Cationic direct dyes

Patent metadata

Field	Value
Publication number	US-10494527-B2
Application number	US-201615557594-A
Country	US
Kind code	B2
Filing date	Mar 18, 2016
Priority date	Mar 19, 2015
Publication date	Dec 3, 2019
Grant date	Dec 3, 2019

Abstract

The invention relates to cationic direct dyes of the formula I (1), wherein m and n are independently from each other 0 or 1, D is an aromatic or a cationic heteroaromatic group, which are further specified, K is an aromatic or heteroaromatic group, E 1 and E 2 are independently from each other ═CH— or ═N—, An is an anion and a is a number from 1 to 6 and R 1 and R 2 are independently from each other and further specified. The compounds show washfastness at hair-dying.

First claim

The invention claimed is:

1. Compounds of formula

wherein
D is a cationic heteroaromatic group having a

K is an aromatic or group;
R 1 and R 2 independently from each other are hydrogen; C 1 -C 12 alkyl; C 1 -C 12 alkyl, which is substituted by hydroxy; amino-C 6 -C 10 aryl; N(R 6 R 7 )—C 1 -C 8 alkyl; N(R 6 R 7 )—C 1 -C 12 alkyl, which is substituted by hydroxy or interrupted by —NR 9 —; C 6 -C 10 aryl; or
R 6 , R 7 and R 9 , independently from each other are hydrogen; C 1 -C 5 alkyl; amino-C 1 -C 5 alkyl; C 1 -C 5 alkylamino-C 1 -C 5 alkyl; or di-C 1 -C 5 alkylamino-C 1 -C 5 alkyl;
R 10 and R 11 independently from each other are hydrogen; C 1 -C 12 alkyl; N(R 13 R 14 )—C 1 -C 12 alkyl; N(R 13 R 14 )—C 1 -C 12 alkyl which is interrupted by phenylene; N + (R 13 R 14 R 15 )—C 1 -C 12 alkyl which is interrupted by phenylene;
R 13 , R 14 , R 15 independently from each other are hydrogen; C 1 -C 5 alkyl; amino-C 1 -C 5 alkyl; C 1 -C 5 alkylamino-C 1 -C 5 alkyl; or di-C 1 -C 5 alkylamino-C 1 -C 5 alkyl;
E 1 and E 2 independently from each other are ═N—;
An is an anion
a is a number from 1 to 3;
m and n are 1;
wherein for group D, at least one of the radicals R 1 , R 2 , R 10 , and R 11 is substituted by radical comprising at least one amino group.

2. Compounds according to claim 1 , wherein D in formula (1a)
R 10 and R 11 independently from each other are C 1 -C 12 alkyl; amino-C 1 -C 12 alkyl; di-C 1 -C 5 alkylamino-C 1 -C 12 alkyl; or N + (R 3 R 4 R 5 )—C 1 -C 12 alkyl.

3. Compounds according to claim 1 , which correspond to formula

wherein
R 1 and R 2 independently from each other are hydrogen; C 1 -C 12 alkyl; C 1 -C 12 alkyl, which is substituted by hydroxy; amino-C 6 -C 10 aryl; N(R 6 R 7 )—C 1 -C 8 alkyl; N(R 6 R 7 )—C 1 -C 8 alkyl, which is interrupted by —NR 9 —;
R 10 and R 11 independently from each other are C 1 -C 12 alkyl; C 1 -C 12 alkyl which is substituted by hydroxy or interrupted by phenylene; amino-C 1 -C 12 alkyl; di-C 1 -C 5 alkyl-amino-C 1 -C 12 alkyl; or N + (R 3 R 4 R 5 )—C 1 -C 12 alkyl;
An is an anion; and
R 3 , R 4 , R 5 , R 6 , R 7 , and R 9 independently from each other are hydrogen; C 1 -C 5 alkyl; amino-C 1 -C 5 alkyl; C 1 -C 5 alkylamino-C 1 -C 5 alkyl; or di-C 1 -C 5 alkylamino-C 1 -C 5 alkyl.

4. Compounds according to claim 1 , wherein
R 1 and R 2 independently from each other are C 1 -C 12 alkyl;
R 6 , R 7 , R 5 , independently from each other are hydrogen; or C 1 -C 6 alkyl; and
R 10 and R 11 independently from each other are C 1 -C 12 alkyl; or N + (R 3 R 4 R 5 )—C 1 -C 12 alkyl; and
R 3 , R 4 and R 5 independently from each other are hydrogen; or C 1 -C 5 alkyl.

5. Compounds according to claim 1 , wherein
R 1 and R 2 are hydrogen; or C 1 -C 5 alkyl;
R 6 , R 7 , R 5 , independently from each other are hydrogen; or C 1 -C 5 alkyl; and
R 10 and R 11 are C 1 -C 5 alkyl; or N + (R 13 R 14 R 15 )—C 1 -C 5 alkyl; or N(R 13 R 14 )—C 1 -C 5 alkyl; and
R 3 and R 4 independently from each other are hydrogen; or C 1 -C 5 alkyl.

6. Compounds according to claim 1 , wherein
R 1 and R 2 independently from each other are C 1 -C 12 alkyl; and
R 11 and R 12 independently from each other are C 1 -C 5 alkyl; or amino-C 1 -C 5 alkyl.

7. A compound selected from the group consisting of:

Assignees

• Basf Se

Inventors

• Bachmann Frank
• Cremer Christian
• Froehling Beate
• Murphy Bryan Patrick
• Zhang Guiru
• Torgerson Peter Marte

Classifications

• A61K8/4926

  having six membered rings · CPC title

• A61K2800/4322

  in preparations for temporarily coloring the hair further containing an oxidizing agent · CPC title

• C09B56/12

  Anthraquinone-azo dyes {(from diazotised aminoanthracene C09B29/0022, azo dyes containing hydroxyl groups acylated with polyfunctional anthraquinone derivatives C09B43/26)} · CPC title

• C09B23/105

  two >CH- groups · CPC title

• C09B44/126

  in a six-membered ring, e.g. pyrridinium, quinolinium · CPC title