Sulfobetaines, synthesis

DAHANAYAKE AND ROSEN Betaine, Sulfobetaine Synthesis, Properties 51... 

While DADMAC is primarily employed in homo- and copolymerization as a monomer to produce cationic or amphoteric polymers or gels, it is also a source for the synthesis of sulfobetains or sulfobetains with additional anionic groups by sulfocyclization, sulfocyclosulfonation, or sulfocyclosulfination [36]. Figure 3 summarizes these reactions. 

Fig. 3. Synthesis of sulfobetaines from diallyldimethylammonium chloride [36] (1 Sulfocy-clization, 2 Sulfocyclosulfonation, 3 Sulfocyclosulfination)...

Snow, S.A., Fenton, W.N. and Owen, M.J. (1991) Zwitterionic organofunctional siloxanes as aqueous surfactants - synthesis and characterization of betaine functional siloxanes and their comparison to sulfobetaine functional siloxanes. Langmuir, 7(5), 868-71. 

Cross-linking of 23b by ethylene dimethacrylate (EDMA) leads to formation of porous monolithic sulfobetaine polymers [258]. Alternatively, grafting of the internal surfaces of porous poly(trimethylpropane trimethacrylate) (polyTRIM) by DMAPS provides grafted monoliths. Both synthesis routes yielded polymers capable of interacting reversibly with proteins in aqueous solutions. The SEM pictures show the copolymerized monolith poly(DMAPS-co-EDMA) comprised of spherical units with average diameter approximately... 

The acidity of the sulfonic group is slightly more pronounced than that of the carboxylic group in the carboxybetaines. This aspect does not differentiate the sulfobetaines distinctly from the carboxybetaines. The synthesis of sulfobetaines either starts with tertiary fatty amines or more commonly with fatty amidopropy-lamines and is in this respect similar to the synthesis of carboxybetaine. The sulfonic group can be introduced... 

Synthesis. Betaine monomers may be prepared in a number of different ways. For sulfobetaines, the most common, and easiest, method is to react a monomer containing a tertiary amine residue with either 1,3-propanesultone or 1,4-butanesultone (268). This is an extremely facile reaction and proceeds readily at RT in common solvents such as THF or CH3CN to srield the corresponding sul-fobetaine monomer. Alternatively, the tertiary amine functionality may be reacted... 

Figure 2.21 Synthesis and composition of the polyurethane with sulfobetaine pendant groups, (a) Feeding ratio of monomers (b) ZPDEM is synthesized by betainization of corresponding PDEM polymer.

Min D, Li Z, Shen J, Lin SC. Research and synthesis of organosihcon nonthrom-bogenic materials containing sulfobetaine group. Colloids Surf B Biointerfaces 2010 79(2) 415-20. 

Polymer Synthesis. Acrylamide-based Polymers, Acrylamide-based polymers were prepared in an 0.5 M NaCl aqueous solution at 30 C using KPS as the free radical initiator. Total monomer concentration was held constant at 0.45 M and the pH adjusted so that all monomers were in die ionized form. Reactions were terminated at <60% conversion by precipitation in acetone. The polymers were fiirther purified by dialysis against deionized water. In the following discussion, the number appended to the polymer series is representative of the mol% of the respective sulfobetaine incorporated into the polymer (See Tables 1,2,3, and 4). 

Ning, J., Li, G., Haraguchi, K., 2013. Synthesis of highly stretchable, mechanically tough, zwitterionic sulfobetaine nanocomposite gels with controlled thermosensitivities. Macromolecules 46, 5317—5328. 

Song, Y., Doomes, E.E., Prindle,)., Tittsworth, R., Hormes, J. and Kumar, C.S.S. (2005) Investigations into sulfobetaine-stabihzed Cu nanopartide formation toward development of a microfluidic synthesis. The Journal of Physical Chemistry B, 109, 9330-8. 

A sulfobetaine, alkylamidopropyl-A,A-dimethy lammonio-1 -propane-sulfonate, as well as starting materials and intermediates in its synthesis Waters pBondapak Ci 90 10 Me0H/H20, containing 0.2% HOAc and 0.0042 M sodium decylbenzenesulfonate, pH 4 RI and inverse UV, 254 nm 199... 

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