Guey‐Sheng Liou, S. Hsiao, Wen‐Chang Chen
Aug 10, 2006
Citations
1
Influential Citations
59
Citations
Journal
Macromolecules
Abstract
A new naphthylamine-derived aromatic dicarboxylic acid, 1-[N,N-di(4-carboxyphenyl)amino]naphthalene (2), was successfully synthesized by the sodium hydride-mediated condensation of 1-aminonaphthalene with 4-fluorobenzonitrile, followed by the alkaline hydrolysis of the intermediate dicyano compound 1. Four poly(amine−hydrazide)s were prepared from the polycondensation reactions of the dicarboxylic acid 2 and 4,4‘-dicarboxytriphenylamine (2‘) with terephthalic dihydrazide (TPH) and isophthalic dihydrazide (IPH), respectively, via the Yamazaki phosphorylation reaction. The poly(amine−hydrazide)s were readily soluble in many common organic solvents and could be solution cast into transparent and flexible films with good mechanical properties. These hydrazide polymers had glass-transition temperatures (Tg) in the range of 182−230 °C and could be thermally cyclodehydrated into the corresponding oxadiazole polymers in the range of 300−400 °C. The resulting poly(amine−1,3,4-oxadiazole)s had useful levels of ther...