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Issue 11, 2011
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Synthesis of glycerin carbonate-based intermediates using thiol–ene chemistry and isocyanate free polyhydroxyurethanes therefrom

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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 thiolene 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−1 to 9000 g mol−1 and degradation temperature for 5% of weight loss (Td 5%) between 227 °C and 250 °C.

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

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Publication details

The article was received on 24 Jun 2011, accepted on 05 Aug 2011 and first published on 06 Sep 2011


Article type: Paper
DOI: 10.1039/C1PY00289A
Polym. Chem., 2011,2, 2661-2667

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

    S. Benyahya, M. Desroches, R. Auvergne, S. Carlotti, S. Caillol and B. Boutevin, Polym. Chem., 2011, 2, 2661
    DOI: 10.1039/C1PY00289A

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