Novel Copolymers of Styrene. 2. Oxy Ring-Substituted Butyl 2-Cyano-3-Phenyl-2-Propenoates |
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Authors: | Gregory B. Kharas Hui Feng Christopher Aranda Maya E. Navarro Stephanie Pacheco Quinn Pazderka |
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Affiliation: | 1. DePaul University, Chemistry Department, 1110 West Belden Avenue, Chicago, IL 60614-3214gkharas@depaul.edu;3. DePaul University, Chemistry Department, 1110 West Belden Avenue, Chicago, IL 60614-3214 |
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Abstract: | Novel trisubstituted ethylenes, oxy ring-substituted butyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2C4H9 (where R is 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 4-propoxy, 4-butoxy, 4-hexyloxy, 3-phenoxy) were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of oxy ring-substituted benzaldehydes and butyl 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. The order of relative reactivity (1/r1) for the monomers is 4-methoxy (6.56) > 3-methoxy (2.97) > 2-methoxy (2.72) > 4-butoxy (2.20) > 3-ethoxy (2.18) > 4-propoxy (2.15) > 4-hexyloxy (1.78) > 4-ethoxy (1.66) > 2-ethoxy (1.48) > 3-phenoxy (1.29). Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500°C range with residue (0.8–3.6% wt.), which then decomposed in the 500–800°C range. |
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Keywords: | Trisubstituted ethylenes radical copolymerization styrene copolymers |
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