Synthesis of Rice Bran Fatty Acids (RBFAs) Based Cationic Surfactants and Evaluation of Their Performance Properties in Combination with Nonionic Surfactant
-
Gunjan
Abstract
Cationic surfactants are mainly used for fabric softening in laundry applications. Esterquats are one class of cationic surfactants and are superseding other existing cationic surfactants on account of their excellent biodegradability. However, indigenous and cost-effective production of esterquats poses new challenges for the researchers. The availability of rice bran fatty acids and its price structure in Indian scenario makes this fatty feedstock quite lucrative for cost-effective synthesis of cationic surfactants. In the present study, esterquats based on rice bran fatty acids (RBFAs) were synthesized by using different alkanolamines i. e. diethanolamine (DEA) and triethanolamine (TEA) and dimethyl sulphate (DMS) for obtaining cationic surfactants which was used as active softener ingredient. For this purpose, esterquats have been synthesized by esterification of RBFAs and alkanolamines to recover diesters followed by the subsequent quaternization of diesters by DMS. It was found that the optimum reaction conditions for esterification of RBFAs and DEA was 140 °C and 3 h of duration. However, for RBFAs and TEA, it was found to be 140 °C and 4 h of duration. The chemical structures of diesters and esterquats were confirmed by FT-IR and NMR spectra. Studies of surface active and performance properties of these surfactants showed that esterquats based on TEA had better surface active and performance properties as compared to DEA based esterquats. The synthesized cationic surfactants when mixed with nonionic surfactant showed better performance properties as compared to the nonionic surfactant alone.
Kurzfassung
Kationische Tenside werden hauptsächlich als Weichspüler bei der Wäsche von Textilien verwendet. Die Esterquats haben die anderen kationischen Tenside aufgrund ihrer hervorragenden biologischen Abbaubarkeit in diesem Bereich abgelöst. Jedoch eine bodenständige und kosteneffektive Produktion der Esterquats stellen für die Forscher neue Herausforderungen dar. Die Verfügbarkeit von Fettsäuren aus Reiskleie und der Preis der Reiskleie in Indien macht dieses Fettausgangsmaterial sehr lukrativ für die kostengünstige Synthese von kationischen Tensiden. In dieser Untersuchung wurden Esterquats auf Basis von Fettsäuren aus Reiskleie (RBFAs) synthetisiert. Hierzu wurden verschiedene Alkanolamine (Diethanolamin, DEA und Triethanolamin TEA) und Dimethylsulfat (DMS) eingesetzt, um für Weichspüler geeignete kationische Tenside zu erhalten. Die Esterquats wurden mittels Veresterung der RBFAs mit Alkanolaminen und nachfolgender Quaternisierung der so erhaltenen Diester mit DMS erzeugt. Die optimale Reaktionsdauer für die Veresterung der RBFAs und DEA betrug 3 Stunden bei 140 °C. Für die Veresterung der RBFAs mit TEA betrug die optimale Dauer 4 Stunden bei 140 °C. Die chemischen Strukturen der Diester und Esterquats wurden mittels FT-IR- und NMR-Spektren gesichert. Untersuchungen der Oberflächenaktivität und der Leistungseigenschaften dieser Tenside zeigten, dass die auf TEA basierten Esterquats im Vergleich zu den auf DEA basierten Esterquats bessere Resultate hatten. In der Mischung mit nichtionischen Tensiden lieferten die synthetisierten kationischen Tenside eine bessere Leistung als die reinen nichtionischen Tenside.
References
1. Ger. Patent DE521035 to IG Farbenindustrie A.G., 1931.Search in Google Scholar
2. Kang, H. H., Peters, R. G. and Knaggs, E. A.: Domestic laundry fabric softener, U.S. patent 3,915,867, 1975.Search in Google Scholar
3. Wahl, E. H., Bacon, D. R., Baker, E. S., Bodet, J. F., Burns, M. E., Demeyere, H. J. M., Hensley, C. A., Mermelstein, R., Severns, J. C., Shaw, J. H., Siklosi, M. P., Vogel, A. M. and Watson, J. W.: Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains, U.S. patent 5,562,849, 1996.Search in Google Scholar
4. Mishra, S. and Tyagi, V. K.: Ester Quats: The Novel Class of Cationic Fabric Softeners, J. Oleo Sci.56(2007) 269;. 10.5650/jos.56.269Search in Google Scholar
5. Levinson, M. I.: Rinse-added fabric softener technology at the close of the twentieth century, J. Surfact. Deterg.2 (1999) 223. 10.1007/s11743-999-0077-4Search in Google Scholar
6. Bigorra Lsosas, J., Cuadrado, F., Humbert, M., Pomares, J. and Trius, A.: PCT Int. Appl. WO9101295 to Henkel K.-G.a.A. Pulcra S.A., 1991.Search in Google Scholar
7. Busch, P., Lange, F. and Thiele, K.: Ger. Patent DE3623215 to Henkel K.-G.a.A. Germany, 1988.Search in Google Scholar
8. Rutzen, H., Bischoff, M. and Wegener, I.: Ger. Patent DE3402146 to Henkel K.-G.a.A., 1985.Search in Google Scholar
9. Bigorra Llosas, J., Bonastre, N., Pi Subirana, R. and Caldero, G.: Ger. Patent DE10019142 to Cognis Deutschland G.m.b.H., Germany, 2001.Search in Google Scholar
10. LettonJ.C.: Detergent composition consisting essentially of biodegradable nonionic surfactant and cationic surfactant containing ester or amide, U. S. Patent 4,260,529, 1981.Search in Google Scholar
11. Indian Standard: 548 (Part I), p. 29, 1964.Search in Google Scholar
12. Indian Standard: 548 (Part I), p. 50, 1964.10.1016/0002-9416(64)90167-8Search in Google Scholar
13. Indian Standard: 548 (Part I), p. 47, 1964.10.1093/jaoac/47.3.548Search in Google Scholar
14. Jamieson, G. R. and Reid, E. H.: The analysis of oils and fats by gas chromatography, J. Chromatog. A17 (1965) 230. 10.1016/S0021-9673(00)99862-5Search in Google Scholar
15. Overkempe, C., Annerling, A., Van Ginkel, C. G., Thomas, P. C., Boltersdorf, D. and Speelman, J.: Esterquats, in: HolmbergK. (Ed.), Novel Surfactants: Preparation, Application and Biodegradability, surfactant science series, Marcel Dekker Inc., New York (2003) 114. 10.1201/9780203911730Search in Google Scholar
16. Indian Standard: 4955, p. 4, 2001.Search in Google Scholar
17. Beal, C. M., Olson, L. A. and Wentz, M.: Property modification of finished textiles by a cationic surfactant, J. Am. Oil Chem. S °C.67 (1990) 689. 10.1007/BF02540424Search in Google Scholar
18. Indian Standard: 4631, 1968.Search in Google Scholar
19. Wrinkle Recovery of Fabrics: Appearance Method, AATCC Test Method 128–2013.Search in Google Scholar
20. Egan, R. R.: Cationic surface active agents as fabric softeners, J. Am. Oil Chem. S °C.55 (1978) 118. 10.1007/BF0267Search in Google Scholar
21. Ginn, M. E., Schenach, T. A. and Jungermann, I.: Performance evaluation of selected fabric softners, J. Am. Oil Chem. S °C.42 (1965) 1084. 10.1007/BF02636915Search in Google Scholar
22. Perez, L., Pinazo, A., Rosen, M. J. and Infante, M. R.: Surface Activity Properties at Equilibrium of Novel Gemini Cationic Amphiphilic Compounds from Arginine, Bis(Args), Langmuir14 (1998) 2307. 10.1021/la971135uSearch in Google Scholar
23. Indian Standard: 5785 (Part IV), p. 3, 1976.Search in Google Scholar
24. Orthoefer, F. T.: Rice Bran Oil, Bailey's industrial oil and fat products, Wiley-Interscience Publication2, 483. 10.1002/047167849X.bio015Search in Google Scholar
25. Rosen, M. J.: Characteristic features of surfactants, Surfactants and Interfacial Phenomena, Wiley-Interscience Publication (2004). 10.1002/0471670561Search in Google Scholar
26. Friedli, F. E., Koehle, H. J., Fender, M., Watts, M., Keys, R., Frank, P., Toney, C. J. and Doerr, M.: Upgrading triethanolamine esterquat performance to new level, J. Surfact. Deterg.5 (2002) 211. 10.1007/s11743-002-0220-2Search in Google Scholar
27. Rosen, M. J.: Foaming and antifoaming by aqueous solutions of surfactants, Surfactants and Interfacial Phenomena, Wiley-Interscience Publication (2004). 10.1002/0471670561Search in Google Scholar
28. Rosen, M. J.: Molecular Interaction and Synergism in Mixture of Two Surfactants, Surfactants and Interfacial Phenomena, Wiley-Interscience Publication (2004). 10.1002/0471670561Search in Google Scholar
© 2014, Carl Hanser Publisher, Munich
Articles in the same Issue
- Contents/Inhalt
- Contents
- Application
- Rapid Assessment of Glass Etching/Corrosion using the Quartz Crystal Microbalance with Dissipation Monitoring, QCM-D
- Micelle Based Spectrofluorimetric Determination of Chloroquine Phosphate in Commercial Formulation and Human Plasma
- Novel Surfactants
- Synthesis of Rice Bran Fatty Acids (RBFAs) Based Cationic Surfactants and Evaluation of Their Performance Properties in Combination with Nonionic Surfactant
- Synthesis and Properties of Guerbet Hexadecyl Sulfate
- Synthesis and Characterization of N-alkyl-N′-glucosylhexanediamine Surfactant
- Mizellar Catalysis
- Methanesulfonic Acid as a More Efficient Catalyst for the Synthesis of Lauraldehyde Glycerol Acetal
- Surfactant Assisted Enhancement of Bioremediation Rate for Hexavalent Chromium by Water Extract of Siris (Albizia lebbeck) Sawdust
- Physical Chemistry
- Synergistic Interactions in Mixed W/O Microemulsions of Cationic Gemini and Anionic Surfactants
- Percolative Behavior Models Based on Artificial Neural Networks for Electrical Percolation of AOT Microemulsions in the Presence of Crown Ethers as Additives
- Junction Characteristics System Based on Composite Organic Semiconductors: Polystyrene/Polyaniline Doped by [BMIM] [BF4] Ionic Liquid
Articles in the same Issue
- Contents/Inhalt
- Contents
- Application
- Rapid Assessment of Glass Etching/Corrosion using the Quartz Crystal Microbalance with Dissipation Monitoring, QCM-D
- Micelle Based Spectrofluorimetric Determination of Chloroquine Phosphate in Commercial Formulation and Human Plasma
- Novel Surfactants
- Synthesis of Rice Bran Fatty Acids (RBFAs) Based Cationic Surfactants and Evaluation of Their Performance Properties in Combination with Nonionic Surfactant
- Synthesis and Properties of Guerbet Hexadecyl Sulfate
- Synthesis and Characterization of N-alkyl-N′-glucosylhexanediamine Surfactant
- Mizellar Catalysis
- Methanesulfonic Acid as a More Efficient Catalyst for the Synthesis of Lauraldehyde Glycerol Acetal
- Surfactant Assisted Enhancement of Bioremediation Rate for Hexavalent Chromium by Water Extract of Siris (Albizia lebbeck) Sawdust
- Physical Chemistry
- Synergistic Interactions in Mixed W/O Microemulsions of Cationic Gemini and Anionic Surfactants
- Percolative Behavior Models Based on Artificial Neural Networks for Electrical Percolation of AOT Microemulsions in the Presence of Crown Ethers as Additives
- Junction Characteristics System Based on Composite Organic Semiconductors: Polystyrene/Polyaniline Doped by [BMIM] [BF4] Ionic Liquid
