Synthesis of novel fluoroalkyl end-capped N-vinyl-2-pyrrolidone-acrylic acid co-oligomers by use of fluoroalkanoyl peroxides, and their properties

Abstract

The reaction of a fluoroalkanoyl peroxide with N-vinyl-2-pyrrolidone was initiated by single electron transfer from the substrate to peroxide to afford the 11 adduct (fluoroalkylated N-vinyl-2-pyrrolidone); however, in the presence of acrylic acid, this peroxide afforded a fluoroalkylated N-vinyl-2-pyrrolidone-acrylic acid co-oligomer via a radical process under very mild conditions. The fluorinated co-oligomers thus obtained were soluble not only in water but also in polar organic solvents such as methanol, ethanol, N,N′-dimethylformamide and dimethylsulfoxide, and were able to reduce effectively the surface tension of water. Furthermore, these co-oligomers showed a high calcium binding power compared to common organic chelating agents, and exhibited antibacterial activity to some extent (from 10 8 to 10 6 colony forming units levels) against Staphylococcus aureus.