Polymerization of free secondary amine bearing monomers by RAFT polymerization and other controlled radical techniques

Authors

  • Tobias Janoschka,

    1. Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
    2. Jena Center for Soft Matter (JCSM), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
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  • Anke Teichler,

    1. Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
    2. Jena Center for Soft Matter (JCSM), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
    3. Dutch Polymer Institute (DPI), P.O. Box 902, 5600 AX Eindhoven, The Netherlands
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  • Andreas Krieg,

    1. Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
    2. Jena Center for Soft Matter (JCSM), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
    3. Dutch Polymer Institute (DPI), P.O. Box 902, 5600 AX Eindhoven, The Netherlands
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  • Martin D. Hager,

    1. Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
    2. Jena Center for Soft Matter (JCSM), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
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  • Ulrich S. Schubert

    Corresponding author
    1. Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
    2. Jena Center for Soft Matter (JCSM), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
    3. Dutch Polymer Institute (DPI), P.O. Box 902, 5600 AX Eindhoven, The Netherlands
    • Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich-Schiller-University Jena, Humboldtstr. 10, D-07743 Jena, Germany
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Abstract

This work describes the polymerization of the free secondary amine bearing monomer 2,2,6,6-tetramethylpiperidin-4-yl methacrylate (TMPMA) by means of different controlled radical polymerization techniques (ATRP, RAFT, NMP). In particular, reversible addition-fragmentation chain transfer (RAFT) polymerization enabled a good control at high conversions and a polydispersity index below 1.3, thereby enabling the preparation of well-defined polymers. Remarkably, the polymerization of the secondary amine bearing methacrylate monomer was not hindered by the presence of the free amine that commonly induces degradation of the RAFT reagent. Subsequent oxidation of the polymer yielded the polyradical poly(2,2,6,6-tetramethylpiperidinyloxy-4-yl methacrylate), which represents a valuable material used in catalysis as well as for modern batteries. The obtained polymers having a molar mass (Mn) of 10,000–20,000 g/mol were used to fabricate well-defined, radical-bearing polymer films by inkjet- printing. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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