Synthesis and properties of new soluble triphenylamine-based aromatic poly(amine amide)s derived from N,N′-Bis(4-carboxyphenyl)-N,N′-diphenyl-1,4-phenylenediamine

A new triphenylamine-containing aromatic dicarboxylic acid, NN'-bis(4-carboxyphenyl)-N,N'-diphenyl-1,4-phenytenediamine, was synthesized by the condensation of NN'-diphenyl-1,4-phenylenediamine with 4-fluorobenzonitrile, followed by the alkaline hydrolysis of the intermediate dinitrile compound. A series of novel triphenylamine-based aromatic poly(amine amide)s with inherent viscosities of 0.50 - 1.02 dL/g were prepared from the diacid and various aromatic diamines by direct phosphorylation polycondensation. All the poly(amine amide)s were amorphous in nature, as evidenced by X-ray diffractograms. Most of the poly(amine amide)s were quite soluble in a variety of organic solvents and could be solution-cast into transparent, tough, and flexible films with good mechanical properties. They had useful levels of thermal stability associated with glass-transition temperatures up to 280 degreesC, 10% weight-loss temperatures in excess of 575 degreesC, and char yields at 800 degreesC in nitrogen higher than 60%. (C) 2002 Wiley Periodicals, Inc.