Polyether polyurethane material containing phosphorylcholine group on side chain and preparation method thereof

A polyurethane material, phosphorylcholine technology, applied in the field of medical polymer materials, can solve the problems of reduced mechanical properties of materials, limited improvement of biocompatibility, complicated methods, etc., achieves high stretching ability and flexibility, and improves biological Compatibility, the effect of simple preparation process

Active Publication Date: 2017-05-17
南通药享科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Among them, the modified method of inserting phosphorylcholine groups on the surface of polyurethane materials is to soak the polyurethane film in a solvent containing phosphorylcholine to react so that the surface first introduces primary amino groups, but the phosphorylcholine that is inserted The group is unstable and easy to fall off under external conditions, and the method is complicated, the cost is high, and it is difficult to industrialize production; the modification method of blending the polymer containing the phosphorylcholine group with the polyurethane material improves the original polyurethane material. However, it is found that when the amount of the polymer containing phosphorylcholine group is large, the mechanical properties of the material will be reduced; the double-terminal hydroxyl compound containing phosphorylcholine group is synthesized and then extended to prepare the main Modification method of polyurethane chain containing phosphorylcholine group 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. It is difficult to enrich on the surface of the material, and the utilization rate of the phosphorylcholine group is reduced, resulting in limited improvement of the biocompatibility of the material, and the preparation is difficult and the cost is high.

Method used

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  • Polyether polyurethane material containing phosphorylcholine group on side chain and preparation method thereof
  • Polyether polyurethane material containing phosphorylcholine group on side chain and preparation method thereof
  • Polyether polyurethane material containing phosphorylcholine group on side chain and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]15g (0.01mol) Poloxamer 188 (M n =1500, PEOwt%=20%) and 8.52g (0.02mol) of HDI-BDO-HDI (dissolved in dimethyl sulfoxide: 10g / 30mL) were placed in a three-necked flask, protected by dry nitrogen, mechanically stirred, and heated to 80 ℃, after reacting for 4 hours, lower the temperature to 20℃, add 3.61g (0.01mol) DAPC, and stir. When the viscosity of the system becomes too high and cannot be stirred normally, add an appropriate amount of dichloromethane. After stirring for 1 hour, add dichloromethane to a concentration of about 15 wt%, settled with glacial ether, filtered with suction, and vacuum-dried at room temperature to constant weight to obtain phosphorylcholine-modified polyurethane P1.

[0041] Preparation of membrane material: Dissolve P1 in the organic solvent dioxane to prepare a solution with a concentration of 6.5% (g / mL), volatilize at 25°C under normal pressure for 80 hours, and then dry in vacuum at normal temperature to obtain the membrane material. The...

Embodiment 2

[0043] 15g (0.01mol) Poloxamer 188 (M n =1500, PEOwt%=20%) and 7.40g (0.02mol) BDI-BDO-BDI (dissolved in dimethyl sulfoxide: 10g / 30mL) were placed in a three-necked flask, protected by dry nitrogen, mechanically stirred, and heated to 80 ℃, after reacting for 3 hours, lower the temperature to 18℃, add 3.61g (0.01mol) DAPC, and stir. When the viscosity of the system becomes too high and cannot be stirred normally, add an appropriate amount of dichloromethane. After stirring for 1 hour, add dichloromethane to a concentration of about 15 wt%, settled with glacial ether, filtered with suction, and vacuum-dried at room temperature to constant weight to obtain phosphorylcholine-modified polyurethane P2.

[0044] Preparation of membrane material: Dissolve P2 in the organic solvent chloroform, make a solution with a concentration of 5.5% (g / mL), volatilize at 24 ° C under normal pressure for 90 hours, and then dry it in vacuum at normal temperature to obtain the membrane material. Th...

Embodiment 3

[0046] 10g (0.01mol) polypropylene oxide (PPO, M n =1000) and 8.52g (0.02mol) of 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 hours. Cool down to 20°C, add 3.61g (0.01mol) DAPC, and stir. When the viscosity of the system becomes too high and cannot be stirred normally, add an appropriate amount of dichloromethane. After stirring for 1.5h, add dichloromethane to a concentration of about 15wt%, ice diethyl ether Sedimentation, suction filtration, vacuum drying at room temperature to constant weight to obtain phosphorylcholine modified polyurethane P3.

[0047] Preparation of membrane material: Dissolve P3 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 membrane out of the mold The membrane material is obta...

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Abstract

The invention relates to a polyether polyurethane material containing a phosphorylcholine group on a side chain and a preparation method thereof. The preparation method comprises the following steps: (1) enabling polyether glycol to react with excess diisocyanate to obtain a two-end isocyanate-based prepolymer; (2) performing chain extension on the two-end isocyanate-based prepolymer by taking a bis-amino phosphorylcholine compound as a chain extender to obtain phosphorylcholine modified polyurethane. The process is simple and feasible; moreover, the phosphorylcholine group is positioned on the side chain of a polymer, and is accumulated on the surface of the material when being applied to an organism, so that the biocompatibility of the material is enhanced greatly, and the absorption of proteins and platelets in blood is very low. A membrane prepared from the material has high mechanical strength and flexibility; the used diisocyanate is fat diisocyanate which contains a plurality of urethane groups, so that a degradation product is non-toxic and can be absorbed by the organism.

Description

technical field [0001] The invention belongs to the field of medical polymer materials, in particular to a polyether type polyurethane material containing phosphorylcholine group in the side chain and a preparation method thereof. Background technique [0002] Polyurethane has the advantages of various design methods, good biocompatibility, high mechanical strength, wear resistance, fatigue resistance, high elasticity, easy processing, non-toxic and harmless, and easy to be absorbed by the human body. It is an environmentally friendly functional material. It has a wide range of applications in the field of biomedical materials such as artificial tissues, bionic skin, medical sponges, postoperative sutures, and slow-release system substrates. However, although artificial organs made of polyurethane or medical devices in contact with the human body have good biocompatibility, it is found in clinical use that the surface of artificial organs made of polyurethane materials, such...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/78C08G18/66C08G18/48C08G18/32C08G18/10
Inventor 侯昭升刘小龙张娜
Owner 南通药享科技有限公司
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