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One-pot enzyme-catalyzed synthesis of dual-functional polyester macromers towards surface-active hydrophobic films

Year: 2017

Journal: RSC Adv., Volume 7, page 50294–50299

Authors: Nameer, Samer; Semlitsch, Stefan; Martinelle, Mats; Johansson, Mats

Organizations: Swedish research council, FORMAS [211-2013-70]; Lantmannen Research Foundation; European Union's Seventh Framework Programme for research, technological development and demonstration [289253]

Selective enzyme catalysis is a valuable tool for the processing of monomers into value-added materials. In the present study natural resources were used to retrieve an omega-hydroxy fatty acid monomer containing an epoxide functionality. A procedure was developed for the synthesis of dual-functional oligomers by utilizing lipase catalysis in a one-pot synthesis route. The chemoselectivity of the enzyme allowed addition of thiol monomers to the retrieved epoxy monomers, without harming the epoxides, achieving a thiol-epoxy functional polyester resin. The synthesis reached full conversion (> 99%) after 8 h. It was possible to selectively crosslink the resin through UV-initiated cationic polymerization of the epoxides into thiol-functional thermosets. The curing performance was followed in situ by real-time FTIR. The thiol groups on the surface of the film were accessible for post-modification.