JP2008074822A - Cationic surfactant containing 4 chains and 4 hydrophilic groups - Google Patents

Cationic surfactant containing 4 chains and 4 hydrophilic groups Download PDF

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JP2008074822A
JP2008074822A JP2006284329A JP2006284329A JP2008074822A JP 2008074822 A JP2008074822 A JP 2008074822A JP 2006284329 A JP2006284329 A JP 2006284329A JP 2006284329 A JP2006284329 A JP 2006284329A JP 2008074822 A JP2008074822 A JP 2008074822A
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cationic surfactant
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Kazuyuki Tsubone
和幸 坪根
Masahiko Abe
正彦 阿部
Hideki Sakai
秀樹 酒井
Hirotoku Nishiyama
広徳 西山
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Abstract

<P>PROBLEM TO BE SOLVED: To provide a cationic surfactant containing 4 chains and 4 hydrophilic groups, which is used as a solubilizing agent, an emulsifier, an antibacterial agent, a disinfectant, a fiber softener, a hair treatment agent, a surface treatment agent for an inorganic carrier, a pigment dispersant or a phase transfer catalyst. <P>SOLUTION: The cationic surfactant containing 4 chains and 4 hydrophilic groups is represented by formula (1) (wherein n is an integer of 8-20; R is a lower alkyl group or a 2-hydroxyethyl group; S is a 2-12C alkylene chain or an alkylene chain containing an aromatic ring; and X is a chlorine or bromine atom). <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

本発明は、４鎖４親水基含有陽イオン界面活性剤に関し、更に詳細には、４つの２−ヒドロキシアルキル基と４つのアンモニウム基を分子内に有する４鎖４親水基含有陽イオン界面活性剤に関する。  The present invention relates to a 4-chain 4-hydrophilic group-containing cationic surfactant, and more specifically, a 4-chain 4-hydrophilic group-containing cationic surfactant having four 2-hydroxyalkyl groups and four ammonium groups in the molecule. About.

現在、従来の１鎖１親水基含有界面活性剤２分子を共有結合で２分子連結させた２鎖２親水基含有界面活性剤が、そのすぐれた界面活性能のために低濃度の配合で済み、環境への負荷が低減化され、皮膚刺激もほとんどないなどの特徴から、研究開発が進められてきている（特許文献１参照）。実際、本願発明者は、２鎖２親水基含有界面活性剤が対応する”モノマー”に比べて皮膚安全性にすぐれることを明らかにした（非特許文献２参照）。一方、界面活性剤の利用面で重要な性能の１つに可溶化がある。この点での２鎖２親水基含有界面活性剤の性能は、被可溶化物をオレンジＯＴとするとき、１鎖１親水基含有界面活性剤の性能の３倍である（非特許文献３参照）。しかし、この可溶化能はまだ必ずしも十分ではなく一層の構造変換が必要である。
特許登録第３４２６４９３号 Ｋａｚｕｙｕｋｉ Ｔｓｕｂｏｎｅら著、ジャーナル オブ サーファクタント アンド ディタージャント（Ｊｏｕｒｎａｌ ｏｆ Ｓｕｒｆａｃｔａｎｔ ＆ Ｄｅｔｅｒｇｅｎｔ，第６巻、１号、３９−４６頁、２００３年） Ｋａｚｕｙｕｋｉ Ｔｓｕｂｏｎｅら著、ジャーナル オブ オレオ サイエンス（Ｊｏｕｒｎａｌ ｏｆ Ｏｌｅｏ Ｓｃｉｅｎｃｅ，第５１巻、６号、３７１−３７８頁、２００２年） Currently, two-chain two-hydrophilic group-containing surfactants in which two molecules of conventional one-chain one-hydrophilic group-containing surfactants are covalently linked to each other need only be formulated at a low concentration due to their excellent surface-active ability. Research and development have been promoted from the viewpoint that the burden on the environment is reduced and there is almost no skin irritation (see Patent Document 1). In fact, the present inventor has clarified that the 2-chain 2-hydrophilic group-containing surfactant is superior to the corresponding “monomer” in terms of skin safety (see Non-Patent Document 2). On the other hand, solubilization is one of the important performances in terms of utilization of surfactants. The performance of the 2-chain 2-hydrophilic group-containing surfactant in this respect is three times the performance of the 1-chain 1-hydrophilic group-containing surfactant when the solubilized product is Orange OT (see Non-Patent Document 3). ). However, this solubilizing ability is not always sufficient, and further structural transformation is required.
Patent registration No. 3426493 Kazuyuki Tsubone et al., Journal of Surfactant and Detergent (Journal of Surfactant & Detergent, Vol. 6, No. 1, pp. 39-46, 2003) Kazuyuki Tsubone et al., Journal of Oreo Science (Journal of Oleo Science, Vol. 51, No. 6, 371-378, 2002)

本発明は、上記現状に鑑みなされたものであり、高性能の可溶化能を持つ４鎖４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 4 chain | strand 4 hydrophilic group containing cationic surfactant with a high performance solubilization ability.

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４鎖４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ものであることを見出し、本発明を完成した。  As a result of intensive studies, the present inventors have found that a 4-chain 4 hydrophilic group-containing cationic surfactant represented by the following general formula (1) is a highly functional surfactant that satisfies the above requirements. As a result, the present invention was completed.

すなわち本発明の請求項１は、下記一般式（１）

Figure 2008074822
（式中、ｎは８から２０までの整数を意味し、Ｒは低級アルキル基又は２−ヒドロキシエチル基を示し、Ｓは炭素原子数２から１２のアルキレン鎖又は芳香環を含むアルキレン鎖、Ｘは塩素原子又は臭素原子を示す。）で表わされることを特徴とする４鎖４親水基含有陽イオン界面活性剤である。That is, claim 1 of the present invention provides the following general formula (1)
Figure 2008074822
 (Wherein n represents an integer of 8 to 20, R represents a lower alkyl group or a 2-hydroxyethyl group, S represents an alkylene chain having 2 to 12 carbon atoms or an alkylene chain containing an aromatic ring, X Represents a chlorine atom or a bromine atom)), and is a cationic surfactant containing a 4-chain 4-hydrophilic group.

本発明の４鎖４親水基含有陽イオン界面活性剤は、可溶化作用だけでなく、抗菌作用を有するので、抗菌剤、殺菌剤として利用することができる。また、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。  Since the 4-chain 4 hydrophilic group-containing cationic surfactant of the present invention has not only a solubilizing action but also an antibacterial action, it can be used as an antibacterial agent and a bactericidal agent. It is also used as a fiber softener, hair treatment agent, inorganic carrier surface treatment agent, pigment dispersant, emulsifier, and phase transfer catalyst.

本発明の４鎖４親水基含有陽イオン界面活性剤は、一般式（１）において、疎水基である２位に水酸基を含むアルキル基の好ましい炭素原子数は８から２０である。２つの４級窒素原子間の連結基は、炭素原子数２から１２のアルキレン鎖又は芳香環を含むアルキレン鎖であり、このとき、炭素原子数１から３のアルキレン鎖と芳香環の結合はメタ又はパラ位である。Ｒは１から３の炭素原子数を持つ短鎖アルキル基又は２−ヒドロキシエチル基である。Ｘは塩素原子又は臭素原子である。  In the general formula (1), the 4-chain 4-hydrophilic group-containing cationic surfactant of the present invention preferably has 8 to 20 carbon atoms in the alkyl group containing a hydroxyl group at the 2-position which is a hydrophobic group. The linking group between two quaternary nitrogen atoms is an alkylene chain having 2 to 12 carbon atoms or an alkylene chain containing an aromatic ring. At this time, the bond between the alkylene chain having 1 to 3 carbon atoms and the aromatic ring is a meta group. Or in the para position. R is a short-chain alkyl group having 1 to 3 carbon atoms or a 2-hydroxyethyl group. X is a chlorine atom or a bromine atom.

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、（２）で表される１，２−エポキシアルカンを有機溶媒中（３）で表されるＮ−メチルアミンと反応させ、（４）で表されるＮ−２−ヒドロキシアルキル，Ｎ−メチルアミンを得た後、（５）で表されるジハロゲン化アルキルを反応させて得られる「ジアミン」を、１，２−エポキシアルカンを有機溶媒中（３）で表されるジメチルアミンと反応させ、（８）で表されるＮ−２−ヒドロキシアルキルジメチルアミンをジハロゲン化アルキル（５）と反応させて得られる「第４級アンモニウム化合物」（９）と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 obtained by, for example, converting the 1,2-epoxyalkane represented by (2) in an organic solvent (3) It is obtained by reacting with an N-methylamine represented by (4) to obtain N-2-hydroxyalkyl and N-methylamine represented by (4), and then reacting with an alkyl dihalide represented by (5). Then, 1,2-epoxyalkane is reacted with dimethylamine represented by (3) in an organic solvent, and N-2-hydroxyalkyldimethylamine represented by (8) is dihalogenated with alkyl (5 ) To obtain a “quaternary ammonium compound” (9).

Figure 2008074822
Figure 2008074822

１，２−エポキシアルカン（１）にメチルアミン（２）又はジメチルアミン（７）を反応させて２級アミン化合物（３）又は３級アミン化合物（８）を得る反応は、有機溶媒中、室温で、攪拌することにより行われる。有機溶媒としては、例えばテトラヒドロフランが好ましい。  The reaction of 1,2-epoxyalkane (1) with methylamine (2) or dimethylamine (7) to give secondary amine compound (3) or tertiary amine compound (8) is carried out at room temperature in an organic solvent. And by stirring. As the organic solvent, for example, tetrahydrofuran is preferable.

２級アミン化合物（３）にジハロゲン化アルキル（５）を反応させ、（６）を得る反応は、有機溶媒中、室温〜７０℃、好ましくは４５℃〜５５℃で、攪拌することにより行われる。有機溶媒としては、例えばジメチルホルムアミドが好ましい。  The reaction for obtaining the alkyl halide (5) by reacting the secondary amine compound (3) to obtain (6) is carried out in an organic solvent by stirring at room temperature to 70 ° C, preferably 45 ° C to 55 ° C. . As the organic solvent, for example, dimethylformamide is preferable.

３級アミン化合物（３）にジハロゲン化アルキル（５）を反応させ、（９）を得る反応は、有機溶媒中、室温〜７０℃、好ましくは４５℃〜５５℃で、攪拌することにより行われる。有機溶媒としては、例えばアセトニトリルが好ましい。  Reaction which makes tertiary amine compound (3) react with dihalogenated alkyl (5) and obtains (9) is performed by stirring at room temperature to 70 ° C, preferably 45 ° C to 55 ° C in an organic solvent. . As the organic solvent, for example, acetonitrile is preferable.

より詳しく、本発明の４鎖４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１，２−エポキシヘキサデカンを用いて説明すれば次の通りである。  More specifically, an embodiment in the case of producing the 4-chain 4 hydrophilic group-containing cationic surfactant of the present invention will be described using 1,2-epoxyhexadecane as follows.

１，２−エポキシヘキサデカン５０ｇ、テトラヒドロフラン１００ｍｌ、メチルアミン４０％水溶液を１６０ｇ量りとり、密栓をして室温で２４時間攪拌する。減圧下溶媒を除去し、ヘキサンを再結晶溶媒として用いて精製後、化３で表される２級アミン化合物（４’）を得る。  Weigh 50 g of 1,2-epoxyhexadecane, 100 ml of tetrahydrofuran, and 160 g of a 40% aqueous solution of methylamine, seal and seal at room temperature for 24 hours. The solvent is removed under reduced pressure, and after purification using hexane as a recrystallization solvent, a secondary amine compound (4 ') represented by Chemical Formula 3 is obtained.

Figure 2008074822
Figure 2008074822

この２級アミノ化合物（４’）２．７ｇ、アセトニトリル３０ｍｌ、ジブロモオクタン０．６３ｇを量りとり、還流下２４時間攪拌する。その後、減圧下溶媒を除去し、アセトンを再結晶溶媒として用いて精製後、化４で表される３級ジアミン化合物（６’）を得る。  2.7 g of this secondary amino compound (4 '), 30 ml of acetonitrile and 0.63 g of dibromooctane are weighed and stirred for 24 hours under reflux. Thereafter, the solvent is removed under reduced pressure, and after purification using acetone as a recrystallization solvent, a tertiary diamine compound (6 ′) represented by Chemical Formula 4 is obtained.

Figure 2008074822
Figure 2008074822

１，２−エポキシヘキサデカン５０ｇ、テトラヒドロフラン１００ｍｌ、ジメチルアミン４０％水溶液を２４０ｇ量りとり、密栓をして室温で２４時間攪拌する。減圧下溶媒を除去し、ヘキサンを再結晶溶媒として用いて精製後、化５で表される３級アミン化合物（８’）を得る。  Weigh 50 g of 1,2-epoxyhexadecane, 100 ml of tetrahydrofuran, and 240 g of a 40% aqueous solution of dimethylamine, close the cap, and stir at room temperature for 24 hours. The solvent is removed under reduced pressure, and after purification using hexane as a recrystallization solvent, a tertiary amine compound (8 ') represented by Chemical Formula 5 is obtained.

Figure 2008074822
Figure 2008074822

化５で表される３級アミン化合物（８’）２．９ｇ、ジブロモオクタン８．３ｇ、アセトニトリル５０ｍｌを量りとり、還流下、２４時間攪拌する。減圧下溶媒を除去し、アセトンを再結晶溶媒として用いて精製後、化６で表される４級アンモニウム化合物（９’）を得る。  2.9 g of the tertiary amine compound (8 ') represented by Chemical formula 5, 8.3 g of dibromooctane and 50 ml of acetonitrile are weighed and stirred for 24 hours under reflux. The solvent is removed under reduced pressure, and after purification using acetone as a recrystallization solvent, a quaternary ammonium compound (9 ') represented by Chemical Formula 6 is obtained.

Figure 2008074822
Figure 2008074822

化６で表される４級アンモニウム化合物１．４ｇと化４で表される３級ジアミン化合物０．４ｇ、ジメチルホルムアミド５０ｍｌを量りとり、５０℃で６日間攪拌する。減圧下溶媒を除去し、アセトンを再結晶溶媒として用いて精製後、化７で表される本発明の４鎖４親水基含有陽イオン界面活性剤を得る。  Weigh 1.4 g of the quaternary ammonium compound represented by Chemical Formula 6, 0.4 g of the tertiary diamine compound represented by Chemical Formula 4 and 50 ml of dimethylformamide, and stir at 50 ° C. for 6 days. The solvent is removed under reduced pressure, and after purification using acetone as a recrystallization solvent, the 4-chain 4-hydrophilic group-containing cationic surfactant of the present invention represented by Chemical Formula 7 is obtained.

Figure 2008074822
Figure 2008074822

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−エポキシオクタデカン、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４鎖４親水基含有陽イオン界面活性剤を得る。また、１，８−ジブロモオクタンの代わりに、１，３−ジブロモプロパン、１，４−ジブロモブタン、１，６−ジブロヘキサン、１，１０−ジブロモデカン、１，１２−ジブロモドデカン、ｍ−キシレンジブロミド、ｐ−キシレンジブロミドを用いることにより一般式（１）でのＳの異なる本発明の４鎖４親水基含有陽イオン界面活性剤を得る。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。メチルアミンの代わりに、エタノールアミン、ジメチルアミンの代わりに、Ｎ−メチルエタノールアミンを用いることにより一般式（１）でのＲとしてメチル基と２−ヒドロキシエチル基を共に含む本発明の４鎖４親水基含有陽イオン界面活性剤を得る。  By using 1,2-epoxydodecane, 1,2-epoxyhexadecane, 1,2-epoxyoctadecane, 1,2-epoxyeicosane, etc., or a mixture thereof instead of the above 1,2-epoxyoctadecane The 4-chain 4 hydrophilic group-containing cationic surfactant of the present invention having a different n in the general formula (1) is obtained. Further, instead of 1,8-dibromooctane, 1,3-dibromopropane, 1,4-dibromobutane, 1,6-dibrohexane, 1,10-dibromodecane, 1,12-dibromododecane, m-xylenediene By using bromide and p-xylene dibromide, the 4-chain 4-hydrophilic group-containing cationic surfactant of the present invention having a different S in the general formula (1) is obtained. A bromine atom or a chlorine atom can be used as the halogen of the alkyl halide (5). By using N-methylethanolamine instead of methylamine instead of ethanolamine and dimethylamine, the 4-chain 4 of the present invention containing both methyl and 2-hydroxyethyl groups as R in the general formula (1) A hydrophilic group-containing cationic surfactant is obtained.

かくして得られる本発明の４鎖４親水基含有陽イオン界面活性剤は、可溶化剤、乳化剤、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、和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４鎖４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）としても利用することができる。  The thus obtained 4-surfactant 4 hydrophilic group-containing cationic surfactant of the present invention comprises a solubilizer, an emulsifier, an antibacterial agent, a disinfectant, a fiber softener, a hair treatment agent, a surface treatment agent for inorganic carriers, a pigment dispersant, In addition to being used as an emulsifier and a sum transfer catalyst, it is also useful in cosmetics, ore flotation and oil well mining. In addition, the 4-chain, 4-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.

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.

参考例１
１，２−エポキシヘキサデカン５０ｇ、メチルアミン４０％水溶液１６０ｇ、テトラヒドロフラン１００ｍｌを活栓つきナスフラスコに量りとり、密栓をして室温で２４時間攪拌する。減圧下溶媒を除去し、ヘキサンを再結晶溶媒として用いて精製後、化３で表される２級アミン化合物を得た（収率８０％）。Reference example 1
Weigh 50 g of 1,2-epoxyhexadecane, 160 g of methylamine 40% aqueous solution, and 100 ml of tetrahydrofuran in an eggplant flask with a stopcock, seal, and stir at room temperature for 24 hours. The solvent was removed under reduced pressure, and after purification using hexane as a recrystallization solvent, a secondary amine compound represented by Chemical Formula 3 was obtained (yield 80%).

参考例２
１，２−エポキシヘキサデカン６４ｇ、ジメチルアミン５０％水溶液２４０ｇ、テトラヒドロフラン１００ｍｌを活栓つきナスフラスコに量りとり、密栓をして室温で２４時間攪拌する。減圧下溶媒を除去した後、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）を用いて化５で表される３級アミン化合物を無色の油性物質として得た（収率８０％）。Reference example 2
Weigh 64 g of 1,2-epoxyhexadecane, 240 g of dimethylamine 50% aqueous solution, and 100 ml of tetrahydrofuran in an eggplant flask with a stopcock, seal, and stir at room temperature for 24 hours. After removing the solvent under reduced pressure, the residue was subjected to silica gel column chromatography using hexane / ethyl acetate (2: 1) to remove unreacted raw materials, and subsequently chloroform / methanol (5: 1) was used as a solvent. The tertiary amine compound represented by Chemical Formula 5 was used as a colorless oily substance (yield 80%).

参考例３
参考例１で得た２級アミン化合物２．７ｇ、ジブロモオクタン０．６３ｇ、アセトニトリル３０ｍｌを量りとり、還流下２４時間攪拌する。その後、減圧下溶媒を除去し、アセトンを再結晶溶媒として用いて精製後、化４で表される３級ジアミン化合物を得た（収率６０％）。Reference example 3
2.7 g of the secondary amine compound obtained in Reference Example 1, 0.63 g of dibromooctane, and 30 ml of acetonitrile are weighed and stirred under reflux for 24 hours. Thereafter, the solvent was removed under reduced pressure, and after purification using acetone as a recrystallization solvent, a tertiary diamine compound represented by Chemical formula 4 was obtained (yield 60%).

参考例４
参考例２で得た３級アミン化合物２．９ｇ、ジブロモオクタン８．３２ｇ、アセトニトリル５０ｍｌを量りとり、還流下、２４時間攪拌する。減圧下溶媒を除去し、アセトンを再結晶溶媒として用いて精製後、化６で表される４級アンモニウム化合物を得た（収率５５％）。Reference example 4
2.9 g of the tertiary amine compound obtained in Reference Example 2, 8.32 g of dibromooctane, and 50 ml of acetonitrile are weighed and stirred for 24 hours under reflux. The solvent was removed under reduced pressure, and after purification using acetone as a recrystallization solvent, a quaternary ammonium compound represented by Chemical Formula 6 was obtained (yield 55%).

実施例１
参考例３で得た３級ジアミン化合物０．４ｇ、参考例４で得た４級アンモニウム化合物１．４ｇをジメチルホルムアミド３０ｍｌ中、５０℃で６日間攪拌する。減圧下溶媒を除去し、アセトンを再結晶溶媒として用いて精製後、得た結晶を１３Ｃ−ＮＭＲ（溶媒：重クロロホルム）測定を行ったところ、４級窒素に結合するメチル基を５２．４８ｐｐｍに確認し、ＦＡＢ−ＭＳ測定の結果、１６８４のピークを確認した。このように、化６で表される本発明の４鎖４親水基含有陽イオン界面活性剤を得た（収率５５％）。Example 1
0.4 g of the tertiary diamine compound obtained in Reference Example 3 and 1.4 g of the quaternary ammonium compound obtained in Reference Example 4 are stirred for 6 days at 50 ° C. in 30 ml of dimethylformamide. The solvent was removed under reduced pressure, and after purification using acetone as a recrystallization solvent, the obtained crystals were subjected to 13C-NMR (solvent: deuterated chloroform) measurement. As a result, the methyl group bonded to the quaternary nitrogen was reduced to 52.48 ppm. It confirmed and the peak of 1684 was confirmed as a result of FAB-MS measurement. Thus, the 4-chain 4 hydrophilic group containing cationic surfactant of this invention represented by Chemical formula 6 was obtained (yield 55%).

参考例５
参考例１で得た２級アミン化合物２．７ｇ、ｐ−キシレンジブロミド０．６ｇ、アセトニトリル３０ｍｌを量りとり、還流下２４時間攪拌する。その後、減圧下溶媒を除去し、アセトンを再結晶溶媒として用いて精製後、化８で表される３級ジアミン化合物を得た（収率６２％）。Reference Example 5
2.7 g of the secondary amine compound obtained in Reference Example 1, 0.6 g of p-xylene dibromide and 30 ml of acetonitrile are weighed and stirred for 24 hours under reflux. Thereafter, the solvent was removed under reduced pressure, and after purification using acetone as a recrystallization solvent, a tertiary diamine compound represented by Chemical Formula 8 was obtained (yield 62%).

Figure 2008074822
Figure 2008074822

参考例６
参考例２で得た３級アミン化合物２．９ｇ、ｐ−キシレンジブロミド８．１ｇ、アセトニトリル５０ｍｌを量りとり、還流下、２４時間攪拌する。減圧下溶媒を除去し、アセトンを再結晶溶媒として用いて精製後、化９で表される４級アンモニウム化合物を得たく収率５２％）。Reference Example 6
2.9 g of the tertiary amine compound obtained in Reference Example 2, 8.1 g of p-xylene dibromide and 50 ml of acetonitrile are weighed and stirred for 24 hours under reflux. The solvent was removed under reduced pressure, and after purification using acetone as a recrystallization solvent, a quaternary ammonium compound represented by Chemical Formula 9 was obtained (yield: 52%).

Figure 2008074822
Figure 2008074822

実施例２
参考例５で得た３級ジアミン化合物０．４ｇ、参考例６で得た４級アンモニウム化合物１．４ｇをジメチルホルムアミド３０ｍｌ中、５０℃で６日間攪拌する。減圧下溶媒を除去し、アセトンを再結晶溶媒として用いて精製後、化１０で表される本発明の４鎖４親水基含有陽イオン界面活性剤を得る。Example 2
0.4 g of the tertiary diamine compound obtained in Reference Example 5 and 1.4 g of the quaternary ammonium compound obtained in Reference Example 6 are stirred in 30 ml of dimethylformamide at 50 ° C. for 6 days. The solvent is removed under reduced pressure, and after purification using acetone as a recrystallization solvent, the 4-chain 4 hydrophilic group-containing cationic surfactant of the present invention represented by Chemical Formula 10 is obtained.

Figure 2008074822
Figure 2008074822

本発明の４鎖４親水基含有陽イオン界面活性剤は、その会合体を鋳型として用いてメソポーラスシリカ、メソポーラス酸化チタン、メソポーラス酸化ジルコニウムを調製することができる。メソポーラス物質は、細孔内に様々なビタミン類、有効成分、薬効成分を取り込ませることができることから、化粧料への応用が可能である。メソポーラスシリカは物質の分離分析のための充填剤としての応用が可能である。  The 4-chain 4 hydrophilic group-containing cationic surfactant of the present invention can prepare mesoporous silica, mesoporous titanium oxide, and mesoporous zirconium oxide using the aggregate as a template. Mesoporous substances can be applied to cosmetics because various vitamins, active ingredients and medicinal ingredients can be taken into the pores. Mesoporous silica can be applied as a filler for separating and analyzing substances.

実施例１で得られた本発明の４鎖４親水基含有陽イオン界面活性剤の１３Ｃ−ＮＭＲスペクトルを示す図である。1 is a diagram showing a 13C-NMR spectrum of a 4-surfactant 4 hydrophilic group-containing cationic surfactant of the present invention obtained in Example 1. FIG. 実施例で得られた本発明の４鎖４親水基含有陽イオン界面活性剤の測ＦＡＢ−ＭＳスペクトルを示す図である。It is a figure which shows the measurement FAB-MS spectrum of the 4-chain 4 hydrophilic group containing cationic surfactant of this invention obtained in the Example.

Claims (1)

下記一般式（１）
Figure 2008074822
（式中、ｎは８から２０までの整数を意味し、Ｒは低級アルキル基又は２−ヒドロキシエチル基を示し、Ｓは炭素原子数２から１２のアルキレン鎖又は芳香環を含むアルキレン鎖、Ｘは塩素原子又は臭素原子を示す。）で表わされることを特徴とする４鎖４親水基含有陽イオン界面活性剤。The following general formula (1)
Figure 2008074822
(Wherein n represents an integer of 8 to 20, R represents a lower alkyl group or a 2-hydroxyethyl group, S represents an alkylene chain having 2 to 12 carbon atoms or an alkylene chain containing an aromatic ring, X Represents a chlorine atom or a bromine atom.) A 4-chain 4-hydrophilic group-containing cationic surfactant characterized by
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017052751A (en) * 2015-09-09 2017-03-16 東ソー株式会社 Gemini type surfactant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017052751A (en) * 2015-09-09 2017-03-16 東ソー株式会社 Gemini type surfactant

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