Skip to content
Research Article Open access CC BY 4.0

The Use of Heterocyclic Azo Dyes on Different Textile Materials: A Review

Lucia Emanuele, Maurizio D’Auria

Organics · pp. 277–289 · Published 20 Aug 2024

10.3390/org5030015

Abstract

The art of dyeing textiles has a long history, as natural dyes have been used since prehistoric times. With the development of synthetic dyes in the 19th century, the focus shifted from natural to synthetic dyes due to their superior properties. Recently, however, interest in natural dyes has increased again due to environmental and health concerns. Among industrial dyes, heterocyclic dyes, especially azo dyes, are of great importance due to their color brilliance and fastness. This review examines the synthesis, application, and analysis of azo dyes, especially heterocyclic dyes. It deals with monoazo, diazo, and polyazo dyes and highlights their structures, synthesis methods, and fastness properties. In addition, the ecological impact of azo dyes and practical solutions for their synthesis and application are discussed.

Textile Pulp and paper industry Chemistry Materials science Composite material Engineering

References (48)

  1. 1 Muthu, S. (2014). Natural Dyes: Sources, Chemistry, Application and Sustainability Issues. Roadmap to Sustainable Textiles and Clothing. Textile Science and Clothing Technology, Springer. [DOI]
  2. 2 Clark, 2011, Natural Dyes
  3. 3 Waring, 1984, Heterocyclic Dyes and Pigments
  4. 4 Winkler, F. (1983). The Colour Science of Dyes and Pigments, Adam Hilger Ltd.
  5. 5 Decelles, 1949, The story of dyes and dyeing [DOI]
  6. 6 Salman, 2023, New heterocyclic azo-disperse dyes; their synthesis, characterization, application, photo physical properties and solvatochromic studies [DOI]
  7. 7 Griffiths, J. (1976). Color and Constitution of Organic Molecules, Academic Press.
  8. 8 Hallas, 1999, Synthesis and properties of novel aziridinyl azo dyes from 2-aminothiophenes—Part 2: Application of some disperse dyes to polyester fibres [DOI]
  9. 9 Baroncini, 2019, Light-Responsive (Supra)Molecular Architectures: Recent Advances [DOI]
  10. 10 Wu, 2011, NIR-light-induced deformation of cross-linked liquid crystalpolymers using upconversion nanophosphors [DOI]
  11. 11 Waring, D.R., and Hallas, G. (1990). Classification of Dyes by Chemical Structure. The Chemistry and Application of Dyes: Topics in Applied Chemistry, Springer. [DOI]
  12. 12 Towns, 1999, Developments in azo disperse dyes derived from heterocyclic diazo components [DOI]
  13. 13 Patel, 2002, Synthesis and application of novel heterocyclic dyes based on 1l-amino-3-bromo-13H-acenaphtho[l,2-e]pyridazino[3,2-b]- quinazoline-13-one [DOI]
  14. 14 Patel, 2010, Synthesis, characterization and application of quinazolinone based reactive dyes for various fibers [DOI]
  15. 15 Patel, 2011, Synthesis of Some New Thermally Stable Reactive Dyes Having 4(3H)-quinazolinone Molecule for the Dyeing of Silk, Wool, and Cotton Fibers [DOI]
  16. 16 Patel, 2015, Synthesis, characterization and in vitro antimicrobial screening of some new MCT reactive dyes bearing nitro quinazolinone moiety [DOI]
  17. 17 Lellis, 2019, Effects of textile dyes on health and the environment and bioremediation potential of living organisms [DOI]
  18. 18 Malinauskiene, 2013, Contact allergy from disperse dyes in textiles: A review [DOI]
  19. 19 Moreau, 2005, Allergic contact dermatitis associated with reactive dyes in a dark garment: A case report [DOI]
  20. 20 Miles, L.W.C. (2003). Textile Printing, Society of Dyers and Colourists. [2nd ed.].
  21. 21 Shaban, 2023, Antibacterial Azo Dyes Containing Sulfa Drug Moieties and Their Colour Assessment on Printing Polyester Fabric [DOI]
  22. 22 National Center for Biotechnology Information (2024, February 22). “PubChem Compound Summary for CID 6249, Ampicillin” PubChem, Available online: https://pubchem.ncbi.nlm.nih.gov/compound/Ampicillin.
  23. 23 Benkhaya, 2020, Classifications, properties, recent synthesis and applications of azo dyes [DOI]
  24. 24 Gunst, R. (1953). Heterocyclic Disazo Dyestuffs. (No 2,686,178), U.S. Patent.
  25. 25 Fabian, 1996, Comparative molecular field analysis (CoMFA) of dye-fibre affinities. Part 2. Symmetrical bisazo dyes [DOI]
  26. 26 Matsui, 1998, Fluorine-containing benzothiazolyl bisazo dyes-their application to guest-host liquid crystal displays [DOI]
  27. 27 2005, Synthesis of disazo dyes derived from heterocyclic components [DOI]
  28. 28 Hadjoudis, 2004, Photochromism and thermochromism of Schiff bases in the solid state: Structural aspects
  29. 29 Gawinecki, 2005, Tautomeric equilibria in relation to pi-electron delocalization [DOI]
  30. 30 2020, Tautomerism of azo dyes in the solid state studied by 15N, 14N, 13C and 1H NMR spectroscopy, X-ray diffraction and quantum-chemical calculations [DOI]
  31. 31 Bakan, 2016, Synthetic Fiber Dyeing with Synthesized Novel Disperse Disazo Dyes Containing Methyl (-CH3) Group as an Auxochrome and Their Color Properties
  32. 32 Elnagdi, 1976, Reactions with the Arylhydrazones of α-Cyanoketones: The Structure of 2-Arylhydrazono-3-ketimino-nitriles [DOI]
  33. 33 Elnagdi, 1985, Recent developments in the synthesis of pyrazole derivatives [DOI]
  34. 34 Naime, 2022, Synthesis, characterization and application of a novel polyazo dye as a universal acid–base indicator [DOI]
  35. 35 2019, Synthesis, characterisation, solvatochromic behaviour and thermal decomposition kinetics of novel polyazo dyes containing amide group and their transition metal complexes [DOI]
  36. 36 Nath, I., Chakraborty, J., Abednatanzi, S., and Van Der Voort, P. (2021). A ‘Defective’ Conjugated Porous Poly-Azo as Dual Photocatalyst. Catalysts, 11. [DOI]
  37. 37 Zhang, 2022, Optimal model evaluation of the proton-exchange membrane fuel cells based on deep learning and modified African Vulture Optimization Algorithm [DOI]
  38. 38 Bo, 2022, Optimum structure of a combined wind/photovoltaic/fuel cell-based on amended Dragon Fly optimization algorithm: A case study [DOI]
  39. 39 Mijin, 2011, Synthesis of azo pyridone dyes [DOI]
  40. 40 Zouari-Mechichi, H., Benali, J., Alessa, A.H., Hadrich, B., and Mechichi, T. (2024). Efficient Decolorization of the Poly-Azo Dye Sirius Grey by Coriolopsis gallica Laccase-Mediator System: Process Optimization and Toxicity Assessment. Molecules, 29. [DOI]
  41. 41 Chung, 2016, Azo Dyes and Human Health: A Review [DOI]
  42. 42 Pereira, L., and Alves, M. (2012). Dyes—Environmental impact and remediation. Environmental Protection Strategies for Sustainable Development, Springer. [DOI]
  43. 43 Hussien, 2021, An eco-friendly methodology for the synthesis of azocoumarin dye using cation exchange resins [DOI]
  44. 44 Amjad, 2009, Synthesis and Spectral Studies of Some Novel Coumarin Based Disperse Azo Dyes: Studies of Coumarin Based Azo Dyes
  45. 45 Al-Harby, N.F., Albahly, E.F., and Mohamed, N.A. (2021). Kinetics, isotherm and thermodynamic studies for efficient adsorption of Congo Red dye from aqueous solution onto novel cyanoguanidine-modified chitosan adsorbent. Polymers, 13. [DOI]
  46. 46 Ali, A.E., Chowdhury, Z.Z., Devnath, R., Ahmed, M.M., Rahman, M.M., Khalid, K., Wahab, Y.A., Badruddin, I.A., Kamangar, S., and Hussien, M. (2023). Removal of Azo Dyes from Aqueous Effluent Using Bio-Based Activated Carbons: Toxicity Aspects and Environmental Impact. Separations, 10. [DOI]
  47. 47 Fernandes, A., Pinto, B., Bonardo, L., Royo, B., Robalo, M.P., and Martins, L.O. (2021). Wasteful Azo dyes as a source of biologically active building blocks. Front. Bioeng. Biotechnol., 9. [DOI]
  48. 48 Ravindiran, 2023, Removal of azo dyes from synthetic wastewater using biochar derived from sewage sludge to prevent groundwater contamination [DOI]

Cited by 48

Harnessing ultrasound for quinonoid colorants extraction: an overview

Sharad R. Patil, K. B. Patil, Mustakim I. Bagwan · Journal of the Iranian Chemical Society · 2026

Quantum Catalysis for the Analysis of Organic Dyes in Textile Wastewater

Vivek Jaiswal, Kumar Ghosh, Chandra Jeet Singh · Sustainable materials and technology · 2026

Sulfadiazine-based pyrazolone azo dyes: Synthesis, characterization and their biological evaluation

Amrutha. M, Yadav D. Bodke · Journal of Molecular Structure · 2026

Synthesis and characterization of a new Azo dye and study of its adsorption mechanism on graphene oxide nanoparticles

Abeer Hussein Ali, Liqaa Hussein Alwan, Diana AbdAlkreem Al-Rifaie · EPJ Web of Conferences · 2026

Diazo retention transformations of aryldiazonium salts towards nitrogen rich heterocycles

Mani Ramanathan, Ziad Moussa, Rama Krishna Peddinti · Organic & Biomolecular Chemistry · 2026

Identification of Exiguobacterium artemiae Strains Tolerant to Xenobiotics in Wastewater from the Bogota River, Colombia

Camilo Torres-Trujillo, Nelson Enrique Arenas, Magdalena Wiesner · Brazilian Archives of Biology and Technology · 2026

Showing 23 of 48 known citations — external sources report more than can currently be individually listed.

Article metrics

Real usage data collected on this platform.

0

Page views

0

PDF downloads

0

Outbound clicks

48

Citations

Views by country

Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".

No views recorded yet.

Traffic sources

Referring site, by host.

No traffic recorded yet.

Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.