Synthesis of High-Molecular-Weight Multifunctional Glycerol Polyhydroxyurethanes PHUs.
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.
Laboratoire de Chimie Agro-industrielle (LCA), Université de Toulouse, INRA, INPT, Toulouse, France. bassam@nohra.net.
Bassam
B
Nohra
Laboratoire de Chimie Agro-industrielle (LCA), Université de Toulouse, INRA, INPT, Toulouse, France. laure.candy@ensiacet.fr.
Laure
L
Candy
Laboratoire de Génie Chimique, Université de Toulouse, CNRS, INPT, UPS, Toulouse, France. jeanfrancois.blanco@ensiacet.fr.
Jean-François
JF
Blanco
Oléon SAS, Venette-BP2069-60206 Compiègne CEDEX, France. Yann.RAOUL@oleon.com.
Yann
Y
Raoul
Laboratoire de Chimie Agro-industrielle (LCA), Université de Toulouse, INRA, INPT, Toulouse, France. zephirin.mouloungui@ensiacet.fr.
Zéphirin
Z
Mouloungui
D002384:Catalysis; D005990:Glycerol / Q000737:chemistry*; D011140:Polyurethanes / Q000138:chemical synthesis* / Q000737:chemistry*
D011140:Polyurethanes; D005990:Glycerol
Aza-Michael; aminolysis; dimethyl carbonate; glycerol carbonate acrylate; polyhydroxyurethanes; type-AB polymerization