Synthesis and Properties of Esterquats as Antibacterial Agent and Fabric Softener
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Mithun G. Mondal
Abstract
A series of cationic surfactants, di-chained esterquat surfactants, was synthesized from triethanolamine, stearic acid and various alkylation agents by two step processes. The quaterisation was carried out with diethyl sulphate, benzyl chloride, 1-chloro-2,4,6-trinitrobenzene, benzoyl chloride. The synthesized surfactants were confirmed by IR spectra. Surface properties, wetting time, softness and antibacterial activity of the synthesized surfactants were investigated. The results showed that the synthesized esterquats exhibit high surface activities, better wetting times and very good softening properties. A synthesized cationic surfactant was further prepared for formulation of hair conditioning and body care. This product can be used in formulations of shampoo, fabric softener and liquid soaps and also it does not have any harmful impact to aquatic life. Further, the synthesized surfactant, prepared from 1-Chloro-2,4,6-trinitrobenzene, exhibit a better antibacterial activity against E. coli and S. aureus. It was found that the alkylation agent and hydrocarbon chain length affected the results.
Kurzfassung
Eine Reihe kationischer Tenside, Esterquat-Tenside mit zwei Ketten, wurde aus Triethanolamin, Stearinsäure und verschiedenen Alkylierungsmitteln in einem zweistufigen Verfahren synthetisiert. Die Quaternisierung erfolgte mit Diethylsulfat, Benzylchlorid, 1-Chlor-2,4,6-trinitrobenzen, und Benzoylchlorid. Die synthetisierten Tenside wurden durch IR-Spektren bestätigt. Oberflächeneigenschaften, wie Benetzungszeit, Weichheit und antibakterielle Aktivität der synthetisierten Tenside, wurden untersucht. Die Ergebnisse zeigten, dass die synthetisierten Esterquats hohe Oberflächenaktivitäten, bessere Benetzungszeiten und sehr gute Weichspülerseigenschaften aufweisen. Die synthetisierten kationischen Tenside wurden in einer Haar- und Körperpflege-Formulierung weiterverarbeitet. Dieses Produkt kann in Formulierungen von Shampoo, Weichspüler und flüssige Seifen verwendet werden und hat auch keinen schädlichen Auswirkungen auf das Leben im Wasser. Ferner zeigte das aus 1-Chlor-2,4,6-trinitrobenzol synthetisierte Tensid eine bessere antibakterielle Aktivität gegenüber E. coli und S. aureus. Es konnte deutlich festgestellt werden, dass das Alkylierungsmittel und die Kohlenwasserstoffkettenlänge die Ergebnisse beeinflussten.
References
1. Huang, L., Xiao, Y. and Xing, X.: Antibacterial activity and cytotoxicity of two novel cross-linking antibacterial monomers on oral pathogens. Arch. Oral. Biol.56 (2012) 367–373. 10.1016/j.archoralbio.2010.10.011Suche in Google Scholar PubMed
2. Guo, X. F. and Jia, L. H.: Synthesis and application of cationic surfactant, Chemical Industry press, Beijing15 (2012) pp 593–599. 10.1007/s11743-012-1347-ySuche in Google Scholar
3. Mohamed, A. S. and Mohamed, M. Z.: preparation of noel cationic surfactants from Epichlorohydrin: their surface properties and biological activities. J. Surfact. Deterg.13 (2010) 159–163. 10.1007/s11743-009-1141-7Suche in Google Scholar
4. Mishra, S. and Tyagi, V. K.: The novel class of cationic fabric softeners. Journal of Oleo Science56(6) (2007) 269–276. 10.5650/jos.56.269Suche in Google Scholar PubMed
5. Guo, X. F. and Jia, L. F.: Synthesis and application of cationic surfactant, Chemical Industry press, Beijing (2003). 10.1007/s11743-014-1597-ySuche in Google Scholar
6. Zhang, G. Y. and Wang, J.: (2002). Synthesis of biodegradable lauric acid ester quaternary ammonium salt cationic surfactant and its utilization as calico softener, Materials Letters62(19) (2008) 3450–3452. 10.1016/j.matlet.2008.02.084Suche in Google Scholar
7. Shenai, V. A. and Mehera, R. H: Technology of Textile Processing, 2nd ed. Sevak Publication: (1996) Bombay, pp. 128–132, OCLC Number: 465089485.Suche in Google Scholar
8. Oremusova, J., Vitcová, Z. and Vitko, A.: Study of Micelle Properties and Thermodynamics of Micellization of the Benzenthionium Chloride. Tenside Surfactants Detergent49(4) (2012) 322–329. 10.3139/113.110198Suche in Google Scholar
9. Tayagi, R., Tayagi, V. K. and Khanna, R. K.: Synthesis, structural properties and application applications of Gemini surfactant. Journal of Oleo Science7 (2006) 337–345. Tenside Surfactants Detergent 49(4) (2012) 322–329. 10.1007/s11743-014-1597-ySuche in Google Scholar
10. Rosen, M. J. and HobokenN.J.: Surfactant and Interfacial Phenomena, 3rd ed., pp. 227–302. John Wiley & Sons (2004), ISBN-13:978-0470541944. 10.1002/0471670561Suche in Google Scholar
11. Saad, A. H. and Khadim, R. B.: Formulation and evaluation of herbal shampoo from zizpus spina leaves extract. IJRP2(6) (2011) 1802–1806, ISSN-2229-3566.Suche in Google Scholar
12. Egan, R. R.: Cationic Surface acting agents as fabric softeners. J. Am. Oil Chem. Soc.55 (1978) 118–121. 10.1007/BF02673399Suche in Google Scholar
13. Kulkarni, V. M., Gangawane, P. D., Patwardhan, A. V. and Adivarekar, R. V.: Dying of Silk/wool using crude pigment extract from an isolated Kocuria flava sp. HO-90412 (2014), 314–320. ISSN 2321 3655.Suche in Google Scholar
14. Pavia, D. L., Lampman, G. M. and Kriz, G. S.: Introduction to Spectroscopy; A Division of Thomson Learning, Inc., Printed & bound in India by Sanat Printers, Kundli Haryana (2007), ISBN: 0495114782.Suche in Google Scholar
15. Pernak, J. and Chwala, P.: Synthesis and anti-microbial activities of choline-like quaternary ammonium chlorides. Eur. J. Med. Chem.38 (2003) 1035–1042. 10.1016/j.ejmech.2003.09.004Suche in Google Scholar PubMed
16. Ciganekvoa, V., Kallova, J., Devinsky, F. and Lacko, I.: Effect of N, N′-bis (alkyldimethyl)-α, ω-alkanediammonium dibromides on bacteria of the genus clostridium. Folia microbial34 (1989) 202–208. 2553558Suche in Google Scholar
17. DizmanB, Elasri, M. O. and Mathias, L. J.: Synthesis and antibacterial activity of water soluble methacrylate polymers containing quaternary ammonium compounds. J. polymer sci part A: Polym. Chem.44 (2006) 5965–5973. 10.1007/s00396-015-3588-6Suche in Google Scholar
18. Cornin, M. T. D., Aptula, A. O., Dearden, J. C., Daffy, J. C., Ntezeva, T. I., Patel, H., Philip, H., Rowe, T., Wayne, S., Andrew, P., Worth Constatinos, V. and Gerrit, S.: Structure-Based Classification of Antibacterial Activity. J. Chem. Inf. Computes Sci.42(4) (2002) 869–878. 10.1021/ci025501dSuche in Google Scholar PubMed
19. Amal, A. H., Badawi, A. M., El-Deeb, F. I., Soliman, E. A., EL-Awady, M. Y. and Mohamed, D. E.: Ferrocene based cationic surfactant: surface and antimicrobial properties. J. Surfact. Deterg.13 (2010) 165–172. 10.1007/s11743-014-1597-ySuche in Google Scholar
20. Papadopoulou, E., Hatjiissaak, A., Estrine, B. and Marinkovic, S.: Novel use of biomass derived alkyl-xylosides in wetting agent for paper impregnation suitable for the wood-based industry, Eur. J. Wood Prod.20 (2010) 20. 10.1007/s00107-010-0513-zSuche in Google Scholar
21. Yuuki, A. and YoshimuneNonomura: Friction and Surface Temperature of Wet Hair Containing Water, Oil, or Oil-in-Water Emulsion, J. Oleo. Sci.65(6) (2016) 493–498. org/10.5650/jos.ess15250.16Suche in Google Scholar
22. Amjad, R., Ali, M. M., Khan, S. R., Naeem, M. and Shoaib, M.: Eco-friendly synthesis of 4-4-diaminodiphenylurea, dye intermediate and direct dyes derived from it. Journal of the Chemical Society of Pakistan33 (2011) 107, ISSN 0253-510.Suche in Google Scholar
23. Christine, H. F. and Michael, H. C.: Comparative in vitro activities of ciprofloxacin and other 4-quinolones against mycobacterium intracellular. Antimicrobial agent chemotherapy29 (1986) 386–388. 10.1007/s11743-012-1406-4Suche in Google Scholar
24. Ahlstrom, B., Thompson, R. A. and Edebo, L.: The effect of hydrocarbon chain length, pH and temperature on the binding and bactericidal effect Betaine esters on Salomonella typhimurium esters on Salomonella typhimurium, APMIS107(3) (1999) 318–24. PMid: 10223305; 10.1111/j.1699-0463.1999.tb01560.xSuche in Google Scholar PubMed
25. Hollenberg, D. and Muller, R.: Seifen Oleo Fette Wachse121 (1995) 82. 10.5650/jos.56.69Suche in Google Scholar
26. Hague, J. D., Khan-Lodhi, A. N. and Reid, E. S.: PCT Int. Appl. WO/96/29/980 to Uniliver NV, (1996.Suche in Google Scholar
27. Villa, C. C., Silber, J. J., Correa, N. M. and Falcone, R. D.: Effect of the cationic surfactant moiety on the structure of water entrapped in two catanionic reverse micelles created from ionic liquid-like surfactants15(14) (2014) 3097–109. 10.1002/cphc.201402307Suche in Google Scholar PubMed
28. Wang, Y. G., Wang, P. W. and Yao, C. Z.: A study on the biodegradation of fabric softener: esterquats (EQ). New Chem. Mater.18(1) (2005) 91–95. 10.1007/s11743-014-1597-ySuche in Google Scholar
29. Baker, I. A., Willing, R. I. and Furlong, D. N.: Sugar fatty acid ester surfactants: biodegradation pathways. J. Surfact. Deterg.3 (2000) 13–27. 10.1007/s11743-000-0108-1Suche in Google Scholar
© 2017, Carl Hanser Publisher, Munich
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Editorial
- Review of the Year 2016
- Review
- Reaction Principle of Alcohol Ether Sulfonates by Sulfonated Alkylation Method – A Review
- Biosurfactants/Novel Surfactants
- Distribution Coefficients of Lipopeptide Biosurfactant in Different Solvents and its Separation from a Surfactant/Polymer Mixture in Aqueous Solutions
- Synthesis and Surface Properties of Anionic Vinylguaiacol Based Surfactants
- Novel Mesoporous ZSM-5 Zeolite with Disparate Morphologies Synthesized by a Double Long-alkyl-chain Organosilane Template
- Environmental Chemistry
- Preparation and Characterization of Glauber's Salt Microcapsules for Thermal Energy Storage
- Physical Chemistry
- Preparation and Characterization of a Humate Surfactant with Hydroxymethylation and Esterification Modification of Lignite
- Properties of Cationic Choline-Derived Surfactant with Photolabile Cinnamate Counterion
- Micellar Catalysis
- Solvent-Free Acetalization of Glycerol with n-Octanal using Combined Brønsted Acid-Surfactant Catalyst
- Synthesis
- Purification, Analysis and Surfactant Synthesis of Waste Cooking Oil
- Application
- Preparation and Properties of Novel Asymmetric Gemini Alkyl Polyglycosides
- Synthesis and Properties of Esterquats as Antibacterial Agent and Fabric Softener
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Editorial
- Review of the Year 2016
- Review
- Reaction Principle of Alcohol Ether Sulfonates by Sulfonated Alkylation Method – A Review
- Biosurfactants/Novel Surfactants
- Distribution Coefficients of Lipopeptide Biosurfactant in Different Solvents and its Separation from a Surfactant/Polymer Mixture in Aqueous Solutions
- Synthesis and Surface Properties of Anionic Vinylguaiacol Based Surfactants
- Novel Mesoporous ZSM-5 Zeolite with Disparate Morphologies Synthesized by a Double Long-alkyl-chain Organosilane Template
- Environmental Chemistry
- Preparation and Characterization of Glauber's Salt Microcapsules for Thermal Energy Storage
- Physical Chemistry
- Preparation and Characterization of a Humate Surfactant with Hydroxymethylation and Esterification Modification of Lignite
- Properties of Cationic Choline-Derived Surfactant with Photolabile Cinnamate Counterion
- Micellar Catalysis
- Solvent-Free Acetalization of Glycerol with n-Octanal using Combined Brønsted Acid-Surfactant Catalyst
- Synthesis
- Purification, Analysis and Surfactant Synthesis of Waste Cooking Oil
- Application
- Preparation and Properties of Novel Asymmetric Gemini Alkyl Polyglycosides
- Synthesis and Properties of Esterquats as Antibacterial Agent and Fabric Softener
