C16077 Marketing Summary
Unmet Need
Although vinyl alcohol-methyl methacrylate (VA-MMA) copolymers have intriguing functionally-rich structure that could impact a polymer’s properties, they are synthetically inaccessible from vinyl acetate (VAc), the traditional precursor to polyvinyl alcohol (PVA). VAc is poorly compatible with early transition metal olefin polymerization catalysts. VAc-derived radicals have the propensity to undergo chain transfer and termination events, presenting a challenge for controlled polymerization techniques such as atom transfer radical polymerization (ATRP). VAc also exhibits poor copolymerization behavior with conjugated monomers like styrene (St), methyl acrylate (MA), and methyl methacrylate (MMA).
Technology Overview
Johns Hopkins inventors report BN 2-vinylnaphthalene (BN2VN), a PVA precursor with versatile reactivity arising from its aromatic structure, for the free radical copolymerization with both MMA and tert-butyl methacrylate (tBMA). This work significantly expands the scope of functionally rich boron-functionalized polymers suitable for oxidative functionalization. This allowed the material to yield copolymers bearing ester and lactone subunits, as well as alcohol functional groups. The functionally rich and polar polymers prepared herein are likely to have several potential applications. As both PMMA and PVA are biocompatible polymers, conjugates could be prepared by covalent attachment of a desired small molecule. The lactone substructures may impart unique mechanical properties to the polymers by reducing degrees of freedom along the backbone.
Stage of Development
Inventors demonstrate BN2VN-MMA copolymerization and structurally characterized the resulting copolymer using nuclear magnetic resonance (NMR) spectroscopy and Fourier transform infrared (FTIR) spectroscopy. They further demonstrated postpolymerization functionalization of BN2VN-MMA copolymers by oxidation to yield copolymers bearing ester and lactone subunits.
Publications
Ji Y, Zhou T, van de Wouw HL, Klausen RS. Organoborane Strategy for Polymers Bearing Lactone, Ester, and Alcohol Functionality. Macromolecules. 2019. doi: 10.1021/acs.macromol.9b02201.
