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Significance Statement
Much effort is nowadays devoted to replacing part of petroleum-derived formulations with plant-based renewable ingredients, including plant/vegetable oils. The oils are considered as abundant and cheaper renewable material available in large quantities. To this end, companies produce technical grade oils for various industrial purposes, such as adhesives, soaps, release agents for molds, replacement to petroleum based resins, etc.
The developed at the Coatings and Polymeric Materials Department of North Dakota State University (NDSU) synthetic approach is a one-step method that converts vegetable/plant oils into acrylic monomers for free radical polymerization. These monomers can be applied directly in the production of biobased latexes for adhesives, coatings and paints, and other polymeric materials that utilize acrylic monomers and polymers. NDSU monomers are uniquely valuable in that they yield linear macromolecules during free radical polymerization, and at the same time, retain reactive sites for post-polymerization cross-linking to generate, in particular, coatings and paints with advanced properties and extended performance.
This combination of facilitating linear polymerization and retaining active sites for secondary reactions distinguishes the new monomers from currently existing biobased counterparts.
In preliminary studies performed by Voronov’s group at Coatings and Polymeric Materials it is found that new monomers can be copolymerized with number of commercially important intermediates including vinyl acetate, methyl methacrylate, styrene, butyl acrylate
The latter feature is very important as it opens wide opportunities in tailoring commercially valuable products such as poly(vinyl acetate) based adhesives, binders and glues, poly(methyl methacrylate) based plastics, coatings and paints, polystyrene resins etc. In addition, especially important is the fact that oil based monomers undergo emulsion polymerization process which is relevant to the waterborne polymer latexes. The newly developed vegetable/plant oils-based monomers might advantageously replace essential part of petroleum-based counterparts in the production of polymers and copolymers.
Journal Reference
ACS Sustainable Chem. Eng., 2015, 3 (7), pp 1618–1622.
Ihor Tarnavchyk, Andriy Popadyuk, Nadiya Popadyuk, Andriy Voronov*
Department of Coatings and Polymeric Materials, North Dakota State University, Fargo, North Dakota 58105-6050, United States
Abstract
A one-step method that converts soybean oil into (acryloylamino)ethyl soyate, a new vinyl monomer of free radical polymerization, was developed. The synthesized monomer combines a vinyl double bond (acryloyl functional group) and nonconjugated (isolated) double bonds of fatty acids. The double bond of the acryloyl group is reactive in a free radical chain polymerization that yields linear macromolecules containing isolated double bonds in side chains. Monomer reactivity ratios (r1, r2) in copolymerization of the new soybean oil-based acrylic monomer (SBA) with styrene, methyl methacrylate, and vinyl acetate, as well as the Q–e parameters of the SBA, were determined. The obtained results indicate that copolymerization can be described with the classical Mayo–Lewis equation. In terms of polymerizability, the SBA can be classified as an acrylic monomer. The double bonds of the fatty acid chains remain mainly unaffected during the free radical polymerization. The remaining unsaturated fragments in the side chains make the resulting macromolecules capable of further oxidative cross-linking and the development of cross-linked polymer coatings.
Copyright © 2015 American Chemical Society
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