Copolymers of xylan-derived furfuryl alcohol and natural oligomeric tung oil derivatives

Author(s)

Ribeiro, Bruna O. ^[1] ; Valerio, Victor S. ^[1] ; Gandini, Alessandro ^[2] ; Lacerda, Talita M. ^[1]

Affiliation

^[1] Univ Sao Paulo, Engn Sch Lorena, Biotechnol Dept, BR-12602810 Lorena, SP - Brazil

^[2] Univ Grenoble Alpes, LGP2, F-38000 Grenoble - France

• Document type: Journal article
• Source: International Journal of Biological Macromolecules; v. 164, p. 2497-2511, DEC 1 2020.
• Web of Science Citations: 0

Abstract

The utilization of vegetable oils as biological oligomers for the synthesis of macromolecular materials has considerably evolved in the last decades, opening the way for the preparation of sophisticated materials based on synthetic processes for the design of polymers with very specific applications. Tung oil (TO), easily obtained from the seeds of the Asian tung tree (Vernicia fordii), is a relatively cheap commodity that has as its main constituent (similar to 85%) a peculiar natural oligomeric triglyceride structure in which each chain bears three conjugated unsaturations corresponding to alpha-eleostearic acid. Following a previous study based on the association of TO with furans for the preparation of linear and cross-linked structures based on the Diels-Alder click reaction, the present study deals with the cationic (co) polymerization of xylan-derived furfuryl alcohol (FA) with TO, in order to combine the high intrinsic flexibility of the crosslinked TO polymers with the stiffness of the FA resin, which should lead to fully bio-based crosslinked materials with a tunable glass transition. Three approaches were investigated using trifluoroacetic acid (TFA) in chloroform, viz. (i) combining crude TO and furfuryl alcohol, (ii) combining methyl alpha-eleostearate and furfuryl alcohol, and (iii) polymerizing furfuryl alpha-eleostearate itself. The polymerization reactions with varying TFA concentrations were followed by H-1 NMR spectroscopy, and it was possible to get valuable information on mechanistic aspects. Also, higher concentrations of TFA were used to synthesize and isolate polymer networks, in order to understand their molecular characteristic as well as access their main thermal properties. (C) 2020 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 18/24407-6 - Sustainable strategies for the development of new macromolecular materials
• Grantee: Talita Martins Lacerda
• Support Opportunities: Research Grants - Visiting Researcher Grant - International
• FAPESP's process: 17/16062-6 - Cationic polymerization of unsaturated vegetable oils and application as matrix in biocomposites with bacterial celulose
• Grantee: Talita Martins Lacerda
• Support Opportunities: Regular Research Grants