JPH08198830A - Production of fatty acid diethanolamide-type surfactant having low diethanolamine content - Google Patents
Production of fatty acid diethanolamide-type surfactant having low diethanolamine contentInfo
- Publication number
- JPH08198830A JPH08198830A JP3178713A JP17871391A JPH08198830A JP H08198830 A JPH08198830 A JP H08198830A JP 3178713 A JP3178713 A JP 3178713A JP 17871391 A JP17871391 A JP 17871391A JP H08198830 A JPH08198830 A JP H08198830A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- diethanolamine
- acid diethanolamide
- general formula
- type surfactant
- 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.)
- Granted
Links
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (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、ジエタノールアミン含
量が低く、経時着色の少ない脂肪酸ジエタノールアミド
型界面活性剤の製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a fatty acid diethanolamide type surfactant which has a low diethanolamine content and is less colored with time.
【０００２】[0002]
【従来の技術】脂肪酸ジエタノールアミド型界面活性剤
は、以前から公知である界面活性剤であり、他の界面活
性剤に配合する事により、その界面活性剤に優れた起泡
力、浸透力、洗浄力、増粘力を与える。また、毒性がき
わめて低く、生分解性が良いことからシャンプー、台所
洗剤等の化粧品、トイレタリー用品には、不可欠な成分
として当業者においては古くから使用されている。BACKGROUND OF THE INVENTION Fatty acid diethanolamide type surfactants have been known for a long time, and by blending with other surfactants, excellent foaming power, penetrating power, Provides detergency and thickening power. Further, since it has extremely low toxicity and good biodegradability, it has long been used by those skilled in the art as an indispensable component in cosmetics such as shampoos and kitchen detergents, and toiletry products.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、脂肪酸
ジエタノールアミド型界面活性剤は、その製造に際し使
用するジエタノールアミンを不純物として２〜８％程度
含有するため、製品の外観が経時的に変化し、着色が起
きる場合がある。However, since the fatty acid diethanolamide type surfactant contains diethanolamine used in the production thereof in an amount of about 2 to 8% as an impurity, the appearance of the product changes with time and the coloration changes. It may happen.
【０００４】エタノールアミン類を除去する方法として
は、蒸留あるいはカラムによる分離精製などがある。し
かし、これらの除去法は脂肪酸ジエタノールアミド型界
面活性剤の物性上から充分な分離、除去が困難であった
り、多大なコスト増となるなど、満足のいくジエタノー
ルアミンの除去方法がないのが現状である。As a method for removing ethanolamines, there are distillation and separation and purification by a column. However, in the present circumstances, there are no satisfactory methods for removing diethanolamine, such as sufficient separation and removal of these fatty acid diethanolamide type surfactants from the viewpoint of physical properties, which is difficult to remove, and a large cost increase. is there.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、従来の脂
肪酸ジエタノールアミド型界面活性剤の不純物であるジ
エタノールアミンの除去を行なうため鋭意研究を行なっ
た結果、脂肪酸ジエタノールアミド型界面活性剤を逆浸
透膜処理する事により容易にジエタノールアミンの除去
が行なえる事を発見し、本発明を完成するに至った。即
ち本発明は、一般式（Ｉ）で表されるジエタノールアミ
ンと ＨＮ（ＣＨ2ＣＨ2ＯＨ）2 （Ｉ） 一般式（ＩＩ） Ｒ1ＣＯＯＲ2 （ＩＩ） （式中Ｒ1ＣＯは、炭素数８〜２２の飽和または不飽和
脂肪酸残基を表し、Ｒ2は、水素原子または炭素数１〜
６のアルキル基を表す。）または、一般式（ＩＩＩ）Means for Solving the Problems The present inventors have conducted diligent research to remove diethanolamine, which is an impurity of conventional fatty acid diethanolamide type surfactants. It was discovered that diethanolamine can be easily removed by treatment with an osmotic membrane, and the present invention has been completed. That is, the present invention relates to diethanolamine represented by the general formula (I) and HN (CH 2 CH 2 OH) 2 (I) general formula (II) R 1 COOR 2 (II) (wherein R 1 CO is a carbon number. 8 to 22 represents a saturated or unsaturated fatty acid residue, R 2 represents a hydrogen atom or a carbon number of 1 to
6 represents an alkyl group. ) Or the general formula (III)
【化３】 （ＩＩＩ） （式中Ｒ3ＣＯは、炭素数８〜２２の飽和または不飽和
脂肪酸残基を表す。）で表される脂肪酸または脂肪酸エ
ステルと反応させて得られる一般式（ＩＶ）Embedded image (III) (wherein R 3 CO represents a saturated or unsaturated fatty acid residue having 8 to 22 carbon atoms) and a general formula (IV) obtained by reacting with a fatty acid or a fatty acid ester.
【化４】 （ＩＶ） （式中Ｒ4ＣＯは、前記Ｒ1ＣＯまたはＲ3ＣＯ）で表さ
れる生成物に対して逆浸透膜処理を行なう事を特徴とす
る、ジエタノールアミン含量の低い脂肪酸ジエタノール
アミド型界面活性剤の製造方法に関する。[Chemical 4] (IV) (wherein R 4 CO is R 1 CO or R 3 CO) is subjected to reverse osmosis membrane treatment, and a fatty acid diethanolamide type interface having a low diethanolamine content is characterized. It relates to a method for producing an activator.
【０００６】本発明に用いられる脂肪酸ジエタノールア
ミド型界面活性剤は、前記一般式（ＩＶ）で表される化
合物である。式中Ｒ1ＣＯおよびＲ3ＣＯは炭素数８ない
し２２の飽和または不飽和の脂肪酸残基を表し、代表的
な脂肪酸残基を例示すれば、ヤシ油脂肪酸、パーム核油
脂肪酸、ラウリル酸、ミリスチル酸、牛脂脂肪酸、硬化
牛脂脂肪酸、オレイン酸、ヒマシ油脂肪酸および硬化ヒ
マシ油脂肪酸などの脂肪酸残基である。The fatty acid diethanolamide type surfactant used in the present invention is a compound represented by the above general formula (IV). In the formula, R 1 CO and R 3 CO represent saturated or unsaturated fatty acid residues having 8 to 22 carbon atoms, and typical fatty acid residues are exemplified by coconut oil fatty acid, palm kernel oil fatty acid, lauric acid, Fatty acid residues such as myristyl acid, tallow fatty acid, hydrogenated tallow fatty acid, oleic acid, castor oil fatty acid and hydrogenated castor oil fatty acid.
【０００７】本発明において用いられる逆浸透膜として
は、例えばセルロースアセテート膜、スルホン化ポリス
ルホン膜、ポリアミド化スルホン膜等があげられる。こ
れらの逆浸透膜を用いて前記脂肪酸ジエタノールアミド
型界面活性剤を処理するには、前記脂肪酸ジエタノール
アミド型界面活性剤濃度を１０〜９０％、好ましくは４
０〜６０％に調整し、圧力は５〜４０Ｋｇ／ｃｍ2 、温
度は逆浸透膜の種類によって異なるが一般的には常温で
処理する。処理時間とともに被処理液量は減少するため
常に水を補充して逆浸透膜処理を行う。Examples of the reverse osmosis membrane used in the present invention include a cellulose acetate membrane, a sulfonated polysulfone membrane, a polyamidated sulfone membrane and the like. To treat the fatty acid diethanolamide type surfactant with these reverse osmosis membranes, the concentration of the fatty acid diethanolamide type surfactant is 10 to 90%, preferably 4%.
It is adjusted to 0 to 60%, the pressure is 5 to 40 Kg / cm 2 , and the temperature varies depending on the type of the reverse osmosis membrane, but generally the treatment is performed at room temperature. Since the amount of liquid to be treated decreases with the treatment time, water is always replenished for reverse osmosis membrane treatment.
【０００８】本発明界面活性剤は、界面活性剤工業で一
般的に使用されている他の界面活性剤と配合することが
できる。それらの界面活性剤としては、例えば脂肪酸石
けん、高級アルコール硫酸エステル塩、ポリオキシエチ
レン高級アルコール硫酸エステル塩、高級アルコールリ
ン酸エステル塩、ポリオキシエチレン高級アルコールリ
ン酸エステル塩、ポリオキシエチレン高級脂肪酸リン酸
エステル塩、スルホン化高級脂肪酸塩、高級アルコール
スルホコハク酸エステル塩、アシルメチルタウレイト、
Ｎ−長鎖アシル−グルタミン酸塩、Ｎ−長鎖アシル−サ
ルコシン塩、Ｎ−長鎖アシル−Ｎ−アルキル−βアラニ
ン塩、アシルイセチオン酸塩、αーオレフィンスルホン
酸塩、などのアニオン界面活性剤、脂肪酸モノエタノー
ルアミド、ポリオキシエチレン脂肪酸モノエタノールア
ミド等のノニオン界面活性剤、アルキルイミダゾリニウ
ムベタイン、脂肪酸アミドプロピルベタイン型等の両性
界面活性剤、第４級アンモニウム塩型カチオン界面活性
剤等のカチオン界面活性剤等がある。The surfactants of this invention can be combined with other surfactants commonly used in the surfactant industry. Examples of such surfactants include fatty acid soap, higher alcohol sulfate ester salt, polyoxyethylene higher alcohol sulfate ester salt, higher alcohol phosphate ester salt, polyoxyethylene higher alcohol phosphate ester salt, polyoxyethylene higher fatty acid phosphorus salt. Acid ester salt, sulfonated higher fatty acid salt, higher alcohol sulfosuccinate ester salt, acylmethyl taurate,
Anionic surfactants such as N-long-chain acyl-glutamate, N-long-chain acyl-sarcosine salt, N-long-chain acyl-N-alkyl-β-alanine salt, acyl isethionate, α-olefin sulfonate, and the like, Nonionic surfactants such as fatty acid monoethanolamide and polyoxyethylene fatty acid monoethanolamide, amphoteric surfactants such as alkylimidazolinium betaine and fatty acid amide propyl betaine type, cations such as quaternary ammonium salt type cationic surfactant There are surfactants and the like.
【０００９】また、必要に応じて、グリコール類等の可
溶化剤、エステル油等のエモリエント剤、ヒアルロン
酸、キチン、キトサン等の保湿剤、アロエエキス、胎盤
抽出液等の細胞賦活剤、アラントイン、グリチルリチン
酸等の消炎剤、ジンクピリチオン、ピロクトンオラミン
等の抗フケ剤及び殺菌剤、香料、色素なども加えること
ができる。If necessary, solubilizers such as glycols, emollients such as ester oils, moisturizers such as hyaluronic acid, chitin and chitosan, cell activating agents such as aloe extract and placenta extract, allantoin, Anti-inflammatory agents such as glycyrrhizinic acid, anti-dandruff agents such as zinc pyrithione and piroctone olamine, and bactericides, fragrances, pigments and the like can also be added.
【００１０】[0010]
【実施例】以下実施例により本発明をさらに詳細に説明
する。The present invention will be described in more detail with reference to the following examples.
【００１１】実施例１ 椰子油脂肪酸メチルエステル ７３４ｇ、ジエタノール
アミン ３６７ｇ、ソジュウムメチラート２８％メタノ
ール溶液 ６ｇを取り、８０℃まで昇温する。徐々に減
圧し、約３時間かけ１０ｍｍＨｇまで減圧を行い、脱メ
タノールを行なう。約１００ｇのメタノールを除いた
後、約１時間同一条件で熟成を行ない椰子油脂肪酸ジエ
タノールアミド１０００ｇを得た。このものの分析値
は、乾燥残分（１０５℃、２時間）９５．５％、ジエタ
ノールアミン含量５．８％であった。この脂肪酸ジエタ
ノールアミドに水１０００ｇを加え、さらに３５％塩酸
１０ｇを加えｐＨ９．５とし濃度５０％に調整した後、
膜面積０．７２４ｍ2 のポリアミド化スルホン膜をセッ
トした逆浸透膜処理装置（商品名「２０型ＲＯ／ＵＦテ
ストモジュール」；テクノユニバース（株）製）に圧力
２０Ｋｇ／ｃｍ2 で循環させ、膜透過液の除去によって
処理液の液量が減少しないように水を加えた。全量で１
０００ｇの透過液を取り処理を完了する。得られたもの
の分析値は、乾燥残分４２．５％、ジエタノールアミン
含量０．５％であった。Example 1 734 g of coconut oil fatty acid methyl ester, 367 g of diethanolamine, and 6 g of 28% sodium methylate methanol solution were taken and heated to 80 ° C. The pressure is gradually reduced, and the pressure is reduced to 10 mmHg over about 3 hours to remove methanol. After removing about 100 g of methanol, the mixture was aged for about 1 hour under the same conditions to obtain 1000 g of palm oil fatty acid diethanolamide. The analytical values of this product were a dry residue (105 ° C., 2 hours) of 95.5% and a diethanolamine content of 5.8%. After adding 1000 g of water to this fatty acid diethanolamide and further adding 10 g of 35% hydrochloric acid to adjust the pH to 9.5 and adjusting the concentration to 50%,
Reverse osmosis membrane treatment apparatus equipped with a polyamide sulfonic film membrane area 0.724M 2 (trade name "20-RO / UF test module", manufactured Techno universe Co.) was circulated at a pressure 20 Kg / cm 2, membrane Water was added so that the amount of the treatment liquid did not decrease due to the removal of the permeated liquid. 1 in total
000 g of permeate is taken to complete the process. The analytical values of the obtained product were a dry residue of 42.5% and a diethanolamine content of 0.5%.
【００１２】実施例２ ジエタノールアミン ３２８ｇ、水酸化ナトリウム
２．５ｇを取り、椰子油６６８ｇを仕込み８０℃、３０
ｍｍＨｇの減圧下で１時間反応させ、椰子油脂肪酸ジエ
タノールアミド１０００ｇを得た。このものの分析値
は、乾燥残分（１０５℃、２時間）９５．６％、ジエタ
ノールアミン含量５．３％であった。この脂肪酸ジエタ
ノールアミドに水１０００ｇを加え、さらに３５％塩酸
１０ｇを加えｐＨ９．７とし濃度５０％に調整した後、
膜面積０．７２４ｍ2 のポリアミド化スルホン膜をセッ
トした逆浸透膜処理装置（商品名「２０型ＲＯ／ＵＦテ
ストモジュール」；テクノユニバース（株）製）に圧力
２０Ｋｇ／ｃｍ2 で循環させ、膜透過液の除去によって
処理液の液量が減少しないように水を加えた。全量で１
０００ｇの透過液を取り処理を完了する。得られたもの
の分析値は、乾燥残分４１．３％、ジエタノールアミン
含量０．６％であった。Example 2 328 g of diethanolamine, sodium hydroxide
Take 2.5 g and charge 668 g of coconut oil at 80 ° C, 30
The mixture was reacted under reduced pressure of mmHg for 1 hour to obtain 1000 g of coconut oil fatty acid diethanolamide. The analytical values of this product were a dry residue (105 ° C., 2 hours) of 95.6% and a diethanolamine content of 5.3%. After adding 1000 g of water to this fatty acid diethanolamide and further adding 10 g of 35% hydrochloric acid to adjust the pH to 9.7 and adjusting the concentration to 50%,
Reverse osmosis membrane treatment apparatus equipped with a polyamide sulfonic film membrane area 0.724M 2 (trade name "20-RO / UF test module", manufactured Techno universe Co.) was circulated at a pressure 20 Kg / cm 2, membrane Water was added so that the amount of the treatment liquid did not decrease due to the removal of the permeated liquid. 1 in total
000 g of permeate is taken to complete the process. The analytical values of the obtained product were a dry residue of 41.3% and a diethanolamine content of 0.6%.
【００１３】[0013]
【発明の効果】本発明によって得られる脂肪酸ジエタノ
ールアミドはジエタノールアミン含量が極めて低いの
で、経時着色が起こりにくい。INDUSTRIAL APPLICABILITY The fatty acid diethanolamide obtained according to the present invention has an extremely low diethanolamine content, so that coloring with time hardly occurs.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｃ 233/20 9547−4Ｈ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display location C07C 233/20 9547-4H
Claims (1)
ミンと ＨＮ（ＣＨ2ＣＨ2ＯＨ）2 （Ｉ） 一般式（ＩＩ） Ｒ1ＣＯＯＲ2 （ＩＩ） （式中Ｒ1ＣＯは、炭素数８〜２２の飽和または不飽和
脂肪酸残基を表し、Ｒ2は水素原子または炭素数１〜６
のアルキル基を表す。）または、一般式（ＩＩＩ） 【化１】 （ＩＩＩ） （式中Ｒ3ＣＯは、炭素数８〜２２の飽和または不飽和
脂肪酸残基を表す。）で表される脂肪酸および脂肪酸エ
ステルと反応させて得られる一般式（ＩＶ） 【化２】 （ＩＶ） （式中Ｒ4ＣＯは、前記Ｒ1ＣＯまたはＲ3ＣＯ）で表さ
れ、未反応ジエタノールアミンを不純物として含有する
生成物に対し、逆浸透膜処理を行うことを特徴とする、
ジエタノールアミン含量の低い脂肪酸ジエタノールアミ
ド型界面活性剤の製造方法。1. A diethanolamine represented by the general formula (I) and HN (CH 2 CH 2 OH) 2 (I) a general formula (II) R 1 COOR 2 (II) (wherein R 1 CO is a carbon number). 8 to 22 represents a saturated or unsaturated fatty acid residue, R 2 is a hydrogen atom or a carbon number of 1 to 6
Represents an alkyl group. ) Or general formula (III) (III) (wherein R 3 CO represents a saturated or unsaturated fatty acid residue having 8 to 22 carbon atoms) and a general formula (IV) obtained by reacting with a fatty acid and a fatty acid ester. ] (IV) (In the formula, R 4 CO is R 1 CO or R 3 CO), and a product containing unreacted diethanolamine as an impurity is subjected to reverse osmosis membrane treatment,
A method for producing a fatty acid diethanolamide type surfactant having a low diethanolamine content.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3178713A JP2972395B2 (en) | 1991-06-24 | 1991-06-24 | Method for producing fatty acid diethanolamide type surfactant having low diethanolamine content |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3178713A JP2972395B2 (en) | 1991-06-24 | 1991-06-24 | Method for producing fatty acid diethanolamide type surfactant having low diethanolamine content |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08198830A true JPH08198830A (en) | 1996-08-06 |
| JP2972395B2 JP2972395B2 (en) | 1999-11-08 |
Family
ID=16053266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3178713A Expired - Lifetime JP2972395B2 (en) | 1991-06-24 | 1991-06-24 | Method for producing fatty acid diethanolamide type surfactant having low diethanolamine content |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2972395B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000036055A1 (en) * | 1998-12-15 | 2000-06-22 | Aae Holdings Plc | Fuel composition |
| JP2013199438A (en) * | 2012-03-23 | 2013-10-03 | Matsumoto Yushi Seiyaku Co Ltd | Method for producing fatty acid alkanolamide |
| JPWO2017006995A1 (en) * | 2015-07-09 | 2018-03-08 | 株式会社日本触媒 | Cement additive, cement composition, and raw material for cement additive |
| US10450525B2 (en) | 2014-08-27 | 2019-10-22 | Chevron Oronite Company Llc | Process for alaknolamide synthesis |
-
1991
- 1991-06-24 JP JP3178713A patent/JP2972395B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000036055A1 (en) * | 1998-12-15 | 2000-06-22 | Aae Holdings Plc | Fuel composition |
| JP2013199438A (en) * | 2012-03-23 | 2013-10-03 | Matsumoto Yushi Seiyaku Co Ltd | Method for producing fatty acid alkanolamide |
| US10450525B2 (en) | 2014-08-27 | 2019-10-22 | Chevron Oronite Company Llc | Process for alaknolamide synthesis |
| JPWO2017006995A1 (en) * | 2015-07-09 | 2018-03-08 | 株式会社日本触媒 | Cement additive, cement composition, and raw material for cement additive |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2972395B2 (en) | 1999-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101497564A (en) | Method for synthesizing aliphatic alcohol polyethenoxy ether carboxylate | |
| EP0690044A2 (en) | Process for producing amidoether carboxylic acid or salt thereof, and surface active agent mixture containing the same | |
| US4478734A (en) | Detergent composition comprising a mixture of an N-acyllysine and anionic surface active agents, possessing unique properties in soft and hard water | |
| JPH0291050A (en) | Production of flowable concentrated betaine aqueous solution | |
| JP2972395B2 (en) | Method for producing fatty acid diethanolamide type surfactant having low diethanolamine content | |
| JPH07233139A (en) | Taurine derivative its production, detergent composition containing the same and its intermediate | |
| JP2932377B2 (en) | Liquid detergent thickening method | |
| JP4030746B2 (en) | Pearl luster imparting agent | |
| WO2000072952A1 (en) | Use of a carboxylate alkyl polyglycoside surfactant to increase the foam of other anionic surfactants | |
| JPH04321656A (en) | Production of n-long-chain acylaminocarboxylic acid or aminosulfonic acid type surfactant and cleaner composition containing the same surfactant | |
| JPH08245984A (en) | Liquid cleaning agent composition | |
| JPH04149169A (en) | Surfactant | |
| JPH0832913B2 (en) | Method for producing amphoteric surfactant | |
| JPH0331263A (en) | Imidazolin polycarboxylate and its manufacture, detergent, cosmetic and body care agent containing said compound | |
| JPH0693289A (en) | Surfactant composition | |
| JPS63161080A (en) | Liquid detergent composition | |
| JP3039817B2 (en) | Shampoo composition | |
| JPH05339597A (en) | Detergent composition | |
| JP2791712B2 (en) | Liquid detergent composition | |
| JPH0318615B2 (en) | ||
| JP2787469B2 (en) | Hypoallergenic cleaning composition containing an amino acid type surfactant containing two or more carboxyl groups in one molecule | |
| JP2975733B2 (en) | Method for producing fatty acid jetanolamide with low content of jetanolamine | |
| JPH06321739A (en) | Shampoo composition | |
| JP2972396B2 (en) | Method for producing fatty acid diethanolamide having low diethanolamine content | |
| JP3064036B2 (en) | Shampoo composition |