Issue 15, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
14 May 2013
Accepted
07 Jun 2013
First published
10 Jun 2013

Polym. Chem., 2013,4, 4113-4119

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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