Cyclopolymerization. 16. Anionic cyclopolymerization of N-methyldiacrylamide: 5-membered ring formation through head-to-head and tail-to-tail additions

Kodaira, Toshiyuki; Tanahashi, Hiromi

doi:10.1021/ma00202a044

Cited by 13 publications

(4 citation statements)

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“…A series of studies has been undertaken on the anionic polymerizations of unconjugated dienes that form highly cyclized polymers with fivemembered rings as their repeat cyclic units in their radical polymerizations. The monomers investigated are N-methyldimethacrylamide [12,13], N-tert-butyl-N-allylacrylamide [14], and 3 [3]. Interestingly, polymers with five-membered rings are formed from all these monomers even in their anionic polymerizations in the case where cyclopolymerization proceeds.…”

Section: Discussionmentioning

confidence: 99%

Cyclopolymerization. Part XXXI. An attempt to control the reaction courses of the polymerizations of N-methyl-N-allyl-2-(ethoxycarbonyl)allylamine by using anionic and radical initiators

Urushisaki

Kodaira

Takahashi

et al. 2003

Polymer

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Section: Discussionmentioning

confidence: 99%

Cyclopolymerization. Part XXXI. An attempt to control the reaction courses of the polymerizations of N-methyl-N-allyl-2-(ethoxycarbonyl)allylamine by using anionic and radical initiators

Urushisaki

Kodaira

Takahashi

et al. 2003

Polymer

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“…However, a relatively large amount of M-BisNVA was required for the gelation of NVA (runs 5-7 in Table I ) . It can be assumed that a part of added M-BisNVA cyclized intramolecularly as similarly as N-methyldiacrylamide ( Nmethydiacryloylamine ) , 28 which was supported by the NMR spectrum of M-BisNVA in the presence of a free-radical initiator at 55°C. When butylene-BisNVA (B-BisNVA) is used as a crosslinker, 0.2% of it is enough for NVA gel formation.…”

Section: Percent Of Crosslinkermentioning

confidence: 91%

Novel nonionic and cationic hydrogels prepared from N‐vinylacetamide

Akashi

Saihata

Yashima

et al. 1993

J. Polym. Sci. A Polym. Chem.

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SYNOPSISPoly (N-vinylacetamide ) ( polyNVA) hydrogels were prepared by the copolymerization of N-vinylacetamide (NVA) with divinyl compounds such as methylene-bis-acrylamide, methylene-bis-NVA, and butylene-bis-NVA in a high yield. The resulting hydrogels were more stable than polyacrylamide gel and showed quite a high swelling property in a wide range of pH ( 1-12) and even in a 5 M NaCl solution. They showed not only typical characteristics nonionic hydrogels, but also an amphiphilic property and they swelled well in some organic solvents. When the gels were partially hydrolyzed, cationic hydrogels, i.e., crosslinked poly ( NVA-co-vinylamine) , were collected. The resulting superabsorbent hydrogels absorbed 400 times of water. 0 1993 John Wiley & Sons, Inc. Keywords: N-vinylacetamide hydrogel crosslinked polymer free radical polymerization poly (vinylamine )

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“…1,6-Dienes such as N -methyldiacrylamide (MDA) (Chart ) and N-tert -butyl- N -allylacrylamide (BAA) form selectively a five-membered ring as a repeating cyclic unit in their anionic polymerizations , as well as in their radical counterparts, , though they have two possible cyclic repeating structures, i.e., five- and six-membered rings. These polymers were essentially free from pendant unsaturations except for poly(BAA) obtained through an anionic mechanism, which contained pendant allyl groups less than 20% in its repeating units .…”

Section: Introductionmentioning

confidence: 99%

Cyclopolymerization. 25. Five-Membered Ring Formation through Head-to-Head and Tail-to-Tail Additions in Radical and Anionic Polymerizations of α-(Allyloxymethyl)acrylates

et al. 1998

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Radical and anionic polymerizations of methyl and tert-butyl α-(allyloxymethyl)acrylates (AMA and ABA, respectively) were undertaken to see whether five-membered ring formation through head-to-head and tail-to-tail additions can occur irrespective of the polymerization mechanism. Both the monomers yielded highly cyclized polymers with a five-membered ring as a repeating cyclic unit in their radical polymerizations. Lithium compounds such as n-butyl- and tert-butyllithiums yielded highly isotactic uncyclized poly(AMA)s, while tert-butylmagnesium chloride afforded polymers with a considerably higher degree of cyclization (70%), the repeating cyclic units of which consist of a five-membered ring. Poly(ABA)s obtained through an anionic mechanism were found to have a five-membered ring as a repeating cyclic unit and degrees of cyclization higher than 80% irrespective of the initiator used. The structure of the anionically obtained cyclopolymers was fundamentally the same as those formed through a radical mechanism. These results along with those obtained from methyl and tert-butyl α-(propoxymethyl)acrylates, one of the monofunctional counterparts of AMA and ABA, respectively, led to the conclusion that anionic cyclopolymerizations proceed in the case where interaction of a countercation with the propagating chain end and the monomer is weak.

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Cyclopolymerization. 16. Anionic cyclopolymerization of N-methyldiacrylamide: 5-membered ring formation through head-to-head and tail-to-tail additions

Cited by 13 publications

References 1 publication

Cyclopolymerization. Part XXXI. An attempt to control the reaction courses of the polymerizations of N-methyl-N-allyl-2-(ethoxycarbonyl)allylamine by using anionic and radical initiators

Cyclopolymerization. Part XXXI. An attempt to control the reaction courses of the polymerizations of N-methyl-N-allyl-2-(ethoxycarbonyl)allylamine by using anionic and radical initiators

Novel nonionic and cationic hydrogels prepared from N‐vinylacetamide

Cyclopolymerization. 25. Five-Membered Ring Formation through Head-to-Head and Tail-to-Tail Additions in Radical and Anionic Polymerizations of α-(Allyloxymethyl)acrylates

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