A double click strategy applied to the reversible polymerization of furan/vegetable oil monomers

Abstract

This investigation describes preliminary results related to the preparation of monomers based on vegetable oil derivatives bearing furan heterocycles appended through thiol-ene click chemistry, and their subsequent polymerization via the Diels-Alder (DA) polycondensation between furan and maleimide complementary moieties, i.e. a second type of click chemistry. Following the optimization of these interactions with model compounds, two basic approaches were considered for these DA polymerizations, namely (i) the use of monomers with two terminal furan rings in conjunction with bismaleimides (AA + BB systems) and (ii) the use of AB monomers incorporating both furan and maleimide end-groups. This ongoing study clearly showed that both approaches were successful, albeit with different outcomes, in terms of the nature of the products. The application of the retro-DA reaction confirmed their thermoreversible character, i.e. the clean-cut return to their respective starting monomers.

Keywords: furan-maleimide Diels-Alder polymers; renewable resources; thermoreversible polymerization; thiol-ene click chemistry; vegetable oil derivatives.