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

Polymer Chemistry, ISSN: 1759-9962, Vol: 2, Issue: 11, Page: 2661-2667
2011
  • 76
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Metrics Details

  • Citations
    76
    • Citation Indexes
      76
  • Captures
    90

Article Description

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 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. © The Royal Society of Chemistry.

Bibliographic Details

Sofia Benyahya; Myriam Desroches; Rémi Auvergne; Sylvain Caillol; Bernard Boutevin; Stéphane Carlotti

Royal Society of Chemistry (RSC)

Chemical Engineering; Biochemistry, Genetics and Molecular Biology; Materials Science; Chemistry

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