Anionic Copolymerization of o-Phthalaldehyde with Epoxides: Facile Access to Degradable Polyacetals and Their Copolymers under Ambient Conditions

Traditionally o-phthalaldehyde (OPA) has to be homopolymerized or copolymerized with other monomers at low temperature due to its very low ceiling temperature (T-c = -36 degrees C). In the presence of a Lewis acid such as triethylborane (TEB) the anionic copolymerization of OPA with various epoxides including ethylene oxide, propylene oxide, 1-butene oxide, 1-octene oxide, allyl glycidyl ether, phenyl glycidyl ether, and styrene oxide could be successfully carried out under ambient conditions, resulting in the formation of a host of polyacetals. The role and effect of TEB, its amount, and also the feeding ratio of OPA to epoxides during their copolymerizations were respectively investigated. The successful living OPA/epoxides copolymerization was further extended to the synthesis of polyether-b-polyacetal block copolymers with different structure and properties.

Automated summary

By adding Lewis acid such as triethylborane (TEB), the copolymerization of o-phthalaldehyde (OPA) with various epoxides has been successfully carried out under ambient conditions, resulting in the formation of polyacetals. The role and effect of TEB, its amount, and the feeding ratio of OPA to epoxides during their copolymerizations were investigated. The successful copolymerization was further extended to the synthesis of polyether-b-polyacetal block copolymers with different structure and properties.