Synthesis and cyclopolymerization of novel allyl-acrylate quaternary ammonium salts

✍ Scribed by Duygu Avci; Lon J. Mathias

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 205 KB
• Volume: 37
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19990401)37:7<901::aid-pola6>3.0.co;2-u

✦ Synopsis

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 ␣-chloromethyl acrylate (ECMA) or tert-butyl ␣-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)allyl allylammonium bromide, and N,N-piperidyl-N-2-(ethoxycarbonyl)allyl allylammonium chloride. Higher purity monomers were obtained with the method 2. Solution polymerizations with 2,2Ј-azobis(2-amidinopropane) dihydrochloride (V-50) in water at 60 -70°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. 1 H-and 13 C-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.