SYNTHETIC DETERGENTS monosulphonyl chloride, 30 per cent disulphonyl dichloride, 20 per cent hydrocarbon) and Metsol H (50 per cent monosulphonyl dichloride, 50 per cent hydrocarbon) were made and used by soapmakers. A purified saponified material was also put out as Mersolat H by the I.G. The most recent development in this field is the U.S. Solway Com- pany's Nytron, which is a complex mixture made by reacting nitrosyl chloride and an olefin and treating this with sodium sulphite in alco- holic solution, -- C = C -- d- NO.C1---• -- C -- C- c1 NO ---+ --C---- C-- I SO•Na NO the reaction mixture being purified by solvent extraction and steam distillation. In this group of alkane sulphonates we have also the petroleum sul- phonates obtained from the action of sulphuric acids on petroleum stocks. Their uses are mainly indus- trial, for example in cutting oils and textile spinning lubricants. The alkane sulphuric acids can have intermediate links between the hydrophobic and sulphonate groups, just as in the case of the sulphuric esters, the important link being ester, amide and ether. The ester- linked alkane sulphonates are exem- plified by Igepon A, AP, and AD made by reaction of a fatty acid or chloride with isethonic acid: R.CO C1 + HO.C•.H,.SO,.Na---- (ethylene oxide on NaHSOa) R.COO.C•H,.SlS,Na + -1- HC1 Typical reactions R.COOH -t7. HO.--X--SO3.H R.COO--X--SO3H d- H,•O R.OH d- HOOC--X--SO•H R.OOC--X--SO,H d- H,O Lissapol L.S. is made from oleic acid chloride and p. anisidine sulphonic acid C•,H•.CO.NHN•-- •/OCH• NS03 -- Na A further type of product has the hydrophobic part derived from a fatty alcohol and the sulphoacetates and dialkyl sulphonamides are repre- sentative of this type: R.OH d- C1CH•.COOH R.OOC.CH,..C1 R.OOC.CH•.C1 d- Na•SO, R.OOC.CH•.SO•Na + NaC1 Oleyl, lauryl, cetyl and stearyl alco- hols are estertried with chloracetic acid, the chlorester is reacted with an alkali metal sulphite to form the sulphoacetate group. Nacconal LAL (made from coconut alcohol) is a typical example, but this product, while it has been used in cosmetics, is not available in this country. The dialkyl sulpho succinates are made by esterifying maleic acid with an alcohol, octyl alcohol being the one of choice: 2ROH. d- HC COOH HC COOIt HC. COOR + 2H•O II HC. COOR 207

JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS The dialkyl maleate is heated with a concentrated aqueous solution of sodium bisulphite, forming the sul- pho succinat e. H 2C. COOR Hc COOR q- NailS03---+ C.COOR HC COOR SO•Na This product is known under various trade names, in the United States as Aerosol OT and in this country as Manoxol OT, etc. Amide-linked alkane sulphuric acids such as the well-known Igepon T made from oleic acid chloride with methyl taurine in aqueous alkali (sodium isethionate plus methyla- mide at 270-290 ø, 200 At.). R.COC1 + H•.C•H•SO3Na------- CH• R.CO.N.C•H•.SO3Na + HC1 I CH, Igepon KT is based on coconut fatty acid plus methyl taurine. Igepon 702K is from palm oil fatty acids. A product which was used as the active matter content of a light duty detergent in the United States is made by reacting a fatty acid chlor- ide with sulphoacetyl monoethanola- mide. The chief ether-linked alkane sul- phonates of interest in cosmetic practice are Triton 720 and Triton X200, made by Rohm and Haas. These are probably made from di- or tri-isobutene condensed with phenol, etherified with dichlorodiethyl ether and reacted with sodium sulphite. These compounds possess great acid and alkali stability. (d) Alt•yl aryl sulphonate. On a tonnage basis this is the most important group of surface-active agents, the main bulk of domestic synthetic detergents being based on this type of product, either built or unbuilt (i.e., with or without the addition of suitable filling or extend- ing agents). The lower alkyl aryl sulphonates comprise the Nekal B.X., Aerosol O.S., Nacconal A., Nansa B.X. types which are, as previously mentioned, essentially wetting agents based on butyl or isopropyl naphthalene sulphonates. The higher alkyl aryl sulphonates are based on dodecyl benzene, keryl benzene or dodecyl toluene. Keryl benzene is produced by chlorination of kerosene fractions and condensa- tion with benzene in the presence of aluminium trichloride as catalyst by the Friedel-Krafts reaction RX q-ArI-t • R-Ar q- HX. Dodecyl benzene and dodecyl toluene are prepared by similar condensation using polyisobutenes or polypropylenes. Whilst industrially these products possess many economic advantages so far they have found no major outlet in cosmetics, although occa- sionally shampoos based on alkyl aryl sulphonate are found. CATIONIC TYPES The cationic type of product can best be divided into the amine salts and quaternary ammonium com- pounds. As representative of the amine 208