Silicone-modified aromatic amine, high-temperature resistant epoxy adhesive and preparation method thereof
Organosilicon-modified aromatic amines were prepared by end-capping aromatic amines with polydimethylsiloxane monoglycidyl ether, which solved the problems of toughness and ease of operation of aromatic amine curing agents, and achieved high toughness, strong adhesion and good heat resistance of high temperature resistant epoxy adhesives.
Patent Information
- Application Number
- CN202411893248.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-20
- Publication Date
- 2026-02-24
- Estimated Expiration
- 2044-12-20
AI Technical Summary
Existing aromatic amine-cured epoxy adhesives significantly reduce glass transition temperature and bond strength when improving toughness, and are solid at room temperature, requiring heating to melt, making them inconvenient to handle.
Aromatic amines with polydimethylsiloxane monoglycidyl ether end-capped modification were prepared to form silicone-modified aromatic amines as curing agents for high-temperature resistant epoxy adhesives. The introduction of silicone segments of appropriate length improves toughness and maintains high bonding strength, while remaining liquid at room temperature for easy application.
It achieves high toughness, strong adhesion, and ease of use in high-temperature resistant epoxy adhesives while maintaining good heat resistance.
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Abstract
Description
Technical Field
[0001] This invention belongs to the field of epoxy adhesive technology, and more specifically, this invention relates to an organosilicon-modified aromatic amine, a high-temperature resistant epoxy adhesive, and a method for preparing the same. Background Technology
[0002] Epoxy adhesives have a wide range of applications, from low to high temperatures. In the field of high-temperature resistant epoxy adhesives, epoxy adhesives cured with aromatic amines are highly favored due to their excellent heat resistance, corrosion resistance, and mechanical strength.
[0003] However, epoxy adhesives cured with aromatic amines are brittle due to the presence of benzene rings in their molecular chains. Toughness is typically improved by adding toughening agents to the system, but the addition of toughening agents significantly reduces their glass transition temperature, heat resistance, and bond strength.
[0004] In addition, aromatic amines have low reactivity, are generally solid at room temperature, require heating to melt, and have high curing temperatures and long curing times, which cause many inconveniences during use. Summary of the Invention
[0005] Based on this, the purpose of the present invention is to provide a high-temperature resistant epoxy adhesive that simultaneously possesses high toughness, strong adhesion, strong heat resistance, and convenient operation.
[0006] The specific technical solutions for achieving the above-mentioned objectives are as follows.
[0007] In a first aspect, the present invention provides an organosilicon-modified aromatic amine, the structural formula of which is shown below:
[0008] n = 10 to 50.
[0009] In a second aspect of the present invention, an organosilicon-modified aromatic amine is provided, which is obtained by reacting polydimethylsiloxane monoglycidyl ether end-capping with an aromatic amine, wherein the molar ratio of the polydimethylsiloxane monoglycidyl ether end-capping to the aromatic amine is 0.95 to 1.05:1;
[0010] The structural formula of the aromatic amine is shown below:
[0011]
[0012] The structural formula of the polydimethylsiloxane monoglycidyl ether-terminated structure is shown below:
[0013] n = 10 to 50.
[0014] A third aspect of the present invention provides a method for preparing an organosilicon-modified aromatic amine, comprising the following steps: adding polydimethylsiloxane monoglycidyl ether dropwise to the melted aromatic amine for end capping, and reacting to obtain the organosilicon-modified aromatic amine.
[0015] A fourth aspect of the present invention provides a high-temperature resistant epoxy adhesive, comprising component A and component B, wherein component A is obtained by mixing the following components in parts by weight:
[0016] 100 parts epoxy resin
[0017] 5 to 25 parts epoxy diluent
[0018] 100 to 250 parts of silica powder;
[0019] Component B is obtained by mixing the following components in parts by weight:
[0020] 100 parts of the above-mentioned organosilicon-modified aromatic amine
[0021] Accelerator 1 to 1.5 parts.
[0022] A fifth aspect of the present invention provides a method for preparing a high-temperature resistant epoxy adhesive, comprising the following steps:
[0023] Epoxy resin, epoxy diluent, and silica powder are stirred and mixed evenly to obtain component A; organosilicon-modified aromatic amine and accelerator are mixed evenly to obtain component B.
[0024] This invention modifies a specific type of aromatic amine by end-capping it with polydimethylsiloxane monoglycidyl ether containing a specific organosilicon chain length, thus introducing organosilicon segments of appropriate length into the aromatic amine. When this organosilicon-modified aromatic amine is used as a curing agent in high-temperature resistant epoxy adhesives, it can improve the toughness of the adhesive while maintaining high bond strength and good high-temperature resistance. Furthermore, the modified aromatic amine with introduced organosilicon segments is liquid at room temperature, making application more convenient. Therefore, the high-temperature resistant epoxy adhesive prepared using the organosilicon-modified aromatic amine of this invention as a curing agent simultaneously possesses excellent properties such as high toughness, high bond strength, strong heat resistance, and ease of use. Attached Figure Description
[0025] Figure 1 The infrared spectrum of the organosilicon-modified aromatic amine of Example 1 of the present invention is shown. Detailed Implementation
[0026] To facilitate understanding of the present invention, a more complete description will be provided below. The present invention can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a thorough and complete understanding of the disclosure of the present invention.
[0027] Unless otherwise defined, all technical and scientific terms used in this invention have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used in this specification is for the purpose of describing particular embodiments only and is not intended to limit the invention. The term "and / or" as used in this invention includes any and all combinations of one or more of the associated listed items.
[0028] Unless otherwise specified, the experimental methods used in the following examples are conventional methods, and the materials and reagents used are commercially available unless otherwise specified.
[0029] In some embodiments of the present invention, an organosilicon-modified aromatic amine is disclosed, the structural formula of which is shown below:
[0030] n = 10 to 50.
[0031] In some embodiments, n = 10 to 26.
[0032] In some embodiments, n = 10 to 18.
[0033] In other embodiments of the present invention, an organosilicon-modified aromatic amine is disclosed, which is obtained by reacting polydimethylsiloxane monoglycidyl ether end-capping with an aromatic amine, wherein the molar ratio of polydimethylsiloxane monoglycidyl ether end-capping to aromatic amine is 0.95 to 1.05:1;
[0034] The structural formula of the aromatic amine is shown below:
[0035]
[0036] The structural formula of the polydimethylsiloxane monoglycidyl ether-terminated structure is shown below:
[0037] n = 10 to 50.
[0038] In some embodiments, n = 10 to 26.
[0039] In some embodiments, n = 10 to 18.
[0040] In some embodiments, the molar ratio of the polydimethylsiloxane monoglycidyl ether end-capping to the aromatic amine is 0.98 to 1.02:1.
[0041] In some embodiments, the molar ratio of the polydimethylsiloxane monoglycidyl ether end-capping to the aromatic amine is 0.99 to 1.01:1.
[0042] In other embodiments of the present invention, a method for preparing the above-mentioned organosilicon-modified aromatic amine is disclosed, comprising the following steps: adding polydimethylsiloxane monoglycidyl ether dropwise to the melted aromatic amine for end capping, and reacting to obtain the organosilicon-modified aromatic amine.
[0043] In some embodiments, the reaction temperature is 150°C to 170°C, and the reaction time is 1.5h to 2.5h.
[0044] In some embodiments, the reaction is carried out under conditions with a promoter. Adding a promoter during the preparation of organosilicon-modified aromatic amines helps to lower the reaction temperature.
[0045] In some embodiments, the method for preparing the organosilicon-modified aromatic amine includes the following steps: adding an accelerator and polydimethylsiloxane monoglycidyl ether end-capping agent to the molten aromatic amine, controlling the temperature at 110℃~130℃, stopping the addition within 1h~3h, and then reacting at 110℃~130℃ for 1.5h~2.5h.
[0046] In some embodiments, the accelerator is 2,4,6-tris(dimethylaminomethyl)phenol, and the molar ratio of the accelerator to the aromatic amine is 0.008 to 0.012:1.
[0047] In other embodiments of the present invention, a high-temperature resistant epoxy adhesive is disclosed, comprising component A and component B, wherein component A is obtained by mixing the following components in parts by weight:
[0048] 100 parts epoxy resin
[0049] 5 to 25 parts epoxy diluent
[0050] 100 to 250 parts of silica powder.
[0051] Component B is obtained by mixing the following components in parts by weight:
[0052] 100 parts of the above-mentioned organosilicon-modified aromatic amine
[0053] Accelerator: 1 to 1.5 parts.
[0054] In some embodiments, the weight ratio of component A to component B is 1:0.5 to 2.
[0055] In some embodiments, the weight ratio of component A to component B is 1:0.5 to 1.5.
[0056] In some embodiments, the weight ratio of component A to component B is 1:0.8 to 1.2.
[0057] In some embodiments, the epoxy diluent is benzyl glycidyl ether.
[0058] In some embodiments, the promoter is 2,4,6-tris(dimethylaminomethyl)phenol.
[0059] In other embodiments of the present invention, a method for preparing the above-mentioned high-temperature resistant epoxy adhesive is disclosed, comprising the following steps: stirring and mixing epoxy resin, epoxy diluent, and silica powder evenly to obtain component A; and mixing organosilicon-modified aromatic amine and accelerator evenly to obtain component B.
[0060] In the following examples, organosilicon-modified aromatic amines were prepared using aromatic amines and polydimethylsiloxane monoglycidyl ether as reaction raw materials. The reaction principle is as follows:
[0061]
[0062] Where n = 10 to 50.
[0063] The present invention will be described in detail below with reference to the accompanying drawings and specific embodiments.
[0064] Example 1
[0065] The high-temperature resistant epoxy adhesive of this embodiment includes the following preparation raw materials (by weight) and steps:
[0066] 1. Add 1 mol of aromatic amine (structural formula: [insert structural formula here]) to a three-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel. Heat to 120℃ and hold for 2 hours until the aromatic amine melts. Add 0.01 mol of 2,4,6-tris(dimethylaminomethyl)phenol and 1 mol of polydimethylsiloxane monoglycidyl ether for end-capping. The temperature was controlled at 120℃, and the addition was completed within 2 hours. The reaction was continued at 120℃ for another 2 hours to obtain component B, which contains organosilicon-modified aromatic amine and 2,4,6-tris(dimethylaminomethyl)phenol. The mass ratio of organosilicon-modified aromatic amine to 2,4,6-tris(dimethylaminomethyl)phenol was 100:1.3.
[0067] The structural formula of organosilicon-modified aromatic amines is as follows:
[0068]
[0069] Its infrared spectrum is as follows Figure 1 As shown in the figure. It can be seen from the figure that the product also contains 1625 cm⁻¹. -1 and 1513cm -1 The raw material absorption peak, and 910 cm⁻¹ -1 The characteristic peaks of epoxy have disappeared, indicating that the epoxy groups have been completely consumed.
[0070] 2. Weigh 100 parts of epoxy resin (Baling Petrochemical CYD-128), 15 parts of benzyl glycidyl ether (epoxy diluent), and 150 parts of silica powder, mix them evenly, and obtain component A;
[0071] 3. When using, mix component A and component B evenly at a weight ratio of 1:0.6.
[0072] Example 2
[0073] The high-temperature resistant epoxy adhesive of this embodiment includes the following preparation raw materials (by weight) and steps:
[0074] 1. Add 1 mol of aromatic amine (same as in Example 1) to a three-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel. Heat to 120°C and maintain this temperature for 2 hours until the aromatic amine melts. Add 0.01 mol of 2,4,6-tris(dimethylaminomethyl)phenol and 1 mol of polydimethylsiloxane monoglycidyl ether dropwise to cap the mixture.
[0075] The temperature was controlled at 110℃, and the addition was completed within 3 hours. The temperature was then maintained at 120℃ for another 2 hours to obtain component B, which contains organosilicon-modified aromatic amine and 2,4,6-tris(dimethylaminomethyl)phenol.
[0076] The structural formula of the obtained organosilicon-modified aromatic amine is as follows:
[0077]
[0078] 2. Weigh 100 parts of epoxy resin (Baling Petrochemical CYD-128), 15 parts of benzyl glycidyl ether (epoxy diluent), and 150 parts of silica powder, mix them evenly, and obtain component A;
[0079] 3. When using, mix component A and component B evenly at a weight ratio of 1:0.9.
[0080] Example 3
[0081] The high-temperature resistant epoxy adhesive of this embodiment includes the following preparation raw materials (by weight) and steps:
[0082] 1. Add 1 mol of aromatic amine (same as in Example 1) to a three-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel. Heat to 120°C and maintain this temperature for 2 hours until the aromatic amine melts. Add 0.01 mol of 2,4,6-tris(dimethylaminomethyl)phenol and 1 mol of polydimethylsiloxane monoglycidyl ether dropwise to cap the mixture.
[0083] The temperature was controlled at 115℃, and the addition was completed within 3 hours. The temperature was then maintained at 120℃ for another 2 hours to obtain component B, which contains organosilicon-modified aromatic amine and 2,4,6-tris(dimethylaminomethyl)phenol.
[0084] The structural formula of the obtained organosilicon-modified aromatic amine is as follows:
[0085]
[0086] 2. Weigh 100 parts of epoxy resin (Baling Petrochemical CYD-128), 15 parts of benzyl glycidyl ether (epoxy diluent), and 150 parts of silica powder, mix them evenly, and obtain component A;
[0087] 3. When using, mix component A and component B evenly at a weight ratio of 1:1.2.
[0088] Example 4
[0089] The high-temperature resistant epoxy adhesive of this embodiment includes the following preparation raw materials (by weight) and steps:
[0090] 1. Add 1 mol of aromatic amine (same as in Example 1) to a three-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel. Heat to 120°C and maintain this temperature for 2 hours until the aromatic amine melts. Add 1 mol of polydimethylsiloxane monoglycidyl ether dropwise to seal the end-capping process. The temperature was controlled at 115℃, and the addition was completed dropwise over 3 hours. The reaction was then carried out at 160℃ for 2 hours to obtain an organosilicon-modified aromatic amine; its structural formula is as follows:
[0091]
[0092] 2. Weigh 100 parts of organosilicon-modified aromatic amine and 1.3 parts of 2,4,6-tris(dimethylaminomethyl)phenol, mix them evenly to obtain component B;
[0093] 3. Weigh 100 parts of epoxy resin (Baling Petrochemical CYD-128), 15 parts of benzyl glycidyl ether (epoxy diluent), and 150 parts of silica powder, mix them evenly, and obtain component A.
[0094] 4. When using, mix component A and component B evenly at a weight ratio of 1:1.5.
[0095] Example 5
[0096] The high-temperature resistant epoxy adhesive of this embodiment includes the following preparation raw materials (by weight) and steps:
[0097] 1. Add 1 mol of aromatic amine (same as in Example 1) to a three-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel. Heat to 120°C and maintain this temperature for 2 hours until the aromatic amine melts. Add 0.01 mol of 2,4,6-tris(dimethylaminomethyl)phenol and 1 mol of polydimethylsiloxane monoglycidyl ether dropwise to cap the mixture.
[0098] The temperature was controlled at 115℃, and the addition was completed within 3 hours. The temperature was then maintained at 120℃ for another 2 hours to obtain component B, which contains organosilicon-modified aromatic amine and 2,4,6-tris(dimethylaminomethyl)phenol.
[0099] The structural formula of the obtained organosilicon-modified aromatic amine is as follows:
[0100]
[0101] 2. Weigh 100 parts of epoxy resin (Baling Petrochemical CYD-128), 15 parts of benzyl glycidyl ether (epoxy diluent), and 150 parts of silica powder, mix them evenly, and obtain component A;
[0102] 3. When using, mix component A and component B evenly at a weight ratio of 1:1.8.
[0103] Example 6
[0104] The high-temperature resistant epoxy adhesive of this embodiment includes the following preparation raw materials (by weight) and steps:
[0105] 1. Add 1 mol of aromatic amine (same as in Example 1) to a three-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel. Heat to 120°C and maintain this temperature for 2 hours until the aromatic amine melts. Add 0.01 mol of 2,4,6-tris(dimethylaminomethyl)phenol and 1 mol of polydimethylsiloxane monoglycidyl ether dropwise to cap the mixture.
[0106] The temperature was controlled at 115℃, and the addition was completed within 3 hours. The temperature was then maintained at 120℃ for another 2 hours to obtain component B, which contains organosilicon-modified aromatic amine and 2,4,6-tris(dimethylaminomethyl)phenol.
[0107] The structural formula of the obtained organosilicon-modified aromatic amine is as follows:
[0108]
[0109] 2. Weigh 100 parts of epoxy resin (Baling Petrochemical CYD-128), 15 parts of benzyl glycidyl ether (epoxy diluent), and 150 parts of silica powder, mix them evenly, and obtain component A;
[0110] 3. When using, mix component A and component B evenly at a weight ratio of 1:2.
[0111] Comparative Example 1
[0112] The high-temperature resistant epoxy adhesive of this comparative example includes the following preparation materials (by weight) and steps:
[0113] 1. Weigh 100 parts of epoxy resin (Baling Petrochemical CYD-128), 15 parts of benzyl glycidyl ether (epoxy diluent), and 150 parts of silica powder, mix them evenly, and obtain component A;
[0114] 2. Weigh 100 parts of aromatic amine (same as in Example 1) and 1.3 parts of 2,4,6-tris(dimethylaminomethyl)phenol, mix them evenly to obtain component B;
[0115] 3. When using, mix component A and component B evenly at a weight ratio of 8:1.
[0116] Comparative Example 2
[0117] The high-temperature resistant epoxy adhesive of this comparative example includes the following preparation materials (by weight) and steps:
[0118] 1. Weigh 100 parts of epoxy resin (Baling Petrochemical CYD-128), 15 parts of benzyl glycidyl ether (epoxy diluent), 150 parts of silica powder, and 15 parts of toughening agent MX154 (Kanekazuchi, Japan), mix them evenly, and obtain component A;
[0119] 2. Weigh 100 parts of aromatic amine (same as in Example 1) and 1.3 parts of 2,4,6-tris(dimethylaminomethyl)phenol, mix them evenly to obtain component B;
[0120] 3. When using, mix component A and component B evenly at a weight ratio of 8:1.
[0121] Comparative Example 3
[0122] The high-temperature resistant epoxy adhesive of this comparative example includes the following preparation materials (by weight) and steps:
[0123] 1. In a three-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel, add 1 mol of aromatic amine (same as in Example 1), heat to 120°C, and maintain the temperature for 2 hours until the aromatic amine melts. Add 0.01 mol of 2,4,6-tris(dimethylaminomethyl)phenol and 1 mol of terminal epoxy tetramethyldisiloxane dropwise, controlling the temperature at 110°C, stopping the addition over 3 hours. Maintain the temperature at 120°C and continue the reaction for 2 hours to obtain component B.
[0124] 2. Component A is prepared in the same manner as in Example 2.
[0125] 3. When using, mix component A and component B evenly at a weight ratio of 5:1.
[0126] Comparative Example 4
[0127] The high-temperature resistant epoxy adhesive of this comparative example includes the following preparation materials (by weight) and steps:
[0128] 1. In a three-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel, add 1 mol of aromatic amine (same as in Example 1), heat to 120°C, and maintain the temperature for 2 hours until the aromatic amine melts. Add 0.01 mol of 2,4,6-tris(dimethylaminomethyl)phenol and 1 mol of terminal epoxy octamethyltetrasiloxane dropwise, controlling the temperature at 110°C, stopping the addition over 3 hours. Maintain the temperature at 120°C and continue the reaction for 2 hours to obtain component B.
[0129] 2. Component A is prepared in the same manner as in Example 2.
[0130] 3. When using, mix component A and component B evenly at a weight ratio of 5:1.
[0131] Comparative Example 5
[0132] The high-temperature resistant epoxy adhesive of this comparative example includes the following preparation materials (by weight) and steps:
[0133] 1. Add 1 mol of p-phenylenediamine to a three-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel. Heat to 120℃ and maintain for 2 hours until the aromatic amine melts. Add 0.01 mol of 2,4,6-tris(dimethylaminomethyl)phenol and 1 mol of polydimethylsiloxane monoglycidyl ether for end-capping.
[0134] The temperature was controlled at 110℃, and the addition was completed within 3 hours. The reaction was then maintained at 120℃ for another 2 hours to obtain component B.
[0135] 2. Weigh 100 parts of epoxy resin (Baling Petrochemical CYD-128), 15 parts of benzyl glycidyl ether (epoxy diluent), and 150 parts of silica powder, mix them evenly, and obtain component A;
[0136] 3. When using, mix component A and component B evenly at a weight ratio of 1:0.8.
[0137] Comparative Example 6
[0138] The high-temperature resistant epoxy adhesive provided in this comparative example, except for the modified aromatic amine, uses polydimethylsiloxane monoglycidyl ether end-capping agent with the following structural formula: In addition, when using, component A and component B are mixed evenly at a weight ratio of 1:0.4, and other preparation methods are the same as in Example 2.
[0139] Comparative Example 7
[0140] The high-temperature resistant epoxy adhesive provided in this comparative example, except for the polydimethylsiloxane monoglycidyl ether end-capping structure used in the preparation of modified aromatic amines, has the following structure: In addition, when using, mix component A and component B evenly at a weight ratio of 1:2.5. All other preparation methods are the same as in Example 2.
[0141] The high-temperature resistant epoxy adhesives prepared in Examples 1-6 and Comparative Examples 1-7 were subjected to the following performance tests:
[0142] Glass transition temperature: Static thermomechanical analysis (TMA)
[0143] Impact strength: Tested according to GB / T 1043.1-2008.
[0144] Shear strength at room temperature: tested according to GB / T7124-2008.
[0145] Shear strength at 80℃: Tested according to GB / T7124-2008.
[0146] The results are shown in Table 1.
[0147] Table 1 Performance results of various high-temperature resistant epoxy adhesives
[0148]
[0149] As shown in Table 1, the high-temperature resistant epoxy adhesives (Examples 1-6) prepared using the organosilicon-modified aromatic amine of the present invention as curing agents simultaneously exhibit high impact strength, bond strength, and glass transition temperature. Furthermore, the high-temperature resistant epoxy adhesives of the present invention can be used by directly mixing components A and B without the need for heating and curing, making operation convenient.
[0150] The high-temperature resistant epoxy adhesive prepared using unmodified aromatic amine curing agent (Comparative Example 1) exhibits very low impact strength and poor toughness. The high-temperature resistant epoxy adhesive prepared by adding conventional toughening agents to the epoxy adhesive system (Comparative Example 2), while showing improved impact strength, suffers a significant decrease in bond strength and glass transition temperature, resulting in a significant reduction in high-temperature resistance. The high-temperature resistant epoxy adhesives prepared using organosilicon-modified aromatic amines (Comparative Examples 3 and 4) modified with tetramethyldisiloxane and octamethyldisiloxane-modified diaminodiphenylmethane (terminated with epoxy tetramethyldisiloxane and epoxy octamethyldisiloxane respectively) as curing agents can improve the toughness of the cured product to some extent, but the improvement is still not ideal, and the shear strength is also insufficient. The epoxy adhesive prepared using polydimethylsiloxane monoglycidyl ether-terminated modified p-phenylenediamine (Comparative Example 5) improves toughness but fails to guarantee good heat resistance and high-temperature adhesion. However, when polydimethylsiloxane monoglycidyl ether is used to end-modify aromatic amines with a lower n value, the epoxy adhesive (Comparative Example 6) prepared with this method shows limited improvement in toughness. When polydimethylsiloxane monoglycidyl ether is used to end-modify aromatic amines with a higher n value, the epoxy adhesive (Comparative Example 7) prepared with this method improves the toughness of the cured system, but at the same time, it is accompanied by a decrease in adhesive strength.
[0151] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.
[0152] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these all fall within the protection scope of the present invention. Therefore, the protection scope of this invention patent should be determined by the appended claims.
Claims
1. An organosilicon-modified aromatic amine, characterized in that, Its structural formula is shown below: ,n=10~50。 2. The organosilicon-modified aromatic amine according to claim 1, characterized in that, n=10~26。 3. The organosilicon-modified aromatic amine according to claim 2, characterized in that, n=10~18。 4. An organosilicon-modified aromatic amine, characterized in that, It is obtained by reacting polydimethylsiloxane monoglycidyl ether end-capping with an aromatic amine, wherein the molar ratio of polydimethylsiloxane monoglycidyl ether end-capping to aromatic amine is 0.95~1.05:1; The structural formula of the aromatic amine is shown below: ; The structural formula of the polydimethylsiloxane monoglycidyl ether-terminated structure is shown below: ,n=10~50。 5. The organosilicon-modified aromatic amine according to claim 4, characterized in that, n=10~26。 6. The organosilicon-modified aromatic amine according to claim 5, characterized in that, n=10~18。 7. The organosilicon-modified aromatic amine according to claim 4, characterized in that, The molar ratio of the polydimethylsiloxane monoglycidyl ether end-capping compound to the aromatic amine is 0.98~1.02:
1.
8. The organosilicon-modified aromatic amine according to claim 7, characterized in that, The molar ratio of the polydimethylsiloxane monoglycidyl ether end cap to the aromatic amine is 0.99~1.01:
1.
9. A method for preparing an organosilicon-modified aromatic amine according to any one of claims 4 to 8, characterized in that, Includes the following steps: Polydimethylsiloxane monoglycidyl ether was added dropwise to the melted aromatic amine for end capping, and the reaction yielded the organosilicon-modified aromatic amine.
10. The method for preparing organosilicon-modified aromatic amines according to claim 9, characterized in that, The reaction temperature is 150℃~170℃, and the reaction time is 1.5 h~2.5 h; And / or, the reaction is carried out under conditions with a accelerator; including the following steps: adding an accelerator and polydimethylsiloxane monoglycidyl ether end-capping agent dropwise to the molten aromatic amine, controlling the temperature at 110℃~130℃, stopping the dropwise addition within 1 h~3 h, and then reacting at 110℃~130℃ for 1.5 h~2.5 h.
11. The method for preparing organosilicon-modified aromatic amines according to claim 10, characterized in that, The accelerator is 2,4,6-tris(dimethylaminomethyl)phenol; And / or, the molar ratio of the promoter to the aromatic amine is 0.008 to 0.012:
1.
12. A high-temperature resistant epoxy adhesive, characterized in that, It includes component A and component B, wherein component A is obtained by mixing the following components in parts by weight: 100 parts epoxy resin 5 to 25 parts epoxy diluent 100-250 parts of silica powder; Component B is obtained by mixing the following components in parts by weight: 100 parts of the organosilicon-modified aromatic amine according to any one of claims 1 to 8 Accelerator: 1 to 1.5 parts.
13. The high-temperature resistant epoxy adhesive according to claim 12, characterized in that, The weight ratio of component A to component B is 1:0.5~2.
14. The high-temperature resistant epoxy adhesive according to claim 13, characterized in that, The weight ratio of component A to component B is 1:0.5~1.
5.
15. The high-temperature resistant epoxy adhesive according to claim 14, characterized in that, The weight ratio of component A to component B is 1:0.8~1.
2.
16. The high-temperature resistant epoxy adhesive according to any one of claims 12 to 15, characterized in that, The epoxy diluent is benzyl glycidyl ether; and / or the accelerator is 2,4,6-tris(dimethylaminomethyl)phenol.
17. A method for preparing a high-temperature resistant epoxy adhesive according to any one of claims 12 to 16, characterized in that, Includes the following steps: Epoxy resin, epoxy diluent, and silica powder are stirred and mixed evenly to obtain component A; organosilicon-modified aromatic amine and accelerator are mixed evenly to obtain component B.
Citation Information
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