Polyesters, polyurethanes and epoxy resins derived from 2,2′‐(1,4‐phenylenedivinylene)bis‐8‐hydroxyquinaldine and 6‐(4‐hydroxystyryl)‐3‐hydroxypyridine

Abstract

New polyesters and polyurethanes as well as diepoxides bearing styrylpyridine segments were prepared utilizing 2,2′‐(1,4‐phenylenedivinylene)bis‐8‐hydroxyquinaldine (PBHQ) and 6‐(4‐hydroxystyryl)‐3‐hydroxypyridine (HSHP) as starting materials. The polyesters were prepared by reacting PBHQ or HSHP with terephthaloyl dichloride in the presence of an acid acceptor utilizing the solution polycondensation method. The polyurethanes were prepared from the reactions of PBHQ and HSHP with tolylene diisocyanate and methylenebis(4‐phenylisocyanate). In addition, model diesters and diurethanes were synthesized by reacting PBHQ and HSHP with benzoyl chloride and phenyl isocyanate, respectively. Model compounds and polymers were characterized by FT‐IR and ¹H‐NMR spectroscopy as well as by DTA and TGA. Diepoxides were also prepared from the reactions of PBHQ and HSHP with epichlorohydrin which were polymerized in the presence of 4,4′‐diaminodiphenylsulfone. The polyesters were the most thermostable polymers obtained. After curing at 240°C for 20 h, they were stable in N₂ up to 345–370°C and afforded anaerobic char yields of 65–75% at 800°C. © 1993 John Wiley & Sons, Inc.