Synthesis and Characterisation of Colorants Derived from 1,4-Diamino Anthraquinone Polyamides


In this study, the polycondensation products of a diamine anthraquinone (1,4-diamino anthraquinone) and some aliphatic diacids with different methylene numbers were synthesised. Their UV-visible spectroscopy and thermal properties were then characterised. The synthesis was achieved by reacting equimolar solutions of the amine and the acid halides. The structure and thermal properties of the products were characterised. FT-IR Spectra of all the three products revealed the formation of amide due to the presence of strong bands at 1565 and 3390 cm?1 assignable to C=O stretching and N-H vibrations. Differential Scanning Calorimetry revealed high melting exotherms for the products. Thermogravimetry revealed moderate thermal stabilities for Poly NAM and Poly NAS and low thermal stability for Poly NAA which indicated 5.9%, 7.1% and 61.2% weight losses at 285℃, 285℃ and 374℃ for the three products respectively. The wavelengths of maximum absorbance for the dye samples are 601.5, 591 and 589 nm respectively with absorptivity coefficients (a1cm1% ) of 11640000, 11610000 and 11560000 respectively.

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Kabir Yakubu, M. , Sani Gumel, M. , Bala Ibrahim, M. and Kumar, R. (2012) Synthesis and Characterisation of Colorants Derived from 1,4-Diamino Anthraquinone Polyamides. Advances in Chemical Engineering and Science, 2, 300-308. doi: 10.4236/aces.2012.22035.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] J. S. Wang, H. J. Chen and S. Evans, EP 1283249, 2003.
[2] H. R. Maradiya and V. S. Patel, “Studies of Novel Monomeric and Polymeric Azo Disperse Dyes,” Journal of Applied Polymer Science, Vol. 84, No. 7, 2002, pp. 1380-1389. doi:10.1002/app.10276
[3] H. R. Maradiya and V. S. Patel, “N-Arylmaleimide Based Monomeric and Polymeric Dyes for Cellulose Triacetate Fiber,” International Journal of Polymeric Materials, Vol. 52, No. 2, 2003, pp. 119-131. doi:10.1080/714975923
[4] X. H. Hu, X. Y. Zhang, J. B. Dai and G. W. Xu, “Synthesis and Characterization of a Novel Aqueous Dispersion Poly[urethane-(disperse blue 14)-urethane] Dye,” Chinese Chemical Letters, Vol. 15, No. 5, 2004, pp. 515-517.
[5] K. H. Shah, M. P. Patel, K. G Amin, R. G. Patel and V. S. Patel, “Synthesis and Characterization of Polymeric Dyes,” Acta Ciencia Indica Chemistry, Vol. 23, 1997, p. 177.
[6] M. M. Tian, G. R. Hawkins and A. C. Chan, US 2003106168, 2003.
[7] L. M. Parrinello, R. Rogers, C. T. Hill, L. E. Lipko, P. L. Benenati and P. Nowakowski, US 2003180523, 2003.
[8] I. Grabchev, “Photophysical Characteristics of Polymerizable 1,8-Naphthalimide Dyes and Their Copolymers with Styrene or Methylmethacrylate,” Dyes and Pigments, Vol. 38. No. 4, 1998, pp. 219-226. doi:10.1016/S0143-7208(97)00117-4
[9] K. Singh, S. Singh and J. A. Taylor, “Monoazo Disperse Dyes—Part 1: Synthesis, Spectroscopic Studies and Technical Evaluation of Monoazo Disperse Dyes Derived from 2-Aminothiazoles,” Dyes and Pigments, Vol. 54, No. 3, 2002, pp. 189-200. doi:10.1016/S0143-7208(02)00053-0
[10] T. Konstantinova, P. Meallier, Hr. Konstantinov and D. Staneva, “Synthesis and Photochemical Properties of Triazinylaminobenzanthrone Derivatives as Dyes for Polymeric Materials,” Polymer Degradation and Stability, Vol. 48, No. 1, 1995, pp. 161-166. doi:10.1016/0141-3910(95)00014-D
[11] M. Qinghua, H. Deyin, W. Shaohua and C. Lin, “Synthesis and Application of Polymeric Dyes Containing the Anthraquinone Structure,” Journal of Applied Polymer Science, Vol. 83, No. 6, 2002, pp. 1252-1257. doi:10.1002/app.2292
[12] K. Sung-Hoon, C. Jian-Zhong, P. Jin-Yong, R. JangHyun, H. S. P. Eun-Mi, J. Sung-Ho, K. Kwangnak and G. Yeong-Soon, “Synthesis and Light Emitting Properties of Polymeric Metal Complex Dyes Based on Hydroxyquinoline Moiety,” Dyes and Pigments, Vol. 55, 2002, pp. 91-97. doi:10.1016/S0143-7208(02)00088-8
[13] J. M. R. C. Fernando and G. K. R. Senadeera, “Synthesis and Characterization of Carboxylated Thiophene CoPolymers and Their Use in Photovoltaic Cells,” Current Science, Vol. 95, No. 6, 2008, pp. 743-750.
[14] B. T. Tang, S. F. Zhang, J. Z. Yang and F. Liu, “Synthesis of a Novel Water-Soluble Crosslinking Polymeric Dye with Good Dyeing Properties,” Dyes and Pigments, Vol. 68, No. 1, 2006, pp. 69-73.
[15] M. G. Patel, K. R. Desai and H. S. Patel, “Synthesis and Characterization of Colored Polyureas,” E-Journal of Chemistry, Vol. 1, No. 1, 2004, pp. 51-56.
[16] M. Joshi, S. Jauhari and K. R. Desai, “Polyureas: Synthesis and Characterization,” International Journal of ChemTech Research CODEN (USA): Vol. 3, No. 1, 2011, pp. 29-32.
[17] J. Park, J. Yang, J. Lee, E. Lim, J. Suh, Y. Huh and S. Haam, “Synthesis and Characterization of Fluorescent Magneto Polymeric Nanoparticles (FMPNs) for Bimodal Imaging Probes,” Journal of Colloid and Interface Science, Vol. 340, 2009, pp. 176-181. doi:10.1016/j.jcis.2009.08.015
[18] H. S. Panah, A. Khosrav, K. Gharanjig, M. Khorassani, M. K. Zadeh and F. A.Taromi, “Synthesis and Characterization of New Fluorescent Polymerizable Dyes Based on Naphthalimide,” Iranian Polymer Journal, Vol. 19, No. 7, 2010, pp. 491-500.
[19] M. Edward and M. Caffery, “Laboratory Preparation of Macromolecular Chemistry,” Mc Graw-Hill, Inc., New York, 1970, pp. 101-113, 247 and 263.
[20] A. A. Caraculacu, N. C. Lungu and G. Caraculacu, “Aromatic Polyamide with Parabanic Structure,” European Polymer Journal, Vol. 24, No. 12, 1988, p. 1207. doi:10.1016/0014-3057(88)90113-9
[21] J. F. Davis, “Synthesis of Aromatic Polyamides, Polymer Chemistry, A practical approach,” Oxford University Press, New York, 2004, pp. 126-127.
[22] H. B. William and S. F. Christopher, “Organic Chemistry Text Book,” 2nd Edition, Saunders College Publishers, United States, 1998, p. 506.
[23] S. M. Gumel, “Study on the Surface Finishing of Leather Using Some Commercial and Novel Polymers,” Ph.D Thesis, Bayero University, Kano, 2001.
[24] F. W. Billmeyer, “A Text Book of Polymer Science,” Second Edition, John Wiley and Sons, Inc., New York, 1984, p. 120.
[25] M. Ibrahim, “Synthesis and Characterisation of Polymeric Dyes Derived from 1, 4-Diamino Anthraquinone,” MSc Thesis, Bayero University, Kano, 2010.
[26] J. A. Dean, “Lange’s Handbook of Chemistry,” McGraw Hill Inc., New York, 1992.
[27] T. M. Robert and N. B. Robert, “A Text Book of Organic Chemistry,” Prentice Hall of India Private Limited, New Delhi, 2001, pp. 585-596.
[28] J. A. Dean, “The Analytical Chemistry Hand Book,” McGraw Hill, Inc., New York, 1995, pp. 15.1-15.5.
[29] K. C. Cole, C. Decker, M. Jutigny, J. M Lefebvre and P. Krawzak, “Biaxial Deformation of Polyamide-6, Assessment of Orientation by Means of IR Trichroism,” Polymer Engineering and Science, Vol. 44, No. 2, 2000, pp. 231-240.
[30] S. Zhang, Z. Wu and J. Yang, “Polymeric Dyes, A New Field of Dye Chemistry,” Dalian University of Technology Press, 1995, pp. 45-46.
[31] E. Pungor, “A Practical Guide to Instrumental Analysis,” Boca Raton, Florida, 1995, pp. 181-191.
[32] A. S Douglas, F. J. Holler and S. R. Crouch, “Principles of Instrumental Analysis,” 5th Edition, Brooks/Cole, Thompson Learning, New York, 1998.
[33] J. Wang, S. Zhang, B. Tang, J. Yang, “Application of Polymeric Dyes in Textile Fields,” The Proceedings of the 3rd International Conference on Functional Molecules, Dalian University of Technology, China, 8-11 September 2005, pp. 8-11.

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