JP2007327052A - Cationic surfactant containing two chains and two hydrophilic groups - Google Patents
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本発明は、陽イオン界面活性剤に関し、更に詳細には、２−ヒドロキシ長鎖アルキル基を有する２鎖２親水基含有陽イオン界面活性剤に関する。 The present invention relates to a cationic surfactant, and more particularly to a two-chain two-hydrophilic group-containing cationic surfactant having a 2-hydroxy long-chain alkyl group.
メソポーラス物質は、１９９２年にＭｏｂｉｌ社が界面活性剤ミセルを構造鋳型剤に用いて新規のシリカ多孔体であるＭＣＭ−４１の報告に始まり、多様な細孔構造を有するメソポーラスシリカが発表され、それ以来、メソポーラス物質の素材としては、シリカに加え、チタニア、ジルコニア等の金属酸化物等が知られるようになっている。触媒活性、吸着活性等の機能性表面を有するメソポーラス物質の効果を発揮させるためには、表面積を大きくした材料が望まれている。このようなメソポーラス物質の調製のために、例えば、ヘキサデシルトリメチルアンモニウム塩のような１鎖１親水基含有陽イオン界面活性剤からなる会合体と金属酸化物前駆体が用いられている（特許文献１、２）。すなわち、メソポーラス物質は、その会合体表面でチタニア前駆体の水和・加水分解反応を生じさせた後、界面活性剤を除去してメソポーラス酸化チタンが調製される。しかし、１鎖１親水基含有陽イオン界面活性剤を用いてメソポーラス酸化チタンを調製するとき、結晶性及び規則性にすぐれたメソポーラス酸化チタンが得られるものの、クラフト点が高いために、調製の際、界面活性剤と酸化チタンの混合水溶液を加熱するという煩雑な操作が必要であり、省エネの観点から望ましくなく、これが欠点であった。 The mesoporous material started in 1992, when Mobil reported on MCM-41, a new porous silica using surfactant micelles as a structural templating agent, and mesoporous silica with various pore structures was announced. Since then, in addition to silica, metal oxides such as titania and zirconia have been known as materials for mesoporous materials. In order to exert the effect of a mesoporous material having a functional surface such as catalytic activity and adsorption activity, a material having a large surface area is desired. For the preparation of such a mesoporous material, for example, an aggregate comprising a 1-chain 1-hydrophilic-containing cationic surfactant such as hexadecyltrimethylammonium salt and a metal oxide precursor are used (Patent Literature). 1, 2). In other words, the mesoporous material causes hydration / hydrolysis reaction of the titania precursor on the surface of the aggregate, and then the surfactant is removed to prepare mesoporous titanium oxide. However, when mesoporous titanium oxide is prepared using a 1-chain 1 hydrophilic group-containing cationic surfactant, although mesoporous titanium oxide with excellent crystallinity and regularity is obtained, the craft point is high. However, a complicated operation of heating a mixed aqueous solution of a surfactant and titanium oxide is necessary, which is not desirable from the viewpoint of energy saving, and this is a drawback.
この欠点を解決するために、クラフト点が低い２鎖２親水基含有陽イオン界面活性剤が検討されており、加熱を必要とせずに室温で調製が可能であることが見出されている。しかし、結晶性及び規則性に十分にすぐれたラメラ状のメソポーラス酸化チタンを与える２鎖２親水基含有陽イオン界面活性剤は得られていない（非特許文献１）。
本発明は、上記現状に鑑みなされたものであり、ラメラ状のメソポーラス酸化チタンを与える２鎖２親水基含有陽イオン界面活性剤を提供することを課題とする。 This invention is made | formed in view of the said present condition, and makes it a subject to provide the 2 chain | strand 2 hydrophilic group containing cationic surfactant which gives a lamellar mesoporous titanium oxide.
本発明者らは、鋭意研究を行った結果、後記一般式（１）で表される２鎖２親水基含有陽イオン界面活性剤が上記要求を満足する高機能の界面活性剤となることを見出し、本発明を完成した。 As a result of intensive studies, the present inventors have found that the 2-chain 2-hydrophilic group-containing cationic surfactant represented by the following general formula (1) is a highly functional surfactant that satisfies the above requirements. The headline and the present invention were completed.
すなわち本発明の請求項１は、下記一般式（１）
本発明の２鎖２親水基含有陽イオン界面活性剤は、光反応触媒、有害物質の除去、吸着剤として利用される、結晶性及び規則性に十分にすぐれたラメラ構造を持つメソポーラス酸化チタンを与える。また本発明の２鎖２親水基含有陽イオン界面活性剤は、抗菌作用を有するので、抗菌剤、殺菌剤、繊維柔軟剤、頭髪処理剤、無機担体の表面処理剤、顔料分散剤、乳化剤、相間移動触媒としても用いられる。 The two-chain, two-hydrophilic group-containing cationic surfactant of the present invention is a mesoporous titanium oxide having a lamellar structure sufficiently excellent in crystallinity and regularity, which is used as a photoreaction catalyst, removal of harmful substances, and an adsorbent. give. Moreover, since the 2 chain | strand 2 hydrophilic group containing cationic surfactant of this invention has an antibacterial action, an antibacterial agent, a disinfectant, a fiber softener, a hair treatment agent, a surface treatment agent of an inorganic carrier, a pigment dispersant, an emulsifier, It is also used as a phase transfer catalyst.
本発明の２鎖２親水基含有陽イオン界面活性剤は、一般式（１）において、２−ヒドロキシ長鎖アルキル基の好ましい炭素原子数は１０から２０であり、４級窒素に結合する短鎖アルキル基は炭素原子数は１から４のアルキル基または２−ヒドロキシエチル基であり、２つの４級窒素原子間の連結基の炭素原子数は２から１２であり、Ｘは塩素原子又は臭素原子である。 In the general formula (1), the 2-hydroxy long-chain alkyl group preferably has 10 to 20 carbon atoms, and the 2-chain 2-hydrophilic group-containing cationic surfactant of the present invention has a short chain bonded to quaternary nitrogen. The alkyl group is an alkyl group having 1 to 4 carbon atoms or a 2-hydroxyethyl group, the linking group between two quaternary nitrogen atoms is 2 to 12, and X is a chlorine atom or a bromine atom It is.
本発明の一般式（１）で表される２鎖２親水基含有陽イオン界面活性剤は、例えば下式において、１，２−エポキシアルカン（２）を有機溶媒中Ｎ，Ｎ’−ジアルキルアルカンジアミン（３）と反応させ、３級アミノ化合物（４）を得た後、ハロゲン化アルキル（５）を反応させて得られる。 The two-chain two-hydrophilic group-containing cationic surfactant represented by the general formula (1) of the present invention is, for example, in the following formula: 1,2-epoxyalkane (2) in an organic solvent, N, N′-dialkylalkane It is obtained by reacting with a diamine (3) to obtain a tertiary amino compound (4) and then reacting with an alkyl halide (5).
（式中、ｍは２から１２までの整数を意味し、ｎは１０から２０までの整数を意味し、Ｒは低級アルキル基を示し、Ｘは塩素原子または臭素原子を示す。 (In the formula, m represents an integer of 2 to 12, n represents an integer of 10 to 20, R represents a lower alkyl group, and X represents a chlorine atom or a bromine atom.
１，２−エポキシアルカン（２）にＮ，Ｎ’−ジアルキルアルカンジアミン（３）を反応させて３級アミノ化合物（４）を得る反応は、有機溶媒中または無溶媒で、５０℃〜１５０℃、好ましくは８０℃〜１３０℃で、攪拌することにより行われる。有機溶媒としては、例えばエタノール、イソプロパノールが好ましい。 The reaction for obtaining the tertiary amino compound (4) by reacting the 1,2-epoxyalkane (2) with the N, N′-dialkylalkanediamine (3) is performed in an organic solvent or without a solvent at 50 ° C. to 150 ° C. It is preferably carried out by stirring at 80 to 130 ° C. As the organic solvent, for example, ethanol and isopropanol are preferable.
３級アミノ化合物（４）にアルキルハライド（５）を反応させ、（１）を得る反応は、有機溶媒中、０℃〜９０℃、好ましくは１５℃〜８０℃で、攪拌することにより行われる。有機溶媒としては、例えばテトラヒドロフラン、エタノール、イソプロパノールが好ましい。 Reaction which makes alkyl halide (5) react with tertiary amino compound (4) and obtains (1) is performed by stirring at 0 ° C. to 90 ° C., preferably 15 ° C. to 80 ° C. in an organic solvent. . As the organic solvent, for example, tetrahydrofuran, ethanol, and isopropanol are preferable.
Ｒ１およびＲ２で表される低級アルキル基としては、メチル基、エチル基、プロピル基、直鎖状ブチル基、分岐状ブチル基等、炭素原子数１〜４のアルキル基が挙げられる。Examples of the lower alkyl group represented by R 1 and R 2 include alkyl groups having 1 to 4 carbon atoms such as a methyl group, an ethyl group, a propyl group, a linear butyl group, and a branched butyl group.
本発明の２鎖２親水基含有陽イオン界面活性剤（１）は、また下式において、１，２−エポキシアルカン（２）を有機溶媒中Ｎ，Ｎ−ジアルキルアミン（６）と反応させ、（７）で表される２−ヒドロキシアルキル基含有の３級アミノ化合物を得た後、ジハロゲン化アルキル（８）を反応させて得られる。 The two-chain two-hydrophilic group-containing cationic surfactant (1) of the present invention is obtained by reacting 1,2-epoxyalkane (2) with N, N-dialkylamine (6) in an organic solvent in the following formula: After obtaining a 2-hydroxyalkyl group-containing tertiary amino compound represented by (7), it is obtained by reacting an alkyl dihalide (8).
１，２−エポキシアルカン（２）にＮ，Ｎ−ジアルキルアミン（６）を反応させて３級アミノ化合物（７）を得る反応は、有機溶媒中または無溶媒で、室温で攪拌することにより行われる。有機溶媒としては、例えば酢酸エチル、テトラヒドロフランが好ましい。 The reaction of 1,2-epoxyalkane (2) with N, N-dialkylamine (6) to give tertiary amino compound (7) is carried out by stirring in an organic solvent or without solvent at room temperature. Is called. As the organic solvent, for example, ethyl acetate and tetrahydrofuran are preferable.
３級アミノ化合物（７）にアルキルジハライド（８）を反応させ、本発明の２鎖２親水基含有陽イオン界面活性剤（１）を得る反応は、有機溶媒中、０℃〜９０℃、好ましくは３５℃〜８０℃で、攪拌することにより行われる。有機溶媒としては、例えばテトラヒドロフラン、エタノール、イソプロパノールが好ましい。 The reaction in which the tertiary amino compound (7) is reacted with an alkyl dihalide (8) to obtain the 2-chain 2-hydrophilic group-containing cationic surfactant (1) of the present invention is carried out in an organic solvent at 0 ° C. to 90 ° C., Preferably, it is carried out by stirring at 35 ° C. to 80 ° C. As the organic solvent, for example, tetrahydrofuran, ethanol, and isopropanol are preferable.
Ｒ１、Ｒ２で表される低級アルキル基としては、メチル基、エチル基、プロピル基、直鎖状ブチル基、分岐状ブチル基等、炭素原子数１〜４のアルキル基または２−ヒドロキシエチル基が挙げられる。Ｒ１がメチル基、Ｒ２が２−ヒドロキシエチル基の場合、Ｎ−メチルエタノールアミンを、Ｒ１およびＲ２が２−ヒドロキシエチル基の場合、ジエタノールアミンをＮ，Ｎ−ジアルキルアミン（６）として用いることができる。Examples of the lower alkyl group represented by R 1 and R 2 include an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, a propyl group, a linear butyl group, a branched butyl group, or 2-hydroxyethyl. Groups. When R 1 is a methyl group and R 2 is a 2-hydroxyethyl group, N-methylethanolamine is used. When R 1 and R 2 are 2-hydroxyethyl groups, diethanolamine is used as an N, N-dialkylamine (6). Can be used.
より詳しく、本発明の２鎖２親水基含有陽イオン界面活性剤を製造する場合の実施態様を説明すれば次の通りである。 In more detail, the embodiment for producing the two-chain, two-hydrophilic group-containing cationic surfactant of the present invention will be described as follows.
Ｎ，Ｎ’−ジメチル−１，６−ヘキサンジアミン及びこれに対して２．１倍モルの１，２−エポキシオクタデカンをエタノール中に溶解する。次に、１２０℃で５時間攪拌する。減圧下溶媒を除去し、シリカゲルを固定相とし、ヘキサン・酢酸エチル（２：１）を移動相とするカラムクロマトグラフィーによって未反応の１，２−エポキシオクタデカンを除去した後、クロロホルム・メタノール（５：１）を移動相として溶出させ、３級アミノ化合物（化４）を得る。 N, N'-dimethyl-1,6-hexanediamine and 2.1 moles of 1,2-epoxyoctadecane are dissolved in ethanol. Next, it stirs at 120 degreeC for 5 hours. The solvent was removed under reduced pressure, unreacted 1,2-epoxyoctadecane was removed by column chromatography using silica gel as the stationary phase and hexane / ethyl acetate (2: 1) as the mobile phase, and then chloroform / methanol (5 1) is eluted as a mobile phase to give a tertiary amino compound (Chemical Formula 4).
この３級アミノ化合物をテトラヒドロフラン（ＴＨＦ）中に溶解する。次に、この溶液に、攪拌下２．５倍当量の臭化メチルを徐々に滴下する。滴下後、５時間攪拌する。減圧下溶媒を除去し、クロロホルム・メタノール混合溶媒を用いて再結晶させ、上記一般式（１）において、ｍは６、ｎは１６、Ｒ１、Ｒ２はメチル基、Ｘは臭素原子である、本発明の２鎖２親水基含有陽イオン界面活性剤（化５）を得る。This tertiary amino compound is dissolved in tetrahydrofuran (THF). Next, 2.5 times equivalent of methyl bromide is gradually added dropwise to this solution with stirring. Stir for 5 hours after dropping. The solvent is removed under reduced pressure, and recrystallization is performed using a chloroform / methanol mixed solvent. In the general formula (1), m is 6, n is 16, R 1 , R 2 are methyl groups, and X is a bromine atom. The 2-chain 2-hydrophilic group-containing cationic surfactant of the present invention (Chemical Formula 5) is obtained.
上記の１，２−エポキシオクタデカンの代わりに、１，２−エポキシドデカン、１，２−エポキシヘキサデカン、１，２−エポキシエイコサンなど、又はそれらの混合物を用いることにより一般式（１）でのｎの異なる本発明の２鎖２親水基含有陽イオン界面活性剤を得る。また、Ｎ，Ｎ’−ジメチル−１，６−ヘキサンジアミンの代わりに、Ｎ，Ｎ’−ジメチル−１，２−エタンジアミン、Ｎ，Ｎ’−ジメチル−１，４−ブタンジアミン、Ｎ，Ｎ’−ジメチル−１，８−オクタンジアミン、Ｎ，Ｎ’−ジメチル−１，８−デカンジアミン、Ｎ，Ｎ’−ジメチル−１，８−ドデカンジアミンを用いることにより一般式（１）でｍの異なる本発明の２鎖２親水基含有陽イオン界面活性剤を得る。さらに、アルキルハライド（５）のハロゲンとして臭素原子又は塩素原子を用いることができる。 In place of the above 1,2-epoxyoctadecane, 1,2-epoxydodecane, 1,2-epoxyhexadecane, 1,2-epoxyeicosane, or the like, or a mixture thereof is used. A two-chain, two-hydrophilic group-containing cationic surfactant of the present invention having a different n is obtained. Further, instead of N, N′-dimethyl-1,6-hexanediamine, N, N′-dimethyl-1,2-ethanediamine, N, N′-dimethyl-1,4-butanediamine, N, N By using '-dimethyl-1,8-octanediamine, N, N'-dimethyl-1,8-decanediamine, N, N'-dimethyl-1,8-dodecanediamine, Different two-chain, two hydrophilic group-containing cationic surfactants of the present invention are obtained. Furthermore, a bromine atom or a chlorine atom can be used as the halogen of the alkyl halide (5).
かくして得られる本発明の２鎖２親水基含有陽イオン界面活性剤は、抗菌剤、殺菌剤、繊維柔軟剤、頭髪処理剤、無機担体の表面処理剤、顔料分散剤、乳化剤、相間移動触媒としても用いられるだけでなく、化粧料、鉱石の浮遊選鉱、油井採掘においても有用である。また、本発明の２鎖２親水基含有陽イオン界面活性剤は、水溶液中で規則性をもって分子状に配列してメソポーラス構造の鋳型（テンプレート）としても利用できる。すなわち、本発明の２鎖２親水基含有陽イオン界面活性剤が分子状に配列した状態で、その表面で、例えばチタンの場合、結晶性チタニアを析出させ、この２鎖２親水基含有陽イオン界面活性剤の会合体を取り除くことによりメソポーラス物質を得ることができる。 The thus obtained two-chain, two-hydrophilic group-containing cationic surfactant of the present invention is an antibacterial agent, bactericidal agent, fiber softener, hair treatment agent, inorganic carrier surface treatment agent, pigment dispersant, emulsifier, phase transfer catalyst. Is also useful in cosmetics, ore flotation and oil well mining. In addition, the two-chain, two-hydrophilic group-containing cationic surfactant of the present invention can be used as a template (template) having a regular molecular arrangement in an aqueous solution and having a regularity. That is, in the state where the two-chain two-hydrophilic group-containing cationic surfactant of the present invention is arranged in a molecular form, for example, in the case of titanium, crystalline titania is precipitated, and this two-chain two-hydrophilic group-containing cation is deposited. By removing the surfactant aggregate, a mesoporous material can be obtained.
以下に実施例を示し、本発明を詳細に説明するが、本発明はこれら実施例のみに限定されない。 EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited only to these examples.
実施例１
Ｎ，Ｎ’−ジメチル−１，６−ヘキサンジアミン（２９ｇ、０．２モル）、１，２−エポキシオクタデカン（１１３ｇ、０．４２モル）を三口フラスコにはかりとり、１２０℃で７時間攪拌する。この後、減圧下溶媒を除去する。その残留物をヘキサン・酢酸エチル（２：１））を用いるシリカゲルカラムクロマトグラフィーによって未反応の原料の除去した後、引き続き、溶媒としてクロロホルム・メタノール（５：１）を用いるシリカゲルカラムクロマトグラフィーと溶媒の除去によって化３で表される３級アミノ化合物（１０９ｇ）を無色粘性物として得た（収率８０％）。この３級アミノ化合物（化３、６８ｇ、０．１モル）をＴＨＦ溶媒（１００ｍＬ）中に溶解し、この溶液に、臭化メチルガスを攪拌下導入しながら、４０℃で１０時間攪拌する。生じた沈殿をろ別した後、クロロホルム・メタノール混合溶媒を用いて再結晶を行い、化５で表される本発明の２鎖２親水基含有陽イオン界面活性剤を白色結晶物（８７ｇ）として得た（収率９０％）。１３Ｃ−ＮＭＲスペクトル（溶媒：重メタノール）を図１に示す。Example 1
N, N′-dimethyl-1,6-hexanediamine (29 g, 0.2 mol) and 1,2-epoxyoctadecane (113 g, 0.42 mol) are weighed in a three-necked flask and stirred at 120 ° C. for 7 hours. . Thereafter, the solvent is removed under reduced pressure. The residue was removed from the unreacted raw material by silica gel column chromatography using hexane / ethyl acetate (2: 1)), followed by silica gel column chromatography using chloroform / methanol (5: 1) as a solvent and the solvent. The tertiary amino compound (109 g) represented by Chemical Formula 3 was obtained as a colorless viscous substance by the removal of (yield 80%). This tertiary amino compound (
実施例２
実施例１において、１，２−エポキシオクタデカン（１１３ｇ、０．４２モル）の代わりに、１，２−エポキシヘキサデカン（１０１ｇ、０．４２モル）を用いる他は、全く同様の操作によって、対応する３級アミノ化合物（９９ｇ）を得る。この３級アミノ化合物（６２ｇ、０．１モル）をＴＨＦ溶媒（１００ｍＬ）中に溶解し、この溶液に、臭化メチルガスを攪拌下導入しながら、４０℃で１０時間攪拌する。生じた沈殿をろ別した後、クロロホルム・メタノール混合溶媒を用いて再結晶を行い、化６で表される本発明の２鎖２親水基含有陽イオン界面活性剤を無色結晶物（７３ｇ）として得た（収率９０％）。Example 2
In Example 1, in place of 1,2-epoxyoctadecane (113 g, 0.42 mol), 1,2-epoxyhexadecane (101 g, 0.42 mol) was used. A tertiary amino compound (99 g) is obtained. The tertiary amino compound (62 g, 0.1 mol) is dissolved in a THF solvent (100 mL), and stirred at 40 ° C. for 10 hours while introducing methyl bromide gas with stirring. After the resulting precipitate was filtered off, recrystallization was performed using a chloroform / methanol mixed solvent, and the 2-chain 2-hydrophilic group-containing cationic surfactant of the present invention represented by Chemical Formula 6 was obtained as a colorless crystal (73 g). Obtained (yield 90%).
実施例３
２−メチルアミノエタノール（７．５ｇ、０．１モル）、１，２−エポキシオクタデカン（３０ｇ、０．１１モル）を三口フラスコにはかりとり、１２０℃で７時間攪拌する。この後、減圧下溶媒を除去する。その残留物をヘキサン・酢酸エチル（２：１）を用いるシリカゲルカラムクロマトグラフィーによって未反応の原料の除去した後、引き続き、溶媒としてクロロホルム・メタノール（５：１）を用いるシリカゲルカラムクロマトグラフィーと溶媒の除去によって化３で表される３級アミノ化合物（２６ｇ）を無色粘性物として得た（収率７５％）。この３級アミノ化合物（１７ｇ、０．０５モル）及び１，８−ジブロモオクタン（６．８ｇ、０．０２５モル）を無水エタノール溶媒（１００ｍＬ）中に溶解し、８０℃で４８時間攪拌する。減圧下溶媒を除去した後、クロロホルム・メタノール混合溶媒を用いて再結晶を行い、化７で表される本発明の２鎖２親水基含有陽イオン界面活性剤を無色結晶物（２１ｇ）として得た（収率８８％）。Example 3
2-Methylaminoethanol (7.5 g, 0.1 mol) and 1,2-epoxyoctadecane (30 g, 0.11 mol) are weighed in a three-necked flask and stirred at 120 ° C. for 7 hours. Thereafter, the solvent is removed under reduced pressure. The residue was removed by silica gel column chromatography using hexane / ethyl acetate (2: 1), followed by silica gel column chromatography using chloroform / methanol (5: 1) as a solvent. Removal gave a tertiary amino compound (26 g) represented by
実施例４
実施例３において、１，２−エポキシオクタデカン（３０ｇ、０．１１モル）の代わりに、１，２−エポキシイコサン（０．１１モル）、２−メチルアミノエタノール（７．５ｇ、０．１モル）の代わりにジエタノールアミン（０．１モル）、１，８−ジブロモオクタン（６．８ｇ、０．０２５モル）の代わりに１，８−ジクロロオクタン（０．０２５モル）を用いる他は、全く同様の操作によって化８で表される本発明の２鎖２親水基含有陽イオン界面活性剤を得た（収率７５％）。Example 4
In Example 3, instead of 1,2-epoxyoctadecane (30 g, 0.11 mol), 1,2-epoxyicosane (0.11 mol), 2-methylaminoethanol (7.5 g, 0.11 mol) Except that diethanolamine (0.1 mol) is used in place of 1 mol) and 1,8-dichlorooctane (0.025 mol) is used in place of 1,8-dibromooctane (6.8 g, 0.025 mol). By the same operation, the 2-chain 2-hydrophilic group-containing cationic surfactant of the present invention represented by Chemical Formula 8 was obtained (yield 75%).
参考例１
水２５ｇに対して実施例１で得た陽イオン界面活性剤（以下、１４−ＯＨ）とこれに対するモル比を種々変化させたトリメチルベンゼンを添加した後、室温で２時間撹拌して６０ｍＭの１４−ＯＨ水溶液を調製した。別に、３Ｍの酸化硫酸チタン水溶液を調製し、１４−ＯＨ水溶液を混合した。その後、室温にて２４時間撹拌し、生成した白色固体を吸引ろ過、水洗、乾燥後、メソポーラス酸化チタン／１４−ＯＨ複合粒子を得た。メソポーラスアナターゼ型酸化チタン／１４−ＯＨ複合粒子のＸＲＤ測定を行った（図２）。この結果から、２θ＝２〜３°付近に規則的構造に由来するブロードなピークを確認した。ＴＭＢ添加比が３〜２０倍の複合粒子においては二つのピークが確認された。これは０．２５倍の１次ピークと３〜２０倍の２次ピークの位置はほぼ一定で、３〜１０倍の範囲ではＴＭＢ添加比が増大するにつれて１次ピークから算出される面間距離が増大していることから、ＴＭＢを取り込み面間距離が拡大した構造（１次ピーク）とＴＭＢを取り込まないまま残った構造（２次ピーク）が共存するためだと考えられる。そこで、面間距離の比を求めると、０倍、２５倍ではその１次ピークと２次ピークから、３〜２０倍では２次ピークと３次ピークから算出される面間距離ｄの比は２であったため、これらはラメラ構造を有していることが判明した（表１）。Reference example 1
After adding the cationic surfactant obtained in Example 1 (hereinafter referred to as 14-OH) and trimethylbenzene having various molar ratios changed thereto with respect to 25 g of water, the mixture was stirred at room temperature for 2 hours and mixed with 14 mM of 14 mM. An —OH aqueous solution was prepared. Separately, a 3M aqueous titanium oxide solution was prepared and mixed with a 14-OH aqueous solution. Thereafter, the mixture was stirred at room temperature for 24 hours, and the produced white solid was subjected to suction filtration, washed with water, and dried to obtain mesoporous titanium oxide / 14-OH composite particles. XRD measurement of mesoporous anatase type titanium oxide / 14-OH composite particles was performed (FIG. 2). From this result, a broad peak derived from a regular structure was confirmed around 2θ = 2 to 3 °. Two peaks were confirmed in the composite particles having a TMB addition ratio of 3 to 20 times. This is because the positions of the primary peak of 0.25 times and the secondary peak of 3 to 20 times are almost constant, and the interplane distance calculated from the primary peak as the TMB addition ratio increases in the range of 3 to 10 times. Therefore, it is considered that the structure (primary peak) in which the inter-plane distance is increased by taking in TMB and the structure (secondary peak) remaining without taking in TMB coexist. Therefore, when the ratio of the inter-plane distance is obtained, the ratio of the inter-plane distance d calculated from the primary peak and the secondary peak at 0 times and 25 times and from the secondary peak and the tertiary peak at 3 to 20 times is as follows. Since it was 2, these were found to have a lamellar structure (Table 1).
比較例１
１４−ＯＨの代わりに下記に示す通常の方の２鎖２親水基含有陽イオン界面活性剤（化８）を用いる他は、参考例１に記載の操作によって得られるメソポーラス酸化チタン／界面活性剤複合粒子は、ヘキサゴナル構造を有するアナターゼ型メソポーラス酸化チタンを与えた。Comparative Example 1
The mesoporous titanium oxide / surfactant obtained by the operation described in Reference Example 1 except that the conventional one-chain two-hydrophilic group-containing cationic surfactant (Chemical Formula 8) shown below is used instead of 14-OH. The composite particles provided anatase-type mesoporous titanium oxide having a hexagonal structure.
本発明の２鎖２親水基含有陽イオン界面活性剤は、光反応触媒、有害物質の除去、吸着剤として利用される、結晶性及び規則性に十分にすぐれたラメラ構造を持つメソポーラスチタニアの調製のための応用が可能である。 The cationic surfactant containing a two-chain two-hydrophilic group of the present invention is a photoreaction catalyst, removal of harmful substances, and preparation of mesoporous titania having a lamellar structure with excellent crystallinity and regularity, which is used as an adsorbent. Application for is possible.
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| JP2014129302A (en) * | 2012-12-28 | 2014-07-10 | Miyoshi Oil & Fat Co Ltd | Novel gemini compound and production method thereof, and cationic surfactant and dispersant that use the novel gemini compound |
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