Organosilicon naphthyl epoxy compound as well as preparation method and application thereof

Abstract

The invention discloses an organic silicon naphthyl epoxy compound and a preparation method thereof, and relates to the technical field of coatings. Wherein n is an integer of 1-3, R1, R2, R3, R4, R5, R6 and R7 are respectively selected from the group consisting of R1, R2, R3, R4, R5, R6 and R7 and alkyl groups and are the same or different, and the number of carbon atoms of the alkyl groups is 1-5; r1, R2, R3, R4, R5, R6 and R7 at least comprise one or more of R1, R2, R3, R4, R5, R6 and R7. According to the organic silicon naphthyl epoxy compound, short-chain organic silicon is introduced into two naphthyl epoxy compounds, when the organic silicon naphthyl epoxy compound serves as a monomer to prepare epoxy resin, an organic silicon flexible chain segment is located in the monomer, and compared with the mode that organic silicon is introduced between the monomers to participate in polymerization, on one hand, the controllability of the length of the flexible chain segment in the epoxy resin is improved; according to the preparation method disclosed by the invention, the distribution uniformity of the organic silicon in the epoxy resin is improved, phase separation in the prepared epoxy resin is avoided under the comprehensive action, and the stability of the prepared epoxy resin is improved.

Description

Technical Field

[0001] This application relates to the field of epoxy resin technology, and in particular to an organosilicon naphthyl epoxy compound, its preparation method, and its application. Background Technology

[0002] Epoxy resins are a class of high-molecular-weight oligomers characterized by epoxy groups, which, after curing, form a three-dimensional network structure of thermosetting plastics. This cross-linked network endows cured epoxy resins with excellent mechanical properties, chemical resistance, and thermal stability, making them crucial in fields such as chemical engineering, electronic packaging, coatings, construction, and defense.

[0003] Currently, bisphenol A type epoxy resin (DGEBA) has achieved large-scale application in aerospace composite materials, electronic packaging substrates, and heavy-duty anti-corrosion coatings due to its excellent three-dimensional cross-linking network characteristics. However, the cured bisphenol A type epoxy resin's high brittleness, insufficient heat resistance, and certain water absorption limit its application in harsh environments. To address this, silicone-modified epoxy resins have been further developed. By introducing long-chain flexible silicone segments (siloxane segment polymerization degree ≥10) between epoxy resin monomers, the strength of epoxy resin is effectively combined with the flexibility, thermal stability, and hydrophobicity of silicone, such as DowSIL. TM EA series, Momentive EPIKOTE TM Modified resins and Shin-Etsu KJR series modified epoxy resins, etc.

[0004] However, if the flexible segments introduced in the above manner are locally too long or unevenly distributed, phase separation will occur in the product, resulting in a significant deterioration in the mechanical strength and hydrophobicity of the cured silicone epoxy resin. Summary of the Invention

[0005] In view of the shortcomings of the above-mentioned related technologies, this application provides an organosilicon naphthyl epoxy compound and its preparation method.

[0006] Firstly, the organosilicon naphthyl epoxy compound provided in this application adopts the following technical solution: An organosilicon naphthyl epoxy compound, with the general structural formula as follows: or ; Where n is an integer from 1 to 3, R 1 R 2 R 3 R 4 R 5 R 6 and R 7 Selected from , , , , And one of the alkyl groups, which may be the same as or different from the alkyl group, wherein the alkyl group has 1-5 carbon atoms; R 1 R 2 R 3 R 4 R 5 R 6 and R 7 At least one or .

[0007] Preferably, its structural formula is as follows: , , and One of them.

[0008] Secondly, the method for preparing an organosilicon naphthyl epoxy compound provided in this application adopts the following technical solution: A method for preparing an organosilicon naphthyl epoxy compound includes the following steps: under an inert gas atmosphere, allyl naphthyl epoxy compound and a catalyst are mixed, organosilicon is added dropwise, the mixture is reacted at a system temperature of 60-110℃, and then purified to obtain the organosilicon naphthyl epoxy compound.

[0009] Preferably, the molar ratio of the allyl naphthalene epoxy compound to the organosilicon is 2-2.2:1.

[0010] Preferably, the allylnaphthalene epoxy compound includes and One or more of the following; Among them, R1, R2, R3, R4, R5, R6 and R7 are respectively selected from , , , , One of the alkyl groups, wherein the alkyl group has 1-5 carbon atoms; R 1 R 2 R 3 R 4 R 5 R 6 and R 7 At least one or .

[0011] Preferably, the organosilicon comprises one or more of 1,1,3,3-tetramethyldisiloxane, 1,1,3,3,5,5-hexamethyltrisiloxane, and 1,1,3,3,5,5,7,7-octamethyltetrasiloxane.

[0012] Preferably, the amount of catalyst used is 4-20 ppm.

[0013] Preferably, the amount of catalyst used is 5 ppm.

[0014] Preferably, the catalyst is a platinum catalyst.

[0015] Preferably, the platinum catalyst comprises one or more of the following: Castells platinum catalyst, chloroplatinic acid-isopropanol solution, platinum-cyclovinylsiloxane complex, supported platinum catalyst, and platinum black.

[0016] Preferably, the platinum catalyst is a Castells platinum catalyst.

[0017] Thirdly, the application of an organosilicon naphthyl epoxy compound in epoxy resin provided in this application adopts the following technical solution.

[0018] The application of an organosilicon naphthyl epoxy compound in epoxy resin, wherein the epoxy resin is obtained by curing a monomer or prepolymer; the monomer or prepolymer includes an organosilicon naphthyl epoxy compound, and one or more of bisphenol A diglycidyl ether, bisphenol F type epoxy resin, bisphenol S type epoxy resin, hydrogenated bisphenol A type epoxy resin, and linear phenolic epoxy resin.

[0019] Preferably, the monomer or prepolymer comprises an organosilicon naphthyl epoxy compound and bisphenol A diglycidyl ether in a weight ratio of 0.25-4:1.

[0020] Preferably, the monomer or prepolymer is composed of an organosilicon naphthyl epoxy compound and bisphenol A diglycidyl ether in a weight ratio of 0.25-4:1.

[0021] Preferably, the prepolymer is composed of an organosilicon naphthyl epoxy compound and bisphenol A diglycidyl ether in a weight ratio of 1.5:1.

[0022] Preferably, the epoxy resin is used as an encapsulation material or a coating material.

[0023] In summary, this application includes at least one of the following beneficial technical effects: 1. The organosilicon naphthyl epoxy compound of the present invention introduces short-chain organosilicon into two naphthyl epoxy compounds. When used as a monomer to prepare epoxy resin, the flexible organosilicon segment is located in the monomer. Compared with introducing organosilicon between monomers to participate in polymerization, on the one hand, it improves the controllability of the length of the flexible segment in the epoxy resin, and on the other hand, it improves the uniformity of the distribution of organosilicon in the epoxy resin. Under the combined effect, phase separation in the obtained epoxy resin is avoided, and the stability of the obtained epoxy resin is improved. 2. When the organosilicon naphthyl epoxy compound of the present invention is applied to epoxy resin encapsulation materials and coatings, it is beneficial to improve the mechanical properties, thermal stability, flame retardancy, hydrophobicity, high temperature resistance, corrosion resistance, wear resistance and other properties of epoxy resin encapsulation materials and coatings. Attached Figure Description

[0024] Figure 1 This is the infrared spectrum of the organosilicon naphthyl epoxy compound from Example 1; Figure 2 This is the 1H NMR spectrum of the organosilicon naphthyl epoxy compound of Example 1; Figure 3 This is the high-resolution mass spectrum of the organosilicon naphthyl epoxy compound in Example 1; Figure 4 The infrared spectrum of the organosilicon naphthyl epoxy compound in Example 4; Figure 5 This is the 1H NMR spectrum of the organosilicon naphthyl epoxy compound in Example 4; Figure 6 This is the high-resolution mass spectrum of the organosilicon naphthyl epoxy compound in Example 4; Figure 7 The graph shows a comparison of the bending stress-strain curves of the epoxy resin encapsulation materials used in Examples 1-4 and Comparative Example 1. Figure 8 The graph shows a comparison of the flexural modulus and flexural strength curves of the epoxy resin encapsulation materials used in Examples 1-4 and Comparative Example 1. Figure 9 This is a comparison chart of the TG analysis curves of the epoxy resin encapsulation materials used in Examples 1-4 and Comparative Example 1. Figure 10 This is a comparison chart of the DTG analysis curves of the epoxy resin encapsulation materials used in Examples 1-4 and Comparative Example 1. Figure 11 The chart shows a comparison of the DSC analysis curves of the epoxy resin encapsulation materials used in Examples 1-4 and Comparative Example 1. Figure 12 This is a comparison chart of the water absorption curves of the epoxy resin encapsulation materials used in Examples 1-4 and Comparative Example 1. Figure 13 The graph shows a comparison of the bending stress-strain curves of the epoxy resin encapsulation materials used in Examples 5-8 and Comparative Example 1. Figure 14 This is a comparison of the flexural modulus and flexural strength curves of the epoxy resin encapsulation materials used in Examples 5-8 and Comparative Example 1. Figure 15 This is a comparison chart of the TG analysis curves of the epoxy resin encapsulation materials used in Examples 5-8 and Comparative Example 1. Figure 16This is a comparison chart of the DTG analysis curves of the epoxy resin encapsulation materials used in Examples 5-8 and Comparative Example 1. Figure 17 The chart shows a comparison of the DSC analysis curves of the epoxy resin encapsulation materials used in Examples 5-8 and Comparative Example 1. Figure 18 This is a comparison chart of the water absorption curves of the epoxy resin encapsulation materials used in Examples 5-8 and Comparative Example 1. Figure 19 The comparison diagram shows the hydrophobicity of the epoxy resin coatings in Application Examples 9-12 and Comparative Example 2. Figure 20 The graphs show a comparison of the wear resistance of the epoxy resin coatings used in Examples 9-12 and Comparative Example 2. Figure 21 These are comparison diagrams showing the adhesion of epoxy resin coatings in Application Examples 9-12 and Comparative Example 2; Figure 22 The static water contact angle comparison diagrams of the epoxy resin coatings used in Examples 9-12 and Comparative Example 2 show the acid resistance of the static water contact angles. Figure 23 The static water contact angle comparison diagrams of the epoxy resin coatings used in Examples 9-12 and Comparative Example 2 show the alkali resistance of the static water contact angles. Figure 24 The comparison diagram shows the salt spray resistance of the epoxy resin coatings in Application Examples 9-12 and Comparative Example 2. Figure 25 This is a comparison chart of the Tafel polarization curves of the epoxy resin coatings in Examples 9-12 and Comparative Example 2. Figure 26 The Nyquist curves of the epoxy resin coatings in Examples 9-12 and Comparative Example 2 are compared. Figure 27 The Bode curves of the epoxy resin coatings in Examples 9-12 and Comparative Example 2 are compared. Figure 28 These are comparison diagrams showing the hydrophobicity of the epoxy resin coatings in Application Examples 13-16 and Comparative Example 2. Figure 29 These are comparison charts showing the wear resistance of epoxy resin coatings in Application Examples 13-16 and Comparative Example 2. Figure 30 These are comparison diagrams showing the adhesion of epoxy resin coatings in Application Examples 13-16 and Comparative Example 2; Figure 31 The static water contact angle comparison diagrams of the epoxy resin coatings in Application Examples 13-16 and Comparative Example 2 show the acid resistance of the static water contact angles. Figure 32 The static water contact angle comparison diagrams of the epoxy resin coatings in Application Examples 13-16 and Comparative Example 2 are shown. Figure 33These are comparison diagrams showing the salt spray resistance of the epoxy resin coatings in Application Examples 13-16 and Comparative Example 2. Figure 34 This is a comparison chart of the Tafel polarization curves of the epoxy resin coatings in Application Examples 13-16 and Comparative Example 2. Figure 35 The Nyquist curves of the epoxy resin coatings in Application Examples 13-16 and Comparative Example 2 are compared. Figure 36 The Bode curves are a comparison of the epoxy resin coatings used in Examples 13-16 and Comparative Example 2. Detailed Implementation

[0025] The present application will be further described in detail below with reference to the embodiments. The following embodiments are for illustrative purposes only and should not be considered as limiting the scope of the invention. Unless otherwise specified, specific conditions in the following embodiments were performed under conventional conditions or conditions recommended by the manufacturer. Unless otherwise specified, the methods used are conventional methods known in the art, and the consumables and reagents used are commercially available. Unless otherwise stated, the technical and scientific terms used herein have the same meaning as those familiar to those skilled in the art. Furthermore, any methods or materials similar to or equivalent to those described herein may also be applied to the present invention.

[0026] The raw materials used in the examples and comparative examples are all commercially available.

[0027] Example 1 Example 1 of this application provides an organosilicon naphthyl epoxy compound with the following structural formula: The compound was prepared by the following steps: Under an argon atmosphere, 10.080 g (0.042 mol) of 2-allyl-1-epoxypropoxynaphthalene and 0.013 g of Castells platinum catalyst (5 ppm platinum content) were added to a 100 mL three-necked flask, and the temperature was raised to 60 °C. 2.830 g (0.021 mol) of 1,1,3,3-tetramethyldisiloxane was slowly added dropwise through a constant-pressure dropping funnel, with the system temperature controlled to not exceed 60 °C, and the reaction was allowed to proceed for 5 h. Low-boiling substances were removed by vacuum distillation to obtain the organosilicon naphthyl epoxy compound.

[0028] The reaction equation for Example 1 is as follows: .

[0029] Example 2 Example 2 of this application provides an organosilicon naphthyl epoxy compound with the following structural formula: The compound was prepared by the following steps: Under an argon atmosphere, 31.881 g (0.042 mol) of 2-allyl-1,6-diepoxypropoxynaphthalene and a chloroplatinic acid-isopropanol solution (platinum content 10 ppm) were added to a 100 mL three-necked flask, and the temperature was raised to 80 °C. 2.960 g (0.022 mol) of 1,1,3,3-tetramethyldisiloxane was slowly added dropwise through a constant-pressure dropping funnel, controlling the system temperature to not exceed 100 °C, and the reaction was allowed to proceed for 5 h. The mixture was then cooled to 60 °C and distilled under reduced pressure to remove low-boiling compounds, yielding the organosilicon naphthyl epoxy compound.

[0030] The reaction equation for Example 2 is as follows: .

[0031] Example 3 Example 3 of this application provides an organosilicon naphthyl epoxy compound with the following structural formula: The compound was prepared by the following steps: Under an argon atmosphere, 31.881 g (0.042 mol) of 2-allyl-1,5-diepoxypropoxynaphthalene and a chloroplatinic acid-isopropanol solution (platinum content 20 ppm) were added to a 100 mL three-necked flask, and the temperature was raised to 100 °C. 2.960 g (0.022 mol) of 1,1,3,3-tetramethyldisiloxane was slowly added dropwise through a constant-pressure dropping funnel, controlling the system temperature to not exceed 110 °C, and the reaction was allowed to proceed for 5 h. The mixture was then cooled to 60 °C and distilled under reduced pressure to remove low-boiling-point compounds, yielding the organosilicon naphthyl epoxy compound.

[0032] The reaction equation for Example 3 is as follows: .

[0033] Example 4 Example 4 of this application provides an organosilicon naphthyl epoxy compound with the following structural formula: The compound was prepared by the following steps: Under an argon atmosphere, 10.080 g (0.042 mol) of 1-allyl-2-epoxypropoxynaphthalene and a chloroplatinic acid-isopropanol solution (platinum content 20 ppm) were added to a 100 mL three-necked flask, and the temperature was raised to 110 °C. 2.560 g (0.019 mol) of 1,1,3,3-tetramethyldisiloxane was slowly added dropwise through a constant-pressure dropping funnel, controlling the system temperature to not exceed 110 °C, and the reaction was allowed to proceed for 5 h. The mixture was then cooled to 60 °C and distilled under reduced pressure to remove low-boiling substances, yielding the organosilicon naphthyl epoxy compound.

[0034] The reaction equation for Example 4 is as follows: .

[0035] Application Examples 1-8 Application Examples 1-8 of this application provide an epoxy resin prepared by the following steps: mixing a prepolymer with 5 wt% of 1,1,3,3-tetramethylguanidine, pouring the mixture into a mold, and then placing it in an oven for high-temperature curing to form an encapsulation material. The composition of the prepolymer in Application Examples 1-8 is shown in Table 1.

[0036] Table 1:

[0037] Application Example 9-16 Application Examples 9-16 of this application provide an epoxy resin prepared by the following steps: mixing a prepolymer with 5 wt% of 1,1,3,3-tetramethylguanidine, coating the mixture, and then placing it in an oven for high-temperature curing to form a coating. The composition of the prepolymer in Application Examples 9-16 is shown in Table 2.

[0038] Table 2:

[0039] Comparative Example 1 Comparative Example 1 of this application provides an epoxy resin prepared by the following steps: mixing bisphenol A diglycidyl ether and 5 wt% of 1,1,3,3-tetramethylguanidine, pouring into a mold, and then placing it in an oven for high-temperature curing to form an encapsulation material.

[0040] Comparative Example 2 Comparative Example 2 of this application provides an epoxy resin, which is prepared by the following steps: mixing bisphenol A diglycidyl ether and 5 wt% of 1,1,3,3-tetramethylguanidine, coating the mixture, and then placing it in an oven for high-temperature curing to form a coating.

[0041] Testing and Inspection (1) The infrared spectrum, proton nuclear magnetic resonance spectrum and high-resolution mass spectrometry of the organosilicon naphthyl epoxy compound of Example 1 were detected, and the results are as follows: Figure 1-3 As shown; the infrared spectrum, 1H NMR spectrum, and high-resolution mass spectrometry of the organosilicon naphthyl epoxy compound in Example 4 were detected, and the results are as follows: Figure 4-6 As shown.

[0042] (2) Comparison of bending stress-strain curves, bending modulus-flexural strength curves, TG analysis curves, DTG analysis curves, DSC analysis curves, and water absorption curves of the epoxy resin encapsulation materials used in Examples 1-4 and Comparative Example 1. The results are as follows: Figure 7-12 As shown; the comparison charts of flexural stress-strain curves, flexural modulus-flexural strength curves, TG analysis curves, DTG analysis curves, DSC analysis curves, and water absorption curves of the epoxy resin encapsulation materials used in Examples 5-8 and Comparative Example 1 are shown in the figure below. Figure 13-18 As shown.

[0043] (3) Comparison charts of hydrophobicity, abrasion resistance, adhesion, static water contact angle (acid resistance), static water contact angle (alkali resistance), salt spray resistance, Tafel polarization curve, Nyquist curve, and Bode curve of epoxy resin coatings in Examples 9-12 and Comparative Example 2 are shown in the following figures. Figure 19-27 As shown; the comparison charts for hydrophobicity, abrasion resistance, adhesion, static water contact angle (acid resistance), static water contact angle (alkali resistance), salt spray resistance, Tafel polarization curves, Nyquist curves, and Bode curves of the epoxy resin coatings in Application Examples 13-16 and Comparative Example 2 are as follows: Figure 28-36 As shown.

[0044] Results Analysis The following combination Figure 1-36 The experimental results provided provide a detailed explanation of this application.

[0045] comprehensive Figure 1 infrared spectrum, Figure 2 The proton NMR spectrum and Figure 3 The high-resolution mass spectrometry results confirmed that the organosilanesenaphthalyl epoxide compound prepared in Example 1 was indeed the target product; In summary... Figure 4 infrared spectrum, Figure 5 The proton NMR spectrum and Figure 6 The high-resolution mass spectrometry results confirmed that the organosilicon naphthyl epoxy compound prepared in Example 4 was the target product.

[0046] Reference Figure 7-12 ,Depend on Figure 7-8 It can be seen that the flexural strength and modulus of the epoxy resin encapsulation materials in Examples 1-4 first increase and then decrease with the increase of the content of the organosilicon naphthyl epoxy compound in Example 1, and the flexural strength and modulus reach their maximum when the content of the organosilicon naphthyl epoxy compound reaches 60 wt%. Figure 9-11 It can be seen that the glass transition temperatures of the epoxy resin encapsulation materials in Examples 1-4 all exhibit only one glass transition step, without significant phase separation. Furthermore, the maximum weight loss rate of the epoxy resin encapsulation materials in Examples 1-4 is significantly lower and the residual carbon content is higher compared to Comparative Example 1, indicating that the thermal stability, flame retardancy, and high-temperature performance of the epoxy resin encapsulation materials in Examples 1-4 are improved. Figure 12 It can be seen that the water absorption rate of the epoxy resin encapsulation materials in Examples 1-4 first decreases and then increases as the content of the organosilicon naphthyl epoxy compound in Example 1 increases, and the water absorption rate reaches its lowest point when the content of the organosilicon naphthyl epoxy compound reaches 60 wt%.

[0047] Reference Figure 13-18 ,Depend on Figure 13-14 It can be seen that the flexural strength and modulus of the epoxy resin encapsulation materials used in Examples 5-8 first increase and then decrease with the increase of the content of the organosilicon naphthyl epoxy compound in Example 1, and the flexural strength and modulus reach their maximum when the content of the organosilicon naphthyl epoxy compound reaches 60 wt%. Figure 15-17 It can be seen that the epoxy resin encapsulation materials in Application Examples 5-8 all exhibit only one glass transition step, without significant phase separation. Furthermore, the maximum weight loss rate of the epoxy resin encapsulation materials in Application Examples 5-8 is significantly lower and the residual carbon content is higher compared to Comparative Example 1, indicating that the thermal stability, flame retardancy, and high-temperature performance of the epoxy resin encapsulation materials in Application Examples 5-8 are improved. Figure 18 It can be seen that the water absorption rate of the epoxy resin encapsulation materials in Examples 4-8 first decreased and then increased as the content of the organosilicon naphthyl epoxy compound in Example 4 increased, and the water absorption rate reached its lowest point when the content of the organosilicon naphthyl epoxy compound reached 40 wt%.

[0048] Reference Figure 19-27 ,Depend on Figure 19 It can be seen that the water contact angle of the epoxy resin coating increases with the increase of the content of the organosilicon naphthyl epoxy compound in Example 1. When the content of the organosilicon naphthyl epoxy compound reaches 60 wt% and 80 wt%, the water contact angle is close to 106°, which is 20.83° higher than that of the epoxy resin coating in Comparative Example 2. Figure 20 It can be seen that the pure DGEBA resin coating, and the resin coatings of Example 1 with a content of 20 wt% and 80 wt%, exhibit obvious friction marks, with a clear boundary between the friction and unfrictioned areas visible under a microscope. However, when the content of Example 1 is 40 wt% and 60 wt%, the friction marks are less noticeable. The wear resistance of the epoxy resin coating shows a trend of first increasing and then decreasing with the increase of the content of the organosilicon naphthyl epoxy compound in Example 1. Figure 21 As can be seen from the standard ASTM D3359, the cross-cut adhesion test shows that the epoxy resin coatings of Application Examples 1-4 and the epoxy resin coating of Comparative Example 2 exhibit the same excellent interfacial adhesion performance, and no obvious coating peeling was observed in any of the samples; Figure 22-23 It can be seen that the acid and alkali resistance of the epoxy resin coating increases with the increase of the content of organosilicon naphthyl epoxy compound in Example 1. When the content of organosilicon naphthyl epoxy compound reaches 60 wt%, the water contact angle remains at its maximum as time increases. Figure 24 The surface morphology of the modified coatings in Application Examples 1-4 after 7 days of continuous salt spray exposure is shown. The observation results indicate that after 168 hours of salt spray exposure, the modified coating systems in Application Examples 1-4 effectively blocked the corrosive medium (Cl). -The penetration and migration into the metal substrate. Figure 25-27 It can be seen that the epoxy resin coating of Example 1 with an organosilicon naphthyl epoxy compound content of 60 wt% exhibited the highest corrosion potential (Ecorr = -0.47 V) and the lowest corrosion current (Icorr = 1.06 × 10⁻⁶ V). -7 A·cm 2 The corrosion resistance of the coating initially increases and then decreases with increasing content of organosilicon naphthyl epoxy compound. In Example 1, when the content of organosilicon naphthyl epoxy compound reaches 60 wt%, the |Z| of the epoxy resin coating... 0.01HZ The value reached 2.01 × 10 4 Ω·cm 2 Compared with the pure DGEBA epoxy resin coating of Comparative Example 2 (|Z| 0.01HZ =3.19×10 3 Ω·cm 2 The content of organosilicon naphthyl epoxy compound was increased by an order of magnitude; and when the content of organosilicon naphthyl epoxy compound was 60 wt%, the epoxy resin coating of Application Example 3 had the largest phase angle and exhibited the best corrosion resistance.

[0049] Reference Figure 28-36 ,Depend on Figure 28 It can be seen that the static water contact angle of the epoxy resin coating increases with the increase of the content of the organosilicon naphthyl epoxy compound in Example 4. When the content of the organosilicon naphthyl epoxy compound reaches 60 wt% and 80 wt%, the water contact angle is close to 102°, which is 17° higher than that of the epoxy resin coating in Comparative Example 2. Figure 29 It can be seen that the pure DGEBA resin coating, and the resin coatings of Example 4 with contents of 20 wt% and 80 wt%, exhibit obvious friction marks, with a clear boundary between the friction and unfrictioned areas visible under a microscope. However, when the content of Example 4 is 40 wt% and 60 wt%, the friction marks are less noticeable. Therefore, the wear resistance of the epoxy resin coating shows a trend of first increasing and then decreasing with the increase of the organosilicon naphthyl epoxy compound content in Example 4. Figure 30 As can be seen from the cross-cut adhesion test according to standard ASTM D3359, the epoxy resin coatings in Application Examples 5-8 and Comparative Example 2 exhibited the same excellent interfacial adhesion properties, and no obvious coating peeling was observed in any of the samples; Figures 31-32 It can be seen that the acid and alkali resistance of the epoxy resin coating increases with the increase of the content of organosilicon naphthyl epoxy compound in Example 4. When the content of organosilicon naphthyl epoxy compound reaches 60 wt%, the water contact angle remains at its maximum as time increases. Figure 33The surface morphology of the modified coating of Example 4 after 7 days of continuous salt spray exposure is shown. The observation results indicate that after 168 hours of salt spray exposure, the modified coating systems of Examples 5-8 all effectively blocked the corrosive medium (Cl). - The penetration and migration into the metal substrate. Figures 34-36 It can be seen that the epoxy resin coating of Example 4, with an organosilicon naphthyl epoxy compound content of 60 wt%, exhibited the highest corrosion potential (Ecorr = -0.55 V) and the lowest corrosion current (Icorr = 1.95 × 10⁻⁶ V). -7 A·cm 2 The corrosion resistance of the coating initially increases and then decreases with increasing content of organosilicon naphthyl epoxy compound. In Example 4, when the content of organosilicon naphthyl epoxy compound reaches 60 wt%, the |Z| of the epoxy resin coating... 0.01HZ The value reached 1.56 × 10 4 Ω·cm 2 Compared with the pure DGEBA epoxy resin coating of Comparative Example 2 (|Z| 0.01HZ =3.19×10 3 Ω·cm 2 The content of organosilicon naphthyl epoxy compound was increased by an order of magnitude; and when the content of organosilicon naphthyl epoxy compound was 60 wt%, the epoxy resin coating of Application Example 7 had the largest phase angle and exhibited the best corrosion resistance.

[0050] This specific embodiment is merely an explanation of this application and is not intended to limit it. After reading this specification, those skilled in the art can make modifications to this embodiment without contributing any inventive step, but such modifications are protected by patent law as long as they fall within the scope of the claims of this application.

Claims

1. An organosilicon naphthyl epoxy compound, characterized in that: Its general structural formula is or ; Where n is an integer from 1 to 3, R 1 R 2 R 3 R 4 R 5 R 6 and R 7 Selected from , , , , And one of the alkyl groups, which may be the same as or different from the alkyl group, wherein the alkyl group has 1-5 carbon atoms; R 1 R 2 R 3 R 4 R 5 R 6 and R 7 At least one or .

2. The organosilicon naphthyl epoxy compound according to claim 1, characterized in that: Its structural formula is , , and One of them.

3. A method for preparing the organosilicon naphthyl epoxy compound as described in any one of claims 1-2, characterized in that: Includes the following steps: Under an inert gas atmosphere, allyl naphthalene epoxy compound and catalyst were mixed, and organosilicon was added dropwise. The mixture was reacted at a system temperature of 60-110℃, purified, and the organosilicon naphthyl epoxy compound was obtained.

4. The method for preparing an organosilicon naphthyl epoxy compound according to claim 3, characterized in that: The molar ratio of the allyl naphthalene epoxy compound to the organosilicon is 2-2.2:

1.

5. The method for preparing an organosilicon naphthyl epoxy compound according to claim 3, characterized in that: The allylnaphthalene epoxy compound includes and One or more of the following; Among them, R1, R2, R3, R4, R5, R6 and R7 are respectively selected from , , , , And one of the alkyl groups, wherein the alkyl group has 1-5 carbon atoms; R 1 R 2 R 3 R 4 R 5 R 6 and R 7 At least one or .

6. The method for preparing an organosilicon naphthyl epoxy compound according to claim 3, characterized in that: The organosilicon includes one or more of 1,1,3,3-tetramethyldisiloxane, 1,1,3,3,5,5-hexamethyltrisiloxane, and 1,1,3,3,5,5,7,7-octamethyltetrasiloxane.

7. The method for preparing an organosilicon naphthyl epoxy compound according to claim 3, characterized in that: The amount of catalyst used is 4-20 ppm.

8. The method for preparing an organosilicon naphthyl epoxy compound according to claim 3, characterized in that: The catalyst includes one or more of the following: Castel platinum catalyst, chloroplatinic acid-isopropanol solution, platinum-cyclovinylsiloxane complex, supported platinum catalyst, and platinum black.

9. The application of an organosilicon naphthyl epoxy compound as described in any one of claims 1-2 in epoxy resin, characterized in that: The epoxy resin is obtained by curing monomers or prepolymers; the monomers or prepolymers include organosilicon naphthyl epoxy compounds, and one or more of bisphenol A diglycidyl ether, bisphenol F type epoxy resin, bisphenol S type epoxy resin, hydrogenated bisphenol A type epoxy resin, and linear phenolic epoxy resin.

10. The application according to claim 9, characterized in that: The monomer comprises an organosilicon naphthyl epoxy compound and bisphenol A diglycidyl ether in a weight ratio of 0.25-4:1.

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