Biodegradable polymeric materials have widespread and growing use in a variety of settings, including, packaging, energy, and medicine. Because of the increasing environmental impacts of non-degradable polymers, there is an acute need for improved and new biodegradable plastics. The practicality and wide-use of polymers for various applications also increase the demand for studying the mechanisms which are responsible for polymer degradability. Highly researched examples would be poly(lactic acid) or poly(lactic-co-glycolic acid). Mandelic acid and its derivatives are especially intriguing compounds because of their biodegradability, polymerizability, and properties similar to polystyrene. These poly(a-hydroxy acid)-type materials all degrade slowly through hydrolysis, with two main mechanisms: backbiting and chain scission. In the backbite mechanism, end-group hydroxyls depolymerize the backbone relatively quickly. While the chain scission degradation occurs by hydrolysis along the polymer backbone decreasing the polymer length and increasing the overall degradation rate. We therefore propose the development of scission-triggering groups for incorporation into poly(mandelic acid) derivatives. In this study, a simple and convenient synthesis of polyesters was prepared via ring opening polymerization of 5-substituted 1,3-dioxolan-4-ones (DOX), assembled from derivatives of mandelic acid. 5-bromophenyl, p-nitrophenyl, and o-nitrophenyl DOX, as well as and the control, phenyl-DOX, were all prepared in high yield. All DOX monomers were polymerized using tin(II) octoate (Sn(Oct)<sub>2</sub>), with concomitant elimination of paraformaldehyde. The resulting polymers were characterized by FT-IR and NMR.

Synthesis and triggered degradation of aliphatic polyesters

256th National Meeting (2018)

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