松香基双子表面活性剂合成及纳米材料制备
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摘要
本文以松香为原料制备了四种双子表面活性剂,并初步探讨了以松香衍生物基表面活性剂作为模板制备纳米、介孔材料的方法与性能。论文主要分为两部分。
第一部分为松香衍生物基双子表面活性剂的制备及分析,取得的研究结果如下：
(1)以松香酸、环氧氯丙烷、四甲基乙二胺为原料,合成了四甲基乙二胺基-二松香基双子表面活性剂Ⅰ,FTIR确证其结构：经单因素实验确定合成目标产物的较佳条件为：摩尔比2.2：1,反应温度85℃,反应时间20h,制备的产物得率为76.70%,纯度为96.10%；
(2)通过化学合成的方法,分别以松香和脱氢松香为原料,并以四甲基丙二胺为联接基：制备了四甲基丙二胺-二松香基双子表面活性剂Ⅱ,得率为70.5%,纯度为95.5%；四甲基丙二胺基-二脱氢松香基双子表面活性剂Ⅲ,得率为71.0%；纯度为95.9%：
(3)以松香酸和脱氢松香为原料,通过酰氯化、酰胺化、成盐的化学方法合成了乙二胺-二松香酰甘氨酸双子表面活性剂Ⅳ和乙二胺-二脱氢松香酰甘氨酸双子表面活性剂,采用FTIR和1HNMR确证了目标产物的结构；
(4)表面活性分析结果表明：Ⅰ、Ⅱ、Ⅲ、Ⅳ的CMC值分别为1.42×104mol/L、4×10-4mol/L、6×10-4和5×10-4mol/L,对应的Ycmc分别为36.69mN·m-1、37.35mN·m-1、36.63mN·m-1、34.208mN/m;计算pC20值分别为4.15、4.43、4.45和3.81：乳化时间分别为：16min、20min、25min和2.5h; Ⅰ、Ⅱ、Ⅲ与阴离子相溶性好,Ⅳ与阴阳离子的相溶性皆好。
第二部分为纳米(介孔)材料的制备及分析,取得的研究结果如下：
(1)以钛酸四丁酯为原料,以乙二胺-二脱氢松香酰甘氨酸双子表面活性剂为模板,通过水热合成的方法制备了三种纳米二氧化钛：Tio(未加表面活性剂)、Tio.5(加入0.5g表面活性剂)、Ti1.o(加入1.0g表面活性剂)；XRD、SEM、TEM分析结果表明：Ti0、Ti0.5、Ti1.0皆为锐钛矿型结构,Ti10的分散性强于Ti0和Ti0.5,且无团聚现象,其粒径约为8.81nm；通过光催化降解RhB实验结果表明：Ti1.0的光催化活性优于Ti0、Ti0.5,且在3h时Ti1.0对RhB的光催化降解率为99.7%,几乎降解完全。
(2)两种二氧化硅的制备：①以双子表面活性剂Ⅳ为模板,正硅酸乙酯为原料,采用溶胶-凝胶法制备了二氧化硅材料,经TEM及XRD分析结果表明二氧化硅为纳米颗粒构成的多孔材料,为无定形结构；经氮气吸附-脱附实验分析其比表面积和累积孔体积分别为116.83m2/g、0.45cm3/g,平均孔径约为15.31nm。②以双子表面活性剂Ⅱ为模板,正硅酸乙酯为原料,采用微乳液法制备了介孔二氧化硅材料,经TEM及XRD分析结果表明二氧化硅为纳米颗粒构成的介孔材料,为无定形结构；经氮气吸附-脱附分析其比表面积和累积孔体积分别为928.10m2/g、1.04cm3/g,平均孔径约为4.49nm。
(3)两种碳酸钙的制备：①以碳酸钠和氯化钙为原料,以磺化脱氢松香酸二钠盐为模板,以油酸为有机质制备了疏水性碳酸钙。经TEM分析得到碳酸钙颗粒为纳米棒状结构,其平均粒径约为64.4nm;XRD分析可知碳酸钙晶型为方解石型。经FTIR分析表明有机酸已成功接上,与水的接触角约为117.49°；②以磺化脱氢松香酸单钠盐为模板,以油酸为有机质制备了疏水性碳酸钙,经SEM及TEM分析其为空心球形结构,球形粒径约为2-3μm,空心直径小于为1μm;XRD分析其为球霰石型与方解石型混合晶型,摩尔含量分别为81.1%和8.9%；经FTIR及TG分析,表明有机质油酸已经成功对碳酸钙表面进行了修饰,其与水的接触角测定值约为95°,两种碳酸钙皆达到了疏水性的特点。
In this paper, we have prepared four types of Gemini surfactant using rosin as raw materials, and discussed preliminarily the methods and properties of nanometer and mesoporous materials which were prepared by using rosin derivatives based surfactants as templates. This thesis is mainly divided into two parts.
The first part concerned the preparation and analysis of the rosin derivative Gemini surfactants and the results are as follows:
(1)We prepared tetramethylethylenediamine-bis rosin based Gemini surfactant I using rosin, epichlorohydrin and bisethane as raw materials and then identified its chemical structure with FTIR analysis. The optimal condition of synthesizing objective product can be determined by single-factor experiments and it can be described as follows:molar ratio is2.2:1, temperature is85℃and time is20h. The product owns the yield of76.70%and purity of96.10%.
(2)We utilized rosin and dehydrogenated rosin respectively to react with N,N,N',N'-Tetramethyl-1,3-propanediamine which was used as connection group and prepared the N,N,N',N'-Tetramethyl-1,3-propanediamine-bis rosin based Gemini surfactant Ⅱ with the yield of70.5%and purity of95.5%and N,N,N',N'-Tetramethyl-1,3-propanediamine-bis dehydroabietyl Gemini surfactant Ⅲ with the yield of71.0%and purity of95.9%, respectively.
(3)We synthesized ethylenediamine-bis abietinylglycine Gemini surfactant IV and ethylenediamine-bis dehydroabietyl Gemini surfactant by the use of acyl chloride, amidation and salifying chemical synthesis methods with rosin and dehydroabietic acid as raw material, respectively. Then, the chemical structure of the objective products was confirmed by FTIR and1H-NMR analysis.
(4)The surface activity analysis results of the four Gemini surfactants shows that the CMC of Ⅰ,Ⅱ,Ⅲ and Ⅳ are1.42×10-4,4×10-4,6×10-4and5×10-4mol/L, the γcmc are36.69mN·m-1,37.35mN·m-1,36.63mN·m-1and34.208mN m-1, the pc20are4.15,4.43,4.45and3.81and the emulsification time are16min,20min,25min and2.5h, respectively. Ⅰ,Ⅱ and Ⅲ have good miscibility with anion, while Ⅳ has good miscibility with anion and cation.
The second part is about the preparation and analysis of nanometer (mesoporous) materials and the results are as follows:
(1) We prepared three types of nanometer TiO2particles:Tio(without surfactant), Ti0.5(adding0.5g surfactant) and Ti1.0(adding1.0g surfactant) using tetrabutyl titanate as raw materials and ethylenediamine-bis dehydroabietyl Gemini surfactant as templates via hydrothermal synthesis method. The XRD, SEM and TEM results analysis shows that three are all anatase structure, the dispersing effect of Ti1.0particles is better than Ti0and Ti0.5and there is no obvious aggregation among them, and the size of which is about8.81nm. The result of the photocatalytic degradation RhB shows that the photocatalytic activity of Ti1.0is better than Tio and Ti0.5and the degradation rate is99.7%for3hours' reaction, almost decomposed completely.
(2) Preparation of two kinds of SiO2particles:①Nanosized SiO2was prepared using Gemini surfactant Ⅳ as template and tetraethyl silicate as raw material via sol-gel method. Analyzed by TEM and XRD, SiO2is kind of porous material constituting by nanometer particles and which corresponds to amorphous structure. Through the nitrogen adsorption-desorption experiment, we can get that the specific surface area, cumulative pore volume and average pore diameter of SiO2is116.83m2/g,0.45cm3/g and15.31nm, respectively.②Preparation of mesoporous SiO2material with Gemini surfactant Ⅱ as templates and tetraethyl silicate as raw material by microemulsion method. It is a kind of mesoporous material and corresponds to amorphous structure, and which is made up with nanometer particles analyzed by TEM and XRD. Through the nitrogen adsorption-desorption experiment, we can get that the specific surface area, cumulative pore volume and average pore diameter of SiO2is928.10m2/g,1.04cm3/g and4.49nm, respectively.
(3) Preparation of two kinds of calcium carbonate particles:①We prepared hydrophobic calcium carbonate particles using disodium sulfodehydroabietate served as templates, sodium carbonate and calcium chloride as raw material and oleic acid as organic matter. Through the analysis of TEM results, we can see that the calcium carbonate is a kind of nanorod structure whose average particle diameter is64.4nm. XRD result analysis shows that it is calcite structure. Besides, FTIR analysis proves that the calcium carbonate particles have been successful modified by organic acid and whose water contact angle is117.49°.②Preparation of hydrophobic calcium carbonate using sulfodehydroabietic acid based monosodium as template and oleic acid as organic matter. Through the analysis of SEM and TEM results shows that the product is hollow sphere made up with nanometer particles, the spherical diameter ranges from2to3μm and the hollow size is less than1μm. The XRD result analysis shows that it is the mixed crystal of aragonite and calcite and the mole content are81.1%and8.9%, respectively. FTIR and TG results analysis proves that the calcium carbonate particles have been successful modified by organic acid oleic acid and whose water contact angle is95°. Two kinds of calcium carbonate particles have reached to hydrophobic property.
第一部分为松香衍生物基双子表面活性剂的制备及分析,取得的研究结果如下：
(1)以松香酸、环氧氯丙烷、四甲基乙二胺为原料,合成了四甲基乙二胺基-二松香基双子表面活性剂Ⅰ,FTIR确证其结构：经单因素实验确定合成目标产物的较佳条件为：摩尔比2.2：1,反应温度85℃,反应时间20h,制备的产物得率为76.70%,纯度为96.10%；
(2)通过化学合成的方法,分别以松香和脱氢松香为原料,并以四甲基丙二胺为联接基：制备了四甲基丙二胺-二松香基双子表面活性剂Ⅱ,得率为70.5%,纯度为95.5%；四甲基丙二胺基-二脱氢松香基双子表面活性剂Ⅲ,得率为71.0%；纯度为95.9%：
(3)以松香酸和脱氢松香为原料,通过酰氯化、酰胺化、成盐的化学方法合成了乙二胺-二松香酰甘氨酸双子表面活性剂Ⅳ和乙二胺-二脱氢松香酰甘氨酸双子表面活性剂,采用FTIR和1HNMR确证了目标产物的结构；
(4)表面活性分析结果表明：Ⅰ、Ⅱ、Ⅲ、Ⅳ的CMC值分别为1.42×104mol/L、4×10-4mol/L、6×10-4和5×10-4mol/L,对应的Ycmc分别为36.69mN·m-1、37.35mN·m-1、36.63mN·m-1、34.208mN/m;计算pC20值分别为4.15、4.43、4.45和3.81：乳化时间分别为：16min、20min、25min和2.5h; Ⅰ、Ⅱ、Ⅲ与阴离子相溶性好,Ⅳ与阴阳离子的相溶性皆好。
第二部分为纳米(介孔)材料的制备及分析,取得的研究结果如下：
(1)以钛酸四丁酯为原料,以乙二胺-二脱氢松香酰甘氨酸双子表面活性剂为模板,通过水热合成的方法制备了三种纳米二氧化钛：Tio(未加表面活性剂)、Tio.5(加入0.5g表面活性剂)、Ti1.o(加入1.0g表面活性剂)；XRD、SEM、TEM分析结果表明：Ti0、Ti0.5、Ti1.0皆为锐钛矿型结构,Ti10的分散性强于Ti0和Ti0.5,且无团聚现象,其粒径约为8.81nm；通过光催化降解RhB实验结果表明：Ti1.0的光催化活性优于Ti0、Ti0.5,且在3h时Ti1.0对RhB的光催化降解率为99.7%,几乎降解完全。
(2)两种二氧化硅的制备：①以双子表面活性剂Ⅳ为模板,正硅酸乙酯为原料,采用溶胶-凝胶法制备了二氧化硅材料,经TEM及XRD分析结果表明二氧化硅为纳米颗粒构成的多孔材料,为无定形结构；经氮气吸附-脱附实验分析其比表面积和累积孔体积分别为116.83m2/g、0.45cm3/g,平均孔径约为15.31nm。②以双子表面活性剂Ⅱ为模板,正硅酸乙酯为原料,采用微乳液法制备了介孔二氧化硅材料,经TEM及XRD分析结果表明二氧化硅为纳米颗粒构成的介孔材料,为无定形结构；经氮气吸附-脱附分析其比表面积和累积孔体积分别为928.10m2/g、1.04cm3/g,平均孔径约为4.49nm。
(3)两种碳酸钙的制备：①以碳酸钠和氯化钙为原料,以磺化脱氢松香酸二钠盐为模板,以油酸为有机质制备了疏水性碳酸钙。经TEM分析得到碳酸钙颗粒为纳米棒状结构,其平均粒径约为64.4nm;XRD分析可知碳酸钙晶型为方解石型。经FTIR分析表明有机酸已成功接上,与水的接触角约为117.49°；②以磺化脱氢松香酸单钠盐为模板,以油酸为有机质制备了疏水性碳酸钙,经SEM及TEM分析其为空心球形结构,球形粒径约为2-3μm,空心直径小于为1μm;XRD分析其为球霰石型与方解石型混合晶型,摩尔含量分别为81.1%和8.9%；经FTIR及TG分析,表明有机质油酸已经成功对碳酸钙表面进行了修饰,其与水的接触角测定值约为95°,两种碳酸钙皆达到了疏水性的特点。
In this paper, we have prepared four types of Gemini surfactant using rosin as raw materials, and discussed preliminarily the methods and properties of nanometer and mesoporous materials which were prepared by using rosin derivatives based surfactants as templates. This thesis is mainly divided into two parts.
The first part concerned the preparation and analysis of the rosin derivative Gemini surfactants and the results are as follows:
(1)We prepared tetramethylethylenediamine-bis rosin based Gemini surfactant I using rosin, epichlorohydrin and bisethane as raw materials and then identified its chemical structure with FTIR analysis. The optimal condition of synthesizing objective product can be determined by single-factor experiments and it can be described as follows:molar ratio is2.2:1, temperature is85℃and time is20h. The product owns the yield of76.70%and purity of96.10%.
(2)We utilized rosin and dehydrogenated rosin respectively to react with N,N,N',N'-Tetramethyl-1,3-propanediamine which was used as connection group and prepared the N,N,N',N'-Tetramethyl-1,3-propanediamine-bis rosin based Gemini surfactant Ⅱ with the yield of70.5%and purity of95.5%and N,N,N',N'-Tetramethyl-1,3-propanediamine-bis dehydroabietyl Gemini surfactant Ⅲ with the yield of71.0%and purity of95.9%, respectively.
(3)We synthesized ethylenediamine-bis abietinylglycine Gemini surfactant IV and ethylenediamine-bis dehydroabietyl Gemini surfactant by the use of acyl chloride, amidation and salifying chemical synthesis methods with rosin and dehydroabietic acid as raw material, respectively. Then, the chemical structure of the objective products was confirmed by FTIR and1H-NMR analysis.
(4)The surface activity analysis results of the four Gemini surfactants shows that the CMC of Ⅰ,Ⅱ,Ⅲ and Ⅳ are1.42×10-4,4×10-4,6×10-4and5×10-4mol/L, the γcmc are36.69mN·m-1,37.35mN·m-1,36.63mN·m-1and34.208mN m-1, the pc20are4.15,4.43,4.45and3.81and the emulsification time are16min,20min,25min and2.5h, respectively. Ⅰ,Ⅱ and Ⅲ have good miscibility with anion, while Ⅳ has good miscibility with anion and cation.
The second part is about the preparation and analysis of nanometer (mesoporous) materials and the results are as follows:
(1) We prepared three types of nanometer TiO2particles:Tio(without surfactant), Ti0.5(adding0.5g surfactant) and Ti1.0(adding1.0g surfactant) using tetrabutyl titanate as raw materials and ethylenediamine-bis dehydroabietyl Gemini surfactant as templates via hydrothermal synthesis method. The XRD, SEM and TEM results analysis shows that three are all anatase structure, the dispersing effect of Ti1.0particles is better than Ti0and Ti0.5and there is no obvious aggregation among them, and the size of which is about8.81nm. The result of the photocatalytic degradation RhB shows that the photocatalytic activity of Ti1.0is better than Tio and Ti0.5and the degradation rate is99.7%for3hours' reaction, almost decomposed completely.
(2) Preparation of two kinds of SiO2particles:①Nanosized SiO2was prepared using Gemini surfactant Ⅳ as template and tetraethyl silicate as raw material via sol-gel method. Analyzed by TEM and XRD, SiO2is kind of porous material constituting by nanometer particles and which corresponds to amorphous structure. Through the nitrogen adsorption-desorption experiment, we can get that the specific surface area, cumulative pore volume and average pore diameter of SiO2is116.83m2/g,0.45cm3/g and15.31nm, respectively.②Preparation of mesoporous SiO2material with Gemini surfactant Ⅱ as templates and tetraethyl silicate as raw material by microemulsion method. It is a kind of mesoporous material and corresponds to amorphous structure, and which is made up with nanometer particles analyzed by TEM and XRD. Through the nitrogen adsorption-desorption experiment, we can get that the specific surface area, cumulative pore volume and average pore diameter of SiO2is928.10m2/g,1.04cm3/g and4.49nm, respectively.
(3) Preparation of two kinds of calcium carbonate particles:①We prepared hydrophobic calcium carbonate particles using disodium sulfodehydroabietate served as templates, sodium carbonate and calcium chloride as raw material and oleic acid as organic matter. Through the analysis of TEM results, we can see that the calcium carbonate is a kind of nanorod structure whose average particle diameter is64.4nm. XRD result analysis shows that it is calcite structure. Besides, FTIR analysis proves that the calcium carbonate particles have been successful modified by organic acid and whose water contact angle is117.49°.②Preparation of hydrophobic calcium carbonate using sulfodehydroabietic acid based monosodium as template and oleic acid as organic matter. Through the analysis of SEM and TEM results shows that the product is hollow sphere made up with nanometer particles, the spherical diameter ranges from2to3μm and the hollow size is less than1μm. The XRD result analysis shows that it is the mixed crystal of aragonite and calcite and the mole content are81.1%and8.9%, respectively. FTIR and TG results analysis proves that the calcium carbonate particles have been successful modified by organic acid oleic acid and whose water contact angle is95°. Two kinds of calcium carbonate particles have reached to hydrophobic property.
引文
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