Azopyridone disperse dyes, their preparation and use

1. A dye of the general formula (I)

where

D is the residue of a diazo component;

X is (C i -C 6 )-alkylene or oxygen-interrupted (C 2 -C 6 )-alkylene;

R 1 is methyl, ethyl or phenyl;

R 2 is hydrogen, cyano or carboxamido;

R 3 is phenyl or substituted phenyl;

R 4 is hydrogen or methyl or R 3 and R 4 combine with the atoms to which they are attached to form a five- or six- membered ring.

2. The dye as claimed in claim 1 wherein D represents a group of the general formula (IIa)

where

T 1 , T 2 and T 3 are independently hydrogen, halogen, —SCN, hydroxyl, (C 1 -C 4 )-alkyl, (C 1 -C 6 )-alkoxy, substituted (C 1 -C 6 )-alkoxy, phenoxy, cyano, —SO 2 (C 1 -C 6 )-alkyl, —OSO 2 (C 1 -C 6 )-alkyl, —SO 2 aryl, —OSO 2 aryl, —OCO(C 1 -C 6 )-alkyl, —OCOaryl, —OCO 2 (C 1 -C 6 -alkyl), —OCO 2 aryl, —CO 2 (C 1 -C 8 -alkyl), —CO 2 (C 1 -C 8 )-alkyl where the alkyl radical is substituted, —CO 2 (C 1 -C 8 )-alkyl where the alkyl radical is oxygen interrupted, —CO 2 (C 1 -C 8 )-alkyl where the alkyl radical is oxygen interrupted and substituted, —CO 2 aryl, —NHCO(C 1 -C 8 -alkyl), —NHCO(C 1 -C 8 )-alkyl where the alkyl radical is oxygen interrupted, —CONH(C 1 -C 8 -alkyl), —CONH(C 1 -C 8 )-alkyl where the alkyl radical is oxygen interrupted, —NHSO 2 (C 1 -C 8 -alkyl), —SO 2 NH(C 1 -C 8 -alkyl), trifluoromethyl, trifluoromethylsulfonyl, trifluoromethoxy or nitro; and

T 4 independently of T 1 to T 3 is hydrogen, hydroxyl, halogen, trifluoromethyl, cyano, —SO 2 CH 3 , —SCN or nitro;

or represents a group of the general formula (IIb)

where T 5 is hydrogen or bromine;

or represents a group of the formula (IIc)

3. The dye as claimed in claim 1 , wherein

X is methylene, ethylene, propylene, butylene or pentylene;

R 1 is methyl;

R 2 is cyano;

R 3 is phenyl, 4-chlorophenyl or 4-methoxyphenyl; and

R 4 is hydrogen.

4. The dye as claimed in claim 2 , wherein

X is methylene, ethylene, propylene, butylene or pentylene;

R 1 is methyl;

R 2 is cyano;

R 3 is phenyl, 4-chlorophenyl or 4-methoxyphenyl; and

R 4 is hydrogen.

5. The dye as claimed in claim 2 , conforming to the general formula (Ia)

where T 1 to T 4 , R 1 , R 3 and X are each as defined in claim 2 .

6. The dye as claimed in claim 5 , conforming to the general formula (Iaa)

where

T 1 , T 2 and T 3 are independently hydrogen, nitro, methyl, methoxy, ethoxy, propoxy, phenoxy, hydroxyl, cyano, chloro, trifluoromethyl, bromine, methyl, ethyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, methylsulfonyloxy, ethylsulfonyloxy, phenylsulfonyloxy, —CO 2 (C 1 -C 8 -alkyl), —CO 2 (C 1 -C 8 )-alkyl where the alkyl radical is substituted, —CO 2 (C 1 -C 8 )-alkyl where the alkyl radical is oxygen interrupted, —CO 2 (C 1 -C 8 )-alkyl where the alkyl radical is oxygen interrupted and substituted, substituted (C 1 -C 8 -(oxygen-interrupted alkyl))oxycarbonyl or (C 1 -C 8 -alkylamino)carbonyl, (C 1 -C 8 -alkylamino)sulfonyl;

T 4 is hydrogen, cyano, nitro, chlorine, bromine, or trifluoromethyl;

X is methylene, ethylene, propylene, butylene or pentylene.

7. The dye as claimed in claim 2 conforming to the general formula (Ib)

where

T 5 is hydrogen or bromine;

X is (C 1 -C 6 )-alkylene or oxygen-interrupted (C 2 -C 6 )-alkylene; and

R 3 is phenyl or substituted phenyl,

or the general formula (Ic),

wherein

X is (C 1 -C 6 )-alkylene or oxygen-interrupted (C 2 -C 6 )-alkylene; and

R 3 is phenyl or substituted phenyl.

8. A process for preparing the dye of the general formula (I) as claimed in claim 1 , which comprises reacting a compound of the general formula (V)

where R I , R 2 , D and X are each as defined in claim 1 , with a haloketone of the general formula (VI)

where Y is chlorine or bromine and R 3 and R 4 are each as defined in claim 1 .

9. A process for dyeing and printing a hydrophobic material which comprises contacting the material with the dye of the general formula (I) as claimed in claim 1 .

10. An ink for digital textile printing by the ink jet process, comprising the dye of the general formula (I) as claimed in claim 1 .