Synthesis and Characterization of Isomeric Biphenyl Containing Poly(aryl ether-bisketone)s II. Polymers Derived from 3, 3′-(4-Fluorobenzoyl)biphenyl and Bisphenols

A series of amorphous and semicrystalline poly(aryl ether-bisketone)s have been synthesized from bisphenols and 3, 3′-(4-fluorobenzoyl)biphenyl via nucleophilic aromatic substitution reactions. Model compound studies were carried out with a variety of substituted phenols, 3, 3′-(4-fluorobenzoyl)biphenyl and 3, 3′-(4-chlorobenzoyl)biphenyl. The bishalide monomers were prepared by the reaction of 3, 3′-biphenyl dicarboxylic acid with thionyl chloride followed by Friedel–Crafts reaction with the appropriate aryl halide. Potassium carbonate mediated reaction of these monomers with a variety of bisphenols in dimethylacetamide or diphenylsulfone gave moderate to high molecular weight polymers in excellent yield. The high molecular weight polymers afforded tough films by compression molding. The glass transition temperatures, melting points and the thermal behaviors of the polymers were compared with the corresponding polymers derived from 4, 4′-(4-fluorobenzoyl)biphenyl.