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Dean Webster - Sustainable Thermosets from High Functionality Bio-based Resins

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Dean Webster - Sustainable Thermosets from High Functionality Bio-based Resins

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Dean Webster

Professor, Department of Coatings and Polymeric Materials, North Dakota State University

Co-Authors: Adlina Paramarta, Arvin Yu, Eric Krall

Abstract

A challenge faced in transitioning from polymer materials derived from petrochemical sources to bio-based sources is in designing materials having the performance properties required for today’s demanding applications. Thermosetting resin systems are used in numerous high performance coating systems. While vegetable oils are a readily available and amenable to functionalization to be used in thermosets, their long aliphatic hydrocarbon chains tend to result in materials that are soft and flexible. However, we have found that by creating multifunctional resins from vegetable oil fatty acids and a highly functional polyol, thermosets can be formed that have the strength and stiffness for use in high performance applications. For example, epoxidized sucrose esters of vegetable oil fatty acids, such as epoxidized sucrose soyate (ESS, Figure 1) crosslinked with cyclic anhydrides yield thermosets having high modulus, solvent resistance, and hardness. Polyurethanes made using highly functional soy polyols have glass transition temperatures exceeding 100 °C, much higher than typical soy-based polyols. In addition, 100% bio-based thermosets can be made from the water-catalyzed crosslinking of epoxidized sucrose soyate with naturally-occurring acids such as citric or tartaric acids. Further functionalization with acrylate or methacrylate groups can lead to systems cured using free radical photopolymerization and via Michael reaction chemistry. We have also discovered a process for synthesizing highly functionalized lignin that can be cured into hard and durable coatings. In all of these examples, the thermosets formed have properties superior to their triglyceride oil counterparts and equivalent to current petrochemical resins.

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