Synthesis and Cyclopolymerization of Novel Allyl-Acrylate Quaternary Ammonium Salts

Document Type

Article

Publication Date

4-1-1999

Department

Polymers and High Performance Materials

Abstract

Novel allyl-acrylate quaternary ammonium salts were synthesized using two different methods. In the first (method 1), N,N-dimethyl-N-2-(ethoxycarbonyl)allyl allylammonium bromide and N, N-dimethyl-N-2- (tert-butoxycarbonyl)allyl allylammonium bromide were formed by reacting tertiary amines with allyl bromide. The second (method 2) involved reacting N,N-dialkyl-N-allylamine with either ethyl alpha-chloromethyl acrylate (ECMA) or tert-butyl alpha-bromomethyl acrylate (TBBMA). The monomers obtained with the method 2 were N,N-diethyl-N-2-(ethoxycarbonyl)allyl allylammonium chloride, N,N-diethyl-N-2-(tert-butoxycarbonyl)all allylammonium bromide, and N,N-piperidyl-N-2-(ethoxycarbonyl)allyl allylammonium chloride. Higher purity monomers were obtained with the method 2. Solution polymerizations with 2,2'-azo-bis(2-amidinopropane) dihydrochloride (V-50) in water at 60-70 degrees C gave soluble cyclopolymers which showed polyelectrolyte behavior in pure water. Intrinsic viscosities measured in 0.09M NaCl ranged from 0.45 to 2.45 dL/g. H-1- and C-13-NMR spectra indicated high cyclization efficiencies. The ester groups of the tert-butyl polymer were hydrolyzed completely in acid to give a polymer with zwitterionic character. (C) 1999 John Wiley & Sons, Inc.

Publication Title

Journal of Polymer Science Part A: Polymer Chemistry

Volume

37

Issue

7

First Page

901

Last Page

907

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