Synthesis and antibacterial activity of novel fluoroalkyl end-capped cooligomers containing dimethyl(octyl)ammonium segments

New fluoroalkyl end-capped cooligomers containing dimethyl(octyl)ammonium segments were prepared by the reactions of fluoroalkanoyl peroxides with 2-(acryloxyethyl)dimethyl(octyl)ammonium chloride (AEMOAC) and comonomers such as N,N-dimethylacrylamide, acrylic acid, and acryloylmorpholine (ACMO). These fluorinated AEMOAC cooligomers thus obtained were in general soluble not only in water but also in organic solvents such as methanol, ethanol, THF, chloroform, DMSO, and DMF. Especially, fluoroalkylated AEMOAC–ACMO cooligomers were readily soluble in these solvents, and were able to reduce the surface tension of water quite effectively with a clear breakpoint resembling a critical micelle concentration, the same as for low-molecular weight fluorinated surfactants. Furthermore, the modified poly(methyl methacrylate) (PMMA) surface treated with these fluorinated AEMOAC–ACMO cooligomers was shown to have a strong hydrophilicity with a good oil repellency. In particular interest, the modified PMMA surface with these cooligomers was clarified to exhibit a high antibacterial activity. Therefore, these new partially fluoroalkylated AEMOAC cooligomers are applicable to new functional materials possessing not only the surface antibacterial activity but also the surface active property imparted by fluorine.