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Synthesis and Characterization of Photosensitive Ionic Liquid Surfactant 4-Butylazobenzene-4′-(Oxyethyl)Methylimidazolium with Br− and BF4− Counterions

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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 55 Issue 3

Abstract

The photo-responsive ionic liquid surfactants 4-Butylazobenzene-4′-(oxyethyl)methylimidazolium with Br− (AZMIMBr) and BF4− (AZMIMBF4) counterions were synthesized, and their structures were characterized by means of 1H NMR. Their properties for pre- or post-UV irradiation were investigated by employing tensiometry, electrical conductance, thermal gravimetry-differential scanning calorimetry (TG-DSC) and small-angle X-ray scattering (SAXS). The effect of UV irradiation time on photoisomerization of two surfactants solutions was evaluated, which showed the photoisomerization efficiency decreases with an increase of their concentrations. After UV irradiation, the CMC value of the two surfactants increased, whereas, the surface tensions at CMC (γCMC) and the fraction of counterion binding (β) were approximately the same. SAXS coupled with polarized optical microscopic studies (POM studies) confirmed that the liquid crystal textures of AZMIMBr could be affected by UV-irradiation. The detailed analysis of thermodynamic parameters revealed that the micellizaton of AZMIMBr was entropy-driven, and the micellization of AZMIMBF4 was enthalpy-driven.

Kurzfassung

Die photoempfindlichen, tensidischen Ionischen Flüssigkeiten 4-Butylazobenzen-4′-(oxyethyl)methylimidazolium mit den Gegenionen Br− (AZMIMBr) und BF4− (AZMIMBF4) wurden synthetisiert. Ihre Strukturen wurden mittels 1H NMR charakterisiert. Ihre Eigenschaften wurden vor- oder nach UV-Bestrahlung mit der Tensiometrie, mit Messungen der elektrischen Leitfähigkeit, der Thermogravimetrie in Kombination mit der dynamischen Differenzkalorimetrie (TG-DSC) und der Kleinwinkelröntgenstreuung (SAXS) untersucht. Der Einfluss der UV-Bestrahlungsdauer auf die Photoisomerisierung von zwei unterschiedlich konzentrierten Tensidlösungen wurde untersucht, wobei gezeigt wurde, dass die Effizienz der Photoisomerisierung mit steigender Tensidkonzentration abnimmt. Nach der UV-Bestrahlung stiegen die CMC-Werte der beiden Tenside an, während die Oberflächenspannungen bei CMC (γCMC) und der Anteil der Gegenionenbindung (β) ungefähr gleich blieben. SAXS-Messungen in Verbindung mit polarisationsmikroskopischen Untersuchungen (POM) bestätigten, dass die Flüssigkristalltexturen von AZMIMBr durch UV-Bestrahlung beeinflusst werden konnten. Die detaillierte Analyse der thermodynamischen Parameter ergab, dass die Mizellenbildung von AZMIMBr entropiegetrieben und die Mizellenbildung von AZMIMBF4 enthalpiegetrieben ist.

Key words: Photosensitivity; ionic liquid surfactant; liquid crystal; surface tension
Stichwörter: Lichtempfindlichkeit; Ionische Flüssigkeit-Tensid; Flüssigkristall; Oberflächenspannung
*Correspondence address, Prof. Dr. Shili Song, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, P.R. China, E-Mail:

Prof. Dr. Shili Song, the Head of Applied Chemistry at Henan Normal University, is being engaged in teaching and scientific research work. His research interest encompasses both surface chemistry and biocatalysis, especially focused on novel surfactants synthesis and characterization.

WenliHao is a master's candidate of Applied Chemistry at Henan Normal University.

Dongxiao Yang, associate Head of Applied Chemistry at Henan Normal University, is being engaged in teaching and scientific research work. His research interest encompasses novel surfactants synthesis and characterization.

Qingqing Tian is a master's candidate of Applied Chemistry at Henan Normal University.

Jingwen Lu is a master's candidate of Applied Chemistry at Henan Normal University.

References

1. Bowers, J., Butts, P., Martin, J., Vergara-Gutierrez, C. and Heenan, K.: Aggregation behavior of aqueous solutions of ionic liquids. Langmuir20 (2004) 2191–2198. 15835670 10.1021/la035940mSearch in Google Scholar PubMed

2. Miskolczy, Z., Sebõk-Nagy, K., Biczók, L. and Gökturk, S.: Aggregation and micelle formation of ionic liquids in aqueous solution. Chem. Phys. Lett.400 (2004) 296–300. 10.1016/j.cplett.2004.10.127Search in Google Scholar

3. Srinivasa Rao, K., Trivedi, Tushar J. and Kumar, A.: Aqueous-biamphiphilic ionic liquid systems: self-assembly and synthesis of gold nanocrystals/microplates. J. Phys. Chem. B116 (2012) 14363–14374. 23171376 10.1021/jp309717nSearch in Google Scholar PubMed

4. Baltazar, Q. Q., Chandawalla, J., Sawyer, K. and Anderson, J. L.: Interfacial and micellar properties of imidazolium-based monocationic and dicationic ionic liquids. Colloids Surf. A302 (2007) 150–156. 10.1016/j.colsurfa.2007.02.012Search in Google Scholar

5. Dong, B., Li, N., Zheng, L., Yu, L. and Inoue, T.: Surface adsorption and micelle formation of surface active ionic liquids in aqueous solution. Langmuir23 (2007) 4178–4182. 17346069 10.1016/j.colsurfa.2013.03.023Search in Google Scholar

6. Shi, L., Li, N., Yan, H., Gao, Y. and Zheng, L.: Aggregation behavior of long-chain N-aryl imidazolium bromide in aqueous solution. Langmuir27 (2011) 1618–1625. 21247213 10.1021/la104719vSearch in Google Scholar PubMed

7. Dong, B., Gao, Y., Su, Y., Zheng, L., Xu, J. and Inoue, T.: Self-aggregation behavior of fluorescent carbazole-tailed imidazolium ionic liquids in aqueous solutions. J. Phys. Chem. B114 (2010) 340–348. 19845319 10.1021/jp908136fSearch in Google Scholar PubMed

8. Liu, X., Dong, L. and Fang, Y.: Synthesis and self-aggregation of a hydroxyl-functionalized imidazolium-based ionic liquid surfactant in aqueous solution. J. Surfact Deterg.14 (2011) 203–210. 10.1007/s11743-010-1234-3Search in Google Scholar

9. Huang, R. T. W., Peng, K. C., Shih, H. N., Lin, G. H., Chang, T. F., Hsu, S. J., Hsu, T. S. T. and Lin, I. J. B.: Antimicrobial properties of ethoxyether-functionalized imidazolium salts. Soft Matter7 (2011) 8392–8400. 10.1039/c1sm05759fSearch in Google Scholar

10. Freire, M. G., Neves, C. M. S. S., Canongia Lopes, J. N., Marrucho, I. M., Coutinho, J. A. P. and Rebelo, L. P. N.: Impact of selfaggregation on the formation of ionic-liquid-based aqueous biphasic systems. J. Phys. Chem. B116 (2012) 7660–7668. 22681668 10.1021/jp211132zSearch in Google Scholar PubMed

11. Pino, V., German-Hernandez, M., Martin-Perez, A. and Anderson, J. L.: Ionic liquid-based surfactants in separation science. Sep. Sci. Technol.47 (2012) 264–276. 10.1080/01496395.2011.620589Search in Google Scholar

12. Galan, M. C., Tran, A. T., Boisson, J., Benito, D., Butts, C., Eastoe, J. and Brown, P.: [R4N][AOT]: A surfactant ionic liquid as a mild glycosylation promoter. J. Carbohydr. Chem.30 (2011) 486–497. 10.1080/07328303.2011.609626Search in Google Scholar

13. Trivedi, T. J., Rao, K. S., Singh, T., Mandal, S. K., Sutradhar, N., Panda, A. B. and Kumar, A.: Task-Specific, Biodegradable amino Acid ionic liquid surfactants. ChemSusChem4 (2011) 604–608. 21506287 10.1002/cssc.201100065Search in Google Scholar PubMed

14. Kim, K., Choi, S., Cha, J., Yeon, S. and Lee, H.: Facile one-pot synthesis of gold nano particles using alcohol ionic liquids. J. Mater. Chem.16 (2006) 1315–1317. 10.1039/B601478JSearch in Google Scholar

15. Bai, X., Gao, Y., Liu, H. and Zheng, L.: Synthesis of amphiphilic ionic liquids terminated gold nanorods and their superior catalytic activity for the reduction of nitro compounds. J. Phys. Chem. C113 (2009) 17730–17736. 10.1021/jp906378dSearch in Google Scholar

16. Souza, B. S., Leopoldino, E. C., Tondo, D. W., Dupont, J. and Nome, F.: Imidazolium-based zwitterionic surfactant: A new amphiphilic Pd nanoparticle Stabilizing agent. Langmuir28 (2012) 833–840. 22126124 10.1021/la203501fSearch in Google Scholar PubMed

17. Shili, S., Yabing, H., Wenli, H., Jingwen, L. and Yuhua, Q.: Properties of choline-derived cationic surfactant with photolabile cinnamate counterion. Tenside Surf. Det.54 (2017) 1–9. 10.3139/113.110479Search in Google Scholar

18. Aydogan, N. and Aldis, N.: Tuning surface tension and aggregate shape via a novel redox active fluorocarbon-hydrocarbon hybrid surfactant. Langmuir, 22(5) (2006) 2028–2033. 16489784 10.1021/la052786qSearch in Google Scholar PubMed

19. Eastoe, J., Dominguez, M. S. and Wyatt, P.: Properties of a stilbenecontaining gemini photosurfactant: light-triggered changes in Surface Tension and Aggregation. Langmuir, 18 (2002) 7837–7844. 10.1021/la0257384Search in Google Scholar

20. Sakai, H., Ebana, H. and Sakai, K.: Photo-isomerization of spiropyran- modified cationic surfactants. J Colloid Interface Sci.316(2) (2007) 1027–1030. 17884070 10.1016/j.jcis.2007.08.042Search in Google Scholar PubMed

21. Ikeda, T. and Tsutsumi, O.: Optical switching and image storage by means of azobenzene liquid-crystal films. Science268 (1995) 1873–1875. 17797528 10.1126/science.268.5219.1873Search in Google Scholar

22. Natansohn, A. and Rochon, P.: Photoinduced motions in azo-containing polymers. Chem Rev102(11) (2002) 4139–4176. 12428986 10.1021/cr970155ySearch in Google Scholar

23. Xie, H. Q., Liu, Z. H. and Huang, X. D.: Synthesis and non-linear optical properties of four polyurethanes containing different chromophore groups. Eur Polym J37 (2001) 497–505. (00)00146–4. 10.1016/S0014-3057Search in Google Scholar

24. Vanden mooter, G., Maris, B., Samyn, C., Augustijns, P. and Kinget, R.: Use of Azo polymers for colon-specific drug delivery. J Pharm Sci6(1) (1997) 1321–1427. 10.1021/js9702630Search in Google Scholar

25. Vollmer, M. S., Clark, T. D. and Steinem, C. M.: Photoswitchable Hydrogen-Bonding in Self-organized cylindrical peptide systems. Angew. Chem., Int. Ed.38(11) (1999) 1598–1601. 10.1002/(SICI)1521-3773(19990601)38:11<1598::AID-ANIE159Search in Google Scholar

26. Cabrera, I., Krongauz, V. and Ringsdorf, H.: Photo- and thermo-chromic liquid crystal polymers with spiropyran groups. Mol Crystal Liq Cryst155(1) (1988) 221–230. 10.1080/00268948808070366Search in Google Scholar

27. Kaempf, G.: Special polymers for data memories. Polym J19(2) (1987) 257–268. 10.1295/polymj.19.257Search in Google Scholar

28. Wang, G., Tong, X. and Zhao, Y.: Preparation of azobenzene-containing amphiphilic diblock copolymers for light-responsive micellar aggregates. Macromolecules37 (2004) 8911–8917. 10.1021/ma048416aSearch in Google Scholar

29. Wang, Y. Y., Lin, S. L., Zang, M. H., Xing, Y. H., He, X. H., LinJ. P. and Chen, T.: Self-assembly and photo-responsive behavior of novel ABC2-type block copolymers containing azobenzene moieties. Soft Matter8 (2012) 3131–3138. 10.1039/C2SM07100BSearch in Google Scholar

30. Miljanic, S., Frkanec, L., Meic, Z. and Zinic, M.: Photoinduced gelation by stilbene oxalyl amide compounds. Langmuir21 (2005) 2754–2760. 15779945 10.1021/la047183dSearch in Google Scholar

31. Eastoe, J., Sanchez-Dominguez, M., Wyatt, P. and Heenan, R. K.: A photo-responsive organogel. Chem. Commun.22 (2004) 2608–2609. 15543303 10.1039/B410158HSearch in Google Scholar PubMed

32. Lee, H.-Y., Diehn, K. K., Sun, K., Chen, T. and Raghavan, S. R.: Reversible photorheological fluids based on spiropyran-doped reverse micelles. J. Am. Chem. Soc.133 (2011) 8461–8463. 21563769 10.1021/ja202412zSearch in Google Scholar PubMed

33. Sakai, H., Orihara, Y., Kodashima, H., Matsumura, A., Ohkubo, T., Tsuchiya, K. and Abe, M.: Photoinduced reversible change of fluid viscosity, J. Am. Chem. Soc.127(39) (2005) 13454–3455. 16190682 10.1021/ja053323Search in Google Scholar

34. Long, J., Tian, S. L., Niu, Y. H., Li, G. and Ning, P.: Reversible solubilization of typical polycyclic aromatic hydrcarbons by a photoresponsive surfactant, Colloids and Surfaces A: Physic Chem. Eng. Aspects454 (2014) 172–179. 2014.04.033. 10.1016/j.colsurfaSearch in Google Scholar

35. Freimanis, J., Markava, E., Matisova, G., Gerca, L., Muzikante, I., Rutkis, M. and Silinsh, E.: (Methylacylamino)azobenzene derivatives for photoresponsive monomolecular layers. Langmuir10 (1994) 3311–3314. 10.1021/la00021a065Search in Google Scholar

36. Tazuke, S., Kurihara, S., Yamaguchi, H. and Ikeda, T.: Photochemically triggered physical amplification of photoresponsiveness. J. Phys. Chem.91 (1987) 249–252. 10.1021/j100286a001Search in Google Scholar

37. Hayashita, T., Kurosawa, T., Miyata, T., Tanako, K. and Igawa, M.: Effect of structural variation within cationic azo-surfactant upon photoresponsive function in aqueous solution. Colloid Polym. Sci.272 (1994) 1611–1619. 10.1007/BF00664729Search in Google Scholar

38. Dunkin, I. R., Gittinger, A., Sherrington, D. C. and Whittaker, P.: A photodestructible surfactant. J. Chem. Soc., Chem. Commun.19 (1994) 2245–2246. 10.1039/C39940002245Search in Google Scholar

39. Sakai, H., Matsumura, A., Yokoyama, S., Saji, T. and Abe, M.: Photochemical switching of vesicle formation using an azobenzene-modified surfactant. J. Phys. Chem. B103 (1999) 10737–10740. 10.1021/jp9927505Search in Google Scholar

40. Matsumura, A., Tsuchiya, K., Torigoe, K., Sakai, K., Sakai, K. and Abe, M.: Photochemical control of molecular assembly formation in a catanionic surfactant system. Langmuir27(5) (2011) 1610–1617. 21244081 10.1021/jp9927505Search in Google Scholar

41. Peng, S. H., Guo, Q. P., Hartley, P. G. and Hughes, T. C.: Azobenzene moiety variation directing selfassembly and photoresponsive behavior of azosurfactants. J. Mater. Chem. C2 (2014) 8303–8312. 10.1039/C4TC00321GSearch in Google Scholar

42. Avó, J., Cunha-Silva, L., Carlos Lima, J. and Jorge Parola, A.: Design and Synthesis of Photoactive Ionic Liquids. Org. Lett.16 (2014) 2582–2585. 24787141 10.1021/ol501111dSearch in Google Scholar PubMed

43. Jie, Y., HuiyongW., Jianji, W.Yue, Z. and Zhongjia, G.: Highly efficient conductivity modulation of cinnamate-based light-responsive ionic liquids in aqueous solutions. Chem. Commun.50 (2014) 14979–14982. 25328142 10.1039/c4cc04274cSearch in Google Scholar PubMed

44. Asaka, T., Akai, N., Kawai, A. and Shibuya, K.: Photochromism of 3-butyl-1-methyl-2-phenylazoimidazolium in room temperature ionic liquids. J. Photochem. Photobiol. A209 (2010) 12–18. 10.1016/j.jphotochem.2009.10.002.Search in Google Scholar

45. Branco, L. C. and Pina, F.: Intrinsically photochromic ionic liquids. Chem. Commun., 41 (2009) 6204–6206. 19826669 10.1039/B907672GSearch in Google Scholar

46. Tamura, H., Shinohara, Y. and Arai, T.: Synthesis and photochemistry of stilbene ionic liquids. Chem. Lett.39 (2010) 240241. 10.1246/cl.2010.240Search in Google Scholar

47. Zhang, S. G., Liu, S. M.,. Zhang, Q. H. and Deng, Y. Q.: Solvent-dependent photoresponsive conductivity of azobenzene- appended ionic liquids. Chem. Commun.47 (2011) 6641–6643. 21566803 10.1039/C1CC11924ASearch in Google Scholar PubMed

48. Harkins, W. D. and Brown, F. E.: The determination of surface tension (free surface energy), and the weight of falling drops: the surface tension of water and benzene by the capillary height method, J. Am. Chem. Soc.4(1) (1919) 499–524. 10.1021/ja01461a003Search in Google Scholar

49. Deleu, M., Paquet, M. and Blecker, C.: Encyclopedia of Surface and Colloid Science, in: T. A.Hubbard (Ed.), Dekker, New York, 2002, pp. 5119.Search in Google Scholar

50. Fredlake, C. P., Crosthwaite, J. M., Hert, D. G., Aki, S. N. V. K. and Brennecke, J. F.: Thermophysical properties of imidazolium-based ionic liquids, J. Chem. Eng. Data49 (2004) 954–964. 0342 61a. 10.1021/jeSearch in Google Scholar

51. Jian, L., Sen-lin, T., Shan-shan, H. and Jun, C.: Synthesis and photochemical behavior of reversible photosensitive surfactant 4-butylazobenzene-4′-(oxyethyl) trimethylammonium bromide, Fine Chemicals30 (2013) 1108–1111. 10.13550/j.jxhg.2013.10.011Search in Google Scholar

52. Yang, L., Takisawa, N., Hayashita, T. and Shirahama, K.: Colloid chemical characterization of the photosurfactant 4-Ethylazobenzene 4′-(0xyethyl)trimethyl ammonium bromide, J. Phys. Chem.99 (1995) 8799–8803. 054. 10.1021/j100021aSearch in Google Scholar

53. Hayashita, T., Kurosawa, T., Miyata, T., Tanaka, K. and Igawa, M.: Effect of structural variation within cationic azo-surfactant upon photoresponsive function in aqueous solution, Colloid Polym Sci272 (1994) 611–1619, http://doi.org/10. 1007/BF00664729.Search in Google Scholar

54. Kang, Ho-Cheol., Lee, B. M., Yoon, J. and Yoony, M.: Synthesis and surface-active properties of new photosensitive surfactants containing the azobenzene group, J Colloid Interface Sci.231 (2000) 255–264. 10.1006/jcis.2000.7158Search in Google Scholar PubMed

55. Zhang, Y., Yu, S., Wang, L. and Li, C.: Synthesis and characterization of conjugated polymer containing azobenzene and oxadiazole units, Chinese Chemical Lett20 (2009) 235–237. 10.1016/j.cclet.2008.10.002Search in Google Scholar

56. Holmqvist, P., Alexandridis, P. and Lindman, B.: Modification of the microstructure in block copolymer–water–“oil” systems by varying the copolymer composition and the “oil” type: small-angle X-ray scattering and deuterium-NMR Investigation, J. Phys. Chem. B102 (1998) 1149–1158. 10.1021/jp9730297Search in Google Scholar

57. Firestone, M. A., Dzielawa, J. A., Zapol, P., Curtiss, L. A., Seifert, S. and Dietz, M. L.: Lyotropic liquid-crystalline gel formation in a room-temperature ionic liquid, Langmuir18 (2002) 7258–7260. 10.1021/la0259499Search in Google Scholar

58. Inoue, T., Dong, B. and Zheng, L.: Phase behavior of binary mixture of 1-dodecyl-3-methylimidazolium bromide and water revealed by differential scanning calorimetry and polarized optical microscopy, J Colloid Interface Sci.307 (2007) 578–581. 17223122 10.1016/j.jcis.2006.12.063Search in Google Scholar PubMed

59. Shang, T. G., Smith, K. A. and Hatton, T. A.: Photoresponsive Surfactants Exhibiting Unusually Large, Reversible Surface Tension Changes under Varying Illumination Conditions, Langmuir19(26) (2003) 10764–10773. 10.1021/la0350958Search in Google Scholar

60. Wei, Y., Wang, F., Zhang, Z., Ren, C. and Lin, Y.: Micellization and thermodynamic Study of 1-alkyl-3- methylimidazolium tetrafluoroborate ionic liquids in aqueous solution, J. Chem. Eng. Date59 (2014) 1120–1129. 10.1021/je400861gSearch in Google Scholar

61. Ted Lee, C. Jr., Smith, K. A. and T. AlanHatton.: Photoreversible viscosity changes and gelation in mixtures of hydrophobically modified polyelectrolytes and photosensitive surfactants, Macromolecules37 (2004) 5397–5405. 10.1021/ma036019eSearch in Google Scholar

62. Geng, F., Liu, J., Zheng, L. Q., Yu, L., Li, Z., Li, G. Z. and Tung, C. H.: Micelle formation of long-chian imidazolium ionic liquids in aqueous solution measured by isothermal titration microcalorimetry. J. Chem. Eng. Date55 (2010) 147–151. 10.1021/je900290wSearch in Google Scholar

63. Orihara, Y., Matsumura, A., Saito, Y., Ogawa, N., Saji, T., Yamaguchi, A., Sakai, H. and Abe, M.: Reversible release control of an oily Substance using photoresponsive micelles, Langmuir17 (2001) 6072–6076./la010360f. 10.1021Search in Google Scholar

64. Wang, H., Zhang, L., Wang, J. J., Lia, Z. and Zhang, S.: the first evidence for unilamellar vesicle formation of ionic liquids in aqueous solutions, Chem. Commun.49 (2013) 5222–5224. 23628851 10.1039/c3cc41908hSearch in Google Scholar PubMed

65. Vila, J., Varela, L. M. and Cabeza, O.: Cation and anion sizes influence in the temperature dependence of the electrical conductivity in nine imidazolium based ionic liquids, Electrochimica Acta52 (2007) 7413–7417. 2007.06.044. 10.1016/j.electactaSearch in Google Scholar

Received: 2017-09-08
Accepted: 2018-02-18
Published Online: 2018-05-07
Published in Print: 2018-05-14

© 2018, Carl Hanser Publisher, Munich

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Physical Chemistry
  4. Morphologic Properties, Texture Transformations and Optical Refracting Properties: Aqueous Bicomponent Amphiphilic Lyotropic Systems
  5. Influence of Cationic Surfactant and Temperature on the Growth of ZnO Nanoparticles
  6. Effect of Surfactants on the Belousov-Zhabotinsky Reaction with Ninhydrin as Organic Substrate
  7. Solubility of Some Mineral Salts in Polyethylene Glycol and Related Surfactants
  8. Novel Surfactants
  9. Solubility Enhancement of Polycyclic Aromatic Hydrocarbons by an Eco-Friendly Ester-Linked Gemini Surfactant and its Mixtures with Conventional Surfactants
  10. Novel Carbohydrate Based Non-Ionic Gemini Surfactants with Flexible Spacer as Reverse Micellar Systems for Encapsulation of D- and L-Enantiomers of Some Aromatic α-Amino Acids in n-Hexane
  11. Synthesis and Characterization of Photosensitive Ionic Liquid Surfactant 4-Butylazobenzene-4′-(Oxyethyl)Methylimidazolium with Br− and BF4− Counterions
  12. Synthesis
  13. Improved Synthesis and Properties of N-(3-octadecylamino-2-hydroxyl) Propyl Trimethyl Ammonium Chloride
  14. Influence of the Hydro/Fluorocarbon Chain Length on CMC and HLB of Surface-Active Nonionic Surfactants Containing Polyethylene Glycol Groups
  15. Application
  16. Ultra-Low Interfacial Tension of a Surfactant under a Wide Range of Temperature and Salinity Conditions for Chemical Enhanced Oil Recovery
https://doi.org/10.3139/113.110558
Keywords for this article
Photosensitivity; ionic liquid surfactant; liquid crystal; surface tension

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Physical Chemistry
  4. Morphologic Properties, Texture Transformations and Optical Refracting Properties: Aqueous Bicomponent Amphiphilic Lyotropic Systems
  5. Influence of Cationic Surfactant and Temperature on the Growth of ZnO Nanoparticles
  6. Effect of Surfactants on the Belousov-Zhabotinsky Reaction with Ninhydrin as Organic Substrate
  7. Solubility of Some Mineral Salts in Polyethylene Glycol and Related Surfactants
  8. Novel Surfactants
  9. Solubility Enhancement of Polycyclic Aromatic Hydrocarbons by an Eco-Friendly Ester-Linked Gemini Surfactant and its Mixtures with Conventional Surfactants
  10. Novel Carbohydrate Based Non-Ionic Gemini Surfactants with Flexible Spacer as Reverse Micellar Systems for Encapsulation of D- and L-Enantiomers of Some Aromatic α-Amino Acids in n-Hexane
  11. Synthesis and Characterization of Photosensitive Ionic Liquid Surfactant 4-Butylazobenzene-4′-(Oxyethyl)Methylimidazolium with Br− and BF4− Counterions
  12. Synthesis
  13. Improved Synthesis and Properties of N-(3-octadecylamino-2-hydroxyl) Propyl Trimethyl Ammonium Chloride
  14. Influence of the Hydro/Fluorocarbon Chain Length on CMC and HLB of Surface-Active Nonionic Surfactants Containing Polyethylene Glycol Groups
  15. Application
  16. Ultra-Low Interfacial Tension of a Surfactant under a Wide Range of Temperature and Salinity Conditions for Chemical Enhanced Oil Recovery
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