季铵盐Gemini表面活性剂的合成及表面活性的研究
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摘要
表面活性剂在工农业生产和日常生活中具有广泛的用途和重要的意义，因此，探索具有高表面活性的新型表面活性剂是摆在科研人员面前的重要课题。
当前，一类新型的表面活性剂——低聚表面活性剂(oligomeric surfactant)成为研究的热点，其中典型的例子是二聚表面活性剂，也称为Gemini表面活性剂。Gemini表面活性剂是一种分子结构新颖的新型表面活性剂，表现出很多奇异的特性。
本论文通过一系列的实验，合成了两个系列的Gemini表面活性剂联结基团为亚甲基的C_(12)-s-C_(12)·2Br(s=3，4，6)和含羟基联结基团的β。测定了其临界胶团浓度cmc、表面张力γ_(cmc)、降低表面张力的效率C_(20)；测定了它们的胶团聚集数，并讨论了影响因素；研究了C_(12)-s-C_(12)·2Br／SDS及B／SDS复配性能；同时，论文还对C_(12)-s-C_(12)·2Br系列Gemini表面活性剂的应用进行了探讨。主要工作和实验结果如下：
1合成了两个系列的季铵盐Gemini表面活性剂，对其结构进行了鉴定，并对影响反应的因素进行了讨论，找出了合成的最佳合成条件。
2测定了两个系列Gemini表面活性剂的临界胶团浓度cmc、表面张力γ_(cmc)、降低水溶液表面张力的效率C_(20)，发现与相应的传统表面活性剂相比，Gemini表面活性剂具有很低的cmc和很强的表面活性。
3研究了Gemini表面活性剂的表面过剩吸附量和分子面积与Gemini表面活性剂结构之间的关系。发现Gemini表面活性剂的表面过剩吸附量随联接基团碳数的增加而减少，而在界面上的分子面积A却相反。对本课题所合成的Gemini表面活性剂的起泡性能进行了比较，其中含羟基的Gemini表面活性剂β具有良好的起泡性和稳泡性。
4采用荧光探针技术测定了两个系列的Gemini表面活性剂的胶团聚集数，发现阳离子Gemini表面活性剂的浓度强烈影响其胶束聚集数，尤其是对较短联结基团时，连接基团越短，其胶束聚集数越大。温度上升，Gemini表面活性剂的胶束聚集数下降。
5Gemini表面活性剂和SDS的复配比相应普通表面活性剂与SOS的复配能更有效地降低溶液的表面张力，混合表面性剂的cmc大大低于普通表面活性剂之间的复配的cmc。
6同DTAB相比，阳离子Gemini型表面活性剂C_(12)-3-C_(12)·2Br对涤纶织物的碱减量处理具有明显的促进作用。因此它可用作印染助剂。
Because surfactants play a very important role in industry and agriculture production and daily life, exploring novel surfactants with high surface activity is an important thesis to research werkers.
At present, a kind of novel surfactant--oligomeric surfactant which have
high surface activity have become one of focus on surfactant research. A typical example of them is dimeric or Gemini surfactant. Quaternary ammonium Gemini surfactants exhibit peculiar properties because of its novel molecular structure.
In this paper, through a series of experiments, two series of quaternary-ammonium Gemini surfactants were synthesized. Their critical micelle concentration(cmc ) values, the surface tension at their cmc( γ cmc) values , the efficiency of decreasing the surface tension(C2o) and the micelle aggregation number were measured; and the factor affected the results were also discussed. The properties of the system of C12-s-C12 2Br/SDS have been investigated. Meanwhile, the use of C12-s-C12 2Br was discussed in this paper. The main results are as follows:
1 Two series of quaternary-ammonium Gemini surfactants have been synthesized with their structures testified. The optimized methods of synthesis were determined by discussing the factors affecting reactions.
2 Their critical micelle concentration(cmc ) values, the surface tension at their cmc( γ cmc) values and the efficiency of decreasing the surface tension(C20) of the two series surfactants were measured. Results show that Gemini surfactants have much lower cmc and stronger surface activity comparing with the corresponding common surfactants.
3 The excess absorption amount at surface and the area of molecule were discussed. A conclusion can be drawn that the excess absorption amount increases and the area of molecule decreases with the increase of space group carbon number. In the foaming properties of the Gemini surfactants synthesized in this paper, β has shown excellent foaming quality and its foam has the most stable properties.
4 The micelle aggregation number were measured by the technique time-resolved fluorescence quenching (TRFQ) and fluorescence polarization. The concentration of quaternary-ammonium Gemini surfactants has great
influences on the micelle aggregation number. The micelle aggregation number increases with the length of spacer group decreased; and the micelle aggregation number decreases with the temperature increasing.
5 The Mixtures of Gemini surfactants and SDS can lower the surface tension of water solutions more effectively, compared with those of the corresponding common surfactants. Their critical micelle concentration(cmc ) values are more small than those of mixtures of common surfactants.
6 Compared with DTAB, C12-3-C12 2Br can promote the rate of the alkali reduction on terylene more efficiently. So it can be used as textile auxiliaries.
当前，一类新型的表面活性剂——低聚表面活性剂(oligomeric surfactant)成为研究的热点，其中典型的例子是二聚表面活性剂，也称为Gemini表面活性剂。Gemini表面活性剂是一种分子结构新颖的新型表面活性剂，表现出很多奇异的特性。
本论文通过一系列的实验，合成了两个系列的Gemini表面活性剂联结基团为亚甲基的C_(12)-s-C_(12)·2Br(s=3，4，6)和含羟基联结基团的β。测定了其临界胶团浓度cmc、表面张力γ_(cmc)、降低表面张力的效率C_(20)；测定了它们的胶团聚集数，并讨论了影响因素；研究了C_(12)-s-C_(12)·2Br／SDS及B／SDS复配性能；同时，论文还对C_(12)-s-C_(12)·2Br系列Gemini表面活性剂的应用进行了探讨。主要工作和实验结果如下：
1合成了两个系列的季铵盐Gemini表面活性剂，对其结构进行了鉴定，并对影响反应的因素进行了讨论，找出了合成的最佳合成条件。
2测定了两个系列Gemini表面活性剂的临界胶团浓度cmc、表面张力γ_(cmc)、降低水溶液表面张力的效率C_(20)，发现与相应的传统表面活性剂相比，Gemini表面活性剂具有很低的cmc和很强的表面活性。
3研究了Gemini表面活性剂的表面过剩吸附量和分子面积与Gemini表面活性剂结构之间的关系。发现Gemini表面活性剂的表面过剩吸附量随联接基团碳数的增加而减少，而在界面上的分子面积A却相反。对本课题所合成的Gemini表面活性剂的起泡性能进行了比较，其中含羟基的Gemini表面活性剂β具有良好的起泡性和稳泡性。
4采用荧光探针技术测定了两个系列的Gemini表面活性剂的胶团聚集数，发现阳离子Gemini表面活性剂的浓度强烈影响其胶束聚集数，尤其是对较短联结基团时，连接基团越短，其胶束聚集数越大。温度上升，Gemini表面活性剂的胶束聚集数下降。
5Gemini表面活性剂和SDS的复配比相应普通表面活性剂与SOS的复配能更有效地降低溶液的表面张力，混合表面性剂的cmc大大低于普通表面活性剂之间的复配的cmc。
6同DTAB相比，阳离子Gemini型表面活性剂C_(12)-3-C_(12)·2Br对涤纶织物的碱减量处理具有明显的促进作用。因此它可用作印染助剂。
Because surfactants play a very important role in industry and agriculture production and daily life, exploring novel surfactants with high surface activity is an important thesis to research werkers.
At present, a kind of novel surfactant--oligomeric surfactant which have
high surface activity have become one of focus on surfactant research. A typical example of them is dimeric or Gemini surfactant. Quaternary ammonium Gemini surfactants exhibit peculiar properties because of its novel molecular structure.
In this paper, through a series of experiments, two series of quaternary-ammonium Gemini surfactants were synthesized. Their critical micelle concentration(cmc ) values, the surface tension at their cmc( γ cmc) values , the efficiency of decreasing the surface tension(C2o) and the micelle aggregation number were measured; and the factor affected the results were also discussed. The properties of the system of C12-s-C12 2Br/SDS have been investigated. Meanwhile, the use of C12-s-C12 2Br was discussed in this paper. The main results are as follows:
1 Two series of quaternary-ammonium Gemini surfactants have been synthesized with their structures testified. The optimized methods of synthesis were determined by discussing the factors affecting reactions.
2 Their critical micelle concentration(cmc ) values, the surface tension at their cmc( γ cmc) values and the efficiency of decreasing the surface tension(C20) of the two series surfactants were measured. Results show that Gemini surfactants have much lower cmc and stronger surface activity comparing with the corresponding common surfactants.
3 The excess absorption amount at surface and the area of molecule were discussed. A conclusion can be drawn that the excess absorption amount increases and the area of molecule decreases with the increase of space group carbon number. In the foaming properties of the Gemini surfactants synthesized in this paper, β has shown excellent foaming quality and its foam has the most stable properties.
4 The micelle aggregation number were measured by the technique time-resolved fluorescence quenching (TRFQ) and fluorescence polarization. The concentration of quaternary-ammonium Gemini surfactants has great
influences on the micelle aggregation number. The micelle aggregation number increases with the length of spacer group decreased; and the micelle aggregation number decreases with the temperature increasing.
5 The Mixtures of Gemini surfactants and SDS can lower the surface tension of water solutions more effectively, compared with those of the corresponding common surfactants. Their critical micelle concentration(cmc ) values are more small than those of mixtures of common surfactants.
6 Compared with DTAB, C12-3-C12 2Br can promote the rate of the alkali reduction on terylene more efficiently. So it can be used as textile auxiliaries.
引文
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2 R. Zana; Y. Talmon; Nature, 1993,362:228.
3 M.J. Rosen; Chemtech, 1993,30.
4 F.M. Menger; C. A. Littau; J. Am. Chem.Soc., 1991,113:1451.
5 R. Zana; M. Benrraou; R. Rueff; Langmuir 1991,7:1072-1075.
6 E. Alami; H. Levy; R. Zana; Langmuir 1993,9:940-944.
7 E. Alami; G. Beinert; P. Marie R. Zana; Langmuir 1993,9:1465-1467.
8 M. Frindi; B. Michels; H. Levy; R. Zana; Langmuir 1994,10:1140-1145.
9 D. Danino; Y. Talmon, R.Zana; Langmuir 1995,11:1448-1456.
10 R. Zana; H. Levy; Colloids Surfaces A, 1997, 127:229-232.
11 Zana R, InM, Levy H, Dupo rtail G, L angmuir, 1997, 13, 5552-5557.
12 RosenM J, Chem tech., 1993, 30-33.
13 Zana R, Levy H, PapoutsiD et al., L angm u ir, 1995, 11, 3694-3698. 1 Devinsky F, L acko I, Imam T, J. Colloid Interface S ci., 1991, 143,336-342.
15 Ro senM J, Gao T, N akatsuji Yet al., Colloid s S u rf. A. P hy sicochem. A sp., 1994, 88, 1-5
16 M enger F M,Lit tau CA,J. Am. Chem. Soc., 1991, 113, 1451-1452.
17 朱步瑶(zhu B Y)，赵国玺(zhao G x)，精细化工(F ine Chem icals)，1985，2(4)，1-4．
18 赵国玺(zhao G x)，表面活性剂物理化学(Phy sical Chem istry of Surf actants)，北京大学出版社(P ek ing U niversity P ress)，1984，241-249，270-286．
19 M eguro K et al., in N onionic S u rf actants, P hy sical Chemistry, S u rf actant Science Series 23, M arcel Dekker Inc., 1987, 138.
20 李学刚(L iX G)，赵国玺(Zhao G x)，物理化学学报(A cta P hy sico2Ch im ica S inica)，1992，8，191-196．
21 Zhu Y2P, M asuyama A, Kirito Y2I et al., J. A m. Oil Chem. S oc., 1992, 69 (7), 626-632.
22 AlamiE,BeinertG,MarieP,ZanaR,Langmuir, 1993,9,1465-1467.
23 Menger F M,Littau C A.Gemini surfactant:a new. class of self-assembling Molecules[J].J Am Chem Soc, 1993,115:10083-10090.
24 Menger F M,Keiper J S.Gemini surfactants[J].Angew Chem Im Ed,2000,39:1906-1920.
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