Antimicrobial agents that are dispersed throughout a polymeric network traditionally suffer from unwanted leaching, low loading, and uncontrolled burst release. In this work, we describe the synthesis of a new acetal containing monomer derived from an antimicrobial p-chlorobenzaldehyde (pCB). Upon polymerization, pCB is fully incorporated within a stable thiol-ene network. However, exposure to aqueous environments results in rapid degradation and release of pCB in its active form. Herein, we demonstrate the synthesis of the monomer, photopolymerization kinetics, degradation kinetics, and antimicrobial evaluation of both the monomer and polymerized films. The antimicrobial activity is shown to increase with increasing concentration of the acetal monomer for gram-positive (S. aureus) and gram-negative (E. coli, P. aeruginosa and B. cenocepacia) bacteria. This thiol-ene system represents a new approach for tailoring the release of antimicrobial agents from crosslinked polymeric materials.

A pro-antimicrobial network via degradable acetals (PANDA) prepared via thiol-ene photopolymerization

255th National Meeting (2018)

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