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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

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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.

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Acknowledgments

The authors thank the Office of Naval Research under grants N00014-06-1-0952 and N00014-07-1-1099.

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Authors and Affiliations

  1. Department of Coatings & Polymeric Materials, North Dakota State University, Fargo, ND, USA

    Alex J. Kugel, Robert J. Pieper, Dean C. Webster & Bret J. Chisholm

  2. Center for Nanoscale Science and Engineering, North Dakota State University, Fargo, ND, USA

    Laura E. Jarabek, Justin W. Daniels, Lyndsi J. Vander Wal, Scott M. Ebert, Michael J. Jepperson, Shane J. Stafslien, Dean C. Webster, James Bahr & Bret J. Chisholm

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  1. Alex J. Kugel
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  2. Laura E. Jarabek
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  3. Justin W. Daniels
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  4. Lyndsi J. Vander Wal
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  5. Scott M. Ebert
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  7. Shane J. Stafslien
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  8. Robert J. Pieper
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  9. Dean C. Webster
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  10. James Bahr
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  11. Bret J. Chisholm
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Corresponding author

Correspondence to Bret J. Chisholm.

Additional information

This paper was awarded First Place in the 2008 Roon Awards competition, held as part of the FutureCoat! conference, sponsored by the Federation of Societies for Coatings Technology, in Chicago, IL, on October 14–16, 2008.

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Kugel, A.J., Jarabek, L.E., Daniels, J.W. et al. 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. J Coat Technol Res 6, 107–121 (2009). https://doi.org/10.1007/s11998-008-9124-6

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  • DOI: https://doi.org/10.1007/s11998-008-9124-6

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