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Synthesis and Styrene Copolymerization of Novel Fluoro and Oxy Ring-Disubstituted Isopropyl Phenylcyanoacrylates

submitted on 10.11.2019, 02:09 and posted on 20.11.2019, 10:55 by Abby R. Krause, Haley E. Aynessazian, Monica C. Gonzalez, Adnan M. Khan, Lara R. Lieberman, Meghan H. McNicholas, Nina M. Pelsi, Zachary S. Pierard, Sara M. Rocus, William S. Schjerven, Gregory Kharas

Novel fluoro and oxy ring-disubstituted isopropyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH(CH3)2 (where R is 2-fluoro-3-methoxy, 2-fluoro-4-methoxy, 2-fluoro-5-methoxy, 2-fluoro-6-methoxy, 3-fluoro-4-methoxy, 4-fluoro-3-methoxy, 5-fluoro-2-methoxy, 4-fluoro-3-phenoxy) were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and isopropyl cyanoacetate and characterized by CHN elemental analysis, IR, 1H- and 13C-NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by IR, 1H and 13C-NMR, GPC, DSC, and TGA.


Chicago Society of Coating Technology


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DePaul University



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No conflict of interest