Synthesis and characterization of new polyamides derived from 4-(4?-aminophenyl)urazole and aliphatic diacid chlorides

Abstract

4-(4′-Aminophenyl)urazole (AmPU) was prepared from 4-nitrobenzoic acid in six steps. The reaction of AmPU with acetyl chloride was performed in N,N-dimethylacetamide solutions at different ratios, and the resulting disubstituted and trisubstituted amide derivatives were obtained in high yields and were used as models for polymerization reactions. Polycondensation reactions of AmPU with succinyl chloride, suberoyl chloride, and sebacoyl chloride were performed with conventional solution polymerization techniques in the presence of different catalysts, such as pyridine, triethylamine, and dibutyltin dilaurate, and led to the formation of novel aliphatic polyamides. The resulting novel polyamides had inherent viscosities of 0.11–0.22 dL/g in dimethylformamide or H2SO4 at 25°C. These polyamides were characterized with IR, 1H-NMR, elemental analysis, and thermogravimetric analysis. Some physical properties and structural characterization of these novel polyamides are reported. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 92: 3173–3185, 2004