1997 Volume 46 Issue 2 Pages 191-203
New fluoroalkylated allyl-, diallyl- and diallyldimethyl-ammonium chloride oligomers with carbon-carbon bonds were prepared under very mild conditions by oligomerization of allyl ammonium chloride and cyclo-oligomerization of diallyl-or diallyldimethyl-ammonium chloride using fluoroalkanoyl peroxides. The co-oligomerization of fluoroalkanoyl peroxides with allylammonium chloride and co-monomers such as acrylic acid, 2- (methacryloxy) ethane sulfonic acid and trimethylvinylsilane afforded the corresponding fluoroalkylated allyl ammonium chloride co-oligomers under similar conditions. Fluoroalkylated allylammonium chloride homo-oligomers were soluble in water. The diallyl- and diallyldimethyl-ammonium chloride homo-oligomers and co-oligomers were soluble not only in water but polar organic solvents such as methanol, ethanol and dimethylsulfoxide, as well. These fluoroalkylated cationic homo- and co-oligomers were capable of reducing the surface tension of water to around 10 mNm-1. They should thus prove useful as new allyl-type cationic oligo-surfactants containing fluoroalkyl groups. Fluoroalkylated allylammonium chloride oligomers were evaluated for activity against HIV-1 replication in MT-4 cells. Fluoroalkylated oligomers in some cases inhibited HIV-1-induced cytopathogenesis, but the growth of MT-4 cells was inhibited in all cases.
