p-aminophenol derivative compounds and dye compositions containing same

A p-aminophenol derivative compound, or a physiologically compatible salt thereof, said p-aminophenol derivative compound being selected from the group consisting of 4-amino-2-(2-thienyl)-phenol;

• 4-amino-2-(2-furyl)-phenol;
• 4-amino-2-(pyrrol-2-yl)-phenol;
• 4-amino-2-(1-methyl-I H-pyrrol-2-yl)phenol;
• 4-amino-3-chloro-2-(2-thienyl)-phenol;
• 4-amino-3-methyl-2-(2-thienyl)-phenol;
• 4-amino-5-chloro-2-(2-thienyl)phenol;
• 4-amlno-5-methyl-2-(2-thienyl)phenol;
• 4-amino-6-chloro-2-(2-thienyl)-phenol;
• 4-amino-6-methyl-2-(2-thienyl)-phenol;
• 4-amino-2-(3-acetyl-2-thienyl)-phenol;
• 4-amino-2-(3-chloro-2-thienyl)-phenol;
• 4-amino-2-(3-formyl-2-thienyl)-phenol;
• 4-amino-2(3-methyl-2-thienyl)-phenol;
• 4-amino-2-(3-nitro-2-thienyl)phenol;
• 4-amino-2-(4-acetyl-2-thienyl)-phenol;
• 4-amino-2-(4-chloro-2-thienyl)phenol;
• 4-amino-2-(4-formyl-2-thienyl)-phenol;
• 4-amino-2-(4-methyl-2-thienyl)phenol;
• 4-amino-2-(4-nitro-2-thienyl)phenol;
• 4-amino-2-(5-acetyl-2-thienyl)-phenol;
• 4-amino-2-(5-chloro-2-thienyl)-phenol;
• 4-amino-2-(5-formyl-2-thienyl)phenol;
• 4-amino-2-(5-methyl-2-thienyl)-phenol and 4-amino-2-(5-nitro-2-thienyl)phenol.

A dye composition for oxidative dyeing of keratin fibers, said dye composition comprising at least one coupler compound and at least one developer compound, said at least one developer compound comprising at least one p-aminophenol derivative compound of formula (I), or a physiologically compatible water-soluble salt thereof,

• 8
• wherein X is oxygen, sulfur or NR5,
• R1 represents hydrogen, a halogen atom, a C1- to C4-alkyl group, a C1- to C4-hydroxyalkyl group or a C1- to C4-alkoxy group;
• R2 and R4, independently of each other, each represent hydrogen, a hydroxy group, a halogen atom, a cyano group, a C1- to C4-alkoxy group, a C1- to C6-alkyl group, a C1- to C4-alkylthioether group, a mercapto group, a nitro group, an amino group, a C1- to C6-alkylamino group, a (C1- to C6)-dialkylamino group, a —C(O)H group, a —C(O)CH3 group, a —C(O)CF3 group, a —Si(CH3)3 group, a C1- to C4-hydroxyalkyl group, a C3- to C4-dihydroxyalkyl group, a —CH═CHR6 group, a —(CH2)p—CO2R7 group or a —(CH2)p—R8 group, with p=1, 2, 3 or 4, a —C(R9)═NR10 group or a C(R 11)H—NR12R13 group;
• R3 represents -hydrogen, a halogen atom, a C1- to C6-alkyl group, or a —C(O)H group;
• R5 represents hydrogen, a C1- to C6-alkyl group, a C1- to C4-hydroxyalkyl group, a phenyl group or an acetyl group;
• R6 represents hydrogen, a hydroxy group, a nitro group, an amino group, a —CO2R7 group or a —C(O)CH3 group;
• R7, R9 and R11 each represent, independently of each other, hydrogen or a C1- to C4-alkyl group;
• R8 represents an amino group or a nitrile group;
• R10, R12 and R13 each represent, independently of each other, hydrogen, a hydroxy group, a C1- to C4-alkyl group, a C1- to C4-hydroxyalkyl group, a 3- to C4-dihydroxyalkyl group or a group of formula (II):
• 9
• and R14 represents hydrogen, an amino group or a hydroxy group.

A hair dye composition for oxidation dyeing of hair, said hair dye composition having a pH of from 6.5 to 11.5 and comprising water, from 0.5 to 30 percent by weight of at least one surfactant compound, 0.1 to 25 percent by weight of a thickener, from 0.1 to 5.0 percent by weight of a hair care substance, from 0.005 to 20 percent by weight of at least one coupler compound and from 0.005 to 20 percent by weight of at least one developer compound, wherein said at least one developer compound comprises at least one p-aminophenol derivative compound of formula (I), or a physiologically compatible water-soluble salt thereof,

• 10
• wherein X is oxygen, sulfur or NR5,
• R1 represents hydrogen, a halogen atom, a C1- to C4-alkyl group, a C1- to C4-hydroxyalkyl group or a C1- to C4-alkoxy group;
• R2 and R4, independently of each other, each represent hydrogen, a hydroxy group, a halogen atom, a cyano group, a C1- to C4-alkoxy group, a C1- to C6-alkyl group, a C1- to C4-alkylthioether group, a mercapto group, a nitro group, an amino group, a C1- to C6-alkylamino group, a (C1- to C6)-dialkylamino group, a —C(O)H group, a —C(O)CH3 group, a —C(O)CF3 group, a —Si(CH3)3 group, a C1- to C4-hydroxyalkyl group, a C3- to C4-dihydroxyalkyl group, a —CH═CHR6 group, a —(CH2)p—CO2R7 group or a —(CH2)p-R8 group, with p=1, 2, 3 or 4, a —C(R9)═NR10 group or a C(R 11)H—NR12R13 group;
• R3 represents hydrogen, a halogen atom, a C1- to C6-alkyl group, or a —C(O)H group;
• R5 represents hydrogen, a C1- to C6-alkyl group, a C1- to C4-hydroxyalkyl group, a phenyl group or an acetyl group;
• R6 represents hydrogen, a hydroxy group, a nitro group, an amino group, a —CO2R7 group or a —C(O)CH3 group;
• R7, R9 and R11 each represent, independently of each other, hydrogen or a C1- to C4-alkyl group;
• R8 represents an amino group or a nitrile group;
• R10, R12 and R13 each represent, independently of each other, hydrogen, a hydroxy group, a C1- to C4-alkyl group, a C1- to C4-hydroxyalkyl group, a C3- to C4-dihydroxyalkyl group or a group of formula (II):
• 11
• and R14 represents hydrogen, an amino group or a hydroxy group.

A method of dyeing hair, said method comprising the steps of:

• a) mixing an oxidation dye composition with an oxidizing agent in a weight ratio of dye composition to oxidizing agent of 5:1 to 1:2 to form a ready-to-apply hair dyeing mixture;
• b) applying the ready-to-apply hair dyeing mixture to the hair;
• c) after the applying of step b), allowing the hair dyeing mixture to act on the hair for from about 10 to 45 minutes at 15 to 50° C.;
• d) subsequently rinsing the hair with water and drying;
• wherein said oxidation dye composition contains water, at least one coupler compound, at least one developer compound, wherein said at least one developer compound comprises at least one p-aminophenol derivative compound of formula (I), or a physiologically compatible water-soluble salt thereof,
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• wherein X is oxygen, sulfur or NR5,
• R1 represents hydrogen, a halogen atom, a C1- to C4-alkyl group, a C1- to C4-hydroxyalkyl group or a C1- to C4-alkoxy group;
• R2 and R4, independently of each other, each represent hydrogen, a hydroxy group, a halogen atom, a cyano group, a C1- to C4-alkoxy group, a C1- to C6-alkyl group, a C1- to C4-alkylthioether group, a mercapto group, a nitro group, an amino group, a C1- to C6-alkylamino group, a (C1- to C6)-dialkylamino group, a —C(O)H group, a —C(O)CH3 group, a —C(O)CF3 group, a —Si(CH3)3 group, a C1- to C4-hydroxyalkyl group, a C3- to C4-dihydroxyalkyl group, a —CH═CHR6 group, a —(CH2)p—CO2R7 group or a —(CH2)p—R8 group, with p=1, 2, 3 or 4, a —C(R9)═NR10 group or a C(R11)H—NR12R13 group;
• R3 represents hydrogen, a halogen atom, a C1- to C6-alkyl group, or a —C(O)H group;
• R5 represents hydrogen, a C1- to C6-alkyl group, a C1- to C4-hydroxyalkyl group, a phenyl group or an acetyl group;
• R6 represents hydrogen, a hydroxy group, a nitro group, an amino group, a —CO2R7 group or a —C(O)CH3 group;
• R7, R9 and R11 each represent, independently of each other, hydrogen or a C1- to C4-alkyl group;
• R8 represents an amirio group or a nitrile group;
• R10, R12 and R13 each represent, independently of each other, hydrogen, a hydroxy group, a C1- to C4-alkyl group, a C1- to C4-hydroxyalkyl group, a C3- to C4-dihydroxyalkyl group or a group of formula (II):
• 13
• and R14 represents hydrogen, an amino group or a hydroxy group.