Novel copolymers of styrene. 8. Fluoro,methoxy, and methyl ring-disubstituted propyl 2-cyano-3-phenyl-2-propenoates |
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Authors: | Gregory B Kharas Yesenia L Soto Emily L Divino Mikaela Donovan Mike D Dotson Deena Kishawi |
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Institution: | 1. Chemistry Department, DePaul University, Chicago, ILgkharas@depaul.edu;3. Chemistry Department, DePaul University, Chicago, IL |
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Abstract: | Novel trisubstituted ethylenes, ring-disubstituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH?C(CN)CO2C3H7 (where R is 2-fluoro-5-methoxy, 2-fluoro-6-methoxy, 3-fluoro-4-methoxy, 4-fluoro-3-methoxy, 5-fluoro-2-methoxy, 2-fluoro-6-methyl, 3-fluoro-2-methyl, 4-fluoro-2-methyl, 4-fluoro-3-methyl, 5-fluoro-2-methyl) were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and propyl cyanoacetate and characterized by CHN elemental analysis, IR, 1H- and 13C-NMR. All the ethylenes were copolymerized with styrene (M1) 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. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200–500°C range with residue (1.4–3.0% wt.), which then decomposed in the 500–800°C range. |
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Keywords: | Radical copolymerization styrene copolymers trisubstituted ethylenes |
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