POLYCATIONIC SALTS. 3. SYNTHESIS, STYRENE BASED TRIALKYLAMMONIUM SALTS AND THEIR POLYMERIZATION1-2 1, 2

Abstract

A number of styrene-based vinylbenzyltrialkylammonium chloride salts were prepared via the Menshutkin reaction of vinylbenzylchloride with selected tert. amines. The vinylbenzyltrinalkylammonium salts were obtained in most cases in nearly quantitative yields. The lower members of the vinyl-benzyltrialkylammonium salts, such as vinylbenzyltrimethyl-ammoniumchloride, vinylbenzyl-triethylammonium chloride are highly water soluble. Vinylbenzyldimethyl(n-octyl or n-dodecyl) ammonium chloride were insoluble in water, but soluble in methanol. These monomers were polymerized and copolymerized in water using water-soluble azo initiators for water soluble monomers or in methanol with 2,2-azobisisobutyronitrile to polyelectrolytes of extremely high molecular weights. Vinylbenzyltri-n-alkylammonium chlorides were also copolymerized and crosslinked with the water soluble crosslinking agent: N,N'di(vinylbenzyl)-N,N,N',N′-tetramethylethylene diammonium dichloride. Monomers and polymers were characterized by 15N NMR spectroscopy. With N,N'-di(vinylbenzyl)-N,N,N',N'-tetramethylethylene-diammonium dichloride, vinylbenzyltri-n-alkylammonium chlorides were polymerized to randomly crosslinked polycations with unusual properties. The polymers were evaluated for their effectiveness a bile acid sequestering agents. 1 Polycationic Salts 1: P. Zarras and O. Vogl, Polymer Preprints, ACS Division of Polymer Chemistry, 34(2), 424 (1993). 2 Polycationic Salts 2: P. Zarras and O. Vogl, Prog. Polym. Sci., 24(3), 485 (1999).