Antibacterial lubricating coatings, medical devices and their preparation methods

Abstract

This application relates to an antibacterial lubricating coating, a medical device, and a method for preparing the same. By weight, the antibacterial lubricating coating comprises: 1-5 parts of a hydrophilic polymer, 2-8 parts of an antibacterial copolymer, 0.2-0.5 parts of an aqueous crosslinking agent, and 0.2-1 parts of an oily crosslinking agent. The antibacterial copolymer includes repeating units A, B, and C, with the following structural formulas: [Structure formulas would be inserted here]. The aqueous crosslinking agent is used to crosslink the repeating unit C in the hydrophilic polymer and the antibacterial copolymer. The oily crosslinking agent is used to crosslink the repeating units A and / or B in the antibacterial copolymer with the substrate. When used in catheters, the above antibacterial lubricating coating can improve the adhesion between the coating and the substrate and enhance long-term antibacterial performance while ensuring lubrication.

Description

Technical Field

[0001] This application relates to the field of medical materials, and in particular to an antibacterial lubricating coating, a medical device, and a method for preparing the same. Background Technology

[0002] Currently, during catheter placement and indwelling, a hydrophilic lubricating coating is typically applied to the catheter surface to reduce friction when entering body cavities. This coating becomes highly lubricating upon contact with bodily fluids or other moisture-containing environments, thus reducing friction during entry into body cavities. Traditional hydrophilic lubricating coatings consist of hydrophilic polymers and antibacterial agents. The hydrophilic polymers possess lubricating properties by binding with water molecules, enhancing the coating's lubricity, while the antibacterial agents provide antibacterial properties. However, the weak adhesion between the hydrophilic polymers and antibacterial agents and the substrate makes the coating prone to peeling off, resulting in insufficient long-term antibacterial performance and increasing the risk of infection with prolonged catheter indwelling. Summary of the Invention

[0003] Based on this, some embodiments of this application provide an antibacterial lubricating coating that can be used in catheters to ensure lubrication while improving the adhesion between the coating and the catheter and the long-term antibacterial properties of the coating.

[0004] In addition, some other embodiments of this application also provide a medical device and a method for preparing the same.

[0005] An antibacterial lubricating coating for forming a coating on a substrate, comprising, by weight parts: 1 to 5 parts of a hydrophilic polymer, 2 to 8 parts of an antibacterial copolymer, 0.2 to 0.5 parts of an aqueous crosslinking agent, and 0.2 to 1 part of an oily crosslinking agent;

[0006] The antibacterial copolymer comprises repeating units A, B, and C connected by covalent bonds, wherein the structural formula of repeating unit A is as follows: The structural formula of the repeating unit B is as follows: The structural formula of the repeating unit C is as follows: R1, R3 and R4 are each independently hydrogen or methyl, R2 is methyl or benzyl, and L is a linking bond or a C1-C3 alkyl group;

[0007] The aqueous crosslinking agent is used to crosslink the hydrophilic polymer and the repeating unit C in the antibacterial copolymer, and the oily crosslinking agent is used to crosslink the repeating unit A and / or repeating unit B in the antibacterial copolymer with the substrate.

[0008] In some embodiments, the molar ratio of repeating unit A, repeating unit B and repeating unit C is (3-10):(1-3):(3-5).

[0009] In some embodiments, R1 is hydrogen, R2 is benzyl, and L is a single bond.

[0010] In some embodiments, the aqueous crosslinking agent contains one or more of the following groups: azid group and amino group.

[0011] In some embodiments, the aqueous crosslinking agent includes one or more of sodium 4,4'-diazidostilbene-2,2'-disulfonate and diethylenetriamine.

[0012] In some embodiments, the oily crosslinking agent contains one or more groups selected from acrylate groups and isocyanate groups.

[0013] In some embodiments, the oily crosslinking agent includes one or more of diphenylmethane diisocyanate and polyethylene glycol diacrylate.

[0014] In some embodiments, the hydrophilic polymer includes one or more of polyvinylpyrrolidone, polyN-vinyl-2-piperidone, polyvinylimidazolium, and hyaluronic acid.

[0015] In some embodiments, the antibacterial lubricating coating further includes 0.1 to 0.5 parts by weight of an interfacial crosslinking agent, which is used to crosslink the hydrophilic polymer and the substrate.

[0016] In some embodiments, the interfacial crosslinking agent contains a first active group and a second active group, wherein the first active group includes a siloxy group and the second active group includes one or more of amino, epoxy, and carbonyl groups.

[0017] In some embodiments, the interfacial crosslinking agent includes one or more of γ-(2,3-epoxypropoxy)propyltrimethoxysilane, 3-aminopropyltrimethoxysilane, (3-aminopropyl)triethoxysilane, and γ-methacryloyloxypropyltrimethoxysilane.

[0018] In some embodiments, the antibacterial lubricating coating further includes 0.5 to 2 parts by weight of an additive, which includes one or more of surfactants and antioxidants.

[0019] In some embodiments, the additives include one or more of sodium lauryl ether sulfate and 2,6-di-tert-butyl-4-methylphenol.

[0020] A method for preparing a medical device includes the following steps:

[0021] An antibacterial lubricating coating is applied to the surface of a substrate to form a coating; wherein the antibacterial lubricating coating is as described above;

[0022] The medical device is prepared by heating to crosslink the hydrophilic polymer and the repeating unit C of the antibacterial copolymer in the coating, and to crosslink the substrate with the repeating unit A and / or repeating unit B of the antibacterial copolymer, and then curing the coating.

[0023] In some embodiments, the heating temperature is 50°C to 85°C, and the heating time is 2 hours to 6 hours.

[0024] In some embodiments, in the step of applying the antibacterial lubricating coating to the surface of the substrate, the substrate is immersed in a solution in which the antibacterial lubricating coating is dispersed for 10 to 20 seconds and then removed. The solvent in the solution in which the antibacterial lubricating coating is dispersed includes one or more of ethanol, acetone, butanone, and ethyl acetate.

[0025] A medical device is prepared by the above-described preparation method.

[0026] The antibacterial lubricating coating provided in some embodiments of this application includes a certain proportion of hydrophilic polymer, antibacterial copolymer, aqueous crosslinking agent, and oily crosslinking agent. The antibacterial copolymer includes repeating units A, B, and C. The hydrophobic portions of repeating units A and B can bond to the hydrophobic substrate surface through the oily crosslinking agent. Repeating unit B, containing a benzene ring, enhances the attractive force between the repeating unit and the cyclic structure in the hydrophilic group, resulting in a tighter network structure. The hydrophilic portion of repeating unit C in the antibacterial copolymer can bond to the hydrophilic polymer through the aqueous crosslinking agent. The antibacterial copolymer can also entangle and connect with the hydrophilic polymer through intermolecular forces, thereby improving the adhesion between the prepared coating and the substrate. Simultaneously, repeating unit A in the antibacterial copolymer contains quaternary ammonium salt groups, which have antibacterial functions. These groups exist as chemical bonds in the antibacterial copolymer, and crosslinking between the antibacterial copolymer, the hydrophilic polymer, and the substrate strengthens the bond between the antibacterial copolymer and the substrate. This prevents detachment during prolonged placement of the catheter, providing long-term antibacterial function. Therefore, the above-mentioned antibacterial lubricating coating addresses the problems of easy peeling and insufficient antibacterial performance of traditional antibacterial lubricating coatings by using an antibacterial copolymer network with quaternary ammonium salt groups and a crosslinking agent, which effectively improves the adhesion and antibacterial performance of the lubricating coating while ensuring its lubrication performance. Attached Figure Description

[0027] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0028] Figure 1 This is a process flow diagram of a method for preparing a medical device in some embodiments of this application;

[0029] Figure 2 This is a schematic diagram of the three-zone streak method during the antibacterial performance test. Detailed Implementation

[0030] To facilitate understanding of this application, a more comprehensive description of the application will be provided below in conjunction with specific embodiments. Preferred embodiments of the application are given in the specific embodiments. However, this application can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a more thorough and complete understanding of the disclosure of this application.

[0031] Unless otherwise defined, 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 application belongs. The terminology used herein in the specification of this application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0032] Unless otherwise stated or in case of conflict, the terms or phrases used in this application shall have the following meanings:

[0033] In this application, the terms "first" and "second" are used for descriptive purposes only and should not be construed as indicating or implying relative importance or implicitly specifying the number of technical features indicated. Therefore, a feature defined with "first" and "second" may explicitly or implicitly include at least one of those features.

[0034] In the description of this application, "multiple" means at least two, such as two, three, etc., unless otherwise expressly and specifically limited.

[0035] In this application, "one or more" refers to any one, any two, or any two or more of the listed items. "Several" refers to any two or more.

[0036] Unless otherwise specified, all percentage concentrations mentioned in this application refer to the final concentration. The final concentration refers to the proportion of the added component in the system after the addition of that component.

[0037] The terms "optionally" and similar expressions used in this application refer to embodiments of this application that may provide certain beneficial effects under certain circumstances. However, other embodiments may also be optional in the same or other circumstances. Furthermore, the description of one or more optional embodiments does not imply that other embodiments are unavailable, nor is it intended to exclude other embodiments from the scope of this application.

[0038] When a numerical range is disclosed in this application, the range is considered continuous and includes the minimum and maximum values ​​of the range, as well as every value between the minimum and maximum values. Furthermore, when the range refers to an integer, it includes every integer between the minimum and maximum values ​​of the range. Additionally, when multiple ranges are provided to describe a feature or characteristic, the ranges may be merged. In other words, unless otherwise specified, all ranges disclosed in this application should be understood to include any and all subranges to which they are included.

[0039] In this application, the technical features described in an open-ended manner include both closed technical solutions consisting of the listed features and open technical solutions that include the listed features.

[0040] The terms "comprising" and "having," and any variations thereof, used in the embodiments of this application, are intended to cover non-exclusive inclusion. For example, a process, method, system, product, or device that includes a series of steps or units is not limited to the steps or units listed, but may optionally include steps or units not listed, or may optionally include other steps or components inherent to such processes, methods, products, or devices.

[0041] In this application, the reference to "embodiment" means that a specific feature, structure, or characteristic described in connection with an embodiment may be included in at least one embodiment of this application. The appearance of this phrase in various places throughout the specification does not necessarily refer to the same embodiment, nor is it a mutually exclusive, independent, or alternative embodiment. It will be explicitly and implicitly understood by those skilled in the art that the embodiments described in this application can be combined with other embodiments.

[0042] The first aspect of this application provides an antibacterial lubricating coating for forming a coating on a substrate, comprising, by weight parts: 1 to 5 parts of a hydrophilic polymer, 2 to 8 parts of an antibacterial copolymer, 0.2 to 0.5 parts of an aqueous crosslinking agent, and 0.2 to 1 part of an oily crosslinking agent;

[0043] The antibacterial copolymer comprises repeating units A, B, and C connected by covalent bonds, wherein the structural formula of repeating unit A is as follows: The structural formula of the repeating unit B is as follows: The structural formula of the repeating unit C is as follows: R1, R3 and R4 are each independently hydrogen or methyl, R2 is methyl or benzyl, and L is a linking bond or a C1-C3 alkyl group;

[0044] The aqueous crosslinking agent is used to crosslink the hydrophilic polymer and the repeating unit C in the antibacterial copolymer, and the oily crosslinking agent is used to crosslink the repeating unit A and / or repeating unit B in the antibacterial copolymer with the substrate.

[0045] The antibacterial lubricating coating provided in some embodiments of this application includes a certain proportion of hydrophilic polymer, antibacterial copolymer, aqueous crosslinking agent, and oily crosslinking agent. The antibacterial copolymer includes repeating units A, B, and C. The hydrophobic portions of repeating units A and B can bond to the hydrophobic substrate surface through the oily crosslinking agent. Repeating unit B, containing a benzene ring, enhances the attractive force between the repeating unit and the cyclic structure in the hydrophilic group, resulting in a tighter network structure. The hydrophilic portion of repeating unit C in the antibacterial copolymer can bond to the hydrophilic polymer through the aqueous crosslinking agent. The antibacterial copolymer can also entangle and connect with the hydrophilic polymer through intermolecular forces, thereby improving the adhesion between the prepared coating and the substrate. Simultaneously, repeating unit A in the antibacterial copolymer contains quaternary ammonium salt groups, which have antibacterial functions. These groups exist as chemical bonds in the antibacterial copolymer, and crosslinking between the antibacterial copolymer, the hydrophilic polymer, and the substrate strengthens the bond between the antibacterial copolymer and the substrate. This prevents detachment during prolonged placement of the catheter, providing long-term antibacterial function. Therefore, the above-mentioned antibacterial lubricating coating addresses the problems of easy peeling and insufficient antibacterial performance of traditional antibacterial lubricating coatings by using an antibacterial copolymer network with quaternary ammonium salt groups and a crosslinking agent, which effectively improves the adhesion and antibacterial performance of the lubricating coating while ensuring its lubrication performance.

[0046] In an optional example, in the antibacterial lubricating coating, the mass fraction of the hydrophilic polymer may be, but is not limited to, 1 part, 1.5 parts, 2 parts, 2.5 parts, 3 parts, 3.5 parts, 4 parts, 4.5 parts, 5 parts, or any combination of these values.

[0047] In some embodiments, the hydrophilic polymer includes one or more of polyvinylpyrrolidone, poly(N-vinyl-2-piperidinone), polyvinylimidazolium, and hyaluronic acid. The hydrophilic polymer enhances the lubricity of the binding with water molecules. Furthermore, the hydrophilic polymer is entangled with the antibacterial copolymer through intermolecular forces such as hydrogen bonding and covalent bonding via crosslinking with an aqueous crosslinking agent.

[0048] In an optional example, in the antimicrobial lubricating coating, the mass fractions of the antimicrobial copolymer may be, but are not limited to, 2 parts, 2.5 parts, 3 parts, 3.5 parts, 4 parts, 4.5 parts, 5 parts, 5.5 parts, 6 parts, 6.5 parts, 7 parts, 7.5 parts, 8 parts, or any combination of these values.

[0049] In some embodiments, the molar ratio of repeating unit A, repeating unit B, and repeating unit C in the antibacterial copolymer is (3-10):(1-3):(3-5). In a specific example, the molar ratio of repeating unit A, repeating unit B, and repeating unit C is 3:1:4.

[0050] The aforementioned antibacterial copolymer forms a three-dimensional network structure comprising repeating units A, B, and C. The hydrophobic portions of repeating units A and / or B can bond to the hydrophobic substrate surface via an oil-based crosslinking agent, while the hydrophilic portions of repeating unit C can bond to the hydrophilic polymer via an aqueous crosslinking agent and can also entangle with the hydrophilic polymer through intermolecular forces, thus improving adhesion and bonding strength. Experiments have shown that using a binary copolymer or replacing components such as repeating unit B in the antibacterial copolymer with chain olefins reduces coating adhesion. Furthermore, repeating unit A in the antibacterial copolymer contains quaternary ammonium salt groups, which have antibacterial properties. These groups exist as chemical bonds in the antibacterial copolymer, and crosslinking between the antibacterial copolymer, hydrophilic polymer, and substrate results in a strong bond, preventing detachment during prolonged catheter placement and providing long-term antibacterial function.

[0051] In some embodiments, R1 is hydrogen, R2 is benzyl, and L is a single bond. In some embodiments, R3 is hydrogen. In some embodiments, R4 is hydrogen or methyl.

[0052] In some embodiments, the structural formula of the monomer corresponding to the repeating unit A is: Specifically, the monomer corresponding to repeating unit A includes one or more of N,N-dimethyl-N-benzyl-N-acrylamidoammonium chloride (DBAAC), methacryloyloxyethyltrimethylammonium chloride (DMC), and acryloyloxyethyltrimethylammonium chloride (DAC). In a specific example, the monomer corresponding to repeating unit A is N,N-dimethyl-N-benzyl-N-acrylamidoammonium chloride (DBAAC).

[0053] In some embodiments, the monomer corresponding to repeating unit B includes one or more of styrene and methylstyrene. In a specific example, the monomer corresponding to repeating unit B includes styrene.

[0054] In some embodiments, the monomer corresponding to the repeating unit C includes one or more of ethylene oxide and propylene oxide.

[0055] In some embodiments, the preparation steps of the antibacterial copolymer include: weighing the monomers corresponding to repeating unit A, repeating unit B and repeating unit C in a molar ratio of (3-10):(1-3):(3-5) and dissolving them in an organic solvent, and carrying out a heating reaction under the action of an initiator, a chain extender and nitrogen protection.

[0056] It is understandable that in the polymerization process of the three monomers, there may be two connection methods: method a: repeating unit A connects with repeating unit B, and then with repeating unit C; method b: repeating unit B connects with repeating unit C, and then with repeating unit A. Under the above reaction process, method a accounts for 30% to 80%.

[0057] In a specific example, the organic solvents include acetone and ethanol. The initiators include azo initiators, such as azobisisobutyronitrile (AIBN). The chain extender includes benzyl thiopropionate.

[0058] In a specific example, the temperature of the heating reaction is 50℃~60℃, and the heating reaction time is 15h~20h.

[0059] In one specific example, the heating reaction is followed by a step of washing and drying with anhydrous ethanol.

[0060] In a specific example, the preparation steps of the antibacterial copolymer include: weighing the monomers corresponding to repeating units A, B, and C in a molar ratio of (3–10):(1–3):(3–5) and dissolving them in a mixed solution of acetone and ethanol; heating the mixture at 50–60°C for 15–20 h under the action of an initiator and a chain extender, and under nitrogen protection. After the reaction, the mixture is washed with anhydrous ethanol and dried to obtain the antibacterial copolymer. Specifically, the initiator includes azo initiators, such as azobisisobutyronitrile (AIBN), and the chain extender includes benzyl thiopropionate.

[0061] In an optional example, in the antibacterial lubricating coating, the mass fraction of the waterborne crosslinking agent may be, but is not limited to, 0.2 parts, 0.25 parts, 0.3 parts, 0.35 parts, 0.4 parts, 0.45 parts, 0.5 parts, or any combination of these values.

[0062] In some embodiments, the aqueous crosslinking agent contains one or more groups selected from diazide groups and amino groups. In one example, the aqueous crosslinking agent includes one or more of sodium 4,4'-diazidostilbene-2,2'-disulfonate and diethylenetriamine. The aqueous crosslinking agent containing diazide groups is capable of thermal decomposition, generating highly reactive free radicals that insert into the polymer chain to achieve crosslinking with hydrophilic polymers and antibacterial copolymers. The aqueous crosslinking agent containing amino groups is capable of crosslinking with hydrophilic polymers via hydrogen bonding and with antibacterial copolymers via covalent bonding.

[0063] In an optional example, in the antibacterial lubricating coating, the mass fraction of the oily crosslinking agent may be, but is not limited to, 0.2 parts, 0.3 parts, 0.4 parts, 0.5 parts, 0.6 parts, 0.7 parts, 0.8 parts, 0.9 parts, 1 part, or a range of any two of these values.

[0064] In some embodiments, the oily crosslinking agent includes one or more of isocyanate crosslinking agents and acrylate crosslinking agents. Specifically, the oily crosslinking agent includes one or more of diphenylmethane diisocyanate and polyethylene glycol diacrylate. The oily crosslinking agent connects to the substrate by reacting with polar groups such as hydroxyl and carboxyl groups on the substrate surface, and connects to the antibacterial copolymer by reacting with hydroxyl groups or unsaturated groups in the antibacterial copolymer.

[0065] In some embodiments, the antibacterial lubricating coating further includes an interfacial crosslinking agent. The interfacial crosslinking agent is used to crosslink the hydrophilic polymer and the substrate. Specifically, the interfacial crosslinking agent contains a first active group and a second active group. The first active group includes a siloxy group, and the second active group includes one or more of amino, epoxy, and carbonyl groups. The interfacial crosslinking agent primarily connects the substrate interface and the hydrophilic polymer, bonding to the substrate surface through its first group and to the hydrophilic polymer through its second group. Adding an interfacial crosslinking agent to the antibacterial lubricating coating helps to further improve the adhesion and bonding strength between the coating and the substrate.

[0066] In one example, the interfacial crosslinking agent includes one or more of γ-(2,3-epoxypropoxy)propyltrimethoxysilane, 3-aminopropyltrimethoxysilane, (3-aminopropyl)triethoxysilane and γ-methacryloyloxypropyltrimethoxysilane.

[0067] In some embodiments, the mass fraction of the interfacial crosslinking agent in the antibacterial lubricating coating is 0.1 to 0.5 parts. For example, in an optional example, the mass fraction of the interfacial crosslinking agent in the antibacterial lubricating coating may be, but is not limited to, 0.1, 0.15, 0.2, 0.25, 0.3, 0.35, 0.4, 0.45, 0.5 parts, or any combination of these values.

[0068] By using three crosslinking agents in combination, the bonding force between the hydrophilic polymer and the antibacterial copolymer, the antibacterial copolymer and the substrate, and the hydrophilic polymer and the substrate surface are improved, which greatly enhances the adhesion of the prepared coating and makes it less likely to fall off.

[0069] In some embodiments, the antibacterial lubricating coating comprises, by weight parts: 1 to 5 parts of hydrophilic polymer, 2 to 8 parts of antibacterial copolymer, 0.2 to 0.5 parts of waterborne crosslinking agent, 0.2 to 1 part of oilborne crosslinking agent, and 0.1 to 0.5 parts of interfacial crosslinking agent.

[0070] In some embodiments, the antibacterial lubricating coating further includes additives. Additives include one or more of surfactants and antioxidants. In some embodiments, the additives include one or more of sodium lauryl ether sulfate and 2,6-di-tert-butyl-4-methylphenol. It is understood that only two commonly used additives are given above, but the invention is not limited to these, and adjustments can be made according to actual needs.

[0071] In some embodiments, the additives in the antibacterial lubricating coating are present in amounts ranging from 0.5 to 2 parts by weight. For example, in the antibacterial lubricating coating, the additives may be, but are not limited to, 0.5 parts, 0.6 parts, 0.8 parts, 1 part, 1.2 parts, 1.4 parts, 1.5 parts, 1.6 parts, 1.8 parts, 2 parts, or any combination of these values. In an optional example, the additives in the antibacterial lubricating coating include 0.5 parts by weight of sodium lauryl polyoxyethylene ether sulfate and 0.5 parts by weight of 2,6-di-tert-butyl-4-methylphenol.

[0072] In some embodiments, the antibacterial lubricating coating comprises, by weight parts: 1 to 5 parts of hydrophilic polymer, 2 to 8 parts of antibacterial copolymer, 0.2 to 0.5 parts of waterborne crosslinking agent, 0.2 to 1 part of oilborne crosslinking agent, 0.1 to 0.5 parts of interfacial crosslinking agent, and 0.5 to 2 parts of additives.

[0073] In some embodiments, the antibacterial lubricating coating may also include a solvent. The mass fraction of the solvent may be, but is not limited to, 83 parts, 84 parts, 85 parts, 86 parts, 87 parts, 88 parts, 89 parts, 90 parts, 91 parts, 92 parts, 93 parts, 94 parts, or any combination of these values.

[0074] In some embodiments, the solvent includes one or more of ethanol, acetone, butanone, and ethyl acetate. In one example, the solvent includes ethanol and butanone.

[0075] In some embodiments, the antibacterial lubricating coating comprises, by weight parts, 1 to 5 parts of hydrophilic polymer, 2 to 8 parts of antibacterial copolymer, 0.2 to 0.5 parts of waterborne crosslinking agent, 0.2 to 1 part of oilborne crosslinking agent, 0.1 to 0.5 parts of interfacial crosslinking agent, 0.5 to 2 parts of additives, and 83 to 94 parts of solvent.

[0076] In some embodiments, the preparation steps of the antibacterial lubricating coating include:

[0077] Weigh out the following raw materials by mass: 1 to 5 parts hydrophilic polymer, 2 to 8 parts antibacterial copolymer, 0.2 to 0.5 parts water-based crosslinking agent, 0.2 to 1 part oil-based crosslinking agent, 0.1 to 0.5 parts interfacial crosslinking agent, 83 to 94 parts solvent, and 0.5 to 2 parts additives.

[0078] Mix and stir the raw materials to prepare an antibacterial lubricating coating.

[0079] It is understood that in some other embodiments, the antibacterial lubricating coating may not contain solvent. When using it, the components of the antibacterial lubricating coating are mixed with the solvent to form a solution. That is, before use, the components of the antibacterial lubricating coating are independent components, and the solvent is added and mixed when using it.

[0080] The second aspect of this application provides a method for preparing a medical device; please refer to [link to relevant documentation]. Figure 1 It includes the following steps:

[0081] Step S110: Apply an antibacterial lubricating coating to the surface of the substrate to form a coating.

[0082] The antibacterial lubricating coating is as described above.

[0083] In some embodiments, the antibacterial lubricating coating contains a solvent, and the antibacterial lubricating coating can be directly applied to the substrate surface. In other embodiments, the antibacterial lubricating coating does not contain a solvent, and the components of the antibacterial lubricating coating are first mixed with a solvent before being applied to the substrate surface.

[0084] In some embodiments, an antibacterial lubricating coating is applied to the surface of a substrate by dip coating. Specifically, the substrate is immersed in a solution in which the antibacterial lubricating coating is dispersed for 10 to 20 seconds and then removed. The solvent in the solution in which the antibacterial lubricating coating is dispersed includes one or more of ethanol, acetone, butanone, and ethyl acetate.

[0085] In some embodiments, the substrate material includes one or more of polyurethane, polyvinyl chloride, silicone, and nylon.

[0086] Step S120: By heating, the repeating unit C of the hydrophilic polymer and the antibacterial copolymer in the coating is crosslinked, and the substrate is crosslinked with the repeating unit A and / or repeating unit B of the antibacterial copolymer, and the coating is cured to prepare a medical device.

[0087] In some embodiments, the heating temperature is 50°C to 85°C, and the time is 2 hours to 6 hours. For example, the curing temperature may be, but is not limited to, 50°C, 52°C, 55°C, 58°C, 60°C, 62°C, 65°C, 68°C, 70°C, 72°C, 75°C, 78°C, 80°C, 82°C, 85°C, or any combination of these values. The curing time may be, but is not limited to, 2 hours, 2.5 hours, 3 hours, 3.5 hours, 4 hours, 4.5 hours, 5 hours, 5.5 hours, 6 hours, or any combination of these values.

[0088] It is understood that in some embodiments, the antibacterial lubricating coating also contains an interfacial crosslinking agent, which is used to crosslink the hydrophilic polymer and the substrate. During the heating process, crosslinking between the hydrophilic polymer and the substrate also occurs.

[0089] Figure 1 This is a schematic flowchart of a method for preparing a medical device according to one embodiment of this application. It should be understood that, although Figure 1 The steps in the flowchart shown are displayed sequentially according to the arrows. However, these steps are not necessarily performed in the order indicated by the arrows. Unless otherwise specified in this document, there is no strict order requirement for the execution of these steps; they can be executed in other orders. Figure 1 At least some of the steps in the process may include multiple sub-steps or multiple stages. These sub-steps or stages are not necessarily completed at the same time, but can be executed at different times. Their execution order is not necessarily sequential, but can be executed in turn or alternately with at least some of other steps or other sub-steps or stages.

[0090] The third aspect of this application provides a medical device prepared by the preparation method of the second aspect described above.

[0091] In some embodiments, the medical device may be, but is not limited to, a medical catheter.

[0092] To make the objectives and advantages of this application clearer, the antibacterial lubricating coating and its effects are further described in detail below with reference to specific embodiments. It should be understood that the specific embodiments described herein are only for explaining this application and should not be used to limit this application. Unless otherwise specified, the following embodiments do not include components other than unavoidable impurities. Unless otherwise specified, the drugs and instruments used in the embodiments are conventional choices in the art. Experimental methods in the embodiments that do not specify specific conditions are implemented according to conventional conditions, such as those described in literature, books, or methods recommended by the manufacturer.

[0093] The preparation steps of the antibacterial copolymers in the following examples and comparative examples are as follows: Each monomer raw material was obtained according to the monomer and molar ratio used in each example and comparative example. These raw materials were dissolved in a mixed solution of acetone and ethanol, and reacted for 15 hours in a water bath at 50°C under the action of azobisisobutyronitrile initiator, benzyl thiopropionate chain extender, and nitrogen protection. After the reaction was completed, the copolymer was removed, washed with anhydrous ethanol, and dried to obtain the antibacterial copolymer.

[0094] Example 1

[0095] This embodiment provides an antibacterial lubricating coating, comprising, by weight parts: 2 parts polyvinylpyrrolidone, 3 parts antibacterial copolymer, 0.25 parts sodium 4,4'-diazidostilbene-2,2'-disulfonate, 0.3 parts diphenylmethane diisocyanate, 0.2 parts γ-(2,3-epoxypropoxy)propyltrimethoxysilane, 0.5 parts sodium lauryl ether sulfate, 0.5 parts 2,6-di-tert-butyl-4-methylphenol, 53.25 parts ethanol, and 40 parts butanone. The antibacterial copolymer is obtained by copolymerizing N,N-dimethyl-N-benzyl-N-acrylamidoammonium chloride (DBAAC), styrene, and ethylene oxide in a molar ratio of 3:1:4.

[0096] Stir and dissolve the above raw materials for half an hour to obtain an antibacterial lubricating coating.

[0097] Example 2

[0098] This embodiment provides an antibacterial lubricating coating, comprising, by weight parts: 2 parts polyvinylpyrrolidone, 3.2 parts antibacterial copolymer, 0.25 parts sodium 4,4'-diazidostilbene-2,2'-disulfonate, 0.3 parts diphenylmethane diisocyanate, 0.2 parts γ-(2,3-epoxypropoxy)propyltrimethoxysilane, 0.5 parts sodium lauryl ether sulfate, 0.5 parts 2,6-di-tert-butyl-4-methylphenol, 53.05 parts ethanol, and 40 parts butanone. The antibacterial copolymer is obtained by copolymerizing N,N-dimethyl-N-benzyl-N-acrylamidoammonium chloride (DBAAC), styrene, and propylene oxide in a molar ratio of 3:1:4.

[0099] Stir and dissolve the above raw materials for half an hour to obtain an antibacterial lubricating coating.

[0100] Example 3

[0101] This embodiment provides an antibacterial lubricating coating, comprising, by weight parts: 2 parts polyvinylpyrrolidone, 3 parts antibacterial copolymer, 0.25 parts sodium 4,4'-diazidostilbene-2,2'-disulfonate, 0.4 parts polyethylene glycol diacrylate, 0.2 parts γ-(2,3-epoxypropoxy)propyltrimethoxysilane, 0.5 parts sodium lauryl polyoxyethylene ether sulfate, 0.5 parts 2,6-di-tert-butyl-4-methylphenol, 53.35 parts ethanol, and 40 parts butanone. The antibacterial copolymer is obtained by copolymerizing N,N-dimethyl-N-benzyl-N-acrylamidoammonium chloride (DBAAC), styrene, and ethylene oxide in a molar ratio of 3:1:4.

[0102] Stir and dissolve the above raw materials for half an hour to obtain an antibacterial lubricating coating.

[0103] Example 4

[0104] This embodiment provides an antibacterial lubricating coating, similar to the antibacterial lubricating coating of Example 1, except that it does not contain an interfacial crosslinking agent. Specifically, by weight, it includes: 2 parts polyvinylpyrrolidone, 3 parts antibacterial copolymer, 0.25 parts sodium 4,4'-diazidostilbene-2,2'-disulfonate, 0.3 parts diphenylmethane diisocyanate, 0.5 parts sodium lauryl polyoxyethylene ether sulfate, 0.5 parts 2,6-di-tert-butyl-4-methylphenol, 53.45 parts ethanol, and 40 parts butanone. The antibacterial copolymer is obtained by copolymerizing N,N-dimethyl-N-benzyl-N-acrylamidoammonium chloride (DBAAC), styrene, and ethylene oxide in a molar ratio of 3:1:4.

[0105] Comparative Example 1

[0106] Comparative Example 1 is a hydrophilic lubricating antibacterial medical catheter from a certain brand on the market.

[0107] Comparative Example 2

[0108] Comparative Example 2 provides an antibacterial lubricating coating, similar to the antibacterial lubricating coating of Example 1, except that it does not contain an aqueous crosslinking agent. Specifically, by weight parts, it comprises: 2 parts polyvinylpyrrolidone, 3 parts antibacterial copolymer, 0.3 parts diphenylmethane diisocyanate, 0.2 parts γ-(2,3-epoxypropoxy)propyltrimethoxysilane, 0.5 parts sodium lauryl polyoxyethylene ether sulfate, 0.5 parts 2,6-di-tert-butyl-4-methylphenol, 53.5 parts ethanol, and 40 parts butanone. The antibacterial copolymer is obtained by copolymerizing N,N-dimethyl-N-benzyl-N-acrylamidoammonium chloride (DBAAC), styrene, and ethylene oxide in a molar ratio of 3:1:4.

[0109] Comparative Example 3

[0110] Comparative Example 3 provides an antibacterial lubricating coating, similar to the antibacterial lubricating coating of Example 1, except that it does not contain an oily crosslinking agent. Specifically, by mass percentage, it comprises: 2 parts polyvinylpyrrolidone, 3 parts antibacterial copolymer, 0.25 parts sodium 4,4'-diazidostilbene-2,2'-disulfonate, 0.2 parts γ-(2,3-epoxypropoxy)propyltrimethoxysilane, 0.5 parts sodium lauryl ether sulfate, 0.5 parts 2,6-di-tert-butyl-4-methylphenol, 53.55 parts ethanol, and 40 parts butanone. The antibacterial copolymer is obtained by copolymerizing N,N-dimethyl-N-benzyl-N-acrylamidoammonium chloride (DBAAC), styrene, and ethylene oxide in a molar ratio of 3:1:4.

[0111] Comparative Example 4

[0112] Comparative Example 4 provides an antibacterial lubricating coating, similar to the antibacterial lubricating coating of Example 1, except that the antibacterial copolymer is different. In Comparative Example 4, the antibacterial copolymer is obtained by copolymerizing three monomers, DBAAC, ethylene, and ethylene oxide, in a molar ratio of 3:1:4.

[0113] Comparative Example 5

[0114] Comparative Example 5 provides an antibacterial lubricating coating, similar to the antibacterial lubricating coating of Example 1, except that the antibacterial copolymer is different. In Comparative Example 5, the antibacterial copolymer is obtained by copolymerizing two monomers, DBAAC and ethylene oxide, in a molar ratio of 2:3.

[0115] The medical catheter substrate was immersed in the antibacterial lubricating coatings of the above embodiments and comparative examples for 15 seconds, and then removed and crosslinked and cured at 65°C for 4 hours to form an antibacterial lubricating coating on the surface of the medical catheter substrate, thus obtaining a medical catheter.

[0116] The following is the specific test section:

[0117] I. Antibacterial ring test

[0118] The method for testing the inhibition zone is as follows:

[0119] The experimental bacteria were Staphylococcus aureus, Candida albicans, Staphylococcus epidermidis, Escherichia coli, and Pseudomonas aeruginosa. The judgment criteria were that the above five bacteria were continuously tested for 30 days (with a new culture medium changed every day), and the diameter of the inhibition zone was greater than the diameter of the duct and the difference between the two was greater than or equal to 2 cm.

[0120] The method for testing inhibition zones is as follows:

[0121] 1. Principle

[0122] The experiment utilizes the continuous dissolution of drug within an antibacterial conduit, diffused through agar to create different concentration gradients, thereby demonstrating its antibacterial effect. The size of the inhibition zone is used to determine whether the drug possesses antibacterial ability and the extent of that ability.

[0123] 2. Reagents and Materials

[0124] 2.1 Experimental Instruments: Induction cooker, electronic balance, bacterial incubator, autoclave

[0125] 2.2 Test reagents: Nutrient broth (dry powder), nutrient agar broth (dry powder), Saburg medium (dry powder), Saburg agar medium (dry powder), physiological saline and 75% ethanol.

[0126] 3. Steps

[0127] 3.1 Preparation of Nutritious Meat Broth

[0128] (1) In a clean conical flask, dissolve 20 grams of nutritional broth powder in 1L of ultrapure water;

[0129] (2) Stir with a glass rod until fully mixed;

[0130] (3) Heat the mixture on an electromagnetic heater until it boils. Be careful to stir while heating to prevent the sediment from burning. Make sure to replenish the water as it evaporates during the heating process.

[0131] (4) Use a glass rod to dip into the nutrient broth obtained in (3) and dissolve it on pH test paper to roughly measure the pH. Try to control the pH of the broth to 7.4 to 7.6. If the difference is large, hydrochloric acid or caustic soda can be used to correct it.

[0132] (5) After the conical flask has cooled down slightly, pour it into another clean conical flask, discard the bottom part, and try to keep the broth clear. If necessary, filter it using a glass funnel and filter paper.

[0133] (6) Divide the broth into each test tube, about 3 mL per test tube, and seal each test tube with a rubber stopper or cap. In subsequent operations, try not to tilt the test tubes excessively.

[0134] (7) Bundle 10 test tubes together as a unit, wrap the head of each bundle with kraft paper and tie it tightly with thread.

[0135] (8) Sterilize the test tubes by high-pressure steam at 121°C for 20 minutes;

[0136] (9) After high-pressure steam sterilization, take out the test tubes and place them on the test tube rack. Put them in a 37°C constant temperature incubator. After 24 hours, observe that the tubes are clear and free of turbidity. They can be used after 3-4 days at 37°C or 1 week at 4°C.

[0137] 3.2 Preparation of Nutrient Agar Broth Plates

[0138] (1) In a clean conical flask, dissolve 33 grams of nutrient agar broth powder in 1L of ultrapure water;

[0139] (2) Stir with a glass rod until fully mixed;

[0140] (3) Heat the mixture on an electromagnetic heater until it boils. Stir constantly while heating to prevent the sediment from burning. Make sure to replenish the water as it evaporates during the heating process.

[0141] (4) Use a glass rod to dip into the nutrient agar broth obtained in (3) and dissolve it on pH test paper to roughly measure the pH. Try to control the pH of the broth to 7.4-7.6. If the difference is large, hydrochloric acid or caustic soda can be used to correct it.

[0142] (5) After the conical flask has cooled down slightly, divide the broth into other conical flasks and filter it with a strainer during the distribution process;

[0143] (6) Wrap the outer mouth of the conical flask with a cloth and kraft paper, and tie it tightly with thread. Wrap the petri dish with newspaper and then wrap it tightly with cloth. Sterilize the petri dish and agar broth by high pressure steam at 121°C for 20 minutes.

[0144] (7) Take out the culture dish and agar broth from the sterilization box. After the temperature drops to 60°C, pour the plates under sterile conditions to about 1 / 2 to 2 / 3 of the plate volume. Shake the plate to distribute the liquid evenly and place it in a cool place to solidify.

[0145] (8) Shake the plate until there is no liquid vibration. Invert it and observe for 24 hours. If no colony growth is observed, it is ready for use. Store at 37°C for 3-4 days or at 4°C for 1 week.

[0146] 3.3. Strain reactivation and inoculation

[0147] 3.3.1 Reactivation of freeze-dried microbial strains (first generation)

[0148] When using frozen bacterial cultures, the freeze-dried cultures must first be revived. Using aseptic technique, break open the ampoule (using a grinding wheel to separate the bottom of the bottle, applying an alcohol lamp to create a burn mark, and then breaking it open by hand). Using a sterile pipette, add 0.2 mL to 0.5 mL of sterile physiological saline or suitable liquid culture medium to the ampoule. Gently rotate the ampoule to ensure the freeze-dried cultures and liquid culture medium are thoroughly mixed and dissolved. Then transfer the bacterial solution from the ampoule to a 3 mL broth test tube and incubate for 24 to 48 hours. In the test tube, place the culture under suitable conditions according to the bacterial type [bacterial culture temperature 30℃-37℃, 18 to 24 hours; fungal culture temperature 23℃-28℃] for 3 to 5 days. Observe whether the liquid culture medium becomes turbid. Turbidity indicates that the cultures have revived and are growing. If it is not turbid, the incubation time can be appropriately extended. If it is still not turbid, sterilize according to relevant regulations and record the results in detail.

[0149] 3.3.2. Preservation of microbial strains

[0150] After identifying the characteristics of the strain, seal the liquid culture medium tube containing the pure bacterial suspension, affix a label indicating the strain name, CMCC number, number of passages, inoculation time, etc., and store it at 2℃~8℃ for later use within 2 months.

[0151] 3.3.3 Inoculation of agar plate culture medium (second generation)

[0152] (1) Under the clean bench, take out the inoculum and burn the inoculation loop with an alcohol lamp;

[0153] (2) Use your pinky finger and hypothenar eminence to unscrew the cap of the inoculum test tube, heat the esophagus opening with the outer flame, insert the inoculation loop, and take the inoculum solution.

[0154] (3) Burn the mouth of the test tube and the bottle cap again, cover the test tube with the inoculum, seal it, and store it at 2-8℃.

[0155] (4) Streak the inoculation loop onto an agar plate in three zones, and incubate the plate at 37°C for 24–48 h. Please refer to the method for streaking the three zones. Figure 2 .

[0156] 3.4. Antibacterial ring test

[0157] All samples, including human hands, must be thoroughly wiped with 75% ethanol before entering the clean bench. Using an inoculation loop or a moistened cotton swab (squeezed dry against the test tube wall until the tip is pointed), take a single bacterial culture and add it to 3 mL of physiological saline or nutrient broth. Use a pipette to take 100 μL and drop it onto a plate containing solid agar medium, spreading it evenly with a spreader until the surface is dry; or moisten a cotton swab and spread it evenly on a solid agar medium (three 60°C intervals, finally circling the plate once).

[0158] Take several small catheter segments (about 5 mm long) from each embodiment and comparative example, and use tweezers (burn them after each use) to press the drug-containing catheter tightly onto the dried plate.

[0159] Place the plate upside down in a constant temperature incubator at 37°C for 18 to 24 hours.

[0160] If the difference between the diameter of the inhibition zone of the five bacteria and the diameter of the catheter is greater than 2 cm after 30 consecutive days of testing, the antibacterial properties of the catheter meet the requirements; otherwise, they do not meet the requirements.

[0161] The results of the inhibition ring experiments for the medical catheters in each embodiment and comparative example are shown in Table 1. In Table 1, each value represents the difference between the diameter of the inhibition ring and the diameter of the catheter, in centimeters.

[0162] Table 1

[0163]

[0164] As shown in Table 1, after 30 days of continuous testing for the five bacteria in the medical catheter of Example 1, the diameter of the inhibition zone was larger than the catheter diameter, and the difference between the two was greater than 2 cm, indicating good antibacterial properties. In contrast, other brands of antibacterial catheters on the market, after 14 days of continuous testing, showed that, except for Staphylococcus epidermidis, the difference between the diameter of the inhibition zone and the catheter diameter for the other bacteria was less than 2 cm, and bacterial growth was observed next to the catheter.

[0165] II. Friction Cyclic Test

[0166] The friction force cyclic test method is as follows:

[0167] (1) Experimental principle: The lubricated catheter in a hydrophilic state is tested by using an axial tension device and a longitudinal clamping device at a set speed to obtain its sliding friction after hydrophilization.

[0168] (2) Test apparatus: axial tension device, longitudinal clamping device (equipped with a silicone pad with a Shore A hardness of 60±10), and constant temperature water bath (water temperature 37±2℃, using secondary test water that conforms to GB / T 6682-2008).

[0169] (3) Experimental steps:

[0170] 1. Immerse the medical catheter in the water tank, ensuring the part being tested is submerged. Adjust the longitudinal clamping device so that the water just covers the silicone pad, and immerse in the water for at least 30 seconds.

[0171] 2. Use the clamps of the stretching device to clamp the upper end of the medical catheter, keeping the sample vertical, and pass the lower end through the middle of the two clamps of the longitudinal clamping device. The two clamps of the longitudinal clamping device close to clamp the medical catheter and apply a clamping force of 300g.

[0172] 3. Start the tensioning device at a tensioning speed of 10 mm / s and a test displacement of 100 mm. Throughout the process, the friction force-displacement curve or friction coefficient-displacement curve of the catheter passing through the catheter clamp is automatically recorded.

[0173] 4. The number of iterations required for the test.

[0174] The frictional force cyclic test results are shown in Table 2 below:

[0175] Table 2

[0176]

[0177] As can be seen from Table 2, when the conduit coated with the hydrophilic lubricating coating of Example 1 was subjected to 50 friction cycle tests, the coefficient of friction remained less than or equal to 0.06 from 0.06 in the first test to 0.06 in the fiftieth test; and when stained with a 0.5% Congo red aqueous solution, the surface was uniformly red, proving that the coating did not peel off.

[0178] Commercially available hydrophilic lubricated medical catheters typically withstand 25 wear cycles. After 25 cycles, the coefficient of friction gradually increases, from 0.06 at the first cycle to 0.09 at the 30th cycle, and reaching approximately 0.25 at the 50th cycle. When stained with a 0.5% Congo red aqueous solution, some areas of the surface failed to stain, indicating that the coating had peeled off.

[0179] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0180] The embodiments described above are merely illustrative of several implementation methods of this application, intended to facilitate a detailed understanding of the technical solutions of this application, but should not be construed as limiting the scope of protection of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of this application, and these all fall within the scope of protection of this application. It should be understood that technical solutions obtained by those skilled in the art based on the technical solutions provided in this application through logical analysis, reasoning, or limited experimentation are all within the scope of protection of the appended claims. Therefore, the scope of protection of this patent application should be determined by the content of the appended claims, and the specification and drawings can be used to interpret the content of the claims.

Claims

1. An antibacterial lubricating coating, characterized in that, Used to form a coating on a substrate, comprising, by weight parts: 1 to 5 parts of hydrophilic polymer, 2 to 8 parts of antibacterial copolymer, 0.2 to 0.5 parts of aqueous crosslinking agent and 0.2 to 1 part of oily crosslinking agent; The antibacterial copolymer comprises repeating units A, B, and C connected by covalent bonds, wherein the structural formula of repeating unit A is as follows: The structural formula of the repeating unit B is as follows: The structural formula of the repeating unit C is as follows: R1, R3 and R4 are each independently hydrogen or methyl, R2 is methyl or benzyl, and L is a linking bond or a C1~C3 alkyl group; The aqueous crosslinking agent is used to crosslink the hydrophilic polymer and the repeating unit C in the antibacterial copolymer, and the oily crosslinking agent is used to crosslink the repeating unit A and / or repeating unit B in the antibacterial copolymer with the substrate. The aqueous crosslinking agent contains one or two groups selected from diazide groups and amino groups, and the oily crosslinking agent contains one or two groups selected from acrylate groups and isocyanate groups. The antibacterial lubricating coating further includes an interface crosslinking agent, which is used to crosslink the hydrophilic polymer and the substrate. The interface crosslinking agent contains a first active group and a second active group. The first active group includes a siloxy group, and the second active group includes one or more of amino, epoxy, and carbonyl groups.

2. The antibacterial lubricating coating according to claim 1, characterized in that, The molar ratio of repeating unit A, repeating unit B and repeating unit C is (3~10):(1~3):(3~5).

3. The antibacterial lubricating coating according to claim 1, characterized in that, R1 is hydrogen, R2 is benzyl, and L is a single bond.

4. The antibacterial lubricating coating according to claim 1, characterized in that, The aqueous crosslinking agent includes one or two of sodium 4,4'-diazidostilbene-2,2'-disulfonate and diethylenetriamine.

5. The antibacterial lubricating coating according to claim 1, characterized in that, The oily crosslinking agent includes one or both of diphenylmethane diisocyanate and polyethylene glycol diacrylate.

6. The antibacterial lubricating coating according to claim 1, characterized in that, The hydrophilic polymer includes one or more of polyvinylpyrrolidone, polyN-vinyl-2-piperidinone, polyvinylimidazolium, and hyaluronic acid.

7. The antibacterial lubricating coating according to any one of claims 1 to 6, characterized in that, In the antibacterial lubricating coating, the mass fraction of the interfacial crosslinking agent is 0.1 to 0.5 parts.

8. The antibacterial lubricating coating according to claim 1, characterized in that, The interface crosslinking agent includes one or more of γ-(2,3-epoxypropoxy)propyltrimethoxysilane, 3-aminopropyltrimethoxysilane, (3-aminopropyl)triethoxysilane and γ-methacryloxypropyltrimethoxysilane.

9. The antibacterial lubricating coating according to any one of claims 1 to 6 and 8, characterized in that, The antibacterial lubricating coating also includes 0.5 to 2 parts by weight of additives, which include one or two of surfactants and antioxidants.

10. The antibacterial lubricating coating according to claim 9, characterized in that, The additives include one or both of sodium lauryl ether sulfate and 2,6-di-tert-butyl-4-methylphenol.

11. A method for preparing a medical device, characterized in that, Includes the following steps: An antibacterial lubricating coating is applied to the surface of a substrate to form a coating; wherein the antibacterial lubricating coating is as described in any one of claims 1 to 10; The medical device is prepared by heating to crosslink the hydrophilic polymer and the repeating unit C of the antibacterial copolymer in the coating, and to crosslink the substrate with the repeating unit A and / or repeating unit B of the antibacterial copolymer, and then curing the coating.

12. The method for preparing the medical device according to claim 11, characterized in that, The heating temperature is 50℃~85℃, and the time is 2h~6h.

13. The method for preparing the medical device according to claim 11 or 12, characterized in that, In the step of applying an antibacterial lubricating coating to the surface of a substrate, the substrate is immersed in a solution in which the antibacterial lubricating coating is dispersed for 10 to 20 seconds and then removed. The solvent in the solution in which the antibacterial lubricating coating is dispersed includes one or more of ethanol, acetone, butanone, and ethyl acetate.

14. A medical device, characterized in that, It is prepared by the preparation method according to any one of claims 11 to 13.

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