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Issue 21, 2014
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Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors

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Abstract

(Bis) 6-membered cyclic carbonates were prepared from methyl 10-undecenoate, which is produced from ricinoleic acid, a main constituent of castor oil. Kinetic studies on these new fatty acid-based 6-membered cyclic carbonates revealed that they are much more reactive than their homologs, 5-membered ones (30 times). Poly(hydroxyurethane)s (PHUs) were then synthesized from these bis 6-membered cyclic carbonates at a temperature as low as room temperature and in the solvent or bulk. Unexpectedly, chemical gels were obtained. The latter were the consequence of side reactions of carbonate ring-opening with the hydroxyl groups of the formed poly(hydroxyurethane)s. Quenching with a large excess of hexylamine enabled the breaking-up of the gel with the formation of urea linkages.

Graphical abstract: Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors

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Publication details

The article was received on 03 Jul 2014, accepted on 14 Jul 2014 and first published on 15 Jul 2014


Article type: Communication
DOI: 10.1039/C4PY00922C
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Polym. Chem., 2014,5, 6142-6147

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    Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors

    L. Maisonneuve, A. Wirotius, C. Alfos, E. Grau and H. Cramail, Polym. Chem., 2014, 5, 6142
    DOI: 10.1039/C4PY00922C

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