The synthesis and characterization of calix[4]arene based azo dyes

  • Shobhana K. Menon
  • Ravindra V. Patel
  • Jayesh G. Panchal
Original Article
First Online:
Received:
Accepted:

Abstract

A series of azocalix[4]arene dyes (1–7) were prepared by linking 2,4-di-chloroaniline, 2,4,5-tri-chloroaniline, 2,4-di-nitroaniline, 2-nitro p-toluidin, 4-nitro o-toluidin, 5-nitro o-toluidin and sulfanilic acid, to calix[4]arene through a diazo-coupling reaction. These compounds were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, MALDI-TOF, UV–Vis., DSC, and DTA. The absorption properties of the synthesized dyes were studied and the application of the water soluble dye on cotton and wool was discussed. Solvent based inks were investigated and the fastness properties of formulated inks were also discussed.

Keywords

Calix[4]arene dyes Spectral properties Application on cotton and wool Fastness studies Ink formulation 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgment

Financial assistance from UGC, New Delhi is gratefully acknowledged. The authors wish to thank Lucknow for spectral data. The facilities provided by Chemical Research and Development Centre and Anar Chemicals Vatva, Ahmedabad are also gratefully acknowledged.

References

  1. 1.
    Stephanie, B.-M., Jacques, B., Monique, P., Roger, L.: Synthesis of new phenylazocalix[n]arenes (n = 4, 5). Tetrahedron Lett. 41, 2563–2567 (2000)CrossRefGoogle Scholar
  2. 2.
    Saedioui, M., Asfari, Z., Vicens, J., Reynier, N., Dozol, J.F.: Synthesis, characterisation and UV–Vis properties of azocalix[4]crowns. J. Incl. Phenom. Macrocycl. Chem. 28, 223–244 (1997)CrossRefGoogle Scholar
  3. 3.
    Shinkai, S., Araki, K., Shibata, J., Tsugawa, D., Manabe, O.: Autoaccelerative diazo coupling with calix[4]arene: substituent effects on the unusual co-operativity of the OH groups. J. Chem. Soc., Perkin Trans. 1, 3333–3337 (1990)CrossRefGoogle Scholar
  4. 4.
    Tuntulania, T., Poompraduba, S., Thavornyutikarna, P., Jaiboona, N., Ruangpornvisutia, V., Chaichitb, N., Asfaric, Z., Vicensc, J.: Aza crown ether calix[4]arenes containing cation and anion binding sites: effects of metal ions towards anion binding ability. Tetrahedron Lett. 42, 5541–5544 (2001)CrossRefGoogle Scholar
  5. 5.
    Memon, S., Ylmaz, M.: A complimentary study of calixarene based bifunctional receptors for alkali or transition metal cations and Cr2O7 2−anions. J. Mol. Struct. 595, 101–109 (2001)CrossRefGoogle Scholar
  6. 6.
    Muhammad, A.: Synthesis and extraction properties of new chromogenic azo-calix[4]dibenzothiacrown ethers. J. Incl. Phenom. Macrocycl. Chem. 59, 315–321 (2007)CrossRefGoogle Scholar
  7. 7.
    Patel, R.V., Panchal, J.G., Rana, V.A., Menon S.K.: Liquid crystals based on calix[4]arene Schiff bases. J. Incl. Phenom. Macrocycl. Chem. (2009). doi:  10.1007/s10847-009-9620-z
  8. 8.
    Ozlem, O.K., Deligoz, H.: Azocalixarenes. 8: Synthesis and investigation of the absorption spectra of di-substituted azocalix[4]arenes containing chromogenic groups. J. Incl. Phenom. Macrocycl. Chem. 61, 288–296 (2008)Google Scholar
  9. 9.
    Karci, F., Senera, I., Deligoz, H.: Azocalixarenes. 1: Synthesis, characterization and investigation of the absorption spectra of substituted azocalix[4]arene. Dyes Pigments 59, 53–61 (2003)CrossRefGoogle Scholar
  10. 10.
    Karci, F., Sener, I., Deligoz, H.: Azocalixarenes. 2: Synthesis, characterization and investigation of the absorption spectra of azocalix[6]arenes containing chromogenic groups. Dyes Pigments 62, 131–140 (2004)CrossRefGoogle Scholar
  11. 11.
    Sener, I., Karci, F., Kılı¸, E., Deligoz, H.: Azocalixarenes. 3: Synthesis and investigation of the absorption spectra of hetarylazo disperse dyes derived from calix[4]arene. Dyes Pigments 62, 141–148 (2004)CrossRefGoogle Scholar
  12. 12.
    Deligoz, H.: Synthesis and properties of a series of novel calix[6]arene diazo derivatives. J. Incl. Phenom. Macrocycl. Chem. 43, 285–289 (2002)CrossRefGoogle Scholar
  13. 13.
    Uma, H., Menon, S.K.: The synthesis, characterization and spectral properties of crown ether based disazo dyes. Dyes Pigments 77, 446–462 (2008)CrossRefGoogle Scholar
  14. 14.
    Gutsche, C.D., Iqbal, M., Stewart, D.: Calixarenes. 19. Syntheses procedures for p-tert-butylcalix[4]arene. J. Org. Chem. 51, 742–745 (1986)CrossRefGoogle Scholar
  15. 15.
    National Institute of Industrial Research Board.: Modern Technology of Printing and Writing Inks. Asia Pacific Business, New Delhi (2001)Google Scholar
  16. 16.
    Assessment of Resistance of Prints to Various Agents. International Organization for Standardization ISO 2836 (2004)Google Scholar
  17. 17.
    Assessment of Light Fastness Using Filtered Xenon Arc Light. International Organization for Standardization ISO 12040 (1997)Google Scholar
  18. 18.
    Agrawal, Y.K., Pandya, B.R.: Ionization constants of crown dyes. Indian J. Chem. Technol. 9, 487–490 (2002)Google Scholar
  19. 19.
    Gordon, P.F., Gregory, P.: Organic Chemistry in Color. Springer-Verlag, New York (1983)Google Scholar
  20. 20.
    Solntsev, K.M., Huppert, D.: Solvatochromism of β-naphthol. J. Phys. Chem. 102, 9599–9606 (1998)Google Scholar

Copyright information

© Springer Science+Business Media B.V. 2009

Authors and Affiliations

  • Shobhana K. Menon
    • 1
  • Ravindra V. Patel
    • 1
  • Jayesh G. Panchal
    • 1
  1. 1.Department of Chemistry, School of SciencesGujarat UniversityAhmedabadIndia

Personalised recommendations