90 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS MASCARAS The desirable bluish greens of these products are often obtained through the use of small significant quantities of certain chlorophyll derivatives. To the best of our knowledge, no one is presently using chlorophyll in lip- sticks, rouges, facial packs, facial creams, cuticle removers, or depilatories or cold waves, although their use in such products is indicated. CONCLUSION The use of chlorophyll in various cosmetics has been described. The ef- tectiveness of chlorophyll as a contact deodorant is clearly proved by recent scientific evidence and the effectiveness of cosmetics containing chlorophyll is due to the use of the sufficient amount or type of chlorophyll. CHEMICALS FROM FATS AND OILS: A SOURCE OF COSMETIC RAW MATERIALS* By Pau• DuBP, ow Product Research Section, •Irmour and Company, Chicago 9, IlL T•E S^TURALL¾ occurring fats and oils offer one of the largest potential sources of raw materials for the preparation of chemical syn- thetics. The total annual world production of these materials is about 25 million tons, although only some 15 per cent of this is generally avail- able for the compounds we are interested in, the so-called fatty acid de- rivatives. Chemically, of course, the fats and oils are triglycerides, which, upon hydrolysis and separation, give rise to our starting fatty acids. These may be separated, in excellent yields, into primarily the lauric, hexadecyl, octadecyl, and octadecenyl acids. From these the range of possible prod- ucts and applications is almost limitless. The fatty acid, chemically, is a combination of a long, non-polar, hydro- phobic hydrocarbon chain and a strongly polar, hydrophilic carboxyl group, a highly favorable combination for surface activity. Both elements of the molecule offer approaches to further derivative formation and modi- fication. Let us consider, first, the preparation of the basically non-nitrogenous derivatives of these compounds, with particular reference to tried and suggested applications in the cosmetic field. Neutralization, with organic amines or inorganic alkalies, offers the * Presented at the November 10, 1953, Meeting of the Chicago Section, Chicago, Ill.

CHEMICALS FROM FATS AND OILS 91 simplest and most direct approach to derivative formation. The alkali metal soaps are basically cleaners and detergents, but function, in cos- metic preparations, as auxiliary emulsifiers and foamers also. Zinc and magnesium stearates have found use in face powders for improving skin adhesion and for supplying smoothness to the touch aluminum stearate has functioned as an oil thickener and gel former. The amine salts or soaps, e.g., the ethanolamine or morpholine derivatives, are known useful emulsifying and permanent waving agents. Esterification, with mono- or polyfunctional alcohols or with amino alcohols, gives the simple or polyfunctional esters. All of these function primarily, in the cosmetic industry at least, as emulsifiers for wax or oil and water emulsions, and have found application in cold creams, vanish- ing creams, and permanent waving creams. The esters, however, are also useful per se as intermediates in fur- ther chemical synthesis. They can be reduced by catalytic hydrogenation or by sodium emulsion to the corresponding alcohols. These, in turn, have found some use as flotation frothers, lubricants, and solvents, and in the cosmetic industry are very familiar auxiliary emulsifiers and skin sof- teners and aid in the emollient action of cold creams. The alcohols func- tion in o/w or w/o emulsions and are excellent for the preparation of lano- lin or petrolatum emulsions. Condensation products of the alcohols with certain cellulose products have been useful for suspending insoluble powders in cosmetic preparations, and oleyl alcohol has been used as a superfarting agent and a dispersing agent for dyes in indelible lipsticks. Sulfation of the alcohols, using sulfuric acid or SOa, gives the corre- sponding long-chain alkyl sulfates which, as the sodium, ammonium, or organic amine salts, are superior detergents, emulsifiers, and foaming agents. They are used as such in the cosmetic industry. The hydroxyl grouping in the alcohols offers another fruitful approach for synthetic purposes, namely the interchange with halogen to give the corresponding long-chain halides. These, in turn, may be used as al- kylating agents, as quaternizing agents, or as chemical intermediates. They will, for example, react with sodium sulfide to give the alkyl mer- captan, which is one means of introducing a sulfur atom into the molecule, This opens up an approach to use in the rubber industry, as a vulcanizer, for example. Another common reaction of the fatty acids is their conversion to the acid chlorides, by way of phosphorous trichloride or thionyl chloride. These are obtained in good yield and are extremely reactive intermediates. They will undergo amide or ester formation, with amines or alcohols with which the free acids often will not react. They will, for example, react with sodium methyl tauride to give the so-called Igepons, synthetic deter- gent additives, and emulsifiers. This is a generalized type of reaction and