Synthesis and dyeing performance of some amphiphilic naphthalimide azo disperse dyes on polyester fabrics
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Abstract
A series of monoazo disperse dyes were synthesized by coupling diazotized 4-amino-N-dodecyl-1,8-naphthalimide with N,N-dialkyl anilines and naphthol derivatives. The synthesized intermediates and the dyes were characterized using FTIR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental analysis (CHN). Visible absorption spectra of the dyes were examined in solvents of different polarities. The electronic absorption spectra cover a wavelength (λmax) range of 515–535 nm in DMF at uniformly absorption intensity between 1.59–3.00×104 L mol-1 cm-1. The dyes gave deep and bright intense hues of light violet, maroon, pink and neon red on polyester fabrics. The dyes generally showed good washing and perspiration rating but poor to moderate light fastness properties on woven polyester fabric and could be recommended for commercial outlets.
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References
A. A. Fadda, H. A. Etman, F. A. Amer, M. Barghout, K. S. Mohamed, J. Chem. Technol. Biotechnol. 61 (1994) 343 (https://doi.org/10.1002/jctb.280610410)
M. M. M. Raposo, A. M. R. C. Sousa, A. M. C. Fonseca, G. Kirsch, Tetrahedron 61 (2005) 8249 (https://doi.org/10.1016/j.tet.2005.06.039)
M. R. Yazdanbakhsh, A. Ghanadzadeh, E. Moradi, J. Mol. Liq. 136 (2007) 165 (https://doi.org/10.1016/j.molliq.2007.03.005)
M. A.Weaver, L. Shuttleworth, Dyes Pigm. 3 (1982) 81 (https://doi.org/10.1016/0143-7208(82)80016-8)
J. A. Mielczarski, G. M. Atenas, E. Mielczarski, Appl. Catal., B 56 (2000) 289 (https://doi.org/10.1016/j.apcatb.2004.09.017)
H. R. Maradiya, V. S. Patel, J. Braz. Chem. Soc. 12 (2001) 710 (http://dx.doi.org/10.1590/S0103-50532001000600004)
L. C. Abbott, S. N. Batchelor, J. Oakes, B. C. Gilbert, A. C. Whitwood, J. R. L. Smith, J. N. Moore, J. Phys. Chem., A 109 (2005) 2894 (https://pubs.acs.org/doi/abs/10.1021/jp045216s)
P. C. Tsai, I. J. Wang, Dyes Pigm. 74 (2007) 578 (https://doi.org/10.1016/j.dyepig.2006.03.022)
A. C. Razus, L. Birzan, N. M. Surugiu, A. C. Corbu, F. Chiraleu, Dyes Pigm. 74 (2007) 26 (https://doi.org/10.1016/j.dyepig.2006.01.041)
M. M. M. Raposo, M. C. R. Castro, A. M. C. Fonseca, P. Schellenberg, M. Belsley, Tetrahedron 67 (2011) 5189 (https://doi.org/10.1016/j.tet.2011.05.053)
J. Griffiths, Color and Constitution of Organic Molecules. Academic Press, London, 1976, p. 32 (https://doi.org/10.1002/col.5080030213)
A. T. Peters, M. J. Bide, Dyes Pigm. 7 (1986) 237 (https://doi.org/10.1016/0143-7208(86)85012-4)
A. R. Khosravi, S. Moradian, K. Gharanjig, F. Afshar Taromi, J. Chin. Chem. Soc. 52 (2005) 495 (https://doi.org/10.1002/jccs.200500071)
K. Gharanjig, M. Arami, S. Rouhani, H. Bahrami, B. Movassagh, N. Mahmoodi, J. Chin. Chem. Soc. 54 (2007) 1021 (https://doi.org/10.1002/jccs.200700147)
P. Parvizi, A. R. Khosravi, S. Moradian, K. Gharanjig, J. Chin. Chem. Soc. 56 (2009) 1035 (https://doi.org/10.1002/jccs.200900150)
A. Khosravi, S. Mordian, K. Gharanjig, F. AfsharTaromi, Dyes Pigm.69 (2006) 79 (https://doi.org/10.1016/j.dyepig.2005.02.007)
T. Konstantinova, A. Spirieva, T. Petkova, Dyes Pigm. 45 (2000) 125 (https://doi.org/10.1016/S0143-7208(00)00014-0)
R. Stolarski, Fibres Text. East. Eur. 17 (2009) 91.
J. Szadowski, K. Wojciechowski, W. Malinowski, Color Technol. 101 (1985) 105 (https://doi.org/10.1111/j.1478-4408.1985.tb01013.x)
M. Okazaki, T. Tanaka, S. Taniguchi, Yuki Gosei Kagaku Kyokaishi 14 (1957) 344 (https://doi.org/10.5059/yukigoseikyokaishi.14.344)
M. Okazaki, Y. Suhara, M. Fujiyama, Yuki Gosei Kagaku Kyokaishi 14 (1956) 394 (https://doi.org/10.5059/yukigoseikyokaishi.14.394)
M. Dong, Y. W. Wang, Y. Peng, Org. Lett. 12 (2010) 5310 (https://doi.org/10.1021/ol1024585)
U. S. Ameuru, M. K. Yakubu, K. A. Bello, P. O. Nkeonye, A. Ziyaei Halimehjani, Dyes Pigm. 157 (2018)190 (https://doi.org/10.1016/j.dyepig.2018.04.050)
R. M. Abd El-Aal, A. I. Koraierm, J. Chin.Chem. Soc. 47 (2000) 389 (https://doi.org/10.1002/jccs.200000052)
V. Bojinov, G. Ivanova, J. M. Chovelon, I. Grabchev, Dyes Pigm. 58 (2003) 65 (https://doi.org/10.1016/S0143-7208(03)00036-6)
K. Wojciechowski, Dyes Pigm. 12 (1990) 273 (https://doi.org/10.1016/0143-7208(90)85018-J)
A. Datyner, J. Soc. Dye Colourist 94 (1978) 256 (https://doi.org/10.1111/j.1478-4408.1978.tb03417.x)
A. M. Al-Etaibi, M. A. El-Apasery, M. R. Ibrahim, N. A. Al-Awadi, Molecules 17 (2012) 13891 (https://doi.org/10.3390/molecules171213891)
H. R. Chipalkatti, N. F. Desai, C. H. Giles, N. Macaulay, J. Soc. Dye Colourist 70 (1954) 487 (https://doi.org/10.1111/j.1478-4408.1954.tb02006.x)
J. Wang, H. Asnes, J. Soc. Dyers Col.107 (1991) 314 (https://doi.org/10.1111/j.1478-4408.1991.tb01364.x).