枝状低聚咪唑表面活性剂的合成与性能研究
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摘要
低聚表面活性剂是表面活性剂领域的最新研究热点之一。本研究以咪唑、长链溴代烷烃等为主要原料，季戊四醇衍生物为连接基，合成了两个系列六种结构的枝状二聚、四聚咪唑表面活性剂，对合成条件进行优化，得到适宜的合成条件。采用核磁共振氢谱、碳谱、红外光谱、元素分析、热重等手段对中间体和产物的结构进行了表征，证明所合成物质确为目标产物。
采用表面张力法、电导率法测定两个系列六种结构的低聚咪唑表面活性剂水溶液的表面性质、反离子结合度和胶束化热力学性质。实验结果显示：随着表面活性剂疏水链长的增加，枝状二聚咪唑表面活性剂([Cn-P-Cnim]Br2)和四聚咪唑表面活性剂([P-(Cnim)4]Br4)临界胶束浓度(cmc)和气液界面最大吸附量(Γcmc)值均逐渐减小，表面活性剂分子在空气/水界面的最小横截面积(Amin)和效率因子(pC20)值均逐渐增大，表现出较高的表面活性。通过比较[Cn-P-Cnim]Br2与连接基为四亚甲基的线状二聚表面活性剂([Cn-4-Cnim]Br2)的表面性能参数，结果表明：疏水链长相同时[Cn-P-Cnim]Br2的Γcmc更小， Amin值更大，降低表面张力的效率更高。比较[P-(Cnim)4]Br4与[Cn-P-Cnim]Br2的表面性能参数可以看出：[P-(Cnim)4]Br4的cmc值更低，在气-液界面所占的单分子面积Amin更大，饱和吸附量Γcmc更小， pC20值更高，表面性能更优。采用相分离模型，结合实验测得的cmc等实验数据，得到了两个系列六种结构的低聚咪唑表面活性剂水溶液的胶束形成过程的热力学参数(G m， H m， S m)，实验数据表明：不同链长的[Cn-P-Cnim]Br2与[P-(Cnim)4]Br4表面活性剂的G m均为负值，说明枝状低聚咪唑表面活性剂在水溶液中胶束化过程是自发进行的。胶束形成的标准焓变H m均为负值，表明胶束化过程是放热过程。 G m是由较大的T S m引起的， H m要远小于T S m，胶束形成过程是熵驱动的。对于同系列低聚咪唑表面活性剂，随疏水链长的增加， G m下降， H m增大，胶束更容易形成，胶束化过程放出的热量更多。对于疏水链长相同的低聚咪唑表面活性剂，聚合度增加，胶束化吉布斯自由能G m增加，胶束形成更困难。
设计了分子动力学系统，在微观水平上对枝状二聚咪唑表面活性剂性质进行研究。并通过自由能微扰、压力张量等方法研究了系列不同疏水烷基链碳原子数及不同连接基团羟基数的二聚咪唑表面活性剂(BGIS)在水溶液中的热力学性质及表面活性。结果表明：所设计的分子动力学体系和模型可以预测二聚咪唑表面活性剂的热力学性质及表面活性。BGIS分子在水溶液中溶剂化自由能均为负值，溶剂化自由能与分子结构中疏水烷基链碳数及连接基中羟基数目有关,二者增加，溶剂化自由能减小，胶束化能力和胶束体系热力学稳定性均提高；胶束形熵变Sm为胶束化过程的主要驱动力，但随着温度的增加焓驱动的作用在逐渐增强。胶束化过程中存在“焓熵补偿”现象；无羟基结构BGIS分子的补偿温度为307±3/K，连接基团含有羟基的BGIS分子补偿温度为297±3/K。压力张量法对BGIS溶液cmc的模拟表明：温度升高，cmc值增加；BGIS分子疏水烷基链长度碳数及连接基团羟基数目增加，cmc值下降，系列BGIS分子在溶液中胶束热力学稳定性和表面活性均逐渐提高。
研究了两亲丙烯酰胺类聚合物的——丙烯酰胺/2-丙烯酰胺基-2-甲基-丙磺酸/4-乙烯苄基壬烷基酚聚氧乙烯醚(PAAV)和枝状二聚咪唑表面活性剂[C14-P-C14im]Br2之间的相互作用，分别从溶液表面张力、溶液流变特性和溶液微观结构等方面初步揭示PAAV/[C14-P-C14im]Br2二元体系的相互作用关系，研究发现：PAAV/[C14-P-C14im]Br2二元体系在气液界面的表面张力受表面活性剂浓度的影响，有明显的表面张力最低值，但二元体系降低表面张力的能力低于纯[C14-P-C14im]Br2；浓度较低时，PAAV和PAAV/[C14-P-C14im]Br2两种溶液黏度增加都较缓慢，而且黏度相差不大，聚合物的浓度达到600ppm后二元体系黏度明显大于PAAV水溶液黏度；PAAV浓度为600ppm时，二元体系即具有弹性存在，PAAV浓度较高时，低频率的时候，聚表二元体系主要以粘性模式占优势，随着频率的增加，逐渐转变为弹性模式占优势；对比PAAV和二元体系的扫描和透射电镜照片，二者均能形成网状结构，前者网孔较大，较为稀疏，后者聚合物和表面活性剂相互缠绕，能形成立体的网状结构。
Oligomeric surfactants are one of the hotspots of the surfactants field. In this thesis, two series with six chemical structures of branched dimeric and oligomeric imidazolium surfactants with pentaerythritol derivatives as spacer are synthesized by the reaction between imidazolium, long chained bromoalkane and so on. Suitable synthesis conditions are obtained through optimizing experimental conditions. Molecular structures of intermediates and objective products are characterized by1HNMR,13CNMR, IR and element alanalyses.
The surface activities, degree of counterion binding to micelles and thermodynamic properties of micellization of branched dimeric and oligomeric imidazolium surfactants are investigated using surface tension and electrical conductivity measurements. The results show that the critical micelle concentration(cmc) and the saturation adsorbed amount at air/water interface(Γcmc) decreases with the increasing carbon atoms of hydrophobic groups, however the area per molecule at the interface(Amin) and the efficiency of adsorption of surfactant at air/water interface(pC20) increase. Branched oligomeric imidazolium surfactants own high surface activities. Comparing the surface properties of branched dimeric imidazolium surfactants ([Cn-P-Cnim]Br2) with the [Cn-4-Cnim]Br2, we find that Γcmc is smaller, Amin and pC20are larger for [Cn-P-Cnim]Br2with the same long hydrophobic chains. The high effciency is obtained for reducing the surface tension. Comparing the surface properties of branched tetrameric imidazolium surfactants ([P-(Cnim)4]Br4) with the [Cn-P-Cnim]Br2, we find that cmc and Γcmc of [P-(Cnim)4]Br4are smaller, Amin and pC20are larger. According to the phase separation model, the thermodynamic parameters of micellization (G m， H m，
S m) of all branched oligomeric imidazolium surfactants are determined using thermodynamic eqations. It is found that the standard Gibbs free energy change of micellization with different hydrophobic chain lengths are all negative, indicating that the formation of micelles is spontaneous for [Cn-P-Cnim]Br2and [P-(Cnim)4]Br4. The values of standard enthalpy change H mfor micellization are negative as well, implying that the micelle formation process is exothermic. The negative values of
G m are mainly due to the large positive S m。 H m is much smaller than the value of T S m. Therefore, the micellization process is entropy-driven. For the same series of branched oligomeric imidazolium surfactants, higher H m and lower
Gm with increasing hydrophobic chain length suggests that the micelle formation is more feasible. For the same hydrophobic chains for oligomeric imidazolium surfactants, the increase of G m with the polymerization degree indicates that the micelle formation is more difficult.
A molecular dynamics system is constructed in order to study the properties of branched demeric imidazolium surfactants at micro-level. It is found that the thermodynamic behavior and surface activity of branched demeric imidazolium surfactants vary with different hydrophobic chain and spacer’s hydroxyl number (BGIS) in spacer in solution by means of the MD-based free energy perturbation(FEP) and pressurer tensor. It is found that the system this construction can be used to discriminate and predict the surface properties, thermodynamic properties of demeric imidazolium surfactants. The solvation free energy changes of BGIS solution, which are related to hydrophobic chain carbon number and spacer’s hydroxyl number, are negative. The tendency and stability of micellization are both positive. It is found that the micellization of BGIS is entropy-driven and enthalpy-entropy compensated with the increasing contribution of enthalpy. The enthalpy-entropy compensation plots exhibit the excellent linearity and the compensation temperature of BGIS are found to be (297±3) K and (307±3) K separately. In the pressurer tensor model, the cmc value increases with temperature and the cmc value decreases with the hydrophobic chain carbon number and spacer’s hydroxyl number. The surface activity and stability of micelle thermodynamics both increase.
The interaction between branched dimeric imidazolium surfactants [C14-P-C14im]Br2and amphiphilic acrylamide polymers—acrylamide/2-acrylamido-2-methyl-propyl sulfonic acid-4-vinyl benzyl nonyl alkylphenol polyoxyethylene ether(PAAV) is studied for surface tension, the rheological properties and the microstructure of the solution. Preliminary results reveals the interaction for the PAAV/[C14-P-C14im]Br2binary systems. It is found that the surface tension of the gas-liquid interface in polymer-surfactant binary system is affected by the surfactant concentration and shows a clear minimum value. But the binary system has lower ability to decrease the interfacial tension than [C14-P-C14im]Br2. At low concentration, the apparent viscosity of PAAV and PAAV/[C14-P-C14im]Br2binary system solution increase slowly. When the concentration of PAAV is600ppm, the apparent viscosity of binary system is higher than PAAV solution. When PAAV’s concentration is high and low frequency, the viscous mode dominates the polymer-surfactant binary systems mainly. With increase frequency, polymer-surfactant binary systems gradually transform into the dominant elastic mode. Comparing SEM and TEM images of PAAV and binary systems, it si found that both can form a mesh structure. The meshs formed by the former is larger, more sparse, coarser, while in the latter polymer and surfactant intertwine, forming a three-dimensional network structure.
采用表面张力法、电导率法测定两个系列六种结构的低聚咪唑表面活性剂水溶液的表面性质、反离子结合度和胶束化热力学性质。实验结果显示：随着表面活性剂疏水链长的增加，枝状二聚咪唑表面活性剂([Cn-P-Cnim]Br2)和四聚咪唑表面活性剂([P-(Cnim)4]Br4)临界胶束浓度(cmc)和气液界面最大吸附量(Γcmc)值均逐渐减小，表面活性剂分子在空气/水界面的最小横截面积(Amin)和效率因子(pC20)值均逐渐增大，表现出较高的表面活性。通过比较[Cn-P-Cnim]Br2与连接基为四亚甲基的线状二聚表面活性剂([Cn-4-Cnim]Br2)的表面性能参数，结果表明：疏水链长相同时[Cn-P-Cnim]Br2的Γcmc更小， Amin值更大，降低表面张力的效率更高。比较[P-(Cnim)4]Br4与[Cn-P-Cnim]Br2的表面性能参数可以看出：[P-(Cnim)4]Br4的cmc值更低，在气-液界面所占的单分子面积Amin更大，饱和吸附量Γcmc更小， pC20值更高，表面性能更优。采用相分离模型，结合实验测得的cmc等实验数据，得到了两个系列六种结构的低聚咪唑表面活性剂水溶液的胶束形成过程的热力学参数(G m， H m， S m)，实验数据表明：不同链长的[Cn-P-Cnim]Br2与[P-(Cnim)4]Br4表面活性剂的G m均为负值，说明枝状低聚咪唑表面活性剂在水溶液中胶束化过程是自发进行的。胶束形成的标准焓变H m均为负值，表明胶束化过程是放热过程。 G m是由较大的T S m引起的， H m要远小于T S m，胶束形成过程是熵驱动的。对于同系列低聚咪唑表面活性剂，随疏水链长的增加， G m下降， H m增大，胶束更容易形成，胶束化过程放出的热量更多。对于疏水链长相同的低聚咪唑表面活性剂，聚合度增加，胶束化吉布斯自由能G m增加，胶束形成更困难。
设计了分子动力学系统，在微观水平上对枝状二聚咪唑表面活性剂性质进行研究。并通过自由能微扰、压力张量等方法研究了系列不同疏水烷基链碳原子数及不同连接基团羟基数的二聚咪唑表面活性剂(BGIS)在水溶液中的热力学性质及表面活性。结果表明：所设计的分子动力学体系和模型可以预测二聚咪唑表面活性剂的热力学性质及表面活性。BGIS分子在水溶液中溶剂化自由能均为负值，溶剂化自由能与分子结构中疏水烷基链碳数及连接基中羟基数目有关,二者增加，溶剂化自由能减小，胶束化能力和胶束体系热力学稳定性均提高；胶束形熵变Sm为胶束化过程的主要驱动力，但随着温度的增加焓驱动的作用在逐渐增强。胶束化过程中存在“焓熵补偿”现象；无羟基结构BGIS分子的补偿温度为307±3/K，连接基团含有羟基的BGIS分子补偿温度为297±3/K。压力张量法对BGIS溶液cmc的模拟表明：温度升高，cmc值增加；BGIS分子疏水烷基链长度碳数及连接基团羟基数目增加，cmc值下降，系列BGIS分子在溶液中胶束热力学稳定性和表面活性均逐渐提高。
研究了两亲丙烯酰胺类聚合物的——丙烯酰胺/2-丙烯酰胺基-2-甲基-丙磺酸/4-乙烯苄基壬烷基酚聚氧乙烯醚(PAAV)和枝状二聚咪唑表面活性剂[C14-P-C14im]Br2之间的相互作用，分别从溶液表面张力、溶液流变特性和溶液微观结构等方面初步揭示PAAV/[C14-P-C14im]Br2二元体系的相互作用关系，研究发现：PAAV/[C14-P-C14im]Br2二元体系在气液界面的表面张力受表面活性剂浓度的影响，有明显的表面张力最低值，但二元体系降低表面张力的能力低于纯[C14-P-C14im]Br2；浓度较低时，PAAV和PAAV/[C14-P-C14im]Br2两种溶液黏度增加都较缓慢，而且黏度相差不大，聚合物的浓度达到600ppm后二元体系黏度明显大于PAAV水溶液黏度；PAAV浓度为600ppm时，二元体系即具有弹性存在，PAAV浓度较高时，低频率的时候，聚表二元体系主要以粘性模式占优势，随着频率的增加，逐渐转变为弹性模式占优势；对比PAAV和二元体系的扫描和透射电镜照片，二者均能形成网状结构，前者网孔较大，较为稀疏，后者聚合物和表面活性剂相互缠绕，能形成立体的网状结构。
Oligomeric surfactants are one of the hotspots of the surfactants field. In this thesis, two series with six chemical structures of branched dimeric and oligomeric imidazolium surfactants with pentaerythritol derivatives as spacer are synthesized by the reaction between imidazolium, long chained bromoalkane and so on. Suitable synthesis conditions are obtained through optimizing experimental conditions. Molecular structures of intermediates and objective products are characterized by1HNMR,13CNMR, IR and element alanalyses.
The surface activities, degree of counterion binding to micelles and thermodynamic properties of micellization of branched dimeric and oligomeric imidazolium surfactants are investigated using surface tension and electrical conductivity measurements. The results show that the critical micelle concentration(cmc) and the saturation adsorbed amount at air/water interface(Γcmc) decreases with the increasing carbon atoms of hydrophobic groups, however the area per molecule at the interface(Amin) and the efficiency of adsorption of surfactant at air/water interface(pC20) increase. Branched oligomeric imidazolium surfactants own high surface activities. Comparing the surface properties of branched dimeric imidazolium surfactants ([Cn-P-Cnim]Br2) with the [Cn-4-Cnim]Br2, we find that Γcmc is smaller, Amin and pC20are larger for [Cn-P-Cnim]Br2with the same long hydrophobic chains. The high effciency is obtained for reducing the surface tension. Comparing the surface properties of branched tetrameric imidazolium surfactants ([P-(Cnim)4]Br4) with the [Cn-P-Cnim]Br2, we find that cmc and Γcmc of [P-(Cnim)4]Br4are smaller, Amin and pC20are larger. According to the phase separation model, the thermodynamic parameters of micellization (G m， H m，
S m) of all branched oligomeric imidazolium surfactants are determined using thermodynamic eqations. It is found that the standard Gibbs free energy change of micellization with different hydrophobic chain lengths are all negative, indicating that the formation of micelles is spontaneous for [Cn-P-Cnim]Br2and [P-(Cnim)4]Br4. The values of standard enthalpy change H mfor micellization are negative as well, implying that the micelle formation process is exothermic. The negative values of
G m are mainly due to the large positive S m。 H m is much smaller than the value of T S m. Therefore, the micellization process is entropy-driven. For the same series of branched oligomeric imidazolium surfactants, higher H m and lower
Gm with increasing hydrophobic chain length suggests that the micelle formation is more feasible. For the same hydrophobic chains for oligomeric imidazolium surfactants, the increase of G m with the polymerization degree indicates that the micelle formation is more difficult.
A molecular dynamics system is constructed in order to study the properties of branched demeric imidazolium surfactants at micro-level. It is found that the thermodynamic behavior and surface activity of branched demeric imidazolium surfactants vary with different hydrophobic chain and spacer’s hydroxyl number (BGIS) in spacer in solution by means of the MD-based free energy perturbation(FEP) and pressurer tensor. It is found that the system this construction can be used to discriminate and predict the surface properties, thermodynamic properties of demeric imidazolium surfactants. The solvation free energy changes of BGIS solution, which are related to hydrophobic chain carbon number and spacer’s hydroxyl number, are negative. The tendency and stability of micellization are both positive. It is found that the micellization of BGIS is entropy-driven and enthalpy-entropy compensated with the increasing contribution of enthalpy. The enthalpy-entropy compensation plots exhibit the excellent linearity and the compensation temperature of BGIS are found to be (297±3) K and (307±3) K separately. In the pressurer tensor model, the cmc value increases with temperature and the cmc value decreases with the hydrophobic chain carbon number and spacer’s hydroxyl number. The surface activity and stability of micelle thermodynamics both increase.
The interaction between branched dimeric imidazolium surfactants [C14-P-C14im]Br2and amphiphilic acrylamide polymers—acrylamide/2-acrylamido-2-methyl-propyl sulfonic acid-4-vinyl benzyl nonyl alkylphenol polyoxyethylene ether(PAAV) is studied for surface tension, the rheological properties and the microstructure of the solution. Preliminary results reveals the interaction for the PAAV/[C14-P-C14im]Br2binary systems. It is found that the surface tension of the gas-liquid interface in polymer-surfactant binary system is affected by the surfactant concentration and shows a clear minimum value. But the binary system has lower ability to decrease the interfacial tension than [C14-P-C14im]Br2. At low concentration, the apparent viscosity of PAAV and PAAV/[C14-P-C14im]Br2binary system solution increase slowly. When the concentration of PAAV is600ppm, the apparent viscosity of binary system is higher than PAAV solution. When PAAV’s concentration is high and low frequency, the viscous mode dominates the polymer-surfactant binary systems mainly. With increase frequency, polymer-surfactant binary systems gradually transform into the dominant elastic mode. Comparing SEM and TEM images of PAAV and binary systems, it si found that both can form a mesh structure. The meshs formed by the former is larger, more sparse, coarser, while in the latter polymer and surfactant intertwine, forming a three-dimensional network structure.
引文
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