Synthesis of isosorbide based polyurethanes: An isocyanate free method

Abstract

The synthesis of isocyanate free polyurethanes is a major concern. This paper first reports the synthesis of new biobased isosorbide dicyclocarbonates from isosorbide. Then polyhydroxyurethanes (PHUs) were synthesized by a cyclocarbonate-amine step growth polyaddition with four commercial diamines (e.g. jeffamine D-400, 1,10 diaminodecane, diethylenetriamine and isophoronediamine). These unprecedented products, obtained with high yield, were characterized by 1H NMR, FTIR, DSC, SEC and TGA analyses. PHUs exhibited glass transition temperatures from -8 °C to 59 °C, and degradation temperatures (Td 5%) between 234 °C and 255 °C. Last but not least, the compounds produced during the degradation of these PHUs were analyzed by ATG-IR technique and showed that carbon dioxide and secondary amines are released. © 2013 Elsevier Ltd. All rights reserved.