Synthesis and Surface Properties of Anionic Vinylguaiacol Based Surfactants
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Prabhakara Rao Darapureddi
Abstract
By changing amino acid head group four biobased anionic surfactants were synthesized using 4-vinylguaiacol and methylbromo undecanoate. The synthesized surfactants were characterized by NMR and mass spectrometry analysis. The surface active properties such as surface tension, wetting power, foaming characteristic, emulsion stability, calcium tolerance were studied and compared with those of sodium lauryl sulfate (SLS). Excellent emulsion stabilities and calcium tolerances were observed for the synthesized surfactants. These surfactants show a lower critical micelle concentration as compared to the conventional surfactants. The bulk micellization properties were studied using dynamic light scattering and fluorescence anisotropy technique. The antimicrobial and cytotoxicity studies were also carried out.
Kurzfassung
Durch Veränderung der Aminosäurekopfgruppe wurden vier anionische biobasierte Tenside aus 4-Vinylguaiacol und Bromdecansäuremethylester synthetisiert. Die synthetisierten Tenside wurden mittels NMR und Massenspektrometrie charakterisiert. Die oberflächenaktiven Eigenschaften wie die Oberflächenspannung, die Benetzungsfähigkeit, die Schaumcharakteristika, die Emulsionsstabilität und die Calciumtoleranz wurden untersucht und mit denen von Natriumlaurylsulfat (SLS) verglichen. Exzellente Emulionsstabilitäten und Calciumtoleranzen wurden für diese Tenside bestimmt. Die Tenside zeigten eine im Vergleich zu konventionellen Tensiden geringere kritische Mizellenbildungskonzentration. Die Mizellisierungseigenschaften der Bulklösungen wurden mit der dynamischen Lichtstreuung und der Fluoreszenzanisotropie untersucht. Antimikrobielle und zytotoxische Studien wurden auch durchgeführt.
References
1. Maqsood, A. M., Mohd, A. H., Firdosa, N., Shaeel, A. A. T. and Zaheer, K.: Anti-Corrosion Ability of Surfactants: A Review; Int. J. Electrochem. Sci.6 (2011) 1927–1948.Suche in Google Scholar
2. Cserháti, T.; Forgács, E. and Oros, G.: Biological activity and environmental impact of anionic surfactants; Environ Int.28 (2002) 337–348. 10.1016/S0160-4120(02)00032-6Suche in Google Scholar
3. Lee, S.-W., Tettey, K. E., Yarovoy, Y. and Lee, D.: Effects of anionic surfactants on the water permeability of a model stratum corneum lipid membrane, Langmuir. 30 (2014) 220–226. 10.1021/la403138aSuche in Google Scholar
4. Yangxin, Y. U., Zhao, J. and Andrew, E. B.: Development of surfactants and builders in detergent formulations, Chinese J Chem Eng.16 (2008) 517–527. 10.1016/S1004-9541(08)60115-9Suche in Google Scholar
5. Sanchez, J. and Valle, M. D.: Determination of anionic surfactants employing potentiometric sensors, Cr. Rev. Anal. Chem.35 (2005)15–29. 10.1080/10408340590947899Suche in Google Scholar
6. Lawrence, M. J.: Surfactant systems: Micro emulsions and vesicles as vehicles for drug delivery, Eur J Drug Metab Ph.19 (1994) 257–270. 10.1007/BF03188929Suche in Google Scholar PubMed
7. Riechers, D. E., Wax, L. M., Liebl, R. A. and Bullock, D. G.: Surfactant effects on glyphosate efficacy, Weed Technol.9 (1995) 281–285.10.1017/S0890037X00023356Suche in Google Scholar
8. Reich, C. and Robbins, C. R.: Interactions of cationic and anionic surfactants on hair surfaces: Light-scattering and radiotracer studies, J. Soc. Cosmet. Chem.44 (1993) 263–278.Suche in Google Scholar
9. Elvers, B., Hawkins, S. and Russey, W.: Ullmann's Encyclopedia of Industrial Chemistry: VCH Verlagsgesellschaft: Weinheim, Vol. A 25 (1994).Suche in Google Scholar
10. Xia, J. and Nnanna, I.: An overview of the basis, technology, and surface phenomena of protein-based surfactants. In Protein-Based Surfactants; Nnanna, I. A., Xia, J., Eds.; Marcel Dekker: New York (2001).Suche in Google Scholar
11. Hayes, D. G., Kitamoto, D., Solaiman, D. and Ashby, R. D.: Biobased Surfactants and Detergents: Synthesis, Properties, and ApplicationsAOCS Press: Urbana, IL. (2009).Suche in Google Scholar
12. Pinazo, A., Pons, R., Perez, L. and Infante, M. R.: Amino acids as raw material for biocompatible surfactants, Ind. Eng. Chem. Res.50 (2011) 4805–4817. 10.1021/ie1014348Suche in Google Scholar
13. Morán, M. C., Pinazo, A., Pérez, L., Clapés, P., Angelet, M., García, M. T., Vinardell, M. P. and Infante, M. R.: Green amino acid–based surfactants, Green Chem.6 (2004) 233–240. 10.1039/B400293HSuche in Google Scholar
14. Chandra, N. and Tyagi, V. K.: Synthesis, properties, and applications of amino acids based surfactants, J Disper Sci Technol.34 (2013) 800–808. 10.1080/01932691.2012.695967Suche in Google Scholar
15. Sreenu, M., Nayak, R. R., Prasad, R. B. N., Poornachandra, Y. and Ganesh, C. K.: Surface and antimicrobial properties of N-palmitoyl amino acid–based surfactants, J Disper Sci Technol.36 (2015) 765–771. 10.1080/01932691.2014.921626Suche in Google Scholar
16. Phani, P. K., Nayak, R. R. and Kanjilal, S.: Synthesis and surface properties of a novel sodium 3-(3-alkyloxy-3-oxopropoxy)-3-oxopropane-1-sulfonate at the air–water interface, J Surfactants Deterg.18 (2015) 689–695. 10.1007/s11743-015-1691-9Suche in Google Scholar
17. Sreenu, M., Nayak, R. R., Prasad, R. B. N. and Sreedhar, B.: Synthesis, surface and micellar properties of sodium N-oleoyl amino acids, Colloid Surface A449 (2014) 74–81. 10.1016/j.colsurfa.2014.02.037Suche in Google Scholar
18. Akula, S., Nayak, R. R. and Kanjilal, S.: Undecanoic and 10-undecenoic acid-based amidobetaines and amidoamine oxides, J Surfactants Deterg.17 (2014) 1021–1026. 10.1007/s11743-014-1578-1Suche in Google Scholar
19. Rosazza, J. P. N., Huang, Z., Dostal, L., Volm, T. and Rousseau, B.: Biocatalytic transformations of ferulic acid: An abundant aromatic natural product, J. Ind. Microbiol.15 (1995) 457–471. 10.1007/BF01570016Suche in Google Scholar
20. Walton, N. J., Narbad, A., Faulds, C. B. and Williamson, G.: Novel approaches to the biosynthesis of vanillin, Curr. Opin. Biotechnol.11 (2000) 490–496. 10.1016/S0958-1669(00)00125-7Suche in Google Scholar
21. Mariod, A. A., Adamu, H. A., Ismail, M. and Ismail, N.: Antioxidative effects of stabilized and unstabilized defatted rice bran methanolic extracts on the stability of rice bran oil under accelerated conditions, Grasas Aceites. 61 (2010) 409–415. 10.3989/gya.110309Suche in Google Scholar
22. Ogunniyi, D. S.: Castor oil: A vital industrial raw material, Bioresource Technol.97 (2006) 1086–1091. 10.1016/j.biortech.2005.03.028Suche in Google Scholar PubMed
23. Adewuyi, A., Oderinde, R. A., Rao, B. V. S. K. and Prasad, R. B. N.: Synthesis of alkanolamide: a nonionic surfactant from the oil of Gliricidia sepium, J. Surfactants Deterg.15 (2012) 89–96. 10.1007/s11743-011-1285-0Suche in Google Scholar
24. Linday, M. E.: Practical Introduction to Microbiology. E and F.N. Spon Ltd., United Kingdom, (1962) p. 177.Suche in Google Scholar
25. Bollu, V. S., Nethi, S. K., Dasari, R. K., Rao, S. S. N., Misra, S. and Patra, C.: Evaluation of in vivo cytogenetic toxicity of europium hydroxide nanorods (EHNs) in male and female Swiss albino mice, Nanotoxicology. 10 (2016) 413–425. 10.3109/17435390.2015.1073398Suche in Google Scholar PubMed
26. Azira, H., Tazerouti, A. and Canselier, J. P.: Study of foaming properties and effect of the isomeric distribution of some anionic surfactants, J. Surfactants Deterg.11 (2008) 279–286. 10.1007/s11743-008-1093-3Suche in Google Scholar
27. Mishra, M., Muthuprasanna, P., Surya Prabha, K., Sobhita Rani, P., Satish Babu, I. A., Chandiran, I. S., Arunachalam, G. and Shalini, S.: Basics and potential applications of surfactants, Int. J. PharmTech Res.1 (2009) 1354–1365.Suche 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