Novel ring-disubstituted isobutyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2CH(CH3)2 (where R is 2-bromo-3-methoxy, 2-bromo-5-methoxy, 3-bromo-4-methoxy, 5-bromo-2-methoxy, 2-bromo-4-methyl, 2-chloro-3-methoxy, 3-chloro-4-methoxy, 3-chloro-4-methyl) were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-disubstituted benzaldehydes and isobutyl cyanoacetate and characterized by CHN analysis, IR, 1H and 13C NMR. The acrylates were copolymerized with styrene in solution with radical initiation (ABCN) at 70C. The compositions of the copolymers were between 19.6 and 32.6 mol% of acrylates. Weight-average molecular masses of the copolymers were 41.3 - 54.5kD. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 248-500ºC range with residue (1.5-6.1% wt), which then decomposed in the 500-800ºC range.
Synthesis and styrene copolymerization of novel bromo, chloro, methoxy, and methyl ring-disubstituted isobutyl phenylcyanoacrylates
02 March 2022, Version 1
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