CN1468923A - Composition of medical coating material for improving biocompatibility of biomedical equipment - Google Patents
Composition of medical coating material for improving biocompatibility of biomedical equipment Download PDFInfo
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- CN1468923A CN1468923A CNA02136138XA CN02136138A CN1468923A CN 1468923 A CN1468923 A CN 1468923A CN A02136138X A CNA02136138X A CN A02136138XA CN 02136138 A CN02136138 A CN 02136138A CN 1468923 A CN1468923 A CN 1468923A
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- biocompatibility
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- 238000000576 coating method Methods 0.000 title claims abstract description 37
- 239000000463 material Substances 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 title description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- -1 Polyoxyethylene Polymers 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 6
- 229920004933 Terylene® Polymers 0.000 claims description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 4
- ZMARGGQEAJXRFP-UHFFFAOYSA-N 1-hydroxypropan-2-yl 2-methylprop-2-enoate Chemical compound OCC(C)OC(=O)C(C)=C ZMARGGQEAJXRFP-UHFFFAOYSA-N 0.000 claims description 3
- XURRMOXZJCIZJU-UHFFFAOYSA-N 2-methylprop-2-enoic acid;trimethoxysilicon Chemical compound CC(=C)C(O)=O.CO[Si](OC)OC XURRMOXZJCIZJU-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 3
- 229940050176 methyl chloride Drugs 0.000 claims description 2
- 230000008023 solidification Effects 0.000 claims 2
- 238000007711 solidification Methods 0.000 claims 2
- 230000002429 anti-coagulating effect Effects 0.000 abstract description 3
- 229920001577 copolymer Polymers 0.000 abstract 2
- 238000010422 painting Methods 0.000 abstract 2
- 238000010382 chemical cross-linking Methods 0.000 abstract 1
- 238000002791 soaking Methods 0.000 abstract 1
- 238000007592 spray painting technique Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 208000007536 Thrombosis Diseases 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 238000003618 dip coating Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 238000005507 spraying Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
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- 238000007710 freezing Methods 0.000 description 2
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- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 101710165595 Mitochondrial pyruvate carrier 2 Proteins 0.000 description 1
- 102100025031 Mitochondrial pyruvate carrier 2 Human genes 0.000 description 1
- 101710101698 Probable mitochondrial pyruvate carrier 2 Proteins 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
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- 229940079593 drug Drugs 0.000 description 1
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- 210000004400 mucous membrane Anatomy 0.000 description 1
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- 229920002959 polymer blend Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Materials For Medical Uses (AREA)
Abstract
The medical coating material for improving biocompatibility of biomedical equipment is one kind of crosslinkable copolymer with hydrophilic side radical. The copolymer consists of polymerized unit A containing hydrophilic side radical in 10-60 wt%, polymerized unit B containing hydrophobic radical in 0-60 wt%, crosslinkable polymerized unit C in 10-40 wt% and crosslinkable polymerized unit D in 10-40 wt%. It may be used in decorating biomedical equipment with complicated structure through rotary painting, soaking painting, spray painting and other industrial mode. Under the temperature of 30-200 deg.c, the unit C and unit D produce chemical crosslinking and curing to form stable polymer coating to improve the surface hydrophilicity, lubricity, anticoagulant property and biocompatibility of the biomedical equipment.
Description
Technical field
The present invention relates to a kind of medical coating material that improves the biomedical devices biocompatibility forms.
Background technology
Along with the develop rapidly of modern medicine, various medical treatment devices are used in the various medical procedure widely.Modern medicine diagnosis and treatment means have greatly been enriched in the use of each base polymer medical catheter (Catheter), surgical guide line (Guidewires), through metal (Stents) and other non-intruding devices.Yet still there are problems such as infection, blood coagulation and postoperative hamartoplasia in conventional device to some extent in clinical application.Uncontrollable interaction that these non-biocompatible reactions are directed to medical device surface and give birth to the body component.By finishing to biomedical devices, keeping under the condition of original performance, improve the biomedical devices biocompatibility and become the major issue of modern medical service device in using.
During present research is used, people adopt the kinds of surface technology such as surface chemistry grafting, surface light chemical graft that comprise, material surface is modified, by regulating the various medicines of surface charge, hydrophilic and hydrophobic, load and the biomolecules of material, improve anticoagulation, the anti-infection property of material, obtained achievement preferably.Yet, because these finishing means ubiquities weakness such as solvent toxicity, complex technical process, adjustability difference, not only limited the designability of material surface greatly, and can't realize modification to medical apparatus with complex geometry profile, cause present surface modification method to rest on finishing to " material " more, physiologically acceptable sex modification means can't be formed, the needs of medical apparatus develop rapidly can not be satisfied in the face of " device ".
Summary of the invention
The purpose of this invention is to provide a kind of medical device surface that can be applicable to have the complex geometry profile, and significantly improve the medical coating material composition material of biomedical devices biocompatibility.
The medical coating material composition that improves the biomedical devices biocompatibility is:
1) a kind of crosslinkable multipolymer that contains hydrophilic side group, this multipolymer comprises the polymerized unit A that contains hydrophilic side group that weight percent is 10-60%, the polymerized unit B that contains hydrophobic grouping of 0-60%, and the crosslinkable polymerized unit C of 10-40% and the crosslinkable polymerized unit D of 10-40%.
2) it to have weight percent is arranged be the crosslinkable multipolymer that 1-20% contains hydrophilic side group, 0.1-30% urethane, terylene, the methyl alcohol of 50-98.9%, ethanol, tetrahydrofuran (THF), methyl chloride; This crosslinkable multipolymer that contains hydrophilic side group comprises the polymerized unit A that contains hydrophilic side group that weight percent is 10-60%, the polymerized unit B that contains hydrophobic grouping of 0-60%, and the crosslinkable polymerized unit C of 10-40% and the crosslinkable polymerized unit D of 10-40%.
Advantage of the present invention is:
1, coated material has excellent biological compatibility;
2, coated material steady chemical structure can adapt to the interior environment of human body;
3, the coating solution preparation is easy, but can adopt the mode of industrial realization such as spin coating, dip-coating, spraying, and the biomedical devices with complex shape structure is carried out coating modifying
4, it is crosslinked to utilize functional group on monomer C and the monomer D to carry out, and forms inierpeneirating network structure, makes coating have excellent physical and mechanical performance;
5, coating form with hydrogel under the human body environment exists, and this character makes biomaterial surface become sliding, reduces rubbing between material surface and the mucosal tissue and connects resistance;
Embodiment
The present invention adopts radical polymerization design, synthetic a kind of crosslinkable multipolymer that contains hydrophilic side group, this multipolymer comprises the polymerized unit that contains hydrophilic side group (A) that weight percent is 10-60%, the polymerized unit that contains hydrophobic grouping (B) of 0-60%, and the crosslinkable polymerized unit (C) of 10-40% and the crosslinkable polymerized unit (D) of 10-40%.The polymerized unit that contains hydrophilic side group can guarantee that coated polymeric has excellent biological compatibility; The polymerized unit that contains hydrophobic grouping guarantees the water stability of polymkeric substance; The crosslinkable polymerized unit guarantees that coating has excellent physical and mechanical performance.The polymerized unit that wherein contains hydrophilic side group is Methylacrylic Acid Polyoxyethylene Ester (MPEO1), CH
2=C (CH
3) COO-[CH
2CH
2O]
n-OH, wherein n=6-200; Or vinylformic acid polyoxyethylene ester (MPEO2), CH
2=CHCOO-[CH
2CH
2O]
n-OH, wherein n=6-200, or methacrylic acid phosphorylcholine ester (MPC1), CH
2=C (CH
3) COO-CH
2CH
2OOPOOCH
2CH
2N (CH
3)
3Or vinylformic acid phosphorylcholine ester (MPC2), CH
2=CHCOO-CH
2CH
2OOPOOCH
2CH
2N (CH
3)
3Crosslinkable polymerized unit is Rocryl 410 (HPMA) (CH
2=C (CH
3) COO-CH
2CH (OH) CH
3) and methacrylic acid trimethoxy silicon propyl ester (TSMA), (CH
2=C (CH
3) COO-CH
2CH
2CH
2Si (OCH
3)
3).The polymerized unit of hydrophobic grouping is alkyl methacrylate (AMA), (CH
2=C (CH
3) COO-CH
2(CH
2)
nCH
3), n=0-16 wherein.But this coated polymeric can adopt the mode of industrial realization such as spin coating, dip-coating, spraying, and the biomedical devices with complex shape structure is carried out coating modifying; And under 30~200 ℃, carry out chemically crosslinked curing, and form stable medical polymer coating, improve surface hydrophilicity, oilness, anticoagulant property and the biocompatibility of biomedical devices.
The present invention adopts above-mentioned crosslinkable multipolymer and medical polymer blend simultaneously, having obtained the another kind of medical coating material that improves the biomedical devices biocompatibility forms, it comprises weight percent is the above-mentioned crosslinkable multipolymer of 1-20%, add urethane, the terylene of 0.1-30%, solvent for use is methyl alcohol or ethanol or tetrahydrofuran (THF) or trichloromethane.But adopt the mode of industrial realization such as spin coating, dip-coating, spraying, the biomedical devices with complex shape structure is carried out coating modifying.And 30~200 ℃ of following chemically crosslinkeds curing, be 1-48 hour set time, forms the medical polymer coating, improves surface hydrophilicity, oilness, anticoagulant property and the biocompatibility of biomedical devices.
Application example 1:
0.5gMPC1,0.939g methacrylic acid fourth fat (BMA), 0.212mlHPMA, 0.06mlTSMA are dissolved in the 27ml dehydrated alcohol; 0.0017gAIBN be dissolved in the 3ml tetrahydrofuran (THF); Gained solution is transferred in the polymerizing pipe of 60ml, uses liquid nitrogen freezing then, to carry out tube sealing with alcohol blast burner, polymerizing pipe is placed 60 ℃ constant temperature shaking table, reaction 20h; Solution after reaction finishes concentrates with Rotary Evaporators, remove most of partial solvent after, add a large amount of freezing anhydrous diethyl ether precipitatings, obtain the product of white powder with the sintered filter funnel suction filtration, under 30 ℃, vacuumize drying.The gained solid is determined its structure with infrared spectra and hydrogen nuclear magnetic resonance, wherein wt degree 26% MPC1,52%BMA, 11% HPMA, 11% TSMA.
Application example 2
Operation is with example 1, and the raw material charging capacity changes 0.5gMPC2,0.918g methacrylic acid fourth fat 18 fat (SMA), 0.212mlHPMA, 0.074ml TSMA into, and the product of gained white powder vacuumizes drying under 30 ℃.The gained solid is determined its structure with infrared spectra and hydrogen nuclear magnetic resonance, and the wherein wt degree is 24% MPC2,54% SMA, 12%HPMA, 10% TSMA.
Application example 3
Operation is with example 1, and the raw material charging capacity changes 0.92gMPC1,0.5gSMA, 0.212mlHPMA, 0.074mlTSMA into, and the product of gained white powder vacuumizes drying under 30 ℃.The gained solid is determined its structure with infrared spectra and hydrogen nuclear magnetic resonance, and the wherein wt degree is 53% MPC1,27% SMA, 10% HPMA, 10% TSMA.
Application example 4
Operation is with example 1, and the raw material charging capacity changes 0.22g MPEO1 (CH into
2=C (CH
3) COO-[CH
2CH
2O]
n-OH, wherein n=10), 0.30g Butyl acrylate 12 fat (DA), 0.5mlHPMA, 0.5TSMA, the product of gained white powder vacuumizes drying under 30 ℃.The gained solid is determined its structure with infrared spectra and hydrogen nuclear magnetic resonance, and the wherein wt degree is 14.6%MPEO1,19.7% DA, 32.8% HPMA, 32.9% TSMA.
Application example 5
Operation is with example 1, and the raw material charging capacity changes 0.6gMPEO2 (CH into
2=CHCOO-[CH
2CH
2O]
n-OH, wherein n=200.), 0.30g methacrylic acid second fat (EMA), 0.mlHPMA, 0.074ml TSMA, the product of gained white powder vacuumizes drying under 30 ℃.The gained solid is determined its structure with infrared spectra and hydrogen nuclear magnetic resonance, and the wherein wt degree is 33.8%MPEO2,26.1%EMA, 21.1%HPMA, 19.0%TSMA.
Application example 6
Operation is with example 1, and the raw material charging capacity changes 0.5gMPEO2 (CH into
2=CHCOO-[CH
2CH
2O]
n-OH, wherein n=370), 0.918gSMA, 0.212mlHPMA, 0.074ml TSMA, the product of gained white powder vacuumizes drying under 30 ℃.The gained solid is determined its structure with infrared spectra and hydrogen nuclear magnetic resonance, and the wherein wt degree is 24% MPEO2,54% SMA, 12%HPMA, 10% TSMA.
Application example 7
Configuration contains the polymkeric substance that weight percent is preparation in 18% application example 1, and solvent for use is a tetrahydrofuran (THF).Adopt spin coating that urethane is carried out coating modifying.And 200 ℃ of following chemically crosslinkeds curing, be 4 hours set time, forms the medical polymer coating.External whole blood experiment shows, no thrombosis, and the platelet adhesion reaction experiment shows that platelet adhesion reaction quantity is lower than 0.64 * 10
3Individual/cm
2
Application example 8
Configuration contains the polymkeric substance that weight percent is preparation in 5% application example 2, and solvent for use is an ethanol.Adopt dip-coating that medical polyurethane is carried out coating modifying.And 150 ℃ of following chemically crosslinkeds curing, be 10 hours set time, forms the medical polymer coating.External whole blood experiment shows, no thrombosis, and the platelet adhesion reaction experiment shows that platelet adhesion reaction quantity is lower than 0.53 * 10
3Individual/cm
2
Application example 9
Configuration contains the polymkeric substance that weight percent is preparation in 10% application example 1, and solvent for use is a tetrahydrofuran (THF), adds 12% urethane.Adopt dip-coating that the 316L stainless steel is carried out coating modifying.And 60 ℃ of following chemically crosslinkeds curing, be 48 hours set time, forms the medical polymer coating.External whole blood experiment shows, no thrombosis, and the platelet adhesion reaction experiment shows that platelet adhesion reaction quantity is lower than 0.62 * 10
3Individual/cm
2
Application example 10
Configuration contains the polymkeric substance that weight percent is preparation in 3% application example 4, and solvent for use is a tetrahydrofuran (THF), adds 26% terylene.But adopt the mode of spin coating industrial realization, the 316L medical stainless steel is carried out coating modifying.And 30~200 ℃ of following chemically crosslinkeds curing, be 1-48 hour set time, forms the medical polymer coating.External whole blood experiment shows, no thrombosis, and the platelet adhesion reaction experiment shows that platelet adhesion reaction quantity is lower than 0.72 * 10
3Individual/cm
2
Application example 11
Configuration contains the polymkeric substance that weight percent is preparation in 1% application example 6, solvent for use tetrahydrofuran (THF), the urethane of adding 3%.Adopt spraying that laser sculpture 316L stainless steel coronary artery bracket is carried out coating modifying.And, form the medical polymer coating 80 ℃ of following chemically crosslinkeds curing 30 hours.External whole blood experiment shows, no thrombosis, and the platelet adhesion reaction experiment shows that platelet adhesion reaction quantity is lower than 1.03 * 10
3Individual/cm
2
Claims (10)
1. a medical coating material that improves the biomedical devices biocompatibility is formed, it is characterized in that it is a kind of crosslinkable multipolymer that contains hydrophilic side group, this multipolymer comprises the polymerized unit A that contains hydrophilic side group that weight percent is 10-60%, the polymerized unit B that contains hydrophobic grouping of 0-60%, and the crosslinkable polymerized unit C of 10-40% and the crosslinkable polymerized unit D of 10-40%.
2. form according to claims 1 described a kind of medical coating material that improves the biomedical devices biocompatibility, it is characterized in that the said polymerized unit A that contains hydrophilic side group is a Methylacrylic Acid Polyoxyethylene Ester, CH
2=C (CH
3) COO-[CH
2CH
2O]
n-OH, wherein n=6-400; Or the vinylformic acid polyoxyethylene ester, CH
2=CHCOO-[CH
2CH
2O]
n-OH, wherein n=6-400; Or methacrylic acid phosphorylcholine ester; Or vinylformic acid phosphorylcholine ester.
3. form according to claims 1 described a kind of medical coating material that improves the biomedical devices biocompatibility, it is characterized in that said hydrophobic grouping polymerized unit B should be alkyl methacrylate, CH
2=C (CH
3) COO-CH
2(CH
2)
nCH
3, n=0-16 wherein.
4. form according to claims 1 described a kind of medical coating material that improves the biomedical devices biocompatibility, it is characterized in that said crosslinkable polymerized unit C is a Rocryl 410; Crosslinkable polymerized unit D is a methacrylic acid trimethoxy silicon propyl ester.
5. form according to claims 1 described a kind of medical coating material that improves the biomedical devices biocompatibility, the solidification value that it is characterized in that crosslinkable polymer unit is 60~200 ℃, and be 1-48 hour set time.
6. a medical coating material that improves the biomedical devices biocompatibility is formed, it is characterized in that it has that weight percent is arranged is the crosslinkable multipolymer that 1-20% contains hydrophilic side group, 0.1-30% urethane, terylene, the methyl alcohol of 50-98.9%, ethanol, tetrahydrofuran (THF), methyl chloride; This crosslinkable multipolymer that contains hydrophilic side group comprises the polymerized unit A that contains hydrophilic side group that weight percent is 10-60%, the polymerized unit B that contains hydrophobic grouping of 0-60%, and the crosslinkable polymerized unit C of 10-40% and the crosslinkable polymerized unit D of 10-40%.
7. form according to claims 6 described a kind of medical coating materials that improve the biomedical devices biocompatibility, it is characterized in that the said polymerized unit A that contains hydrophilic side group is a Methylacrylic Acid Polyoxyethylene Ester, CH
2=C (CH
3) COO-[CH
2CH
2O]
n-OH, wherein n=6-400; Or the vinylformic acid polyoxyethylene ester, CH
2=CHCOO-[CH
2CH
2O]
n-OH, wherein n=6-400, or methacrylic acid phosphorylcholine ester; Or vinylformic acid phosphorylcholine ester.
8. form according to claims 6 described a kind of medical coating materials that improve the biomedical devices biocompatibility, it is characterized in that said hydrophobic grouping polymerized unit B should be alkyl methacrylate, CH
2=C (CH
3) COO-CH
2(CH
2)
nCH
3, n=0-16 wherein.
9. form according to claims 6 described a kind of medical coating materials that improve the biomedical devices biocompatibility, it is characterized in that said crosslinkable polymerized unit C is a Rocryl 410; Crosslinkable polymerized unit D is a methacrylic acid trimethoxy silicon propyl ester.
10. form according to claims 6 described a kind of medical coating materials that improve the biomedical devices biocompatibility, the solidification value that it is characterized in that crosslinkable polymer unit is 60~200 ℃, and be 1-48 hour set time.
Priority Applications (1)
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CNB02136138XA CN1182216C (en) | 2002-07-18 | 2002-07-18 | Composition of medical coating material for improving biocompatibility of biomedical equipment |
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CNB02136138XA CN1182216C (en) | 2002-07-18 | 2002-07-18 | Composition of medical coating material for improving biocompatibility of biomedical equipment |
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CN1468923A true CN1468923A (en) | 2004-01-21 |
CN1182216C CN1182216C (en) | 2004-12-29 |
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2002
- 2002-07-18 CN CNB02136138XA patent/CN1182216C/en not_active Expired - Fee Related
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CN112789065A (en) * | 2018-10-01 | 2021-05-11 | 微仙美国有限公司 | Medical device |
CN111514379A (en) * | 2019-02-02 | 2020-08-11 | 江苏百赛飞生物科技有限公司 | Central venous catheter placed through peripheral vein and preparation method thereof |
CN111514379B (en) * | 2019-02-02 | 2022-03-15 | 江苏百赛飞生物科技有限公司 | Central venous catheter placed through peripheral vein and preparation method thereof |
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