Synthesis of a Novel Acid Dye to Impart Mosquito Repellency and UV Protection to Nylon

Document Type : Original Article

Authors

Department of Textile and Fibre Engineering, Indian Institute of Technology, P.O.Box: 110016, Hauz Khas, New Delhi-110016, India

Abstract

Novel routes are continuously innovated in the textile industry to obtain high-performance products, and the development of functional textiles using functional dyes is an attractive alternative to existing methods. In this context, the current study reports the synthesis of a new acid dye to develop mosquito-repellent and UV-protective nylon. The acid dye was synthesized by reacting a diazotized derivative of ethyl anthranilate (ethyl 2-aminobenzoate) with H-acid (4-Amino-5-hydroxy-2,7-naphthalenedisulfonic acid). The synthesized dye was thoroughly characterized through Fourier-transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1H NMR),13C NMR (Carbon-13 NMR) spectroscopy, elemental analysis (CHN analyzer), and UV-Vis spectroscopy. The dye was used to dye nylon, and dyeing characteristics (exhaustion and fixation) were examined. The functional effects and coloring properties of dyed fabrics were further investigated. The dyed fabrics were also characterized by X-ray diffraction (XRD) and thermogravimetric analysis (TGA). The dyed fabrics were imparted with 100 % mosquito repellency and excellent UV protection.

Keywords

References

  1. A. G. Rodrigues, P. J. Romano de Oliveira Gonçalves, C. A. Ottoni, R. de Cássia Ruiz, M. A. Morgano, W. L. de Araújo, I. S. de Melo, A. O. De Souza, Functional textiles impregnated with biogenic silver nanoparticles from Bionectria ochroleuca and its antimicrobial activity, Biomed. Microdevices., 21(2019), 56. 
  2. Q. Qiu, S. Chen, Y. Li, Y. Yang, H. Zhang, Z. Quan, X. Qin, R. Wang, J. Yu, Functional nanofibers embedded into textiles for durable antibacterial properties, Chem. Eng. J., 384(2020), 123241. 
  3. A. Bashari, A. H. S. Koohestani, N. Salamatipour, Eco-friendly dual-functional textiles: green water-repellent & anti-bacterial, Fibers Polym., 21(2020), 317-323..
  4. A. Asar, M. S. Irfan, K. A. Khan, W. Zaki, R. Umer, Self-sensing shape memory polymer composites reinforced with functional textiles, Compos. Sci. Technol., 221(2022), 109219.
  5. M. Gupta, J. Sheikh, Annu, A. Singh, An eco-friendly route to develop cellulose-based multifunctional finished linen fabric using ZnO NPs and CS network, J. Ind. Eng. Chem., 97(2021), 383-389. 
  6. A. Singh, J. Sheikh, Cleaner functional dyeing of wool using Kigelia Africana natural dye and Terminalia chebula bio-mordant, Sustain. Chem. Pharm., 17(2020), 100286. 
  7. A. Singh, J. Sheikh, Development of mosquito repellent, antibacterial, Antioxidant and UV protective cotton using a novel method of azoic dyeing with terminalia chebula, J. Nat. Fibers., 19(2021), 1-14. 
  8. A. Singh, J. Sheikh, Development of multifunctional polyester using disperse dyes based through a combination of mosquito repellents, J. Mol. Struct., 1232(2021), 129988. h
  9. S. Tambi, A. Mangal, N. Singh, J. Sheikh, Cleaner production of dyed and functional polyester using natural dyes vis-a-vis exploration of secondary shades, Prog. Color. Color. Coatings., 14(2021), 121-128.
  10. V. Selvaraj, T. Swarna Karthika, C. Mansiya, M. Alagar, An over review on recently developed techniques, mechanisms and intermediate involved in the advanced azo dye degradation for industrial applications, J. Mol. Struct., 1224(2021), 129195. 
  11. A. Pielesz, The process of the reduction of azo dyes used in dyeing textiles on the basis of infrared spectroscopy analysis, J. Mol. Struct., 511-512 (1999), 337-344. 
  12. F. Eyduran, N. Süleymanoğlu, R. Ustabaş, Synthesis, spectroscopic and computational investigation of N1,N4-bis(3-oxobutanoyl)benzene-1,4-dicarbohydra-zide as a coupling component for azo dyes from waste poly(ethyleneterephthalate) bottle, J. Mol. Struct., 1244(2021), 130985. 
  13. H. Shaki, A. Khosravi, K. Gharanjig, Novel cationic dye based on naphthalimide: Part 1: Synthesis, characterization and evaluation of biology efficacy as antimicrobial agent, Prog. Color. Colorant Coatings., 9(2016), 261-268.
  14. A. Mohammadi, H. Ghafoori, M. Rassa, Aryl azo 5-arylidene-2,4-thiazolidinone dyes as novel antioxidant and antibacterial compounds, Prog. Color. Colorant Coat., 8(2015), 145–152.
  15. A. Mohammadi, H. Ghafoori, Naphthalene-based azo dyes: Synthesis, characterization and dyeing performance on polyester fibers, Prog. Color Colorant Coat., 8(2015), 317-327. 
  16. K. Gharanjig, F. Ameri, F. S. Dadras, A. Khosravi, Novel naphthalimide based azo disperse dyes for dyeing of polyester fabrics, Prog. Color Colorant Coat., 4(2011), 27-37.
  17. A. Khosravi, S. Moradian, K. Gharanjig, F.A. Taromi, Synthesis and spectroscopic studies of some naphthalimide based disperse azo dyestuffs for the dyeing of polyester fibres, Dyes Pigm., 69(2006), 79-92. 
  18. S. Bait, S. Shinde, R. Adivarekar, N. Sekar, Multifunctional properties of benzophenone based acid dyes: Synthesis, spectral properties and computational study, Dyes Pigm., 180(2020), 108420. 
  19. P. Cowper, A. Pockett, G. Kociok-Köhn, P.J. Cameron, S.E. Lewis, Azulene – Thiophene – Cyanoacrylic acid dyes with donor-π-acceptor structures. Synthesis, characterisation and evaluation in dye-sensitized solar cells, Tetrahedron, 74(2018), 2775-2786. 
  20. J. Sun, H. Wang, C. Zheng, G. Wang, Synthesis of some surfactant-type acid dyes and their low-temperature dyeing properties on wool fiber, J. Clean. Prod., 218(2019), 284-293. 
  21. K. Blus, Synthesis and properties of disazo acid dyes, Dyes Pigm., 43(1999), 183-188.
  22. A. M. Api, D. Belsito, S. Bhatia, M. Bruze, P. Calow, M.L. Dagli, W. Dekant, A.D. Fryer, L. Kromidas, S. La Cava, J.F. Lalko, A. Lapczynski, D.C. Liebler, Y. Miyachi, V.T. Politano, G. Ritacco, D. Salvito, J. Shen, T.W. Schultz, I.G. Sipes, B. Wall, D.K. Wilcox, RIFM fragrance ingredient safety assessment, ethyl anthranilate, CAS registry number 87-25-2, Food Chem. Toxicol., 82(2015), 97-104. 
  23. J. Islam, K. Zaman, S. Chakrabarti, P. Chattopadhyay, Exploration of toxicological impacts following acute and sub-chronic exposure to ethyl anthranilate-loaded mosquito repellent patch, Regul. Toxicol. Pharmacol., 97(2018), 209-224. 
  24. Z. Ruizhen, W. Rulin, Z. Lianshun, Z. Yating, W. Lizhi, Z. Fei, H. Babar, X. Yijuan, Toxicity and repellency of two anthranilates against Aedes albopictus Skuse (Diptera: Culicidae), Acta Trop., 200(2019), 105171. 
  25. J. Islam, K. Zaman, V. Tyagi, S. Duaraha, S.Dhiman, P. Chattopadhyay, Protection against mosquito vectors Aedes aegypti, Anopheles stephensi and Culex quinquefasciatus using a novel insect repellent, ethyl anthranilate, Acta Trop., 174(2017), 56-63. 
  26. A. Afify , B. Horlacher, J. Roller ,C.G Galizia ,, Different repellents for Aedes aegypti against blood-feeding and oviposition, PLoS One., 9(2014), e103765. 
  27. M. D. Teli, P. P. Chavan, Synthesis of reactive dye to impart mosquito repellency to nylon, J. Text. Inst., 108(2017), 226-232. 
  28. M. D. Teli, P. P. Chavan, Dyeing of cotton fabric for improved mosquito repellency, J. Text. Inst., 109(2018), 427-434. 
  29. A. Singh, J. Sheikh, Synthesis and application of a novel cold brand reactive dye to impart colouration, mosquito repellency, and UV protection to nylon, Arab. J. Chem., 15(2022), 104339. 
  30. ISO manual 2006. ISO Technical manual ,Geneva, switerzland. (2006).
  31. AS/NZS,4399.1996-AS/NZS 4399.Sun protective clothing evaluation and classification. (1996)
  32. AATCC technical manual 2007. Association of Textile Chemists and Colorists; AATCC technical manual.Research Triangle Park. (2007).
  33. R. M .Silverstein, R. M., G. C. Bassler,T. C. Morrill. Spectrometric Identification of Organic Compounds. 3rd ed. New York: John Wiley & Sons. (1974).
  34. A. N. M. A. Haque, M. A. Islam, The contribution of different vinyl sulphone-reactive dyes to an effluent, J. Taibah Univ. Sci., 9(2015), 594-600. 
  35. M. Rahman, A.K.M. A.H Asif, Md. A. B. Siddiquee, M.d. Rokonuzzaman, Effect of shade percentage on various properties of cotton knitted fabric dyed with reactive dyes, Int. J. Res. Eng. Technol., 03(2014), 339-343. 
  36. S. M. Burkinshaw, O. Kabambe, Attempts to reduce water and chemical usage in the removal of bifunctional reactive dyes from cotton: Part 2 bis(vinyl sulfone), aminochlorotriazine/vinyl sulfone and bis(aminochlorotriazine/vinyl sulfone) dyes, Dyes Pigm., 88(2011), 220-229. 
  37. Y. Wang, B. Tang, W. Ma, S. Zhang, Synthesis and UV-protective properties of monoazo acid dyes based on 2-hydroxy-4-methoxybenzophenone, Procedia Eng., 18(2011), 162-167. 
  38. N. J. Bhatt, E. H. Daruwalla, Studies in the mechanism of dyeing of polyamide fibers with acid dyes, Textile Res. J., 34(1964), 435-444
  39. T. M. Ting, M. M. Nasef, K. Hashim, Modification of nylon-6 fibres by radiation-induced graft polymerisation of vinylbenzyl chloride, Radiat. Phys. Chem., 109(2015), 54-62.
  40. H. R. Pant, W. Il Baek, K.T. Nam, I.S. Jeong, N.A.M. Barakat, H.Y. Kim, Effect of lactic acid on polymer crystallization chain conformation and fiber morphology in an electrospun nylon-6 mat, Polymer., 52(2011), 4851-4856. 
  41. C. B. Giller, D. B. Chase, J.F. Rabolt, C. M. Snively, Effect of solvent evaporation rate on the crystalline state of electrospun Nylon 6, Polymer., 51(2010), 4225-4230. 
  42. S. Pashaei, Siddaramaiah, M. M. Avval, A. A. Syed, Thermal degradation kinetics of nylon6/gf/crysnano nanoclay nanocomposites by TGA, Chem. Ind. Chem. Eng. Q., 17(2011), 141-151. 
  43. K. Liu, Y. Li, L. Tao, R. Xiao, Preparation and characterization of polyamide 6 fibre based on a phosphorus-containing flame retardant, RSC Adv., 8(2018), 9261-9271. 
Progress in Color, Colorants and Coatings
Volume 16, Issue 2
May 2023
Pages 207-219

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