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Issue 7, 2016
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Activated lipidic cyclic carbonates for non-isocyanate polyurethane synthesis

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Abstract

Activated 5-membered cyclic carbonates were prepared from glycerol and fatty acid derivatives. Ester and ether moieties were introduced in the β position to the cyclic carbonate, in order to enhance its reactivity towards amines. 1H NMR kinetic investigation of the aminolysis of these cyclic carbonates demonstrated a higher reactivity compared to the one of alkyl substituted cyclic carbonates. In the case of ester-activated carbonates, a reactivity similar to the one of 6-membered ring cyclic carbonates was observed. Moreover, these carbonates exhibited amidation side-reactions with amines that could be however prevented by decreasing the temperature to room temperature. Poly(hydroxyurethane)s (PHUs) were then synthesized from these activated 5-membered ring cyclic carbonates at 70 °C in DMF (1 mol L−1) and exhibited molar masses up to 13 700 g mol−1 with Tg in the range −26 to −10 °C.

Graphical abstract: Activated lipidic cyclic carbonates for non-isocyanate polyurethane synthesis

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Publication details

The article was received on 09 Dec 2015, accepted on 11 Jan 2016 and first published on 11 Jan 2016


Article type: Paper
DOI: 10.1039/C5PY01964H
Polym. Chem., 2016,7, 1439-1451

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    Activated lipidic cyclic carbonates for non-isocyanate polyurethane synthesis

    O. Lamarzelle, P. Durand, A. Wirotius, G. Chollet, E. Grau and H. Cramail, Polym. Chem., 2016, 7, 1439
    DOI: 10.1039/C5PY01964H

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