Synthesis of aliphatic polyamides containing 4-phenylurazole linkages

4-Phenylurazole (1) was reacted with excess acetyl chloride in N,N-dimethylacetamide (DMAc) solution at room temperature. The reaction occurred in quantitative yield with acetylation of both of the N? H bonds of the urazole group. This compound was characterized by IR, ¹ H NMR and elemental analysis, and was used as a model compound for the polymerization reaction. Solution polymerization of monomer (1) with adipoyl chloride (AC) and suberoyl chloride (SC) was performed in DMAc and chloroform in the presence of pyridine, and lead to the formation of a novel aliphatic polyamide with an inherent viscosity in the range of 0.108–0.396 dl g^?1. When interfacial polymerization of monomer (1) with suberoyl chloride was performed in DMAc/cyclohexane, a lower viscosity resulted. The resulting polymers are soluble in most organic solvents. Some structural characterization and physical properties of these novel polymers are reported. © 1999 Society of Chemical Industry