REVIEW OF CHLORINE-HAIR INTERACTION 367 is dependent on the form in which the halogens are present, which is determined by the pH of the solution. Once the halogen penetrates into the fiber, the reaction proceeds in a fashion similar to those found in amino acids and simple peptides. In the acid and neutral regions, cysteic acid is the main oxidation product. In the alkaline region, C-S bond fission results in the formation of lanthionine. Evidence indicates that peptide bonds are cleaved at all pH levels. Changes from these reactions occurring in the chem- ical, physical, and mechanical properties of the fibers can be explained in terms of disulfide bond oxidation and peptide bond cleavage. Although the literature cited in this paper does not pertain directly to hair, the infor- mation presented should serve as a useful body of knowledge in light of which the chlorine-hair interaction can be examined. Basic reactions will most likely remain the same, but the extent of reaction, and consequently the extent of effects on fiber proper- ties, may be different. There is, thus, a need for research which focuses on conditions more specific to the chlorine-hair interaction. Variables which should be studied in- clude chlorine concentration, pH of the solution, temperature of the solution, time of exposure, and the combination of chlorination with popular cosmetic and care treat- ments. REFERENCES (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16) S. R. Trotman, The use of aqueous solutions of chlorine and bromine for the production of unshrink- able finish on knitted woolen goods, J. Soc. Chem. Ind., 52, 159-164T (1933). M. Harris and D. Frishman, Some aspects of the chlorination of wool to produce shrink resistance, Am. DyestuffReptr., 37, P52-56 (1948). P. Alexander, D. Gough, and R. R. Hudson, Reaction of oxidizing agents with wool. 3. The influ- ence of the morphology on the rate of reaction, Biochem, J., 48, 20-27 (1951). L. Shapiro, Shrinkage control of wool by wet chlorination, Am. DyestuffReptr., 37, 376-381 (1948). D. Frishman, L. Hornstein, A. L. Smith, and M. Harris, Reaction between wool and active chloride, Ind. Engng. Chem., 40, 2280-2284 (1948). A. Kantouch and S. H. Abdel-Fattah, Oxidation of wool with chlorine and some chlorinated com- pounds, Appl. Polym. Syrup., 18, 317-323 (1971). H. Zimmerman, Felt resistant wool by wet chlorination, Am. DyestuffReptr., 36, 473-475 (1947). R. C. Landwehr and D. Stigter, A simple and qualitative electrophoretic technique for fibrous mate- rial, Text. Res. J., 44, 45-47 (1974). J. R. McLaughlin and W. S. Simpson, "Rate Studies of the Chlorination of Wool," in Fibrous Pro- teins: Scientific Industrial and Medical Aspects, D. A.D. Parry and L. K. Creamer, Eds. (Academic Press, New York, 1980), Vol. 2, pp. 213-225. P. Alexander, D. Gough, and R. F. Hudson, The reaction kinetics of wool with chlorine solutions. II. Diffusion within the fibre, Trans. Faraday Soc., 45, 1109- l 118 (1949). J. R. McLaughlin, Liquid-layer diffusion during chlorination of wool, J. Text. Inst., 70, 214-216 (1979). P. Nordom and N. W. Bainbridge, A laboratory study of dry chlorination of wool at atmospheric pressure. I. Conditions of treatment, J. Soc. Dyers Colour., 84, 26-29 (1968). A. Kantouch and S. H. Abdel-Fattah, Oxidation of wool with chlorine and some chlorinated com- pounds, Kolor. Ertes, 14, 2-9 (1972). I. J. O'Donnell and E. F. Woods, The preparation of wool protein solutions, Proc Intl. Wool Text. Res. Conf., Aust., B, 48-55 (1955). P. Alexander and R. F. Hudson, Wool--Its Chemistry and Physics (Reinhold Publishing, New York, 1954), pp 271-281. H. Vom Hove, The processes in the reaction of halogens upon wool, Angew. Chem., 47, 756-762 (1934).

368 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS (17) (18) (19) (20) (21) (22) (23) (24) (25) (26) (27) (28) (29) (30) (31) (32) (33) (34) (35) (36) (37) (38) (39) (40) (41) (42) R. Consden, A. H. Gordon, and A. J. P. Martin, The identification of amino acids derived from cystine in chemically modified wool, Blochem. J., 40, 580-582 (1946). P. Alexander, M. Fox, and R. F. Hudson, The reaction of oxidizing agents with wool. 5. The oxidation products of the disulfide bond and the formation of a sulphonamide in the peptide chain, BiochemJ., 49, 129- 138 (1951). P. Alexander, R. F. Hudson, and M. Fox, Reaction of oxidizing agents with wool. 1. The division of cystine into two fractions of widely differing reactivities, Biochem. J., 46, 27-32 (1950). C. Earland and D. J. Raven, Studies on the structure of keratin. III. The reaction of wool and horn keratins with solutions of sodium hypochlorite, Blochim. Biophys Acta, 25, 41-45 (1958). M. W. Andrews, A. S. Inglis, and V. A. Williams, Chemical changes in the cuticle of oxidized wool, Text. Res. J., 36, 407-412 (1966). G. Valk, Reaction between chlorine and wool proteins. Part I: Nature of the chemical modification of wool including proteins from reaction liquors, Proc. 3rd Intl. Wool Text. Res. Conf., Paris, 2, 371-381 (1965). R. W. Moncrieff, Chemical changes in the keratin when wool is chlorinated, Text. Mfg., 93, 145-147 (1967). I. B. Douglass and B. S. Farah, Chlorination of alkyl disulfides and the preparation of thiolsulfonate esters,_/. Org. Chem., 24, 973-975 (1959). P. Alexander and M. Fox, A comparison of the reactivity of the disulfide bond in wool and peptides, Proc. Intl. Wool Text. Res. Conf., Aust., C, 35-48 (1955). R. S. Asquith and N. H. Leon, "Chemical Reactions of Keratin Fibers," in Chemistry of Natural Protein Fibers, R. S. Asquith, Ed. (Plenum Press, New York, 1977), pp. 193-265. P. Alexander, D. Carter, and C. Earland, The role of the disulfide bond in reactions which render wool non-felting, J. Soc. Dyers Colour., 67, 23-27 (1951). P. Alexander and D. Gough, The reaction of oxidizing agents with wool. 4. The reactivity of tyro- sine, Biochem. J., 48, 504-511 (1951). S. R. Trotman, E. R. Trotman, and J. Brown, The action of chlorine and hypochlorous acid on wool, J. Soc. Chem. Ind., 47, 4-8T (1928). S. R. Trotman and C. R. Wyche, The amino-nitrogen content of wool in relation to chlorination, J. Soc. Chem. Ind., 43, T293-295 (1924). A. Kantouch and S. H. Abdel-Fattah, Action of sodium hypochlorite on tx-amino acids, Chemickg Zvesti, 25, 222-230 (1971). N. C. Wright, The action of hypochlorite on amino acids and proteins, Blochem J., 20, 524-532 (1926). N. C. Wright, The action of hypochlorites on amino acids and proteins. The effect of acidity and alkalinity, Biochem. J., 30, 1661-1667 (1936). L. Stankovic, Effect of amino acids on the amount of free chlorine in chlorine water, Chemickg Zvesti, 14, 275-281 (1960). L. Stankovic and J. Vasatko, The effect of oxidation and chlorination process on amino acids and proteins, Chemickg Zvesti, 14, 434-449 (1961). E. T. Gray, Jr., D. W. Margerum, and R. P. Huffman, Chloramine equilibria and the kinetics of disproportionation in aqueous solution, ACS Syrup. Ser., 82, 264-277 (1978). D. W. Margerum, E. T. Gray, Jr., and R. P. Huffman, Chlorination and formation of N-chloro compounds in water treatment, ACS Syrup. Ser., 82, 278-290 (1978). F. Lieben and B. Bauminger, The effect of sodium hypochlorite on amino acids and proteins, Biochem. Z., 261, 387-392 (1933). W. E. Pereira, Y. Hoyano, R. E. Summons, V. A. Bacon, and A.M. Duffield, Chlorination studies. II. The reaction of aqueous hypochlorous acid with tx-amino acids and dipeptides, Biochim. Biophys. Acta, 313, 170-180 (1973). J. C. Morris, "Kinetics of Reactions between Aqueous Chlorine and Nitrogen Compounds," in Prin- ciples and Applications of Water Chemistry, S. D. Faust and J. V. Hunter, Eds. (John Wiley and Sons, New York, 1967), pp. 23-53. S. Goldschmidt, E. Wiberg, F. Nagel, and K. Martin, Proteins IV. The degradation of polypeptides and amino acids by hypobromite, Ann., 461, 1-38 (1927). E. J. Corey and L. F. Haefele, Oxidative cleavage of amides. A method for selective chemical degra- dation of peptide, J. Am. Chem. $oc., 81, 2225-2228 (1959).