WO2021254348A1 - 一种介入瓣膜输送系统的超润滑涂层及其制备方法 - Google Patents

一种介入瓣膜输送系统的超润滑涂层及其制备方法 Download PDF

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WO2021254348A1
WO2021254348A1 PCT/CN2021/100184 CN2021100184W WO2021254348A1 WO 2021254348 A1 WO2021254348 A1 WO 2021254348A1 CN 2021100184 W CN2021100184 W CN 2021100184W WO 2021254348 A1 WO2021254348 A1 WO 2021254348A1
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parts
super
delivery system
valve delivery
interventional valve
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PCT/CN2021/100184
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English (en)
French (fr)
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王云兵
高帅
雷洋
武迪蒙
杨立
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杭州启明医疗器械股份有限公司
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    • 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
    • A61L29/04—Macromolecular materials
    • A61L29/041—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L2420/02—Methods for coating medical devices
    • 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

Definitions

  • the invention relates to the technical field of medical materials, in particular to a super-lubricating coating of an interventional valve delivery system and a preparation method thereof.
  • the application of interventional valve systems to patients with valve diseases has been promoted year by year.
  • the interventional valve system includes the main functional components such as the delivery system, the valve holder, and the valve leaflet.
  • the interventional valve system delivery systems are mainly composed of dilatation catheters and sheaths, and the dilatation catheters are made of polypropylene (PP) or polyethylene (PE) materials.
  • PP polypropylene
  • PE polyethylene
  • the above problems can be solved by attaching a lubricating coating to the surface of the dilatation catheter.
  • the main technical measures for the lubricity of the catheter surface are: one is to coat paraffin oil or complex iodine on the surface of the catheter; the other is to form a super-lubricating coating on the surface of the catheter. Among them, forming a super-lubricating coating on the surface of the catheter is a better solution.
  • the material of the expansion catheter of the interventional valve delivery system is PP or PE with low surface energy, it is difficult to form a strong super-lubricating coating on the surface, and the resulting coating has poor biocompatibility.
  • the present invention provides a super-lubricant coating for interventional valve delivery systems and a preparation method thereof.
  • the surface of the polypropylene or polyethylene dilation catheter has good adhesion, which greatly reduces the friction between the catheter and the sheath, which can effectively ensure the smooth operation of the delivery system during use, shorten the operation time, and reduce Surgery risks.
  • the technical solution adopted by the present invention to solve its technical problems is to provide a super-lubricating coating for interventional valve delivery systems, including the following parts by mass of raw materials: 2.5-16.8 parts of unsaturated oligomers, active diluent 2 ⁇ 8 parts, UV light initiator 1 ⁇ 4.5 parts, silicone tackifier 1 ⁇ 3 parts, leveling agent 0.3 ⁇ 2.4 parts, 2-methacryloxyethyl phosphocholine 0.2 ⁇ 2.3 parts, poly 1-10 parts of vinylpyrrolidone and 50-89 parts of solvent.
  • the ultra-lubricating coating of the interventional valve delivery system includes the following parts by mass of raw materials: 12 parts of unsaturated oligomer, 2 parts of active diluent, 4 parts of ultraviolet light initiator, 2.5 parts of silicone tackifier, and leveling agent 1 part, 1.5 parts of 2-methacryloyloxyethyl phosphoric acid choline, 10 parts of polyvinylpyrrolidone, and 60 parts of solvent.
  • the unsaturated oligomer is at least one of monofunctional or polyfunctional epoxy acrylic resin, urethane acrylic resin, polyester acrylic resin, polyether acrylic resin, acrylated acrylate resin, and vinyl resin. kind.
  • the reactive diluent is at least one of monofunctional or multifunctional acrylic, methacrylate, vinyl, vinyl ether, or epoxy.
  • the ultraviolet light initiator is benzoin/acyl and its derivatives, benzophenone and its derivatives, thioxanthone and its derivatives, anthraquinone and its derivatives, acetophenone derivatives, ⁇ - Hydroxy/amino ketone derivatives, benzoyl formates, acyl phosphine oxides, aryl diazonium salts, diaryliodonium salts, triaryl sulfonium salts, fumerocene salts, macromolecular benzophenones, macromolecules At least one of thioxanthone, macromolecular aminoacetophenone, macromolecular ⁇ -hydroxy ketone, macromolecular benzoyl formate, macromolecular oxime ketone ester, macromolecular acyl phosphinated oxygen and macromolecular amine alkyl ketone kind.
  • organosilicon tackifier is prepared by the following method:
  • Vinyl hydroxy silicone oil and silane coupling agent are prepared by reaction under the catalysis of titanate compound.
  • the vinyl content in the vinyl hydroxy silicone oil is 1-20 wt%, and the hydroxyl content is 1-20 wt%.
  • the molar ratio of the hydroxyl group in the vinyl hydroxy silicone oil to the silane coupling agent is 1-10:1.
  • the amount of titanate compound used is 0.05 to 1 wt%.
  • the vinyl hydroxy silicone oil and the silane coupling agent are mixed uniformly at room temperature, the titanate compound is added dropwise, and the temperature is raised to 60-120° C. to react for 1 to 5 hours, and after post-treatment, the organosilicon tackifier is obtained.
  • the post-treatment includes: cooling to 60-90° C. under reduced pressure distillation for 1 to 5 hours to obtain the organosilicon tackifier.
  • the post-treatment includes: cooling to 60-90° C. under reduced pressure distillation for 1 to 5 hours, and then lowering to room temperature in a vacuum to obtain an organosilicon tackifier.
  • the organosilicon tackifier is prepared by the following method: mixing vinyl hydroxy silicone oil and silane coupling agent at room temperature, adding 0.05-1wt% titanate compound dropwise, stirring and heating to 60-120 under the protection of nitrogen React at °C for 1 ⁇ 5h, then lower the temperature to 60 ⁇ 90°C and distill under reduced pressure for 1 ⁇ 5h, and then lower to room temperature in vacuum to obtain the organosilicon tackifier.
  • the vinyl content in the vinyl hydroxy silicone oil is 1-20 wt%, and the hydroxyl content is 1-20 wt%; and the molar ratio of the hydroxyl group and the silane coupling agent in the vinyl hydroxy silicone oil is 1-10:1.
  • the silane coupling agent is vinyl trimethoxy silane, vinyl triethoxy silane, methacryloxy propyl trimethoxy silane, acryloxy propyl trimethoxy silane, methacryloyl At least one of oxytriethoxysilane, acryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane and 3-mercaptopropyltriethoxysilane;
  • the titanate compound is titanium Tetrabutyl titanate, tetraethyl titanate, tetraisopropyl titanate, tetra-tert-butyl titanate, di(acetylacetone) diisopropyl titanate, acetylacetone complex isopropyl titanate, ethyl acetoacetate At least one of ester complexed with isopropyl titanate and ethyl acetoacetate complexed with propylene glycol titanate.
  • the leveling agent is at least one of polyether/polyester/aralkyl modified silicone polysiloxane, acrylates, and fluorine-modified acrylates;
  • the solvent is methanol, ethanol, isopropanol, normal At least one of propanol, allyl alcohol, isobutanol, n-butanol, and ethylene glycol methyl ether.
  • the above-mentioned preparation method of the super-lubricating coating of the interventional valve delivery system includes the following steps:
  • the present invention has the following advantages:
  • the super-lubricating coating of the present invention has good biocompatibility, and can have good adhesion on the surface of dilatation catheters made of polypropylene or polyethylene with low surface energy and difficult to adhere, which greatly reduces catheters and sheaths.
  • the friction force between them can effectively ensure the smooth operation of the delivery system during use, shorten the operation time, avoid problems such as poor operation and prolong operation time, and reduce the risk of surgery; and the ultra-lubricant coating is mixed in sequence during preparation , Coating and UV curing, the preparation process is simple, the super lubricating coating can be quickly prepared, the preparation efficiency is improved, and the preparation time of the super lubricating coating is shortened.
  • unsaturated oligomer is used as the matrix resin to participate in the photo-curing reaction as the main component to improve the mechanical strength of the cured coating, and to a certain extent improve the adhesion of the coating; the active diluent participates in the photo-curing reaction.
  • the curing reaction becomes a part of the cross-linking network structure of the coating after curing, and at the same time, the viscosity of the coating liquid is adjusted;
  • the photoinitiator can initiate the polymerization, cross-linking and curing of unsaturated oligomers, reactive diluents and silicone tackifiers to promote the curing reaction
  • the new structure of silicone tackifier prepared, containing active vinyl, sulfhydryl and hydroxyl, can participate in the photo-curing reaction, and can improve the adhesion of the coating to the substrate (polypropylene or polyethylene) after curing Adhesive ability; leveling agent can reduce the surface energy of the coating liquid, so that the coating liquid adheres evenly on the surface of the substrate; 2-methacryloyloxyethyl phosphoric acid choline can participate in the photocuring reaction and improve the biological phase of the coating liquid Compatibility: In the cured coating, polyvinylpyrrolidone can form a hydrogel after
  • the preparation method of the super-lubricant coating is simple and feasible, and the coating has good biocompatibility after UV curing; synthetic silicone tackifier, used in the super-lubricant coating, can significantly improve the curing and expansion of the coating Catheter bonding ability; after the super-lubricating coating is activated by water, it can greatly reduce the friction between the catheter and the sheath.
  • a super-lubricating coating for interventional valve delivery system including the following parts by mass: 10 parts of multifunctional acrylate (Dymax BR-970), 1,6-hexanediol propoxy (2) diacrylate (HD2PODA Photomer) 4362) 5 parts, bifunctional ⁇ -hydroxy ketone oligomer 3 parts, silicone tackifier 2 parts, leveling agent (BYK-378) 2.4 parts, 2-methacryloxyethyl phosphate choline 0.2 Parts, 5 parts of polyvinylpyrrolidone (K-90) and 67.4 parts of ethanol.
  • the organosilicon tackifier is prepared by the following method: at room temperature 85g vinyl hydroxy silicone oil (containing 0.3 mol of hydroxyl group, vinyl content of 6.5% wt, hydroxyl content of 6% wt) and 8.89 g of vinyl trimethoxy Mix silane (0.06mol) uniformly, add 0.047g of tetrabutyl titanate dropwise, stir and heat up to 70°C for 2h under the protection of nitrogen, then reduce the temperature to 65°C and distill under reduced pressure for 1.5h, and then reduce to room temperature in a vacuum. Silicone tackifier.
  • the above-mentioned preparation method of the super-lubricating coating of the interventional valve delivery system includes the following steps:
  • a super lubricating coating for interventional valve delivery system including the following parts by mass: 6 parts of aliphatic urethane acrylate (NeoRad U-25-20D), 4 parts of fatty acid modified epoxy acrylate (AgiSyn 2020-80), Dipropylene glycol diacrylate (DPGDA Photomer 4226) 8 parts, bifunctional ⁇ -hydroxy ketone oligomer 2 parts, silicone tackifier 3 parts, leveling agent (BYK-3560) 1.5 parts, 2-methyl propylene 0.5 parts of acyloxyethyl phosphocholine, 2 parts of polyvinylpyrrolidone (K-120), 30 parts of isopropanol and 43 parts of ethanol.
  • the silicone tackifier is prepared by the following method: at room temperature 85g vinyl hydroxy silicone oil (containing 0.15 mol of hydroxyl group, 3% wt vinyl content, 3% wt hydroxyl content) and 28.55g vinyl triethoxy Add 0.43 g of tetraethyl titanate dropwise, stir and warm to 80°C for 2.5 hours under nitrogen protection, then cool to 70°C and distill under reduced pressure for 2 hours, and then reduce to room temperature in a vacuum. Get organosilicon tackifier.
  • the above-mentioned preparation method of the super-lubricating coating of the interventional valve delivery system includes the following steps:
  • a super-lubricating coating for interventional valve delivery system including the following parts by mass: 9 parts of polyester acrylate (AgiSyn 730), 3 parts of amine-modified epoxy acrylate (Photomer 3317), and polyethylene glycol (600) Diacrylate (PEG600DA AgiSyn 2835) 6 parts, 2-isopropylthioxanthone 1 part, silicone tackifier 1 part, leveling agent (TEGO Dispers 710) 0.8 part, 2-methacryloyloxyethane 0.7 parts of phosphorylcholine, 6 parts of polyvinylpyrrolidone (K-90) and 72.5 parts of ethanol.
  • the silicone tackifier is prepared by the following method: at room temperature 85g vinyl hydroxy silicone oil (containing 0.3 mol of hydroxy Trimethoxysilane (0.03mol) was mixed, 0.92g acetylacetone complex isopropyl titanate was added dropwise, stirred and heated to 90°C for 3h under nitrogen protection, then cooled to 75°C and distilled under reduced pressure for 2.5h, and then Reduce to room temperature in a vacuum to obtain a silicone tackifier.
  • the above-mentioned preparation method of the super-lubricating coating of the interventional valve delivery system includes the following steps:
  • a super-lubricating coating for interventional valve delivery system including the following parts by mass: 12 parts of amine-modified polyether acrylate (Photomer 5850), 2 parts of modified epoxy diacrylate (Photomer 3072), and triethylene glycol 4 parts of divinyl ether (DVE-3), 4 parts of polymerized benzophenone derivatives, 2.5 parts of silicone tackifier, 1 part of leveling agent (TEGO Dispers 672), 2-methacryloyloxyethane 1.5 parts of phosphocholine phosphate, 10 parts of polyvinylpyrrolidone (K-30), 3 parts of polyvinylpyrrolidone (K-120) and 60 parts of isopropanol.
  • the silicone tackifier is prepared by the following method: at room temperature, 85g of vinyl hydroxy silicone oil (containing 0.3 mol of hydroxy group, 5% wt of vinyl content, and 6% wt of hydroxy Oxysilane (0.1mol) and mix well, add 0.64g of tetra-tert-butyl titanate dropwise, stir under the protection of nitrogen and raise the temperature to 100°C to react for 3.5h, then reduce the temperature to 80°C and distill under reduced pressure for 3h, then reduce to At room temperature, the silicone tackifier can be obtained.
  • the above-mentioned preparation method of the super-lubricating coating of the interventional valve delivery system includes the following steps:
  • a super-lubricating coating for interventional valve delivery system including the following parts by mass: 7 parts of pure acrylate (AgiSyn 260-163), 1 part of low-viscosity modified epoxy acrylate (Photomer 3316), 7 parts of lauric acid acrylate Parts, 4.5 parts of aminoalkyl phenone containing piperazinyl group, 1.5 parts of silicone tackifier, 2 parts of (BYK-UV 3500), 1 part of 2-methacryloxyethyl phosphoric acid choline, polyethylene 2 parts of pyrrolidone (K-90), 1 part of polyvinylpyrrolidone (K-120) and 50 ⁇ 89 parts of isopropanol.
  • the silicone tackifier is prepared by the following method: at room temperature, 85g of vinyl hydroxy silicone oil (containing 0.15 mol of hydroxyl group, 2% by weight of vinyl content, and 3% by weight of hydroxyl group) and 14.73g of mercaptopropyl trimethoxy Silane (0.075mol), add 0.74g of di(acetylacetone) diisopropyl titanate dropwise, stir and heat up to 110°C for 5h under nitrogen protection, then cool to 85°C and distill under reduced pressure for 4h, then vacuum It is lowered to room temperature to obtain organosilicon tackifier.
  • the above-mentioned preparation method of the super-lubricating coating of the interventional valve delivery system includes the following steps:
  • Comparative Example 1 lacks a silicone tackifier.
  • the super-lubricity coating prepared in Examples 1 to 5 of the present invention has a high cell survival rate for the dilatation catheter, and the introduction of the coating basically does not have a negative impact on the biocompatibility; compared with the uncoated dilatation catheter In comparison, the friction of Examples 1 to 5 is significantly reduced. After hundreds of tests, the friction is still less than 0.3N, and the adhesion of the coating to the dilatation catheter is good; while the dilatation catheter of Comparative Example 1 has no added organic For silicon tackifiers, with the increase of the number of tests, the frictional force shows an obvious upward trend.

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Abstract

本发明公开了一种介入瓣膜输送系统的超润滑涂层及其制备方法，超润滑涂层，包括以下质量份原料：不饱和低聚物2.5~16.8份、活性稀释剂2~8份、紫外光引发剂1~4.5份、有机硅增粘剂1~3份、流平剂0.3~2.4份、2-甲基丙烯酰氧乙基磷酸胆碱0.2~2.3份、聚乙烯吡咯烷酮1~10份和溶剂50~89份。本发明还提供了超润滑涂层的制备方法。本发明的超润滑涂层具有良好生物相容性，可以在低表面能、难粘附的聚丙烯或聚乙烯材质的扩张导管表面有良好的附着，极大程度的降低了导管和鞘管之间的摩擦力，从而可以有效保证输送系统使用过程中的顺滑操作，缩短手术时间，降低手术风险。

Description

一种介入瓣膜输送系统的超润滑涂层及其制备方法 技术领域
本发明涉及医用材料技术领域，具体涉及一种介入瓣膜输送系统的超润滑涂层及其制备方法。
 背景技术
介入瓣膜系统对于瓣膜疾病患者的应用逐年推广。介入瓣膜系统包括输送系统、瓣架、瓣叶等主要功能部件。目前市场上，国内外介入瓣膜系统输送系统主要由扩张导管和鞘管组成，其中扩张导管由聚丙烯（PP）或聚乙烯（PE）材料制备而成。临床使用中，扩张导管和鞘管之间存在较大摩擦力，可能导致出现操作不顺畅、延长手术时间等问题，加大了患者的手术风险。
通过在扩张导管表面附着润滑涂层可以解决上述问题。导管表面具有润滑性的技术措施主要有：一是在导管的表面涂覆石蜡油或络合碘；二是在导管的表面形成超润滑涂层。其中在导管表面形成超润滑涂层是较优的解决方案。但是由于介入瓣膜输送系统扩张导管材料是低表面能的PP或PE，很难在其表面形成牢固的超润滑涂层，且所得涂层生物相容性较差。
 技术问题
针对现有技术中的上述不足，本发明提供了一种介入瓣膜输送系统的超润滑涂层及其制备方法，超润滑涂层具有良好生物相容性，可以在低表面能、难粘附的聚丙烯或聚乙烯材质的扩张导管表面有良好的附着，极大程度的降低了导管和鞘管之间的摩擦力，从而可以有效保证输送系统使用过程中的顺滑操作，缩短手术时间，降低手术风险。
 技术解决方案
为实现上述目的，本发明解决其技术问题所采用的技术方案是：提供一种介入瓣膜输送系统的超润滑涂层，包括以下质量份原料：不饱和低聚物2.5~16.8份、活性稀释剂2~8份、紫外光引发剂1~4.5份、有机硅增粘剂1~3份、流平剂0.3~2.4份、2-甲基丙烯酰氧乙基磷酸胆碱0.2~2.3份、聚乙烯吡咯烷酮1~10份和溶剂50~89份。
进一步，介入瓣膜输送系统的超润滑涂层，包括以下质量份原料：不饱和低聚物12份、活性稀释剂2份、紫外光引发剂4份、有机硅增粘剂2.5份、流平剂1份、2-甲基丙烯酰氧乙基磷酸胆碱1.5份、聚乙烯吡咯烷酮10份和溶剂60份。
进一步，不饱和低聚物为单官能度或多官能度的环氧丙烯酸树脂、聚氨酯丙烯酸树脂、聚酯丙烯酸树脂、聚醚丙烯酸树脂、丙烯酸酯化的丙烯酸酯树脂和乙烯基树脂中的至少一种。
进一步，活性稀释剂为单官能度或多官能度的丙烯酸酯类、甲基丙烯酸酯类、乙烯基类、乙烯基醚类或环氧类中至少一种。
进一步，紫外光引发剂为苯偶姻/酰及其衍生物、二苯甲酮及其衍生物、硫杂蒽酮及其衍生物、蒽醌及其衍生物、苯乙酮衍生物、α-羟基/氨基酮衍生物、苯甲酰甲酸酯类、酰基膦氧化物、芳基重氮盐、二芳基碘鎓盐、三芳基硫鎓盐、方茂铁盐、大分子二苯甲酮、大分子硫杂蒽酮、大分子氨基苯乙酮、大分子α-羟基酮、大分子苯甲酰甲酸酯、大分子肟酮酯、大分子酰基膦化氧和大分子胺烷基酮中至少一种。
进一步，所述有机硅增粘剂通过以下方法制备得到：
乙烯基羟基硅油和硅烷偶联剂在钛酸酯化合物的催化作用下，反应制备得到。
进一步，所述乙烯基羟基硅油中乙烯基含量为1~20wt%，羟基含量为1~20wt%。
进一步，所述乙烯基羟基硅油中羟基和所述硅烷偶联剂摩尔比为1~10:1。
进一步，钛酸酯化合物的用量为0.05~1wt%。
进一步，室温下将乙烯基羟基硅油和硅烷偶联剂混匀，滴加钛酸酯化合物，升温至60~120℃反应1~5h，经后处理，得到所述有机硅增粘剂。
进一步，后处理包括：降温至60~90℃减压蒸馏1~5h，得到所述有机硅增粘剂。
进一步，后处理包括：降温至60~90℃减压蒸馏1~5h，再在真空中降至室温，得有机硅增粘剂。
进一步，有机硅增粘剂通过以下方法制备得到：室温下将乙烯基羟基硅油和硅烷偶联剂混匀，滴加0.05~1wt%的钛酸酯化合物，在氮气保护下搅拌升温至60~120℃反应1~5h，然后降温至60~90℃减压蒸馏1~5h，再在真空中降至室温，得有机硅增粘剂。
进一步，乙烯基羟基硅油中乙烯基含量为1~20wt%，羟基含量为1~20wt%；且乙烯基羟基硅油中羟基和硅烷偶联剂摩尔比为1~10:1。
进一步，硅烷偶联剂为乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、甲基丙烯酰氧基丙基三甲氧基硅烷、丙烯酰氧基丙基三甲氧基硅烷、甲基丙烯酰氧基三乙氧基硅烷、丙烯酰氧基丙基三甲氧基硅烷、3-巯丙基三甲氧基硅烷和3-巯丙基三乙氧基硅烷中至少一种；钛酸酯化合物为钛酸四丁酯、钛酸四乙酯、钛酸四异丙酯、钛酸四叔丁酯、二（乙酰丙酮）钛酸二异丙酯、乙酰丙酮络合钛酸异丙酯、乙酰乙酸乙酯络合钛酸异丙酯、乙酰乙酸乙酯络合钛酸丙二醇酯中至少一种。
进一步，流平剂为聚醚/聚酯/芳烷基改性有机硅聚硅氧烷、丙烯酸酯类、氟改性丙烯酸酯类中至少一种；溶剂为甲醇、乙醇、异丙醇、正丙醇、烯丙醇、异丁醇、正丁醇和乙二醇甲醚中至少一种。
上述的介入瓣膜输送系统的超润滑涂层的制备方法，包括以下步骤：
在室温下，将所有原料搅拌均匀，然后涂覆在扩张导管上，在10~30 mW/cm 2的紫外光强度下固化0.25~30min，得介入瓣膜输送系统的超润滑涂层。
有益效果
综上所述，本发明具有以下优点：
1、本发明超润滑涂层具有良好生物相容性，可以在低表面能、难粘附的聚丙烯或聚乙烯材质的扩张导管表面有良好的附着，极大程度的降低了导管和鞘管之间的摩擦力，从而可以有效保证输送系统使用过程中的顺滑操作，缩短手术时间，避免出现操作不畅和延长手术时间等问题，降低手术风险；且超润滑涂层制备时依次混匀、涂覆和紫外固化，制备流程简单，可以快速制得超润滑涂层，提高制备效率，缩短超润滑涂层制备时间。
2、在超润滑涂层中，以不饱和低聚物为基体树脂，作为主要成分参与光固化反应，提高固化后涂层力学强度，一定程度上提高涂层的附着能力；活性稀释剂参与光固化反应，成为固化后涂层交联网络结构的一部分，同时调节涂层液粘度；光引发剂能够引发不饱和低聚物、活性稀释剂和有机硅增粘剂聚合交联固化，促进固化反应的进行；制得的新型结构的有机硅增粘剂，含有活性乙烯基、巯基和羟基，既可以参与光固化反应，又可以提高涂层固化后与基材（聚丙烯或聚乙烯）的附着粘接能力；流平剂能够降低涂层液表面能，使涂层液在基材表面附着均匀；2-甲基丙烯酰氧乙基磷酸胆碱能够参与光固化反应，提高涂层液生物相容性；在固化后的涂层中，聚乙烯吡咯烷酮遇水激活后可以形成水凝胶，赋予涂层超润滑性能；而溶剂溶解涂层液各组分，起到调节粘度的作用。
3、超润滑涂层制备方法简单可行，涂层经过紫外光固化后具有良好的生物相容性；合成的有机硅增粘剂，用于超润滑涂层中可以显著提高涂层固化后与扩张导管粘接附着能力；超润滑涂层经水激活后，可极大降低导管和鞘管之间的摩擦力。
 本发明的实施方式
实施例1
一种介入瓣膜输送系统的超润滑涂层，包括以下质量份原料：多功能丙烯酸酯（Dymax BR-970）10份、1,6-己二醇丙氧基（2）二丙烯酸酯（HD2PODA Photomer 4362）5份、双官能度α-羟基酮低聚物3份、有机硅增粘剂2份、流平剂（BYK-378）2.4份、2-甲基丙烯酰氧乙基磷酸胆碱0.2份、聚乙烯吡咯烷酮（K-90）5份和乙醇67.4份。
其中，有机硅增粘剂通过以下方法制备得到：室温下将85g乙烯基羟基硅油（含羟基0.3mol，乙烯基含量为6.5%wt，羟基含量为6%wt）和8.89g乙烯基三甲氧基硅烷（0.06mol）混匀，滴加0.047g钛酸四丁酯，在氮气保护下搅拌升温至70℃反应2h，然后降温至65℃减压蒸馏1.5h，再在真空中降至室温，得有机硅增粘剂。
上述的介入瓣膜输送系统的超润滑涂层的制备方法，包括以下步骤：
在室温下，将所有原料搅拌均匀，然后涂覆在聚丙烯扩张导管上，在25 mW/cm 2的紫外光强度下固化10min，得介入瓣膜输送系统的超润滑涂层。
实施例2
一种介入瓣膜输送系统的超润滑涂层，包括以下质量份原料：脂肪族聚氨酯丙烯酸酯（NeoRad U-25-20D）6份、脂肪酸改性环氧丙烯酸酯（AgiSyn 2020-80）4份、二丙二醇二丙烯酸酯（DPGDA Photomer 4226）8份、双官能度α-羟基酮低聚物2份、有机硅增粘剂3份、流平剂（BYK-3560）1.5份、2-甲基丙烯酰氧乙基磷酸胆碱0.5份、聚乙烯吡咯烷酮（K-120）2份、异丙醇30份和乙醇43份。
其中，有机硅增粘剂通过以下方法制备得到：室温下将85g乙烯基羟基硅油（含羟基0.15mol，乙烯基含量为3%wt，羟基含量为3%wt）和28.55g乙烯基三乙氧基硅烷（0.15mol）混匀，滴加0.43 g钛酸四乙酯，在氮气保护下搅拌升温至80℃反应2.5h，然后降温至70℃减压蒸馏2h，再在真空中降至室温，得有机硅增粘剂。
上述的介入瓣膜输送系统的超润滑涂层的制备方法，包括以下步骤：
在室温下，将所有原料搅拌均匀，然后涂覆在聚丙烯扩张导管上，在10 mW/cm 2的紫外光强度下固化20min，得介入瓣膜输送系统的超润滑涂层。
实施例3
一种介入瓣膜输送系统的超润滑涂层，包括以下质量份原料：聚酯丙烯酸酯（AgiSyn 730）9份、胺改性环氧丙烯酸酯（Photomer 3317）3份、聚乙二醇（600）二丙烯酸酯（PEG600DA AgiSyn 2835）6份、2-异丙基硫杂蒽酮1份、有机硅增粘剂1份、流平剂（TEGO Dispers 710）0.8份、2-甲基丙烯酰氧乙基磷酸胆碱0.7份、聚乙烯吡咯烷酮（K-90）6份和乙醇72.5份。
其中，有机硅增粘剂通过以下方法制备得到：室温下将85g乙烯基羟基硅油（含羟基0.3mol，乙烯基含量为3%wt，羟基含量为6%wt）和7.44g甲基丙烯酰氧基三甲氧基硅烷（0.03mol）混匀，滴加0.92g乙酰丙酮络合钛酸异丙酯，在氮气保护下搅拌升温至90℃反应3h，然后降温至75℃减压蒸馏2.5h，再在真空中降至室温，得有机硅增粘剂。
上述的介入瓣膜输送系统的超润滑涂层的制备方法，包括以下步骤：
在室温下，将所有原料搅拌均匀，然后涂覆在聚乙烯扩张导管上，在30 mW/cm 2的紫外光强度下固化5min，得介入瓣膜输送系统的超润滑涂层。
实施例4
一种介入瓣膜输送系统的超润滑涂层，包括以下质量份原料：胺改性聚醚丙烯酸酯（Photomer 5850）12份、改性的环氧二丙烯酸酯（Photomer 3072）2份、三甘醇二乙烯基醚（DVE-3）4份、聚合的二苯甲酮衍生物4份、有机硅增粘剂2.5份、流平剂（TEGO Dispers 672）1份、2-甲基丙烯酰氧乙基磷酸胆碱1.5份、聚乙烯吡咯烷酮（K-30）10份、聚乙烯吡咯烷酮（K-120）3份和异丙醇60份。
其中，有机硅增粘剂通过以下方法制备得到：室温下将85g乙烯基羟基硅油（含羟基0.3mol，乙烯基含量为5%wt，羟基含量为6%wt）和23.4g丙烯酰氧基三甲氧基硅烷（0.1mol）混匀，滴加0.64g钛酸四叔丁酯，在氮气保护下搅拌升温至100℃反应3.5h，然后降温至80℃减压蒸馏3h，再在真空中降至室温，得有机硅增粘剂。
上述的介入瓣膜输送系统的超润滑涂层的制备方法，包括以下步骤：
在室温下，将所有原料搅拌均匀，然后涂覆在聚乙烯扩张导管上，在20 mW/cm 2的紫外光强度下固化8min，得介入瓣膜输送系统的超润滑涂层。
实施例5
一种介入瓣膜输送系统的超润滑涂层，包括以下质量份原料：纯丙烯酸酯（AgiSyn 260-163）7份、低粘度改性环氧丙烯酸酯（Photomer 3316）1份、月桂酸丙烯酸酯7份、含哌嗪基的胺基烷基苯酮4.5份、有机硅增粘剂1.5份、（BYK-UV 3500）2份、2-甲基丙烯酰氧乙基磷酸胆碱1份、聚乙烯吡咯烷酮（K-90）2份、聚乙烯基吡咯烷酮（K-120）1份和异丙醇50~89份。
其中，有机硅增粘剂通过以下方法制备得到：室温下将85g乙烯基羟基硅油（含羟基0.15mol，乙烯基含量为2%wt，羟基含量为3%wt）和14.73g巯丙基三甲氧基硅烷（0.075mol）混匀，滴加0.74g二（乙酰丙酮）钛酸二异丙酯，在氮气保护下搅拌升温至110℃反应5h，然后降温至85℃减压蒸馏4h，再在真空中降至室温，得有机硅增粘剂。
上述的介入瓣膜输送系统的超润滑涂层的制备方法，包括以下步骤：
在室温下，将所有原料搅拌均匀，然后涂覆在聚丙烯扩张导管上，在15 mW/cm 2的紫外光强度下固化15min，得介入瓣膜输送系统的超润滑涂层。
对比例1
对比例1与实施例的不同之处在于，对比例1缺少有机硅增粘剂。
分别对实施1~5所得超润滑涂层、对比例1所得涂层和两个空白对照组（无涂层聚丙烯管、无涂层聚乙烯管）进行细胞毒性、摩擦力测试，其结果见表1。
表1   细胞毒性和摩擦力测试结果统计表
Figure dest_path_image001
注：1、细胞存活率按照GB/T 16886.5-2017《医疗器械生物学评价第5部分：体外细胞毒性试验》规定的方法测试。
2、摩擦力按照YY/T 1536-2017 《非血管内导管表面滑动性能评价用标准试验模型》规定的方法测试。
由表1可知，本发明中实施例1~5中制备的超润滑涂层的扩张导管细胞存活率高，涂层的引入基本不会对生物相容性产生负面影响；与无涂层扩张导管相比，实施例1~5的摩擦力显著降低，经过上百次测试，摩擦力仍然低于0.3N，涂层与扩张导管的附着力好；而对比例1的扩张导管，由于没有添加有机硅增粘剂，随着测试次数的增加，摩擦力呈明显的上升趋势。
虽然本发明的具体实施方式对本发明进行了详细地描述，但不应理解为对本专利的保护范围的限定。在权利要求书所描述的范围内，本领域技术人员不经创造性劳动即可作出的各种修改和变形仍属本专利的保护范围。

Claims (17)

  1. 一种介入瓣膜输送系统的超润滑涂层，其特征在于，包括以下质量份原料：不饱和低聚物2.5~16.8份、活性稀释剂2~8份、紫外光引发剂1~4.5份、有机硅增粘剂1~3份、流平剂0.3~2.4份、2-甲基丙烯酰氧乙基磷酸胆碱0.2~2.3份、聚乙烯吡咯烷酮1~10份和溶剂50~89份。
  2. 如权利要求1所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述有机硅增粘剂通过以下方法制备得到：
    乙烯基羟基硅油和硅烷偶联剂在钛酸酯化合物的催化作用下，反应制备得到。
  3. 如权利要求2所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述乙烯基羟基硅油中乙烯基含量为1~20wt%，羟基含量为1~20wt%。
  4. 如权利要求2所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述乙烯基羟基硅油中羟基和所述硅烷偶联剂摩尔比为1~10:1。
  5. 如权利要求2所述的介入瓣膜输送系统的超润滑涂层，其特征在于，钛酸酯化合物的用量为0.05~1wt%。
  6. 如权利要求2所述的介入瓣膜输送系统的超润滑涂层，其特征在于，室温下将乙烯基羟基硅油和硅烷偶联剂混匀，滴加钛酸酯化合物，升温至60~120℃反应1~5h，经后处理，得到所述有机硅增粘剂。
  7. 如权利要求6所述的介入瓣膜输送系统的超润滑涂层，其特征在于，后处理包括：降温至60~90℃减压蒸馏1~5h，得到所述有机硅增粘剂。
  8. 如权利要求6所述的介入瓣膜输送系统的超润滑涂层，其特征在于，后处理包括：降温至60~90℃减压蒸馏1~5h，再在真空中降至室温，得有机硅增粘剂。
  9. 如权利要求1所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述有机硅增粘剂通过以下方法制备得到：室温下将乙烯基羟基硅油和硅烷偶联剂混匀，滴加0.05~1wt%的钛酸酯化合物，在氮气保护下搅拌升温至60~120℃反应1~5h，然后降温至60~90℃减压蒸馏1~5h，再在真空中降至室温，得有机硅增粘剂。
  10. 如权利要求2~9任一项所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述硅烷偶联剂为乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、甲基丙烯酰氧基丙基三甲氧基硅烷、丙烯酰氧基丙基三甲氧基硅烷、甲基丙烯酰氧基三乙氧基硅烷、丙烯酰氧基丙基三甲氧基硅烷、3-巯丙基三甲氧基硅烷和3-巯丙基三乙氧基硅烷中至少一种。
  11. 如权利要求2~9任一项所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述钛酸酯化合物为钛酸四丁酯、钛酸四乙酯、钛酸四异丙酯、钛酸四叔丁酯、二（乙酰丙酮）钛酸二异丙酯、乙酰丙酮络合钛酸异丙酯、乙酰乙酸乙酯络合钛酸异丙酯、乙酰乙酸乙酯络合钛酸丙二醇酯中至少一种。
  12. 如权利要求1所述的介入瓣膜输送系统的超润滑涂层，其特征在于，包括以下质量份原料：不饱和低聚物12份、活性稀释剂2份、紫外光引发剂4份、有机硅增粘剂2.5份、流平剂1份、2-甲基丙烯酰氧乙基磷酸胆碱1.5份、聚乙烯吡咯烷酮10份和溶剂60份。
  13. 如权利要求1~9任一项所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述不饱和低聚物为单官能度或多官能度的环氧丙烯酸树脂、聚氨酯丙烯酸树脂、聚酯丙烯酸树脂、聚醚丙烯酸树脂、丙烯酸酯化的丙烯酸酯树脂和乙烯基树脂中的至少一种。
  14. 如权利要求1~9任一项所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述活性稀释剂为单官能度或多官能度的丙烯酸酯类、甲基丙烯酸酯类、乙烯基类、乙烯基醚类或环氧类中至少一种。
  15. 如权利要求1~9任一项所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述紫外光引发剂为苯偶姻/酰及其衍生物、二苯甲酮及其衍生物、硫杂蒽酮及其衍生物、蒽醌及其衍生物、苯乙酮衍生物、α-羟基/氨基酮衍生物、苯甲酰甲酸酯类、酰基膦氧化物、芳基重氮盐、二芳基碘鎓盐、三芳基硫鎓盐、方茂铁盐、大分子二苯甲酮、大分子硫杂蒽酮、大分子氨基苯乙酮、大分子α-羟基酮、大分子苯甲酰甲酸酯、大分子肟酮酯、大分子酰基膦化氧和大分子胺烷基酮中至少一种。
  16. 如权利要求1~9任一项所述的介入瓣膜输送系统的超润滑涂层，其特征在于，所述流平剂为聚醚/聚酯/芳烷基改性有机硅聚硅氧烷、丙烯酸酯类、氟改性丙烯酸酯类中至少一种；所述溶剂为甲醇、乙醇、异丙醇、正丙醇、烯丙醇、异丁醇、正丁醇和乙二醇甲醚中至少一种。
  17. 权利要求1~16任一项所述的介入瓣膜输送系统的超润滑涂层的制备方法，其特征在于，包括以下步骤：
    在室温下，将所有原料搅拌均匀，然后涂覆在扩张导管上，在10~30 mW/cm 2的紫外光强度下固化0.25~30min，得介入瓣膜输送系统的超润滑涂层。
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