Novel Copolymers of Styrene. 6. Alkoxy Ring-Substituted Ethyl 2-Cyano-3-Phenyl-2-Propenoates

Kharas, Gregory B.; Delgado, Alexander A.; Anderson, Nathan E.; Bajor, Agnieszka; Colbert, Acheera C.; Coleman, Adrienne; Gregory, Carine E.; Hayes, John C.; Lantin, Jason; Malecki, Joseph M.; Murphy, Timothy C.; Oprescu, Anda; Rydzon, Brett F.; Timoshevskaya, Irina

doi:10.1080/10601325.2013.755409

Cited by 31 publications

(7 citation statements)

References 10 publications

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“…Copolymerization of TSE having double bonds substituted with halo, cyano, and carbonyl groups and electron-rich monosubstituted ethylenes such as styrene, N-vinylcarbazole, and vinyl acetate (10)(11)(12) show a tendency toward the formation of alternating copolymers. Thus, some ringsubstituted MCPP and ECPP monomers were copolymerized with styrene (13,14) and vinyl acetate (15,16). Ring-unsubstituted BCPP was copolymerized with styrene (17) and terpolymerized with styrene and acrylonitrile (18).…”

Section: Introductionmentioning

confidence: 99%

Novel copolymers of styrene. 14. Halogen ring-trisubstituted butyl 2-cyano-3-phenyl-2-propenoates

Kharas

Rocus

Locke

et al. 2016

Journal of Macromolecular Science, Part A

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Novel trisubstituted ethylenes, halogen ring-trisubstituted butyl 2-cyano-3-phenyl-2-propenoates, RPhCH HC(CN)CO 2 C 4 H 9 (where R is 3-bromo-4,5-dimethoxy, 5-bromo-2,4-dimethoxy, 2-bromo-3-hydroxy-4-methoxy, 3-chloro-2,6-difluoro, 4-chloro-2,6-difluoro, 2,3,5-trichloro, 2,3,6-trichloro, 2,4,5-trifluoro) were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and butyl cyanoacetate, and characterized by CHN analysis, IR, 1 H and 13 C-NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70 C. The compositions of the copolymers were calculated from nitrogen analysis and the structures were analyzed by IR, 1 H and 13 C-NMR. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500 C range with residue (3-5% wt.), which then decomposed in the 500-800 C range.

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Section: Introductionmentioning

confidence: 99%

Novel copolymers of styrene. 14. Halogen ring-trisubstituted butyl 2-cyano-3-phenyl-2-propenoates

Kharas

Rocus

Locke

et al. 2016

Journal of Macromolecular Science, Part A

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show abstract

“…Copolymerization of TSE having double bonds substituted with halo, cyano, and carbonyl groups and electron-rich monosubstituted ethylenes such as styrene, N-vinylcarbazole, and vinyl acetate (10)(11)(12) show a tendency toward the formation of alternating copolymers. Thus, some ring-substituted MCPP and ECPP monomers were copolymerized with styrene (13,14) and vinyl acetate (15,16). Ringunsubstituted BCPP was copolymerized with styrene (17) and terpolymerized with styrene and acrylonitrile (18).…”

Section: Introductionmentioning

confidence: 99%

Novel copolymers of styrene. 13. Methyl and methoxy ring-trisubstituted butyl 2-cyano-3-phenyl-2-propenoates

Kharas

Gao

Clara

et al. 2016

Journal of Macromolecular Science, Part A

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Novel electrophilic trisubstituted ethylenes, methyl and methoxy ring-trisubstituted butyl 2-cyano-3-phenyl-2-propenoates, RPhCHDC(CN)CO 2 C 4 H 9 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, 2,3,4-trimethoxy, 2,4,5-trimethoxy, 2,4,6-trimethoxy, 3,4,5-trimethoxy were prepared and copolymerized with styrene. The monomers were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-trisubstituted benzaldehydes and butyl cyanoacetate, and characterized by CHN analysis, IR, 1 H and 13 C-NMR. All the ethylenes were copolymerized with styrene (M 1 ) in solution with radical initiation (ABCN) at 70 C. The compositions of the copolymers were calculated from nitrogen analysis and the structures were analyzed by IR, 1 H and 13 C-NMR. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200-500 C range with residue (2-5% wt), which then decomposed in the 500-800 C range.

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“…Thus, copolymerization of electrophylic TSE monomers having double bonds substituted with halo, cyano, and carbonyl groups and electron-rich monosubstituted ethylenes such as styrene, N-vinylcarbazole, and vinyl acetate [15][16][17] show a tendency toward the formation of alternating copolymers -thus suggesting a way of functionalization of commercial polymers via introduction of isolated monomer units in copolymers. Earlier we have reported synthesis and styrene copolymerization a number of methyl and oxy ringsubstituted PCAs, such esters as methyl [18,19], ethyl [20][21][22], propyl [23,24], isopropyl [25][26][27], and butyl [28,29].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and styrene copolymerization of novel oxy ring-disubstituted isobutyl phenylcyanoacrylates

Bailey¹,

Barcinski²,

Galloway³

et al. 2020

Preprint

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Novel oxy ring-disubstituted isobutyl phenylcyanoacrylates, RPhCH=C(CN)CO2CH2CH(CH3)2 (where R is 4-methoxy-2-methyl, 4-methoxy-3-methyl, 3-ethoxy-4-methoxy, 4-ethoxy-3-methoxy, 3,4-dibenzyloxy, 2-benzyloxy-3-methoxy, 3-benzyloxy-4-methoxy, 2,3-methylenedioxy) 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 calculated from nitrogen analysis and the structures were analyzed by FTIR, 1H and 13C NMR.

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Novel Copolymers of Styrene. 6. Alkoxy Ring-Substituted Ethyl 2-Cyano-3-Phenyl-2-Propenoates

Cited by 31 publications

References 10 publications

Novel copolymers of styrene. 14. Halogen ring-trisubstituted butyl 2-cyano-3-phenyl-2-propenoates

Novel copolymers of styrene. 14. Halogen ring-trisubstituted butyl 2-cyano-3-phenyl-2-propenoates

Novel copolymers of styrene. 13. Methyl and methoxy ring-trisubstituted butyl 2-cyano-3-phenyl-2-propenoates

Synthesis and styrene copolymerization of novel oxy ring-disubstituted isobutyl phenylcyanoacrylates

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