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Polyester type polyurethane material with side chain containing phosphorylcholine group and preparation method thereof

A polyester polyurethane and polyurethane material technology, applied in the field of medical polymer materials, can solve the problems of limited biocompatibility, degradation of toxic substances, and difficulty in enrichment, etc., and achieve high biocompatibility, high mechanical Strength, thrombus avoidance effect

Active Publication Date: 2017-05-17
南通捷事达新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The material obtained by this preparation method has good biocompatibility, but the phosphorylcholine group contained in the material is completely located on the main chain, and a considerable part of the choline group is embedded in the material during the use of the material. Inside, it is difficult to enrich on the surface of the material, so the material has limited biocompatibility, and the double-terminal hydroxyl compound of the synthetic phosphorylcholine group uses a phenolic substance containing a benzene ring, which leads to the long-term use of the material There will be toxic substances degraded out and other disadvantages

Method used

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  • Polyester type polyurethane material with side chain containing phosphorylcholine group and preparation method thereof
  • Polyester type polyurethane material with side chain containing phosphorylcholine group and preparation method thereof
  • Polyester type polyurethane material with side chain containing phosphorylcholine group and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 0.01mol poly-L-lactide (PLLA, M n =2000) and 0.02mol HDI-BDO-HDI (dissolved in dimethyl sulfoxide: 10g / 30mL) were placed in a three-necked flask, protected by dry nitrogen, mechanically stirred, heated to 80 ° C, after 4.0 hours of reaction, cooled to 18 ℃, add 0.01mol Lys-PC, stir, when the viscosity of the system becomes too high to stir normally, add an appropriate amount of dichloromethane, after stirring for 1 hour, add dichloromethane to a concentration of about 15wt%, settle with glacial ether, suction filter, and store at room temperature Vacuum-dried to constant weight to obtain the polyurethane material A1 containing phosphorylcholine groups in the side chain.

[0041] Preparation of film material: Dissolve A1 in the organic solvent dioxane to make a solution with a concentration of 6.5% (g / mL), use a polytetrafluoroethylene mold to volatilize at 25°C under normal pressure for 80 hours, and remove the film from the mold After taking it off, dry it under norma...

Embodiment 2

[0043] 0.01mol polyε-caprolactone (PCL, M n =2000) and 0.02mol HDI-BDO-HDI (dissolved in dimethyl sulfoxide: 10g / 30mL) were placed in a three-necked flask, protected by dry nitrogen, mechanically stirred, heated to 85 ° C, after 3.5 hours of reaction, cooled to 18 ℃, add 0.01mol Lys-PC, stir, when the viscosity of the system becomes too high to stir normally, add an appropriate amount of dichloromethane, after stirring for 1 hour, add dichloromethane to a concentration of about 15wt%, settle with glacial ether, suction filter, and store at room temperature Vacuum-dried to constant weight to obtain the polyurethane material A2 containing phosphorylcholine groups in the side chain.

[0044] Preparation of film material: Dissolve A2 in the organic solvent chloroform to make a solution with a concentration of 5.5% (g / mL), use a polytetrafluoroethylene mold to volatilize at 24°C under normal pressure for 90 hours, and take the film from the mold After drying under normal temperatu...

Embodiment 3

[0046] 0.01mol polyε-caprolactone (PCL, M n =1500) and 0.02mol HDI-BDO-HDI (dissolved in dimethyl sulfoxide: 10g / 30mL) were placed in a three-necked flask, protected by dry nitrogen, mechanically stirred, heated to 85°C, and reacted for 3.5h, then cooled to 18°C ℃, add 0.01mol Lys-PC, and stir. When the viscosity of the system becomes too high to be stirred normally, add dichloromethane in an appropriate amount. After stirring for 1.5h, add dichloromethane to a concentration of about 15wt%, settle with glacial ether, and suction filter. Vacuum drying at room temperature to constant weight to obtain the polyurethane material A3 containing phosphorylcholine groups in the side chain.

[0047] Preparation of film material: Dissolve A3 in the organic solvent chloroform to make a solution with a concentration of 4% (g / mL), use a polytetrafluoroethylene mold to volatilize at 15°C under normal pressure for 60 hours, and take the film from the mold The membrane material is obtained by...

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Abstract

The invention relates to a polyester type polyurethane material with a side chain containing a phosphorylcholine group and a preparation method thereof. The preparation method comprises the following steps of: (1) causing polyester glycol react with excessive diisocyanate, thereby acquiring a double-end isocyanate group prepolymer; and (2) adopting a phosphorylcholine compound containing two amino groups for expanding the chain of the double-end isocyanate group prepolymer, thereby acquiring a biodegradable polyurethane material with the side chain containing the phosphorylcholine group. The phosphorylcholine group in the polyurethane material is located on the side chain of the polymer, so that the biocompatibility of the material can be effectively promoted under the condition of low content of the phosphorylcholine group. Soft segments of the material are all made from polyester; the degree of crystallinity is higher; the higher mechanical strength of the material is guaranteed; the main chain is fully hydrophobic; the degradation velocity is low; the polyurethane material, which is used as a tissue engineering repairing holder material, and the like, can be long-term applied to organism; after the material acts, the material can be gradually degraded into non-toxic products and then absorbed by the organism, so that the injury of the second operation can be avoided.

Description

technical field [0001] The invention belongs to the field of medical polymer materials, and specifically relates to a side chain phosphorylcholine group-containing polyester polyurethane material and a preparation method thereof. Background technique [0002] Since Bayer's invention, polyurethane (PU) has been widely used in the field of medical devices, from medical catheters to artificial hearts. Polyurethane has unique properties, such as relatively excellent biocompatibility, chemical properties, excellent mechanical properties and processing properties, etc., and has become an ideal choice for many medical product raw materials, especially when the selected material must simultaneously solve complex mechanical properties and When biocompatibility issues, such as the preparation of blood contact devices such as interventional catheters, interventional device coatings, hemodialysis membranes, artificial hearts and ventricular assist circulatory systems, medical polyuretha...

Claims

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Application Information

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IPC IPC(8): C08G18/80C08G18/66C08G18/42C08G18/32C08G18/10A61L27/18A61L27/58
Inventor 侯昭升张娜刘小龙
Owner 南通捷事达新材料有限公司
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