Skip to main content
Log in

A Novel Alkyl Sulphobetaine Gemini Surfactant Based on S-triazine: Synthesis and Properties

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

A series of alkyl sulphobetaine Gemini surfactants C n -GSBS (n = 8, 10, 12, 14, 16) was synthesized, using aliphatic amine, cyanuric chloride, ethylenediamine, N,N′-dimethyl-1,3-propyldiamine and sodium 2-chloroethane sulfonate as main raw materials. The chemical structures were confirmed by FT-IR, 1H NMR and elemental analysis. The Krafft points differ markedly with different carbon chain length, for C8-GSBS, C10-GSBS and C12-GSBS are considered to be below 0 °C and C14-GSBS, C16-GSBS are higher than 0 °C but lower than room temperature. Surface-active properties were studied by surface tension and electrical conductivity. Critical micelle concentrations were much lower than dodecyl sulphobetaine (BS-12) and decreased with increasing length of the carbon chain from 8 to 16, and can reach a minimum as low as 5 × 10−5 mol L−1 for C16-GSBS. Effects of carbon chain length and concentration of C n -GSBS on crude oil emulsion stability were also investigated and discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Rosen MJ, Kunjappu JT. Surfactants and interfacial phenomena. 4th ed. Hoboken: John; 2012.

    Book  Google Scholar 

  2. Xu Q, Wang L, Xing F. Synthesis and properties of dissymmetric Gemini surfactants. J Surfactants Deterg. 2011;14(1):85–90.

    Article  CAS  Google Scholar 

  3. Murguía MC, Cristaldi MD, Porto A, Di Conza J, Grau RJ. Synthesis, surface-active properties, and antimicrobial activities of new neutral and cationic trimeric surfactants. J Surfactants Deterg. 2008;11(1):41–8.

    Article  Google Scholar 

  4. Zhou M, Zhao J, Hu X. Synthesis of Bis [N, N′-(alkylamideethyl) ethyl] triethylenediamine bromide surfactants and their oilfield application investigation. J Surfactants Deterg. 2012;15(3):309–15.

    Article  CAS  Google Scholar 

  5. Dharaiya N, Patriati A, Kuperkar K, Putra EGR, Bahadur P. Spectral and scattering microstructural investigation in cationic gemini surfactants(12-s-12) induced by p-tolulidine. Colloids Surf A. 2012;396(7):1–7.

    Article  CAS  Google Scholar 

  6. Zana R, Xia J. Gemini surfactants: synthesis, interfacial and solution-phase behavior, and applications. New York: Marcel Dekker; 2004.

    Google Scholar 

  7. Hujun X, Hui G, Peng K, Dandan C. Synthesis and properties of a novel liner alkylated diphenylmethane sulfonate Gemini surfactant. J Surfactants Deterg. 2013;16:57–61.

    Article  Google Scholar 

  8. Chen H, Zhu B. A new anionic oxalamide lauryl succinate sodium sulfonate gemini surfactant: microwave-assisted synthesis and surface activities. J Surfactants Deterg. 2014;17:937–42.

    Article  CAS  Google Scholar 

  9. Zhu YP, Masuyama A, Okahara M. Preparation and surface-active properties of amphipathic compounds with two sulfate groups and two lipophilic alkyl chains. J Am Oil Chem Soc. 1990;67:459–63.

    Article  CAS  Google Scholar 

  10. Yoshimura T, Esumi K. Synthesis and surface properties of anionic gemini surfactants with amide groups. J Colloid Interface Sci. 2004;276:231–8.

    Article  CAS  Google Scholar 

  11. Du X, Lu Y, Li L, Wang J, Yang Z. Synthesis and unusual properties of novel alkylbenzene sulfonate gemini surfactants. Colloids Surf A. 2007;290:132–7.

    Article  Google Scholar 

  12. Li X, Hu ZY, Zhao HL, Zhao SF, Cao DL. Synthesis and properties of novel alkyl sulfonate gemini surfactants. J. Surfactants Deterg. 2010;13:353–9. doi:10.1007/s11743-010-1188-5.

    Article  CAS  Google Scholar 

  13. Qiao W, Peng H, Zhu Y, Cai H. Synthesis and surface activity properties of symmetric double chains alkylbetaine surfactants derived from s-triazine. Colloids Surf A. 2012;405:45–50. doi:10.1016/j.colsurfa.2012.04.034.

    Article  CAS  Google Scholar 

  14. Xie KL, Sun Y, Hou AQ. Diffusion properties of reactive dyes into net modified cotton cellulose with triazine derivative. J Appl Polym Sci. 2007;103:2166–71. doi:10.1002/app.25097.

    Article  CAS  Google Scholar 

  15. Xue Z, Hu Z, Zhu H, Chen L. Synthesis and surface activity properties of cleavable s-triazine fatty sulfonate surfactants. China Surfactant Detergent Cosmet. 2008;3:151–5.

    Google Scholar 

  16. Petrova-Meladinova PM, Konstantinova TN. On the synthesis of some reactive triazine azo dyes containing tetramethylpiperidine fragment. Dyes Pigm. 2005;67:63–9.

    Article  Google Scholar 

  17. Konstantionova TN, Petrova P. On the synthesis of some bifunctional reactive triazine dyes. Dyes Pigm. 2002;52:115–20.

    Article  Google Scholar 

  18. Zana R, Lévy H, Danino D, Talmon Y, Kwetkat K. Mixed micellization of cetyltrimethyl ammonium bromide and an anionic dimeric (Gemini) surfactant in aqueous solution. Langmuir. 1997;13:402–8.

    Article  CAS  Google Scholar 

  19. Van Biesen G, Bottaro CS. Linear solvation energy relationships of anionic dimeric surfactants in micellar electrokinetic chromatography I. Effect of the length of a hydrophobic spacer. J Chromatogr A. 2007;1157:437–45.

    Article  Google Scholar 

  20. Van Biesen G, Bottaro CS. Liner solvation energy relationships of anionic dimeric surfactants in micellar electrokinetic chromatography II. Effect of the length of a hydrophilic spacer. J Chromatogr A. 2008;1180:171–8.

    Article  Google Scholar 

  21. Tai S, Gao Z, Liu X, Zhang Q. Synthesis and properties of novel alkyl sulfate Gemini surfactants. Eur J Lipid Sci Technol. 2012;114:1062–9.

    Article  CAS  Google Scholar 

  22. Wang Q, Zhang SX, Geng B, Zhang L, Zhao J, Shi J. Synthesis and surface activities of novel monofluoroalkyl phosphate surfactants. J Surfactants Deterg. 2012;15:83–8.

    Article  CAS  Google Scholar 

  23. Chen L, Hu Z, Zhu H, Xue Z. Synthesis of cleavable aryl sulfonate anionic surfactants and a study of their surface activity. J Surfactants Deterg. 2008;11(2):97–102.

    Article  CAS  Google Scholar 

  24. Yoshimura T, Sakato A, TsuchiyaK Ohkubo T, Sakai H, Abe M, Esumi K. Adsorption and aggregation properties of amino acid-based N-alkyl cysteine monomeric and N,N′-dialkyl cystine gemini surfactants. J Colloid Interface Sci. 2007;308(2):466–73.

    Article  CAS  Google Scholar 

  25. Chai M, Zheng Z, Bao L, Qiao W. CO2/N2 triggered switchable surfactants with imidazole group. J Surfactants Deterg. 2014;17(3):383–90.

    Article  CAS  Google Scholar 

  26. Huber K. Interactions in mixed interfaces of binary surfactant solutions. J Colloid Interface Sci. 1991;147(2):321–32.

    Article  CAS  Google Scholar 

  27. Chauhan V, Singh S, Bhadani A. Synthesis, characterization and surface properties of long chain β-hydroxy-γ-alkyloxy-N-methylimidazolium surfactants. Colloids Surf A. 2012;395(395):1–9.

    Article  CAS  Google Scholar 

  28. Li XW, Gao YA, Liu J, et al. Aggregation behavior of a chiral long-chain ionic liquid in aqueous solution. J Colloid Interface Sci. 2010;343(1):94–101.

    Article  CAS  Google Scholar 

  29. MiZhou M, Zhong X, Zhao J, Wang X. Synthesis and surface active properties of 1,1,1,1-tetra-(2-oxypropyl sulfonate-3-alkylether -propoxy) neopentanes. J Surfactants Deterg. 2013;16(3):285–90.

    Article  Google Scholar 

  30. Li P, Chen Q, Zhao J, Wang H, Li C, Hu Z, Cao D, et al. Synthesis and properties of X-type alkyl sulfonate gemini surfactants derived from cyanuric chloride. J Surfactants Deterg. 2011;15(4):449–56.

    Article  Google Scholar 

  31. Cui ZG. Fundamentals of surfactants, colloids, and interface chemistry. 1st ed. Beijing: Chemical Industry Press; 2013.

    Google Scholar 

  32. Rosen MJ. Surfactants and interfacial phenomena. 2nd ed. New York: Wiley; 1989.

    Google Scholar 

  33. Fu Z, Liu M, Xu J, Wang Q, Fan Z. Stabilization of water-in-octane nano-emulsion. Part I. Stabilized by mixed surfactant systems. Fuel. 2010;89(10):2838–43.

    Article  CAS  Google Scholar 

  34. Kang L, Xu B, Wang Y, Li Y, Shan X, An F, Liu J. Stability mechanism of W/O crude oil emulsion stabilized by polymer and surfactant. Colloids Surf A Physicochem Eng Asp. 2011;384(1–3):555–60.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ruixia Niu.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Niu, R., Wang, C., Sun, Z. et al. A Novel Alkyl Sulphobetaine Gemini Surfactant Based on S-triazine: Synthesis and Properties. J Surfact Deterg 20, 1255–1262 (2017). https://doi.org/10.1007/s11743-017-1996-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-017-1996-y

Keywords

Navigation