CN115779157A - Reactive biomedical coating and preparation method thereof - Google Patents
Reactive biomedical coating and preparation method thereof Download PDFInfo
- Publication number
- CN115779157A CN115779157A CN202211441482.5A CN202211441482A CN115779157A CN 115779157 A CN115779157 A CN 115779157A CN 202211441482 A CN202211441482 A CN 202211441482A CN 115779157 A CN115779157 A CN 115779157A
- Authority
- CN
- China
- Prior art keywords
- coating
- reactive
- biomedical
- base material
- thioxanthone
- 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.)
- Pending
Links
- 239000011248 coating agent Substances 0.000 title claims abstract description 116
- 238000000576 coating method Methods 0.000 title claims abstract description 116
- 238000002360 preparation method Methods 0.000 title abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 55
- 239000003519 biomedical and dental material Substances 0.000 claims abstract description 42
- 239000000178 monomer Substances 0.000 claims abstract description 36
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 23
- 229920000642 polymer Polymers 0.000 claims abstract description 16
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 15
- -1 quaternary ammonium olefin salt Chemical class 0.000 claims description 30
- 239000000758 substrate Substances 0.000 claims description 28
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 14
- 239000004094 surface-active agent Substances 0.000 claims description 11
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical class 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 description 10
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 10
- 239000012965 benzophenone Substances 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- 150000002576 ketones Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims description 7
- 229920003225 polyurethane elastomer Polymers 0.000 claims description 7
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 6
- 150000008366 benzophenones Chemical class 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002280 amphoteric surfactant Substances 0.000 claims description 4
- 239000003945 anionic surfactant Substances 0.000 claims description 4
- 239000003093 cationic surfactant Substances 0.000 claims description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 239000002736 nonionic surfactant Substances 0.000 claims description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 4
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 3
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 claims description 3
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 claims description 3
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 claims description 3
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 claims description 3
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims description 3
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- DYQUGFRRGGOYCA-UHFFFAOYSA-N 2-bromoxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3OC2=C1 DYQUGFRRGGOYCA-UHFFFAOYSA-N 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 claims description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
- LFEWXDOYPCWFHR-UHFFFAOYSA-N 4-(4-carboxybenzoyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C=C1 LFEWXDOYPCWFHR-UHFFFAOYSA-N 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 3
- ZWPWLKXZYNXATK-UHFFFAOYSA-N bis(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(C)C=C1 ZWPWLKXZYNXATK-UHFFFAOYSA-N 0.000 claims description 3
- KFUJUTFTRXYQMG-UHFFFAOYSA-N bis[4-(dimethylamino)phenyl]methanethione Chemical compound C1=CC(N(C)C)=CC=C1C(=S)C1=CC=C(N(C)C)C=C1 KFUJUTFTRXYQMG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 3
- 239000000806 elastomer Substances 0.000 claims description 3
- 238000005286 illumination Methods 0.000 claims description 3
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920002530 polyetherether ketone Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- 239000004800 polyvinyl chloride Substances 0.000 claims description 3
- 229940047670 sodium acrylate Drugs 0.000 claims description 3
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 claims description 3
- GEXVUFWVPUWPJB-UHFFFAOYSA-N ClC1=CC=2SC3=CC=CC=C3S(C2C=C1)=O Chemical compound ClC1=CC=2SC3=CC=CC=C3S(C2C=C1)=O GEXVUFWVPUWPJB-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 59
- 210000001772 blood platelet Anatomy 0.000 abstract description 6
- 230000009471 action Effects 0.000 abstract description 5
- 238000011065 in-situ storage Methods 0.000 abstract description 4
- 241000894006 Bacteria Species 0.000 abstract description 3
- 102000009123 Fibrin Human genes 0.000 abstract description 3
- 108010073385 Fibrin Proteins 0.000 abstract description 3
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 3
- 230000010100 anticoagulation Effects 0.000 abstract description 3
- 230000004888 barrier function Effects 0.000 abstract description 3
- 229950003499 fibrin Drugs 0.000 abstract description 3
- 238000004140 cleaning Methods 0.000 description 39
- 238000002156 mixing Methods 0.000 description 28
- 239000008213 purified water Substances 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 229920000056 polyoxyethylene ether Polymers 0.000 description 17
- 229940051841 polyoxyethylene ether Drugs 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 238000002791 soaking Methods 0.000 description 16
- 238000001035 drying Methods 0.000 description 11
- 229920000307 polymer substrate Polymers 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000006757 chemical reactions by type Methods 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 9
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 238000002036 drum drying Methods 0.000 description 8
- 235000011069 sorbitan monooleate Nutrition 0.000 description 8
- 239000001593 sorbitan monooleate Substances 0.000 description 8
- 229940035049 sorbitan monooleate Drugs 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 229960002897 heparin Drugs 0.000 description 7
- 229920000669 heparin Polymers 0.000 description 7
- 239000010410 layer Substances 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 230000010065 bacterial adhesion Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ZBUXMZFLCYRTOB-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C.CNC(=O)C=C ZBUXMZFLCYRTOB-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000007333 cyanation reaction Methods 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000009832 plasma treatment Methods 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 238000007348 radical reaction Methods 0.000 description 3
- 238000001338 self-assembly Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012620 biological material Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- VPASWAQPISSKJP-UHFFFAOYSA-N ethyl prop-2-enoate;isocyanic acid Chemical compound N=C=O.CCOC(=O)C=C VPASWAQPISSKJP-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- ZWGTVKDEOPDFGW-UHFFFAOYSA-N hexadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[NH3+] ZWGTVKDEOPDFGW-UHFFFAOYSA-N 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002954 polymerization reaction product Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 229920006268 silicone film Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- BKVAAWMQOQLENB-UHFFFAOYSA-N 15-hydroxy stearic acid Chemical compound CCCC(O)CCCCCCCCCCCCCC(O)=O BKVAAWMQOQLENB-UHFFFAOYSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- LIFHMKCDDVTICL-UHFFFAOYSA-N 6-(chloromethyl)phenanthridine Chemical compound C1=CC=C2C(CCl)=NC3=CC=CC=C3C2=C1 LIFHMKCDDVTICL-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- GWTCIAGIKURVBJ-UHFFFAOYSA-L dipotassium;dodecyl phosphate Chemical compound [K+].[K+].CCCCCCCCCCCCOP([O-])([O-])=O GWTCIAGIKURVBJ-UHFFFAOYSA-L 0.000 description 1
- 229940079868 disodium laureth sulfosuccinate Drugs 0.000 description 1
- YGAXLGGEEQLLKV-UHFFFAOYSA-L disodium;4-dodecoxy-4-oxo-2-sulfonatobutanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCOC(=O)CC(C([O-])=O)S([O-])(=O)=O YGAXLGGEEQLLKV-UHFFFAOYSA-L 0.000 description 1
- TWFQJFPTTMIETC-UHFFFAOYSA-N dodecan-1-amine;hydron;chloride Chemical compound [Cl-].CCCCCCCCCCCC[NH3+] TWFQJFPTTMIETC-UHFFFAOYSA-N 0.000 description 1
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000003670 easy-to-clean Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 150000002191 fatty alcohols Chemical group 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 description 1
- 229940048848 lauryl glucoside Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- VHDPPDRSCMVFAV-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine;hydrobromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[NH+](C)C VHDPPDRSCMVFAV-UHFFFAOYSA-N 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229940033623 potassium lauryl phosphate Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- IWIUXJGIDSGWDN-UQKRIMTDSA-M sodium;(2s)-2-(dodecanoylamino)pentanedioate;hydron Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-UQKRIMTDSA-M 0.000 description 1
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Images
Abstract
The invention provides a reactive biomedical coating and a preparation method thereof, belonging to the technical field of medical instruments. The hydrophilic monomer in the reactive coating is in situ in the hydrogen abstraction photoinitiator and generates polymerization reaction under the action of the photoinitiator to form a coating, and the hydrophilic monomer in the reactive coating and the high polymer base material also generate polymerization reaction to form covalent bonds between the coating and the base material, so that the formed covalent bonds enhance the bonding force between the base material and the coating, the coating is not easy to peel off, and the durability of the biomedical material is improved. In addition, after the hydrophilic coating disclosed by the invention meets water, the hydrophilic coating can be combined with water molecules, a layer of water film is formed on the surface of the hydrophilic coating, and the formed water film can form barrier to bacteria, blood platelets and fibrin, so that the biomedical material has good antibacterial adhesion and anticoagulation performances. In addition to this, the water film formed also has friction-reducing properties.
Description
Technical Field
The invention belongs to the technical field of medical instruments, and particularly relates to a reactive biomedical coating and a preparation method thereof.
Background
The biomedical polymer material has the characteristics of chemical structure similar to that of organisms, good physical and mechanical properties, certain biocompatibility and easy production and processing forming, and has unique advantages and wide application in the field of biological materials. As a biomedical polymer material, it is necessary to have good biocompatibility. Biocompatibility is the essence of distinguishing biological materials from other materials, and a major problem in the research and development of biomedical polymer materials is how to improve the biocompatibility of the materials.
The coating technology is an effective way for improving the biocompatibility of the medical material. The current commonly used coating technologies comprise plasma treatment, silane treatment, layer-by-layer self-assembly, solvent etching and the like, but the coating prepared by the technologies has the defect of poor durability caused by easy falling of the coating.
Disclosure of Invention
The invention aims to provide a reactive biomedical coating and a preparation method thereof.
The invention provides a reactive coating which comprises the following components in parts by weight:
preferably, the aqueous monomer comprises one or more of water-soluble vinyl monomer, modified heparin and olefin quaternary ammonium salt.
Preferably, the water-soluble vinyl monomer comprises one or more of acrylamide, N' N-dimethylacrylamide, N-methylolacrylamide, N- (2-hydroxyethyl) acrylamide, N-isopropylacrylamide, methacryloylethylsulfonobetaine, 2-acrylamido-2-methylpropanesulfonic acid, acrylic acid, sodium acrylate, methacrylic acid, hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, poly (ethylene glycol) methacrylate, N-vinylpyrrolidone, diethylene glycol ethyl ether acrylate, sodium styrenesulfonate, and vinyl ether.
Preferably, the hydrogen abstraction-type photoinitiator includes at least one of benzophenone, benzophenone derivatives, thioxanthone, and thioxanthone derivatives.
Preferably, the benzophenone derivative comprises one or more of 2,2' -dihydroxybenzophenone, 2,4,6-trimethylbenzophenone, 2-hydroxybenzophenone, 4-methoxybenzophenone, 4,4' -dimethyl benzophenone, benzophenone-4,4 ' -dicarboxylic acid, 4,4' -bis (dimethylamino) thiobenzophenone, tetraethylmichler's ketone, methylethylmichler's ketone, and thiomersler's ketone;
the thioxanthone derivatives comprise one or more of 2-chlorothianthrone, 2-isopropyl thioxanthone, 2-methyl thioxanthone, 2,4-diethyl thioxanthone, 2-bromo 9-xanthone and 2,4-diisopropyl thioxanthone.
Preferably, the co-initiator comprises one or more of an alkylamine compound, an alcoholamine compound and an ester compound.
Preferably, the surfactant comprises one or more of an anionic surfactant, a cationic surfactant, an amphoteric surfactant and a nonionic surfactant.
The invention also provides a biomedical material, which comprises a high polymer base material and a hydrophilic coating connected with the high polymer base material through a covalent bond; the hydrophilic coating is obtained by polymerizing the reactive paint according to any one of claims 1 to 7.
Preferably, the polymeric substrate comprises one of polydimethylsiloxane, polyurethane elastomer, VHB commercial elastomer, polypropylene, polyethylene, polyvinyl chloride, polyetheretherketone, and polycarbonate.
The invention also provides a preparation method of the biomedical material, which comprises the following steps:
and immersing the high polymer substrate into the reactive coating, and carrying out polymerization reaction under the condition of ultraviolet illumination to obtain the biomedical material.
The hydrophilic monomer in the reactive coating is subjected to polymerization reaction in situ under the action of the hydrogen abstraction photoinitiator and the auxiliary photoinitiator to form a coating, and the hydrophilic monomer in the reactive coating and the high polymer base material are also subjected to polymerization reaction under the action of the hydrogen abstraction photoinitiator and the auxiliary photoinitiator to form a covalent bond between the coating and the high polymer base material, so that the formed covalent bond enhances the bonding force between the high polymer base material and the coating, the coating is not easy to peel off, and the durability of the biomedical material is improved. In addition, after the hydrophilic coating disclosed by the invention meets water, the hydrophilic coating can be combined with water molecules, a layer of water film is formed on the surface of the hydrophilic coating, and the formed water film can form barrier to bacteria, blood platelets and fibrin, so that the biomedical material has good antibacterial adhesion and anticoagulation performances. In addition, the water film formed also has friction-reducing properties. The results of the examples show that the coefficient of friction of the coating according to the invention before mechanical rubbing is 0.04 and after 1K mechanical rubbing is 0.08, which still maintains the low-friction state, indicating that the coating according to the invention has good durability.
In addition, the surface active agent is added, so that the hydrogen abstraction type photoinitiator can be dispersed into water under the condition of not adding an organic solvent, and the hydrogen abstraction type photoinitiator realizes the preparation of the hydrophilic coating by initiating the free radical reaction of the water-based monomer;
the preparation method of the coating has universality, and the coating can be endowed with functionality by adjusting the type of the hydrophilic monomer.
Compared with the prior art in which the coating is prepared by adopting the technologies of plasma treatment, silane treatment, layer-by-layer self-assembly, solvent etching and the like, the preparation method of the biomedical material is simple to operate, can be used for polymerization in an aerobic environment, is beneficial to large-scale production, and has wide application prospects in the field of medical appliances. The coating prepared by the invention has a smaller contact angle, and the super-lubricity of the high polymer substrate is endowed.
Compared with the prior art that the surface of the material is modified by adopting a hydrophilic material or simultaneously adopting the hydrophilic material and the sterilizing substance, or simultaneously adopting a lubricant and the sterilizing substance, and the surface of the material is treated by corrosive chemical substances such as strong acid, potassium permanganate and the like in the treatment process, the reactive coating provided by the invention has simple proportioning and does not contain the corrosive chemical substances.
Drawings
FIG. 1 is a graph of the surface morphology of a silica gel substrate used in example 1;
FIG. 2 is a graph of the biomedical material of example 1;
FIG. 3 is the hydrophilicity of the biomedical material of example 1;
FIG. 4 is a graph showing the frictional properties of the biomedical material of example 1;
FIG. 5 shows the results of platelet adhesion of the silica gel substrate used in example 6;
FIG. 6 is a graph showing the platelet adhesion effect of the biomedical material of example 6;
FIG. 7 shows the effect of bacterial adhesion on the silica gel substrate used in example 7;
FIG. 8 shows the effect of bacterial adhesion of the commercial silica gel membrane of example 7;
FIG. 9 shows the effect of bacterial adhesion on the layer of biomedical material according to example 7.
Detailed Description
The invention provides a reactive coating which is characterized by comprising the following components in parts by mass:
the reactive coating comprises 100 parts of water by mass. In the present invention, water functions as a solvent. In the present invention, the water is preferably purified water.
The reactive coating comprises 3-50 parts of water-based monomer, preferably 10-30 parts of water-based monomer, and more preferably 15-20 parts of water-based monomer. In the present invention, the aqueous monomer preferably includes one or more of water-soluble vinyl monomer, modified heparin, and olefin quaternary ammonium salt; the water-soluble vinyl monomer preferably includes one or more of acrylamide, N' N-dimethylacrylamide, N-methylolacrylamide, N- (2-hydroxyethyl) acrylamide, N-isopropylacrylamide, methacryloylethylsulfonobetaine, 2-acrylamido-2-methylpropanesulfonic acid, acrylic acid, sodium acrylate, methacrylic acid, hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, poly (ethylene glycol) methacrylate, N-vinylpyrrolidone, diethylene glycol ethyl ether acrylate, sodium styrenesulfonate, and vinyl ether.
In the present invention, the method for preparing the modified heparin is preferably as follows: and carrying out esterification reaction on polyethylene glycol monoacrylate and heparin to obtain the modified heparin. In the invention, the molar ratio of the polyethylene glycol monoacrylate to the heparin is preferably 1-5:1; the number of repeating units in the polyethylene glycol is preferably 2 to 13, more preferably 6 to 9; the temperature of the esterification reaction is preferably 40 to 80 ℃, more preferably 50 to 60 ℃, and the time is preferably 4 to 8 hours, more preferably 5 to 6 hours. The process of the esterification reaction is as follows:
in the present invention, the method for preparing the olefinic quaternary ammonium salt preferably comprises: and (3) carrying out cyanation reaction on the isocyanate ethyl acrylate and the hydroxypropyl quaternary ammonium salt to obtain the olefin quaternary ammonium salt. In the invention, the molar ratio of the isocyanate ethyl acrylate to the hydroxypropyl quaternary ammonium salt is preferably 1-3:1; the temperature of the cyanation reaction is preferably 20 to 80 ℃, more preferably 50 to 60 ℃, and the time is preferably 4 to 8 hours, more preferably 5 to 6 hours. The cyanation reaction proceeds as follows:
based on the mass part of the water, the reactive coating comprises 0.002-0.02 part of hydrogen abstraction type photoinitiator, preferably 0.005-0.015 part of hydrogen abstraction type photoinitiator, and more preferably 0.008-0.012 part of hydrogen abstraction type photoinitiator. In the present invention, the hydrogen abstraction-type photoinitiator preferably includes at least one of benzophenone, a benzophenone derivative, thioxanthone and a thioxanthone derivative; the benzophenone derivatives preferably comprise one or more of 2,2' -dihydroxybenzophenone, 2,4,6-trimethylbenzophenone, 2-hydroxybenzophenone, 4-methoxybenzophenone, 4,4' -dimethylbenzophenone, benzophenone-4,4 ' -dicarboxylic acid, 4,4' -bis (dimethylamino) thiobenzophenone, tetraethylmichler's ketone, methylethylmichler's ketone and thiomersler's ketone; the thioxanthone derivative preferably includes one or more of 2-chlorothioxanthone, 2-isopropylthioxanthone, 2-methylthioxanthone, 2,4-diethylthioxanthone, 2-bromo 9-xanthone and 2,4-diisopropylthioxanthone.
Based on the mass part of the water, the reactive coating comprises 0.002-0.02 part of assistant photoinitiator, preferably 0.005-0.015 part, and more preferably 0.008-0.012 part. In the present invention, the co-initiator includes one or more of an alkylamine compound, an alcoholamine compound and an ester compound; the alkylamine compound preferably includes one or more of diethylamine, triethylamine and dodecylamine; the alcohol amine compound preferably comprises one or more of diethanolamine, triethanolamine, dimethylethanolamine, N-methylethanolamine and N, N-diethylethanolamine; the ester compound preferably comprises one or more of ethyl 4-dimethylaminobenzoate, ethyl N, N-dimethyl benzoate and dimethylaminoethyl benzoate.
The reactive coating comprises 1-10 parts of surfactant, preferably 4-8 parts of surfactant, and more preferably 5-6 parts of surfactant based on the mass parts of water. In the present invention, the surfactant preferably includes one or more of an anionic surfactant, a cationic surfactant, an amphoteric surfactant, and a nonionic surfactant. In the present invention, the anionic surfactant preferably includes one or more of sodium lauryl sulfate, triethanolamine lauryl sulfate, sodium fatty alcohol isethionate, sodium N-lauroyl glutamate, sodium laureth carboxylate, disodium laureth sulfosuccinate, lauryl phosphate, potassium lauryl phosphate, and glyceryl stearate; the cationic surfactant preferably comprises one or more of dodecyl ammonium chloride, octadecyl trimethyl ammonium chloride, hexadecyl trimethyl ammonium bromide and hexadecyl dimethyl ammonium bromide; the nonionic surfactant preferably comprises one or more of polysorbate-20, sorbitan monolaurate, sorbitan monooleate, polyoxyethylene ether phosphotriester, lauryl glucoside polyglycerin-2 dipolyhydroxystearate, sorbitan monooleate polyoxyethylene ether, and polyethylene glycol 15-hydroxystearate; the amphoteric surfactant preferably comprises dodecyl dimethyl amine oxide.
Compared with the prior art that the surface of the material is modified by adopting a hydrophilic material or by simultaneously using the hydrophilic material and the sterilizing substance, or by simultaneously adopting a lubricant and the sterilizing substance, and corrosive chemical substances such as strong acid, potassium permanganate and the like are required in the treatment process to treat the surface of the material, the reactive coating provided by the invention has simple proportioning and does not contain the corrosive chemical substances. In addition, the surfactant is added, so that the hydrogen abstraction type photoinitiator can be dispersed into water under the condition of not adding an organic solvent, and the hydrogen abstraction type photoinitiator realizes the preparation of the hydrophilic coating by initiating the free radical reaction of the water-based monomer; the preparation method of the coating has universality, and the coating can be endowed with functionality by adjusting the type of the hydrophilic monomer.
In the present invention, the method for preparing the reactive paint preferably comprises the steps of: and mixing the surfactant, water and the hydrogen abstraction type photoinitiator for the first time, and mixing the obtained first mixed solution with the water-based monomer and the auxiliary photoinitiator for the second time to obtain the reactive coating. In the present invention, the first mixing mode is preferably stirring, the stirring temperature is preferably room temperature, the stirring speed is preferably 500 to 3000rpm, more preferably 1000 to 2000rpm, and even more preferably 1500 to 1800rpm, and the stirring time is preferably 30 to 240min, more preferably 50 to 200min, and even more preferably 100 to 150min. In the present invention, the second mixing mode is preferably stirring, the stirring temperature is preferably room temperature, the stirring speed is preferably 500 to 3000rpm, more preferably 1000 to 2000rpm, and even more preferably 1500 to 1800rpm, and the stirring time is preferably 5 to 60min, more preferably 10 to 50min, and even more preferably 20 to 40min.
The invention also provides a biomedical material, which comprises a high polymer base material and a hydrophilic coating connected with the high polymer base material through a covalent bond; the hydrophilic coating is obtained by polymerizing the reactive coating in the scheme. In the present invention, the high polymer substrate preferably includes one of polydimethylsiloxane, polyurethane elastomer, VHB commercial elastomer, polypropylene, polyethylene, polyvinyl chloride, polyetheretherketone, and polycarbonate.
The invention also provides a preparation method of the biomedical material in the scheme, which comprises the following steps:
and immersing the high polymer substrate into the reactive coating, and carrying out polymerization reaction under the condition of ultraviolet illumination to obtain the biomedical material.
In the present invention, before the polymer substrate is immersed in the reactive coating, the polymer substrate is preferably subjected to first cleaning, second cleaning, and drying. In the present invention, the first cleaning is preferably performed by immersing the polymer substrate in an aqueous solution containing a detergent component, and performing ultrasonic treatment at a power of preferably 80 to 120W, more preferably 90 to 110W, for 20 to 60 min. In the present invention, the mass concentration of the aqueous solution containing a detergent component is preferably 0.5 to 2%, more preferably 1 to 1.5%; the decontamination component is preferably a fatty alcohol ether sodium sulfate surfactant; the fatty alcohol ether sulfonate surfactant preferably comprises one or more of fatty acid methyl ester sulfonate, fatty alcohol-polyoxyethylene ether sodium sulfate, sodium alkyl benzene sulfonate, propane sultone and sodium hydroxyethyl sulfonate. The second cleaning is preferably to ultrasonically clean the polymer substrate after the first cleaning in water for 40-50 min, wherein the power of ultrasonic is preferably 90-110W. In the present invention, the temperature of the drying is preferably 40 to 80 ℃, more preferably 50 to 60 ℃. In the present invention, the drying time is not particularly limited, and the drying may be carried out until no moisture is present. After the first cleaning and the second cleaning, grease dirt and dust on the surface of the base material are removed.
In the present invention, the polymerization reaction is preferably carried out at a temperature of 20 to 40 ℃, more preferably 25 to 30 ℃ and for a time of 1 to 3 hours, more preferably 2 to 2.5 hours. In the polymerization reaction process, an initiator in the reactive coating captures hydrogen of methyl in a base material to generate free radicals under the condition of ultraviolet irradiation, the methyl free radicals are combined with olefin monomers to generate free radical transfer, and then chain type free radical polymerization reaction is initiated, so that covalent bonds are formed between the coating and the high polymer base material, the formed covalent bonds enhance the bonding force between the high polymer base material and the coating, the coating is not easy to peel off, and the durability of the biomedical material is improved. In the present invention, the polymerization reaction is preferably carried out under light-shielding conditions.
After the polymerization reaction, the polymerization reaction product is preferably soaked in water and then cleaned to obtain the biomedical material. In the present invention, the soaking time is preferably 3 to 5 days. The present invention can remove unreacted monomers by soaking the polymerization reaction product and make the linear polymer which is not firmly combined with the high polymer substrate easy to clean. The washing is preferably carried out with water, and the number of times of the washing is not particularly limited in the present invention, and it is sufficient to completely wash the linear polymer that is not firmly bonded to the high polymer substrate.
The hydrophilic monomer in the reactive coating is subjected to polymerization reaction in situ under the action of the hydrogen abstraction photoinitiator and the assistant photoinitiator to form a coating, and the hydrophilic monomer in the reactive coating and the high polymer base material are subjected to polymerization reaction in situ under the action of the hydrogen abstraction photoinitiator and the assistant photoinitiator to form a covalent bond between the coating and the high polymer base material, so that the formed covalent bond enhances the bonding force between the high polymer base material and the coating, the coating is not easy to peel off, and the durability of the biomedical material is improved. In addition, after the hydrophilic coating disclosed by the invention meets water, the hydrophilic coating can be combined with water molecules, a layer of water film is formed on the surface of the hydrophilic coating, and the formed water film can form barrier to bacteria, blood platelets and fibrin, so that the biomedical material has good antibacterial adhesion and anticoagulation performances. In addition to this, the water film formed also has friction-reducing properties.
Compared with the prior art in which the coating is prepared by the technologies of plasma treatment, silane treatment, layer-by-layer self-assembly, solvent etching and the like, the preparation method of the biomedical material is simple to operate, can be used for polymerization in an aerobic environment, is beneficial to large-scale production, and has wide application prospects in the field of medical appliances. The coating prepared by the preparation method has a smaller contact angle, and the super-lubricity of the high polymer substrate is endowed. In addition, the hydrogen abstraction type photoinitiator realizes the preparation of the hydrophilic coating by initiating the free radical reaction of the water-based monomer; the preparation method of the coating has universality, and the functionality of the coating can be endowed by adjusting the type of the hydrophilic monomer.
In order to further illustrate the present invention, a reactive biomedical coating and a method for preparing the same according to the present invention will be described in detail with reference to the accompanying drawings and examples, which should not be construed as limiting the scope of the present invention.
Example 1
In this example, sodium dodecyl sulfate is used as a dispersant, acrylamide is used as a monomer, and a hydrophilic coating is prepared on the surface of a commercially available silica gel membrane (marked as PDMS) with a width of 2.5cm, a length of 8cm and a thickness of 1 mm.
1) 100 parts of purified water, 3 parts of sodium dodecyl sulfate and 0.01 part of benzophenone are subjected to first mixing for 60min under the condition that the rotating speed is 2000rmp, and then the obtained first mixed solution, 30 parts of acrylamide and 0.002 part of diethanolamine are subjected to second mixing for 60min under the condition that the rotating speed is 2000rmp to obtain a reactive coating;
2) Soaking the silica gel substrate in an aqueous solution containing fatty alcohol-polyoxyethylene ether sodium sulfate with the mass concentration of 2% and carrying out first cleaning for 30min under the condition that the ultrasonic power is 100W; ultrasonically cleaning the substrate subjected to the first cleaning in purified water at the power of 100W for 20min for the second time, and performing drum drying at the blast drying temperature of 60 ℃ for later use;
3) Immersing the base material treated in the step 2) into the reaction type coating obtained in the step 1) and uniformly mixing, carrying out polymerization reaction for 1h under the conditions of 365nm ultraviolet light and 25 ℃, taking out the base material treated by ultraviolet, soaking in purified water for 3 days, and then repeatedly cleaning the surface of the base material to obtain the biomedical material (marked as PAAm).
SEM analysis was performed on the silica gel membrane and biomedical material commercially available in example 1, and the results are shown in fig. 1 and 2. As can be seen from fig. 1 and 2, the present invention prepares a coating on the surface of a substrate.
The biomedical material of example 1 was subjected to a hydrophilicity test, and the results are shown in fig. 3. As can be seen from FIG. 3, the contact angle of the biomedical material coating of example 1 is 16 °, and the hydrophilic effect is good.
The friction properties of the commercially available silicone film and biomedical material of rheometer example 1 were tested separately and the coefficient of friction (COF) was calculated using the following equation:
wherein the content of the first and second substances,
to test the torque; r is the radius of the test plate;
a test for normal force. The results of the coefficient of friction are shown in FIG. 4. The coefficient of friction of the commercially available silicone film was 0.14, and the coefficient of friction of the biomedical material of example 1 was 0.04. As can be seen from FIG. 4, the biomedical material of example 1The material has low friction properties.
The change in the coefficient of friction before and after 1K mechanical friction tests was performed on the coating layer of the biomedical material prepared in example 1 using a rheometer under conditions of constant normal force (1N), constant amplitude (1%), constant frequency (0.15 HZ), and constant temperature (25 ℃), and the results are shown in fig. 5. As can be seen from FIG. 5, the coefficient of friction of the coating of the present invention before mechanical friction was 0.04, and after 1K mechanical friction, the coefficient of friction of the coating of the present invention was 0.08, and the low friction state was maintained, indicating that the coating of the present invention has good durability.
Example 2
In this example, sodium dodecyl sulfate is used as a dispersant, acrylamide is used as a monomer, and a hydrophilic coating is prepared on the surface of a commercially available silica gel membrane with a width of 2.5cm, a length of 8cm and a thickness of 1 mm.
1) 100 parts of purified water, 3 parts of sodium dodecyl sulfate and 0.01 part of 2-methyl thioxanthone are subjected to first mixing for 60min under the condition that the rotating speed is 2000rmp, and then the obtained first mixed solution, 30 parts of acrylamide and 0.002 part of diethanolamine are subjected to second mixing for 60min under the condition that the rotating speed is 2000rmp to obtain a reactive coating;
2) Soaking the silica gel substrate in an aqueous solution containing fatty alcohol-polyoxyethylene ether sodium sulfate with the mass concentration of 2% and carrying out first cleaning for 30min under the condition that the ultrasonic power is 100W; ultrasonically cleaning the substrate subjected to the first cleaning in purified water at the power of 100W for 20min for the second time, and performing drum drying at the blast drying temperature of 60 ℃ for later use;
3) Immersing the base material treated in the step 2) into the reaction type coating obtained in the step 1) and uniformly mixing, carrying out polymerization reaction for 1h under the conditions of 365nm ultraviolet light and 25 ℃, taking out the base material treated by ultraviolet, soaking in purified water for 3 days, and then repeatedly cleaning the surface of the base material to obtain the biomedical material.
Example 3
In the embodiment, sorbitan monooleate polyoxyethylene ether is used as a dispersing agent, acrylamide is used as a monomer, and a hydrophilic coating is prepared on the surface of a silica gel substrate with the width of 2.5cm, the length of 8cm and the thickness of 1 mm.
1) 100 parts of purified water, 3 parts of sorbitan monooleate polyoxyethylene ether and 0.01 part of benzophenone are subjected to first mixing for 60min under the condition that the rotating speed is 2000rmp, and then the obtained first mixed solution, 30 parts of acrylamide and 0.002 part of diethanolamine are subjected to second mixing for 60min under the condition that the rotating speed is 2000rmp to obtain a reactive coating;
2) Soaking the silica gel substrate in an aqueous solution containing fatty alcohol-polyoxyethylene ether sodium sulfate with the mass concentration of 2% and carrying out first cleaning for 30min under the condition that the ultrasonic power is 100W; ultrasonically cleaning the base material subjected to the first cleaning in purified water at the power of 100W for 20min for the second time, and performing drum drying for later use at the forced air drying temperature of 60 ℃;
3) Immersing the base material treated in the step 2) into the reaction type coating obtained in the step 1) and uniformly mixing, carrying out polymerization reaction for 1h under the conditions of 365nm ultraviolet light and 25 ℃, taking out the base material after ultraviolet treatment, immersing in purified water for 3 days, and then repeatedly cleaning the surface of the base material to obtain the biomedical material.
Example 4
In this example, a hydrophilic coating was prepared on the surface of a commercially available silica gel substrate having a width of 2.5cm, a length of 8cm and a thickness of 1mm using cetylammonium chloride as a dispersant and acrylamide as a monomer.
1) Carrying out first mixing on 100 parts of purified water, 3 parts of hexadecyl ammonium chloride and 0.01 part of benzophenone for 60min under the condition of the rotating speed of 2000rmp, and then carrying out second mixing on the obtained first mixed solution, 30 parts of acrylamide and 0.002 part of diethanolamine for 60min under the condition of the rotating speed of 2000rmp to obtain a reactive coating;
2) Soaking the silica gel substrate in an aqueous solution containing fatty alcohol-polyoxyethylene ether sodium sulfate with the mass concentration of 2% and carrying out first cleaning for 30min under the condition that the ultrasonic power is 100W; ultrasonically cleaning the substrate subjected to the first cleaning in purified water at the power of 100W for 15min for the second time, and performing drum drying at the blast drying temperature of 60 ℃ for later use;
3) Immersing the base material treated in the step 2) into the reaction type coating obtained in the step 1) and uniformly mixing, carrying out polymerization reaction for 1h under the conditions of 365nm ultraviolet light and 25 ℃, taking out the base material after ultraviolet treatment, immersing in purified water for 3 days, and then repeatedly cleaning the surface of the base material to obtain the biomedical material.
Example 5
In this example, sodium dodecyl sulfate is used as a dispersant, acrylamide is used as a monomer, and a hydrophilic coating is prepared on the surface of a commercially available polyurethane elastomer film with a width of 2.5cm, a length of 8cm and a thickness of 0.5 mm.
1) 100 parts of purified water, 3 parts of sodium dodecyl sulfate and 0.01 part of benzophenone are subjected to first mixing for 60min under the condition that the rotating speed is 2000rmp, and then the obtained first mixed solution, 30 parts of acrylamide and 0.002 part of diethanolamine are subjected to second mixing for 60min under the condition that the rotating speed is 2000rmp to obtain a reactive coating;
2) Soaking the polyurethane elastomer substrate in an aqueous solution with the mass concentration of 2% and containing fatty alcohol-polyoxyethylene ether sodium sulfate, and carrying out first cleaning for 30min under the condition that the ultrasonic power is 100W; ultrasonically cleaning the substrate subjected to the first cleaning in purified water at the power of 100W for 20min for the second time, and performing drum drying at the blast drying temperature of 60 ℃ for later use;
3) Immersing the base material treated in the step 2) into the reaction type coating obtained in the step 1) and uniformly mixing, carrying out polymerization reaction for 1h under the conditions of 365nm ultraviolet light and 25 ℃, taking out the base material treated by ultraviolet, soaking in purified water for 3 days, and then repeatedly cleaning the surface of the base material to obtain the biomedical material.
Example 6
In this example, a hydrophilic coating was prepared on the surface of a commercially available silica gel substrate having a width of 2.5cm, a length of 8cm and a thickness of 1mm, using sorbitan monooleate polyoxyethylene ether as a dispersant and vinyl heparin as a monomer.
The preparation process of the vinyl heparin comprises the following steps: and carrying out esterification reaction on polyethylene glycol monoacrylate and heparin to obtain the modified heparin. The molar ratio of the polyethylene glycol monoacrylate to the heparin is 1.5; the number of repeating units in the polyethylene glycol is 12; the temperature of the esterification reaction is preferably 80 ℃ and the time is 8h.
1) 100 parts of purified water, 3 parts of sorbitan monooleate polyoxyethylene ether and 0.01 part of benzophenone are subjected to first mixing for 60min under the condition that the rotating speed is 2000rmp, and then the obtained first mixed solution is subjected to second mixing for 60min with 20 parts of acrylamide, 10 parts of vinyl heparin and diethanolamine under the condition that the rotating speed is 2000rmp to obtain a reaction type coating;
2) Soaking the silica gel substrate in an aqueous solution containing fatty alcohol-polyoxyethylene ether sodium sulfate with the mass concentration of 2% and carrying out first cleaning for 30min under the condition that the ultrasonic power is 100W; ultrasonically cleaning the substrate subjected to the first cleaning in purified water at the power of 100W for 20min for the second time, and performing drum drying at the blast drying temperature of 60 ℃ for later use;
3) Immersing the base material treated in the step 2) into the reaction type coating obtained in the step 1) and uniformly mixing, carrying out polymerization reaction for 1h under the conditions of 365nm ultraviolet light and 25 ℃, taking out the base material treated by ultraviolet, soaking in purified water for 3 days, and then repeatedly cleaning the surface of the base material to obtain the biomedical material.
Platelet adhesion experiments were performed on the commercially available silicone membrane and biomedical material of example 6, and the results are shown in fig. 6 and 7. As can be seen from fig. 6 and 7, the hydrophilic coating of the present invention has anti-platelet adhesion properties. In addition, the preparation method of the coating has universality, and the functionality of the coating can be endowed by adjusting the type of the hydrophilic monomer.
Example 7
In this example, sodium dodecyl sulfate is used as a dispersant, and N, N-dimethyl bisacrylamide and N- (2-hydroxyethyl) acrylamide are used as monomers, and a hydrophilic coating is prepared on the surface of a commercially available silica gel substrate having a width of 2.5cm, a length of 8cm, and a thickness of 1 mm.
1) 100 parts of purified water, 3 parts of sodium dodecyl sulfate and 0.01 part of benzophenone are subjected to first mixing for 60min under the condition that the rotating speed is 2000rmp, and then the obtained first mixed solution is subjected to second mixing for 60min with 10 parts of N, N-dimethyl bisacrylamide, 10 parts of N- (2-hydroxyethyl) acrylamide and 0.002 part of diethanolamine under the condition that the rotating speed is 2000rmp to obtain a reaction type coating;
2) Soaking the silica gel substrate in an aqueous solution containing fatty alcohol-polyoxyethylene ether sodium sulfate with the mass concentration of 2% and carrying out first cleaning for 30min under the condition that the ultrasonic power is 100W; ultrasonically cleaning the substrate subjected to the first cleaning in purified water at the power of 100W for 20min for the second time, and performing drum drying at the blast drying temperature of 60 ℃ for later use;
3) Immersing the base material treated in the step 2) into the reaction type coating obtained in the step 1) and uniformly mixing, carrying out polymerization reaction for 1h under the conditions of 365nm ultraviolet light and 25 ℃, taking out the base material treated by ultraviolet, soaking in purified water for 3 days, and then repeatedly cleaning the surface of the base material to obtain the biomedical material.
The bacterial adhesion experiments were performed on the commercially available silicone membranes and biomedical materials in example 7: after culturing in E.coli solution for 7 days, the cells were stained with a fluorescent dye and photographed with a fluorescent microscope. The results are shown in fig. 8 and 9. As can be seen from fig. 8 and 9, the biomedical material of example 7 can reduce bacterial adhesion.
Example 8
In this example, sorbitan monooleate polyoxyethylene ether is used as a dispersant, and N, N-dimethyl bisacrylamide and N- (2-hydroxyethyl) acrylamide are used as monomers, and a hydrophilic coating is prepared on the surface of a commercially available polyurethane elastomer substrate with a width of 2.5cm, a length of 8cm and a thickness of 0.5 mm.
1) Carrying out first mixing on 100 parts of purified water, 3 parts of sorbitan monooleate polyoxyethylene ether and 0.01 part of benzophenone for 60min under the condition of the rotating speed of 2000rmp, and then carrying out second mixing on the obtained first mixed solution, 10 parts of N, N-dimethyl bisacrylamide, 10 parts of N- (2-hydroxyethyl) acrylamide and 0.002 part of diethanolamine for 60min under the condition of the rotating speed of 2000rmp to obtain a reactive coating;
2) Soaking the polyurethane elastomer substrate in an aqueous solution with the mass concentration of 2% and containing fatty alcohol-polyoxyethylene ether sodium sulfate, and carrying out first cleaning for 30min under the condition that the ultrasonic power is 100W; ultrasonically cleaning the substrate subjected to the first cleaning in purified water at the power of 100W for 20min for the second time, and performing drum drying at the blast drying temperature of 60 ℃ for later use;
3) Immersing the base material treated in the step 2) into the reaction type coating obtained in the step 1) and uniformly mixing, carrying out polymerization reaction for 1h under the conditions of 365nm ultraviolet light and 25 ℃, taking out the base material treated by ultraviolet, soaking in purified water for 3 days, and then repeatedly cleaning the surface of the base material to obtain the biomedical material.
Although the above embodiments have been described in detail, they are only a part of the embodiments of the present invention, not all of the embodiments, and other embodiments can be obtained without inventive step according to the embodiments, and all of the embodiments belong to the protection scope of the present invention.
Claims (10)
1. The reactive coating is characterized by comprising the following components in parts by mass:
2. the reactive coating of claim 1, wherein the aqueous monomer comprises one or more of a water-soluble vinyl monomer, a modified heparin, and a quaternary ammonium olefin salt.
3. The reactive paint of claim 2, wherein the water-soluble vinyl monomer comprises one or more of acrylamide, N' N-dimethylacrylamide, N-methylolacrylamide, N- (2-hydroxyethyl) acrylamide, N-isopropylacrylamide, methacryloylethylsulfonobetaine, 2-acrylamido-2-methylpropanesulfonic acid, acrylic acid, sodium acrylate, methacrylic acid, hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, poly (ethylene glycol) methacrylate, N-vinylpyrrolidone, diethylene glycol ethyl ether acrylate, sodium styrene sulfonate, and vinyl ether.
4. The reactive coating of claim 1, wherein the hydrogen abstraction photoinitiator comprises at least one of benzophenone, a benzophenone derivative, thioxanthone, and a thioxanthone derivative.
5. The reactive coating of claim 4, wherein the benzophenone derivative comprises one or more of 2,2' -dihydroxybenzophenone, 2,4,6-trimethylbenzophenone, 2-hydroxybenzophenone, 4-methoxybenzophenone, 4,4' -dimethylbenzophenone, benzophenone-4,4 ' -dicarboxylic acid, 4,4' -bis (dimethylamino) thiobenzophenone, tetraethylmichler's ketone, methylethylmichler's ketone, and thiomersler's ketone;
the thioxanthone derivatives comprise one or more of 2-chlorothianthrone, 2-isopropyl thioxanthone, 2-methyl thioxanthone, 2,4-diethyl thioxanthone, 2-bromo 9-xanthone and 2,4-diisopropyl thioxanthone.
6. The reactive coating of claim 1, 4 or 5, wherein the co-initiator comprises one or more of an alkylamine compound, an alcoholamine compound, and an ester compound.
7. A reactive coating according to claim 1, wherein the surfactant comprises one or more of an anionic surfactant, a cationic surfactant, an amphoteric surfactant and a nonionic surfactant.
8. A biomedical material comprising a polymeric substrate and a hydrophilic coating covalently attached to said polymeric substrate; the hydrophilic coating is obtained by polymerizing the reactive coating according to any one of claims 1 to 7.
9. The biomedical material according to claim 8, wherein said polymeric substrate comprises one of polydimethylsiloxane, polyurethane elastomer, VHB commercial elastomer, polypropylene, polyethylene, polyvinyl chloride, polyetheretherketone, and polycarbonate.
10. A method for preparing a biomedical material according to claim 8 or 9, characterized in that it comprises the following steps:
and immersing the high polymer base material into the reactive coating, and carrying out polymerization reaction under the ultraviolet illumination condition to obtain the biomedical material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211441482.5A CN115779157A (en) | 2022-11-17 | 2022-11-17 | Reactive biomedical coating and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211441482.5A CN115779157A (en) | 2022-11-17 | 2022-11-17 | Reactive biomedical coating and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115779157A true CN115779157A (en) | 2023-03-14 |
Family
ID=85438586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211441482.5A Pending CN115779157A (en) | 2022-11-17 | 2022-11-17 | Reactive biomedical coating and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115779157A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116640617A (en) * | 2023-05-10 | 2023-08-25 | 西北工业大学 | High-temperature antioxidant lubricating oil and application thereof in realizing high-temperature super-slip behavior on surface of metal material |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0762267A (en) * | 1993-08-31 | 1995-03-07 | Sony Chem Corp | Ultraviolet-curing paint composition |
| US5429590A (en) * | 1992-12-01 | 1995-07-04 | Nitto Denko Corporation | Medical water-absorptive polymer and dressing for wound and medical bandage using the same |
| CN101622020A (en) * | 2007-02-28 | 2010-01-06 | 帝斯曼知识产权资产管理有限公司 | Hydrophilic coating |
| WO2011058171A1 (en) * | 2009-11-16 | 2011-05-19 | Dsm Ip Assets B.V. | Hydrophilic copolymer |
| CN104857572A (en) * | 2014-12-05 | 2015-08-26 | 美昕医疗器械（上海）有限公司 | Method for preparing hydrophilic lubrication coating layer on surface of inert high-molecular material and medical instrument |
| CN104857571A (en) * | 2014-12-03 | 2015-08-26 | 美昕医疗器械（上海）有限公司 | Hydrophilic lubrication silicone rubber catheter and preparation method for hydrophilic lubrication coating layer |
| CN111514378A (en) * | 2019-02-02 | 2020-08-11 | 江苏百赛飞生物科技有限公司 | Central venous catheter, preparation method thereof and medical device comprising same |
| CN113631203A (en) * | 2019-01-28 | 2021-11-09 | 微仙美国有限公司 | Coating layer |
| US20220031914A1 (en) * | 2020-07-30 | 2022-02-03 | Microvention, Inc. | Antimicrobial Coatings |
-
2022
- 2022-11-17 CN CN202211441482.5A patent/CN115779157A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5429590A (en) * | 1992-12-01 | 1995-07-04 | Nitto Denko Corporation | Medical water-absorptive polymer and dressing for wound and medical bandage using the same |
| JPH0762267A (en) * | 1993-08-31 | 1995-03-07 | Sony Chem Corp | Ultraviolet-curing paint composition |
| CN101622020A (en) * | 2007-02-28 | 2010-01-06 | 帝斯曼知识产权资产管理有限公司 | Hydrophilic coating |
| WO2011058171A1 (en) * | 2009-11-16 | 2011-05-19 | Dsm Ip Assets B.V. | Hydrophilic copolymer |
| CN104857571A (en) * | 2014-12-03 | 2015-08-26 | 美昕医疗器械（上海）有限公司 | Hydrophilic lubrication silicone rubber catheter and preparation method for hydrophilic lubrication coating layer |
| CN104857572A (en) * | 2014-12-05 | 2015-08-26 | 美昕医疗器械（上海）有限公司 | Method for preparing hydrophilic lubrication coating layer on surface of inert high-molecular material and medical instrument |
| CN113631203A (en) * | 2019-01-28 | 2021-11-09 | 微仙美国有限公司 | Coating layer |
| CN111514378A (en) * | 2019-02-02 | 2020-08-11 | 江苏百赛飞生物科技有限公司 | Central venous catheter, preparation method thereof and medical device comprising same |
| US20220031914A1 (en) * | 2020-07-30 | 2022-02-03 | Microvention, Inc. | Antimicrobial Coatings |
Non-Patent Citations (1)
| Title |
|---|
| 李桂林;: "UV固化涂料", 涂料工业, no. 05, pages 24 - 38 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116640617A (en) * | 2023-05-10 | 2023-08-25 | 西北工业大学 | High-temperature antioxidant lubricating oil and application thereof in realizing high-temperature super-slip behavior on surface of metal material |
| CN116640617B (en) * | 2023-05-10 | 2024-04-12 | 西北工业大学 | High-temperature antioxidant lubricating oil and application thereof in realizing high-temperature super-slip behavior on surface of metal material |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Yang et al. | Antifouling and antibacterial hydrogel coatings with self-healing properties based on a dynamic disulfide exchange reaction | |
| JP4458557B2 (en) | Process for surface modification of polymer substrate and polymer formed from the process | |
| CN107236143B (en) | Cationic-zwitterionic copolymer coating, preparation method and application thereof | |
| WO2006064810A1 (en) | Process for production of organic-inorganic hybrid hydrogel, cell culture substrate comprising the same, and antifogging material comprising dried product thereof | |
| CN105295073B (en) | A kind of high-flexibility amphoteric ion hydrogel preparation method | |
| CA2666919C (en) | Method for treating surfaces containing si-h groups | |
| JP2003510378A (en) | Graft polymerization of substrate surface | |
| Zhao et al. | Polypropylene modified with 2-hydroxyethyl acrylate-g-2-methacryloyloxyethyl phosphorycholine and its hemocompatibility | |
| CN115779157A (en) | Reactive biomedical coating and preparation method thereof | |
| CN106421906B (en) | Amphoteric ion random copolymer surface modification coating and preparation method and application with epoxy-functional | |
| CN112708075B (en) | Anti-swelling and anti-adhesion hydrogel as well as preparation method and application thereof | |
| Yin et al. | Photoinitiator-grafted polymer chains for integrating hydrogels with various materials | |
| CN114031879B (en) | Hydrogel for marine antifouling and preparation method thereof | |
| CN114230719B (en) | Double-crosslinking cellulose-based hydrogel prepared by cold plasma and preparation method and application thereof | |
| JP2008237088A (en) | Base medium and method for cell culture | |
| CN110028614B (en) | Antibacterial micro-nano gel and fiber with protein adsorption function and preparation method thereof | |
| JP5349728B2 (en) | Cell culture substrate and cell culture method | |
| Zhao et al. | Surface modification of polyethylene film by acrylamide graft and alcoholysis for improvement of antithrombogenicity | |
| JP2006288217A (en) | Cell culture substrate and cell culture method | |
| Song et al. | High-Density Zwitterionic Polymer Brushes Exhibit Robust Lubrication Properties and High Antithrombotic Efficacy in Blood-Contacting Medical Devices | |
| JP4979199B2 (en) | Cell culture substrate and cell culture method | |
| JP2011213793A (en) | Method for producing organic-inorganic composite hydrogel | |
| JP2006280206A (en) | Substrate for cell culture and method for cell culture | |
| CN115746475B (en) | Anti-adhesion high polymer material and preparation method thereof | |
| Sasai et al. | Effects of Plasma Surface Treatment on Cell Adhesion to Biocompatible Polymer Brushes |
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 |