CN107638612A - A kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe and preparation method thereof - Google Patents
A kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe and preparation method thereof Download PDFInfo
- Publication number
- CN107638612A CN107638612A CN201711089844.8A CN201711089844A CN107638612A CN 107638612 A CN107638612 A CN 107638612A CN 201711089844 A CN201711089844 A CN 201711089844A CN 107638612 A CN107638612 A CN 107638612A
- Authority
- CN
- China
- Prior art keywords
- sleeve pipe
- needle sleeve
- remaining needle
- quaternary ammonium
- ammonium salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 107
- 230000010100 anticoagulation Effects 0.000 title claims abstract description 101
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 92
- 239000001257 hydrogen Substances 0.000 claims abstract description 92
- 229920000669 heparin Polymers 0.000 claims abstract description 85
- 239000011248 coating agent Substances 0.000 claims abstract description 76
- 238000000576 coating method Methods 0.000 claims abstract description 76
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims abstract description 63
- -1 Hydrogen quaternary ammonium salt Chemical class 0.000 claims abstract description 63
- 229960002897 heparin Drugs 0.000 claims abstract description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 claims description 21
- 229960001008 heparin sodium Drugs 0.000 claims description 21
- 239000012266 salt solution Substances 0.000 claims description 19
- 241000894006 Bacteria Species 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 238000012545 processing Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 235000019270 ammonium chloride Nutrition 0.000 claims description 5
- 229910001882 dioxygen Inorganic materials 0.000 claims description 5
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 claims description 3
- 229940107816 ammonium iodide Drugs 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000011068 loading method Methods 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 239000011159 matrix material Substances 0.000 abstract description 18
- 238000010494 dissociation reaction Methods 0.000 abstract description 12
- 230000005593 dissociations Effects 0.000 abstract description 12
- 210000003462 vein Anatomy 0.000 abstract description 8
- 231100000419 toxicity Toxicity 0.000 abstract description 7
- 230000001988 toxicity Effects 0.000 abstract description 7
- 230000017531 blood circulation Effects 0.000 abstract description 6
- 238000005406 washing Methods 0.000 abstract description 5
- 239000008199 coating composition Substances 0.000 abstract description 4
- 230000000845 anti-microbial effect Effects 0.000 description 18
- 210000001772 blood platelet Anatomy 0.000 description 17
- 210000004369 blood Anatomy 0.000 description 12
- 239000008280 blood Substances 0.000 description 12
- 230000001954 sterilising effect Effects 0.000 description 12
- 206010018910 Haemolysis Diseases 0.000 description 11
- 230000008588 hemolysis Effects 0.000 description 11
- 230000014759 maintenance of location Effects 0.000 description 11
- 229910021642 ultra pure water Inorganic materials 0.000 description 10
- 239000012498 ultrapure water Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000001580 bacterial effect Effects 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000007710 freezing Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 230000006870 function Effects 0.000 description 6
- 238000004659 sterilization and disinfection Methods 0.000 description 6
- 239000003146 anticoagulant agent Substances 0.000 description 5
- 229940127219 anticoagulant drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 4
- 238000002679 ablation Methods 0.000 description 4
- 230000023555 blood coagulation Effects 0.000 description 4
- 230000003292 diminished effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000004108 freeze drying Methods 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 239000013049 sediment Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000012901 Milli-Q water Substances 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 230000002429 anti-coagulating effect Effects 0.000 description 3
- 230000002924 anti-infective effect Effects 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 210000003743 erythrocyte Anatomy 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000012088 reference solution Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 230000004913 activation Effects 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000012447 hatching Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000002949 hemolytic effect Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229940127554 medical product Drugs 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000013215 result calculation Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- VNFVKWMKVDOSKT-LREBCSMRSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;piperazine Chemical compound C1CNCCN1.OC(=O)[C@H](O)[C@@H](O)C(O)=O VNFVKWMKVDOSKT-LREBCSMRSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WFJIVOKAWHGMBH-UHFFFAOYSA-N 4-hexylbenzene-1,3-diol Chemical compound CCCCCCC1=CC=C(O)C=C1O WFJIVOKAWHGMBH-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 0 C[C@@]1[C@]2(CS=C)C1CC*2 Chemical compound C[C@@]1[C@]2(CS=C)C1CC*2 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- 239000004812 Fluorinated ethylene propylene Substances 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- UWMYPAGPLYUAMK-UHFFFAOYSA-M [4-[4-(diethylamino)benzoyl]phenyl]-diethyl-octylazanium iodide Chemical class [I-].C(C)N(C1=CC=C(C(=O)C2=CC=C(C=C2)[N+](CCCCCCCC)(CC)CC)C=C1)CC UWMYPAGPLYUAMK-UHFFFAOYSA-M 0.000 description 1
- AEEAZFQPYUMBPY-UHFFFAOYSA-N [I].[W] Chemical compound [I].[W] AEEAZFQPYUMBPY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000010065 bacterial adhesion Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000010523 cascade reaction Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229920009441 perflouroethylene propylene Polymers 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 208000001297 phlebitis Diseases 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Materials For Medical Uses (AREA)
Abstract
The invention provides a kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe and preparation method thereof, anti-coagulation anti-bacterial type remaining needle sleeve pipe includes remaining needle sleeve pipe and passes through the light-initiated anti-coagulation anti-bacterial coating being grafted on remaining needle sleeve pipe；Coating includes liquaemin and takes out Hydrogen quaternary ammonium salt with structure shown in formula I.Take out Hydrogen quaternary ammonium salt and take out hydrogen and recombining reaction with remaining needle sleeve pipe matrix surface, heparin molecule so that coating adherence is higher, and adhesion stability is good, has stronger universality and practicality；Anticoagulation and antibacterial effect with non-release type, it is pierced into sleeve pipe, coating composition dissociation does not occur during washing away etc. and comes off for transfusion, blood flow, anticoagulation and durable antibacterial effect, and avoid after the quaternary ammonium salt that dissociation leaches enters vein and the risk for triggering general toxicity be present.Formula I；R is selected from OrR1And R2Independently selected from H or C1~C4 alkyl；R3Selected from C8~C16 alkyl；X‑Selected from Cl‑、Br‑Or I‑。
Description
Technical field
The present invention relates to medical instruments field, more particularly to a kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe and its preparation side
Method.
Background technology
Venous detaining needle is also known as trochar, is made up of critical pieces such as draw point, sleeve pipe, needle stands.It is a kind of when puncturing
Transfusion instrument when nook closing member and sleeve pipe are pierced into blood vessel together, and extracting nook closing member out by sleeve pipe delay in the blood vessel.Venous indwelling
Pin has abandoned the shortcomings that traditional daily venipuncture, can be retained in for a long time in vein, has both reduced patient and has been made because puncturing repeatedly
Into injury of blood vessel and mental suffering, mitigate the work load in terms of the venipuncture of nursing staff again, save the operation of nurse
Time.Especially when rescuing state of an illness critical patient, can timing, multiple dosing, transfusion time is long, amount of infusion is big, and advantage is brighter
It is aobvious.30~80% inpatient uses venous detaining needle according to statistics, therefore such products application is extensive.
But in actual use, easily generation phlebitis, bacterium infection, set pipe choking etc. be present and ask in venous detaining needle
Topic, shorten the usage time of remaining needle.Because remaining needle sleeve pipe is with that after contacting blood, can cause plasma proteins leading
The absorption and denaturation of pipe surface, then trigger intrinsic clotting cascade reaction, cause the local thrombus of intubation intervention near sites
Generation, seriously endanger the health of patient.In addition, remaining needle sleeve pipe, during storage, intervention human body etc., bacterium is easily in conduit
Surface adhesion, and propagation forms bacterial biof iotalm quickly, and then medical infection accident can occur, severe patient causes death.
In fact, the bacterial adhesion infection and Coagulation test in apparatus experiment can mutually promote and produce complications, cause 4~6% apparatuses
The life-span is shortened in failure, is related to millions of patient healths, even results in death.In summary, the synchronous vein that improves stays
The surface anticoagulant and anti-microbial property of needle cannula are put, is extremely important.
In order to assign the anti-infective and anticoagulant performance of venous detaining needle sleeve surface, it is necessary to targetedly in conduit table
Face builds antibacterial and anticoagulant functions layer.There are substantial amounts of document and patent report to realize surface anticoagulant antibacterial functions at present
A kind of simple and effective method, by compounding to form heparin complex heparin and quaternary ammonium material, select appropriate organic molten
Agent dissolves compound and realizes its load in medical apparatus surface by dipping or spraying method.Research shows, in coating
Heparin can effectively improve the blood compatibility on surface, and assign medicine equipment anticoagulation function.In addition, the season with antibiotic property
Ammonium salt species also correspondingly assign the anti-infective function of coating.But surface modification is carried out to remaining needle sleeve pipe in this way,
The anti-coagulation anti-bacterial coating of sleeve surface is easily pierced into conduit, decoction transport, blood flow occur dissociation during washing away etc. and come off, from
And the anticoagulation of remaining needle sleeve pipe and antibacterial effect is caused drastically to shorten.In addition, the heparin that dissociation leaches enters after vein easily
The side effects such as initiation is lost blood, allergy, decrease of platelet；And the quaternary surfactant discharged then can be to peripheral cell and tissue
Bio-toxicity is caused, or even exists and triggers general toxicity.
Several patent reports for developing in recent years significantly improve the stability of the type coating.Such as Chinese patent
Zl03116747.0 realizes coating by way of adding esters of acrylic acid and hot setting in heparin quaternary ammonium compound
Internal crosslinking.Chinese patent 200910069886.4 is using bifunctional group reagent glutaraldehyde immersion treatment with cross-linked heparin season
Ammonium salt coating.Although above-mentioned patent effectively increases the stability of coat inside by way of building cross-linked network, due to
The missing of reactable functional group in heparin and quaternary ammonium salt component, the essence of the releasable property of the type coating do not change.Secondly,
Interaction mode between above-mentioned coating and base material is still physical effect, and bond strength therebetween is weak, by ring
Border influences greatly, the risk that coating integrally comes off be present.In addition, existing research primarily focuses on the sound to coating anticoagulant functions
Bright, the antibacterial functions exploration to coating is less.
The content of the invention
In view of this, it is an object of the invention to provide a kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe and preparation method thereof,
The coating adherence of the anti-coagulation anti-bacterial type remaining needle sleeve pipe is higher.
The invention provides a kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe, including remaining needle sleeve pipe and pass through light-initiated grafting
Anti-coagulation anti-bacterial coating on to remaining needle sleeve pipe；
The anti-coagulation anti-bacterial coating includes liquaemin and takes out Hydrogen quaternary ammonium salt；
The Hydrogen quaternary ammonium salt of taking out has structure shown in formula I：
In formula I, R independently selected from
R1And R2Independently selected from H or C1~C4 alkyl；R3Independently selected from C8~C16 alkyl；
X-Independently selected from Cl-、Br-Or I-。
Preferably, the anti-coagulation anti-bacterial coating accounts for the 0.1~20% of remaining needle sleeve pipe quality.
Preferably, the molecular weight of the liquaemin is 3000~25000g/mol.
Preferably, the R1And R2Independently selected from H ,-CH3、-CH2CH3、-C3H7Or-C4H9；R3Independently selected from-
C8H17、-C10H21、-C12H25、-C14H19Or-C16H33。
Preferably, the Hydrogen quaternary ammonium salt of taking out is chosen in particular from N- (4- benzoylbenzyls)-N, N- dimethyl dodecyl base -1-
Ammonium bromide, 4- (4- (diethylamino) benzoyl)-N, N- diethyl-N- octyl phenyls ammonium iodide, N, N- dimethyl-N -s are pungent
Base -9- oxygen -9H- thioxanthene -3- ammonium bromides and N- decyls-N, N- dimethyl -9,10- dioxygen -9,10- dihydroanthracene -2- ammonium chlorides
In one or more.
Preferably, the glutinous Alginic Sodium Diester repeat unit in the liquaemin and the mol ratio for taking out Hydrogen quaternary ammonium salt are 100：
5~120.
The invention provides a kind of preparation method of anti-coagulation anti-bacterial type remaining needle sleeve pipe described in above-mentioned technical proposal, including
Following steps：
A) Hydrogen quaternary ammonium salt solution and heparin sodium aqua reaction will be taken out with structure shown in formula I, obtains taking out Hydrogen quaternary ammonium salt liver
Plain compound；
In formula I, R is selected from
R1And R2Independently selected from H or C1~C4 alkyl；R3Alkyl selected from C8~C16；
X-Selected from Cl-、Br-Or I-；
B) by the step A) obtained Hydrogen quaternary ammonium salt heparin complex of taking out is dissolved in organic solvent, then answered what is obtained
Polymer solution is supported on remaining needle sleeve pipe；
C) by the step B) obtain be attached with compound remaining needle sleeve pipe carry out ultra-violet curing processing, obtain anti-freezing
Blood antibacterial remaining needle sleeve pipe.
Preferably, the main wavelength that passes through for the ultraviolet light that the ultra-violet curing processing uses is 180~420nm；It is described ultraviolet
The time of curing process is 1~10min.
Preferably, the concentration of the complex solution is 0.01~20g/mL；
The concentration for taking out Hydrogen quaternary ammonium salt solution with structure shown in formula I is 1~30g/mL；
The concentration of the heparin sodium aqua is 1~50g/mL.
Preferably, the organic solvent in chloroform, acetone, methanol, ethanol, isopropanol and dimethyl sulfoxide one
Kind is a variety of.
The invention provides a kind of preparation method of anti-coagulation anti-bacterial type remaining needle sleeve pipe described in above-mentioned technical proposal, including
Following steps：
A) Hydrogen quaternary ammonium salt solution and heparin sodium aqua reaction will be taken out with structure shown in formula I, obtains taking out Hydrogen quaternary ammonium salt liver
Plain compound；
In formula I, R is selected from
R1And R2Independently selected from H or C1~C4 alkyl；R3Alkyl selected from C8~C16；
X-Selected from Cl-、Br-Or I-；
B) by the step A) obtained Hydrogen quaternary ammonium salt heparin complex of taking out is dissolved in organic solvent, then answered what is obtained
Polymer solution is supported on remaining needle sleeve pipe；
C) by the step B) obtain be attached with compound remaining needle sleeve pipe carry out ultra-violet curing processing, obtain anti-freezing
Blood antibacterial remaining needle sleeve pipe.
Preferably, the main wavelength that passes through for the ultraviolet light that the ultra-violet curing processing uses is 180~420nm；It is described ultraviolet
The time of curing process is 1~10min.
Preferably, the concentration of the complex solution is 0.01~20g/mL；
The concentration for taking out Hydrogen quaternary ammonium salt solution with structure shown in formula I is 1~30g/mL；
The concentration of the heparin sodium aqua is 1~50g/mL.
Preferably, the mode of the load is selected from dipping, spraying, spin coating or wiping.
Preferably, the organic solvent in chloroform, acetone, methanol, ethanol, isopropanol and dimethyl sulfoxide one
Kind is a variety of.
The invention provides a kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe, including remaining needle sleeve pipe and pass through light-initiated grafting
Anti-coagulation anti-bacterial coating on to remaining needle sleeve pipe；The anti-coagulation anti-bacterial coating includes liquaemin and takes out Hydrogen quaternary ammonium salt；Institute
State and take out Hydrogen quaternary ammonium salt there is structure shown in formula I.In anti-coagulation anti-bacterial type remaining needle sleeve pipe Hydrogen quaternary ammonium salt is taken out with structure shown in formula I
Hydrogen and recombining reaction can be taken out with remaining needle sleeve pipe matrix surface, heparin molecule, realize coating covalently connecing in matrix surface
The internal crosslinking of branch and coating itself so that coating adherence is higher, and adhesion stability is good, suitable for various surface naturies and again
The medicine equipment of miscellaneous shape, there is stronger universality and practicality.In addition, anti-coagulation anti-bacterial type remaining needle provided by the invention
Sleeve pipe has the anticoagulation and antibacterial effect of non-release type, is pierced into sleeve pipe, during washing away etc. coating does not occur for transfusion, blood flow
Composition dissociation comes off, anticoagulation and durable antibacterial effect, and avoids the quaternary surfactant that dissociation leaches and enter vein
The risk for triggering general toxicity afterwards be present.Test result indicates that：The coating Retention of the anti-coagulation anti-bacterial type remaining needle sleeve pipe exists
99.6%, 99.3% is up to after ultrasonic 10min, 60min respectively；The bacterium bacterial membrane of Antimicrobial type lien needle sleeve surface presents dry
Flat, ablation damaged form, for obvious dead state；The sterilizing rate of Escherichia coli and staphylococcus aureus is up to respectively
98.8% and 99.9%, sterilization of high efficiency, bactericidal range is wide；The blood for being stained with minority of Antimicrobial type lien needle sleeve surface is small
Plate, and the circular, unactivated state of fusiformis is presented in blood platelet, illustrates the probability of happening that can reduce blood coagulation phenomenon；Hemolysis rate is low
To 0.1%.
Brief description of the drawings
Fig. 1 is the bacterium pattern photo of non-antimicrobial treatment sleeve surface；
Fig. 2 is the bacterium pattern photo for the Antimicrobial type lien needle sleeve surface that the embodiment of the present invention 1 obtains；
Fig. 3 is the blood platelet pattern photo that non-anticoagulation handles sleeve surface；
Fig. 4 is the blood platelet pattern photo for the anti-coagulation anti-bacterial type Injector Bushing pipe surface that the embodiment of the present invention 1 obtains.
Embodiment
The invention provides a kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe, including remaining needle sleeve pipe and pass through light-initiated grafting
Anti-coagulation anti-bacterial coating on to remaining needle sleeve pipe；
The anti-coagulation anti-bacterial coating includes liquaemin and takes out Hydrogen quaternary ammonium salt；
The Hydrogen quaternary ammonium salt of taking out has structure shown in formula I：
In formula I, R independently selected from
R1And R2Independently selected from H or C1~C4 alkyl；R3Independently selected from C8~C16 alkyl；
X-Independently selected from Cl-、Br-Or I-。
The Hydrogen quaternary ammonium salt of taking out with structure shown in formula I in anti-coagulation anti-bacterial type remaining needle sleeve pipe can be with remaining needle sleeve pipe matrix
Surface, heparin take out hydrogen and recombining reaction, realize coating in the covalence graft and coating of the matrix surface internal crosslinking of itself,
So that coating adherence is higher, adhesion stability is good, suitable for various surface naturies and the medicine equipment of complicated shape, have compared with
Strong universality and practicality.In addition, anti-coagulation anti-bacterial type Injector Bushing pipe provided by the invention has the anti-freezing of non-release type
Blood and antibacterial effect, during being pierced into, transfusion, blood flow wash away etc. coating composition dissociation does not occur comes off, anticoagulation and antibacterial
Effect is lasting, and avoids after the quaternary surfactant that dissociation leaches enters vein and the risk for triggering general toxicity be present.
Anti-coagulation anti-bacterial type remaining needle sleeve pipe provided by the invention includes remaining needle sleeve pipe.The matrix of the remaining needle sleeve pipe
Material is medical macromolecular materials well known to those skilled in the art.The present invention is to used medical macromolecular materials
Species and its physical and chemical performance are not particularly limited, using the macromolecule material well known to those skilled in the art available for medical field
Material.In one embodiment provided by the invention, the medical macromolecular materials include polyurethane elastomer, nylon elastic
One or more in body, polyvinyl chloride, polytetrafluoroethylene (PTFE), fluorinated ethylene-propylene copolymer and silicon rubber.The present invention is to the anti-freezing
The concrete structure and size of blood Antimicrobial type lien needle sleeve pipe are not particularly limited, and those skilled in the art design according to the actual requirements
The structure of remaining needle sleeve pipe and the size of selection remaining needle sleeve pipe.
Anti-coagulation anti-bacterial type remaining needle sleeve pipe provided by the invention includes being grafted on remaining needle sleeve pipe by light-initiated
Anti-coagulation anti-bacterial coating.The anti-coagulation anti-bacterial coating to act as making Injector Bushing pipe provided by the invention to have anticoagulant
Effect, while the probability of bacterium infection generation is reduced, extend the service life of remaining needle sleeve pipe.The anti-coagulation anti-bacterial coating bag
Include liquaemin and take out Hydrogen quaternary ammonium salt.
In the present invention, it is described take out the functional group such as benzophenone, thioxanthone and anthraquinone in Hydrogen quaternary ammonium salt can be with indwelling
C-H groups capture hydrogen in needle cannula matrix surface, heparin, and Norrish II reactions occur and recombining reaction forms the spy of C-C keys
Property, realize that coating is high in the covalence graft and coating of the matrix surface internal crosslinking of itself, coating adherence, adhesion stability
It is good；The contact sterilization characteristic for taking out Hydrogen quaternary ammonium salt, so as to get anti-coagulation anti-bacterial coating there is higher anti-infective characteristic,
Which reduce the bio-toxicity to surrounding tissue.
The Hydrogen quaternary ammonium salt of taking out has structure shown in formula I：
In formula I, R is selected from
In the group of R selections, horizontal line represents connecting key；
Wherein,With-CH2- it is linking group.
R1And R2Independently selected from H or C1~C4 alkyl；Preferably, R1And R2Independently selected from H ,-CH3、-CH2CH3、-
CH2CH2CH3Or-CH2CH2CH2CH3；
R3Alkyl selected from C8~C16；Preferably, R3Independently selected from-C8H17、-C10H21、-C12H25、-C14H19Or-
C16H33。
X-Selected from Cl-、Br-Or I-。
In the present invention, the Hydrogen quaternary ammonium salt of taking out specifically is preferably selected from N- (4- benzoylbenzyls)-N, N- dimethyl ten
Dialkyl group -1- ammonium bromides, 4- (4- (diethylamino) benzoyl)-N, N- diethyl-N- octyl phenyls ammonium iodide, N, N- bis-
Methyl-N-octyl -9- oxygen -9H- thioxanthene -3- ammonium bromides and N- decyls-N, N- dimethyl -9,10- dioxygen -9,10- dihydroanthracenes -
One or more in 2- ammonium chlorides.The present invention does not have special limitation to the above-mentioned source for taking out Hydrogen quaternary ammonium salt, using ability
Mentioned kind known to field technique personnel takes out Hydrogen quaternary ammonium salt, can such as use its commercial goods.
The structural formula of N- (4- benzoylbenzyls)-N, N- the dimethyl dodecyl base -1- ammonium bromides is：
Wherein, the structure of 4- (4- (diethylamino) benzoyl)-N, the N- diethyl-N- octyl phenyl ammonium iodides
Formula is：
Wherein, the N, N- dimethyl-N-octyl group -9- oxygen -9H- thioxanthene -3- ammonium bromide structural formulas are：
Wherein, N- decyls-N, N- dimethyl -9,10- dioxygen -9,10- dihydroanthracene -2- ammonium chloride structural formulas are：
The present invention does not have special limitation to the source of the liquaemin, using liquaemin well known to those skilled in the art
, can such as use its commercial goods.The molecular weight of the liquaemin is preferably 3000~25000g/mol, more preferably
5000~22000g/mol, most preferably 7500~20000g/mol.
In the present invention, the glutinous Alginic Sodium Diester repeat unit in the liquaemin and the mol ratio for taking out Hydrogen quaternary ammonium salt are excellent
Elect 100 as:5~120, more preferably 100:25~110, most preferably 100:50~100.
The anti-coagulation anti-bacterial coating preferably accounts for the 0.1~20% of remaining needle sleeve pipe quality, and more preferably 5~10%.
The invention provides a kind of preparation method of anti-coagulation anti-bacterial type remaining needle sleeve pipe described in above-mentioned technical proposal, including
Following steps：
A) Hydrogen quaternary ammonium salt solution and heparin sodium aqua reaction will be taken out with structure shown in formula I, obtains taking out Hydrogen quaternary ammonium salt liver
Plain compound；
In formula I, R is selected from
R1And R2Independently selected from H or C1~C4 alkyl；R3Alkyl selected from C8~C16；
X-Selected from Cl-、Br-Or I-；
B) by the step A) obtained Hydrogen quaternary ammonium salt heparin complex of taking out is dissolved in organic solvent, then answered what is obtained
Polymer solution is supported on remaining needle sleeve pipe；
C) by the step B) obtain be attached with compound remaining needle sleeve pipe carry out ultra-violet curing processing, obtain anti-freezing
Blood antibacterial remaining needle sleeve pipe.
The present invention will take out Hydrogen quaternary ammonium salt solution and heparin sodium aqua reaction with structure shown in formula I, obtain taking out Hydrogen quaternary ammonium
Salt heparin complex.The process preferably specifically includes：
Hydrogen quaternary ammonium salt solution will be taken out to be added drop-wise in heparin sodium aqua, until having a large amount of whites or pale yellow precipitate from solution
Middle precipitation, with distilled water or milli-Q water sediment, obtain taking out Hydrogen quaternary ammonium salt heparin complex after drying.
In the present invention, the concentration for taking out Hydrogen quaternary ammonium salt solution with structure shown in formula I is preferably 1~30g/mL；Institute
The concentration for stating heparin sodium aqua is preferably 1~50g/mL.The present invention is to the dosage for taking out Hydrogen quaternary ammonium salt solution and liquaemin
There is no special limitation, the reaction product can be precipitated complete.
The Hydrogen quaternary ammonium salt heparin complex of taking out is dissolved in organic solvent by the present invention, the complex solution that then will be obtained
It is supported on remaining needle sleeve pipe.The process preferably specifically includes：
Hydrogen quaternary ammonium salt heparin complex will be taken out and be dissolved in organic solvent, made with dipping, spraying, spin coating and the mode of wiping multiple
Compound is attached to Injector Bushing pipe surface, obtains intermediate coating.
In the present invention, the organic solvent is in chloroform, acetone, methanol, ethanol, isopropanol and dimethyl sulfoxide
One or more.The concentration of the complex solution is preferably 0.01~20g/mL；More preferably 0.1~15g/mL.
The mode of the load is preferably selected from impregnating, sprayed, spin coating or wiping.
It is of the invention by the remaining needle sleeve pipe for being attached with compound after what is obtained is attached with the remaining needle sleeve pipe of compound
Ultra-violet curing processing is carried out, obtains anti-coagulation anti-bacterial remaining needle sleeve pipe.
In the present invention, the light source of the ultraviolet light be preferably low pressure mercury lamp, medium pressure mercury lamp, high-pressure sodium lamp, iodine-tungsten lamp and
Add the one or more in optical filter.It is described take out Hydrogen quaternary ammonium salt under the excitation of ultraviolet simultaneously with matrix surface and liver
Association reaction, the anti-coagulation anti-bacterial coating being crosslinked occur for plain sodium molecule.The ultraviolet light that the ultra-violet curing processing uses
The main wavelength that passes through is preferably 180~420nm, more preferably 200~400nm；The time of ultra-violet curing processing is preferably 1~
10min, more preferably 2~8min.
After ultra-violet curing processing, ultra-violet curing processing product is preferably cleaned and dried successively by the present invention.The present invention
It is preferred that under conditions of water-bath vibration, cleaned successively using ethanol and deionized water, the coating after being cleaned.In this hair
In bright, the frequency of the water-bath vibration is preferably 100~150Hz, more preferably 120~130Hz；The time of the ethanol cleaning
Preferably 20~50min, more preferably 25~40min；The time of the deionized water cleaning is preferably 20~50min, more excellent
Elect 25~40min as.The present invention does not have special limitation to the ethanol of the cleaning and the dosage of deionized water.In the present invention
In, the drying is preferably to be dried in vacuo, and the time of the drying is preferably 20~30 hours, more preferably 24~28 hours；
The temperature of the drying is preferably 40~80 DEG C, more preferably 60~70 DEG C.
The invention provides a kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe, including remaining needle sleeve pipe and pass through light-initiated grafting
Anti-coagulation anti-bacterial coating on to remaining needle sleeve pipe；The anti-coagulation anti-bacterial coating includes liquaemin and takes out Hydrogen quaternary ammonium salt；Institute
State and take out Hydrogen quaternary ammonium salt there is structure shown in formula I.In anti-coagulation anti-bacterial type remaining needle sleeve pipe Hydrogen quaternary ammonium salt is taken out with structure shown in formula I
Hydrogen and recombining reaction can be taken out with remaining needle sleeve pipe matrix surface, heparin, realize coating matrix surface covalence graft and
The internal crosslinking of coating itself so that coating adherence is higher, and adhesion stability is good, suitable for various surface naturies and complex shape
The medicine equipment of shape, there is stronger universality and practicality.In addition, anti-coagulation anti-bacterial type remaining needle sleeve pipe provided by the invention
Anticoagulation and antibacterial effect with non-release type, coating composition dissociation does not occur during transfusion, blood flow wash away etc. and comes off,
Anticoagulation and durable antibacterial effect, and avoid after the quaternary surfactant that dissociation leaches enters vein and initiation whole body be present
The risk of toxicity.Test result indicates that：The coating Retention of the anti-coagulation anti-bacterial type remaining needle sleeve pipe is in ultrasonic 10min, 60min
It is up to 99.6%, 99.3% respectively afterwards；The damaged shape of shrivelled ablation is presented in the bacterium bacterial membrane of Antimicrobial type lien needle sleeve surface
State, for obvious dead state；98.8% and 99.9% is up to respectively to the sterilizing rate of Escherichia coli and staphylococcus aureus,
Sterilization of high efficiency, bactericidal range are wide；The blood platelet for being stained with minority of Antimicrobial type lien needle sleeve surface, and circle is presented in blood platelet
The unactivated state of shape, fusiformis, illustrate the probability of happening that can reduce blood coagulation phenomenon；Hemolysis rate as little as 0.1%.
In order to further illustrate the present invention, with reference to embodiment to a kind of anti-coagulation anti-bacterial type indwelling provided by the invention
Needle cannula and preparation method thereof is described in detail, but they can not be interpreted as into limiting the scope of the present invention.
In the examples below, remaining needle sleeve pipe uses the 22G remaining needles of Weihai Jierui Medical Products Co., Ltd.'s production
Sleeve pipe.
Embodiment 1
Prepare anti-coagulation anti-bacterial type remaining needle sleeve pipe
A) N- (4- benzoylbenzyls)-N, N- dimethyl dodecyl base -1- ammonium bromides are dissolved in ultra-pure water, are configured to dense
Spend and take out Hydrogen quaternary ammonium salt solution for 0.1g/ml；Liquaemin (7500~20000g/mol of molecular weight) is dissolved in ultra-pure water, matched somebody with somebody
The heparin sodium aqua that concentration is 0.1g/ml is made；By the above-mentioned heparin sodium aqua taken out Hydrogen quaternary ammonium salt solution and be added drop-wise to 5ml dropwise
In, until there are a large amount of white precipitates to separate out from solution, after standing 30min, it is filtered under diminished pressure to obtain white depositions.Use ultra-pure water
Washing precipitate obtains taking out Hydrogen quaternary ammonium salt heparin complex three times, after freeze-drying.
B) by the step A) obtained Hydrogen quaternary ammonium salt heparin complex of taking out is dissolved in chloroform, and the concentration of preparation is
2% takes out Hydrogen quaternary ammonium salt heparin complex solution；By remaining needle sleeve pipe (weight W0) impregnated in above-mentioned complex solution
30min, then at room temperature evaporates into solvent dry, obtains the indwelling that Hydrogen quaternary ammonium salt heparin complex intermediate coating is taken out in load
Needle cannula (weight W1)。
C) the remaining needle sleeve pipe for being loaded with taking out Hydrogen quaternary ammonium salt heparin complex is placed under 300W high-pressure sodium lamps and irradiated
5min, take out Hydrogen quaternary ammonium salt and association reaction occur with matrix surface and heparin sodium molecule simultaneously under the excitation of ultraviolet,
In the anti-coagulation anti-bacterial coating that Injector Bushing pipe surface is crosslinked.Bar then is vibrated into water-bath of the remaining needle sleeve pipe in 120Hz
Under part, after successively respectively cleaning 25min using ethanol, deionized water, at 60 DEG C, anti-coagulation anti-bacterial is obtained after being dried in vacuo 24h
Type remaining needle sleeve pipe (weight W2)。
Embodiment 2
A 4- (4- (diethylamino) benzoyl)-N, N- diethyl-N- octyl phenyl ammonium iodides) are dissolved in ultra-pure water
In, it is configured to concentration and takes out Hydrogen quaternary ammonium salt solution for 0.125g/ml；Liquaemin (7500~20000g/mol of molecular weight) is molten
In ultra-pure water, the heparin sodium aqua that concentration is 0.125g/ml is configured to；Above-mentioned Hydrogen quaternary ammonium salt solution of taking out is added drop-wise to dropwise
In 5ml heparin sodium aqua, until there is a large amount of white precipitates to be separated out from solution.After standing 30min, it is filtered under diminished pressure to obtain white
Sediment.Obtained taking out Hydrogen quaternary ammonium salt heparin complex three times, after freeze-drying with milli-Q water sediment.
B) by the step A) obtained Hydrogen quaternary ammonium salt heparin complex of taking out is dissolved in chloroform, and the concentration of preparation is
2% takes out Hydrogen quaternary ammonium salt heparin complex solution；By remaining needle sleeve pipe (weight W0) impregnated in above-mentioned complex solution
30min, then at room temperature evaporates into solvent dry, obtains the indwelling that Hydrogen quaternary ammonium salt heparin complex intermediate coating is taken out in load
Needle cannula (weight W1)。
C) the remaining needle sleeve pipe for being loaded with taking out Hydrogen quaternary ammonium salt heparin complex is placed under 300W high-pressure sodium lamps and irradiated
8min, take out Hydrogen quaternary ammonium salt and association reaction occur with matrix surface and heparin sodium molecule simultaneously under the excitation of ultraviolet,
In the anti-coagulation anti-bacterial coating that Injector Bushing pipe surface is crosslinked.Bar then is vibrated into water-bath of the remaining needle sleeve pipe in 120Hz
Under part, after successively respectively cleaning 25min using ethanol, deionized water, at 60 DEG C, anti-coagulation anti-bacterial is obtained after being dried in vacuo 24h
Type remaining needle sleeve pipe (weight W2)。
Embodiment 3
A) N, N- dimethyl-N-octyl group -9- oxygen -9H- thioxanthene -3- ammonium bromides are dissolved in ultra-pure water, are configured to concentration
Hydrogen quaternary ammonium salt solution is taken out for 0.1g/mL；Liquaemin (7500~20000g/mol of molecular weight) is dissolved in ultra-pure water, prepared
Into the heparin sodium aqua that concentration is 0.15g/ml；By the above-mentioned heparin sodium aqua taken out Hydrogen quaternary ammonium salt solution and be added drop-wise to 5ml dropwise
In, until there is a large amount of white precipitates to be separated out from solution.After standing 30min, it is filtered under diminished pressure to obtain white depositions.Use ultra-pure water
Washing precipitate obtains taking out Hydrogen quaternary ammonium salt heparin complex three times, after freeze-drying.
B) by the step A) obtained Hydrogen quaternary ammonium salt heparin complex of taking out is dissolved in chloroform, and the concentration of preparation is
2% takes out Hydrogen quaternary ammonium salt heparin complex solution；By remaining needle sleeve pipe (weight W0) impregnated in above-mentioned complex solution
15min, then at room temperature evaporates into solvent dry, obtains the indwelling that Hydrogen quaternary ammonium salt heparin complex intermediate coating is taken out in load
Needle cannula (weight W1)。
C) the remaining needle sleeve pipe for being loaded with taking out Hydrogen quaternary ammonium salt heparin complex is placed under 300W high-pressure sodium lamps and irradiated
6min, take out Hydrogen quaternary ammonium salt and association reaction occur with matrix surface and heparin sodium molecule simultaneously under the excitation of ultraviolet,
In the anti-coagulation anti-bacterial coating that Injector Bushing pipe surface is crosslinked.Bar then is vibrated into water-bath of the remaining needle sleeve pipe in 120Hz
Under part, after successively respectively cleaning 25min using ethanol, deionized water, at 60 DEG C, anti-coagulation anti-bacterial is obtained after being dried in vacuo 24h
Type remaining needle sleeve pipe (weight W2)。
Embodiment 4
A) N- decyls-N, N- dimethyl -9,10- dioxygen -9,10- dihydroanthracene -2- ammonium chlorides are dissolved in ultra-pure water, prepared
Into concentration Hydrogen quaternary ammonium salt solution is taken out for 0.1g/ml；Liquaemin (7500~20000g/mol of molecular weight) is dissolved in ultra-pure water
In, it is configured to the heparin sodium aqua that concentration is 0.15g/ml；By the above-mentioned heparin taken out Hydrogen quaternary ammonium salt solution and be added drop-wise to 5ml dropwise
In sodium solution, until there is a large amount of white precipitates to be separated out from solution.After standing 30min, it is filtered under diminished pressure to obtain white depositions.With
Milli-Q water sediment obtains taking out Hydrogen quaternary ammonium salt heparin complex three times, after freeze-drying.
B) by the step A) obtained Hydrogen quaternary ammonium salt heparin complex of taking out is dissolved in chloroform, and the concentration of preparation is
2% takes out Hydrogen quaternary ammonium salt heparin complex solution；By remaining needle sleeve pipe (weight W0) impregnated in above-mentioned complex solution
15min, then at room temperature evaporates into solvent dry, obtains the indwelling that Hydrogen quaternary ammonium salt heparin complex intermediate coating is taken out in load
Needle cannula (weight W1)。
C) the remaining needle sleeve pipe for being loaded with taking out Hydrogen quaternary ammonium salt heparin complex is placed under 300W high-pressure sodium lamps and irradiated
10min, take out Hydrogen quaternary ammonium salt and association reaction occur with matrix surface and heparin sodium molecule simultaneously under the excitation of ultraviolet,
In the anti-coagulation anti-bacterial coating that Injector Bushing pipe surface is crosslinked.Bar then is vibrated into water-bath of the remaining needle sleeve pipe in 120Hz
Under part, after successively respectively cleaning 25min using ethanol, deionized water, at 60 DEG C, anti-coagulation anti-bacterial is obtained after being dried in vacuo 24h
Type remaining needle sleeve pipe (weight W2)。
The performance test of embodiment 5
1) coating Retention is tested：
By remaining needle sleeve pipe (the weight W of the obtained load intermediate coating of embodiment 1~41) and anti-coagulation anti-bacterial type stay
Put needle cannula (weight W2) respectively in supersonic wave cleaning machine after processing 10min and 60min, at 60 DEG C, it is dried in vacuo 24h
Afterwards, weighing, (weight is W3And W4).Coating Retention is calculated, its calculation formula is for intermediate coating remaining needle sleeve pipe：Apply
Layer retention ratio (%)=(W3-W0/W1-W0) × 100%；For anti-coagulation anti-bacterial type remaining needle sleeve pipe, its calculation formula is：Coating
Retention ratio (%)=(W4-W0/W2-W0) × 100%.As a result as shown in table 1, table 1 is the anti-freezing that the embodiment of the present invention 1~4 obtains
The coating Retention of blood Antimicrobial type lien needle sleeve pipe.
The coating Retention for the anti-coagulation anti-bacterial type remaining needle sleeve pipe that the embodiment of the present invention 1~4 of table 1 obtains
As can be seen from Table 1, present invention employs the painting of the anti-coagulation anti-bacterial type remaining needle sleeve pipe of light-initiated crosslinking technology
Layer Retention is up to 99.6%, 99.3% respectively after ultrasonic 10min, 60min, and the intermediate only loaded for physically applies
The Injector Bushing pipe coating Retention of layer is respectively 43.5%, 24.6%, illustrates that new anti-coagulation anti-bacterial provided by the invention applies
Layer has the stability of higher matrix adhesive force and coating itself.
2) antibiotic property is tested：
New anti-coagulation anti-bacterial type remaining needle sleeve pipe made from embodiment 1~4 is contained into bacterial concentration in 1mL is
107After cultivating 24h in Cells/mL LB nutrient solutions, Injector Bushing pipe surface bacterium pattern is shot using SEM
Change；Remaining needle sleeve pipe is determined by the way of supersound process-dilution-flat board culture；Remaining needle sleeve pipe is determined using ELIASA
The OD values (solution optical density) of place bacterial solution.To ensure that experiment is true, reliable, experiment accidental error is reduced, 3 weights must be used
The average value tested again draws data, test result calculations：Sterilizing rate=(the average bacterium of control group average colony number-test group
Fall number)/control group average colony number × 100%, wherein, control group is the remaining needle sleeve pipe (producer for not carrying out antimicrobial treatment：Prestige
Hai Jierui Medical Products Co., Ltd.s, Bi Di Medical Devices Co., Ltd.s).As a result as shown in Fig. 1~2 and table 2~3, Fig. 1 is not
The bacterium pattern photo of antimicrobial treatment sleeve surface, Fig. 2 are the Antimicrobial type lien needle sleeve surface that the embodiment of the present invention 1 obtains
Bacterium pattern photo, table 2 are the sterilizing rate of the anti-coagulation anti-bacterial type remaining needle sleeve pipe arrived of the embodiment of the present invention 1~4, and table 3 is
The OD values of bacterial solution where remaining needle sleeve pipe and control sample that the embodiment of the present invention 1~4 obtains.
Non- antimicrobial treatment Injector Bushing pipe surface grows a large amount of bacteriums it can be seen from Fig. 1~2, and bacterium presentation is full
, unmarred state.The bacterium bacterial membrane of the Antimicrobial type lien needle sleeve surface that the embodiment of the present invention 1 obtains present it is shrivelled,
The damaged form of ablation, for obvious dead state.
The sterilizing rate of the anti-coagulation anti-bacterial type remaining needle sleeve pipe of table 2
As can be seen from Table 2, anti-coagulation anti-bacterial type remaining needle sleeve pipe provided by the invention to Escherichia coli and golden yellow
Staphylococcic sterilizing rate is up to 98.8% and 99.9% respectively, illustrates anti-coagulation anti-bacterial type remaining needle sleeve pipe provided by the invention
Sterilization of high efficiency, bactericidal range are wide.
The OD values of bacterial solution where remaining needle sleeve pipe and control sample that the embodiment of the present invention 1~4 of table 3 obtains
Contrast table 2 and table 3 are as can be seen that the Antibacterial Mechanism of anti-coagulation anti-bacterial type remaining needle sleeve pipe provided by the invention is to connect
The type of touching sterilizes (contact-killing) pattern and unconventional release type (releasing) is sterilized, only to remaining needle sleeve pipe table
The bacterium in face has lethal effect, without being discharged into surrounding environment, this life that will effectively avoid free quaternary ammonium salt molecular band from
Thing toxicity spreads.
3) anticoagulant property is tested：
New anti-coagulation anti-bacterial type remaining needle sleeve pipe made from embodiment 1~4 obtained is rich in blood platelet blood fresh
In slurry after 37 DEG C of hatching 60min, the blood platelet pattern of needle guard pipe surface is put using SEM shooting.To ensure to test
Truly, reliably, experiment accidental error is reduced, data must be drawn with the average value of 3 repetition experiments, wherein, control group is not
Carry out the remaining needle sleeve pipe (producer of anticoagulation processing：Medical High Molecular Product Co., Ltd., Shandong Weigao Group).As a result
As shown in figs. 34, Fig. 3 is the blood platelet pattern photo that non-anticoagulation handles sleeve surface, and Fig. 4 is that the embodiment of the present invention 1 obtains
Anti-coagulation anti-bacterial type Injector Bushing pipe surface blood platelet pattern photo.
Non- anticoagulation processing Injector Bushing pipe surface is stained with a large amount of blood platelets, and blood platelet it can be seen from Fig. 3~4
The state of activation sprawled, sprawled completely is presented.Being stained with for the Antimicrobial type lien needle sleeve surface that the embodiment of the present invention 1 obtains is few
Several blood platelets, and the circular, unactivated state of fusiformis is presented in blood platelet.Consider platelet adhesion reaction and activation in coagulation process
Play an important role, illustrate that the generation that anti-coagulation anti-bacterial type remaining needle sleeve pipe provided by the invention can reduce blood coagulation phenomenon is general
Rate.
4) hemolytic is tested：
By new anti-coagulation anti-bacterial type remaining needle sleeve pipe made from embodiment 1~4 in fresh obtained 2% red blood cell suspension
In liquid after 37 DEG C of hatching 60min, the OD values of centrifuged supernatant are determined using ELIASA.Test result calculations：Hemolysis rate=(survey
Test agent solution O D values-negative reference solution O D values)/(positive reference solution O D values-negative reference solution O D values) × 100%,
Wherein positive reference is that red blood cell is added in deionized water, and negative reference selection red blood cell is added in PBS solution.In order to say
Influence of Mingguang City's initiation grafting technology to remaining needle sleeve pipe hemolytic, physical load made from this experimental selection embodiment 1~4 have
The Injector Bushing of intermediate coating is respectively as comparative example 1~4.As a result as shown in table 4, table 4 obtains for the embodiment of the present invention 1~4
The remaining needle sleeve pipe and the hemolysis rate of comparative example arrived.
The remaining needle sleeve pipe and the hemolysis rate of comparative example that the embodiment of the present invention 1~4 of table 4 obtains
| Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | |
| Hemolysis rate (%) | 3.1 | 2.7 | 2.4 | 2.8 |
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | |
| Hemolysis rate (%) | 0.3 | 0.2 | 0.1 | 0.3 |
As can be seen from Table 4, present invention employs the molten of the anti-coagulation anti-bacterial type remaining needle sleeve pipe of light-initiated crosslinking technology
Blood rate as little as 0.1%, and the hemolysis rate of the Injector Bushing pipe coating of the intermediate coating only loaded for physically may be up to
3.1%, illustrate that new anti-coagulation anti-bacterial coating provided by the invention under ultraviolet irradiation effect, will can easily trigger haemolysis securely
Quaternary surfactant chemistry be fixed on matrix surface and coat inside, so as to significantly reduce the haemolysis of remaining needle sleeve pipe
Rate.
As seen from the above embodiment, the invention provides a kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe, including Injector Bushing
Manage and pass through the light-initiated anti-coagulation anti-bacterial coating being grafted on remaining needle sleeve pipe；The anti-coagulation anti-bacterial coating includes liquaemin
With take out Hydrogen quaternary ammonium salt；The Hydrogen quaternary ammonium salt of taking out has structure shown in formula I.There is formula I in anti-coagulation anti-bacterial type remaining needle sleeve pipe
Taking out Hydrogen quaternary ammonium salt and can taking out hydrogen and recombining reaction with remaining needle sleeve pipe matrix surface, heparin for structure, realizes coating in base
The internal crosslinking of the covalence graft and coating itself in body surface face so that coating adherence is higher, and adhesion stability is good, suitable for each
The medicine equipment of kind surface nature and complicated shape, has stronger universality and practicality.In addition, anti-freezing provided by the invention
Blood Antimicrobial type lien needle sleeve pipe has the anticoagulation and antibacterial effect of non-release type, during being pierced into, transfusion, blood flow wash away etc.
Coating composition dissociation does not occur to come off, anticoagulation and durable antibacterial effect, and avoid the quaternary ammonium salt surface-active that dissociation leaches
The risk for triggering general toxicity be present after entering vein in agent.Test result indicates that：The painting of the anti-coagulation anti-bacterial type remaining needle sleeve pipe
Layer Retention is up to 99.6%, 99.3% respectively after ultrasonic 10min, 60min；The bacterium of Antimicrobial type lien needle sleeve surface is thin
The damaged form of shrivelled ablation is presented in mycoderm, for obvious dead state；Sterilization to Escherichia coli and staphylococcus aureus
Rate is up to 98.8% and 99.9% respectively, and sterilization of high efficiency, bactericidal range is wide；Being stained with for Antimicrobial type lien needle sleeve surface is few
Several blood platelets, and the circular, unactivated state of fusiformis is presented in blood platelet, illustrates the probability of happening that can reduce blood coagulation phenomenon；
Hemolysis rate as little as 0.1%.
Described above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (10)
1. a kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe, including remaining needle sleeve pipe and it is grafted to by light-initiated on remaining needle sleeve pipe
Anti-coagulation anti-bacterial coating；
The anti-coagulation anti-bacterial coating includes liquaemin and takes out Hydrogen quaternary ammonium salt；
The Hydrogen quaternary ammonium salt of taking out has structure shown in formula I：
In formula I, R is selected from
R1And R2Independently selected from H or C1~C4 alkyl；R3Alkyl selected from C8~C16；
X-Selected from Cl-、Br-Or I-。
2. anti-coagulation anti-bacterial type remaining needle sleeve pipe according to claim 1, it is characterised in that the anti-coagulation anti-bacterial coating
Account for the 0.1~20% of remaining needle sleeve pipe quality.
3. anti-coagulation anti-bacterial type remaining needle sleeve pipe according to claim 1, it is characterised in that the molecular weight of the liquaemin
For 3000~25000g/mol.
4. anti-coagulation anti-bacterial type remaining needle sleeve pipe according to claim 1, it is characterised in that the R1And R2Independently select
From H ,-CH3、-CH2CH3、-C3H7Or-C4H9；R3Selected from-C8H17、-C10H21、-C12H25、-C14H19Or-C16H33。
5. anti-coagulation anti-bacterial type remaining needle sleeve pipe according to claim 1, it is characterised in that described to take out Hydrogen quaternary ammonium salt tool
Body is selected from N- (4- benzoylbenzyls)-N, N- dimethyl dodecyl base -1- ammonium bromides, 4- (4- (diethylamino) benzoyls
Base)-N, N- diethyl-N- octyl phenyls ammonium iodide, N, N- dimethyl-N -s octyl group -9- oxygen -9H- thioxanthene -3- ammonium bromides and N-
One or more in decyl-N, N- dimethyl -9,10- dioxygen -9,10- dihydroanthracene -2- ammonium chlorides.
6. anti-coagulation anti-bacterial type remaining needle sleeve pipe according to claim 1, it is characterised in that glutinous more in the liquaemin
Sugared sulfuric acid ester repeat unit and the mol ratio for taking out Hydrogen quaternary ammonium salt are 100：5~120.
7. the preparation method of anti-coagulation anti-bacterial type remaining needle sleeve pipe described in a kind of claim 1~6 any one, including following step
Suddenly：
A Hydrogen quaternary ammonium salt solution and heparin sodium aqua reaction) will be taken out with structure shown in formula I, obtains taking out Hydrogen quaternary ammonium salt heparin and answers
Compound；
In formula I, R independently selected from
R1And R2Independently selected from H or C1~C4 alkyl；R3Independently selected from C8~C16 alkyl；
X-Independently selected from Cl-、Br-Or I-；
B) by the step A) obtained Hydrogen quaternary ammonium salt heparin complex of taking out is dissolved in organic solvent, the compound that then will be obtained
Solution loadings are on remaining needle sleeve pipe；
C) by the step B) obtain be attached with compound remaining needle sleeve pipe carry out ultra-violet curing processing, obtain anticoagulation and resist
Bacterium remaining needle sleeve pipe.
8. preparation method according to claim 7, it is characterised in that the master for the ultraviolet light that the ultra-violet curing processing uses
It is 180~420nm through wavelength；The time of the ultra-violet curing processing is 1~10min.
9. preparation method according to claim 7, it is characterised in that the concentration of the complex solution is 0.01~20g/
mL；
The concentration for taking out Hydrogen quaternary ammonium salt solution with structure shown in formula I is 1~30g/mL；
The concentration of the heparin sodium aqua is 1~50g/mL.
10. preparation method according to claim 7, it is characterised in that the organic solvent be selected from chloroform, acetone,
One or more in methanol, ethanol, isopropanol and dimethyl sulfoxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711089844.8A CN107638612B (en) | 2017-11-08 | 2017-11-08 | Anticoagulation antibacterial indwelling needle cannula and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711089844.8A CN107638612B (en) | 2017-11-08 | 2017-11-08 | Anticoagulation antibacterial indwelling needle cannula and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107638612A true CN107638612A (en) | 2018-01-30 |
| CN107638612B CN107638612B (en) | 2020-09-25 |
Family
ID=61125498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711089844.8A Active CN107638612B (en) | 2017-11-08 | 2017-11-08 | Anticoagulation antibacterial indwelling needle cannula and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107638612B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109517204A (en) * | 2018-11-27 | 2019-03-26 | 威高集团有限公司 | A kind of superslide anti-biotic material and preparation method thereof and superslide anti-microbial catheter |
| CN110372869A (en) * | 2019-08-24 | 2019-10-25 | 思必康（厦门）新材料有限公司 | A kind of polyvinyl alcohol-heparin polymer and its preparation method and application |
| CN110669243A (en) * | 2019-10-14 | 2020-01-10 | 中国科学院长春应用化学研究所 | Antibacterial coating with pH monitoring function, functional material of antibacterial coating with pH monitoring function and preparation method of functional material |
| CN114699564A (en) * | 2022-04-20 | 2022-07-05 | 威高集团有限公司 | Adhesion-enhanced lubricating coating, application thereof and medical interventional catheter |
| CN114788897A (en) * | 2021-01-25 | 2022-07-26 | 苏州林华医疗器械股份有限公司 | Preparation method and application of antibacterial joint |
| CN114848923A (en) * | 2022-04-20 | 2022-08-05 | 威高集团有限公司 | Double-modulus multifunctional self-adaptive coating, application thereof and medical interventional catheter |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1986616A (en) * | 2006-12-15 | 2007-06-27 | 清华大学 | Preparing process of antiseptic graft polymer in micron and nanometer composite structure |
| CN101829374A (en) * | 2009-03-09 | 2010-09-15 | 石学银 | Novel medical blood vessel remaining needle |
| CN204840492U (en) * | 2014-12-08 | 2015-12-09 | 上海普益医疗器械股份有限公司 | Antibiotic needle of keeping somewhere |
| CN105194742A (en) * | 2015-09-17 | 2015-12-30 | 协和同仁科技（天津）有限责任公司 | Anticoagulation method for surface of medical high molecular material or product |
| CN105802192A (en) * | 2016-04-29 | 2016-07-27 | 苏州林华医疗器械股份有限公司 | Novel material applied to indwelling needle catheter and preparation method thereof |
-
2017
- 2017-11-08 CN CN201711089844.8A patent/CN107638612B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1986616A (en) * | 2006-12-15 | 2007-06-27 | 清华大学 | Preparing process of antiseptic graft polymer in micron and nanometer composite structure |
| CN101829374A (en) * | 2009-03-09 | 2010-09-15 | 石学银 | Novel medical blood vessel remaining needle |
| CN204840492U (en) * | 2014-12-08 | 2015-12-09 | 上海普益医疗器械股份有限公司 | Antibiotic needle of keeping somewhere |
| CN105194742A (en) * | 2015-09-17 | 2015-12-30 | 协和同仁科技（天津）有限责任公司 | Anticoagulation method for surface of medical high molecular material or product |
| CN105802192A (en) * | 2016-04-29 | 2016-07-27 | 苏州林华医疗器械股份有限公司 | Novel material applied to indwelling needle catheter and preparation method thereof |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109517204A (en) * | 2018-11-27 | 2019-03-26 | 威高集团有限公司 | A kind of superslide anti-biotic material and preparation method thereof and superslide anti-microbial catheter |
| CN109517204B (en) * | 2018-11-27 | 2021-04-30 | 威高集团有限公司 | Super-smooth antibacterial material, preparation method thereof and super-smooth antibacterial catheter |
| CN110372869A (en) * | 2019-08-24 | 2019-10-25 | 思必康（厦门）新材料有限公司 | A kind of polyvinyl alcohol-heparin polymer and its preparation method and application |
| CN110372869B (en) * | 2019-08-24 | 2021-08-27 | 思必康（厦门）新材料有限公司 | Polyvinyl alcohol-heparin polymer and preparation method and application thereof |
| CN110669243A (en) * | 2019-10-14 | 2020-01-10 | 中国科学院长春应用化学研究所 | Antibacterial coating with pH monitoring function, functional material of antibacterial coating with pH monitoring function and preparation method of functional material |
| CN110669243B (en) * | 2019-10-14 | 2023-12-19 | 中国科学院长春应用化学研究所 | Antibacterial coating with pH monitoring function, functional material of antibacterial coating with pH monitoring function and preparation method of functional material |
| CN114788897A (en) * | 2021-01-25 | 2022-07-26 | 苏州林华医疗器械股份有限公司 | Preparation method and application of antibacterial joint |
| CN114699564A (en) * | 2022-04-20 | 2022-07-05 | 威高集团有限公司 | Adhesion-enhanced lubricating coating, application thereof and medical interventional catheter |
| CN114848923A (en) * | 2022-04-20 | 2022-08-05 | 威高集团有限公司 | Double-modulus multifunctional self-adaptive coating, application thereof and medical interventional catheter |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107638612B (en) | 2020-09-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107638612A (en) | A kind of anti-coagulation anti-bacterial type remaining needle sleeve pipe and preparation method thereof | |
| US5004461A (en) | Methods for rendering plastics thromboresistant and product | |
| CN105263536B (en) | Fixation of the activating agent on substrate | |
| Ma et al. | Mussel-inspired self-coating at macro-interface with improved biocompatibility and bioactivity via dopamine grafted heparin-like polymers and heparin | |
| DE60013890T2 (en) | BIOKOMPATIBLE MEDICAL ARTICLES AND METHOD FOR THE PRODUCTION THEREOF | |
| ES2550147T3 (en) | Biological entities immobilized | |
| DE19716606A1 (en) | Bacteria-repellent and blood-compatible modified surfaces | |
| CN114699564B (en) | Adhesion-enhanced lubricating coating, application thereof and medical intervention catheter | |
| Wang et al. | Hemocompatibility and oxygenation performance of polysulfone membranes grafted with polyethylene glycol and heparin by plasma‐induced surface modification | |
| WO1987005812A1 (en) | Filter medium for selectively removing leucocytes | |
| Wang et al. | Significantly reduced adsorption and activation of blood components in a membrane oxygenator system coated with crosslinkable zwitterionic copolymer | |
| CN114805897B (en) | Super-hydrophilic antibacterial silicone tube and preparation method and application thereof | |
| CN110665071B (en) | Antibacterial and anticoagulant type coating, functional material with antibacterial and anticoagulant type coating and preparation method of functional material | |
| CN110437374A (en) | A kind of amphipathic cationic polymer of quaternary ammonium salt and its application | |
| Singha et al. | Multipronged approach to combat catheter-associated infections and thrombosis by combining nitric oxide and a polyzwitterion: A 7 day in vivo study in a rabbit model | |
| CN104830135A (en) | Antibacterial coating and preparation method thereof | |
| WO1998046648A1 (en) | Interactive system for substance presentation and elimination | |
| JPWO2002098344A1 (en) | Antithrombotic composition and medical device having the same | |
| Zhang et al. | Construction of the mussel-inspired PDAM/lysine/heparin composite coating combining multiple anticoagulant strategies | |
| CN105664253B (en) | Sulfonated fibroin protein film modified Teflon artificial blood vessel and preparation method thereof | |
| CN110947056A (en) | Inner and outer wall anti-infection anticoagulant remaining needle hose and preparation method thereof | |
| Song et al. | High-density zwitterionic polymer brushes exhibit robust lubrication properties and high antithrombotic efficacy in blood-contacting medical devices | |
| Qin et al. | Improving the Blood Compatibility and the Gas Permeability of Polyether Ether Ketone Hollow Fiber Membrane Used for Membrane Oxygenator via Grafting Hydrophilic Components | |
| JP2008194363A (en) | Antithrombogenic coating agent and medical tool | |
| NO319026B1 (en) | Polymers and Products with Bacteriophobic and Optionally Cell Proliferation Inhibitory Properties and Methods of Preparation thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |