JPS6168454A - Preparation of n-2-hydroxyethylacrylamide or n-2-hydroxyethylmethacrylamide - Google Patents
Preparation of n-2-hydroxyethylacrylamide or n-2-hydroxyethylmethacrylamideInfo
- Publication number
- JPS6168454A JPS6168454A JP19028084A JP19028084A JPS6168454A JP S6168454 A JPS6168454 A JP S6168454A JP 19028084 A JP19028084 A JP 19028084A JP 19028084 A JP19028084 A JP 19028084A JP S6168454 A JPS6168454 A JP S6168454A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- methacrylate
- hydroxyethylacrylamide
- aminoethanol
- hydroxyethylmethacrylamide
- 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.)
- Pending
Links
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業の利用分野〉
本発明は高分子界面活性剤、抗血液凝固剤等の組底物に
用いる重置性単量体等として使用さｎる新規−化会物Ｎ
−２−ヒドロキ７エチル（メタ）アクリルアミドに関す
る。[Detailed Description of the Invention] <Field of Industrial Application> The present invention is directed to a novel chemical compound that is used as a superpositionable monomer for use in composite materials such as polymeric surfactants and anticoagulants. N
-Relating to 2-hydroxy 7ethyl (meth)acrylamide.
〈従来の技術〉
近年、臨床医学の発達にエフ予防医学又は治療の状況判
断として血液検量のにた丁役割に極めて大きいものとな
っている。この工うな状況にともなって採血血液の凝固
？防止する抗凝固剤の開発が盛んであり一部市販さｎて
いる。しかしながら市販品にある特定の検査にしか用い
らｎないことと、高価といり欠点に！している。<Prior Art> In recent years, with the development of clinical medicine, blood assays have played an extremely important role in determining the status of preventive medicine or treatment. Due to this unfortunate situation, is the collected blood coagulating? Development of anticoagulants to prevent this is active, and some are commercially available. However, the downside is that it can only be used for certain tests on the market, and it is expensive! are doing.
又検量に用いらｎる器具の開発も盛んであり、それらの
大半にガラス製のものが用いら１一部合成樹脂品が用い
らｎている。ところがガラス合成樹脂ともに血液との親
和性は悪く、表面で血液が凝固してしまい、この防止の
ためヘバリ／ナトリウムがコーティングされている。し
かしながらヘバリ／ナトリウムは動物の腸細胞から抽出
分離さ几るため高価であるのと、長期保存すると活性か
失わｎるとい９欠点がある。そこで安価で抗血凝固性′
！１１−肩する物質の開発が望まｎている。In addition, the development of instruments used for calibration is active, and most of them are made of glass, while some are made of synthetic resin. However, both glass synthetic resins have poor affinity with blood, and blood coagulates on the surface, and to prevent this, they are coated with Hebari/sodium. However, hebari/sodium is expensive because it is extracted and separated from animal intestinal cells, and it has the disadvantage that it loses its activity when stored for a long period of time. Therefore, it is inexpensive and anticoagulant.
! 11 - It is desired to develop a substance that can do the same.
一万、メタクリル酸メチル、アクリル酸メチル等のエス
テル類はメタクリル酸又はアクリル酸とメチルアルコー
ルとのエステル化反応で得らｎることに良く知られてい
るが、比較的安価且つ容易罠得らｎる水溶性のモノマー
であって抗血液凝固性會肩する重合性モノマーについて
は殆ど矧らｎていないのが現状である。It is well known that esters such as methyl methacrylate and methyl acrylate can be obtained by the esterification reaction of methacrylic acid or acrylic acid with methyl alcohol, but they are relatively inexpensive and not easily obtained. At present, there are hardly any polymerizable monomers which are water-soluble monomers and have anti-blood coagulation properties.
〈発明が解決しょうとする問題点〉
本発明者らは容易に入手出来る汎用性ビニルモノマーを
用いて、抗血液凝固性ＫＷする重合性モノマー？安価且
つ容易に得ることを目的としている、
く問題点を解決する友めの手段〉
本発明の要旨とするところに汎用などニルモノマーｔ２
−アミンエタノールと接触反応さすことにエフ水溶性ビ
ニルモノマー金得る合成法であって、具体的には炭素数
１〜２２のアルキル（メタ）アクリレートもしくニ（メ
タ）アクリル酸と２−アミノエタノール全反応させて。<Problems to be Solved by the Invention> The present inventors have developed a polymerizable monomer that exhibits anti-blood coagulability KW using an easily available general-purpose vinyl monomer. The purpose of the present invention is to obtain a general-purpose monomer t2 that is inexpensive and easy to obtain.
- Synthesis method for obtaining F water-soluble vinyl monomer gold by contact reaction with amine ethanol, specifically, alkyl (meth)acrylate having 1 to 22 carbon atoms or di(meth)acrylic acid and 2-aminoethanol Let it fully react.
Ｎ−２−ヒドロキ７エチル（メタ）アクリルアはドを製
造する方法である。N-2-Hydroxy7ethyl (meth)acryla is a method for producing d.
本発明で合成反応に供されるビニルモノマーに炭素数１
〜２２のアルキルメタクリレート、アルキルアクリレー
ト例えばメチルメタクリレート、エチルメタクリレート
、ｎ−プロピルメタクリレート、イソプロピルメタクリ
レート１、ｎ−ブチルメタクリレート、インブチルメタ
クリレート、ター７ヤリプチルメタクリレート、シクロ
ヘキシルメタクリレート、メチルアクリレート、エチル
アクリレート、ｎ−グロビルアクリレート、イソプロピ
ルアクリレート、ｎ−ブチルアクリレート、シクロヘキ
フルアクリレート、２−エチルへキシルアクリレート等
いずれでも工いが、その中でもメチルメタクリレート、
エチルメタクリレート、メチルアクリレート、エチルア
クリレートが好ましくメチルメタクリレート、メチルア
クリレートが特に好ましい。お工びアクリル酸、メタク
リル酸か好ましく使用される。The vinyl monomer used in the synthesis reaction in the present invention has 1 carbon atom.
~22 alkyl methacrylates, alkyl acrylates such as methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate 1, n-butyl methacrylate, inbutyl methacrylate, ter7-yalibutyl methacrylate, cyclohexyl methacrylate, methyl acrylate, ethyl acrylate, n- Globyl acrylate, isopropyl acrylate, n-butyl acrylate, cyclohexyfluacrylate, 2-ethylhexyl acrylate, etc. can be used, but among them, methyl methacrylate,
Ethyl methacrylate, methyl acrylate, and ethyl acrylate are preferred, and methyl methacrylate and methyl acrylate are particularly preferred. Preferably, processed acrylic acid or methacrylic acid is used.
また２−アミノエタノールは試薬特級？そのまま使用で
きる。台底反応は次式にエフ進行すると考えらｎる。Also, is 2-aminoethanol a special grade reagent? It can be used as is. The bottom reaction is thought to proceed as follows.
Ｒ：）ＬＯＨ３，ｆ：ｃ！！（、、ｃ２馬等Ｒ：ＥＬＣ
！Ｈ。R:)LOH3,f:c! ! (,,c2 horse etc.R:ELC
! H.
ビニル七ツマー１モルに対し２−アミノエタノール（Ｌ
５〜（１９モル′ｆｒ７Ｘ応させ生成するアルコール又
は水を系外に除去することにエフ、反応に目動的に進行
する。又反応は無触媒で進み重付防止の為・・イドロキ
ノ７等の重合禁止剤を１００ ｐｐｍ程度添加して合成
する。2-aminoethanol (L
5~(19 mol' fr7 It is synthesized by adding about 100 ppm of polymerization inhibitor.
該反応は■無触媒■室温付近での反応■空気中での反応
といり丁ぐｆＬ７ｊ特徴全育する。The reaction is characterized by the following characteristics: 1) Non-catalytic 2) Reaction near room temperature 2) Reaction in air.
反応式（１）、 （２）に工９得られる七ツマ−に新規
な化合物であって抗血栓性ポリマーの原料に使用さｎ、
得られるポリマーは水、血液と親和性’？ＷＬ、 高価
なヘパリンナトリウム等の代替物として使用することが
可能である。The reaction formulas (1) and (2) yield a completely new compound, which is used as a raw material for antithrombotic polymers.
Is the resulting polymer compatible with water and blood? WL can be used as an alternative to expensive heparin sodium, etc.
尚１合放物の構造に核磁気共鳴スペクトル。In addition, nuclear magnetic resonance spectrum of the structure of the paraboloid.
元素分析、赤外線吸収スペクトルにＬり確認した。It was confirmed by elemental analysis and infrared absorption spectrum.
〈実施例〉
実施例１
メチルメタクリレート１０（）？（１モル）全５００＋
ｄナス型フラスコに入ｎ攪拌しなから２−アミノエタノ
ール６１Ｆ（１モル）ｔα５ＩＩ！７！／分の割合で加
え室温で反応させた。、１時間後、氷冷下１０ｗｍＨｇ
の減圧で副生丁・るメチルアルコール全除去したところ
、Ｎ−２−ヒドロキシエチルメタクリルアミドの収率に
９７％であつた。<Example> Example 1 Methyl methacrylate 10()? (1 mol) Total 500+
dPour 2-aminoethanol 61F (1 mol) into an eggplant-shaped flask and stir without stirring.Tα5II! 7! The mixture was added at a rate of 1/min and allowed to react at room temperature. , 1 hour later, 10wmHg under ice cooling
When all of the by-product methyl alcohol was removed under reduced pressure, the yield of N-2-hydroxyethyl methacrylamide was 97%.
実施例２
メタクリル酸８６ｆ（４モル）’ｒ５ａｏゴナス型フラ
スコに入れ攪拌しながら水冷下２−アミノエタノ−ｎ、
４２．７ ｆ （Ｑ、 ７モル） ｋ ａ、 ｓ ｍ
ｔ／分の割付で加えて１時間反応させた。反応終了後、
氷冷下１０＋ｍｍＨｇ減圧下で副生する水及び未反応の
メタクリル酸？除去したところＮ〜２−ヒドロキシエチ
ルメタクリルアミドの収率は９８％であった。Example 2 Methacrylic acid 86f (4 mol) was added to a Gonas-type flask and cooled with water while stirring.
42.7 f (Q, 7 mol) ka, s m
It was added at a rate of t/min and allowed to react for 1 hour. After the reaction is complete,
By-produced water and unreacted methacrylic acid under ice-cooling and 10+mmHg vacuum? Upon removal, the yield of N-2-hydroxyethyl methacrylamide was 98%.
実施例３
メチルアクリレート８６９（１モル） ’ｋ ５００−
ナス塁フ之スコに入ｎ２攪拌しながら２−アミノエタノ
ール６１ｒ（１モル）ｔ−［ｌＬ８ｗｔ／分の速さで加
え室温で反応させた。１時間後水冷下ｊＱｍＨｇ の減
圧で副生するメチルアルコール奮除去し友ところ、Ｎ−
２−ヒトミキシエチルアクリルアミドの収ｆ４ｄ９６％
であった。Example 3 Methyl acrylate 869 (1 mol) 'k 500-
2-Aminoethanol (61r) (1 mol) was added to an eggplant base fusco at a rate of 8 wt/min while stirring for 2 hours, and the mixture was allowed to react at room temperature. After 1 hour, the by-produced methyl alcohol was thoroughly removed by reducing the pressure to JQmHg under water cooling, and the N-
Yield of 2-human mixyethyl acrylamide f4d96%
Met.
実施例４
アクリル酸７２１（０，１モル）全３００−ナス型フラ
スコに入れ攪拌しながら水冷下２−アミノエタノール６
、ＩＰ（１１モル）全α５−７分の速さで加えて１時間
反応させた。＆応終了後、氷冷下１０ｗａ＊Ｈｇ減圧下
で副生する水會除去し次ところ、Ｎ−２−ヒトミキシエ
チルアクリルアミドの収率は９５％であった。Example 4 Acrylic acid 721 (0.1 mol) was added to a total of 300 ml of 2-aminoethanol 6 while cooling with water while stirring.
, IP (11 mol) total α was added at a rate of 5-7 minutes and reacted for 1 hour. After the reaction, the by-product aqueous solution was removed under ice-cooling and reduced pressure of 10 wa*Hg, and the yield of N-2-human mixiethylacrylamide was 95%.
Claims (1)
メタクリレート、アクリル酸、もしくはメタクリル酸と
２−アミノエタノールとを反応させることモ特徴とする
Ｎ−２ヒドロキシエチルアクリルアミドもしくはＮ−２
−ヒドロキシエチルメタクリルアミドの製造方法。 ２、アルキルアクリレート、アルキルメタクリレート、
アクリル酸、もしくはメタクリル酸１モルに対する２−
アミノエタノールのモル数が１以下であることを特徴と
する特許請求の範囲第１項記載の製造方法。[Scope of Claims] 1. N-2 hydroxyethyl acrylamide or N-2 characterized by reacting an alkyl acrylate, alkyl methacrylate, acrylic acid, or methacrylic acid having 1 to 22 carbon atoms with 2-aminoethanol.
- A method for producing hydroxyethyl methacrylamide. 2. Alkyl acrylate, alkyl methacrylate,
2- to 1 mole of acrylic acid or methacrylic acid
2. The manufacturing method according to claim 1, wherein the number of moles of aminoethanol is 1 or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19028084A JPS6168454A (en) | 1984-09-11 | 1984-09-11 | Preparation of n-2-hydroxyethylacrylamide or n-2-hydroxyethylmethacrylamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19028084A JPS6168454A (en) | 1984-09-11 | 1984-09-11 | Preparation of n-2-hydroxyethylacrylamide or n-2-hydroxyethylmethacrylamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6168454A true JPS6168454A (en) | 1986-04-08 |
Family
ID=16255534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19028084A Pending JPS6168454A (en) | 1984-09-11 | 1984-09-11 | Preparation of n-2-hydroxyethylacrylamide or n-2-hydroxyethylmethacrylamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6168454A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6333339A (en) * | 1986-07-29 | 1988-02-13 | Asahi Chem Ind Co Ltd | Antitumor immunocyte inducer for extracorporeal circulation therapy |
| US6117293A (en) * | 1998-07-31 | 2000-09-12 | Biowhittaker Molecular Applications, Inc. | Method for producing hydrophilic monomers and uses thereof |
| US6464850B1 (en) | 1998-07-31 | 2002-10-15 | Biowhittaker Molecular Applications, Inc. | Method for producing hydrophilic monomers and uses thereof |
| WO2018086556A1 (en) * | 2016-11-09 | 2018-05-17 | 普瑞博生技股份有限公司 | Polymer and device for capturing or separating leucocytes, manufacturing method and use thereof |
-
1984
- 1984-09-11 JP JP19028084A patent/JPS6168454A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6333339A (en) * | 1986-07-29 | 1988-02-13 | Asahi Chem Ind Co Ltd | Antitumor immunocyte inducer for extracorporeal circulation therapy |
| US6117293A (en) * | 1998-07-31 | 2000-09-12 | Biowhittaker Molecular Applications, Inc. | Method for producing hydrophilic monomers and uses thereof |
| US6464850B1 (en) | 1998-07-31 | 2002-10-15 | Biowhittaker Molecular Applications, Inc. | Method for producing hydrophilic monomers and uses thereof |
| WO2018086556A1 (en) * | 2016-11-09 | 2018-05-17 | 普瑞博生技股份有限公司 | Polymer and device for capturing or separating leucocytes, manufacturing method and use thereof |
| TWI661864B (en) * | 2016-11-09 | 2019-06-11 | 普瑞博生技股份有限公司 | Leukocyte capture or separation polymer, apparatus, manufacturing method and use thereof |
| US11833289B2 (en) | 2016-11-09 | 2023-12-05 | Puriblood Medical Co., Ltd. | Polymer and device for capturing or separating leucocytes, manufacturing method and use thereof |
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