Date of Thesis



Current methods of drug delivery such as oral tablets or injections suffer from problems with patient compliance, toxic side effects, and inefficient treatment. In addition, the development of new drugs and protein therapeutics is driving research into new and improved methods of controlled drug delivery. Controlled delivery devices aim to eliminate or reduce the previously mentioned problems by maintaining a constant drug concentration over an extended period of time. This research aimed to synthesize novel pyrrolidone containing polyanhydrides for use in controlled drug delivery devices. Such polymers would possess both the labile hydrolytic degradation property of anhydrides and the bonding and stabilization capabilities of pyrrolidones. Combined, these molecules give promise for a controlled drug delivery method that maintains constant drug concentration within the body while also stabilizing drugs to maximize the efficiency and efficacy of a pharmaceutical. To explore the effect of different monomer structures on the final polymers, we have conducted this reaction with three different primary amines: hexamethylenediamine, Jeffamine EDR-176, and p-phenylenediamine. The neat reaction of these diamines with itaconic acid yielded pyrrolidone carboxylic diacids that could be acetylated and polymerized to form polyanhydrides. This thesis focuses on the synthesis of the novel polyanhydrides, characterization of the polymer properties, and the development of a novel polymerization technique to overcome challenges faced with traditional melt polycondensation to form polyanhydrides.


pyrrolidones, polyanhydrides, polymers, controlled drug delivery, diacid, organic synthesis, chemistry, chemical engineering, soxhlet, polycondensation, melt polymerization, solution polymerization, pharmaceuticals, protein delivery, carboxylic acid, degradation, polymer erosion, drug release, nmr, high molecular weight polyanhydrides

Access Type

Masters Thesis (Bucknell Access Only)

Degree Type

Master of Science in Chemical Engineering


Chemical Engineering

First Advisor

Brandon M. Vogel