Skip to main content

Advertisement

SpringerLink
Log in

Sustainable dyeing of cotton fabric with reactive dye in silicone oil emulsion for improving dye uptake and reducing wastewater

  • Original Research
  • Published:
Cellulose Aims and scope Submit manuscript

Abstract

From sustainable chemistry and engineering perspectives, water and energy consumption are arguably the main issues in the textile industry. Thus, a silicone reverse emulsion dyeing system is developed to dye cellulosic textile with reactive dye. When the amount of dye is the same, the color depth of dyed cotton fiber is 13.82 and the fixation of dye is 87.76% in the silicone reverse emulsion dyeing system. In traditional water-based dyeing system, the color depth of dyed cotton fiber and the fixation of dye is only 9.31, 56.63% respectively. The silicone reverse emulsion dyeing technology does not consumes salts, but it can improve the dye fixation by 31.13%, and decreases the dye discharge by 72.41%. For the hydrolysis of bifunctional reactive dye, the main hydrolysis reaction is the individual hydrolysis of monochlorotriazine or vinyl sulfone at the prophase of hydrolysis. After 30 min, the additional β-hydroxyethyl sulfone and hydroxyl triazine dye are hydrolyzed to dihydroxyl dye. To confirm the hydrolytic reaction energy of dye in different dyeing system, the optimization of molecular structure, the hydrolysis reaction gap and the distribution of electron density on the dye were investigated using density functional theory. The hydrolytic reaction energy gap of bifunctional reactive dye is higher in silicone reverse emulsion dyeing system than that in traditional aqueous dyeing system, resulting the hydrolysis of dye is difficult in silicone oil emulsion dyeing system. The electron density is distributed almost entirely on the carbon–carbon double bond and triazine group in the HOMO of the dye, resulting in the LUMO of dyes can attacked by HOMO of hydroxyl anion. These successful investigations of the dyeing performance and the hydrolysis mechanism of dye explain that reactive dye can keep a long reactivity to fiber and effectively reduce the number of washing times, which greatly reduces the discharge of dyeing waste water.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  • Aldib M, Christie RM (2013) Textile applications of photochromic dyes. Part 5: application of commercial photochromic dyes to polyester fabric by a solvent-based dyeing method. Color Technol 29:131–143

    Google Scholar 

  • Amin MN, Blackburn RS (2015) Sustainable chemistry method to improve the wash-off process of reactive dyes on cotton. ACS Sustainable Chem Eng 3:725–732

    CAS  Google Scholar 

  • Aouchiche HA, Djennane S, Boucekkine A (2004) DFT study of conjugated biheterocyclic oligomers exhibiting a very low HOMO–LUMO energy gap. Synthetic Met 140:127–133

    Google Scholar 

  • Banchero M (2013) Supercritical fluid dyeing of synthetic and natural textiles–a review. Color Technol 129:2–17

    CAS  Google Scholar 

  • Banchero M (2020) Recent advances in supercritical fluid dyeing. Color Technol 136(4):317–335

    CAS  Google Scholar 

  • Bhavsar PS, Marina Z, Alessia P, Montarsolo A, Mossotti R, Giansetti M, Rovero G, Maier SS, Muresan A, Tonin C (2017) Superheated water hydrolyzed keratin: a new application as a foaming agent in foam dyeing of cotton and wool fabrics. ACS Sustainable Chem Eng 5:9150–9159

    CAS  Google Scholar 

  • Domoradzki JY, Sushynski CM, Sushynski JM, Mcnett DA, Van Landingham C, Plotzke KP (2017a) Metabolism and disposition of [C-14]—methycyclosiloxanes in rats. Toxicol Lett 279:98–114

    CAS  PubMed  Google Scholar 

  • Domoradzki JY, Sushynski JM, Thackery LM, Springer TA, Ross TL, Woodburn KB et al (2017b) Metabolism of C-14-octamethylcyclotetrasiloxane ([(C-14]D-4) or (C-14)-decamethylcyclopentasiloxane ([(C-14]D-5) orally gavaged in rainbow trout (Oncorhynchus mykiss). Toxicol Lett 279:115–124

    CAS  PubMed  Google Scholar 

  • Cai Y, Pailthorpe MT, David SK (1999) A new method for improving the dyeability of cotton with reactive dyes. Text Res J 69:440–446

    CAS  Google Scholar 

  • Chandra R, Ewanick S, Hsieh C, Saddler JN (2008) The characterization of pretreated lignocellulosic substrates prior to enzymatic hydrolysis, part 1: a modified Simons’ staining technique. Biotechnol Progr 24:1178–1185

    CAS  Google Scholar 

  • Cheng M, Yang X, Zhang F, Zhao J, Sun L (2013) Tuning the HOMO and LUMO energy levels of organic dyes with N-carboxomethylpyridinium as acceptor to optimize the efficiency of dye-sensitized solar cells. J Phys Chem C 117:9076–9083

    CAS  Google Scholar 

  • Deng L, Ziegler T (1994) The determination of Intrinsic Reaction Coordinates by density functional theory. Int J Quantum Chem 52:731–765

    CAS  Google Scholar 

  • Fu CC, Wang JP, Liu JQ (2015) A non-aqueous dyeing process of reactive dye in cotton. J Text Inst 106:152–161

    CAS  Google Scholar 

  • Gao XY, Liu JQ, Li YQ (2007) The impact of D5-washing on the fabric performance. J Zhejiang Sci-Tech Univ 24:6–10

    Google Scholar 

  • Huang P, Xia D, Kazlauciunas A, Thornton PD, Lin L, Menzel R (2019) Dye-mediated interactions in chitosan-based polyelectrolyte/organo-clay hybrids for enhanced adsorption of industrial dyes. ACS Appl Mater Inter 11:11961–11969

    CAS  Google Scholar 

  • Jaxel J, Gusenbauer C, Bhmdorfer S, Liebner F, Hansmann C (2020) Improving single-step scCO2 dyeing of wood by DMSO-induced micro-swelling. J Supercrit Fluid 165:104978

    CAS  Google Scholar 

  • Jóźwiak T, Brym UFS, Zysk M (2020) The use of aminated cotton fifibers as an unconventional sorbent to remove anionic dyes from aqueous solutions. Cellulose 27:3957–3969

    Google Scholar 

  • Jung J, Sun G (2001) Recovery of sodium sulfate from farm drainage salt for use in reactive dyeing of cotton. Environ Sci Technol 16:3391–3395

    Google Scholar 

  • Klančnik M (2006) The influence of temperature on the kinetics of concurrent hydrolysis and methanolysis reactions of a monochlorotriazine reactive dye. Dyes Pigments 46:9–15

    Google Scholar 

  • Klančnik M (2008) Kinetics of hydrolysis of halogeno-s-triazine reactive dyes as a function of temperature. Chem Biochem Eng Q 22:81–88

    Google Scholar 

  • Klančnik M, Gorenšek M (1997) Kinetics of hydrolysis of monofunctional and bifunctional monochloro-s-triazine reactive dyes. Dyes Pigments 33:337–350

    Google Scholar 

  • Koh J (2005) Alkali-hydrolysis kinetics of alkali-clearable azo disperse dyes containing a fluorosulphonyl group and their fastness properties on PET/cotton blends. Dyes Pigments 64:17–23

    CAS  Google Scholar 

  • Kono T, Kumaki D, Nishida JI, Tokito S, Yamashita Y (2010) Dithienylbenzobis (thiadiazole) based organic semiconductors with low LUMO levels and narrow energy gaps. Chem Commun 46:3265–3267

    CAS  Google Scholar 

  • Kuo WG (1992) Decolorizing dye wastewater with Fenton’s reagent. Water Res 26:881–886

    CAS  Google Scholar 

  • Luo XJ, White J, Thompson R, Rayner C, Kulik BM, Kazlauciunas A, He WD, Lin L (2018) Novel sustainable synthesis of dyes for clean dyeing of wool and cotton fibres in supercritical carbon dioxide. J Clean Prod 199:1–10

    CAS  Google Scholar 

  • Manavi N, Kazemi AS, Bonakdarpour B (2017) The development of aerobic granules from conventional activated sludge under anaerobic-aerobic cycles and their adaptation for treatment of dyeing wastewater. Chem Eng J 312:375–384

    CAS  Google Scholar 

  • Mazziotti DA (2000) Geminal functional theory: a synthesis of density and density matrix methods. J Chem Phys 112:10125–10130

    CAS  Google Scholar 

  • Melo AT, Brito DWS, Lima AF, Lalic MV (2020) Non-collinear spin DFT study of the ground state magnetic structure, optical and electronic properties of the hexagonal LuFeO3 multiferroic. J Alloy Compnd 813:152227

    CAS  Google Scholar 

  • Mohsin M, Sardar S, Hassan M, Akhtar N, Sufyan M (2020) Novel, sustainable and water efficient nano bubble dyeing of cotton fabric. Cellulose. https://doi.org/10.1007/s10570-020-03187-6

    Article  Google Scholar 

  • Moores A, Ricard L, Le Floch P (2003) A 1-Methyl-phosphininium compound: synthesis, X-Ray crystal structure, and DFT calculations. Angew Chem Int Edit 42:4940–4944

    CAS  Google Scholar 

  • Pei LJ, Liu JJ, Cai GQ, Wang JP (2017a) Study of hydrolytic kinetics of vinyl sulfone reactive dye in siloxane reverse micro-emulsion. Text Res J 87:2368–2378

    CAS  Google Scholar 

  • Pei LJ, Liu JJ, Wang JP (2017b) Study of Dichlorotriazine Reactive Dye Hydrolysis in Siloxane Reverse Micro-emulsion. J Clean Prod 165:994–1004

    CAS  Google Scholar 

  • Pei LJ, Luo YN, Gu XM, Dou HS, Wang JP (2019) Diffusion mechanism of aqueous solutions and swelling of cellulosic fibers in silicone non-aqueous dyeing system. Polymers 11(3):411

    PubMed Central  Google Scholar 

  • Pei LJ, Luo YN, Saleem MA, Wang JP (2021) Sustainable pilot scale reactive dyeing based on silicone oil for improving dye fixation and reducing discharges. J Clean Prod 279:123831

    CAS  Google Scholar 

  • Radei S, Carrión-Fité FJ, Ardanuy M, Canal JM (2018) Kinetics of low temperature polyester dyeing with high molecular weight disperse dyes by solvent microemulsion and agrosourced auxiliaries. Polymers 10(2):200

    PubMed Central  Google Scholar 

  • Ramkumaar GR, Srinivasan S, Bhoopathy TJ, Gunasekaran S (2012) Molecular geometry, vibrational spectra, atomic charges, frontier molecular orbital and Fukui function analysis of antiviral drug zidovudine. Spectrochim Acta A 99:189–195

    CAS  Google Scholar 

  • Reddy MB, Looney RJ, Utell MJ, Plotzke KP, Andersen MZ (2007) Modeling of human dermal absorption of octamethylcyclotetrasiloxane (D4) and decamethylcyclopentasiloxane (D5). Toxicol Sci 99:422–431

    CAS  PubMed  Google Scholar 

  • Sapari N (1996) Treatment and reuse of textile wastewater by overland flow. Desalination 106(1-3):179–182.

    CAS  Google Scholar 

  • Sawada K, Takagi T, Jun JH, Ueda M, Lewis DM (2002) Dyeing natural fibres in supercritical carbon dioxide using a nonionic surfactant reverse micellar system. Color Technol 118:233–237

    CAS  Google Scholar 

  • Schlücker S, Singh RK, Asthana BP, Popp J, Kiefer W (2001) Hydrogen-bonded pyridine—water complexes studied by density functional theory and Raman spectroscopy. J Phys Chem A 105:9983–9989

    Google Scholar 

  • Schmidt A, Bach E, Schollmeyer E (2003) The dyeing of natural fibres with reactive disperse dyes in supercritical carbon dioxide. Dyes Pigments 56:27–35

    CAS  Google Scholar 

  • Su S, Liang Y, Yin G, Wang Q, Cai Y, Peng X, Pervez MdN, Lin L (2019) Anhydrous dyeing processes of ramie fiber in liquid ammonia. Cellulose 26:8109–8120

    CAS  Google Scholar 

  • Sye FW, Lu CL, Tai WJ, Wang IC (2008) Applications of chitosan beads and porous crab shell powder combined with solid-phase microextraction for detection and the removal of colour from textile wastewater. Carbohyd Polym 72:550–556

    CAS  Google Scholar 

  • Tang AYL, Lee CH, Wang YM, Kan CW (2019) A study of peg-based reverse micellar dyeing of cotton fabric: reactive dyes with different reactive groups. Cellulose 26(6):4159–4173

    CAS  Google Scholar 

  • Thorat KG, Kamble P, Mallah R, Ray AK, Sekar N (2015) Congeners of pyrromethene-567 dye: perspectives from synthesis, photophysics, photostability, laser, and TD-DFT theory. J Org Chem 80:6152–6164

    CAS  PubMed  Google Scholar 

  • Wang JP, Zhang YB, Dou HS, Pei LJ (2018) Influence of ethylene oxide content in nonionic surfactant to the hydrolysis of reactive dye in silicone non-aqueous dyeing System. Polymers 10(10):1158

    PubMed Central  Google Scholar 

  • Wang ML, Wang QW, Qu PY, Liu Y, Xu YZ (2011) Supercritical fluid spray dyeing: a new method of dyeing and simulations of its flow field. Adv Mater Res 396–398:2038–2043

    Google Scholar 

  • Wang Y, Tang YL, Lee CH, Kan CW (2019) Reverse micellar dyeing of wool fabric with reactive dyes. Fiber Polym 20(11):2367–2375

    CAS  Google Scholar 

  • Weber EJ, Stickney VC (1993) Hydrolysis kinetics of reactive blue 19-vinyl sulfone. Water Res 27:63–67

    CAS  Google Scholar 

  • Zhan YZ, Zhao X, Wang BJ, Wang W (2018) Computational modelling of the influence of substituent effects on phthalimidylazo disperse dye hydrolysis and interaction energy. Color Technol 134:24–32

    CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (22072089), the National Key Research and Development Program of China (2017YFB0309600) and Key Research and Development Program of Xinjiang Production and Construction Corps (2019AA001).

Author information

Authors and Affiliations

  1. Engineering Research Center of Textile Chemistry and Clean Production, Shanghai University of Engineering Science, No. 333 Longteng Road, Songjiang District, Shanghai, 201620, People’s Republic of China

    Liujun Pei, Xiaomin Gu & Jiping Wang

  2. School of Textiles and Fashion, Shanghai University of Engineering Science, Shanghai, 201620, People’s Republic of China

    Liujun Pei, Xiaomin Gu & Jiping Wang

Authors
  1. Liujun Pei
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xiaomin Gu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jiping Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jiping Wang.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pei, L., Gu, X. & Wang, J. Sustainable dyeing of cotton fabric with reactive dye in silicone oil emulsion for improving dye uptake and reducing wastewater. Cellulose 28, 2537–2550 (2021). https://doi.org/10.1007/s10570-020-03673-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10570-020-03673-x

Keywords

Search

Navigation