A highly biocompatible phosphorylcholine modified polyurethane material and preparation method thereof

A biocompatible, polyurethane material technology, applied in the field of high biocompatibility phosphorylcholine modified polyurethane material and its preparation, can solve the problems of complex, only applicable, limited application, etc., and achieve the effect of good mechanical properties

Active Publication Date: 2019-06-28
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

[0004] In the prior art, the polymer containing phosphorylcholine group is blended with polyurethane material to prepare the modification method of polyurethane material containing phosphorylcholine group, which will greatly reduce the mechanical properties of polyurethane material and affect the surface of polyurethane film. The method of surface modification of grafted phosphorylcholine groups is very complicated and only applicable to some polyurethane materials
The choline group of the polyurethane containing phosphorylcholine group in the main chain prepared by diisocyanate chain extension is embedded in the material, and it is difficult to enrich the surface of the material, resulting in low utilization of phosphorylcholine group, The biocompatibility of the material is limited, and there will be problems such as degradation of toxic substances
The modified polyurethane material obtained by free radical copolymerization of double-bond-terminated polyurethane block copolymer and methacryloyloxyethyl phosphorylcholine monomer has poor biodegradability and cannot be absorbed by organisms, and only hydrogel can be prepared , which greatly limits the application of the material in medicine

Method used

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  • A highly biocompatible phosphorylcholine modified polyurethane material and preparation method thereof
  • A highly biocompatible phosphorylcholine modified polyurethane material and preparation method thereof
  • A highly biocompatible phosphorylcholine modified polyurethane material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Preparation of double-terminated hydroxyl prepolymer:

[0037] Put 15g (0.05mol) of PEG300 in a vacuum reaction bottle, stir with a magnet, remove water in a vacuum (30Pa) at a reaction temperature of 100°C for 4 hours, cool to room temperature, and pass nitrogen gas into the vacuum reaction bottle for balance. Then add 60g of L-lactide and 0.3g of dibutyltin diacetate in the vacuum reaction bottle. Then vacuumize the vacuum reaction bottle, and then pass dry nitrogen to balance, repeat three times. Finally, evacuate to 30Pa, seal the vacuum reaction bottle, heat the oil bath to 130°C, and react for 24 hours to obtain the double-terminated hydroxyl prepolymer poly L-lactide-polyethylene glycol-poly L-lactide (PLLA- PEG-PLLA, Mn = 1500, PEG wt% = 20%).

[0038] (2) Preparation of double-terminated isocyanate-based prepolymers

[0039] Place 15g (0.01mol) of PLLA-PEG-PLLA prepared in (1) and 2.52g (0.015mol) of 1,6-hexamethylene diisocyanate in a three-necked flask...

Embodiment 2

[0045] (1) Preparation of double-terminated hydroxyl prepolymer:

[0046]Put 10.0g (0.05mol) of PEG200 in a vacuum reaction bottle, stir with a magnet, and remove water under vacuum (30Pa) at a reaction temperature of 100°C for 4 hours, then cool to room temperature, and pass nitrogen gas into the vacuum reaction bottle for balance. Then add 40g ε-caprolactone and 0.2g stannous octoate into the vacuum reaction bottle. Then vacuumize the vacuum reaction bottle, and then pass dry nitrogen to balance, repeat three times. Finally, vacuumize to 30Pa, seal the vacuum reaction bottle, heat the oil bath to 140°C, and react for 24 hours to obtain the double-terminated hydroxyl prepolymer polyε-caprolactone-polyethylene glycol-polyε-caprolactone (PCL- PEG-PCL, Mn = 1000, PEG wt% = 20%).

[0047] (2) Preparation of double-terminated isocyanate-based prepolymers

[0048] Put 10g (0.01mol) of PCL-PEG-PCL prepared in (1) and 3.39g (0.015mol) of L-lysine diisocyanate in a three-necked fla...

Embodiment 3

[0054] (1) Preparation of double-terminated hydroxyl prepolymer:

[0055] Put 10.0g (0.05mol) of PEG200 in a vacuum reaction bottle, stir with a magnet, and remove water under vacuum (30Pa) at a reaction temperature of 100°C for 4 hours, then cool to room temperature, and pass nitrogen gas into the vacuum reaction bottle for balance. Then add 40g ε-caprolactone and 0.2g stannous octoate into the vacuum reaction bottle. Then vacuumize the vacuum reaction bottle, and then pass dry nitrogen to balance, repeat three times. Finally, evacuate to 30Pa, seal the vacuum reaction bottle, heat the oil bath to 130°C, and react for 36 hours to obtain the double-terminated hydroxyl prepolymer poly(L-lactide-glycolide)-polyethylene glycol-poly(L - lactide-glycolide) (PLGA-PEG-PLGA, Mn = 1000, PEG wt% = 20%).

[0056] (2) Preparation of double-terminated isocyanate-based prepolymers

[0057] Put 10g (0.01mol) of PLGA-PEG-PLGA prepared in (1) and 3.39g (0.015mol) of L-lysine diisocyanate in...

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Abstract

The invention relates to a high-biocompatibility phosphorylcholine-modified polyurethane material and a preparation method thereof. The prepration method comprises the following steps that (1) a isocyanate group-terminated prepolymer is prepared, specifically, a hydroxyl-terminated prepolymer is blended with excess diisocyanate for reaction, and the isocyanate group-terminated prepolymer is obtained; and (2) phosphorylcholine-modified polyurethane is prepared, specifically, a propyl dimethicone phosphorylcholine compound is dissolved into a solvent, and dropwise added into the isocyanate group-terminated prepolymer, the isocyanate group-terminated prepolymer is subjected to a chain extension reaction, and the phosphorylcholine-modified polyurethane material is obtained. A membrane prepared through the material is excellent in mechanical property, side-chained phosphorylcholine groups can form a hydrophilic interface in an aqueous solution, and the absorbing capacity for protein in blood is low; and meanwhile, the material has biodegradability. The material can be applied to a living body for a long term as a tissue engineering repair stent material and the like, and degradation products at the later stage can be absorbed by the living body.

Description

technical field [0001] The invention belongs to the field of medical polymer materials, in particular to a highly biocompatible phosphorylcholine modified polyurethane material and a preparation method thereof. Background technique [0002] Due to its excellent mechanical properties, polyurethane materials have been widely used as biomaterials in the field of biomedicine. The main products of medical polyurethane are: artificial heart valve, artificial lung, bone adhesive, artificial skin, burn dressing, cardiac pacemaker, insulating wire, suture, various splints, catheter, graft blood vessel, trachea, tooth Branch materials, insert materials, etc. However, although polyurethane has better biocompatibility compared with other materials, it has been found through long-term clinical use that vascular restenosis and thrombosis caused by polyurethane materials are still the main problems that limit its wide application. [0003] As a component of the cell membrane, the phospho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G18/66C08G18/10C08G18/42C08G18/32
CPCC08G18/10C08G18/428C08G18/6651C08G2230/00C08G18/3889
Inventor 侯昭升张娜刘小龙
Owner 南通药享科技有限公司
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