Advertisement

Cellulose

pp 1–10 | Cite as

Prospects of silatranyl dye derivatives in cotton dyeing process and dye effluent treatment: a comparative study of methyl red and its silatranyl derivative

  • Hemant Singh
  • Raghubir Singh
  • Varinder KaurEmail author
Communication
  • 15 Downloads

Abstract

Herein, the prospect of using a silatranyl derivative of dye for dyeing purpose is discussed. Firstly, a silatranyl derivative of methyl red was synthesized and characterized by spectroscopic and elemental analysis. Then, a comparative examination on the fixation of methyl red and its silatranyl derivative on cotton cloth was done after optimizing various parameters. Dye fixation studies, FT-IR, and scanning electron microscopic studies revealed better fixation of silatranyl dye derivative as compared to parent dye. Silanized methyl red was fixed on fiber via covalent interactions whereas methyl red exhibited physical sorption. Covalent fixation of dye on the cotton cloth prevented leaching of dye from cloth even after water and soap treatment for longer periods. Moreover, hydrolysis of silatranyl cage of silanized dye in excessive water (i.e. water fraction fw = 50% v/v in methanol–water mixture) to form dye incorporated silica offers an advantage for pretreatment of dye remains. Thus, the silatranyl derivative of methyl red has prospects as a dyeing agent in the future as it offers benefits to improve colour impression and treatment of dye effluent.

Graphical abstract

Keywords

Methyl red Silatrane Amide linkage Dye fixation Cotton dyeing Treatment of effluent 

Notes

Acknowledgments

Authors are thankful to UGC, New Delhi (No.: 2061510021, Ref. No.: 21/06/2015(i)EU-V) and Dr. Raghubir Singh DST-FIST (no. SR/FST/college-335/2016).

Supplementary material

10570_2019_2293_MOESM1_ESM.docx (929 kb)
Supplementary material 1 (DOCX 928 kb)

References

  1. Abidi N (2017) Dyeing of cotton fabric. In: Cotton fibres: characteristics, user and performance, pp 303–322Google Scholar
  2. Afkhami A, Moosavi R (2010) Adsorptive removal of Congo red, a carcinogenic textile dye, from aqueous solutions by maghemite nanoparticles. J Hazard Mater 174:398–403.  https://doi.org/10.1016/j.jhazmat.2009.09.066 CrossRefGoogle Scholar
  3. Ayati A, Shahrak MN, Tanhaei B, Sillanpää M (2016) Emerging adsorptive removal of azo dye by metal–organic frameworks. Chemosphere 160:30–44.  https://doi.org/10.1016/j.chemosphere.2016.06.065 CrossRefGoogle Scholar
  4. Batchelor SN (2015) New insights into dye chemistry and physics. Color Technol 131:81–93.  https://doi.org/10.1111/cote.12138 CrossRefGoogle Scholar
  5. Brown MA, De Vito SC (1993) Predicting azo dye toxicity. Crit Rev Environ Sci Technol 23:249–324.  https://doi.org/10.1080/10643389309388453 CrossRefGoogle Scholar
  6. Craig MR, Hutchings MG, Claridge TDW, Anderson HL (2001) rotaxane-encapsulation enhances the stability of an azo dye, in solution and when bonded to cellulose. This work was supported by the Engineering and Physical Sciences Research Council (UK) and by BASF plc. Angew Chem Int Ed Engl 40:1071–1074.  https://doi.org/10.1002/1521-3773(20010316)40:6%3c1071:AID-ANIE10710%3e3.0.CO;2-5 CrossRefGoogle Scholar
  7. Fleischmann C, Lievenbrück M, Ritter H (2015) Polymers and dyes: developments and applications. Polymers (Basel) 7:717–746.  https://doi.org/10.3390/polym7040717 CrossRefGoogle Scholar
  8. Gorenšek M (1999) Dye–fibre bond stabilities of some reactive dyes on cotton. Dye Pigment 40:225–233.  https://doi.org/10.1016/S0143-7208(98)00052-7 CrossRefGoogle Scholar
  9. Guo N, Chen Y, Rao Q et al (2015) Fabrication of durable hydrophobic cellulose surface from silane-functionalized silica hydrosol via electrochemically assisted deposition. J Appl Polym Sci.  https://doi.org/10.1002/app.42733 Google Scholar
  10. Khatri A, Peerzada MH, Mohsin M, White M (2015) A review on developments in dyeing cotton fabrics with reactive dyes for reducing effluent pollution. J Clean Prod 87:50–57.  https://doi.org/10.1016/j.jclepro.2014.09.017 CrossRefGoogle Scholar
  11. Kim K-H, Kabir E, Jahan SA (2016) The use of personal hair dye and its implications for human health. Environ Int 89–90:222–227.  https://doi.org/10.1016/j.envint.2016.01.018 CrossRefGoogle Scholar
  12. Lewis DM (2008) The dyeing of wool with reactive dyes. J Soc Dye Colour 98:165–175.  https://doi.org/10.1111/j.1478-4408.1982.tb03631.x CrossRefGoogle Scholar
  13. Mahmood S, Khalid A, Arshad M et al (2015) Detoxification of azo dyes by bacterial oxidoreductase enzymes. Crit Rev Biotechnol 36:1–13.  https://doi.org/10.3109/07388551.2015.1004518 CrossRefGoogle Scholar
  14. Meng L-Z, Du C-Q, Chen Y-Y, He Y-B (2002) Preparation, characterization, and behavior of cellulose–titanium(IV) oxide modified with organosilicone. J Appl Polym Sci 84:61–66.  https://doi.org/10.1002/app.10188 CrossRefGoogle Scholar
  15. Morris KF, Lewis DM, Broadbent PJ (2008) Design and application of a multifunctional reactive dye capable of high fixation efficiency on cellulose. Color Technol 124:186–194.  https://doi.org/10.1111/j.1478-4408.2008.00140.x CrossRefGoogle Scholar
  16. Mutneja R, Singh R, Kaur V et al (2014) Development of new precursors for immobilizing dyes onto silica surfaces. Dye Pigment 108:41–49.  https://doi.org/10.1016/j.dyepig.2014.04.002 CrossRefGoogle Scholar
  17. Mutneja R, Singh R, Kaur V et al (2016) Schiff base tailed silatranes for the fabrication of functionalized silica based magnetic nano-cores possessing active sites for the adsorption of copper ions. New J Chem 40:1640–1648.  https://doi.org/10.1039/C5NJ02287H CrossRefGoogle Scholar
  18. Mutneja R, Singh R, Kaur V et al (2017) Proton transfer assisted facile encapsulation of picric acid in sol-gel derived silica decorated with azo-azomethine hosts. Dye Pigment 139:635–643.  https://doi.org/10.1016/j.dyepig.2016.12.060 CrossRefGoogle Scholar
  19. Nallathambi A, Venkateshwarapuram Rengaswami GD (2016) Salt-free reactive dyeing of cotton hosiery fabrics by exhaust application of cationic agent. Carbohydr Polym 152:1–11.  https://doi.org/10.1016/j.carbpol.2016.06.087 CrossRefGoogle Scholar
  20. Ngulube T, Gumbo JR, Masindi V, Maity A (2017) An update on synthetic dyes adsorption onto clay based minerals: a state-of-art review. J Environ Manage 191:35–57.  https://doi.org/10.1016/j.jenvman.2016.12.031 CrossRefGoogle Scholar
  21. Peng X, Lou K, Zhang Y et al (2017) Ammonified modification and dyeing of ramie fabric in liquid ammonia. Dye Pigment 138:154–161.  https://doi.org/10.1016/j.dyepig.2016.11.042 CrossRefGoogle Scholar
  22. Pinjari DV, Pandit AB (2010) Cavitation milling of natural cellulose to nanofibrils. Ultrason Sonochem 17:845–852.  https://doi.org/10.1016/j.ultsonch.2010.03.005 CrossRefGoogle Scholar
  23. Rawat D, Mishra V, Sharma RS (2016) Detoxification of azo dyes in the context of environmental processes. Chemosphere 155:591–605.  https://doi.org/10.1016/j.chemosphere.2016.04.068 CrossRefGoogle Scholar
  24. Saladino R, Guazzaroni M, Crestini C, Crucianelli M (2013) Dye degradation by layer-by-layer immobilised peroxidase/redox mediator systems. ChemCatChem 5:1407–1415.  https://doi.org/10.1002/cctc.201200660 CrossRefGoogle Scholar
  25. Sayyed AJ, Mohite LV, Deshmukh NA, Pinjari DV (2018) Effect of ultrasound treatment on swelling behavior of cellulose in aqueous N-methyl-morpholine-N-oxide solution. Ultrason Sonochem 49:161–168.  https://doi.org/10.1016/j.ultsonch.2018.07.042 CrossRefGoogle Scholar
  26. Sayyed AJ, Mohite LV, Deshmukh NA, Pinjari DV (2019) Structural characterization of cellulose pulp in aqueous NMMO solution under the process conditions of lyocell slurry. Carbohydr Polym 206:220–228.  https://doi.org/10.1016/j.carbpol.2018.11.004 CrossRefGoogle Scholar
  27. Seu G (1995) Spectrophotometric study of the prototropic equilibrium of methyl red in organic solvents. Dye Pigment 29:227–240.  https://doi.org/10.1016/0143-7208(95)00050-P CrossRefGoogle Scholar
  28. Singh R, Puri JK, Chahal VK et al (2010) Synthesis and reactivity of novel 3-isothiocyanatopropylsilatrane derived from aminopropylsilatrane: X-ray crystal structure and theoretical studies. J Organomet Chem 695:183–188.  https://doi.org/10.1016/j.jorganchem.2009.10.013 CrossRefGoogle Scholar
  29. Singh R, Mutneja R, Kaur V et al (2013) Derivatization of 3-aminopropylsilatrane to introduce azomethine linkage in the axial chain: synthesis, characterization and structural studies. J Organomet Chem 724:186–191.  https://doi.org/10.1016/j.jorganchem.2012.11.009 CrossRefGoogle Scholar
  30. Singh RL, Singh PK, Singh RP (2015) Enzymatic decolorization and degradation of azo dyes: a review. Int Biodeterior Biodegrad 104:21–31.  https://doi.org/10.1016/j.ibiod.2015.04.027 CrossRefGoogle Scholar
  31. Tawarah KM, Abu-Shamleh HM (1991) A spectrophotometric study of the acid-base equilibria of o-methyl red in aqueous solutions. Dye Pigment 17:203–215.  https://doi.org/10.1016/0143-7208(91)80027-7 CrossRefGoogle Scholar
  32. Varadarajan G, Venkatachalam P (2016) Sustainable textile dyeing processes. Environ Chem Lett 14:113–122.  https://doi.org/10.1007/s10311-015-0533-3 CrossRefGoogle Scholar
  33. Wu Z, Zhong H, Yuan X et al (2014) Adsorptive removal of methylene blue by rhamnolipid-functionalized graphene oxide from wastewater. Water Res 67:330–344.  https://doi.org/10.1016/j.watres.2014.09.026 CrossRefGoogle Scholar
  34. Wu Z, Yuan X, Zhang J et al (2017) Photocatalytic decontamination of wastewater containing organic dyes by metal-organic frameworks and their derivatives. ChemCatChem 9:41–64.  https://doi.org/10.1002/cctc.201600808 CrossRefGoogle Scholar
  35. Yeo J-S, Kim OY, Lee S-W, Hwang S-H (2017) The effect of cellulose surface treatment on the fracture toughness of microfibrillated cellulose reinforced unsaturated polyester composites. Polym Korea 41:157.  https://doi.org/10.7317/pk.2017.41.1.157 CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of ChemistryPanjab UniversityChandigarhIndia
  2. 2.DAV CollegeChandigarhIndia

Personalised recommendations