Publication : Functionalizable thermoresponsive polymers synthesized from renewable 5-hydroxymethylfurfural derivative via the thiol-Michael addition reaction
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Thermoresponsive copoly(β-thioether ester)s were efficiently synthesized from 2,5-furan diacrylate (2,5-FDA) via the thiol-Michael addition reaction under mild reaction conditions. The structures, compositions and thermal properties of copoly(β-thioether ester)s were analyzed by FTIR, 1H NMR, DSC and TGA. The resulting copoly(β-thioether ester)s exhibited a reversible thermal-induced phase transition in aqueous medium. The adjustment of cloud point temperatures (Tcp) were performed by varying the ratio of 2,5-FDA in the copolymers, and their values are in the range of ~20 to 53 oC. Furthermore, the polymer concentration and the addition of sodium chloride influenced the Tcp. 1H NMR analysis confirmed the occurrence of Diels-Alder reaction. The Tcp decreased due to the enhanced hydrophobicity after the modification. These results indicated that the thiol-Michael addition reaction could be used to synthesize potentially biodegradable and functionalizable thermoresponsive polymers.