Perylene amidine imide dyes, a process for preparing them, and their use
AssigneeCiba-Geigy Corporation
InventorHeinz Langhals
Life of this patent
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Abstract
Certain perylene-3,4:9,10-tetracarboxylic monoanhydride monoimides are condensed with primary diamines or with imidazoles. The products obtained are amidine imides of the formula I ##STR1## where, for example, R.sub.1 is 1-hexylheptyl, R.sub.2 to R.sub.5 are each H and A is 1,2-phenylene. Compounds of the formula I are very light-fast dyes which show strong fluorescence in solution and whose fluorescence occurs at a longer wavelength than that of the bisimides (perylene dyes). The perylene amidine imides of the invention are suitable for example for use as colorants for the mass coloration of macromolecular organic material, as fluorescent dyes or as photoconductors.
Claims13
A perylene amidine imide of the formula I ##STR24## where R.sub.1 is a secondary C.sub.7 -C.sub.41 alkyl radical or a radical of the formula II ##STR25## where R is a branched C.sub.3 -C.sub.8 alkyl radical and m is 1, 2 or 3;
- A is C.sub.5 -C.sub.7 cycloalkylene, phenylene, naphthylene, pyridylene, a more highly fused aromatic carbocyclic or heterocyclic radical or a bivalent radical of the formula III, IV or V ##STR26## and R.sub.1 and A may each be substituted by halogen, alkyl, cyano or nitro;
- R.sub.2 to R.sub.5 are each independently of the others hydrogen, alkyl, aryl, hetaryl, halogen, cyano, nitro, --OR.sub.8, --COR.sub.8, --COOR.sub.8, --OCOR.sub.8, --CONR.sub.8 R.sub.9, --OCONR.sub.8 R.sub.9, --NR.sub.8 R.sub.9, --NR.sub.8 COR.sub.9, --NR.sub.8 COOR.sub.9, --NR.sub.8 SO.sub.2 R.sub.9, --SO.sub.2 R.sub.8, --SO.sub.3 R.sub.8, --SO.sub.2 NR.sub.8 R.sub.9 or --N.dbd.N--R.sub.8 ;
- and R.sub.6 to R.sub.9 are each independently of the others C.sub.1 -C.sub.4 alkyl, phenyl or 4-tolyl.
Dependencies are inferred from the claim text.