Sustainable Reactive Dyeing of Cotton Fabric in Green Non-Aqueous Medium: A Density Function Theory (DFT) Modeling Study

Abstract:

Sustainable reactive dyeing of cotton in green non-nucleophilic solvents was investigated. Dye fixation in the new medium was modeled using DFT calculations with the aim of understanding the role of organic bases. The novel procedure uses non-nucleophilic green solvents instead of water to eliminate the dye hydrolysis. All residuals in the spent dye bath could be conveniently recycled and reused. The three major stages in cotton reactive dyeing, cellulose swelling, dye adsorption and dye fixation were optimized respectively. Two organic bases and potassium carbonate were studied for dye fixation. The mechanisms of the amine-promoted dye fixation were modeled using density function theory (DFT) calculations. The formation of the amine-dye intermediate was elucidated and analyzed using high performance liquid chromatography (HPLC) analysis. The quaternary ammonium catalysis effect on intermediates forming was observed. A 10-cycle repeated dyeing sequence was demonstrated using Reactive orange 5 to give consistently high shade buildup, excellent colorfastness and dramatic reduction in resource consumption. The results have implications for better understanding the new hydrolysis-free and recyclable solvent dyeing process.

• Periodical: Key Engineering Materials (Volume 671)
• Pages: 139-148
• DOI: https://doi.org/10.4028/www.scientific.net/KEM.671.139
• Online since: November 2015
• Authors: Lu Yi Chen, Jian Gang Chen, Xin Hui Ruan, Su Xin Xu, Yi Qi Yang, Bi Jia Wang*
• Keywords: Cotton Fabrics, Density Functional Theory (DFT), Hydrolysis-Free Reactive Dyeing, Sustainable Dyeing

References

[1] A. Khatri, M.H. Peerzada, M. Mohsin, M. White, A review on developments in dyeing cotton fabrics with reactive dyes for reducing effluent pollution, Cleaner Prod. 87 (2015) 50-57.

DOI: 10.1016/j.jclepro.2014.09.017

[2] C. Allegre, P. Moulin, M. Maisseu, F. Charbit, Treatment and reuse of reactive dyeing effluents, Membr. Sci. 269 (2006) 15-34.

DOI: 10.1016/j.memsci.2005.06.014

[3] R. Jiraratananon, A. Sungpet, P. Luangsowan, Performance evaluation of nanofiltration membranes for treatment of effluents containing reactive dye and salt, Desalination. 130 (2000) 177-183.

DOI: 10.1016/s0011-9164(00)00085-0

[4] Y. Yang, L. Xu, Reusing hydrolyzed reactive dyebath for nylon and wool dyeing, Am. Dyest. Rep. 85 (1996) 27-34.

[5] M. Banchero, Supercritical fluid dyeing of synthetic and natural textiles–a review, Color. Technol. 129 (2013) 2-17.

[6] G.B. Montero, C.B. Smith, W.A. Hendrix, D.L. Butcher, Supercritical fluid technology in textile processing: an overview, Ind. Eng. Chem. Res. 39 (2000) 4806-4812.

DOI: 10.1021/ie0002475

[7] T. Hori T, A. Kongdee, Dyeing of PET/co-PP composite fibers using supercritical carbon dioxide, Dyes Pigm. 105 (2014) 163-166.

DOI: 10.1016/j.dyepig.2014.01.023

[8] J. Long, H. Xu, C. Cui, X. Wei, F. Chen, A. Cheng, A novel plant for fabric rope dyeing in supercritical carbon dioxide and its cleaner production, J. Cleaner Prod. 65 (2014) 574-582.

DOI: 10.1016/j.jclepro.2013.08.008

[9] G. Cocoros, T.V. Chambers, J. J. Hirshfeld. U.S. Patents, (1978).

[10] B. Wang, X Ruan, L. Chen, J. Chen, Y. Yang, Heterogeneous Chemical Modification of Cotton Cellulose with Vinyl Sulfone Dyes in Non-Nucleophilic Organic Solvents, Ind. Eng. Chem. Res. 53 (2014) 15802-15810.

DOI: 10.1021/ie503173m

[11] O. Acevedo, W.L. Jorgensen, Solvent effects and mechanism for a nucleophilic aromatic substitution from QM/MM simulations, Org. Lett. 6 (2004) 2881-2884.

DOI: 10.1021/ol049121k

[12] Cid M.V. Fernandez, W. Buijs, G. Witkamp, Application of molecular modeling in the optimization of reactive cotton dyeing in supercritical carbon dioxide, Ind. Eng. Chem. Res. 46 (2007) 3941-3944.

DOI: 10.1021/ie061076s

[13] C.C.R. Sutton, G.V. Franks, G. Da Silva, First principles pKa calculations on carboxylic acids using the SMD solvation model: effect of thermodynamic cycle, model chemistry, and explicit solvent molecules, J. Phys. Chem. B. 116 (2012).

DOI: 10.1021/jp305876r

[14] E. Kissa, Lightfastness of reactive dyes, Text. Res. J. 41 (1971) 715-719.

[15] F. Aricò, P. Tundo, Dimethyl carbonate: a modern green reagent and solvent, Russ. Chem. Rev. 79 (2010) 479-489.

DOI: 10.1070/rc2010v079n06abeh004113

[16] G. Koller,U. Fischer, K. Hungerbühler, Assessing safety, health, and environmental impact early during process development, Ind. Eng. Chem. Res. 39 (2000) 960-972.

DOI: 10.1021/ie990669i

[17] T.L. Dawson, The reaction mechanism and fixation of monochloro-s-triazine dyes on cellulose using tertiary amine catalysts, J. Soc. Dyers Colour. 80 (1964) 134-143.

DOI: 10.1111/j.1478-4408.1964.tb02584.x