Abstract
This paper describes the synthesis of polymers having spiro orthoester side groups, starting from lactones with methacrylate side groups. The spiro orthoester polymers are synthesized by a reaction with an oxirane. The hydroxy-functional lactones 3-hydroxy-4,4-dimethyl-2-oxotetrahydrofuran (1) and 5-hydroxymethyl-2-oxotetrahydrofuran (13) were esterificated with methacryloyl chloride. The esterification of 5-oxotetrahydrofuran-2-carboxylic acid (6) and 2,2-dimethyl-5-oxotetrahydrofuran-3-carboxylic acid (11) with 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate yielded the functionalized precursors for the synthesis of polymeric spiro orthoesters. These monomers were polymerized and copolymerized with methyl methacrylate and characterized. Furtheron, the obtained polymers with lactone groups were converted to the corresponding spiro orthoesters using 2,3-epoxypropyl phenyl ether in the presence of boron trifluoride.
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