Date of Thesis
Polyanhydrides have emerged as an attractive biomaterial for use in controlled drug delivery applications for the release of designed therapeutics. These polymers are ideal vehicles for controlled drug delivery due to their tailorable erosion and degradation characteristics. However, current methods of synthesis possess several limitations that make them undesirable for synthesis of thermally-sensitive molecules. This research sought to develop two novel synthesis routes for the formation of thermally-sensitive molecules that remain unsuited for synthesis in conventional melt polycondensation. These methods would allow for the synthesis of polyanhydrides at milder conditions while also providing the desired high molecular weight offered by traditional methods. To this effort, the first method explored using p-toluenesulfonyl chloride as a potential dehydrative coupling agent that would induce polymerization of dicarboxylic acids when in the presence of a base at ambient temperatures. The reaction of p-toluenesulfonyl chloride with triethylamine and diisopropylethylamine resulted in successful polymerization aliphatic and aromatic diacids with high molecular weights. The second method explored the use of solid-phase extractive polymerization with a Soxhlet extractor to polymerize aliphatic and aromatic diacids with high molecular weight. This method incorporated a solvent as a way of modifying conventional melt polycondensation as a means of controlling the driving forces of the reaction in the form of byproduct removal and temperature control. This thesis focused on the successful synthesis of polyanhydrides, the characterization of the polymer products, and the development of these methods.
Polyanhydrides, Polymers, Soxhlet, Tosyl Chloride, Solution Polycondensation, Extractive Polymerization
Masters Thesis (Bucknell Access Only)
Master of Science in Chemical Engineering
Dr. Brandon Vogel
Titman, Joe, "Synthesis of Aliphatic and Aromatic Polyanhydrides via Tosyl Chloride-Mediated Solution Polycondensation and Solid-Phase Extractive Polymerization" (2020). Master’s Theses. 243.
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