Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Applications of Some Azo Dyes Derived from Various Aromatic Amines
Corresponding Author(s) : V. Sadasivan
Asian Journal of Chemistry,
Vol. 30 No. 9 (2018): Vol 30 Issue 9
Abstract
In this work, we report the synthesis of metal free dyes and their fastness properties. A series of monoazo dyes obtained by diazotization of various aromatic primary amines and coupling with different components. One coloured Schiff base derived from triethylene tetramine and N,N-dimethylbenzaldehyde was also synthesized. These coloured compounds were characterized by FTIR, UV-visible, 1H, 13C NMR and ESI mass spectroscopic methods. The dyeing performance of all the compounds were evaluated on cotton fabric. They were applied on bleached cotton fabric and their dyeing and fastness properties were assessed. The absorption spectra of the dyes are discussed with regard to their structure. The structure of coloured dyes and Schiff base are proposed based on various spectroscopic data. The newly synthesized group of monoazo dyes gives shades ranging from yellow to reddish orange with good light fastness and excellent wash fastness.
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- V.A. Shenai, Chemistry of Dyes and Principles of Dyeing, Sevak Publication, Bombay, India (1973).
- Anon, Standard Methods for Determination of Colour Fastness of Textiles and Leather, Society of Dyers and Colourists Publication Bradford, England (1990).
- AATCC Test method, p. (1961).
- Indian Standard ISO, p. 765 (1979).
- Standard Rest Method BS 1006-1978; UK, ISO 105-1995.
- B.C. Dixit, H.M. Patel and D.J. Desai, J. Serb. Chem. Soc., 72, 119 (2007); https://doi.org/10.2298/JSC0702119D.
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- P.F. Gordon and P. Gregory, Organic Chemistry in Colour, Springer-Verlag, New York (1983).
- H.R. Maradiya, Turk. J. Chem., 25, 441 (2001).
References
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A. Navarro and F. Sanz, Dyes Pigments, 40, 131 (1999); https://doi.org/10.1016/S0143-7208(98)00048-5.
K.L. Georgiadou and E.G. Tsatsaroni, Dyes Pigments, 50, 93 (2001); https://doi.org/10.1016/S0143-7208(01)00034-1.
J.A. Mikroyannidis, D.V. Tsagkournos, S. Sharma, A. Kumar, Y.K. Vijay and G.D. Sharma, Sol. Energy Mater. Sol. Cells, 94, 2318 (2010); https://doi.org/10.1016/j.solmat.2010.08.001.
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D. Zhang, M. Zhang, Z. Liu, M. Yu, F. Li, T. Yi and C. Huang, Tetrahedron Lett., 47, 7093 (2006); https://doi.org/10.1016/j.tetlet.2006.07.080.
B.A. Trofimov, E.Y. Schmidt, A.I. Mikhaleva, A.M. Vasil’tsov, A.B. Zaitsev, N.S. Smolyanina, E.Y. Senotrusova, A.V. Afonin, I.A. Ushakov, K.B. Petrushenko, O.N. Kazheva, O.A. Dyachenko, V.V. Smirnov, A.F. Schmidt, M.V. Markova and L.V. Morozova, Eur. J. Org. Chem., 4021 (2006); https://doi.org/10.1002/ejoc.200600357.
M. Bhaskar, A. Gnanamani, R.J. Ganeshjeevan, R. Chandrasekar, S. Sadulla and G. Radhakrishnan, J. Chromatogr. A, 1018, 117 (2003); https://doi.org/10.1016/j.chroma.2003.08.024.
M. Dakiky and I. Nemcova, Dyes Pigments, 44, 181 (2000); https://doi.org/10.1016/S0143-7208(99)00086-8.
M.M. Russew and S. Hecht, Adv. Mater., 22, 3348 (2010); https://doi.org/10.1002/adma.200904102.
E. Kleinpeter, U. Bolke and J. Kreicberga, Tetrahedron, 66, 4503 (2010); https://doi.org/10.1016/j.tet.2010.04.067.
X. Li, Y. Wu, D. Gu and F. Gan, Dyes Pigments, 86, 182 (2010); https://doi.org/10.1016/j.dyepig.2010.01.002.
J. Griffiths, Colour and Constitution of Organic Molecules; Academic Press, London, p. 186 (1976).
A.D. Towns, Dyes Pigments, 42, 3 (1999); https://doi.org/10.1016/S0143-7208(99)00005-4.
V. Arun, P.P. Robinson, S. Manju, P. Leeju, G. Varsha, V.K.K.M. Digna and K.K.M. Yusuff, Dyes Pigments, 82, 268 (2009); https://doi.org/10.1016/j.dyepig.2009.01.010.
H.S. Bhatti and S. Seshadri, Color. Technol., 120, 151 (2004); https://doi.org/10.1111/j.1478-4408.2004.tb00221.x.
V.H. Patel, M.P. Patel and R.G. Patel, Dyes Pigments, 52, 191 (2002); https://doi.org/10.1016/S0143-7208(01)00068-7.
D.R. Patel and K.C. Patel, Dyes Pigments, 90, 1 (2011); https://doi.org/10.1016/j.dyepig.2010.10.013.
D.R. Patel and K.C. Patel, Arab. J. Chem., 76, 1 (2011).
D.R. Patel and K.C. Patel, Serb. Chem. Soc., 76, 177 (2011); https://doi.org/10.2298/JSC090225021P.
M.M. Parekh and K.C. Maheria, J. Sci. Ind. Res., 70, 525 (2010).
G.B. Bagihalli, P.G. Avaji, S.A. Patil and P.S. Badami, Eur. J. Med. Chem., 43, 2639 (2008); https://doi.org/10.1016/j.ejmech.2008.02.013.
E. Rodríguez-Fernández, J.L. Manzano, J.J. Benito, R. Hermosa, E. Monte and J.J. Criado, J. Inorg. Biochem., 99, 1558 (2005); https://doi.org/10.1016/j.jinorgbio.2005.05.004.
Z.H. Chohan, S.H. Sumrra, M.H. Youssoufi and T.B. Hadda, Eur. J. Med. Chem., 45, 2739 (2010); https://doi.org/10.1016/j.ejmech.2010.02.053.
J. Park and D.J. Smith, J. Soc. Dyers Colourists, 90, 431 (1974); https://doi.org/10.1111/j.1478-4408.1974.tb03179.x.
C.L. Bird, J. Soc. Dyers Colourists, 70, 68 (1954); https://doi.org/10.1111/j.1478-4408.1954.tb02017.x.
V. Sadasivan and M. Alaudeen, Indian J. Chem., 46A, 1959 (2007).
G. Kaupp, J. Schmeyers and J. Boy, J. Prakt. Chem., 342, 269 (2000); https://doi.org/10.1002/(SICI)1521-3897(200003)342:3<269::AIDPRAC269>3.0.CO;2-0.
V.G. Vidya, S.S. Meena, P. Bhatt, V. Sadasivan and S. Mini, AIP Conf. Proc., 1536, 1009 (2013); https://doi.org/10.1063/1.4810574.
S. Mini, S.S. Meena, P. Bhatt, V. Sadasivan and V.G. Vidya, AIP Conf. Proc., 1620, 1011 (2013); https://doi.org/10.1063/1.4810575.
V.G. Vidya, V. Sadasivan, S.S. Meena and P. Bhatt, AIP Conf. Proc., 1620, 622 (2014); https://doi.org/10.1063/1.4898308.
S. Mini, V. Sadasivan, S.S. Meena and P. Bhatt, AIP Conf. Proc., 1536, 322 (2014); https://doi.org/10.1063/1.4898259.
M.A. Metwally, Dyes Pigments, 60, 249 (2004); https://doi.org/10.1016/S0143-7208(03)00153-0.
H.R. Maradiya, J. Saudi Chem. Soc., 14, 77 (2010); https://doi.org/10.1016/j.jscs.2009.12.012.
V.A. Shenai, Chemistry of Dyes and Principles of Dyeing, Sevak Publication, Bombay, India (1973).
Anon, Standard Methods for Determination of Colour Fastness of Textiles and Leather, Society of Dyers and Colourists Publication Bradford, England (1990).
AATCC Test method, p. (1961).
Indian Standard ISO, p. 765 (1979).
Standard Rest Method BS 1006-1978; UK, ISO 105-1995.
B.C. Dixit, H.M. Patel and D.J. Desai, J. Serb. Chem. Soc., 72, 119 (2007); https://doi.org/10.2298/JSC0702119D.
H.R. Maradiya and V.S. Patel, Bull. Chem. Technol., 21, 57 (2002).
G. Hallas and A.D. Towns, Dyes Pigments, 35, 45 (1997); https://doi.org/10.1016/S0143-7208(96)00088-5.
M.R. Massafra, E. Selli, S. Salsa and B. Marcandalli, Dyes Pigments, 40, 171 (1999); https://doi.org/10.1016/S0143-7208(98)00045-X.
P.F. Gordon and P. Gregory, Organic Chemistry in Colour, Springer-Verlag, New York (1983).
H.R. Maradiya, Turk. J. Chem., 25, 441 (2001).