Synthesis, characterization, and comparison of properties of new fluorinated poly(arylene ether)s containing phthalimidine moiety in the main chain

Abstract

Four new poly(arylene ether)s have been prepared by the reaction of N‐phenyl‐3,3‐bis(4‐hydroxyphenyl)phthalimidine (PA) with four different perfluoroalkylated monomers namely 1,3‐bis(4′‐fluoro‐3′‐trifluoromethyl benzyl) benzene, 4,4′‐bis(4′‐fluoro‐3′‐trifluoromethyl benzyl) biphenyl, 2,6‐bis(4′‐fluoro‐3′‐trifluoromethyl benzyl) pyridine, and 2,5‐bis(4′‐fluoro‐3′‐trifluoromethyl benzyl) thiophene. The poly(arylene ether)s were characterized by different spectroscopic, thermal, mechanical, and electrical techniques. The poly(arylene ether) containing quadriphenyl unit in the main chain showed very high glass transition temperature of 291°C and outstanding thermal stability upto 556°C for 10% weight loss under a 4:1 nitrogen:oxygen mixture. The polymers were soluble in a wide range of organic solvents. Transparent thin films of these polymers exhibited tensile strengths upto 75 MPa and elongation at break upto 32%. The films of these polymers showed low water absorption of 0.26%. Copyright © 2009 John Wiley & Sons, Ltd.

Fluorinated Poly(Arylene Ether)s

“…Banerjee et al [60,61] reported on PAEs with phthalimidine moiety (2-34 to 2-38) ( Table 2.4) with the aim of increasing both T g and thermo-oxidative stability and also improving solubility. The polymers had good solubility in polar aprotic solvents such as NMP, DMF, THF, and chloroform.…”

Carboxylic acid functionalized fluorinated sulfonated poly(arylene ether sulfone) copolymers with enhanced oxidative stability

“…The stressstrain behaviour of all the copolymer membranes is also shown inFigure 4. The -COOH functionalized non-sulfonated TPQ-COOH polymer exhibits higher tensile strength value (92 MPa) than that of previously reported phthalimidine based fluorinated homopolymer (PAQ, 75 MPa)[40]. For the sulfonated copolymers TPQSH-COOH-XX, in the dry state, the tensile strength value are gradually decreasing with the increase of the DS and the membranes show tensile stresses of 24-52 MPa, Young's modulus of 1.01-1.68 GPa, and elongation at break…”

Processable high Tg high strength fluorinated new poly(arylene ether)s containing imido aryl group

“…Poly(arylene ether)s 7a–7c exhibited good solubility in common organic solvents like other semifluorinated poly(arylene ether)s 20, 21. It was attempted to obtain 10% (w/v) solution of all polymers in several organic solvents.…”

“…In continuation of our research for the preparation of high temperature, high T g , and high strength materials, we designed number of new semifluorinated poly(arylene ether)s 20, 21. In this article we report six new poly(arylene ether)s derived from the polycondensation of six different fluorinated bisfluoro monomers with the imidoaryl biphenol ( 5 ).…”