino-4-(2- carboxamidophenyl)benzol; 1,2-Diamino-4-(4-benzophenon)benzol; 1,2-Diamino-4-(4-cyano-methyl-phenyl)benzol; 1,2-Diamino-4-(3-cyano­ methyl-phenyl)benzol; 1,2-Diamino-4-(2-cyanomethyl-phenyl)benzol; 1,2-Diamino-4-(2-pyridinyl)-benzol; 1,2-Diamino-4-(3-pyridinyl)benzol; 1,2-Diamino-4-(4-pyridinyl)-benzol; 1,2-Diamino-4-(3-methyl-2-pyridinyl)- benzol; 1,2-Diamino-4-(4-methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(5- methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(6-methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(5-nitro-2-pyridinyl)benzol und 1,2-Diamino-4-(5- pyrimidinyl)-benzol sowie deren physiologisch verträglichen Salzen.
2. Mittel nach Anspruch 1, dadurch gekennzeichnet, dass das 1,2-Diaminobenzol-Derivat ausgewählt ist aus 1,2-Diamino-4-(2- thienyl)benzol; 1,2-Diamino-4-(3-thienyl)benzol; 1,2-Diamino-4-(3- furyl)benzol; 1,2-Diamino-4-(4-methyl-3-thienyl)benzol; 1,2-Diamino-4- phenyl-benzol; 1,2-Diamino-4-(4-methylphenyl)benzol; 1,2-Diamino-4-(3- methylphenyl)benzol; 1,2-Diamino-4-(3,4-dimethyl-phenyl)benzol; 1,2-Diamino-4-(4-methoxyphenyl)benzol; 1,2-Diamino-4-(3- methoxyphenyl)benzol; 1,2-Diamino-4-(2,4-dimethoxyphenyl)benzol; 1,2-Diamino-4-(3,4-dimethoxyphenyl)benzol; 1,2-Diamino-4-(1,3-benzo­ dioxol-5-yl)benzol; 1,2-Diamino-4-(4-methylthiophenyl)benzol; 1,2-Diamino-4-(4-cyanophenyl)benzol; 1,2-Diamino-4-(4-hydroxyphenyl)­ benzol; 1,2-Diamino-4-(3-hydroxyphenyl)benzol; 1,2-Diamino-4-(4- hydroxy-2-methylphenyl)benzol; 1,2-Diamino-4-(4-cyanomethyl­ phenyl)benzol; 1,2-Diamino-4-(3-cyanomethyl-phenyl)benzol; 1,2-Diamino-4-(2-cyano-methyl-phenyl)benzol; 1,2-Diamino-4-(2- pyridinyl)benzol; 1,2-Diamino-4-(3-pyridinyl)benzol; 1,2-Diamino-4-(5- methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(6-methyl-2-pyridinyl)benzol und 1,2-Diamino-4-(5-pyrimidinyl)benzol sowie deren physiologisch verträglichen Salze.
3. Mittel nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass das 1,2-Diaminobenzol-Derivat in einer Menge von 0,005 bis 20 Gewichtsprozent enthalten ist.
4. Mittel nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass es zusätzlich mindestens eine weitere bekannte Entwicklersubstanz und/oder Kupplersubtanz enthält.
5. Mittel nach Anspruch 4, dadurch gekennzeichnet, dass die Entwicklersubstanzen und Kupplersubstanzen, bezogen auf die Gesamtmenge des Oxidationsfärbemittel jeweils in einer Gesamtmenge von 0,005 bis 20 Gewichtsprozent enthalten sind.
6. Mittel nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass es zusätzlich mindestens einen direktziehenden Farbstoff enthält.
7. Mittel nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass es einen pH-Wert von 5 bis 11,5 aufweist.
8. Mittel nach einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass es in Form einer wässrigen oder wässrig-alkoholischen Lösung, einer Creme, eines Gels oder einer Emulsion vorliegt.
9. Mittel nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass es ein Haarfärbemittel ist.
10. 1,2-Diaminobenzol-Derivate welche ausgewählt sind aus der Gruppe bestehend aus 1,2-Diamino-4-(2-thienyl)benzol; 1,2-Diamino-4-(3- thienyl)benzol; 1,2-Diamino-4-(3-furyl)benzol; 1,2-Diamino-4-(pyrrol-3- yl)benzol; 1,2-Diamino-4-(1-methyl-1H-pyrrol-3-yl)benzol; 1,2-Diamino-4- (3-methyl-2-thienyl)benzol; 1,2-Diamino-4-(5-methyl-2-thienyl)benzol; 1,2-Diamino-4-(3-brom-2-thienyl)benzol; 1,2-Diamino-4-(5-chlor-2-thienyl)­ benzol; 1,2-Diamino-4-(5-acetyl-2-thienyl)benzol; 1,2-Diamino-4-(5-nitro- 2-thienyl)benzol; 1,2-Diamino-4-(3,4-dinitro-2-thienyl)benzol; 1,2-Diamino- 4-(5-formyl-2-thienyl)benzol; 1,2-Diamino-4-(2-methyl-3-thienyl)benzol; 1,2-Diamino-4-(2-methyl-3-furyl)benzol; 1,2-Diamino-4-(4-methyl-3- thienyl)benzol; 1,2-Diamino-4-(4-methyl-3-furyl)benzol; 1,2-Diamino-4-(5- methyl-3-thienyl)benzol; 1,2-Diamino-4-(5-methyl-3-furyl)benzol; 1,2-Diamino-4-(2-ethyl-3-thienyl)benzol; 1,2-Diamino-4-(2-ethyl-3- furyl)benzol; 1,2-Diamino-4-(4-ethyl-3-thienyl)benzol; 1,2-Diamino-4-(4- ethyl-3-furyl)benzol; 1,2-Diamino-4-(5-ethyl-3-thienyl)benzol; 1,2-Diamino- 4-(5-ethyl-3-furyl)benzol; 1,2-Diamino-4-(2-chlor-3-thienyl)benzol; 1,2-Diamino-4-(2-chlor-3-furyl)benzol; 1,2-Diamino-4-(4-chlor-3-thienyl)­ benzol; 1,2-Diamino-4-(4-chlor-3-furyl)benzol; 1,2-Diamino-4-(5-chlor-3- thienyl)benzol; 1,2-Diamino-4-(5-chlor-3-furyl)benzol; 1,2-Diamino-4-(2- dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(2-dimethylamino-3- furyl)benzol; 1,2-Diamino-4-(4-dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(4-dimethylamino-3-furyl)benzol; 1,2-Diamino-4-(5- dimethylamino-3-thienyl)benzol; 1,2-Diamino-4-(5-dimethylamino-3- furyl)benzol; 1,2-Diamino-4-(2-formyl-3-thienyl)benzol; 1,2-Diamino-4-(2- formyl-3-furyl)benzol; 1,2-Diamino-4-(4-formyl-3-thienyl)benzol; 1,2-Diamino-4-(4-formyl-3-furyl)benzol; 1,2-Diamino-4-(5-formyl-3- thienyl)benzol; 1,2-Diamino-4-(5-formyl-3-furyl)benzol; 1,2-Diamino-4-(2- acetyl-3-thienyl)benzol; 1,2-Diamino-4-(2-acetyl-3-furyl)benzol; 1,2-Diamino-4-(4-acetyl-3-thienyl)benzol; 1,2-Diamino-4-(4-acetyl-3- furyl)benzol; 1,2-Diamino-4-(5-acetyl-3-thienyl)benzol; 1,2-Diamino-4-(5- acetyl-3-furyl)benzol; 1,2-Diamino-4-(2-cyano-3-thienyl)benzol; 1,2-Diamino-4-(1,3-thiazol-2-yl)benzol; 1,2-Diamino-4-(5-nitro-1,3-thiazol- 2-yl)benzol; 1,2-Diamino-4-(1H-pyrazol-4-yl)benzol; 1,2-Diamino-4-(3- methyl-1H-pyrazol-4-yl)benzol; 1,2-Diamino-4-(3,5-dimethyl-1H-pyrazol-4- yl)benzol; 1,2-Diamino-4-(4-methylphenyl)-benzol; 1,2-Diamino-4-(3- methylphenyl)-benzol; 1,2-Diamino-4-(2-methyl-phenyl)-benzol; 1,2-Diamino-4-(2,3-dimethylphenyl)benzol; 1,2-Diamino-4-(2,4- dimethylphenyl)benzol; 1,2-Diamino-4-(2,5-dimethylphenyl)benzol; 1,2-Diamino-4-(2,6-dimethylphenyl)benzol; 1,2-Diamino-4-(3,4-dimethyl­ phenyl)benzol; 1,2-Diamino-4-(3,5-dimethylphenyl)benzol; 1,2-Diamino-4- (2,4,5-trimethylphenyl)benzol; 1,2-Diamino-4-(2,4,6-trimethylphenyl)­ benzol; 1,2-Diamino-4-(3-chlorphenyl)-benzol; 1,2-Diamino-4-(2- chlorphenyl)-benzol; 1,2-Diamino-4-(4-fluor-phenyl)benzol; 1,2-Diamino-4- (3-fluor-phenyl)benzol; 1,2-Diamino-4-(2-fluorphenyl)benzol; 1,2-Diamino- 4-(4-bromphenyl)benzol; 1,2-Diamino-4-(3-bromphenyl)benzol; 1,2-Diamino-4-(2-bromphenyl)benzol; 1,2-Diamino-4-(4-jodphenyl)benzol; 1,2-Diamino-4-(3-jodphenyl)benzol; 1,2-Diamino-4-(2 jodphenyl)benzol; 1,2-Diamino-4-(3,5-dichlorphenyl)benzol; 1,2-Diamino-4-(2,3-dichlor­ phenyl)benzol; 1,2-Diamino-4-(3,4-dichlorphenyl)benzol; 1,2-Diamino-4- (4-(trifluormethyl-phenyl)benzol; 1,2-Diamino-4-(3-(trifluor-methylphenyl)­ benzol; 1,2-Diamino-4-(2-(trifluormethylphenyl)benzol; 1,2-Diamino-4-(4- chlor-3-trifluoromethyl-phenyl)benzol; 1,2-Diamino-4-(4-methoxyphenyl)­ benzol; 1,2-Diamino-4-(3-methoxyphenyl)benzol; 1,2-Diamino-4-(2- methoxy-phenyl)benzol; 1,2-Diamino-4-(4-ethoxy-phenyl)benzol; 1,2-Diamino-4-(3-ethoxyphenyl)-benzol; 1,2-Diamino-4-(2-ethoxyphenyl)- benzol; 1,2-Diamino-4-(2,4-dimethoxyphenyl)benzol; 1,2-Diamino-4-(2,5- dimethoxyphenyl)-benzol; 1,2-Diamino-4-(3,4-dimethoxy-phenyl)benzol; 1,2-Diamino-4-(1,3-benzodioxol-5-yl)benzol; 1,2-Diamino-4-(4-methyl­ thiophenyl)benzol; 1,2-Diamino-4-(3-methylthio-phenyl)benzol; 1,2-Diamino-4-(2-methylthio-phenyl)benzol; 1,2-Diamino-4-(4-methoxy-2- methylphenyl)benzol; 1,2-Diamino-4-(4-cyanophenyl)benzol; 1,2-Diamino- 4-(3-cyanophenyl)-benzol; 1,2-Diamino-4-(4-hydroxy-phenyl)benzol; 1,2- Diamino-4-(3-hydroxyphenyl)-benzol; 1,2-Diamino-4-(2-hydroxyphenyl)- benzol; 1,2-Diamino-4-(4-hydroxy-2-methylphenyl)benzol; 1,2-Diamino-4- (4-nitrophenyl)benzol; 1,2-Diamino-4-(3-nitrophenyl)benzol; 1,2-Diamino- 4-(2-nitrophenyl)benzol; 1,2-Diamino-4-(2-methyl-4-nitro-phenyl)benzol; 1,2-Diamino-4-(4-methyl-3-nitro-phenyl)-benzol; 1,2-Diamino-4-(4-methyl- 2-nitro-phenyl)benzol; 1,2-Diamino-4-(4-methoxy-2-nitro-phenyl)benzol; 1,2-Diamino-4-(3-aminophenyl)-benzol; 1,2-Diamino-4-(4-aminophenyl)- benzol; 1,2-Diamino-4-(4-amino-3-methyl-phenyl)benzol; 1,2-Diamino-4- (4-dimethylamino-phenyl)benzol; 1,2-Diamino-4-(3-dimethyl­ aminophenyl)-benzol; 1,2-Diamino-4-(4-di(2-hydroxyethyl)amino­ phenyl)benzol; 1,2-Diamino-4-(3-di(2-hydroxyethyl)-amino-phenyl)benzol; 1,2-Diamino-4-(2,4-dimethyl-aminophenyl)-benzol; 1,2-Diamino-4-(2,4- di(2-hydroxyethyl)amino-phenyl)benzol; 1,2-Diamino-4-(4- formylphenyl)benzol; 1,2-Diamino-4-(3-formylphenyl)-benzol; 1,2-Diamino-4-(2-formylphenyl)-benzol; 1,2-Diamino-4-(4-acetylphenyl)­ benzol; 1,2-Diamino-4-(3-acetylphenyl)benzol; 1,2-Diamino-4-(2-acetyl­ phenyl)-benzol; 1,2-Diamino-4-(4-(trimethylsilyl)-phenyl)benzol; 1,2-Diamino-4-(3-(trimethylsilyl)-phenyl)benzol; 1,2-Diamino-4-(2- (trimethylsilyl)-phenyl)-benzol; 1,2-Diamino-4-(4-hydroxycarbonylphenyl)­ benzol; 1,2-Diamino-4-(3-hydroxycarbonylphenyl)benzol; 1,2-Diamino-4- (2-hydroxycarbonyl-phenyl)benzol; 1,2-Diamino-4-(4-ethoxycarbonyl­ phenyl)-benzol; 1,2-Diamino-4-(3-ethoxycarbonylphenyl)benzol; 1,2-Diamino-4-(2-ethoxycarbonylphenyl)benzol; 1,2-Diamino-4-(4- methoxy-carbonylphenyl)benzol; 1,2-Diamino-4-(3-methoxycarbonyl­ phenyl)benzol; 1,2-Diamino-4-(2-methoxycarbonylphenyl)benzol; 1,2- Diamino-4-(4-carboxamidophenyl)benzol; 1,2-Diamino-4-(3-carboxamido­ phenyl)benzol; 1,2-Diamino-4-(2-carboxamidophenyl)benzol; 1,2-Diamino- 4-(4-benzophenon)benzol; 1,2-Diamino-4-(4-cyanomethyl-phenyl)benzol; 1,2-Diamino-4-(3-cyano-methyl-phenyl)benzol; 1,2-Diamino-4-(2- cyanomethyl-phenyl)benzol; 1,2-Diamino-4-(2-pyridinyl)-benzol; 1,2-Diamino-4-(3-pyridinyl)benzol; 1,2-Diamino-4-(3-methyl-2-pyridinyl)­ benzol; 1,2-Diamino-4-(4-methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(5- methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(6-methyl-2-pyridinyl)benzol; 1,2-Diamino-4-(5-nitro-2-pyridinyl)benzol und 1,2-Diamino-4-(5- pyrimidinyl)-benzol sowie deren physiologisch verträgliche Salze.
DE2001114970 2001-03-27 2001-03-27 1,2-Diaminobenzol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 1,2-Diaminobenzol-Derivate Expired - Fee Related DE10114970C2 (de)

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DE4422603A1 (de) * 1994-06-28 1996-01-04 Wella Ag Mittel zum oxidativen Färben von Haaren auf der Basis von 4,5-Diaminopyrazolen und m-Phenylendiaminderivaten
DE19812059C1 (de) * 1998-03-19 1999-09-23 Wella Ag Diaminobenzol-Derivate sowie diese Diaminobenzol-Derivate enthaltende Haarfärbemittel
DE19812058C1 (de) * 1998-03-19 1999-10-07 Wella Ag Diaminobenzol-Derivate und diese Verbindungen enthaltende Haarfärbemittel
DE19822041A1 (de) * 1998-05-16 1999-12-23 Wella Ag 2,5-Diamino-1-phenylbenzol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 2,5-Diamino-1-phenylbenzol-Derivate
DE19923392C1 (de) * 1999-05-21 2001-02-01 Ackermann Albert Gmbh Co Hand-Bediengerät für den Pflegebereich
DE10031695A1 (de) * 2000-06-29 2002-01-24 Wella Ag Mittel und Verfahren zur Färbung keratinischer Fasern

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4422603A1 (de) * 1994-06-28 1996-01-04 Wella Ag Mittel zum oxidativen Färben von Haaren auf der Basis von 4,5-Diaminopyrazolen und m-Phenylendiaminderivaten
DE19812059C1 (de) * 1998-03-19 1999-09-23 Wella Ag Diaminobenzol-Derivate sowie diese Diaminobenzol-Derivate enthaltende Haarfärbemittel
DE19812058C1 (de) * 1998-03-19 1999-10-07 Wella Ag Diaminobenzol-Derivate und diese Verbindungen enthaltende Haarfärbemittel
DE19822041A1 (de) * 1998-05-16 1999-12-23 Wella Ag 2,5-Diamino-1-phenylbenzol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 2,5-Diamino-1-phenylbenzol-Derivate
DE19923392C1 (de) * 1999-05-21 2001-02-01 Ackermann Albert Gmbh Co Hand-Bediengerät für den Pflegebereich
DE10031695A1 (de) * 2000-06-29 2002-01-24 Wella Ag Mittel und Verfahren zur Färbung keratinischer Fasern

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