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

Patent metadata

Field	Value
Publication number	US-9376570-B2
Application number	US-201314413583-A
Country	US
Kind code	B2
Filing date	Jun 26, 2013
Priority date	Jul 27, 2012
Publication date	Jun 28, 2016
Grant date	Jun 28, 2016

Abstract

The present invention relates to azo dyes of formula (1), 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—, —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. A process for the preparation of an azo dye of formula (1)

which comprises reacting an azo dye of the formula (3)

with a mixture of at least one alkali metal cyanide and at least one heavy metal cyanide, wherein R 1 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—, —NR 4 —, —COO— or —OOC—;
R 4 is hydrogen or C 1 -C 12 alkyl;
either R 7 is cyano and R 3 is halogen or R 2 is halogen and R 3 is cyano;
Ar represents a carbocyclic or heterocyclic aromatic radical; and
Hal represents halogen and wherein a total amount of 0.5 mol-1.5 mol of cyanide is applied per mol of dye of formula (3).

2. A mixture comprising an azo dye of the formula

an azo dye of the formula

and
an azo dye of the formula

wherein
R 1 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—, —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;
Ar represents a carbocyclic or heterocyclic aromatic radical;
and Hal represents halogen.

3. A dye mixture comprising
(A) 10-90% by weight, of a dye of the formula (1)

wherein R 1 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—, —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
and
(B) 10-90% by weight, of a dye of the formula (1) as defined above which is structurally different from the dye according to component (A).

4. A process for dyeing or printing semi-synthetic hydrophobic fibre material comprising applying a mixture according to claim 2 to the semi-synthetic hydrophobic fibre material.

5. A semi-synthetic hydrophobic fibre material dyed or printed by the process according to claim 4 .

6. A process for dyeing or printing synthetic hydrophobic fibre material comprising applying a mixture according to claim 2 to the synthetic hydrophobic fibre material.

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

8. A process for dyeing or printing semi-synthetic hydrophobic fibre material comprising applying the dye mixture according to claim 3 to the semi-synthetic hydrophobic fibre material.

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

10. A process for dyeing or printing synthetic hydrophobic fibre material comprising applying the dye mixture according to claim 3 to the synthetic hydrophobic fibre material.

11. A synthetic hydrophobic fibre material dyed or printed by the process according to claim 10 .

Assignees

• Huntsman Int Llc

Inventors

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

Classifications

• C09B67/0051

  mixture of two or more monoazo dyes · CPC title

• C09B43/42

  by substituting radicals containing hetero atoms for —CN radicals · CPC title

• C09B29/0007

  containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof · CPC title

• C09B29/0085

  Thiazoles or condensed thiazoles · CPC title

• C09B29/0048

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