Silicon-Modified Carbohydrate Surfactants III: Cationic and Anionic Compounds

Ionic siloxanyl-modified carbohydrate surfactants have been synthesized by alkylation/esterification of precursors containing tertiary amino functions. Depending on the reaction strategy, the siloxanyl moiety is part of the alkylating agent or the substrate. Polyhydroxylated tertiary amines can be quaternized by siloxanyl-modified chloroacetic acid esters or epoxysiloxanes in the presence of glacial acetic acid. The esterification of tertiary amines bearing carbohydrate and siloxanyl subunits by cyclic acid anhydrides yields, after neutralization, carboxylate salts. The reaction of hydroxyl groups and sulfamic acid leads to sulfates. The new substances were characterized by means of ¹³C NMR spectroscopy, gas chromatography, elemental analysis and their solubility profile. © 1997 John Wiley & Sons, Ltd.