Complex, Degradable Polyester Materials via Ketoxime Ether-Based Functionalization: Amphiphilic, Multifunctional Graft Copolymers and Their Resulting Solution-State Aggregates
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abstract
Degradable, amphiphilic graft copolymers of poly(-caprolactone)- grarf-poly(ethylene oxide), PCL-g-PEO, were synthesized via a grafting onto strategy taking advantage of the ketones presented along the backbone of the statistical copolymer poly(-caprolactone)-co-(2-oxepane-1, 5-dione), (PCLco-OPD). Through the formation of stable ketoxime ether linkages, 3 kDa PEO grafts and p-methoxybenzyl side chains were incorporated onto the polyester backbone with a high degree of fidelity and efficiency, as verified by NMR spectroscopies and GPC analysis (90% grafting efficiency in some cases). The resulting block graft copolymers displayed significant thermal differences, specifically a depression in the observed melting transition temperature, T m, in comparison with the parent PCL and PEO polymers. These amphophilic block graft copolymers undergo self-assembly in aqueous solution with the P(CL-coOPD-co-(OPD-g-PEO)) polymer forming spherical micelles and a P(CL-co-OPD-co-(OPD-g-PEO)-co-(OPD-g-pMeOBn)) forming cylindrical or rod-like micelles, as observed by transmission electron microscopy and atomic force microscopy. 2010 Wiley Periodicals, Inc.
