含硼表面活性剂的合成、性质及应用研究
摘要
N-烷基硼酸二乙醇胺酯(N_xB)和酰胺硼酸二乙醇胺酯(N_xOB)表面活性剂是含硼特种表面活性剂。它们将长碳链通过N烷基化和酰化联接在一起的一类含硼表面活性剂，由于是含四配位硼氧杂环结构的表面活性剂和结合长碳链的基本性质从而极大的提高了表面活性。
本文以脂肪酸，脂肪醇，二乙醇胺，硼酸等为主要原料，经过酰化、卤代、酯化、烷基化等经典反应合成了本论文的目的产物，即硼螺环结构化合物。并探讨了各步反应的条件及收率影响。
测定了该系列含硼表面活性剂的基本性质，如溶解性，乳化力，亲水亲油平衡值(HLB)等。研究了该系列表面活性剂的水解稳定性，考察了其水溶液在不同pH值和不同温度下该系列化合物的临界胶团浓度的变化和表面张力的变化，研究了含硼表面活性剂与离子表面活性剂的复配性能。并计算了混合胶团的组成及正负离子表面活性剂的相互作用参数，用量子化学方法计算了N_xB和N_xOB的结构性能规律。
为了探讨该系列含硼表面活性剂的应用性能，论文主要对该表面活性剂的作为离子液体的催化、相转移催化剂和抗静电剂进行了考察。首先作为离子液体催化合成了2-羟基-4正辛氧基二苯甲酮和作为相转移催化剂合成了2-羟基-4甲氧基二苯甲酮。探讨了其动力学性能，考察了添加于聚丙烯(PP)材料中的表面电阻。并探讨了其抗静电的机理。主要工作和实验结果如下：
1、采用PCl_3为酰化剂，合成了脂肪酰氯，并采用通入干燥的HBr气体合成了溴代烷，同时讨论了其反应条件及反应物的影响。
2、合成了硼酸二乙醇胺酯(NB)、N_xB和N_xOB系列产品，并确定了最佳反应条件，用FTIR、~1H-NMR对其结构进行了鉴定。
3、测定了N_xB和N_xOB基本性质，表明N_xB和N_xOB在极性溶剂中有较好的溶解度，对有机物都有良好的乳化能力，通过戴维斯方法计算的HLB值与溶度法测得的基本一致，并且在中性和碱性条件下N_xB和N_xOB系列的表面张力最佳。
4、25℃，N_xB系列都有较低的表面张力，并随碳原子数的增加而最低表面张力下降。N_(12)B比同碳原子数的十二烷基苯磺酸钠(LAS)的最低表面张力34.5mN／m低，且临界胶束浓度为4.1×10~(-5)mol／L，也比LAS低，且随着NaCl浓度的增加而略有下降，比较N_(12)B和N_(16)B，由于C_(16)疏水基的异构体使N_(12)B的临界胶束浓度(cmc)和临界胶束浓度时的表面张力(γ_(cmc))都低，由于增加了亲水基团使得N_(12)OB和N_(16)OB的表面张力和临界胶束浓度都要高于N_(12)B和N_(16)B。
N_xB and N_xOB surfactant is a borate surfactants .Which is made up of long carbon chain by N-alkylation or acylation,The surface activity is greatly enhanced because of structure of borate surfactants and the basic property of long carbon chain.
The borate surfactants was synthesized from the main starting materrals such as: Aliphaticacid 、 alkanol、 diethanolamine by acylation 、 halohydrocarbon、 esterification、N-alkylation.The factors, which influenced on every reaction ,were also discussed.
The basic properties were detected such as dissolvability、emulsification、 HLB et.,the stabilition of hydrolysis were studied.The varies of critical micelle concentration(cmc) and surface tension were investigated in a queons solution with different PH and tempertation.The properties of the system of borate surfactant and cationic surfactant have been investigated and parameters of molecular interaction were calculated .The rules about structure and properties of N_xB and N_xOB were calculated by quantum chemistry.
In order to investigate the application, the catalysis as ion liquid and anlistating have been investigated .Firstly, 2-Hydroxy-4-octyloxybenzophenone was synthesized from 2,4-dihydroxybenzophenone and octyl chloride in the presence of N-octyl-diethanolamine borate as ion liquid, and 2-Hydroxy-4-methyloxybenzo phenone was synthesized from 2,4-dihydroxybenzophenone and dimehylsulfate in the presence of N-octyl-diethanolamine borate as catalysis. The dynamics property was discussed, the surface resistance was measured in PP, and the antistatic mechanism was investigated initially .The main results are as follows:
1 .Aliphatic acid acylchlorides were synthesized in PCl_3 as acylating agent, and the bromic alkylradical were synthesized in olry HBr ,The affecting factors were discussed.
2. NB 、 N_xB and N_xOB were synthesized , The optimized methods of synthesis were determined by discussing the factors affecting reactions, their structures were testified by FTIR、 ~1H-NMR.
3. The property research indicated that,the N_xB and N_xOB can easily dissolved in water, and emulsifying test showed the surfactant has emulsifying ability and the value of HLB is same by Davr's. as by the solubility method .The surface tension of the N_xB and N_xOB solution is better in neutrality or basicity.
4. The lowest surface tension of N_xB solution was better at 25℃, and lowest surface tension would down with carbon . cmc( critical micelle concentration) and γ_(cmc) in N_(12)B are 4.1 × 10~(-4)mol/L, 24.5 mN.m~(-1),what was smaller than LAS . The cmc of N_(12)B- NaCl are down with NaCl up.The surface tension and cmc of N_(12)B and N_(16)B are higher than that of N_(12)OB and N_(16)OB because of hydrophilic group ,but that of N_(12)B is lower than that of N_(16)B because of hydrophobic group .
5. The borate structure and semipolar bond were studied in different pH by infrared spectrum .It indicated that N_xB and N_xOB have not semipolar bond at pH<
本文以脂肪酸，脂肪醇，二乙醇胺，硼酸等为主要原料，经过酰化、卤代、酯化、烷基化等经典反应合成了本论文的目的产物，即硼螺环结构化合物。并探讨了各步反应的条件及收率影响。
测定了该系列含硼表面活性剂的基本性质，如溶解性，乳化力，亲水亲油平衡值(HLB)等。研究了该系列表面活性剂的水解稳定性，考察了其水溶液在不同pH值和不同温度下该系列化合物的临界胶团浓度的变化和表面张力的变化，研究了含硼表面活性剂与离子表面活性剂的复配性能。并计算了混合胶团的组成及正负离子表面活性剂的相互作用参数，用量子化学方法计算了N_xB和N_xOB的结构性能规律。
为了探讨该系列含硼表面活性剂的应用性能，论文主要对该表面活性剂的作为离子液体的催化、相转移催化剂和抗静电剂进行了考察。首先作为离子液体催化合成了2-羟基-4正辛氧基二苯甲酮和作为相转移催化剂合成了2-羟基-4甲氧基二苯甲酮。探讨了其动力学性能，考察了添加于聚丙烯(PP)材料中的表面电阻。并探讨了其抗静电的机理。主要工作和实验结果如下：
1、采用PCl_3为酰化剂，合成了脂肪酰氯，并采用通入干燥的HBr气体合成了溴代烷，同时讨论了其反应条件及反应物的影响。
2、合成了硼酸二乙醇胺酯(NB)、N_xB和N_xOB系列产品，并确定了最佳反应条件，用FTIR、~1H-NMR对其结构进行了鉴定。
3、测定了N_xB和N_xOB基本性质，表明N_xB和N_xOB在极性溶剂中有较好的溶解度，对有机物都有良好的乳化能力，通过戴维斯方法计算的HLB值与溶度法测得的基本一致，并且在中性和碱性条件下N_xB和N_xOB系列的表面张力最佳。
4、25℃，N_xB系列都有较低的表面张力，并随碳原子数的增加而最低表面张力下降。N_(12)B比同碳原子数的十二烷基苯磺酸钠(LAS)的最低表面张力34.5mN／m低，且临界胶束浓度为4.1×10~(-5)mol／L，也比LAS低，且随着NaCl浓度的增加而略有下降，比较N_(12)B和N_(16)B，由于C_(16)疏水基的异构体使N_(12)B的临界胶束浓度(cmc)和临界胶束浓度时的表面张力(γ_(cmc))都低，由于增加了亲水基团使得N_(12)OB和N_(16)OB的表面张力和临界胶束浓度都要高于N_(12)B和N_(16)B。
N_xB and N_xOB surfactant is a borate surfactants .Which is made up of long carbon chain by N-alkylation or acylation,The surface activity is greatly enhanced because of structure of borate surfactants and the basic property of long carbon chain.
The borate surfactants was synthesized from the main starting materrals such as: Aliphaticacid 、 alkanol、 diethanolamine by acylation 、 halohydrocarbon、 esterification、N-alkylation.The factors, which influenced on every reaction ,were also discussed.
The basic properties were detected such as dissolvability、emulsification、 HLB et.,the stabilition of hydrolysis were studied.The varies of critical micelle concentration(cmc) and surface tension were investigated in a queons solution with different PH and tempertation.The properties of the system of borate surfactant and cationic surfactant have been investigated and parameters of molecular interaction were calculated .The rules about structure and properties of N_xB and N_xOB were calculated by quantum chemistry.
In order to investigate the application, the catalysis as ion liquid and anlistating have been investigated .Firstly, 2-Hydroxy-4-octyloxybenzophenone was synthesized from 2,4-dihydroxybenzophenone and octyl chloride in the presence of N-octyl-diethanolamine borate as ion liquid, and 2-Hydroxy-4-methyloxybenzo phenone was synthesized from 2,4-dihydroxybenzophenone and dimehylsulfate in the presence of N-octyl-diethanolamine borate as catalysis. The dynamics property was discussed, the surface resistance was measured in PP, and the antistatic mechanism was investigated initially .The main results are as follows:
1 .Aliphatic acid acylchlorides were synthesized in PCl_3 as acylating agent, and the bromic alkylradical were synthesized in olry HBr ,The affecting factors were discussed.
2. NB 、 N_xB and N_xOB were synthesized , The optimized methods of synthesis were determined by discussing the factors affecting reactions, their structures were testified by FTIR、 ~1H-NMR.
3. The property research indicated that,the N_xB and N_xOB can easily dissolved in water, and emulsifying test showed the surfactant has emulsifying ability and the value of HLB is same by Davr's. as by the solubility method .The surface tension of the N_xB and N_xOB solution is better in neutrality or basicity.
4. The lowest surface tension of N_xB solution was better at 25℃, and lowest surface tension would down with carbon . cmc( critical micelle concentration) and γ_(cmc) in N_(12)B are 4.1 × 10~(-4)mol/L, 24.5 mN.m~(-1),what was smaller than LAS . The cmc of N_(12)B- NaCl are down with NaCl up.The surface tension and cmc of N_(12)B and N_(16)B are higher than that of N_(12)OB and N_(16)OB because of hydrophilic group ,but that of N_(12)B is lower than that of N_(16)B because of hydrophobic group .
5. The borate structure and semipolar bond were studied in different pH by infrared spectrum .It indicated that N_xB and N_xOB have not semipolar bond at pH<
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