Organosoluble optically transparent poly(ether imide)s based on atert-butylhydroquinone bis(ether anhydride)

Abstract

Full Paper: A novel bis(ether anhydride) monomer, 1,4-bis(3,4-dicarboxyphenoxy)-2-tert-butylbenzene dianhydride, was synthesized from the nitro displacement of 4-nitrophthalodinitrile by the phenoxide ion of tert-butylhydroquinone, followed by alkaline hydrolysis of the intermediate bis(ether dinitrile) and dehydration of the resulting bis(ether diacid). A series of colorless and organosoluble poly(ether imide)s (PEIs) bearing pendent tert-butyl 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 chemical or thermal cyclodehydration to the PEIs. The inherent viscosities of these PEIs are in the range of 0.70-1.44 dL/g. Most PEIs show excellent solubilities in amide polar solvents, m-cresol and chlorohydrocarbons. The glass transition temperatures (T g ) of these PEIs were recorded between 217-278°C, and the decomposition temperatures at 10% weight loss are all above 460°C in air or nitrogen atmosphere. Solvent-cast films have high tensile moduli and strengths. The PEIs obtained from long chain diamines exhibit high extension to break.