Fluorinated and un-fluorinated N-halamines as antimicrobial and biofilm-controlling additives for polymers

Abstract

The objective of this study was to evaluate the effects of fluorination on the antimicrobial and biofilm-controlling activities of N-halamine-based additives for polymers. A fluorinated N-halamine, 1-chloro-3-1H,1H,2H,2H-perflurooctyl-5,5-dimetylhydantoin (Cl-FODMH), and its un-fluorinated counterpart, 1-chloro-3-octyl-5,5-dimethylhydantoin (Cl-ODMH), were synthesized and characterized with FT-IR, 1H-NMR, and DSC studies. Polyurethane (PU) films containing Cl-ODMH and Cl-FODMH as antimicrobial additives were fabricated through solvent casting. With the same additive contents (1wt%-5 wt%), PU films with Cl-FODMH showed higher contact angle values. AFM, SEM and DSC results revealed that while Cl-ODMH distributed evenly within PU, Cl-FODMH aggregated and formed macro-domains in PU. Antimicrobial studies showed that PU films with Cl-ODMH had higher antimicrobial and biofilm-controlling potency against Gram-positive and Gram-negative bacteria than PU samples with Cl-FODMH. These results demonstrated the importance of distribution of additives in polymers on antimicrobial performances, shedding lights on future antimicrobial material design strategies.

Controlling bacterial fouling with polyurethane/N-halamine semi-interpenetrating polymer networks

“…Gram-positive bacteria S. epidermidis ( Staphylococcus epidermidis , ATCC 35984) and Gram-negative bacteria A. calcoaceticus ( Acinetobacter calcoaceticus , ATCC 31926) were used as model microorganisms to evaluate the antimicrobial activity of the N -halamine semi-IPN 17 due to their biofilm formation capability and their important roles in inducing biofilms on medical devices and dental tubing. The bacteria were cultured following the instruction provided by ATCC.…”

“…The disk was “sandwiched” using another identical disk. 20 After different periods of contact time, the “sandwich” was immersed into sterile PBS, vortexed to separate the “sandwich,” and then sonicated 17 for 10 min to transfer the adherent bacteria into the solution, which was vortexed and then serially diluted. A total of 100 µL of each dilution was placed onto agar plates and after 24 h of incubation, CFUs on the plates were counted.…”

“…10 With the similar biocidal efficacy as chlorine bleach, N-halamines are much more stable, less corrosive, and have no-documented resistant species, making them attractive candidates for the preparation of antimicrobial polymers. 11 To date, various methods, including copolymerization, 12,13 surface grafting, 14,15 functional group transformation, 16 blending, [17][18][19] and coating, [20][21][22] have been developed to incorporate N-halamines into conventional polymers to achieve biocidal effects.…”

Potential biofilm control strategies for extended spaceflight missions

“… Rechargeable coatings Antimicrobial characteristic capable of being regenerated by in situ chemical or physical treatment Lab-based tests against model organisms show promise. Based on literature, still in development stage, but notable potential N-halamine [ 100 , 101 ] Compounds contain nitrogen-halogen covalent bonds. Often used to coat polyurethane and other polymers Similar disinfecting characteristics to hypochlorite.…”

A New Strategy for the Synthesis of Fluorinated Polyurethane

“…Fluorinated polyurethanes, a new class of functional materials, combine some virtues of fluorinated polymer and polyurethane, such as high thermal stability, good mechanical properties, excellent chemical resistance (to acids, alkalis, and solvents), and attractive surface properties. [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16] As a result, they have attracted considerable interest in recent years.…”