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Cellulose

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Facile synthesis of a novel, highly effective, more sustainable and cost-effective cationic bleach activator for cotton: N-[4-(N,N,N)-triethylammoniumchloride-butyryl] caprolactam

  • Pelin Altay
  • Peter J. Hauser
  • Nevin Cigdem Gursoy
  • Ahmed El-ShafeiEmail author
Original Research
  • 26 Downloads

Abstract

Compared to conventional peroxide bleaching, using a bleach activator in a peroxide bleaching bath is an effective and kinetically more potent oxidation generating highly reactive peracid in situ, providing low-temperature bleaching with shorter dwelling time. In the presence of an activator, bleaching can be achieved at lower temperatures and reduced time relative to the conventional peroxide bleaching, resulting in decrease in energy consumption and reduced fabric damage. Cationic bleach activators were investigated as the next generation bleach activators that exhibit inherent substantivity towards cellulosic fibers. In this study, facile synthesis of a more sustainable and cost-effective bleach activator, based on an aliphatic acyl chloride (4-chlorobutyryl chloride), was reported: Compared to aromatic-based bleach activator, it showed comparable bleaching results at lower temperature. Fourier transform infrared and high resolution mass spectrometry confirmed the molecular structure of the named activator: N-[4-(N,N,N)-triethylammoniumchloride-butyryl] caprolactam, TBUCC. Bleaching performance of TBUCC was evaluated in terms of whiteness index, water absorbency and fiber damage and compared with conventional peroxide system. Results revealed that our developed TBUCC-activated bleaching system provided comparable whiteness index, water absorbency with a higher degree of polymerization at significantly lower temperature (70 °C) as compared to conventional peroxide bleaching.

Graphical abstract

Keywords

Peracetic acid Low temperature bleaching Hydrogen peroxide N-[4-(N,N,N)-triethylammoniumchloride-butyryl] caprolactam TBUCC 

Notes

Acknowledgments

This study is supported by TUBITAK (The Scientific and Technological Research Council of Turkey) for 2214/A – International Doctoral Research Fellowship Program.

References

  1. AATCC (2009a) Test method 110: whiteness of textiles. American Association of Textile Chemists and Colorists Technical ManualGoogle Scholar
  2. AATCC (2009b) Test method 79: absorbency of textiles. American Association of Textile Chemists and Colorists Technical ManualGoogle Scholar
  3. AATCC TM 82 (2009c) Fluidity of dispersions of cellulose from bleached cotton cloth. American Association of Textile Chemists and Colorists Technical ManualGoogle Scholar
  4. Brown WH, Poon T (2016) Introduction to organic chemistry, 6th edn. Wiley, HobokenGoogle Scholar
  5. Cai JY, Evans DJ (2007) Guanidine derivatives used as peroxide activators for bleaching cellulosic textiles. Color Technol 123(2):115–118.  https://doi.org/10.1111/j.1478-4408.2007.00070.x Google Scholar
  6. Cai JY, Evans DJ, Smith SM (2001) Bleaching of natural fibers with TAED and NOBS activated peroxide systems. AATCC Rev 1(12):31–34Google Scholar
  7. Chen W, Wang L, Wang D, Zhang J, Sun C, Xu C (2016) Recognizing a limitation of the TBLC-activated peroxide system onlow-temperature cotton bleaching. Carbohyd Polym 140:1–5.  https://doi.org/10.1016/j.carbpol.2015.12.013 Google Scholar
  8. Clark M (2011) Handbook of textile and industrial dyeing: principles, processes and types of dyes. Woodhead Publishing Series in Textiles, New DelhiGoogle Scholar
  9. Clayden J, Greeves N, Warren S (2012) Organic chemistry, 2nd edn. Oxford University Press, OxfordGoogle Scholar
  10. Fei X, Yao J, Du J, Sun C, Xiang Z, Xu C (2015) Analysis of factors affecting the performance of activated peroxide systems on bleaching of cotton fabric. Cellulose 22:1379–1388Google Scholar
  11. Hauser PJ, Hinks D, Lee JJ, Lim SH (2007) Cationic bleach activator with enhanced hydrolytic stability. US Patent No: 7179779Google Scholar
  12. Hebeish A, Hashem M, Shaker N, Ramadan M, El-Sadek B, Hady MA (2009) New development for combined bioscouring and bleaching of cotton-based fabrics. Carbohydr Polym 78(4):961–972.  https://doi.org/10.1108/RJTA-17-01-2013-B010 Google Scholar
  13. Hickman WS (2002) Peracetic acid and its use in fibre bleaching. Rev Prog Color 32:13–27.  https://doi.org/10.1111/j.1478-4408.2002.tb00247.x Google Scholar
  14. Kamakar S (1999) Chemical technology in the pre-treatment processes of textiles, 1st edn. Elsevier, New YorkGoogle Scholar
  15. Lee JJ, Hinks D, Lim SH, Hauser P (2010) Hydrolytic stability of a series of lactam-based cationic bleach activators and their impact on cellulose peroxide bleaching. Cellulose 17(3):671–678.  https://doi.org/10.1007/s10570-009-9390-1 Google Scholar
  16. Lim SH, Gürsoy NÇ, Hauser P, Hinks D (2004) Performance of a new cationic bleach activator on a hydrogen peroxide bleaching system. Color Technol 120:114–118.  https://doi.org/10.1111/j.1478-4408.2004.tb00216.x Google Scholar
  17. Long X, Xu C, Du J, Fu S (2013) The TAED/H2O2/NaHCO3 system as an approach to low-temperature and near-neutral pH bleaching of cotton. Carbohydr Polym 95(1):107–113.  https://doi.org/10.1016/j.carbpol.2013.02.061 Google Scholar
  18. Luo X, Sui X, Yao J, Fei X, Du J, Sun C, Xiang Z, Xu C, Wang S (2015) Performance modelling of the TBCC-activated peroxide. Cellulose 22:3491–3499.  https://doi.org/10.1007/s10570-015-0741-9 Google Scholar
  19. Ouellette R, Rawn JD (2015) Principles of organic chemistry, 1st edn. Elsevier, AmsterdamGoogle Scholar
  20. Scarborough SJ, Mathews AJ (2000) Using TAED in bleaching fiber blends to improve fiber quality. Text Chem Color Am Dyest Rep 32(3):33–37Google Scholar
  21. Scialla S, Sheets CN, Burckett-St. Laurent JCTR, Brown MD (2005) Dual-compartment laundry composition containing peroxyacids. The Procter and Gamble Company, US Patent No: WO 2005035707 A1Google Scholar
  22. Shao J, Yi H, Wang Z, Liu J (2010) Cold pad-batch bleaching of cotton fabrics with a TAED/H2O2 activating system. Color Technol 126:103–108.  https://doi.org/10.1111/j.1478-4408.2010.00234.x Google Scholar
  23. Sigma-Aldrich (2017). https://www.sigmaaldrich.com/united-states.html. Accessed Jan 2017
  24. Špička N, Zupin Z, Kovač J, Tavčer PEF (2015) Enzymatic scouring and low-temperature bleaching of fabrics constructed from cotton, regenerated bamboo, poly(lactic acid), and soy protein fibers. Fibers Polym 16(8):1723–1733.  https://doi.org/10.1007/s12221-015-5140-1 Google Scholar
  25. Wang G (2012) Synthesis of bleach activators with varying cationic groups. Master of Science Thesis, Graduate Faculty of North Carolina State UniversityGoogle Scholar
  26. Wang J, Washington NM (2002) Hydrophobic bleach systems and textile preparation: a discontinuity in fabric care. AATCC Rev 2(6):21–24Google Scholar
  27. Wang S, Li S, Zhu Q, Yang CQ (2014) A novel low temperature approach for simultaneous scouring and bleaching of knitted cotton fabric at 60 °C. Ind Eng Chem Res 53(24):9985–9991.  https://doi.org/10.1021/ie500062f Google Scholar
  28. Wang G, Umbuzeiro GDA, Vendemiatti JA, Oliveira ACD, Vacchi FI, Hussain M, Hauser PJ, Freeman HS, Hinks D (2017) Synthesis, characterization, and toxicological properties of new cationic bleach activators. J Surfact Deterg 20:277–285.  https://doi.org/10.1007/s11743-016-1899-3 Google Scholar
  29. Wei D, Sun C, Wang M, Du J, Xu C (2014) Synthesis of N-[4-(dimethylalky- lammoniomethyl) benzoyl]caprolactam chlorides as cationic bleach activators for low-temperature bleaching of cotton fabric under near-neutral pH conditions. Society of Dyers and Colourists. Color Technol 130:432–436.  https://doi.org/10.1111/cote.12116 Google Scholar
  30. Xu C, Shamey R, Hinks D, El-Shafei A (2012) Cotton bleaching optimization using a butyrolactam-based cationic bleach activator. AATCC Rev 12:66–70Google Scholar
  31. Xu C, Hinks D, Sun C, Wei Q (2015) Establishment of an activated peroxide system for low temperature cotton bleaching using N-[4 (triethylammoniomethyl) benzoyl]butyrolactam chloride. Carbohyd Polym 119:71–77.  https://doi.org/10.1016/j.carbpol.2014.11.054 Google Scholar
  32. Yu J, Shao D, Sun C, Xu C, Hinks D (2017) Pilot-plant investigation on low-temperature bleaching of cotton fabric with TBCC-activated peroxide system. Cellulose 24:2647–2655.  https://doi.org/10.1007/s10570-017-1276-z Google Scholar
  33. Zeng H, Tang RC (2015) Application of a novel bleach activator to low temperature bleaching of raw cotton fabrics. J Text Inst 106(8):807–813.  https://doi.org/10.1080/00405000.2014.945764 Google Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Textile Engineering Department, Faculty of Textile Technologies and DesignIstanbul Technical UniversityIstanbulTurkey
  2. 2.Fiber and Polymer Science, College of TextilesNorth Carolina State UniversityRaleighUSA

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