Synthesis and self-aggregation of a hydroxyl-functionalized imidazolium-based ionic liquid surfactant in aqueous solution

Journal of Surfactants and Detergents

Volumn 14, Issue 2, 2011, Pages 203-210

  Liu, Xue Feng ^a   Dong, Li Li ^a   Fang, Yun ^a,b  

^a JIANGNAN UNIVERSITY   (China)

^b Jiangsu Key Laboratory of Fine Chemicals   (China)

Author keywords

Hydroxyl functionalized; Imidazolium based; Ionic liquid surfactant; The critical aggregation number; The second CMC

Indexed keywords

CRITICAL MICELLE CONCENTRATION; ELECTRODEPOSITION; ELECTROSPRAY IONIZATION; IONIC LIQUIDS; LIQUIDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; SOLUTIONS; SURFACE ACTIVE AGENTS; SURFACE TENSION;

CRITICAL AGGREGATION; FUNCTIONALIZED; IMIDAZOLIUM-BASED; IONIC LIQUID SURFACTANTS; THE SECOND CMC;

AGGLOMERATION;

EID: 85027933207     PISSN: 10973958     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11743-010-1234-3     Document Type: Article

References (58)

1. Dupont J, Souza RF, Suarez PAZ (2002) Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev 102:3667-3692 (Pubitemid 35353956)
2. Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071-2083 (Pubitemid 129585179)
3. Huddleston JG, Willauer HD, Swatloski RP, Visser AE, Rogers RD (1998) Room temperature ionic liquids as novel media for 'clean' liquid-liquid extraction. Chem Commun 16:1765-1766 (Pubitemid 128675787)
4. Xia H, Yu J, Jiang Y, Mahmood I, Liu H (2007) Physicochemical features of ionic liquid solutions in phase separation of Penicillin (II): Winsor II reversed micelle. Ind Eng Chem Res 46:2112-2116 (Pubitemid 46588083)
5. Byme N, Howlett C, MacFarlane R, Forsyth M (2005) The zwitterion effect in ionic liquids: Towards rechargeable lithiummetal batteries. Adv Mater 17:2497-2501 (Pubitemid 41504986)
6. Rebelo LPN, Lopes JNC, Esperança JMSS, Guedes HJR, Łachwa J, Najdanovic-Visak V, Visak ZP (2007) Accounting for the unique, doubly dual nature of ionic liquids from a molecular thermodynamic and modeling standpoint. Acc Chem Res 40:1114-1121
7. Dorbritz S, Ruth W, Kragl U (2005) Investigation on aggregate formation of ionic liquids. Adv Synth Catal 347:1273-1279 (Pubitemid 41044817)
8. Merrigan TL, Bates ED, Dorman SC Jr, Davis JH (2000) New fluorous ionic liquids function as surfactants in conventional room-temperature ionic liquids. Chem Commun 20:2051-2052
9. Miskolczy Z, Sebök-Nagy K, Biczók L, Göktürk S (2004) Aggregation and micelle formation of ionic liquids in aqueous solution. Chem Phys Lett 400:296-300
10. Baltazar QQ, Chandawalla J, Sawyer K, Anderson JL (2007) Interfacial and micellar properties of imidazolium-based monocationic and dicationic ionic liquids. Colloids Surf A 302:150-156 (Pubitemid 46719875)
11. Jungnickel C, Łuczak J, Ranke J, Fernández JF (2008) Micelle formation of imidazolium ionic liquids in aqueous solution. Colloids Surf A 316:278-284 (Pubitemid 351173730)
12. Łuczak J, Hupka J, Thöming J, Jungnickel C (2008) Self-organization of imidazolium ionic liquids in aqueous solution. Colloids Surf A 329:125-133
13. Blesic M, Marques MH, Plechkova NV, Seddon KR, Rebelo LPN, Lopes A (2007) Self-aggregation of ionic liquids: Micelle formation in aqueous solution. Green Chem 9:481-490
14. Smirnova NA, Vanin AA, Safonova EA, Pukinsky IB, Anufrikov YA, Makarov AL (2009) Self-assembly in aqueous solutions of imidazolium ionic liquids and their mixtures with an anionic surfactant. J Colloid Interface Sci 336:793-802
15. Goodchild I, Collier L, Millar SL, Prokeš I, Lord JCD, Butts CP, Bowers J, Webster JRP, Heenan RK (2007) Structural studies of the phase, aggregation and surface behaviour of 1-alkyl-3-methylimidazolium halide + watermixtures. J Colloid Interface Sci 307:455-468 (Pubitemid 46175834)
16. Inoue T, Ebina H, Dong B, Zheng L (2007) Electrical conductivity study on micelle formation of long-chain imidazolium ionic liquids in aqueous solution. J Colloid Interface Sci 314:236-241 (Pubitemid 47187444)
17. El Seoud OA, Pires PAR, Abdel-Moghny T, Bastos E (2007) Synthesis and micellar properties of surface-active ionic liquids: 1-alkyl-3-methylimidazolium chlorides. J Colloid Interface Sci 313:296-304 (Pubitemid 47042782)
18. Ao M, Xu G, Zhu Y, Bai Y (2008) Synthesis and properties of ionic liquid-type gemini imidazolium surfactants. J Colloid Interface Sci 326:490-495
19. Thomaier S, Kunz W (2007) Aggregates in mixtures of ionic liquids. J Mol Liq 130:104-107 (Pubitemid 44894584)
20. 16mimCl in ethylammonium nitrate. J Phys Chem B 113:2024-2030
21. Blesic M, Lopes A, Melo E, Petrovski Z, Plechkova NV, Lopes JNC, Seddon KR, Rebelo LPN (2008) On the self-aggregation and fluorescence quenching aptitude of surfactant ionic liquids. J Phys Chem B 112:8645-8650
22. Zhao Y, Gao S, Wang J, Tang J (2008) Aggregation of ionic liquids [Cnmim]Br (n = 4, 6, 8, 10, 12) in D2O: A NMR study. J Phys Chem B 112:2031-2039 (Pubitemid 351316326)
23. Gaillon L, Sirieix-Plenet J, Letellier P (2004) Volumetric study of binary solvent mixtures constituted by amphiphilic ionic liquids at room temperature (1-alkyl-3-methylimidazolium bromide) and water. J Solution Chem 33:1333-1347 (Pubitemid 40238886)
24. Dong B, Li N, Zheng L, Yu L, Inoue T (2007) Surface adsorption and micelle formation of surface active ionic liquids in aqueous solution. Langmuir 23:4178-4182 (Pubitemid 46643138)
25. Wang J, Wang H, Zhang S, Zhang H, Zhao Y (2007) Conductivities, volumes, fluorescence, and aggregation behavior of ionic liquids [C4mim][BF4] and [Cnmim]Br (n = 4, 6, 8, 10, 12) in aqueous solutions. J Phys Chem B 111:6181-6188 (Pubitemid 46970038)
26. Pino V, Yao C, Anderson J (2009) Micellization and interfacial behavior of imidazolium-based ionic liquids in organic solventwater mixtures. J Colloid Interface Sci 333:548-556
27. Łuczak J, Jungnickel C, Joskowska M, Thöming J, Hupka J (2009) Thermodynamics of micellization of imidazolium ionic liquids in aqueous solutions. J Colloid Interface Sci 336:111-116
28. Wang H, Wang J, Zhang S, Xuan X (2008) Structural effects of anions and cations on the aggregation behavior of ionic liquids in aqueous solution. J Phys Chem B 112:16682-16689
29. Dong B, Zhang J, Zheng L, Wang S, Li X, Inoue T (2008) Saltinduced viscoelastic wormlike micelles formed in surface active ionic liquid aqueous solution. J Colloid Interface Sci 319:338-343
30. Zech O, Thomaier S, Bauduin P, Rück T, Touraud D, Kunz W(2009) Microemulsions with an ionic liquid surfactant and roomtemperature ionic liquids as polar pseudo-phase. J Phys Chem B 113:465-473
31. Safavi A, Maleki N, Farjami F (2010) Phase behavior and characterization of ionic liquids based microemulsions. Colloid Surf A 355:61-66
32. Yan F, Texter J (2006) Surfactant ionic liquid-based microemulsions for polymerization. Chem Commun 25:2696-2698
33. Qiu Z, Texter J (2008) Ionic liquids in microemulsions. Curr Opin Colloid Interface Sci 13:252-262 (Pubitemid 351814830)
34. Firestone MA, Dzielawa JA, Zapol P, Curtiss LA, Seifert S, Dietz ML (2002) Lyotropic liquid-crystalline gel formation in a roomtemperature ionic liquid. Langmuir 18:7258-7260 (Pubitemid 35383134)
35. Li XW, Zhang J, Dong B, Zheng LQ, Tung CH (2009) Characterization of lyotropic liquid crystals formed in the mixtures of 1-alkyl-3-methylimidazolium bromide/p-xylene/water. Colloid Surf A 335:80-87
36. Ao M, Xu G, Pang J, Zhao T (2009) Comparison of aggregation behaviors between ionic liquid-type imidazolium Gemini surfactant [C12-4-C12im]Br2 and its monomer [C12 mim]Br on silicon wafer. Langmuir 25:9721-9727
37. Ding YS, Zha M, Zhang J, Wang SS (2007) Synthesis, characterization and properties of geminal imidazolium ionic liquids. Colloid Surf A 298:201-205 (Pubitemid 46441801)
38. Liu Y, Yu L, Zhang S, Yuan J, Shi L, Zheng L (2010) Dispersion of multiwalled carbon nanotubes by ionic liquid-type gemini imidazolium surfactants in aqueous solution. Colloid Surf A 359:66-70
39. 3]: Mesomorphism and aggregation. Phys Chem Chem Phys 11:4260-4268
40. Li XW, Gao YA, Liu J, Zheng LQ, Chen B, Wu LZ, Tung CH (2010) Aggregation behavior of a chiral long-chain ionic liquid in aqueous solution. J Colloid Interface Sci 343:94-101
41. Branco LC, Rosa JN, Ramos JJM, Afonso CAM (2002) Preparation and characterization of new room temperature ionic liquids. Chem Eur J 8:3671-3677 (Pubitemid 34951455)
42. Yang X, Yan N, Fei Z, Crespo-Quesada RM, Laurenczy G, Kiwi-Minsker L, Kou Y, Li Y, Dyson PJ (2009) Biphasic hydrogenation over PVP stabilized Rh nanoparticles in hydroxyl functionalized ionic liquids. Inorg Chem 47:7444-7446
43. Dorjnamjin D, Ariunaa M, Shim YK (2008) Synthesis of silver nanoparticles using hydroxyl functionalized ionic liquids and their antimicrobial activity. Int J Mol Sci 9:807-820
44. Aguiar J, Carpena P, Molina-Bolívar JA, Ruiz CC (2003) On the determination of the critical micelle concentration by the pyrene 1:3 ratio method. J Colloid Interface Sci 258:116-122 (Pubitemid 36228364)
45. Dong B, Zhao X, Zheng L, Zhang J, Li N, Inoue T (2008) Aggregation behavior of long-chain imidazolium ionic liquids in aqueous solution: Micellization and characterization of micelle microenvironment. Colloids Surf A 317:666-672
46. Geng F, Liu J, Zheng L, Yu L, Li Z, Li G, Tung C (2010) Micelle formation of long-chain imidazolium ionic liquids in aqueous solution measured by isothermal titration microcalorimetry. J Chem Eng Data 55:147-151
47. Osanai S, Yamada G, Hidano R, Beppu K, Namiwa K (2010) Preparation and properties of phosphate surfactants containing ether and hydroxy groups. J Surfact Deterg 13:41-49
48. May S, Ben-Shaul A (2001) Molecular theory of the sphere-torod transition and the second CMC in aqueous solutions. J Phys Chem 105:630-640
49. Romani AP, de Hora Machado AE, Hioka N, Severino D, Baptista MS, Codognoto L, Rodrigues MR, de Oliveira HPM (2009) Spectrofluorimetric determination of second critical micellar concentration of SDS and SDS/Brij 30 systems. J Fluoresc 19:327-332
50. González-Pérez A, Czapkiewicz J, Prieto G, Rodríguez JR (2003) Second critical micelle concentration of dedecyldimethylbenzylammonium chloride in aqueous solution at 25 °C. Colloid Polym Sci 281:1191-1195 (Pubitemid 37441627)
51. Mu JH, Li GZ, Zhang WC, Wang ZW (2001) Determination of the second CMCs of dodecyl polyoxyethylene polyoxypropylene ether by the methods of cloud point, fluorescence, and viscosity. Colloid Surf A 194:1-6
52. González-Pérez A, Czapkiewicz J, Ruso JM, Rodríguez JR (2004) Temperature dependence of second critical micelle concentration of dedecyldimethylbenzyl ammonium bromide in aqueous solution. Colloid Polym Sci 282:1169-1173 (Pubitemid 39193844)
53. Kalyansundaram K, Thomas JK (1977) Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J Am Chem Soc 99:2039-2044
54. Bezzobotnov VY, Borbély S, Cser L, Faragó B, Gladkih IA, Ostanevich YM, Vass S (1988) Temperature and concentration dependence of properties of sodium dodecyl sulfate micelles determined from small-angle neutron scattering experiments. J Phys Chem 92:5738-5743
55. Fang Y, Liu XF, Xia YM, Yang Y, Cai K, Suh JM, Cho HY (2001) Determination of critical micellar aggregation numbers by steady-state fluorescence probe method. Acta Phys Chim Sin 17(9):828-831 (Pubitemid 33339086)
56. Bellare JR, Kaneko T, Evans DF (1988) Seeing micelles. Langmuir 4:1066-1067
57. Rosen MJ (2004) Surfactants and interfacial phenomena. Wiley, New Jersey, pp 108-113
58. Tanford C (1972) Micelle shape and size. J Phys Chem 76(21): 3020-3024