Gemini表面活性剂—聚甘油类非离子表面活性剂的合成与应用研究
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摘要
以单辛酸乙酯、甲酸乙酯和1,2-二溴乙烷,通过克莱森缩合、酮酸酯烃化、酮酸酯的碱式裂解合成中间体:2,5-二己基己二酸乙酯。中间体经分离提纯后用红外和核磁共振氢谱等手段进行分析和表征,结果表明,所合成的表面活性剂中间体的结构与设计的结构基本吻合。进而,对中间体进行酯交换反应,成功地合成了三种非离子型Gemini表面活性剂G121、G222和G323。
测定非离子Gemini表面活性剂G121、G222和G323水溶液的表面张力,结果分别为:28.8、30.0、31.5mN m~(-1),进而得出临界胶束浓度0.0045、0.0040和0.0038mmol L~(-1),表明该类表面活性剂比普通的单头基表面活性剂,具有更优异的表面活性。另外测定其其它性能,结果如下:乳化力分别为:4.83、6.12和6.93min,润湿力分别为36、33和28s,钙皂分散力(LSDR%)分别为:20、18和15,从而表明非离子Gemini表面活性剂G121、G222和G323的性能均优于单辛酸甘油酯。
将非离子Gemini表面活性剂G121、G222和G323作为塑料薄膜流滴剂使用,测定各表面活性剂的初滴时间和十滴时间,初滴时间分别为:7.11、5.69和5.66 min,十滴时间分别为:1.46、1.20和0.75min,进而表明非离子Gemini表面活性剂G121、G222和G323可作为流滴剂使用。
Two kind of intermediates are synthesized through Claisen condensation, and substitution using ethyl caprylate, ethyl formate, metallic sodium, 1,2-dibromoehane, 1,6-dibromohexane, and absolute alcohol as materials. After the intermediates are separated and purified, they are analyzed by the following examining methods: IR and 1H NMR and proved to be the intermediates as originally expected. The final products (G121, G222 and G323) of nonionic Gemini surfactant can be synthesized by transesterification the intermediates with the glycerol or polyglycerol.
The non-ionic Gemini surfactants G121, G222 and G323 have more excellent properties compared with conventional single-chain surfactant glycerol caprylate, the surface tension of theirs are 28.8, 30.0 and 31.5mN m~(-1), respectively, the CMC values of theirs were 0.0045, 0.0040 and 0.0038mmol L~(-1), respectively, the properties of theirs, including wetting ability (are 36, 33 and 28s, respectively), soap dispersancy(are 20%, 18%, 15%, respectively), emulsifying capability (are 7.11, 5.69 and 5.66min, respectively) and anti-drop property are better.
测定非离子Gemini表面活性剂G121、G222和G323水溶液的表面张力,结果分别为:28.8、30.0、31.5mN m~(-1),进而得出临界胶束浓度0.0045、0.0040和0.0038mmol L~(-1),表明该类表面活性剂比普通的单头基表面活性剂,具有更优异的表面活性。另外测定其其它性能,结果如下:乳化力分别为:4.83、6.12和6.93min,润湿力分别为36、33和28s,钙皂分散力(LSDR%)分别为:20、18和15,从而表明非离子Gemini表面活性剂G121、G222和G323的性能均优于单辛酸甘油酯。
将非离子Gemini表面活性剂G121、G222和G323作为塑料薄膜流滴剂使用,测定各表面活性剂的初滴时间和十滴时间,初滴时间分别为:7.11、5.69和5.66 min,十滴时间分别为:1.46、1.20和0.75min,进而表明非离子Gemini表面活性剂G121、G222和G323可作为流滴剂使用。
Two kind of intermediates are synthesized through Claisen condensation, and substitution using ethyl caprylate, ethyl formate, metallic sodium, 1,2-dibromoehane, 1,6-dibromohexane, and absolute alcohol as materials. After the intermediates are separated and purified, they are analyzed by the following examining methods: IR and 1H NMR and proved to be the intermediates as originally expected. The final products (G121, G222 and G323) of nonionic Gemini surfactant can be synthesized by transesterification the intermediates with the glycerol or polyglycerol.
The non-ionic Gemini surfactants G121, G222 and G323 have more excellent properties compared with conventional single-chain surfactant glycerol caprylate, the surface tension of theirs are 28.8, 30.0 and 31.5mN m~(-1), respectively, the CMC values of theirs were 0.0045, 0.0040 and 0.0038mmol L~(-1), respectively, the properties of theirs, including wetting ability (are 36, 33 and 28s, respectively), soap dispersancy(are 20%, 18%, 15%, respectively), emulsifying capability (are 7.11, 5.69 and 5.66min, respectively) and anti-drop property are better.
引文
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[2] 沈钟, 王果庭. 胶体与表面化学[M].北京: 化学工业出版社, 1997: 313.
[3] 赵小莉, 黄建滨, 李子臣等. Bola 型表面活性剂. 表面性质与胶团[J]. 日用化学工业, 2000, 30(5): 26-29.
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[5] 水玲玲, 郑利强, 赵剑曦等. 双子表面活性剂的研究进展[J]. 日用化学工业, 2001, 18(2): 67-69.
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[9] Alami E., Levy H., Zana R. structure of the lyotropic mesophase in the pres2ence of water[J]. Languamir, 1993, 10: 940-944.
[10] Zana R., Benrraou M., Rueff R. Alkanediyl-α, ω-bis (dimethyl alkyl ammonium bromide) Surfactants Effect of the Spacer Chain Length on the Critical Micelle Concentration and Micelle Ionization Degree[J]. Langmuir, 1991, 7: 1072-1075.
[11] Huo Q., Rosa L., Pierre M.P. Meso structure DesigneithGeminiSurfactants: Supercage Formation in a Three-Dimensional Hexag-onal Array[J]. Science, 1995, 268: 1324-1327.
[12] Hou Q. Generalized synthesis of periodic surfactant/inorganic composite materials[J]. Nature, 1994, 368: 317-321.
[13] Aurora P., Lourdes P., Maria R.I. et al. Relation of foam stability to solution and surface properties of Gemini cationic surfactants derived from arginine[J ]. Colloids and Surfaces A, 2001, 189(1-3): 225-235.
[14] Reiko O., Ivan H. Aggregation properties and mixing behavior of hydrocarbon, fluorocarbon, and hlybrid hydrocarbon-fluorocarbon cationic dimeric surfactants[J] . Langmuir, 2000, 16(2): 9759-9769.
[15] Renouf P., Mioshowski C., Lebeau L. First Synthesis of an Asymmetrical Gemini Compound[J]. Tetrahedron Letters, 1998, 39:1357-1360.
[16] Mariano J., Castro L., Kovensky J. et al. New dimeric surfactants from alkyl glucosides[J]. Tetrahedron, 1999, 55: 12711~12722.
[17] Aswal V.K., Goyal P.S., Bhattacharya S. et al. Characterization of Novel Gemini Surfactant Micelles with Phosphate Head Groups by SANS and FluorescenceSpectroscopy[J]. Chem. Phys .Lett., 1999, (303):295-303.
[18] 曹亚峰. 双烷基 γ-双季铵盐的合成[J]. 表面活性剂工业, 1993, 4: 22-23.
[19] 赵剑曦. Gemini 表面活性剂研究的新进展[J]. 化学进展, 1999, 11(4): 348-357.
[20] 陈功, 黄鹏程, 马云容等. 新型双联阳离子活性剂的合成与表征[J]. 石油化工, 2002, 31(3): 194.
[21] Metthew L., Fielden, Christele P., Andreas K. et al. Sugar-based tertiary amino Gemini surfactants with a vesicle-to-micelle transition in the endosomal pH range mediate efficient transfection in vitro[J]. European Journal of Biochemistry,2001,268: 1269-1279.
[22] James T.D., Li R., Yang J. Nonionic Gemini surfactants having multiple hydrophobic and hydrophilic sugar groups[P]. US:5863886,1999-01-26.
[23] 史俊, 谢炜. 直接胺化缩合制备葡萄糖胺类化合物[J]. 化学试剂,2002,24(2):93-94, 118.
[24] 史俊, 李谦定, 夏小春. Gemini 表面活性剂的研究进展[J]. 化学研究与应用,2005,17(3): 293-298.
[25] 陈文君, 顾强, 姚发业等. 一种用于识别肌酸酐分子的荧光化学敏感器[J]. 化学学报, 2002, 60(5):810-814.
[26] Liang Z., Wang C., Huang J. The research on the vesicle formation and transformation in novel Gemini surfactant systems[J]. Colloids and Surfaces A 2003, 224, 213-220.
[27] Grosmaire L., Chorro M., Chorro C., Partyka S. Influence of the Chemical Surface State of Silica on Adsorption Process of Conventional Cationic and Gemini Surfactants: Thermodynamic Investigations[J]. Journal of Colloid and Interface Science, 2001, 242(2): 395-403.
[28] Meziani M.J., Benalla H., Zajac J. et al. Adsorption of a cationic Gemini surfactant from aqueous solution onto alumino silicate powders of the MCM-41 type: effect of pore size and co-adsorption of phenol[J]. Journal of Colloid and Interface Science, 2003, 262(2): 362-371.
[29] Esumi K., Goino M., Koide Y. Adsorption and Adsolubilization by Monomeric, Dimeric, or Trimeric Quaternary Ammonium Surfactant at Silica/Water Interface [J]. Journal of Colloid and Interface Science, 1996, 183(2): 539-545.
[30] Kazuyuki Tsubone. The interaction of an anionic Gemini surfactant with conventional anionic surfactants[J]. Journal of Colloid and Interface Science, 2003, 261(2): 524-528.
[31] Terri A., Camesano R.N. Micelle formation and CMC ofGeminisurfactants: a thermodynamic model[J]. Colloid and Surfaces A, 2000, (167): 165-177.
[32] De S., Aswal V.K., Goyal P.S., Bhattacharya S. Characterization of new Gemini surfactant micelles with phosphate headgroups by SANS and fluorescence spectroscopy[J]. Chem. Phys. Lett., 1999, (303): 295-303.
[33] Scheibel J., Connor D.S., Fu Y.C. Gemini polyhydroxy fatty acid amides[P]. US: 5534197, 1996-07-09.
[34] James T.D., Li R.X., Yang J. Nonionic Gemini surfactants having hydrophilic sugar groups[P]. AU: 7246198, 1998-10-30.
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