Binding of Organic Antimicrobial Agents to Cotton Fabric as Zirconium Complexes

Abstract

Solutions of zirconium(IV) complexes were used to bind organic antimicrobial agents to cotton fabric by one- or two-bath processes. In the one-bath process, a water-soluble complex of the organic agent was prepared from a carbonatozirconate or zirconyl chloride and applied to fabric by a conventional pad-cure procedure. In the two-bath process, fabric was treated successively with a solution of zirconyl acetate and a solution of a salt of the antimicrobial agent. The fabrics were tested for activity against the bacteria Staphylococcus aureus and S. epidermidis and the fungus Trichophyton mentagrophytes. Fabrics given a two-bath treatment with pyrithione (1-hydroxy-2-pyridinethione), tetracycline, or oxytetracycline retained excellent bacteriostatic activity after fifty launderings, and the one treated with pyrithione still had excellent antifungal activity after twenty launderings. Antimicrobial activity imparted by some of the one-bath treatments was initially extremely high but was less durable to laundering.

Get full access to this article

View all access options for this article.

References

Bernstein, J. and Losee, K.A. , (to Olin Mathieson Chemical Corp.), "Derivatives of 2-mercaptopyridine 1-oxide," U.S. Pat. 2,742,476 (1956); Chem. Abstr. 50, 16877b, 1956.

Black, J.G. and Howes, D. , Toxicity of Pyrithiones, Clin. Toxicol. 13, 1-26 (1978).

Edrissi, M. , Kooshkabadi, H. , and Lalezari, I. , Formation of 1,6-Diazathianthrene by Photolysis of 1-Hydroxy-2-pyridinethione , Microchem. J. 19, 282-284 (1974); Chem. Abstr. 81, 77856 (1974).

Edrissi, M. , Massoumi, A. , and Dalzeil, J.A.W. , Comparative Studies of 1-Hydroxy-2-pyridine-thione and Its Methyl Derivatives as Analytical Reagents for Metal Ions, Microchem. J. 16, 538-547 (1971).

Evans, P.G.E. , Sugden, J.K. , and Van Abbe , N.J. , Photochemical Behavior of 1-Hydroxypyridine-2-thione, Pharm. Acta Helv. 50(4), 94-99 (1975); Chem. Abstr. 83, 23692 (1975).

Gonzales, E.J. , Welch, C.M. , and Guthrie, J.D. , The Bonding of Phenols to Cotton with Zirconium Acetate, Textile Res. J. 33, 600-608 (1963).

Hock, A.L. , Zirconium Compounds : The Industrial Importance of Their Aqueous Chemistry, Chem. Ind. (London), pp. 864-870 (1974).

Intorre, B.I. and Martell, A.E. , Zirconium Complexes in Aqueous Solution. I. Reaction with Multidentate Ligands, J. Am. Chem. Soc. 82, 358-364 (1960).

Kawabe, Y. , Kanazawa, T. , Takimoto, G. , Ikeda, T. , Sato, M. , and Kano, S. , Antibacterial Activity of bis(2-pyridyl N-oxide) Disulfide, Nippon Kagaku Ryohogakukai Zasshi 15, 224-227 ( 1967); Chem. Abstr. 68, 1827 ( 1968).

10.

Kennedy, J.F. , Transition-Metal Oxide Chelates of Carbohydrate-Directed Macromolecules, Chem. Soc. Rev. 8, 221-257 (1979).

11.

Kennedy, J.F. , Barker, S.A. , and Zamir, A. , Active Insolubilized Antibiotics Based on Cellulose-Metal Chelates, Antimicrob. Agents Chemother. 6, 777-782 (1974).

12.

Kepert, D.L. , "The Early Transition Metals," Academic Press, New York, 1972, pp. 48-51, 104-114.

13.

Lifland, L. and Stanley, L. A., (to The Kendall Co.), "Bacteriostatic Finish for Cellulosic Fabrics," U.S. Pat. 3,594,113, 1971.

14.

Mirnigmatova, Sh. , Rakhmanberdiev, G. , and Gafurov, T.G. , Sintez Fiziologicheski Aktivhykh Proizvodnykh Tsellyulozy S Nekotorymi Nizkomolekulyarnymi Lekarstvennymi Preparatami, Uzb. Khim. Zh. 18(1),60-62 (1974).

15.

Quinn, H. , A Method for the Determination of the Antimicrobial Properties of Treated Fabrics, Appl. Microbiol. 10, 74-78 (1962).

16.

Sakaguchi, T. , Taguchi, K. , Fukushima , S. , and Obi, N. , Metal Chelate Compounds of Tetracycline Derivatives. VI. Behavior of Separated Metal Chelate Compounds of Chlortetracycline and Oxytetracycline, Yakugaku Zasshi 78, 177-182 (1958); Chem. Abstr. 52, 10990c ( 1958).

17.

Simionescu, C. , Dumitriu, S. , Bulacovschi , V. , and Popa, V.I. , Bioactive Polymers. III. Cellulose Derivatives as Support for Biologically Active Compounds, J. Polym. Sci., Polym. Symp. 66, 171-183 (1979).

18.

Tripp, V.W. , Piccolo, B. , Mitcham , D. , and O'Connor, R.T. , X-Ray Fluorescence Analysis of Modified Cottons, Textile Res. J. 34, 733-777 (1964).

19.

Vigo, T.L. , Danna, G.F. , and Welch, C.M. , Antibacterial Cotton Fabrics Containing Peroxide Complexes of Zirconyl Acetate , Textile Chem. Color. 9,77-80 (1977).

20.

Welch, C.M. , Danna, G.F. , and Vigo, T.L. , (to the United States of America as represented by the Secretary of Agriculture), "Antibacterial Textile Finishes Utilizing Zirconyl Acetate Complexes of Inorganic Peroxides," U.S. Pat. 4,115,422, 1978.