Synthesis of glycerin carbonate-based intermediates using thiol-ene chemistry and isocyanate free polyhydroxyurethanes therefrom

Abstract

A new synthesis of 4-[(prop-2-en-1-yloxy)methyl]-1,3-dioxolan-2-one (AGC) was performed by Williamson ether synthesis from 4-(hydroxymethyl)-1,3-dioxolan- 2-one. Dicyclocarbonates were synthesized by UV thiol-ene coupling of allyl-cyclocarbonate with a 2,2′-oxydiethanethiol. This photochemical thiol-ene reaction was carried out under air, with neither solvent nor photoinitiator. The products, obtained with high yield, were characterized by 1 H NMR and FTIR analysis. The synthesized dicyclocarbonates were used without purification to synthesize polyhydroxyurethanes without isocyanate by step growth polyaddition with 1,10-diaminodecane. The synthesized polyhydroxyurethanes were characterized by 1 H NMR, FTIR, ATG and DSC analysis. These polyhydroxyurethanes exhibited glass transition temperatures from -31 °C to -14 °C, molecular weight from 7,000 g mol -1 to 9000 g mol -1 and degradation temperature for 5% of weight loss (T d 5%) between 227 °C and 250 °C. © The Royal Society of Chemistry.