Poly(lactic acid) (PLA) is currently an attractive material as a promising alternative to commodity petroleum-based plastics. It is biodegradable and derived from renewable resources. However, PLA has some synthetic limitations: the only two convenient locations for functionalization are the end groups. To overcome this problem, we currently copolymerize lactic acid with 2-bromo-3-hydroxypropionic acid by a step-growth mechanism using p-toluene sulfonic acid as a catalyst. 1-3 This 2-bromo-3-hydroxypropionic acid comonomer provides a unique site for functionalization along the polymer backbone: the halogen alpha to the carbonyl is activated to a variety of chemistries. Another approach to synthesize higher Mn and lower polydisperse PLA is through the ring-opening polymerization (ROP) of lactide. We are looking at ROP as an approach to produce this functional PLA by using this 2-bromo-3-hydroxypropionic acid as a starting material to synthesize both polyester macrocycles and a 6-membered carboxyanhydride ring. Polymerization routes of these molecules are currently being established. References: 1. Pugh, C.; Singh, A. "Synthesis of Inimers and Hyperbranched Polymers", WO2008045299-A1; EP2079844-A1; IN200902573-P1; CA2665607-A1; CN101553571-A; JP2010506000-W, filed April 17, 2008. US Patent 8,524,942 issued September 3, 2013. 2. Pugh, C.; Singh, A.; Samuel, R.; Bernal Ramos, K.M. Macromolecules 2010, 43, 5222-5232. 3. Pugh, C.; Banerjee, A.; Storms, W; Wright, C. "Functional Biodegradable Polyesters", WO 2012/015481, filed July 28, 2011.

Synthesis and functionalization of PLA-based systems

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.