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Issue 15, 2013
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Polymerization of long chain [meth]acrylates by Cu(0)-mediated and catalytic chain transfer polymerisation (CCTP): high fidelity end group incorporation and modification

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Abstract

The Cu(0)-mediated polymerization of lauryl (C12) and stearyl (C18) acrylate is reported under a range of reaction conditions. Good first order kinetics, a linear evolution of number average molecular weight (Mn) with conversion and dispersity (∼1.10) are observed. The polymerization of lauryl acrylate proceeds either homogenously or in a self-generated biphasic system, depending on the solvent employed, with little deviation in overall polymerization control. The near quantitative retention of ω-bromo end groups is exploited via nucleophilic thio-bromine substitution with thioglycerol to yield highly hydrophobic polymers with polar head groups. Modification is spectroscopically confirmed by both NMR and MALDI-TOF-MS. Highly ω-chain end functional methacrylic analogues have also been prepared by Co(II) mediated catalytic chain transfer polymerisation (CCTP). Reactive vinyl groups at the ω-chain end of poly(lauryl methacrylate) have been targeted with thioglycerol for nucleophilic thio-Michael addition with quantitative modification possible.

Graphical abstract: Polymerization of long chain [meth]acrylates by Cu(0)-mediated and catalytic chain transfer polymerisation (CCTP): high fidelity end group incorporation and modification

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Supplementary files

Article information


Submitted
14 May 2013
Accepted
07 Jun 2013
First published
10 Jun 2013

Polym. Chem., 2013,4, 4113-4119
Article type
Paper

Polymerization of long chain [meth]acrylates by Cu(0)-mediated and catalytic chain transfer polymerisation (CCTP): high fidelity end group incorporation and modification

A. Anastasaki, C. Waldron, V. Nikolaou, P. Wilson, R. McHale, T. Smith and D. M. Haddleton, Polym. Chem., 2013, 4, 4113
DOI: 10.1039/C3PY00618B

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