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Synthesis and radical copolymerization of novel propyl cyanoacrylate monomers

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Abstract

Novel phenyl-trisubstituted propyl 3-(R-phenyl)-2-cyanoacrylates (where R is 2,4,5-trimethyl, 2,4,6-trimethyl, 2,3-dimethyl-4-methoxy, 2,5-dimethyl-4-methoxy, 2,4-dimethoxy-3-methyl, 2,4-dimethoxy-6-methyl, 4-hydoxy-3,5-dimethyl, 2,3,4-trimethoxy, 2,4,5-trimethoxy, 2,4,6-trimethoxy, 3,4,5-trimethoxy) were prepared using piperidine-catalyzed condensation of substituted benzoic aldehydes and propyl ester of cyanoacetic acid with good yields (72–97 wt%). The ethenylbenzene copolymerization of cyanoacrylates (at 3/1 mol feed ratio) in solution with radical initiation at 70 °C resulted in formation of copolymers having MW 3.9 to 27.8 kD and 8.4–25.8 mol% of cyanoacrylate. FTIR, 1H and 13C NMR were used to analyze the structure. Thermal behavior of the copolymers was analyzed by DSC, Tg (81–129 °C) and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200–500 °C range with residue (0.5–7.3 wt%)and then in the 500–800 °C range.

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Correspondence to Gregory B. Kharas.

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Knight, J.D., Arellano, L., Conger, K.O. et al. Synthesis and radical copolymerization of novel propyl cyanoacrylate monomers. Polym. Bull. 77, 1433–1448 (2020). https://doi.org/10.1007/s00289-019-02810-2

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