Radical polymerization behavior of N‐vinylsaccharin

Koizumi, Toru; Saeki, Nobuyoshi; Abematsu, Hisatoshi; Terada, Shu‐Ichi; Moriya, Osamu; Endō, Takeshi

doi:10.1002/(sici)1099-0518(19990815)37:16<3419::aid-pola41>3.3.co;2-e

Cited by 6 publications

(6 citation statements)

References 2 publications

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“…The different behavior in the copolymerization of NVNPI with styrene (Q ) 1.0, e ) -0.8), compared with other conjugated monomers (MA; Q ) 0.45, e ) 0.64, 62 DMAAm; Q ) 0.41, e ) -0.26 may be related to the polarity of the polymerizable double bonds. Although there was no report on the Q and e values of NVNPI, the monomer may have a electron-donating property, on the basis of the reported value of N-vinylphthalimide (Q ) 0.36, e ) -1.52), 63 which is an analogue of NVNPI having similar N-vinyl structure. In contrast, various Q and e values were reported on NIPAAm: Q ) 0.26, e ) -0.26 with maleic anhydride and Q ) 0.70, e ) -0.26 64 with methacrylic acid.…”

Section: Raft Copolymerizations Of Nvnpi With Variousmentioning

confidence: 99%

Synthesis of Well-Defined Alternating Copolymers by RAFT Copolymerization of N-Vinylnaphthalimide

2008

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A novel nonconjugated N-vinyl monomer, N-vinylnaphthalimide (NVNPI), was copolymerized with various comonomers via reversible addition-fragmentation chain transfer process. Two different chain transfer agents (CTAs), O-ethyl-S-(1-ethoxycarbonyl) ethyldithiocarbonate (CTA 1) and benzyl 1-pyrrolecarbodithioate (CTA 2), were compared for these copolymerizations with 2,2′-azobis(isobutyronitrile) as an initiator. The structures of the resulting copolymers were characterized by 1 H and 13 C NMR spectroscopy, suggesting the sufficient incorporation of NVNPI, when methyl acrylate and N-isopropylacrylamide (NIPAAm) were used as comonomers.

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Section: Raft Copolymerizations Of Nvnpi With Variousmentioning

confidence: 99%

Synthesis of Well-Defined Alternating Copolymers by RAFT Copolymerization of N-Vinylnaphthalimide

2008

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“…The stabilizing effect of NVPI (Q ¼ 0.36, e ¼ À1.52) [44] is comparable to that of N-vinylcarbazole (Q ¼ 0.26, e ¼ À1.29) [45] with a higher electron-donating property, while the Q value is slightly lower than that of N-vinylindole (Q ¼ 0.53, e ¼ À1.30). [45] Similar to propagating radicals derived from N-vinylcarbazole and N-vinylindole, the NVPI propagating radical is a reactive species having a higher electron density at the radical center.…”

Section: Full Papermentioning

confidence: 99%

Controlled RAFT Polymerization of N‐Vinylphthalimide and its Hydrazinolysis to Poly(vinyl amine)

Maki

Mori

Endō

2007

Macro Chemistry & Physics

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Polymerization of NVPI was carried out by a RAFT process using five xanthate‐type, a dithiocarbamate‐type, and a dithioester‐type CTA. The xanthate‐type [O‐ethyl‐S‐(1‐ethoxy carbonyl) ethyl dithiocarbonate and O‐ethyl‐S‐(1‐ethoxycarbonyl‐1‐methyl)ethyl dithiocarbonate] and the dithiocarbamate‐type CTA (benzyl‐1‐pyrrolecarbodithioate) were the most efficient to obtain poly(NVPI) with controlled molecular weights ($\overline M _{\rm n}$ = 4 100–13 000) and low polydispersities ($\overline M _{\rm w} /\overline M _{\rm n}$ = 1.29–1.38). The effects of parameters such as solvent, temperature, and CTA‐to‐initiator molar ratio, were examined in order to determine the conditions leading to optimal control of the polymerization.magnified image

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“…Note that NVPI may have a electron-donating property (Q ¼ 0.36, e ¼ -1.52). [52] In contrast, various Q and e values were reported on NIPAAm:…”

Section: Raft Copolymerizations Of Nvpi With Various Comonomersmentioning

confidence: 99%

Controlled Synthesis of Alternating Copolymers by RAFT Copolymerization of N‐Vinylphthalimide with N‐Isopropylacrylamide

Maki¹,

Mori

Endō

2010

Macro Chemistry & Physics

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A nonconjugated N‐vinyl monomer, N‐vinylphthalimide (NVPI), was copolymerized with various comonomers via reversible addition‐fragmentation chain transfer (RAFT) process. Two different chain transfer agents (CTAs), O‐ethyl‐S‐(1‐ethoxycarbonyl) ethyldithiocarbonate (CTA 1) and benzyl 1‐pyrrolecarbodithioate (CTA 2), were compared for these copolymerizations with 2,2′‐azobis(isobutyronitrile) as an initiator. The effects of the nature of CTA, the comonomer structure, and solvent on the copolymerization were investigated in terms of the controlled character of the copolymerization and alternating structure. The copolymerization of NVPI and N‐isopropylacrylamide using CTA 2 in DMF or MeOH afforded well‐defined copolymers with predominantly alternating structure, controlled molecular weights, and low molecular mass distributions.magnified image

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Radical polymerization behavior of N‐vinylsaccharin

Cited by 6 publications

References 2 publications

Synthesis of Well-Defined Alternating Copolymers by RAFT Copolymerization of N-Vinylnaphthalimide

Synthesis of Well-Defined Alternating Copolymers by RAFT Copolymerization of N-Vinylnaphthalimide

Controlled RAFT Polymerization of N‐Vinylphthalimide and its Hydrazinolysis to Poly(vinyl amine)

Controlled Synthesis of Alternating Copolymers by RAFT Copolymerization of N‐Vinylphthalimide with N‐Isopropylacrylamide

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