JP2000053625A - New amide compound - Google Patents
New amide compoundInfo
- Publication number
- JP2000053625A JP2000053625A JP10375613A JP37561398A JP2000053625A JP 2000053625 A JP2000053625 A JP 2000053625A JP 10375613 A JP10375613 A JP 10375613A JP 37561398 A JP37561398 A JP 37561398A JP 2000053625 A JP2000053625 A JP 2000053625A
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- Prior art keywords
- compound
- formula
- acid
- ion
- diamine
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Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、生分解性にすぐれ
る新規アミド化合物に関する。[0001] The present invention relates to a novel amide compound having excellent biodegradability.
【0002】[0002]
【従来の技術】従来より洗浄剤、乳化剤、コンディショ
ニング剤として有用な種々の陰イオン界面活性剤が知ら
れている。近年多鎖多親水基含有陰イオン界面活性剤が
そのすぐれた界面活性能から注目されている。しかし、
生分解性にすぐれ、環境保護の点で満足されるものはま
だないのが実状で、その改良が望まれていた。2. Description of the Related Art Various anionic surfactants useful as detergents, emulsifiers and conditioning agents have hitherto been known. In recent years, multi-chain and multi-hydrophilic group-containing anionic surfactants have attracted attention due to their excellent surface activity. But,
As a matter of fact, there is still no biodegradable material that is satisfactory in terms of environmental protection, and improvement has been 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、生分解性にすぐれる新規アミド化合物を提
供することである。An object of the present invention is to provide a novel amide compound having excellent biodegradability.
【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、後記特定の新規アミド化合
物が生分解性に顕著にすぐれることを見出し、本発明を
完成した。The present inventors have SUMMARY OF THE INVENTION As a result of intensive research in view of the above circumstances, found significantly superior thing below certain novel amide compounds biodegradability, the present invention has been completed.
【0005】即ち、本発明の請求項1は、一般式That is, claim 1 of the present invention is a general formula
【0006】[0006]
【化2】 Embedded image
【0007】(式中、mは2から10、n+1は8〜2
0、Xは水素イオン、1価又は2価のアルカリ金属イオ
ン、アルカリ土類金属イオン、アンモニウムイオン又は
有機アンモニウムイオンの1種又は2種以上)で表され
る新規アミド化合物である。(Where m is 2 to 10 and n + 1 is 8 to 2)
0 and X are novel amide compounds represented by one or more of hydrogen ion, monovalent or divalent alkali metal ion, alkaline earth metal ion, ammonium ion and organic ammonium ion).
【0008】[0008]
【発明の実施の形態】次に本発明の実施の形態を説明す
る。本発明の新規アミド化合物は、例えば化3の反応ス
キームに従って得ることができる。Next, an embodiment of the present invention will be described. The novel amide compound of the present invention can be obtained, for example, according to the reaction scheme of Chemical formula 3.
【0009】[0009]
【化3】 Embedded image
【0010】すなわち、水とアセトンの混合溶媒(6:
4,容量比)に原料ジアミン(〔S,S〕エチレンジア
ミンジコハク酸)と4倍当量の水酸化ナトリウムを投入
し、溶解させる。その後、10〜60℃でジアミンに対
して2倍当量の酸クロリドを攪拌しながら徐々に滴下す
る。このとき、水酸化ナトリウムを滴下して系のpHを
アルカリに保つ。酸クロリドの滴下終了後、数時間室温
で攪拌を継続し、反応を終える。その後、塩酸で系のp
Hを1として生じた沈澱を濾過、水洗後、乾燥する。こ
の反応物をベンゼン/アセトンの混合溶媒を用いて再結
晶する。このようにして〔S,S〕エチレンジアミンジ
コハク酸のジアシル化物を得た。尚、〔S,S〕エチレ
ンジアミンジコハク酸の合成方法は、Chem.Zvesti, 20
(6):414-422(1966)に示されている。That is, a mixed solvent of water and acetone (6:
(4, volume ratio), a raw material diamine ([S, S] ethylenediaminedisuccinic acid) and 4 times equivalent of sodium hydroxide are added and dissolved. Thereafter, at 10 to 60 ° C., acid chloride in an amount equivalent to twice the amount of the diamine is gradually added dropwise with stirring. At this time, the pH of the system is kept alkaline by adding sodium hydroxide dropwise. After completion of the dropwise addition of the acid chloride, stirring is continued at room temperature for several hours to complete the reaction. Then, the system p
The precipitate formed with H as 1 is filtered, washed with water and dried. The reaction product is recrystallized using a mixed solvent of benzene / acetone. Thus, a diacylated [S, S] ethylenediaminedisuccinic acid was obtained. The method for synthesizing [S, S] ethylenediaminedisuccinic acid is described in Chem. Zvesti, 20
(6): 414-422 (1966).
【0011】また、〔S,S〕エチレンジアミンジコハ
ク酸の代わりに〔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を用いて水とジエチルエーテルの
混合溶媒(6:4,容量比)中で同様の方法で酸クロリ
ドと反応させた後、塩酸でpHを1としてから静置して
ジエチルエーテル層を分取する。水洗後、無水炭酸カリ
ウムで乾燥する。ジエチルエーテルを減圧下除去し、得
られる〔S,S〕エチレンジアミンジコハク酸テトラメ
チルエステルジアシル化物の4倍当量の水酸化ナトリウ
ム水溶液中で90℃3時間攪拌する。その後、室温下、
塩酸でpHを1に調整後、放冷して析出する結晶物を濾
過して〔S,S〕エチレンジアミンジコハク酸のジアシ
ル化物を得た。Further, [S, S] ethylenediaminedisuccinic acid tetramethyl ester is used in place of [S, S] ethylenediaminedisuccinic acid in a mixed solvent of water and diethyl ether (6: 4, volume ratio). After the reaction with acid chloride by the method described above, the pH is adjusted to 1 with hydrochloric acid and the mixture is allowed to stand to separate a diethyl ether layer. After washing with water, it is dried over anhydrous potassium carbonate. The diethyl ether is removed under reduced pressure, and the mixture is stirred at 90 ° C. for 3 hours in an aqueous sodium hydroxide solution equivalent to 4 times the equivalent of the obtained [S, S] ethylenediaminedisuccinic acid tetramethyl ester diacylate. Then, at room temperature,
After adjusting the pH to 1 with hydrochloric acid, the mixture was allowed to cool and the precipitated crystal was filtered to obtain a diacylated [S, S] ethylenediaminedisuccinic acid.
【0012】本発明の新規アミド化合物の連結基は炭素
原子数2〜10のポリメチレン鎖が適用される。界面活
性の点から連結基は炭素原子数2のエチレン鎖が好まし
い。疎水基は、炭素原子数(n+1)8〜20のものが
適用され、洗浄を目的とする場合、12、14が好まし
く、用途に応じて直鎖状、分岐状のものが選択される。
対イオンは、水素イオン、1価又は2価のアルカリ金属
イオン、アルカリ土類金属イオン、アンモニウムイオン
又は有機アンモニウムイオンから1種又は2種以上が適
宜選択される。The connecting group of the novel amide compound of the present invention is a polymethylene chain having 2 to 10 carbon atoms. From the viewpoint of surface activity, the linking group is preferably an ethylene chain having 2 carbon atoms. As the hydrophobic group, one having 8 to 20 carbon atoms (n + 1) is applied, and for the purpose of washing, 12 or 14 is preferable, and a linear or branched one is selected depending on the use.
The counter ion is appropriately selected from one or more of a hydrogen ion, a monovalent or divalent alkali metal ion, an alkaline earth metal ion, an ammonium ion and an organic ammonium ion.
【0013】本発明の新規アミド化合物は生分解性に顕
著にすぐれる。また、本発明のアミド化合物は、中和率
を調節することにより、例えば、不整炭素に対してα位
の2つのカルボキシルのみを中和するとき、通常の2鎖
2親水基含有陰性界面活性剤と同様の界面活性能を発現
する。したがって、皮膚、毛髪、食器、衣料用などの各
種洗浄剤、皮膚、毛髪用化粧料の乳化剤、コンデイショ
ニング剤等として使用することができる。この場合の配
合量は特に限定されず、その用途等に応じて0.1〜8
0重量%、好ましくは1〜50重量%の範囲で使用する
ことができる。The novel amide compound of the present invention is remarkably excellent in biodegradability. Further, the amide compound of the present invention can adjust the neutralization rate, for example, when neutralizing only two carboxyls at the α-position with respect to an asymmetric carbon, a normal two-chain two-hydrophilic group-containing negative surfactant. Expresses the same surface activity. Therefore, it can be used as various cleaning agents for skin, hair, tableware, clothing, etc., emulsifiers for skin and hair cosmetics, conditioning agents and the like. The blending amount in this case is not particularly limited, and may be 0.1 to 8 depending on the use or the like.
It can be used in an amount of 0% by weight, preferably 1 to 50% by weight.
【0014】本発明の新規アミド化合物をこれらの用途
に使用する場合、必要に応じて各種界面活性剤、保湿
剤、殺菌剤、粘剤、二価金属イオン封鎖剤、無機塩、色
素、香料等の公知の化粧料用原料を配合することができ
る。When the novel amide compound of the present invention is used for these purposes, various surfactants, humectants, bactericides, viscosity agents, divalent metal ion sequestering agents, inorganic salts, pigments, fragrances, etc., if necessary. The known raw materials for cosmetics can be blended.
【0015】[0015]
【実施例】以下、実施例にて本発明を説明する。The present invention will be described below with reference to examples.
【0016】実施例1(〔S,S〕エチレンジアミンジ
コハク酸のジアシル化物(C12)の製造) 〔S,S〕エチレンジアミンジコハク酸29.0g
(0.11モル)を水/アセトン(4:6)の混合溶媒
500mlに入れ、その後、100mlの水に溶解した
水酸化ナトリウム17.6g(0.44モル)を入れて
攪拌下〔S,S〕エチレンジアミンジコハク酸を溶解さ
せる。ドデカノイルクロリド95.9g(0.44モ
ル)を攪拌下滴下する。このとき、このとき、水酸化ナ
トリウムを滴下して系のpHをアルカリに保つ。アシル
クロリドの滴下終了後、数時間室温で攪拌を継続し、反
応を終える。その後、塩酸で系のpHを1として生じた
沈澱を濾過、水洗後.乾燥する。この反応物をベンゼン
/アセトンの混合溶媒を用いて再結晶する。精製物の元
素分析結果は次の通りであった。炭素:62.15(6
2.17)、水素9.20(9.21)、窒素4.26
(4.27)。カッコ内の数値は理論値である。Example 1 (Production of diacylated [S, S] ethylenediaminedisuccinic acid (C12)) [S, S] ethylenediaminedisuccinic acid 29.0 g
(0.11 mol) was added to 500 ml of a mixed solvent of water / acetone (4: 6), and then 17.6 g (0.44 mol) of sodium hydroxide dissolved in 100 ml of water was added and stirred [S, S] Dissolve ethylenediaminedisuccinic acid. 95.9 g (0.44 mol) of dodecanoyl chloride are added dropwise with stirring. At this time, the pH of the system is kept alkaline by adding sodium hydroxide dropwise. After the completion of the dropwise addition of the acyl chloride, the stirring is continued at room temperature for several hours to complete the reaction. Thereafter, the precipitate formed with hydrochloric acid at a pH of 1 was filtered and washed with water. dry. The reaction product is recrystallized using a mixed solvent of benzene / acetone. The results of elemental analysis of the purified product were as follows. Carbon: 62.15 (6
2.17), hydrogen 9.20 (9.21), nitrogen 4.26
(4.27). The values in parentheses are theoretical values.
【0017】実施例2 (〔S,S〕エチレンジアミン
ジコハク酸のジアシル化物(C12)の製造) 水/ジエチルエーテル(1:1)200ミリリットルに
(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
によって精製物を得た。水200ミリリットルにこの
(S,S)エチレンジアミンジコハク酸テトラメチルエ
ステルのアミド化物(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。そ
の後、塩酸によってpHを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。放置後、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〔S,S〕エチレン
ジアミンジコハク酸のジアシル化物(C12)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:62.15%(62.17%),水素:9.10
(9.21%),窒素:4.10(4.27%)。尚、
赤外吸収スペクトルにおいて、アミドカルボニルとα,
β位のカルボキシカルボニルが1608.8cm-1,1
743.9cm-1,1718.8cm-1にそれぞれ観察
された。Example 2 (Production of diacylated [S, S] ethylenediaminedisuccinic acid (C12)) Tetramethyl (S, S) ethylenediaminedisuccinic acid (200 ml) in water / diethyl ether (1: 1) 0.01 mol) and sodium hydroxide (0.04
Mol), and lauric chloride (0.02 mol) 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 obtained residue was purified by column chromatography using silica gel as the stationary phase and chloroform as the mobile phase to obtain a purified product. The amidated (S, S) ethylenediaminedisuccinic acid tetramethyl ester (0.1 mol) and sodium hydroxide (0.4 mol) were added to 200 ml of water, and the mixture was stirred at 80 ° C. for 3 hours. Thereafter, the pH was adjusted to 1 with hydrochloric acid, and the mixture was cooled. The resulting precipitate was filtered and dissolved with heating using a mixed solvent of tetrahydrofuran and water. After standing, the resulting precipitate was filtered. The obtained amorphous crystals were further recrystallized under the same conditions. After drying, the molecular structure of the diacylated [S, S] ethylenediaminedisuccinic acid (C12) was confirmed by the elemental analysis results. The numbers in parentheses are theoretical values. Carbon: 62.15% (62.17%), hydrogen: 9.10
(9.21%), nitrogen: 4.10 (4.27%). still,
In the infrared absorption spectrum, the amide carbonyl and α,
The carboxycarbonyl at the β-position is 1608.8 cm −1 , 1
It was observed at 743.9 cm -1 and 1718.8 cm -1 , respectively.
【0018】参考例1(〔R,R〕エチレンジアミンジ
コハク酸のジアシル化物(C12)の製造) 実施例2において用いた〔S,S〕エチレンジアミンジ
コハク酸の代わりに、〔R,R〕エチレンジアミンジコ
ハク酸を用いる他は同様の操作で〔R,R〕エチレンジ
アミンジコハク酸のアシル化物(C12)を得た。Reference Example 1 (Production of diacylated [R, R] ethylenediaminedisuccinic acid (C12)) In place of [S, S] ethylenediaminedisuccinic acid used in Example 2, [R, R] ethylenediamine An acylated product of [R, R] ethylenediaminedisuccinic acid (C12) was obtained by the same operation except that disuccinic acid was used.
【0019】参考例2(〔S,R〕エチレンジアミンジ
コハク酸のジアシル化物(C12)の製造) 実施例2において用いた〔S,S〕エチレンジアミンジ
コハク酸の代わりに、〔S,R〕エチレンジアミンジコ
ハク酸を用いる他は同様の操作で〔S,R〕エチレンジ
アミンジコハク酸のジアシル化物(C12)を得た。Reference Example 2 (Production of diacylated [S, R] ethylenediaminedisuccinic acid (C12)) Instead of [S, S] ethylenediaminedisuccinic acid used in Example 2, [S, R] ethylenediamine A diacylated [S, R] ethylenediaminedisuccinic acid (C12) was obtained by the same operation except that disuccinic acid was used.
【0020】〔S,S〕エチレンジアミンジコハク酸の
ジアシル化物(C12)、〔R,R〕エチレンジアミン
ジコハク酸のジアシル化物(C12)、〔S,R〕エチ
レンジアミンジコハク酸のジアシル化物(C12)につ
いて生分解性試験(JIS生分解度試験方法K−336
3法)を行った。その結果、〔S,S〕エチレンジアミ
ンジコハク酸のジアシル化物(C12)、〔R,R〕エ
チレンジアミンジコハク酸のジアシル化物(C12)、
〔S,R〕エチレンジアミンジコハク酸のジアシル化物
(C12)のそれぞれの生分解率は99.5%、74.
2%、45.8%であった。この結果から、エチレンジ
アミンジコハク酸のジアシル化物の生分解性は〔S,
S〕異性体に対して特異的であることがわかる。[S, S] Diacylated ethylenediaminedisuccinic acid (C12), [R, R] Diacylated ethylenediaminedisuccinic acid (C12), [S, R] Diacylated ethylenediaminedisuccinic acid (C12) About biodegradability test (JIS biodegradability test method K-336)
3 method). As a result, diacylated [S, S] ethylenediaminedisuccinic acid (C12), diacylated [R, R] ethylenediaminedisuccinic acid (C12),
The biodegradation rates of the diacylated [S, R] ethylenediaminedisuccinic acid (C12) are 99.5% and 74.
2% and 45.8%. From these results, the biodegradability of the diacylated product of ethylenediaminedisuccinic acid was [S,
[S] isomer is found to be specific.
【0021】実施例2(〔S,S〕プロピレンジアミン
ジコハク酸のアシル化物(C12)の製造) 実施例2において用いた〔S,S〕エチレンジアミンジ
コハク酸の代わりに、〔S,S〕プロピレンジアミンジ
コハク酸を用いる他は同様の操作で〔S,S〕プロピレ
ンジアミンジコハク酸のアシル化物(C12)を得た。
精製物の元素分析結果は次の通りであった。炭素:6
2.67(62.66)、水素9.30(9.32)、
窒素4.17(4.18)。カッコ内の数値は理論値で
ある。本化合物の生分解率は98.8%であった。これ
らのように生分解性にすぐれた2鎖2親水基含有陰イオ
ン界面活性剤は本発明のアミド化合物を除いてまだ存在
しない。Example 2 (Production of acylated product of [S, S] propylenediaminedisuccinic acid (C12)) Instead of [S, S] ethylenediaminedisuccinic acid used in Example 2, [S, S] An acylated product of [S, S] propylenediaminedisuccinic acid (C12) was obtained in the same operation except that propylenediaminedisuccinic acid was used.
The results of elemental analysis of the purified product were as follows. Carbon: 6
2.67 (62.66), hydrogen 9.30 (9.32),
Nitrogen 4.17 (4.18). The values in parentheses are theoretical values. The biodegradation rate of this compound was 98.8%. These two-chain two-hydrophilic group-containing anionic surfactants having excellent biodegradability do not yet exist except for the amide compound of the present invention.
【0022】処方例1 本発明の化合物を用いて以下の組成のシャンプーを調製
した。配合量は重量%である。 (組成) 実施例2の化合物の2Na塩 15.8 ラウロイルジエタノールアミド 2.5 ラウリルジメチルアミンオキシド 0.5 ヒドロキシメチルセルロース 0.1 安息香酸ナトリウム 0.2 色素 適量 クエン酸 適量 香料 適量 水 残余Formulation Example 1 A shampoo having the following composition was prepared using the compound of the present invention. The compounding amount is% by weight. (Composition) 2Na salt of the compound of Example 2 15.8 Lauroyldiethanolamide 2.5 Lauryldimethylamine oxide 0.5 Hydroxymethylcellulose 0.1 Sodium benzoate 0.2 Dye qs Citric acid qs Flavor qs Water balance
【0023】処方例1のシャンプーは、起泡性、洗浄性
に優れていた。The shampoo of Formulation Example 1 was excellent in foaming properties and detergency.
【0024】処方例2 以下の組成のシャンプーを調製した。 (組成) 特開平9−2931号公報において一般式(B)で示される2疎水基2親水基型 陰イオン界面活性剤の2Na塩(但し、R2COがラウロイル、アミノ酸がグル タミン酸、X2がエチレン基) 15.8 ラウロイルジエタノールアミド 2.5 ラウリルジメチルアミンオキシド 0.5 ヒドロキシメチルセルロース 0.1 安息香酸ナトリウム 0.2 色素 適量 クエン酸 適量 香料 適量 水 残余Formulation Example 2 A shampoo having the following composition was prepared. (Composition) In JP-A-9-2931, 2Na salt of a two-hydrophobic group-two hydrophilic group type anionic surfactant represented by the general formula (B) (provided that R2CO is lauroyl, amino acid is glutamic acid, and X2 is ethylene) Group) 15.8 lauroyldiethanolamide 2.5 lauryldimethylamine oxide 0.5 hydroxymethylcellulose 0.1 sodium benzoate 0.2 dye proper amount citric acid proper amount perfume proper amount water residue
【0025】処方例1のシャンプーは、起泡性、洗浄
性、洗い上がり後の感触において処方例2のシャンプー
より優れていた。The shampoo of Formulation Example 1 was superior to the shampoo of Formulation Example 2 in foaming properties, detergency, and feel after washing.
【0026】[0026]
【発明の効果】以上記載の如く、本発明は、生分解性に
すぐれる新規アミド化合物を提供することは明らかであ
る。As described above, it is apparent that the present invention provides a novel amide compound having excellent biodegradability.
Claims (1)
イオン、1価又は2価のアルカリ金属イオン、アルカリ
土類金属イオン、アンモニウムイオン又は有機アンモニ
ウムイオンの1種又は2種以上)で表される新規アミド
化合物。1. A compound of the general formula (Wherein m is 2 to 10, n + 1 is 8 to 20, X is one or more of hydrogen ion, monovalent or divalent alkali metal ion, alkaline earth metal ion, ammonium ion or organic ammonium ion) The novel amide compound represented by the formula:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP37561398A JP3576416B2 (en) | 1998-06-03 | 1998-12-15 | New amide compounds |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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JP10-154231 | 1998-06-03 | ||
JP15423198 | 1998-06-03 | ||
JP37561398A JP3576416B2 (en) | 1998-06-03 | 1998-12-15 | New amide compounds |
Publications (2)
Publication Number | Publication Date |
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JP2000053625A true JP2000053625A (en) | 2000-02-22 |
JP3576416B2 JP3576416B2 (en) | 2004-10-13 |
Family
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Family Applications (1)
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JP37561398A Expired - Lifetime JP3576416B2 (en) | 1998-06-03 | 1998-12-15 | New amide compounds |
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JP (1) | JP3576416B2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003057662A3 (en) * | 2002-01-11 | 2003-10-02 | Cognis Deutschland Gmbh | Acylated ethylenediamine disuccinate |
JP6005863B2 (en) * | 2013-08-02 | 2016-10-12 | 富士フイルム株式会社 | Liquid detergent composition |
-
1998
- 1998-12-15 JP JP37561398A patent/JP3576416B2/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003057662A3 (en) * | 2002-01-11 | 2003-10-02 | Cognis Deutschland Gmbh | Acylated ethylenediamine disuccinate |
JP6005863B2 (en) * | 2013-08-02 | 2016-10-12 | 富士フイルム株式会社 | Liquid detergent composition |
Also Published As
Publication number | Publication date |
---|---|
JP3576416B2 (en) | 2004-10-13 |
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