Synthesis and characterization of novel antimicrobial polymers containing pendent triclosan moieties

Abstract

Novel antimicrobial copolymers were produced by first converting the commodity biocide, triclosan (TCS), to an epoxy-functional derivative, 2-((5-chloro-2-(2,4-dichlorophenoxy)phenoxy) methyl)oxirane (ETCS), and then reacting ETCS with polyethylenimine (PEI). While neither ETCS or PEI showed high antimicrobial activity toward either the Gram-positive bacterium, Staphylococcus epidermidis, or the Gram-negative bacterium, Escherichia coli, some the copolymers showed very high activity toward both bacteria. Antimicrobial activity for these copolymers was found to be highly dependent on both the molecular weight of the PEI utilized and the concentration of pendent groups derived from ETCS. In general, decreasing PEI molecular weight and increasing TCS pendent group concentration increased antimicrobial activity. Surface tension measurements showed that the molecular parameters affecting antimicrobial activity also affected surface activity in a similar fashion. Thus, it was speculated that the mechanism of antimicrobial activity associated with these copolymers involves interaction of the copolymers with the bacterial cell wall. A comparison of the antimicrobial activity of the most effective copolymers to TCS showed that the copolymers were more effective toward E. coli than pure TCS when compared using an equivalent TCS content (i.e. TCS pendent group content for the copolymers). This characteristic coupled with the fact that the TCS-containing copolymers are highly aqueous soluble liquids as opposed to a crystalline solid of limited solubility may afford utility of these copolymers for a variety of applications.