Innovative and Strategic Program Initiatives for Research and Education

Innovative and Strategic Program Initiatives for Research and Education-North Dakota INSPIRE North Dakota, National Science Foundation EPSCoR RII Track-1

Sub-Project Summary (Waterborne Polymeric Materials from Plant Oils)

Most currently available syntheses of polymers from plant oils are limited to polycondensation and oxypolymerization. Both mechanisms result in the formation of exclusively cross-linked polymers, widely applicable in industrial coatings. This project targets development of novel waterborne polymeric materials (latexes, dispersions, emulsions etc.) from plant oils for coatings, paints, adhesives etc. Due to highly hydrophobic nature of plant oils (triglycerides), their use for development of such materials has been challenging.

To overcome this hydrophobicity, converting oils into vinyl monomers to synthesize latexes via classic radical chain polymerization in emulsion was invented in the PI’s group. Novel plant oil-based acrylic monomers are synthesized in a one-step direct transesterification (alcoholysis) of oil triglycerides. While the vinyl bond of the monomers is reactive in radical chain polymerization, the double bonds of the fatty acid fragments are unaffected and capable of post-polymerization oxidative reactions. In copolymerization, new monomers behave similar to their petroleum-based vinyl counterparts, and it is described with the classical Mayo−Lewis equation.

New acrylic monomers are synthesized from soybean, linseed, sunflower and olive oil, possessing remarkably different compositions of fatty acids in triglycerides. While length of fatty acid carbon chains is similar (mostly oleic, linoleic and linolenic acids), average number of double bonds per oil triglyceride (degree of unsaturation) varies significantly.

In this project, specifically, degree of unsaturation in fatty acids will be utilized as a criterion for understanding fundamental behavior of new monomers in radical chain (co)polymerization. Key questions we will address include understanding of i. how degree of unsaturation impacts new acrylic fatty monomers reactivity in (co)polymerization as well as the resulting latex properties, and ii. do polymer latexes, based on monomers from different plant oils, demonstrate different performance in coatings, paints, adhesives, once they are copolymerized with a variety of petroleum-based counterparts?

If successful, the proposed work will allow us to (i) compare reactivity of plant oil-based acrylic monomers derived from different plant oils in free radical copolymerization (both binary and ternary) and potentially extend plant oil-based monomer library by choosing other plant oils for monomer synthesis, (ii) understand the mechanism of emulsion (co)polymerization of the highly hydrophobic plant oil-based acrylic monomers, and (iii) learn about the impact of plant oil compositions on formation, properties, and performance of polymeric materials derived from the fabricated latexes.


July,1,2016 – June,30,2019 (in collaboration with multiple PIs),  $111,663 (current year)