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

Abstract

A new monomer, bis[4-(p-phenoxybenzoyl)-1,2-benzenedioyl]-N,N,N′,N′-4,4′-diaminodiphenyl sulfone (BPBDADPS), was prepared by the Friedel–Crafts reaction of bis(4-chloroformyl-1,2-benzenedioyl)-N,N,N′,N′-4,4′-diaminodiphenyl sulfone (BCBDADPS) with diphenyl ether (DPE). Novel poly(aryl ether ketone)s containing sulfone and imide linkages in the main chains (PAEKSI) were synthesized by electrophilic solution polycondensation of terephthaloyl chloride (TPC) with a mixture of DPE and BPBDADPS under mild conditions. The copolymers obtained were characterized by different physico-chemical techniques. The copolymers with 10–30 mol% BPBDADPS are semi-crystalline and had remarkably increased Tg values over commercially available PEEK and PEKK due to the incorporation of sulfone and imide linkages in the main chains. The copolymers III and IV with 20–30 mol% BPBDADPS had not only high Tg values of 180–187 °C, but also moderate Tm values of 338–341 °C, having good potential for the melt processing. The copolymers III and IV had tensile strengths of 100.7–104.2 MPa, Young’s moduli of 2.31–2.44 GPa, and elongations at break of 12.2–14.7% and exhibited high thermal stability and good resistance to organic solvents.