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

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Pounder, Ryan J., Fox, David J., Barker, Ian A., Bennison, Michael J. and Dove, Andrew P. (2011) Ring-opening polymerization of an O-carboxyanhydride monomer derived from l-malic acid. Polymer Chemistry, Vol.2 (No.10). pp. 2204-2212. doi:10.1039/c1py00254f ISSN 1759-9954.

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Official URL: http://dx.doi.org/10.1039/c1py00254f

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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(a-malic acid) was observed to fully degrade within 7 days in aqueous solution.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH): Ring-opening polymerization, Monomers
Journal or Publication Title: Polymer Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1759-9954
Official Date: October 2011
Dates:
DateEvent
October 2011Published
Volume: Vol.2
Number: No.10
Page Range: pp. 2204-2212
DOI: 10.1039/c1py00254f
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access

Data sourced from Thomson Reuters' Web of Knowledge

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