JPH0616608A - Novel diamidoamine and method for producing the same - Google Patents
Novel diamidoamine and method for producing the sameInfo
- Publication number
- JPH0616608A JPH0616608A JP4175265A JP17526592A JPH0616608A JP H0616608 A JPH0616608 A JP H0616608A JP 4175265 A JP4175265 A JP 4175265A JP 17526592 A JP17526592 A JP 17526592A JP H0616608 A JPH0616608 A JP H0616608A
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- group
- reaction
- carbon atoms
- alkyl group
- diamidoamine
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
(57)【要約】
【目的】 柔軟性に優れかつ生分解性のより優れた柔軟
剤として適した化合物を提供する。
【構成】 一般式（Ｉ）で表されるジアミドアミン
【化１】
〔式中、R1、R2は炭素数１〜４のアルキル基もくしはヒ
ドロキシアルキル基、又はR1とR2が一緒になって−CR2
−、−NR−あるいは−O−を介して環を形成する基を示
す。ここで、R はH 又は炭素数１〜４のアルキル基を示
す。R3は炭素数２〜６のアルキレン基又はアルケニレン
基、R4は炭素数７〜35の直鎖もしくは分岐鎖のアルキル
基又はアルケニル基、m 、n は１〜５の整数を示す。〕(57) [Summary] [Object] To provide a compound having excellent flexibility and biodegradability, which is suitable as a softening agent. [Structure] Diamidoamine represented by the general formula (I): [In the formula, R 1 and R 2 are each an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group, or R 1 and R 2 are combined to form --CR 2
A group forming a ring via —, —NR— or —O— is shown. Here, R represents H or an alkyl group having 1 to 4 carbon atoms. R 3 represents an alkylene group having 2 to 6 carbon atoms or an alkenylene group, R 4 represents a linear or branched alkyl group or alkenyl group having 7 to 35 carbon atoms, and m and n each represent an integer of 1 to 5. ]
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規なジアミドアミン及
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、毛髪などの柔軟剤として使用される
新規なジ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 diamidoamine and a method for producing the same. More specifically, the present invention relates to a novel diamidoamine used 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、
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剤を開発する必要がある。従っ
て、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 an alkyl group, it is necessary to develop a softening agent having higher biodegradability. Therefore, an object of the present invention is to obtain a compound having excellent flexibility and biodegradability, which is suitable as a softening agent.
【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、特定の新規ジアミドア
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
るジアミドアミン及びその製造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 diamidoamine is optimal for the above purpose, and completed the present invention. That is, the present invention provides a diamidoamine represented by the general formula (I) and a method for producing the same.
【０００４】[0004]
【化４】 [Chemical 4]
【０００５】〔式中、R1、R2：同一又は異なって、炭素
数１〜４のアルキル基もくしはヒドロキシアルキル基、
又はR1とR2が一緒になって−CR2−、−NR−あるいは−O
−を介して環を形成する基を示す。ここで、R はH 又は
炭素数１〜４のアルキル基を示す。 R3：炭素数２〜６のアルキレン基又はアルケニレン基を
示す。 R4：炭素数７〜35の直鎖もしくは分岐鎖のアルキル基又
はアルケニル基を示し、２つのR4は同一でも異なってい
ても良い。 m 、n ：同一又は異なって、１〜５の整数を示す。〕 一般式（Ｉ）で表されるジアミドアミンとしては、例え
ば次のようなものが挙げられる。[Wherein R 1 and R 2 are the same or different and are an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group,
Or R 1 and R 2 together form --CR 2- , --NR-- or --O
A group forming a ring via-is shown. Here, R represents H or an alkyl group having 1 to 4 carbon atoms. R 3 : represents an alkylene group having 2 to 6 carbon atoms or an alkenylene group. R 4 represents a linear or branched alkyl group or alkenyl group having 7 to 35 carbon atoms, and two R 4 may be the same or different. m and n: the same or different and each represents an integer of 1 to 5. Examples of the diamidoamine represented by the general formula (I) include the following.
【０００６】[0006]
【化５】 [Chemical 5]
【０００７】本発明の一般式（Ｉ）で表されるジアミド
アミン（以下ジアミドアミン（Ｉ）と略記する）は次の
方法により製造される。一般式（II）The diamidoamine represented by the general formula (I) of the present invention (hereinafter abbreviated as diamidoamine (I)) is produced by the following method. General formula (II)
【０００８】[0008]
【化６】 [Chemical 6]
【０００９】〔式中、R1、R2、R3は前記の意味を示
す。〕で表されるアミン（以下アミン（II）と略記す
る）を、アクリロニトリルを用いたシアノエチル化反
応、ついで触媒を用いた水素化反応により、アミノプロ
ピル化し、要すれば、シアノエチル化反応及び水素化反
応を任意に繰り返すことによって、一般式（III)[In the formula, R 1 , R 2 and R 3 have the above-mentioned meanings. ] Amine represented by the following (abbreviated as amine (II) below) is aminopropylated by cyanoethylation reaction using acrylonitrile and then hydrogenation reaction using a catalyst, and if necessary, cyanoethylation reaction and hydrogenation By arbitrarily repeating the reaction, the general formula (III)
【００１０】[0010]
【化７】 [Chemical 7]
【００１１】〔式中、R1、R2、R3、m 、n は前記の意味
を示す。〕で表されるアミン（以下アミン(III) と略記
する）を得、このアミン(III) を、一般式（IV） R4COOR5 （IV） 〔式中、R4は前記の意味を示し、R5はH 又は炭素数１〜
３のアルキル基を示す。〕で表される脂肪酸又はそのエ
ステル（以下脂肪酸又はそのエステル (IV) と略記す
る）でアシル化を行い、ジアミドアミン（Ｉ）を得る。[In the formula, R 1 , R 2 , R 3 , m and n have the above-mentioned meanings. ] An amine represented by the following (hereinafter abbreviated as amine (III)) is obtained, and this amine (III) is represented by the general formula (IV) R 4 COOR 5 (IV) [wherein R 4 has the above-mentioned meaning. , R 5 is H or 1 to 1 carbon atoms
3 represents an alkyl group. ] Acylation is performed with a fatty acid represented by the following formula or its ester (hereinafter abbreviated as fatty acid or its ester (IV)) to obtain diamidoamine (I).
【００１２】ジアミドアミン（Ｉ）の製造法について更
に詳しく説明する。アミン（II）のアクリロニトリルを
用いるシアノエチル化反応においては、アミン（II）に
対して 0.5〜20倍モルのアクリロニトリルを40〜80℃に
保ちながら添加し、１〜10時間かけて反応を終了させ、
シアノエチル化物を得る。このシアノエチル化物の触媒
を用いる水素化反応においては、このシアノエチル化物
をNi等の触媒の存在下、50〜200 ℃、１〜30時間かけて
水素化反応を行う。要すれば、このシアノエチル化反応
及び水素化反応を任意に繰り返すことにより、アミン(I
II) を得る。得られたアミン(III) に、アミン(III) に
対して 1.2〜３倍モルの脂肪酸又はそのエステル (IV)
を用いて無触媒または触媒の存在下、 100〜220 ℃で１
〜30時間かけて常圧もしくは減圧下でアシル化を行い、
ジアミドアミン（Ｉ）を得る。The method for producing diamidoamine (I) will be described in more detail. In the cyanoethylation reaction of amine (II) with acrylonitrile, 0.5 to 20 times mol of acrylonitrile with respect to amine (II) is added while maintaining at 40 to 80 ° C., and the reaction is completed over 1 to 10 hours,
A cyanoethylated product is obtained. In the hydrogenation reaction using the cyanoethylated catalyst, the cyanoethylated hydrogenation reaction is carried out at 50 to 200 ° C. for 1 to 30 hours in the presence of a catalyst such as Ni. If necessary, this cyanoethylation reaction and hydrogenation reaction can be optionally repeated to obtain the amine (I
II) get 1.2 to 3 moles of fatty acid or its ester (IV) is added to the obtained amine (III) with respect to the amine (III).
With or without catalyst in the presence of a catalyst at 100-220 ℃ 1
Acylation is performed under atmospheric pressure or reduced pressure for ~ 30 hours,
Diamidoamine (I) is obtained.
【００１３】本発明においてアシル化に使用される脂肪
酸又はそのエステル (IV) 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
いはこれらの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。本発明のアシル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、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 ester (IV) thereof used for acylation in the present invention includes octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid,
Octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2-butyloctanoic acid, 2-hexyldecanoic acid, 2-octyldodecanoic acid, 2-decyltetradecanoic acid, 2-dodecylhexadecanoic acid, 2-tetradecyloctadecanoic acid , 2-hexadecyl eicosanoic acid or methyl ester, ethyl ester, propyl ester of these fatty acids, or a mixture thereof. Examples of the catalyst used in the acylation of the present invention include sodium methylate, sodium ethylate, potassium methylate, sodium hydroxide, potassium hydroxide and the like.
【００１４】本発明のジアミドアミン（Ｉ）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 the diamidoamine (I) of the present invention can be confirmed by infrared absorption spectrum and nuclear magnetic resonance spectrum.
【００１５】[0015]
【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。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.
【００１６】実施例１ 攪拌機、温度計、滴下ロートを備えた４つ口フラスコに
N,N−ジメチルプロパンジアミン 102ｇを入れ、60℃ま
で昇温した。液温を55〜65℃に保ちながら４時間かけて
アクリロニトリル 530ｇを滴下した。反応終了後、減圧
し過剰分のアクリロニトリルを留去した後、反応液を攪
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 10 ｇを添加し、水素圧20kg／cm
2G、温度を７０℃に保ちながら１０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 125ｇのアミンを得た。攪拌機、温度計、脱水
管を備えた４つ口フラスコに上記のアミン 100ｇとオク
タデカン酸 240ｇを入れ、 180℃まで昇温した。そのま
まの温度で８時間、生成する水を留去しながらアシル化
反応を行い、目的物を 256ｇ得た。1H−NMR スペクト
ル、IRスペクトルから以下の構造を確認した。Example 1 In a four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel.
102 g of N, N-dimethylpropanediamine was added and the temperature was raised to 60 ° C. While maintaining the liquid temperature at 55 to 65 ° C, 530 g of acrylonitrile was added dropwise over 4 hours. After completion of the reaction, the pressure was reduced to distill off excess acrylonitrile, and then the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Then, Raney Ni 10 g was added, and the hydrogen pressure was 20 kg / cm.
The hydrogenation reaction was carried out for 10 hours while maintaining the temperature at 2 G and the temperature at 70 ° C. After completion of the reaction, Raney Ni was filtered and the reaction solution was distilled to obtain 125 g of amine. 100 g of the above amine and 240 g of octadecanoic acid were placed in a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube, and the temperature was raised to 180 ° C. The acylation reaction was carried out at the same temperature for 8 hours while distilling off the produced water to obtain 256 g of the desired product. The following structure was confirmed from the 1 H-NMR spectrum and IR spectrum.
【００１７】[0017]
【化８】 [Chemical 8]
【００１８】・1H−NMR スペクトル(CDCl3、内部標準TM
S) 2.2ppm(s,6H) (CH3)2N- 1 H-NMR spectrum (CDCl 3 , internal standard TM
S) 2.2ppm (s, 6H) (CH 3 ) 2 N-
【００１９】[0019]
【化９】 [Chemical 9]
【００２０】・IRスペクトル(KBr、錠剤） 1644cm-1、1542cm-1 実施例２ 攪拌機、温度計、滴下ロートを備えた４つ口フラスコに
Ｎ−（３−アミノプロピル）モルホリン 200ｇを入れ、
60℃まで昇温した。液温を55〜75℃に保ちながら３時間
かけてアクリロニトリル 736ｇを滴下した。反応終了
後、減圧し過剰分のアクリロニトリルを留去した後、反
応液を攪拌機、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 14 ｇを添加し、水素圧20kg
／cm2G、温度を70℃に保ちながら10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 212ｇのアミンを得た。攪拌機、温度計、脱水
管を備えた４つ口フラスコに上記のアミン 100ｇとドデ
カン酸79ｇとドコサン酸 138ｇを入れ、 180℃まで昇温
した。そのままの温度で５時間、生成する水を留去しな
がらアシル化反応を行い、目的物を 276ｇ得た。1H−NM
R スペクトル、IRスペクトルから以下の構造を確認し
た。また FABマススペクトルより分子量を 762、 622、
902（生成比：２／１／１）と確認した。IR spectrum (KBr, tablet) 1644 cm -1 , 1542 cm -1 Example 2 200 g of N- (3-aminopropyl) morpholine was placed in a four-necked flask equipped with a stirrer, a thermometer and a dropping funnel,
The temperature was raised to 60 ° C. Acrylonitrile (736 g) was added dropwise over 3 hours while maintaining the liquid temperature at 55 to 75 ° C. After completion of the reaction, the pressure was reduced to distill off excess acrylonitrile, and then the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Then, 14 g of Raney Ni was added, and the hydrogen pressure was 20 kg.
The hydrogenation reaction was carried out for 10 hours while maintaining the temperature at 70 ° C./cm 2 G. After completion of the reaction, Raney Ni was filtered and the reaction solution was distilled to obtain 212 g of amine. 100 g of the above amine, 79 g of dodecanoic acid and 138 g of docosanoic acid were placed in a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube, and the temperature was raised to 180 ° C. The acylation reaction was carried out at the same temperature for 5 hours while distilling off the produced water to obtain 276 g of the desired product. 1 H-NM
The following structure was confirmed from the R spectrum and IR spectrum. From the FAB mass spectrum, the molecular weight is 762, 622,
It was confirmed to be 902 (generation ratio: 2/1/1).
【００２１】[0021]
【化１０】 [Chemical 10]
【００２２】[0022]
【化１１】 [Chemical 11]
【００２３】・IRスペクトル(KBr、錠剤） 1640cm-1、1542cm-1 実施例３ 攪拌機、温度計、滴下ロートを備えた４つ口フラスコに
Ｎ−（２−アミノエチル）ピペリジン 150ｇを入れ、60
℃まで昇温した。液温を55〜65℃に保ちながら２時間か
けてアクリロニトリル1240ｇを滴下した。反応終了後、
減圧し過剰分のアクリロニトリルを留去した後、反応液
を攪拌機、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 14 ｇを添加し、水素圧20kg／cm
2G、温度を70℃に保ちながら10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 141ｇのアミンを得た。これを、攪拌機、温度計、
滴下ロートを備えた４つ口フラスコに移し、60℃まで昇
温した。液温を55〜65℃に保ちながら２時間かけてアク
リロニトリル62ｇを滴下した。反応終了後、反応液を攪
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Ni10ｇを添加し、水素圧20kg／cm2G、
温度を70℃に保ちながら10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、 180ｇのアミンを
得た。攪拌機、温度計、脱水管を備えた４つ口フラスコ
に上記のアミン 100ｇとヘキサデカン酸 130ｇを入れ、
180℃まで昇温した。そのままの温度で９時間、生成す
る水を留去しながらアシル化反応を行い、目的物を 260
ｇ得た。1H−NMR スペクトル、IRスペクトルから以下の
構造を確認した。IR spectrum (KBr, tablet) 1640 cm -1 , 1542 cm -1 Example 3 150 g of N- (2-aminoethyl) piperidine was placed in a four-necked flask equipped with a stirrer, a thermometer and a dropping funnel, and 60
The temperature was raised to ° C. 1240 g of acrylonitrile was added dropwise over 2 hours while maintaining the liquid temperature at 55 to 65 ° C. After the reaction,
After depressurizing to distill off excess acrylonitrile, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Then, 14 g of Raney Ni was added, and the hydrogen pressure was 20 kg / cm.
The hydrogenation reaction was carried out for 10 hours while keeping the temperature at 2 G and 70 ° C. After completion of the reaction, Raney Ni was filtered and the reaction solution was distilled to obtain 141 g of amine. This, stirrer, thermometer,
The mixture was transferred to a four-necked flask equipped with a dropping funnel and heated to 60 ° C. 62 g of acrylonitrile was added dropwise over 2 hours while maintaining the liquid temperature at 55 to 65 ° C. After the reaction was completed, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Then add Raney Ni10g, hydrogen pressure 20kg / cm 2 G,
The hydrogenation reaction was carried out for 10 hours while maintaining the temperature at 70 ° C. After completion of the reaction, Raney Ni was filtered to obtain 180 g of amine. Put 100 g of the above amine and 130 g of hexadecanoic acid into a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube,
The temperature was raised to 180 ° C. The acylation reaction was carried out at the same temperature for 9 hours while distilling off the produced water to obtain the desired product.
g was obtained. The following structure was confirmed from the 1 H-NMR spectrum and IR spectrum.
【００２４】[0024]
【化１２】 [Chemical 12]
【００２５】・1H−NMR スペクトル(CDCl3、内部標準TM
S) ２．２５−２．３５ｐｐｍ（ｍ，４Ｈ） ＞Ｎ−ＣＨ
２−ＣＨ２−Ｎ＜ 1 H-NMR spectrum (CDCl 3 , internal standard TM
S) 2.25-2.35 ppm (m, 4H)> N-CH
2 -CH 2 -N <
【００２６】[0026]
【化１３】 [Chemical 13]
【００２７】・ＩＲスペクトル(KBr、錠剤） 1644cm-1、1538cm-1 実施例４ 攪拌機、温度計、滴下ロートを備えた４つ口フラスコに
N,N−ジメチル−1,2エチレンジアミン 352ｇを入れ、6
0℃まで昇温した。液温を55〜65℃に保ちながら５時間
かけてアクリロニトリル2120ｇを滴下した。反応終了
後、減圧し過剰分のアクリロニトリルを留去した後、反
応液を攪拌機、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 39 ｇを添加し、水素圧20kg
／cm2G、温度を70℃に保ちながら12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 600ｇのアミンを得た。これを、攪拌機、温度
計、滴下ロートを備えた４つ口フラスコに移し、60℃ま
で昇温した。液温を55〜65℃に保ちながら１時間かけて
アクリロニトリル 157ｇを滴下した。反応終了後、反応
液を攪拌機、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 38 ｇを添加し、水素圧20kg／
cm2G、温度を70℃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 153ｇのアミンを得た。攪拌機、温度計、脱水管
を備えた４つ口フラスコに上記のアミン 100ｇとドデカ
ン酸 153ｇを入れ、 180℃まで昇温した。そのままの温
度で５時間、生成する水を留去しながらアシル化反応を
行い、目的物を 230ｇ得た。1H−NMR スペクトル、IRス
ペクトルから以下の構造を確認した。IR spectrum (KBr, tablets) 1644 cm -1 , 1538 cm -1 Example 4 In a four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel.
Put 352 g of N, N-dimethyl-1,2 ethylenediamine,
The temperature was raised to 0 ° C. 2120 g of acrylonitrile was added dropwise over 5 hours while maintaining the liquid temperature at 55 to 65 ° C. After completion of the reaction, the pressure was reduced to distill off excess acrylonitrile, and then the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Then Raney Ni 39 g was added and hydrogen pressure was 20 kg.
The hydrogenation reaction was carried out for 12 hours while maintaining the temperature at 70 ° C./cm 2 G. After completion of the reaction, Raney Ni was filtered and the reaction solution was distilled to obtain 600 g of amine. This was transferred to a four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, and the temperature was raised to 60 ° C. While maintaining the liquid temperature at 55 to 65 ° C, 157 g of acrylonitrile was added dropwise over 1 hour. After the reaction was completed, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Then Raney Ni 38 g was added, hydrogen pressure 20 kg /
The hydrogenation reaction was carried out for 6 hours while maintaining cm 2 G and the temperature at 70 ° C. After completion of the reaction, Raney Ni was filtered and the reaction solution was distilled to obtain 153 g of amine. 100 g of the above amine and 153 g of dodecanoic acid were placed in a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube, and the temperature was raised to 180 ° C. Acylation reaction was carried out at the same temperature for 5 hours while distilling off the produced water to obtain 230 g of the desired product. The following structure was confirmed from the 1 H-NMR spectrum and IR spectrum.
【００２８】[0028]
【化１４】 [Chemical 14]
【００２９】・1H−NMR スペクトル(CDCl3、内部標準TM
S) 2.2ppm(s,6H) (CH3)2N- 1 H-NMR spectrum (CDCl 3 , internal standard TM
S) 2.2ppm (s, 6H) (CH 3 ) 2 N-
【００３０】[0030]
【化１５】 [Chemical 15]
【００３１】・IRスペクトル(KBr、錠剤） 1647cm-1、1542cm-1 IR spectrum (KBr, tablets) 1647 cm -1 , 1542 cm -1
【００３２】[0032]
【発明の効果】本発明のジアミドアミンは、柔軟性に優
れかつ生分解性のより優れた界面活性剤として有用であ
り、特に布、毛髪などの柔軟剤として極めて有用であ
る。INDUSTRIAL APPLICABILITY The diamidoamine of the present invention is useful as a surfactant having excellent flexibility and biodegradability, and is particularly useful as a softening agent for cloth, hair and the like.
Claims (2)
ルキル基もくしはヒドロキシアルキル基、又はR1とR2が
一緒になって−CR2−、−NR−あるいは−O−を介して環
を形成する基を示す。ここで、R はH 又は炭素数１〜４
のアルキル基を示す。 R3：炭素数２〜６のアルキレン基又はアルケニレン基を
示す。 R4：炭素数７〜35の直鎖もしくは分岐鎖のアルキル基又
はアルケニル基を示し、２つのR4は同一でも異なってい
ても良い。 m 、n ：同一又は異なって、１〜５の整数を示す。〕1. A diamidoamine represented by the general formula (I): [Wherein R 1 and R 2 are the same or different and are an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group, or R 1 and R 2 are taken together to form --CR 2- , --NR-- or The group which forms a ring via -O- is shown. Where R is H or 1 to 4 carbon atoms
Is an alkyl group. R 3 : represents an alkylene group having 2 to 6 carbon atoms or an alkenylene group. R 4 represents a linear or branched alkyl group or alkenyl group having 7 to 35 carbon atoms, and two R 4 may be the same or different. m and n: the same or different and each represents an integer of 1 to 5. ]
アミンを、アクリロニトリルによるシアノエチル化反
応、ついで触媒を用いた水素化反応により、アミノプロ
ピル化し、要すれば、シアノエチル化反応及び水素化反
応を任意に繰り返すことによって得られる、一般式（Ｉ
ＩＩ） 【化３】 〔式中、Ｒ１、R2、R3、m 、n は前記の意味を示す。〕
で表されるアミンを、一般式（IV） R4COOR5 （IV） 〔式中、R4は前記の意味を示し、R5はH 又は炭素数１〜
３のアルキル基を示す。〕で表される脂肪酸又はそのエ
ステルでアシル化することを特徴とする、請求項１記載
の一般式（Ｉ）で表されるジアミドアミンの製造法。2. A compound represented by the general formula (II): [In the formula, R 1 , R 2 and R 3 have the above-mentioned meanings. ] The amine represented by the following formula is aminopropylated by a cyanoethylation reaction with acrylonitrile and then a hydrogenation reaction using a catalyst, and, if necessary, can be obtained by optionally repeating the cyanoethylation reaction and the hydrogenation reaction. (I
II) [In the formula, R 1 , R 2 , R 3 , m and n have the above-mentioned meanings. ]
The amine represented by the general formula (IV) R 4 COOR 5 (IV) [In the formula, R 4 represents the above meaning, R 5 represents H or a carbon number of 1 to 1.
3 represents an alkyl group. ] The fatty acid represented by these or its ester is acylated, The manufacturing method of the diamido amine represented by General formula (I) of Claim 1 characterized by the above-mentioned.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4175265A JP2610752B2 (en) | 1992-07-02 | 1992-07-02 | Novel diamidoamine and its production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4175265A JP2610752B2 (en) | 1992-07-02 | 1992-07-02 | Novel diamidoamine and its production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0616608A true JPH0616608A (en) | 1994-01-25 |
| JP2610752B2 JP2610752B2 (en) | 1997-05-14 |
Family
ID=15993133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4175265A Expired - Fee Related JP2610752B2 (en) | 1992-07-02 | 1992-07-02 | Novel diamidoamine and its production method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2610752B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010108108A3 (en) * | 2009-03-20 | 2011-04-07 | Egen, Inc. | Polyamine derivatives |
-
1992
- 1992-07-02 JP JP4175265A patent/JP2610752B2/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010108108A3 (en) * | 2009-03-20 | 2011-04-07 | Egen, Inc. | Polyamine derivatives |
| US8900621B2 (en) | 2009-03-20 | 2014-12-02 | Clsn Laboratories, Inc. | Polyamine derivatives |
| US8932638B2 (en) | 2009-03-20 | 2015-01-13 | Clsn Laboratories, Inc. | Polyamine derivatives |
| JP2015147927A (en) * | 2009-03-20 | 2015-08-20 | エーゲン、インコーポレイテッド | Polyamine derivatives |
| US9254334B2 (en) | 2009-03-20 | 2016-02-09 | Clsn Laboratories, Inc. | Polyamine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2610752B2 (en) | 1997-05-14 |
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