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

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 T (g)s 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 T (g)s of 182-183 A degrees C, but also moderate T (m)s of 341-343 A degrees C, having good potential for melt processing and exhibited high thermal stability and good resistance to common organic solvents.