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Method for preparing polyurethane material grafted by methoxy polyethylene glycol

A technology of polyethylene glycol monomethyl ether and polyurethane materials, applied in the direction of coating, etc., can solve the problems of easy peeling off of coating, inability to apply and promote, and insufficient firmness, and achieve the effect of simple process

Inactive Publication Date: 2012-05-09
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In China, some of the samples with lubricating coatings studied have the main problem that the coatings are easy to fall off and cannot be widely used and promoted.
These new attempts can overcome the shortcomings of polyurethane surface lubricating coatings such as low lubricating performance and insufficient firmness, and are expected to break the monopoly of foreign companies on the production technology of high-end medical catheters, and provide theoretical and experimental basis for the development of high-end medical catheters in my country. Has great potential economic value

Method used

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Examples

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Effect test

preparation example Construction

[0025] A preparation method utilizing polyethylene glycol monomethyl ether grafted polyurethane material, comprising the following steps:

[0026] Step 1: First react dimethyl 5-hydroxyisophthalate with 3-bromopropyne to convert the hydroxyl on the benzene ring into propargyloxy to obtain dimethyl 5-propargyloxyisophthalate , the solvent is acetone, ethanol, methylene chloride, chloroform, the action temperature is 0oC to 70oC, and the action time is 30 minutes to 24 hours;

[0027] Step 2: Slowly add the tetrahydrofuran solution of the above product into the tetrahydrofuran solution of lithium aluminum hydride to react to obtain 3,5-dimethylol-1-propargyloxybenzene, which is a diol with an alkynyl structure, and a solvent For ether, toluene, n-hexane and tetrahydrofuran, the action temperature is 0oC to 90oC, and the action time is 30 minutes to 20 hours;

[0028] Step 3: use the hydroxyl group of polyethylene glycol monomethyl ether to react with 2-bromoisobutyryl bromide t...

Embodiment 1

[0039]1) Preparation of diol 3,5-dimethylol-1-propargyloxybenzene (PBM) with an alkynyl structure: under nitrogen protection, 2 g (9.52 mmol) of 5-hydroxyisophthalic acid Dimethyl ester, 1.6 g (11.4 mmol) potassium carbonate, 0.026 g (0.098 mmol) 18-crown-6 and 1.26 mL (11.4 mmol) 3-bromopropyne were added to a two-necked round bottom filled with 40 mL of acetone In the flask, the temperature is 70 oC. After 30 minutes, the solution became turbid, and after 90 minutes, the solution was milky white. After 12 hours of continuous reaction, a milky yellow solution was obtained. The acetone in the solution was removed by rotary evaporation to obtain a light yellow solid, and then recrystallized with ethanol to obtain white needle crystals. Take 1.01g (4.07mmol) of the 5-propargyloxyisophthalate obtained above and dissolve it in 15mL of reflux-dried tetrahydrofuran (THF), and then slowly add it to a tank containing 0.58g (15.3mmol) of lithium hydride Aluminum (LiAlH 4 ) and 15 mL ...

Embodiment 2

[0044] 1) Preparation of diol 3,5-dimethylol-1-propargyloxybenzene (PBM) with an alkynyl structure: under nitrogen protection, 2 g (9.52 mmol) of 5-hydroxyisophthalic acid Dimethyl ester, 1.6 g (11.4 mmol) potassium carbonate, 0.026 g (0.098 mmol) 18-crown-6 and 1.26 mL (11.4 mmol) 3-bromopropyne were added to a two-necked round bottom filled with 40 mL of acetone In the flask, the temperature is 70 oC. After 30 minutes, the solution became turbid, and after 90 minutes, the solution was milky white. After 12 hours of continuous reaction, a milky yellow solution was obtained. The acetone in the solution was removed by rotary evaporation to obtain a light yellow solid, and then recrystallized with ethanol to obtain white needle crystals. Take 1.01g (4.07mmol) of the 5-propargyloxyisophthalate obtained above and dissolve it in 15mL of reflux-dried tetrahydrofuran (THF), and then slowly add it to a tank containing 0.58g (15.3mmol) of lithium hydride Aluminum (LiAlH 4 ) and 15 mL...

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Abstract

The invention discloses a method for preparing a polyurethane material grafted by methoxy polyethylene glycol, comprising the following steps: first, reacting dimethyl 5-hydroxyisophthalate with 3-propargyl bromide to obtain 5- propargyloxy dimethyl isophthalate; slowly adding a tetrahydrofuran solution in a tetrahydrofuran solution of lithium aluminum hydride for reacting to obtain 3,5-dihydroxytoluene-1-propargyloxy benzene; reacting methoxy polyethylene glycol with bromo-2-methylpropionyl bromide to obtain methoxy polyethylene glycol having an end group of bromine atoms; converting methoxy polyethylene glycol having the end group of bromine atoms into methoxy polyethylene glycol having an end group of azido by using sodium azide; reacting methoxy polyethylene glycol having the end group of azido by using sodium azide with dihydric alcohol 3,5-dihydroxytoluene-1-propargyloxy benzene by click chemistry; and reacting dihydric alcohol containing methoxy polyethylene glycol long tail with diisocyanate to obtain polyurethane having a main chain grafted by methoxy polyethylene glycol.

Description

technical field [0001] The invention belongs to the field of surface functionalization of medical polymer materials, and specifically relates to the preparation of a highly stable hydrophilic and adjustable coating on the surface of medical polyurethane materials such as high-end medical catheters, guide wires and cardiovascular stents. method. Background technique [0002] Polyurethane (PU) is mainly obtained by polyaddition of diisocyanates and diols or polyols as basic raw materials. It was first synthesized by Bayer in 1947 and has a development history of more than 60 years so far. The diversity of the main chain structure of PU determines that it has very rich and unique physical and chemical properties. Surface functionalized PU has been widely used as biomedical materials. It is grafted with polyethylene glycol (PEG) or heparin to enhance the hydrophilic lubricity of the catheter surface, anticoagulant and anti-protein deposition, and can be applied to the blood ves...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/50C08G65/48A61L29/08A61L31/10
Inventor 张天柱薛云燕周雪锋顾宁
Owner SOUTHEAST UNIV
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