CN115572502B - Multifunctional coating based on interaction of cation and pi, preparation method and application thereof - Google Patents
Multifunctional coating based on interaction of cation and pi, preparation method and application thereof Download PDFInfo
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- CN115572502B CN115572502B CN202211233345.2A CN202211233345A CN115572502B CN 115572502 B CN115572502 B CN 115572502B CN 202211233345 A CN202211233345 A CN 202211233345A CN 115572502 B CN115572502 B CN 115572502B
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- polyethylene glycol
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- 238000000576 coating method Methods 0.000 title claims abstract description 103
- 239000011248 coating agent Substances 0.000 title claims abstract description 102
- 230000003993 interaction Effects 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 150000001768 cations Chemical class 0.000 title claims description 15
- 239000000758 substrate Substances 0.000 claims abstract description 62
- 239000000463 material Substances 0.000 claims abstract description 49
- 229920000768 polyamine Polymers 0.000 claims abstract description 28
- 150000008442 polyphenolic compounds Chemical class 0.000 claims abstract description 19
- 235000013824 polyphenols Nutrition 0.000 claims abstract description 19
- 230000003373 anti-fouling effect Effects 0.000 claims abstract description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 56
- 239000002202 Polyethylene glycol Substances 0.000 claims description 46
- 239000011550 stock solution Substances 0.000 claims description 37
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 36
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 28
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229940079877 pyrogallol Drugs 0.000 claims description 18
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 14
- 239000007853 buffer solution Substances 0.000 claims description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical group OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 229960003638 dopamine Drugs 0.000 claims description 10
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000008363 phosphate buffer Substances 0.000 claims description 10
- LEAHFJQFYSDGGP-UHFFFAOYSA-K trisodium;dihydrogen phosphate;hydrogen phosphate Chemical compound [Na+].[Na+].[Na+].OP(O)([O-])=O.OP([O-])([O-])=O LEAHFJQFYSDGGP-UHFFFAOYSA-K 0.000 claims description 10
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 239000000872 buffer Substances 0.000 claims description 8
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 8
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 8
- 239000010931 gold Substances 0.000 claims description 8
- 229910052737 gold Inorganic materials 0.000 claims description 8
- 239000002105 nanoparticle Substances 0.000 claims description 8
- 239000013154 zeolitic imidazolate framework-8 Substances 0.000 claims description 8
- MFLKDEMTKSVIBK-UHFFFAOYSA-N zinc;2-methylimidazol-3-ide Chemical compound [Zn+2].CC1=NC=C[N-]1.CC1=NC=C[N-]1 MFLKDEMTKSVIBK-UHFFFAOYSA-N 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 239000010703 silicon Substances 0.000 claims description 7
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000005119 centrifugation Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 238000005530 etching Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920002873 Polyethylenimine Polymers 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- 229940074391 gallic acid Drugs 0.000 claims description 4
- 235000004515 gallic acid Nutrition 0.000 claims description 4
- 229960004337 hydroquinone Drugs 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 4
- 229960001553 phloroglucinol Drugs 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 claims description 4
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 239000010445 mica Substances 0.000 claims description 3
- 229910052618 mica group Inorganic materials 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 3
- 229910001220 stainless steel Inorganic materials 0.000 claims description 3
- 239000010935 stainless steel Substances 0.000 claims description 3
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 claims description 2
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 2
- -1 3-morpholinopropionic acid-sodium hydroxide Chemical compound 0.000 claims description 2
- 239000001263 FEMA 3042 Substances 0.000 claims description 2
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 claims description 2
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 2
- 108010039918 Polylysine Proteins 0.000 claims description 2
- KVBCYCWRDBDGBG-UHFFFAOYSA-N azane;dihydrofluoride Chemical compound [NH4+].F.[F-] KVBCYCWRDBDGBG-UHFFFAOYSA-N 0.000 claims description 2
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 claims description 2
- 229960004679 doxorubicin Drugs 0.000 claims description 2
- 229940030275 epigallocatechin gallate Drugs 0.000 claims description 2
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 claims description 2
- 229940124669 imidazoquinoline Drugs 0.000 claims description 2
- 239000004005 microsphere Substances 0.000 claims description 2
- 229920000083 poly(allylamine) Polymers 0.000 claims description 2
- 229920000656 polylysine Polymers 0.000 claims description 2
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 claims description 2
- 229960001755 resorcinol Drugs 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 229940033123 tannic acid Drugs 0.000 claims description 2
- 235000015523 tannic acid Nutrition 0.000 claims description 2
- 229920002258 tannic acid Polymers 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- IBHWREHFNDMRPR-UHFFFAOYSA-N phloroglucinol carboxylic acid Natural products OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 7
- 230000004048 modification Effects 0.000 abstract description 7
- 238000012986 modification Methods 0.000 abstract description 7
- 125000003172 aldehyde group Chemical group 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
- 239000003519 biomedical and dental material Substances 0.000 abstract description 2
- 239000002775 capsule Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000002791 soaking Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 229920001690 polydopamine Polymers 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000021164 cell adhesion Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229960001124 trientine Drugs 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 238000000089 atomic force micrograph Methods 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 230000008614 cellular interaction Effects 0.000 description 2
- 230000012202 endocytosis Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000003380 quartz crystal microbalance Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PRDFBSVERLRRMY-UHFFFAOYSA-N 2'-(4-ethoxyphenyl)-5-(4-methylpiperazin-1-yl)-2,5'-bibenzimidazole Chemical compound C1=CC(OCC)=CC=C1C1=NC2=CC=C(C=3NC4=CC(=CC=C4N=3)N3CCN(C)CC3)C=C2N1 PRDFBSVERLRRMY-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- DEGAKNSWVGKMLS-UHFFFAOYSA-N calcein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(O)=O)CC(O)=O)=C(O)C=C1OC1=C2C=C(CN(CC(O)=O)CC(=O)O)C(O)=C1 DEGAKNSWVGKMLS-UHFFFAOYSA-N 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001218 confocal laser scanning microscopy Methods 0.000 description 1
- 238000004624 confocal microscopy Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000002073 fluorescence micrograph Methods 0.000 description 1
- 150000002343 gold Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960002378 oftasceine Drugs 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000010069 protein adhesion Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4816—Wall or shell material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Materials Engineering (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Plant Pathology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Materials For Medical Uses (AREA)
- Paints Or Removers (AREA)
Abstract
The invention discloses a multifunctional coating based on a cation-pi interaction, and a preparation method and application thereof, and belongs to the technical field of biomedical material surface modification. The invention uses polyphenol and polyamine to prepare the coating in one step, and the material can be coated on the surfaces of various substrates and has universality. In addition, the coating has outstanding antibacterial effect. While constructing the coating, functional molecules capable of reacting with amino or aldehyde groups are added to endow the coating with multiple functions such as biological antifouling.
Description
Technical Field
The invention belongs to the technical field of biomedical material surface modification, and particularly relates to a multifunctional coating based on a cation-pi interaction, and a preparation method and application thereof.
Background
The surface modification technology plays an important role in the fields of biomedical science, material manufacturing, industrial production and the like. In recent years, researchers have developed a variety of simple and versatile surface modification techniques, such as coating with polydopamine. However, existing coating techniques suffer from lower coating rates; the functional molecules with immobilized surface energy are limited in variety and require multiple steps; the problem of inability to achieve multiple functions (e.g., antimicrobial and antifouling properties) has greatly limited their further use.
Chinese patent document CN112587734a discloses a multifunctional coating of bionic dopamine, firstly, a layer of polydopamine is coated on a substrate, and then functional molecules containing amino groups are further grafted, so as to prepare a coating which has multiple functions of antibacterial, anticoagulation and the like. However, the rate of formation of this coating is low and requires multiple steps, which is time consuming and labor intensive.
Disclosure of Invention
In order to solve the defects in the prior art, the invention aims to provide a multifunctional coating based on the interaction of the cation and pi, and a preparation method and application thereof. The invention utilizes polyphenol and polyamine to prepare the coating in one step. The material can be coated on the surfaces of various substrates and has universality. In addition, the coating has outstanding antibacterial effect. And functional molecules which react with amino or aldehyde groups can be added while constructing the coating, so that the coating can be endowed with multiple functions such as biological antifouling and the like.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
in a first aspect of the invention, a multifunctional coating based on a cation-pi interaction comprises: dissolving polyphenol and polyamine in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution;
adding a substrate into the stock solution, reacting under stirring, and washing after the reaction is finished.
In a second aspect of the invention, the multifunctional coating is obtained by the preparation method.
In a third aspect of the invention, the use of the multifunctional coating described above in biomedical materials.
The beneficial effects of the invention are as follows:
the invention adopts polyphenol and polyamine as raw materials, and water as solvent to prepare the polyphenol-polyamine coating, and the materials are safe, easy to obtain and environment-friendly. The coating is prepared by one step through a soaking method, multiple steps are not needed, and the operation is simple and easy to implement. The coating material can be coated on the surfaces of various substrates and has universality. Due to the electropositivity of the amino group and the existence of polyphenol, the coating material has outstanding antibacterial effect. The polyphenol-polyamine coating has high forming rate, and the thickness of the coating can reach 180nm after 24 hours of reaction.
According to the invention, polyphenols, polyamines and functional molecules are used as raw materials, and water is used as a solvent to prepare the multifunctional coating based on the interaction of the cation-pi, and the functional molecules are grafted through covalent or non-covalent interaction, so that a plurality of steps are not needed, the preparation is carried out by a one-step method, and the operation is simple, convenient and easy to implement; wherein the polyphenol and the polyamine achieve adhesion through synergistic effect without forming an adhesion layer on the substrate in advance; the resulting multifunctional coating was successful in resisting 75% protein and cell adhesion. The strategy can also be successfully coated on a three-dimensional substrate, and the obtained capsule material can obviously reduce endocytosis.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the invention.
FIG. 1 is a graph showing the growth curves of a polyphenol-polyamine coating and a dopamine coating on a planar substrate prepared in example 1 and comparative example 1 according to the present invention;
FIG. 2 is an image of a planar substrate coated with a polyphenol-polyamine coating prepared in example 2 of the present invention;
FIG. 3 is an antimicrobial photograph of a polyphenol-polyamine coating material on a planar substrate prepared in accordance with example 3 of the present invention;
FIG. 4 is an Atomic Force Microscope (AFM) image of a multifunctional coating based on the interaction of cation-pi on a planar substrate prepared in example 4 of the present invention;
FIG. 5 shows the protein adsorption amount of the multifunctional coating surface based on the interaction of the cation-pi on the planar substrate prepared in example 5 of the present invention;
FIG. 6 is a fluorescence microscope image of cell adhesion on the surface of a multifunctional coating based on the interaction of cation-pi on a planar substrate prepared in example 6 of the present invention;
FIG. 7 is a Transmission Electron Microscope (TEM) image of the capsule material prepared in example 7, comparative example 2 of the present invention;
FIG. 8 is a laser Confocal (CLSM) image of interactions between the capsule material prepared in example 7, comparative example 2 of the present invention and cells;
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the invention. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the present invention. As used herein, the singular is also intended to include the plural unless the context clearly indicates otherwise, and furthermore, it is to be understood that the terms "comprises" and/or "comprising" when used in this specification are taken to specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof.
In view of the low coating rate of the existing coating preparation method, the complex modification process of functional molecules and harsh reaction conditions, the invention provides a multifunctional coating based on the interaction of the cation and pi, and a preparation method and application thereof.
The invention provides a preparation method of a multifunctional coating based on a cation-pi interaction, which comprises the following steps: dissolving polyphenol and polyamine in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution;
adding a substrate into the stock solution, reacting under stirring, and washing after the reaction is finished.
In some examples of this embodiment, the stock solution further comprises a functional molecule, specifically: and dissolving polyphenol, polyamine and functional molecules in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution. By adding functional molecules which react with amino or aldehyde groups, the coating can be endowed with multiple functions such as biological antifouling and the like.
In some examples of this embodiment, the substrate comprises a planar substrate, a three-dimensional substrate.
When the substrate is a plane substrate, adding the plane substrate into the stock solution, reacting under stirring, washing and drying after the reaction is finished, and obtaining the functional coating.
Preferably, when the substrate is a planar substrate, the reaction time is 1 to 48 hours, preferably 6 to 24 hours.
Preferably, the planar substrate is one of a silicon wafer, glass, mica sheet, gold sheet, stainless steel substrate, polystyrene substrate, polymethyl methacrylate substrate and 24 pore plate, and preferably one of a silicon wafer, gold sheet and 24 pore plate.
When the substrate is a three-dimensional substrate, adding the three-dimensional substrate into the stock solution, reacting under stirring, etching to remove the template after the reaction is finished, centrifuging, and washing to obtain the capsule material.
Preferably, when the substrate is a three-dimensional substrate, the reaction time is 1 to 48 hours, preferably 6 to 12 hours.
Preferably, the specific conditions of centrifugation are 1000-10000 rpm for 1-10 min, preferably 6000-10000 rpm for 5-10 min.
Preferably, the solution used for etching and removing the template is ethylenediamine tetraacetic acid solution, hydrofluoric acid-ammonium fluoride solution or tetrahydrofuran solution, and preferably is ethylenediamine tetraacetic acid solution. The raw material ethylenediamine can compete with zinc ions in ZIF-8 nano particles for coordination, so that the template is etched and removed.
Preferably, the three-dimensional substrate is one of calcium carbonate particles, silicon dioxide particles, polystyrene microspheres and ZIF-8 nanoparticles, preferably calcium carbonate particles or ZIF-8 nanoparticles, and more preferably ZIF-8 nanoparticles.
In some examples of this embodiment, the polyphenol is one or a combination of two or more of phenol, catechol, resorcinol, hydroquinone, pyrogallol, phloroglucinol, gallic acid, tannic acid, epigallocatechin gallate, preferably one or a combination of two or more of catechol, hydroquinone, pyrogallol, phloroglucinol, gallic acid.
The polyamine is one or more of ammonia water, ethylenediamine, diethylenetriamine, triethylenetetramine, tri (2-aminoethyl) amine, polyethyleneimine, polylysine and polyallylamine, preferably one or more of ethylenediamine, diethylenetriamine, triethylenetetramine, tri (2-aminoethyl) amine and polyethyleneimine.
The functional molecule is one of methoxy polyethylene glycol benzaldehyde, methoxy polyethylene glycol aldehyde group, methoxy polyethylene glycol active ester, methoxy polyethylene glycol amino group, methoxy polyethylene glycol hydroxyl group, methoxy polyethylene glycol fluorescein isothiocyanate, methoxy polyethylene glycol dopamine, four-arm polyethylene glycol benzaldehyde, four-arm polyethylene glycol aldehyde group, four-arm polyethylene glycol active ester, four-arm polyethylene glycol amino group, four-arm polyethylene glycol fluorescein isothiocyanate, four-arm polyethylene glycol dopamine, eight-arm polyethylene glycol benzaldehyde, eight-arm polyethylene glycol aldehyde group, eight-arm polyethylene glycol active ester, eight-arm polyethylene glycol amino group, eight-arm polyethylene glycol hydroxyl group, eight-arm polyethylene glycol fluorescein isothiocyanate, eight-arm polyethylene glycol dopamine, fluorescein isothiocyanate, doxorubicin and imidazoquinoline, preferably one of methoxy polyethylene glycol benzaldehyde, four-arm polyethylene glycol benzaldehyde and eight-arm polyethylene glycol benzaldehyde.
The alkaline buffer solution is one of a tris (hydroxymethyl) aminomethane-hydrochloric acid buffer water solution, a 3-morpholinopropionic acid-sodium hydroxide buffer water solution, a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer water solution, a sodium hydroxide water solution, a potassium hydroxide water solution or an ammonia water solution, and preferably one of a tris (hydroxymethyl) aminomethane-hydrochloric acid buffer water solution and a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer water solution.
In some examples of this embodiment, the concentration of polyphenols in the stock solution is 0.1-100 mg/mL, preferably 1-25 mg/mL.
The polyamine concentration in the stock solution is 5 to 100mmol/L, preferably 15 to 100mmol/L.
In some examples of this embodiment, the functional molecule has a molecular weight of 1 to 20kDa, preferably 2 to 10kDa.
In some examples of this embodiment, the concentration of the functional molecule in the stock solution is 1 to 100mg/mL, preferably 2 to 20mg/mL.
In some examples of this embodiment, the alkaline buffer solution has a pH of 7 to 9.5, preferably 7.5 to 9.5.
In another embodiment of the present invention, a coating material obtained by any one of the above preparation methods is provided.
In a third embodiment of the present invention, there is provided the use of the above-described coating material for the preparation of biomedical materials.
In order to enable those skilled in the art to more clearly understand the technical scheme of the present invention, the technical scheme of the present invention will be described in detail with reference to specific embodiments.
Example 1
A method for preparing a polyphenol-polyamine coating on a planar substrate comprising the steps of:
6mg of Pyrogallol (PG) and 7. Mu.L of Ethylenediamine (EDA) were dissolved in 4mL of a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8) to prepare a stock solution; immersing the silicon wafer into the stock solution, and carrying out soaking reaction for 2 hours, 6 hours, 12 hours and 24 hours under the stirring condition; and (3) performing three times of water washing and nitrogen drying to obtain the PG-EDA coating material.
Example 2
A process for the preparation of a polyphenol-polyamine coating on a planar substrate, which differs from example 1 in that: the substrates were replaced with mica sheets, glass, gold sheets, stainless steel substrates, polystyrene substrates, and polymethyl methacrylate substrates, respectively. Other steps and conditions were consistent with example 1 to produce PG-EDA coating materials.
Example 3
A method for preparing a polyphenol-polyamine coating on a planar substrate comprising the steps of:
20mg of Pyrogallol (PG) and 30. Mu.L of Ethylenediamine (EDA) were dissolved in 1mL of a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8) to prepare a stock solution; adding the stock solution into a 24-hole plate, and soaking and reacting for 12 hours under the stirring condition; and (3) performing three times of water washing and nitrogen drying to obtain the PG-EDA coating material.
Example 4
A preparation method of a multifunctional coating based on the interaction of a cation-pi on a planar substrate comprises the following steps:
6mg of Pyrogallol (PG), 7. Mu.L of Ethylenediamine (EDA) and 20mg of methoxypolyethylene glycol benzaldehyde (mPEG-PhCHO) were dissolved in 4mL of a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8) to prepare a stock solution; immersing the silicon wafer into the stock solution, and carrying out soaking reaction for 6h and 12h under the stirring condition; and (3) performing three times of water washing and nitrogen drying to obtain the PG-EDA-PEG coating material.
Example 5
A preparation method of a multifunctional coating based on the interaction of a cation-pi on a planar substrate comprises the following steps:
8mg of Pyrogallol (PG), 14. Mu.L of triethylene tetramine (TETA) and 40mg of methoxypolyethylene glycol benzaldehyde (mPEG-PhCHO) are dissolved in 4mL of disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8) to prepare a stock solution; immersing the gold slice into the stock solution, and carrying out soaking reaction for 6 hours; and (3) performing three times of water washing and nitrogen drying to obtain the PG-TETA-PEG coating material.
Example 6
A preparation method of a multifunctional coating based on the interaction of a cation-pi on a planar substrate comprises the following steps:
2mg of Pyrogallol (PG), 10. Mu.L of Ethylenediamine (EDA), 5mg of methoxypolyethylene glycol benzaldehyde (mPEG-PhCHO) were dissolved in 1mL of a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8.5) to prepare a stock solution; adding the stock solution into a 24-hole plate, and soaking and reacting for 12 hours under the stirring condition; and (3) performing three times of water washing and nitrogen drying to obtain the PG-EDA-PEG coating material.
Example 7
A preparation method of a multifunctional coating based on the interaction of a cation-pi on a three-dimensional substrate comprises the following steps:
7mg of Pyrogallol (PG), 6. Mu.L of Ethylenediamine (EDA), 17.5mg of methoxypolyethylene glycol benzaldehyde (mPEG-PhCHO) were dissolved in 3.5mL of a buffer aqueous solution (pH 8.5) of tris-hydrochloric acid to prepare a stock solution; then 500 mu L ZIF-8 nano particles are added, and the mixture is soaked and reacted for 6 hours under the stirring condition; centrifuging the reaction solution at 8000rpm for 5min, and washing for three times to obtain PG-EDA-PEG capsule material.
Comparative example 1
In order to compare the coating rates of a polyphenol-polyamine coating and a polydopamine coating, a method for preparing a polydopamine coating on a planar substrate comprises the following steps:
6mg of Dopamine (DA) was dissolved in 4mL of disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8) to prepare a stock solution; immersing the silicon wafer into the stock solution, and carrying out soaking reaction for 2 hours, 6 hours, 12 hours and 24 hours under the stirring condition; and (3) performing three times of water washing and nitrogen drying to obtain the polydopamine coating material.
Comparative example 2
In order to compare the cell interaction degree of the capsule after PEG grafting, a preparation method of a polyphenol biological antifouling material on a three-dimensional substrate comprises the following steps:
7mg of Pyrogallol (PG) and 6. Mu.L of Ethylenediamine (EDA) were dissolved in 3.5mL of a buffer aqueous solution (pH 8.5) of tris-hydroxymethyl aminomethane-hydrochloric acid to prepare a stock solution; then 500 mu L ZIF-8 nano particles are added, and the mixture is soaked and reacted for 6 hours under the stirring condition; centrifuging the reaction solution at 8000rpm for 5min, and washing for three times to obtain PG-EDA capsule material.
Polyphenol-polyamine coating performance test
(1) The coating materials obtained in the embodiment 1 and the comparative example 1 are subjected to AFM test, the thicknesses of the coating materials obtained in the soaking reactions for 2h, 6h, 12h and 24h are measured, a curve of the thickness and time is formed, as shown in figure 1, the coating thickness of the embodiment 1 can reach 180nm after the reaction for 24h, and the forming rate of the coating is high.
(2) Antibacterial property detection of planar coating material
The coating material obtained in example 3 of the present invention was evaluated for in vitro antibacterial activity against gram-negative E.coli (E.coli) and gram-positive Staphylococcus aureus (S.aureus). As shown in fig. 3, the coating prepared in example 3 has outstanding antibacterial properties.
Multifunctional coating material performance detection based on interaction of cation-pi
(1) The coating material obtained in example 4 of the present invention was subjected to AFM test, and AFM images were shown in fig. 4, with a 6h formation coating thickness of about 14nm and a 12h formation coating thickness of about 18nm, and successful formation of the coating was seen.
(2) Detection of protein adsorption resistance of planar functional coating material
Mounting the PG-TETA-PEG coating material modified gold piece prepared in the example 5 on a Quartz Crystal Microbalance (QCM), and introducing water for three times to clean the surface of the gold piece; then introducing Bovine Serum Albumin (BSA) solution for 10min; then water is introduced to wash out protein with weak surface adsorption; the anti-protein adsorption properties of the coatings were evaluated by comparing the frequency change before and after protein passage. As shown in FIG. 5, the PG-TETA-PEG coating material prepared by the invention can resist 75% of protein adsorption compared with a bare gold surface.
(3) Cell adhesion resistance detection of planar functional coating material
10X 10 plates were seeded in blank 24 well plates and PG-EDA-PEG coated material modified 24 well plates prepared in example 6, respectively 4 The MDA-MB-231 cells are cultured for 6 hours at 37 ℃; then, the cells with weak adhesion are washed off by washing three times with PBS; then, 100. Mu.L of calcein dye was added and the mixture was stained in the dark at room temperature for 15 minutes. The results of the inverted fluorescence microscope observation are shown in FIG. 6, and the PG-EDA-PEG coating material was resistant to 75% cell adhesion.
(4) TEM tests were carried out on the capsule materials obtained in example 7 and comparative example 2 of the present invention, and TEM images are shown in FIG. 7, indicating that example 7 successfully forms capsules having a hollow structure.
(5) Detection of cell interaction performance of capsule material
Inoculating 10×10 in confocal dish 4 MDA-MB-231 cells are cultured for 12 hours at 37 ℃ to adhere the cells; immediately after adding 500. Mu.L of Fluorescein Isothiocyanate (FITC) -labeled capsule materials prepared in example 7 and comparative example 2, the materials were incubated for 6 hours and then washed three times with PBS; the nuclei were stained with Hoechst 33342 for 20min and the cell membranes were stained with WGA-AF633 for 10min, fixed with 4% paraformaldehyde. Confocal microscopy observations are shown in fig. 8, the PG-EDA-PEG capsule material can significantly reduce the degree of endocytosis compared to the PG-EDA capsule material.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (15)
1. The preparation method of the multifunctional coating based on the interaction of the cation and pi is characterized by comprising the following steps of: dissolving polyphenol and polyamine in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution;
adding a substrate into the stock solution, reacting under stirring, and washing after the reaction is finished to obtain the composite material;
the cation-pi interaction is an interaction between a protonated polyamine and the benzene ring of a polyphenol;
the pH value of the alkaline buffer solution is 7-9.5;
the stock solution also comprises functional molecules, specifically: dissolving polyphenol, polyamine and functional molecules in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution;
the concentration of polyphenol in the stock solution is 0.1-100 mg/mL; the concentration of polyamine in the stock solution is 5-100 mmol/L;
the polyphenol is one or more of phenol, catechol, resorcinol, hydroquinone, pyrogallol, phloroglucinol, gallic acid, tannic acid and epigallocatechin gallate;
the polyamine is one or the combination of more than two of ammonia water, ethylenediamine, diethylenetriamine, triethylenetetramine, tri (2-aminoethyl) amine, polyethyleneimine, polylysine and polyallylamine;
the functional molecule is one of methoxy polyethylene glycol benzaldehyde, methoxy polyethylene glycol aldehyde group, methoxy polyethylene glycol active ester, methoxy polyethylene glycol amino group, methoxy polyethylene glycol hydroxyl group, methoxy polyethylene glycol fluorescein isothiocyanate, methoxy polyethylene glycol dopamine, four-arm polyethylene glycol benzaldehyde, four-arm polyethylene glycol aldehyde group, four-arm polyethylene glycol active ester, four-arm polyethylene glycol amino group, four-arm polyethylene glycol fluorescein isothiocyanate, four-arm polyethylene glycol dopamine, eight-arm polyethylene glycol benzaldehyde, eight-arm polyethylene glycol aldehyde group, eight-arm polyethylene glycol active ester, eight-arm polyethylene glycol amino group, eight-arm polyethylene glycol hydroxyl group, eight-arm polyethylene glycol fluorescein isothiocyanate, eight-arm polyethylene glycol dopamine, fluorescein isothiocyanate, doxorubicin and imidazoquinoline;
the molecular weight of the functional molecule is 1-20 kDa; the concentration of the functional molecules in the stock solution is 1-100 mg/mL;
the alkaline buffer solution is one of a tris-hydrochloric acid buffer water solution, a 3-morpholinopropionic acid-sodium hydroxide buffer water solution, a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer water solution, a sodium hydroxide water solution, a potassium hydroxide water solution or an ammonia water solution;
the substrate comprises a plane substrate and a three-dimensional substrate.
2. The method for preparing the multifunctional coating based on the interaction of the cation and pi as claimed in claim 1, wherein when the substrate is a planar substrate, the planar substrate is added into the stock solution, the reaction is carried out under the stirring condition, and the functional coating material is obtained by washing and drying after the reaction is finished; the reaction time is 1-48 and h.
3. The method for preparing the multifunctional coating based on the interaction of the cation and pi as claimed in claim 2, wherein the reaction time is 6-24 h.
4. The method for preparing the multifunctional coating based on the interaction of the cation and pi as claimed in claim 1, wherein when the substrate is a three-dimensional substrate, the three-dimensional substrate is added into the stock solution, the reaction is carried out under the stirring condition, and after the reaction is finished, the template is removed by etching, and then the functional coating material is obtained by centrifugation and washing; the reaction time is 1-48 h; the solution used for etching and removing the template is ethylenediamine tetraacetic acid solution, hydrofluoric acid-ammonium fluoride solution or tetrahydrofuran solution; the specific conditions of the centrifugation are 1000-10000 rpm, and the centrifugation is carried out for 1-10 min.
5. The method for preparing a multifunctional coating based on the interaction of the cation and pi as claimed in claim 4, wherein the reaction time is 6-12 h; the solution used for removing the template by etching is ethylenediamine tetraacetic acid solution; the specific conditions of the centrifugation are 6000-10000 rpm, and the centrifugation is carried out for 5-10 min.
6. The method for preparing the multifunctional coating based on the interaction of the cation and pi as claimed in claim 1, wherein the planar substrate is a silicon wafer, glass, mica sheet, gold sheet, stainless steel substrate, polystyrene substrate, polymethyl methacrylate substrate or 24-pore plate;
the three-dimensional substrate is calcium carbonate particles, silicon dioxide particles, polystyrene microspheres or ZIF-8 nano particles.
7. The method for preparing the multifunctional coating based on the interaction of the cation and pi as claimed in claim 6, wherein the planar substrate is a silicon wafer, a gold wafer or a 24-pore plate.
8. The method for preparing the multifunctional coating based on the interaction-pi interaction according to claim 1, wherein the three-dimensional substrate is calcium carbonate particles or ZIF-8 nano particles.
9. The method for preparing the multifunctional coating based on the interaction of the cation and pi as claimed in claim 1, wherein the polyphenol is one or more of catechol, hydroquinone, pyrogallol, phloroglucinol and gallic acid;
the polyamine is one or the combination of more than two of ethylenediamine, diethylenetriamine, triethylenetetramine, tri (2-aminoethyl) amine and polyethyleneimine;
the functional molecule is one of methoxy polyethylene glycol benzaldehyde, four-arm polyethylene glycol benzaldehyde and eight-arm polyethylene glycol benzaldehyde;
the alkaline buffer solution is one of a tris-hydrochloric acid buffer aqueous solution and a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution.
10. The method for preparing a multifunctional coating based on the interaction of the cation and pi as claimed in claim 1, wherein the concentration of polyphenol in the stock solution is 1-25 mg/mL; the concentration of polyamine in the stock solution is 15-100 mmol/L.
11. The method for preparing a multifunctional coating based on the interaction of the cation and pi as claimed in claim 1, wherein the molecular weight of the functional molecule is 2-10 kDa; the concentration of the functional molecules in the stock solution is 2-20 mg/mL.
12. The method for preparing a multifunctional coating based on the interaction of the cation and pi as claimed in claim 1, wherein the pH value of the alkaline buffer solution is 7.5-9.5.
13. The multifunctional coating material obtained by the preparation method of the multifunctional coating based on the interaction of the cation-pi as claimed in any one of claims 1 to 12.
14. The multifunctional coating material obtained by the preparation method of the multifunctional coating based on the interaction of the cation-pi, as claimed in claim 13, is a polyphenol-polyamine coating or a biological antifouling coating.
15. Use of the multifunctional coating material of claim 13 or 14 in biomedical materials.
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| CN110016089A (en) * | 2019-04-17 | 2019-07-16 | 西南交通大学 | Rich amine base catecholamine compound and preparation method thereof, rich amine primary surface modified product, material and its dip-coating method |
| CN112691238A (en) * | 2021-01-18 | 2021-04-23 | 成都鼎峰前瞻科技有限公司 | Material with biological anti-fouling function, preparation method and application thereof |
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| CN109867822A (en) * | 2019-01-08 | 2019-06-11 | 中国人民解放军东部战区总医院 | A kind of alkylating chitosan multifunctional water gel and its preparation method and application |
| CN110016089A (en) * | 2019-04-17 | 2019-07-16 | 西南交通大学 | Rich amine base catecholamine compound and preparation method thereof, rich amine primary surface modified product, material and its dip-coating method |
| CN112691238A (en) * | 2021-01-18 | 2021-04-23 | 成都鼎峰前瞻科技有限公司 | Material with biological anti-fouling function, preparation method and application thereof |
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