Synthesis of Novel Polyurethanes and Polyureas by Polyaddition Reactions of Dianhydrohexitol Configurated Diisocyanates

Abstract

The 2,5-diamino compounds of the three isomeric 1,4 : 3,6-dianhydrohexitols with D-gluco- (1), D-manno- (2) and L-ido (3) configuration were efficiently transformed into the corresponding diisocyanates 7, 8 and 10 as well as the L-ido diisothiocyanate 9 by a hot phosgenation procedure. Catalytic homogenous polyaddition procedures yielded various novel carbohydrate-derived polyurethanes and polyureas. The polymers were characterized using IR and 1H/ 13C NMR spectroscopy, viscosimetry and DSC. Number-average molecular weights were obtained from gel-permeation chromatography to be M̄n 8 900–20 600 g/mol.