Synthesis and properties of polyimides derived from 1,7-bis(4-aminophenoxy)naphthalene and aromatic tetracarboxylic dianhydrides

The novel diamine, 1,7-bis(4-aminophenoxy)naphthalene (1,7-BAPON), was synthesized and used to prepared polyimides. 1,7-BAPON was synthesized through the nucleophilic displacement of 1,7-dihydroxynaphthalene with p-fluoronitrobenzene in the presence of K₂CO₃ followed by catalytic-reduction. Polyimides were prepared from 1,7-BAPON and various aromatic tetracarboxylic dianhydrides by the usual two-step procedure that included ring-opening polyaddition to give poly(amic acid)s, followed by cyclodehydration to polyimides. The poly(amic acid)s had inherent viscosities of 0.74-2.48 dL/g. Most of the polyimides formed tough, creasible films. These polyimides had glass transition temperatures between 247–278°C and their 10% weight loss temperatures were recorded in the range of 515–575°C in nitrogen atmosphere. © 1995 John Wiley & Sons, Inc.