Amide-Based Cationic Polymeric N-Halamines: Synthesis, Characterization, and Antimicrobial and Biofilm-Binding Properties

A series of amide-based N-halamine precursors, poly 3-(4′-vinylbenzyl)-5,5-dimethylhydantoin-co-trimethyl-2-methacryloxyethylammonium chloride (PVPT), were synthesized by copolymerizing 3-(4′-vinylbenzyl)-5,5-dimethylhydantoin (VBDMH) and trimethyl-2-methacryloxyethylammonium chloride (TMAC) with different compositions. Chlorine bleach treatment was used to transform the VBDMH moieties in the copolymers into amide N-halamines (Cl-PVPT). 1H NMR, FT-IR, and dynamic light scattering (DLS) analysis were used to characterize the copolymers. With lower than 50% of VBDMH, the Cl-PVPT copolymers could be dissolved in water, and provided powerful antimicrobial function in killing Gram-positive as well as Gram-negative bacteria. Furthermore, Cl-PVPTs rapidly bound onto preexisting bacterial biofilms and eradicated adherent bacteria. The biofilm-binding kinetics were studied, and the parameters of the kinetics were provided.