JPH0543527A - Amide amine and its production - Google Patents
Amide amine and its productionInfo
- Publication number
- JPH0543527A JPH0543527A JP3206844A JP20684491A JPH0543527A JP H0543527 A JPH0543527 A JP H0543527A JP 3206844 A JP3206844 A JP 3206844A JP 20684491 A JP20684491 A JP 20684491A JP H0543527 A JPH0543527 A JP H0543527A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- carbon atoms
- amine
- general formula
- alkyl group
- 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)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規なアミドアミン及び
その製造法に関するものである。更に詳しくは、界面活
性剤、更には布、毛髪等の柔軟剤として有用な新規なア
ミドアミン及びその製造法に関するものである。FIELD OF THE INVENTION The present invention relates to a novel amidoamine and a method for producing the same. More specifically, the present invention relates to a novel amidoamine which is useful as a surfactant and also as a softening agent for cloth, hair and the like, and a method for producing the same.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来、
布及び毛髪等の柔軟剤として使用されている化合物は、
２本の長鎖アルキル基を有する第４級アンモニウム塩で
あるが、生分解性のより優れた柔軟基剤を開発する必要
がある。本発明の課題は、柔軟性に優れかつ生分解性の
より優れた柔軟基剤として適した化合物を得ることであ
る。2. Description of the Related Art Conventionally, the problems to be solved by the invention
Compounds used as softeners for cloth and hair are
Although it is a quaternary ammonium salt having two long-chain alkyl groups, it is necessary to develop a soft base having higher biodegradability. An object of the present invention is to obtain a compound having excellent flexibility and biodegradability, which is suitable as a soft base.
【０００３】[0003]
【課題を解決するための手段】本発明者らは、上記課題
を解決すべく鋭意検討した結果、特定の新規なアミドア
ミンが上記目的に最適であることを見いだし、本発明を
完成した。すなわち、本発明は、一般式（Ｉ）で表され
るアミドアミン及びその製造方法を提供するものであ
る。As a result of intensive studies to solve the above problems, the present inventors have found that a specific novel amidoamine is optimal for the above purpose, and completed the present invention. That is, the present invention provides an amidoamine represented by the general formula (I) and a method for producing the same.
【０００４】[0004]
【化４】 [Chemical 4]
【０００５】（式中、R1は炭素数１〜６のアルキル基ま
たはヒドロキシアルキル基、R2は炭素数８〜36の直鎖も
しくは分岐鎖のアルキル基またはアルケニル基、R3は炭
素数７〜35の直鎖もしくは分岐鎖のアルキル基またはア
ルケニル基、n は１〜３の整数を示す。)一般式（Ｉ）
で表される化合物としては、例えば次のようなものが挙
げられる。(Wherein R 1 is an alkyl group or hydroxyalkyl group having 1 to 6 carbon atoms, R 2 is a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms, and R 3 is 7 carbon atoms. To a linear or branched alkyl group or alkenyl group of 35, and n is an integer of 1 to 3.) General formula (I)
Examples of the compound represented by are as follows.
【０００６】[0006]
【化５】 [Chemical 5]
【０００７】上記一般式（Ｉ）で表される本発明のアミ
ドアミンは、次の方法により製造される。即ち、まず一
般式（II)The amidoamine of the present invention represented by the above general formula (I) is produced by the following method. That is, first the general formula (II)
【０００８】[0008]
【化６】 [Chemical 6]
【０００９】（式中、R1, R2は前記と同じ意味を示
す。）で表される２級アミンを、アクリロニトリルを用
いてシアノエチル化した後、水素化反応を行いニトリル
基のアミノ化を行う。必要とあれば、シアノエチル化、
水素化反応を繰り返し、一般式（III)で表されるアミン
を得る。The secondary amine represented by the formula (wherein R 1 and R 2 have the same meanings as described above) is cyanoethylated with acrylonitrile and then hydrogenated to aminate the nitrile group. To do. Cyanoethylation if necessary,
The hydrogenation reaction is repeated to obtain the amine represented by the general formula (III).
【００１０】[0010]
【化７】 [Chemical 7]
【００１１】（式中、R1, R2, n は前記と同じ意味を示
す。)続いて、一般式（III)で表されるアミンを、一般
式（IV) R3COOR4 （IV） （式中、R3は前記と同じ意味を示し、R4はH または炭素
数１〜３のアルキル基を示す。)で表される脂肪酸もし
くは脂肪酸エステルを用いてアミド化を行い、前記一般
式（Ｉ）で表されるアミドアミンを製造する。(In the formula, R 1 , R 2 and n have the same meanings as described above.) Then, the amine represented by the general formula (III) is converted to the general formula (IV) R 3 COOR 4 (IV) (In the formula, R 3 has the same meaning as described above, and R 4 represents H or an alkyl group having 1 to 3 carbon atoms.) Amidation is performed using a fatty acid or a fatty acid ester, and the above general formula is used. The amidoamine represented by (I) is produced.
【００１２】更に詳しく述べるなら、本発明のアミドア
ミンの製造は次のように説明できる。一般式（II) で表
される２級アミンへのアクリロニトリルの付加反応にお
いて、２級アミンに対し、0.8 〜５倍モルのアクリロニ
トリルを 0.5〜５時間かけて、反応温度を50〜90℃に保
ちながら添加する。次いで、この付加物を触媒の存在
下、60〜150℃、１〜10時間かけて水素化反応を行う。
必要とあればアクリロニトリルの付加反応、水素化反応
を繰り返し、一般式（III)で表されるアミンを得る。得
られたアミン（III)に、アミン（III)に対して0.8 〜２
倍モルの一般式（IV) で表される脂肪酸もしくは脂肪酸
エステルを用いて、無触媒又は触媒の存在下、100 〜22
0 ℃で１〜20時間かけて常圧もしくは減圧下でアミド化
反応を行い、一般式（Ｉ）で表されるアミドアミンを得
る。More specifically, the production of the amidoamine of the present invention can be explained as follows. In the addition reaction of acrylonitrile to the secondary amine represented by the general formula (II), the reaction temperature is kept at 50 to 90 ° C. for 0.5 to 5 hours by adding 0.8 to 5 times mol of acrylonitrile to the secondary amine. While adding. Then, this adduct is subjected to hydrogenation reaction in the presence of a catalyst at 60 to 150 ° C. for 1 to 10 hours.
If necessary, the addition reaction of acrylonitrile and the hydrogenation reaction are repeated to obtain the amine represented by the general formula (III). The obtained amine (III) has 0.8 to 2 with respect to the amine (III).
Using a double mole of the fatty acid or fatty acid ester represented by the general formula (IV), 100 to 22 in the presence of a catalyst or no catalyst.
The amidation reaction is carried out at 0 ° C. for 1 to 20 hours under normal pressure or reduced pressure to obtain an amidoamine represented by the general formula (I).
【００１３】本発明において使用される一般式（II) で
表される２級アミンとしてはＮ−メチルオクチルアミ
ン、Ｎ−メチルデシルアミン、Ｎ−メチルドデシルアミ
ン、Ｎ−メチルテトラデシルアミン、Ｎ−メチルヘキサ
デシルアミン、Ｎ−メチルオクタデシルアミン、Ｎ−メ
チルエイコシルアミン、Ｎ−メチルドコシルアミン、Ｎ
−メチル−２−エチルヘキシルアミン、Ｎ−メチル−２
−ブチルオクチルアミン、Ｎ−メチル−２−ヘキシルデ
シルアミン、Ｎ−メチル−２−オクチルドデシルアミ
ン、Ｎ−メチル−２−デシルテトラデシルアミン、Ｎ−
メチル−２−デシルヘキサデシルアミン、Ｎ−メチル−
２−ヘキサデシルエイコシルアミン、Ｎ−プロピルヘキ
サデシルアミン、Ｎ−プロピルオクタデシルアミン、Ｎ
−ヘキシルヘキサデシルアミン、Ｎ−ヘキシルオクタデ
シルアミン、Ｎ−ヒドロキシエチルヘキサデシルアミ
ン、Ｎ−ヒドロキシエチルオクタデシルアミン等、また
はそれらの混合物が挙げられる。The secondary amine represented by the general formula (II) used in the present invention is N-methyloctylamine, N-methyldecylamine, N-methyldodecylamine, N-methyltetradecylamine, N- Methyl hexadecyl amine, N-methyl octadecyl amine, N-methyl eicosyl amine, N-methyl docosyl amine, N
-Methyl-2-ethylhexylamine, N-methyl-2
-Butyloctylamine, N-methyl-2-hexyldecylamine, N-methyl-2-octyldodecylamine, N-methyl-2-decyltetradecylamine, N-
Methyl-2-decylhexadecylamine, N-methyl-
2-hexadecyl eicosyl amine, N-propyl hexadecyl amine, N-propyl octadecyl amine, N
-Hexylhexadecylamine, N-hexyloctadecylamine, N-hydroxyethylhexadecylamine, N-hydroxyethyloctadecylamine and the like, or a mixture thereof.
【００１４】本発明においてアミド化に使用される一般
式（IV) で表される脂肪酸もしくは脂肪酸エステルとし
ては、オクタン酸、デカン酸、ドデカン酸、テトラデカ
ン酸、ヘキサデカン酸、オクタデカン酸、エイコサン
酸、ドコサン酸、２−エチルヘキサン酸、２−ブチルオ
クタン酸、２−ヘキシルデカン酸、２−オクチルドデカ
ン酸、２−デシルテトラデカン酸、２−ドデシルヘキサ
デカン酸、２−テトラデシルオクタデカン酸、２−ヘキ
サデシルエイコサン酸あるいはこれら脂肪酸のメチルエ
ステル、エチルエステル、プロピルエステルなど、また
はこれらの混合物が挙げられる。本発明のアミド化に使
用される触媒としては、ナトリウムメチラート、ナトリ
ウムエチラート、カリウムメチラート、カリウムエチラ
ート、水酸化ナトリウム、水酸化カリウムなどが挙げら
れる。The fatty acid or fatty acid ester represented by the general formula (IV) used for amidation in the present invention includes octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, docosane. Acid, 2-ethylhexanoic acid, 2-butyloctanoic acid, 2-hexyldecanoic acid, 2-octyldodecanoic acid, 2-decyltetradecanoic acid, 2-dodecylhexadecanoic acid, 2-tetradecyloctadecanoic acid, 2-hexadecyleicosane Examples thereof include acids, methyl esters, ethyl esters, propyl esters, and the like of these fatty acids, or a mixture thereof. Examples of the catalyst used for the amidation of the present invention include sodium methylate, sodium ethylate, potassium methylate, potassium ethylate, sodium hydroxide, potassium hydroxide and the like.
【００１５】本発明の一般式（Ｉ）で表されるアミドア
ミンは赤外吸収スペクトル、核磁気共鳴スペクトルでそ
の構造を確認することができる。The structure of amidoamine represented by the general formula (I) of the present invention can be confirmed by infrared absorption spectrum and nuclear magnetic resonance spectrum.
【００１６】[0016]
【発明の効果】本発明が提供する一般式（Ｉ）で表され
るアミドアミンは、新規な界面活性剤であり、生分解性
の優れた柔軟剤基剤として有用である。INDUSTRIAL APPLICABILITY The amidoamine represented by the general formula (I) provided by the present invention is a novel surfactant and useful as a softening agent base having excellent biodegradability.
【００１７】[0017]
【実施例】以下に実施例により本発明を更に詳細に説明
するが、本発明はこれらに限定されるものではない。 実施例１N −〔３−（N'−オクタデシル−N'−メチルアミノ）プ
ロピル〕オクタデシルアミドの合成 撹拌機、温度計、滴下ロートを備えた４つ口フラスコに
N−メチルオクタデシルアミン100 ｇを入れ、60℃まで
昇温した。液温を60〜65℃に保ちながらアクリロニトリ
ル19ｇを 0.5時間かけて滴下した。滴下終了後、そのま
まの温度で10時間熟成を行った。熟成終了後、反応液を
撹拌機、温度計、圧力計を備えたオートクレーブに移し
た。続いてラネーNi 24 ｇを添加し、水素圧を20kg／cm
2 に保ちながら６時間かけて水素化反応を行った。反応
終了後、ラネーNiを濾過し、反応液を蒸留して92ｇの N
−（３−アミノプロピル）−N −メチルオクタデシルア
ミンを得た。沸点は180 ℃／0.2 mmHgであった。撹拌
機、温度計、脱水管を備えた４つ口フラスコに N−（３
−アミノプロピル）−N −メチルオクタデシルアミン69
ｇとオクタデカン酸55ｇを入れ、180 ℃まで昇温した。
そのままの温度で６時間、生成する水を留去しながらア
ミド化反応を行い、目的とする標題化合物を119 ｇ得
た。 NMR スペクトル、IRスペクトルから以下の構造を確認し
た。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto. Example 1 N- [3- (N'-octadecyl-N'-methylamino) propyl
Ropil] octadecylamide synthesis In a four-necked flask equipped with a stirrer, thermometer, dropping funnel
100 g of N-methyloctadecylamine was added and the temperature was raised to 60 ° C. 19 g of acrylonitrile was added dropwise over 0.5 hours while maintaining the liquid temperature at 60 to 65 ° C. After the completion of dropping, the mixture was aged at the same temperature for 10 hours. After completion of aging, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Subsequently, Raney Ni 24 g was added, and the hydrogen pressure was 20 kg / cm.
While maintaining at 2 , the hydrogenation reaction was carried out for 6 hours. After the reaction was completed, Raney Ni was filtered, and the reaction solution was distilled to obtain 92 g of N 2.
-(3-Aminopropyl) -N-methyloctadecylamine was obtained. The boiling point was 180 ° C / 0.2 mmHg. A four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube was equipped with N- (3
-Aminopropyl) -N-methyloctadecylamine 69
g and 55 g of octadecanoic acid were added and the temperature was raised to 180 ° C.
The amidation reaction was carried out at the same temperature for 6 hours while distilling off the produced water to obtain 119 g of the desired title compound. The following structure was confirmed from the NMR spectrum and IR spectrum.
【００１８】[0018]
【化８】 [Chemical 8]
【００１９】・NMR スペクトル（CDCl3 、内部標準TMS)
δ： 2.1ppm(t,2H) CH2 -CO-NH, 2.2ppm(s,3H) N-CH3 3.3ppm(q,2H) CH2 -NH-CO-, 7.2ppm(t,1H) NH-CO ・IRスペクトル (KBr 錠剤) ： 1660 cm-1、1570cm-1 実施例２ 撹拌機、温度計、滴下ロートを備えた４つ口フラスコに
N−メチルオクタデシルアミン 100ｇを入れ、60℃まで
昇温した。液温を60〜65℃に保ちながらアクリロニトリ
ル19ｇを 0.5時間かけて滴下した。滴下終了後、そのま
まの温度で10時間熟成を行った。熟成終了後、反応液を
撹拌機、温度計、圧力計を備えたオートクレーブに移し
た。続いてラネーNi 24ｇを添加し、水素圧を20kg／cm2
に保ちながら６時間かけて水素化反応を行った。続い
て、アクリロニトリル19ｇを60℃で加えそのままの温度
で１時間熟成を行った。熟成終了後、水素圧20kg／cm2
に保ちながら６時間かけて水素化反応を行った。反応終
了後ラネーNiを濾過し、110ｇの N−メチル−N −オク
タデシルジプロピレントリアミンを得た。撹拌機、温度
計、脱水管を備えた４つ口フラスコに N−メチル−N −
オクタデシルジプロピレントリアミン76ｇとオクタデカ
ン酸55ｇを入れ、180℃まで昇温した。そのままの温度
で６時間、生成する水を留去しながらアミド化反応を行
い、目的物を125 ｇ得た。 NMR スペクトル、IRスペクトルから以下の構造を確認し
た。NMR spectrum (CDCl3, Internal standard TMS)
δ: 2.1ppm (t, 2H) CH 2 -CO-NH, 2.2ppm (s, 3H) N-CH 3 3.3ppm (q, 2H) CH 2 -NH-CO-, 7.2ppm (t, 1H)NH-CO / IR spectrum (KBr tablet): 1660 cm-1, 1570 cm-1 Example 2 In a four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel.
Add 100 g of N-methyloctadecylamine to 60 ℃
The temperature was raised. Acrylonitri while maintaining the liquid temperature at 60-65 ℃
(19 g) was added dropwise over 0.5 hour. After the dropping is complete,
It was aged at that temperature for 10 hours. After aging,
Transfer to an autoclave equipped with stirrer, thermometer, pressure gauge
It was Then, Raney Ni 24g was added and the hydrogen pressure was 20kg / cm.2
The hydrogenation reaction was carried out for 6 hours while maintaining the above. Continued
Then, add 19g of acrylonitrile at 60 ℃ and keep the same temperature.
It was aged for 1 hour. After aging, hydrogen pressure 20kg / cm2
The hydrogenation reaction was carried out for 6 hours while maintaining the above. End of reaction
After that, Raney Ni was filtered and 110 g of N-methyl-N-octane was added.
Tadecyl dipropylene triamine was obtained. Stirrer, temperature
N-methyl-N-in a four-necked flask equipped with a meter and a dehydration tube.
Octadecyl dipropylene triamine 76g and octadeca
55 g of acid was added and the temperature was raised to 180 ° C. Temperature as it is
The amidation reaction is performed for 6 hours while distilling off the produced water.
125 g of the desired product was obtained. The following structure was confirmed from the NMR spectrum and IR spectrum.
It was
【００２０】[0020]
【化９】 [Chemical 9]
【００２１】・NMR スペクトル（CDCl3 、内部標準TMS)
δ： 2.1ppm(t,2H) CH2 -CO-NH, 2.2ppm(s,3H) N-CH3 2.6ppm(t,4H) CH2 -NH-CH2 , 3.3ppm(q,2H) CH2 -NH-CO 7.2ppm(t,1H) NH-CO ・IRスペクトル (KBr 錠剤) ： 1655 cm-1、１５４０ｃｍ−１ NMR spectrum (CDCl 3 , internal standard TMS)
δ: 2.1ppm (t, 2H) C H 2 -CO-NH, 2.2ppm (s, 3H) NC H 3 2.6ppm (t, 4H) C H 2 -NH-C H 2 , 3.3ppm (q, 2H ) C H 2 -NH-CO 7.2ppm (t, 1H) NH -CO IR spectrum (KBr tablet): 1655 cm -1 , 1540 cm -1
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｃ 233/38 7106−4Ｈ Ｄ０６Ｍ 13/402 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI Technical display location C07C 233/38 7106-4H D06M 13/402
Claims (2)
シアルキル基、R2は炭素数８〜36の直鎖もしくは分岐鎖
のアルキル基またはアルケニル基、R3は炭素数７〜35の
直鎖もしくは分岐鎖のアルキル基またはアルケニル基、
n は１〜３の整数を示す。)1. An amidoamine represented by the general formula (I). [Chemical 1] (In the formula, R 1 is an alkyl group or a hydroxyalkyl group having 1 to 6 carbon atoms, R 2 is a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms, and R 3 is an alkyl group having 7 to 35 carbon atoms. A linear or branched alkyl group or alkenyl group,
n shows the integer of 1-3. )
シアルキル基、R2は炭素数８〜36の直鎖もしくは分岐鎖
のアルキル基またはアルケニル基を示す。）で表される
２級アミンにアクリロニトリルを付加反応させ、ついで
水素化反応を行い、必要とあらばこの操作を繰り返して
得られる、一般式（III) 【化３】 （式中、R1, R2は上記と同じ意味を示し、n は１〜３の
整数を示す。)で表されるアミンを、一般式（IV） R3COOR4 （IV） （式中、R3は炭素数７〜35の直鎖もしくは分岐鎖のアル
キル基またはアルケニル基、R4はH または炭素数１〜３
のアルキル基を示す。)で表される脂肪酸もしくは脂肪
酸エステルでアミド化することを特徴とする、請求項１
記載のアミドアミンの製造法。2. A compound represented by the general formula (II): (In the formula, R 1 represents an alkyl group or a hydroxyalkyl group having 1 to 6 carbon atoms, and R 2 represents a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms.) Acrylonitrile is added to an amine to carry out an addition reaction, then a hydrogenation reaction is carried out, and if necessary, this operation is repeated to obtain a compound of the general formula (III) (In the formula, R 1 and R 2 have the same meanings as described above, and n represents an integer of 1 to 3. ) The amine represented by the general formula (IV) R 3 COOR 4 (IV) (wherein , R 3 is a linear or branched alkyl or alkenyl group having 7 to 35 carbon atoms, R 4 is H or 1 to 3 carbon atoms
Represents an alkyl group of. ) Is amidated with a fatty acid or fatty acid ester represented by the formula (1),
A method for producing the amidoamine described.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3206844A JP3067852B2 (en) | 1991-08-19 | 1991-08-19 | Amidoamine and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3206844A JP3067852B2 (en) | 1991-08-19 | 1991-08-19 | Amidoamine and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0543527A true JPH0543527A (en) | 1993-02-23 |
| JP3067852B2 JP3067852B2 (en) | 2000-07-24 |
Family
ID=16529999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3206844A Expired - Fee Related JP3067852B2 (en) | 1991-08-19 | 1991-08-19 | Amidoamine and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3067852B2 (en) |
-
1991
- 1991-08-19 JP JP3206844A patent/JP3067852B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP3067852B2 (en) | 2000-07-24 |
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