INTRODUCTION OF AMINO, ALIPHATIC, AND ALIPHATIC CARBOXYLIC-ACID SIDE-GROUPS ONTO POLY(ARYLENE ETHER SULFONE)S VIA TRANSIMIDIZATION REACTIONS

A versatile approach for the functionalization of a bisphenolic monome r, ,8-bis(4-hydroxyphenyl)-N-phenyl-1,2-naphthalimide (1) as well as i ts corresponding poly(N-phenyl imido aryl ether sulphone) via transimi dization reactions with hydrazine monohydrate, aliphatic amines, and a n amino acid (11-amino undecanoic acid) is reported. The reactions pro ceeded in high conversion and high isolated yield to the desired novel functionalized monomers or polymers with N-amino, N-aliphatic, and N- aliphatic acid pendant groups. The N-amino functionalized monomer, 2, was reacted cleanly with naphthalic anhydride to form a bisimide. Poly mers with phthalimide (7), 3-carboxy phthalimide (9), and bisphenol-A- (monoimide monoanhydride) (8) pendant groups were also formed by imidi zation of 6. A polymer with a cyclopropyl amide functional group, 10, was formed by reacting 6 with cyclopropyl carbonyl chloride. A brief d escription of the transimidization reactions and the properties of the functionalized polymers is included. (C) 1997 John Wiley & Sons, Inc.