An antifouling developing coating material, a preparation method and application thereof

The antifouling and developing coating material prepared by polymerization reaction, combined with phosphocholine and siloxane, solves the contradiction between antifouling and developing efficiency in developing coatings, achieving high-efficiency antifouling performance and developing effect. It is suitable for various substrate surfaces, and has important applications, especially in medical devices and medical imaging.

CN119219844BActive Publication Date: 2025-11-11SUZHOU SILVER MARS NEW MATERIALS TECHNOLOGY CO LTD
View PDF 2 Cites 0 Cited by

Patent Information

Application Number
CN202411332501.X
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-09-24
Publication Date
2025-11-11
Estimated Expiration
2044-09-24

AI Technical Summary

Technical Problem

Existing medical imaging coatings, when combining imaging and antifouling functions, suffer from reduced imaging efficiency, making it difficult to simultaneously achieve excellent antifouling performance and imaging effect.

Method used

An antifouling and developing coating material is prepared by covalently combining phosphocholine, siloxane, and developing monomers through a polymerization reaction. The modified phosphocholine polymer is used as an antifouling agent component, which combines with siloxane to form covalent or hydrophobic bonds with the substrate surface, ensuring the stability and developing performance of the coating.

Benefits of technology

It achieves excellent anti-fouling performance and stable imaging effect of the developing coating, significantly improving the safety of medical devices and the accuracy of medical imaging. It is suitable for a variety of substrate surfaces and is widely used in medical devices and medical imaging.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN119219844B_ABST
    Figure CN119219844B_ABST
Patent Text Reader

Abstract

The application provides an antifouling developing coating material and a preparation method and application thereof. The antifouling developing coating material has a structure shown in formula I. The antifouling developing coating material combines antifouling and developing through a covalent binding technology, has excellent antifouling performance and developing performance, can ensure the stability and durability of the developing effect, has good safety, and has a wider application range, and provides strong support for the safety of medical equipment and the accuracy of medical images.
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

[0001] This invention belongs to the field of medical materials technology, and relates to an antifouling and radiopaque coating material, its preparation method and application. Background Technology

[0002] In medical imaging, medical imaging coatings are of paramount importance. With the continuous development of medical imaging, the requirements for imaging coatings are becoming increasingly stringent. In addition to possessing excellent imaging capabilities, they also need outstanding antifouling properties to resist the adhesion of bacteria and proteins, prevent infection, and maintain a clean and transparent surface, thereby ensuring the acquisition of clear and accurate images.

[0003] The development of antifouling radiopaque coatings for medical use stems from improvements to traditional radiopaque coatings. While traditional radiopaque coatings provide radiopaque function, their antifouling performance is limited. With the increasing use of medical devices, scientists urgently need to research the addition of antifouling materials to improve antifouling performance. The antifouling principle mainly involves the hydrophilicity and hydrophobicity of the material surface. Hydrophilic surfaces can form a large water contact angle, preventing the retention of moisture and impurities, while hydrophobic surfaces can prevent the adhesion of organic matter or oils and reduce the adsorption of biomolecules.

[0004] In recent years, significant progress has been made in the research of medical antifouling coatings. Excellent antifouling coatings have been developed by adjusting surface properties. For example, the introduction of superhydrophobic polymers gives the surface a superhydrophobic effect, achieving highly efficient self-cleaning and antifouling. Simultaneously, special surface structures, such as micro-nano bumps and honeycomb structures, are designed using biomimetic techniques to reduce the surface contact area and decrease the adhesion of contaminants. Furthermore, embedding bioactive molecules into the coating forms a "sterilizing zone," which can inhibit the growth of microorganisms and improve the antifouling effect.

[0005] The imaging performance of medical antifouling and radiopaque coatings has a crucial impact on the clarity and diagnostic accuracy of medical images. These coatings need to be sensitive to X-rays to ensure good imaging results under X-ray irradiation. Radiopaque techniques are widely used in medical imaging, generating clear images through the imaging action of photosensitive materials. X-ray radiopaque imaging is a commonly used technique that relies on the absorption and scattering of X-rays, and the radiopaque coating plays a key role in this process, forming images by absorbing and scattering X-rays.

[0006] Nevertheless, the interaction between the developer and the antifouling agent can reduce developing efficiency. Therefore, effectively combining developing and antifouling functions remains a challenging problem that requires further research. Summary of the Invention

[0007] To address the shortcomings of existing technologies, the present invention aims to provide an antifouling and developing coating material, its preparation method, and its application.

[0008] To achieve this objective, the present invention adopts the following technical solution:

[0009] On one hand, the present invention provides an antifouling and developing coating material, the antifouling and developing coating material having the structure shown in Formula I:

[0010]

[0011] Where 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 = 1–4 (e.g., 1, 2, 3, or 4), R1 is hydrogen or methyl, R2 is a single bond, C1-C8 (e.g., C1, C2, C3, C4, C5, C6, C7, or C8) alkyl or... R4 is a C1-C5 (e.g., C1, C2, C3, C4, or C5) alkyl group, R3 is a C1-C5 (e.g., C1, C2, C3, C4, or C5) alkyl group, or -O-Si-R5, R5 is a C1-C5 (e.g., C1, C2, C3, C4, or C5) alkyl group; R is a hydroxyl group or The wavy line represents the connection site of the functional group.

[0012] In this invention, the antifouling and developing coating material covalently combines phosphocholine, siloxane, and developing monomers through a polymerization reaction, thereby combining antifouling and developing properties in the resulting material. This ensures the stability of the material and the stability of its antifouling and developing performance, resulting in outstanding performance in both antifouling and developing effects. Consequently, the material has broad application prospects in the field of medical imaging, providing strong support for the safety of medical equipment and the accuracy of medical imaging.

[0013] In some preferred embodiments, m:n = 1:1 to 4:1, for example 1:1, 2:1, 3:1 or 4:1.

[0014] In this invention, m, n, and k represent the number of structural units, where R can be the same or different for k structural units.

[0015] Preferably, the antifouling and developing coating material is any one of the compounds with the structure shown in Formulas II-IV below:

[0016]

[0017]

[0018] The constraints for m, n, k, and R are the same as in Equation I.

[0019] On the other hand, the present invention provides a method for preparing a novel antifouling and developing coating material as described above, the method comprising the following steps:

[0020] (1) The hydrolysate of iohexol reacts with ethyl isocyanate to obtain the developer monomer described in Formula II, as shown in the following reaction formula:

[0021]

[0022] (2) 2-Methacryloxyethylphosphocholine reacts with the developer monomer of Formula II and the siloxane compound of Formula A to obtain the antifouling developer coating material of Formula I, as shown in the following reaction formula:

[0023]

[0024] Where R is a hydroxyl group or

[0025] Preferably, the reaction in step (1) is carried out in the presence of a catalyst;

[0026] Preferably, the catalyst is any one or a combination of at least two of dibutyltin dilaurate, ethylenediamine, polyethyleneimine, triethylenediamine, or bis(2-dimethylaminoethyl) ether.

[0027] Preferably, the molar ratio of the iohexol hydrolysate to 2-isocyanoethyl acrylate is 1:1 to 1:4; for example, 1:1, 1:1.5, 1:2, 1:2.5, 1:3, 1:3.5, or 1:4.

[0028] Preferably, the reaction temperature in step (1) is 30-50℃ (e.g., 30℃, 35℃, 38℃, 40℃, 43℃, 45℃, 48℃ or 50℃), and the reaction time is 24-48h (e.g., 24h, 28h, 30h, 33h, 35h, 38h, 40h, 42h, 46h or 48h).

[0029] Preferably, the solvent for the reaction in step (1) is any one or a combination of at least two of N,N-dimethylformamide, isopropanol, methanol, diethyl ether or ethyl acetate.

[0030] Preferably, the reaction in step (1) is carried out under nitrogen protection.

[0031] Preferably, the siloxane compound in step (2) is methacryloyloxypropyltris(trimethylsiloxane), methacryloyloxypropyltris(trimethoxy)silane, or vinyltrimethoxysilane;

[0032] Preferably, the molar ratio of 2-methacryloyloxyethyl phosphocholine to the siloxane compound in step (2) is 1:1 to 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.

[0033] Preferably, the molar ratio of the siloxane-modified phosphocholine polymer to the developer monomer of Formula II in step (2) is 2:1-8:1, for example 2:1, 2.3:1, 2.5:1, 2.8:1, 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.

[0034] Preferably, the reaction in step (2) is carried out in the presence of 4-cyano-4-(thiobenzoyl)valerate;

[0035] Preferably, the molar ratio of 2-methacryloyloxyethyl phosphocholine to 4-cyano-4-(thiobenzoyl)valerate in step (2) 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.

[0036] Preferably, the reaction in step (2) is carried out in the presence of an initiator;

[0037] Preferably, the initiator is selected from azobisisobutyronitrile;

[0038] Preferably, the molar ratio of 2-methacryloyloxyethyl phosphocholine to the initiator is 1:1 to 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.

[0039] Preferably, the reaction temperature in step (2) is 60℃-70℃ (e.g., 60℃, 63℃, 65℃, 68℃ or 70℃), 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).

[0040] Preferably, after the reaction in step (2) is completed, a post-processing step is further included, wherein the obtained reaction solution is precipitated in diethyl ether and then filtered and dried.

[0041] On the other hand, the present invention provides the application of the novel antifouling and developing coating material as described above in the coating of a substrate surface.

[0042] Preferably, the substrate surface includes a silicon-based surface, a glass-based surface, a metal-based surface, or a polymer-based surface.

[0043] The antifouling and developing coating material of this invention can be applied to the surface of various substrates, including glass substrates, metal substrates, and various plastic and polymer substrates (silicone rubber, polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyurethane, etc.).

[0044] The antifouling and radiopaque coating material of the present invention has universality. It can covalently bond with any silicon-based substrate through silicon-oxygen bonds to hydroxyl groups on the substrate surface, including various silicon-based surfaces such as glass, silicone sheets, and marble. It can also bond with other substrate surfaces through hydrophobic interactions or van der Waals forces, making it widely applicable to different clinical and laboratory scenarios and meeting the needs of different users.

[0045] On the other hand, the present invention provides an anti-fouling developing coating, wherein the raw materials for preparing the anti-fouling developing coating include the anti-fouling developing coating material as described above.

[0046] On the other hand, the present invention provides the application of the antifouling and imaging coating material as described above in medical devices or medical materials, optical lenses or industrial printing.

[0047] Compared with the prior art, the present invention has the following beneficial effects:

[0048] First, the antifouling and radiopaque coating material of this invention has been successfully applied to medical devices, forming a coating with excellent antifouling properties. Compared with traditional radiopaque coatings, this material achieves a significant improvement in antifouling performance. Its unique feature lies in the presence of a modified phosphocholine polymer as an antifouling agent, which effectively resists the adhesion of bacteria and proteins, preventing bacterial infection and cross-infection. This characteristic is crucial for medical safety, ensuring that medical devices remain hygienic and safe during use. This material is suitable for various medical scenarios, and is particularly important in high-hygiene-standard equipment such as operating rooms and medical catheters.

[0049] Furthermore, the antifouling and radiopaque coating material of this invention exhibits superior radiopaque performance. Compared to conventional methods, this coating is in the form of a water-insoluble elastomer, which will not be lost during human metabolism, ensuring the stability and durability of the radiopaque effect. This eliminates potential side effects caused by radiopaque coatings and improves the safety of medical radiopaque coatings, which has positive implications for patient health and medical experience.

[0050] The antifouling and radiopaque coating material of this invention also has wide applicability. Through silicon-oxygen bonds with the hydroxyl groups on the substrate surface, it can covalently bond with various silicon-based surfaces, including glass, silicone sheets, and marble. It bonds with other substrate surfaces through hydrophobic interactions or van der Waals forces, making it widely applicable to different clinical and laboratory scenarios and meeting the needs of various users. Compared to traditional coatings, its preparation method is simpler and less expensive, providing a feasible path for the large-scale application of radiopaque coatings. Attached Figure Description

[0051] Figure 1 This is an NMR data graph of the developing monomer.

[0052] Figure 2 The image shows the 1H NMR spectrum of the polymer prepared in Example 1.

[0053] Figure 3 The image shows the 1H NMR spectrum of the polymer prepared in Example 2.

[0054] Figure 4 This image shows the anticoagulant effect of a novel antifouling and developing coating material.

[0055] Figure 5A A fluorescence microscope image showing the anti-protein adhesion test results of the novel antifouling and developing coating material of this invention;

[0056] Figure 5B The fluorescence quantitative analysis results of the total amount of protein molecules adsorbed by the novel antifouling and developing coating material of this invention are shown in the figure.

[0057] Figure 6A This is a graph showing the results of the antibacterial adhesion test of the novel antifouling and developing coating material of this invention;

[0058] Figure 6B This is a graph showing the quantitative analysis results of the antibacterial adhesion test of the novel antifouling and developing coating material of this invention;

[0059] Figure 7A The image shows the imaging test results of the novel antifouling and developing coating inside a rat.

[0060] Figure 7B This image shows the results of quantitative imaging analysis of the novel antifouling and imaging coating inside rat tissue. Detailed Implementation

[0061] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0062] Example 1

[0063] This embodiment provides an antifouling and developing coating material, which is prepared by a method including the following steps:

[0064] (1) Preparation of developer monomers:

[0065]

[0066] 1.34 mmol of iohexol hydrolysate was added to 20 mL of ultra-dry DMF and stirred until suspended. Two drops of catalyst DBTL and 5.36 mmol of 2-isocyanoethyl acrylate were added dropwise, and the mixture was magnetically stirred. The reaction was carried out at 30 °C for 24 h. The reaction was quenched by adding 1 mL of ethanol. The reaction solution was poured into 200 mL of diethyl ether, resulting in a white precipitate. After standing until the layers separated, the supernatant was removed, and the ether was evaporated at room temperature or dried in a vacuum oven at room temperature to obtain the developing monomer product. The NMR results are shown below. Figure 1 As shown.

[0067] 2) Preparation of antifouling and developing coating materials:

[0068]

[0069] Where R is

[0070] 0.75 mol of 2-methacryloyloxyethyl phosphocholine, 0.4 mol of 4-cyano-4-(thiobenzoyl)valerate, and 0.4 mol of azobisisobutyronitrile were dissolved in n-propanol. The mixture was slowly heated to 65 °C under nitrogen protection and stirred for 24 h. Then, 0.125 mol of methacryloyloxypropyltris(trimethylsiloxane)silane and 0.075 mol of a developing monomer were added, and the reaction was continued for another 24 h. The resulting n-propanol solution was added to diethyl ether to precipitate the precipitate. After filtration and drying, the modified phosphocholine polymer was obtained. The NMR of the obtained polymer was as follows: Figure 2 As shown, a peak of trimethylsiloxane was detected at 3.55 ppm.

[0071] Example 2

[0072] This embodiment provides an antifouling developing coating material, which is prepared by a method including the following steps: the preparation of the developing monomer is the same as in Example 1.

[0073] 0.75 mol of 2-methacryloyloxyethyl phosphocholine, 0.4 mol of 4-cyano-4-(thiobenzoyl)valerate, and 0.4 mol of azobisisobutyronitrile were dissolved in n-propanol. The mixture was slowly heated to 60 °C under nitrogen protection and stirred for 24 h. Then, 0.125 mol of 3-(triethoxysilyl)methacrylate and 0.075 mol of a developing monomer were added, and the reaction was continued for another 24 h. The resulting n-propanol solution was added to diethyl ether to precipitate the precipitate. After filtration and drying, the modified phosphocholine polymer was obtained. The NMR of the obtained polymer was as follows: Figure 3 As shown, a peak of methoxysilane was detected at 3.55 ppm.

[0074] Example 3

[0075] The antifouling and developing coating material obtained in Example 1 of this invention was used to test its anticoagulant effect. Regarding anticoagulant properties, the adsorption capacity of rat whole blood on the antifouling and developing coating was measured and characterized. The antifouling and developing coating solution was prepared by dissolving the antifouling and developing coating material in DMF at a concentration of 300 mg / mL. This solution was used to coat silicone tubing, which was then cured in an oven at 60°C. The silicone tubing coated with the antifouling and developing coating was then immersed in freshly extracted rat whole blood for five minutes, after which it was removed and rinsed three times with physiological saline. The control group was a blank control without the antifouling and developing coating. The results are as follows: Figure 4 As shown.

[0076] like Figure 4 As shown, compared to the blank control, this coating exhibits excellent anticoagulant properties. Blood hardly adheres to the coating, while the blank control group is covered with whole blood adhering to it.

[0077] Example 4

[0078] Anti-protein adhesion tests were conducted using the antifouling and developing coating material from Example 1.

[0079] Regarding the prevention of protein adsorption, the adsorption capacity of fibrin (FIB), serum albumin (HB), and collagen (Col) on the antifouling and developing coating was measured and characterized.

[0080] Protein molecules were pre-labeled with fluorescent agents, and an adsorption experiment was conducted over 21 days. On days 3, 14, and 21, the adsorption of various molecules on the coating was observed using a fluorescence microscope (Nikon Eclipse TE / Ti). The control group consisted of a blank control without the antifouling and developing coating. Results are as follows: Figure 5A and Figure 5B As shown.

[0081] like Figure 5AAs shown, compared to the blank control, this coating exhibited superior anti-protein adsorption capacity. Serum proteins were hardly adsorbed onto the coating, and fibrinogen adsorption on the antifouling and developing coating was also minimal, while the blank control group was saturated with adsorbed protein molecules. Furthermore, the total amount of adsorbed molecules was quantitatively analyzed using fluorescence, such as... Figure 5B As shown, compared with the blank control group, the total amount of protein adsorbed on the antifouling developing coating was significantly reduced, demonstrating the strong anti-protein adsorption ability of the antifouling developing coating.

[0082] Example 5

[0083] Antibacterial adhesion tests were conducted using the antifouling and developing coating material from Example 1.

[0084] Regarding antibacterial adhesion, the antifouling and developing coating's antibacterial adsorption capacity was characterized using Candida albicans, Escherichia coli, and Staphylococcus aureus. The samples were immersed in a high concentration (10...) of... 8 Three viable bacterial solutions (number of bacteria / mL) were prepared, with the viable bacteria changed daily. After soaking for one week, the solutions were removed, air-dried, and the bacterial count was observed using a scanning electron microscope (SEM, Japan Hitachi; S-3400N). Dialysis buffer was used as the solvent to ensure bacterial viability, and a blank control group was used. Results are as follows: Figure 6A and Figure 6B As shown.

[0085] like Figure 6A As shown, after one week of adsorption by three different bacteria, large colonies were observed on the control group without the antifouling and developing coating, while no significant colony growth was observed on the sample with the antifouling and developing coating. Further quantitative analysis of the adsorbed colonies was performed, and the results are as follows: Figure 6B As shown, the samples treated with the antifouling developing coating significantly reduced bacterial adhesion, with a 90% reduction in bacterial adhesion after one week.

[0086] Example 6

[0087] X-ray imaging tests were performed using the antifouling and radiopaque coating material of Example 1. The antifouling and radiopaque coating material of the present invention was coated onto silicone tubing and placed in rats at concentrations (solution concentrations) of 100 mg / mL and 200 mg / mL, with the uncoated group serving as a control. X-ray imaging was performed using a medical X-ray irradiation system (manufacturer: Frameview Technology; model: XVS2530). The results are as follows. Figure 7A and Figure 7B As shown, where, Figure 7A X-ray images of developing materials of different concentrations; Figure 7BThe figures represent the grayscale values ​​of different concentrations of developing materials. It is evident that the developing effect of the antifouling developing coating material of this invention is significantly higher than that of the blank control group. Quantitative analysis of the developed portion using ImageJ software reveals that the developing intensity inside the rat increases with increasing concentration. Therefore, the antifouling developing coating material of this invention exhibits strong X-ray developing effect.

[0088] As can be seen from the above, the antifouling and radiopaque coating material of the present invention has excellent coating performance, antifouling performance and X-ray radiopaque effect.

[0089] The modified phosphocholine polymer portion of the antifouling and developing coating material of this invention serves as the antifouling unit, while the bound iohexol serves as the developing unit, exhibiting both excellent antifouling and developing properties. The siloxane groups in the antifouling unit can form covalent bonds with the substrate surface, thus firmly bonding the coating to the substrate. This ensures the bonding stability and security of the antifouling and developing coating material of this invention on the substrate. For example, the siloxane groups can covalently bond with silicon-based substrate materials, exhibiting excellent stability and not migrating or detaching over time, significantly improving the durability and reliability of the developing coating. Furthermore, the siloxane groups can also bond with other substrate surfaces through hydrophobic interactions and van der Waals forces, thereby providing flexibility and applicability for the wide application of the developing coating. The antifouling and imaging coating material of the present invention can be coated on the surface of various substrates, including silicon-based substrates (e.g., glass substrates), metal substrates, and various plastic and polymer substrates (e.g., silicone rubber, polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyurethane, etc.), and has wide applicability; it has a wide range of applications, such as in medical devices, optical lenses, and industrial printing. This coating gives the coated object the dual functions of antifouling and X-ray imaging, exhibits excellent X-ray absorption performance during imaging, and in particular, can provide accurate and clear imaging results for medical imaging and provide reliable image information for medical contrast imaging.

[0090] The applicant declares that the present invention is illustrated by the above embodiments to demonstrate the antifouling and developing coating material and its application, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A stain-resistant developing coating material, characterized in that, The antifouling and developing coating material has the structure shown in Formula I: ; Formula I Where m = 1~40, n = 1~40, k = 1~4, R1 is hydrogen or methyl, and R2 is a single bond, C1-C8 alkylene, or... R4 is a C1-C5 alkylene group, R3 is a C1-C5 alkyl group or -Si-(CH3)3; R is a hydroxyl group or The wavy line represents the connection site of the functional group.

2. The antifouling and developing coating material according to claim 1, characterized in that, m:n = 1:1 ~ 4:

1.

3. The antifouling and developing coating material according to claim 1, characterized in that, The antifouling and developing coating material is any one of the compounds with the structure shown in Formulas II-IV below: ; Formula II ; Formula III ; Formula IV The constraints for m, n, k, and R are the same as in Equation I.

4. The method for preparing the antifouling and developing coating material according to any one of claims 1-3, characterized in that, The preparation method includes the following steps: (1) The hydrolysate of iohexol reacts with ethyl isocyanate to obtain the developer monomer shown in formula V. The reaction formula is as follows: ; (2) 2-Methacryloxyethylphosphocholine reacts with the developer monomer shown in Formula V and the siloxane compound shown in Formula A to obtain the antifouling developer coating material shown in Formula I. The reaction formula is as follows: ; Where R is a hydroxyl group or .

5. The preparation method according to claim 4, characterized in that, The reaction described in step (1) is carried out in the presence of a catalyst.

6. The preparation method according to claim 5, characterized in that, The catalyst is any one or a combination of at least two of the following: dibutyltin dilaurate, ethylenediamine, polyethyleneimine, triethylenediamine, or bis(2-dimethylaminoethyl) ether.

7. The preparation method according to claim 4, characterized in that, The molar ratio of the iohexol hydrolysate to 2-isocyanoethyl acrylate is 1:1 to 1:

4.

8. The preparation method according to claim 4, characterized in that, The reaction temperature in step (1) is 30-50℃, and the reaction time is 24-48 h.

9. The preparation method according to claim 4, characterized in that, The solvent for the reaction in step (1) is any one or a combination of at least two of N,N-dimethylformamide, isopropanol, methanol, diethyl ether or ethyl acetate.

10. The preparation method according to claim 4, characterized in that, The reaction described in step (1) is carried out under nitrogen protection.

11. The preparation method according to claim 4, characterized in that, The siloxane compound in step (2) is methacryloyloxypropyltris(trimethylsiloxane), 3-(methacryloyloxy)propyltrimethoxysilane, or vinyltrimethoxysilane.

12. The preparation method according to claim 4, characterized in that, The molar ratio of 2-methacryloyloxyethyl phosphocholine to the siloxane compound in step (2) is 1:1 to 8:

1.

13. The preparation method according to claim 4, characterized in that, The reaction described in step (2) is carried out in the presence of 4-cyano-4-(thiobenzoyl)valerate.

14. The preparation method according to claim 13, characterized in that, The molar ratio of 2-methacryloyloxyethyl phosphocholine to 4-cyano-4-(thiobenzoyl)valerate in step (2) is 1:1-5:

1.

15. The preparation method according to claim 4, characterized in that, The reaction described in step (2) is carried out in the presence of an initiator.

16. The preparation method according to claim 15, characterized in that, The initiator is selected from azobisisobutyronitrile.

17. The preparation method according to claim 15, characterized in that, The molar ratio of 2-methacryloyloxyethyl phosphocholine to the initiator is 1:1 to 5:

1.

18. The preparation method according to claim 4, characterized in that, The reaction temperature in step (2) is 60℃-70℃, and the reaction time is 16-64h.

19. The preparation method according to claim 4, characterized in that, After the reaction in step (2) is completed, a post-processing step is also included, which involves precipitating the obtained reaction solution in diethyl ether, filtering and drying.

20. The application of the antifouling and developing coating material according to claim 1 on the surface of a coated substrate.

21. The application according to claim 20, characterized in that, The substrate surface includes a silicon-based surface, a metal-based surface, and a polymer-based surface.

22. A stain-resistant developing coating, characterized in that, The raw materials for preparing the antifouling developing coating include the antifouling developing coating material as described in claim 1.

23. The application of the antifouling and imaging coating material according to claim 1 in the preparation of medical devices or medical material products, optical lenses or industrial printing.

Citation Information

Patent Citations

  • Novel antibacterial antifouling coating material as well as preparation method and application thereof

    CN117736618A

  • Copolymers Containing Phosphorylcholine Groups and Methods of Preparing and Using the Same

    US20130231400A1