S. Hsiao, Chien-Wei Chen, Guey‐Sheng Liou
Jul 1, 2004
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Journal of Polymer Science Part A
Abstract
Two new diamines, 2,4-diaminotriphenylamine (3) and N-(2,4-diaminophe- nyl)carbazole (4), were synthesized via the cesium fluoride-mediated aromatic substi- tution reactions of 1-fluoro-2,4-dinitrobenzene with diphenylamine and carbazole, fol- lowed by palladium-catalyzed hydrazine reduction. Amorphous and soluble aramids having pendent diphenylamino and carbazolyl groups were prepared by the phosphor- ylation polycondensation of aromatic dicarboxylic acids with diamines 3 and 4, respec- tively. The aramids derived from diamine 3 had sufficiently high molecular weights to permit the casting of flexible and tough films. They exhibited excellent mechanical properties and moderately high softening temperatures in the 221-298 °C range. However, the reactions of diamine 4 with aromatic diacids gave relatively lower mo- lecular weights products that could not afford flexible films. For a comparative purpose, the parent aramids derived from m-phenylenediamine and aromatic diacids were also prepared and characterized. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3302-3313, 2004