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Abstract

2-Amino-4(4′-nitro phenyl)-1,3-thiazole was used to couple with diazotized 2-amino-5(4′-nitro phenyl)-1,3,4-thiadiazole to gave mono azo disperse dye with good yield. This mono azo disperse dye was further diazotized and coupled with different tertiary amines which were couplers that yielded bis azo disperse dyes (AJ1-AJ15). The synthesized dyes were analyzed via elemental analysis, IR, 1H NMR spectral analysis. All the synthesized dyes were applied on polyester fiber by using HTHP method and their dyeing performance and their fastness characteristics were studied.

Keywords

2-Amino-5(4′-nitro phenyl)-1 3 4-thiadiazole 2-Amino-4(4′-nitro phenyl)-1 3-thiazole bis azo dyes Polyester.

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A. Kucha, N., J. Tank, M., M. Mitchla, S., T. Patel, F., & Malik, G. (2022). Synthesis of bis Azo Disperse Dyes derived from 2-Amino-4(4′-nitro phenyl)thiazole having tertiary-Amines as Coupling Component, their Characterization and Evolution of Dyeing Characteristics. Asian Journal of Organic & Medicinal Chemistry, 7(1), 131–136. https://doi.org/10.14233/ajomc.2022.AJOMC-P375
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References

  1. C.R. Meena, G. Singh, N. Sekar and R. Adivarekar, Synthesis and Application of Vinyl Sulphone Disperse Reactive Edyes for Polyester, Int. J. Chemtech Res., 5, 585 (2013).
  2. T.R. Desai and K.R. Desai, Synthesis of Azo Disperse Dyes with 2-Amino-5-phenyl-1,3,4-thiadiazole Moiety for Dyeing Polyester Fibre, J. Fibers Text. Res., 23, 185 (1998).
  3. S. Benkhaya, S. M'rabet and A. El-Harfi, Classifications, Properties, Recent Synthesis and Applications of Azo Dyes, Heliyon, 6, e03271 (2020); https://doi.org/10.1016/j.heliyon.2020.e03271
  4. G. Feng, H.-F. Qian, G. Bai, Y.-C. Liu and L.-L. Hu, Synthesis, Characterization and Application of Diester/Diurethane Tethered Azo Disperse Dyes: A New Strategy to Improve Dye’s Fastness Properties, Dyes Pigments, 129, 54 (2016); https://doi.org/10.1016/j.dyepig.2016.02.010
  5. J. Koh, H. Kim and J. Park, Synthesis and Spectral Properties of Phthalimide based Alkali-Clearable Azo Disperse Dyes, Fibers Polym., 9, 143 (2008); https://doi.org/10.1007/s12221-008-0024-2
  6. K.A. Bello and J. Griffiths, Violet to Cyan Azo Dyes Derived from 4-Amino-3-nitrobenzaldehyde as Diazo Component, Dyes Pigments, 11, 65 (1989); https://doi.org/10.1016/0143-7208(89)85026-0
  7. H. Jordan, 1,3-Thiazolyl Azo Dyes, their Preparation and Use, US Patent 7892295 (2008).
  8. H.-C. Tsien, K.-P. Chu and H. Chang, 2-Amino-5-nitrothiazole derived Monoazo Disperse Dyes, US Patent 5652344A (1997).
  9. H. Jordan and S. Neubauer, Disperse Dyes, their Preparation and their Use, EP2113011B1 (2006).
  10. M. Özkütük, E. Ipek, B. Aydiner, S. Mamas, and Z. Seferoglu, Synthesis, Spectroscopic, Thermal and Electrochemical Studies on Thiazolyl Azo Based Disperse Dyes Bearing Coumarin, J. Mol. Struct., 1108, 521 (2016); https://doi.org/10.1016/j.molstruc.2015.12.032
  11. M.A. Metwally, E. Abdel-latif, F.A. Amer and G. Kaupp, Synthesis of New 5-Thiazolyl Azo-Disperse Dyes for Dyeing Polyester Fabrics, Dyes Pigments, 60, 249 (2004); https://doi.org/10.1016/S0143-7208(03)00153-0
  12. H.R. Maradiya and V.S. Patel, Synthesis and Application of Disperse Dyes Based on 2-Aminothiazole Derivatives, Chem. Heterocycl. Compd., 39, 357 (2003); https://doi.org/10.1023/A:1023923012278
  13. N.A. Kucha, M.J. Tank and G.M. Malik, Synthesis, Characterization and Dyeing Performance of Mono Azo Disperse Dyes Based on 2-Amino 5-(4¢-nitrophenyl)-1,3,4-thiadiazole Moiety, Indian J. Appl. Res., 11, 54 (2021).
  14. S.K. Patel, P.K. Patel and G.M. Malik, Synthesis of Monoazo Disperse Dyes, their Dyeing Performance on Polyester Fibers and Antimicrobial Activity, IOSR J. Appl. Chem., 7, 8 (2014); https://doi.org/10.9790/5736-071020813
  15. S.M. Mitchla, F.T. Patel and G.M. Malik, Synthesis and Characterization of Monoazo Pyrazolone Dyes Based on 1,3,4-thiadiazole and their Dyeing Performance On Polyester Fabric, J. Ultra Chem., 14, 8 (2018); https://doi.org/10.22147/juc/140102
  16. G.M. Malik, P.C. Patel, J.H. Tailor and S.S. Patel, Fibers Polym., 19, 1670 (2018); https://doi.org/10.1007/s12221-018-7310-4
  17. P.C. Patel and G.M. Malik, Synthesis, Characterization and Fastness Properties of 2-Amino-5-methyl-1,3,4-thiadiazole, J. Appl. Chem., 8, 1739 (2019).
  18. S.K. Zadafiya, J.H. Tailor and G.M. Malik, Disperse Dyes Based on Thiazole, Their Dyeing Application on Polyester Fiber and their Antimicrobial Activity, J. Chem., 2013, 851418 (2013); https://doi.org/10.1155/2013/851418
  19. G.M. Malik, S.S. Patel and J.H. Tailor, Synthesis, Characterization, Dyeing Performance and Fastness Properties of 2-Amino 4-Phenyl Thiazole based Bisazo Disperse Dyes having Different Tertiary Amine as a Coupling Component, Chem. Biol. Interf., 6, 83 (2016).
  20. J.H. Tailor, P.C. Patel and G.M. Malik, Synthesis, Characterization and Antimicrobial Activity of 2-(11-Oxodibenzo [b,f][1,4]thiazepin-10-(11H)-yl)-N (Substituted phenyl)acetamide Derivatives, Indian J. Chem., 53B, 1263 (2014).
  21. S.M. Mitchla, F.T. Patel and G.M. Malik, Aminothienochromene based Bisazo Disperse Dyes: Synthesis, Characterization and Dyeing Application, J. Appl. Chem., 8, 1953 (2019).
  22. Standard Methods of Determining Fastness of Textile & Leather Bradford SOG, Ed.: 4 (1978).
  23. Indian Standard Methods for Determination of Colour Fastness of Textile Materials to Washing: Test 1 IS: 687-1979; Test 2 IS: 3361-1979; Test 3 IS: 764-1979; Test 4 IS: 765- 1979; Test 5 IS: 3417-1979.
  24. H.R. Maradiya and V.S. Patel, Thiazole based Disperse Dyes for Nylon and Polyester Fibers, Fibers Polym., 2, 153 (2001); https://doi.org/10.1007/BF02875329
  25. L. Shuttlewarth, M.A.Weaver, D.R. Warning and G. Halls, The Chemistry and Application of Dyes, Plenum Press: New York, p. 107 (1990).
  26. A.B. Patel, P.I. Vashi, V.D. Patel, D.H. Patel, K.C. Patel and P.S. Patel, Synthesis and Application of Monoazo Reactive Dyes on Silk, Wool and Cotton Fibers, J. Appl. Chem., 8, 1091 (2019).