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United States Department of Agriculture

Agricultural Research Service

Research Project: FUNCTIONALIZATION OF VEGETABLE OILS FOR USE IN THE POLYMER, OLEOCHEMICAL, AND LUBRICANT INDUSTRIES

Location: Bio-oils Research Unit

Title: Epoxy monomers derived from tung oil fatty acids and its regulable thermosets cured in two synergistic ways

Authors
item Huang, Kun -
item Liu, Zengshe
item Zhang, Jinwen -
item Xia, Jianling -
item Zhou, Yonghong -

Submitted to: Biomacromolecules
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 1, 2014
Publication Date: March 14, 2014
Citation: Huang, K., Liu, Z., Zhang, J., Xia, J., Zhou, Y. 2014. Epoxy monomers derived from tung oil fatty acids and its regulable thermosets cured in two synergistic ways. Biomacromolecules. 15:837-843.

Interpretive Summary: The utilization of renewable raw materials wherever and whenever possible is one necessary step towards sustainable development as petroleum feedstocks dwindle and prices increase. In this research, a new bio-based epoxy monomer with more reactive sites from tung oil has been converted to biodegradable polymers. The properties of the polymers are adjustable by changing the composition of two sorts of curing agents. The formed polymers will be tested by end users such as agricultural equipment manufacturers (tractors and farming machines), the automotive industry (car and truck parts), and civil engineering.

Technical Abstract: A new bio-based epoxy monomer with conjugated double bonds, glycidyl ester of eleostearic acid (GEEA), was synthesized from tung oil fatty acids and characterized by 1H-NMR, 13C-NMR and Mass Spectrometry Analysis (MSA). Differential Scanning Calorimetry (DSC) analysis and FT-IR were utilized to investigate the curing process of GEEA cured by both dienophiles and anhydrides. DSC indicated that GEEA could crosslink with both dienophiles and anhydrides through the Diels-Alder reaction and epoxy/anhydride ring-opening reaction. Furthermore, the Diels-Alder crosslink is much more active than the ring-opening of epoxy/anhydride in the curing process. FT-IR also revealed that GEEA successively reacted with dienophiles and anhydrides in these two crosslinking modes. Dynamic Mechanical Analysis (DMA) and the Tensile test were used to study the thermal and mechanical properties of GEEA cured by maleic anhydride, nadic methyl anhydride, and 1,1'-(methylenedi-4,1-phenylene)bismaleimide, respectively. Due to the independence between the curing agents, dienophile and anhydride, a series of thermosetting polymers with various properties could be obtained by adjusting the composition of these two sorts of curing agents.

Last Modified: 8/21/2014
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