Conidine—Synthesis, Polymerization and Derivatives

Lavagnino, E. R.; Chauvette, Robert R.; Cannon, William N.; Kornfeld, Edmund C.

doi:10.1021/ja01495a054

Cited by 43 publications

(6 citation statements)

References 2 publications

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“…The synthesis and homopolymerization of this monomer was first published in I960. Several authors studied the mechanism (Equation I6a,b) and kinetics of the polymerization (84)(85)(86).…”

Section: Linear Crystalline Polvflthvteniminamentioning

confidence: 99%

Synthetic Methods for Water-Soluble Monomers and Polymers

Butler

Zhang

1991

ACS Symposium Series

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This review is based on a lecture that has been presented over the past several years by one of us (GBB) in connection with certain well-established short courses. Although the major water-soluble non-polyelectrolytes are covered briefly in this review, the major emphasis is placed on well-studied and either commercially available polyelectrolyte monomers or such monomers which have the potential for commercial development.The latter judgment is based on availability of raw materials, monomer and polymer yields, and/or quality of derivable polymers or copolymer. In many cases, only the monomers are emphasized, since methods for their polymerization generally parallel each other, all being predominantly initiated and polymerized via free radical mechanisms. No distinction is generally made among the several polymerization techniques such as aqueous or other solution processes, suspension or emulsion processes. In many cases all types have been studied. In most of the others, success in the application of the several techniques to the polymerization process can reasonably be predicted.Organic compounds having hydrophilic groups are soluble in water provided the hydrophobic-hydrophilic balance is favorable. Alcohols of low molecular weight are soluble in water; however, those of higher molecular weight are no longer soluble. The same principles apply to polymers. Table I includes the more common functional groups which impart water-solubility to organic compounds as well as to polymers. Non-polyelectrolytesAside from the naturally occurring water-soluble polysaccharides or their synthetically modified derivatives, the major contributors to the non-polyelectrolyte group of water-soluble polymers are: poly(acrylamide), poly(acrylic) or (methacrylic acids), poly(ethylene oxides), poly(methyl vinyl ether) and poly(vinyl alcohols). Polyacrylamide (PAM). Acrylamide polymerizes easily in aqueous solution inpresence of a wide variety of free-radical initiators (J_). Many added salts affect polymerization rate and molecular weight. Often, commercially produced poly(acrylamides) may contain a fraction that appears to be insoluble in water, a property which presents a problem for many uses. Much attention

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“…The synthesis and homopolymerization of this monomer was first published in I960. Several authors studied the mechanism (Equation I6a,b) and kinetics of the polymerization (84)(85)(86).…”

Section: Linear Crystalline Polvflthvteniminamentioning

confidence: 99%

Synthetic Methods for Water-Soluble Monomers and Polymers

Butler

Zhang

1991

ACS Symposium Series

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“…Unsurprisingly, most of this work on the polymerization of azetidines focuses on the polymerization of N-substituted azetidines. 4,[111][112][113][114][115] While the first polymerization of an azetidine ring was reported by Kornfeld, in 1960, regarding the polymerization of conidine, 113 Goethals provided the greatest contributions to the field due to his studies of multiple azetidines. 4,5,99,[115][116][117][118] In 1974, Goethals reported of the polymerization of unsubstituted azetidine (Scheme 9).…”

Section: Cationic Ring-opening Polymerization Of Azetidinesmentioning

confidence: 99%

Aziridines and azetidines: building blocks for polyamines by anionic and cationic ring-opening polymerization

et al. 2019

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“…The synthesis of this monomer and a few alkyl-substituted derivatives has been described by Lavagnino et al in 1960 and in Polymer J., Vol. 12, No.…”

Section: N-alkyl-substituted Azetidinesmentioning

confidence: 99%

“…9, 1980 the same paper the authors describe that these compounds yield amorphous polymers when treated with a trace amount of methyl iodide or boron trifluoride etherate. 10 Toy and Price 15 prepared the ·two pure enantiomers of conidine, which were also polymerized with boron trifluoride etherate. The polymer, with a strong optical rotation of opposite sign to that of the monomer from which it was formed, gave a sharply crystalline X-ray pattern and had a crystalline mp of 94°C.…”

Section: N-alkyl-substituted Azetidinesmentioning

confidence: 99%

The Polymerization of Azetidines and Azetidine Derivatives

Goethals

Schacht

Bogaert

et al. 1980

Polym J

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ABSTRACT:The cationic ring-opening polymerization of azetidine, N-alkylazetidines and a number of azetidines carrying a second functional group is reviewed. Some of these monomers lead to "living" polymers. The rate constants for the polymerization of different azetidines are discussed and compared with the rate constants for the polymerization of other four-membered heterocycles. The nucleophilic ring-opening polymerization of azetidinium salts is discussed. A new polymer with azetidinium endgroups is described. The synthesis, chemical properties, and applications of a number of polymers with pendant azetidinium substituents are described.

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Conidine—Synthesis, Polymerization and Derivatives

Cited by 43 publications

References 2 publications

Synthetic Methods for Water-Soluble Monomers and Polymers

Synthetic Methods for Water-Soluble Monomers and Polymers

Aziridines and azetidines: building blocks for polyamines by anionic and cationic ring-opening polymerization

The Polymerization of Azetidines and Azetidine Derivatives

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