Colloid and Polymer Science

, Volume 291, Issue 4, pp 855–866 | Cite as

Synthesis and surface active properties of a gemini-type surfactant linked by a quaternary ammonium group

Original Contribution

Abstract

In this study, cationic surfactants having multi-hydroxyl groups were synthesized by the condensation reaction of octadec-9-enyl glycidyl ether and methyl amine followed by the quaternization with dimethyl sulfate. The structure of the product was elucidated by 1H-NMR and FT-IR. The minimum critical micelle concentration (CMC) and surface tension achieved using C18:1-BHDM surfactant were 1.24 × 10−4 mol/L and 43.36 mN/m, respectively. The interfacial tensions measured between 1 wt% surfactant solution and n-decane were found to be in the same order of magnitude as those exhibited between micellar solutions and nonpolar hydrocarbon oils. The contact angle measurement result suggests that C18:1-BADM is the best wetting agent among the surfactants tested during this study. It has been observed that the results for foam stability measurement are consistent with those of CMC and contact angle. That is, the percentage of foam volume decrease has been observed to increase with an increase in number of hydroxyl group.

Keywords

Cationic surfactant Hydroxyl group Critical micelle concentration (CMC) Surface tension Interfacial tension Contact angle 

Notes

Acknowledgments

This study was supported by a grant of the Korea Healthcare technology R&D Project, Ministry of Health and Welfare, Republic of Korea (grant no. A103017).

References

  1. 1.
    Han L, Ye Z, Chen H, Luo P (2009) The interfacial tension between cationic gemini surfactant solution and crude oil. J Surfactant Deterg 12(3):185–190CrossRefGoogle Scholar
  2. 2.
    Sharma KS, Patil SR, Rakshit AK, Glenn K, Doiron M, Palepu RM, Hassan PA (2004) Self-aggregation of a cationic-nonionic surfactant mixture in aqueous media: tensiometric, conductometric, density, light scattering, potentiometric, and fluorometric studies. J Phys Chem B 108(34):12804–12812CrossRefGoogle Scholar
  3. 3.
    Lu T, Li Z, Huang J, Fu H (2008) Aqueous surfactant two-phase systems in a mixture of cationic gemini and anionic surfactants. Langmuir 24(19):10723–10728CrossRefGoogle Scholar
  4. 4.
    Prez L, Pinazo A, Infante MR, Pons R (2007) Investigation of the micellization process of single and gemini surfactants from arginine by SAXS, NMR self-diffusion, and light scattering. J Phys Chem B 111(40):11379–11387CrossRefGoogle Scholar
  5. 5.
    Souguir Z, Roudesli S, About-Jaudet E, Picton L, Cerf DL (2010) Novel cationic and amphiphilic pullulan derivatives II: pH dependant physicochemical properties. Carbohydr Polym 80(1):123–129CrossRefGoogle Scholar
  6. 6.
    Rosen MJ (1988) Surfactants and interfacial phenomena. Wiley, New YorkGoogle Scholar
  7. 7.
    Das D, Roy S, Mitra RN, Dasgupta A, Das PK (2005) Head-group size or hydrophilicity of surfactants: the major regulator of lipase activity in cationic water-in-oil microemulsions. Chem Eur J 11(17):4881–4889CrossRefGoogle Scholar
  8. 8.
    Zana R (2002) Dimeric (gemini) surfactants: effect of the spacer group on the association behavior in aqueous solution. J Colloid Interface Sci 248(2):203–220CrossRefGoogle Scholar
  9. 9.
    Badawi AM, Mekawi MA, Mohamed AS, Mohamed MZ, Khowdairy MM (2007) Surface and biological activity of some novel cationic surfactants. J Surfactant Deterg 10(4):243–255CrossRefGoogle Scholar
  10. 10.
    Vinson PK, Bellare JR, Davis HT, MilleR WG, Scriven LE (1991) Direct imaging of surfactant micelles, vesicles, discs, and ripple phase structures by cryo-transmission electron microscopy. J Colloid Interface Sci 142(1):74–91CrossRefGoogle Scholar
  11. 11.
    Hirata H, Sato M, Sakaiguchi Y, Katsube Y (1988) Small angle X-ray scattering study of an extremely elongated micelle system of CTAB-p-toluidine solution. Colloid Polym Sci 266(9):862–864CrossRefGoogle Scholar
  12. 12.
    Jaeger DA, Li B, Clark T (1996) Cleavable double-chain surfactants with one cationic and one anionic head group that form vesicles. Langmuir 12(18):4314–4316CrossRefGoogle Scholar
  13. 13.
    Mohamed AS, Mohamed MZ (2010) Preparation of novel cationic surfactants from epichlorohydrin: their surface properties and biological activities. J Surfactant Deterg 13(2):159–163CrossRefGoogle Scholar
  14. 14.
    Shukla D, Tyagi VK (2006) Cationic gemini surfactants: a review. J Oleo Sci 55(8):381–390CrossRefGoogle Scholar
  15. 15.
    Parvinzadeh M, Memari N, Shaver M, Katozian B, Ahmadi S, Ziadi I (2010) Influence of ultrasonic waves on the processing of cotton with cationic softener. J Surfactant Deterg 13(2):135–141CrossRefGoogle Scholar
  16. 16.
    Jungermann E (1970) Cationic surfactants. Marcel Dekker, New YorkGoogle Scholar
  17. 17.
    Wang CY, Huang L (1987) pH-sensitive immunoliposomes mediate target-cell-specific delivery and controlled expression of a foreign gene in mouse. Proc Natl Acad Sci USA 84(15):7851–7855CrossRefGoogle Scholar
  18. 18.
    De la Maza A, Parra JL (1995) Solubilization of unilamellar liposomes caused by quaternary ammonium surfactants. J Control Release 37(1–2):33–42CrossRefGoogle Scholar
  19. 19.
    Bajpai D, Tyagi VK (2008) Microwave synthesis of cationic fatty imidazolines and their characterization. J Surfactant Deterg 11(1):79–87CrossRefGoogle Scholar
  20. 20.
    Cross J, Singer EJ (1994) Cationic surfactants. Marcel Dekker, New YorkGoogle Scholar
  21. 21.
    Giolando ST, Rapaport RA, Larson RJ, Federle TW, Stalmans M, Masscheleyn P (1995) Environmental fate and effects of DEEDMAC: a new rapidly biodegradable cationic surfactant for use in fabric softeners. Chemosphere 30(6):1067–1083CrossRefGoogle Scholar
  22. 22.
    Kirk O, Pedersen FD, Fuglsang CC (1998) Preparation and properties of a new type of carbohydrate-based cationic surfactant. J Surfactant Deterg 1(1):37–40CrossRefGoogle Scholar
  23. 23.
    Tatsumi T, Zhang W, Kida T, Nakatsuji Y, Ono D, Takeda T, IIkeda I (2000) Novel hydrolyzable and biodegradable cationic gemini surfactants: 1,3-bis[(acyloxyalkyl)-dimethylammonio]-2-hydroxypropane dichloride. J Surfactant Deterg 3(2):167–172CrossRefGoogle Scholar
  24. 24.
    Hellberg PE (2002) Ortho ester-based cleavable cationic surfactants. J Surfactant Deterg 5(3):217–227CrossRefGoogle Scholar
  25. 25.
    Miao Z, Yang J, Wang L, Liu Y, Zhang L, Li X, Peng L (2008) Synthesis of biodegradable lauric acid ester quaternary ammonium salt cationic surfactant and its utilization as calico softener. Mater Lett 62(19):3450–3452CrossRefGoogle Scholar
  26. 26.
    Kang EK, Lee BM, Hwang HA, Lim JC (2011) A novel cationic surfactant having two quaternary ammonium ions. J Ind Eng Chem 17(5–6):845–852Google Scholar
  27. 27.
    Lim JC, Kang EK, Lee BM (2012) Syntheses and surface active properties of cationic surfactants having multi ammonium and hydroxyl groups. J Ind Eng Chem. doi: 10.1016/j.jiec.2012.01.040
  28. 28.
    Lee BM, Kang HC, Park JM, Yoon J (2002) US Patent 6392064Google Scholar
  29. 29.
    Park JM, Kim HC, Lee BM, Kim DP (2003) Efficient synthetic method of diepoxide compound containing amino group in the connecting part. J Korean Ind Eng Chem 14(2):249–252Google Scholar
  30. 30.
    Lim JC, Han DS (2011) Synthesis of dialkylamidoamine oxide surfactant and characterization of its dual function of detergency and softness. Colloid Surf A 389(1–3):166–174CrossRefGoogle Scholar
  31. 31.
    Kielman HS, Van Steen PHF (1979) Surface active agents. Society Chemical Industry, LondonGoogle Scholar
  32. 32.
    Miller CA, Neogi P (1985) Interfacial phenomena: equilibrium and dynamic effects. Marcel Dekker, New YorkGoogle Scholar
  33. 33.
    Kim TS, Kida T, Nakatsuji Y, Hirao T, Ikeda I (1996) Surface-active properties of novel cationic surfactants with two alkyl chains and two ammonium groups. JAOCS 73(7):907–911CrossRefGoogle Scholar
  34. 34.
    Chung DW, Lim JC (2009) Study on the effect of structure of polydimethylsiloxane grafted with polyethyleneoxide on surface activities. Colloids Surf A 336(1–3):35–40CrossRefGoogle Scholar
  35. 35.
    Mori F, Lim JC, Miller CA (1990) Equilibrium and dynamic behavior of a system containing a mixture of anionic and nonionic surfactants. Progr Colloid Polym Sci 82:114–121CrossRefGoogle Scholar
  36. 36.
    Mori F, Lim JC, Raney OG, Elsik CM, Miller CA (1989) Phase behavior, dynamic contacting and detergency in systems containing triolein and nonionic surfactants. Colloid Surf 40:323–345CrossRefGoogle Scholar
  37. 37.
    Miller CA (2008) Antifoaming in aqueous foams. Curr Opin Colloid Interface Sci 13(3):177–182CrossRefGoogle Scholar
  38. 38.
    Zhang H, Miller CA, Garrett PR, Raney KH (2005) Lauryl alcohol and amine oxide as foam stabilizers in the presence of hardness and oily soil. J Surfactant Deterg 8(1):99–107CrossRefGoogle Scholar
  39. 39.
    Kim JS, Lim JC (2009) Effect of pH on physical properties of triethanolamine-ester quaternary ammonium salt cationic surfactant system. J Korean Ind Eng Chem 20(5):479–485Google Scholar

Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  1. 1.Department of Chemical and Biochemical EngineeringDongguk University-SeoulSeoulSouth Korea
  2. 2.Environment and Resources Research Center, Green Chemistry DivisionKorea Research Institute of Chemical TechnologyDaeJeonSouth Korea
  3. 3.Center for Chemical AnalysisKorea Research Institute of Chemical TechnologyDaeJeonSouth Korea
  4. 4.Department of Green Chemistry and Environmental BiotechnologyUniversity of Science and TechnologyDaeJeonSouth Korea

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