POLYESTERS, POLYCARBONATE, AND POLYURETHANES FROM A NOVEL MONOMER - ALPHA, ALPHA, ALPHA', ALPHA'-TETRAMETHYL-1, 4-TETRAFLUOROBENZENEDIMETHANOL

The novel diol monomer, pha'-tetramethyl-1,4-tetrafluorobenzenedimetha nol, has been synthesized by a convenient route which involves the add ition of acetone to 1,4-dilithiotetrafluorobenzene and can be purified by washing with hexanes. It does not directly undergo condensation po lymerizations with diacid chlorides. Its disodium salt, prepared by it s reaction with sodium hydride, similarly fails to undergo such polyme rizations readily. However, the dilithium salt, prepared in situ by th e reaction of the title diol with 2 equiv of n-butyllithium in tetrahy drofuran, is suitable for the preparation of various classes of conden sation polymers. Four polyesters and one polycarbonate derived from th e reactions of the dilithium salt of the diol with adipoyl dichloride, sebacoyl dichloride, isophthaloyl dichloride, terephthaloyl dichlorid e, and phosgene and two polyurethanes derived from its reactions with tolylene-2,4-diisocyanate and methylene-di-1,4-phenyl diisocyanate wer e prepared. Each was fully characterized by GPC, NMR, IR, and UV-visib le spectroscopies, and the results of these studies are reported herei n.