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Synthesis of polymers with pendant spiro orthoester groups
Author(s) -
Zamzow Manfred,
Höcker Hartwig
Publication year - 1994
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.1994.021950708
Subject(s) - orthoester , methacrylate , polymer chemistry , chemistry , acrylate , monomer , hydroxymethyl , ether , methyl methacrylate , polymer , moiety , polymerization , organic chemistry
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.