 Surface eroding materials are increasingly sought after in the biomedical area as a consequence of their potential application in drug delivery or tissue engineering. Poly(orthoester)s (POEs) are an ideal example of polymers that exhibit surface erosion with relatively mild degradation products compared to those of other surface erodible polymers, for example, poly(anhydride)s. However, POEs have previously proven difficult to synthesize, with general techniques for POE production involving the polymerization of highly unstable diketene acetal monomers, that are highly sensitive to air and moisture. Herein, an alternate method for the production of POEs via the use of air- and moisture-stable vinyl acetal monomers is discussed. POEs were successfully produced using a ruthenium-based catalyst through the 1,3-dihydride shift of the vinyl acetal monomers. A range of vinyl acetal monomers, including hetero- and homo-difunctional monomers, are readily shown to polymerize via this method. Furthermore, the technique was expanded to produce a range of POEs that have previously proven challenging to obtain. The efficient installation of functional groups viaan ortho ester linkage to a degradable aliphatic poly(carbonate) backbone is also realized.

Improved synthesis of poly(orthoester)s for biomedical application

248th National Meeting (2014)

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