Structural analysis of polyhydroxyurethane obtained by polyaddition of bifunctional five-membered cyclic carbonate and diamine based on the model reaction

This article focuses on the structural analysis of polyhydroxyurethane obtained by the reaction of 2,2-bis[p-(1,3-dioxolan-2-one-4-yl-methoxy)phenyl]propane with a diamine based on the model reaction. The compounds obtained in the model reaction could be separated into hydroxyurethanes containing primary and secondary alcohol groups by preparative gel permeation chromatography with a recycling technique to determine the structures by 1H NMR, 13C NMR, distortionless enhancement by polarization transfer (DEPT) and CH correlation spectroscopy to obtain hydroxyurethane carrying the primary alcohol structure moiety dominantly. The ratios were independent of the reaction temperature but somewhat dependent on the solvents and amines.