JPH08295657A - Intermediate for surfactant - Google Patents
Intermediate for surfactantInfo
- Publication number
- JPH08295657A JPH08295657A JP12922795A JP12922795A JPH08295657A JP H08295657 A JPH08295657 A JP H08295657A JP 12922795 A JP12922795 A JP 12922795A JP 12922795 A JP12922795 A JP 12922795A JP H08295657 A JPH08295657 A JP H08295657A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- integer
- group
- fatty acid
- 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.)
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- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、化粧品用の種々の２鎖
２親水基含有界面活性剤の中間体として有用な化合物に
関する。TECHNICAL FIELD The present invention relates to a compound useful as an intermediate for various 2-chain 2-hydrophilic group-containing surfactants for cosmetics.
【０００２】[0002]
【従来の技術】従来より（イ）脂肪族高級アルコールの
硫酸エステル、脂肪族高級アルコールのリン酸エステ
ル、Ｎ−長鎖アシルグルタミン酸等と苛性ソーダ、苛性
カリ、トリエタノールアミン等の塩基性物質からなる塩
であるアニオン型界面活性剤、（ロ）脂肪族高級アルコ
ールの酸化エチレン付加物等のエーテル型非イオン界面
活性剤、（ハ）高級脂肪酸と多価アルコールとからなる
エステル型非イオン界面活性剤等が知られている。しか
し、これらの界面活性剤は、敏感肌症の消費者に対して
十分な皮膚安全性を持つとは言えず、その改良が必要で
あり、すぐれた界面活性剤の開発が望まれている。2. Description of the Related Art Conventionally, (a) salts of sulfuric acid esters of aliphatic higher alcohols, phosphoric acid esters of aliphatic higher alcohols, N-long chain acylglutamic acid, etc. and basic substances such as caustic soda, caustic potash, triethanolamine, etc. Anionic surfactants, (b) ether type nonionic surfactants such as ethylene oxide adducts of aliphatic higher alcohols, (c) ester type nonionic surfactants composed of higher fatty acids and polyhydric alcohols, etc. It has been known. However, these surfactants cannot be said to have sufficient skin safety for consumers with sensitive skin disorders, and their improvement is necessary, and development of excellent surfactants is desired.
【０００３】[0003]
【発明が解決しようとする課題】本発明が解決しようと
する課題は、すぐれた物性を持ち、敏感肌症の消費者も
満足するような十分な皮膚安全性を持つ界面活性剤の中
間体を開発することである。The problem to be solved by the present invention is to provide an intermediate of a surfactant having excellent physical properties and having sufficient skin safety to satisfy consumers with sensitive skin disorders. It is to develop.
【０００４】[0004]
【課題を解決するための手段】本発明者等は、上記の事
情に鑑み鋭意研究した結果、後記特定の化合物がこのよ
うな界面活性剤の中間体として有用であることを見出
し、本発明を完成した。Means for Solving the Problems As a result of intensive studies in view of the above circumstances, the present inventors have found that a specific compound described below is useful as an intermediate for such a surfactant, and completed.
【０００５】即ち、本発明は、一般式（１）That is, the present invention has the general formula (1)
【０００６】[0006]
【化２】 Embedded image
【０００７】（但し、式中のｍが２から３の整数であ
り、ｎが２から４の整数であり、アシル基の炭素数は８
から２０である）で表されることを特徴とする界面活性
剤の中間体である。(However, in the formula, m is an integer of 2 to 3, n is an integer of 2 to 4, and the carbon number of the acyl group is 8
To 20) are intermediates of the surfactant.
【０００８】次に本発明の構成を説明する。本発明の界
面活性剤の中間体は、例えば下記表１に示す反応式に従
って製造することができる。すなわち、先ず、ハロゲン
化アルコールとアルキレンジアミンとを炭酸ナトリウム
の存在下で還流下エタノールを反応溶媒に用いて数時間
反応させる。得られる第２級ジアミンを例えば第２級ジ
アミンに対して４倍当量の脂肪酸クロリドとピリジンの
存在下ベンゼンを反応溶媒に用いて数時間反応させる。
得られるアミド基とエステル基含有化合物をアルカリで
加水分解して本発明の界面活性剤の中間体を得る。ここ
で用いられるハロゲン化アルコールの炭素数は２から３
であり、アルキレンジアミンの炭素数は２から４の整数
である。また、脂肪酸クロリドのアシル基の炭素数は８
から２０が適用される。Next, the structure of the present invention will be described. The intermediate of the surfactant of the present invention can be produced, for example, according to the reaction formula shown in Table 1 below. That is, first, a halogenated alcohol and an alkylenediamine are reacted in the presence of sodium carbonate under reflux with ethanol as a reaction solvent for several hours. The resulting secondary diamine is reacted for several hours using benzene as a reaction solvent in the presence of, for example, 4-fold equivalent of fatty acid chloride and pyridine with respect to the secondary diamine.
The resulting amide group- and ester group-containing compound is hydrolyzed with an alkali to obtain an intermediate for the surfactant of the present invention. The halogenated alcohol used here has 2 to 3 carbon atoms.
And the carbon number of the alkylenediamine is an integer of 2 to 4. The number of carbon atoms in the acyl group of fatty acid chloride is 8
To 20 apply.
【０００９】[0009]
【表１】 [Table 1]
【００１０】本発明の化合物は新規であり、これを用い
て種々の型の有用な２疎水基２親水基含有界面活性剤に
変換することができる。The compounds of the present invention are new and can be used to convert various types of useful 2 hydrophobic 2 hydrophilic groups containing surfactants.
【００１１】[0011]
【実施例】以下、実施例にて本発明を説明する。EXAMPLES The present invention will be described below with reference to examples.
【００１２】実施例１〔一般式（１）でｍ＝２、ｎ＝
２、アシル基の炭素数が１２の化合物の合成〕 ２−ブロムエタノール５０グラム（０．４モル）と炭酸
ナトリウム４２グラム（０．４モル）をエタノール２０
０ミリリットルに混合し、エチレンジアミン１２グラム
（０．２モル）のエタノール（５０ミリリットル）溶液
に３０分間を要して室温下滴下する。滴下後、加熱還流
しながら６時間攪拌する。この反応液をろ過し、ろ液を
エパポレーターによってエタノールを除去し、得られる
残さを蒸留精製する（沸点は約３２０℃）。得られる無
色粘性液体の13Ｃ−ＮＭＲスペクトル（溶媒：重クロロ
ホルム、ＴＭＳ標準）を測定し、３種のメチレン基の炭
素に由来する吸収を認めた。このアミノ基含有化合物
（１７ミリモル）とピリジン６．１グラム（７７ミリモ
ル）をベンゼン３０ミリリットルに混合し、これをドデ
カノイルクロリド１７グラム（７７ミリモル）のベンゼ
ン３０ミリリットル溶液に室温下攪拌しながら滴下す
る。滴下後、還流下で５時間反応させて生じる沈殿物を
デカンテーションによって除去し、エバポレーションに
よってろ液から溶媒を除去する。残さにｎ−ヘキサン３
０ミリリットルを加え、３時間放置後、生じる沈殿物を
デカンテーションによって取り出す。この沈殿物をさら
にｎ−ヘキサン３０ミリリットルで洗浄し、乾燥する。
得られる無色固体の13Ｃ−ＮＭＲスペクトル（溶媒：重
クロロホルム、ＴＭＳ標準）を測定するとアミドカルボ
ニル炭素、エステルカルボニル炭素に由来する吸収をそ
れぞれ認めた。このアミノ基とエステル基含有化合物
（０．１ミリモル）のメタノール（２０ミリリットル）
溶液を６０度Ｃに加熱攪拌しながら、水酸化ナトリウム
４．８ミリグラム（０．１２ミリモル）の１５％水溶液
（１ミリリットル）を徐々に滴下する。３０分間加熱攪
拌を継続した後、氷水中に投入し、生じる沈殿物をろ過
する。この沈殿物を水２０ミリリットル、次いでベンゼ
ン２０ミリリットルで洗浄し、乾燥する。得られる無色
固体の13Ｃ−ＮＭＲスペクトル（溶媒：重クロロホル
ム、ＴＭＳ標準）を測定するとアミドカルボニル炭素に
由来する吸収を認め、エステルカルボニル炭素に由来す
る吸収を認めなかった。Example 1 [In the general formula (1), m = 2, n =
2. Synthesis of compound having 12 carbon atoms in acyl group] 2-Brom ethanol 50 g (0.4 mol) and sodium carbonate 42 g (0.4 mol) were added to ethanol 20
It is mixed with 0 ml and added dropwise to a solution of 12 g (0.2 mol) of ethylenediamine in ethanol (50 ml) at room temperature over 30 minutes. After the dropping, the mixture is stirred for 6 hours while heating under reflux. The reaction solution is filtered, ethanol is removed from the filtrate by an evaporator, and the resulting residue is purified by distillation (boiling point: about 320 ° C.). The 13 C-NMR spectrum (solvent: deuterated chloroform, TMS standard) of the obtained colorless viscous liquid was measured, and absorption derived from carbons of three methylene groups was observed. This amino group-containing compound (17 mmol) and 6.1 g (77 mmol) of pyridine were mixed with 30 ml of benzene, and this was added dropwise to a solution of 17 g (77 mmol) of dodecanoyl chloride in 30 ml of benzene at room temperature with stirring. To do. After the dropping, the precipitate formed by reacting under reflux for 5 hours is removed by decantation, and the solvent is removed from the filtrate by evaporation. N-hexane 3 in the residue
After adding 0 ml, the resulting precipitate is removed by decantation after standing for 3 hours. The precipitate is further washed with 30 ml of n-hexane and dried.
When the 13 C-NMR spectrum (solvent: deuterated chloroform, TMS standard) of the obtained colorless solid was measured, absorptions derived from amide carbonyl carbon and ester carbonyl carbon were recognized, respectively. This amino group- and ester group-containing compound (0.1 mmol) in methanol (20 ml)
A 15% aqueous solution (1 milliliter) of 4.8 milligrams (0.12 millimoles) of sodium hydroxide is gradually added dropwise while the solution is heated and stirred at 60 ° C. After continuing heating and stirring for 30 minutes, the mixture is poured into ice water and the resulting precipitate is filtered. The precipitate is washed with 20 ml of water, then 20 ml of benzene and dried. When the 13 C-NMR spectrum of the obtained colorless solid (solvent: deuterated chloroform, TMS standard) was measured, absorption derived from amide carbonyl carbon was observed, and absorption derived from ester carbonyl carbon was not recognized.
【００１３】実施例２〔一般式（１）中でｍ＝３、ｎ＝
４、アシル基の炭素数が１２の化合物の合成〕 実施例１のエチレンジアミン１２グラム（０．２モル）
と２−ブロムエタノール５０グラム（０．４モル）の代
わりに、ブチレンジアミン１８グラム（０．２モル）と
３−ブロムプロパノール５６グラム（０．４モル）を用
いる他は同様の操作で一連の反応、すなわちＮ−アルキ
ル化、アシル化、エステル加水分解反応と各過程での精
製を行う。最終的に得られる無色液体の13Ｃ−ＮＭＲス
ペクトル（溶媒：重クロロホルム、ＴＭＳ標準）を測定
するとアミドカルボニル炭素に由来する吸収を認め、エ
ステルカルボニル炭素に由来する吸収を認めなかった。Example 2 [m = 3, n = in the general formula (1)]
4. Synthesis of compound having 12 carbon atoms in acyl group] 12 g (0.2 mol) of ethylenediamine of Example 1
In place of 50 g (0.4 mol) of 2-bromoethanol and 18 g (0.2 mol) of butylenediamine and 56 g (0.4 mol) of 3-bromopropanol, the same procedure was repeated. Reaction, that is, N-alkylation, acylation, ester hydrolysis reaction and purification in each step are performed. When the 13 C-NMR spectrum (solvent: deuterated chloroform, TMS standard) of the finally obtained colorless liquid was measured, absorption derived from amide carbonyl carbon was observed and absorption derived from ester carbonyl carbon was not recognized.
【００１４】実施例３〔一般式（１）中でｍ＝２、ｎ＝
２、アシル基の炭素数が１６の化合物の合成〕 実施例１のドデカノイルクロリド（７７ミリモル）の代
わりに、パルミトイルクロリド（７７ミリモル）を用い
る他は同様の原料と同様の操作で一連の反応、すなわち
Ｎ−アルキル化、アシル化、エステル加水分解反応と各
過程での精製を行う。最終的に得られる無色液体の13Ｃ
−ＮＭＲスペクトル（溶媒：重クロロホルム、ＴＭＳ標
準）を測定するとアミドカルボニル炭素に由来する吸収
を認め、エステルカルボニル炭素に由来する吸収を認め
なかった。Example 3 [m = 2, n = in the general formula (1)]
2. Synthesis of compound having an acyl group having 16 carbon atoms] A series of reactions using the same raw material as in Example 1 except that palmitoyl chloride (77 mmol) was used instead of dodecanoyl chloride (77 mmol). That is, N-alkylation, acylation, ester hydrolysis reaction and purification in each step are performed. 13 C of colorless liquid finally obtained
When the NMR spectrum (solvent: deuterated chloroform, TMS standard) was measured, absorption derived from amide carbonyl carbon was observed, and absorption derived from ester carbonyl carbon was not detected.
【００１５】実施例４〔一般式（１）中でｍ＝３、ｎ＝
４、アシル基の炭素数が１８の化合物の合成〕 実施例１のエチレンジアミン１２グラム（０．２モ
ル）、２−ブロムエタノール５０グラム（０．４モ
ル）、ドデカノイルクロリド（７７ミリモル）の代わり
に、ブチレンジアミン１８グラム（０．２モル）、３−
ブロムプロパノール５６グラム（０．４モル）、オクタ
デカノイルクロリド（７７ミリモル）を用いる他は同様
の操作で一連の反応、すなわちＮ−アルキル化、アシル
化、エステル加水分解の各反応と各精製を行う。最終的
に得られる無色液体の13Ｃ−ＮＭＲスペクトル（溶媒：
重クロロホルム、ＴＭＳ標準）を測定するとアミドカル
ボニル炭素に由来する吸収を認め、エステルカルボニル
炭素に由来する吸収を認めなかった。Example 4 [m = 3, n = in the general formula (1)]
4. Synthesis of compound having acyl group having 18 carbon atoms] In place of ethylene diamine 12 g (0.2 mol), 2-bromoethanol 50 g (0.4 mol) and dodecanoyl chloride (77 mmol) of Example 1. 18 g (0.2 mol) of butylenediamine, 3-
56 g (0.4 mol) of bromopropanol and octadecanoyl chloride (77 mmol) were used in the same manner to carry out a series of reactions, that is, N-alkylation, acylation, ester hydrolysis and each purification. To do. The 13 C-NMR spectrum of the finally obtained colorless liquid (solvent:
When deuterated chloroform, TMS standard) was measured, absorption derived from amide carbonyl carbon was observed, and absorption derived from ester carbonyl carbon was not recognized.
【００１６】[0016]
【発明の効果】以上記載の本発明の界面活性剤中間体
は、末端水酸基への親水基又は極性基の導入などが可能
であり、化粧品用の種々の２鎖２親水基含有界面活性剤
の開発に有用である。INDUSTRIAL APPLICABILITY The above-described surfactant intermediate of the present invention is capable of introducing a hydrophilic group or a polar group into the terminal hydroxyl group, and can be used as a cosmetic for various 2-chain 2-hydrophilic group-containing surfactants. Useful for development.
Claims (1)
４の整数であり、アシル基の炭素数は８から２０であ
る）で表されることを特徴とする界面活性剤の中間体。1. A compound represented by the general formula (1): (Wherein, m is an integer of 2 to 3, n is an integer of 2 to 4, and the carbon number of the acyl group is 8 to 20). Intermediate of.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12922795A JPH08295657A (en) | 1995-04-27 | 1995-04-27 | Intermediate for surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12922795A JPH08295657A (en) | 1995-04-27 | 1995-04-27 | Intermediate for surfactant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08295657A true JPH08295657A (en) | 1996-11-12 |
Family
ID=15004309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12922795A Pending JPH08295657A (en) | 1995-04-27 | 1995-04-27 | Intermediate for surfactant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08295657A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2757853A1 (en) * | 1996-12-26 | 1998-07-03 | Pacific Corp | New soluble ceramide-type compounds |
| US6458343B1 (en) * | 1999-05-07 | 2002-10-01 | Goldschmidt Chemical Corporation | Quaternary compounds, compositions containing them, and uses thereof |
| WO2009007636A2 (en) * | 2007-07-05 | 2009-01-15 | L'oreal | Novel cationic surfactant, composition containing same, use thereof as conditioner, and cosmetic treatment method |
| US10167253B2 (en) | 2015-06-24 | 2019-01-01 | Nitto Denko Corporation | Ionizable compounds and compositions and uses thereof |
-
1995
- 1995-04-27 JP JP12922795A patent/JPH08295657A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2757853A1 (en) * | 1996-12-26 | 1998-07-03 | Pacific Corp | New soluble ceramide-type compounds |
| US6458343B1 (en) * | 1999-05-07 | 2002-10-01 | Goldschmidt Chemical Corporation | Quaternary compounds, compositions containing them, and uses thereof |
| WO2009007636A2 (en) * | 2007-07-05 | 2009-01-15 | L'oreal | Novel cationic surfactant, composition containing same, use thereof as conditioner, and cosmetic treatment method |
| WO2009007636A3 (en) * | 2007-07-05 | 2009-02-26 | Oreal | Novel cationic surfactant, composition containing same, use thereof as conditioner, and cosmetic treatment method |
| US10167253B2 (en) | 2015-06-24 | 2019-01-01 | Nitto Denko Corporation | Ionizable compounds and compositions and uses thereof |
| US11384051B2 (en) | 2015-06-24 | 2022-07-12 | Nitto Denko Corporation | Ionizable compounds and compositions and uses thereof |
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