Home Synthesis and Properties of Cationic Gemini Surfactants with Amide Groups
Article
Licensed
Unlicensed Requires Authentication

Synthesis and Properties of Cationic Gemini Surfactants with Amide Groups

  • Zheng Zhu , Xiaohao Lu , Liangliang Lin , Hujun Xu and Haiyan Gao
Published/Copyright: July 8, 2020
Become an author with De Gruyter Brill
Author Information
Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 57 Issue 4

Abstract

In the present study, a series of gemini surfactants with amide group (abbreviated as (m = 12–16, n = 1, 2)) were synthesized. Complementary characterizations of their structure by spectroscopic methods such as IR, 1H-NMR, MS, and investigations of their properties such as measurements of the conductivity, the surface tension, the foaming and the emulsifying capacity were performed. The results showed that almost all products had a Krafft point below 0°C, except the C16–(EO)–E–C16 surfactant. Furthermore, the equilibrium surface tension (γCMC) of the synthesized Gemini surfactants at the CMC was determined. For C12-(EO)-E-C12 it is 41.0 mNm–1, for C14-(EO)-E-C14 43.8 mNm–1, for C16-(EO)-E-C16 46.7 mNm–1 and for C12-(EO)2-E-C12 41.9 mNm–1. The addition of the inorganic salt NaBr could significantly increase their surface activities. In addition, the thermodynamics of the micelle formation between 25°C–45°C was investigated. The results indicated that the micellization process was spontaneous. Finally, the obtained Gemini surfactants proved to be good emulsifiers, while their foaming properties were influenced by the self-coiling of the associated long alkyl tails.

Kurzfassung

In der vorliegenden Studie wurde eine Reihe von Gemini-Tensiden mit Amidgruppen (abgekürzt als Cm–(EO)n–E–Cm (m = 12–16, n = 1, 2)) synthetisiert. Ergänzende Charakterisierungen zu ihrer Struktur mittels spektroskopischer Methoden wie z.B. IR, 1H-NMR, MS, und zur Untersuchung ihrer Eigenschaften wie z.B. Messungen der Leitfähigkeit, der Oberflächenspannung, des Schaum- und Emulgiervermögens wurden durchgeführt. Die Ergebnisse zeigten, dass fast alle Produkte einen Krafft-Punkt unterhalb von 0°C hatten, mit Ausnahme des Tensids C16–(EO)–E–C16. Des Weiteren wurde die Gleichgewichts-Oberflächenspannung (γCMC) der synthetisierten Gemini-Tensiden bei der CMC bestimmt. Für C12–(EO)–E–C12 beträgt sie 41,0 mNm–1, für C14–(EO)–E–C14 43,8 mNm–1, für C16–(EO)–E–C16 46,7 mNm–1 und für C12–(EO)2–E–C12 41,9 mNm–1. Die Zugabe eines anorganischen Salzes (NaBr) konnte ihre Oberflächenaktivitäten signifikant erhöhen. Darüber hinaus wurde die Thermodynamik der Mizellenbildung zwischen 25°C–45°C untersucht. Die Ergebnisse deuten darauf hin, dass es sich bei der Mizellisierung um einen spontanen Prozess handelt. Schließlich erwiesen sich die erhaltenen Gemini-Tenside als gute Emulgatoren, während ihr Schaumvermögen aufgrund der Eigenverknäulung ihr langen Alkylkettenschwänze beeinflusst wurde.

Key words: Cationic Gemini surfactant; surface activities; thermodynamic parameters; performance properties
Stichwörter: Kationisches Gemini-Tensid; Oberflächenaktivitäten; thermodynamische Parameter; Leistungseigenschaften
∗ Correspondence address Mrs Prof. Haiyan Gao School of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, 214122 Wuxi, P.R. China, E-Mail:

Zheng Zhu: postgraduate. School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, P.R. China. E-Mail:

Xiaohao Lu: postgraduate. School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, P.R. China. E-Mail:

Liangliang Lin: Associate professor, he has published several papers in internationally renowned chemical journals such as AIChE Journal, Chemical Engineering Science, and Chemical Engineering Journal. School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, P.R. China. E-Mail:

Hujun Xu: Associate professor, he received his Ph.D. degree in 2005 from Nanjing University of Science and Technology, P.R. China. He has been involved in surfactants and detergents for over 30 years. He has published over 70 papers in the field of surfactants and detergents. School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, P.R. China. E-Mail:

Haiyan Gao: Associate professor, she received a doctorate in science from the Institute of Coal Chemistry, Chinese Academy of Sciences in 2003. Research direction is physical chemistry, synthesis and application of chemicals. School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, P.R. China. E-Mail:

References

1. Li, F., Rosen, M. J. and Sulthana, S. B.: Surface Properties of Cationic Gemini Surfactants and Their Interaction with Alkylglucoside or -maltoside Surfactants, Langmuir.17 (2001) 1037–1042. 10.1021/la001162bSearch in Google Scholar

2. Rosen, M. J. and Tracy, D. J.: Gemini Surfactants, J. Surfactants Deterg.1 (1998) 547–554. 10.1007/s11743-998-0057-8Search in Google Scholar

3. Garcia, M. T., Ribosa, I., Guindulain, T., Sanchez-Leal, J. and Vives-Rego, J.: Fate and Effect of Monoalkyl Quaternary Ammonium Surfactants in the Aquatic Environment. Environ, Pollut.111 (2001) 169–175. 10.1016/s0269-7491(99)00322-xSearch in Google Scholar PubMed

4. Weihs, D., Danino, D., Pinazo-Gassol, A., Perez, L., Franses, E. I. and Talmon, Y.: Self-aggregation in Dimeric Arginine-based Cationic Surfactants Solutions, Colloids Surf., A.255 (2005) 73–78. 10.1016/j.colsurfa.2004.11.035Search in Google Scholar

5. Perez, L., Torres, J. L., Manresa, A., Solans, C. and InfanteM. R.: Synthesis, Aggregation, and Biological Properties of a New Class of Gemini Cationic Amphiphilic Compounds from Arginine, bis(Args), Langmuir.12 (1996) 5296–5301. 10.1021/la960301fSearch in Google Scholar

6. Fisicaro, E., Compari, C., Duce, E., Donofrio, G., Rozycka-Roszak, B. and Wozniak, E.: Biologically Active Bisquaternary Ammonium Chlorides: Physico–chemical Properties of Long Chain Amphiphiles and Their Evaluation as Non-viral Vectors for Gene Delivery, Biochim. Biophys. Acta, Gen. Sub.1722 (2005) 224–233. 15725392 10.1016/j.bbagen.2004.12.013Search in Google Scholar PubMed

7. Gaucheron, J., Wong, T., Wong, K. F., Maurer, N. and Cullis, P. R.: Synthesis and Properties of Novel Tetraalkyl Cationic Lipids, Bioconjugate Chem.13 (2002) 671–675. 12009960 10.1021/bc0101259Search in Google Scholar PubMed

8. Akbaş, H., Kocaoğlu, S., Boz, M. and Dikmen, A.: A Novel Cationic Gemini Surfactant with Amide Group: Synthesis and Micellization Behavior in Aqueous Solutions, Colloid Polym. Sci.294 (2016) 1439–1451. 10.1007/s00396-016-3905-8Search in Google Scholar

9. Tatsumi, T., Zhang, W., Kida, T., Nakatsuji, Y., Ono, D., Takeda, D. and Ikeda, I.: Novel Hydrolyzable and Biodegradable Cationic Gemini Surfactants: Bis(ester-ammonium) Dichloride Having a Butenylene or a Butynylene Spacer, J. Surfactants Deterg.4 (2001) 279–285. 10.1007/s11743-001-0180-6Search in Google Scholar

10. Muslim, A. A., Ayyash, D., Gujral, S. S., Mekhail, G. M., Rao, P. P. N. and Wettig, S. D.: Synthesis and Characterization of Asymmetrical Gemini Surfactants, Phys. Chem. Chem. Phys.19 (2017) 1953–1962. 28009906 10.1039/c6cp07688bSearch in Google Scholar PubMed

11. Li, X., Hu, Z. Y., Zhu, H. L. and Zhao, S. F.: Synthesis and Properties of Novel Alkyl Sulfonate Gemini Surfactants, J. Surfactants Deterg.13 (2010) 353–359. 10.1007/s11743-010-1188-5Search in Google Scholar

12. Islam, M. S., Shortall, S. M., Mekhail, G. M., Callender, S. P., Madkhali, O., Bharwani, Z., Ayyash, D., Kobernyk, K. and Wettig, S. D.: Effect of Counterions on the Micellization and Monolayer Behaviour of Cationic Gemini Surfactants, Phys. Chem. Chem. Phys.19 (2017) 10825–10834. 28393936 10.1039/c7cp00775bSearch in Google Scholar PubMed

13. Zhang, Q., Gao, Z. N., Xu, F., Tai, S. X., Liu, X. G., Mo, S. B. and Niu, F.: Surface Tension and Aggregation Properties of Novel Cationic Gemini Surfactants with Diethylammonium Headgroups and a Diamido Spacer, Langmuir.28 (2012) 11979–11987. 22799465 10.1021/la3011212Search in Google Scholar PubMed

14. Dahanayake, M., Cohen, A. W. and Rosen, M. J.: Relationship of Structure to Properties of Surfactants. 13. Surface and Thermodynamic Properties of Some Oxyethylenated Sulfates and Sulfonates, J. Phys. Chem.90 (1986) 2413–2418. 10.1021/j100402a032Search in Google Scholar

15. Corrin, M. L. and Harkins, W. D.: The Effect of Salts on the Critical Concentration for the Formation of Micelles in Colloidal Electrolytes, J. Am. Chem. Soc.69 (1947) 683–688. 20289458 10.1021/ja01195a065Search in Google Scholar PubMed

16. Sakai, K., Wada, M., Matsuda, W. and Tsuchiya, K.: Polymerizable Anionic Gemini Surfactants: Physicochemical Properties in Aqueous Solution and Polymerization Behavior. J. Oleo. Sci.58 (2009) 403–413. 19584566 10.5650/jos.58.403Search in Google Scholar PubMed

17. Zhong, X., Guo, J. W., Feng, L. J., Xu, X. J. and Zhu, D. Y.: Cationic Gemini Surfactants Based on Adamantane: Synthesis, Surface Activity and Aggregation Properties, Colloids Surf., A.441 (2014) 572–580. 10.1016/j.colsurfa.2013.10.016Search in Google Scholar

18. Song, Y. B., Li, Q. X., Li, Y. L. and Zhi, L. F.: Surface and Aggregation Properties of HeteroGemini Surfactants Containing Quaternary Ammonium and Guanidine Moiety, Colloids Surf., A.417 (2013) 236–242. 10.1016/j.colsurfa.2012.11.004Search in Google Scholar

19. Sardar, N., Kamil, M. and Kabir-ud-Din.: Interaction between Nonionic Polymer Hydroxypropyl Methyl Cellulose (HPMC) and Cationic Gemini/Conventional Surfactants, Ind. Eng. Chem. Res.51 (2012) 1227–1235. 10.1021/ie2010725Search in Google Scholar

20. Hirata, H., Hattori, N., Ishida, M., Okabayashi, H., Frusaka, M. and Zana, R.: Small-Angle Neutron-Scattering Study of Bis(quaternary ammonium bromide) Surfactant Micelles in Water. Effect of the Spacer Chain Length on Micellar Structure, J. Phys. Chem.99 (1995) 17778–17784. 10.1021/j100050a017Search in Google Scholar

21. Michele, A. D., Brinchi, L., Profio, P. D., Germani, R., Savelli, G. and Onori, G.: Effect of Head Group Size, Temperature and Counterion Specificity on Cationic Micelles, J. Colloid Interface Sci.358 (2011) 160–166. 21440896 10.1016/j.jcis.2010.12.028Search in Google Scholar PubMed

22. Hu, D. H., Guo, X. F. and Jia, L. H.: Synthesis, Surface Active Properties of Novel Gemini Surfactants with Amide Groups and Rigid Spacers, J. Surfactants Deterg.16 (2013) 913–919. 10.1007/s11743-013-1502-0Search in Google Scholar

23. You, Y., Wu, X. N., Zhao, J. X., Ye, Y. Z. and Zou, W. S.: Effect of Alkyl Tail Length of Quaternary Ammonium Gemini Surfactants on Foaming Properties, Colloids Surf., A.384 (2011) 164–171. 10.1016/j.colsurfa.2011.03.050Search in Google Scholar
Received: 2019-05-27
Accepted: 2019-09-19
Published Online: 2020-07-08
Published in Print: 2020-07-15

© 2020, Carl Hanser Publisher, Munich

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Novel Surfactants
  4. The Effects of the Glucose-Based Cationic-Nonionic Surfactant with Ag-SiO2 Nanocomposites on Interfacial and Foam Ability Properties
  5. Synthesis and Properties of Alkyl Polyglycoside Polyoxypropylene Ethers
  6. Surface Properties and Adsorption Behavior of Alkyl Glycoside Tartarate
  7. Micellar Catalysis
  8. Trivalent Ruthenium and Iridium Salt: Excellent Homogeneous Catalysts for Cyclic Alcohol Oxidation in Micellar Media
  9. Application
  10. Preparation and Release Properties of Cationic Flavor Microcapsules with Tetradecyl Allyldimethyl Ammonium Bromide (TADAB) as Main Shell Material
  11. Synthesis, Characterization, Flocculation and Antistatic Properties of Poly(Methacryloyloxyethyl trimethyl Ammonium Chloride)
  12. Physical Chemistry
  13. Removal of Toxic Eosin Y Dye from Water Samples by Cloud Point Extraction using Triton X-114 as Nonionic Surfactant
  14. Synthesis
  15. Synthesis and Properties of Cationic Gemini Surfactants with Amide Groups
  16. Synthesis, Characterization, and Properties of Acyl Glycine, Alanine, Valine, and Leucine Derived from Vegetable Oils and Beef Tallow
https://doi.org/10.3139/113.110690
Keywords for this article
Cationic Gemini surfactant; surface activities; thermodynamic parameters; performance properties

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Novel Surfactants
  4. The Effects of the Glucose-Based Cationic-Nonionic Surfactant with Ag-SiO2 Nanocomposites on Interfacial and Foam Ability Properties
  5. Synthesis and Properties of Alkyl Polyglycoside Polyoxypropylene Ethers
  6. Surface Properties and Adsorption Behavior of Alkyl Glycoside Tartarate
  7. Micellar Catalysis
  8. Trivalent Ruthenium and Iridium Salt: Excellent Homogeneous Catalysts for Cyclic Alcohol Oxidation in Micellar Media
  9. Application
  10. Preparation and Release Properties of Cationic Flavor Microcapsules with Tetradecyl Allyldimethyl Ammonium Bromide (TADAB) as Main Shell Material
  11. Synthesis, Characterization, Flocculation and Antistatic Properties of Poly(Methacryloyloxyethyl trimethyl Ammonium Chloride)
  12. Physical Chemistry
  13. Removal of Toxic Eosin Y Dye from Water Samples by Cloud Point Extraction using Triton X-114 as Nonionic Surfactant
  14. Synthesis
  15. Synthesis and Properties of Cationic Gemini Surfactants with Amide Groups
  16. Synthesis, Characterization, and Properties of Acyl Glycine, Alanine, Valine, and Leucine Derived from Vegetable Oils and Beef Tallow
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 13.10.2025 from https://www.degruyterbrill.com/document/doi/10.3139/113.110690/html
Scroll to top button