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Issue 42, 2015
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Controlling the synthesis of degradable vinyl polymers by xanthate-mediated polymerization

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Abstract

The copolymerization of vinyl acetate (VAc) and 2-methylene-1,3-dioxepane (MDO), as well as the homopolymerization of MDO in the presence of a p-methoxyphenyl xanthate chain transfer agent (CTA) is reported and comparison of the homopolymerization of MDO with other known xanthates was also investigated. In depth investigation showed loss of the xanthate functionality was a result of Z-group fragmentation leading to the formation of carbonodithioate groups, as confirmed by 13C NMR spectroscopy. The use of the xanthate with a substituted phenyl Z-group drastically reduces fragmentation through the Z-group and hence significantly increases chain-end retention during the polymerization using the RAFT/MADIX technique. Post-polymerization modification of the chain-end of poly(MDO) was achieved by in situ aminolysis and base-catalyzed Michael addition of propargyl methacrylate onto the terminal thiol to form alkyne functional poly(MDO).

Graphical abstract: Controlling the synthesis of degradable vinyl polymers by xanthate-mediated polymerization

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The article was received on 23 Jul 2015, accepted on 29 Aug 2015 and first published on 02 Sep 2015


Article type: Paper
DOI: 10.1039/C5PY01156F
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Citation: Polym. Chem., 2015,6, 7447-7454
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    Controlling the synthesis of degradable vinyl polymers by xanthate-mediated polymerization

    C. A. Bell, G. G. Hedir, R. K. O'Reilly and A. P. Dove, Polym. Chem., 2015, 6, 7447
    DOI: 10.1039/C5PY01156F

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