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

A new triphenylamine-containing aromatic dicarboxylic acid, N,N-bis(4- carboxyphenyl)-N,N-diphenyl-1,4-phenylenediamine, was synthesized by the conden- sation of N,N-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 transpar- ent, tough, and flexible films with good mechanical properties. They had useful levels of thermal stability associated with glass-transition temperatures up to 280 °C, 10% weight-loss temperatures in excess of 575 °C, and char yields at 800 °C in nitrogen higher than 60%. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 94 -105,