Degradable Materials from Sugar-Derived Feedstocks

Abstract

Sugar-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.