Combinatorial materials research applied to the development of new surface coatings XII: Novel, environmentally friendly antimicrobial coatings derived from biocide-functional acrylic polyols and isocyanates

Abstract

Novel, environmentally friendly antimicrobial coatings containing tethered biocide moieties derived from the ubiquitous biocide, triclosan, were synthesized and characterized using a high-throughput workflow. Triclosan was first modified with an acrylate functionality and, subsequently, copolymerized with hydroxyethyl acrylate and butyl acrylate using conventional free radical polymerization to form an array of acrylic polyol terpolymers. The polyols were characterized using nuclear magnetic resonance spectroscopy, differential scanning calorimetry, and gel permeation chromatography. Arrays of urethane coatings were produced from the array of acrylic polyol terpolymers and, subsequently, characterized using parallel dynamic mechanical thermal analysis, surface energy measurements, and various biological assays. The results of the biological assays showed that the coatings were effective toward inhibiting Staphylococcus epidermidis biofilm retention without leaching triclosan or other toxic components from the coating. The level of antimicrobial activity was found to increase with the content of triclosan moieties incorporated into the coating matrix. These results indicate that triclosan moieties tethered to a polymer matrix can impart antimicrobial properties via a contact-active, nonleaching (i.e., environmentally friendly) mechanism. Since S. epidermidis is one of the primary microorganisms associated with infection and failure of implanted medical devices, such as prosthetic heart valves, urinary catheters, and a variety of orthopedic implants, these coatings may have good potential for commercialization in some of these applications.

Novel, UV‐curable coatings containing a tethered biocide: Synthesis, characterization, and antimicrobial activity

“…The results of this study are somewhat similar to those reported by Kugel et al12 in which urethanes containing tethered triclosan moieties exhibited a high degree of antimicrobial activity toward the Gram‐positive bacterium, S. epidermidis , with little to no effect toward the Gram‐negative bacterium, E. coli . According to the authors, one potential explanation for the high antimicrobial specificity of the urethane‐based coatings toward S. epidermidis was that these coating systems released a sufficient amount of triclosan to inhibit biofilm formation by this bacterium.…”

“…Triclosan (5‐chloro‐2‐(2,4‐dichlorophenoxy)phenol) is a low‐cost, widely used broad‐spectrum biocide that possesses a phenol group that can be functionalized and subsequently used to tether to a polymer backbone 10. A tethered triclosan approach has been previously investigated in variety of polymeric coatings 11, 12. For example, polyurethane coatings derived from acrylic polyols containing pendant triclosan moieties showed high antimicrobial activity toward Staphylococcus epidermidis 12…”

“…A tethered triclosan approach has been previously investigated in variety of polymeric coatings 11, 12. For example, polyurethane coatings derived from acrylic polyols containing pendant triclosan moieties showed high antimicrobial activity toward Staphylococcus epidermidis 1213, 14.…”

Effects of pigmentation on siloxane–polyurethane coatings and their performance as fouling-release marine coatings

“…[23][24][25] The wells of the coating array plates were inoculated with 1.0 mL of C. lytica suspension (10 7 cells/mL) in BGM. The plates were incubated at 28°C for 24 h. The growth media and planktonic growth were discarded after incubation was complete, and the coatings were rinsed three times with ASW to remove unattached or weakly adhered biofilm.…”

A Combination of Phenotype MicroArrayTM Technology with the ATP Assay Determines the Nutritional Dependence of Escherichia coli Biofilm Biomass

“…In a second step, crystal violet is solubilized with a mix of ethanol and acetone (80:20) and measured spectrophotometrically (O'Toole et al, 1999;Pratt & Kolter, 1998). The assay was developed as a high-throughput assay that is suitable for robotic instrumentation (Kugel et al, 2009;Stafslien et al, 2006Stafslien et al, , 2007. ATP (adenosine triphosphate) (Sule et al, 2008(Sule et al, , 2009) and XTT (4-nitro-5-sulfophenyl-5-[(phenylamino) carbonyl]-2H-tetrazolium hydroxide) (Cerca et al, 2005) are both assays that quantify the energy metabolism of the bacteria.…”