New bio-based materials obtained by thiol-ene/thiol-epoxy dual curing click procedures from eugenol derivates. (August 2017)

• Record Type: Journal Article
• Authors: Guzmán, Dailyn; Ramis, Xavier; Fernández-Francos, Xavier; De la Flor, Silvia; Serra, Angels
• Is Part Of: European polymer journal. Volume 93(2017)
• Page Start: 530
• Page End: 544
• Publication Date: 2017-08
• Subjects: Green chemistry -- Bio-based -- Eugenol -- Dual curing -- Click reaction -- Thermosets; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; Polymerization; Polymers; Periodicals; Electronic journals; 547.705
• DOI: 10.1016/j.eurpolymj.2017.06.026
• Languages: English
• ISSNs: 0014-3057

Abstract

Graphical abstract: Highlights: A new diallylglycidyl derivative of eugenol has been prepared. Bio-based thermosets have been prepared by thiol-ene/thiol-epoxy dual curing. Dual cured materials showed better thermomechanical performance than purely photocured. Abstract: 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 Tg s than the materials obtained by a simple thiol-ene process and presented higher mechanical and thermomechanical performance.