New bio-based materials obtained by thiol-ene/thiol-epoxy dual curing click procedures from eugenol derivates
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Novel bio-based and dual-curable thermosets were prepared from eugenol derivatives. The curing sequence combined two click reactions, a photoinduced radical thiol-ene reaction followed by a thermally activated thiol-epoxy reaction. Eugenol was transformed into a triallyl (3A-EU) and a diallyl glycidyl derivative (2AG-EU) with high yields, and they were used as starting monomers in order to study the thiol-ene reaction and the dual-curing process, respectively. Three different thiol crosslinkers were tested, one commercially available tetrathiol derived from pentaerythritol (PETMP) and two other that were also synthesized: a trithiol derived from eugenol (3SH-EU) and a hexathiol derived from squalene (6SH-SQ). FTIR and DSC were used to monitor both curing stages and analyze the obtained materials. The results evidenced the occurrence of side reactions that led to incomplete thiol-ene reaction. The dual-curable materials showed higher Tgs than the materials obtained by a simple thiol-ene process and presented higher mechanical and thermomechanical performance.
CitationGuzman, D., Ramis, X., Fernandez-Francos, X., de la Flor, S., Serra, À. New bio-based materials obtained by thiol-ene/thiol-epoxy dual curing click procedures from eugenol derivates. "European polymer journal", Agost 2017, vol. 93, p. 530-544.