Phthalimidyl azo dyes, process for the preparation thereof and the use thereof
View Patent ↗The present invention relates to dyes of formula (I) wherein R is hydrogen or bromine, R 1 is hydrogen, methyl or —NHCO—C 1 –C 4 alkyl, R 2 is C 1 –C 4 alkyl substituted by C 1 –C 4 alkoxy and R 3 has, independently of R 2 , any of the meanings of R 2 , and to the process for the preparation thereof and to the use thereof in dyeing or printing semi-synthetic and especially synthetic hydrophobic fiber materials, especially textile materials.
1. A dye of formula
wherein R is hydrogen or bromine, R 1 is hydrogen, methyl or —NHCO—C 1 –C 4 alkyl, R 2 is C 1 –C 4 alkyl substituted by C 1 –C 4 alkoxy and R 3 has, independently of R 2 , any of the meanings of R 2 .
2. A dye according to claim 1 , wherein R 1 is —NHCO—C 1 –C 4 alkyl.
3. A dye according to claim 1 , wherein R 2 and R 3 have the same meaning and are the radical —CH 2 CH 2 —OCH 3 .
4. Dye according to claim 1 of formula
5. Dye according to claim 1 of formula
6. A process for the preparation of a dye of formula (1) according to claim 1 , in which process a phthalimide of formula
is nitrated in the acid range, the resulting nitro compound is then alkylated and, by means of reductive treatment, converted into an intermediate of formula
the intermediate of formula (51) is mono- or di-halogenated in an acid medium, and the resulting compound is then diazotised and is coupled to a compound of formula
wherein R 1 , R 2 and R 3 are as defined for formula (1).
7. A dye mixture comprising at least one azo dye of formula (1) according to claim 1 and at least one azo dye of formula
wherein R 1 is hydrogen, methyl or —NHCO—C 1 –C 4 alkyl, R 2 is C 1 –C 4 alkyl, it being possible for the alkyl chain, from C 2 upwards, optionally to be interrupted by an oxygen atom, and R 3 has, independently of R 2 , any of the meanings of R 2 .
8. A process for dyeing or printing semi-synthetic or synthetic hydrophobic fibre materials, comprising applying to the said materials or incorporating into said materials a dye of formula (1) according to claim 1 .
9. A semi-synthetic or synthetic hydrophobic fibre material, dyed or printed by the process according to claim 8 .
10. A dye according to claim 2 , wherein R 2 and R 3 have the same meaning and are the radical —CH 2 CH 2 —OCH 3 .
11. A process for dyeing or printing semi-synthetic or synthetic hydrophobic fibre materials, comprising applying to the said materials or incorporating into said materials a dye mixture according to claim 7 .