Kinetics and mechanism of free-radical polymerization reaction of acrylic monomers based on triglycerides of plant oils

1Kirianchuk, VF, 2Demchuk, ZI, 2Tarnavchyk, IT, 2Kingsley, K, 1Kohut, AM, 1Shevchuk, OM, 1Voronov, SA, 2Voronov, AS
1Lviv Polytechnic National University
2North Dakota State University, Fargo, USA
Dopov. Nac. akad. nauk Ukr. 2018, 3:95-103
https://doi.org/10.15407/dopovidi2018.03.095
Section: Chemistry
Language: Ukrainian
Abstract: 

A new acrylic monomer (acryloylamino)ethyl oleate ("olive" monomer, OM) is synthesized, by using the transesterification of olive oil with N-(hydroxyethyl)acrylamide. The structures of OM and its homopolymer are confirmed, by using FTIR and 1H NMR-spectroscopy. The special feature of the structure of OM is the presence of only one double bond, in contrast to the known acrylic monomer based on the triglycerides of soybean oil, (acryloylamino) ethyl soyate ("soybean monomer", SM), which has two double bonds in the acyl fragment of the fatty acid. In the radical polymerization of OM, this leads to the simultaneous chain growth reaction and a less pronounced chain transfer reaction, as compared with SM, as well as to the formation of poly-OM with a higher molecular weight than poly-SM. The reaction orders with respect to the monomer and the initiator, as well as kinetic peculiarities for the polymerization of OM and SM, are determined. Monomer reactivity ratios (r1, r2) for the copolymerization of the newly synthesized olive oil-based acrylic monomer with styrene, as well as the Q−e values for OM, are determined.

Keywords: free radical polymerization, monomers from vegetable oils, olive oil, transesterification
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