Soap based detergent formulation: XXIV. Sulfobetaine derivatives of fatty amides

Abstract and Summary Sulfobetaines were prepared from the reaction of fatty acids, fatty acid methyl esters or fatty glycerides with N,N‐dimethyl‐1,3‐propanediamine to form an aminoamide which could be allowed to react further with either sodium 3‐chloro‐2‐hydroxy‐1‐propanesulfonate (from epichlorohydrin and sodium bisulfite) or with allyl chloride followed by addition of sodium bisulfite to form sulfobetaines. The conditions for the reaction between aminoamide and sodium 3‐chloro‐2‐hydroxyl‐1‐propanesulfonate were studied in an effort to minimize the extent of hydrolysis of the 3‐chloro‐compound and thus increase the yield of desired compound. Investigation of the quaternization of the aminoamide with allyl chloride showed that this reaction proceeded readily at pressures above atmospheric. The addition of sodium bisulfite to the resulting allyl quaternary ammonium compound took place readily in the presence of certain free radical initiators. Solution properties and detergency performance of the compounds are reported. Detergency of ternary formulations of soap, glassy silicate builder, and the above sulfobetaines was the same as that obtained with ternary formulations containing the analogous sulfobetaines obtained from the reaction of propanesultone with the aminoamide. We have developed a synthetic scheme for fatty amino sulfobetaines that requires no purification, avoids the use of carcinogenic 1,3‐propanesultone and expensive fatty tertiary amines, and produces detergents that perform as well as the previously described purified sulfobetaines [Parris et al., JAOCS 50:509 (1973); Paris et al., Ibid. 53:60 (1976)].