Synthesis and characterization of novel 1,2,3-triazole-bridged oxime polyurethanes obtained from an isomannide derivative

Abstract

Polyurethanes (PUs) are synthesized by the reaction of diisocyanates and diols and are widely used in furniture foams, thermal insulation, coatings, and adhesives. In this work, a 1,2,3-triazole-bridged dioxime (compound 6) as a diol source was synthesized from isomannide via tosylation, azidation, and cyclization-addition and used in the syntheses of new PUs. A new carbohydrate-based linear P-1 was synthesized by the reaction of 6 and 1,6-hexamethylene diisocyanate (1,6-HMDI). Besides, three new linear PUs (P-2, P-3, and P-4) were synthesized by the reaction of 6, isomannide compound (used in different molar ratios), and 1,6-HMDI. The thermal properties of the new PUs were determined by thermogravimetry (TG), their molecular structures were characterized by FTIR, 1H- and 13C-NMR, and the molecular weights of some polymers were determined by GPC/SEC. Additionally, the surface characteristics of the synthesized PUs were examined via scanning electron microscopy (SEM).