Soybean Oil Based Thermoset Materials with High Biorenewable Content

In recent years, there has been growing interest in substituting petroleum-based materials with bio-renewable feedstock due to concerns of environmental pollution and the depletion of fossil fuel resources. Thus, the conversion of various bio-sourced monomer precursors into useful polymeric materials has emerged as an attractive strategy. Vegetable oils are a prime example onto which many useful chemical functionalities have been introduced to make them suitable alternatives to petroleum-based monomers. While a large number of vegetable oil derivatives have been blended/incorporated with petroleum-based materials to prepare thermosetting polymers, existing examples normally incorporate low total biorenewable content into the final product. With the goal of generating thermosets with high biorenewable content, recent work [1] from our group will be described where two different soybean oil derivatives with different functional groups (e.g., one as a multifunctional thiol and the other as a multifunctional ene) were photocured to prepare cross-linked thermosets. For example, thiol functional groups were introduced to produce mercaptanized soybean oil by reaction of commercially available epoxidized soybean oil with cysteine functionalities. Then, as-prepared mercaptanized soybean oil was mixed with the commercially available acrylated counterpart, diluent, and photoinitiator, followed by UV irradiation under ambient conditions to produce crosslinked films and fibers. Not only do the resulting materials possess high biorenewable content (e.g., as high as 90 % biosourced carbon) but the fact that they are thermosets makes them potentially suitable for high performance applications.

[1] Soybean Oil Based Fibers Made Without Solvent or Heat, D.W. Janes, K. Shanmuganathan, D.Y. Chou and C.J. Ellison, ACS Macro Letters, 1, 1138-1142 (Sept. 2012).

http://pubs.acs.org/doi/abs/10.1021/mz300325g