CN107118305B - A kind of preparation method of anti-adhesion medical polypropylene tissue patching material - Google Patents
A kind of preparation method of anti-adhesion medical polypropylene tissue patching material Download PDFInfo
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- CN107118305B CN107118305B CN201710275552.7A CN201710275552A CN107118305B CN 107118305 B CN107118305 B CN 107118305B CN 201710275552 A CN201710275552 A CN 201710275552A CN 107118305 B CN107118305 B CN 107118305B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/048—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
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- Heart & Thoracic Surgery (AREA)
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Abstract
The object of the present invention is to provide a kind of preparation methods of anti-adhesion medical polypropylene tissue patching material, and this method is simple and easy, are modified to polypropylene surface, to obtain the performance of specific hydrophily and Anti cell adhesion.The present invention the following steps are included: 1) by polypropylene material be placed in methylene chloride ultrasonic cleaning or stirring and washing 3~24 hours to remove various additives, then 25 DEG C~40 DEG C dryings in an oven；2) above-mentioned polypropylene material is passed through oxygen plasma treatment 30 seconds~2 minutes；3) derivatives monomer of dopamine is synthesized；4) caused by free radical and form the coating with anti-adhesion properties on polypropylene material surface；5) above-mentioned surface-functionalized polypropylene material PP/PEGMA-DMA is taken out, and is thoroughly cleaned with deionized water, to remove unreacted PEGMA-DMA, after above-mentioned processing routine, just obtains the hydrophilic anti-adhesion medical polypropylene material of apparent height.
Description
Technical field
The present invention relates to the surface modification technology of medical polypropylene material, in particular to it is a kind of with DOPA it is amine-modified poly- third
The preparation method of alkene film, net, particle or micro-sphere material.
Background technique
Polypropylene (PP) is a kind of thermoplastic resin, is one of current global five big general-purpose plastics, can be divided into isotactic poly- third
Alkene (isotaetic polyprolene), random polypropylene (atactic polypropylene) and syndiotactic polypropylene
Three kinds of (syndiotatic polypropylene).PP is a kind of semi-crystalline material, than polyethylene (polyethylene,
PE) there are bigger hardness and higher fusing point.Since the polypropylene of homopolymerization type has certain brittleness, so usually adding when polymerization
Enter 1%~4% or higher amount ethylene as comonomer to obtain the copolymer of polypropylene-polyethylene.Homopolymer type and
The PP material of copolymer type all has excellent resistance to water soak, antiacid caustic corrosion and antilysis.Polypropylene for medical article has been made
It is widely used for medical device materials, such as other than being used as manufacture medical catheter and blood purification filter membrane, also in hernia surgery
Hernia patching material is widely used as in operation.However under the premise of keeping its ontology mechanical property not to be remarkably decreased, how
The hydrophily, anti-adhesive and biocompatibility etc. for improving this kind of material, are still technological difficulties and research hotspot.
Polyethylene glycol (Polyethylene glycol, PEG), non-toxic and tasteless, biocompatibility with higher.PEG is molten
Solution has good anti-tissue adhesion performance.It can effectively reduce post-operation adhesion for coating corresponding position between art under normal circumstances
Generation.And have the commercialized PEG listing that prevents adhesion now, so PEG is safe and reliable for from raw material.
Summary of the invention
Technical problem: the purpose of the present invention is make patching material surface by way of a kind of novel surface biological modification
Performance changes, and prevents the occurrence probability of adhesion, reduces the generation of complication to the full extent.
Technical solution: to solve the above-mentioned problems, a kind of anti-adhesion medical polypropylene tissue repairing material provided by the invention
Material the preparation method is as follows:
Step 1: polypropylene material is placed in methylene chloride ultrasonic cleaning or stirring and washing to remove various additives, so
It dries in an oven afterwards；
Step 2: spare by above-mentioned polypropylene material by oxygen plasma treatment；
Step 3: it takes sodium tetraborate decahydrate and sodium bicarbonate to be put into round-bottomed flask, is passed through nitrogen gas stirring；
Step 4: Dopamine hydrochloride monomer is added；
Step 5: methacrylic anhydride is added in tetrahydrofuran after being sufficiently mixed and is slowly added dropwise to the solution of step 4
In, sodium hydroxide solution adjust pH value, make pH > 8.0, and in environment temperature, react under the conditions of nitrogen protection；
Step 6: ethyl acetate is added into the solution of step 5 and washes twice, discards ethyl acetate layer, is added thereto
Salt acid for adjusting pH value makes pH < 2.0, and is extracted with ethyl acetate；
Step 7: merging the extract in step 6, and it is dry that anhydrous magnesium sulfate is added；
Step 8: the liquid in rotation in step 7 being evaporated, and is added into n-hexane, after standing, discards n-hexane,
It collects and precipitates and be dried in vacuo；Obtain dopamine methacrylate DMA；
Step 9: it takes poly(ethylene glycol) methyl methacrylate to be added in n,N-Dimethylformamide, is passed through nitrogen gas stirring；
Step 10: taking DMA to be dissolved in solution described in step 9, and is separately added into azodiisobutyronitrile AIBN and step 2
Processed polypropylene material is greater than 65 DEG C of reactions；
Step 11: taking out the polypropylene material after reacting in step 10, and cleans in distilled water, is dry；Through above-mentioned
After processing routine, the hydrophilic anti-adhesion medical polypropylene tissue patching material of apparent height is just obtained.
Wherein, the polypropylene material includes isotactic polypropylene isotaeticpolyprolene, random polypropylene
Atacticpolypropylene or syndiotactic polypropylene syndiotaticpolypropylene and addition 1~4wt% ethylene
Random copolymer RCP or more high proportion ethylene contents blocked copolymer,
The polypropylene material shape includes one or more of combinations of film, net, silk, particle or microballoon.
The Dopamine hydrochloride monomer is the Dopamine hydrochloride monomer powders that purity is 98%.
PH=1.0~2.0 in the step six.
PH=8.0~9.0 in the step five.
Used in the step ten be greater than 65 DEG C be stirred to react temperature be 65 DEG C~70 DEG C, the reaction time be 8~
24 hours；
Molecular weight used in the poly(ethylene glycol) methyl methacrylate is Mw=360.
The concentration that the sodium hydroxide solution of pH value is adjusted in the step five is 1mol/L.
It is 6mol/L that the concentration of hydrochloric acid that pH value is added is adjusted in the step six.
The utility model has the advantages that hernia incidence rises year by year in today's society, medically mainly Using prosthesis is taken to repair at present
Mode solve the problems, such as this, most repairing prosthetic materials now are exactly propene polymer patch, but due to material itself
Characteristic extends at any time after making Using prosthesis, sticks together in patient's body and internal organs, cause patient feel internal foreign body sensation or
Bring serious complication, such as chronic ache, intestinal obstruction, bowel narrow etc..The purpose of the present invention is pass through a kind of novel table
Face bio-modification mode, makes patching material surface property change, and prevents the occurrence probability of adhesion, reduces to the full extent simultaneously
Send out the generation of disease.
Specific embodiment
Embodiment 1
1. 0.5g PP GRANULES (or microballoon) is cleaned three times with methylene chloride, each 20mL, scavenging period 3 hours,
And it is 24 hours dry under the conditions of 40 DEG C.
2. above-mentioned polypropylene material is passed through oxygen plasma treatment 2 minutes.
3. 10g sodium tetraborate decahydrate and 4g sodium bicarbonate is taken to be put into 500ml round-bottomed flask, it is passed through nitrogen gas stirring 20min.
4. 5g Dopamine hydrochloride monomer is added in step 3.
It is slowly added dropwise 5. 5ml methacrylic anhydride is added in 20ml tetrahydrofuran after being sufficiently mixed to the solution of step 4
In, and pH is adjusted with the sodium hydroxide solution of 1mol/L, make pH=8.0, and in 25 DEG C of environment, react under the conditions of nitrogen protection
14 hours.
6. 100ml ethyl acetate is added into the solution of step 5 to wash twice, ethyl acetate layer is discarded.It is added thereto
The salt acid for adjusting pH of 6mol/L makes pH=2.0, and is extracted 3 times with 100ml ethyl acetate.
7. merging the extract in step 6, and it is 24 hours dry that 2g anhydrous magnesium sulfate is added.
8. the liquid in rotation in step 7 is evaporated to 50ml, and it is added dropwise in 400ml n-hexane, is placed in 4 DEG C
24 hours, n-hexane is discarded, collect precipitating and is dried in vacuo 24 hours at 25 DEG C；It obtains dopamine methacrylate (DMA).
9. 0.0055mol polyethylene glycol methyl methacrylate is taken to be added in 30ml n,N-Dimethylformamide, it is passed through nitrogen
Gas agitating 20 minutes.
10. the DMA of 0.0011mol is taken to be dissolved in solution described in step 9, and it is separately added into 0.033g azodiisobutyronitrile
(AIBN), the polypropylene material in step 2 reacts 8 hours in 65 DEG C of environment.
11. taking out the polypropylene material in step 10, and cleaned 10 minutes in distilled water, dry 12 is small in 40 DEG C of environment
When.Obtain apparent height hydrophily and the PP GRANULES for preventing cell adherence after above-mentioned processing routine.
Embodiment 2
1. PP GRANULES is laid on one piece of flake aluminum, it is heated to melting in magnetic heating stirrer, then will
Another aluminium flake is pressed on the PP GRANULES of thawing, controls thickness, and polypropylene screen is made.Film thickness is about 0.1mm, and diameter is big
Small about 2cm.
2. by step 1 or polypropylene screen is cleaned three times with methylene chloride, each 20mL, scavenging period 3 hours, and 40
It is 24 hours dry under the conditions of DEG C.
3. above-mentioned polypropylene sheet is passed through oxygen plasma treatment 2 minutes.
4. 10g sodium tetraborate decahydrate and 4g sodium bicarbonate is taken to be put into 500ml round-bottomed flask, it is passed through nitrogen gas stirring 20min.
5. 5g Dopamine hydrochloride monomer is added in step 3.
It is slowly added dropwise 6. 5ml methacrylic anhydride is added in 20ml tetrahydrofuran after being sufficiently mixed to the solution of step 5
In, and pH is adjusted with the sodium hydroxide solution of 1mol/L, make pH=9.0, and in 25 DEG C of environment, react under the conditions of nitrogen protection
14 hours.
7. 100ml ethyl acetate is added into the solution of step 6 to wash twice, ethyl acetate layer is discarded.It is added thereto
The salt acid for adjusting pH of 6mol/L makes pH=2.0, and is extracted 3 times with 100ml ethyl acetate.
8. merging the extract in step 7, and it is 24 hours dry that 2g anhydrous magnesium sulfate is added.
9. the liquid in rotation in step 8 is evaporated to 50ml, and it is added dropwise in 400ml n-hexane, is placed in 24 in 4 DEG C
Hour, n-hexane is discarded, precipitating is collected and is dried in vacuo 24 hours at 25 DEG C；It obtains dopamine methacrylate (DMA).
10. 0.0055mol polyethylene glycol methyl methacrylate is taken to be added in 30ml n,N-Dimethylformamide, it is passed through
Nitrogen gas stirring 30 minutes.
11. the DMA of 0.0011mol is taken to be dissolved in solution described in step 10, and it is separately added into 0.033g azodiisobutyronitrile
(AIBN), the polypropylene material in step 3 reacts 8 hours in 70 DEG C of environment.
12. taking out the polypropylene material in step 11, and cleaned 10 minutes in distilled water, dry 12 is small in 40 DEG C of environment
When.It obtains after above-mentioned processing routine, just obtains apparent height hydrophily and prevent the polypropylene sheet of cell adherence.
Embodiment 3
1. under room temperature, by polypropylene net (2cm × 2cm) 50g/m2It is cleaned three times with methylene chloride or acetone, each 20mL,
Scavenging period 3 hours, and it is 24 hours dry under the conditions of 40 DEG C.
2. above-mentioned polypropylene net is passed through oxygen plasma treatment 2 minutes.
3. 10g sodium tetraborate decahydrate and 4g sodium bicarbonate is taken to be put into 500ml round-bottomed flask, it is passed through nitrogen gas stirring 20min.
4. 5g Dopamine hydrochloride monomer is added in step 3.
It is slowly added dropwise 5. 5ml methacrylic anhydride is added in 20ml tetrahydrofuran after being sufficiently mixed to the solution of step 4
In, and pH is adjusted with the sodium hydroxide solution of 1mol/L, make pH=9.0, and in 25 DEG C of environment, react under the conditions of nitrogen protection
14 hours.
6. 100ml ethyl acetate is added into the solution of step 5 to wash twice, ethyl acetate layer is discarded.It is added thereto
The salt acid for adjusting pH of 6mol/L makes pH=2.0, and is extracted 3 times with 100ml ethyl acetate.
7. merging the extract in step 6, and it is 24 hours dry that 2g anhydrous magnesium sulfate is added.
8.: the liquid in rotation in step 7 is evaporated to 50ml, and is added dropwise in 400ml n-hexane, is placed in 4 DEG C
24 hours, n-hexane is discarded, collect precipitating and is dried in vacuo 24 hours at 25 DEG C；It obtains dopamine methacrylate (DMA).
9. 0.0055mol polyethylene glycol methyl methacrylate is taken to be added in 30ml n,N-Dimethylformamide, it is passed through nitrogen
Gas agitating 20 minutes.
10. the DMA of 0.0011mol is taken to be dissolved in solution described in step 9, and it is separately added into 0.033g azodiisobutyronitrile
(AIBN), the polypropylene material in step 2 reacts 14 hours in 65 DEG C of environment.
11. taking out the polypropylene material in step 10, and cleaned 15 minutes in distilled water, dry 24 is small in 40 DEG C of environment
When.After above-mentioned processing routine, just obtains apparent height hydrophily and prevent the polypropylene net of cell adherence.
Claims (10)
1. a kind of preparation method of anti-adhesion medical polypropylene tissue patching material, it is characterised in that this method includes following step
It is rapid:
Step 1: polypropylene material is placed in methylene chloride ultrasonic cleaning or stirring and washing to remove various additives, is then existed
It is dry in baking oven；
Step 2: spare by above-mentioned polypropylene material by oxygen plasma treatment；
Step 3: it takes sodium tetraborate decahydrate and sodium bicarbonate to be put into round-bottomed flask, is passed through nitrogen gas stirring；
Step 4: Dopamine hydrochloride monomer is added；
Step 5: methacrylic anhydride being added in tetrahydrofuran after being sufficiently mixed and be slowly added dropwise into the solution of step 4, and
Sodium hydroxide solution adjusts pH value, makes pH >=8.0, and in environment temperature, react under the conditions of nitrogen protection；
Step 6: ethyl acetate is added into the solution of step 5 and washes twice, discards ethyl acetate layer, hydrochloric acid is added thereto
PH value is adjusted, makes pH≤2.0, and extracted with ethyl acetate；
Step 7: merging the extract in step 6, and it is dry that anhydrous magnesium sulfate is added；
Step 8: the liquid in rotation in step 7 being evaporated, and is added into n-hexane, after standing, discards n-hexane, is collected
It precipitates and is being dried in vacuo；Obtain dopamine Methacrylamide DMA；
Step 9: it takes poly(ethylene glycol) methyl methacrylate to be added in n,N-Dimethylformamide, is passed through nitrogen gas stirring；
Step 10: taking DMA to be dissolved in step 9 solution, and is separately added into processed in azodiisobutyronitrile AIBN and step 2
Polypropylene material is greater than or equal to 65 DEG C of reactions；
Step 11: taking out the polypropylene material after reacting in step 10, and cleans in distilled water, is dry；It is handled above
After program, the hydrophilic anti-adhesion medical polypropylene tissue patching material of apparent height is just obtained.
2. the preparation method of anti-adhesion medical polypropylene tissue patching material according to claim 1, which is characterized in that institute
The polypropylene material stated include isotactic polypropylene, random polypropylene or syndiotactic polypropylene and be added 1~4wt% ethylene it is random
The then blocked copolymer of copolymer or more high proportion ethylene contents.
3. the preparation method of anti-adhesion medical polypropylene tissue patching material according to claim 1, which is characterized in that institute
The polypropylene material shape stated includes that the one or more of of film, net, silk, particle or microballoon combine.
4. the preparation method of anti-adhesion medical polypropylene tissue patching material according to claim 1, which is characterized in that institute
The Dopamine hydrochloride monomer stated is the Dopamine hydrochloride monomer powders that purity is 98%.
5. the preparation method of anti-adhesion medical polypropylene tissue patching material according to claim 1, which is characterized in that institute
PH=1.0~2.0 in the step of stating six.
6. the preparation method of anti-adhesion medical polypropylene tissue patching material according to claim 1, which is characterized in that institute
PH=8.0~9.0 in the step of stating five.
7. the preparation method of anti-adhesion medical polypropylene tissue patching material according to claim 1, which is characterized in that institute
Reaction temperature is 65 DEG C~70 DEG C in the step of stating ten, and the reaction time is 8~24 hours.
8. the preparation method of anti-adhesion medical polypropylene tissue patching material according to claim 1, which is characterized in that institute
Molecular weight used in the poly(ethylene glycol) methyl methacrylate stated is Mw=360.
9. the preparation method of anti-adhesion medical polypropylene tissue patching material according to claim 1, which is characterized in that institute
The concentration that the sodium hydroxide solution of pH value is adjusted in the step of stating five is 1mol/L.
10. the preparation method of anti-adhesion medical polypropylene tissue patching material according to claim 1, which is characterized in that
It is 6mol/L that the concentration of hydrochloric acid that pH value is added is adjusted in the step six.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102515273A (en) * | 2011-11-24 | 2012-06-27 | 武汉理工大学 | Preparation method of surface functionalized zirconia nano particle for dental repair resin |
| CN104194023A (en) * | 2014-08-12 | 2014-12-10 | 东南大学 | Dopamine-based method for improving surface hydrophilicity and biocompatibility of medical polyurethane material |
| CN104800889A (en) * | 2015-05-07 | 2015-07-29 | 王辉 | Preparation method of anti-adhesion polypropylene mesh coated with polydopamine for abdominal wall defect repair and obtained mesh material |
| CN105949491A (en) * | 2016-05-13 | 2016-09-21 | 东南大学 | Preparation method of anti-adhesion medical PP (polypropylene) material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6566345B2 (en) * | 2000-04-28 | 2003-05-20 | Fziomed, Inc. | Polyacid/polyalkylene oxide foams and gels and methods for their delivery |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102515273A (en) * | 2011-11-24 | 2012-06-27 | 武汉理工大学 | Preparation method of surface functionalized zirconia nano particle for dental repair resin |
| CN104194023A (en) * | 2014-08-12 | 2014-12-10 | 东南大学 | Dopamine-based method for improving surface hydrophilicity and biocompatibility of medical polyurethane material |
| CN104800889A (en) * | 2015-05-07 | 2015-07-29 | 王辉 | Preparation method of anti-adhesion polypropylene mesh coated with polydopamine for abdominal wall defect repair and obtained mesh material |
| CN105949491A (en) * | 2016-05-13 | 2016-09-21 | 东南大学 | Preparation method of anti-adhesion medical PP (polypropylene) material |
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