Synthesis and Characterization of Some New Azo-imine Dyes and their Applications


Farouq E. Hawaiz, Darya J. Raheem and Mohammed K. Samad

College of Education/ University of Salahadin-Hawler, Kurdistan Region, Iraq

DOI: https://doi.org/10.17656/jzs.10532

Abstract

Some new azo-imine dyes have been synthesized via the diazotization of sulphanilic acid and its coupling reaction with salicylaldehyde giving a starting material 4-((3-formyl-4-hydroxyphenyl)diazenyl)benzenesulfonic acid. The later reacted with different substituted anilines to give the target azo-imine dyes [4-((3-((4-substitutedphenylimino)methyl)-4-hydroxyphenyl)diazenyl)benzenesulfonic acid] which were confirmed by using FT-IR, 1H-NMR and 13C-NMR spectra. The synthesized dyes are used for dyeing performance on acetate, cotton, nylon, wool, acrylic and polyester fibers, along with the effect of mordant on dyeing process. All the synthesized dyes gave moderate to excellent fastness properties on each fiber. The effect of cationic and anionic surfactants on the wash fastness has been studied.




Key Words:  Azo-imines, Dyeing, Mordant, Multi-fiber strip, Fastness.


References

 

[1] Zarei M., and Jarrahpour A., "Green and efficient synthesis of azo Schiff bases. Iranian Journal of  Science and Technology", Vol.35, No.3, pp.235-242, (2011).

[2] Hussain Z., Yousif E., Ahmed A., and Altaie A., "Synthesis and characterization of Schiff's bases of  sulfamethoxazole". Organic and medicinal chemistry letters, Vol. 4, pp.1-4, (2014).

[3] Patel P.S., and Hathi M.V., "Studies on synthesis and dyeing performance of disperse azo dyes based on Schiff base of ninhydrin and 3-amino phenol". Arch. Appl. Sci. Res, Vol.4, No.2, pp. 846-51,(2012).

[4] Brodowska K., and LodygaChruscinska E., " Schiff Bases Interesting Range of Applications in Various Fields of Science".  CHEMIK, Vol. 68, No.2, pp.129–134, (2014).

[5]Prakash A., and Adhikari D., "Application of Schiff bases and their metal complexes-A Review". International Journal of Chem Tech Research, Vol.3, No.4, pp. 1891-1896, (2011).

[6] Hawaiz F.E., and  Samad M.K.., "Synthesis and Spectroscopic Characterization of Some New Biological Active Azo–Pyrazoline Derivatives". E. Journal of Chemistry, Vol.9, No.3, pp. 1613-1622, (2012).

[7]Hussein A.J., and Aziz H. J., "Synthesis and spectroscopic characterization of some new azo- thiazolidinone derivatives". Der ChemicaSinica, Vol.2, No.5, pp. 136-146, (2011).

[8] Abuamer K.M., Maihub A.A., El-Ajaily M.M., Etorki A.M., Abou-Krisha M.M., and Almagani M.A.., "The Role of Aromatic Schiff Bases in the Dyes Techniques". International Journal of Organic  Chemistry, Vol. 4, pp.7-15, ( 2014).

[9] Hawaiz F.E., Hussein A.J., and Samad, M.K., "One-pot three-component synthesis of some new azo- pyrazoline derivatives". European Journal of Chemistry, Vol.5, No.2, pp.233-236, (2014).

[10] Hawaiz F.E., Samad M.K., and Aziz M.Y., "Synthesis of some new heterocyclic compounds derived from 4-(4-hydroxy-3-chlorophenyl) azoacetophenone".Journal of Zankoi Sulaimani, JZS Vol.17, No.2, pp.85-91, (2015).

[11] Hussein A.J., "Synthesis and Characterization of Some New Pyrazoline Compounds Derived from Azo- Benzaldehyde". Journal of Pure and Applied Sciences, Vol. 27, No.1, pp. 51-58, (2014).

[12] Karaer H.,  andGümrükçüoglu I.E., "Synthesis and spectral characterisation of novel azo- azomethine dyes". Turkish Journal of Chemistry, Vol.23, pp.67-72, (1999).

[13] Zarkogianni M., Mikropoulou E., Varella E., and Tsatsaroni E., "Colour and fastness of natural dyes: revival of traditional dyeing techniques". Coloration Technology, Vol.127, No.1, pp. 18-27, (2011).

[14] Cristea D., and Vilarem G., "Improving light fastness of natural dyes on cotton yarn". Dyes and  pigments, Vol.70, No.3, pp. 238-245, (2006).

[15] Tehrani-Bagha A.R., and Holmberg K., "Solubilization of hydrophobic dyes in surfactant  Solutions". Materials, Vol.6, No.2, pp. 580-608, (2013).