Bis[3-(diethoxyphosphoryl)propyl]diallylammonium chloride: Synthesis and use of its cyclopolymer as an antiscalant



A new symmetrically substituted cationic monomer bis[3-(diethoxyphosphoryl)propyl]diallylammonium chloride has been synthesized and cyclopolymerized to give the corresponding cationic polyelectrolyte (+) (CPE) bearing two identical (diethoxyphosphoryl)propyl penedents on the pyrrolidinium repeating units. The hydrolysis of the phosphonate ester in (+) (CPE) gave a pH-responsive cationic polyacid (+) (CPA) bearing the motifs of a tetrabasic acid. The (+) (CPA) under pH-induced transformation was converted into a water-insoluble polyzwitterion acid (±) (PZA) or water-soluble polyzwitterion/monoanion (± −) (PZMAN) or polyzwitterion/dianion (± =) (PZDAN) or polyzwitterion/trianion (± ≡) (PZTAN), all having identical degree of polymerization. The interesting solubility and viscosity behaviors of the polymers have been investigated in some detail. The apparent protonation constants of the anionic centers in (± ≡) (PZTAN) and its corresponding monomer (± ≡) (ZTAN) have been determined. Evaluation of antiscaling properties of the PZA using supersaturated solutions of CaSO4 revealed ≈100% scale inhibition efficiency at a meager concentration of 10 ppm for a duration over 71 h at 40°C. The PZA has the potential to be an effective antiscalant in Reverse Osmosis plants. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40615.