JP2983360B2 - Surfactant - Google Patents
SurfactantInfo
- Publication number
- JP2983360B2 JP2983360B2 JP3331201A JP33120191A JP2983360B2 JP 2983360 B2 JP2983360 B2 JP 2983360B2 JP 3331201 A JP3331201 A JP 3331201A JP 33120191 A JP33120191 A JP 33120191A JP 2983360 B2 JP2983360 B2 JP 2983360B2
- Authority
- JP
- Japan
- Prior art keywords
- trehalose
- surfactant
- undecylenyl
- present
- skin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Description
【０００１】[0001]
【産業上の利用分野】本発明は、優れた界面活性能力を
もち、且つ皮膚に対する安全性の高い界面活性剤に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a surfactant having excellent surfactant activity and high safety to skin.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来、
界面活性剤として数多くの化合物が知られており、多方
面に使用されている。しかしながら、これらの界面活性
剤の中には、人体に直接接触するシャンプー、リンス、
石鹸等の香粧品に用いた場合、皮膚に対して刺激を与え
るものも多い。このため、より刺激性の低い界面活性剤
の開発が望まれていた。2. Description of the Related Art
Numerous compounds are known as surfactants and are widely used. However, some of these surfactants include shampoos, rinses,
When used in cosmetics such as soaps, many of them give irritation to the skin. For this reason, development of a surfactant having lower irritation has been desired.
【０００３】一方、アルキルエステル化した多糖類は、
食品、化粧品等に広く汎用されている界面活性剤であ
り、中でも糖骨格としてショ糖を用いたショ糖アルキル
エステルに関する報告は多く、また広く用いられてい
る。また、トレハロース誘導体を界面活性剤として用い
ることを目的とした報告もあるが（特開昭６０−２５８
１９５号公報、特開昭６２−９１２３６号公報）、これ
らはトレハロース−６，６’−ジアルキルエステルに限
られている。On the other hand, alkyl esterified polysaccharides are
It is a surfactant widely used in foods, cosmetics and the like, and among others, there are many reports on sucrose alkyl esters using sucrose as a sugar skeleton, and they are widely used. There is also a report aimed at using a trehalose derivative as a surfactant (JP-A-60-258).
195, JP-A-62-91236), which are limited to trehalose-6,6'-dialkyl esters.
【０００４】一方、界面活性剤としての界面活性、起泡
性や洗浄力等を考えると、一般に親油基としてのアルキ
ル基は、単一の方が好ましいためグルコース脂肪酸モノ
エステルが開発されているが（特開平３−１５７３４９
号公報）、親水基部が単糖であることから親水性が弱い
と考えられる。[0004] On the other hand, considering the surface activity as a surfactant, foaming properties, detergency, etc., it is generally preferable to use a single alkyl group as a lipophilic group, so glucose fatty acid monoesters have been developed. (Japanese Unexamined Patent Publication No. 3-157349)
Publication), the hydrophilicity is considered to be weak because the hydrophilic group is a monosaccharide.
【０００５】[0005]
【課題を解決するための手段】本発明者等は、上記事情
に鑑み鋭意研究を行った結果、下記の一般式で示される
化合物が、優れた界面活性能力をもつとともに皮膚に対
して高い安全性を有することを見出し、本発明を完成し
た。即ち、本発明は、下記一般式で示される６−（１１
−ウンデシレニル）−トレハロースからなる界面活性剤
である。Means for Solving the Problems The present inventors have conducted intensive studies in view of the above circumstances, and as a result, it has been found that a compound represented by the following general formula has excellent surface activity and high safety against skin. The present invention was found to have the property, and the present invention was completed. That is, the present invention provides 6- (11) represented by the following general formula:
-Undecylenyl) -trehalose.
【化２】Embedded image
【０００６】以下、本発明の構成の詳細について説明す
る。本発明の６−（１１−ウンデシレニル）−トレハロ
ースとは、トレハロースと１１−ウンデシレン酸の低級
アルキルエステルとを縮合することにより得ることがで
きる。Hereinafter, the configuration of the present invention will be described in detail. The 6- (11-undecylenyl) -trehalose of the present invention can be obtained by condensing trehalose with a lower alkyl ester of 11-undecylenic acid.
【０００７】即ち、通常のショ糖アルキルエステルを製
造する方法を用いることにより得ることができる（ＵＳ
Ｐ２８９３９９０号公報、特開昭３６−２１７１７号公
報、ＵＳＰ３４８０６１６号公報、特公昭５３−６１３
０号公報、ＵＳＰ３９６３６９９号公報）。そして、こ
れらの方法により得られた主反応生成物として、本発明
の６−（１１−ウンデシレニル）−トレハロースを得る
ことができる。尚、６，６’−ジ−（１１−ウンデシレ
ニル）−トレハロースも少量生成されるが、これが混在
した状態でも本発明の６−（１１−ウンデシレニル）−
トレハロースの界面活性剤としての特徴は維持されるた
め、問題にはならない。また、本発明の６−（１１−ウ
ンデシレニル）−トレハロースからなる界面活性剤は、
様々な洗浄剤、化粧料等に利用することが可能である。That is, it can be obtained by using a conventional method for producing a sucrose alkyl ester (US Pat.
P2893990 JP, Sho 36-21717, JP-USP3480616 JP, Sho JP publicly 53-613
0, US Pat. No. 3,963,699). And 6- (11-undecylenyl) -trehalose of the present invention can be obtained as a main reaction product obtained by these methods. It should be noted that a small amount of 6,6′-di- (11-undecylenyl) -trehalose is also produced, but even in a mixed state, 6- (11-undecylenyl)-of the present invention is used.
This is not a problem because the characteristics of trehalose as a surfactant are maintained. Further, the surfactant comprising 6- (11-undecylenyl) -trehalose of the present invention comprises:
It can be used for various cleaning agents and cosmetics.
【０００８】[0008]
【実施例】以下、実施例について説明する。この実施例
において、ｗｔ％は重量％を意味する。 実施例１ （１）６−（１１−ウンデシレニル）−トレハロースの
製造 トレハロース１００ｇを４００ｍｌのジメチルフォルム
アミドに溶解した。この溶液に１１−ウンデシレン酸メ
チル５２，４ｇと水酸化カリウム１．０ｇを加え、１０
０℃まで昇温した後、１２時間撹拌した。この反応溶液
を冷却した後、４００ｍｌのヘキサンで３回抽出して未
反応の１１−ウンデシレン酸メチルを除去した。ジメチ
ルフォルムアミド溶液を減圧下において約２００ｍｌ程
度まで濃縮した後、１０００ｍｌのアセトンを加え、未
反応のトレハロースを沈澱させ濾別除去した。沈澱を１
００ｍｌのｎ−ブタノールにて洗浄し、洗浄液を濾液に
加えた。濾液を減圧蒸留する事により淡黄色な粘性シロ
ップを得た。この粘性シロップをシリカゲルカラムクロ
マトグラフィー（展開溶媒 クロロホルム／メタノール
＝４／１）にて残留未反応物を除去することにより２
４．３ｇの淡黄色粘性シロップを得た。Embodiments will be described below. In this example, wt% means weight%. Example 1 (1) Production of 6- (11-undecylenyl) -trehalose 100 g of trehalose was dissolved in 400 ml of dimethylformamide. To this solution were added 52.4 g of methyl 11-undecylenate and 1.0 g of potassium hydroxide, and 10
After the temperature was raised to 0 ° C., the mixture was stirred for 12 hours. After cooling the reaction solution, it was extracted three times with 400 ml of hexane to remove unreacted methyl 11-undecylenate. After the dimethylformamide solution was concentrated to about 200 ml under reduced pressure, 1000 ml of acetone was added to precipitate unreacted trehalose, which was removed by filtration. 1 precipitate
After washing with 00 ml of n-butanol, the washing solution was added to the filtrate. The filtrate was distilled under reduced pressure to obtain a pale yellow viscous syrup. The viscous syrup was subjected to silica gel column chromatography (developing solvent: chloroform / methanol = 4/1) to remove residual unreacted substances, thereby obtaining 2
4.3 g of a pale yellow viscous syrup were obtained.
【０００９】（２）６−（１１−ウンデシレニル）−ト
レハロースの特性 得られたシロップの１３Ｃ−ＮＭＲペクトル測定におい
て、１７５．５ｐｐｍにカルボニル基、１４０．１１及
び１１４．７３ｐｐｍに末端メチレン基、また６４．４
及び６２．６４ｐｐｍにトレハロース６及び６’位のシ
グナルを確認したことから、本発明の６−（１１−ウン
デシレニル）−トレハロースの生成を確認した。(2) Characteristics of 6- (11-undecylenyl) -trehalose In a 13 C-NMR spectrum measurement of the obtained syrup, a carbonyl group was found at 175.5 ppm, a terminal methylene group at 140.11 and 114.73 ppm, and 64 .4
And signals of trehalose 6 and 6 ′ at 62.64 ppm, the production of 6- (11-undecylenyl) -trehalose of the present invention was confirmed.
【００１０】（３）安全性 皮膚に対する刺激性を以下の方法で調べた。２０人の被
験者に界面活性剤の０．２％水溶液１ｍｌをしみこませ
たパッチテスト用絆創膏を２４時間貼布し、貼布除去後
２４時間後に刺激性を判定した。判定結果は、はっきり
と紅斑を示したものを陽性とし、その陽性率で示した。
その結果を表１に示す。但し、ラウリルリン酸エステル
１ナトリウム塩は通常用いられている界面活性剤であ
る。(3) Safety The irritation to the skin was examined by the following method. A patch test adhesive bandage impregnated with 1 ml of a 0.2% aqueous solution of a surfactant was applied to 20 subjects for 24 hours, and the irritation was determined 24 hours after removing the adhesive. As a judgment result, those which clearly showed erythema were defined as positive and the positive rate was shown.
Table 1 shows the results. However, lauryl phosphate monosodium salt is a commonly used surfactant.
【００１１】[0011]
【表１】 [Table 1]
【００１２】表１の如く、本発明の６−（１１−ウンデ
シレニル）−トレハロースは、皮膚刺激性がなく、皮膚
安全性は明らかに優れている。[0012] As shown in Table 1, the 6- (11-undecylenyl) -trehalose of the present invention has no skin irritation and clearly has excellent skin safety.
【００１３】応用例１ 下記表２の組成からなる液状洗浄剤を調製した。尚、用
いた６−（１１−ウンデシレニル）−トレハロースは、
実施例１にて得られたものである。この洗浄剤で洗顔し
た結果、汚れがきれいに落ち、感触も良好であった。Application Example 1 A liquid detergent having the composition shown in Table 2 below was prepared. In addition, 6- (11-undecylenyl) -trehalose used was
This is obtained in Example 1. As a result of washing the face with this detergent, the stains were cleanly removed and the feel was good.
【００１４】[0014]
【表２】 [Table 2]
【００１５】応用例２ 下記表３の組成からなる水中油型スキンクリームを調製
した。尚、用いた６−（１１−ウンデシレニル）−トレ
ハロースは、実施例１にて得られたものである。このク
リームの乳化状態は極めて良好で、べたつかず肌なじみ
も良好であった。Application Example 2 An oil-in-water skin cream having the composition shown in Table 3 below was prepared. In addition, 6- (11-undecylenyl) -trehalose used was obtained in Example 1. The emulsified state of this cream was extremely good, and it was not sticky and had good skin familiarity.
【００１６】[0016]
【表３】 [Table 3]
【００１７】応用例３ 下記表４の組成からなる頭髪洗浄剤を調製した。尚、用
いた６−（１１−ウンデシレニル）−トレハロースは、
実施例１にて得られたものである。この洗浄剤で洗髪し
た結果、泡立ちは優れており感触も良好であった。Application Example 3 A hair cleansing composition having the composition shown in Table 4 below was prepared. In addition, 6- (11-undecylenyl) -trehalose used was
This is obtained in Example 1. As a result of washing the hair with this detergent, the foaming was excellent and the feel was good.
【００１８】[0018]
【表４】 [Table 4]
【００１９】[0019]
【発明の効果】以上述べた通り、本発明によれば、界面
活性能力及び皮膚安全性に極めて優れた新規な界面活性
剤が得られることは明らかである。As described above, according to the present invention, it is apparent that a novel surfactant having extremely excellent surfactant activity and skin safety can be obtained.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ // Ｃ０７Ｈ 13/06 Ｃ０７Ｈ 13/06 (58)調査した分野(Int.Cl.6，ＤＢ名) B01F 17/56 A61K 7/00 C07H 13/06 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 6 identification symbol FI // C07H 13/06 C07H 13/06 (58) Field surveyed (Int. Cl. 6 , DB name) B01F 17/56 A61K 7 / 00 C07H 13/06
Claims (1)
デシレニル）−トレハロースからなる界面活性剤。 【化１】 1. A surfactant comprising 6- (11-undecylenyl) -trehalose represented by the following general formula. Embedded image
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3331201A JP2983360B2 (en) | 1991-11-19 | 1991-11-19 | Surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3331201A JP2983360B2 (en) | 1991-11-19 | 1991-11-19 | Surfactant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05137994A JPH05137994A (en) | 1993-06-01 |
| JP2983360B2 true JP2983360B2 (en) | 1999-11-29 |
Family
ID=18241026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3331201A Expired - Lifetime JP2983360B2 (en) | 1991-11-19 | 1991-11-19 | Surfactant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2983360B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9102945D0 (en) * | 1991-02-12 | 1991-03-27 | Unilever Plc | Detergent composition |
| JP3187622B2 (en) * | 1993-10-07 | 2001-07-11 | カネボウ株式会社 | Liposome |
| JPH1045560A (en) * | 1996-08-06 | 1998-02-17 | Kanebo Ltd | Skin mucous membrane-stimulation emollient |
| JP4168170B2 (en) | 2002-10-10 | 2008-10-22 | 独立行政法人産業技術総合研究所 | Arbutin ester compound and method for producing the same |
-
1991
- 1991-11-19 JP JP3331201A patent/JP2983360B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05137994A (en) | 1993-06-01 |
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