Mechanism of Photolytic Decomposition of N-Halamine Antimicrobial Siloxane Coatings

Date

2010-08-01

Author

Kocer, Hasan B.
Akdağ, Akın
Worley, S. D.
Acevedo, Orlando
Broughton, R. M.
Wu, Yonnie

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Generally, antimicrobial N halamine siloxane coatings can be rehalogenated repetitively upon loss of their biocidal efficacies, a marked advantage over coatings containing other antimicrobial materials. However, the N halamine materials tend to slowly decompose upon exposure to ultraviolet irradiation as in direct sunlight. In this work the mechanism of photolytic decomposition for the N halamine siloxanes has been studied using spectroscopic and theoretical methods. It was found that the N chlorinated coatings slowly decomposed upon UVA irradiation, whereas the unhalogenated coatings did not. Model compound evidence in this work suggests that upon UVA irradiation, the N-Cl bond dissociates homolytically, followed by a Cl radical migration to the alkyl side chain connected to the siloxane tethering group. An alpha and/or beta scission then occurs causing partial loss of the biocidal moiety from the surface of the coated material thus precluding complete rechlorination. NMR, FTIR, GCMS, and computation at the DFT (U)B3LYP/6-311++G(2d,p) level of theory have been employed in reaching this conclusion.

Subject Keywords

Antimicrobial materials, Decomposition products, UVA irradiation, N halamines, Siloxanes

URI

https://hdl.handle.net/11511/56889

Journal

ACS APPLIED MATERIALS & INTERFACES

DOI

https://doi.org/10.1021/am100511x

Collections

Department of Chemistry, Article

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Citation Formats

H. B. Kocer, A. Akdağ, S. D. Worley, O. Acevedo, R. M. Broughton, and Y. Wu, “Mechanism of Photolytic Decomposition of N-Halamine Antimicrobial Siloxane Coatings,” ACS APPLIED MATERIALS & INTERFACES, pp. 2456–2464, 2010, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56889.