Polymerization via Zwitterion. 9. Alternating Copolymerizations of 2-Phenyl-1,3,2-dioxaphospholane with Electrophilic Monomers of Acrylic Acid, β-Propiolactone, and Acrylamide

Sàegusa, Takeo; Kimura, Yoshiharu; Ishikawa, Noriaki; Kobayashi, Shiro

doi:10.1021/ma60053a008

Cited by 39 publications

(16 citation statements)

References 7 publications

(14 reference statements)

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“…Solvents, benzonitrile, nitrobenzene, chlorobenzene, and toluene, were all purified as previously reported. 13 Pyruvic acid was a commercial reagent, which was purified by repeated distillation under nitrogen. Phenylglyoxylic acid was prepared by acid hydrolysis of commercially available benzoyl cyanide,24 which was then purified by recrystallization from carbon tetrachloride, mp, 65-67 °C (lit.24 64-66 °C).…”

Section: Methodsmentioning

confidence: 99%

“…Anal. Found: C, 29.97; H, 4.73; P, 13.20. Received April 13,1977 ABSTRACT: Methyl -n-alkylacrylates (alkyl = CmHas and CigHav) were copolymerized with methyl methacrylate in bulk at 50 °C using a free-radical catalyst (AIBNhmd anionically (sodium) in toluene at room temperature. Freeradical copolymerizations yielded polymers having Mn from 11 600 to 29 000 (22-83% yield).…”

Section: Methodsmentioning

confidence: 99%

“…Spontaneous alternating copolymerization, in which a nucleophilic monomer Mn and an electrophilic monomer Mg are mixed with each other to produce the key intermediate of "genetic zwitterion", +Mn-Me~, has been developed by us. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] Mn monomers which have hitherto been explored are cyclic imino ethers2-10 (five-and six-membered), N-alkyliminotetrahydrofuran,11 cyclic amine,12 cyclic phosphonite, 13-15 and Schiff base, 16 and Me monomers are ß-propiolactone, cyclic anhydride of dibasic acid,4-16 sulfo-lactone (sultone) of 7hydroxypropanesulfonic acid,5•14 acrylic acid,6•10-13,16 acrylamide,7,13 hydroxyalkyl acrylates,8 and ethylenesulfonamide.9,15 Many new copolymerizations have been developed by the combinations of the above Mn and Me monomers. In addition, the alternating copolymerization of cyclic phosphonite with acrylates17 as well as the 1:1:1 alternating terpolymerization of cyclic phosphonite, acrylate, and carbon dioxide18 are known.…”

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confidence: 99%

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Polymerization via Zwitterion. 16. Alternating Copolymerization of Cyclic Phosphite with α-Keto Acid

Sàegusa¹,

Yokoyama²,

Kimura³

et al. 1977

Macromolecules

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This paper describes a new spontaneous copolymerization between the cyclic phosphite of 2-phenoxy-1,3,2-dioxaphospholane and an -keto acid such as pyruvic acid and phenylglyoxylic acid. The copolymerization occurred at temperatures above 100 °C without added catalyst to produce alternating copolymers. During copolymerization, the phosphite Pm in monomer was oxidized to phosphate Pv in the copolymer unit. Thus, it may well be termed "oxidation-reduction copolymerization". A scheme of polymerization involving a phosphonium zwitterion was presented.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Polymerization via Zwitterion. 16. Alternating Copolymerization of Cyclic Phosphite with α-Keto Acid

Sàegusa¹,

Yokoyama²,

Kimura³

et al. 1977

Macromolecules

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“…(25) in Ether in fast quantitativer Ausbeute ein kristallines Material, Fp=SO"C, rnit der Struktur (46)[251. Die ambifunktionelle anionische Gruppe des Zwitterions ( 4 7 ) reagiert bei der Copolymerisation von (16) …”

Section: Copolymerisation Von Cyclischen Phosphorverbindungen Rnit Elunclassified

Spontan ablaufende alternierende Copolymerisation über Zwitterion‐Zwischenstufen

Sàegusa

1977

Angewandte Chemie

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In diesem Aufsatz wird ein neuer Copolymerisationstyp beschrieben, der sich dadurch auszeichnet, dalj das Kettenwachstum spontan ohne Zusatz eines Katalysators ablauft. Ein nucleophiles (MN) und ein elektrophiles Monomer (ME) reagieren zu einem Zwitterion ('MN-ME), von dem Start-und Wachstumsreaktionen ausgehen. 23 neuartige Copolymerisationen wurden auf der Basis dieses Konzepts ausgearbeitet. Als MN-Monomere wurden funf-und sechsgliedrige cyclische Iminoether, Dihydro-2(3H)-furanimin, ein Azetidin, ein cyclischer Phosphinsaureester und eine Schiff-Base untersucht, als ME-Monomere a-Propiolacton, ein cyclisches Dicarbonsaureanhydrid, ein Sulton, Acrylsaure, Acrylamid, ein a-Hydroxyalkylarylat und Ethylensulfonamid. Bei den meisten Kombinationen entstehen alternierende 1 : I-Copolymere. Auljerdem wurde die alternierende 1 : 1 -Copolymerisation eines cyclischen Phosphits mit cc-Ketosauren entdeckt.

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“…Figure3. NMR spectra of (a) the alkaline hydrolysis product of the EPO-ESAm cooligomer and (b) a mixture of the Na salt of4 and ethylene glycol in D20.…”

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confidence: 99%

Polymerization via Zwitterion. 18. Alternating Cooligomerizations of Ethylenesulfonamide with Cyclic Phosphorus Compounds

Sàegusa¹,

Kobayashi²,

Furukawa³

1978

Macromolecules

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Polymerization via Zwitterion. 9. Alternating Copolymerizations of 2-Phenyl-1,3,2-dioxaphospholane with Electrophilic Monomers of Acrylic Acid, β-Propiolactone, and Acrylamide

Cited by 39 publications

References 7 publications

Polymerization via Zwitterion. 16. Alternating Copolymerization of Cyclic Phosphite with α-Keto Acid

Polymerization via Zwitterion. 16. Alternating Copolymerization of Cyclic Phosphite with α-Keto Acid

Spontan ablaufende alternierende Copolymerisation über Zwitterion‐Zwischenstufen

Polymerization via Zwitterion. 18. Alternating Cooligomerizations of Ethylenesulfonamide with Cyclic Phosphorus Compounds

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