Reaction Product of Poly(ethyl vinyl malonate) and Aniline, and Polymeric Azo Dyes Derived from the Product

Abstract

In an attempt to deepen the color shade and to improve light-fastness of polymeric azo dyes (named, polymeric dye E), which were prepared by reactions of poly (ethyl vinyl malonate) [l] with aromatic diazonium salts, new polymeric azo dyes (named, polymeric dye A) containing anilide groups were synthesized by coupling of polymer [3] which was obtained by reaction of [l] with aniline, with aromatic diazonium salts in the presence of sodium acetate in dimethylformamide. It was presumed by infrared spectra that polymer C3D was consisted of a terpolymer of vinyl malonanilate, ethyl vinyl malonate and vinyl alcohol, and that polymeric dye A was consisted of a terpolymer of vinyl mesoxylanilate arylhydrazone, ethyl vinyl meso- xalate arylhydrazone and vinyl alcohol. Both the amounts of vinyl malonanilate part in [3] and of chromophore (ArNH-N.) in polymeric dye A were estimated by nitrogen analysis. The following polymeric dyes were prepared, namely, aryl group -=C6I-1 yellow; 4-CH3C6H4, yellow; 3-CH3C6H4, orange-yellow; 2-CH3C6H4, yellow; 2-CH3OC6F14, orange; 4-C106I-14, orange; 4- CHP-2-NO, C, H3, orange; 2-CHs-5-NO2C61-13, brown; 4-C1-13-2-NO2C6H8, orange; aCH io--7, dark-brown; 8-C10H7, brown.
All of these products were bathochromic as compared with polymeric dye E, but the lightfastness was scarcely improved.