US 2003/0110578 A1Published application

Substituted 1,4-diaminobenzene compounds and oxidation dye precursor compositions containing same

AssigneeWella Aktiengesellschaft

InventorsLaurent Chassot, Hans-Juergen Braun

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Abstract

New substituted 2,5-diamino-1-aminomethylbenzene compounds of formula (I), or physiologically compatible water-soluble salts thereof, 1 are described as well as methods for preparing them. In addition, oxidation dye precursor compositions for dyeing keratin fibers, especially human hair, which each contain from 0.005 to 20 percent by weight of at least one of the new substituted 2,5-diamino-1-aminomethylbenzene compounds of formula (I), or their physiologically compatible water-soluble salts, are described. Methods for dyeing hair with ready-to-apply dye mixtures made by mixing these oxidation dye precursor compositions with an oxidizing agent, such as hydrogen peroxide solution, are also described.

Claims15

Dependent claims

A substituted 2,5-diamino-1-aminomethylbenzene compound of formula (I), or a physiologically compatible water-soluble salt thereof,

7
wherein R1, R2, R3, R4, R5, R6 and R7, independently of each other, each represent hydrogen, a C1- to C6-alkyl group, a C1- to C4-hydroxyalkyl group, a C2- to C4-dihydroxyalkyl group or a C1- to C4-alkoxy-(C1- to C2-)alkyl group or at least one pair selected from the group consisting of R1 and R2;
R3 and R4;
and R5 and R6 together with the N atom form a four-member to eight-member aliphatic ring, with the proviso that at least two of said R1 to R6 each represent said hydrogen;
R8 represents hydrogen, a halogen atom, a C1- to C4-alkyl group, a C1- to C4-hydroxyalkyl group or a C1- to C4-alkoxy group;
R9 represents hydrogen, a halogen atom, a cyano group, a hydroxy group, a C1- to C4-alkoxy group, a C1- to C4-hydroxyalkoxy group, a C1- to C6-alkyl group, a C1- to C4-alkylthioether group, a mercapto group, an amino group, a C1- to C4-alkylamino group, a C1- to C4-hydroxyalkylamino group, a di(C1- to C4-alkyl)amino group, a di(C1- to C4-hydroxyalkyl)amino group, a {dihydroxy(C2- to C4)-alkyl}amino group, a (C1- to C4-hydroxyalkyl)-C1-C4-alkylamino group, a trifluoromethane group, a C1-C4-hydroxyalkyl group or a C3-C4 dihydroxyalkyl group;
and R10 represents hydrogen or a C1- to C6-alkyl group.

4 more elements

A substituted 2,5-diamino-1-aminomethylbenzene compound selected from the group consisting of 2-((2-amino-phenylamino)-methyl)-1,4-diaminobenzene;

2-((3-aminophenyl-amino)-methyl)-1,4-diaminobenzene;
2-((4-aminophenylamino)methyl)-1,4-diaminobenzene;
2-((4-bis(2-hydroxyethyl)aminophenylamino)-methyl)-1,4-diaminobenzene;
2-((4-dimethylamino-phenylamino)methyl)-1,4-diamino-benzene;
N1,N1-bis(hydroxyethyl)-2-((3-aminophenylamino)-methyl)-1,4-diaminobenzene;
N1,N1-bis(hydroxyethyl)-2-((4-amino-phenylamino)-methyl)-1,4-diaminobenzene, N1,N1-bis(hydroxyethyl)-2-((4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
N1-dihydroxypropyl-2-((4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
N1-dihydroxypropyl-2-((4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
N1-dihydroxy-propyl-2-((4-dimethylaminophenylamino)-methyl)-1,4-diaminobenzene;
N4,N4-bis(hydroxyethyl)-2-((3-aminophenylamino)-methyl)-1,4-diaminobenzene;
N4, N4-bis(hydroxyethyl)-2-((4-aminophenylamino)-methyl)-1,4-diaminobenzene;
N4, N4-bis(hydroxy-ethyl)-2-((4-bis(2-hydroxyethyl)-amino-phenylamino)-methyl)-1,4-diaminobenzene;
N4, N4-bis(hydroxyethyl)-2-((4-dimethylamino-phenyl-amino)-methyl)-1,4-diaminobenzene;
N4-dihydroxypropyl-2-((4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
N4-dihydroxypropyl-2-((4-bis(2-hydroxy-ethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
N4-dihydroxypropyl-2-((4-dimethylamino-phenylamino)-methyl)-1,4-diamino-benzene;
2-((2-(2-hydroxyethyl)aminophenylamino)-methyl)-1,4-diamino-benzene;
2-((2-(pyrrolidin-1-yl)-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-dihydroxypropylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-(2-hydroxyethyl)-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-(pyrrolidin-1-yl)-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-dihydroxypropylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-methylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-(pyrrolidin-1-yl)-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-dihydroxypropylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-methylamino-phenylamino)-methyl)-1,4-diamino-benzene;
2-((2-(2-hydroxyethyl)-4-amino-phenylamino) methyl)-1,4-diamino-benzene, 2-((2-(2-hydroxyethyl)-4-bis(2-hydroxyethyl)-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-chloro-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-chloro-4-bis(2-hydroxyethyl)-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methoxy-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methoxy-4-bis(2-hydroxyethyl)-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methyl-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methyl-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-(2-hydroxyethyl)-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-(2-hydroxyethyl)-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-chloro-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-chloro-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-methoxy-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-methoxy-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-methyl-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-methyl-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-(2-hydroxyethoxy)-3-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-(2-hydroxyethoxy)-3-bis(2-hydroxyethyl)amino-phenyl amino)-methyl)-1,4-diaminobenzene;
2-((4-(2-hydroxyethyl)-3-amino-phenylamino)-methyl)-1,4-diaminobenzene and 2-((4-(2-hydroxyethyl)-3-bis(2-hydroxyethyl)-amino-phenylamino)-methyl)-1,4-diaminobenzene.

43 more elements

An oxidation dye precursor composition for dyeing keratin fibers, said oxidation dye precursor composition containing at least one substituted 2,5-diamino-1-aminomethylbenzene compound of formula (I), or a physiologically compatible water-soluble salt thereof,

8
wherein R1, R2, R3, R4, R5, R6 and R7, independently of each other, each represent hydrogen, a C1- to C6-alkyl group, a C1- to C4-hydroxyalkyl group, a C2- to C4-dihydroxyalkyl group or a C1- to C4-alkoxy-(C1- to C2-)alkyl group or at least one pair selected from the group consisting of R1 and R2;
R3 and R4;
and R5 and R6 together with the N atom form a four-member to eight-member aliphatic ring, with the proviso that at least two of said R1 to R6 each represent said hydrogen;
R8 represents hydrogen, a halogen atom, a C1- to C4-alkyl group, a C1- to C4-hydroxyalkyl group or a C1- to C4-alkoxy group;
R9 represents hydrogen, a halogen atom, a cyano group, a hydroxy group, a C1- to C4-alkoxy group, a C1- to C4-hydroxyalkoxy group, a C1- to C6-alkyl group, a C1- to C4-alkylthioether group, a mercapto group, an amino group, a C1- to C4-alkylamino group, a C1- to C4-hydroxyalkylamino group, a di(C1- to C4-alkyl)amino group, a di(C1- to C4-hydroxyalkyl)amino group, a {dihydroxy(C2- to C4)-alkyl}amino group, a (C1- to C4-hydroxyalkyl)-C1-C4-alkylamino group, a trifluoromethane group, a C1-C4-hydroxyalkyl group or a C3-C4 dihydroxyalkyl group;
and
R10 represents hydrogen or a C1- to C6-alkyl group.

5 more elements

An aqueous or aqueous-alcoholic oxidation dye precursor composition for dyeing keratin fibers, said oxidation dye precursor composition comprising:

water;
at least one additive ingredient selected from the group consisting of aliphatic alcohols, glycerol, glycols, anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, thickeners, care materials, antioxidants, perfume oils, complex formers and pH adjusting agents;
and
from 0.1 to 10 percent by weight of at least one substituted 2,5-diamino-1-aminomethylbenzene compound, or a physiologically compatible water-soluble salt thereof, wherein said at least one substituted 2,5-diamino-1-aminomethylbenzene compound is selected from the group consisting of 2-((2-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-aminophenyl-amino)-methyl)-1,4-diaminobenzene;
2-((4-amino-phenylamino)methyl)-1,4-diaminobenzene;
2-((4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-dimethylamino-phenylamino)methyl)-1,4-diaminobenzene;
N1,N1-bis(hydroxyethyl)-2-((3-aminophenylamino)-methyl)-1,4-diaminobenzene;
N1,N1-bis(hydroxyethyl)-2-((4amino-phenylamino)-methyl)-1,4-diaminobenzene;
N1,N1-bis(hydroxyethyl)-2-((4-bis(2-hydroxyethyl)aminophenyl-amino)-methyl)-1,4-diaminobenzene;
N1-dihydroxypropyl-2-((4-aminophenylamino)-methyl)-1,4-diaminobenzene;
N1-dihydroxypropyl-2-((4-bis(2-hydroxyethyl)amino-phenylamino)methyl)-1,4-diaminobenzene;
N1-dihydroxypropyl-2-((4-dimethylamino-phenylamino)-methyl)-1,4-diaminobenzene;
N4,N4-bis(hydroxyethyl)-2-((3-amino-phenylamino)-methyl)-1,4-diaminobenzene;
N4,N4-bis(hydroxyethyl)-2-((4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
N4,N4-bis(hydroxy-ethyl)-2-((4-bis(2-hydroxyethyl)-amino-phenylamino)-methyl)-1,4-diaminobenzene;
N4,N4-bis(hydroxyethyl)-2-((4-dimethylamino-phenyl-amino)-methyl)-1,4-diamino-benzene;
N4-dihydroxypropyl-2-((4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
N4-dihydroxypropyl-2-((4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
N4-dihydroxypropyl-2-((4-dimethylamino-phenylamino)-methyl)-1,4-diamino-benzene;
2-((2-(2-hydroxyethyl)aminophenyl-amino)-methyl)-1,4-diamino-benzene;
2-((2-(pyrrolidin-1-yl)-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-dihydroxypropylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-(2-hydroxyethyl)-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-(pyrrolidin-1-yl)-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-dihydroxypropylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-methylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-(pyrrolidin-1-yl)-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-dihydroxypropylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-methylamino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-(2-hydroxyethyl)-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-(2-hydroxyethyl)-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-chloro-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-chloro-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methoxy-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methoxy-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methyl-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((2-methyl-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-(2-hydroxyethyl)-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-(2-hydroxyethyl)-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-chloro-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-chloro-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-methoxy-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-methoxy-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene, 2-((3-methyl-4-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((3-methyl-4-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-(2-hydroxyethoxy)-3-amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-(2-hydroxyethoxy)-3-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene;
2-((4-(2-hydroxyethyl)-3-amino-phenylamino)-methyl)-1,4-diaminobenzene and 2-((4-(2-hydroxyethyl)-3-bis(2-hydroxyethyl)amino-phenylamino)-methyl)-1,4-diaminobenzene.

48 more elements

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

a) mixing an oxidation dye precursor composition with an oxidizing agent in a weight ratio of 5:1 to 1:2 to form a ready-to-apply hair dyeing mixture, said oxidation dye precursor composition comprising at least one substituted 2,5-diamino-1-aminomethylbenzene compound of formula (I), or a physiologically compatible water-soluble salt thereof,
9
wherein R1, R2, R3, R4, R5, R6 and R7, independently of each other, each represent hydrogen, a C1- to C6-alkyl group, a C1- to C4-hydroxyalkyl group, a C2- to C4-dihydroxyalkyl group or a C1- to C4-alkoxy-(C1- to C2-)alkyl group or at least one pair selected from the group consisting of R1 and R2;
R3 and R4;
and R5 and R6 together with the N atom form a four-member to eight-member aliphatic ring, with the proviso that at least two of said R1 to R6 each represent said hydrogen;
R8 represents hydrogen, a halogen atom, a C1- to C4-alkyl group, a C1- to C4-hydroxyalkyl group or a C1- to C4-alkoxy group;
R9 represents hydrogen, a halogen atom, a cyano group, a hydroxy group, a C1- to C4-alkoxy group, a C1- to C4-hydroxyalkoxy group, a C1- to C6-alkyl group, a C1- to C4-alkylthioether group, a mercapto group, an amino group, a C1- to C4-alkylamino group, a C1- to C4-hydroxyalkylamino group, a di(C1- to C4-alkyl)amino group, a di(C1- to C4-hydroxyalkyl)amino group, a {dihydroxy(C2- to C4)-alkyl}amino group, a (C1- to C4-hydroxyalkyl)-C1-C4-alkylamino group, a trifluoromethane group, a C1-C4-hydroxyalkyl group or a C3-C4 dihydroxyalkyl group;
and R10 represents hydrogen or a C1- to C6-alkyl group;
b) applying a sufficient amount of the ready-to-apply hair dyeing mixture to hair in order to dye the hair;
c) after the applying of step b), allowing the ready-to-apply hair dyeing mixture to act on the hair for 10 to 45 minutes at 15 to 50° C.
d) after the allowing of step c), rinsing the hair with water and washing the hair with a shampoo as needed;
and
e) subsequently drying the hair.

10 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/251,765Filed 20 Sep 2002
Priority: DE 199 61 274.918 Dec 1999
Published: 19 Jun 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

A61K 8/411
Amines: aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
A61Q 5/10
Preparations for care of the hair: preparations for permanently dyeing the hair
C07C 211/51
With at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton: phenylenediamines
C07C 215/68
Compounds containing amino and hydroxy groups bound to the same carbon skeleton: having amino groups bound to carbon atoms of six-membered…

Family

Application09/706,000Continuation · filed 3 Nov 2000
Application10/251,765Continuation · filed 20 Sep 2002
US 6,602,302 B1Related patent
US 6,685,751 B2Related patent
US 2003/0110578 A1This patent

From the US filing history. Foreign family members aren’t listed.