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

Sofia Benyahya (1) , Myriam Desroches (1) , Rémi Auvergne (1) , Stéphane Carlotti (2, 3) , Sylvain Caillol (1) , Bernard Boutevin (1)

1 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 LCPO - Laboratoire de Chimie des Polymères Organiques
3 Team 1 LCPO : Polymerization Catalyses & Engineering

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 2,20-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 1H 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 1H 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 to 9000 g/mol and degradation temperature for 5% of weight loss (Td 5%) between 227°C and 250°C.

Mots clés: non isocyanates polyurethanes; thiol-ene; biobased polymers

Domaines: Polymères

Sofia Benyahya, Myriam Desroches, Rémi Auvergne, Stéphane Carlotti, Sylvain Caillol, et al.. Synthesis of glycerin carbonate-based intermediates using thiol-ene chemistry and isocyanate free polyhydroxyurethanes therefrom. Polymer Chemistry, 2011, 2, pp.2661-2667. ⟨10.1039/c1py00289a⟩. ⟨hal-00631583⟩