SYNTHESIS OF NOVEL FLUOROALKYL END-CAPPED N-VINYL-2-PYRROLIDONE-ACRYLIC ACID CO-OLIGOMERS BY USE OF FLUOROALKANOYL PEROXIDES, AND THEIR PROPERTIES

The reaction of a fluoroalkanoyl peroxide with N-vinyl-2-pyrrolidone w as initiated by single electron transfer from the substrate to peroxid e to afford the 1:1 adduct (fluoroalkylated N-vinyl-2-pyrrolidone); ho wever, in the presence of acrylic acid, this peroxide afforded a fluor oalkylated N-vinyl-2-pyrrolidone-acrylic acid co-oligomer via a radica l process under very mild conditions. The fluorinated co-oligomers thu s obtained were soluble not only in water but also in polar organic so lvents such as methanol, ethanol, N,N'-dimethylformamide and dimethyls ulfoxide, and were able to reduce effectively the surface tension of w ater. Furthermore, these co-oligomers showed a high calcium binding po wer compared to common organic chelating agents, and exhibited antibac terial activity to some extent (from 10(8) to 10(6) colony forming uni ts levels) against Staphylococcus aureus. (C) 1997 Elsevier Science S. A.