Browsing by Subject "isosorbide"
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Item Degradable Materials from Sugar-Derived Feedstocks(2019-01) Lillie, LeonSugar-derived molecules have excellent potential to serve as building blocks in the development of sustainable polymers with high performance and rich functionality. This thesis focuses on the utilization of carbohydrate-derived molecules (bicyclic sugar derivatives and sugar metabolites) to enhance the degradability of polymeric materials. The first area of research presented describes the synthesis of a novel GDL-based α,ω-diene (glucarodilactone 10-undecenoate, GDLU). This molecule and its congener (isosorbide undecenoate, IU), were found to be highly suitable monomers for acyclic diene metathesis polymerization and were used to produce a family of homopolymers and copolymers of various GDLU:IU ratios. The structure/property implications of these similar sugar-derived diols on the materials physical performance and hydrolytic stability were explored. The second area of research expanded the usage of GDLU to a new class of materials, poly(ester-thioethers), with the use of photo-initiated thiol-ene polymerization. The impact of dithiol chemistry on material thermal and mechanical properties were investigated. Finally, the third area of research details the synthesis of novel methacrylic anhydride-like monomers obtained from the two-step synthetic modification of itaconic acid. These monomers were polymerized via thiol-ene polymerizations to obtain degradable, polyanhydride-based thermoset materials, with rapid neutral water degradation.Item Ring-Opening Polymerization as a Platform for Tailored Polymers from Isosorbide and Other Renewable Feedstocks(2020-10) Saxon, DerekTo withstand the critical need for plastics, we must innovate how polymers are constructed and deconstructed. Isosorbide and other renewable feedstocks have shown exceptional promise as replacements for commodity plastics. The work in thesis describes ring-opening polymerization as a previously unexplored strategy to synthesize polymers primarily from isosorbide, as well as several other renewable feedstocks. We describe traditional and contemporary approaches to synthesizing polymers from isosorbide along with the current challenges faced (Chapter 1). Initial efforts were aimed at developing polyethers with isosorbide in the backbone through ring-opening polymerization of an annulated isosorbide derivative, ultimately providing control over both the polymer microstructure and macromolecular architecture, enabling cyclic or linear polymers to be targeted (Chapter 2). This work is a stepping-stone for polymerization of complex heterocycles from renewable feedstocks. We then turned our focus to polycarbonate analogs to the poly(meth)acrylates previously developed in our lab (Chapter 3). Specifically, we established a method for the rapid synthesis of chemically recyclable, functional (co)polycarbonates with tailored thermal properties from isosorbide and other renewably derived alcohols. The polycarbonates were then redesigned to exploit industrial waste streams—specifically glycerol and carbon dioxide—to construct the value-added polymer backbone (Chapter 4). Tandem functionalization and ring-opening polymerization is being pursued to afford polycarbonates with 100% renewable content. These efforts may facilitate the development of commercially relevant sustainable polycarbonates with tailored properties that work toward eliminating plastic waste streams.