Azo dyes, a process for their preparation and their use in the production of colored plastics or polymeric color particles, and in the dyeing or printing of hydrophobic fiber materials
View Patent ↗The present invention relates to an azo dye of formula wherein D is the radical of a diazo component of the benzene, naphthalene, diphenyl, thiophene, benzothiazole, benzisothiazole, thiadiazole, indazole, benzotriazole, pyrazole, anthraquinone, naphthalic acid imide, chromone, phthalimide or diphenylene oxide series, R 1 is an unsubstituted or substituted aryl radical and R 2 is an unsubstituted or substituted aryl radical, with the exception of the compounds of formulae (1a) and (1b) to a process for its preparation and to its use in a process for the production of mass-colored plastics or polymeric color particles, and in the dyeing or printing of semi-synthetic or synthetic hydrophobic fiber materials.
1. An azo dye of formula
wherein
D is 2-trifluoromethyl-4-nitrophenyl, 2-cyano-4-nitrophenyl, 2-trifluoromethylphenyl, 2-trifluoromethyl-4-chlorophenyl, 2-cyano-4-nitro-6-chlorophenyl, 2-trifluoromethyl-4-nitro-6-bromophenyl, 2-phenoxysulfonylphenyl, 2-cyano-4-nitro-1-naphthyl, 2-nitro-4-phenylaminocarbonylphenyl, 2-(N-phenyl-N-ethylaminosulfonyl)phenyl, 2-nitro-4-phenoxysulfonylphenyl, 2-chloro-4-methylsulfonylphenyl, 2-phenylsulfonylphenyl, 2-nitro-4-methylsulfonylphenyl or 3,5-dicyano-4-methyl-2-thienyl and
R 1 and R 2 are m-tolyl, o-tolyl, p-tolyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,5-dimethylphenyl, mesityl or 4-methoxyphenyl.
2. An azo dye according to claim 1 of formula
3. A process for the preparation of an azo dye of formula (1) according to claim 1 , wherein a compound of formula
D-NH 2 (50)
is diazotised in accordance with a customary procedure and then coupled to a coupling component of formula
D, R 1 and R 2 being as defined in claim 1 .
4. A process for the preparation of coloured plastics or polymeric colour particles, which comprises mixing together a high molecular weight organic material and a tinctorially effective amount of at least one azo dye of formula (1).
5. A process for the dyeing or printing of semi-synthetic or synthetic hydrophobic fibre materials, wherein at least one dye of formula (1) according to claim 1 is applied to the said materials or is incorporated into those materials.
6. Plastics or polymeric colour particles coloured by the process according to claim 4 .
7. A semi-synthetic or synthetic hydrophobic fibre material dyed or printed by the process according to claim 5 .
8. An azo dye according to claim 1 wherein R 1 and R 2 denote p-tolyl.