JP3576417B2 - Novel amide compound and method for producing the same - Google Patents
Novel amide compound and method for producing the same Download PDFInfo
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- JP3576417B2 JP3576417B2 JP37591898A JP37591898A JP3576417B2 JP 3576417 B2 JP3576417 B2 JP 3576417B2 JP 37591898 A JP37591898 A JP 37591898A JP 37591898 A JP37591898 A JP 37591898A JP 3576417 B2 JP3576417 B2 JP 3576417B2
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Description
【０００１】
【発明の属する技術分野】
本発明は、２鎖２親水基含有陰イオン界面活性剤の中間体として有用な新規アミド化合物及びその製造方法に関する。
【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。
このような背景にあって、近年、高性能界面活性剤として２鎖２親水基含有陰イオン界面活性剤が注目され、特開平９−２９３１号公報、特開平８−３１１００３号公報、ＷＯ９６／１４９２６号公報、ＷＯ９６／２５３８８号公報等で既に開示されている。しかし、これらのものを詳細に検討すると着色や副生成物の存在によって実用に耐えられないものであったり、実際には目的物が得られないもの等の問題があることが判明し、現状での課題となっていた。
【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、生分解性にすぐれる新規２鎖２親水基含有陰イオン界面活性剤の中間体として有用な新規アミド化合物及びその製造方法を開発することである。
【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、後記特定の新規アミド化合物及びその製造方法がこのような界面活性剤の中間体及びその製造方法として有用であることを見出し、本発明を完成した。
【０００５】
即ち、本発明の請求項１は、一般式（１）
【０００６】
【化３】
（ｎ＋１は８〜２０の整数で、ｍは１〜８の整数である。）で表される（Ｓ，Ｓ）体であることを特徴とする新規アミド化合物である。
【００１３】
またさらに、本発明の請求項２は、（Ｓ，Ｓ）エチレンジアミンジコハク酸テトラアルキルエステル（アルキル基の炭素原子数は１〜８の整数である。）と、一般式（４）
【００１４】
【化４】
（ｎ＋１は８〜２０の整数、Ｘはハロゲン原子、ヒドロキシル基又は炭素原子数１〜３のアルコキシル基である。）で表されるアシル化合物とを反応させることを特徴とする請求項１記載の新規アミド化合物の製造方法である。
【００１６】
【発明の実施の形態】
次に本発明の実施の形態を説明する。本発明の一般式（１）で表される新規アミド化合物は公知のアミノ化合物と一般式（４）のアシル化合物を反応させることにより得られる。一般式（４）においてＸで示されるハロゲン原子としては塩素原子、臭素原子、沃素原子等が挙げられるが、なかでも塩素原子が望ましい。また、Ｘで示されるアルコキシル基としては、メチル基、エチル基。プロピル基等が挙げられる。この反応は、水／アセトン、水／エチルエーテル等の混合溶媒、又はトルエン、キシレン等の溶媒を用い、それぞれ水酸化ナトリウム、炭酸ナトリウム、アルコキシド等の塩基性触媒の存在下で行う。これらの反応は０〜２００℃で、任意に選択される。また、下記一般式（２）で表されるアミド化合物は、一般式（１）で表される新規アミド化合物をアルカリ加水分解後、得られる。
【化５】
【化６】
上記のアミド化合物いずれも、生分解性に顕著にすぐれる。アミド化合物（２）は皮膚等に低刺激で好ましい感触を与え、皮膚、毛髪用化粧料の洗浄剤、乳化剤として使用することができる。アミド化合物（３）は皮膚等に低刺激で好ましい感触を与え、皮膚、毛髪用化粧料のコンデイショニング剤として使用することができる。これらのアミド化合物をこれらの用途に使用する場合、必要に応じて公知の各種界面活性剤、乳化剤、可溶化剤、保湿剤、油成分、殺菌剤、増粘剤、無機塩等を配合することができる。また、本発明のアミド化合物は、必要に応じ、アルカリ加水分解、中和により高性能の陰イオン界面活性剤である２疎水基２親水基含有陰イオン界面活性剤に変換することができる。
【００１８】
【実施例】
以下、実施例にて本発明を説明する。
実施例１ 上記一般式（１）においてｎ＋１が１２で、ｍが１であるアミド化合物の合成
水／ジエチルエーテル（１：１）２００ミリリットルに
【００１９】
【化７】
で表されるアミノ化合物、（Ｓ，Ｓ）エチレンジアミンジコハク酸テトラメチルエステル（０．０１モル）と水酸化ナトリウム（０．０４モル）を溶解した後、ラウリン酸クロリド（０．０２モル）を室温で攪拌下、滴下した。その後、１時間、攪拌した。塩酸によってｐＨを酸性に調整し、静置した。エーテル層を分取し、エバポレーターによって溶媒を除去した。得られた残分を固定相としてシリカゲル、移動相としてクロロホルムを用いたカラムクロマトグラフィーによって精製して得られた本アミド化合物の分子構造は次の元素分析結果によって確認された。かっこ内の数字は理論値である。炭素：６４．０３％（６４．０２％），水素：９．７２（９．６１％），窒素：４．００（３．９３％）。赤外吸収スペクトルでアミドカルボニルの吸収が１６４０ｃｍ−１に確認された。
【００２１】
参考例１ 上記一般式（２）においてｎ＋１が１２であるアミド化合物の合成
水２００ミリリットルに実施例１で得られたアミド化合物（０．１モル）と水酸化ナトリウム（０．４モル）を加え、３時間、８０℃で攪拌した。水を凍結乾燥器によって除去し、本アミド化合物を得た。本アミド化合物の分子構造は次の元素分析結果によって確認された。かっこ内の数字は理論値である。炭素：５４．６７％（５４．７８％），水素：７．６２（７．５２％），窒素：３．７５（３．７６％）
【００２２】
参考例２ 上記一般式（３）においてｎ＋１が１２であるアミド化合物の合成
参考例１で得られたアミド化合物（０．１モル）の水溶液のｐＨを塩酸によって１に調整し、冷却した。生じる沈澱を濾過し、テトラヒドロフランと水の混合溶媒を用いて熱時溶解した。生じる沈澱物を濾過した。得られた不定形結晶をさらに同様の条件で再結晶した。乾燥後、元素分析結果によって本アミド化合物の分子構造が確認された。かっこ内の数字は理論値である。炭素：６３．４５％（６３．５１％），水素：９．１０（８．８８％），窒素：４．１０（４．１１％）。赤外吸収スペクトルでアミドカルボニル、カルボキシルカルボニルが１６０８．８ｃｍ-1、１７４３．９ｃｍ-1、１７１８ｃｍ-1がそれぞれ確認された。
【００２３】
【発明の効果】
以上の通り、本発明は２鎖２親水基含有陰イオン界面活性剤の製造に有用な新規アミド化合物及びその製造方法を提供することができる。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a novel amide compound useful as an intermediate of a two-chain two-hydrophilic group-containing anionic surfactant and a method for producing the same.
[0002]
[Prior art]
Conventionally, (a) an anionic interface which is a salt composed of a sulfuric acid ester of an aliphatic higher alcohol, a phosphoric acid ester of an aliphatic higher alcohol, N-long-chain acylglutamic acid, and a basic substance such as caustic soda, caustic potash, and triethanolamine. Activators, (ii) ether-type nonionic surfactants such as ethylene oxide adducts of aliphatic higher alcohols, and (iii) ester-type nonionic surfactants comprising higher fatty acids and polyhydric alcohols are known. .
However, these surfactants cannot be said to have sufficient skin safety for consumers with sensitive skin disorders, and need to be improved, and development of excellent surfactants is desired.
Against this background, attention has recently been paid to two-chain, two-hydrophilic group-containing anionic surfactants as high-performance surfactants, which are disclosed in JP-A-9-2931, JP-A-8-31003, and WO96 / 14926. No., WO96 / 25388 and the like. However, when these are examined in detail, it has been found that there are problems such as coloring or by-products that cannot be practically used due to the presence of by-products, or that the intended product cannot be actually obtained. Was an issue.
[0003]
[Problems to be solved by the invention]
The problem to be solved by the present invention is to develop a novel amide compound useful as an intermediate of a novel two-chain two-hydrophilic group-containing anionic surfactant having excellent biodegradability and a method for producing the same.
[0004]
[Means for Solving the Problems]
The present inventors have conducted intensive studies in view of the above circumstances, and as a result, have found that the specific novel amide compound described below and a method for producing the same are useful as an intermediate for such a surfactant and a method for producing the same. Was completed.
[0005]
That is, claim 1 of the present invention relates to general formula (1)
[0006]
Embedded image
(N + 1 is an integer of 8 to 20 and m is an integer of 1 to 8), which is a (S, S) form represented by the following formula:
[0013]
Furthermore, claim 2 of the present invention relates to a tetraalkyl (S, S) ethylenediaminedisuccinate (the alkyl group has an integer of 1 to 8 carbon atoms) and a general formula (4).
[0014]
Embedded image
(N + 1 is an integer of 8 to 20, X is a halogen atom, a hydroxyl group or an alkoxyl group having 1 to 3 carbon atoms). This is a method for producing a novel amide compound.
[0016]
BEST MODE FOR CARRYING OUT THE INVENTION
Next, an embodiment of the present invention will be described. The novel amide compound of the present invention represented by the general formula (1) can be obtained by reacting a known amino compound with an acyl compound of the general formula (4). Examples of the halogen atom represented by X in the general formula (4) include a chlorine atom, a bromine atom, and an iodine atom. Among them, a chlorine atom is preferable. Examples of the alkoxyl group represented by X include a methyl group and an ethyl group. And a propyl group. This reaction is carried out using a mixed solvent such as water / acetone or water / ethyl ether, or a solvent such as toluene or xylene in the presence of a basic catalyst such as sodium hydroxide, sodium carbonate or alkoxide. These reactions are optionally selected at 0-200 ° C. Moreover, an amide compound represented by the following general formula (2) after alkaline hydrolysis of the novel amide compounds represented by the general formula (1), is obtained.
Embedded image
Embedded image
Any of the above amide compound, significantly excellent in biodegradability. The amide compound (2) gives a good feeling to the skin and the like with low irritation, and can be used as a detergent and an emulsifier for skin and hair cosmetics. The amide compound (3) gives a good feeling to the skin and the like with low irritation, and can be used as a conditioning agent for cosmetics for skin and hair. When these amide compounds are used for these applications, various known surfactants, emulsifiers, solubilizers, humectants, oil components, bactericides, thickeners, inorganic salts, and the like may be added as necessary. Can be. Further, the amide compound of the present invention can be converted to a high-performance anionic surfactant-containing anionic surfactant having two hydrophobic groups and two hydrophilic groups by alkali hydrolysis and neutralization, if necessary.
[0018]
【Example】
Hereinafter, the present invention will be described with reference to examples.
Example 1 Synthesis of an amide compound in which n + 1 is 12 and m is 1 in the general formula (1) In 200 ml of water / diethyl ether (1: 1)
Embedded image
After dissolving the amino compound represented by the formula (S, S) ethylenediaminedisuccinic acid tetramethyl ester (0.01 mol) and sodium hydroxide (0.04 mol), lauric chloride (0.02 mol) is added. The mixture was added dropwise at room temperature with stirring. Thereafter, the mixture was stirred for 1 hour. The pH was adjusted to acidic with hydrochloric acid and allowed to stand. The ether layer was separated, and the solvent was removed by an evaporator. The molecular structure of the amide compound obtained by purifying the obtained residue by column chromatography using silica gel as a stationary phase and chloroform as a mobile phase was confirmed by the following elemental analysis results. The numbers in parentheses are theoretical values. Carbon: 64.03% (64.02%), hydrogen: 9.72 (9.61%), nitrogen: 4.00 (3.93%). In the infrared absorption spectrum, the absorption of amide carbonyl was confirmed at 1640 cm -1 .
[0021]
Reference Example 1 Synthesis of amide compound in which n + 1 is 12 in the above general formula (2) To 200 ml of water was added the amide compound (0.1 mol) obtained in Example 1 and sodium hydroxide (0.4 mol). Stirred at 80 ° C. for 3 hours. The water was removed by a freeze dryer to obtain the present amide compound. The molecular structure of this amide compound was confirmed by the following elemental analysis results. The numbers in parentheses are theoretical values. Carbon: 54.67% (54.78%), Hydrogen: 7.62 (7.52%), Nitrogen: 3.75 (3.76%)
[0022]
Reference Example 2 Synthesis of amide compound in which n + 1 is 12 in the above general formula (3)
The pH of the aqueous solution of the amide compound (0.1 mol) obtained in Reference Example 1 was adjusted to 1 with hydrochloric acid and cooled. The resulting precipitate was filtered and dissolved with heating using a mixed solvent of tetrahydrofuran and water. The resulting precipitate was filtered. The obtained amorphous crystals were further recrystallized under the same conditions. After drying, the molecular structure of the amide compound was confirmed by the elemental analysis results. The numbers in parentheses are theoretical values. Carbon: 63.45% (63.51%), hydrogen: 9.10 (8.88%), nitrogen: 4.10 (4.11%). Infrared absorption spectrum in the amide carbonyl, carboxyl carbonyl 1608.8cm -1, 1743.9cm -1, 1718cm -1 was confirmed, respectively.
[0023]
【The invention's effect】
As described above, the present invention can provide a novel amide compound useful for producing a two-chain two-hydrophilic group-containing anionic surfactant and a method for producing the same.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP37591898A JP3576417B2 (en) | 1998-12-11 | 1998-12-18 | Novel amide compound and method for producing the same |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP37509098 | 1998-12-11 | ||
| JP10-375090 | 1998-12-11 | ||
| JP37591898A JP3576417B2 (en) | 1998-12-11 | 1998-12-18 | Novel amide compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000229924A JP2000229924A (en) | 2000-08-22 |
| JP3576417B2 true JP3576417B2 (en) | 2004-10-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP37591898A Expired - Fee Related JP3576417B2 (en) | 1998-12-11 | 1998-12-18 | Novel amide compound and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3576417B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10200726A1 (en) * | 2002-01-11 | 2003-07-24 | Cognis Deutschland Gmbh | Acylated ethylenediamine succinate |
| JP4518367B2 (en) * | 2002-03-25 | 2010-08-04 | 株式会社資生堂 | Pore reducing agent |
-
1998
- 1998-12-18 JP JP37591898A patent/JP3576417B2/en not_active Expired - Fee Related
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| JP2000229924A (en) | 2000-08-22 |
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