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Synthesis of fluoroalkyl end‐capped preoligomers containing succinimidyl segments—Application to novel fluorinated oligomers possessing surface antibacterial activity
Authors:Hideo Sawada  Kenta Yanagida  Tokuzo Kawase  Yoshiko Inaba  Kazuo Sasazawa  Masashi Sugiya
Abstract:Fluoroalkyl end‐capped N‐acryloxysuccinimide (ASuI) cooligomers were prepared under very mild conditions by the cooligomerizations of fluoroalkanoyl peroxides with ASuI and comonomers such as N,N‐dimethylacrylamide (DMAA) and acryloylmorpholine (ACMO). These fluorinated ASuI cooligomers thus obtained were in general easily soluble in water and common organic solvents. These fluorinated ASuI cooligomers were also able to reduce the surface tension of water quite effectively to around 20 mN/m with a clear break point resembling a critical micelle concentration (CMC), although the corresponding nonfluorinated ASuI cooligomers were not effective for reducing the surface tension of water. Fluorinated ASuI cooligomers were applicable to new fluorinated precooligomers, and these precooligomers could react with several amino compounds such as aniline, cytosine, and cyclohexylamine to afford fluorinated cooligomer‐bound aromatic and cyclohexyl segments under mild conditions. Of particular interest, these fluorinated precooligomers were able to react with low molecular weight biocides such as sulfathiazole (STZ) and 3‐amino‐5‐hydroxypyrazole (AHP) to give the corresponding fluorinated cooligomers containing antibacterial segments under similar conditions. These cooligomers were shown to have not only a good oleophobicity imparted by fluorine but also surface antibacterial activity against Staphylococcus aureus. Therefore, our present fluorinated cooligomers containing antibacterial segments are suggested to have high potential for new fluorinated functional materials through their surface active property and surface antibacterial activity. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 92: 3874–3880, 2004
Keywords:biomaterials  fluoropolymers  self‐assembly  surfaces  surfactants
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