JPS6172730A - Novel vinyl monomer having blood coagulation inhibiting activity, and its preparation - Google Patents

Novel vinyl monomer having blood coagulation inhibiting activity, and its preparation

Info

Publication number
JPS6172730A
JPS6172730A JP59195924A JP19592484A JPS6172730A JP S6172730 A JPS6172730 A JP S6172730A JP 59195924 A JP59195924 A JP 59195924A JP 19592484 A JP19592484 A JP 19592484A JP S6172730 A JPS6172730 A JP S6172730A
Authority
JP
Japan
Prior art keywords
formula
compound
vinyl monomer
preparation
blood coagulation
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
Application number
JP59195924A
Other languages
Japanese (ja)
Inventor
Yoshio Murashige
村重 義雄
Junko Fujimoto
藤本 順子
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Rayon Co Ltd
Original Assignee
Mitsubishi Rayon Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Rayon Co Ltd filed Critical Mitsubishi Rayon Co Ltd
Priority to JP59195924A priority Critical patent/JPS6172730A/en
Publication of JPS6172730A publication Critical patent/JPS6172730A/en
Pending legal-status Critical Current

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

NEW MATERIAL:The vinyl monomer of formula I (R1 is H or methyl; R2 is alkylene). USE:Useful as a polymerizable monomer used in the composition of e.g. polymeric surfactant, anticoagulant, etc. Also useful as a component of copolymer when used in combination with other polymerizable monomer. PREPARATION:The compound of formula I can be prepared by reacting acrylic acid or methacrylic acid with an alkylenediamine at <=10 deg.C. For example, the compound of formula II which is one of the compound of formula I can be produced by the reaction of acrylic acid with ethylenediamine under ice cooling, or the compound of formula III is produced by reacting methacrylic acid with 1,3-propanediamine.

Description

【発明の詳細な説明】 く産業の利用分野〉 本発明に高分子界面活性剤・抗血液凝固剤等の組成物に
用いる重合性単量体等として使用さn る新mなどニル
モノマーに関する。
DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to new monomers used as polymerizable monomers for use in compositions such as polymeric surfactants and anticoagulants.

〈従来の技術〉 近年、臨床医学の発達にLり予防医学又ぼ治療の状況判
断として血柩検食のにた丁役割に極めて大きいものとな
っている。この、l:うな状況にともなって採血血液の
凝固全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はある特定の検査にしか
用いらnないことと、高帥という欠点に肩している。
<Prior Art> In recent years, with the development of clinical medicine, the role of blood sampling has become extremely important in determining the situation of preventive medicine and treatment. In response to this situation, anticoagulants that completely prevent coagulation of collected blood have been actively developed, and some are commercially available. However, commercially available products suffer from the disadvantages of being used only for certain specific tests and being expensive.

又検査に用いらnる器具の開・発も盛んであり、そルら
の大半にガラス製のものが用いらn、−都合!ft、樹
脂品が用いらnている。ところがガラス・@成樹脂とも
に・血液との親和性に芦〈表面で血液が凝固してしまい
、この防止のためヘパリンナトリウムがコーティングさ
nている。しかしながらヘパリンナトリウムは動物のp
&細胞から抽出分離さnる几め高価であるのと長期保存
すると活性が失わnるという欠点がある、そこで安価で
抗血液凝固性?Mする物質の開発が望まnている。しか
しながら□現状でにこの工うな化合物はほとんどない。
In addition, the development and development of instruments used for inspection is active, and most of them are made of glass. ft, resin products are used. However, both glass and resin have an affinity for blood, which causes blood to coagulate on the surface, and to prevent this, they are coated with heparin sodium. However, heparin sodium
&The drawback is that it is expensive to extract and separate from cells and loses its activity when stored for a long time, so it is cheap and has anticoagulant properties? It is desired to develop a substance that has M. However, at present, there are almost no compounds that can do this.

〈発明が解決しエラとする問題点〉 本発明者らに容易に入手出来る汎用の化合物を用い、抗
血液凝固性tWする重合住モノマー7安価且つ容易に得
ることケ目的としている。
<Problems to be Solved and Disadvantaged by the Invention> The purpose of the present invention is to inexpensively and easily obtain a polymerized biomonomer 7 having anti-blood coagulation properties using a general-purpose compound that is easily available to the present inventors.

く問題点?解決するだめの手段〉 不発明は下記一般式で示さ扛る(メタ)アクリル酸から
肪導される新規などニルモノマー及びその製造法である
Is there a problem? Means to Solve the Problem> The invention is a novel monomer derived from (meth)acrylic acid represented by the following general formula and a method for producing the same.

R,=水素又はメチル基 R2=アルキレン基 不発明の新規とニルモノマーに水可溶性の無色油状の物
質であり、重せ性?有するものである。またこの化合物
にアクリル酸もしくセメタクリル酸とアルキレ7ジアミ
/好ましくは炭素数2−18のアルキレンジアミンとケ
10℃以下好ましくは5℃以下で反応させることに工っ
て得ることができる、 たとえばアクリル酸とエチレンジアミノと全水冷下で反
応させることにエフ、下記式(1)で示さnる新規ビニ
ルモノマー全得ることができる。
R, = hydrogen or methyl group R2 = alkylene group An uninvented novel monomer is a colorless oily substance that is soluble in water and is superimposable. It is something that you have. It can also be obtained by reacting this compound with acrylic acid or semethacrylic acid and an alkylene diamine/preferably an alkylene diamine having 2 to 18 carbon atoms at a temperature of 10°C or lower, preferably 5°C or lower, for example. A novel vinyl monomer represented by the following formula (1) can be obtained by reacting acrylic acid and ethylene diamino under cooling with water.

またメタクリル酸と1.3−プロパンジアミ/と衾反応
させることに19、下記式(2)で示さnる新規ビニル
モノマー全得ることができる。
Further, by reacting methacrylic acid and 1,3-propanediamine/19, all of the new vinyl monomers represented by the following formula (2) can be obtained.

OH。Oh.

く作 用〉 本発明の化付物?重合させると下記式(3)で示さnる
ポリマーが得らn。
Effects of the present invention? When polymerized, a polymer represented by the following formula (3) is obtained.

R,、R2げ前記と同じ n:10以上 水・血液と親和性ケ育し血液抗凝固性?有し、ヘパリン
ナトリウム代替組成物として使用しうる。
R,, R2 same as above n: 10 or more has affinity with water/blood and blood anticoagulant? and can be used as a heparin sodium replacement composition.

またこの化合物に′M合注性単量体して前記の如く単独
で使用することができるはη為に、他の重付性単量体と
共に共重合体の一反分として用いることもでき、こnら
単独重せ体又は共重合体に血液抗凝固剤、血液検食用器
具の表面親水化剤として使用し得る。
In addition, since this compound can be used alone as a polymerizable monomer as described above, it can also be used as part of a copolymer with other polymerizable monomers. , these monopolymers or copolymers can be used as blood anticoagulants and surface hydrophilic agents for blood sampling instruments.

く実施例〉 実施例−1 重付禁止剤・〜イドロキノン1000 ppm 含bア
クリル酸Z2り(0,1モル)紮ナス型フラスコ100
−に入n、こnに氷冷下でエチレンジアミ/6t(rl
、1モル)?徐々に加え、そのままの温度で20分間攪
拌し7t、、この時のフラスコ内温は2℃であった。次
いで減圧下α℃で水金除去し無色の化合物12.7f(
収率96%)全書た。
Examples> Example-1 Heavy loading inhibitor - Hydroquinone 1000 ppm Containing B acrylic acid Z2 (0.1 mol) Eggplant shaped flask 100
- Add ethylenediamine/6t (rl) under ice cooling.
, 1 mole)? The mixture was gradually added and stirred for 20 minutes at the same temperature for 7 tons.The internal temperature of the flask at this time was 2°C. Next, water and gold were removed under reduced pressure at α°C to obtain a colorless compound 12.7f (
Yield: 96%).

元素分析 (41111202N2  Mw : 15
2CHON 理論値: 45.45% 9.09% 24.24チ 
21.21%実測値:45.32% 9.51% 24
.29% 2(1138%実施例2 重置禁止剤・・イドロキノン1000 ppm含むアク
リル酸7.2P(C11モル)全ナス型フラスコ100
−に入n、こnに氷冷下で1,4ブタンジアミンE18
P((L1モル)?徐々に加え、そのままの温度を維持
したまま15分間攪拌した。
Elemental analysis (41111202N2 Mw: 15
2CHON Theoretical value: 45.45% 9.09% 24.24ch
21.21% Actual value: 45.32% 9.51% 24
.. 29% 2 (1138%Example 2) Acrylic acid 7.2P (C11 mol) containing 1000 ppm of superposition inhibitor...hydroquinone 100 all eggplant shaped flasks
- Add 1,4-butanediamine E18 under ice cooling.
P((L 1 mol)?) was gradually added and stirred for 15 minutes while maintaining the same temperature.

次いで減圧下0℃で水音除去し無色の化せ物1S、2t
(収率95%)を得た。
Next, water was removed under reduced pressure at 0°C to remove colorless debris 1S and 2t.
(yield 95%).

元素分析 07H1602N2  Mw : 160c
         HON 理論値:52.50% 1[1,00% 2G、00%
 1150%実測値:51.70% 1[145% 2
[109% 1Z76%実施例5 実施例1.2と同様にしてただレジアミン會1、37”
ロパンジアミ7.1.6−ヘキサメチレンジアミン等と
変えて行つ之、いずnも収率95%以上で新規モノマー
が得らnた。表1に結果を載せた。
Elemental analysis 07H1602N2 Mw: 160c
HON Theoretical value: 52.50% 1[1,00% 2G, 00%
1150% actual value: 51.70% 1 [145% 2
[109% 1Z76%Example 5 Same as Example 1.2 except for the resin amine 1,37''
When lopanediamine was used instead of 7.1.6-hexamethylene diamine, etc., new monomers were obtained in a yield of 95% or more. The results are listed in Table 1.

表     1Table 1

Claims (1)

【特許請求の範囲】 1、下記式で表わせる新規なビニルモノマー▲数式、化
学式、表等があります▼ R_1:水素又はメチル基 R_2:アルキレン基 2、アクリル酸もしくはメタクリル酸とアルキレンジア
ミンとを10℃以下の温度で反応させることを特徴とす
る特許請求の範囲第1項記載の化合物を製造する方法。
[Claims] 1. A novel vinyl monomer represented by the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ R_1: hydrogen or methyl group R_2: alkylene group 2, acrylic acid or methacrylic acid and alkylene diamine 10 A method for producing the compound according to claim 1, characterized in that the reaction is carried out at a temperature of .degree. C. or lower.
JP59195924A 1984-09-19 1984-09-19 Novel vinyl monomer having blood coagulation inhibiting activity, and its preparation Pending JPS6172730A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP59195924A JPS6172730A (en) 1984-09-19 1984-09-19 Novel vinyl monomer having blood coagulation inhibiting activity, and its preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP59195924A JPS6172730A (en) 1984-09-19 1984-09-19 Novel vinyl monomer having blood coagulation inhibiting activity, and its preparation

Publications (1)

Publication Number Publication Date
JPS6172730A true JPS6172730A (en) 1986-04-14

Family

ID=16349243

Family Applications (1)

Application Number Title Priority Date Filing Date
JP59195924A Pending JPS6172730A (en) 1984-09-19 1984-09-19 Novel vinyl monomer having blood coagulation inhibiting activity, and its preparation

Country Status (1)

Country Link
JP (1) JPS6172730A (en)

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