CN107412883B - hydrophilic super-smooth coating for surface of medical instrument and preparation method thereof - Google Patents
hydrophilic super-smooth coating for surface of medical instrument and preparation method thereof Download PDFInfo
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- CN107412883B CN107412883B CN201710284736.XA CN201710284736A CN107412883B CN 107412883 B CN107412883 B CN 107412883B CN 201710284736 A CN201710284736 A CN 201710284736A CN 107412883 B CN107412883 B CN 107412883B
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- 239000011248 coating agent Substances 0.000 title claims abstract description 98
- 238000000576 coating method Methods 0.000 title claims abstract description 98
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000010410 layer Substances 0.000 claims abstract description 37
- 239000002344 surface layer Substances 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 24
- 239000002202 Polyethylene glycol Substances 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 20
- 229920001223 polyethylene glycol Polymers 0.000 claims description 20
- 229920002635 polyurethane Polymers 0.000 claims description 18
- 239000004814 polyurethane Substances 0.000 claims description 18
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 14
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 125000004386 diacrylate group Chemical group 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- -1 hydroxypropyl Chemical group 0.000 claims description 9
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 8
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 7
- 239000012965 benzophenone Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 6
- 238000007598 dipping method Methods 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 claims description 6
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 4
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- YSVQGHIOJPVICX-UHFFFAOYSA-N 1-(1-hydroxycyclohexyl)-1-phenylpropan-2-one Chemical compound C1CCCCC1(O)C(C(=O)C)C1=CC=CC=C1 YSVQGHIOJPVICX-UHFFFAOYSA-N 0.000 claims description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001661 Chitosan Polymers 0.000 claims description 2
- 102000008186 Collagen Human genes 0.000 claims description 2
- 108010035532 Collagen Proteins 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 239000000783 alginic acid Substances 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 229960001126 alginic acid Drugs 0.000 claims description 2
- 150000004781 alginic acids Chemical class 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 235000010980 cellulose Nutrition 0.000 claims description 2
- 229940045110 chitosan Drugs 0.000 claims description 2
- 229920001436 collagen Polymers 0.000 claims description 2
- 229960005188 collagen Drugs 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- 229920002674 hyaluronan Polymers 0.000 claims description 2
- 229960003160 hyaluronic acid Drugs 0.000 claims description 2
- 239000000017 hydrogel Substances 0.000 claims description 2
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims 1
- 239000012957 2-hydroxy-2-methyl-1-phenylpropanone Substances 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000003780 insertion Methods 0.000 abstract 1
- 230000037431 insertion Effects 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 239000002987 primer (paints) Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000003814 drug Substances 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- GKDLTXYXODKDEA-UHFFFAOYSA-N 1-phenylbutan-2-one Chemical compound CCC(=O)CC1=CC=CC=C1 GKDLTXYXODKDEA-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- UMNVUZRZKPVECS-UHFFFAOYSA-N 2-propanoyloxyethyl propanoate Chemical compound CCC(=O)OCCOC(=O)CC UMNVUZRZKPVECS-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- UCIDWECIRUUWHM-UHFFFAOYSA-N [2-(hydroxymethyl)-3-propanoyloxy-2-(propanoyloxymethyl)propyl] propanoate Chemical compound CCC(=O)OCC(CO)(COC(=O)CC)COC(=O)CC UCIDWECIRUUWHM-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
- A61L29/085—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/06—Coatings containing a mixture of two or more compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/08—Coatings comprising two or more layers
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Materials For Medical Uses (AREA)
- Paints Or Removers (AREA)
Abstract
The invention provides a hydrophilic super-smooth coating for the surface of a medical instrument and a preparation method thereof. The surface of the medical appliance is firstly dipped in the bottom layer solution by adopting a dipping-lifting technology, and partial curing is carried out by utilizing ultraviolet radiation; and then the medical apparatus and instruments of the partially cured bottom layer are dipped in the surface layer coating, and after the medical apparatus and instruments are completely cured under ultraviolet light, the surface layer is uniformly and stably distributed on the bottom layer. The hydrophilic super-smooth coating can be quickly cured under ultraviolet light, the obtained hydrophilic coating has excellent lubricity and durability, friction and damage to tissues in the insertion process can be effectively reduced, and the hydrophilic super-smooth coating is easy to obtain raw materials and low in price.
Description
Technical Field
The invention belongs to the field of medical instruments, and relates to a hydrophilic ultra-smooth coating and a preparation method thereof.
Background
Interventional medicine is a low-invasive or minimally invasive technique that has formed one of three major clinical medicine paralleling surgery and medicine, while imaging devices and interventional instruments are the mainstay of interventional medicine.
Lubricity is one of the very important properties of interventional devices (catheters, guidewires). When inserted or extracted from the human body, the surfaces of these instruments are required to have lubricity so as to reduce the damage and adhesion to the tissues and relieve the pain of the patient. At present, two ways to solve the problem of lubricity are available, one is to use lubricating oil, but the lubricity obtained by the treatment method is poor, difficult to last and unfavorable for operation. One is to form a hydrophilic coating with lubricity on the surface of the instrument.
Because the interventional device moves in the body and stays for a period of time, the hydrophilic coating on the interventional device has both hydrophilic lubricating performance and stability, namely the coating does not fall off after repeated friction, and good comprehensive performance is maintained. Such techniques have been widely used, because they can fix hydrophilic compounds by chemical bond or physical entanglement.
At present, the hydrophilic ultra-smooth coating products used on the surfaces of medical instruments are few in China, and most of the products are monopolized abroad.
Disclosure of Invention
aiming at the problems in the prior art, the invention provides a hydrophilic super-smooth coating for the surface of a medical instrument and a preparation method thereof.
The technical scheme of the invention is as follows: a hydrophilic super-slippery coating comprises a bottom layer and a surface layer, wherein the two layers are connected through chemical bonds and intermolecular force. The bottom layer is a cross-linked network structure, is a connecting layer for providing bonding cross-linking points for the surface layer, is obtained by dipping the surface of the medical instrument in the bottom layer coating and performing ultraviolet curing. The surface layer is a hydrophilic layer, is a hydrogel coating with an interpenetrating network structure, is obtained by dipping the surface of the medical instrument coated with the bottom layer in the surface layer coating and performing ultraviolet curing. The bottom layer and the substrate are firmly combined by utilizing similar compatible principles.
the primer consists of polyurethane acrylate, a reactive diluent, a first photoinitiator and a first organic solvent. The mass ratio of the polyurethane acrylate to the reactive diluent is 1:0.1-10, the mass of the first photoinitiator is 2% -8% of the total mass of the primer after curing, and the mass of the first organic solvent is 70% -99% of the total mass of the primer.
The surface layer coating consists of a monomer and/or a polymer with two or more than two photopolymerisable functional groups, a biocompatible hydrophilic polymer, a second photoinitiator and a second organic solvent. The mass ratio of the monomer and/or polymer with functional groups to the biocompatible hydrophilic polymer is 1:0.1-10, the mass of the second photoinitiator is 0.5-5% of the total mass of the surface layer coating after curing, and the mass of the second organic solvent is 60-99% of the total mass of the surface layer coating.
the preparation method of the hydrophilic ultra-smooth coating comprises the following steps:
First, preparing a primer
1.1) preparation of a urethane acrylate prepolymer
The method comprises the following steps: under the mechanical stirring, adding diisocyanate and hydroxyl acrylate into a reactor, and reacting for 2-24h at 15-60 ℃ to obtain an intermediate; and heating to 60-90 ℃, adding polyether/ester dihydric alcohol and a catalyst stannous octoate, and reacting for 1-24h under the action of the stannous octoate to obtain the polyurethane acrylate prepolymer.
The second method comprises the following steps: under the mechanical stirring, adding diisocyanate and polyether/ester dihydric alcohol into a reactor, and reacting for 1-24h at 60-90 ℃ to obtain an intermediate; and cooling to 15-60 ℃, adding hydroxyl acrylate and a catalyst stannous octoate, and reacting for 2-24h under the action of the stannous octoate to obtain the polyurethane acrylate prepolymer.
The diisocyanates described in both processes include: 2, 4-toluene diisocyanate, isophorone diisocyanate, hexamethylene-1, 6-diisocyanate, and diphenylmethane diisocyanate. The acrylic acid hydroxyl ester comprises: one or more of hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate and hydroxybutyl (meth) acrylate. The polyether/ester dihydric alcohol comprises: one or more of polyethylene glycol, polypropylene glycol, polytetrahydrofuran diol, polycarbonate diol and polycaprolactone diol, and the number average molecular weight is 200-200000.
1.2) dissolving the urethane acrylate prepolymer, the reactive diluent and the first photoinitiator in a first organic solvent, and stirring the mixture for 1 to 2 hours in the dark at room temperature to form a mixture with the viscosity of 1 to 10mm2And (6) transparent and uniform bottom layer solution is obtained, and the bottom layer coating is obtained. The mass ratio of the polyurethane acrylate to the reactive diluent is
1 (0.1-10); the first photoinitiator accounts for 2-8% of the total mass of the primer after curing, and the first organic solvent accounts for 70-99% of the total mass of the primer.
The active diluent is selected from one or more of tripropylene glycol diacrylate, polyethylene glycol diacrylate, 1, 6-hexanediol diacrylate, pentaerythritol tripropionate and pentaerythritol tetraacrylate. The first organic solvent is one or more than two of water, ethanol, isopropanol, acetone, butanone and ethyl acetate. The first photoinitiator is selected from one or more than two of 2-hydroxy-4' (2-hydroxyethoxy) -2-methyl propiophenone (Irgacure 2959), 1-hydroxycyclohexyl phenyl acetone (Irgacure 184), 2-hydroxy-2 methyl-1-phenyl acetone (Irgacure 1173), 2-methyl-1- [4- (methylthiophenyl) -2 morpholinyl-1-acetone ] (Irgacure 907), 2-benzyl-2-dimethylamine-1- (4-morpholinyl benzyl phenyl) butanone (Irgacure 369), phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide (Irgacure 819), benzophenone and the like.
Second, preparing a top coating
Dissolving a monomer and/or polymer with more than two functional groups capable of performing photopolymerization, a biocompatible hydrophilic polymer and a second photoinitiator in a second organic solvent, and stirring at room temperature in a dark place for 1-2h to form a solution with the viscosity of 17-55mm2And (6) transparent and uniform surface layer solution is obtained, and the surface layer coating is obtained. The mass ratio of the monomer and/or polymer with functional groups to the biocompatible hydrophilic polymer is 1 (0.1-10), the mass of the second photoinitiator is 0.5-5% of the total mass of the surface layer coating after curing, and the mass of the second organic solvent is 60-99% of the total mass of the surface layer coating.
The monomers and/or polymers having more than two functional groups capable of photopolymerization are selected from unsaturated esters and unsaturated ethers such as tripropylene glycol diacrylate, polyethylene glycol diacrylate, 1, 6-hexanediol diacrylate, pentaerythritol tripropionate, pentaerythritol tetraacrylate. The biocompatible hydrophilic polymer is selected from one or more than two of polyvinylpyrrolidone, polyvinyl alcohol, polyurethane, polyethylene glycol, sodium polyacrylate, polyacrylamide, polyacrylic acid-acrylamide partial sodium salt, starch, cellulose, alginic acid, hyaluronic acid, chitosan and collagen; the number average molecular weight of the hydrophilic polymer is in the range of 2000-5000000. The second organic solvent is one or more than two of water, ethanol, isopropanol, acetone, butanone and ethyl acetate. The second photoinitiator is selected from one or more than two of 2-hydroxy-4' (2-hydroxyethoxy) -2-methyl propiophenone (Irgacure 2959), 1-hydroxycyclohexyl phenyl acetone (Irgacure 184), 2-hydroxy-2 methyl-1-phenyl acetone (Irgacure 1173), 2-methyl-1- [4- (methylthiophenyl) -2 morpholinyl-1-acetone ] (Irgacure 907), 2-benzyl-2-dimethylamine-1- (4-morpholinyl benzyl phenyl) butanone (Irgacure 369), phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide (Irgacure 819), benzophenone and the like.
thirdly, preparing a hydrophilic ultra-smooth coating
Coating the primer on the surface of the medical instrument, radiating ultraviolet for 1-60 s, curing the primer to form a primer on the surface of the medical instrument, coating the surface coating on the primer, radiating ultraviolet for 60-360 s, curing the surface coating, and forming a hydrophilic super-smooth coating on the surface of the medical instrument. The ultraviolet energy density is 10mw/cm2~120mw/cm2。
The coating mode is a dipping-pulling mode, the dipping time is 1-30s, and the pulling speed is 5-150 mm/min. The bottom layer and the surface layer are solidified in a rotating mode, and the rotating speed is 3-60 rpm/min.
The invention has the beneficial effects that:
According to the hydrophilic super-smooth coating and the preparation method thereof, a double-layer (bottom layer and surface layer) coating system is constructed, the bottom layer is used as an intermediate connecting layer, on one hand, the coating is firmly attached to a base material by virtue of acting force generated by similar compatibility, and on the other hand, bonding cross-linking points are provided for the surface layer. And because the primer coating and the surface coating contain the same components, the intermolecular force combination generated by the two layers due to similar compatibility is firmer. So that the hydrophilic coating has excellent hydrophilic lubricating property and excellent adhesive force.
The invention utilizes the ultraviolet curing technology, can shorten the curing time to several minutes, greatly increases the production efficiency and is beneficial to reducing the production cost.
The invention is a layer of transparent film in dry state, which is convenient for packaging and storage.
Detailed Description
In order to make the technical solution and advantages of the present invention more apparent, the following is further detailed by examples, but does not represent a limitation of the present patent.
Preparation examples
Preparation of urethane acrylate prepolymer 1
10.45g of 2, 4-toluene diisocyanate and 30g of polytetrahydrofuran 1000 (the number average molecular weight is 1000) are added into a reactor, the mixture is mechanically stirred at 60 ℃ to react for 4 hours to obtain an intermediate, the temperature is reduced to 40 ℃, 7.69g of hydroxybutyl (meth) acrylate and 0.077g of stannous octoate are added, and the reaction is carried out for 3 hours to obtain the urethane acrylate prepolymer 1.
Preparation of urethane acrylate prepolymer 2
10.45g of 2, 4-toluene diisocyanate and 7.69g of hydroxybutyl (meth) acrylate are added into a reactor, mechanically stirred at 40 ℃ for 3 hours to obtain an intermediate prepolymer, heated to 60 ℃, added with 60g of polytetrahydrofuran 2000 (number average molecular weight 2000) and 0.077g of stannous octoate, and reacted for 6 hours to obtain a polyurethane acrylate prepolymer 2.
Preparation of urethane acrylate prepolymer 3
adding 13.34g of isophorone diisocyanate and 60g of polyethylene glycol 2000 into a reactor, mechanically stirring for 6h at 60 ℃ to obtain an intermediate prepolymer, cooling to 40 ℃, adding 7.809g of hydroxyethyl methacrylate and 0.078g of stannous octoate, and reacting for 3h to obtain polyurethane acrylate prepolymer 3.
Preparation of urethane acrylate prepolymer 4
Adding 13.34g of 13.34g g isophorone diisocyanate and 30g of polyethylene glycol 1000 into a reactor, mechanically stirring for 4h at 60 ℃ to obtain an intermediate prepolymer, cooling to 40 ℃, adding 7.809g of hydroxyethyl methacrylate and 0.078g of stannous octoate, and reacting for 3h to obtain polyurethane acrylate prepolymer 4.
The following examples 1 to 3 all used the urethane acrylates prepared in the preparation examples as reaction raw materials.
Example 1
(1) Dissolving the urethane acrylate prepolymer 1, polyethylene glycol dipropionate 1000 (obtained by capping polyethylene glycol with the number average molecular weight of 1000) and Irgacure 2959 in a mixed solvent of ethanol and deionized water, and stirring for 1-2h at room temperature in a dark place to obtain a primer; wherein the mass ratio of the polyurethane acrylate to the polyethylene glycol dipropionate 1000 is 2:1, the Irgacure 2959 accounts for 5% of the total mass of the primer after curing, and the ethanol and the water account for 94% of the mass of the primer.
Dissolving polyethylene glycol diacrylate 1000, polyethylene glycol 20000 (number average molecular weight is 20000) and Irgacure 2959 in deionized water, and stirring at room temperature in a dark place for 1-2h to obtain a surface coating; wherein the mass ratio of the polyethylene glycol diacrylate 1000 to the polyethylene glycol 20000 is 1:4, the photoinitiator is 3% of the total mass of the surface layer coating after curing, and the deionized water accounts for 80% of the surface layer coating.
(2) and coating the bottom layer coating on the surface of the medical instrument, radiating ultraviolet for 10s, coating the surface layer coating on the cured bottom layer, and performing ultraviolet curing for 300 s. The required coating can be obtained on the surface of the medical appliance.
And (3) lubricity test: the medical instrument coated with the hydrophilic coating is placed on a self-made and modified universal testing machine, one end of the medical instrument is fixed in a clamp applying clamping force, the other end of the medical instrument is connected with a sensor, testing is carried out at room temperature, the clamping force is 5N, and a testing medium is water. In contrast to the uncoated samples, the magnitude of the difference in the friction values reflects the hydrophilic lubricating properties of the hydrophilic coating.
And (3) durability test: the lubricating property is repeatedly detected, and the repeatability of the friction force reflects the durability and the wear resistance of the hydrophilic coating.
The test result shows that: after the hydrophilic coating is prepared on the surface of the medical instrument in the embodiment, the friction force amplitude is reduced by more than 95%, which shows that the coating has excellent lubricity, and after multiple times of friction, the friction force amplitude is still more than 95%, which shows that the coating has excellent durability and wear resistance.
Example 2
(1) Dissolving the polyurethane acrylate prepolymer 2, pentaerythritol tetraacrylate and benzophenone in ethanol, and stirring at room temperature in the dark for 1-2h to obtain a primer; wherein the mass ratio of the urethane acrylate to the pentaerythritol tetraacrylate is 1:1, the photoinitiator is 5% of the total mass of the primer after curing, and the ethanol accounts for 85% of the mass of the primer.
Dissolving pentaerythritol tetraacrylate, polyvinylpyrrolidone K30 (the number average molecular weight is 45000-; wherein the mass ratio of the pentaerythritol tetraacrylate to the polyvinylpyrrolidone is 3:1, and the deionized water accounts for 85% of the surface layer coating.
(2) And (3) coating the bottom layer coating on the surface of the medical instrument, radiating ultraviolet for 20s, coating the surface layer coating on the cured bottom layer, and performing ultraviolet curing for 320 s. The required coating can be obtained on the surface of the medical appliance.
The lubricity and durability test methods in this example were the same as those in example 1, and the test results showed that: after the hydrophilic coating is prepared on the surface of the medical instrument in the embodiment, the friction force amplitude is reduced by more than 95%, which shows that the coating has excellent lubricity, and after multiple times of friction, the friction force amplitude is still more than 95%, which shows that the coating has excellent durability and wear resistance.
Example 3
(1) Dissolving the urethane acrylate prepolymer 3, the polyethylene glycol diacrylate 600 and the benzophenone in ethanol, and stirring at room temperature in a dark place for 1-2 hours to obtain a primer; wherein the mass ratio of the urethane acrylate to the polyethylene glycol diacrylate 600 is 1:1, the benzophenone is 4% of the cured primer, and the ethanol accounts for 75% of the mass of the primer.
Dissolving polyethylene glycol diacrylate 600, polyacrylic acid-acrylamide partial sodium salt and benzophenone in a mixed solvent of ionic water and ethanol, and stirring at room temperature in a dark place for 1-2 hours to obtain a surface coating; wherein the mass ratio of the polyethylene glycol diacrylate 600 to the polyacrylic acid-acrylamide partial sodium salt is 1:4, the photoinitiator is 4% of the total mass of the cured surface coating, the deionized water and the ethanol account for 93% of the surface coating, and the mass ratio of the deionized water to the ethanol is 1: 1.
Wherein the sodium salt of polyacrylic acid-acrylamide is a product with a sigma-aldrich and a number average molecular weight of 150000.
(2) And coating the bottom layer coating on the surface of the medical instrument, radiating ultraviolet for 15s, coating the surface layer coating on the cured bottom layer, and performing ultraviolet curing for 360 s. The required coating can be obtained on the surface of the medical appliance.
the lubricity and durability test methods in this example were the same as those in example 1, and the test results showed that: after the hydrophilic coating is prepared on the surface of the medical instrument in the embodiment, the friction force amplitude is reduced by more than 95%, which shows that the coating has excellent lubricity, and after multiple times of friction, the friction force amplitude is still more than 95%, which shows that the coating has excellent durability and wear resistance.
Claims (8)
1. A hydrophilic super-slip coating for the surface of a medical instrument is characterized by comprising a bottom layer and a surface layer, wherein the two layers are connected through a chemical bond formed by ultraviolet grafting and intermolecular force; the bottom layer is of a cross-linked network structure, is used for providing a connecting layer of bonding cross-linking points for the surface layer, is obtained by dipping the surface of the medical instrument in the bottom layer coating and performing ultraviolet curing; the surface layer is a hydrophilic layer, is a hydrogel coating with an interpenetrating network structure, is obtained by dipping the surface of the medical instrument coated with the bottom layer in the surface layer coating and performing ultraviolet curing;
The primer consists of polyurethane acrylate, a reactive diluent, a first photoinitiator and a first organic solvent;
The surface layer coating consists of monomers and/or polymers with two or more than two photopolymerization functional groups, a biocompatible hydrophilic polymer, a second photoinitiator and a second organic solvent;
The viscosity of the bottom coating is 1-10mm2The mass ratio of the polyurethane acrylate to the reactive diluent is 1:0.1-10, the mass of the first photoinitiator is 2% -8% of the total mass of the primer after curing, and the mass of the first organic solvent is 70% -99% of the total mass of the primer;
The viscosity of the surface coating is 17-55mm2And/or the mass ratio of the monomer with the functional group and/or the polymer to the biocompatible hydrophilic polymer is 1:0.1-10, the mass of the second photoinitiator is 0.5-5% of the total mass of the surface layer coating after curing, and the mass of the second organic solvent is 60-99% of the total mass of the surface layer coating.
2. A method for preparing a hydrophilic ultra-slip coating according to claim 1, characterized by the steps of:
First, preparing a primer
1.1) preparation of a urethane acrylate prepolymer
The method comprises the following steps: after uniformly mixing diisocyanate and hydroxyl acrylate, reacting for 2-24h at 15-60 ℃ to obtain an intermediate; heating to 60-90 ℃, adding polyether/ester dihydric alcohol and a catalyst stannous octoate, and reacting for 1-24h to obtain a polyurethane acrylate prepolymer;
The second method comprises the following steps: reacting diisocyanate and polyether/ester dihydric alcohol at 60-90 ℃ for 1-24h to obtain an intermediate; cooling to 15-60 ℃, adding hydroxyl acrylate and stannous octoate serving as a catalyst, and reacting for 2-24 hours to obtain a polyurethane acrylate prepolymer;
1.2) dissolving the polyurethane acrylate prepolymer, the reactive diluent and the first photoinitiator in a first organic solvent, and stirring at room temperature in the dark for 1-2 hours to form a bottom layer solution, thus obtaining a bottom layer coating; the mass ratio of the polyurethane acrylate to the reactive diluent is 1: 0.1-10; the first photoinitiator accounts for 2-8% of the total mass of the primer after curing, and the first organic solvent accounts for 70-99% of the total mass of the primer;
Second, preparing a top coating
Dissolving a monomer and/or polymer with more than two functional groups capable of performing photopolymerization, a biocompatible hydrophilic polymer and a second photoinitiator in a second organic solvent, and stirring at room temperature in the dark for 1-2 hours to form a surface layer solution, thereby obtaining a surface layer coating; the mass ratio of the monomer with the functional group and/or the polymer to the biocompatible hydrophilic polymer is 1:0.1-10, the mass of the second photoinitiator is 0.5-5% of the total mass of the surface layer coating after curing, and the mass of the second organic solvent is 60-99% of the total mass of the surface layer coating;
The monomer and/or polymer with more than two functional groups capable of carrying out photopolymerization is selected from unsaturated esters and unsaturated ethers including tripropylene glycol diacrylate, polyethylene glycol diacrylate, 1, 6-hexanediol diacrylate, pentaerythritol triacrylate and pentaerythritol tetraacrylate;
Thirdly, preparing a hydrophilic ultra-smooth coating
Coating the primer on the surface of the medical instrument, radiating ultraviolet for 1-60 s, and curing the primer to form a primer on the surface of the medical instrument; coating the surface layer coating on the bottom layer, radiating the surface layer coating for 60-360 seconds by ultraviolet light, and curing the surface layer coating to form a hydrophilic ultra-smooth coating on the surface of the medical instrument; the ultraviolet energy density is 10mw/cm2~120mw/cm2。
3. The method of claim 2, wherein the diisocyanate in the two methods of preparing the urethane acrylate prepolymer in the first step 1.1) comprises: one of 2, 4-toluene diisocyanate, isophorone diisocyanate, hexamethylene-1, 6-diisocyanate, and diphenylmethane diisocyanate; the acrylic acid hydroxyl ester comprises: one or more of hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate and hydroxybutyl (meth) acrylate; the polyether/ester dihydric alcohol comprises: one or more of polyethylene glycol, polypropylene glycol, polytetrahydrofuran diol, polycarbonate diol and polycaprolactone diol, and the number average molecular weight is 200-200000.
4. the method for preparing a hydrophilic ultra-smooth coating according to claim 3, characterized in that the reactive diluent in the first step 1.2) is one or more selected from the group consisting of tripropylene glycol diacrylate, polyethylene glycol diacrylate, 1, 6-hexanediol diacrylate, pentaerythritol triacrylate, and pentaerythritol tetraacrylate.
5. The method of claim 4, wherein the biocompatible hydrophilic polymer in the second step is selected from one or more of polyvinylpyrrolidone, polyvinyl alcohol, polyurethane, polyethylene glycol, sodium polyacrylate, polyacrylamide, sodium polyacrylate-acrylamide moiety, starch, cellulose, alginic acid, hyaluronic acid, chitosan, and collagen, and the number average molecular weight of the hydrophilic polymer is in the range of 2000-5000000.
6. The method for preparing the hydrophilic ultra-smooth coating according to claim 5, wherein the first organic solvent and the second organic solvent are respectively one or more than two selected from ethanol, isopropanol, acetone, butanone and ethyl acetate.
7. the method of claim 6, wherein the first and second photoinitiators are selected from the group consisting of 2-hydroxy-4' (2-hydroxyethoxy) -2-methylpropiophenone, 1-hydroxycyclohexylphenylacetone, 2-hydroxy-2-methyl-1-phenylpropanone, 2-methyl-1- [4- (methylthiophenyl) -2 morpholinyl-1-propanone ], 2-phenylbenzyl-2-dimethylamine-1- (4-morpholinylbenzylphenyl) butanone, phenylbis (2,4, 6-trimethylbenzoyl) phosphine oxide, and benzophenone.
8. The method for preparing the hydrophilic ultra-smooth coating according to claim 7, wherein the coating mode in the third step is a dipping-pulling mode, the dipping time is 1-30s, and the pulling speed is 5-150 mm/min; and thirdly, curing the bottom layer and the surface layer in a rotating mode, wherein the rotating speed is 3-60 rpm/min.
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