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Synthesis and characterization of novel sulfobetaines derived from 2,4-tolylene diisocyanate



Novel sulfobetaines were synthesized from two urethanes derived from 2,4-tolylene diisocyanate (TDI) blocked with 2-hydroxyethyl methacrylate (HEMA) and either N,N-dimethylaminopropylamine (DMAPA) or N,N-dimethylaminoethanolamine (DMAEA). The first-stage reaction of TDI with HEMA was carried out in petroleum ether heterogeneously with the precipitation of the intermediate monoadduct product in the reaction solution. The second stage is a homogeneous reaction of the monoadduct with the blocking agent, DMAPA or DMAEA, in tetrahydrofuran (THF). In both reactions, an inhibitor, hydroquinone, and a catalyst, dibutyltin diacetate (DBDAc), were used. The tertiary amine urethanes were quaternized by 1,3-propane sultone to form the two novel sulfobetaines. The results of the elemental analysis of those products along with their 1H-NMR and IR spectra indicated that these materials were, indeed, the compounds expected. The products dissolved in strongly polar organic solvents. The copolymerization of these two monomers with comonomers such as styrene, methyl methacrylate, acrylamide, and HEMA was investigated. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 82: 3447–3459, 2001