Synthesis of novel fluoroalkyl end-capped oligomers/silica gel polymer hybrids possessing antibacterial activity

New fluoroalkyl end-capped oligomers/silica gel polymer hybrids-low-molecular weight biocide (hibitane) composites were prepared by the reactions of tetraethoxysilane (TEOS) with fluoroalkyl end-capped N-(1,1-dimethyl-3-oxobutyl)acrylamide oligomer, N,N-dimethylacrylamide oligomers, and acrylic acid oligomers in methanol under acidic conditions at room temperature. The presence of hibitane in the composites was clarified by the use of elementary analyses of nitrogen in fluorinated acrylic acid oligomer composite and thermogravimetric analysis (TGA) of these fluorinated composites. Thermal stability of fluorinated composites thus obtained were found to increase significantly compared to those of the parent fluorinated oligomers. Thermal stability of fluorinated N,N-dimethylacrylamide oligomer, acrylic acid oligomer/silica gel polymers hybrid-hibitane composites decreased compared to those of the corresponding fluorinated oligomers/silica gel polymer hybrids; however, the thermal stability of fluorinated N-(1,1-dimethyl-3-oxobutylacryl)amide oligomer/silica gel polymer hybrid-hibitane composite increased significantly compared to that of the corresponding fluorinated oligomer hybrid. The sol methanol solutions of these fluorinated composites were applied to the surface modification of glass to exhibit not only a strong oleophobicity imparted by end-capped fluoroalkyl groups in oligomers but also a good hydrophilicity on the glass surface. Fluorinated oligomers/silica gel polymer hybrids-hibitane composites were found to exhibit high anti-bacterial activity against Pseudomonas aeruginosa and Staphylococcus aureus. Therefore, these fluorinated hibitane composites are suggested to have high potential for new attractive functional materials through not only their excellent surface active property imparted by fluorine and their thermal stability but also through their anti-bacterial activity. Copyright (c) 2005 John Wiley & Sons, Ltd.