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Synthesis and Surface Active Properties of tri[(N-alkyl-N-ethyl-N-Sodium carboxymethyl)-2-Ammonium bromide ethylene] Amines

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Journal of Surfactants and Detergents

Abstract

Trimeric betaine surfactants tri[(N-alkyl-N-ethyl-N-sodium carboxymethyl)-2-ammonium bromide ethylene] amines were prepared with raw materials containing tris(2-aminoethyl) amine, alkyloyl chloride, lithium aluminium hydride, sodium chloroacetate, and bromoethane by alkylation, Hoffman degradation reaction, carboxymethylation and quaternary amination reaction. The chemical structures of the prepared compounds were confirmed by FTIR, 1H NMR, MS and elemental analysis. With the increasing length of the carbon chain, the values of their critical micelle concentration initially decreased. Surface active properties of these compounds were superior to general carboxylate surfactants C10H21CHN+(CH3)2COONa. The minimum cross-sectional area per surfactant molecule (A min), standard Gibbs free energy adsorption (ΔG ads) and standard Gibbs free energy micellization (ΔG mic) are notably influenced by the chain length n, and the trimeric betaine surfactants have greater ability to adsorb at the air/water interface than form micelles in solution. The efficiency of adsorption at the water/air interface (pC20) of these surfactants increased with the increasing length of the alkyl chain. Their foaming properties, wetting ability of a felt chip, and lime-soap dispersing ability were also investigated.

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References

  1. Zana R (2002) Dimeric (gemini) surfactants: effect of spacer group on the association behavior in aqueous solution. J Colloid Interface Sci 248:203–220

    Article  CAS  Google Scholar 

  2. Li X, Hu ZY, Zhu HL, Zhao SF, Cao DL (2010) Synthesis and properties of novel alkyl sulfonate gemini surfactants. J Surf Deterg 13:353–359

    Article  CAS  Google Scholar 

  3. Marcelo C, Murguía, Mariano Cristaldi D, Ayele´n Porto, José Di Conza, Ricardo Grau J (2008) Synthesis, surface-active properties, and antimicrobial activities of new neutral and cationic tetrameric surfactants. J Surf Deterg 1(11):41–48

    Google Scholar 

  4. Magdassi S, Ben Moshe M, Talmon Y, Danino D (2003) Microemulsions based on anionic gemini surfactant. Colloids Surf A 212:1–7

    Article  CAS  Google Scholar 

  5. Du X, Lu Y, Li L, Wang J, Yang Z (2007) Synthesis and unusual properties of novel alkylbenzene sulfonate gemini surfactants. Colloids Surf A 290:132–137

    Article  Google Scholar 

  6. Yaseen M, Lu JR, Webster JRP, Penfold J (2006) The structure of zwitterionic phosphocholine surfactant monolayers. Langmuir 22:5825–5832

    Article  CAS  Google Scholar 

  7. El-Aila HJY (2005) Effect of urea and salt on micelle formation of zwitterionic surfactants. J Surf Deterg 8:165–168

    Article  CAS  Google Scholar 

  8. Yoshimura T, Nyuta K, Esumi K (2005) Zwitterionic heterogemini surfactants containing ammonium and carboxylate headgroups. 1. adsorption micellization. Langmuir 21:2682–2688

    Article  CAS  Google Scholar 

  9. Yaseen A, Wang Y, Su TJ, Lu JR (2005) Surface adsorption of zwitterionic surfactants: n-alkyl phosphocholines characterized by surface tensiometry and neutron reflection. J Colloid Interf Sci 288:361–370

    Article  CAS  Google Scholar 

  10. Zhou M, Zhao JZ, Hu XQ (2012) Synthesis of bis[N, N-(alkylamideethyl) ethyl] triethylenediamine bromide surfactants and their oilfield application investigation. J Surf Deterg 15:309–315

    Article  CAS  Google Scholar 

  11. Geng XF, Hu XQ, Jia XC, Luo LJ (2014) Effects of sodium salicylate on the microstructure of a novel zwitterionic gemini surfactant and its rheological responses. Colloid Polym Sci 292:915–921

    Article  CAS  Google Scholar 

  12. Quan HP, Zhang X, Lu HS, Huang ZY (2012) Synthesis and acid solution properties of a novel betaine zwitterionic surfactant. Cent Eur J Chem 10:1624–1632

    Article  CAS  Google Scholar 

  13. Cui ZG, Du XR, Pei XM, Jiang JZ, Wang F (2012) Synthesis of didodecylmethylcarboxyl betaine and its application in surfactant–polymer flooding. J Surf Deterg 15:685–694

    CAS  Google Scholar 

  14. Tomokazu Yoshimura, Nobuhiro Kimura, Emika Onitsuka, Hideto Shosenji, Kunio Esumi (2004) Synthesis and surface-active properties of trimeric-type anionic Surfactants derived from tris(2-aminoethyl)amine. J Surf Deterg 1(7):67–74

    Article  Google Scholar 

  15. Qi LY, Fang Y, Wang ZY, Ma N, Jiang LY, Wang YY (2008) Synthesis and physicochemical investigation of long alkylchain betaine zwitterionic surfactant. J Surf Deterg 11:55–59

    Article  CAS  Google Scholar 

  16. Zana R (1996) Critical micellization concentration of surfactants in aqueous solution and free energy of micellization. Langmuir 12:1208–1211

    Article  CAS  Google Scholar 

  17. Yoshimura T, Sakato A, Tsuchiya K, Ohkubo T, Sakai H, Abe M, Esumi K (2007) Adsorption and aggregation properties of amino acid-based N-alkyl cysteine monomeric and N, N’-dialkyl cysteine gemini surfactants. J Colloid Interface Sci 308:466–473

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by Project of State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation (Projects No. PLN1419) and Project of Sichuan Province College Key Laboratory of Oil and Gas Field Materials (No. x151514kcl16).

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Authors and Affiliations

  1. State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation, School of Material Science and Engineering, Southwest Petroleum University, Chengdu, Sichuan, 610500, China

    Ming Zhou

  2. School of Material Science and Engineering, Southwest Petroleum University, Chengdu, Sichuan, 610500, China

    Gang Luo, Xingwen Wang, Ze Zhang & Gang Wang

Authors
  1. Ming Zhou
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  2. Gang Luo
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  3. Xingwen Wang
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  4. Ze Zhang
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  5. Gang Wang
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Correspondence to Ming Zhou.

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Zhou, M., Luo, G., Wang, X. et al. Synthesis and Surface Active Properties of tri[(N-alkyl-N-ethyl-N-Sodium carboxymethyl)-2-Ammonium bromide ethylene] Amines. J Surfact Deterg 18, 837–844 (2015). https://doi.org/10.1007/s11743-015-1716-4

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  • DOI: https://doi.org/10.1007/s11743-015-1716-4

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