Method for preparing 4-trimethoxysilyl styrene and application of 4-trimethoxysilyl styrene

Abstract

The invention belongs to the technical field of organosilicon compounds, and particularly relates to a method for preparing 4-trimethoxysilyl styrene and application of the 4-trimethoxysilyl styrene. The preparation method comprises the following steps: taking 4-iodobenzene ethane and trimethoxysilane as raw materials, and carrying out a coupling reaction to synthesize 4-trimethoxysilyl phenyl ethane; the preparation method comprises the following steps: reacting 4-trimethoxysilyl phenyl ethane with NBS (N-bromosuccinimide), and synthesizing 4-trimethoxysilyl phenyl bromoethane through a free radical bromination reaction; and carrying out hydrogen bromide removal on the 4-trimethoxysilyl phenyl bromoethane, so as to prepare the 4-trimethoxysilyl styrene. According to the application, (1) the 4-trimethoxysilyl styrene is used as a modifier, and (2) the 4-trimethoxysilyl styrene is applied to preparation of a resin compound; and (3) the 4-trimethoxysilyl styrene can improve the adhesive force between the heat-resistant resin and the substrate. According to the invention, the 4-trimethoxysilyl styrene is successfully prepared through different inventive concepts and new routes, so that more possibilities for synthesizing the compound are given, and the yield is also improved.

Description

Technical Field

[0001] The invention belongs to the technical field of organosilicon compounds, and specifically relates to a method for preparing 4-trimethoxysilylstyrene and its application. Background Art

[0002] In the prior art, 4-trimethoxysilylstyrene (CAS No.: 18001-13-3) can be prepared by a variety of methods, including Grignard reaction, addition reaction of silane and olefin, etc. The Grignard reaction includes the following routes: 1. Using p-chlorostyrene, magnesium, THF, and trimethylchlorosilane as raw materials to react to prepare 4-trimethoxysilylstyrene; 2. Using p-bromostyrene, magnesium, THF, and tetramethoxysilane as raw materials to react to prepare 4-trimethoxysilylstyrene; however, the yields of these two routes are relatively low. For example, the relevant yield disclosed in the document (PMID: 15875849) is 46%, and the relevant yield disclosed in the patent document with application No. DE10159859 is about 35%.

[0003] The present invention aims to try different inventive concepts and new routes to prepare 4-trimethoxysilylstyrene, which not only provides more possibilities for synthesizing the aforementioned compound, but also improves the yield of the preparation route. Summary of the invention

[0004] The present invention aims at the deficiencies of the prior art, provides a new method for preparing 4-trimethoxysilylstyrene, and provides related applications of the above-mentioned compound.

[0005] The technical solution of the present invention is as follows:

[0006] In a first aspect, the present invention provides a method for preparing 4-trimethoxysilylstyrene, comprising the steps of:

[0007] 4-Trimethoxysilylbenzene was synthesized by coupling reaction of 4-iodophenylethane and trimethoxysilane.

[0008] 4-Trimethoxysilylphenylethyl bromide is synthesized by reacting 4-trimethoxysilylphenylethyl with NBS via free radical bromination reaction;

[0009] 4-Trimethoxysilylphenylethyl bromide was used to dehydrobrominate 4-trimethoxysilylphenylethyl bromide to prepare 4-trimethoxysilylphenylethyl bromide.

[0010] More specific steps include:

[0011] The steps of synthesizing 4-trimethoxysilylphenylethane are as follows: 4-iodophenylethane and trimethoxysilane are used as raw materials, and a coupling reaction is carried out in a polar aprotic solvent under alkaline conditions and under the catalysis of a catalyst to synthesize 4-trimethoxysilylphenylethane.

[0012] In some embodiments, the polar aprotic solvent includes at least one of DMF, DMSO, and NMP, the catalyst includes Pd(t-Bu3P)2, and the base used in the alkaline condition includes an inorganic base, and the inorganic base includes at least one of K3PO4, Na2CO3, NaOAc, KOAc, and Na3PO4.

[0013] More specific steps include:

[0014] The steps of synthesizing 4-trimethoxysilylphenylethyl bromide are as follows: 4-trimethoxysilylphenylethyl bromide is reacted with NBS, a free radical initiator and an inert solvent are added, and 4-trimethoxysilylphenylethyl bromide is synthesized through a free radical bromination reaction.

[0015] In some embodiments, the free radical initiator includes at least one of BPO and AIBN, and the inert solvent includes at least one of carbon tetrachloride, petroleum ether, carbon disulfide, and ethyl acetate.

[0016] More specifically, the steps include: the step of synthesizing 4-trimethoxysilylstyrene is: 4-trimethoxysilylphenylethyl bromide is dehydrobrominated with sodium hydroxide in alcohol to obtain 4-trimethoxysilylstyrene.

[0017] The specific synthetic route is as follows:

[0018]

[0019] Wherein, Formula 1 is 4-trimethoxysilylphenylethane, Formula 2 is 4-trimethoxysilylphenylethyl bromide, and Formula 3 is 4-trimethoxysilylphenylethane.

[0020] In a second aspect, the present invention provides related applications of 4-trimethoxysilylstyrene:

[0021] Related application 1: Application of 4-trimethoxysilylstyrene as a modifier, wherein the 4-trimethoxysilylstyrene is prepared according to the aforementioned method for preparing 4-trimethoxysilylstyrene, and the modifier includes a silane coupling agent and a heat-resistant resin modifier.

[0022] Furthermore, 4-trimethoxysilylstyrene can be used to improve the adhesion of heat-resistant resins.

[0023] Related application 2: A resin composite, comprising a heat-resistant resin and 4-trimethoxysilylstyrene, wherein the 4-trimethoxysilylstyrene is prepared according to the aforementioned method for preparing 4-trimethoxysilylstyrene.

[0024] In some embodiments, the amount of 4-trimethoxysilylstyrene used is preferably 0.1-20% of the mass of the heat-resistant resin, and more preferably 0.5-10%.

[0025] Related application 3: A method for improving the adhesion between a heat-resistant resin and a substrate, wherein a heat-resistant resin and 4-trimethoxysilylstyrene are mixed and then coated on the substrate, wherein the 4-trimethoxysilylstyrene is prepared according to the aforementioned method for preparing 4-trimethoxysilylstyrene.

[0026] In some embodiments, the substrate comprises silicon, silicon dioxide, ceramic, or metal, and the metal is preferably aluminum.

[0027] The amount of 4-trimethoxysilylstyrene used is preferably 0.1 to 20% of the mass of the heat-resistant resin, and more preferably 0.5 to 10%.

[0028] The aforementioned heat-resistant resin includes resins such as polyimide resins and polybenzoxazole.

[0029] It should be noted that in the prior art, polyimide resins, polybenzoxazoles, etc. are generally used as heat-resistant resins in the semiconductor industry. However, with the continuous improvement of semiconductor integration, the development of microcircuit structures in the direction of three-dimensional multilayers, and the gradual trend of equipment towards miniaturization and multifunctionality, higher requirements are also placed on the physical and chemical properties of heat-resistant resins: it is necessary to improve the bonding force between the heat-resistant resin and the substrate. Among them, the simplest and most direct way is to add a modifier, such as a silane coupling agent, to the resin. However, although there are a variety of silane coupling agents that can be used in conjunction with heat-resistant resins, most silane coupling agents have poor high temperature resistance and are easily partially or completely decomposed during the thermal curing process. The related applications of 4-trimethoxysilylstyrene mentioned above in the present invention can just solve the defects of existing silane coupling agents.

[0030] Compared with the prior art, the present invention has the following beneficial effects:

[0031] 1. The present invention successfully prepares 4-trimethoxysilylstyrene through different inventive concepts and new routes, which not only provides more possibilities for synthesizing the aforementioned compounds, but also improves the yield of preparing 4-trimethoxysilylstyrene, and the yield can reach 89%.

[0032] 2. More specifically: The 4-trimethoxysilylstyrene prepared by the present invention has a styrene structure directly connected to an alkoxysilane, and also has an active group double bond. The preparation process is simple and low-cost, successfully avoiding the use of Grignard reaction, without the need to use dangerous Grignard reagents, and the reaction conditions are mild and easy to control, which greatly improves safety and is suitable for industrial production. In addition, each step of the reaction in the present invention is a common chemical reaction, which is easy to operate, significantly improves the reaction yield, and the raw materials are cheap and easy to obtain, which significantly reduces the production cost.

[0033] 3. The present invention has also been verified by experiments that the prepared 4-trimethoxysilylstyrene has a significant promoting effect on the adhesion of polyimide and polybenzoxazole heat-resistant resins to various substrates, can improve the adhesion of heat-resistant resin films to different substrates, and also solves the defects of existing silane coupling agents. Compared with existing silane coupling agents, the 4-trimethoxysilylstyrene of the present invention shows better compatibility and synergy with heat-resistant resins, significantly improving the performance of the modified heat-resistant resins in different environments, making them more reliable and competitive in industrial applications. In addition, the present invention significantly improves the industrial application potential of heat-resistant resins. The heat-resistant resins modified with 4-trimethoxysilylstyrene can be widely used in the fields of semiconductor packaging materials, high-temperature resistant adhesives and other high-performance composite materials, greatly improving their market competitiveness.

[0034] In summary, the present invention successfully prepares 4-trimethoxysilylstyrene through an innovative route, greatly improves the yield, and adopts safe and mild reaction conditions, with simple process and low cost, suitable for industrial production, and significantly improves the adhesion performance of heat-resistant resin to various substrates. Therefore, the present invention overcomes many defects of the prior art and has extremely high industrial application potential. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the accompanying drawings required for describing the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other accompanying drawings can be obtained based on these accompanying drawings without paying creative work.

[0036] Figure 1 The NMR spectrum of 4-trimethoxysilylphenylethane prepared by the present invention;

[0037] Figure 2 The liquid chromatogram of 4-trimethoxysilylphenylethyl bromide prepared by the present invention;

[0038] Figure 3 This is a liquid chromatogram of 4-trimethoxysilylstyrene prepared in the present invention. DETAILED DESCRIPTION

[0039] In order to make the purpose, technical scheme and advantages of the present invention more clearly understood, the present invention is further described in detail below in conjunction with the embodiments and the accompanying drawings. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not intended to limit the present invention. The experimental methods used below are conventional methods unless otherwise specified, and the materials, reagents, etc. used, unless otherwise specified, can all be obtained from commercial sources.

[0040] (I) Preparation of 4-trimethoxysilylstyrene

[0041] The method for preparing 4-trimethoxysilylstyrene comprises the following steps:

[0042] Step 1: Preparation of 4-trimethoxysilylphenylethane (Formula 1)

[0043] 4-Iodophenylethane and trimethoxysilane are used as raw materials, and a coupling reaction is carried out in a polar aprotic solvent under alkaline conditions and catalyzed by a catalyst Pd(t-Bu3P)2 to synthesize 4-trimethoxysilylphenylethane (Formula 1).

[0044] Wherein, the polar aprotic solvent includes at least one of DMF, DMSO, and NMP, and the base used in the alkaline condition is an inorganic base, and the inorganic base includes K3PO4, Na2CO3, NaOAc, KOAc, and Na3PO4.

[0045] The first step of the synthetic route is as follows:

[0046]

[0047] Step 2: Preparation of 4-trimethoxysilylphenylethyl bromide (Formula 2)

[0048] 4-Trimethoxysilylphenylethyl bromide (Formula 2) is synthesized by reacting 4-trimethoxysilylphenylethyl bromide with NBS, adding a free radical initiator and an inert solvent, and performing a free radical bromination reaction.

[0049] The inert solvent includes at least one of carbon tetrachloride, petroleum ether, carbon disulfide, and ethyl acetate, and the free radical initiator includes at least one of BPO and AIBN.

[0050] The second step synthesis route is as follows:

[0051]

[0052] Step 3: Preparation of 4-trimethoxysilylstyrene (Formula 3)

[0053] 4-Trimethoxysilylphenylethyl bromide is added to alcohol and dehydrobrominated with sodium hydroxide to obtain 4-trimethoxysilylstyrene (Formula 3).

[0054] Wherein, the alcohol includes at least one of methanol and ethanol.

[0055] The third step synthesis route is as follows:

[0056]

[0057] A more specific implementation is given below:

[0058] Example 1

[0059] Preparation of 4-trimethoxysilylphenylethane (Formula 1)

[0060] Under nitrogen atmosphere, 122.2 g (1 mol) of trimethoxysilane, 25.1 g (0.01 mol) of Pd(t-Bu3P), 318 g (1.5 mol) of potassium phosphate, 1200 ml of NMP, and 232 g (1 mol) of 4-iodophenylethane were added to the reaction vessel. After the addition was completed, the system was reacted at room temperature for 6 h. After the reaction was completed, 3000 ml of deionized water was added to quench the reaction, 1000 ml of ethyl acetate was extracted twice, the organic layer was washed three times with 500 ml of deionized water, and then the organic layer was dried with 50 g of anhydrous sodium sulfate, the desiccant was filtered out, the solvent was recovered under reduced pressure, and the residue was distilled under reduced pressure to obtain 210 g of colorless liquid with a yield of 92%. The product structure was detected, and the nuclear magnetic spectrum is shown in the attached figure. Figure 1 As shown, it can be seen that 4-trimethoxysilylphenylethane is obtained through the preparation.

[0061] Example 2

[0062] Preparation of 4-trimethoxysilylphenylethyl bromide (Formula 2)

[0063] Take 113 grams of 4-trimethoxysilylbenzene ethane, dissolve it in 600 milliliters of carbon tetrachloride, add 6 grams of BPO, add 106 grams of NBS in batches, heat to 90° for reaction, react for 4 hours, filter after the reaction, wash the filtrate with water, specifically: wash with 5% sodium bicarbonate aqueous solution, wash twice. Then dry the organic layer with anhydrous sulfuric acid, filter, recover the solvent by decompression of the filtrate, and distill the residue under reduced pressure to obtain 137 grams of light yellow liquid, with a yield of 90%. The product structure was detected, and the NMR spectrum is shown in the attached figure. Figure 2 As shown, it can be seen that 4-trimethoxysilylphenylethyl bromide is obtained through the preparation.

[0064] Example 3

[0065] Preparation of 4-trimethoxysilylstyrene (Formula 3)

[0066] Take 30.4 g of 4-trimethoxysilylphenyl bromoethane, dissolve it in 120 ml of methanol, add 6 g of sodium hydroxide, heat and reflux for 7 hours, after the reaction is over, slowly pour it into 500 ml of ice water, extract it twice with 100 ml of ethyl acetate, wash the organic layer with water until neutral, then dry the organic layer with anhydrous sulfuric acid, filter, recover the solvent by decompression of the filtrate, and distill the residue under reduced pressure to obtain 19.9 g of light yellow liquid, with a yield of 89%. The product structure was detected, and the NMR spectrum is as shown in the attached figure. Figure 3 As shown, it can be seen that 4-trimethoxysilylstyrene is obtained through the preparation.

[0067] (II) Application

[0068] The prepared 4-trimethoxysilylstyrene is used as a silane coupling agent in the thermal curing films of resins such as polyimide and polybenzoxazole to improve the adhesion to different substrates (silicon, ceramics, metals, etc.).

[0069] The specific implementation method is given below:

[0070] Example 4

[0071] The resin composite is prepared, wherein the raw materials of the resin composite include a polybenzoxazole precursor resin and homemade 4-trimethoxysilylstyrene, and the specific steps are as follows:

[0072] In a 500 ml flask equipped with a stirrer and a thermometer, 120 g of N-methylpyrrolidone was placed. Then 20.14 g (55 mmol) of bis(3-amino-4-hydroxyphenyl)hexafluoropropane was added and stirred to dissolve. Subsequently, 9.48 g (120 mmol) of pyridine was added. The flask was cooled to 5°C, and then 10.15 g (50 mmol) of isophthaloyl chloride was slowly added in batches, the temperature was kept at 0-5°C, and stirring was continued at room temperature for 16 hours to obtain a reaction solution. The reaction solution was poured into 3 L of 10 wt% methanol aqueous solution, a polymer was precipitated, a white precipitate was obtained, and the precipitate was filtered, washed three times with deionized water after filtering, and then placed in a vacuum oven and dried under reduced pressure at 60°C for 72 hours to obtain a polybenzoxazole precursor resin A1.

[0073] 10.00 g of the polybenzoxazole precursor resin A1 and 30.00 g of γ-butyrolactone (GBL) solvent were added to a 100 ml three-necked flask and stirred. After the resin was completely dissolved, 1.00 g of 4-trimethoxysilylstyrene obtained in Example 3 was added. After it was fully dissolved, it was filtered using a 1 μm filter membrane to obtain a resin composite.

[0074] Example 5

[0075] The resin composite is prepared, wherein the raw materials of the resin composite include polyimide resin and homemade 4-trimethoxysilylstyrene, and the specific steps are as follows:

[0076] Under nitrogen protection, in a 500 ml flask equipped with a stirrer, thermometer, condenser and water separator, add 150 g of N-methylpyrrolidone and 20.14 g (55 mmol) of bis(3-amino-4-hydroxyphenyl)hexafluoropropane, and stir to dissolve. Then cool the flask to 5 ° C, then slowly add 15.51 g (50 mmol) of 4,4'-oxydiphthalic anhydride in batches, keep the temperature at 0-5 ° C, and then continue to stir at room temperature for 16 hours. Then add 0.5 g of isoquinoline and 20 ml of toluene, heat to 160 ° C, reflux azeotropic dehydration for 5 hours, evaporate toluene, and keep warm for 2 hours before cooling to room temperature to obtain a reaction solution. Pour the reaction solution into 3L of 10wt% methanol aqueous solution, precipitate the polymer, obtain a light yellow precipitate, filter, wash with deionized water three times after filtration, put it in a vacuum oven, and dry it under reduced pressure at 60 ° C for 72 hours to obtain polyimide resin B1.

[0077] 10.00 g of the above-mentioned polyimide resin B1 and 30.00 g of γ-butyrolactone (GBL) solvent were added to a 100 ml three-necked flask and stirred. After the resin was completely dissolved, 1.00 g of 4-trimethoxysilylstyrene obtained in Example 3 was added. After it was fully dissolved, it was filtered using a 1 μm filter membrane to obtain a resin composite.

[0078] Example 6

[0079] Different from Example 4, 0.1 g of 4-trimethoxysilylstyrene obtained in Example 3 was added, and the rest was the same as in Example 4 to obtain a resin composite.

[0080] Example 7

[0081] Different from Example 5, 0.1 g of 4-trimethoxysilylstyrene obtained in Example 3 was added, and the rest was the same as in Example 5 to obtain a resin composite.

[0082] Comparative Example 1

[0083] Different from Example 4, 4-trimethoxysilylstyrene was replaced by KBM-403 (Shin-Etsu Chemical), and the rest was the same as Example 4 to obtain a resin composite.

[0084] Comparative Example 2

[0085] Different from Example 5, 4-trimethoxysilylstyrene was replaced by KBM-573 (Shin-Etsu Chemical), and the rest was the same as Example 5 to obtain a resin composite.

[0086] Comparative Example 3

[0087] Different from Example 4, 4-trimethoxysilylstyrene was replaced with KBM-503 (Shin-Etsu Chemical), and the rest was the same as Example 4 to obtain a resin composite.

[0088] Comparative Example 4

[0089] Different from Example 5, 4-trimethoxysilylstyrene was replaced by KBM-903 (Shin-Etsu Chemical), and the rest was the same as Example 5 to obtain a resin composite.

[0090] Comparative Example 5

[0091] Different from Example 4, 1.00 g of 4-trimethoxysilylstyrene obtained in Example 3 was not added, and the rest was the same as in Example 4 to obtain a resin composite.

[0092] (III) Detection

[0093] The following are the steps of preparing cured films using the resin composites of Examples 4 to 7 and Comparative Examples 1 to 5, and then conducting an adhesion peeling test between the cured films and the substrate. The specific steps are as follows:

[0094] The resin composites prepared in the above-mentioned embodiments and comparative examples were coated on different substrates (Si, SiO2, SiN, Al2O3, TiNiAg), and then baked at 120°C for 3 minutes using a hot plate to obtain a resin film. Then, the prepared resin film was placed on a heating plate for staged temperature increase heat treatment, specifically: first heat treatment at 90°C for 60 minutes, then heat treatment at 150°C for 60 minutes, heat treatment at 240°C for 60 minutes, and then heat treatment at 320°C for 60 minutes to obtain a cured film.

[0095] The cured film was cut into a checkerboard shape with 10 rows and 10 columns (a total of 100) at intervals of 2 mm, and a peeling test was performed using a special transparent 3M tape in accordance with the national standard GB / T 9286-1998 (scratch test of paint and varnish films), and the number of peeled grids was recorded.

[0096] The cured film with squares was placed in a high pressure accelerated aging test chamber (Xiamen Easy Instrument Technology ST-PCT40) for 100 hours of PCT test (conditions: 121°C, 2 atmospheres of saturated steam). After the PCT test, the same peeling test was performed using the tape and the results were recorded. Standard: If the number of peeled pieces is less than 10, it is considered good, and if it is 10 or more, it is considered bad.

[0097] The adhesion between the cured film samples prepared above and the substrate was tested, and the results are shown in Table 1 below:

[0098] Table 1

[0099]

[0100] It should be noted that "0 / 100" in the above Table 1 means that the number of peeled cells in 100 grids is 0, and the other results refer to the above meanings.

[0101] Analysis: From the data in Table 1, it can be seen that the silane coupling agent 4-trimethoxysilylstyrene prepared by the present invention significantly improves the adhesion of different resins to various substrates when applied to polyimide and polybenzoxazole resins, and still exhibits excellent adhesion to different substrates even after PCT treatment. Although the silane coupling agent in the comparative example also improves the adhesion between the resin and the substrate to a certain extent, the effect is significantly lower than that of the 4-trimethoxysilylstyrene of the present invention.

[0102] Finally, it should be noted that the above content is only used to illustrate the technical solution of the present invention, rather than to limit the scope of protection of the present invention. Simple modifications or equivalent substitutions of the technical solution of the present invention by ordinary technicians in this field do not deviate from the essence and scope of the technical solution of the present invention.

Claims

1. A method for preparing 4-trimethoxysilylstyrene, characterized in that: The steps include: 4-Trimethoxysilylbenzene was synthesized by coupling reaction of 4-iodophenylethane and trimethoxysilane. 4-Trimethoxysilylphenylethyl bromide is synthesized by reacting 4-trimethoxysilylphenylethyl with NBS via free radical bromination reaction; 4-Trimethoxysilylphenylethyl bromide was used to dehydrobrominate 4-trimethoxysilylphenylethyl bromide to prepare 4-trimethoxysilylphenylethyl bromide.

2. The method for preparing 4-trimethoxysilylstyrene according to claim 1, characterized in that: The steps of synthesizing 4-trimethoxysilylphenylethane are as follows: 4-iodophenylethane and trimethoxysilane are used as raw materials, and a coupling reaction is carried out in a polar aprotic solvent under alkaline conditions and under the catalysis of a catalyst to synthesize 4-trimethoxysilylphenylethane.

3. The method for preparing 4-trimethoxysilylstyrene according to claim 2, characterized in that: The polar aprotic solvent includes at least one of DMF, DMSO, and NMP, the catalyst includes Pd(t-Bu3P)2, and the base used in the alkaline condition includes an inorganic base, which includes at least one of K3PO4, Na2CO3, NaOAc, KOAc, and Na3PO4.

4. The method for preparing 4-trimethoxysilylstyrene according to claim 1, characterized in that: The steps of synthesizing 4-trimethoxysilylphenylethyl bromide are as follows: 4-trimethoxysilylphenylethyl bromide is reacted with NBS, a free radical initiator and an inert solvent are added, and 4-trimethoxysilylphenylethyl bromide is synthesized through a free radical bromination reaction.

5. The method for preparing 4-trimethoxysilylstyrene according to claim 4, characterized in that: The free radical initiator includes at least one of BPO and AIBN, and the inert solvent includes at least one of carbon tetrachloride, petroleum ether, carbon disulfide, and ethyl acetate.

6. The method for preparing 4-trimethoxysilylstyrene according to claim 1, characterized in that: The steps for synthesizing 4-trimethoxysilyl styrene are as follows: 4-trimethoxysilyl phenyl ethyl bromide is dehydrobrominated with sodium hydroxide in alcohol to obtain 4-trimethoxysilyl styrene.

7. The method for preparing 4-trimethoxysilylstyrene according to claim 1, characterized in that: The specific synthetic route is as follows: Wherein, Formula 1 is 4-trimethoxysilylphenylethane, Formula 2 is 4-trimethoxysilylphenylethyl bromide, and Formula 3 is 4-trimethoxysilylphenylethane.

8. The use of 4-trimethoxysilylstyrene as a modifier, characterized in that: The 4-trimethoxysilylstyrene is prepared according to the method for preparing 4-trimethoxysilylstyrene according to any one of claims 1 to 7, and the modifier comprises a silane coupling agent and a heat-resistant resin modifier.

9. A resin composite, characterized in that The resin composite comprises a heat-resistant resin and 4-trimethoxysilylstyrene, wherein the 4-trimethoxysilylstyrene is prepared according to the method for preparing 4-trimethoxysilylstyrene according to any one of claims 1 to 7; wherein the amount of the 4-trimethoxysilylstyrene used is 0.1 to 20% of the mass of the heat-resistant resin.

10. A method for improving the adhesion between a heat-resistant resin and a substrate, characterized in that: A heat-resistant resin and 4-trimethoxysilylstyrene are mixed and then coated on a substrate, wherein the 4-trimethoxysilylstyrene is prepared by the method for preparing 4-trimethoxysilylstyrene according to any one of claims 1 to 7; and the substrate comprises silicon, silicon dioxide, ceramics, and metal.

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