Premium
Synthesis and cyclopolymerization of diallylammoniomethanesulfonate
Author(s) -
Ali Shaikh A.,
AlHamouz Othman Charles S.O.
Publication year - 2013
Publication title -
polymer engineering and science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.503
H-Index - 111
eISSN - 1548-2634
pISSN - 0032-3888
DOI - 10.1002/pen.23482
Subject(s) - copolymer , monomer , polymer chemistry , polyelectrolyte , sodium bisulfite , polymer , chemistry , sodium hydroxide , hydroxide , dissolution , saponification , materials science , organic chemistry
N , N ‐Diallylammoniomethanesulfonate, a new zwitterionic monomer having a sulfobetaine (SB) motif, has been synthesized by reacting diallylamine with formaldehyde and sodium bisulfite. While the monomer underwent cyclopolymerization to give the unstable polysulfobetaine (PSB) in low yields, copolymerization with sulfur dioxide gave the stable PSB/SO 2 copolymer in excellent yields. The polymers, as a consequence of having unquenched nitrogen valency in the repeating units, are pH‐responsive. The PSB/SO 2 copolymer, upon treatment with sodium hydroxide, was converted into a water‐soluble anionic polyelectrolyte (APE). The strong zwitterionic interactions inherent in the PSB/SO 2 made it insoluble in salt‐free water; the presence of large concentration (>3M) of low molecular weight salts (e.g., NaCl, KI etc,) was required to neutralize the intragroup zwitterionic interactions and promote dissolution. The PSB/SO 2 represents the first example of a sulfobetaine polymer having a single methylene spacer separating the charge centers. The stability of the copolymer is explained in terms of electron density on the nitrogens. POLYM. ENG. SCI., 53:2378–2388, 2013. © 2013 Society of Plastics Engineers