New-type antifouling developing coating material, and preparation method therefor and use thereof

Abstract

A new-type antifouling developing coating material, and a preparation method therefor and the use thereof. In the antifouling developing coating material, choline phosphate is bonded with an ionic developer by means of a covalent bonding technology, which ensures the stability of antifouling and developing properties, such that the antifouling developing coating material has wide application prospects in the field of medical imaging.

Description

A new antifouling developing coating material and its preparation method and application Technical Field

[0001] The present application relates to the field of medical material technology, for example, a new anti-fouling developing coating material and its preparation method and application. Background Art

[0002] Medical developer coatings play an indispensable role in the field of medical imaging. With the continuous advancement of medical imaging technology, the requirements for developer coatings are also increasing. In addition to excellent development effects, they must also possess excellent anti-fouling properties to prevent the adhesion of bacterial proteins, thereby preventing bacterial infection and cross-infection, and maintain a clean and transparent surface to ensure clear and accurate images.

[0003] The developing performance of medical anti-fouling developer coatings is crucial to the clarity and diagnostic accuracy of medical images, helping doctors diagnose diseases and guide treatment. They can not only reveal the condition of skeletal structure, soft tissue, and organs, but also detect lesions such as tumors, fractures, and infections. Therefore, medical developer coatings play an indispensable role in medical fields such as radiodiagnosis and interventional radiotherapy. In X-ray imaging, human tissue has varying degrees of absorption capacity for X-rays. Denser tissues, such as bone and metal, absorb X-rays more strongly, while soft tissue absorbs less. Medical developer coatings enhance the absorption or scattering of X-rays in certain areas, thereby forming a clear image on X-ray film or digital detectors. Typically, these coatings contain one or more chemicals that absorb X-rays and convert them into visible images.

[0004] Developers are one of the most important components of medical developer coatings. There are many different types, with iodides, tungstates, and lead compounds being common. Each developer has its own unique advantages and disadvantages. For example, iodide developers have high absorption capacity and produce clear images, but they are somewhat irritating to skin and tissues, have low biocompatibility, and are difficult to use for long-term internal imaging, requiring more stringent dosage concentrations. Tungstate developers, on the other hand, are less irritating and suitable for use in certain sensitive areas, but their image clarity is slightly inferior to that of iodide developers. Therefore, we are committed to improving the compatibility of iodide developers by introducing modified phosphorylcholine polymer molecules with excellent biocompatibility. This improves their antifouling properties and biocompatibility without compromising the developer's visual quality.

[0005] In the field of medical imaging, integrating imaging and antifouling technologies is a challenging task. While both are of practical significance, effectively integrating them is not easy. The fundamental challenge lies in the potential constraints between the two. Traditional imaging technologies often require specific chemical compositions to achieve clear and accurate images, and these chemical compositions can interact adversely with the materials used in antifouling technologies. For example, some coatings designed to enhance antifouling properties can affect the adsorption and diffusion of developer, thereby reducing imaging efficiency. Conversely, certain developers can affect the antifouling properties of the coating, causing it to lose its original functionality. Therefore, achieving antifouling properties without compromising imaging, or achieving imaging without weakening the coating's antifouling properties, remains a primary challenge in integrating imaging and antifouling technologies. To address this challenge, researchers are focusing on optimizing the coating's composition and structure, and optimizing their proportions. For example, nanomaterials with antimicrobial properties are introduced to enhance the coating's antimicrobial capabilities while maintaining the developer's adsorption and diffusion properties. Furthermore, the scientific team is exploring ways to optimize the developer's formulation and process, minimizing its impact on the coating's antifouling properties by modifying its chemical composition and concentration. For example, the pH value of the developer can be adjusted to reduce its corrosion and damage to the coating.

[0006] Although the integration of imaging and antifouling technologies faces numerous challenges, with the continuous advancement of science and technology and the continuous improvement of theories, we believe that these challenges will eventually be overcome. In the future, we can expect the integration of imaging and antifouling technologies to become a key technology in the field of medical imaging, bringing new breakthroughs in medical image clarity and diagnostic accuracy.

[0007] Summary of the Invention

[0008] The following is a summary of the subject matter described in detail herein. This summary is not intended to limit the scope of the claims.

[0009] The present application provides a novel anti-fouling developing coating material and a preparation method and application thereof.

[0010] In one aspect, the present application provides a novel anti-fouling and developing coating material, wherein the anti-fouling and developing coating material has a structure as shown in the following formula I:

[0011] wherein m=1-40 (e.g., 1, 2, 3, 5, 8, 10, 13, 15, 18, 20, 22, 25, 28, 30, 32, 34, 36, 38, or 40, etc.), n=1-40 (e.g., 1, 2, 3, 5, 8, 10, 13, 15, 18, 20, 22, 25, 28, 30, 32, 34, 36, 38, or 40, etc.), and k=1-4 (e.g., 1, 2, 3, or 4), and the ionic developer is covalently bound to the modified phosphorylcholine.

[0012] The anti-fouling and developing coating material described in this application combines anti-fouling and developing through covalent bonding technology, thereby ensuring the stability of the material and the stability of the anti-fouling and developing properties, so that the material has outstanding performance in both anti-fouling performance and developing effect, making it have broad application prospects in the field of medical imaging, and providing strong support for the safety of medical equipment and the accuracy of medical images.

[0013] In some optional embodiments, the ionic imaging agent is selected from one or a combination of at least two of diatrizoate, iodalafil, iodixanol, and cholangiocarbamide.

[0014] In some alternative embodiments, the ionic imaging agent is diatrizoate.

[0015] In some optional embodiments, the ionic developer is connected to the siloxane via a linking group.

[0016] In some optional embodiments, the ionic developer is connected to the siloxane by forming a Si—O—Si bond.

[0017] In some optional embodiments, the ionic developer is connected to the aminosilane coupling agent through an amide condensation reaction; the connection method is based on an O═C—N—H amide bond.

[0018] In some optional embodiments, the silane-containing ionic developer is connected to the anti-fouling molecule-modified phosphorylcholine polymer via a linking group through a silane hydrolysis polymerization reaction.

[0019] In some optional embodiments, the linking group is selected from any one of a methylsilyl group, a vinylsilyl group, an aminosilyl group, a triphenylphosphine group, an olefin phosphine ligand group, and a mercaptophosphine ligand group.

[0020] In some optional embodiments, the anti-fouling developing coating material has a structure shown in the following formula II:

[0021] wherein m=1-40 (e.g., 1, 2, 3, 5, 8, 10, 13, 15, 18, 20, 22, 25, 28, 30, 32, 34, 36, 38, or 40), n=1-40 (e.g., 1, 2, 3, 5, 8, 10, 13, 15, 18, 20, 22, 25, 28, 30, 32, 34, 36, 38, or 40), k=1-3 (e.g., 1, 2, or 3), R is selected from a C1-C5 alkyl group, and L is

[0022] In some optional embodiments, m:n=1:1-4:1, for example, 1:1, 2:1, 3:1 or 4:1. In the present application, the ratio of m:n is within 1:1-4:1, which can make the material have both good developing effect and good anti-fouling effect.

[0023] In some alternative embodiments, m:n=3:1.

[0024] On the other hand, the present application provides a method for preparing the novel anti-fouling developing coating material as described above, the preparation method comprising the following steps:

[0025] The novel anti-fouling developing coating material is obtained by reacting an ionic developer containing a silane group with a modified phosphorylcholine polymer modified by siloxane.

[0026] Optionally, the molar ratio of the silane-containing ionic developer to the siloxane-modified modified phosphorylcholine polymer is 1:1 to 4:1, for example, 1:1, 1.5:1, 1.8:1, 2:1, 2.3:1, 2.5:1, 2.8:1, 3:1, 3.5:1, 3.8:1 or 4:1.

[0027] Optionally, the reaction is carried out at room temperature, and the reaction time is 6-24 h, such as 6 h, 8 h, 10 h, 12 h, 15 h, 18 h, 20 h, 22 h or 24 h, optionally 12 h.

[0028] Optionally, the silane-containing ionic developer is prepared by the following preparation method: an ionic developer is reacted with a siloxane compound to obtain the silane-containing ionic developer.

[0029] Optionally, the siloxane compound is selected from any one or a combination of at least two of 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane or 3-aminopropyltriethoxysilane.

[0030] Optionally, the molar ratio of the ionic developer to the siloxane compound is 1:1 to 1:3, for example, 1:1, 1:1.2, 1:1.5, 1:1.8, 1:2, 1:2.2, 1:2.5, 1:2.8 or 1:3.

[0031] Optionally, the reaction of the ionic developer with the siloxane compound is carried out in the presence of O-benzotriazole-tetramethyluronium hexafluorophosphate.

[0032] Optionally, the reaction of the ionic developer with the siloxane compound is carried out in the presence of triethylamine.

[0033] Optionally, the reaction temperature of the ionic developer and the siloxane compound is 50-80°C, for example, 50°C, 55°C, 60°C, 65°C, 70°C, 75°C or 80°C, and the reaction time is 6-24h, for example, 6h, 8h, 10h, 12h, 15h, 18h, 20h, 22h or 24h.

[0034] Optionally, the reaction of the ionic developer and the siloxane compound is carried out in a solvent, and the solvent is N,N-dimethylformamide.

[0035] Optionally, the preparation method of the modified phosphorylcholine polymer comprises the following steps:

[0036] 2-Methacryloyloxyethyl phosphorylcholine reacts with a siloxane compound to obtain the siloxane-modified modified phosphorylcholine polymer.

[0037] Optionally, the siloxane compound is methacryloxypropyltris(trimethylsiloxy)silane and / or 3-(methacryloxy)propyltrimethoxysilane.

[0038] Optionally, the molar ratio of the 2-methacryloyloxyethyl phosphorylcholine to the siloxane compound is 1:1-8:1, for example, 1:1, 1.5:1, 2:1, 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1, 5:1, 5.5:1, 6:1, 6.5:1, 7:1, 7.5:1 or 8:1.

[0039] Optionally, the reaction of 2-methacryloyloxyethyl phosphorylcholine with the siloxane compound is carried out in the presence of 4-cyano-4-(thiobenzoyl)valeric acid.

[0040] Optionally, the molar ratio of 2-methacryloyloxyethyl phosphorylcholine to 4-cyano-4-(thiobenzoyl)pentanoic acid is 1:1-5:1, for example 1:1, 1.5:1, 2:1, 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1 or 5:1.

[0041] Optionally, the reaction of 2-methacryloyloxyethyl phosphorylcholine with the siloxane compound is carried out in the presence of an initiator.

[0042] Optionally, the initiator is selected from azobisisobutyronitrile.

[0043] Optionally, the molar ratio of the 2-methacryloyloxyethyl phosphorylcholine to the initiator is 1:1-5:1, for example 1:1, 1.5:1, 2:1, 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1 or 5:1.

[0044] Optionally, the reaction temperature of the 2-methacryloyloxyethyl phosphorylcholine and the siloxane compound is 60°C-70°C (e.g., 60°C, 63°C, 65°C, 68°C or 70°C), and the reaction time is 16-64h (e.g., 16h, 18h, 20h, 24h, 28h, 30h, 36h, 40h, 42h, 48h, 50h, 55h, 58h, 60h or 64h).

[0045] Optionally, the reaction of 2-methacryloyloxyethyl phosphorylcholine and the siloxane compound is carried out in a solvent selected from n-propanol.

[0046] Optionally, the reaction of 2-methacryloyloxyethyl phosphorylcholine and the siloxane compound is carried out under nitrogen protection.

[0047] Optionally, the specific operation of the preparation method of the modified phosphorylcholine polymer is as follows: dissolving 2-methacryloyloxyethyl phosphorylcholine, 4-cyano-4-(thiobenzoyl)valeric acid, and azobisisobutyronitrile in n-propanol, heating to 60°C-70°C under nitrogen protection, stirring and reacting for 16-32 hours, and then adding a siloxane compound, and continuing the reaction for 16-32 hours to obtain the modified phosphorylcholine polymer.

[0048] As a further preferred technical solution, the preparation method of the modified phosphorylcholine polymer comprises the following steps:

[0049] 0.5-1 mol of 2-methacryloyloxyethyl phosphorylcholine, 0.2-0.5 mol of 4-cyano-4-(thiobenzoyl)valeric acid, and 0.2-0.5 mol of azobisisobutyronitrile are dissolved in n-propanol, and the temperature is slowly raised to 60-70°C under nitrogen protection. The mixture is stirred and reacted for 16-32 hours. Then, 0.125-0.25 mol of methacryloyloxypropyltris(trimethylsiloxy)silane or 0.125-0.25 mol of 3-(methacryloyloxy)propyltrimethoxysilane is added, and the reaction is continued for 16-32 hours. The obtained n-propanol solution is added to ether for precipitation, and filtered and dried to obtain the product.

[0050] In another aspect, the present application provides use of the novel antifouling developing coating material described above in coating a substrate surface.

[0051] Optionally, the substrate surface includes a silicon-based surface, a glass-based surface, a metal-based surface, or a high-molecular polymer-based surface.

[0052] The material of the present application can be applied to the surfaces of various substrates, including glass substrates, metal substrates and various plastic and polymer substrates (silicone rubber, polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyurethane, etc.).

[0053] In the present application, the developing functional monomer and the antifouling functional polymer in the novel antifouling developing coating material are connected by a silicon oxide compound, and the silicon oxide compound can be more firmly bonded to the substrate, thereby ensuring the stability and safety of the coating material of the present application on the substrate. Especially in the case of a silicon-based substrate, the silicon oxide compound can be incorporated into the substrate material, or even covalently bonded to the substrate material, to further ensure safety.

[0054] The present application provides a design and preparation concept for a new antifouling developing coating that can be applied to any substrate surface, including an optional silicon-based substrate surface. The structural design principle of its molecular structure is shown in Figure 1. The molecular structure of the new antifouling developing coating material involved in this application mainly includes two parts, namely a developing functional monomer and an antifouling functional polymer. The developing functional monomer uses a compound that can covalently bind to phosphorylcholine, such as an intermediate molecule obtained by reacting an iodine-containing compound (such as iohexol hydrolyzate) with epoxy silane. The developing functional monomer has excellent X-ray absorption properties and can produce accurate and clear developing effects in medical imaging, providing reliable imaging information for medical angiography. The developing functional monomer is tightly combined with the antifouling polymer modified phosphorylcholine that also contains silane groups through silane hydrolysis polymerization to form a composite structure while maintaining their respective properties. The introduction of the antifouling functional monomer gives the coating excellent antifouling properties, which can effectively inhibit the adhesion of protein bacteria, thereby preventing bacterial infection and cross-infection. In scenarios with high hygiene standards such as medical equipment and catheters, this antifouling property is of great significance to ensure the hygienic safety of medical equipment. Through the combined action of developer-functional monomers and antifouling monomers, the new antifouling developer coating forms a product with silane groups. This covalent bonding ensures exceptional stability on silicon-based surfaces, preventing loss or detachment over time, significantly improving the durability and reliability of the developer coating. Furthermore, due to the universality of the silane groups, the coating can bond to a variety of substrates, including glass, metal, and various plastic and polymer substrates (silicone rubber, polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyurethane, etc.), providing broad applicability and flexibility for the developer coating's application areas.

[0055] The design concept of this application's antifouling developer material cleverly combines developer and antifouling functions. By rationally selecting monomers and achieving covalent bonding, the coating possesses both developer and antifouling properties. This design concept is universal and operational, providing a new direction for the research and development and application of medical imaging developer materials, and bringing further progress and breakthroughs to the fields of medical diagnosis and treatment.

[0056] On the other hand, the present application provides an anti-fouling developing coating, wherein the raw materials for preparing the anti-fouling developing coating include the novel anti-fouling developing coating material as described above.

[0057] On the other hand, the present application provides the use of the novel antifouling developing coating material as described above in medical devices or medical materials, optical lenses or industrial printing.

[0058] The coating material of this application can be applied to antifouling and developing functional coatings for medical devices, giving the coated objects both antifouling and X-ray imaging functions. The novel antifouling and developing coating of this application can also be further applied to optical lens coatings and antifouling and developing functional coatings in the field of industrial printing.

[0059] Compared with the related art, this application has the following beneficial effects:

[0060] First, this new antifouling developer coating material has been successfully applied to medical devices, creating a highly effective antifouling coating. Compared to traditional developer coatings, it offers significant improvements in antifouling performance. The coating contains a modified phosphorylcholine polymer, a unique antifouling agent that effectively resists the adhesion of bacterial proteins, thereby preventing bacterial infection and cross-infection. This property is crucial for medical safety, ensuring the hygienic and safe use of medical devices. It is suitable for a variety of medical scenarios and is particularly important for equipment requiring high hygiene standards, such as operating rooms and medical catheters.

[0061] Secondly, this new anti-fouling developer coating material demonstrates superior development performance. Compared to traditional developer coatings, it is a water-insoluble elastomeric coating that is not absorbed by the body's metabolism. This ensures a stable and long-lasting development effect, eliminates potential side effects of developer coatings, and improves the safety of medical developer coatings, which has positive implications for patient health and the medical experience.

[0062] Furthermore, this new antifouling developing coating material is universally applicable. By binding to the hydroxyl groups on the substrate surface, it can achieve covalent bonding with any silicon-based substrate, including glass, silicone sheets, marble, and other silicon-based surfaces. Furthermore, through hydrophobic interactions or van der Waals forces, it is also suitable for bonding with other substrate surfaces. It is widely applicable in various clinical and laboratory scenarios, meeting the needs of different users. Compared with traditional coatings, its preparation method is simpler and less expensive, providing a feasible path for the large-scale application of developing coatings.

[0063] In summary, this new antifouling and developing coating material not only achieves significant improvements in antifouling performance but also demonstrates excellent developing performance and universal applicability. It incorporates a modified phosphorylcholine polymer to effectively prevent bacterial protein adhesion, ensuring the hygiene and safety of medical devices. Furthermore, its water-insoluble coating ensures stable developing performance, reduces side effects, and improves the safety of medical developing coatings. Its broad applicability allows it to be combined with various silicon-based substrates, and its simple and low-cost preparation method provides a reliable solution for ensuring the accuracy of medical images and the maintenance of medical devices. Therefore, the emergence of this new antifouling and developing coating represents a breakthrough in the maintenance of medical devices and the accuracy of medical images, with enormous market potential and broad application prospects.

[0064] Still other aspects will become apparent upon reading and understanding the accompanying drawings and detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0065] The accompanying drawings are used to provide a further understanding of the technical solution of this article and constitute a part of the specification. Together with the embodiments of this application, they are used to explain the technical solution of this article and do not constitute a limitation on the technical solution of this article.

[0066] Figure 1 is a schematic diagram of the design principle of the new anti-fouling developing coating material.

[0067] Figure 2 shows the nuclear magnetic resonance test results of the new anti-fouling developing coating material.

[0068] FIG3 shows the anticoagulation test results of the novel antifouling developing coating material;

[0069] FIG4A is a photograph showing the results of a novel antifouling developing coating material antibacterial adhesion test;

[0070] FIG4B is a diagram showing the quantitative analysis results of bacterial colonies adsorbed by the novel antifouling developing coating material;

[0071] FIG5A is a graph showing the results of an anti-platelet adhesion test of a novel anti-fouling developing coating;

[0072] FIG5B is a graph showing the quantitative analysis results of the number of platelets adhered to the novel anti-fouling developing coating. DETAILED DESCRIPTION

[0073] The technical solution of the present application is further described below through specific implementation methods. Those skilled in the art should understand that the embodiments are only used to help understand the present application and should not be regarded as specific limitations of the present application.

[0074] Example 1 Synthesis example of modified phosphorylcholine polymer.

[0075] 0.75 mol of 2-methacryloyloxyethyl phosphorylcholine, 0.4 mol of 4-cyano-4-(thiobenzoyl)valeric acid, and 0.4 mol of azobisisobutyronitrile were dissolved in n-propanol. Under nitrogen, the temperature was slowly raised to 65°C and stirred for 24 hours. Then, 0.125 mol of methacryloxypropyltris(trimethylsiloxy)silane was added and the reaction continued for 24 hours. The resulting n-propanol solution was added to diethyl ether for precipitation, filtered, and dried to obtain a phosphorylcholine polymer. The reaction is shown below.

[0076] Example 2 Synthesis example of a new antifouling developing coating.

[0077] 1) Dissolve diatrizoate (1g) in 10mL N,N-dimethylformamide solvent, then add O-benzotriazole-tetramethyluronium hexafluorophosphate (0.7g) and triethylamine (200μL) and stir at 60°C and ultrasonicate to fully dissolve to obtain a colorless solution; dissolve 3-aminopropyltrimethoxysilane (330μL) in 10mL N,N-dimethylformamide solvent, then mix it with the colorless solution in the previous step and stir in a 60°C oil bath overnight. Then, separate the target product by column chromatography. Then, remove the organic solvent by rotary evaporation, and further dialyze and liquid phase purification to obtain the silicon-modified developing functional monomer C. 20 H 30 I3N3O6Si.

[0078] 2) The above-mentioned developer-functional monomer and the antifouling functional polymer modified phosphorylcholine synthesized in Example 1 were mixed in a methanol / water binary solvent at a ratio of 1:2 to a concentration of 400 mg / ml. The mixture was stirred at room temperature for 6 hours to allow for complete hydrolysis and polymerization of the silyl groups of the modified phosphorylcholine antifouling molecule, thereby forming an antifouling developer polymer that can be coated on any silicon-based substrate (Figure 1).

[0079] Example 3 Tests of the present application on basic characterization of compounds.

[0080] The new antifouling developer coating in this application was used for basic characterization nuclear magnetic resonance testing, and deuterated dimethyl sulfoxide was selected as the solvent. Figure 2 shows the results of the nuclear magnetic resonance test. The peak at 3.55ppm shows the successful polymerization of the silane bond, and the peak formed at 8.44ppm proves the condensation of the amide bond, indicating that the diatrizoate is successfully polymerized with the silane group. The peaks formed at 3.3 and 4.5ppm are the side chain groups of the modified phosphorylcholine, which proves the successful polymerization of the modified phosphorylcholine and the ionic developer. In summary, the nuclear magnetic resonance results verify that the ionic developer monomer C with a silane bond 20 H 30 Successful polymerization of I3N3O6Si with modified phosphorylcholine.

[0081] Example 4 Test of the anticoagulant effect of this application

[0082] The novel antifouling and developing coating described in this application was used to test its anticoagulant effect. The adsorption capacity of rat whole blood on the coating was measured and characterized. The coating used contained a 1:2 mass ratio of diatrizoate glucosamine to antifouling functional polymer-modified phosphorylcholine. The coating solution was prepared by dissolving the coating material in isopropyl alcohol to obtain solutions with concentrations of 10 mg / mL and 20 mg / mL, respectively. This solution was then coated on a silicone hose. The hose, coated with the coating, was then immersed in freshly drawn rat whole blood, removed after five minutes, and rinsed three times with saline. A control group consisted of a blank sample without the coating. The results are shown in Figure 3.

[0083] As shown in Figure 3, the coating exhibited excellent anti-coagulation ability compared to the blank control. Blood hardly adsorbed on the coating, while the blank control was completely covered with whole blood.

[0084] Example 5 Test of the present application in terms of anti-bacterial adhesion

[0085] The antibacterial adhesion test was conducted using the novel antifouling developer coating material in this application. In this test, the antibacterial adsorption ability of the antifouling developer polymer coating was characterized, and the test involved Candida albicans (C.albicans), Escherichia coli (E.coli), and Staphylococcus aureus (S.aureus). In the antifouling developer coating used, the mass ratio of diatrizoate glucosamine to antifouling functional polymer modified phosphorylcholine was 1:2 (prepared in Example 2), and the total concentration was 400 mg / mL. The sample was exposed to high concentration (10 8After soaking in three live bacterial solutions (100 μg / mL) for two weeks, the samples were removed and air-dried, and the bacterial counts were observed using a scanning electron microscope (SEM, S-3400N). The live bacteria were replaced every three days to ensure bacterial activity. The control group served as a blank control. The results are shown in Figures 4A and 4B ("Uncoating" indicates the results without anti-fouling developer coating, and "Coating" indicates the results with anti-fouling developer coating).

[0086] Figure 4A shows that after two weeks of adsorption of three different bacteria, large colonies were evident on the control sample without the anti-fouling developer coating, while no significant colony growth was observed on the sample coated with the anti-fouling developer coating. Further quantitative analysis of the adsorbed colonies, as shown in Figure 4B, demonstrates that the anti-fouling developer coating significantly reduced bacterial adhesion, with the amount of bacteria adhered reduced by 95% after two weeks.

[0087] Example 6 Testing of the present application in terms of anti-platelet adhesion

[0088] The anti-platelet adhesion performance test was carried out using the new anti-fouling developing coating material in this application. The coating was coated on different matrix materials such as NiTi, PVC and TPU, and then the platelets were exposed to the surface of the test material, washed and observed under a scanning electron microscope (SEM) to explore the effect of the anti-fouling developing coating on platelet adhesion. The coating concentrations used in the experimental group were 100 mg / mL, 200 mg / mL and 300 mg / mL (concentration in isopropanol), and the control group used a blank negative control. According to the results of Figure 5A, the anti-fouling developing coating significantly reduced the adhesion of platelets on the surfaces of various materials. According to the quantitative analysis results of Figure 5B, it can be seen that with the increase of the coating concentration, the anti-platelet adhesion effect of the anti-fouling developing coating is significantly enhanced (in Figures 5A and 5B, Uncoating is the result of not coating the anti-fouling developing coating, and different concentrations represent the results of coating the anti-fouling developing coating of the concentration).

[0089] The applicant declares that while the above-mentioned embodiments are used to illustrate the process of the present application, the present application is not limited to the above-mentioned process steps, which does not mean that the present application must rely on the above-mentioned process steps in order to be implemented. Those skilled in the art should understand that any improvements to the present application, equivalent replacements for the raw materials used in the present application, addition of auxiliary components, and selection of specific methods, etc., fall within the scope of protection and disclosure of the present application.

Claims

1. A novel antifouling developing coating material, wherein: The anti-fouling developing coating material has a structure as shown in the following formula I: Among them, m=1~40, n=1~40, k=1~4.

2. The novel antifouling developing coating material according to claim 1, wherein: The ionic developer is selected from one or a combination of at least two of diatrizoate, iodalafil, iodixanol and choledochal meglumine, and diatrizoate may be selected.

3. The novel antifouling developing coating material according to claim 1 or 2, wherein: The ionic developer and the siloxane are connected via a connecting group; Optionally, the ionic developer is connected to the siloxane by forming a Si—O—Si bond.

4. The novel antifouling developing coating material according to any one of claims 1 to 3, wherein: The ionic developer is connected to the aminosilane coupling agent through an amide condensation reaction; the connection method is based on an O=C—N—H amide bond; Optionally, the silane-containing ionic developer reacts with the antifouling molecule through a silane hydrolysis polymerization reaction. The sexual phosphorylcholine polymers are connected by linking groups; Optionally, the linking group is selected from any one of a methylsilyl group, a vinylsilyl group, an aminosilyl group, a triphenylphosphine group, an olefin phosphine ligand group, and a mercaptophosphine ligand group.

5. The novel antifouling developing coating material according to any one of claims 1 to 4, wherein: The anti-fouling developing coating material has a structure shown in the following formula II: Wherein, m=1-40, n=1-40, k=1-3, R is selected from C1-C5 alkyl, L is Optionally, m:n=1:1~4:1, and optionally m:n=3:

1.

6. The method for preparing the novel antifouling developing coating material according to any one of claims 1 to 5, comprising the following steps: The novel antifouling developing coating material is obtained by reacting an ionic developer containing a silane group with a modified phosphorylcholine polymer modified by siloxane.

7. The preparation method according to claim 6, wherein: The molar ratio of the silane-containing ionic developer to the siloxane-modified modified phosphorylcholine polymer is 1:1 to 4:

1.

8. The preparation method according to claim 6 or 7, wherein: The reaction is carried out at room temperature, and the reaction time is 6-24 hours, and can be 12 hours.

9. The preparation method according to any one of claims 6 to 8, wherein: The ionic developer containing a silane group is prepared by the following preparation method: an ionic developer reacts with a siloxane compound to obtain the ionic developer containing a silane group.

10. The preparation method according to claim 9, wherein: The siloxane compound is selected from any one of 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane or 3-aminopropyltriethoxysilane, or a combination of at least two thereof; Optionally, the molar ratio of the ionic developer to the siloxane compound is 1:1 to 1:3; Optionally, the reaction of the ionic developer with the siloxane compound is carried out in the presence of O-benzotriazole-tetramethyluronium hexafluorophosphate; Optionally, the reaction of the ionic developer with the siloxane compound is carried out in the presence of triethylamine; Optionally, the temperature of the reaction between the ionic developer and the siloxane compound is 50 to 80° C., and the reaction time is 6 to 24 hours; Optionally, the reaction of the ionic developer and the siloxane compound is carried out in a solvent, and the solvent is N,N-dimethylformamide.

11. The preparation method according to any one of claims 6 to 10, wherein: The preparation method of the modified phosphorylcholine polymer comprises the following steps: 2-Methacryloyloxyethyl phosphorylcholine reacts with a siloxane compound to obtain the siloxane-modified modified phosphorylcholine polymer.

12. The preparation method according to claim 11, wherein: The siloxane compound is methacryloxypropyl tris(trimethylsiloxy)silane and / or 3-(methacryloxy)propyl trimethoxysilane; Optionally, the molar ratio of the 2-methacryloyloxyethyl phosphorylcholine to the siloxane compound is 1:1-8:1; Optionally, the reaction of 2-methacryloyloxyethyl phosphorylcholine with the siloxane compound is carried out in the presence of 4-cyano-4-(thiobenzoyl)pentanoic acid; Optionally, the molar ratio of the 2-methacryloyloxyethyl phosphorylcholine to 4-cyano-4-(thiobenzoyl)pentanoic acid is 1:1-5:1; Optionally, the reaction of 2-methacryloyloxyethyl phosphorylcholine and the siloxane compound is carried out in the presence of an initiator; Optionally, the initiator is selected from azobisisobutyronitrile; Optionally, the molar ratio of the 2-methacryloyloxyethyl phosphorylcholine to the initiator is 1:1-5:1; Optionally, the reaction temperature of the 2-methacryloyloxyethyl phosphorylcholine and the siloxane compound is 60° C.-70° C., and the reaction time is 16-64 h; Optionally, the reaction of 2-methacryloyloxyethyl phosphorylcholine and the siloxane compound is carried out in a solvent, and the solvent is selected from n-propanol; Optionally, the reaction of 2-methacryloyloxyethyl phosphorylcholine and the siloxane compound is carried out under nitrogen protection; Optionally, the specific operation of the preparation method of the modified phosphorylcholine polymer is: dissolving 2-methacryloyloxyethyl phosphorylcholine, 4-cyano-4-(thiobenzoyl)valeric acid, and azobisisobutyronitrile in n-propanol, heating to 60°C-70°C under nitrogen protection, stirring and reacting for 16-32 hours, and then adding a siloxane compound, continuing the reaction for 16-32 hours to obtain the modified phosphorylcholine polymer.

13. Use of the novel antifouling developing coating material according to any one of claims 1 to 5 in coating a substrate surface; Optionally, the substrate surface includes a silicon-based surface, a glass-based surface, a metal-based surface, or a high-molecular polymer-based surface.

14. An antifouling developing coating, wherein: The raw materials for preparing the anti-fouling developing coating include the novel anti-fouling developing coating material according to any one of claims 1 to 5.

15. Use of the novel antifouling developing coating material according to any one of claims 1 to 5 in medical devices or medical materials, optical lenses or industrial printing.

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