Alternating copolymerization of vinylphosphonic acid monoethyl ester with cyclic phosphonites involving proton-transfer

Jun Ichi Kadokawa; I. Fang Yen; Shin Ichiro Shoda; Hiroshi Uyama; Shiro Kobayashi

doi:10.1295/polymj.24.1205

Alternating copolymerization of vinylphosphonic acid monoethyl ester with cyclic phosphonites involving proton-transfer

Jun Ichi Kadokawa, I. Fang Yen, Shin Ichiro Shoda, Hiroshi Uyama, Shiro Kobayashi

ENG - Biomolecular Engineering

Research output: Contribution to journal › Article › peer-review

Abstract

This paper describes the alternating copolymerization of vinylphosphonic acid monoethyl ester 1 with five-, six-, and seven-membered cyclic phosphonites (2a, 2b, and 2c). The copolymerization took place without any catalyst. Reaction of the 1:1 monomer feed ratio gave alternating copolymers having the phosphonite-phosphonate unit. During the copolymerization the proton-transfer in monomer 1 took place and the oxidation-reduction process is involved. The copolymerization is reasonably explained by a mechanism which involves zwitterion intermediates. The apparent monomer reactivity ratios determined in benzonitrile at 150°C are r1=0.00 and r_2b=0.16. A kinetic study of the Michael-type addition in the initiation stage showed that 2b was more reactive than 2a or 2c.

Original language	English
Pages (from-to)	1205-1214
Number of pages	10
Journal	Polymer Journal
Volume	24
Issue number	11
DOIs	https://doi.org/10.1295/polymj.24.1205
Publication status	Published - 1992 Nov

Keywords

Alternating copolymerization
Cyclic phosphonite
Proton-transfer
Vinylphosphonic acid monoethyl ester
Zwitterion mechanism

ASJC Scopus subject areas

Polymers and Plastics
Materials Chemistry

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10.1295/polymj.24.1205

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title = "Alternating copolymerization of vinylphosphonic acid monoethyl ester with cyclic phosphonites involving proton-transfer",

abstract = "This paper describes the alternating copolymerization of vinylphosphonic acid monoethyl ester 1 with five-, six-, and seven-membered cyclic phosphonites (2a, 2b, and 2c). The copolymerization took place without any catalyst. Reaction of the 1:1 monomer feed ratio gave alternating copolymers having the phosphonite-phosphonate unit. During the copolymerization the proton-transfer in monomer 1 took place and the oxidation-reduction process is involved. The copolymerization is reasonably explained by a mechanism which involves zwitterion intermediates. The apparent monomer reactivity ratios determined in benzonitrile at 150°C are r1=0.00 and r2b=0.16. A kinetic study of the Michael-type addition in the initiation stage showed that 2b was more reactive than 2a or 2c.",

keywords = "Alternating copolymerization, Cyclic phosphonite, Proton-transfer, Vinylphosphonic acid monoethyl ester, Zwitterion mechanism",

author = "Kadokawa, {Jun Ichi} and Yen, {I. Fang} and Shoda, {Shin Ichiro} and Hiroshi Uyama and Shiro Kobayashi",

year = "1992",

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doi = "10.1295/polymj.24.1205",

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T1 - Alternating copolymerization of vinylphosphonic acid monoethyl ester with cyclic phosphonites involving proton-transfer

AU - Kadokawa, Jun Ichi

AU - Yen, I. Fang

AU - Shoda, Shin Ichiro

AU - Uyama, Hiroshi

AU - Kobayashi, Shiro

PY - 1992/11

Y1 - 1992/11

N2 - This paper describes the alternating copolymerization of vinylphosphonic acid monoethyl ester 1 with five-, six-, and seven-membered cyclic phosphonites (2a, 2b, and 2c). The copolymerization took place without any catalyst. Reaction of the 1:1 monomer feed ratio gave alternating copolymers having the phosphonite-phosphonate unit. During the copolymerization the proton-transfer in monomer 1 took place and the oxidation-reduction process is involved. The copolymerization is reasonably explained by a mechanism which involves zwitterion intermediates. The apparent monomer reactivity ratios determined in benzonitrile at 150°C are r1=0.00 and r2b=0.16. A kinetic study of the Michael-type addition in the initiation stage showed that 2b was more reactive than 2a or 2c.

AB - This paper describes the alternating copolymerization of vinylphosphonic acid monoethyl ester 1 with five-, six-, and seven-membered cyclic phosphonites (2a, 2b, and 2c). The copolymerization took place without any catalyst. Reaction of the 1:1 monomer feed ratio gave alternating copolymers having the phosphonite-phosphonate unit. During the copolymerization the proton-transfer in monomer 1 took place and the oxidation-reduction process is involved. The copolymerization is reasonably explained by a mechanism which involves zwitterion intermediates. The apparent monomer reactivity ratios determined in benzonitrile at 150°C are r1=0.00 and r2b=0.16. A kinetic study of the Michael-type addition in the initiation stage showed that 2b was more reactive than 2a or 2c.

KW - Alternating copolymerization

KW - Cyclic phosphonite

KW - Proton-transfer

KW - Vinylphosphonic acid monoethyl ester

KW - Zwitterion mechanism

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JO - Polymer Journal

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Alternating copolymerization of vinylphosphonic acid monoethyl ester with cyclic phosphonites involving proton-transfer

Abstract

Keywords

ASJC Scopus subject areas

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