A coating composition, coating material, and stain resistant coating

Abstract

The application discloses a coating composition, a coating material and an anti-fouling coating, and the coating composition comprises: pentaerythritol tetra-3-mercapto propionate (PETMP), hexamethylene diisocyanate (HDI), an indole derivative containing a carbon-carbon double bond and an initiator. The indole derivative containing the carbon-carbon double bond is a Friedel-Crafts alkylation product of N-hydroxymethyl acrylamide and the indole derivative. The anti-fouling coating obtained after curing of the coating composition provided by the application has excellent mechanical properties, high anti-biofouling adhesion and strong adhesion between the coating and a substrate. The indole derivative can act on transmembrane transport of calcium ions in cells, trigger Ca 2+ efflux in the intracellular environment, destroy the homeostasis of Ca 2+ in the cells, and have an adverse effect on the growth and development of the cells, thereby inhibiting the adhesion and growth and reproduction of biofouling organisms such as microalgae.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of coating technology, in particular to a coating composition, a coating material and an anti-fouling coating. BACKGROUND

[0002] Marine biofouling refers to the phenomenon that bacteria, algae, barnacles and other organisms adhere, grow and accumulate on the surface of engineering equipment and infrastructure immersed in seawater, which has certain harm to strategic fields such as environmental protection, energy and national defense. The complexity of marine environment and the diversity of fouling organisms have led to the fact that global marine equipment and facilities are facing this major challenge. After long-term exploration, more and more scholars have realized that coating anti-fouling coating is the most effective protection technology. However, the toxicity of the currently used anti-fouling coating still pollutes the environment, and there is a lack of substitutes or environmentally friendly anti-fouling coating. Therefore, balancing the high efficiency of the coating and environmental friendliness is the development trend of the marine anti-fouling field.

[0003] Low surface energy coating based on the release mechanism of fouling makes use of its low surface energy and low elastic modulus characteristics to make it difficult for fouling organisms to adhere to the surface or for them to easily fall off the surface after adhesion. Since no toxic substances are released, low surface energy coating is considered to be a promising anti-fouling system. Silicon-containing polymers are the main research type of low surface energy coating, and the silicon-based low surface energy coating has the following defects: low adhesion of the coating, insufficient mechanical properties; the need to rely on seawater shear force to play the anti-fouling performance, resulting in poor static anti-fouling effect; the adhesion of diatoms and other fouling organisms on the surface of silicon-containing polymer materials is more serious.

[0004] Chinese invention patent CN202010284345.X reports a silicon-containing polyurethane low surface energy marine anti-fouling coating, and CN202011443159.2 discloses a nano-enhanced organosiloxane low surface energy anti-fouling coating. However, the above-mentioned patents only improve the adhesion, mechanical properties and static anti-fouling performance, and do not address the more serious adhesion of diatoms and other fouling organisms on the surface of silicon-containing polymer materials. SUMMARY

[0005] In view of the above technical problems, the present application provides a coating composition, a coating material and an anti-fouling coating, which overcome the problems of low adhesion, insufficient mechanical properties, poor static anti-fouling effect and serious diatom adhesion of low surface energy anti-fouling coating.

[0006] To achieve the above-mentioned purpose, the technical solution adopted by the present application is as follows:

[0007] On the one hand, the present application provides a coating composition, which comprises: pentaerythritol tetra-3-mercaptopropionate (PETMP), hexamethylene diisocyanate (HDI), an indole derivative containing a carbon-carbon double bond and an initiator;

[0008] wherein the indole derivative having a carbon-carbon double bond has a structure represented by the following formula (1):

[0009]

[0010] In formula (1), R1, R2 are each independently selected from any one of halogen, H and nitro; and R3 is selected from any one of phenyl, hydrogen and methyl.

[0011] As a preferred embodiment, the coating composition comprises: pentaerythritol tetra-3-mercaptopropionate (PETMP) 45-100 parts by mass, hexamethylene diisocyanate (HDI) 80-130 parts by mass, an indole derivative having a carbon-carbon double bond 4-25 parts by mass, and an initiator 0.8-4 parts by mass.

[0012] In some specific embodiments, the pentaerythritol tetra-3-mercaptopropionate (PETMP) is in a mass fraction of 45 parts by mass, 55 parts by mass, 65 parts by mass, 75 parts by mass, 85 parts by mass, 90 parts by mass, 95 parts by mass, 100 parts by mass, or any mass fraction therebetween.

[0013] In some specific embodiments, the hexamethylene diisocyanate (HDI) is in a mass fraction of 80 parts by mass, 90 parts by mass, 100 parts by mass, 110 parts by mass, 120 parts by mass, 130 parts by mass, or any mass fraction therebetween.

[0014] In some specific embodiments, the indole derivative having a carbon-carbon double bond is in a mass fraction of 4 parts by mass, 8 parts by mass, 12 parts by mass, 16 parts by mass, 20 parts by mass, 25 parts by mass, or any mass fraction therebetween.

[0015] In some specific embodiments, the initiator is in a mass fraction of 0.8 parts by mass, 1 part by mass, 2 parts by mass, 3 parts by mass, 4 parts by mass, or any mass fraction therebetween.

[0016] As a preferred embodiment, it further comprises a vinyl-terminated dimethyl polysiloxane;

[0017] In the technical solution of the present application, the vinyl-terminated dimethyl polysiloxane is selected from at least one of a mono-terminal vinyl dimethyl polysiloxane and a double-terminal vinyl dimethyl polysiloxane;

[0018] Preferably, the mass fraction of the vinyl-terminated dimethyl polysiloxane is 70-300 parts by mass;

[0019] In some specific embodiments, the vinyl-terminated dimethyl polysiloxane is 70 parts by weight, 100 parts by weight, 150 parts by weight, 200 parts by weight, 250 parts by weight, 300 parts by weight, or any number of parts by weight between them.

[0020] Preferably, the vinyl-terminated dimethylpolysiloxane has a molecular weight of 1500 to 3000.

[0021] As a preferred embodiment, zinc oxide is also included;

[0022] Preferably, the zinc oxide is micro-nano tetrapod zinc oxide (t-ZnO);

[0023] Preferably, the micro-nano tetrapod zinc oxide is present in a mass fraction of 2 to 25 parts by mass;

[0024] In some specific embodiments, the mass fraction of the micro-nano tetrapod zinc oxide is 2 parts by mass, 5 parts by mass, 10 parts by mass, 15 parts by mass, 20 parts by mass, 25 parts by mass, or any mass fraction between them.

[0025] In some specific embodiments, the arm length of the micro-nano tetrapod zinc oxide is 10-50 μm, and the diameter of the arm tip of the micro-nano tetrapod zinc oxide is ≤100 nm.

[0026] In a preferred embodiment, the indole derivative containing a carbon-carbon double bond is selected from at least one of N-(1H-5-bromoindole-3-methylene)acrylamide, N-(1H-6-chloroindole-3-methylene)acrylamide, N-(1H-2-methylindole-3-methylene)acrylamide, N-(1H-5-nitroindole-3-methylene)acrylamide and N-(1H-2-phenylindole-3-methylene)acrylamide;

[0027] In some specific embodiments, the indole derivative containing a carbon-carbon double bond is prepared by Friedel-Crafts alkylation of N-hydroxymethylacrylamide and an indole derivative; wherein the indole derivative has the structure shown in formula (2):

[0028]

[0029] Preferably, the mass ratio of N-hydroxymethylacrylamide to indole derivative is 1–4:0.8–3.5;

[0030] Preferably, the Friedel-Crafts alkylation reaction is carried out in the presence of a catalyst; the catalyst is aluminum trichloride or concentrated sulfuric acid; in some specific embodiments, the mass ratio of aluminum trichloride to N-hydroxymethylacrylamide is 1-6:3.2-14;

[0031] Preferably, the Friedel-Crafts alkylation reaction is carried out in a solvent; the solvent is preferably dichloromethane; the mass ratio of dichloromethane to N-hydroxymethylacrylamide is 5-20:0.8-3.5.

[0032] In a preferred embodiment, the initiator is selected from at least one of 1,1'-azobis(cyclohexaneformitrile) and azobisisobutyronitrile.

[0033] In another aspect, the present invention provides a coating material prepared from the above-mentioned coating composition, wherein pentaerythritol tetra-3-mercaptopropionate (PETMP) and an indole derivative containing carbon-carbon double bonds are subjected to a mercapto-olefin click reaction under the action of an initiator to obtain a prepolymer, and then subjected to a polycondensation reaction with hexamethylene diisocyanate (HDI) to obtain the coating material.

[0034] In a preferred embodiment, the temperature of the mercapto-olefin click reaction is 80–90°C, and the time is 2–5 hours.

[0035] In some specific embodiments, the polycondensation reaction is carried out under stirring conditions at room temperature for a reaction time of 10 to 30 minutes.

[0036] In another aspect, the present invention provides a coating material prepared from the above-mentioned coating composition, wherein pentaerythritol tetra-3-mercaptopropionate (PETMP), an indole derivative containing carbon-carbon double bonds, and vinyl-terminated dimethyl polysiloxane undergo a mercapto-olefin click reaction under the action of an initiator to obtain a prepolymer, which is then subjected to a polycondensation reaction with hexamethylene diisocyanate (HDI).

[0037] In another aspect, the present invention provides a composite coating material prepared from the above coating composition, wherein pentaerythritol tetra-3-mercaptopropionate (PETMP), an indole derivative containing carbon-carbon double bonds, and vinyl-terminated dimethyl polysiloxane are subjected to a mercapto-olefin click reaction under the action of an initiator to obtain a prepolymer; zinc oxide is dispersed in the prepolymer, and then subjected to a polycondensation reaction with hexamethylene diisocyanate (HDI);

[0038] Preferably, the dispersion is ultrasonic dispersion.

[0039] In another aspect, the present invention provides an antifouling coating prepared from the above-mentioned coating material or the above-mentioned composite coating material.

[0040] In the technical solution of the present invention, the above coating composition does not require heating and can be cured at room temperature to obtain an anti-fouling coating.

[0041] The above technical solution has the following advantages or beneficial effects:

[0042] This invention provides a coating composition, a coating material, and an antifouling coating. The coating composition can be further prepared into a composite coating material using indole-functionalized low-surface-energy polysulfuron as a substrate and doped with micro / nano tetrapod zinc oxide. After curing, an antifouling coating with excellent mechanical properties, high resistance to biofouling adhesion, and strong adhesion to the substrate is obtained. In the technical solution of this invention, the introduction of an organosilicon monomer (vinyl-terminated dimethyl polysiloxane) helps to reduce the surface free energy of the coating. Due to its low surface energy characteristics, the interaction between fouling organisms and the material surface can be reduced. Even if fouling organisms adhere to the coating surface, they can be easily removed under the shear force of seawater. Furthermore, the indole derivative can act on the transmembrane transport of calcium ions in cells and trigger the release of calcium ions in the intracellular environment. 2+ Excretion, disrupting intracellular calcium 2+ The stable state of indole can negatively impact cell growth and development, thereby inhibiting the attachment and growth of fouling organisms such as microalgae. Regarding adhesion, the introduction of indole derivatives did not weaken the adhesion strength of the coating material; rather, the unique structure of micro / nano tetrapod zinc oxide further increased the adhesion strength of the coating.

[0043] Compared with the prior art, the present invention has the following advantages:

[0044] 1. The anti-fouling coating preparation process provided by the present invention is simple, adopts a solvent-free system, and avoids the adverse effects of volatile organic substances.

[0045] 2. The coating molecular structure provided by this invention contains an active indole-derived structure, which further enhances the coating's inhibitory effect on the adhesion of fouling organisms such as diatoms.

[0046] 3. This invention uses polyurethane, an environmentally friendly polymer matrix with high tensile strength, excellent wear resistance, and high adhesion strength to the substrate, as the coating. Combined with the characteristic of micro-nano tetrapod zinc oxide that can significantly improve the adhesion of the material, the invention achieves the improvement of the mechanical properties and adhesion of the target coating. Attached Figure Description

[0047] Figure 1 This is the 1H NMR spectrum of N-(1H-5-bromoindole-3-methylene)acrylamide prepared in Manufacturing Example 1 of this invention.

[0048] Figure 2 This is the 1H NMR spectrum of N-(1H-6-chloroindole-3-methylene)acrylamide prepared in Manufacturing Example 1 of this invention.

[0049] Figure 3 This is the 1H NMR spectrum of N-(1H-2-phenylindole-3-methylene)acrylamide prepared in Manufacturing Example 1 of this invention.

[0050] Figure 4 This is the 1H NMR spectrum of N-(1H-2-methylindole-3-methylene)acrylamide prepared in Manufacturing Example 1 of this invention.

[0051] Figure 5 This is the 1H NMR spectrum of N-(1H-5-nitroindole-3-methylene)acrylamide prepared in Manufacturing Example 1 of this invention.

[0052] Figure 6 This is a process synthesis route diagram of the coating composition in Example 2 of the present invention. Detailed Implementation

[0053] The following embodiments are merely some, not all, of the embodiments of the present invention. Therefore, the detailed descriptions of the embodiments provided below are not intended to limit the scope of the claimed invention, but merely to illustrate selected embodiments. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without inventive effort are within the scope of protection of the present invention.

[0054] In this invention, unless otherwise specified, all equipment and raw materials are commercially available or commonly used in the industry. The methods described in the following embodiments are conventional methods in the art, unless otherwise specified.

[0055] Manufacturing example:

[0056] Manufacturing Example 1: N-(1H-5-bromoindole-3-methylene)acrylamide

[0057] In this manufacturing example, the preparation process of N-(1H-5-bromoindole-3-methylene)acrylamide is as follows:

[0058] Under stirring conditions, 5-bromoindole (9.80 g) and N-methylacrylamide (11.1 g) were dissolved in 100 g of dichloromethane. Under ice bath conditions, 3.2 g of anhydrous aluminum trichloride was added to the above solution. After stirring in the ice bath for 2 h, the solution was gradually heated to room temperature and stirred for another 48 h at room temperature. After filtration, the solution was washed with deionized water until the pH of the filtrate was 7. Finally, N-(1H-5-bromoindole-3-methylene)acrylamide was obtained by recrystallization from ethanol.

[0059] Manufacturing Example 2: N-(1H-6-chloroindole-3-methylene)acrylamide

[0060] In this manufacturing example, the preparation process of N-(1H-6-chloroindole-3-methylene)acrylamide is as follows:

[0061] Using 150g of dichloromethane as a solvent, 6.7g of anhydrous aluminum trichloride was added to the solvent under ice bath conditions, with the temperature controlled below 40℃. Then, 20.7g of 6-chloroindole and 26.2g of N-hydroxymethylacrylamide were added, and the reaction was carried out at room temperature under electromagnetic stirring. After the reaction was completed, the reaction solution was poured into ice-cold dilute hydrochloric acid, and the crude product was washed with deionized water until neutral. The purified product was obtained by column chromatography, dried, and stored.

[0062] Manufacturing Example 3: N-(1H-2-phenylindole-3-methylene)acrylamide

[0063] In this manufacturing example, the preparation process of N-(1H-2-phenylindole-3-methylene)acrylamide is as follows:

[0064] Using 150g of dichloromethane as a solvent, 5g of anhydrous aluminum trichloride was added to the solvent under ice bath conditions, with the temperature controlled below 40℃. Then, 19.3g of 2-phenylindole and 20.5g of N-hydroxymethylacrylamide were added, and the reaction was carried out at room temperature under electromagnetic stirring. After the reaction was completed, the reaction solution was poured into ice-cold dilute hydrochloric acid, and the crude product was washed with deionized water until neutral. The purified product was obtained by column chromatography, dried, and stored.

[0065] The proton NMR spectrum of the indole derivative containing carbon-carbon double bonds prepared in the above manufacturing example is shown below. Figures 1-3 .

[0066] Examples 1-5:

[0067] Example 1

[0068] (1) 97.7 g of pentaerythritol tetra-3-mercaptopropionate (PETMP), 13.9 g of N-(1H-5-bromoindole-3-methylene)acrylamide (BIAM) and 2.4 g of 1,1′-azobis(cyclohexaneformitrile) were added to a beaker. After the above materials were evenly dispersed by electromagnetic stirring, the system was heated to 85°C and reacted for 3 hours to obtain the prepolymer.

[0069] (2) 11.5g of micro-nano tetrapod zinc oxide (purchased from Chengdu Tianyou Jingchuang Technology Co., Ltd., model JC-01) was added to the prepolymer, and after ultrasonic dispersion treatment, it was degassed.

[0070] (3) Add 117.7g of hexamethylene diisocyanate (HDI) to the sample obtained above, disperse it evenly, degas it for 10-30 minutes, and then cure it at room temperature to obtain the coating sample.

[0071] Example 2

[0072] like Figure 4 As shown, the method for preparing the antifouling coating in this embodiment includes the following steps:

[0073] (1) 97.7g pentaerythritol tetra-3-mercaptopropionate (PETMP), 13.9g N-(1H-5-bromoindole-3-methylene)acrylamide (BIAM) and 100g vinyl-terminated dimethyl polysiloxane (purchased from Aladdin, trade name or brand name V304361, molecular weight 2000) were added to a beaker and mixed evenly at room temperature. Then, 2.4g of initiator 1,1′-azobis(cyclohexanecarboxynitrile) was added. The above materials were evenly dispersed by electromagnetic stirring. The system was heated to 85°C and reacted for 3 hours to obtain the prepolymer.

[0074] (2) 16.5g of micro-nano tetrapod zinc oxide (purchased from Chengdu Tianyou Jingchuang Technology Co., Ltd., model JC-01) was added to the prepolymer, and after ultrasonic dispersion treatment, it was degassed.

[0075] (3) Add 117.7g of hexamethylene diisocyanate (HDI) to the sample obtained above, disperse it evenly, degas it for 10-30 minutes, and then cure it at room temperature to obtain the coating sample.

[0076] Example 3

[0077] (1) 122.2g pentaerythritol tetra-3-mercaptopropionate (PETMP), 5.6g N-(1H-5-bromoindole-3-methylene)acrylamide (BIAM) and 200g vinyl-terminated dimethyl polysiloxane (purchased from Aladdin, trade name or brand name V304361, molecular weight 2000) were added to a beaker and mixed evenly at room temperature. Then, 2.9g of initiator 1,1′-azobis(cyclohexaneformitrile) was added. The above materials were evenly dispersed by electromagnetic stirring. The system was heated to 85°C and reacted for 3 hours to obtain the prepolymer.

[0078] (2) Add 8.7g of micro-nano tetrapod zinc oxide (purchased from Chengdu Tianyou Jingchuang Technology Co., Ltd., model JC-01) to the prepolymer, perform ultrasonic dispersion treatment, and then degas the prepolymer.

[0079] (3) Add 106.0g of hexamethylene diisocyanate (HDI) to the sample obtained above, disperse it evenly, degas it for 10-30 minutes, and then cure it at room temperature to obtain the coating sample.

[0080] Example 4

[0081] The preparation process of the coating sample in this embodiment is the same as that in Example 2, except that 11.7g of N-(1H-5-bromoindole-3-methylene)acrylamide is used instead of N-(1H-6-chloroindole-3-methylene)acrylamide in Example 2.

[0082] Example 5

[0083] The preparation process of the coating sample in this embodiment is the same as that in Example 2, except that 13.8g of N-(1H-5-bromoindole-3-methylene)acrylamide is used instead of N-(1H-2-phenylindole-3-methylene)acrylamide in Example 2.

[0084] Effect test:

[0085] The coating samples prepared in the above embodiments were subjected to surface wettability and surface energy tests, mechanical property tests, and adhesion tests.

[0086] The surface wettability and surface free energy of the coated samples were determined by measuring the contact angle at room temperature (using water and diiodomethane as reference solutions). Specifically, seven points were randomly selected from different regions of the coated sample surface, and the surface energy (γ) was calculated using the Owens-Wendt-Rabel-Kaelble method. s ), dispersive surface energy (γ) sd ) and polar surface energy (γ) sp )

[0087] Mechanical property testing was conducted via tensile testing according to ISO 527 standard: dog bone-shaped samples (20 mm long, 5 mm wide, and 1 mm thick) were prepared using silicone mold casting. The testing instrument was a Zwick universal testing machine with a preload of 5 N and a constant speed of 1 mm / min. Five tests were performed for each material.

[0088] Adhesion testing was conducted according to DIN EN ISO 462 to evaluate the adhesion between the coated samples and the AlMg3 aluminum alloy substrate. The coating composition was brushed onto an AlMg3 aluminum alloy substrate (80mm × 80mm). After curing, a cylindrical AlMg3 (50mm high, 20mm diameter) was adhered to the center of the cured coating using ethyl-2-cyanoacrylate adhesive (Henkel AG&Co. KgaA, Düsseldorf, Germany). After drying at room temperature for 24 hours, the coating around the cylindrical AlMg3 was cut with a knife to determine the test area. Adhesion testing was performed using a Zwick universal testing machine with a preload of 30N and a constant speed of 1mm / min. Five tests were conducted for each material.

[0089] Using *Phaeodactylum tricornutum* (diatoms) as the test algae species, the algal solution cultured to the exponential growth phase was diluted with f / 2 medium to an algal solution concentration of 1×10⁻⁶. 5Approximately 100 mL of the diluted algal solution was collected and added to a sterilized glass container. The prepared coating sample was then placed in the algal solution. Untreated containers containing algal solution served as a blank control group. All test containers were placed in a light incubator at 20°C, a light intensity of 4000 lux, and a light-dark ratio of 12 h:12 h. After 72 h of incubation, the surface of the suspended algal solution was gently rinsed with a certain amount of deionized water. The treated coating was then ultrasonically treated to detach the algal cells adhering to the surface. The absorbance value of each algal solution was measured, and the inhibition rate of the coating sample against the algal solution was calculated.

[0090] The test results are shown in Table 1:

[0091] Table 1:

[0092]

[0093] In the above tests, the surface energy of the vinyl-terminated dimethylpolysiloxane coating sample was approximately 21, which is close to the surface energy range (22-24 mJ / m²) corresponding to the optimal antifouling performance in the Baier curve. 2 Therefore, the coating preparation provided by the present invention has good antifouling performance, environmental compatibility, good mechanical properties, and strong adhesion to the substrate.

[0094] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A coating material, characterized in that, The coating material is prepared from a coating composition comprising: pentaerythritol tetra-3-mercaptopropionate, hexamethylene diisocyanate, an indole derivative containing a carbon-carbon double bond, and an initiator; The indole derivative containing carbon-carbon double bonds has the structure shown in formula (1): In formula (1), R1 and R2 are each independently selected from any one of halogen, H and nitro; R3 is selected from any one of phenyl, hydrogen and methyl. The pentaerythritol tetra-3-mercaptopropionate and the indole derivative containing carbon-carbon double bonds undergo a mercapto-olefin click reaction under the action of an initiator to obtain a prepolymer, which is then subjected to a polycondensation reaction with hexamethylene diisocyanate to obtain the coating material.

2. The coating material according to claim 1, characterized in that, The coating composition comprises: 45-100 parts by weight of pentaerythritol tetra-3-mercaptopropionate, 80-130 parts by weight of hexamethylene diisocyanate, 4-25 parts by weight of an indole derivative containing carbon-carbon double bonds, and 0.8-4 parts by weight of an initiator.

3. The coating material according to claim 1, characterized in that, The coating composition further includes vinyl-terminated dimethylpolysiloxane.

4. The coating material according to claim 3, characterized in that, The vinyl-terminated dimethylpolysiloxane is present in parts by weight of 70 to 300.

5. The coating material according to claim 3, characterized in that, The vinyl-terminated dimethylpolysiloxane has a molecular weight of 1500-3000.

6. The coating material according to claim 3, characterized in that, The coating composition also includes zinc oxide.

7. The coating material according to claim 6, characterized in that, The zinc oxide is micro-nano tetrapod zinc oxide.

8. The coating material according to claim 7, characterized in that, The micro-nano tetrapod zinc oxide has a mass fraction of 2 to 25 parts by mass.

9. The coating material according to claim 1, characterized in that, The indole derivative containing a carbon-carbon double bond is selected from at least one of N-(1H-5-bromoindole-3-methylene)acrylamide, N-(1H-6-chloroindole-3-methylene)acrylamide, N-(1H-2-methylindole-3-methylene)acrylamide, N-(1H-5-nitroindole-3-methylene)acrylamide, and N-(1H-2-phenylindole-3-methylene)acrylamide.

10. The coating material according to claim 1, characterized in that, The initiator is selected from at least one of 1,1'-azobis(cyclohexanenitrile) and azobisisobutyronitrile.

11. The coating material according to claim 1, characterized in that, The click reaction of the mercapto-olefin is carried out at a temperature of 80–90 °C for 2–5 h.

12. The coating material according to claim 3, characterized in that, Pentaerythritol tetra-3-mercaptopropionate, an indole derivative containing carbon-carbon double bonds, and vinyl-terminated dimethyl polysiloxane were subjected to a mercapto-olefin click reaction under the action of an initiator to obtain a prepolymer, which was then subjected to a polycondensation reaction with hexamethylene diisocyanate.

13. The coating material according to claim 4, characterized in that, Pentaerythritol tetra-3-mercaptopropionate, an indole derivative containing carbon-carbon double bonds, and vinyl-terminated dimethyl polysiloxane were subjected to a mercapto-olefin click reaction under the action of an initiator to obtain a prepolymer; zinc oxide was dispersed in the prepolymer and then subjected to a polycondensation reaction with hexamethylene diisocyanate.

14. The coating material according to claim 13, characterized in that, The dispersion is ultrasonic dispersion.

15. An antifouling coating prepared from the coating material according to any one of claims 1-14.

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