Study on a Class of Cationic Gemini Surfactants
-
, , and
Abstract
Four cationic Gemini surfactants with different length of the hydrophobic chain (abbreviated as C12-CGB, C14-CGB, C16-CGB and C18-CGB) have been synthesized. The structures were confirmed by MS and 1H NMR. Their basic surface chemical properties and antistatic properties were investigated. The result indicated that upon increasing the number of carbon, the critical micelle concentration (CMC) and the equilibrium surface tension (γCMC) decreased initially and then increased. The products' Krafft points were all below 0°C except that of C18-CGB, it was 16.5°C. Emulsifying properties were determined by the water separation time method. The data show that the emulsifying capability increased gradually with the increase of concentration and then stabilized. In addition, the static voltage and static half period values of the calicoes treated with the four products were measured. These products exhibited excellent antistatic properties.
Kurzfassung
Es wurden vier kationische Gemini-Tenside mit unterschiedlicher Länge der hydrophoben Kette (abgekürzt als C12-CGB, C14-CGB, C16-CGB und C18-CGB) synthetisiert. Die Strukturen wurden durch MS und 1H-NMR bestätigt. Ihre grundlegenden oberflächenchemischen Eigenschaften und antistatischen Eigenschaften wurden untersucht. Das Ergebnis zeigte, dass bei Erhöhung der Kohlenstoffanzahl die kritische Mizellenbildungskonzentration (CMC) und die Oberflächenspannung bei der CMC (γCMC) anfänglich abnahmen und dann zunahmen. Die Krafft-Punkte der Produkte lagen alle unter 0°C, mit Ausnahme des von C18-CGB mit 16,5°C. Die Emulgiereigenschaften wurden nach der Methode der Wassertrennungszeit bestimmt. Die Daten zeigen, dass die Emulgierfähigkeit mit zunehmender Konzentration allmählich anstieg und sich dann stabilisierte. Außerdem wurden die statischen Spannungswerte und die statischen Halbperiodenwerte der mit den vier Produkten behandelten Kattunstoffe gemessen. Diese Produkte zeigten hervorragende antistatische Eigenschaften.
References
1. Zana, R.: Dimeric (Gemini) Surfactant: Effect of the Spacer Group on the Association Behavior in Aqueous Solution, J. Colloid Interface Sci.248 (2002) 203–220. PMid:16290524; 10.1006/jcis.2001.8104Search in Google Scholar
2. Zana, R.: Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: a review, Adv Colloid Interface Sci97 (2002) 205–53. 10.1016/S0001-8686(01)00069-0Search in Google Scholar
3. Menger, F. M. and Littau, C. A.: Gemini surfactants: a new class of self-assembling molecules, J.Am.Chem Soc.115 (1993) 10083–10090. 10.1021/ja00075a025Search in Google Scholar
4. Menger, F. M., Keiper, J. S. and Sazov, V.: Gemini surfactants with acetylenic spacers, Langmuir.16 (2000) 2062–2067. 10.1021/la9910576Search in Google Scholar
5. Rosen, M. J., J., H. M., and Davenport, L.: Aberrant Aggregation Behavior in Cationic Gemini Surfactants Investigated by Surface Tension, Interfacial Tension, and Fluorescence Methods, Langmuir.15 (1999) 7340–7346. 10.1021/la9904096Search in Google Scholar
6. Li, F., Rosen, M. J. and Sulthana, S. B.: Surface properties of cationic gemini surfactants and their interaction with alkylglucoside or maltoside surfactants, Langmuir17 (2001) 1037–1042. 10.1021/la001162bSearch in Google Scholar
7. Menger, F. M. and Keiper, J. S.: Gemini Surfactants, Angew Chem Int Ed Engl.39(2000) 1906–1920. 10.1002/1521-3773Search in Google Scholar
8. Menger, F. M. and Littau, C. A.: Gemini surfactants: a new class of self-assembling molecules, J.am.chem Soc.115 (1993) 10083–10090. 10.1021/ja00075a025Search in Google Scholar
9. Taleb, K., Mohamed-Benkada, M., Benhamed, N., Saidi-Besbes, S., Grohens, Y. and Derdour, A.: Benzene ring containing cationic gemini surfactants: synthesis, surface properties and antibacterial activity, J MOL LIQ.241 (2017) 81–90. 10.1016/j.molliq.2017.06.008Search in Google Scholar
10. Fisicaro, E., Compari, C., Bacciottini, F., Contardi, L., Pongiluppi, E. and Barbero, N., et al.: Nonviral gene-delivery by highly fluorinated gemini bispyridinium surfactant-based DNA nanoparticles, J. Colloid Interface Sci.487(2017) 182–191. PMid:27769002; 10.1016/j.jcis.2016.10.032Search in Google Scholar PubMed
11. Wang, Y. X., Gao, Y. Q., Zhang, Q. and Meng, Q.: A Novel Cationic Emulsifier Used for Preparing Slow-Cracking and Rapid-Setting Asphalt: Synthesis, Surface Activity and Emulsification Ability, J Disper Sci Technol.39 (2018) 478–483. 10.1080/01932691.2015.1120676Search in Google Scholar
12. Yuan, T., Liu, Z., Gao, R., Hu, G., Zhang, G. and Zhao, J.: Enhanced oil recovery from high-salinity reservoirs by cationic gemini surfactants, J. Appl Polym Sci.135 (2017) 46086. 10.1002/app.46086Search in Google Scholar
13. Rajput, S. M., Kumar, S., Aswal, V. K., Seoud, O. A. E., Malek, N. A. I. and Kailasa, S. K.: Drug-Induced Micelle-to-Vesicle Transition of a Cationic Gemini Surfactant: Potential Applications in Drug Delivery, Chemphyschem.19 (2018) 865–872. PMid:29319220; 10.1002/cphc.201701134Search in Google Scholar PubMed
14. El-Said, W. A., Moharram, A. S., Hussein, E. M. and El-Khawaga, A. M.: (2018) Design, synthesis, anticorrosion efficiency, and applications of novel gemini surfactants for preparation of small-sized hollow spheres mesoporous silica nanoparticles, Mater Chem Phys.211 (2018) 123–136. 10.1016/j.matchemphys.2018.02.013Search in Google Scholar
15. Khan, A. A. P., Khan, A., Rahman, M. M., Asiri, A. M. and Oves, M.: Chemical Sensor Development and Antibacterial Activities Based on Polyaniline/Gemini Surfactants for Environmental Safety, J Polym Environ.26 (2018) 1673–1684. 10.1007/s10924-017-1055-9Search in Google Scholar
16. Pukale, D. D., Bansode, A. S., Pinjari, D. V., Kulkarni, R. R. and Sayed, U.: Application of Silicone Surfactant Along with Hydrocarbon Surfactants to Textile Washing for the Removal of Different Complex Stains, J Surfact Deterg.20 (2017) 287–295. 10.1007/s11743-016-1901-0Search in Google Scholar
17. Wang, Z., Wang, D., Fang, Y. and Shen, J.: Preparation and Properties of Antistatic Polyethylene Film Coated Polypropylene Non-woven Fabrics, Fiber Polym.19 (2018) 934–940. 10.1007/s12221-018-8048-8Search in Google Scholar
18. Lv, B.Gao, J. J., Ma, J. Z, Fan, Q. Q. and Wang, H. D.: Synthesis and properties of zwitterionic Gemini surfactant, China Surfactant Detergent & Cosmetics.45 (2015) 76–80. 10.13218/j.cnki.csdc.2015.02.004Search in Google Scholar
19. Wang, P., Shen, Y., Zhang, H. F. and Zhu, T. L.: Synthesis and performance of Gemini surfactant bis-(sodium N-ethylene dodecylamide ethyl sulfonate, China Surfactant Detergent & Cosmetics. 12 (2005) 76–80. 10.13218/j.cnki.csdc.2015.12.003Search in Google Scholar
20. Dai, Q.: Antistatic fabric and test method thereof for antistatic performance. China Fiber Inspection. (2008) 844–46. 10.14162/j.cnki.11-4772/t.2008.08.006Search in Google Scholar
21. Gottlieb, H. E., Kotlyar, V. and Nudelman, A.: NMR chemical shifts of common laboratory solvents as trace impurities, J Org Chem.62 (1997) 7512–7515. PMid:11671879; 10.1021/jo971176vSearch in Google Scholar PubMed
22. Li, P.Q.: Progress in the application of cationic Gemini surfactant, China Surfactant Soap and Detergent Industries.7 (2015) 46–51. 10.16054/j.cnki.cci.2015.07.013Search in Google Scholar
23. Rosen, M. J. and Kunjappu, J. T.: Surfactants and interfacial phenomena, 4th edition, Colloids & Surfaces, 40 (2004) (June). 10.1002/0471670561Search in Google Scholar
24. Lu, T., and Huang, J. B.: Synthesis and properties of novel Gemini surfactant with short spacer, Chinese Science Bulletin (English). 52(2007) 2618–2620. 10.1007/s11434-007-0398-3Search in Google Scholar
25. Ahire, M. B., and Bhagwat, S. S.: Novel Ester-linked Anionic Gemini Surfactant: Synthesis, Surface-Active Properties and Antimicrobial Study, J Surfact Deterg.20 (2017) 789–797. 10.1007/s11743-017-1977-1Search in Google Scholar
26. Liu, X. P., Feng, J., Zhang, L., Gong, Q. T., Zhao, S., and Yu, J. Y.: Synthesis and properties of a novel class of anionic gemini surfactants with polyoxyethylene spacers, Colloid Surface A.362 (2010) 39–46. 10.1016/j.colsurfa.2010.03.037Search in Google Scholar
27. People's Republic of China Textile Industry Standard.: Textile materials-Electrostatic properties-Determination of static voltage half-life, China Standard Press, Beijing (1997).Search in Google Scholar
28. Wang, G. H. and Yu, J. L.: Performance research and product development of antistatic fabrics. Silk. (2001) 236–38. 10.3969/j.issn.1001-7003.2001.02.013Search in Google Scholar
29. State Administration of Quality Supervision, Inspection and Quarantine of the People's Republic of China, China National Standardization Administration.: GB/T 12703.1–2008 Textiles-Evaluation of electrostatic properties-Static voltage half-life method China Standard Press, Beijing (2008).Search in Google Scholar
© 2019, Carl Hanser Publisher, Munich
Articles in the same Issue
- Contents/Inhalt
- Contents
- Review Article
- Review on Silicone Surfactants: Silicone-based Gemini Surfactants, Physicochemical Properties and Applications
- Cleaning Agents
- Evaluation of Ethoxylated Rapeseed Oil Fatty Acids Methyl Esters as Nonionic Co-Surfactants in Hand Dishwashing Liquids
- Evaluation of the Bactericidal Activity of Didecyl Dimethyl Ammonium Chloride in 2-Propanol against Pseudomonas aeruginosa Strains with Adaptive Resistance to this Active Substance According to European Standards
- Environmental Chemistry
- Production of Bioemulsifier by Yeast from the Meyerozyma guilliermondii Complex Isolated from Soil Contaminated with Diesel Oil
- Physical Chemistry
- Fluorescence Study of Aggregation Behaviour of Cationic Surfactant Carbethopendecinium Bromide and its Comparison with Cetyltrimethylammonium Bromide
- Wettability of Phosphonium Benzene Sulfonate on Parafilm
- Study of Zinc-glycylglycine Complex with Ninhydrin in Aqueous and Cationic Micellar Media: A Spectrophotometric Technique
- Study on a Class of Cationic Gemini Surfactants
- Application
- The Performance Comparison Of Branched Methyl Stearate Ethoxylate and Linear Methyl Stearate Ethoxylate
- Study of the Rheological Behavior of a Spent Solution of Viscoelastic Surfactant in the Presence of Iron Ions
- Micellar Catalysis
- Synthesis of 2-(Prop-2-ynyloxy) Benzaldehyde using Salicyl Aldehyde and Propargyl Bromide in Aqueous Micellar Media
- Novel Surfactant
- Synthesis and Properties of Amphoteric Amide Surfactants with Reactive Group
Articles in the same Issue
- Contents/Inhalt
- Contents
- Review Article
- Review on Silicone Surfactants: Silicone-based Gemini Surfactants, Physicochemical Properties and Applications
- Cleaning Agents
- Evaluation of Ethoxylated Rapeseed Oil Fatty Acids Methyl Esters as Nonionic Co-Surfactants in Hand Dishwashing Liquids
- Evaluation of the Bactericidal Activity of Didecyl Dimethyl Ammonium Chloride in 2-Propanol against Pseudomonas aeruginosa Strains with Adaptive Resistance to this Active Substance According to European Standards
- Environmental Chemistry
- Production of Bioemulsifier by Yeast from the Meyerozyma guilliermondii Complex Isolated from Soil Contaminated with Diesel Oil
- Physical Chemistry
- Fluorescence Study of Aggregation Behaviour of Cationic Surfactant Carbethopendecinium Bromide and its Comparison with Cetyltrimethylammonium Bromide
- Wettability of Phosphonium Benzene Sulfonate on Parafilm
- Study of Zinc-glycylglycine Complex with Ninhydrin in Aqueous and Cationic Micellar Media: A Spectrophotometric Technique
- Study on a Class of Cationic Gemini Surfactants
- Application
- The Performance Comparison Of Branched Methyl Stearate Ethoxylate and Linear Methyl Stearate Ethoxylate
- Study of the Rheological Behavior of a Spent Solution of Viscoelastic Surfactant in the Presence of Iron Ions
- Micellar Catalysis
- Synthesis of 2-(Prop-2-ynyloxy) Benzaldehyde using Salicyl Aldehyde and Propargyl Bromide in Aqueous Micellar Media
- Novel Surfactant
- Synthesis and Properties of Amphoteric Amide Surfactants with Reactive Group