Synthesis and properties of novel poly(aryl ether ketone)s containing imide linkages in the main chains

Abstract

A new monomer containing imide linkages, bis[4-(p-phenoxybenzoyl)-1,2-benzenedioyl]-N,N,N′,N′-4,4′-diaminodiphenyl ether (BPBDADPE), was prepared by the Friedel–Crafts reaction of bis(4-chloroformyl-1,2-benzenedioyl)-N,N,N′,N′-4,4′-diaminodiphenyl ether (BCBDADPE) with diphenyl ether (DPE). Novel poly(aryl ether ketone)s containing imide linkages in the main chains (PEK-I) were synthesized by electrophilic Friedel–Crafts solution copolycondensation of terephthaloyl chloride (TPC) with a mixture of DPE and BPBDADPE. The polymers were characterized by different physico-chemical techniques. The polymers with 10–40 mol% BPBDADPE are semicrystalline and had increased Tgs over commercially available poly(ether ether ketone) (PEEK) and poly(ether ketone ketone) (PEKK) (70/30) due to the incorporation of imide linkages in the main chains. The polymers IV and V with 30–40 mol% BPBDADPE had not only high Tgs of 182–183 °C, but also moderate Tms of 341–343 °C, having good potential for melt processing and exhibited high thermal stability and good resistance to common organic solvents.