Dyeing Properties of Some New Disperse Dyes Containing Piperazine Moiety

Journal: Vol.8, No.3, Summer 2015 - Article 3   Pages :  197 Until 206

Article Code:

A. Mohammadi: University of Guilan - Department of Chemistry,Faculty of Sciences
Marzeih Sadat Tahavor: University of Guilan - Department of Chemistry, Faculty of Sciences
Zahra Dehghan: University of Guilan - Department of Chemistry, Faculty of Sciences

Article's abstract:

Four novel azo disperse dyes based on 1-4-bromobenzyl-4-phenylpiperazine were synthesized in two steps, using alkylation and azo coupling reactions. Chemical structure of the dyes was characterized and confirmed by the Ultraviolet Visible UV-Visible, Fourrier Transform Infrared FT-IR, Proton Nuclear Magnetic Resonance 1H NMR and Carbon Nuclear Magnetic Resonance 13C NMR analyses. The solvatochromic behavior of the dyes was studied in a set of 10 solvents with different polarity and considerable results were obtained. The prepared dyes were applied as disperse dyes for dyeing polyester fibers and their dyeing properties were evaluated. The fastness properties of the dyed fabrics such as wash, light and rubbing fastness degrees were measured by standard methods. Investigation of antioxidant activity of compounds was carried out by ferric reducing antioxidant power FRAP method. The activity data show that the synthesized dyes B1-B4 have promising antioxidant activity, comparable with their precursor B.

Azo disperse dye; N-phenylpiperazine; Dying; Spectroscopy; Antioxidant activity

1. H. S. Freeman, A. T. Peters, Colorants for Non-Textile Applications, Elsevier, Amsterdam, 2000.#2. H. Zollinger. Color chemistry: syntheses, properties and application of organic dyes and pigments. 2nd ed. Weinheim: VCH; 1991.#3. R. M. Christie, Colour Chemistry. Royal Society of Chemistry, Cambridge, UK; 2001. 4. J. Griffiths, Photochemistry of azobenzene and its derivatives, Chem. Soc. Rev, 1 (1972), 481-493.#5. H. S. Bhatti, S. Seshadri, Synthesis and fastness properties of styryl and azo disperse dyes derived from 6-nitro substituted 3-aryl-2-methyl-4(3H)-quinazolinone, Color Technol., 120 (2004), 151-155.#6. D.M. Marmion, Handbook of US. Colorants, third ed., John Wiley and Sons, Inc., New York, 1991.#7. K. Hunger, Industrial Dyes (Chemistry, Properties, Applications), WILEY-VCH, 2003.#8. M. A Metwally, E Abdel-latif, F. A. Amer, G. Kaupp, Synthesis of new 5-thiazolyl azo-disperse dyes for dyeing polyester fabrics, Dyes Pigments, 60 (2004), 249-264.#9. R. W. Sabnis, D. W. Rangnekar, Synthesis of azo benzo[b]thiophene derivatives and their application as disperse dyes, Dyes Pigments, 10 (1989), 295-302.#10. C. Novotny, N. Dias, A. Kapanen, K. Malachova, M. Vandrovcova, M. Itavaara, N. Lima, Comparative use of bacterial, algal and protozoan tests to study toxicity of azo- and anthraquinone dyes, Chemosphere, 63 (2006), 1436-1442.#11. P. C. H. Hollman, M. B Katan, Dietary Flavonoids: Intake, Health Effects and Bioavailability, Food Chem. Toxicol. 37 (1999), 937-942.#12. M. K. Prashanth, H. D. Revanasiddappa, K. M. Lokanatha Rai, B. Veeresh, Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues, Bioorg. Med. Chem. Lett., 22 (2012), 7065-7070.#13. A. Mohammadi, Novel triazene dyes based on N-phenylpiperazine: Synthesis, anti-bacterial activity and solvatochromic properties, J. Mol. Liq., 193 (2014), 69-73.#14. A. A. Fadda, K. M. Elattar, Synthesis of Novel Azo Disperse dyes Derived from 4-Aminoantipyrine and their Applications to Polyester Fabrics, Am. J. Org. Chem., 2 (2012), 52-57.#15. C. J. Dinsmore, D. C. Beshore, Recent advances in the synthesis of diketopiperazines, Tetrahedron, 58 (2002), 3297-3312.#16. M. Cincioglu, G. Kismali, S. A. Ugur, P. Kelicen-Ugur, Indinavir inhibits the expression of cytoplasmic aromatase and nuclear SREBP in the hippocampus of reperfusion injury-induced ischemic rats, J Steroid Biochem Mol Biol., 130 (2012), 81-89.#17. J. Béahdy, Recent developments of antibiotic research and classification of antibiotics according to chemical structure, Adv. Appl. Microbiol. 18 (1974), 309-406.#18. T. Saito, K. Koyama, S. Natori, Y. Iitaka, Chetracin A, a new epipolythiodioxopiperazine having a tetrasulfide bridge from chaetomium abuense and C. retardatum, Tetrahedron Lett., 26 (1985), 4731-4734.# 19. M. R. Yazdanbakhsh, A. Mohammadi, Synthesis, substituent effects and solvatochromic properties of some disperse azo dyes derived from N-phenyl-2, 2′-iminodiethanol, J. Mol. Liq., 148 (2009), 35-39.#20. I. F. F. Benzie, J. J. Strain, The ferric reducing ability of plasma (FRAP) as a measure of antioxidant power: the FRAP assay, Anal. Biochem., 239 (1996) 70-76.#21. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3rd ed., WileyVCH, Weinheim, 2003.#22. S. Adeel, M. Usman, W. Haider, M. Saeed, M. Muneer, M. Ali, Dyeing of gamma irradiated cotton using Direct Yellow 12 and Direct Yellow 27: improvement in colour strength and fastness properties, Cellulose, (2015), DOI: 10.1007/s10570-015-0596-0.#23. I. A. Bhatti, S. Adeel, H. Taj, Application of Vat Green-1 dye on Gamma ray Treated Cellulosic Fabric, Radiat Phys Chem., 102 (2014), 124-127.#24. I. A. Bhatti, S. Adeel, S. Siddique, M. Abbas, Effect of UV radiations on dyeing of cotton fabric with Reactive Blue 13. J. Saudi Chem. Soc., 18 (2014), 606-609.#25. K. Thaipong, U. Boonprakob, K. Crosby, L. Cisneros-Zevallos, D. H. Byrne, Comparison of ABTS, DPPH, FRAP, and ORAC assays for estimating antioxidant activity from guava fruit extracts, J. Food Compost Anal., 19 (2006), 669-675.#26. E. J. Baron, S. M. Finegold, Bailey and Scotts’s diagnostic microbiology, 8th Ed. The C.V. Mosby Company, St. Louis. Baltimore. Philadelphia. Toronto. 1990, PP. 363-407.#27. M. Kimura, T. Masuda, K. Yamada, N. Kawakatsu, N. Kubota, M. Mitani, K. Kishii, M. Inazu, Y. Kiuchi, K. Oguchi, T. Namiki, Antioxidative activities of novel diphenylalkyl piperazine derivatives with high affinities for the dopamine transporter, Bioorg. Med. Chem. Lett., 14 (2004), 4287-4290.

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