Synthesis and Applications of Heterocyclic Based Dyes Derived From Substituted 1, 3-Benzothiazole on Chrome and Vegetable Tanned Leather

Obadahun J., Bukar P. H., Agho O. B., Adams D. A., Enyeribe C., Ibrahim Y. M.

Abstract


Synthesis and applications of heterocyclic based dyes derived from substituted 1, 3-benzothiazole on chrome and vegetable tanned leather were carried out. The intermediate were diazotized, coupled and the dyes were purified by re-crystallization. The melting points were found to span from 143°C- 186°C and spectroscopic assessment such as FT-IR, GC-MS and NMR spectroscopy were carried out to elucidate their structures. The vibrational frequency obtained for the synthesized dyes shows the characteristics absorption peaks due to stretching frequency of the NH-group in the region 3198.1-3459 cm-1. The IR spectra of the prepared azo dye also showed an absorption peak in the region 1490.9-1543.1 cm-1 attributed to azo chromophoric group (N=N), while the observed peak in the region 1602.8-1695.9. Also the GC-MS analysis of Dye BZT 1, BZT 2, BZT 3 and BZT 4 showed molecular ion peaks at m/z 327.3 328.3, 328.3 and 329.3 respectively which is consistent with the molecular formula of the dyes. The 1H and 13C- NMR spectra  for the synthesized dye  showed eight signals with a highly deshielded signal at 10.39 ppm (IH, singlet) which is attributed to the presence of the OH of the carboxylic group, 7.73 – 8.27  ppm due to the presence of amino (-NH2) protons. Two signals were observed for two pairs of aromatic proton in the (6.84 – 7.81) ppm range with a coupling constant of 8 – 12 Hz. Also a distinct signal was observed up field at 3.06 ppm due to the presence of methyl (CH3) proton. The 13C-NMR spectrum of the Dyes showed the signal at 162.26 ppm for the carbon atom in the COOH group. Thus a signal at 141.41 ppm for carbon atom in the thiazole ring was also observed while the signal at 140.06 -115.56 ppm for aromatic carbon. The heterocyclic dye BZT 1, BZT 2, BZT 3 and BZT 4 were applied at 2 % depth on chrome and vegetable tanned leather.  The dyes on application gave pink, dark red, brown and dark brown hues with brighter and deeper shades, tinctorial strength and excellent levelness on the leather. The variation in the shade of dyed fabric results from alteration in the diazo and coupling component. The remarkable degree of levelness and brightness indicate good penetration and excellent affinity of the dyes to the leather. In addition the result obtained showed that the dyed leather have excellent fastness  to washing which may be due to the absence of solubilizing group, which affect solubility and washing ability of the dye-out of the leather.


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