新型三联季铵盐表面活性剂合成与性能研究
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摘要
低聚表面活性剂是近年来出现的一类新型的表面活性剂。它是将两个或两个以上的两亲分子,在头基或靠近头基处由联接基团通过化学键连接在一起而形成的。和传统的表面活性剂相比,它具有很高的表面活性,很低的克拉夫特点和很好的水溶性,被誉为是新一代的表面活性剂。研究低聚表面活性剂的合成及其性能具有重要意义。
本文合成了一种三聚阳离子表面活性剂——三(2-氯化十二烷基二甲铵基乙基)胺(TCDAEA)。以三乙醇胺、氯化亚砜和N,N-二甲基十二烷基叔胺为原料,应用二步法合成了TCDAEA,优化了各步反应条件,确定了较佳的合成工艺条件,并测定了产品的表面活性。
在二步法的合成工艺中,第一步以三乙醇胺、氯化亚砜为原料,经分子内亲核取代反应合成了中间体三(2-氯乙基)胺,并通过单因素条件实验考察了反应温度、反应时间、溶剂质量分数、氯化亚砜和三乙醇胺的物质的量比等因素对三乙醇胺转化率的影响。结果表明:反应温度为60℃、反应时间为4h、溶剂质量分数为20%、nN,N-氯化亚砜:n三乙醇胺=3.9时,三乙醇胺的转化率达到了95.71%;第二步以三(2-氯乙基)胺与N,N-二甲基十二烷基叔胺经季铵化反应合成了目的产物TCDAEA,并通过单因素条件实验考察了催化剂质量分数、反应温度、反应时间、溶剂质量分数、N,N-二甲基十二烷基叔胺与三(2-氯乙基)胺物质的量比等因素对产品产率的影响及其对产品溶液表面张力的影响。结果表明:当氢氧化钾质量分数为0.3%、nN,N-二甲基十二烷基叔胺:n三(2-氯乙基)胺=3.9、溶剂质量分数为20%、反应温度为80℃、反应时间为6h、时,产品收率可达96.56%;当氢氧化钾质量分数为0.3%、nN,N-二甲基十二烷基叔胺:n三(2-氯乙基)胺=3.9、溶剂质量分数为20%、反应温度为80℃、反应时间为6h时,在25℃、临界胶束浓度为4.2×10-4mol/L时,产品溶液的表面张力降低至25.2mN/m。
利用FT-IR、1H-NMR方法表征了中间体三(2-氯乙基)胺和三(2-氯化十二烷基二甲铵基乙基)胺。
三(2-氯化十二烷基二甲铵基乙基)胺是一种新型的三聚季铵盐阳离子表面活性剂。其分子中有3个亲油基和3个亲水基,它比传统的表面活性剂有足够的亲水性和更强的疏水性,具有更高的表面活性。
Oligomeric surfactants are a new type of surfactant emerged in recent years. It is linked with two or more amphiphilic molecules by a spacer group jointed through chemical bonds in the first or near first base. Compared to conventional surfactants, it has a very high surface activity, low clough characteristics and good water-solubility. It is hailed as a new generation of surfactants. Study of oligomeric surfactant synthesis and properties is very significant.
This dissertation had synthesized a kind of trimeric cationic surfactant- tris(2-chlorododecyl dimethylammoniumethyl)amine(TCDAEA)。TCDAEA was prepared by two-step synthesis, in which triethanolamine, thionyl chloride and N,N-dimethyl-dodecylamine as main materials, and optimized the reaction conditions of each step to determine a better synthesis conditions, and determined the product surface activity.
In the two-step synthesis technology, the tris(2-chloroethyl)amine was prepared by intramolecular nucleophilic substitution reactions in which triethanolamine and thionyl chloride as main materials and studied the effect of reaction temperature, reaction time, solvent mass fraction, the molar ratio of thionyl chloride and triethanolamine on the conversion rate of triethanolamine through single-factor conditions of the first step. The results show that the conversion rate of triethanolamine was 95.71% when the reaction temperature was 60℃, reaction time was 4h, solvent mass fraction was 20% and the molar ratio of thionyl chloride and triethanolamine was 3.9. The end products TCDAEA was prepared by quaternization reaction in which tris(2-chloroethyl)amine and N,N-dimethyl-dodecylamine as main materials and studied the effect of mass fraction of catalyst, reaction temperature, reaction time, solvent mass fraction, the molar ratio of tris(2-chloroethyl)amine and N,N-dimethyl-dodecylamine on the yield of product through single-factor conditions and the surface activity of the second step. The results show that the yield of product was 96.56% when the mass fraction of catalyst was 0.3%, the molar ratio of tris(2-chloroethyl)amine and N,N-dimethyl-dodecylamine was 3.9, solvent mass fraction was 20%, the reaction temperature was 80℃and the reaction time was 4h. The surface tension of the products solution reduced to 25.2mN / m at 25℃and the critical micelle concentration of 4.2×10-4mol/L when the when the mass fraction of catalyst was 0.3%, the molar ratio of tris(2-chloroethyl)amine and N,N-dimethyl-dodecylamine was 3.9, solvent mass fraction was 20%, the reaction temperature was 80℃and the reaction time was 4h.
Tris(2-chloroethyl)amine and the end products were characterized by FT-IR, 1H-NMR methods.
TCDAEA is a new type of trimeric cationic quaternary ammonium salts surfactant. Its molecule has three pro-oil-based and three hydrophilic so that it has sufficient hydrophilic, more hydrophobic and higher surface activity than the traditional surfactant.
本文合成了一种三聚阳离子表面活性剂——三(2-氯化十二烷基二甲铵基乙基)胺(TCDAEA)。以三乙醇胺、氯化亚砜和N,N-二甲基十二烷基叔胺为原料,应用二步法合成了TCDAEA,优化了各步反应条件,确定了较佳的合成工艺条件,并测定了产品的表面活性。
在二步法的合成工艺中,第一步以三乙醇胺、氯化亚砜为原料,经分子内亲核取代反应合成了中间体三(2-氯乙基)胺,并通过单因素条件实验考察了反应温度、反应时间、溶剂质量分数、氯化亚砜和三乙醇胺的物质的量比等因素对三乙醇胺转化率的影响。结果表明:反应温度为60℃、反应时间为4h、溶剂质量分数为20%、nN,N-氯化亚砜:n三乙醇胺=3.9时,三乙醇胺的转化率达到了95.71%;第二步以三(2-氯乙基)胺与N,N-二甲基十二烷基叔胺经季铵化反应合成了目的产物TCDAEA,并通过单因素条件实验考察了催化剂质量分数、反应温度、反应时间、溶剂质量分数、N,N-二甲基十二烷基叔胺与三(2-氯乙基)胺物质的量比等因素对产品产率的影响及其对产品溶液表面张力的影响。结果表明:当氢氧化钾质量分数为0.3%、nN,N-二甲基十二烷基叔胺:n三(2-氯乙基)胺=3.9、溶剂质量分数为20%、反应温度为80℃、反应时间为6h、时,产品收率可达96.56%;当氢氧化钾质量分数为0.3%、nN,N-二甲基十二烷基叔胺:n三(2-氯乙基)胺=3.9、溶剂质量分数为20%、反应温度为80℃、反应时间为6h时,在25℃、临界胶束浓度为4.2×10-4mol/L时,产品溶液的表面张力降低至25.2mN/m。
利用FT-IR、1H-NMR方法表征了中间体三(2-氯乙基)胺和三(2-氯化十二烷基二甲铵基乙基)胺。
三(2-氯化十二烷基二甲铵基乙基)胺是一种新型的三聚季铵盐阳离子表面活性剂。其分子中有3个亲油基和3个亲水基,它比传统的表面活性剂有足够的亲水性和更强的疏水性,具有更高的表面活性。
Oligomeric surfactants are a new type of surfactant emerged in recent years. It is linked with two or more amphiphilic molecules by a spacer group jointed through chemical bonds in the first or near first base. Compared to conventional surfactants, it has a very high surface activity, low clough characteristics and good water-solubility. It is hailed as a new generation of surfactants. Study of oligomeric surfactant synthesis and properties is very significant.
This dissertation had synthesized a kind of trimeric cationic surfactant- tris(2-chlorododecyl dimethylammoniumethyl)amine(TCDAEA)。TCDAEA was prepared by two-step synthesis, in which triethanolamine, thionyl chloride and N,N-dimethyl-dodecylamine as main materials, and optimized the reaction conditions of each step to determine a better synthesis conditions, and determined the product surface activity.
In the two-step synthesis technology, the tris(2-chloroethyl)amine was prepared by intramolecular nucleophilic substitution reactions in which triethanolamine and thionyl chloride as main materials and studied the effect of reaction temperature, reaction time, solvent mass fraction, the molar ratio of thionyl chloride and triethanolamine on the conversion rate of triethanolamine through single-factor conditions of the first step. The results show that the conversion rate of triethanolamine was 95.71% when the reaction temperature was 60℃, reaction time was 4h, solvent mass fraction was 20% and the molar ratio of thionyl chloride and triethanolamine was 3.9. The end products TCDAEA was prepared by quaternization reaction in which tris(2-chloroethyl)amine and N,N-dimethyl-dodecylamine as main materials and studied the effect of mass fraction of catalyst, reaction temperature, reaction time, solvent mass fraction, the molar ratio of tris(2-chloroethyl)amine and N,N-dimethyl-dodecylamine on the yield of product through single-factor conditions and the surface activity of the second step. The results show that the yield of product was 96.56% when the mass fraction of catalyst was 0.3%, the molar ratio of tris(2-chloroethyl)amine and N,N-dimethyl-dodecylamine was 3.9, solvent mass fraction was 20%, the reaction temperature was 80℃and the reaction time was 4h. The surface tension of the products solution reduced to 25.2mN / m at 25℃and the critical micelle concentration of 4.2×10-4mol/L when the when the mass fraction of catalyst was 0.3%, the molar ratio of tris(2-chloroethyl)amine and N,N-dimethyl-dodecylamine was 3.9, solvent mass fraction was 20%, the reaction temperature was 80℃and the reaction time was 4h.
Tris(2-chloroethyl)amine and the end products were characterized by FT-IR, 1H-NMR methods.
TCDAEA is a new type of trimeric cationic quaternary ammonium salts surfactant. Its molecule has three pro-oil-based and three hydrophilic so that it has sufficient hydrophilic, more hydrophobic and higher surface activity than the traditional surfactant.
引文
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[3]方战强.表面活性剂在工业中的应用[J].日用化学品学,2000,23(1):35-37.
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