Novel trisubstituted ethylenes, ring-substituted isobutyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2CH(CH3)2 (where R is 3-(3,4-dichlorophenoxy), 3-(3,5-dichlorophenoxy), 4-(2,4-dichlorophenoxy), 2-benzyloxy, 3-benzyloxy, 4-benzyloxy, 2-acetyl, 3-acetyl, 4-acetyl) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and isobutyl 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 70C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by FTIR, 1H and 13C NMR. Thermal properties of the copolymers are characterized by DSC and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500C range with a residue, which then decomposed in the 500-800C range.

Synthesis and styrene copolymerization of novel ring-substituted isobutyl phenylcyanoacrylates

ACS Fall 2020 Virtual Meeting

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