Synthesis and Self-association Property of a Novel Hydrotrope Amphiphilic Compound

doi:10.7517/j.issn.1674-0475.2009.04.287

Abstract

Abstract: A novel polymerizable amphiphilic compound having analogous structure of hydrotrope,4-(2-(acryloyloxy) ethoxy)benzyl tri-ethyl ammonium bromide(AEBA),was synthesized.The solution property and self-association of AEBA were studied by UV-absorption spectra and fluorescence technique The experimental results showed that AEBA exhibits high self-associative capacity in aqueous solution,pronounced surface activity and solubilization.The MHC(minimum hydrotrope concentration) of AEBA was determined around 0.05 mol/L for fluorescein diacetate(FDA).AEBA molecules associate into stack-type of aggregate resulting from intermolecular association,which is different from the surfactant micelle structure.The aggregation number increased gradually with AEBA concentration that becomes more considerable at higher concentration.

Key words: amphiphilic compound, self-association, aggregation structure

CLC Number:

LI Jing, WU Fei-peng, WANG Er-jian. Synthesis and Self-association Property of a Novel Hydrotrope Amphiphilic Compound[J]. Imaging Science and Photochemistry, 2009, 27(4): 287-295.

References

[1] Neuberg C.Hydrotropy[J].Biochem.Z.,1916,76:107-176.
[2] Neuberg C.Hydrotropic phenomena[J].J.Chem.Soc.,1916,110(II):555-559.
[3] Travis K H,Eric W K.Hydrotropic solution[J].Curr.Opin.Colloid Interface Sci.,2007,12(3):121-128.
[4] Roy B K,Moulik S P.Effect of hydrotropes on solution behavior of amphiphiles[J].Curr.Sci.,2003,85(8):1148-1155.
[5] Gonzalez Y I,Stjemdahl M,Dsnino D,Kaler E W.Spontaneous vesicle imidasoline compounds[J].Langmuir,2004,20(17):7053-7063.
[6] Dhara D,Chatterji P R.Effect of hydrotropes on volume phase transition in poly(N-isopropylacrylamide)hydrogel[J].Langrnuir,1999,15(4):930-935.
[7] Oyaizu K,Shiba Y,Nakamura Y,Yuasa M.Highly stable polymerizabh vesicles in anionic surfactant/ammonium salt mixtures in the presence of cross-linkingmonomers for oonvenient preparation of hollow nanospheres[J].Langmuir,2006,22(12):5261-5265.
[8] Balasubramanian D,Srinivas V.Aggregation behavior of hydrotmplc compounds in aqueous solution[J].J.Phys.Chem.,1989,93(9):3865-3870.
[9] Srinivas V,Rodley G A,Raviktamr K,Robinson W T,Tumbull M M,Balasubramanian D.Molecular organization in hydrotmpe assemblies[J].Langmuir,1997,13(12):3235-3239.
[10] Huh K M,Lee S C,Cho Y W,Lee J.Jcong J H,Park K.Hydmtropic polymermicelle system for delivery of paclitaxel[J].J.Control Release,2005,101(1-3):59-68.
[11] Lee S C,Huh K M,Park J H,Park K.Pharmaceutical applicationsof hydrotrope polymer micelles[P].US Patent,50 158 271.2005-07-21.
[12] Lee S C,Acberya G,Lee J,Park K.Hydrotropic polymers:synthesis and characterization of polymers conuaning picolylnicotinamide moieties[J].Macromolecules,2003,36(7):2248-2255.
[13] Ooya T,Lee J,Park K.Hydrotroic dendrimers of gengerations 4 and 5:synthesis,characterization and hydrotropic solubilization of paclitaxd[J].Bioconjug.Chem.,2004,15(6):1221-1229.
[14] Ooya T,Moo H K,Saitoh M,Tamiya E,Park K.Self-assembly of cholesterol-hydrotropic dendfimers conjugates into micelle-like structure:preparation and hydrotropic solubilization of paclitaxel[J].Sci.Technol.Adv.Mater.,2005,6(5):452-456.
[15] Zhu Z Y,Gonzalez Y I,Xu H X,Kaler E W,Liu S Y.Polymerization of anionic wormlike micelles[J].Langmuir,2006,22(3):949-955.
[16] Liu S,Gonzalez Y I,Danino D,Kahr E W.Polymerization of wormlike mieelles induced by hydrotropie salt[J].Macromolecules,2005,38(6):2482-2491.
[17] Souza T P,Zanette D,Kawanami A E,Rezande L D,lshiki H M,Amaral A T.pH at the micellar interface:synthesis of pH probes derived from salicylic acid,acid-base dissociation in sodium dodecyl sulfate mieelles,and Possion-Boltzmann simulation[J].J Colloid Interface Sci.,2006,297(1):292-302.
[18] Li J,Wu F P,Wang E J.Studies on self-associative behavior of a novel cation amphiphilic polymer[J].Chinese J.Polym.Sci.,(in the press).
[19] Li J,wu F P,Wang E J.Hydmphobically associating polyacrylamide modified by a novel sdf-associative cationic monomer[J].Chinese J.Polym.Sci.,(in the press).
[20] Kawashima Y,Zanleo K,Kato M.Hasegawa M,kazuyuki T,Katuo H,Hirono S,Moriguchi I.Structure-activity studies of 3-benzoylpropionic acid derivatives suppressing adjvant arthritis[J].Chem.Pharm.Bull.,1992,40(3):774-777.
[21] Corbin T F,Hahn R C,Shechter H.Cyclopropylbenzene[J].Organic Synthes.,1964,44(5):30-33.
[22] Wang L J,Liu X J,Li Y Z.Synthesis and evaluation of a surface-active phominitiator for microemulsion polymerization[J].Macromolecules.1998,31(11):3446-3453.
[23] 赵国玺.表面活性剂物理化学[M].第一版.北京:北京大学出版社,1984.Zhao G X.Physical Omnistry of Surfacetant[M].1st ed.Beijing:Perking Universyty Press,1984.
[24] Srinivas V,13alasubramanian D.When does the switch from hydrotropy to micellar behavior occur[J].Langmuir,1998,14(23):6658-6661.
[25] Bauduin P,Rermncourt A,Kopf A,Touraud D,Kum W.Unified concept of solubilization in water by hydrotropes and cosolvents[J].Langrnuir,2005,21(15):6769-6775.
[26] Valdes-Aguilera O,Neckers D C.Aggregation phenomena in xanthene dyes[J].Acc.Chem.Res.,1989,22(5):171-177.
[27] Kalyamsundararn K,Thomas J K.Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems[J].J,.Am.Chem.Soc.,1977,99(7):2039-2044.
[28] Nicholas J T,Ahmad Y.Luminescent probes for detergent solutions.A simple procedure for determination of the mean aggregation number of micelles[J].J.Am.Chem.Soc.,1978,100(18):5951-5952.
[29] Infelta P P.Fluoreseence quenching in micellar solutions and application to the determinafium of aggregation numbers[J].Chem.Phys.Lat.,1979,61(1):88-91.