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Synthesis and Properties of Sodium Salts of Sulfonated Cardanol Polyethoxylates

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Published/Copyright: January 24, 2019
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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 56 Issue 1

Abstract

Sodium salts of sulfonated cardanol polyethoxylates (NSF–nSO, with n = 3 or 6 for the average ethylene oxide number) were synthesized using cardanol polyethylene oxides from renewable cardanol and sodium isethionate as reagents. The surface tension, interfacial tension (IFT), foaming, wetting ability and emulsifying ability of NSF–nSO were investigated. It was found that there was no significant difference between NSF–3SO and NSF–6SO in the critical micelle concentration (CMC), but the surface tension of NSF–3SO at CMC was lower than that of NSF–6SO. The diffusion coefficient (Deff) decreases with the increase of the NSF–nSO concentration. The IFT between NSF–3SO solution and dodecane is lower than that of NSF–6SO at studied salt concentrations. The foaming, wetting and emulsifying abilities of NSF–3SO are better than those of NSF–6SO. The above results show that NSF–3SO has better surface/interface activity than NSF–6SO.

Kurzfassung

Natriumsalze sulfonierter Cardanolpolyethoxylate (NSF–nSO, mit n = 3 oder 6 für die durchschnittliche Ethylenoxidzahl) wurden unter Verwendung von Car-danol-Polyethylenoxiden aus erneuerbarem Cardanol und Natriumisethionat als Reagenzien synthetisiert. Untersucht wur-den die Oberflächenspannung, Grenzflächenspannung (IFT), Schaumbildung, Benetzungs- und Emulgierfähigkeit von NSF–nSO. Es wurde gefunden, dass es keinen signifikanten Unterschied zwischen NSF–3SO und NSF–6SO hinsichtlich der kritischen Mizellenbildungskonzentration (CMC) gab, aber die Oberflächenspannung von NSF–3SO bei der CMC war niedriger als die von NSF–6SO. Der Diffusionskoeffizient (Deff) nimmt mit steigender NSF–nSO-Konzentration ab. Die IFT zwischen NSF–3SO-Lösung und Dodecan ist bei den untersuchten Salzkonzentrationen niedriger als die von NSF–6SO. Die Schaum-, Benetzungs- und Emulgierfähigkeiten von NSF–3SO sind besser als die von NSF–6SO. Die obigen Ergebnisse zeigen, dass NSF–3SO eine bessere Oberflächen und Grenzflächenaktivität als aufweist NSF–6SO.

Key words: Cardanol-based surfactants; interfacial properties; surface tension; interfacial tension
Stichwörter: Cardanol-basierte Tenside; Grenzflächeneigenschaften; Oberflächenspannung; Grenzflächenspannung
*Correspondence address, Dr. Jinping Niu, China Research Institute of Daily Chemical Industry, Taiyuan, Shanxi 030001, P.R. China, Tel.: 00 86-3 51-4 19 28 78, E-Mail: ,

Xiaochen Liu received his PhD in Physical Chemistry from Shanxi University and is an engineer at the China Research Institute of the Daily Chemical Industry. His research interests in the synthesis and application of novel sulfonate surfactants for EOR. Address: China Research Institute of Daily Chemical Industry, 34 Wenyuan Street, Taiyuan, Shanxi Province, 030001 P. R. China. E-Mail: .

Yueqing Huo is an engineer at the China Research Institute of the Daily Chemical Industry. Her research interest is the application of surfactants in EOR. Address: China Research Institute of Daily Chemical Industry, 34 Wenyuan Street, Taiyuan, Shanxi Province, 030001 P. R. China. E-Mail: .

Jinping Niu is a professor at the China Research Institute of Daily Chemical Industry. Her research interests are the sulfonation/sulfation of organic materials and the application of surfactants for EOR. Address: China Research Institute of Daily Chemical Industry, 34 Wenyuan Street, Taiyuan, Shanxi Province, 030001 P. R. China. Tel.: 00 86-3 51-4 19 28 78; E-Mail: .

References

1. Natarajan, M., and Murugavel, S. C.: Cure kinetics of bio-based epoxy resin developed from epoxidized cardanol-formaldehyde and diglycidyl ether of bisphenol-A networks, J Therm Anal Calorim.125 (2016) 387–396. 10.1007/s10973-016-5417-7Search in Google Scholar

2. Sakulsaknimitr, W., Wirasate, S., Pipatpanyanugoon, K. and Atorngitjawat, P.: Structure and thermal properties of polyurethanes synthesized from cardanol diol, J Polym Environ.23 (2015) 216–226. 10.1007/s10924-014-0707-2Search in Google Scholar

3. Paiva, G. M. S., Freitas, A. R., Nobre, F. X., Leite, C. M. S., Matos, J. M. E. and Rios, M. A. S.: Kinetic and thermal stability study of hydrogenated cardanol and alkylated hydrogenated cardanol. J Therm Anal Calorim, 120 (2015)1617–1625. 10.1007/s10973-015-4528-xSearch in Google Scholar

4. Balgude, D. and Sabnis, A. S.: CNSL: an environment friendly alternative for the modern coating industry, J. Coat. Technol. Res, 11 (2014) 169–183. 10.1007/s11998-013-9521-3Search in Google Scholar

5. Kattimuttathu, I. S., Foerst, G., Schubert, R. and Bartsch, E.: Synthesis and micellization properties of new anionic reactive surfactants based on hydrogenated cardanol, J Surfact Deterg.15 (2012) 207–215. 10.1007/s11743-011-1294-zSearch in Google Scholar

6. Ravichandran, S., Bouldin, R. M., Kumar, J. and Nagarajan, R.: A renewable waste material for the synthesis of a novel non-halogenated flame retardant polymer, J Clean Prod.19 (2011) 454–458. 10.1016/j.jclepro.2010.09.010Search in Google Scholar

7. Scorzza, C., Nieves, J., Vejar, F. and Bullo‧n, J.: Synthesis and physicochemical characterization of anionic surfactants derived from cashew nut shell oil, J Surfact Deterg.13 (2010) 27–31. 10.1007/s11743-009-1143-5Search in Google Scholar

8. Bruce, I. E., Mehta, L., Porter, M. J., Stein, B. K. and Tyman, J. H. P.: Anionic surfactants synthesized from replenishable phenolic lipids, J Surfact Deterg.12 (2009) 337–344. 10.1007/s11743-009-1116-8Search in Google Scholar

9. Peungjitton, P., Sangvanich, P., Pornpakakul, S., Petsom, A. and Roengsumran, S.: Sodium cardanol sulfonate surfactant from cashew nut shell liquid, J Surfact Deterg.12 (2009) 85–89. 10.1007/s11743-008-1082-6Search in Google Scholar

10. Tyman, J. H. P. and Bruce, I. E.: Surfactant properties and biodegradation of polyethoxylates from phenolic lipids. J Surfact Deterg.7 (2004) 169–173. 10.1007/s11743-004-0300-3Search in Google Scholar

11. Tyman, J. H. P. and Bruce, I. E.: Synthesis and characterization of polyethoxylates surfactants derived from phenolic lipids, J Surfact Deterg.6 (2003) 291–297. 10.1007/s11743-003-0272-3Search in Google Scholar

12. Wang, X. G., Yan, F., Li, Z. Q., Zhang, L., Zhao, S., An, J. Y. and Yu, J. Y.: Synthesis and surface properties of several nonionic-anionic surfactants with straight chain alkyl-benzyl hydrophobic group, Colloids Surf. A.302 (2007) 532–539. 10.1016/j.colsurfa.2007.03.026Search in Google Scholar

13. Liu, Z. Y., Li, Z. Q., Song, X. W., Zhang, J. C., Zhang, L. and Zhao, S.: Dynamic interfacial tensions of binary nonionic-anionic and nonionic surfactant mixtures at water-alkane interfaces, Fuel.135 (2014) 91–98. 10.1016/j.fuel.2014.06.031Search in Google Scholar

14. Zhang, Y. M., Niu, J. P. and Li, Q. X.: Synthesis and properties evaluation of sodium fatty alcohol polyoxyethylene ether sulfonate, Tenside Surf. Det.47 (2010) 34–39. 10.3139/113.110051Search in Google Scholar

15. Aoudia, M., Al-Harthi, Z., Al-Maamari, R. S., Lee, C. and Berger, P.: Novel alkyl ether sulfonates for high salinity reservoir: effect of concentration on transient ultralow interfacial tension at the oil-water Interface, J Surfact Deterg.13 (2010) 233–242. 10.1007/s11743-010-1182-ySearch in Google Scholar

16. Al-Faraji, S., Al-Maamari, R. S. and Aoudia, M.: Sodium alkyl ether sulfonates (SAES): dual anionic-nonionic behavior in synthetic brine having high salinity and hardness, J Surfact Deterg.18 (2015) 113–121. 10.1007/s11743-014-1593-2Search in Google Scholar

17. Liu, X. C., Zhao, Y. X., Li, Q. X., Jiao, T. L. and Niu, J. P.: Surface and interfacial tension of nonylphenol polyethylene oxides sulfonate, J Mol Liq.216 (2016) 185–191. 10.1016/j.molliq.2016.01.009Search in Google Scholar

18. Luan, H. X., Wu, Y. Q., Wu, W. X., Zhang, W., Chen, Q. S., Zhang, H. L., Yuan, D. D., Qu, G. M. and Ding, W.: Study on cardanolbetaine surfactants for ultralow interfacial tension in a low range of surfactant concentration and wide range of temperature applied in compound flooding, Tenside Surf. Det.52 (2015)29–34. 10.3139/113.110345Search in Google Scholar

19. Li, C. Q., Wang, F. F., Guo, S. y., Huang, J., Shi, W. G. and Wang, J.: Interface activity and thermodynamic properties of cardanol polyoxyethylene ether carboxylates, Tenside Surf. Det.53 (2016) 304–312. 10.3139/113.110444Search in Google Scholar

20. Zhou, Y. W., Su, P. Q., Han, F, Zhang, G. J. and Xu, B. C.: Synthesis and characterization of saturated cardanol sulfonate salt gemini surfactant, Tenside Surf. Det.54 (2017) 322–326. 10.3139/113.110504Search in Google Scholar

21. Jiao, T. L., Liu, X. C. and Niu, J. P.: Effects of sodium chloride on adsorption at different interfaces and aggregation behaviors of disulfonate gemini surfactants, Rsc Advances.6 (2016) 13881–13889. 10.1039/C5RA25727ASearch in Google Scholar

22. Gao, Y. Y., Yang, X. Q., Bai, L. and Zhang, J.: Preparation and physicochemical properties of disodium lauryl glucoside sulfosuccinate, J Surfact Deterg.17 (2014) 603–608. 10.1007/s11743-013-1561-2Search in Google Scholar

23. Rosen, M. J. and Kunjappu, J. T.: Surfactants and interfacial phenomena, John Wiley & Son, New York, (2012). 10.1002/9781118228920Search in Google Scholar

24. Ward, A. F. H. and Tordai, L.: Time dependence of boundary tensions of solutions. 1. The role of diffusion in time effects, J Chem Phys.14 (1946) 453–461. 10.1063/1.1724167Search in Google Scholar

25. Eastoe, J. and Dalton, J. S.: Dynamic surface tension and adsorption mechanisms of surfactants at the air/water interface, Adv. Colloid Interface Sci.85 (2000) 103–144. 10.1016/S0001-8686(99)00017-2Search in Google Scholar PubMed

26. Fainerman, V. B., Makievski, A. V. and Miller, R.: The analysis of dynamic surface tension of sodium alkyl sulphate solutions, based on asymptotic equations of adsorption kinetic theory, Colloids Surf. A87 (1994) 61–75. 10.1016/0927-7757(94)02747-1Search in Google Scholar

27. Jiang, Y. G., Geng, T., Li, Q. X., Li, G. J. and Ju, H. B.: Equilibrium and dynamic surface tension properties of salt-free catanionic surfactants with different hydrocarbon chain lengths, J Mol Liq.204 (2015) 126–131. 10.1016/j.molliq.2015.01.026Search in Google Scholar

28. Gao, Y. Y. and Yang, X. Q.: Equilibrium and dynamic surface properties of sulfosuccinate surfactants, J Surfact Deterg.17(2014)1117–1123. 10.1007/s11743-014-1612-3Search in Google Scholar

29. Soontravanich, S. and Scamehorn, J. F.: Use of a nonionic surfactant to inhibit precipitation of anionic surfactants by calcium, J Surfact Deterg.13 (2010) 13–18. 10.1007/s11743-009-1149-zSearch in Google Scholar

30. Soontravanich, S. and Scamehorn, J. F.: Relation of supersaturation ratio in mixed anionic surfactant solutions to kinetics of precipitation with calcium, J Surfact Deterg.13 (2010) 1–11. 10.1007/s11743-009-1150-6Search in Google Scholar

31. Liu, Z. Y., Zhang, L. and Cao, X. L.: Effect of electrolytes on interfacial tensions of alkyl ether carboxylate solutions, Energy Fuels.27(2013) 3122–3129. 10.1021/ef400458qSearch in Google Scholar

32. Cao, Y., Zhao, R. H., Xu, Z. C., Jin, Z. Q., Luo, L., Zhang, L. and Zhao, S.: Effect of electrolyte and temperature on interfacial tensions of alkylbenzene sulfonate solutions, Energy fuels.26 (2012) 2175–2181. 10.1021/ef201982sSearch in Google Scholar

33. Zhao, Z. K., Bi, C. G., Li, Z. S., Qiao, W. H. and Cheng, L. B.: Interfacial tension between crude oil and decylmethylnaphthalene sulfonate surfactant alkali-free flooding systems, Colloids Surf A.276 (2006) 186–191. 10.1016/j.colsurfa.2005.10.036Search in Google Scholar

Received: 2017-09-19
Accepted: 2017-11-21
Published Online: 2019-01-24
Published in Print: 2019-01-21

© 2019, Carl Hanser Publisher, Munich

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Editorial
  4. Review of the Year 2018
  5. Short Communication
  6. How Can Online Tools Help One Learn About and Improve Consumer Behaviour: Exemplarily, Laundry and Dishwashing Treatments?
  7. Review Article
  8. Novel Methods for Efficacy Testing of Disinfectants – Part I
  9. Detergent Analysis
  10. Simultaneous Determination of Two Alcohols and One Anionic Surfactant in Commercial Liquid Cleaners Using Partial Least Square Regression by Fourier Transform Infrared Spectrometry
  11. Novel Surfactants
  12. Synthesis of Nitrogen Containing Biocompatible Non-ionic Surfactants and Investigation for Their Self-Assembly Based Nano-Scale Vesicles
  13. Synthesis and Properties of Sodium Salts of Sulfonated Cardanol Polyethoxylates
  14. Synthesis of Mesoporous ZSM-5 Zeolite Crystals by a New Organosilane Template with Double-carbamate Carbon Chains
  15. Physical Chemistry
  16. Micellization and Counterion Binding Behavior of Cetylpyridinium Chloride in Aqueous Solutions of Sodium Bromide and Tetrabutylammonium Bromide
  17. Synergistic Properties of a Mixed Micelle System Consisting of a Nonionic Fluorinated Surfactant and a Cationic Surfactant
  18. Synthesis
  19. Optimization of Formation Reaction Conversions of Fatty Acid Amidopropyl Dimethylamines
https://doi.org/10.3139/113.110603
Keywords for this article
Cardanol-based surfactants; interfacial properties; surface tension; interfacial tension

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Editorial
  4. Review of the Year 2018
  5. Short Communication
  6. How Can Online Tools Help One Learn About and Improve Consumer Behaviour: Exemplarily, Laundry and Dishwashing Treatments?
  7. Review Article
  8. Novel Methods for Efficacy Testing of Disinfectants – Part I
  9. Detergent Analysis
  10. Simultaneous Determination of Two Alcohols and One Anionic Surfactant in Commercial Liquid Cleaners Using Partial Least Square Regression by Fourier Transform Infrared Spectrometry
  11. Novel Surfactants
  12. Synthesis of Nitrogen Containing Biocompatible Non-ionic Surfactants and Investigation for Their Self-Assembly Based Nano-Scale Vesicles
  13. Synthesis and Properties of Sodium Salts of Sulfonated Cardanol Polyethoxylates
  14. Synthesis of Mesoporous ZSM-5 Zeolite Crystals by a New Organosilane Template with Double-carbamate Carbon Chains
  15. Physical Chemistry
  16. Micellization and Counterion Binding Behavior of Cetylpyridinium Chloride in Aqueous Solutions of Sodium Bromide and Tetrabutylammonium Bromide
  17. Synergistic Properties of a Mixed Micelle System Consisting of a Nonionic Fluorinated Surfactant and a Cationic Surfactant
  18. Synthesis
  19. Optimization of Formation Reaction Conversions of Fatty Acid Amidopropyl Dimethylamines
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