Features of synthesis and copolymerization of vinyl monomer based on olive oil

Authors

DOI:

https://doi.org/10.31548/bio2018.03.014

Abstract

During the last two decades, interest in bioresources has grown significantly. The formation of polymeric materials from renewable resources, especially vegetable oils, today attracts considerable attention due to the current high cost of petroleum products, as well as their negative impact on the environment. Renewable materials, mainly vegetable oils, have become widely used in the synthesis of new polymer materials, due to their availability, biodegradability and low cost. An important task of modern research is the search for ways to create waterproof protective coatings. Hydrophobic monomers based on vegetable oils can be used in the production of waterproof polymer coatings, plasticizers, paints, adhesives, etc.

The purpose of the work was synthesis of monomer based on triglycerides of olive oil - (acryloylamino)ethyl oleate, study of miniemulsion copolymerization and physico-mechanical properties of latex films based on the copolymers.

The monomer structure was confirmed by 1H NMR spectroscopy. Through miniеmulsion copolymerization, latex copolymers of (acryloylamino)ethyl oleate with methyl methacrylate and styrene were obtained. Increasing of the content of (acryloylamino)ethyl oleate fragments in latex polymers provides the plasticizing effect and a corresponding decreasing of the glass transition temperature of the latex copolymers. With an increase of the plant oil-based monomers content in the latex polymer, the Young's modulus decreases and the relative tensile strength at the break increases, which confirms the appearance of the intramolecular plasticizing effect. It has been shown that the presence of the (acryloylamino)ethyl oleate fragments in latex copolymers enhances the hydrophobicity of latex films, which implies their use in polymeric coatings as additives with good barrier properties.

(Acryloylamino)ethyl oleate and its copolymers derived from renewable raw materials have good prospects for the synthesis of aqueous dispersions of polymers (latexes) and coatings on their basis, providing highly effective protective properties: hydrophobicity, atmospheric resistance.

References

Mirna, A. Mosiewicki, Mirta, I. Aranguren. (2010). A short review on novel biocomposites based on plant oil precursors. European Polymer Journal. 49, 1243–1256.

Xia, Y., Larock, RC. (2010). Vegetable oil-based polymeric materials: synthesis, properties, and applications. Green Chemistry. 12 (11), 1893–909. https://doi.org/10.1039/c0gc00264j

Yuan, L., Wang, Z., Trenor, N. M., Tang, C. (2015). Robust Amidation Transformation of Plant Oils into Fatty Derivatives for Sustainable Monomers and Polymers. Macromolecules. 48, 1320−1328. https://doi.org/10.1021/acs.macromol.5b00091

Moreno, M., Miranda, J. I., Goikoetxea. M., Barandiaran, M. (2014). Sustainable polymer latexes based on linoleic acid for coatings applications. Progress in Organic Coatings. 77, 1709−1714. https://doi.org/10.1016/j.porgcoat.2014.05.016

Tarnavchyk, I., Popadyuk, A., Popadyuk, N., Voronov, A. (2015). Synthesis and Free Radical Copolymerization of a Vinyl Monomer from Soybean Oil. ACS Sustainable Chemistry & Engineering. 3, 1618−1622. https://doi.org/10.1021/acssuschemeng.5b00312

Demchuk, Z., Shevchuk, O., Tarnavchyk, I., Kirianchuk, V., Lorenson, M., Kohut, A., Voronov, S., Voronov, A. (2016). Free Radical Copolymerization Behavior of Plant Oil-Based Vinyl Monomers and Their Feasibility in Latex Synthesis. ACS Omega. 1, 1374−1382. https://doi.org/10.1021/acsomega.6b00308

Barison, A., Silva, C., Campos, F., Simonelli, F., Lenz, C., Ferreira, A. (2010). A simple methodology for the determination of fatty acid composition in edible oils through 1H NMR spectroscopy. Magnetic Resonance in Chemistry. 48 (8), 571-659. https://doi.org/10.1002/mrc.2629

Boskou, D. (2006). Olive Oil Chemistry and Technology, 2nd Edition. New York. AOCS Publishing, 288. https://doi.org/10.1201/9781439832028

Published

2018-08-14

Issue

Section

Chemistry