Synthesis and characterization of soluble polyimides derived from 2′,5′-bis(3,4-dicarboxyphenoxy)-p -terphenyl dianhydride

Abstract

A novel bis(ether anhydride) monomer, 2′,5′-bis(3,4-dicarboxyphenoxy)-p-terphenyl dianhydride, was synthesized from the nitro displacement of 4-nitrophthalonitrile by the phenoxide ion of 2′,5′-dihydroxy-p-terphenyl, followed by alkaline hydrolysis of the intermediate bis(ether dinitrile) and cyclodehydration of the resulting bis(ether diacid). A series of new poly(ether imide)s bearing laterally attached p-terphenyl groups were prepared from the bis(ether anhydride) with various aromatic diamines via a conventional two-stage process that included ring-opening polyaddition to form the poly(amic acid)s followed by thermal or chemical imidization to the poly(ether imide)s. The inherent viscosities of the poly(amic acid) precursors were in the range of 0.62–1.26 dL/g. Most of the poly(ether imide)s obtained from both routes were soluble in polar organic solvents, such as N,N-dimethylacetamide. All the poly(ether imide)s could afford transparent, flexible, and strong films with high tensile strengths. The glass-transition temperatures of these poly(ether imide)s were recorded as between 214 and 276 °C by DSC. The softening temperatures of all the poly(ether imide) films stayed in the 207–265 °C range according to thermomechanical analysis. For all the polymers significant decomposition did not occur below 500 °C in nitrogen or air atmosphere. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 1008–1017, 2004