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

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

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.

<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.

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.

<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.

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, = 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.

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.

Effects of the present invention? When polymerized, a polymer represented by the following formula (3) is obtained.

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.

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.

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%).

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.

Next, water was removed under reduced pressure at 0°C to remove colorless debris 1S and 2t.
(yield 95%).

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.

Table 1

Claims (1)

[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.