Synthesis and characterization of new polyamides containing symmetrical and unsymmetrical thiadiazole rings

Abstract

Diamino derivatives of thiadiazole namely, 2,5-diamino-1,3,4-thiadiazole and 3,5-diamino-1,2,4-thiadiazole were synthesized and characterized. Polyamides were synthesized by condensation of the two diamino derivatives with diacide chlorides. The structures of polyamides were verified by elemental analysis, FTIR, 1H-NMR, 13C-NMR and mass spectroscopy. The polyamides possess good solubility in aprotic organic solvents such as DMF, DMAC, DMSO and NMP at room temperature. Intrinsic viscosity measurements indicate that the polyamides synthesized have moderate molecular weights. The thermal stability of these polyamides in nitrogen atmosphere is relatively good, especially for those polyamides containing phenylene ring in the backbone. Compared to the structurally related Kevlar aramide, using 2,5-diamino-1,3,4-thiadiazole and 3,5-diamino-1,2,4-thiadiazole instead of p-phenylene diamine results in reducing the melting points of polyamides to below 350 °C.