CN105418953B - A method of in medical polyurethane material surface modification phosphocholine - Google Patents
A method of in medical polyurethane material surface modification phosphocholine Download PDFInfo
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- CN105418953B CN105418953B CN201511024667.6A CN201511024667A CN105418953B CN 105418953 B CN105418953 B CN 105418953B CN 201511024667 A CN201511024667 A CN 201511024667A CN 105418953 B CN105418953 B CN 105418953B
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- polyurethane material
- phosphocholine
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- medical polyurethane
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2207/00—Foams characterised by their intended use
- C08J2207/10—Medical applications, e.g. biocompatible scaffolds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/06—Polyurethanes from polyesters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/08—Polyurethanes from polyethers
Abstract
The invention discloses one kind medical polyurethane material surface modification phosphocholine (PC) method, the pretreatment mode that clean, dry medical polyurethane material passes through ozone activation, active reaction sites are obtained on surface, surface grafting is carried out in phosphocholine reaction solution, obtains the medical polyurethane material of surface modification phosphocholine.Using the medical polyurethane material of the bionic function, surface hydrophilicity is significantly improved, and has good histocompatbility and blood compatibility.The simple process of the method for the present invention, reaction condition is mild, easily controllable, is easy to further industry amplification, carries out industrialization production.
Description
Technical field
The present invention relates to medical polymer field of material technology, and in particular to one kind is in medical polyurethane material surface modification
The method of phosphocholine
Background technique
With the rapid development of the ambits such as the past few decades material science, medicine, biology, bio-medical material exists
The fields such as diagnosis, reparation, the enhancement function of tissue and organ have obtained in-depth study and have been widely applied.Biomaterial
An important application field be the medical instrument prepared with contacting blood, as artificial blood vessel, artificial heart, interventional therapy are led
Pipe etc..It can plant in artificial synthesized high molecular material all, the block polyurethane with micro phase separation structure is high-elastic because having
Property and high-intensitive, good wear resistance, caking property, solvent resistance, nontoxicity, easily molded processing, the advantages that performance is controllable, especially
It is its good biology performance, occupies considerable status in field of biomedicine.It is currently widely used for various doctors
Treat product, such as artificial heart and heart-assist device, artificial blood vessel, artificial skin, orthopaedic bandage, adhesive of medical, drain
Pipe, family planning articles, pharmaceutical carrier etc..
Although polyurethane elastomer is the relatively good high-molecular biologic medical material of generally acknowledged blood compatibility,
Blood compatibility is ideal not enough, when it is as in allosome implantation organism, it would still be possible to generate blood coagulation and thrombotic phenomena.This is
Due to the extremely strong hydrophobicity of polyurethane and bioadhesive, nonspecific proteins can be irreversibly adsorbed when being in contact with blood,
To cause the adverse reactions such as blood coagulation.Therefore, surface is carried out to polyurethane to be modified, improve its biocompatibility, and widen it and answer
It is widely paid close attention to researchers are received.
Wherein, in the way of imitative biofilm structure, phosphocholine is introduced in polyurethane surface, makes phospholipid surface.Make
Material surface puppet decorations, can avoid the attack for exempting from vivo immunization identifying system as the own cells of human body, reach raising life
The purpose of object compatibility.Phosphocholine (PC) is a kind of critically important phospholipid substance, has double-hydrophilic structure, polar head
It is existing positively charged and have negative electrical charge, it is small between the effect force-disturbance hydrone, it can be in conjunction with a large number of water molecules, in surface shape
At layer is firmly hydrated very much, certain biologically inert is kept, to reduce the absorption to protein.And phospholipid molecule is with soft
Property hydrophobic tail, thus natural phospholipid film is substantially reversible adsorption to the suction-operated of albumen, and albumen is made to maintain its day
Right conformation.In addition, phospholipid molecule in Phospholipids polar group (PC) energy strong adsorption blood, forms the phosphorus of similar organism surface
Rouge layer, to weaken the interaction of protein and material surface.Meanwhile the surface of the end group containing PC is inert to haemocyte, it can
To inhibit the bonding of bacterial adhesion and cell, the haemolysis of red blood cell will not be caused, there is excellent anticoagulation function.
Summary of the invention
Technical problem: it is an object of the present invention to provide a kind of method in medical polyurethane material surface modification phosphocholine,
This method can introduce phosphocholine group in polyurethane surface, improve the parent of polyurethane surface by simple graft reaction
Aqueous and biocompatibility.This method of modifying process is simple, mild condition is easily controllable, is suitble to industrial amplification production.
Technical solution: a kind of method in medical polyurethane material surface modification phosphocholine of the invention, including it is as follows
Step:
Step 1: medical polyurethane material ultrasonic cleaning, vacuum drying are obtained clean medical polyurethane material table
Face；
Step 2: carrying out ozone activation pretreatment to medical polyurethane material surface；
Step 3: the medical polyurethane material that step 2 is obtained, which is placed in phosphocholine solution, carries out graft reaction, and
Polymerization inhibitor, which is added, prevents homopolymer from generating；
Step 4: the medical polyurethane material after grafting is cleaned up, is dried in vacuo, surface modification phosphocholine is obtained
Medical polyurethane material.
The method for carrying out phosphocholine modification on medical polyurethane material surface, which is characterized in that step 1 institute
Stating medical polyurethane material is medical Polyester polyurethane, medical polyether system polyurethane, medical aromatic urethane, medical fat
One or more of adoption urethane；It is cleaned by ultrasonic frequency in 30KHZ~80KHZ.
Step 2 ozone concentration is 20~50mgL-1, activation time is 20~60min.
Phosphocholine described in step 3 includes choline glycerophosphatide, trainingization phosphatidyl-ethanolamine (MPEG2000-DSPE)；
Step 3 is the phosphocholine solution that the medical polyurethane material for obtaining step 2 is placed in 1wt%~10wt%
In, the graft reaction 6~for 24 hours at 30~70 DEG C.
Heating stirring carries out the requirement of graft reaction described in step 3 in the absence of oxygen, in water solution system.
Polymerization inhibitor described in step 3 includes hydroquinone, stannous chloride, iron ammonium sulfate or ferric trichloride.
Phosphocholine solution described in step 3 the preparation method comprises the following steps: under condition of heating and stirring, sequentially add distilled water, phosphoric acid
Compound choline, polymerization inhibitor are uniformly mixed.
The distillation including the medical polyurethane material after graft reaction to be used to 30~70 DEG C is cleaned up described in step 4
Water washing 2~for 24 hours, 1~2h replaces primary distilled water, cleans 0.2h~1h with EtOH Sonicate later.
The medical polyurethane material that step 4 cleans up is placed in a vacuum drying oven, 30~70 DEG C of drying temperature, dry
Time 2~for 24 hours.
The utility model has the advantages that
1, present invention side has many advantages, such as that process is simple, mild condition is easily controllable, is suitble to industrial amplification production；
2, it after material surface introduces phosphocholine, is confirmed through testing and analyzing, the medical polyurethane material that the method for the present invention obtains
Material has good hydrophily and biocompatibility.
Specific embodiment
The present invention is done below and is further explained.The invention is not limited in any way for following embodiments, all uses
The mode of equivalent substitution or equivalent transformation technical solution obtained, is among protection scope of the present invention.
A method of in medical polyurethane material surface modification phosphocholine, include the following steps:
Step 1: medical polyurethane material is medical Polyester polyurethane, medical polyether system polyurethane, medical fragrant adoption
One or more of urethane, medical fat adoption urethane.Material can be the forms such as conduit, film and instrument.Cleaning doctor
The impurity of adsorption is removed with polyurethane material surface, is dried in vacuo.It is cleaned by ultrasonic frequency in 30KHZ~80KHZ, drying
Temperature is at 30~70 DEG C.
Step 2: being activated by ozone to clean medical polyurethane material surface, it is therefore intended that polyurethane
Surface obtains the peroxy radicals isoreactivity reaction position of enough surface reactions.Control ozone activation processing time and concentration (or
Person's intensity), the structure of material itself is not destroyed.Ozone concentration is 20~50mgL-1, activation time is 20~60min.
Step 3: the medical polyurethane material after step 2 is activated is placed in phosphocholine solution reaction solution,
The graft reaction is carried out in the case where heating stirring, nitrogen protection (anaerobic) in mild water solution system.Reaction process
It needs that polyurethane material is allowed to come into full contact with reaction solution.In general, phosphocholine solution concentration is 1wt%~10wt%, reaction
Temperature be 30~70 DEG C, the graft reaction time be 6~for 24 hours.For raising grafting rate and reaction efficiency, suitable polymerization inhibitor is added,
Such as benzenediol, stannous chloride, iron ammonium sulfate or ferric trichloride prevent the generation of homopolymer.
Step 4: by the medical polyurethane material after graft reaction using 30~70 DEG C distillation water washing 2~for 24 hours, 1~
2h replaces primary distilled water, cleans 0.2h~1h with EtOH Sonicate later.Clean up postposition in a vacuum drying oven, dry temperature
30~70 DEG C of degree, drying time 2~for 24 hours, obtain the medical polyurethane material that surface carries out phosphocholine modification.
Choline glycerophosphatide that following embodiment is related to, trainingization phosphatidyl-ethanolamine (MPEG2000-DSPE) are purchased from Suzhou
Southeast medicine company limited liability company.
Due to its hydrophobicity, the water before grafting connects the thin polyurethane membrane material and polyurethane guide tube material that following embodiment is related to
Feeler is 95.93 ± 2 °.
Embodiment 1
The medical polyurethane film of 2cm × 2cm is cleaned by ultrasonic clean and is dried in vacuo at 60 DEG C.Film is placed in
50min is activated in the ozone that concentration is 20mg/L.The 30ml choline glycerophosphatide solution water of 10wt% is prepared in three-necked flask
Solution is placed in 60 DEG C of oil bath pan, under magnetic stirring, film is added in reaction system first, then slowly use dropper
It is 6 × 10 that concentration, which is added,-4The FeSO of mol/L4·7H2O is passed through nitrogen protection as polymerization inhibitor, and the reaction time is for 24 hours.Grafting
After reaction, 8h is cleaned in about 60 DEG C of hot water, 2h replaces a water, and subsequent EtOH Sonicate cleans 30min.Poly- ammonia after cleaning
Ester film material is dried overnight spare in 60 DEG C of vacuum oven.
The present embodiment medical polyurethane material introduces phosphoglycerol rear surface hydrophily and improves, and water contact angle is down to 60 ° of left sides
It is right.Although hek293 cell can be grown on original medical polyurethane material surface, more sparse, show its surface biological
Performance is general.Hek293 cell can be sprawled preferably in the material surface of grafting choline glycerophosphatide.Show its bio-compatible
Property significantly improve, illustrate grafting after material surface have good biocompatibility.
Embodiment 2
The medical polyurethane film of 2cm × 2cm is cleaned by ultrasonic clean and is dried in vacuo at 60 DEG C.Film is placed in
50min is activated in the ozone that concentration is 20mg/L.The MPEG2000-DSPE that the 30ml of 10wt% is prepared in three-necked flask is water-soluble
Liquid is placed in 60 DEG C of oil bath pan, and under magnetic stirring, film is added in reaction system first, then is slowly added with dropper
Entering concentration is 6 × 10-4The FeSO of mol/L4·7H2O is passed through nitrogen protection as polymerization inhibitor, and the reaction time is for 24 hours.Grafting is anti-
Ying Hou cleans 8h in about 60 DEG C of hot water, and 2h replaces a water, and subsequent EtOH Sonicate cleans 30min.Polyurethane after cleaning
Thin-film material is dried overnight spare in 60 DEG C of vacuum oven.
The present embodiment medical polyurethane material grafting MPEG2000-DSPE rear surface hydrophily significantly improves, water contact angle
It is down to 40 ° or so.L929 cell grows more sparse on original medical polyurethane material surface, shows its surface biological performance
Generally.Material surface of the L929 cell in grafting MPEG2000-DSPE can largely be grown, and be paved with entire substrate.Show it
Biocompatibility significantly improves, and material surface has good biocompatibility after illustrating grafting.
Embodiment 3
The medical polyurethane catheter-based ultrasound of 5cm is cleaned up and is dried in vacuo at 60 DEG C.It is 100W in power,
Oxygen flow is that 50mL/min carries out plasma activation 30min.Choline glycerophosphatide solution aqueous solution is transferred quickly to after taking-up
In, it is placed in 60 DEG C of oil bath pan, under magnetic stirring, film is added in reaction system first, then is slowly added with dropper
Entering concentration is 6 × 10-4The FeSO of mol/L4·7H2O is passed through nitrogen protection as polymerization inhibitor, and the reaction time is for 24 hours.Grafting is anti-
Ying Hou cleans 8h in about 60 DEG C of hot water, and 2h replaces a water, and subsequent EtOH Sonicate cleans 30min.Polyurethane after cleaning
Thin-film material is dried overnight spare in 60 DEG C of vacuum oven.
The present embodiment medical polyurethane material grafting rear surface hydrophily significantly improves, and water contact angle is lower than 50 °.And it is grafted
Material surface has good biocompatibility afterwards, and L929 cell being capable of normal growth.
Embodiment 4
The medical polyurethane catheter-based ultrasound of 5cm is cleaned up and is dried in vacuo at 60 DEG C.It is 100W in power,
Oxygen flow is that 50mL/min carries out plasma activation 30min.It is transferred quickly to after taking-up in MPEG2000-DSPE aqueous solution,
It is placed in 60 DEG C of oil bath pan, under magnetic stirring, film is added in reaction system first, then is slowly dense with dropper addition
Degree is 6 × 10-4The FeSO of mol/L4·7H2O is passed through nitrogen protection as polymerization inhibitor, and the reaction time is for 24 hours.After graft reaction,
8h is cleaned in about 60 DEG C of hot water, 2h replaces a water, and subsequent EtOH Sonicate cleans 30min.Polyurethane film after cleaning
Material is dried overnight spare in 60 DEG C of vacuum oven.
The present embodiment medical polyurethane material grafting rear surface hydrophily significantly improves, and water contact angle is lower than 60 °.And it is grafted
Material surface has good biocompatibility afterwards, and L929 cell being capable of normal growth.
Claims (7)
1. a kind of method in medical polyurethane material surface modification phosphocholine, which is characterized in that this method includes following step
It is rapid:
Step 1: medical polyurethane material ultrasonic cleaning, vacuum drying are obtained clean medical polyurethane material surface；
Step 2: carrying out ozone activation pretreatment to medical polyurethane material surface；
Step 3: the medical polyurethane material that step 2 is obtained, which is placed in phosphocholine solution, carries out graft reaction, and it is added
Polymerization inhibitor prevents homopolymer from generating；
Step 4: the medical polyurethane material after grafting is cleaned up, is dried in vacuo, the doctor of surface modification phosphocholine is obtained
Use polyurethane material；
Wherein,
Medical polyurethane material described in step 1 is medical Polyester polyurethane, medical polyether system polyurethane, medical fragrant adoption
One or more of urethane or medical fat adoption urethane；It is cleaned by ultrasonic frequency in 30KHz~80KHz；
Step 2 ozone concentration is 20~50mgL-1, activation time is 20~60min；
Phosphocholine described in step 3 is choline glycerophosphatide, trainingization phosphatidyl-ethanolamine MPEG2000-DSPE.
2. the method according to claim 1 in medical polyurethane material surface modification phosphocholine, which is characterized in that step
Phosphocholine solution concentration is 1wt%~10wt% in rapid three.
3. the method according to claim 1 in medical polyurethane material surface modification phosphocholine, which is characterized in that step
Rapid three graft reaction requires to heat graft reaction 6 at 30~70 DEG C~for 24 hours in the absence of oxygen, in water solution system.
4. the method according to claim 1 in medical polyurethane material surface modification phosphocholine, which is characterized in that institute
The polymerization inhibitor stated is hydroquinone, stannous chloride, iron ammonium sulfate or ferric trichloride.
5. the method according to claim 1 in medical polyurethane material surface modification phosphocholine, which is characterized in that institute
State phosphocholine solution the preparation method comprises the following steps: sequentially add distilled water, phosphocholine compound, polymerization inhibitor under condition of heating and stirring
Agent is uniformly mixed.
6. the method according to claim 1 in medical polyurethane material surface modification phosphocholine, which is characterized in that step
Cleaned up described in rapid four including by the medical polyurethane material after graft reaction using 30~70 DEG C distillation water washing 2~
For 24 hours, 1~2h replaces primary distilled water, cleans 0.2h~1h with EtOH Sonicate later.
7. the method according to claim 1 in medical polyurethane material surface modification phosphocholine, which is characterized in that step
Rapid four medical polyurethane materials cleaned up are placed in a vacuum drying oven, and 30~70 DEG C of drying temperature, drying time 2~for 24 hours.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105820543A (en) * | 2016-03-31 | 2016-08-03 | 青岛百瑞吉生物工程有限公司 | Preparation method of biological medical polyurethane material |
| CN111234170A (en) * | 2020-01-15 | 2020-06-05 | 中国科学院长春应用化学研究所 | Polyurethane material, preparation method thereof and application of polyurethane material in artificial meniscus material |
| CN113388147A (en) * | 2021-06-29 | 2021-09-14 | 杨欣 | Preparation method of biomaterial phosphorylcholine modified polyurethane |
| CN113667173A (en) * | 2021-08-20 | 2021-11-19 | 宁波健世科技股份有限公司 | Method for manufacturing high polymer valve leaflet with phosphorylcholine anticoagulation surface |
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| CN1775313A (en) * | 2005-10-14 | 2006-05-24 | 浙江大学 | Polymer brush for improving biomedical material compatibility and its preparing method |
| CN101181988A (en) * | 2007-11-08 | 2008-05-21 | 浙江大学 | Preparation method of carbon-nano tube-phosphorylcholine polymer composite material for blood environment |
| CN104672483A (en) * | 2015-02-05 | 2015-06-03 | 广州华弘生物科技有限公司 | Method for preparing polymer liquid crystal membrane material with biomimic structure and use of material |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1775313A (en) * | 2005-10-14 | 2006-05-24 | 浙江大学 | Polymer brush for improving biomedical material compatibility and its preparing method |
| CN101181988A (en) * | 2007-11-08 | 2008-05-21 | 浙江大学 | Preparation method of carbon-nano tube-phosphorylcholine polymer composite material for blood environment |
| CN104672483A (en) * | 2015-02-05 | 2015-06-03 | 广州华弘生物科技有限公司 | Method for preparing polymer liquid crystal membrane material with biomimic structure and use of material |
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