title: Fatty acid sulphoalkyl amides and esters as cosmetic surfactants.
abstract: Synopsis A review is given of the manufacture, properties and applications of the anionic surfactants commonly known as taurates and isethionates (fatty acid sulphoalkyl amides and esters, respectively). Originally developed in the 1930s for textile processing, these surfactants are used increasingly in the cosmetic field, particularly those derived from coconut fatty acid. Both types are produced from sodium isethionate, HO degrees C(2)H(4)SO(3)Na. The acyl isethionate, R degrees COO degrees C(2)H(4)SO(3)Na, is obtained by reaction with a fatty acid ('direct process'). or fatty acid chloride ('indirect process'). The direct process is cheaper but requires extreme conditions which can lead to discoloration of the product and a loss of shorter chain fatty acid components. The N-methyl-N-acyltaurate, R degrees CON(R(1))C(2)H(4)SO(3)Na, is obtained by Schotten-Baumann reaction of a fatty acid chloride with N-methyltaurine, which is derived from sodium isethionate via methylamine. Taurates and isethionates retain the benefits of the soaps to which they are structurally similar, but chemical modifications have eliminated many undesirable features. Thus they combine good detergency and wetting with high foaming, and maintain their performance in hard or salt water. Taurates are stable to hydrolysis over the whole pH range. Isethionates are prone to hydrolysis at high (>8) or low (<5) pH, but this does not normally present a problem in cosmetic formulations. Above all, these surfactants are characterized by their extreme mildness to skin. Syndet and syndet/soap bars based on isethionate can be formulated at neutral pH ('Dove type'bars) instead of the alkaline pH of soap, and have been shown in various studies to be milder than soap and better tolerated by the young, the old and those with sensitive skins. Similarly, isethionates have been shown to be less irritating than other anionic or amphoteric surfactants used in cosmetics. The difference has been related to the negligible effect of isethionate on the water-binding capacity of stratum corneum. Other cosmetic applications besides toilet bars include shampoos (excellent cleaning, mild to scalp, some hair conditioning effects), liquid soaps (mild for all-over body use), bubble baths (copious stable foam, efficient lime soap dispersal, low irritancy), skin creams and lotions (emulsification, alleviation of 'dry skin'), baby care products (ultra-mild cleansing bars and milks, impregnated baby wipes) and oral products (foaming agents with low toxicity for toothpastes and mouthwashes).
authors.affiliation: GAF Europe, Cosmetic Applications Laboratory, Rythe House, 2 Littleworth Road, Esher, Surrey, KT10 9PD, England.
authors.forename: P J
authors.initials: PJ
authors.lastname: Petter