New Perfluorocyclobutyl Ether-Based Polymers with High Thermostability and Adjustable Mechanical Properties Derived from Biorenewable Eugenol

Abstract

Three novel trifluorovinyl ether (TFVE) monomers, ES-TFVE, EPS-TFVE, and EOS-TFVE, were synthesized by haloalkane, eugenol and different siloxane coupling agents. These TFVE monomers can transfer to perfluorocyclobutyl ether (PFCB) polymers by heat induced [2π + 2π] cycloaddition reaction. EOS-TFVE contains four TFVE groups while ES-TFVE and EPS-TFVE have two. Bulk polymerization of ES-TFVE or EPS-TFVE produces linear polymer which exhibits as viscous liquid while polymerization of EOS-TFVE forms polymeric network which is in solid state and shows brittle mechanical behaviors at room temperature. Co-polymers of EOS-TFVE and ES-TFVE (EPS-TFVE) have network structure and show rubber-like elastic behaviors. The glass transition temperature (Tg) of the co-polymers can be tuned by the ratio of the monomers. These co-polymers show excellent thermostability, and have potential to be used as elastomer in wide temperature range.

Keywords: Eugenol, perfluorocyclobutyl ether, Thermostability