Synthesis and properties of cross-linkable poly(arylene ether nitrile)s containing side propenyl groups

Abstract

Cross-linkable poly(arylene ether nitrile)s containing side propenyl groups (DPEN) were synthesized through nucleophilic aromatic substitution polymerization from biphenol, 2,2′-diallylbisphenol A (DBA), and 2,6-dichlorobenzonitrile. The structures of resultant copolymers were characterized by Fourier transform infrared and proton nuclear magnetic resonance spectroscopies. The properties of copolymers were investigated by thermal (differential scanning calorimetry and thermogravimetric analysis) analysis, inherent viscosity measurements, and mechanical tests. The results showed that allyl groups rearranged into propenyl groups during the polymerization. The copolymers with increasing content of DBA had high glass transition temperatures ranging from 207°C to 169°C and good thermal and thermo-oxidative stability with the 5 wt% loss temperatures in the range of 511–423°C under nitrogen and 471–402°C in air atmospheres, respectively. They also exhibited good mechanical property with tensile strength of 105–79 MPa. Meanwhile, the cross-linking reaction was studied through heat treatment. The result showed that the properties of DPEN containing side propenyl groups changed obviously after heat treatment, due to the fact that the double bond of PEN can be readily cross-linked to form net-shape polymers at high temperature.