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Molecules 2016, 21(9), 1220; doi:10.3390/molecules21091220

Synthesis of High-Molecular-Weight Multifunctional Glycerol Polyhydroxyurethanes PHUs

1
Laboratoire de Chimie Agro-industrielle (LCA), Université de Toulouse, INRA, INPT, Toulouse, France
2
Laboratoire de Génie Chimique, Université de Toulouse, CNRS, INPT, UPS, Toulouse, France
3
Oléon SAS, Venette-BP2069-60206 Compiègne CEDEX, France
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 25 July 2016 / Revised: 8 September 2016 / Accepted: 8 September 2016 / Published: 11 September 2016
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Abstract

Glycerol carbonate acrylate is a 5-membered cyclic carbonate synthesized from glycerol that is used as a chemical coupling agent and has proven highly suitable for use in the synthesis of multifunctional polyhydroxyurethanes (PHUs). The multifunctionality of the structure of PHUs is determined by the density of the carbon-amine groups generated by the Aza-Michael reaction and that of the urethane groups and adjacent primary and secondary hydroxyl groups generated by aminolysis. Glycerol carbonate acrylate is polymerized with polyfunctional mono-, di-, tri, and tetra-amines, by type-AB polyaddition, either in bulk or in solution, through stepwise or one-pot reaction strategies in the absence of added catalysts. These approaches result in the generation of linear, interchain, and crosslinked structures, through the polyaddition of linear and branched amines to the ethylene and cyclic carbonate sites of glycerol carbonate acrylate. The resulting collection of organic molecules gives rise to polyethylene amino ester PHUs with a high molar mass, exceeding 20,000 g·mol−1, with uniform dispersity. View Full-Text
Keywords: polyhydroxyurethanes; glycerol carbonate acrylate; dimethyl carbonate; Aza-Michael; aminolysis; type-AB polymerization polyhydroxyurethanes; glycerol carbonate acrylate; dimethyl carbonate; Aza-Michael; aminolysis; type-AB polymerization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Nohra, B.; Candy, L.; Blanco, J.-F.; Raoul, Y.; Mouloungui, Z. Synthesis of High-Molecular-Weight Multifunctional Glycerol Polyhydroxyurethanes PHUs. Molecules 2016, 21, 1220.

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