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.
Highlights
In 2011, Keul et al [1] introduced the concept of using bifunctional coupling agents in the development of multifunctional polymers
In the stepwise strategy, the first step is the formation of a bicyclic carbonate compound through the stoichiometric Aza-Michael addition of diamine groups to the glycerol carbonate acrylate
We initially investigated the effects of certain experimental parameters, by studying the self-reaction of glycerol carbonate acrylate (GCA) at a temperature of 90 ◦ C under mechanical stirring
Summary
In 2011, Keul et al [1] introduced the concept of using bifunctional coupling agents in the development of multifunctional polymers. The nitrogen of the primary amine forms new secondary and tertiary intermolecular bonds This increases the density of the carbon-nitrogen bonds and of ethylene and carboxyester sites on GCA. During this condensation, the cyclic carbonate core of the molecule remains closed. We investigated the potential of GCA for use as a cyclic carbonate based chemical coupling agent in the production of multifunctional high-molar mass PHUs. The Aza-Michael reaction generates functional linear and branched mono, di-, tri-, and tetra-amines and increases the density of nitrogen-carbon bonds. Interchain, and crosslinked structures result from this increase in urethane unit density and from increases in the densities of adjacent primary and secondary hydroxyl groups, and ethylene and carboxyester groups, favoring the formation of multifunctional PHUs
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