Colloid and Polymer Science

, 289:1579 | Cite as

Synthesis and properties of new polymeric surfactant with quaternary ammonium salt

  • Lei Zhang
  • Xin Lv
  • Yuejun Zhu
  • Jian Zhang
  • Hong Wang
  • Yebang Tan
Original Contribution

Abstract

The polymeric surfactant with quaternary ammonium salt (PQ) was synthesized by cationic ring-open polymerization using boron trifluoride diethyletherate as cationic catalyst. The chemical structure and aggregation behavior of PQ were studied by 1H NMR, surface tension, static light scattering, dynamic laser light scattering, electrical conductivity, and fluorescence measurement. The results show the surface tension (γcmc) and critical micelle concentration (cmc) of PQ decrease with increasing of sodium chloride concentration. The cmc and γcmc values of PQ measured by electrical conductivity and fluorescence measurements mainly identify with that obtained by surface tension measurements. The thermodynamic parameters (\( \Delta G_m^0 \),\( \Delta H_m^0 \),\( \Delta S_m^0 \)) from electrical conductivity indicated that the micellization of PQ was mainly the process of entropy-driven. In addition, the results from the viscosity stability between hydrolyzed polyacrylamide (HPAM) and PQ showed that the viscosities of mixed system for HPAM and PQ are higher than the viscosity of HPAM.

Keywords

Polymeric surfactant Quaternary ammonium salt Water-soluble polymer aggregation behavior Viscosity stabilizer 

Notes

Acknowledgments

The authors gratefully acknowledge the financial support from Major Research of the Ministry of Science and Technology, China (grant no. 2008zx05024-02-007) and the Scientific Research Project of Shandong Province (grant no. 2008GG2TC01011-12).

References

  1. 1.
    Para G, Hamerska-Dudra A, Wilk KA, Warszynski P (2010) Surface activity of cationic surfactants, influence of molecular structure. Colloids Surface Physicochem Eng Aspect 365(1–3):215–221CrossRefGoogle Scholar
  2. 2.
    Lukác M, Pisárcik M, Lacko I, Devínsky F (2010) Surface-active properties of nitrogen heterocyclic and dialkylamino derivates of hexadecylphosphocholine and cetyltrimethylammonium bromide. J Colloid Interface Sci 347(2):233–240CrossRefGoogle Scholar
  3. 3.
    Ao MQ, Xu GY, Pang JY, Zhao TT (2009) Comparison of aggregation behaviors between ionic liquid-type imidazolium gemini surfactant C-12-4-C(12)im Br-2 and its monomer C(12)mim Br on silicon wafer. Langmuir 25(17):9721–9727CrossRefGoogle Scholar
  4. 4.
    Para G, Jarek E, Warszynski P (2006) The Hofmeister series effect in adsorption of cationic surfactants–theoretical description and experimental results. Adv Colloid Interface Sci 122(1–3):39–55CrossRefGoogle Scholar
  5. 5.
    Rosen MJ (2004) Characteristic features of surfactants. Surfactants and interfacial phenomena. John Wiley & Sons, pp 20–40Google Scholar
  6. 6.
    Yoshimura T, Yoshida H, Ohno A, Esumi K (2003) Physicochemical properties of quaternary ammonium bromide-type trimeric surfactants. J Colloid Interface Sci 267(1):167–172CrossRefGoogle Scholar
  7. 7.
    Bell PC, Bergsma M, Dolbnya IP, Bras W, Stuart MCA, Rowan AE, Feiters MC, Engberts JBFN (2003) Transfection mediated by gemini surfactants: engineered escape from the endosomal compartment. J Am Chem Soc 125(6):1551–1558CrossRefGoogle Scholar
  8. 8.
    Babadagli T (2003) Selection of proper enhanced oil recovery fluid for efficient matrix recovery in fractured oil reservoirs. Colloids Surface Physicochem Eng Aspect 223(1–3):157–175CrossRefGoogle Scholar
  9. 9.
    Zana R (2002) Dimeric and oligomeric surfactants. Behavior at interfaces and in aqueous solution: a review. Adv Colloid Interface Sci 97(1–3):205–253CrossRefGoogle Scholar
  10. 10.
    Kim SS, Zhang W, Pinnavaia TJ (1998) Ultrastable mesostructured silica vesicles. Science 282(5392):1302CrossRefGoogle Scholar
  11. 11.
    Deen GR, Gan LH (2009) New piperazine-based polymerizable monoquaternary cationic surfactants: synthesis, polymerization, and swelling characteristics of gels. J Polymer Sci Polymer Chem 47(8):2059–2072Google Scholar
  12. 12.
    Hayamizu K, Tsuzuki S, Seki S, Ohno Y, Miyashiro H, Kobayashi Y (2008) Quaternary ammonium room-temperature ionic liquid including an oxygen atom in side chain/lithium salt binary electrolytes: ionic conductivity and 1H, 7Li, and 19 F NMR studies on diffusion coefficients and local motions. J Phys Chem B 112(4):1189–1197CrossRefGoogle Scholar
  13. 13.
    Dopierala K, Prochaska K (2008) The effect of molecular structure on the surface properties of selected quaternary ammonium salts. J Colloid Interface Sci 321(1):220–226CrossRefGoogle Scholar
  14. 14.
    Chlebicki J, Wegrzynska J, Wilk KA (2008) Surface-active, micellar, and antielectrostatic properties of bis-ammonium salts. J Colloid Interface Sci 323(2):372–378CrossRefGoogle Scholar
  15. 15.
    Ao MQ, Xu GY, Zhu YY, Bai Y (2008) Synthesis and properties of ionic liquid-type Gemini imidazolium surfactants. J Colloid Interface Sci 326(2):490–495CrossRefGoogle Scholar
  16. 16.
    Muzzalupo R, Infante MR, Perez L, Pinazo A, Marques EF, Antonelli ML, Strinati C, La Mesa C (2007) Interactions between gemini surfactants and polymers: thermodynamic studies. Langmuir 23(11):5963–5970CrossRefGoogle Scholar
  17. 17.
    Jendric M, Filipovic-Vincekovic N, Vincekovic M, Bujan M, Primozik I (2005) Phase behavior of bis(quaternary ammonium bromide)/sodium cholate/H2O system. Journal of Dispersion Science and Technology 26(1):39–51CrossRefGoogle Scholar
  18. 18.
    Yoshimura T, Nagata Y, Esumi K (2004) Interactions of quaternary ammonium salt-type gemini surfactants with sodium poly(styrene sulfonate). J Colloid Interface Sci 275(2):618–622CrossRefGoogle Scholar
  19. 19.
    Kumar A, Alami E, Holmberg K, Seredyuk V, Menger FM (2003) Branched zwitterionic gernini surfactants micellization and interaction with ionic surfactants. Colloids Surface Physicochem Eng Aspect 228(1–3):197–207CrossRefGoogle Scholar
  20. 20.
    Sikiric M, Primozic I, Filipovic-Vincekovic N (2002) Adsorption and association in aqueous solutions of dissymmetric Gemini surfactant. J Colloid Interface Sci 250(1):221–229CrossRefGoogle Scholar
  21. 21.
    Li ZY, Chau Y (2009) Synthesis of linear polyether polyol derivatives as new materials for bioconjugation. Bioconjug Chem 20(4):780–789CrossRefGoogle Scholar
  22. 22.
    Mortensen K (2001) PEO-related block copolymer surfactants. Colloids Surface Physicochem Eng Aspect 183:277–292CrossRefGoogle Scholar
  23. 23.
    Mochizuki A, Senshu K, Seita Y, Fukuoka T, Yamashita S, Koshizaki N (1998) Polyether-segmented nylon hemodialysis membrane. VI. Effect of polyether segment on morphology and surface structure of membrane. J Appl Polymer Sci 69(8):1645–1659CrossRefGoogle Scholar
  24. 24.
    Hirasaki GJ, Miller CA, Raney OG, Poindexter MK, Nguyen DT, Hera J (2011) Separation of produced emulsions from surfactant enhanced oil recovery processes. Energ Fuel 25:555–561CrossRefGoogle Scholar
  25. 25.
    Deng ML, Cao MW, Wang YL (2009) Coacervation of cationic gemini surfactant with weakly charged anionic polyacrylamide. J Phys Chem B 113(28):9436–9440CrossRefGoogle Scholar
  26. 26.
    Zhang HX, Xu GY, Wu D, Wang SW (2008) Aggregation of cetyltrimethylammonium bromide with hydrolyzed polyacrylamide at the paraffin oil/water interface: interfacial rheological behavior study. Colloids Surface Physicochem Eng Aspect 317(1–3):289–296CrossRefGoogle Scholar
  27. 27.
    Khan MY, Samanta A, Ojha K, Mandal A (2008) Interaction between aqueous solutions of polymer and surfactant and its effect on physicochemical properties. Asia Pac J Chem Eng 3(5):579–585CrossRefGoogle Scholar
  28. 28.
    Luo L, Wang DX, Zhang L, Zhao S, Yu JY (2007) Interactions between hydrophobically modified associating polyacrylamide and cationic surfactant at the water-octane interface: interfacial dilational viscoelasticity. Journal of Dispersion Science and Technology 28(2):263–269CrossRefGoogle Scholar
  29. 29.
    Yuan SL, Cai ZT, Xu GY, Jiang YS (2003) Mesoscopic simulation study on the interaction between polymer and C12NBr or C(9)phNBr in aqueous solution. Colloid and Polymer Science 281(11):1069–1075CrossRefGoogle Scholar
  30. 30.
    Huang JB, Zhu Y, Zhu BY, Li RK, Fu HI (2001) Spontaneous vesicle formation in aqueous mixtures of cationic surfactants and partially hydrolyzed polyacrylamide. J Colloid Interface Sci 236(2):201–207CrossRefGoogle Scholar
  31. 31.
    Brackman JC, Engberts JBFN (1991) Influence of polymers on the micellization of cetyltrimethylammonium salts. Langmuir 7(10):2097–2102CrossRefGoogle Scholar
  32. 32.
    Turro NJ, Baretz BH, Kuo PL (1984) Photoluminescence probes for the investigation of interactions between sodium dodecylsulfate and water-soluble polymers. Macromolecules 17(7):1321–1324CrossRefGoogle Scholar
  33. 33.
    Shirahama K, Tsujii K, Takagi T (1974) Free-boundary electrophoresis of sodium dodecyl sulfate-protein polypeptide complexes with special reference to SDS-polyacrylamide gel electrophoresis. J Biochem 75(2):309–319Google Scholar
  34. 34.
    Muller G, Fenyo JC, Selegny E (1980) High molecular weight hydrolyzed polyacrylamides. III. Effect of temperature on chemical stability. J Appl Polymer Sci 25(4):627–633CrossRefGoogle Scholar
  35. 35.
    Del Rio E, Galià M, Cádiz V, Lligadas G, Ronda JC (2010) Polymerization of epoxidized vegetable oil derivatives: ionic-coordinative polymerization of methylepoxyoleate. J Polymer Sci Polymer Chem 48(22):4995–5008Google Scholar
  36. 36.
    Rahm M, Westlund R, Eldsäter C, Malmström E (2009) Tri-block copolymers of polyethylene glycol and hyperbranched poly-3-ethyl-3-(hydroxymethyl)oxetane through cationic ring opening polymerization. J Polymer Sci Polymer Chem 47(22):6191–6200Google Scholar
  37. 37.
    Endo T (2009) Handbook of ring-opening polymerization. Wiley-VCH Verlag GmbH & Co., pp 56,141–142Google Scholar
  38. 38.
    Magnusson H, Malmstrom E, Hult A (1999) Synthesis of hyperbranched aliphatic polyethers via cationic ring-opening polymerization of 3-ethyl-3-(hydroxymethyl)oxetane. Macromol Rapid Comm 20(8):453–457CrossRefGoogle Scholar
  39. 39.
    Wang T-T, Iou Q-L (2002) The solvent effect and the structural effect of halides on the quaternization Et3N + RX– > Et3RNX. Chem Eng J 87(2):197–206CrossRefGoogle Scholar
  40. 40.
    Li X, Mya KY, Ni XP, He CB, Leong KW, Li J (2006) Dynamic and static light scattering studies on self-aggregation behavior of biodegradable amphiphilic poly(ethylene oxide)-poly (R)-3-hydroxybutyrate -poly(ethylene oxide) triblock copolymers in aqueous solution. J Phys Chem B 110(12):5920–5926CrossRefGoogle Scholar
  41. 41.
    Gracia CA, Gómez-Barreiro S, González-Pérez A, Nimo J, RodrIguez JR (2004) Static and dynamic light-scattering studies on micellar solutions of alkyldimethylbenzylammonium chlorides. J Colloid Interface Sci 276(2):408–413CrossRefGoogle Scholar
  42. 42.
    Zimm BH (1948) The scattering of light and the radial distribution function of high polymer solutions. J Chem Phys 16(12):1093–1099CrossRefGoogle Scholar
  43. 43.
    Zana R, In M, Lévy H, Duportail G (1997) Alkanediyl-α,ω-bis(dimethylalkylammonium bromide) 7. fluorescence probing studies of micelle micropolarity and microviscosity. Langmuir 13(21):5552–5557CrossRefGoogle Scholar
  44. 44.
    Weissenborn PK, Pugh RJ (1996) Surface tension of aqueous solutions of electrolytes: relationship with ion hydration, oxygen solubility, and bubble coalescence. J Colloid Interface Sci 184(2):550–563CrossRefGoogle Scholar
  45. 45.
    Turro NJ, Yekta A (1978) Luminescent probes for detergent solutions. A simple procedure for determination of the mean aggregation number of micelles. J Am Chem Soc 100(18):5951–5952CrossRefGoogle Scholar
  46. 46.
    Koyanagi M (1968) Effect of dispersion forces of solventsII. On the O–O band of the near ultraviolet absorption spectrum of benzene in fluid solutions. J Mol Spectrosc 25(3):273–290CrossRefGoogle Scholar
  47. 47.
    Ao MQ, Huang PP, Xu GY, Yang XD, Wang YJ (2009) Aggregation and thermodynamic properties of ionic liquid-type gemini imidazolium surfactants with different spacer length. Colloid and Polymer Science 287(4):395–402CrossRefGoogle Scholar
  48. 48.
    Zana R (1996) Critical micellization concentration of surfactants in aqueous solution and free energy of micellization. Langmuir 12(5):1208–1211CrossRefGoogle Scholar
  49. 49.
    Nusselder JJH, Engberts JBFN (1992) Toward a better understanding of the driving force for micelle formation and micellar growth. J Colloid Interface Sci 148(2):353–361CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Lei Zhang
    • 1
    • 2
  • Xin Lv
    • 3
  • Yuejun Zhu
    • 3
  • Jian Zhang
    • 3
  • Hong Wang
    • 1
    • 2
  • Yebang Tan
    • 1
    • 2
  1. 1.School of Chemistry and Chemical EngineeringShandong UniversityJinanPeople’s Republic of China
  2. 2.Key laboratory of Special Functional Aggregated MaterialsShandong University, Ministry of EducationJinanPeople’s Republic of China
  3. 3.Technology Research Department CNOOC Research CenterState Key Laboratory of Offshore Oil ExploitationBeijingPeople’s Republic of China

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