Synthesis and characterization of new soluble cardo polyesters derived from 1,1-bis-[4-(4-chlorocarboxyphenoxy)phenyl]-4-tert-butylcyclohexane with various bisphenols by solution polycondensation

Anew cardo diacid chloride, 1,1-bis-[4-(4-chlorocarboxyphenoxy)phenyll-4-te rt-butylcyclohexane (4), was synthesized from 1,1-bis-[4-(4-carboxyphenoxy) phenyl]-4-tert-butylcyclohexane in refluxing thionyl chloride. Subsequently , various new polyesters were prepared from 4 with various bisphenols by so lution polycondensation in nitrobenzene using pyridine as a hydrogen chlori de quencher at 150 degreesC. These polyesters were produced with inherent v iscosities of 0.32-0.50 dL.g(-1). Most of these polyesters exhibited excell ent solubility in a variety of solvents such as N,N-dimethylformamide, totr ahydrofuran, tetrachloroethane, dimethyl sulfoxide, N,N-dimethylacetamide, N-methyl-2-pyrrolidinone, m-cresol, o-chlorophenol, and chloroform. These p olymers showed glass-transition temperatures (Tg's) between 144 and 197 deg reesC. The polymer containing the adamantane group exhibited the highest T- g value. The 10% weight loss temperatures of the polyesters, measured by th ermogravimetric analysis, were found to be in the range of 426-451 degreesC in nitrogen. These cardo polyesters exhibited higher T-g's and better solu bility than bisphenol A-based polyesters. (C) 2001 John Wiley & Sons, Inc.