982 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS The new radical can then react with another peroxidic radical to produce the final hydroperoxide. --CH-- + AH--CH-- + A i I I 6-0- OOH During the progress of these reactions methyl oleate molecules are practi- cally immune from attack. In some cases antioxidants are found to be more effective in combination of two or more different agents. The phenomenon is an example of syner- gism for example, phosphoric acid enhances the effect of phenolic anti- oxidants. The antioxidants for soaps must not develop a colour of their own when they are exposed to light and air and must not be inactivated by water or alkalis. In recent years p-tert-amylphenol, ethylenediaminetetracetic acid, and various derivatives of thiourea have been used in soaps. The most popular additives in the past are the straightforward reducing agents which I have called inhibitors. They are added at a higher concentration than is neces- sary with what I have called the antioxidants. In my opinion it is clear that the steps taken to protect soap against ran- cidity are on the whole unsatisfactory. On the whole they accept the posi- tion that soap is susceptible to rancidity and merely attempt to prevent access of oxygen under conditions in which the soap is most susceptible. The addition of an inhibitor or an antioxidant gives a temporary measure of protection but it merely prolongs the induction period for a limited period. There is no fundamental protection in any of these measures. In other words the methods of providing protection from rancidity consti- tute an art and not a science. Fourth proposition: That commercial soaps to be used in the Toilet and Cosmetic Industry should be subject to a specification limiting the content of un- saturated fatty acids and unsaponifiable matter. Some guarantee should be obtained that the fatty matter used in manufacture was free from incipient rancidity. We have seen that many factors influence the rancidity stability of soap and that many of these factors are beyond the control of the user who de- pends upon commercial soap. However careful he may be in processing, packaging, and storing, he can never depend upon a soap having an un- suitable composition or one in which incipient rancidity is present. Having described and explained the four propositions I now submit them for discussion. REFERENCES (1) Farmer, E. H., and Sutton, D. A., y. Chem. Soc., 1942, 116. Farmer, E. H., and Sun- dralingham, A., Ibid., 1942, 121. Farmer, E. H., Koch, H. P., and Sutton, D. A., Ibid.,

INFRARED C--H FREQUENCIES, THEIR SIGNIFICANCE 283 1943, 541. Farmer, E. H., and Sutton, D. A., Ibid., 19•4, 242. Bollond, J. L., and Koch, H. P., Ibid., 1945, 445. Atherton, D., and Hilditch, T. P., Ibid., 19•4, 105. (2) Patton, S., Kenney, M., and Kurtz, G. W., 7./lm. Oil Chemists' $oc., 28, 391 (1951). (3) Patton, S., and Kurtz, G. W., )'. Dairy Sci., 34, 669 (1951). (4) Bernheim, F., Bernheim, M. L. C., and Wilbur, K. M., )'. Biooe Chem., 174, 257 (1947). (5) Prill, E. A., Oil and Soap, 19, 107 (1942). (6) Myddleton, W. W., 7. Inst. Petroleum, 37, 45 (1951). (7) Rothenbach, E., 14•ochenschriftfiir Brauerei, 56, 273 (1939). THE INFRARED C-H FREQUENCIES AT 13.8•, AND THEIR SIGNIFICANCE* By F. C. NACHOD, E. T. HINKEL, JP.., and M. PRIZN^R Sterling-Winthrop Research Institute, Rensselaer, N.Y. As ^BSORPT•O•r B^m) in the 13.8/z region of hydrocarbons and its unusual behavior in a series of compounds have been the subject of theory and speculation for some time. A doublet at about 13.85/z was first pointed out by Thompson and Torkington (1) who ascribed it to a deformation vibration in the CH2 group of long straight-chain molecules. They also pointed out that liquid paraffins do not exhibit the doublet which appears in the spectrum of polyethylene. Molecular weight changes from 500 to 13,000 of the polymer did not alter the shape of the doublet significantly. Elliot, Ambrose, and Temple (2) found that using polarized infrared radiation caused the disappearance of the doublet and the formation of a single broad band. The disappearing component was ascribed to the rock- ing vibration mode of the CH2 groups across the chain. Simanouti (3) considered this perturbation (at 728•) as perpendicular to the chain axis. * Received for publication, Aug. 9, 1954. TABIra 1--CH• BA•ro API'EAR.-X•rCE Doublet Single Band Inflection Point (13.723, and 13.923,) (13.923,) (13.79u) Adurco Wax Palm Wax Bayberry Wax Barnsdall Amber Plio Wax Butyl Stearate Beeswax Polyethylene Glyceryl Monostearate Carnauba Wax Spermatine Wax Japan Wax Candelilla Spermaceti Lanolin Crown 1035 Stearic Acid Shellac I G Wax B unbleached StearylAlcohol I G Wax E Sugar Cane I G Wax OP Utah Wax I G Wax S Petrolatum I G Wax Z Vegetable Wax Ozokerite Raphia Wax White Ceresine Wax