表面活性离子液体在水溶液中的聚集行为
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摘要
表面活性剂是一大类有机化合物,与我们的日常生活密切相关。在实际应用中,表面活性剂往往是复配使用的。表面活性剂与添加剂以及不同种类表面活性剂之间混合形成的体系在结构、形状、性质等方面,与单纯的表面活性剂相比,往往发生了很大的变化。比如单纯的阳离子型或阴离子型表面活性剂在水中形成球形胶束,但是两者以不同浓度复配,从相行为来说,能形成均一相、双水相或者沉淀；从溶液中形成的聚集体方面来说,则含有球形或蠕虫状胶束、囊泡等。除此之外,复配体系在温度、光、电、pH等外界因素影响下还会发生相转变。因此,表面活性剂复配性质的研究,具有重要的理论价值。
离子液体作为一种新兴的绿色溶剂,由于在众多领域的应用,引起人们广泛的关注。通过增长疏水链的链长,可以使其成为具有表面活性的离子液体,从而构建出不同类型的有序分子聚集体。离子液体参与构筑的有序分子聚集体,既可以将离子液体的特性引入到传统的有序分子聚集体中,有助于改善聚集体的性质,又可以进一步拓展离子液体自身的应用。这类研究不仅丰富了离子液体的种类,也为离子液体应用于不同领域提供了理论依据和技术支持,因此具有重要的意义。
本文以具有表面活性的离子液体为研究对象,讨论了吡咯烷类的表面活性离子液体分别与外加盐、阴离子型表面活性剂混合时体系的相行为；咪唑类表面活性离子液体和苯丙烯酸混合体系在紫外光照下,相行为发生的变化。论文的内容分为四个部分：
第一章简介了表面活性剂的溶液性质和具有表面活性的离子液体参与构筑的有序分子聚集体,并重点介绍了蠕虫状胶束的性质及典型的体系。
第二章研究了表面活性离子液体[C16mim]Br和具有光敏感的物质苯丙烯酸的混合体系。苯丙烯酸具有顺反结构,在紫外光照下反式结构可以转化为顺式结构。紫外光谱图证明了结构的转化,通过核磁谱图可以进一步计算出转化率为60%。而顺式结构在光照下,并不能转化为反式结构,说明苯丙烯酸结构转化是不可逆的。在自然界中,苯丙烯酸主要以反式结构存在,所以本章研究了反式苯丙烯酸(trans-CA)和[C16mim]Br混合体系。当[C16mim]Br浓度在40mmol/L以下时,混合体系中的聚集体为球形胶束,并且和trans-CA的浓度无关；[C16mim]Br浓度在40mmol/L和90mmol/L之间时,体系先是溶液,随着trans-CA的浓度增加到一定程度之后,溶液变为具有粘弹性、双折射现象的均一相,流变数据表明是蠕虫状胶束；在[C16mim]Br浓度超过90mmol/L后,形成沉淀区，但是在trans-CA超过一定浓度之后,体系又转变为有粘弹性的均一相,为蠕虫状胶束。所以从浓度角度来划分,在研究的范围内混合体系分为均一相(球形胶束)、多相区和均一相(蠕虫状胶束)。在紫外光照下,[C16mim]Br和trans-CA形成的蠕虫状胶束可以转化为球形胶束,流变数据和Cryo-TEM都证明了这一变化。这是由于在紫外光照下,trans-CA发生光异构化转变为cis-CA,造成有效截面积αs增大,引起临界堆积参数降低,混合体系从蠕虫状胶束转化为球形胶束。
第三章讨论了有机盐诱导吡咯烷类表面活性离子液体形成蠕虫状胶束。以吡咯烷离子液体(C16MPB)的对甲苯磺酸钠(NaTos)水溶液为研究体系,固定C16MPB的浓度,改变NaTos浓度,用流变学方法、低温透射电镜和蠕虫状胶束理论模型进行研究讨论。研究表明：C16MPB/NaTos体系形成粘弹性溶液,在剪切速率作用下,初始阶段剪切应力随剪切速率线性增加,然后趋向平台区,且没有屈服应力,属于假塑性流体；在低频时,体系的粘性性质是主要的,到了高频,则表现为弹性性质,符合Maxwell模型；体系的剪切粘度和复合粘度在相应的剪切速率和振荡频率下具有相似值,符合Cox-Merz规则；稳态剪切表现出剪切变稀现象,Cryo-TEM也进一步印证了流变的结果,说明体系形成了蠕虫状胶束。本章的研究工作扩展了表面活性离子液体的应用范围。
第四章研究了阴阳离子复配体系。阴阳离子表面活性剂复配具有很高的表面活性,可以产生丰富的相行为,但是二者混合又容易产生沉淀,限制了其应用。本章研究了具有表面活性的吡咯烷离子液体(C16MPB)和阴离子表面活性剂十二烷基苯磺酸钠(SDBS)复配体系。研究内容包括两方面：当C16MPB与SDBS混合比例较高时,形成均一相,包括普通溶液和高粘弹性溶液；当二者在等摩尔比例附近时,形成双水相。
(1)在高摩尔混合比例条件下,C16MPB和SDBS可以形成均一相。当C16MPB与SDBS摩尔比例大于10时,形成无偏光、没有粘弹性的普通溶液；当二者比例在7.3～5之间时,可以形成有粘弹性的溶液,流变数据表明体系的粘弹性符合Maxwell模型。这种粘弹性体系的形成,是带不同电荷的极性头基之间静电作用的结果。
(2)在等摩尔比例附近很窄的范围内,C16MPB与SDBS形成双水相。双水相的形成时间和浓度有关,浓度越高,形成双水相所需时间也就越长。在实验范围内,最长需要两周才能形成双水相。而形成之后的双水相很稳定,25℃下可以保持一年以上。通过偏光、TEM、DLS、表面张力等手段表征,确认双水相的上下相中都含有囊泡。不同的是上相是表面活性剂富集的以松散的、类似网状结构形式存在的囊泡相,而下相是含有少量分散囊泡的表面活性剂稀溶液。
The self-assembly of surfactant molecules is of fundamental interest and is important in many applications such as nanomaterial synthesis, drug delivery, separation, pharmaceutical formulation, and other dispersant technologies. Recently, the mixed systems of surfactants with salt or other surfactants have received many attentions due to their higher surface activity than individual surfactant. The cationic and anionic surfactants mixed system, generally called catanionic system, is taken as a typical example, which has unique characteristics. Many catanionic systems have their own specialty in forming aggregates with various morphologies. The mixed surfactant systems can also transform from one phase to another phase under external stimuli, such as light, redox reaction, pH. and temperature. Therefore, the study of mixed surfactant systems is valuable in the theoretical research.
As a novel kind of green solvents, ionic liquids (ILs) have attracted a lot of attentions due to their unique properties. Their physicochemical properties can be easily modulated by suitable selection of cations and anions. An interesting characteristic of ILs is that the cations possess an inherent amphiphilicity, such as1-alkyl-3-methylimidazolium ([C17mim]+),. Therefore, these ILs can exhibit as novel surfactants to self-assemble to form aggregates with specific structure, shape, and properties. The investigations of surface active ILs can enrich the species of ILs and also establish the basis for their applications in different fields. There are four main parts in this dissertation.
Chapter one is a brief introduction of the research background of this work, in which the basic knowledge of surfactant solution and aggregates of surface active ILs are introduced. Especially, the properties of wormlike micelles and the typical system of formed wormlike micelles are focused on.
In Chapter two, a photo-responsive system composed of an imidazolium-type surfactant1-hexadecyl-3-methylimidazolium bromide ([C16mim]Br) and a commonly photosensitive aromatic compound cinnamic acid (CA) is investigated. There are several isoforms and analogs of CA in nature. The trans-and cis-forms are two configurational stereoisomers of CA, and trans-CA is the predominate form of natural CA. So in this work, the mixed system of [C16mim]Br and trans-CA is studied.. Under the UV irradiation, trans-CA can transform to cis-CA. UV spectra proves that the structural transformation of CA, and the conversion ratio calculated by the1H NMR spectrum is60%. In aqueous solution, the compounds [C16mim]Br and trans-CA can form three phase regions:homogeneous phase (spherical micelles), heterogeneous phase (precipitation), and homogeneous phase (wormlike micelles). When the concentration of [C16mim]Br and trans-CA reaches a certain value, the mixed system shows highly viscous, viscoelastic, and flow-birefringence phenomenon. All these phenomenon and rheological results indicate the presence of wormlike micelles. After the UV irradiation, the flow-birefringence phenomenon disappears, meanwhile the viscosity drops. The rheological and visual observations indicate a phase transition from long, wormlike micelles to much shorter micelles upon UV irradiation. Cryo-TEM pictures further proves the phase transition intuitively. This transition is due to the molecular photoisomerization of CA molecules from trans-to cis-, which results in the increase of effective cross-sectional. Then the molecular critical packing decreases and wormlike micelles transform to spherical micelles.
In Chapter three, the formation of wormlike micelle of surface active ILs induced by organic salts in water is investigated. Rheological methods and cryo-TEM measurement were employed to study the viscoelastic properties and formation of wormlike micelles, which are formed by N-hexadecyl-N-methylpyrrolidinium bromide (C16MPB) in aqueous solution in the presence of sodium tosylate (NaTos). The NaTos concentration is varied while the C16MPB concentration is fixed.
The surface active ILs can form wormlike micelles in the presence of organic salts, which is similar to the conventional ionic surfactants (e.g., alkyltrimethylammonium bromide) in aqueous solution. At low shear rates, the relationship between stress and shear rate is linear. There is almost no stress yield value for the C16MPB/NaTos wormlike micelles, exhibiting pseudoplastic fluids. The modulus G' is initially smaller than G", indicating that the system is more viscous than elastic. Then, as frequency increases, G'> G", showing the elastic behavior. The steady-shear viscosity (η) and the absolute value of the complex viscosity (η*) are superimposed at equivalent values of shear rate(γ) and frequency (ω), suggesting that C16MPB/NaTos wormlike micelles obeys the Cox-Merz rule. The C16MPB/NaTos wormlike micelles also follow the Maxwell behavior. The Cryo-TEM images confirms the formation of wormlike micelles in aqueous solution. The effect of hydrocarbon chain length of ILs on the wormlike micelles formation is also studied.
In Chapter four, the mixed system of cationic and anionic surfactants is studied. The mixtures of cationic and anionic surfactant generally have great industrial significance. They exhibit a wide range of unique properties, aggregate morphologies, and interesting phase behaviors. However, except for few systems, most of the mixtures of catanionic surfactant form precipitates or become turbid, which limits their research and application. In this work, we investigated the mixed system of C16MPB and sodium dodecylbenzenes sulfonate (SDBS). The work can be divided into two parts:the homogeneous phase and aqueous two-phase system (ATPS) at different mixture molar ratios. The results are listed below:
(1) C16MPB and SDBS can form homogeneous phase at high molar ratio. When the molar ratio of C16MPB:SDBS is greater than10, the homogeneous phase is ordinary solutions without polarized light and viscoelasticity. When the ratio of C16MPB: SDBS is between7.3and5. the solution shows high viscoelasticity. Typical rheological results indicate that the viscoelasticity of system follows the Maxwell model. This is due to the strong electrostatic interactions between the oppositely charged headgroups.
(2) The system of C16MPB/SDBS forms ATPS within a narrow range near equimolar ratio. Time of ATPS formation is related to total concentration of surfactant. The higher the concentrations are, the longer the formation time becomes. The longest formation time of ATPS in experiment range is about two week. The formed ATPS is very stable and can be maintained for more than one year at25℃. All the POM, DLS, TEM, and surface tension results confirm that the aggregates are in the upper phase, and lower phase of ATPS contains vesicles. The possible formation mechanism of ASTP can be explained as follows. When C16MPB and SDBS are mixed at equimolar ratio, vesicles are formed. More and more vesicles aggregate together. Then the aggregated vesicles form a type of network structure containing water and the network structure separates from the original phase. Compared with the other dispersed vesicles, the surface charge of aggregated vesicles is closer to1:1which led to lower density. As a result, the network structure composed of aggregated vesicles formed the upper part of ATPS, while those dispersed vesicles formed the lower part.
离子液体作为一种新兴的绿色溶剂,由于在众多领域的应用,引起人们广泛的关注。通过增长疏水链的链长,可以使其成为具有表面活性的离子液体,从而构建出不同类型的有序分子聚集体。离子液体参与构筑的有序分子聚集体,既可以将离子液体的特性引入到传统的有序分子聚集体中,有助于改善聚集体的性质,又可以进一步拓展离子液体自身的应用。这类研究不仅丰富了离子液体的种类,也为离子液体应用于不同领域提供了理论依据和技术支持,因此具有重要的意义。
本文以具有表面活性的离子液体为研究对象,讨论了吡咯烷类的表面活性离子液体分别与外加盐、阴离子型表面活性剂混合时体系的相行为；咪唑类表面活性离子液体和苯丙烯酸混合体系在紫外光照下,相行为发生的变化。论文的内容分为四个部分：
第一章简介了表面活性剂的溶液性质和具有表面活性的离子液体参与构筑的有序分子聚集体,并重点介绍了蠕虫状胶束的性质及典型的体系。
第二章研究了表面活性离子液体[C16mim]Br和具有光敏感的物质苯丙烯酸的混合体系。苯丙烯酸具有顺反结构,在紫外光照下反式结构可以转化为顺式结构。紫外光谱图证明了结构的转化,通过核磁谱图可以进一步计算出转化率为60%。而顺式结构在光照下,并不能转化为反式结构,说明苯丙烯酸结构转化是不可逆的。在自然界中,苯丙烯酸主要以反式结构存在,所以本章研究了反式苯丙烯酸(trans-CA)和[C16mim]Br混合体系。当[C16mim]Br浓度在40mmol/L以下时,混合体系中的聚集体为球形胶束,并且和trans-CA的浓度无关；[C16mim]Br浓度在40mmol/L和90mmol/L之间时,体系先是溶液,随着trans-CA的浓度增加到一定程度之后,溶液变为具有粘弹性、双折射现象的均一相,流变数据表明是蠕虫状胶束；在[C16mim]Br浓度超过90mmol/L后,形成沉淀区，但是在trans-CA超过一定浓度之后,体系又转变为有粘弹性的均一相,为蠕虫状胶束。所以从浓度角度来划分,在研究的范围内混合体系分为均一相(球形胶束)、多相区和均一相(蠕虫状胶束)。在紫外光照下,[C16mim]Br和trans-CA形成的蠕虫状胶束可以转化为球形胶束,流变数据和Cryo-TEM都证明了这一变化。这是由于在紫外光照下,trans-CA发生光异构化转变为cis-CA,造成有效截面积αs增大,引起临界堆积参数降低,混合体系从蠕虫状胶束转化为球形胶束。
第三章讨论了有机盐诱导吡咯烷类表面活性离子液体形成蠕虫状胶束。以吡咯烷离子液体(C16MPB)的对甲苯磺酸钠(NaTos)水溶液为研究体系,固定C16MPB的浓度,改变NaTos浓度,用流变学方法、低温透射电镜和蠕虫状胶束理论模型进行研究讨论。研究表明：C16MPB/NaTos体系形成粘弹性溶液,在剪切速率作用下,初始阶段剪切应力随剪切速率线性增加,然后趋向平台区,且没有屈服应力,属于假塑性流体；在低频时,体系的粘性性质是主要的,到了高频,则表现为弹性性质,符合Maxwell模型；体系的剪切粘度和复合粘度在相应的剪切速率和振荡频率下具有相似值,符合Cox-Merz规则；稳态剪切表现出剪切变稀现象,Cryo-TEM也进一步印证了流变的结果,说明体系形成了蠕虫状胶束。本章的研究工作扩展了表面活性离子液体的应用范围。
第四章研究了阴阳离子复配体系。阴阳离子表面活性剂复配具有很高的表面活性,可以产生丰富的相行为,但是二者混合又容易产生沉淀,限制了其应用。本章研究了具有表面活性的吡咯烷离子液体(C16MPB)和阴离子表面活性剂十二烷基苯磺酸钠(SDBS)复配体系。研究内容包括两方面：当C16MPB与SDBS混合比例较高时,形成均一相,包括普通溶液和高粘弹性溶液；当二者在等摩尔比例附近时,形成双水相。
(1)在高摩尔混合比例条件下,C16MPB和SDBS可以形成均一相。当C16MPB与SDBS摩尔比例大于10时,形成无偏光、没有粘弹性的普通溶液；当二者比例在7.3～5之间时,可以形成有粘弹性的溶液,流变数据表明体系的粘弹性符合Maxwell模型。这种粘弹性体系的形成,是带不同电荷的极性头基之间静电作用的结果。
(2)在等摩尔比例附近很窄的范围内,C16MPB与SDBS形成双水相。双水相的形成时间和浓度有关,浓度越高,形成双水相所需时间也就越长。在实验范围内,最长需要两周才能形成双水相。而形成之后的双水相很稳定,25℃下可以保持一年以上。通过偏光、TEM、DLS、表面张力等手段表征,确认双水相的上下相中都含有囊泡。不同的是上相是表面活性剂富集的以松散的、类似网状结构形式存在的囊泡相,而下相是含有少量分散囊泡的表面活性剂稀溶液。
The self-assembly of surfactant molecules is of fundamental interest and is important in many applications such as nanomaterial synthesis, drug delivery, separation, pharmaceutical formulation, and other dispersant technologies. Recently, the mixed systems of surfactants with salt or other surfactants have received many attentions due to their higher surface activity than individual surfactant. The cationic and anionic surfactants mixed system, generally called catanionic system, is taken as a typical example, which has unique characteristics. Many catanionic systems have their own specialty in forming aggregates with various morphologies. The mixed surfactant systems can also transform from one phase to another phase under external stimuli, such as light, redox reaction, pH. and temperature. Therefore, the study of mixed surfactant systems is valuable in the theoretical research.
As a novel kind of green solvents, ionic liquids (ILs) have attracted a lot of attentions due to their unique properties. Their physicochemical properties can be easily modulated by suitable selection of cations and anions. An interesting characteristic of ILs is that the cations possess an inherent amphiphilicity, such as1-alkyl-3-methylimidazolium ([C17mim]+),. Therefore, these ILs can exhibit as novel surfactants to self-assemble to form aggregates with specific structure, shape, and properties. The investigations of surface active ILs can enrich the species of ILs and also establish the basis for their applications in different fields. There are four main parts in this dissertation.
Chapter one is a brief introduction of the research background of this work, in which the basic knowledge of surfactant solution and aggregates of surface active ILs are introduced. Especially, the properties of wormlike micelles and the typical system of formed wormlike micelles are focused on.
In Chapter two, a photo-responsive system composed of an imidazolium-type surfactant1-hexadecyl-3-methylimidazolium bromide ([C16mim]Br) and a commonly photosensitive aromatic compound cinnamic acid (CA) is investigated. There are several isoforms and analogs of CA in nature. The trans-and cis-forms are two configurational stereoisomers of CA, and trans-CA is the predominate form of natural CA. So in this work, the mixed system of [C16mim]Br and trans-CA is studied.. Under the UV irradiation, trans-CA can transform to cis-CA. UV spectra proves that the structural transformation of CA, and the conversion ratio calculated by the1H NMR spectrum is60%. In aqueous solution, the compounds [C16mim]Br and trans-CA can form three phase regions:homogeneous phase (spherical micelles), heterogeneous phase (precipitation), and homogeneous phase (wormlike micelles). When the concentration of [C16mim]Br and trans-CA reaches a certain value, the mixed system shows highly viscous, viscoelastic, and flow-birefringence phenomenon. All these phenomenon and rheological results indicate the presence of wormlike micelles. After the UV irradiation, the flow-birefringence phenomenon disappears, meanwhile the viscosity drops. The rheological and visual observations indicate a phase transition from long, wormlike micelles to much shorter micelles upon UV irradiation. Cryo-TEM pictures further proves the phase transition intuitively. This transition is due to the molecular photoisomerization of CA molecules from trans-to cis-, which results in the increase of effective cross-sectional. Then the molecular critical packing decreases and wormlike micelles transform to spherical micelles.
In Chapter three, the formation of wormlike micelle of surface active ILs induced by organic salts in water is investigated. Rheological methods and cryo-TEM measurement were employed to study the viscoelastic properties and formation of wormlike micelles, which are formed by N-hexadecyl-N-methylpyrrolidinium bromide (C16MPB) in aqueous solution in the presence of sodium tosylate (NaTos). The NaTos concentration is varied while the C16MPB concentration is fixed.
The surface active ILs can form wormlike micelles in the presence of organic salts, which is similar to the conventional ionic surfactants (e.g., alkyltrimethylammonium bromide) in aqueous solution. At low shear rates, the relationship between stress and shear rate is linear. There is almost no stress yield value for the C16MPB/NaTos wormlike micelles, exhibiting pseudoplastic fluids. The modulus G' is initially smaller than G", indicating that the system is more viscous than elastic. Then, as frequency increases, G'> G", showing the elastic behavior. The steady-shear viscosity (η) and the absolute value of the complex viscosity (η*) are superimposed at equivalent values of shear rate(γ) and frequency (ω), suggesting that C16MPB/NaTos wormlike micelles obeys the Cox-Merz rule. The C16MPB/NaTos wormlike micelles also follow the Maxwell behavior. The Cryo-TEM images confirms the formation of wormlike micelles in aqueous solution. The effect of hydrocarbon chain length of ILs on the wormlike micelles formation is also studied.
In Chapter four, the mixed system of cationic and anionic surfactants is studied. The mixtures of cationic and anionic surfactant generally have great industrial significance. They exhibit a wide range of unique properties, aggregate morphologies, and interesting phase behaviors. However, except for few systems, most of the mixtures of catanionic surfactant form precipitates or become turbid, which limits their research and application. In this work, we investigated the mixed system of C16MPB and sodium dodecylbenzenes sulfonate (SDBS). The work can be divided into two parts:the homogeneous phase and aqueous two-phase system (ATPS) at different mixture molar ratios. The results are listed below:
(1) C16MPB and SDBS can form homogeneous phase at high molar ratio. When the molar ratio of C16MPB:SDBS is greater than10, the homogeneous phase is ordinary solutions without polarized light and viscoelasticity. When the ratio of C16MPB: SDBS is between7.3and5. the solution shows high viscoelasticity. Typical rheological results indicate that the viscoelasticity of system follows the Maxwell model. This is due to the strong electrostatic interactions between the oppositely charged headgroups.
(2) The system of C16MPB/SDBS forms ATPS within a narrow range near equimolar ratio. Time of ATPS formation is related to total concentration of surfactant. The higher the concentrations are, the longer the formation time becomes. The longest formation time of ATPS in experiment range is about two week. The formed ATPS is very stable and can be maintained for more than one year at25℃. All the POM, DLS, TEM, and surface tension results confirm that the aggregates are in the upper phase, and lower phase of ATPS contains vesicles. The possible formation mechanism of ASTP can be explained as follows. When C16MPB and SDBS are mixed at equimolar ratio, vesicles are formed. More and more vesicles aggregate together. Then the aggregated vesicles form a type of network structure containing water and the network structure separates from the original phase. Compared with the other dispersed vesicles, the surface charge of aggregated vesicles is closer to1:1which led to lower density. As a result, the network structure composed of aggregated vesicles formed the upper part of ATPS, while those dispersed vesicles formed the lower part.
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