Synthesis and properties of new soluble aromatic polyamines and polyimides on the basis of N,N′-bis(3-aminobenzoyl)-N,N′-diphenyl-1,4-phenylenediamine

A new N-phenylated amide (N-phenylamide) unit containing aromatic diamine, N,N'-bis(3-aminobenzoyl)-N,N'-diphenyl-1,4-phenylenediamine, was prepared by the condensation of N,N'-diphenyl-1,4-phenylenediamine with 3-nitrobenzoyl chloride, followed by catalytic reduction. Two series of organosoluble aromatic poly(N-phenylamide-imide)s and poly(N-phenylamide-amide)s with inherent viscosities of 0.58-0.82 and 0.56-1.21 dL/g were prepared by a conventional two-stage method and the direct phosphorylation polycondensation, respectively, from the diamine with various aromatic dianhydrides and aromatic dicarboxylic acids. All polyimides and polyamides are amorphous and readily soluble in many organic solvents such as N,N-dimethylacetamide and N-methyl-2-pyrrolidone. These polymers could be solution cast into transparent, tough, and flexible films with high tensile strengths. These polyimides and polyamides had glass-transition temperatures in the ranges of 230-258 and 196-229 degreesC, respectively. Decomposition temperatures of the polyimides for 10% weight loss all occurred above 500 degreesC in both nitrogen and air atmospheres. (C) 2002 Wiley Periodicals, Inc.