Disperse azo dyestuffs

1. A dyestuff of the formula (I)

wherein

D is of the formula (IIa)

wherein

G 1 is hydrogen, halogen, cyano or nitro;

G 2 is hydrogen, halogen or nitro;

G 3 is hydrogen, halogen, methylsulfonyl, fluorosulfonyl or nitro; and

G 4 is hydrogen, halogen, trifluoromethyl, cyano or nitro;

or of the formula (IIb)

wherein

G 5 is hydrogen or halogen; and

G 6 is hydrogen, halogen, nitro, —SO 2 CH 3 or —SCN;

or of the formula (IIc)

wherein

G 7 is hydrogen or halogen,

or of the formula (IId)

wherein

G 8 is nitro, cyano, —CHO or a group of the formula (IIe)

wherein G 11 and G 12 are independently hydrogen, halogen, nitro or cyano;

G 9 is hydrogen or halogen; and

G 10 is nitro, cyano, —COCH 3 or —COO—G 13 , wherein G 13 is C 1 -C 4 alkyl;

or of the fomula (IIf);

R 1 is hydrogen, (C 1 -C 4 )-alkyl, hydroxy, —NHCOR 6 or —NHSO 2 R 6 ;

R 2 is hydrogen, halogen or (C 1 -C 4 )-alkoxy;

R 3 is hydrogen or methyl;

R 4 is hydrogen, (C 1 -C 6 )-alkyl, substituted (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkyl, which is interrupted by 1, 2 or 3 heteroatoms wherein said heteroatoms are —O—, —S— or —NR 7 , substituted (C 2 -C 6 )-alkyl, which is interrupted by 1, 2 or 3 heteroatoms wherein said heteroatoms are —O—, —S— or —NR 7 , (C 2 -C 6 )-alkenyl, substituted (C 2 -C 6 )-alkenyl, benzyl or phenethyl;

R 5 is hydrogen or methyl;

R 6 is (C 1 -C 4 )-alkyl, phenyl or substituted phenyl;

R 7 is (C 1 -C 4 )-alkyl, phenyl or substituted phenyl;

m is 0, 1 or 2; and

n is 0 or 1 with a proviso that when D represents formula (IIa), m is 0.

2. The dyestuff according to claim 1 , wherein D derives from the following amines: 3,4-dichloroaniline, 2-trifluoromethyl-4-nitroaniline, 2-nitroaniline, 3-nitroaniline, 4-nitroaniline, 2-chloro-4-nitroaniline, 4-chloro-2-nitroaniline, 2-bromo-4-nitroaniline, 2-chloro-4-methylsulfonylaniline, 2,6-dichloro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitroaniline, 2,5-dichloro-4-nitroaniline, 2-cyano-4-nitroaniline, 2-cyano-6-chloro-4-nitroaniline, 2-cyano-6-bromo-4-nitroaniline, 2,4-dintroaniline, 2-chloro-4,6-dinitroaniline, 2-bromo-4,6-dinitroaniline, 2-amino-5-nitrothiazole, 2-amino-3,5-dinitrothiophene, 2-amino-5-nitrothiophene-3-carboxylic acid ethyl ester, 2-amino-3-cyano-4-chloro-5-formylthiophene, 2-amino-5-(4-nitrophenylazo)-thiophene-3-carbonitrile, 7-amino-5-nitrobenzoisothiazole, 2-amino-6-nitrobenzothiazole, 2-amino-6-methylsulfonyl-benzothiazole, 2-amino-6-thiocyanatobenzothiazole or 2-amino-6,7-dichlorobenzothiazole.

3. The dyestuff according to claim 1 , wherein

R 1 is hydrogen, methyl or —NHCOCH 3 ;

R 2 is hydrogen, chloro, methoxy or ethoxy;

R 3 is hydrogen or methyl;

R 4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, tert. -butyl, benzyl, —CH 2 —O—CH 2 — or —(CH 2 ) 2 —O—(CH 2 ) 2 -;

R 5 is hydrogen or methyl;

m is 0, 1 or 2;

n is 0 or 1.

4. The dyestuff according to claim 1 , wherein

R 1 is hydrogen, methyl or —NHCOCH 3 ;

R 2 is hydrogen, chloro, methoxy or ethoxy;

R 3 is hydrogen or methyl;

R 4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, tert. -butyl, benzyl, —CH 2 —O—CH 2 — or —(CH 2 ) 2 —O—(CH 2 ) 2 -;

R 5 is hydrogen or methyl;

m is 1 or 2;

n is 0 or 1.

5. The dyestuff according to claim 2 , wherein

R 1 is hydrogen, methyl or —NHCOCH 3 ;

R 2 is hydrogen, chloro, methoxy or ethoxy;

R 3 is hydrogen or methyl;

R 4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, tert. -butyl, benzyl, —CH 2 —O—CH 2 — or —(CH 2 ) 2 —O—(CH 2 ) 2 —;

R 5 is hydrogen or methyl;

m is 1 or 2;

n is 0 or 1.

6. The dyestuff according to claim 1 , wherein m is 2 and n is 0.

7. The dyestuff according to claim 1 , wherein m is 2,

n is 0 and

D is of the formula (IIb).

8. The dyestuff according to claim 1 , wherein

m is 2,

n is 0,

D is of the formula (IIc) and

G 7 is hydrogen.

9. The dyestuff according to claim 1 , wherein

m is 2,

n is 0 and

D is of the formula (IId).

10. The dyestuff according to claim 1 , wherein

m is 2,

n is 0 and

D is of the formula (IIe).

11. The dyestuff according to claim 1 , wherein

m is 2,

n is 0 and

D is of the formula (IIf).

12. A process for the preparation of the dyestuff as claimed in claim 1 , which comprises diazotisation of an amine of the formula (III)

D-NH 2   (III)

wherein D is of the formula (IIa), (IIb), (IIe), (IId), (IIe) or (IIf);

and coupling onto a compound of the formula (IV)

wherein

R 1 is hydrogen, (C 1 -C 4 )-alkyl, hydroxy, —NHCOR 6 or —NHSO 2 R 6 ;

R 2 is hydrogen, halogen or (C 1 -C 4 )-alkoxy;

R 3 is hydrogen or methyl;

R 4 is hydrogen, (C 1 -C 6 )-alkyl, substituted (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkyl, which is interrupted by 1, 2 or 3 heteroatoms wherein said heteroatoms are —O—, —S— or —NR 7 , substituted (C 2 -C 6 )-alkyl, which is interrupted by 1, 2 or 3 heteroatoms wherein said heteroatoms are —O—, —S— or —NR 7 , (C 2 -C 6 )-alkenyl, substituted (C 2 -C 6 )-alkenyl, benzyl or phenethyl;

R 5 is hydrogen or methyl;

R 6 is (C 1 -C 4 )-alkyl, phenyl or substituted phenyl;

R 7 is (C 1 -C 4 )-alkyl, phenyl or substituted phenyl;

m is 0, 1 or 2; and

n is 0 or 1 with a proviso that when D represents formula (IIa), m is 0.

13. The process as claimed in claim 12 , wherein D is of the formula (IIa)

wherein

G 1 is hydrogen, halogen, cyano or nitro;

G 2 is hydrogen, halogen or nitro;

G 3 is hydrogen, halogen, methylsulfonyl, fluorosulfonyl or nitro; and

G 4 is hydrogen, halogen, trifluoromethyl, cyano or nitro;

or of the formula (IIb)

wherein

G 5 is hydrogen or halogen; and

G 6 is hydrogen, halogen, nitro, —SO 2 CH 3 or —SCN;

or of the formula (IIc)

wherein

G 7 is hydrogen or halogen;

or of the formula (IId)

wherein

G 8 is nitro, cyano, —CHO or a group of the formula (IIe)

wherein G 11 and G 12 are independently hydrogen, halogen, nitro or cyano;

G 9 is hydrogen or halogen; and

G 10 is nitro, cyano, —COCH 3 or —COO—G 13 , wherein G 13 is C 1 -C 4 alkyl;

or of the fomula (IIf)

m is 2 and

n is 0 with a proviso that when D represents formula (IIa), m is 0.

14. A process for dyeing and printing of synthetic textile material and fibre blends thereof which comprises contacting the material with the dyestuff as claimed in claim 1 .

15. An ink for injet printing which contains at least one dyestuff of the formula (I) according to claim 1 .