JPH05163218A - Production of acylated amine - Google Patents
Production of acylated amineInfo
- Publication number
- JPH05163218A JPH05163218A JP33482691A JP33482691A JPH05163218A JP H05163218 A JPH05163218 A JP H05163218A JP 33482691 A JP33482691 A JP 33482691A JP 33482691 A JP33482691 A JP 33482691A JP H05163218 A JPH05163218 A JP H05163218A
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- Prior art keywords
- group
- reaction
- formula
- acylated
- fatty acid
- 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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- 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、柔軟剤基材に有用なア
シル化アミンの製造方法に関する。更に詳細には、反応
中及び反応後、又は反応後に系内にスチームの吹き込み
（以下、スチーミングと称す）を行うことにより、匂い
の良好な柔軟剤基材を得る製造方法に関する。FIELD OF THE INVENTION The present invention relates to a method for producing an acylated amine useful as a softener base material. More specifically, the present invention relates to a method for producing a softener base material having a good odor by blowing steam into the system during the reaction, after the reaction, or after the reaction (hereinafter referred to as steaming).
【０００２】[0002]
【従来の技術】従来の技術として、特開昭63−150288号
公報に、化粧料の製造でジメチルポリシロキサンジオー
ルと脂肪酸とをエステル化反応させた後、生成物に脱色
及び水蒸気による脱臭精製を順次施すとあるが、これは
エステル化反応の反応終了後、精製を行うと記載されて
いる。又、特開昭63−198648号公報にメタクリル酸を主
成分として含有する蒸留缶残液に特定量のメタノール及
び硫酸を加えて、エステル化しつつ、水蒸気蒸留して、
メタクリル酸をメタクリル酸メチルとして容易に効率良
く回収する方法が記載され、更に特開昭53−13698 号公
報に、アルキド樹脂の製法にて多塩基性酸及び多価アル
コールをエステル化反応する際に水又は水蒸気を加えて
ゲル化を逆転又は遅延させると記載されている。2. Description of the Related Art As a conventional technique, Japanese Unexamined Patent Publication (Kokai) No. 63-150288 discloses an esterification reaction of dimethylpolysiloxanediol and a fatty acid in the production of cosmetics, followed by decolorization of the product and purification by deodorization with steam. It is described that the purification is carried out after the completion of the esterification reaction, although the treatments are sequentially carried out. Further, in Japanese Patent Laid-Open No. 63-198648, a specific amount of methanol and sulfuric acid is added to a distillation bottom liquid containing methacrylic acid as a main component, and steam distillation is carried out while esterifying.
A method for easily and efficiently recovering methacrylic acid as methyl methacrylate is described. Further, JP-A-53-13698 discloses a method for esterifying a polybasic acid and a polyhydric alcohol in the method for producing an alkyd resin. It is described that water or steam is added to reverse or delay the gelation.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、匂いの
良好なアシル化アミンの製造方法はなく、従来のアシル
化アミンは柔軟剤基材としては使用不可能であった。本
発明はこのような問題を解決する為になされたもので、
スチーミングを反応中及び反応後、又は反応後に行うこ
とにより問題点を解決することを目的としている。However, there is no method for producing an acylated amine having a good odor, and conventional acylated amines cannot be used as a softener base material. The present invention has been made to solve such a problem,
The purpose is to solve the problems by performing steaming during the reaction, after the reaction, or after the reaction.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、一般式
(I) 、(II)及び(III) で示されるアミンと一般式(IV)で
示される脂肪酸との反応中及び反応後、又は反応後にス
チーミングを行うことで、匂いの良好なアシル化アミン
を得られることに着目して鋭意研究を行い、本発明を完
成するに至ったものである。即ち、本発明は、下記に示
す一般式(I) 、(II)、及び(III) で示されるアミンと、
一般式(IV)で示される脂肪酸との反応中及び反応後、又
は反応後にスチームを反応系内に吹き込み、一般式(V)
、(VI)及び(VII) で示されるアシル化アミンを得るこ
とを特徴とするアシル化アミンの製造方法に関する。The inventors of the present invention have described the general formula
(I), (II) and (III) with the fatty acid represented by the general formula (IV) and the fatty acid represented by the general formula (IV) during or after the reaction, or by steaming after reaction, an acylated amine with a good odor The present invention has been completed by paying attention to the fact that the above can be obtained. That is, the present invention, an amine represented by the following general formula (I), (II), and (III),
During the reaction with the fatty acid represented by the general formula (IV) and after the reaction, or after the reaction steam is blown into the reaction system, the general formula (V)
, (VI) and (VII) to obtain an acylated amine.
【０００５】[0005]
【化８】 [Chemical 8]
【０００６】（式中、R ：直鎖又は分岐鎖のC8〜C22の
アルキル基、又はアルケニル基、R1：C1〜C6のアルキル
基、又はアルケニル基、R2：C2〜C6のアミノアルキル
基、又はC2〜C6のヒドロキシアルキル基である。）(In the formula, R is a linear or branched C 8 to C 22 alkyl group or alkenyl group, R 1 : C 1 to C 6 alkyl group or alkenyl group, R 2 : C 2 ~ It is a C 6 aminoalkyl group or a C 2 to C 6 hydroxyalkyl group.)
【０００７】[0007]
【化９】 [Chemical 9]
【０００８】（式中、R1 ：C1〜C6のアルキル基、又
はアルケニル基、R2，R3：それぞれ同一又は異なってい
ても良いC2〜C6のアミノアルキル基、又はC2〜C6のヒド
ロキシアルキル基である。）(In the formula, R 1 is a C 1 to C 6 alkyl group or alkenyl group, R 2 and R 3 are C 2 to C 6 aminoalkyl groups which may be the same or different, or C 2 it is a hydroxyalkyl group -C 6.)
【０００９】[0009]
【化１０】 [Chemical 10]
【００１０】（式中、R2，R3，R4：それぞれ同一又は異
なっていても良いC2〜C6のアミノアルキル基、又はC2〜
C6のヒドロキシアルキル基である。）(In the formula, R 2 , R 3 and R 4 : C 2 to C 6 aminoalkyl groups which may be the same or different, or C 2 to
It is a C 6 hydroxyalkyl group. )
【００１１】[0011]
【化１１】 [Chemical 11]
【００１２】（式中、R5：直鎖又は分岐鎖のC8〜C22の
アルキル基、又はアルケニル基である。）(In the formula, R 5 is a linear or branched C 8 to C 22 alkyl group or alkenyl group.)
【００１３】[0013]
【化１２】 [Chemical 12]
【００１４】（式中、R ：直鎖又は分岐鎖のC8〜C22
のアルキル基、又はアルケニル基、R1 ：C1〜C6のアル
キル基、又はアルケニル基、R2' ：C2〜C6のアミノアル
キル基、又はC2〜C6のヒドロキシアルキル基と式(IV)で
示される脂肪酸との縮合反応で得られるアシル化アミノ
アルキル基又はアシル化オキシアルキル基である。）(In the formula, R: linear or branched C 8 to C 22
An alkyl group or an alkenyl group, R 1 : C 1 to C 6 alkyl group, or an alkenyl group, R 2 ′: a C 2 to C 6 aminoalkyl group, or a C 2 to C 6 hydroxyalkyl group and a formula An acylated aminoalkyl group or an acylated oxyalkyl group obtained by a condensation reaction with a fatty acid represented by (IV). )
【００１５】[0015]
【化１３】 [Chemical 13]
【００１６】（式中、R1 ：C1〜C6のアルキル
基、又はアルケニル基、R2' ，R3' ：それぞれ同一又は
異なっていても良いC2〜C6のアミノアルキル基、又はC2
〜C6のヒドロキシアルキル基と式(IV)で示される脂肪酸
との縮合反応で得られるアシル化アミノアルキル基又は
アシル化オキシアルキル基である。）(In the formula, R 1 is a C 1 to C 6 alkyl group or alkenyl group, R 2 ′ and R 3 ′ are the same or different C 2 to C 6 aminoalkyl groups, or C 2
To C 6 hydroxyalkyl groups and acylated aminoalkyl groups or acylated oxyalkyl groups obtained by the condensation reaction of the fatty acid represented by the formula (IV). )
【００１７】[0017]
【化１４】 [Chemical 14]
【００１８】（式中、R2',R3',R4':それぞれ同一又は異
なっていても良いC2〜C6のヒドロキシアルキル基、又は
C2〜C6のヒドロキシアルキル基と式(IV)で示される脂肪
酸との縮合反応で得られるアシル化アミノアルキル基又
はアシル化オキシアルキル基である。）以下、本発明を
詳細に説明する。本発明において、反応原料であるアミ
ンとしては、上記の一般式(I) 、(II)及び(III) で示さ
れる化合物が挙げられ、具体的には、 N−ヒドロキシエ
チル− N−メチルステアリルアミン、 N,N−ビス（ 2−
ヒドロキシエチル）ステアリルアミン、トリエタノール
アミン、 N−(2−ヒドロキシエチル）− N−メチル−
1,3−プロピレンジアミン等が挙げられる。もう一方の
反応原料である脂肪酸としては、上記の一般式(IV)で示
される化合物が挙げられ、具体的には、ステアリン酸、
パルミチン酸、ラウリン酸、オレイン酸、エルシン酸等
が挙げられる。(In the formula, R 2 ', R 3 ', R 4 ': C 2 to C 6 hydroxyalkyl groups which may be the same or different, or
An acylated aminoalkyl group or an acylated oxyalkyl group obtained by the condensation reaction of a C 2 -C 6 hydroxyalkyl group with a fatty acid represented by the formula (IV). ) Hereinafter, the present invention will be described in detail. In the present invention, examples of the amine as a reaction raw material include compounds represented by the above general formulas (I), (II) and (III), and specifically, N-hydroxyethyl-N-methylstearylamine. , N, N-bis (2-
(Hydroxyethyl) stearylamine, triethanolamine, N- (2-hydroxyethyl) -N-methyl-
Examples include 1,3-propylenediamine and the like. Examples of the fatty acid which is the other reaction raw material include compounds represented by the above general formula (IV), and specifically, stearic acid,
Examples thereof include palmitic acid, lauric acid, oleic acid, erucic acid and the like.
【００１９】アシル化反応の反応温度は 100℃〜300
℃、好ましくは 160℃〜220 ℃が良い。反応温度が 100
℃より低い場合は、反応時間が長くなり、生産性が著し
く低下する。一方 300℃より高い場合は、熱による色相
の劣化が避けられない。反応圧力は常圧から減圧の範囲
の何れでも良いが、反応は脱水反応であることから、減
圧の方が反応速度が向上し反応時間はより短くて済む。The reaction temperature of the acylation reaction is 100 ° C to 300 ° C.
℃, preferably 160 ℃ ~ 220 ℃ is good. Reaction temperature is 100
When the temperature is lower than ℃, the reaction time becomes long and the productivity is remarkably reduced. On the other hand, when the temperature is higher than 300 ° C, deterioration of hue due to heat cannot be avoided. The reaction pressure may be in the range of atmospheric pressure to reduced pressure, but since the reaction is a dehydration reaction, reduced pressure improves the reaction rate and requires a shorter reaction time.
【００２０】反応系内に吹き込むスチームの総量は、反
応に供される上記の一般式(I) 、(II)及び(III) で示さ
れるアミンと一般式(IV)で示される脂肪酸の合計量１Kg
当り、0.01〜10Kgが好ましく、0.05〜５Kgが更に好まし
い。スチームの総量が0.01Kg未満では匂いの良好なもの
が得られなく、一方10Kgを超えてもスチームを反応系内
に吹き込む効果が10Kg未満の場合と変わらないので、ス
チームの経済的ロスが大きく、好ましくない。The total amount of steam blown into the reaction system is the total amount of the amines represented by the above general formulas (I), (II) and (III) and the fatty acids represented by the general formula (IV), which are used in the reaction. 1 kg
Therefore, 0.01 to 10 kg is preferable, and 0.05 to 5 kg is more preferable. If the total amount of steam is less than 0.01 kg, a good odor cannot be obtained, while even if it exceeds 10 kg, the effect of blowing steam into the reaction system is the same as when it is less than 10 kg, so the economic loss of steam is large, Not preferable.
【００２１】[0021]
【実施例】以下、本発明を実施例により説明するが、本
発明はこれらの実施例に制限されるものではない。実施例１ N−ヒドロキシエチル− N−メチルステアリルアミン165
gとステアリン酸285gとを１リットルの四つ口フラスコ
に仕込み、200Torr の減圧下で180 ℃に昇温後10時間反
応させた。その後、 200Torr、 100℃の条件下でスチー
ムを78g/Hrの供給量で10時間吹き込んだ。得られた反応
生成物の色相、匂いは、それぞれガードナー３と○であ
り、色相、匂いとも良好であった。尚、反応生成物の色
相はガードナー比色管で測定し、又匂いは官能試験を行
い、下記の二段階で評価した。 ○ ： 匂いが良好である。 × ： 匂いが悪い。EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. Example 1 N-hydroxyethyl-N-methylstearylamine 165
g and stearic acid (285 g) were charged into a 1-liter four-necked flask, heated to 180 ° C. under reduced pressure of 200 Torr, and reacted for 10 hours. Then, steam was blown for 10 hours under the conditions of 200 Torr and 100 ° C. at a supply rate of 78 g / Hr. The hue and odor of the obtained reaction product were Gardner 3 and O, respectively, and the hue and odor were good. The hue of the reaction product was measured with a Gardner colorimetric tube, and the odor was subjected to a sensory test, and evaluated according to the following two stages. ○: Good odor ×: Bad smell.
【００２２】実施例２ 実施例１と同様に N−ヒドロキシエチル− N−メチルス
テアリルアミン165gとステアリン酸285gとを１リットル
の四つ口フラスコに仕込み、200Torr の減圧下で180 ℃
に昇温し、５時間反応を行った後、スチームを78g/Hrの
供給量で吹き込み始めた。その後、５時間反応を行い反
応時間の合計を10時間とした。次に、 100℃まで冷却し
た後、同供給量でスチームを更に５時間吹き込んだ。得
られた反応生成物の色相、匂いは、それぞれガードナー
３と○であり、色相、匂いとも良好であった。 Example 2 As in Example 1, 165 g of N-hydroxyethyl-N-methylstearylamine and 285 g of stearic acid were placed in a 1-liter four-necked flask, and the pressure was reduced to 200 Torr at 180 ° C.
After the temperature was raised to 0 and the reaction was carried out for 5 hours, steam was started to be blown in at a supply amount of 78 g / Hr. Then, the reaction was carried out for 5 hours, and the total reaction time was 10 hours. Next, after cooling to 100 ° C., steam was blown in at the same amount for 5 hours. The hue and odor of the obtained reaction product were Gardner 3 and O, respectively, and the hue and odor were good.
【００２３】実施例３ N−メチル− N−オレイル− 1,3−プロピレンジアミン1
70gとオレイン酸140gとを１リットルの四つ口フラスコ
に仕込み、50Torrの減圧下で 180℃に昇温後、５時間反
応させた。その後50Torr、 100℃の条件下で30g/Hrの供
給量で、５時間スチームを吹き込んだ。得られた反応生
成物の色相、匂いは、それぞれガードナー３と○であ
り、色相、匂いとも良好であった。 Example 3 N-methyl-N-oleyl-1,3-propylenediamine 1
70 g and 140 g of oleic acid were placed in a 1-liter four-necked flask, heated to 180 ° C. under reduced pressure of 50 Torr, and reacted for 5 hours. After that, steam was blown for 5 hours at a supply rate of 30 g / Hr under conditions of 50 Torr and 100 ° C. The hue and odor of the obtained reaction product were Gardner 3 and O, respectively, and the hue and odor were good.
【００２４】実施例４ トリエタノールアミン75ｇとステアリン酸428gとを１リ
ットルの四つ口フラスコに仕込み、760Torr の常圧下で
160 ℃に昇温し、５時間反応を行った後、スチームを50
g/Hrの供給量で吹き込み始めた。その後、５時間反応を
行い反応時間の合計を10時間とした。次に、 100℃まで
冷却した後、同供給量でスチームを更に５時間吹き込ん
だ。得られた反応生成物の色相、匂いは、それぞれガー
ドナー１と○であり、色相、匂いとも良好であった。 Example 4 75 g of triethanolamine and 428 g of stearic acid were placed in a 1-liter four-necked flask, and under normal pressure of 760 Torr.
After heating to 160 ° C and reacting for 5 hours, steam is added to 50
It started to blow with the supply amount of g / Hr. Then, the reaction was carried out for 5 hours, and the total reaction time was 10 hours. Next, after cooling to 100 ° C., steam was blown in at the same amount for 5 hours. The hue and odor of the obtained reaction product were Gardner 1 and O, respectively, and both the hue and odor were good.
【００２５】比較例１ 実施例１と同様に N−ヒドロキシエチル− N−メチルス
テアリルアミン165gとステアリン酸300gとを１リットル
の四つ口フラスコに仕込み、200Torr の減圧下で 180℃
に昇温後、10時間反応させた。得られた反応生成物の色
相はガードナー２であったが、匂いは×であり、使用不
可能であった。 Comparative Example 1 In the same manner as in Example 1, 165 g of N-hydroxyethyl-N-methylstearylamine and 300 g of stearic acid were placed in a 1-liter four-necked flask and placed under a reduced pressure of 200 Torr at 180 ° C.
After the temperature was raised to 10, the reaction was carried out for 10 hours. The hue of the obtained reaction product was Gardner 2, but the odor was x and it was unusable.
【００２６】[0026]
【表１】 [Table 1]
【００２７】表１の結果より、スチーミングを行う本発
明の製造方法を用いれば、色相と匂いの良好なアシル化
アミンが得られることが判る。From the results shown in Table 1, it can be seen that an acylated amine having a good hue and odor can be obtained by using the production method of the present invention in which steaming is performed.
【００２８】[0028]
【発明の効果】本発明のアシル化アミンの製造方法によ
れば、匂い及び色相の良好なアシル化アミンを得ること
ができる。According to the method for producing an acylated amine of the present invention, an acylated amine having a good odor and hue can be obtained.
─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成４年２月２１日[Submission date] February 21, 1992
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００２６[Correction target item name] 0026
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００２６】[0026]
【表１】 [Table 1]
───────────────────────────────────────────────────── フロントページの続き (72)発明者 加藤 徹 和歌山県和歌山市西浜1450 花王水軒社宅 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Toru Kato 1450 Nishihama, Wakayama City, Wakayama Kao Suisensha House
Claims (1)
I) で示されるアミンと、一般式(IV)で示される脂肪酸
との反応中及び反応後、又は反応後にスチームを反応系
内に吹き込み、一般式(V) 、(VI)及び(VII) で示される
アシル化アミンを得ることを特徴とするアシル化アミン
の製造方法。 【化１】 （式中、R ：直鎖又は分岐鎖のC8〜C22のアルキル基、
又はアルケニル基、 R1：C1〜C6のアルキル基、又はアルケニル基、 R2：C2〜C6のアミノアルキル基、又はC2〜C6のヒドロキ
シアルキル基である。） 【化２】 （式中、R1 ：C1〜C6のアルキル基、又はアルケニル
基、 R2，R3：それぞれ同一又は異なっていても良いC2〜C6の
アミノアルキル基、又はC2〜C6のヒドロキシアルキル基
である。） 【化３】 （式中、R2，R3，R4：それぞれ同一又は異なっていても
良いC2〜C6のアミノアルキル基、又はC2〜C6のヒドロキ
シアルキル基である。） 【化４】 （式中、R5：直鎖又は分岐鎖のC8〜C22のアルキル基、
又はアルケニル基である。） 【化５】 （式中、R ：直鎖又は分岐鎖のC8〜C22のアルキル
基、又はアルケニル基、 R1 ：C1〜C6のアルキル基、又はアルケニル基、 R2' ：C2〜C6のアミノアルキル基、又はC2〜C6のヒドロ
キシアルキル基と式(IV)で示される脂肪酸との縮合反応
で得られるアシル化アミノアルキル基又はアシル化オキ
シアルキル基である。） 【化６】 （式中、R1 ：C1〜C6のアルキル基、又はアルケ
ニル基、 R2' ，R3' ：それぞれ同一又は異なっていても良いC2〜
C6のアミノアルキル基、又はC2〜C6のヒドロキシアルキ
ル基と式(IV)で示される脂肪酸との縮合反応で得られる
アシル化アミノアルキル基又はアシル化オキシアルキル
基である。） 【化７】 （式中、R2',R3',R4':それぞれ同一又は異なっていても
良いC2〜C6のヒドロキシアルキル基、又はC2〜C6のヒド
ロキシアルキル基と式(IV)で示される脂肪酸との縮合反
応で得られるアシル化アミノアルキル基又はアシル化オ
キシアルキル基である。）1. The following general formulas (I), (II), and (II
Steam is blown into the reaction system during and after the reaction of the amine represented by I) with the fatty acid represented by the general formula (IV), or by the reaction of the general formulas (V), (VI) and (VII). A method for producing an acylated amine, which comprises obtaining the acylated amine shown. [Chemical 1] (In the formula, R is a linear or branched C 8 to C 22 alkyl group,
Or an alkenyl group, R 1 : C 1 to C 6 alkyl group, or alkenyl group, R 2 : C 2 to C 6 aminoalkyl group, or C 2 to C 6 hydroxyalkyl group. ) [Chemical 2] (In the formula, R 1 : C 1 -C 6 alkyl group or alkenyl group, R 2 , R 3 : each may be the same or different C 2 -C 6 aminoalkyl group, or C 2 -C 6 Is a hydroxyalkyl group of). (In the formula, R 2 , R 3 and R 4 are each a C 2 to C 6 aminoalkyl group which may be the same or different, or a C 2 to C 6 hydroxyalkyl group.) (In the formula, R 5 is a linear or branched C 8 to C 22 alkyl group,
Or an alkenyl group. ) [Chemical 5] (In the formula, R: a linear or branched C 8 to C 22 alkyl group or an alkenyl group, R 1 : a C 1 to C 6 alkyl group, or an alkenyl group, R 2 ′: C 2 to C 6 Is an acylated aminoalkyl group or an acylated oxyalkyl group obtained by a condensation reaction of a C 2 -C 6 hydroxyalkyl group with a fatty acid represented by the formula (IV). (In the formula, R 1 : C 1 -C 6 alkyl group or alkenyl group, R 2 ′, R 3 ′: C 2 ˜which may be the same or different.
An acylated aminoalkyl group or an acylated oxyalkyl group obtained by a condensation reaction of a C 6 aminoalkyl group or a C 2 -C 6 hydroxyalkyl group with a fatty acid represented by the formula (IV). ) [Chemical 7] (In the formula, R 2 ′, R 3 ′, R 4 ′: each may be the same or different, a C 2 to C 6 hydroxyalkyl group, or a C 2 to C 6 hydroxyalkyl group and the formula (IV) The acylated aminoalkyl group or acylated oxyalkyl group obtained by the condensation reaction with the fatty acid shown.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3334826A JP2538733B2 (en) | 1991-12-18 | 1991-12-18 | Method for producing acylated amine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3334826A JP2538733B2 (en) | 1991-12-18 | 1991-12-18 | Method for producing acylated amine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05163218A true JPH05163218A (en) | 1993-06-29 |
| JP2538733B2 JP2538733B2 (en) | 1996-10-02 |
Family
ID=18281651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3334826A Expired - Lifetime JP2538733B2 (en) | 1991-12-18 | 1991-12-18 | Method for producing acylated amine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2538733B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998047860A1 (en) * | 1997-04-22 | 1998-10-29 | Akzo Nobel N.V. | Process for making carboxylic amides |
| US5939059A (en) * | 1997-08-13 | 1999-08-17 | Akzo Nobel Nv | Hair conditioner and 2 in 1 conditioning shampoo |
| JP2002069047A (en) * | 2000-08-29 | 2002-03-08 | Kao Corp | Method for producing monoalkanolamide |
-
1991
- 1991-12-18 JP JP3334826A patent/JP2538733B2/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998047860A1 (en) * | 1997-04-22 | 1998-10-29 | Akzo Nobel N.V. | Process for making carboxylic amides |
| EP1236710A3 (en) * | 1997-04-22 | 2004-01-02 | Akzo Nobel N.V. | Process for making carboxylic amides |
| US5939059A (en) * | 1997-08-13 | 1999-08-17 | Akzo Nobel Nv | Hair conditioner and 2 in 1 conditioning shampoo |
| US6264931B1 (en) | 1997-08-13 | 2001-07-24 | Akzo Nobel Nv. | Hair conditioner and 2 in 1 conditioning shampoo |
| JP2002069047A (en) * | 2000-08-29 | 2002-03-08 | Kao Corp | Method for producing monoalkanolamide |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2538733B2 (en) | 1996-10-02 |
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