Abstract
The novel reactive photochromic spirooxazine dye containing a permanent chromophore and a reversible spirooxazine part was synthesized. The prepared dye was characterized by spectral analysis viz. FTIR, 1H-NMR, UV-Vis, mass spectroscopy, and elemental analysis. The results obtained from spectral data are strongly indicating that the research work was successful. The synthesized dye showed reversible color change from reddish-orange to violet under a UV light due to conversion of the colorless spirooxazine moiety to the merocyanine form which is blue. The dye was then applied on cotton. Color strength (K/S) values of the synthesized dye on cotton at various amounts of salt, alkali, and dye concentration were measured. Optimal amounts of salt (15 g/l), alkali (15 g/l) and dye concentrations (4 %) were obtained. The color change properties and the technical performance of the photochromic cotton samples were evaluated using color measurement methods. The data were analyzed in terms of color difference before and after exposure and K/S curves as a function of irradiation time. The fading speed was found to be slower than the photocoloration and the samples generally showed good wash fastness. The synthesized dye showed migration index of 67 %.
Similar content being viewed by others
References
G. H. Brown, “Photochromism (Techniques of Chemistry)”, pp.1–13, John Wiley & Sons, Inc., New York, 1971.
L. Song, Y. Yang, Q. Zhang, H. Tian, and W. Zhu, J. Phys. Chem. B, 115, 14648 (2011).
X. Meng, W. Zhu, Z. Guo, J. Wang, and H. Tian, Tetrahedron, 62, 9840 (2006).
V. Lokshin, A. Samat, and A. V. Metelitsa, Russ. Chem. Rev., 71, 893 (2002).
H. B. Laurent and H. Durr, Pure Appl. Chem., 73, 639 (2001).
S. Wang, C. Yu, M. S. Choi, and S. H. Kim, Dyes Pigment., 77, 245 (2008).
S. Wang, C. Yu, M. S. Choi, and S. H. Kim, Dyes Pigment., 78, 8 (2008).
B. Sun, Q. Hou, Z. He, Z. Liu, and Y. Ni, Carbohydr. Polym., 111, 419 (2014).
K. Ock, N. Jo, J. Kim, S. Kim, and K. Koha, Synth. Met., 117, 131 (2001).
J. C. Crano, T. Flood, D. Knowles, A. Kumar, and B. V. Gemert, Pure Appl. Chem., 68, 1395 (1996).
T. P. I. Saragi, T. Spehr, A. Siebert, T. F. Lieker, and J. Salbeck, Chem. Rev., 107, 1011 (2007).
M. Irie, Pure Appl. Chern., 62, 1495 (1990).
T. Feczko, O. Varga, M. Kovlcs, T. Vidoczy, and B. Voncina, J. Photochem. Photobiol. A-Chem., 222, 293 (2011).
M. Aldib and R. M. Christie, Color. Technol., 129, 131 (2012).
A. Perrier, F. Maurel, E. A. Perpete, V. Wathelet, and D. Jacquemin, J. Phys. Chem. A, 113, 13004 (2009).
A. Akbarzadeh, J. Mokhtari, S. Kolkoohi, and M. A. Sarli, J. Appl. Polym. Sci., 126, 1097 (2012).
R. M. Christie, “Colour Chemistry”, p.45, Royal Society of Chemistry, UK, 2001.
Y. A. Son, M. Y. Park, Y. S. Park, J. C. Shin, and H. S. Kim, Dyes Pigment., 73, 76 (2007).
W. H. Foster, and J. Kazan, Text. Res. J., 37, 376 (1967).
Y. A. Son, M. Y. Park, S. M. Choi, and H. S. Kim, Dyes Pigment., 75, 279 (2007).
T. Kakishita, K. Matusumoto, T. Kiyotsukuri, K. Matsumura, and M. Hosoda, J. Heterocycl. Chem., 29, 1709 (1992).
J. Mokhtari, D. Phillips, and J. A. Taylor, Dyes Pigment., 63, 51 (2004).
E. Allen in “Optical Radiation Measurements” (F. Grum and C. J. Bartleson Eds.), Vol. 2, Academic Press, New York, 1980.
M. S. Javadi, J. Mokhtari, M. Nouri, and F. Mazaheri, Fiber. Polym., 14, 920 (2013).
M. J. Bradbury, P. S. Collishaw, and S. Moorhouse, Text. Chem. Color., 27, 19 (1995).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mokhtari, J., Akbarzadeh, A., Shahrestani, Z. et al. Synthesis, characterization, and evaluation of a novel spirooxazine based photochromic reactive dye on cotton. Fibers Polym 16, 2299–2307 (2015). https://doi.org/10.1007/s12221-015-5265-2
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12221-015-5265-2