Polymerizability of 1,3-Disubstituted 1,3-Butadiene and Preparation of New Alternating Copolymer

Kamachi, Mikiharu; Miwa, Reijiro; Nozakura, Shun‐ichi

doi:10.1295/polymj.12.899

Cited by 12 publications

(6 citation statements)

References 7 publications

(3 reference statements)

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“…However, several 1,3‐substituted butadienes have been synthesized, including ethylene/vinyl alcohol, [ 82 ] styrene/ethylene, [ 77 ] and vinyl ether/acrylate. [ 83 ]…”

Section: Selection Of Monomersmentioning

confidence: 99%

Controlled Synthesis of Polymers^†

2023

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“…However, several 1,3‐substituted butadienes have been synthesized, including ethylene/vinyl alcohol, [ 82 ] styrene/ethylene, [ 77 ] and vinyl ether/acrylate. [ 83 ]…”

Section: Selection Of Monomersmentioning

confidence: 99%

Controlled Synthesis of Polymers^†

2023

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“…Each peak of poly-(EEP) was resonably assigned by the 1 ,4-addition unit as previously reported. 15 In poly(EP) (Figure 4), no signal could be detected in the region from 4.5 ppm to 5.2 ppm where vinilidene protons of the vinyl group binding to a carbon atom gave a resonance peak. 20 Therefore, the possibility of a 1,2-addition is ruled out.…”

Section: Esr Spectra Of Propagating Radicalsmentioning

confidence: 99%

“…EXPERIMENTAL Ethyl 4-ethoxy-2,4-pentadienoate (EEP, trans: cis= 92 : 8) was prepared as shown in a previous paper. 15 Bp 60°C/0.5 mm. Ethyl trans-4-methyl-2,4-pentadienoate (EMP) and ethyl 2,4-pentadienonate (EP) were similarly prepared from methacrolein and acrolein, respectively.…”

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confidence: 99%

ESR Study of the Propagating Radicals of Diene Compounds in Frozen State. Conformations, Spin Densities, and Reactivities of the Propagating Radicals

Kamachi

Umetani

Kuwae

et al. 1983

Polym J

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An ESR study on the radical polymerization of diene compounds was carried out in frozen aromatic solvents, using benzoyl peroxide as a photoinitiator. The diene compounds were CH2 =CHX-CH=CHY (X=OCH3 and Y=COOCH2CH3, X=CH3 and Y=COOCH2CH3, X= H and Y = COOCH2CH3 , and X= H and Y = OCOCH3). Spectra were observed at-l20°C. The hyperfine splitting constants show that the propagating radical ends are allylic radicals whose unpaired electrons were completely delocalized over the three carbons of their chain ends. The conformation and spin density of the radical ends were estimated from the hyperfine splitting constants of methylene protons adjacent to the radicals and ()(-protons. The conformations could be explained by a single conformation. The reactivity of the propagating radicals was estimated from the propagation rate constants for radical polymerizations and reactivity ratios in the copolymerizations with styrene. The relation between the spin density and reactivity of the propagating radicals is discussed. KEY WORDS ESR I Ethyl 4-Ethoxy-2,4-pentadienoate I Ethyl 4-Methyl-2,4-pentadienoate I Ethyl 2,4-Pentadienoate I 1-Acetoxybutadiene I

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“…reported the radical polymerizations of ethyl trans ‐4‐ethoxy‐2,4‐pentadienoate and trans ‐4‐ethoxyl‐2,4‐pentadienonitrile. The resulting polymers were hydrogenated to give alternating copolymers of ethyl vinyl ether/ethyl acrylate and of ketene/acrylonitrile, respectively . Li et al .…”

Section: Introductionmentioning

confidence: 99%

“…The resulting polymers were hydrogenated to give alternating copolymers of ethyl vinyl ether/ethyl acrylate and of ketene/ acrylonitrile, respectively. 23 Li et al reported anionic polymerization of 1-phenyl-3-isopropyl-1,3-butadiene (PhiPrBu). The polymerization was highly regioselective and the resulting product was dehydrogenated into substituted polyacetylene with alternating sequence of the substituents.…”

mentioning

confidence: 99%

Synthesis of asymmetrically substituted head‐to‐head polyacetylenes from 2,3‐disubstituted‐1,3‐butadienes

2018

J. Polym. Sci. Part A: Polym. Chem.

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Asymmetrically substituted head‐to‐head polyacetylenes with phenyl and triphenylamine, thienyl or pyrenyl side groups were synthesized through anionic or controlled radical polymerization of 2,3‐disubstituted‐1,3‐butadienes and subsequent dehydrogenation process. Anionic polymerizations of the designed monomers bearing pendent triphenylamine and thienyl group gave narrow disperse disubstituted precursor polybutadienes with exclusive 1,4‐ or 4,1‐structure, which were confirmed by GPC and NMR measurements. In addition, the monomers possessing pyrenyl group were polymerized via nitroxide mediated radical polymerization and the resulting polymers were obtained with controlled molecular weight and low polydispersities. These polybutadiene precursors were then dehydrogenated in the presence of 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone. Thus asymmetrically substituted head‐to‐head polyacetylenes were obtained as indicated by 1H NMR. The properties of polybutadiene precursors and the corresponding polyacetylenes were analyzed by UV–vis, DSC, and TGA. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 395–402

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Polymerizability of 1,3-Disubstituted 1,3-Butadiene and Preparation of New Alternating Copolymer

Cited by 12 publications

References 7 publications

Controlled Synthesis of Polymers^†

Controlled Synthesis of Polymers^†

ESR Study of the Propagating Radicals of Diene Compounds in Frozen State. Conformations, Spin Densities, and Reactivities of the Propagating Radicals

Synthesis of asymmetrically substituted head‐to‐head polyacetylenes from 2,3‐disubstituted‐1,3‐butadienes

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Polymerizability of 1,3-Disubstituted 1,3-Butadiene and Preparation of New Alternating Copolymer

Cited by 12 publications

References 7 publications

Controlled Synthesis of Polymers†

Controlled Synthesis of Polymers†

ESR Study of the Propagating Radicals of Diene Compounds in Frozen State. Conformations, Spin Densities, and Reactivities of the Propagating Radicals

Synthesis of asymmetrically substituted head‐to‐head polyacetylenes from 2,3‐disubstituted‐1,3‐butadienes

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Controlled Synthesis of Polymers^†

Controlled Synthesis of Polymers^†