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Issue 4, 2015
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Accelerated living cationic ring-opening polymerization of a methyl ester functionalized 2-oxazoline monomer

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Abstract

Kinetic studies on the homo- and copolymerization of 2-methoxycarboxyethyl-2-oxazoline (MestOx) with 2-methyl-2-oxazoline (MeOx) and 2-ethyl-2-oxazoline (EtOx) were performed. For the homopolymerisation of MestOx an increased propagation rate constant was observed compared to MeOx and EtOx while the copolymerization of MestOx with MeOx or EtOx unexpectedly revealed slower incorporation of MestOx. Density functional theory (DFT) calculations show that nearby MestOx residues in the living chain can activate both the oxazolinium chain end and the attacking monomer, stabilizing the propagation transition state, leading to faster homopolymerisation of MestOx. These effects also accelerate incorporation of both monomers in the copolymerisations. However, since MeOx is shown to be more nucleophilic than MestOx, the incorporation order is reversed in the copolymerisations.

Graphical abstract: Accelerated living cationic ring-opening polymerization of a methyl ester functionalized 2-oxazoline monomer

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Publication details

The article was received on 08 Oct 2014, accepted on 27 Oct 2014 and first published on 28 Oct 2014


Article type: Communication
DOI: 10.1039/C4PY01373E
Polym. Chem., 2015,6, 514-518

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    Accelerated living cationic ring-opening polymerization of a methyl ester functionalized 2-oxazoline monomer

    P. J. M. Bouten, D. Hertsen, M. Vergaelen, B. D. Monnery, M. A. Boerman, H. Goossens, S. Catak, J. C. M. van Hest, V. Van Speybroeck and R. Hoogenboom, Polym. Chem., 2015, 6, 514
    DOI: 10.1039/C4PY01373E

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