Functionality-containing silane coupling agent as well as preparation method and application thereof

Abstract

The invention discloses a silane coupling agent containing functionality and a preparation method and application thereof, the silane coupling agent has the following structure: H2C = CX-A-B-(MZ) n-N-Si (O-Y) 3, in the formula, X is a hydrogen atom, alkyl or alkoxy; a is an alkylene group or a derivative thereof, an amide group or a derivative thereof, an acyloxy group or an oxygen atom; b, M and N are one or more of alkylene and derivatives thereof, alkyleneoxy and derivatives thereof, alkyleneamine and derivatives thereof or arylene and derivatives thereof; y is alkyl; z is a hydrogen atom, a vinyl group, an acylamino group, an acyloxy group, an alkyl group and a derivative thereof, an alkylene group and a derivative thereof, an alkyloxy group and a derivative thereof, an alkylamino group and a derivative thereof, or an arylene group and a derivative thereof; n is a natural integer. The nano composite resin with high refractive index, high light transmittance and low haze can be formed by applying the nano composite resin to surface modification of nano oxide and then dispersing the nano oxide into different acrylic resin monomers.

Description

Technical Field

[0001] This invention relates to the field of optical materials, specifically to a functionalized silane coupling agent, its preparation method, and its application. Background Technology

[0002] With the rapid development of information technology, optical film materials for display devices with high refractive index and high transmittance are increasingly widely used. Currently, nanocomposite resins are the preferred choice for preparing high-refractive-index optical film materials, which are doped with inorganic nanomaterials with high refractive index and other organic resin monomers. However, pure inorganic nanomaterials are incompatible with organic matter, which leads to phase separation when the two are mixed, resulting in opaque optical films. According to the principle of "like dissolves like," substances with similar polarities can dissolve together. Therefore, in order to disperse inorganic nanomaterials in organic matter, it is necessary to graft some organic matter onto the surface of inorganic nanomaterials through chemical bonds or hydrogen bonds, thereby encapsulating the inorganic nanomaterials. Inorganic nanomaterials encapsulated by organic matter acquire lipophilic properties and can be dispersed in organic matter. This process of changing the properties of inorganic nanomaterials is called modification, and the organic matter that makes inorganic nanomaterials lipophilic is called a modifier. Currently, most reported modifiers are simple alkyl derivatives. For example, US patents No. 6,376,590 (Kolb et al.), No. 7,241,437, and No. 7,429,422 (both granted to Davidson et al.) utilize short-chain carboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, or combinations thereof to modify nano-zirconia. However, these modifiers are acidic and corrosive to equipment, and they do not contain unsaturated bonds, making cross-linking polymerization impossible. Silane coupling agents are non-acidic, non-corrosive to equipment, and exhibit good modification effects on inorganic nanoparticles, making them an ideal modifier. In China, Sun Mingke et al. (CN.201410841971.9) used silane coupling agents such as KH-550 and KH-560 to modify the surface of zirconia, obtaining well-dispersed nanocomposite resins. Currently, the silane coupling agents sold on the market have simple molecular structures, and the high proportion of weakly polar groups leads to poor compatibility between composite resins and polyalkoxyl-based organic resin monomers, which limits their application range. Summary of the Invention

[0003] The purpose of this invention is to overcome the shortcomings of the prior art and provide a functional silane coupling agent, its preparation method, and its application.

[0004] The technical solution of the present invention is as follows:

[0005] A functionalized silane coupling agent has the following structure:

[0006] H2C = CX - AB - (MZ) n-N-Si(OY)3

[0007] Wherein, X is a hydrogen atom, alkyl or alkoxy group; A is an alkylene group or its derivative, amide group or its derivative, acyloxy group or oxygen atom; B, M, N are one or more of alkylene groups and their derivatives, alkoxy groups and their derivatives, alkylamino groups and their derivatives or aryl groups and their derivatives; Y is an alkyl group; Z is a hydrogen atom, vinyl group, amide group, acyloxy group, alkyl group and its derivatives, alkylene groups and their derivatives, alkoxy groups and their derivatives, alkylamino groups and their derivatives or aryl groups and their derivatives; n is a natural integer.

[0008] Optionally, A is an alkylene group having the following structure:

[0009] -(CH2) m1 -(CHR1) m2 -(CH2) m3 -

[0010] Wherein, R1 is selected from 1 to 10 alkyl chains, and m1, m2, and m3 each take natural integer values.

[0011] Optionally, B is an alkylene group having the following structure:

[0012] -(CH2) m1 -(CHR1) m2 -(CH2) m3 -

[0013] Wherein, R1 is selected from 1 to 10 alkyl chains, and m1, m2, and m3 each take natural integer values.

[0014] Optionally, B is an alkylene derivative having the following structure:

[0015] -(CHR2) m1 -(CHR1) m2 -(CHR3) m3 -

[0016] Wherein, R1 is selected from 1 to 10 alkyl chains or alkoxy chains, R2 and R3 are each selected from hydrogen atoms, fluorine atoms, chlorine atoms, bromine atoms or iodine atoms, and m1, m2 and m3 are each natural integers.

[0017] A method for preparing the above-mentioned functionalized silane coupling agent involves sequentially adding N1-methyl-N2-[3-(trimethoxysilyl)propyl]ethane-1,2-diamine, triethylamine, and dichloromethane to a flask, controlling the temperature below -10°C. Acrylamide chloride is then added to a constant-pressure dropping funnel, and after replacing the air with nitrogen, the mixture is continuously added with stirring to maintain the reaction temperature below 10°C. After the addition is complete, the reaction continues. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. The solvent is then removed to obtain the functionalized silane coupling agent.

[0018] A method for preparing the above-mentioned functionalized silane coupling agent involves sequentially adding 3,3-dimethoxy-2,7,10-trioxa-3-sildodecane-12-ol, triethylamine, and dichloromethane to a flask, controlling the temperature below -10°C. Acrylamide chloride is then added to a constant-pressure dropping funnel, and after replacing the air with nitrogen, the mixture is continuously added with stirring to maintain the reaction temperature below 10°C. After the addition is complete, the reaction continues. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, the functionalized silane coupling agent is obtained.

[0019] A method for preparing the above-mentioned functionalized silane coupling agent involves sequentially adding N-methyl-2-[3-(trimethoxysilyl)propoxy]ethyl-1-amine, triethylamine, and dichloromethane to a flask, controlling the temperature below -10°C, adding acrylate chloride to a constant-pressure dropping funnel, replacing the air with nitrogen, and continuously adding and stirring to keep the reaction temperature below 10°C. After the addition is complete, the reaction continues. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, the functionalized silane coupling agent is obtained.

[0020] A method for preparing the above-mentioned functionalized silane coupling agent involves sequentially adding 6-(trimethoxysilyl)hexane-1,3-diol, triethylamine, and dichloromethane to a flask, controlling the temperature below -10°C, adding acrylate chloride to a constant-pressure dropping funnel, replacing the air with nitrogen, and continuously adding and stirring to keep the reaction temperature below 10°C. After the addition is complete, the reaction continues. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, the functionalized silane coupling agent is obtained.

[0021] A method for preparing the above-mentioned functionalized silane coupling agent involves sequentially adding 3,3-dimethoxy-2-oxa-7,10-diaza-3-sildodecane-12-ol, triethylamine, and dichloromethane to a flask, controlling the temperature below -10°C. Acrylamide chloride is then added to a constant-pressure dropping funnel, and after replacing the air with nitrogen, the mixture is continuously added with stirring to maintain the reaction temperature below 10°C. After the addition is complete, the reaction continues. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, the functionalized silane coupling agent is obtained.

[0022] According to the above-mentioned application of functionalized silane coupling agents, the functionalized silane coupling agents are applied to the surface modification of nano-oxides, and then the modified nano-oxides are dispersed in different acrylic resin monomers to form nanocomposite resins.

[0023] Compared with the prior art, the beneficial effects of the present invention are as follows: The present invention prepares a silane coupling agent containing multiple highly polar groups such as acryloyloxy or acrylamide, secondary or tertiary amine, alkoxy or alkeneoxy, alkyl or alkylene, siloxane, aryl and their derivatives, which can meet the application requirements of optical film materials. When applied to the surface modification of nano-oxides, the modified nano-oxides can be dispersed in different acrylic resin monomers to form nanocomposite resins with high refractive index, high transmittance and low haze. Attached Figure Description

[0024] To more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0025] Figure 1 A preferred structural diagram of a functionalized silane coupling agent provided by the present invention. Figure 1 ;

[0026] Figure 2 A preferred structural diagram of a functionalized silane coupling agent provided by the present invention. Figure 2 ;

[0027] Figure 3 A preferred structural diagram of a functionalized silane coupling agent provided by the present invention. Figure 3 ;

[0028] Figure 4 This is a schematic diagram illustrating the synthesis of a functional silane coupling agent according to Example 1 of the present invention.

[0029] Figure 5 This is a schematic diagram illustrating the synthesis of a functional silane coupling agent according to Example 2 of the present invention.

[0030] Figure 6 This is a schematic diagram illustrating the synthesis of a functional silane coupling agent provided in Example 3 of the present invention.

[0031] Figure 7 This is a schematic diagram illustrating the synthesis of a functional silane coupling agent provided in Example 4 of the present invention.

[0032] Figure 8 This is a schematic diagram illustrating the synthesis of a functional silane coupling agent provided in Example 5 of the present invention.

[0033] Figure 9 This is a schematic diagram illustrating the synthesis of a functional silane coupling agent provided in Example 6 of the present invention.

[0034] Figure 10 This is a schematic diagram illustrating the synthesis of a functional silane coupling agent provided in Example 7 of the present invention. Detailed Implementation

[0035] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the invention.

[0036] This invention provides a functionalized silane coupling agent having the following structure:

[0037] H2C = CX - AB - (MZ) n -N-Si(OY)3

[0038] Wherein, X is a hydrogen atom, alkyl or alkoxy group; A is an alkylene group or its derivative, amide group or its derivative, acyloxy group or oxygen atom; B, M, N are one or more of alkylene groups and their derivatives, alkoxy groups and their derivatives, alkylamino groups and their derivatives or aryl groups and their derivatives; Y is an alkyl group; Z is a hydrogen atom, vinyl group, amide group, acyloxy group, alkyl group and its derivatives, alkylene groups and their derivatives, alkoxy groups and their derivatives, alkylamino groups and their derivatives or aryl groups and their derivatives; n is a natural integer.

[0039] Optionally, A is an alkylene group having the following structure:

[0040] -(CH2) m1 -(CHR1) m2 -(CH2) m3 -

[0041] Wherein, R1 is selected from 1 to 10 alkyl chains, and m1, m2, and m3 each take natural integer values.

[0042] Optionally, B is an alkylene group having the following structure:

[0043] -(CH2) m1 -(CHR1) m2 -(CH2) m3 -

[0044] Wherein, R1 is selected from 1 to 10 alkyl chains, and m1, m2, and m3 each take natural integer values.

[0045] Optionally, B is an alkylene derivative having the following structure:

[0046] -(CHR2) m1 -(CHR1) m2 -(CHR3) m3 -

[0047] Wherein, R1 is selected from 1 to 10 alkyl chains or alkoxy chains, R2 and R3 are each selected from hydrogen atoms, fluorine atoms, chlorine atoms, bromine atoms or iodine atoms, and m1, m2 and m3 are each natural integers.

[0048] Better, combination Figures 1-3 The diagram shows a preferred structure of the functionalized silane coupling agent of the present invention.

[0049] To illustrate the technical solution described in this invention, specific embodiments are described below.

[0050] Example 1

[0051] This embodiment provides a method for preparing the above-mentioned functionalized silane coupling agent. In a 300ml round-bottom flask, 23.63g of N1-methyl-N2-[3-(trimethoxysilyl)propyl]ethane-1,2-diamine (0.1mol), 20g of triethylamine, and 150g of dichloromethane are added sequentially. The temperature is controlled below -10℃. 18.1g of acrylate chloride (0.2mol) is added to a 250ml constant-pressure dropping funnel. After purging the air with nitrogen, the mixture is continuously added with stirring, maintaining the reaction temperature below 10℃. After the addition is complete, the reaction continues for 3 hours. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, 26.92g of the functionalized silane coupling agent (e.g., ...) is obtained. Figure 4 As shown), the yield was 64.5%, the refractive index was 1.458 (25℃), and the viscosity was 124 cp (25℃).

[0052] 1H NMR(500MHz,Chloroform-d)δ6.55,6.36,6.12,6.10,6.09,6.06,5.87,5.85,5.84,5.83,3. 57,3.51,3.49,3.27,3.25,3.19,3.16,2.98,1.67,1.64,1.61,1.58,1.04,1.01,0.97,0.94.

[0053] 13C NMR (125MHz, Common NMR Solvents)δ229.69,225.78,206.26,198.43,190.62,170.50,169.98,160.70,130.52,129.27,127.98,127.83,120.29 ,112.51,112.48,81.25,81.23,51.97,50.94,49.98,48.55,46.05,45.40,35.69,24.20,18.72,10.21,-8.62,-10.53.

[0054] Example 2

[0055] This embodiment provides a method for preparing the above-mentioned functionalized silane coupling agent. In a 300ml round-bottom flask, 27.84g of N1-methyl-N2-[3-(trimethoxysilyl)propyl]ethane-1,2-diamine (0.1mol), 20g of triethylamine, and 150g of dichloromethane are added sequentially. The temperature is controlled below -10℃. 18.1g of acrylate chloride (0.2mol) is added to a 250ml constant-pressure dropping funnel. After purging the air with nitrogen, the mixture is continuously added with stirring, maintaining the reaction temperature below 10℃. After the addition is complete, the reaction continues for 3 hours. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, 29.13g of the functionalized silane coupling agent (e.g., ...) is obtained. Figure 5 As shown), the yield was 63.4%, the refractive index was 1.456 (25℃), and the viscosity was 160cp (25℃).

[0056] 1H NMR(500MHz,Chloroform-d)δ6.55,6.36,6.12,6.10,6.09,6.06,5.87,5.85,5.84,5.83,3.65, 3.51,3.49,3.27,3.25,3.19,3.16,2.98,1.74,1.71,1.64,1.61,1.24,1.21,1.18,1.15,1.12.

[0057] 13C NMR (125MHz, Common NMR Solvents) δ 170.50, 169.98, 130.52, 129.27, 127.98, 127.83, 59.21, 51.97, 48.55, 45.40, 35.69, 24.37, 18.88, 12.82.

[0058] Example 3

[0059] This embodiment provides a method for preparing the above-mentioned functionalized silane coupling agent. In a 500ml round-bottom flask, 48.04g of 3,3-dimethoxy-2,7,10-trioxa-3-siladenodecane-12-ol (0.2mol), 20g of triethylamine, and 200g of dichloromethane are added sequentially. The temperature is controlled below -10℃. 18.1g of acryloyl chloride (0.2mol) is added to a 250ml constant-pressure dropping funnel. After purging the air with nitrogen, the mixture is continuously added with stirring, maintaining the reaction temperature below 10℃. After the addition is complete, the reaction continues for 2 hours. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, 41.46g of the functionalized silane coupling agent (e.g., ...) is obtained. Figure 6 As shown), the yield was 66.3%, the refractive index was 1.435 (25℃), and the viscosity was 144cp (25℃).

[0060] 1H NMR (500MHz, Chloroform-d) δ6.14,6.12,6.10,5.96,5.94,4.23,3.63,3.59,3.57,3.55,3.54,1.75,1.73,1.63,1.61,1.10,1.08,1.02,0.99.

[0061] 13C NMR (125MHz, Common NMR Solvents) δ 170.01, 130.60, 129.93, 72.23, 71.45, 70.98, 70.55, 65.02, 50.36, 27.05, 10.55.

[0062] Example 4

[0063] This embodiment provides a method for preparing the above-mentioned functionalized silane coupling agent. In a 300ml round-bottom flask, 20.92g of N-methyl-2-[3-(trimethoxysilyl)propoxy]ethyl-1-amine (0.1mol), 10g of triethylamine, and 150g of dichloromethane are added sequentially. The temperature is controlled below -10℃. 9.05g of acrylate chloride (0.1mol) is added to a 250ml constant-pressure dropping funnel. After purging the air with nitrogen, the mixture is continuously added with stirring, maintaining the reaction temperature below 10℃. After the addition is complete, the reaction continues for 3 hours. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, 17.3g of the functionalized silane coupling agent (such as...) is obtained. Figure 7 As shown), the yield was 61.4%, the refractive index was 1.437 (25℃), and the viscosity was 180cp (25℃).

[0064] 1H NMR (500MHz, Chloroform-d) δ6.36,6.09,6.06,5.85,5.83,3.57,3.57,3.54,3.47,2.99,1.74,1.71,1.66,1.64,1.10,1.08,1.02,0.99.

[0065] 13C NMR (125MHz, Common NMR Solvents) δ 169.96, 129.57, 127.83, 71.98, 69.85, 50.36, 48.99, 36.25, 27.73, 10.55.

[0066] Example 5

[0067] This embodiment provides a method for preparing the above-mentioned functionalized silane coupling agent. In a 300ml round-bottom flask, 20.73g of N-methyl-2-[3-(trimethoxysilyl)propoxy]ethyl-1-amine (0.1mol), 00g of triethylamine, and 150g of dichloromethane are added sequentially. The temperature is controlled below -10℃. 18.1g of acrylate chloride (0.1mol) is added to a 250ml constant-pressure dropping funnel. After purging the air with nitrogen, the mixture is continuously added with stirring, maintaining the reaction temperature below 10℃. After the addition is complete, the reaction continues for 2 hours. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, 23.64g of the functionalized silane coupling agent (e.g., ...) is obtained. Figure 8 As shown), the yield was 67.1%, the refractive index was 1.457 (25℃), and the viscosity was 210cp (25℃).

[0068] 1H NMR(500MHz,Chloroform-d)δ6.56,6.14,6.12,6.10,6.09,5.96,5.94,5.87,5.84,4. 26,3.57,3.50,3.25,3.23,3.18,3.16,1.72,1.69,1.61,1.59,1.04,1.01,0.97,0.94.

[0069] 13C NMR (125MHz, Common NMR Solvents) δ170.12, 169.97, 130.60, 130.54, 129.76, 127.87, 64.55, 51.16, 49.98, 49.85, 24.11, 10.21.

[0070] Example 6

[0071] This embodiment provides a method for preparing the above-mentioned functionalized silane coupling agent. In a 300ml round-bottom flask, 71.49g of 6-(trimethoxysilyl)hexane-1,3-diol (0.3mol), 60g of triethylamine, and 300g of dichloromethane are added sequentially. The temperature is controlled below -10℃. 54.3g of acrylate chloride is added to a 250ml constant-pressure dropping funnel. After purging the air with nitrogen, the mixture is continuously added with stirring, maintaining the reaction temperature below 10℃. After the addition is complete, the reaction continues for 2 hours. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, 74.52g of functionalized silane coupling agent (such as...) is obtained. Figure 9 As shown), the yield was 64.8%, the refractive index was 1.444 (25℃), and the viscosity was 1454 cp (25℃).

[0072] 1H NMR(500MHz,Chloroform-d)δ6.14,6.12,6.07,6.06,6.05,6.01,5.96,5.94,5.91,5.88,4.81,4.33,4.30,4. 21,4.18,3.57,2.23,2.20,2.07,2.05,1.95,1.92,1.73,1.70,1.67,1.64,1.61,1.58,1.17,1.15,1.14,1.12.

[0073] 13C NMR (125MHz, Common NMR Solvents) δ170.05, 169.25, 130.95, 130.57, 129.70, 129.57, 81.14, 65.15, 50.31, 36.94, 35.31, 21.77, 14.97.

[0074] Example 7

[0075] This embodiment provides a method for preparing the above-mentioned functionalized silane coupling agent. In a 300ml round-bottom flask, 39.95g of 3,3-dimethoxy-2-oxa-7,10-diaza-3-sildodecane-12-ol (0.15mol), 45g of triethylamine, and 150g of dichloromethane are added sequentially. The temperature is controlled below -10℃. 40.73g of acrylate chloride (0.45mol) is added to a 250ml constant-pressure dropping funnel. After replacing the air with nitrogen, the mixture is continuously added dropwise with stirring, maintaining the reaction temperature below 10℃. After the addition is complete, the reaction continues for 2 hours. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, 47.03g of the functionalized silane coupling agent is obtained, with a yield of 64.8%, a refractive index of 1.467 (25℃), and a viscosity of 240cp (25℃).

[0076] 1H NMR(500MHz,Chloroform-d)δ6.56,6.55,6.14,6.12,6.12,6.10,6.09,5.96,5.94,5.87,5.84,4. 26,3.57,3.53,3.49,3.46,3.27,3.25,3.19,3.16,1.67,1.64,1.61,1.58,1.04,1.01,0.97,0.94.

[0077] 13C NMR (125MHz, Common NMR Solvents) δ170.50,170.12,169.92,130.60,130.52,130.42,129.76,127.98,127.87,64.49,51.97,49.98,49.93,44.44,43.91,24.20,10.21.

[0078] The functionalized silane coupling agent prepared in Examples 1 to 7 was applied to the surface modification of nano-oxides. The modified nano-oxides could be dispersed in different acrylic resin monomers to form nanocomposite resins with high refractive index, high transmittance, and low haze. The measurement results are shown in the table below:

[0079]

[0080]

[0081] The above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, and improvements made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A silane coupling agent containing functionality, characterized in that, It has the following structure: H2C=CX-AB-(MZ) n -N-Si(OY)3 Wherein, X is a hydrogen atom, alkyl or alkoxy group; A is an alkylene group or its derivative, amide group or its derivative, acyloxy group or oxygen atom; B, M, N are one or more of alkylene groups and their derivatives, alkoxy groups and their derivatives, alkylamino groups and their derivatives or aryl groups and their derivatives; Y is an alkyl group; Z is a hydrogen atom, vinyl group, amide group, acyloxy group, alkyl group and its derivatives, alkylene groups and their derivatives, alkoxy groups and their derivatives, alkylamino groups and their derivatives or aryl groups and their derivatives; n is a natural integer.

2. The silane coupling agent containing functionality according to claim 1, characterized in that, A is an alkylene group, which has the following structure: -(CH2) m1 -(CHR1) m2 -(CH2) m3 - Wherein, R1 is selected from 1 to 10 alkyl chains, and m1, m2, and m3 each take natural integer values.

3. The silane coupling agent containing functionality according to claim 1, characterized in that, The B is an alkylene group, which has the following structure: -(CH2) m1 -(CHR1) m2 -(CH2) m3 - Wherein, R1 is selected from 1 to 10 alkyl chains, and m1, m2, and m3 each take natural integer values.

4. A silane coupling agent containing functionality according to claim 1, characterized in that, B is an alkylene derivative having the following structure: -(CHR2) m1 -(CHR1) m2 -(CHR3) m3 - Wherein, R1 is selected from 1 to 10 alkyl chains or alkoxy chains, R2 and R3 are each selected from hydrogen atoms, fluorine atoms, chlorine atoms, bromine atoms or iodine atoms, and m1, m2 and m3 are each natural integers.

5. A method for preparing the functionalized silane coupling agent according to any one of claims 1 to 4, characterized in that, In a flask, N1-methyl-N2-[3-(trimethoxysilyl)propyl]ethane-1,2-diamine, triethylamine, and dichloromethane are added sequentially. The temperature is controlled below -10°C. Acrylamide chloride is added to a constant-pressure dropping funnel. After replacing the air with nitrogen, the mixture is continuously added with stirring to keep the reaction temperature below 10°C. After the addition is complete, the reaction continues. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, the functional silane coupling agent is obtained.

6. A method for preparing the functionalized silane coupling agent according to any one of claims 1 to 4, characterized in that, 3,3-Dimethoxy-2,7,10-trioxa-3-sildodecane-12-ol, triethylamine, and dichloromethane were added sequentially to a flask, and the temperature was controlled below -10°C. Acrylamide chloride was added to a constant-pressure dropping funnel, and after replacing the air with nitrogen, the mixture was continuously added dropwise with stirring to keep the reaction temperature below 10°C. After the addition was complete, the reaction continued. After the reaction was complete, the solid was removed by filtration, the reaction solution was desolventized, and the solution was decolorized and purified by column chromatography. After removing the solvent, the functional silane coupling agent was obtained.

7. A method for preparing the functionalized silane coupling agent according to any one of claims 1 to 4, characterized in that, In a flask, N-methyl-2-[3-(trimethoxysilyl)propoxy]ethyl-1-amine, triethylamine, and dichloromethane are added sequentially. The temperature is controlled below -10°C. Acrylamide chloride is added to a constant-pressure dropping funnel. After replacing the air with nitrogen, the mixture is continuously added with stirring to keep the reaction temperature below 10°C. After the addition is complete, the reaction continues. After the reaction is complete, the solid is removed by filtration, the reaction solution is desolventized, and the solution is decolorized and purified by column chromatography. After removing the solvent, the functional silane coupling agent is obtained.

8. A method for preparing the functionalized silane coupling agent according to any one of claims 1 to 4, characterized in that, 6-(trimethoxysilyl)hexane-1,3-diol, triethylamine, and dichloromethane were added sequentially to a flask, and the temperature was controlled below -10°C. Acrylamide chloride was added to a constant pressure dropping funnel, and after replacing the air with nitrogen, the mixture was continuously added dropwise with stirring to keep the reaction temperature below 10°C. After the addition was complete, the reaction continued. After the reaction was complete, the solid was removed by filtration, the reaction solution was desolventized, and the solution was decolorized and purified by column chromatography. After removing the solvent, the functional silane coupling agent was obtained.

9. A method for preparing the functionalized silane coupling agent according to any one of claims 1 to 4, characterized in that, 3,3-Dimethoxy-2-oxa-7,10-diaza-3-sildodecane-12-ol, triethylamine, and dichloromethane were added sequentially to a flask, and the temperature was controlled below -10°C. Acrylamide chloride was added to a constant pressure dropping funnel, and after replacing the air with nitrogen, the mixture was continuously added dropwise with stirring to keep the reaction temperature below 10°C. After the addition was complete, the reaction continued. After the reaction was complete, the solid was removed by filtration, the reaction solution was desolventized, and the solution was decolorized and purified by column chromatography. After removing the solvent, the functional silane coupling agent was obtained.

10. The application of a silane coupling agent containing functionality according to any one of claims 1 to 4, characterized in that, A functional silane coupling agent is applied to the surface modification of nano-oxides, and then the modified nano-oxides are dispersed in different acrylic resin monomers to form a nanocomposite resin.

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