季铵化聚芳醚砜酮纳滤膜及阴离子交换膜的研究
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摘要
含二氮杂萘酮结构的聚芳醚砜酮(PPESK)是本研究组开发的新材料，具有较高的玻璃化转变温度，良好的溶解性、成膜性、机械性能和化学稳定性，是一类用于制备分离膜的新型材料。
本文在98％的浓硫酸中，以氯甲基辛醚(CMOE)对PPESK进行氯甲基化改性，制备了氯甲基化聚芳醚砜酮(CMPPESK)。系统研究了反应温度、反应时间、CMOE浓度以及聚合物浓度等因素对PPESK氯甲基化反应程度的影响，优化反应工艺条件，实现了氯甲基化程度的可控制备，氯甲基化程度可高达1.99 mmol·g~(-1)。考察了CMPPESK的溶解性和热性能。CMPPESK在NMP、DMAc、CH_3Cl等极性有机溶剂中具有良好的溶解性。氯甲基基团的引入降低了聚合物的初始失重温度，而且氯甲基化程度越高，初始失重温度越低。在CMPPESK热降解的过程中，氯甲基基团脱落的同时可能伴随交联反应的发生，从而导致氯甲基化程度越高，最终残留量越多。以三甲胺对CMPPESK进行季铵化改性，制备了不同离子交换容量(IEC)的季铵化聚芳醚砜酮(QAPPESK)。考察了QAPPESK的溶解性和热性能。发现离子交换容量(IEC)越高，其耐溶剂性能越好。QAPPESK(IEC=1.18 mmol·g~)(-1))部分溶解于98％的浓硫酸和溶胀于DMF中，在NMP、DMAo等其它的有机溶剂中基本不溶。QAPPESK的季铵基团在200～250℃之间发生失重，而且IEC值越高，热失重就越显著。
由于QAPPESK的溶解性较差，而CMPPESK具有较好的溶解性，因此制备QAPPESK纳滤膜分为两步：首先通过相转化法制备CMPPESK非对称膜，然后对CMPPESK非对称膜进行季铵化改性，制备荷正电的QAPPESK纳滤膜。在相转化法制备CMPPESK非对称膜的过程中，溶剂、非溶剂添加剂的选择与膜的结构和性能紧密相关。采用浊点滴定法，系统考察聚合物、溶剂、非溶剂对铸膜液体系相分离的影响，实验测得了CMPPESK／Solvent／NSA(nonsolvent additive)三相体系在25℃下的浊点，并将实验测定的数据进行了线性模拟，根据线性浊点(LCP)关系外推计算出了三相体系的双节线，由此可得铸膜液体系中非溶剂添加剂的上限含量，为CMPPESK铸膜液体系组成的构建提供了可靠的科学依据。
以CMPPESK为膜材料，制备了CMPPESK非对称膜，对其进行季铵化改性制备了荷正电的QAPPESK纳滤膜，考察了铸膜液溶剂、非溶剂添加剂、季铵化条件等工艺条件对膜性能的影响，优化了制膜工艺条件。在优化的工艺条件下制备的QAPPESK纳滤膜在0.4 MPa下对MgCl_2的截留率可达88％，溶液通量高达56 L·m~(-2)·h~(-1)。季铵化条件对膜的IEC值和溶胀度具有较大的影响，季铵化时间越长，三甲胺浓度越高，使得生成的季铵基团越多，膜的IEC值就越大，同时膜的溶胀度也增大。而且，反应温度越高，膜的溶胀度越大。当三甲胺浓度为5.0 mol·L~(-1)，季铵化时间为5 h，季铵化温度为30℃时，QAPPESK纳滤膜具有较好的膜分离性能。
根据优化的工艺条件，制备了综合性能优异的QAPPESK纳滤膜。由非平衡热力学模型以及静电位阻模型(ES模型)计算出了QAPPESK纳滤膜的膜孔结构参数。考察了QAPPESK纳滤膜对不同无机盐的分离性能以及其耐热性、化学稳定性和对阳离子染料MB的浓缩脱盐研究。QAPPESK纳滤膜对不同无机盐的脱除顺序为：MgCl_2＞MgSO_4＞NaCl＞Na_2SO_4，是典型的荷正电纳滤膜的分离特性。QAPPESK纳滤膜具有良好的耐热性和耐污染性能，在60℃下运行120 h，QAPPESK纳滤膜的分离效果基本不变。QAPPESK纳滤膜具较好耐氯性和耐氧化性能，且在pH值低于10的溶液介质中使用，分离效果基本不变。其对阳离子染料MB具有较好的分离性能和抗污染性能，当对含盐阳离子染料MB进行脱盐精制时，对染料MB的截留率始终保持在99％以上，通量在40 L·m~(-2)·h~(-1)左右波动。经过7次循环的恒容脱盐后，染料中的盐基本除净。
以CMPPESK为膜材料，制备了CMPPESK均质膜，通过对CMPPESK均质膜进行季铵化改性制备了QAPPESK阴离子交换膜，考察了其特征参数、化学稳定性以及电池性能。QAPPESK阴离子交换膜具有较好的化学稳定性，用做全钒氧化还原液流电池隔膜，其能量效率达88.3％，在相同的测试条件下较Nafion112和Nafion117的高，说明QAPPESK用于全钒氧化还原电池隔膜具有较好的应用前景。
Poly(phthalazinone ether sulfone ketone) (PPESK) is a novel membrane material for filtration membrane with high glass-transition temperature, good solubility, well membrane-forming ability, good mechanical performance and chemical stability.
Chloromethylated poly(phthalazinone ether sulfone ketone) (CMPPESK) was prepared from PPESK and chloromethyl octyl ether (CMOE) in concentrated sulfuric acid. The effects of reaction temperature, reaction time, the concentration of CMOE and polymer concentration on the degree of chloromethylation were investigated in detail. The technology conditions were optimized and the degree of chloromethylation could be controllable. The degree of chloromethylation could get to1.99 mmol·g~(-1). The solubility and thermal properties of CMPPESK were also examined. CMPPESK had well solubility, which was soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), and chloroform. It was found that the introduction of chloromethyl groups and quaternary ammonium groups into the polymer chains led to a decrease in the decomposition temperature. And with the increase of the degree of chloromethylation, the initial degradation temperature declined. The decomposition of CMPPESK maybe occurred by both the elimination of chloromethyl functional groups and a cross-linking reaction. The higher the degree of chloromethylation was, the more the residual quantity was. Quaternized poly(phthalazinone ether sulfone ketone) (QAPPESK) with different the ion exchange capacity (IEC) was prepared from CMPPESK and trimethylamine by quaternized modification. The solubility and thermal properties of QAPPESK were also examined. It was found that QAPPESK had better solvent resistance with the increase of the IEC. QAPPESK (IEC=1.18 mmol·g~(-1)) had excellent solvent resistance, which was partly soluble in sulfuric acid (98%) and swollen in N, N-dimethylformamide (DMF) and wan not soluble in NMP, DMAc and other organic solvents. The elimination of quaternary ammonium groups occurred at between 200 and 250℃. And with the increase of the IEC, the weight loss of QAPPESK was much more obvious.
CMPPESK had good solubility, whereas QAPPESK had excellent solvent resistance. Therefore, positively charged QAPPESK NF membrane couldn't be directly prepared from QAPPESK, but could be obtained through the following two steps: (1) The preparation of CMPPESK asymmetric membrane by a phase inversion method. (2) QAPPESK NF membrane was prepared form CMPPESK asymmetric membrane by quaternized modification. Solvent and nonsolvent additives selected had effects on membrane structure and performance in the phase inversion process of preparing CMPPESK asymmetric membrane. The effects of polymer, solvent and nonsolvent on casting systems were investigated in detail by cloud titration method. The cloud of ternary phase system of CMPPESK/Solvent/NS A was tested at 25℃and the data were simulated linearly. The binodal lines of the ternary phase systems were calculated according to the linerized cloud point (LCP) correlation. Therefore, the maximum content of NSA in the casting solution can be calculated according to the bimodal lines of the system, which is a reliable basis for the establishment for the composition of casting solution.
CMPPESK asymmetric membrane was prepared form CMPPESK membrane material. And positively charged quaternized poly(phthalazinone ether sulfone ketone) (QAPPESK) nanofiltration (NF) membranes were prepared from CMPPESK asymmetric membrane by quaternized modification. The effects of preparation conditions, such as casting solvent, nonsolvent additives, quaternization conditions and so on, were investigated and the technology conditions were optimized. QAPPESK NF membranes were obtained by optimal technology conditions, which the MgCl_2 rejection was 88% and the flux was 56 L·m~(-2)·h~(-1) at 0.4 MPa. Quaternization conditions had much larger effects on the EEC and swelling rate of QAPPESK NF membrane. When much more quaternary ammonium groups were introduced, the membrane would get much more positive charges and the IEC of membrane would become much larger. At the same time, the swelling rate of membrane increased. And the swelling rate of membrane also increased with the reaction temperature. when trimethylamine concentration is 5.0 mol·L~(-1), and quaternization time is about 5h, and quaternization temperature is 30℃, QAPPESK NF membrane had much better membrane performance.
QAPPESK NF membranes with good integrated properties were prepared by optimal technology condition. Membrane parameters were calculated according to the irreversible thermodynamic model and the electrostatic and steric-hindrance (ES) model. The properties of QAPPESK NF membrane were studied, such as separating different inorganic salt, the thermal stability, chemical stability and desalination-purification for cation dye MB. The inorganic electrolytes rejection of QAPPESK NF membrane ranks: MgCl_2> MgSO_4> NaCl> Na_2SO_4, which is typical characteristics of a positively charged NF membrane. QAPPESK NF membranes exhibited good thermal stability and fouling resistance. QAPPESK NF membrane held the stable membrane separation performance in 120 h at 60℃. QAPPESK NF membrane showed good free chlorine resistance and oxide resistance, and could hold stable membrane separation performance when the pH of media solution was lower than 10. QAPPESK NF membrane was applied in the desalination-purification for cation dye MB, and the rejection for MB was kept at more than 99% and the flux waved about 40 L·m~(-2)·h~(-1). The cation dye MB was almost desalinized through 7 times cycle.
CMPPESK homogeneous membrane was prepared form CMPPESK membrane material. And QAPPESK anion-exchange membrane was prepared from CMPPESK homogeneous membrane by quaternized modification. The characteristic parameters, chemical stability and battery performance of QAPPESK anion-exchange membrane were investigated. QAPPESK membranes had good chemical stability. The vanadium redox flow battery (V-RFB) using QAPPESK anion-exchange membrane had better performance with 88.3% of overall energy efficiency, which had much higher energy efficiency than Nafion 112 and Nafion 117 at the same test conditions. So QAPPESK anion-exchange membrane is very useful as a separator for the V-RFB with high overall energy efficiency and has promising application prospect in the V-RFB.
本文在98％的浓硫酸中，以氯甲基辛醚(CMOE)对PPESK进行氯甲基化改性，制备了氯甲基化聚芳醚砜酮(CMPPESK)。系统研究了反应温度、反应时间、CMOE浓度以及聚合物浓度等因素对PPESK氯甲基化反应程度的影响，优化反应工艺条件，实现了氯甲基化程度的可控制备，氯甲基化程度可高达1.99 mmol·g~(-1)。考察了CMPPESK的溶解性和热性能。CMPPESK在NMP、DMAc、CH_3Cl等极性有机溶剂中具有良好的溶解性。氯甲基基团的引入降低了聚合物的初始失重温度，而且氯甲基化程度越高，初始失重温度越低。在CMPPESK热降解的过程中，氯甲基基团脱落的同时可能伴随交联反应的发生，从而导致氯甲基化程度越高，最终残留量越多。以三甲胺对CMPPESK进行季铵化改性，制备了不同离子交换容量(IEC)的季铵化聚芳醚砜酮(QAPPESK)。考察了QAPPESK的溶解性和热性能。发现离子交换容量(IEC)越高，其耐溶剂性能越好。QAPPESK(IEC=1.18 mmol·g~)(-1))部分溶解于98％的浓硫酸和溶胀于DMF中，在NMP、DMAo等其它的有机溶剂中基本不溶。QAPPESK的季铵基团在200～250℃之间发生失重，而且IEC值越高，热失重就越显著。
由于QAPPESK的溶解性较差，而CMPPESK具有较好的溶解性，因此制备QAPPESK纳滤膜分为两步：首先通过相转化法制备CMPPESK非对称膜，然后对CMPPESK非对称膜进行季铵化改性，制备荷正电的QAPPESK纳滤膜。在相转化法制备CMPPESK非对称膜的过程中，溶剂、非溶剂添加剂的选择与膜的结构和性能紧密相关。采用浊点滴定法，系统考察聚合物、溶剂、非溶剂对铸膜液体系相分离的影响，实验测得了CMPPESK／Solvent／NSA(nonsolvent additive)三相体系在25℃下的浊点，并将实验测定的数据进行了线性模拟，根据线性浊点(LCP)关系外推计算出了三相体系的双节线，由此可得铸膜液体系中非溶剂添加剂的上限含量，为CMPPESK铸膜液体系组成的构建提供了可靠的科学依据。
以CMPPESK为膜材料，制备了CMPPESK非对称膜，对其进行季铵化改性制备了荷正电的QAPPESK纳滤膜，考察了铸膜液溶剂、非溶剂添加剂、季铵化条件等工艺条件对膜性能的影响，优化了制膜工艺条件。在优化的工艺条件下制备的QAPPESK纳滤膜在0.4 MPa下对MgCl_2的截留率可达88％，溶液通量高达56 L·m~(-2)·h~(-1)。季铵化条件对膜的IEC值和溶胀度具有较大的影响，季铵化时间越长，三甲胺浓度越高，使得生成的季铵基团越多，膜的IEC值就越大，同时膜的溶胀度也增大。而且，反应温度越高，膜的溶胀度越大。当三甲胺浓度为5.0 mol·L~(-1)，季铵化时间为5 h，季铵化温度为30℃时，QAPPESK纳滤膜具有较好的膜分离性能。
根据优化的工艺条件，制备了综合性能优异的QAPPESK纳滤膜。由非平衡热力学模型以及静电位阻模型(ES模型)计算出了QAPPESK纳滤膜的膜孔结构参数。考察了QAPPESK纳滤膜对不同无机盐的分离性能以及其耐热性、化学稳定性和对阳离子染料MB的浓缩脱盐研究。QAPPESK纳滤膜对不同无机盐的脱除顺序为：MgCl_2＞MgSO_4＞NaCl＞Na_2SO_4，是典型的荷正电纳滤膜的分离特性。QAPPESK纳滤膜具有良好的耐热性和耐污染性能，在60℃下运行120 h，QAPPESK纳滤膜的分离效果基本不变。QAPPESK纳滤膜具较好耐氯性和耐氧化性能，且在pH值低于10的溶液介质中使用，分离效果基本不变。其对阳离子染料MB具有较好的分离性能和抗污染性能，当对含盐阳离子染料MB进行脱盐精制时，对染料MB的截留率始终保持在99％以上，通量在40 L·m~(-2)·h~(-1)左右波动。经过7次循环的恒容脱盐后，染料中的盐基本除净。
以CMPPESK为膜材料，制备了CMPPESK均质膜，通过对CMPPESK均质膜进行季铵化改性制备了QAPPESK阴离子交换膜，考察了其特征参数、化学稳定性以及电池性能。QAPPESK阴离子交换膜具有较好的化学稳定性，用做全钒氧化还原液流电池隔膜，其能量效率达88.3％，在相同的测试条件下较Nafion112和Nafion117的高，说明QAPPESK用于全钒氧化还原电池隔膜具有较好的应用前景。
Poly(phthalazinone ether sulfone ketone) (PPESK) is a novel membrane material for filtration membrane with high glass-transition temperature, good solubility, well membrane-forming ability, good mechanical performance and chemical stability.
Chloromethylated poly(phthalazinone ether sulfone ketone) (CMPPESK) was prepared from PPESK and chloromethyl octyl ether (CMOE) in concentrated sulfuric acid. The effects of reaction temperature, reaction time, the concentration of CMOE and polymer concentration on the degree of chloromethylation were investigated in detail. The technology conditions were optimized and the degree of chloromethylation could be controllable. The degree of chloromethylation could get to1.99 mmol·g~(-1). The solubility and thermal properties of CMPPESK were also examined. CMPPESK had well solubility, which was soluble in N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), and chloroform. It was found that the introduction of chloromethyl groups and quaternary ammonium groups into the polymer chains led to a decrease in the decomposition temperature. And with the increase of the degree of chloromethylation, the initial degradation temperature declined. The decomposition of CMPPESK maybe occurred by both the elimination of chloromethyl functional groups and a cross-linking reaction. The higher the degree of chloromethylation was, the more the residual quantity was. Quaternized poly(phthalazinone ether sulfone ketone) (QAPPESK) with different the ion exchange capacity (IEC) was prepared from CMPPESK and trimethylamine by quaternized modification. The solubility and thermal properties of QAPPESK were also examined. It was found that QAPPESK had better solvent resistance with the increase of the IEC. QAPPESK (IEC=1.18 mmol·g~(-1)) had excellent solvent resistance, which was partly soluble in sulfuric acid (98%) and swollen in N, N-dimethylformamide (DMF) and wan not soluble in NMP, DMAc and other organic solvents. The elimination of quaternary ammonium groups occurred at between 200 and 250℃. And with the increase of the IEC, the weight loss of QAPPESK was much more obvious.
CMPPESK had good solubility, whereas QAPPESK had excellent solvent resistance. Therefore, positively charged QAPPESK NF membrane couldn't be directly prepared from QAPPESK, but could be obtained through the following two steps: (1) The preparation of CMPPESK asymmetric membrane by a phase inversion method. (2) QAPPESK NF membrane was prepared form CMPPESK asymmetric membrane by quaternized modification. Solvent and nonsolvent additives selected had effects on membrane structure and performance in the phase inversion process of preparing CMPPESK asymmetric membrane. The effects of polymer, solvent and nonsolvent on casting systems were investigated in detail by cloud titration method. The cloud of ternary phase system of CMPPESK/Solvent/NS A was tested at 25℃and the data were simulated linearly. The binodal lines of the ternary phase systems were calculated according to the linerized cloud point (LCP) correlation. Therefore, the maximum content of NSA in the casting solution can be calculated according to the bimodal lines of the system, which is a reliable basis for the establishment for the composition of casting solution.
CMPPESK asymmetric membrane was prepared form CMPPESK membrane material. And positively charged quaternized poly(phthalazinone ether sulfone ketone) (QAPPESK) nanofiltration (NF) membranes were prepared from CMPPESK asymmetric membrane by quaternized modification. The effects of preparation conditions, such as casting solvent, nonsolvent additives, quaternization conditions and so on, were investigated and the technology conditions were optimized. QAPPESK NF membranes were obtained by optimal technology conditions, which the MgCl_2 rejection was 88% and the flux was 56 L·m~(-2)·h~(-1) at 0.4 MPa. Quaternization conditions had much larger effects on the EEC and swelling rate of QAPPESK NF membrane. When much more quaternary ammonium groups were introduced, the membrane would get much more positive charges and the IEC of membrane would become much larger. At the same time, the swelling rate of membrane increased. And the swelling rate of membrane also increased with the reaction temperature. when trimethylamine concentration is 5.0 mol·L~(-1), and quaternization time is about 5h, and quaternization temperature is 30℃, QAPPESK NF membrane had much better membrane performance.
QAPPESK NF membranes with good integrated properties were prepared by optimal technology condition. Membrane parameters were calculated according to the irreversible thermodynamic model and the electrostatic and steric-hindrance (ES) model. The properties of QAPPESK NF membrane were studied, such as separating different inorganic salt, the thermal stability, chemical stability and desalination-purification for cation dye MB. The inorganic electrolytes rejection of QAPPESK NF membrane ranks: MgCl_2> MgSO_4> NaCl> Na_2SO_4, which is typical characteristics of a positively charged NF membrane. QAPPESK NF membranes exhibited good thermal stability and fouling resistance. QAPPESK NF membrane held the stable membrane separation performance in 120 h at 60℃. QAPPESK NF membrane showed good free chlorine resistance and oxide resistance, and could hold stable membrane separation performance when the pH of media solution was lower than 10. QAPPESK NF membrane was applied in the desalination-purification for cation dye MB, and the rejection for MB was kept at more than 99% and the flux waved about 40 L·m~(-2)·h~(-1). The cation dye MB was almost desalinized through 7 times cycle.
CMPPESK homogeneous membrane was prepared form CMPPESK membrane material. And QAPPESK anion-exchange membrane was prepared from CMPPESK homogeneous membrane by quaternized modification. The characteristic parameters, chemical stability and battery performance of QAPPESK anion-exchange membrane were investigated. QAPPESK membranes had good chemical stability. The vanadium redox flow battery (V-RFB) using QAPPESK anion-exchange membrane had better performance with 88.3% of overall energy efficiency, which had much higher energy efficiency than Nafion 112 and Nafion 117 at the same test conditions. So QAPPESK anion-exchange membrane is very useful as a separator for the V-RFB with high overall energy efficiency and has promising application prospect in the V-RFB.
引文
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