1,3-Dihydroxybenzene derivatives and colorants containing said compounds

A 1,3-Dihydroxybenzene derivative of formula (Ia), or a physiologically tolerated, water-soluble salt thereof:

• wherein R′1 denotes a substituted pyridyl group, a pyrimidyl group, a group of formula (IIa):
• or a group of formula (IIIa):
• wherein R′2, R′3, R′4, R′5 and R′6, independently of each other, denote hydrogen, a halogen atom, a cyano group, a hydroxyl group, a C1–C4-alkoxy group, a C1–C4-hydroxyalkoxy group, a C1–C6-alkyl group, a C1–C4-alkylthioether group, a mercapto group, a nitro group, an amino group, a C1–C4-alkylamino group, a hydroxy-(C1–C4)alkylamino group, a di(C1–C4)alkylamino group, a di[hydroxy(C1–C4)-alkyl]amino group, a dihydroxy-(C3–C4->alkylamino group, a [hydroxy-(C1–C4)alkyl]-C1–C4-alkylamino group, a trifluoromethyl group, a —C(O)H group, a —C(O)CH3 group, a —C(O)CF3 group, a —Si(CH3)3 group, a C1–C4-hydroxyalkyl group or a C2–C4-dihydroxyalkyl group, or two adjacent R′2 to R′6 groups form an —O—CH2—O— bridge;
• X′1 denotes sulfur, nitrogen, oxygen, C—R′9 or N—R′8;
• X′2 denotes sulfur, nitrogen, oxygen, C—R′10 or N—R′8;
• X′3 denotes sulfur, nitrogen, oxygen, C—R′11 or N—R′8;
• R′7, R′9, R′10 and R′11, independently of each other, denote hydrogen, a halogen atom, a cyano group, a C1–C4-alkoxy group, a C1–C6-alkyl group, a C1–C4-alkylthioether group, a mercapto group, a nitro group, an amino group, a C1–C4-alkylamino group, a di(C1–C4)-alkylamino group, a di(C1–C4-hydroxyalkyl)amino group, a C1–C4-hydroxyalkylamino group, a trifluoromethyl group, a —C(O)CH3 group, a —C(O)CF3 group, an —Si(CH3)3 group, a C1–C4-hydroxyalkyl group or a C3–C4-dihydroxyalkyl group;
• and
• R′8 denotes hydrogen, a C1–C6-alkyl group, a C2–C4-hydroxyalkyl group, a phenyl group or an acetyl group, provided that at least one and at the most two of the X′1 to X′3 groups denote CR′9, C—R′10 or C—R′11 and at the most one of the X′1 to X′3 groups denotes sulfur, oxygen or N—R′8, and R′1 does not stand for a phenyl group or hydroxyphenyl group and provided that, when R′1 is the group of the formula IIIa, X′2 is not oxygen when X′1 and X′3 are CH and R′7 is hydrogen and also X′1 is not oxygen when X′2 and X′3 are CH and R′7 is hydrogen.

A composition for oxidative dyeing of keratin fibers containing a combination of developer substance and coupler substance, wherein said coupler substance comprises at least one 1,3-dihydroxy-4-heteroarylbenzene derivative of formula (I), or a physiologically tolerated, water-soluble salt thereof:

• wherein X denotes oxygen, sulfur or N—R5;
• R1 and R2 are equal or different and, independently of each other, denote hydrogen, a halogen atom, a hydroxyl group, a C1–C4-alkoxy group, a C1–C4-hydroxyalkoxy group, a C1–C6-alkyl group, a C1–C4-alkylthioether group, a trifluoromethyl group, a —Si(CH3)3 group, a C1–C4-hydroxyalkyl group or a C2–C4-dihydroxyalkyl group;
• R3 and R4 are equal or different and, independently of each other, denote hydrogen, a hydroxyl group, a halogen atom, a cyano group, a C1–C4-alkoxy group, a C1–C8-alkyl group, a C1–C4-alkylthioether group, a mercapto group, a nitro group, an amino group, a C1–C4-alkylamino group, a di(C1–C4)alkylamino group, a —C(O)H group, a —C(O)CH3 group, a —C(O)CF3 group, a di(CH3)3 group, a C1–C4-hydroxyalkyl group or a C2–C4-dihydroxyalkyl group;
• and
• R5 denotes hydrogen, a C1–C6-alkyl group, a C2–C4-hydroxyalkyl group, a phenyl group or an acetyl group.

A composition for dyeing keratin fibers containing a combination of developer substance and coupler substance, wherein said coupler substance comprises at least one 1,3-dihydroxybenzene derivative of formula (Ia), or a physiologically tolerated, water-soluble salt thereof:

• wherein R′1 denotes a substituted pyridyl group, a pyrimidyl group, a group of formula (IIa):
• or a group of formula (IIIa):
• wherein R′2, R′3, R′4, R′5 and R′6, independently of each other, denote hydrogen, a halogen atom, a cyano group, a hydroxyl group, a C1–C4-alkoxy group, a C1–C4— hydroxyalkoxy group, a C1–C6-alkyl group, a C1–C4-alkylthioether group, a mercapto group, a nitro group, an amino group, a C1–C4-alkylamino group, a hydroxy-(C1–C4)alkylamino group, a di(C1–C4)-alkylamino group, a di[hydroxy(C1–C4)-alkyl]amino group, a dihydroxy-(C3–C4-alkylamino group, a [hydroxy-(C1–C4)-alkyl]-C1–C4-alkylamino group, a trifluoromethyl group, a —C(O)H group, a —C(O)CH3 group, a —C(O)CF3 group, a —Si(CH3)3 group, a C1–C4-hydroxyalkyl group or a C2–C4-dihydroxyalkyl group, or two adjacent R2 to R6 groups form an —O—CH2-bridge;
• X′1 denotes sulfur, nitrogen, oxygen, C—R′9 or N—R′8;
• X′2 denotes sulfur, nitrogen, oxygen, C—R′10 or N—R′8;
• X′3 denotes sulfur, nitrogen, oxygen, C—R′11 or N—R′8;
• R′7, R′9, R′10 and R′11, independently of each other, denote hydrogen, a halogen atom, a cyano group, a C1–C4-alkoxy group, a C1–C6-alkyl group, a C1–C4-alkylthioether group, a mercapto group, a nitro group, an amino group, a C1–C4-alkylamino group, a di(C1–C4)-alkylamino group, a di(C1–C4-hydroxyalkyl)amino group, a C1–C4-hydroxyalkylamino group, a trifluoromethyl group, a —C(O)CH3 group, a —C(O)CF3 group, an —Si(CH3)3 group, a C1–C4-hydroxyalkyl group or a C3–C4-dihydroxyalkyl group;
• and
• R′8 denotes hydrogen, a C1–C6-alkyl group, a C2–C4-hydroxyalkyl group, a phenyl group or an acetyl group, provided that at least one and at the most two of the X′1 to X′3 groups denote C—R′9, C—R′10 or C—R′11 and at the most one of the X′1 to X′3 groups denotes sulfur, oxygen or N—R′8, and R′1 does not stand for a phenyl group or hydroxyphenyl group.

The composition as defined in calm 15, wherein, in addition to said at least one 1,3-dihydroxybenzene derivative, said coupler substance includes at least one member selected from the group consisting of N-(3-dimethylaminophenyl)-urea;

• 2,6-diaminopyridine;
• 2-amino-4-[(2-hydroxy-ethyl)-amino]anisole;
• 2,4-diamino-1-fluoro-5-methylbenzene;
• 2,4-diamino-1-methoxy-5-methyl-benzene;
• 2,4-diamino-1-ethoxy-5-methylbenzene;
• 2,4-diamino-1-(2-hydroxyethoxy)-5-methylbenzene;
• 2,4-di[(2-hydroxyethyl)-amino]-1,5-dimethoxybenzene;
• 2,3-diamino-6-methoxypyridine;
• 3-amino-6-methoxy-2-(methylamino)pyridine;
• 2,6-diamino-3,5-dimethoxypyridine;
• 3,5-diamino-2,6-dimethoxypyridine;
• 1,3-diaminobenzene;
• 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-(2-aminoethoxy)-2,4-diaminobenzene;
• 2-amino-1-(2-hydroxyethoxy)-4-methyl-aminobenzene;
• 2,4-diaminophenoxyacetic acid;
• 3-[di(2-hydroxyethyl)-amino]aniline;
• 4-amino-2-di[(2-hydroxyethyl)amino]-1-ethoxybenzene;
• 5-methyl-2-(1-methylethyl)phenol;
• 3-[(2-hydroxyethyl)amino]aniline;
• 3[(2-aminoethyl)-amino]aniline;
• 1,3-di-(2,4-diamino-phenoxy)propane;
• di(2,4-diaminophenoxy)-methane;
• 1,3-diamino-2,4-dimethoxybenzene;
• 2,6-bis(2-hydroxyethyl)aminotoluene;
• 4-hydroxyindole;
• 3-dimethylaminophenol;
• 3-diethyl-aminophenol;
• 5-amino-2-methylphenol;
• 5-amino-4-fluoro-2-methylphenol;
• 5-amino-4-methoxy-2-methylphenol;
• 5-amino-4-ethoxy-2-methylphenol;
• 3-amino-2,4-dichlorophenol;
• 5-amino-2,4-dichlorophenol;
• 3-amino-2-methylphenol;
• 3-amino-2-chloro-6-methylphenol;
• 3-aminophenol;
• 2-[(3-hydroxy-phenyl)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-hydroxypyridine;
• 2,6-dihydroxy-3,4-dimethylpyridine;
• 5-amino-4-chloro-2-methylphenol;
• 1-naphthol;
• 2-methyl-1-naphthol;
• 1,5-dihydroxynaphthalene;
• 1,7-dihydroxynaphthalene;
• 2,3-dihydroxynaphthalene;
• 2,7-dihydroxynaphthalene;
• 2-methyl-1-naphthol acetate;
• 1,3-dihydroxybenzene;
• 1-chloro-2,4-dihydroxybenzene;
• 2-chloro-1,3-dihydroxybenzene;
• 1,2-dichloro-3,5-dihydroxy-4-methylbenzene;
• 1,5-dichloro-2,4-dihydroxybenzene;
• 1,3-dihydroxy-2-methylbenzene;
• 3,4-methylenedioxyphenol;
• 3,4-methylene-dioxyaniline;
• 5-[(2-hydroxyethyl)amino]-1,3-benzodioxole;
• 6-bromo-1-hydroxy-3,4-methylenedioxybenzene;
• 3,4-diaminobenzoic 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-dihydroxyindole;
• 5,6-dihydroxyindoline;
• 5-hydroxyindole;
• 6-hydroxyindole;
• 7-hydroxyindole and 2,3-indolinedione.