Polyesters, polyurethanes, and epoxy resin derived from 2,2′‐(1,4‐phenylenedivinylene)bis‐5‐hydroxypyridine

Abstract

Abstract2,2′‐(1,4‐Phenylenedivinylene)bis‐5‐hydroxypyridine (PBHP) was used as a starting material for preparing new polyesters and polyurethanes as well as a diepoxide‐bearing styrylpyridine segments. The diesters were prepared by reacting PBHP with terephthaloyl or adipoyl dichloride utilizing the interfacial polycondensation method. The diesters were prepared from the reaction of PBHP with tolylene diisocyanate or methylenebis(4‐phenylisocyanate). In addition, a model diester and diurethane were synthesized by reacting PBHP with benzoyl chloride and phenyl isocyanate, respectively. Both model compounds and polymers were characterized by IR and 1H‐NMR spectroscopy, as well as by DTA and TGA. A diepoxide was also prepared from the reaction of PBHP with epichlorohydrin which was polymerized in the presence of 4,4′‐diaminodiphenylsulfone. The polyester derived from PBHP and terephthaloyl dichloride was the most thermostable polymer obtained. It was stable in N2 up to 355°C and afforded an anaerobic char yield of 59% at 800°C. The thermal stabilities of polymers were improved by curing.