Disperse azo dyes, a process for the preparation thereof and the use thereof

Patent metadata

Field	Value
Publication number	US-10023742-B2
Application number	US-201615151624-A
Country	US
Kind code	B2
Filing date	May 11, 2016
Priority date	Jul 27, 2012
Publication date	Jul 17, 2018
Grant date	Jul 17, 2018

Abstract

The present invention relates to azo dyes of formula

wherein
R 1 denotes C 1 -C 12 alkyl which is unsubstituted or substituted by one or more C 1 -C 12 alkoxy groups, hydroxyl groups, amino groups, cyano groups or halogen atoms and which may be interrupted one or more times by the radical —O—, —S—, —NR 4 —, —COO— or —OOC—; R 4 is hydrogen or C 1 -C 12 alkyl; either R 2 is cyano and R 3 is halogen or R 2 is halogen and R 3 is cyano; and Ar represents a carbocyclic or heterocyclic aromatic radical, to the process for the preparation thereof, to mixtures containing said dyes and to the use thereof in dyeing or printing semi-synthetic and especially synthetic hydrophobic fiber materials, more especially textile materials.

First claim

What is claimed is:

1. An azo dye of formula

wherein
R 1 denotes ethyl, propyl or i-propyl;
either R 2 is cyano and R 3 is halogen or R 2 is halogen and R 3 is cyano; and
Ar is a radical of the formula

wherein
R 5 denotes hydrogen, chloro, methyl, methoxy, 2-hydroxyethyl or —COOR 19 , wherein R 19 has one of the meanings given for R 1 above;
R 6 is —NH—CO—R 20 wherein R 20 denotes a C 1 -C 12 alkyl which is unsubstituted or substituted by one or more C 1 -C 12 alkoxy groups, C 1 -C 12 alkylcarbonyl groups, C 7 -C 25 arylcarbonyl groups, hydroxyl groups, amino groups, cyano groups or halogen atoms and which may be interrupted one or more times by the radical —O—, —S—or —NR 4 —;
R 7 is ethyl and R 8 is methyl, ethyl, n-propyl, n-butyl, allyl, benzyl, 4-nitrobenzyl, 4-methoxybenzyl, 3-methoxybenzyl, 2-cyanoethyl, 2-methoxyethyl, 2-phenylethyl, 2-hydroxy-3 -phenoxypropyl, or 2-hydroxy-3 -i-propoxyethyl;
X denotes ethylene, trimethylene or oxyethylene;
R 9 is vinyl, allyl, benzyl or has one of the meanings given for R 1 above;
R 10 is hydroxy or phenylamino;
R 11 is hydrogen, —COOR 21 or C 6 -C 24 aryl that is unsubstituted or substituted by one or more C 1 -C 12 alkyl groups, C 1 -C 12 alkoxy groups, hydroxyl groups, amino groups, cyano groups or halogen atoms wherein R 21 has one of the meanings given for R 1 above;
R 12 is hydrogen or —SO 2 —NHR 22 , wherein R 22 has one of the meanings given for R 1 above;
R 13 is hydrogen or hydroxy;
R 14 denotes C 1 -C 12 alkyl or trifluoromethyl:
R 15 is cyano or —CONH 2 ;
R 16 has one of the meanings given for R 1 above;
R 23 and R 24 are each independently of the other hydrogen, vinyl, allyl or C 1 -C 6 alkyl which is unsubstituted or substituted by cyano, carboxy, hydroxy, C 1 -C 6 alkoxy-, C 2 -C 8 alkoxyalkoxy- or C 6 -C 24 aryl; and
R 18 is hydrogen, C 1 -C 12 alkyl, C 1 -C 12 alkoxy or C 6 -C 24 aryl that is unsubstituted or substituted by one or more C 1 -C 12 alkyl groups, C 1 -C 12 alkoxy groups, hydroxyl groups, amino groups, cyano groups or halogen atoms with the proviso that R 8 in the claimed formula (2a) is chosen from 2-methoxyethyl and 2-methoxycarbonylethyl group.

2. The azo dye of formula (1) according to claim 1 , wherein R 1 denotes ethyl.

3. The azo dye of formula (1) according to claim 1 , wherein R 2 is cyano and R 3 is bromo.

4. The azo dye of formula (1) according to claim 1 , wherein Ar is a radical of the formula (2a) wherein R 5 is hydrogen, methyl or methoxy.

5. A dichromatic or trichromatic dye mixture comprising at least one azo dye of formula (1) according to claim 1 and at least one further disperse dye.

6. A process for dyeing or printing semi-synthetic hydrophobic fibre material comprising applying a dye of formula (1) according to claim 1 to the semi-synthetic hydrophobic fibre material.

7. A semi-synthetic hydrophobic fibre material dyed or printed by the process according to claim 6 .

8. A process for dyeing or printing synthetic hydrophobic fibre material comprising applying a dye of formula (1) according to claim 1 to the synthetic hydrophobic fibre material.

9. A synthetic hydrophobic fibre material dyed or printed by the process according to claim 8 .

Assignees

• Huntsman Int Llc

Inventors

• Lauk Urs
• Nowack Patric
• Petermann Ralf
• Dreier Romeo

Classifications

• C09B29/0809

  substituted amino group · CPC title

• C09B29/0003 Primary

  from diazotized anilines · CPC title

• C09B29/095

  Amino naphthalenes · CPC title

• C09B29/0033 Primary

  containing a five-membered heterocyclic ring with one nitrogen atom · CPC title

• D10B2331/04

  polyesters, e.g. polyethylene terephthalate [PET] · CPC title