This Is AuburnElectronic Theses and Dissertations

Synthesis and Application of Novel N-halamine Antimicrobial Materials




Song, Hao

Type of Degree



Chemistry and Biochemistry


Several novel antimicrobial N-halamines have been synthesized and were incorporated into water-soluble latex paint. These paints were expected to render good biocidal capability and the antimicrobial activity to be long-lasting. The physical properties of these paints have been examined. These paints were coated onto different materials. Chlorine loading was monitored by a potassium iodide/thiosulfate procedure. A chlorine stability study was completed under different conditions: lab light and UVA light. The rechargeability of these paints has also been studied. The biocidal test result was also obtained. The second part of the research was designed to study the chlorine activities if bonded to different kinds of nitrogen atoms in 5,5-dimethylhydantoin. Selective chlorination was done, first, by blocking the each nitrogen atom in turn with a methyl group. Thus, 1-chloro-3,5,5-trimethylhydantoin and 3-chloro-1,5,5-trimethylhydantoin were the examined compounds. The solubility of these two compounds was tested. Research has also been done to study the chlorine stabilities and biocidal efficacies of these two compounds. During the UVA stability test, an interesting hydrogen atom migration reaction was observed. Further experiments were used to propose several mechanisms for this kind of reaction.