This paper characterizes reaction products from the oxidoreductase enzymatic conver sion of aromatic amines to dyes that have an affinity for wool fibers. The dyes are identified with the aid of mass spectrometry, FRIR, 1H-NMR, combustion analysis, and by comparison of experimental and calculated λmax data. The results of these analyses indicate that the dyes are binuclear and trinuclear aromatic compounds, depending on the number of available coupling sites in the precursor molecules and the number of reactants employed in the coupling step. Pathways associated with this enzyme-induced formation of dyes are proposed that involve a two-electron oxidation of 1.4-diamines to electrophilic diimines.
Get full access to this article
View all access options for this article.
References
1.
Barfoed, M., Kirk, O., and Salmon, S., Enzymatic Method for Textile Dyeing, U.S. patent 6,296,672, 2001.
2.
Bourbonnais, Robert, and Paice, Michael G., Oxidation of Non-phenolic Substrates: An Expanded Role for Laccase in Lignin Biodegradation, FEBS Lett.267, 99-102 ( 1990).
Corbett, J.F. , TheChemistry of Hair-care Products. J. Soc. Dyers Color.92, 285-302 (1976).
5.
Corbett, John F., Hair Colouring, Rev. Prog. Color.15, 52-65 (1985).
6.
Corbett, John F., Synthetic Dyes for Human Hair, ch. 10 in "Colorants for Non-Textile Applications," H. S. Freeman and A. T. Peters, Eds., Elsevier Science B.V., Amsterdam. 2000.
7.
Freeman, H.S. , and Mohamed El-Zayatie, personal communication.
8.
Geiger, J.P. , Huguenin, B., Nicole , M., and Nanders, D., Laccases of Rigidoporus lignases and Phenellinus noxious, Appl. Biochem. Biophys.13, 97-110 (1986).
9.
James, T.H., "The Theory of the Photographic Process," 4th ed., T. H. James, Ed., MacMillan Publishing, NY, 1977.
10.
Kawai, Shingo , Imezawa, Toshiaki, and Higuchi , Takayoshi, Degradation Mechanisms of Phenolic β-1 Lignin Substructure Model Compounds by Laccase of Coriolus versicolor, Arch. Biochem. Biophys.262, 99-110 (1988).
