A Y-type amphiphilic diene monomer, its preparation method, and its application in polymer microspheres.

Abstract

This invention discloses a Y-type amphiphilic diene monomer, its preparation method, and its application in polymer microspheres. This Y-type amphiphilic diene monomer possesses both hydrophilic and hydrophobic groups, which can induce interfacial polymerization and cross-linking to form microspheres. The Y-type monomer is obtained by a substitution reaction between an alkyl primary amine and a halomethyl methacrylate to yield an intermediate; the intermediate is then hydrolyzed under alkaline conditions. Applying this Y-type monomer to the preparation of polymer microspheres and nano-silica sol composites to form a self-cleaning antireflective film significantly improves the coating's self-cleaning performance and transmittance.

Description

Technical Field

[0001] This invention relates to a Y-type amphiphilic diene monomer, its preparation method, and its application in polymer microspheres. It also relates to a method for preparing a self-cleaning antireflective film using polymer microspheres, belonging to the field of coating materials. Background Technology

[0002] The photovoltaic effect is the most direct way to utilize solar energy, and solar panels are commonly used to achieve this conversion. However, when sunlight shines on a solar panel, about 8% of the sunlight is reflected by the glass cover, which significantly reduces the conversion efficiency. Furthermore, for outdoor applications, the adsorption of dust and organic pollutants can drastically reduce the light transmittance of the glass cover. Therefore, designing and fabricating a thin-film layer that reduces light reflection on the glass surface and has self-cleaning properties is crucial and has broad application value.

[0003] SiO2 is a common low-refractive-index material with excellent optical properties and stable chemical properties, and is therefore often used to prepare antireflective films. By appropriately modifying SiO2 films, such as adding low-surface-energy substances to make them superhydrophobic, or increasing surface roughness to enhance their hydrophilicity, and by creating pores to lower their refractive index, researchers have obtained films that possess both good antireflective effects and a certain degree of self-cleaning properties.

[0004] Common methods to increase porosity include using pore-forming agents such as polyurethane particles (PU) and polyethylene glycol (PEG), but these often require high-temperature calcination. Patent CN202010581005.3 uses PEG as a pore-forming agent, and the self-cleaning antireflective coating needs to be annealed in a tube furnace at 450-550°C for 2-3 hours, which is cumbersome and costly.

[0005] Dust accumulation is one of the main reasons for reduced energy conversion efficiency. When superhydrophilic water coatings are used as coatings for solar panels, they can easily achieve self-cleaning through natural rainwater, thus greatly reducing the daily maintenance costs of the equipment. Currently, almost all methods for synthesizing hollow spherical SiO2 nanoparticles require the introduction of a polymer template agent during the preparation process to first form core-shell structured nanoparticles of template SiO2. Therefore, when preparing hollow spherical SiO2 antireflective films on glass, researchers generally use a high-temperature annealing process at 300°C or higher to remove the template agent encapsulated in the hollow spherical SiO2 nanoparticles. On the one hand, this increases energy consumption, leading to higher costs; on the other hand, this high-temperature calcination process for removing the template agent is not suitable for most flexible polymer substrates because the glass transition temperature of polymer materials is generally below 200°C.

[0006] Therefore, developing a method for preparing hollow nanospheres at low temperatures has significant practical value. Summary of the Invention

[0007] To address the shortcomings of existing technologies that use single SiO2 thin films to prepare self-cleaning reflective films, such as low transmittance and the need for high-temperature calcination, which is demanding and energy-intensive, the first objective of this invention is to provide a Y-type amphiphilic diene monomer. This Y-type amphiphilic diene monomer not only possesses both hydrophilic and hydrophobic groups, which can induce interfacial polymerization to form microspheres, but also exhibits a Y-shaped symmetrical structure with olefin groups on both sides, which is beneficial for forming chain structures and can increase cross-linking to form a three-dimensional network structure.

[0008] The second objective of this invention is to provide a method for preparing Y-type amphiphilic diene monomers, which has the advantages of a short process flow and mild reaction conditions.

[0009] The third objective of this invention is to provide a method for preparing polymer microspheres. Due to the large hydrophilic head and long hydrophobic alkyl chain in the Y-type molecular structure, which satisfies the geometric configuration for assembling into spherical micelles, it can serve as a structure-directing molecule to guide the preparation of polymer microspheres.

[0010] The fourth objective of this invention is to provide a polymer microsphere containing a large number of hydrophilic groups, which can effectively improve the self-cleaning performance of the coating.

[0011] The fifth objective of this invention is to provide a method for preparing a self-cleaning antireflective film. By mixing the polymer microspheres prepared in this invention with nano-silica sol and volatilizing the oil phase encapsulated in the polymer microspheres at low temperature to form hollow polymer microspheres, the self-cleaning performance and transmittance of the coating can be greatly improved.

[0012] To achieve the above-mentioned technical objectives, the present invention provides a Y-type amphiphilic diene monomer having the structure shown in Formula I:

[0013]

[0014] Wherein, R is a saturated aliphatic hydrocarbon group with 8 to 18 carbon atoms.

[0015] The monomer of this invention has a Y-shaped symmetrical structure, with a central hydrophobic alkyl chain as the axis, and two hydrophilic carboxyl groups and two olefin groups on each side. Because this monomer simultaneously possesses hydrophilic and hydrophobic groups, it satisfies the geometric configuration for assembling into spherical micelles, and thus can act as a structure-directing molecule to guide the binding of hydrophilic molecules to form polymer microspheres. Furthermore, the two olefin groups can not only undergo addition reactions to obtain long-chain structures, but also participate in cross-linking between monomers to form complex three-dimensional network structures.

[0016] This invention also provides a method for preparing a Y-type amphiphilic diene monomer, which involves reacting an alkyl primary amine with a halomethyl methacrylate via a substitution reaction to obtain an intermediate; the intermediate is then hydrolyzed under alkaline conditions to obtain the final product; the alkyl primary amine has the structure shown in Formula II:

[0017] R-NH2

[0018] Formula II

[0019] The intermediate has a structure as shown in Formula III:

[0020]

[0021] Wherein, R is a saturated aliphatic hydrocarbon group with 8 to 18 carbon atoms.

[0022] The reaction for preparing Y-type amphiphilic diene monomers in this invention can be obtained solely through substitution and hydrolysis reactions, offering advantages such as a short process flow, mild reaction conditions, and ease of industrial production. The specific reaction equations are shown in Formulas IV and V:

[0023] 1) Synthesis of intermediates

[0024]

[0025] 2) The intermediate hydrolyzes to form a Y-type monomer.

[0026]

[0027] As a preferred option, X is a halogen (such as Cl, Br, I).

[0028] As a preferred embodiment, the molar ratio of the alkyl primary amine to the methyl halogenated methacrylate is 1:(2-3). By controlling the molar amount of methyl halogenated methacrylate to be two times or more than that of the alkyl primary amine, two hydrogen atoms on the primary amine can be substituted, thereby forming a Y-shaped symmetrical structure.

[0029] As a preferred embodiment, the alkyl primary amine is first added to a mixed solution of dichloromethane and triethylamine, stirred and mixed, and then methyl halomethacrylate is dissolved in dichloromethane and added dropwise to the mixed solution over an ice-water bath for 1 hour.

[0030] As a preferred embodiment, the molar ratio of the alkyl primary amine to triethylamine is 1:(1-2).

[0031] As a preferred embodiment, the substitution reaction conditions are: temperature 25–35°C, time 1–3 h. The substitution reaction of this invention can proceed rapidly at room temperature. After the reaction is complete, water is added for extraction, the organic phase is dried with anhydrous sodium sulfate, then purified by column chromatography, and finally the solvent is removed under reduced pressure to obtain a pale yellow oily liquid, which is the intermediate.

[0032] As a preferred embodiment, the hydrolysis reaction is performed under the following conditions: a temperature of 60–100°C and a reaction time of 4–6 hours.

[0033] As a preferred embodiment, the specific steps for hydrolyzing the intermediate to form a Y-type amphiphilic diene monomer are as follows: Sodium hydroxide and the intermediate are weighed into a round-bottom flask, then water and ethanol are added, and the mixture is heated to 60–100°C for reaction. After the reaction is complete, the solution becomes clear, the ethanol is evaporated under reduced pressure, and then acidified with dilute hydrochloric acid. The precipitate is then filtered and collected.

[0034] As a preferred embodiment, the molar ratio of sodium hydroxide to the intermediate is (2-4):1.

[0035] As a preferred embodiment, the concentration of the intermediate, water, and ethanol is 0.2–0.4 g / ml.

[0036] The present invention also provides a method for preparing polymer microspheres, which involves thoroughly mixing the above-mentioned Y-type amphiphilic diene monomer, sodium p-styrene sulfonate, and a counterionizing agent in an aqueous phase and an oil phase to form a homogeneous emulsion, and then adding a redox initiation system to initiate an interfacial polymerization reaction to obtain the polymer microspheres.

[0037] In the technical solution of this invention, during the mixing of the aqueous and oil phases, the Y-type amphiphilic diene monomer provided by this invention possesses both hydrophilic and hydrophobic groups, resulting in the olefin groups of the Y-type amphiphilic diene monomer being located at the interface between the aqueous and oil phases. A counterionizing agent can ionize the carboxyl groups of the Y-type amphiphilic diene monomer, while simultaneously causing interfacial polymerization and cross-linking of the carbon-carbon double bonds of sodium styrene sulfonate and the symmetrical olefin groups of the Y-type amphiphilic diene monomer, thus forming a polymer microsphere structure. Furthermore, this polymer microsphere possesses a unique structure consisting of a shell layer formed by the Y-type amphiphilic diene monomer and sodium styrene sulfonate, and an internal encapsulation of the oil phase. During the subsequent coating process, after the oil phase evaporates at low temperature, the polymer microsphere can form a hollow structure, further improving the coating's transmittance.

[0038] As a preferred embodiment, the oil phase is an organic reagent with a boiling point of 60–100 °C, such as n-heptane and n-hexane. If the boiling point of the oil phase is too low, it is prone to volatilization during the preparation of polymer microspheres, causing structural collapse. Conversely, if the boiling point of the oil phase is too high, it is impossible to achieve oil phase volatilization at low temperatures during the subsequent preparation of the antireflective film, resulting in a hollow polymer structure and thus reducing the transmittance of the antireflective film.

[0039] As a preferred embodiment, the redox initiation system includes a reducing agent such as sodium thiosulfate pentahydrate (1% of the molar amount of the Y-type monomer) and an oxidizing agent such as potassium persulfate (1% of the molar amount of the Y-type monomer).

[0040] As a preferred embodiment, the counterionizing agent is one of tetramethylguanidine, sodium hydroxide, and potassium hydroxide.

[0041] As a preferred embodiment, the molar ratio of the Y-type amphiphilic diene monomer to sodium p-styrene sulfonate is 1:(0.2-3). This molar ratio directly affects the structure of the prepared polymer microspheres. If the content of the Y-type amphiphilic diene monomer is too high, the alkyl content will be too high, resulting in larger pores after the film layer dries and the oil phase is removed, making it prone to "collapse" and reducing the light transmittance of the coating. Conversely, if the content of the Y-type amphiphilic diene monomer is too low, the sodium sulfonate content on the coating surface will be too high. Although this improves the hydrophilicity of the coating, it reduces its water resistance, thus shortening its service life. A further preferred molar ratio of the Y-type amphiphilic diene monomer to sodium p-styrene sulfonate is 1:(1-3).

[0042] As a preferred embodiment, the polymerization reaction conditions are: a temperature of 30–50°C and a reaction time of 16–24 h.

[0043] As a preferred embodiment, the volume ratio of the oil phase to the water phase is (0.01 to 0.03):1.

[0044] This invention also provides polymer microspheres obtained by the above-described preparation method. These polymer microspheres possess a unique structure consisting of a spherical shell layer formed from a Y-type amphiphilic diene monomer and sodium p-styrene sulfonate, and an internally encapsulated oil phase. Furthermore, these polymer microspheres contain a large number of hydrophilic groups, which effectively improve the self-cleaning properties of the coating.

[0045] This invention also provides a method for preparing a self-cleaning antireflective film. The method involves dispersing the aforementioned polymer microspheres in water to form a microsphere dispersion. This microsphere dispersion is then mixed with nano-silica sol, cast, and dried to obtain the self-cleaning antireflective film. By mixing the polymer microspheres prepared according to this invention with nano-silica sol and then volatilizing the oil phase encapsulated within the polymer microspheres at low temperature to form hollow polymer microspheres, the self-cleaning performance and transmittance of the coating can be greatly improved.

[0046] As a preferred embodiment, the mass ratio of the microsphere dispersion to the nano-silica sol is (1-3):1;

[0047] As a preferred embodiment, the solid content of the microsphere dispersion is 0.5% to 2%.

[0048] As a preferred embodiment, the nano-silica sol is obtained by hydrolysis of methyltriethoxysilane and tetraethyl orthosilicate in a mass ratio of 1:(1-2).

[0049] The specific steps for preparing a self-cleaning antireflective film using polymer microspheres in this invention are as follows:

[0050] 1) Preparation of nano-silica: Anhydrous ethanol was used as the solvent and ammonia (NH3·H2O) was used as the catalyst to prepare network SiO2 nanoparticles. First, a certain amount of ethanol, NH3·H2O and H2O were weighed and added to a three-necked flask in sequence. The reaction temperature of the oil bath was adjusted to 40-80℃. Then, a mixed solution of methyltriethoxysilane (MTES) and tetraethyl orthosilicate (TEOS) as a common silicon source was slowly added to the mixture. After the addition was completed, the mixture was stirred for 8-12 hours. The mass ratio of (TEOS+MTES):anhydrous ethanol:NH3·H2O:H2O = 1:(36-40):(2-4):(3-5). After aging for 2-3 days, nano-silica sol was obtained.

[0051] 2) Prepare SiQ2 mixed sol by mixing polymer microsphere dispersion and nano silica sol at a mass ratio of (1-3):1.

[0052] 3) The substrate is immersed in a beaker containing a SiO2 mixed sol at a constant speed. After standing in the sol for 10 minutes, it is pulled out at a constant speed of 50 mm / min. Once the substrate is completely removed from the SiO2 mixed sol, the pulling is stopped, and the substrate is allowed to stand for about 5 minutes to allow the solution on the substrate surface to evaporate fully, resulting in a relatively stable gel film. Finally, the gel film is dried in an 80℃ forced-air drying oven for 15 minutes to obtain the composite self-cleaning antireflective film.

[0053] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0054] 1) This invention provides a Y-type amphiphilic diene monomer, which not only has both hydrophilic and hydrophobic groups, which can induce monomer polymerization to form a hollow sphere structure, but also has a Y-shaped symmetrical structure with olefin groups on both the left and right sides, which is conducive to forming a chain structure and can increase its cross-linking to form a three-dimensional network structure.

[0055] 2) This invention provides a polymer microsphere and its preparation method. The polymer microsphere has a unique structure consisting of a spherical shell layer formed by a Y-type amphiphilic diene monomer and sodium p-styrene sulfonate, and an internal oil phase encapsulation. Its preparation utilizes the unique structure of the Y-type amphiphilic diene monomer, namely, a large hydrophilic head and a long hydrophobic alkyl chain, which satisfies the geometric configuration for assembly into spherical micelles. The monomer is used as a structure-directing molecule to guide the interfacial polymerization and crosslinking of sodium p-styrene sulfonate and the Y-type amphiphilic diene monomer at the interface between the aqueous and oil phases.

[0056] 3) This invention also provides an application of an organic-inorganic composite self-cleaning antireflective film prepared at low temperature based on polymer microspheres. A SiO2 mixed sol with a low refractive index is prepared using the mature sol-gel method. Furthermore, the oil phase encapsulated in the polymer microspheres is volatilized at low temperature during the coating process to form a hollow polymer microsphere structure. The presence of hydrophilic sodium styrene sulfonate in the polymer significantly improves the self-cleaning performance of the coating. In addition, the nanostructure of the hollow polymer spheres achieves higher transmittance than ordinary single SiO2 films. Attached Figure Description

[0057] Figure 1 The 1H NMR spectra of the intermediate (DBMD) and the Y-type amphiphilic diene monomer (DBMDA) prepared in Example 1 are shown below. Figure 1 (a) shows the chemical structural formula and 1H NMR spectrum of DBMD; Figure 1 (b) shows the chemical structure and 1H NMR spectrum of DBMDA.

[0058] Figure 2 Microscopic morphology images of polymer hollow spheres prepared with different contents of Y-type amphiphilic diene monomers; among which... Figure 2(a) is a TEM image of a solution with DBMDA at 5 mg / mL; Figure 2 (b) is a SEM image of the polymer powder when the molar ratio of DBMDA to SSS is 1:1 (SSS refers to sodium p-styrene sulfonate); Figure 2 (c) is a SEM image of polymer powder with a DBMDA:SSS molar ratio of 1:3; Figure 2 (d) is a SEM image of the polymer powder when the molar ratio of DBMDA to SSS is 3:1.

[0059] Figure 3 This is a SEM image of the self-cleaning antireflective film prepared in Example 2 of the present invention. Detailed Implementation

[0060] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0061] Examples 1-4

[0062] 1) Synthesis of intermediates

[0063] Dodecylamine (1.594 g, 8.6 mmol) was weighed into a round-bottom flask, and dichloromethane (5 mL) and triethylamine (2.3 mL, 16.5 mmol) were added and stirred. Methyl 2-bromomethacrylate (2 mL, 18.5 mmol) and dichloromethane (5 mL) were added dropwise into a dropping funnel over an ice-water bath for 1 hour. After the addition was complete, the reaction was continued at room temperature for 2 hours. After the reaction was complete, water was added for extraction, and the organic phase was dried over anhydrous sodium sulfate. The mixture was then purified by column chromatography, and finally, the solvent was removed under reduced pressure to obtain a pale yellow oily intermediate (DBMD) in 72% yield.

[0064] 2) Synthesis of Y-type amphiphilic diene monomers

[0065] Weigh sodium hydroxide (0.876 g, 21.9 mmol) and DBMD (2.783 g, 7.3 mmol) into a round-bottom flask, add water (6 mL) and ethanol (6 mL), and heat to 80 °C to react. After the reaction is complete, the solution becomes clear. After the ethanol is evaporated under reduced pressure, the solution is acidified with dilute hydrochloric acid. The precipitate is filtered and collected to obtain the Y-type amphiphilic diene monomer (DBMDA).

[0066] 3) Preparation of polymer nanospheres

[0067] Weigh out 0.6 mmol of DBMDA and sodium p-styrene sulfonate (SSS, 90% purity) at a molar ratio of 1:0–3.0 and add them to 10 mL of water. Then add 18 μL of tetramethylguanidine (TMG) and stir until the solution is clear. After three gas exchange cycles of freezing-evacuation-thawing-nitrogen purging, add n-heptane and stir until the solution is stable. Then add sodium thiosulfate pentahydrate (0.0015 g, 0.006 mmol) as a reducing agent and potassium persulfate (0.0019 g, 0.006 mmol) as an oxidizing agent. React at 40 °C and 500 rpm for 20 hours with a magnetic stirrer.

[0068] The specific formulations for preparing polymer nanospheres in Examples 1-4 are shown in Table 1:

[0069] Table 1. Specific formulations for the assembly copolymerization of DDBMDA-TMG and SSS.

[0070]

[0071] Application Examples 1-4

[0072] The polymer microspheres prepared in Examples 1-4 were used to prepare organic-inorganic composite self-cleaning antireflective films. The specific steps are as follows:

[0073] 1) Preparation of nano-silica: Networked SiO2 nanoparticles were prepared using anhydrous ethanol as solvent and ammonia (NH3·H2O) as catalyst. First, a certain amount of ethanol, NH3·H2O and H2O were weighed and added sequentially to a three-necked flask. The reaction temperature of the oil bath was adjusted to 60℃. Then, a mixed solution of methyltriethoxysilane (MTES) and tetraethyl orthosilicate (TEOS) (mass ratio 1:1) as a common silicon source was slowly added to the mixture. After the addition was completed, the mixture was stirred for 10 hours. The mass ratio of (TEOS+MTES):anhydrous ethanol:NH3·H2O:H2O = 1:37.98:3:4. After aging for 2 days, nano-silica sol was obtained.

[0074] 2) Prepare a SiO2 mixed sol by mixing polymer microsphere dispersion and nano silica sol at a mass ratio of 2:1, wherein the concentration of polymer microsphere dispersion is 10 mg / mL.

[0075] 3) The substrate is immersed in a beaker containing a SiO2 mixed sol at a constant speed. After standing in the sol for 10 minutes, it is pulled out at a constant speed of 50 mm / min. Once the substrate is completely removed from the SiO2 mixed sol, the pulling is stopped, and the substrate is allowed to stand for about 5 minutes to allow the solution on the substrate surface to evaporate fully, resulting in a relatively stable gel film. Finally, the gel film is dried in an 80℃ forced-air drying oven for 15 minutes to obtain the composite self-cleaning antireflective film.

[0076] Meanwhile, only the nano-silica sol prepared in step 1 was used to prepare the antireflection film control group, and the preparation of the antireflection film was the same as in step 3.

[0077] Table 2 Comparison of Test Results of Different Composite Self-Cleaning Antireflective Films

[0078]

[0079] Hydrophobic angle test method: The static contact angle of the coating was measured using a JGW-360a contact angle meter. The test liquid volume was 2 μL, and the test environment was 24±1℃ and 45±1% relative humidity. Five points were measured for the water droplet contact angle, and the average value was taken.

[0080] Transmittance test method: Transmittance is measured by a TH-110 transmittance haze meter. After construction, place the glass on the test platform, press the HOLD button on the instrument, and wait for the instrument to complete self-calibration before starting the test and recording the test results.

[0081] like Figure 2 As shown in Figure (a), in Example 1, when the DBMDA concentration was 5 mg / mL, TEM images showed that DBMDA assembled into a small number of spherical nanoparticles in water molecules. This was due to the large hydrophilic head and long hydrophobic alkyl chain in its molecular structure, which met the geometric configuration of assembling into spherical micelles. Since no hydrophilic monomer was added, the self-cleaning performance was poor, and the water droplet angle was 20°.

[0082] Y-type amphiphilic diene monomers were used as structure-directing molecules to guide the preparation of hollow polymer spheres from sodium styrene sulfonate. Characterization of the lyophilized polymer revealed that, due to the boiling point of n-heptane (98℃), small amounts of n-heptane could be easily removed during the drying process, forming hollow nanoparticles, which was confirmed in the SEM images. Figure 2 (c) and Figure 2 As shown in (d), when the molar ratio of DBMDA to SSS is 1:3 and 3:1, a large number of flattened spherical nanoparticles can be observed. However, due to the dense film layer, the porosity is significantly reduced and the surface is irregular, so the transmittance is not significantly improved.

[0083] The antireflection film sample prepared in Example 2 was subjected to electron microscopy scanning, and the morphology image (SEM image) is shown below. Figure 3 As shown, from Figure 3 As can be seen, the surface of the film is composed of polymer particles with a regular circular particle structure. This structure is beneficial to improving the superhydrophilicity and thus the self-cleaning performance of the coating. On the other hand, it can also be used to adjust the refractive index of the film, thereby significantly improving the transmittance of the film.

[0084] As shown in Table 2, when the polymer microspheres prepared in this invention are not added to the control group, the antireflective film prepared by using only nano-silica sol has a significantly increased water droplet angle, indicating that its self-cleaning effect is poor. At the same time, the light transmittance of the film is also significantly reduced.

Claims

1. A method for preparing a self-cleaning antireflective film, characterized in that: Polymer microspheres are dispersed in water to form a microsphere dispersion. The microsphere dispersion is then mixed with nano-silica sol, cast into a film, and dried to obtain the final product. The polymer microspheres are prepared by: thoroughly mixing an aqueous phase containing a Y-type amphiphilic diene monomer, sodium p-styrene sulfonate, and a counterionizing agent with an oil phase to form a homogeneous emulsion, and then adding a redox initiation system to initiate an interfacial polymerization reaction, thereby obtaining the polymer microspheres. The Y-type amphiphilic diene monomer has the structure shown in Formula I: ； Formula I; Wherein, R is a saturated aliphatic hydrocarbon group with 8 to 18 carbon atoms; The molar ratio of the Y-type amphiphilic diene monomer to sodium p-styrene sulfonate is 1:(0.2~3).

2. The method for preparing a self-cleaning antireflective film according to claim 1, characterized in that: The Y-type amphiphilic diene monomer is prepared by: subjecting an alkyl primary amine and a halomethyl methacrylate to a substitution reaction to obtain an intermediate; the intermediate is then hydrolyzed under alkaline conditions to obtain the final product. The alkyl primary amine has the structure shown in Formula II: ； Formula II; The intermediate has the structure shown in Formula III: ； Formula III; Wherein, R is a saturated aliphatic hydrocarbon group with 8 to 18 carbon atoms.

3. The method for preparing a self-cleaning antireflective film according to claim 2, characterized in that: The molar ratio of the alkyl primary amine to the methyl halogenated methacrylate is 1:(2~3). The conditions for the substitution reaction are: temperature 25~35℃, time 1~3h; The conditions for the hydrolysis reaction are: temperature of 60~100℃ and reaction time of 4~6h.

4. The method for preparing a self-cleaning antireflective film according to claim 1, characterized in that: The volume ratio of the oil phase to the water phase is (0.01~0.03):

1.

5. The method for preparing a self-cleaning antireflective film according to claim 4, characterized in that: The polymerization reaction conditions are: temperature of 30~50℃ and reaction time of 16~24h.

6. The method for preparing a self-cleaning antireflective film according to claim 1, characterized in that: The mass ratio of the microsphere dispersion to the nano silica sol is (1~3):1; The solid content of the microsphere dispersion is 0.5-2%.

7. The method for preparing a self-cleaning antireflective film according to claim 6, characterized in that: The nano-silica sol is obtained by hydrolysis of methyltriethoxysilane and tetraethyl orthosilicate in a mass ratio of 1:(1~2).

Images