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

1. An azo dye of formula

wherein

D is a radical of formula

R 1 and R 2 independently denote hydrogen; C 6 -C 10 aryl which is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C 1 -C 6 alkyl, or C 1 -C 6 alkoxy; C 1 -C 12 alkyl which may be interrupted one or more times by —O—, —S—, —NR 4 —, —CO—, —COO— or —OOC—, and is unsubstituted or substituted by cyano, carboxy, hydroxy, C 6 -C 10 aryl, or C 6 -C 10 aryloxy, which C 6 -C 10 aryl or C 6 -C 10 aryloxy is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C 1 -C 6 alkyl, or C 1 -C 6 alkoxy;

R 3 and R 4 are each independently of the other hydrogen, halogen, nitro, cyano, trifluoromethyl, carboxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 6 -C 10 arylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfonylamino or C 1 -C 4 alkanoylamino, and

R 5 is halogen, nitro, cyano, trifluoromethyl, carboxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 6 -C 10 arylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfonylamino or C 1 -C 4 alkanoylamino; and

R 6 , R 7 , R 8 and R 9 independently of each other are hydrogen, hydroxy, halogen, cyano, nitro or C 1 -C 4 alkanoylamino, and

the radicals X independently denote N or C—H, with the proviso that at least one radical X denotes C—H.

2. An azo dye of formula (1) according to claim 1 , wherein R 1 and R 2 independently denote hydrogen, methyl, ethyl, n-propyl, i-propyl or n-butyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-ethoxyethyl, 3-ethoxypropyl, 4-ethoxybutyl, phenyl, tolyl, benzyl, or 2-phenylethyl.

3. An azo dye of formula (1) according to claim 1 , wherein R 1 is hydrogen and R 2 denotes hydrogen, methyl, ethyl, n-propyl, i-propy n-butyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-ethoxyethyl, 3-ethoxypropyl, 4-ethoxybutyl, phenyl, tolyl, benzyl, or 2-phenylethyl.

4. An azo dye of formula (1) according to claim 1 , wherein R 1 and R 2 are hydrogen.

5. An azo dye of formula (1) according to claim 1 , wherein both radicals X denote C—H.

6. An azo dye of formula (1) according to claim 1 , wherein R 3 and R 4 are each independently of the other hydrogen, halogen, nitro, cyano, trifluoromethyl, methylsulfonyl, ethylsulfonyl, acetylamino, or propionylamino and wherein R 5 is halogen, nitro, cyano, trifluoromethyl, methylsulfonyl, ethylsulfonyl, acetylamino, or propionylamino.

7. An azo dye of formula (1) according to claim 6 , wherein R 3 and R 4 are each independently of the other hydrogen, halogen, nitro, cyano, or trifluoromethyl and wherein R 5 is halogen, nitro, cyano, or trifluoromethyl.

8. An azo dye of formula (1) according claim 1 , wherein R 6 , R 7 , R 8 and R 9 independently of each other are hydrogen, hydroxy, halogen, acetylamino, or propionylamino.

9. An azo dye of formula (1) according to claim 1 , wherein D is a radical of formula (2).

10. A process for the preparation of an azo dye of formula (1) according to claim 1 , which comprises diazotizing an amine compound of formula

to form a diazotized amine and then coupling the diazotized amine to a coupling component of the formula

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and X are as defined in claim 1 .

11. A process for dyeing semi-synthetic or synthetic hydrophobic fibre materials comprising applying an aqueous composition comprising a dye of formula (1) according to claim 1 to the semi-synthetic or synthetic hydrophobic fibre materials.

12. A semi-synthetic or synthetic hydrophobic fibre material, dyed by the process according to claim 11 .

13. A process for printing semi-synthetic or synthetic fibre materials comprising spraying an aqueous composition comprising a dye of formula (1) according to claim 1 onto the semi-synthetic or synthetic hydrophobic fibre materials.

14. A semi-synthetic or synthetic hydrophobic fibre material printed by the process according to claim 13 .