Polycationic salts. VI. Synthesis and in vitro studies of 2-ionene oligomer derivatives of styrene as bile acid sequestering agents

Several vinylbenzyltri-n-alkylammonium salts were prepared via the Menshutkin reaction in high yields by the reaction of vinyl benzyl chloride (VBC) and tertiary amines. Additional salts based on 2-ionene oligomers were synthesized via a sequential Menshutkin reaction. The 2-ionene oligomers were further reacted with VBC to afford the vinyl benzyl chloride-2-ionene halide monomers in nearly quantitative yield. The monomers were polymerized in either aqueous or organic solvents with azo initiators in high yield with correspondingly high inherent viscosities. The polymers were measured spectrophotometrically for their bile acid sequestering activity with an in vitro enzymatic reaction. Several of the measured polymers exhibited 15–28% greater activity relative to cholestyramine. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 701–713, 2004