Useful properties are imparted to textile fabrics by regioselective derivatization without significantly impairing their quality. Woven cotton and wool fabrics and a woolen knit were brominated at the primary hydroxyl (C-6 and L-serine residue, respectively) with Hanessian's N-bromosuccinimide/triphenylphosphine reagent, giving a degree of substitution of 5% and 94%, respectively, for cotton and wool. Addition of sodium bromide to the reaction mixture did not enhance the bromine content of the product. The brominated textiles were of excellent quality and stability, and no odor was detected. 72% of the bromine incorporated into the wool was stable to five drycleaning cycles. Ten aqueous launderings removed all the bromine from the wool. The brominated fabrics exhibited a diminished flammability. The brominated wool was moth-resistant.
Get full access to this article
View all access options for this article.
References
1.
Anisuzzaman, A.K.M. and Whistler , R.L., Selective Replacement of Primary Hydroxyl Groups in Carbohydrates: Preparation of Some Carbohydrate Derivatives Containing Halomethyl Groups, Carbohyd. Res. 61, 511-518 ( 1978).
2.
Anon., "Peroxide Bomb Apparatus and Methods ," Parr Instrument Company, Moline, Ill., 1950, pp. 30-31.
3.
Basch, A. and Wasserman, T., TheDetermination of Phosphorus in Cellulosic Fabrics, Textile Res. J.20, 676 (1970).
4.
Castro, B., Chapleur, Y., and Gross, B., Sels d'alkyloxyphosphonium. Partie VII Activation Selective de 1'α,α-trehalose et du Saccharose, Carbohyd. Res. 36, 412-419 (1974).
5.
Friedman, M., Flame-Resistant Wool and Wool Blends, in: "Flame Retardant Polymeric Materials," M. Lewin, S. M. Atlas, and E. M. Pearce , Eds, Vol. 2, Plenum Press , N.Y., 1978, pp. 229-284.
6.
Gold, V., Ed., Commission on Physical Organic Chemistry, International Union of Pure and Applied Chemistry, Glossary of Terms Used in Physical Organic Chemistry, Pure and Appl. Chem.51, 1725-1801 (1979).
7.
Hanessian, S. , Ponpipom, M.M., and Lavallee , P., Procedures for the Direct Replacement of Primary Hydroxyl Groups in Carbohydrates by Halogen , Carbohyd. Res. 24, 45-56 (1972).
8.
Isaacs, P., Lewin, M., Sello, S.B., and Stevens, C.V., Flame-Resistant Cellulose Enters, Textile Res. J.44, 700-707 ( 1974).
9.
Kikugama, K. and Ichino, M., Direct Halogenation of Sugar Moiety of Nucleosides , Tetrahed. Lett., 87-90 (1971).
10.
Koenig, N.H. and Friedman, M., Comparison of Wool Reactions with Selected Mono- and Bifunctional Reagents , in: "Protein Crosslinking: Biochemical and Molecular Aspects ," M. Friedman , Ed., Plenum Press, N.Y., 1977, pp. 355-382.
11.
Pacsu, E. and Schwenker, R.F., The Effect of Chemical Modification on the Flame and Glow Resistance of Cotton Cellulose, Textile Res. J.27, 173-175 (1957); Schwenker, R.F. and Pacsu, E., Chemically Modifying Cellulose for Flame Resistance, Ind. Eng. Chem.50, 91-96 (1958).
12.
Parisot, A. and Derminot, J., in: "Proc. 4th International Wool Textile Res. Conf." Part 1, L. Rebenfeld, Ed., Interscience Publishers, 1971, p.47.
13.
Rath, H., Rau, J.H., and Brink, G., UberHalogenderivate der Cellulose, Melliand Textilber.47, 909-912 (1966).
14.
Saunders, W.H. , Jr. and Cockerill , A.F., "Mechanisms of Elimination Reactions," Wiley, N.Y., 1973.
15.
Lewin, M., Isaacs, P.K., and Segal, N., Flameproofing of Cellulose with Phosphoraruide and its Derivatives and Properties of the Products, Internal Report #C70 (1971), Israel Fiber Institute, p. 23 (Heb.).
16.
Takeo, K., Sumimoto, T., and. Kuge, T., An Improved Synthesis of 6-Deoxy-Analogues of Cyclodextrins and Amylose , Die Staerke26, 111-118 (1974).
17.
Touloupis, C. and Vassiliadis, A., Lysinoalanine Formation in Wool After Treatments with Some Phosphate Salts , in: "Protein Crosslinking: Nutritional and Medical Consequences ," M. Friedman, Ed., Plenum Press, N.Y., 1977, pp. 187-195.
18.
Trippett, S. , A New Synthesis of Acetylenes. Part II. The Reaction of Triphenylphosphine with α-Halogeno-Carboxyl Compounds, J. Chem. Soc., 2337-2340 (1962 ).
19.
Usov, A.I., Krylova, R.G., and Suleimanova, F.R. , Preparation of 6-Bromo-6-Desoxycellulose and 6-Desoxycellulose, Izv. Akad. Nauk SSSR, Ser. Khim., 2122-2123 ( 1975 ); Bull. Acad. Sci. USSR,Div. Chem. Sci.24, 2009-2011 (1975).
20.
Vigo, T.L., Daigle, D.J., and Welch, C.M., Reaction of Cellulose with Chlorodimethylformiminium Chloride and Subsequent Reaction with Halide Ions, J. Polym. Sci. B (Polym. Lett. ) 10, 397-406 (1972).
21.
von Bergen, V., Ed., "Wool Handbook," Vol. 1, 3rd Enlarged Edn., Interscience Publishers, 1963 , p. 225.
22.
Ziderman, I.I., The Displacement of Serine Hydroxyl Groups in Wool Keratin by Bromine , Abstr. Proc. 44th Meeting, Israel Chem. Soc, June 1977 (Ramat Gan), Polymers Section, p. 6
