Soap‐based detergent formulations: XII. Alternate syntheses of surface active sulfobetaines

Sulfopropylated amphoteric surfactants, previously reported in this journal, displayed excellent surface active properties and were good detergents in combination with soap. New synthetic routes were investigated for the preparation of such types of compounds to provide a more economical process and eliminate the hazards due to propanesultone, which was used in the previously reported synthetic procedure. A series of 2‐hydroxy‐3‐sulfopropyl amphoteric surfactants was prepared by reacting sodium 3‐chloro‐2‐hydroxy‐1‐propanesulfonate (the addition product of sodium bisulfite to epichlorophydrin) with various primary fatty amines as well as with fat derived N,N‐dimethylalkylamines. Quaternary sulfobetaines not possessing a hydroxyl group were obtained from tertiary amines by reaction with allyl chloride followed by bisulfite addition. The solubility behavior (Krafft points) of these compounds indicated that they were not identical with the sulfobetaines prepared with the aid of propanesultone. The secondary and quaternary ammonium compounds exhibited limited water solubility but were good lime soap dispersing agents. They displayed good detergency in combination with soap. The quaternary ammonium derivatives were particularly effective on cottonpolyester blend fabrics.