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One-Pot Synthesis of Sustainable High-Performance Thermoset by Exploiting Eugenol Functionalized 1,3-Dioxolan-4-one
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology. Univ Milan, Dept Chem, Via Golgi 19, I-20133 Milan, Italy.;Univ Milan, Dept Chem, CRC Mat Polimerici LaMPO, Via Golgi 19, I-20133 Milan, Italy..
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.ORCID iD: 0000-0002-7790-8987
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
Univ Milan, Dept Chem, Via Golgi 19, I-20133 Milan, Italy.;Univ Milan, Dept Chem, CRC Mat Polimerici LaMPO, Via Golgi 19, I-20133 Milan, Italy..
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2018 (English)In: ACS SUSTAINABLE CHEMISTRY & ENGINEERING, ISSN 2168-0485, Vol. 6, no 11, p. 15201-15211Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2018. Vol. 6, no 11, p. 15201-15211
Keywords [en]
DOX, Biobased, Thermoset, PLA, Eugenol
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-239787DOI: 10.1021/acssuschemeng.8b03655ISI: 000449577200173Scopus ID: 2-s2.0-85055160019OAI: oai:DiVA.org:kth-239787DiVA, id: diva2:1276655
Note

QC 20190108

Available from: 2019-01-08 Created: 2019-01-08 Last updated: 2019-01-08Bibliographically approved

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Hakkarainen, MinnaAdolfsson, Karin H.

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