PREPARATION AND PROPERTIES OF AROMATIC POLYAMIDES AND POLYIMIDES DERIVED FROM 3,3-BIS[4-(4-AMINOPHENOXY)PHENYL]PHTHALIDE

3,3-Bis [4-(4-aminophenoxy) phenyl] phthalide (II) was used as a monomer with various aromatic dicarboxylic acids and dianhydrides to synthesize polyamides and polyimides, respectively. The diamine II was derived by a nucleophilic substitution of phenolphthalein with p -chloronitrobenzene in the presence of K2CO3. Polyamides IV(a-g) having inherent viscosities of 0.77-2.46 dL/g were prepared by the direct polycondensation of diamine II with diacids III(a-g) using triphenyl phosphite and pyridine as condensing agents. The polyamides were readily soluble in a variety of solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), and N-methyl-2-pyrrolidinone (NMP) and afforded transparent and flexible films from the polymer solutions. These polymers had glass transition temperatures (T(g)s) in the 227-307-degrees-C range and 10% weight loss temperatures occurred up to 450-degrees-C. Polyimides VI(a-e) based on diamine II and various aromatic dianhydrides V(a-e) were synthesized by the two-stage procedure that included ring-opening, followed by thermal or chemical conversion to polyimides. Most of the polyimides obtained by chemical cyclodehydration procedure were found to soluble in DMF, NMP, o-chlorophenol, and m-cresol. The T(g)s of these polyimides were in the 260-328-degrees-C range and showed almost no weight loss up to 500-degrees-C under air and nitrogen atmosphere. (C) 1994 John Wiley & Sons, Inc.