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

Ryan J. Pounder, David J. Fox, Ian A. Barker, Michael J. Bennison, Andrew P. Dove

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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.

Original languageEnglish
Pages (from-to)2204-2212
Number of pages9
JournalPolymer Chemistry
Volume2
Issue number10
DOIs
Publication statusPublished - Oct 2011
Externally publishedYes

Cite this

Pounder, R. J., Fox, D. J., Barker, I. A., Bennison, M. J., & Dove, A. P. (2011). Ring-opening polymerization of an O-carboxyanhydride monomer derived from L-malic acid. Polymer Chemistry, 2(10), 2204-2212. https://doi.org/10.1039/c1py00254f