Synthesis and Evaluation of Non-genotoxic Direct Dyes

  • Bae, Jin-Seok (Department of Textile Engineering, Chemistry and Science, North Carolina State University) ;
  • Freeman, Harold S. (Department of Textile Engineering, Chemistry and Science, North Carolina State University)
  • Published : 2002.12.01

Abstract

Non-genotoxic diamines 2,2'-dimethyl-5,5'-dipropoxybenzidine and 5,5'-dipropoxy-benzidine were employed as potential alternatives to benzidine in the synthesis and evaluation of new direct dyes for cotton. Assessment of the resultant dyes indicated that both diamines can be used to prepare new direct dyes having colors and fastness properties that make them comparable to commercial direct dyes, and that the structures of the new direct dyes can be confirmed by negative ion electrospray mass spectrometry (ESMS). The mutagenic properties of new direct dyes were established using the standard Ames Salmonella mammalian mutagenicity assay.

Keywords

References

  1. W. S. Perkins, Textile Coloration and Finishins, 123 (1996)
  2. J. Shore, Colorants and Auxiliaries, 1, 174 (1990)
  3. A. Haddow, New Scientist, 25, 348 (1965)
  4. C. E. Searle, Chemistry in Britain, 6, 5 (1970)
  5. IARC 'Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man', 8, 1975
  6. Case, RAM, Brit, J. Ind. Med,, 75, 11 (1954)
  7. M. V. Barsontti, EC. AMA Arch. Ind. Hyg. Occup. Med., 5, 234(1962)
  8. T. S. Scott, Brit. J. Ind. Med., 9, 27 (1952)
  9. C. P. Hartman, G. E. Fulk, and A. W. Andrews, Mutation Research, 58, 125 (1978) https://doi.org/10.1016/0165-1218(78)90001-0
  10. E. A. Messerly, J. E. Fekete, D. R. Wade, and J. E. Sinsheimer, Environmental and Molecular Mutagenesis, 10, 263 (1987) https://doi.org/10.1002/em.2850100305
  11. H. S. Freeman, M. K. Esancy, J. F. Esancy, and L. D. Claxton, Chemtech, 21(7), 438 (1991)
  12. W. Bauer and J. Ritter in 'Chemistry of Functional Dyes', Vol. 2, p.649, 1993
  13. H. S. Freeman, D. Hinks, and J. Essancy in 'Advances in Color Chemistry Series', (A. T. Peters and H. S. Preeman Eds.) Vol. 4, pp.254-292, Blackie Academic and Professional, London, 1996
  14. OSHA, 'Carcinogens: Occupational Health and Safety Standards', US Federal Register 39, 3756-97, 1974
  15. The Carcinogenic Substances Regulations, UK Statutory Instrument, No. 879, 1967
  16. Fishbein in 'The Handbook of Environmental Chemistry', (D. Hutzinger, Ed.), 3, C, pp. 1-40, Springer-Verlag, New York, 1984
  17. E. Clark, Int. Dyer and Text. Printer, 5, 250 (1984)
  18. T. L. Vigo, Textile Science and Technology, 11, 118 (1994)
  19. M. M. Shahin, D. Rovers, A. Buguat, and G. Kalopissis, Mutation Research, 79(4), 289 (1980) https://doi.org/10.1016/0165-1218(80)90153-6
  20. M. M. Shahin, A. Buguat, and G. Kalopissis, Mutation Research, 78(1), 25 (1980) https://doi.org/10.1016/0165-1218(80)90022-1
  21. M. M. Shahin, C. Chopy, and N. Lequesne, Environmental Mutagenesis, 7(4), 535 (1985) https://doi.org/10.1002/em.2860070412
  22. K. Hunger, H. Frolich, H. Hertel, and H. Habig, DE 3511544 (1986)
  23. K. Hunger, H. Frolich, H. Hertel, and H. Habig, DE 3511545 (1986)
  24. W. Bauer and K. Hunger, DE 3534634 (1987)
  25. H. S. Freeman, D. Hinks, and S. Jolanta, Dyes and Pigments, 44(3), 199 (2000) https://doi.org/10.1016/S0143-7208(99)00078-9
  26. D. Hinks, H. S. Freeman, and S. G. Jolanta, Dyes and Pigments, 48, 15 (2001) https://doi.org/10.1016/S0143-7208(00)00088-7
  27. AATCC Technical Manual, 75, 23, 88 (2000)
  28. M. Maron and B. N. Ames, Mutation Research, 113, 173 (1983) https://doi.org/10.1016/0165-1161(83)90010-9