1,3-Dioxolan-4-one (DOX) chemistry was explored for production of "one-pot" biobased polyester thermosets. DOX monomer was first functionalized by naturally occurring eugenol to introduce a structural element, which could induce cross-linking reaction through cationic polymerization of the double bond. The feasibility of polymerizing DOX monomers bearing bulky side groups was proven by model phenol-substituted DOX monomer (PhDOX). Once the reaction was shown to be effective, the same protocol was applied to eugenol-substituted monomer (EuDOX). A brief screening of the optimal catalyst concentration was performed, to obtain a highly cross-linked product. The synthesized thermoset showed good thermal resistance and high mechanical strength probably due to the rich aromatic content. The obtained thermoset was further subjected to microwave-assisted hydrothermal degradation test, which demonstrated complete recyclability to water or methanol soluble products. NMR and matrix-assisted laser desorption/ionization-mass spectroscopy analyses of the obtained degradation products unveiled the structure of the thermoset, strongly indicating that the polymerization of eugenol-functionalized DOX monomer resulted in polylactide-like chains connected with aromatic-aliphatic segments resulting from the reaction of the eugenol double bonds. The presence of free hydroxyl and carboxyl groups sheds light on the mechanism behind the observed shape-memory and self-healing properties.

One-Pot Synthesis of Sustainable High-Performance Thermoset by Exploiting Eugenol Functionalized 1,3-Dioxolan-4-one / S. Gazzotti, M. Hakkarainen, K.H. Adolfsson, M.A. Ortenzi, H. Farina, G. Lesma, A. Silvani. - In: ACS SUSTAINABLE CHEMISTRY & ENGINEERING. - ISSN 2168-0485. - 6:11(2018 Nov 05), pp. 15201-15211. [10.1021/acssuschemeng.8b03655]

One-Pot Synthesis of Sustainable High-Performance Thermoset by Exploiting Eugenol Functionalized 1,3-Dioxolan-4-one

S. Gazzotti
Primo
;
M.A. Ortenzi;H. Farina;G. Lesma
Penultimo
;
A. Silvani
Ultimo
2018-11-05

Abstract

1,3-Dioxolan-4-one (DOX) chemistry was explored for production of "one-pot" biobased polyester thermosets. DOX monomer was first functionalized by naturally occurring eugenol to introduce a structural element, which could induce cross-linking reaction through cationic polymerization of the double bond. The feasibility of polymerizing DOX monomers bearing bulky side groups was proven by model phenol-substituted DOX monomer (PhDOX). Once the reaction was shown to be effective, the same protocol was applied to eugenol-substituted monomer (EuDOX). A brief screening of the optimal catalyst concentration was performed, to obtain a highly cross-linked product. The synthesized thermoset showed good thermal resistance and high mechanical strength probably due to the rich aromatic content. The obtained thermoset was further subjected to microwave-assisted hydrothermal degradation test, which demonstrated complete recyclability to water or methanol soluble products. NMR and matrix-assisted laser desorption/ionization-mass spectroscopy analyses of the obtained degradation products unveiled the structure of the thermoset, strongly indicating that the polymerization of eugenol-functionalized DOX monomer resulted in polylactide-like chains connected with aromatic-aliphatic segments resulting from the reaction of the eugenol double bonds. The presence of free hydroxyl and carboxyl groups sheds light on the mechanism behind the observed shape-memory and self-healing properties.
Biobased; DOX; Eugenol; PLA; Thermoset; Chemistry (all); Environmental Chemistry; Chemical Engineering (all); Renewable Energy, Sustainability and the Environment
Settore CHIM/05 - Scienza e Tecnologia dei Materiali Polimerici
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/607830
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