Method of conditioning azo pigments containing carboxylic ester groups

1. A method of conditioning an azo pigment containing carboxylic ester groups, comprising the step of subjecting a crude azo pigment, wherein the crude azo pigment contains carboxylic ester groups, to a treatment with glycol monoalkyl ethers or with mixtures of glycols and glycol dialkyl ethers and, optionally, glycol monoalkyl ethers and wherein the crude azo pigment containing carboxylic ester groups is a pigment selected from the group consisting of C.I. Pigment Yellow, 182, C.I. Pigment Red 119, 139, 175, 188, 208, 220, 221, 248, a diazo pigment of the general formula (1)

where

R 1 , R 2 , R 3 , and R 4 are identical or different and are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 5 -alkoxycarbonyl, nitro, cyano, halogen, phenoxy or trifluoromethyl;

R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 14 are identical or different and are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, cyano, halogen, phenoxy, trifluoromethyl, COOH, COOR 15 , CONH 2 , CONCH 3 , CON(CH 3 ) 2 or SO 2 NR 15 R 16 , where

R 15 is C 1 -C 4 -alkyl and R 16 is hydrogen, C 1 -C 4 -alkyl or phenyl,

and at least one radical from R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 or R 14 is an ester group —COOR 15 ; and a monoazo pigment of the general formula (2)

where

R 1 , R 2 , and R 3 are identical or different and are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 5 -alkoxycarbonyl, nitro, cyano, halogen, phenoxy or trifluoromethyl;

R 5 , R 6 , R 7 , R 8 , and R 9 are identical or different and are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, nitro, cyano, halogen, phenoxy or trifluoromethyl, COOH, COOR 15 , CONH 2 , CONCH 3 , CON(CH 3 ) 2 or SO 2 NR 15 R 16 , where

R 15 is C 1 -C 4 -alkyl and

R 16 is hydrogen, C 1 -C 4 -alkyl or phenyl,

and at least one radical from R 5 , R 6 , R 7 , R 8 , and R 9 is an ester group —COOR 15 ,

A is a fused heterocyclic ring in 3,4- or 4,5- or 5,6-position and is constructed from the groups of the general formula (3), (4), (5) or (6):

where

R 17 and R 18 independently of one another are hydrogen, C 1 -C 8 -alkyl, C 5 -C 6 -cycloalkyl, benzyl, phenyl or naphthyl, wherein, optionally, the phenyl and naphthyl are substituted by one or more of the radicals halogen, nitro, C 1 -C 8 -alkyl, C 5 -C 6 -cycloalkyl, benzyl, phenyl, naphthyl, COO(C 1 -C 6 )alkyl, C 1 -C 3 -alkoxy or trifluoromethyl.

2. The method as claimed in claim 1 , wherein the subjecting step is carried out in the presence of glycol monoalkyl ethers of the general formula (7)

where

n is an integer between 0 and 3,

R 19 and R 20 independently of one another are hydrogen or C 1 -C 6 -alkyl; and

R 21 is C 1 -C 6 -alkyl.

3. The method as claimed in claim 1 , wherein the subjecting step takes place in a mixture of a glycol of the general formula (8)

where

n is an integer between 0 and 3 and

R 19 and R 29 independently of one another are hydrogen or C 1 -C 6 -alkyl,

and a glycol dialkyl ether of the general formula (9)

where

n is an integer between 0 and 3,

R 19 and R 29 independently of one another are hydrogen or C 1 -C 6 -alkyl; and

R 21 is C 1 -C 6 -alkyl.

4. The method as claimed in claim 1 , wherein the subjecting step is carried out in a temperature range between 30 and 200° C.

5. The method as claimed in claim 1 , wherein the subjecting step is carried out in 2(2-methoxyethoxy)ethanol, 2(2-ethoxyethoxy)ethanol, 2-butoxyethanol, a mixture of diethylene glycol and diethylene glycol dimethyl ether or a mixture of diethylene glycol and diethylene glycol diethyl ether.

6. A method of conditioning an azo pigment containing carboxylic ester groups, comprising the step of subjecting a crude azo pigment, wherein the crude azo pigment contains carboxylic ester groups, to a treatment with glycol monoalkyl ethers or with mixtures of glycols and glycol dialkyl ethers and, optionally, glycol monoalkyl ethers and wherein the crude azo pigment containing carboxylic ester groups is a pigment selected from the group consisting of C.I. Pigment Yellow 155, and 219.

7. A method of conditioning an azo pigment containing carboxylic ester groups, comprising the step of subjecting a crude azo pigment, wherein the crude azo pigment contains carboxylic ester groups, to a treatment with glycol monoalkyl ethers or with mixtures of glycols and glycol dialkyl ethers and, optionally, glycol monoalkyl ethers and wherein the crude azo pigment containing carboxylic ester groups is a pigment selected from the group consisting of C.I. Pigment Yellow 120, 175 and 213.

8. The method as claimed in claim 1 , wherein the crude azo pigment includes at least one alkoxycarbonyl group located on a terminal phenyl ring.

9. The method as claimed in claim 6 , wherein the crude azo pigment includes at least one alkoxycarbonyl group located on a terminal phenyl ring.

10. The method as claimed in claim 7 , wherein the crude azo pigment includes at least one alkoxycarbonyl group located on a terminal phenyl ring.

11. The method as claimed in claim 8 , wherein the alkoxycarbonyl group is a C 1 -C 4 -alkoxy-carbonyl group.

12. The method as claimed in claim 9 , wherein the alkoxycarbonyl group is a C 1 -C 4 -alkoxy-carbonyl group.

13. The method as claimed in claim 1 , wherein the alkoxycarbonyl group is a C 1 -C 4 -alkoxy-carbonyl group.