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Issue 10, 2011
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Ring-opening polymerization of an O-carboxyanhydride monomer derived from l-malic acid

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Abstract

The synthesis and ring-opening polymerization (ROP) of an O-carboxyanhydride (OCA) monomer derived from L-malic acid (L-malOCA) is reported. Application of 4-dimethylaminopyridine as catalyst led to the observation of a number of undesirable side products. Investigation of different para-substituted pyridines as catalysts identified 4-methoxypyridine to have the ideal balance of activity and selectivity to enable the controlled ROP of L-malOCA. Deprotection of the benzyl ester side groups of the resultant polymers was achieved by hydrogenolysis and the resulting hydrophilic poly(α-malic acid) was observed to fully degrade within 7 days in aqueous solution.

Graphical abstract: Ring-opening polymerization of an O-carboxyanhydride monomer derived from l-malic acid

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Article information


Submitted
02 Jun 2011
Accepted
20 Jun 2011
First published
19 Jul 2011

Polym. Chem., 2011,2, 2204-2212
Article type
Paper

Ring-opening polymerization of an O-carboxyanhydride monomer derived from L-malic acid

R. J. Pounder, D. J. Fox, I. A. Barker, M. J. Bennison and A. P. Dove, Polym. Chem., 2011, 2, 2204
DOI: 10.1039/C1PY00254F

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