A high-temperature resistant anaerobic adhesive with a functionalized cage-type silsesquioxane structure, its preparation method and application

Abstract

The present invention belongs to the technical field of the synthesis of industrial high-molecular adhesives, and discloses a high-temperature resistant anaerobic adhesive with a functionalized cage-shaped silsesquioxane structure, a preparation method thereof and an application. The high-temperature resistant anaerobic adhesive is composed of the following components in parts by weight: 2-40 parts of methacryloxypropyl cage-shaped silsesquioxane, 50-100 parts of methacrylate monomer, 0.1-10 parts of inhibitor, 0.1-10 parts of metal chelating agent, 1-20 parts of initiator, 0.5-10 parts of accelerator, and 1-5 parts of auxiliary material. The present invention can prepare a high-purity functionalized cage-shaped silsesquioxane, and by adding the functionalized cage-shaped silsesquioxane, the crosslinking density of the anaerobic adhesive is increased, and the heat resistance is improved, so as to synthesize a high-temperature resistant anaerobic adhesive with a functionalized cage-shaped silsesquioxane structure, and the high temperature resistance can reach 350 °C, which can meet the requirements of industry for anaerobic adhesives in high-temperature environments.

Description

Technical Field

[0001] The present invention belongs to the technical field of the synthesis of industrial high molecular adhesives, and particularly relates to a high temperature resistant anaerobic adhesive with a functionalized cage-shaped silsesquioxane structure, a preparation method thereof and an application thereof. Background Art

[0002] Anaerobic adhesives have anaerobic curing characteristics and remain liquid in an oxygen-rich environment without curing. When the oxygen in the environment where the anaerobic adhesive is located is consumed or there is no oxygen, a curing reaction will occur. Due to the mild curing conditions, excellent bonding and sealing properties, and good corrosion resistance, anaerobic adhesives are widely used in thread locking, micro-hole sealing, and mechanical manufacturing. With the continuous improvement of industry and the rapid development of the aerospace, machinery, and transportation industries, the industrial requirements for the heat resistance of anaerobic adhesives have increased accordingly. Currently, improving the heat resistance of anaerobic adhesives mainly starts from three aspects. The first aspect is to synthesize acrylate monomers with heat-resistant structures. The second aspect is to add resins with high temperature resistance, such as benzoxazine, polyimide, and bismaleimide. The third aspect is to modify the anaerobic adhesive by adding inorganic materials to the anaerobic adhesive. Currently, due to the rise of inorganic materials, adding inorganic materials or inorganic-organic hybrid materials to organic polymers has obvious effects on modifying polymer materials. Polyhedral oligomeric silsesquioxane (POSS) has long been used as an important functionalized technical material and is widely used to improve the properties of thermosetting and thermoplastic materials to enhance the heat resistance of the materials. Polyhedral oligomeric silsesquioxane (POSS) is composed of a general formula (RSiO 3 / 2A structurally well-defined compound composed of a silicon-oxygen framework, where R is H, alkyl, alkylene, aryl, aromatic group or their derivatives, which are reactive or inert functional groups. In the research of polymer-modified materials, functionalized POSS exhibits unique advantages as an inorganic-organic hybrid material. POSS has a unique nano-cage structure with unique physical and chemical properties, such as chemical resistance, mechanical toughness, thermal stability and hydrophobicity. It is precisely this nano-cage structure that is comparable to the segment size of most polymers, so POSS can be used to modify the local microstructure and chain mobility of polymers. The nanostructured POSS is dissolved in the polymer matrix at the molecular level, and the cage-shaped silsesquioxane can increase the maximum decomposition temperature and thermal oxidation resistance of the composite material. The reason for the improved thermal stability of the composite material is that the formation of the SiO2 protective layer can rigidify the polymer material and prevent the further degradation of the original polymer. Based on the current general anaerobic structural adhesives having good bonding strength at room temperature, but being not ideal in terms of heat resistance, mainly manifested in that at working conditions of 150 °C or above, the bonding strength will drop significantly, making it difficult to meet the bonding requirements of industries such as metal machinery, electronics and electrical, and aerospace under high-temperature conditions. Therefore, it is necessary to synthesize a high-temperature-resistant anaerobic adhesive to meet the industrial demand for anaerobic adhesives in high-temperature environments. Summary of the Invention

[0003] In view of the above-mentioned drawbacks and deficiencies of the prior art, the primary object of the present invention is to provide a high-temperature-resistant anaerobic adhesive having a functionalized cage-shaped silsesquioxane structure.

[0004] Another object of the present invention is to provide a preparation method of a high-temperature-resistant anaerobic adhesive having a functionalized cage-shaped silsesquioxane structure.

[0005] Another object of the present invention is to provide the application of the above-mentioned high-temperature-resistant anaerobic adhesive having a functionalized cage-shaped silsesquioxane structure.

[0006] The technical problems to be solved by the present invention are achieved through the following technical solutions:

[0007] A high-temperature-resistant anaerobic adhesive having a functionalized cage-shaped silsesquioxane structure, wherein the high-temperature-resistant anaerobic adhesive is composed of the following components in parts by weight:

[0008]

[0009] Preferably, the high-temperature-resistant anaerobic adhesive is composed of the following components in parts by weight:

[0010]

[0011] Preferably, the methacryloxypropylcaged silsesquioxane is γ-methacryloxypropylcaged silsesquioxane, which is prepared by the hydrolysis and condensation reaction of γ-methacryloxypropyltrimethoxysilane (KH570) under acidic conditions.

[0012] Preferably, the preparation method of the γ-methacryloxypropylcaged silsesquioxane is as follows: Drop the mixed acid solution into the ethanol aqueous solution until the pH is 4-5, drop γ-methacryloxypropyltrimethoxysilane, adjust the temperature to 35-40 °C, keep the temperature constant for reaction for 72-90 h. After obtaining a homogeneous and transparent solution, adjust the pH of the solution to 7 and distill to obtain γ-methacryloxypropylcaged silsesquioxane.

[0013] Preferably, the structural formula of the γ-methacryloxypropylcaged silsesquioxane is as follows:

[0014]

[0015] Preferably, the mass ratio of absolute ethanol to water in the ethanol aqueous solution is 6-7:10, and the mixed acid solution is prepared by mixing nitric acid and trifluoromethanesulfonic acid according to a volume ratio of 1:1-3.

[0016] Preferably, the mass ratio of γ-methacryloxypropyltrimethoxysilane to the ethanol aqueous solution is 1:8-10.

[0017] Preferably, the methacrylate monomer is one or a mixture of several of diethylene glycol dimethacrylate, bisphenol A epoxy dimethacrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate;

[0018] The inhibitor is one or a mixture of several of hydroquinone, maleic acid, p-methoxyphenol, p-tert-butylphenol.

[0019] Preferably, at least one of the metal chelating agents sodium ethylenediaminetetraacetate and disodium ethylenediaminetetraacetate;

[0020] The initiator is one or a mixture of several of cumene hydroperoxide, diisopropylbenzene hydroperoxide, tert-butyl hydroperoxide.

[0021] The accelerator is one or a mixture of several of phthalimide, acetylphenylhydrazine, triethylamine.

[0022] The auxiliary material is one or a mixture of glycerol and water.

[0023] A method for preparing the above high-temperature anaerobic adhesive includes the following steps:

[0024] (1) Under the stirring condition of 80°C to 90°C, the methacrylate monomer and methacryloxypropylcage silsesquioxane are stirred evenly in proportion, and then a metal chelating agent, a polymerization inhibitor, and a promoter are added in proportion and stirred for 1 to 2 hours. The temperature is lowered to 50°C to 55°C, and auxiliary materials and an initiator are added, and stirring is continued for 1 to 2 hours. After stirring evenly, a high-temperature resistant anaerobic adhesive with a functionalized cage silsesquioxane structure is obtained.

[0025] The application of the above high-temperature resistant anaerobic adhesive in chemical pipelines, automobile assembly, locking, sealing, and holding of metal parts.

[0026] Compared with the prior art, the present invention has the following advantages and beneficial effects:

[0027] (1) The present invention successfully prepares a high-purity functionalized cage silsesquioxane. By adding the functionalized cage silsesquioxane, the crosslinking density of the anaerobic adhesive is increased, and the heat resistance is improved. High-purity functionalized cage silsesquioxane is extremely important for the heat resistance of materials because impure functionalized cage silsesquioxane will cause phase separation of the materials and is prone to cracking in high-temperature environments, which is not conducive to improving the heat resistance of materials.

[0028] (2) The high-temperature resistant anaerobic adhesive with a functionalized cage silsesquioxane structure prepared by the method of the present invention can be adjusted into various forms of anaerobic adhesives as needed and applied to the locking, sealing, and holding of metal parts in the fields of chemical pipelines, automobile assembly, machinery manufacturing, and maintenance. It is particularly suitable for high-temperature locking and sealing occasions of such components, and can also be applied to the locking, sealing, and holding of parts with oil stains on the surface. The cured adhesive has good high-temperature resistance and can withstand temperatures up to 350°C. The specific thermogravimetric data and mechanical properties tested are shown in Figure 1 , Figure 2 and Table 2, Table 3. Description of the Drawings

[0029] Figure 1 It is the thermogravimetric test result of the anaerobic adhesives obtained in the examples and comparative examples.

[0030] Figure 2 It is a partial enlarged view of the thermogravimetric curve of the anaerobic adhesives obtained in the examples and comparative examples.

[0031] Figure 3 a, Figure 3 b, Figure 3 c, Figure 3 d are respectively the infrared spectrum, nuclear magnetic resonance hydrogen spectrum, thermogravimetric curve, and specific chemical structural formula of γ-methacryloxypropylcage silsesquioxane. Detailed Embodiments

[0032] The present invention will be further described below in conjunction with embodiments. The embodiments are only the preferred embodiments of the present invention and do not limit the present invention.

[0033] Example 1

[0034] The preparation method of γ-methacryloxypropylcage silsesquioxane is as follows:

[0035] In a four-necked flask equipped with a stirring device, add 60 grams of absolute ethanol and 100 g of deionized water. Start the stirring device and stir the absolute ethanol and deionized water evenly. Then, dropwise add a mixed acid solution (preparation method of the mixed acid solution: nitric acid and trifluoromethanesulfonic acid are prepared according to a volume ratio of 1:1) until the pH of the solution environment in the reaction flask is 5. Finally, slowly dropwise add 16.5 g of γ-methacryloxypropyltrimethoxysilane (KH570) using a peristaltic pump. After the addition of KH570 is completed, set the temperature of the reaction device to 35 °C and carry out a constant-temperature reaction for 72 h. After obtaining a homogeneous and transparent solution, add sodium hydroxide to adjust the pH of the solution to 7. Perform a liquid vacuum distillation operation on the neutral solution to remove soluble impurities, and finally obtain γ-methacryloxypropylcage silsesquioxane. Table 1 shows the GPC test data of γ-methacryloxypropylcage silsesquioxane. Figure 3 a, Figure 3 b, Figure 3 c are respectively the infrared spectrum, nuclear magnetic resonance hydrogen spectrum, and thermogravimetric curve of γ-methacryloxypropylcage silsesquioxane. Figure 3 d is the specific chemical structural formula of γ-methacryloxypropylcage silsesquioxane (γMA-POSS).

[0036] Table 1

[0037]

[0038] According to the GPC data, the synthesized product conforms to the cage silsesquioxane structure and is in good agreement with the theoretically designed molecular weight of 1434, and high-purity cage silsesquioxane can be obtained. Combining the infrared and nuclear magnetic resonance data, the analysis is as follows: Through the infrared spectrum, a broad and strong absorption peak can be observed at 1010 cm -1 . The peak at this position can be attributed to the absorption peak of the Si-O-Si bond, indicating the presence of a large amount of Si-O-Si structure in the product. A vibration absorption peak of C=C can be observed at a wave number of 1610 cm -1 . The absorption peak at a wave number of 1300 cm -1 can be attributed to the bending vibration absorption peak of -CH3. The sharp peak at 790 cm -1 in the infrared spectrum belongs to the out-of-plane deformation stretching vibration peak of =CH2. The wave number 1430 cm -1 in the spectrum corresponds to the bending vibration absorption peak of -CH2-. 1710 cm -1The peak at [specific location] corresponds to the C=O vibration absorption peak in the product structure. At 2950 cm -1 The stretching vibration peaks of the C-H bonds on -CH3 and -CH2 can be observed. Through the analysis of the spectrum, no absorption peak of Si-OH was found, indicating that the hydrolysis and condensation of KH-570 were complete. By analyzing the spectrum, the hydrogen signals in the spectrum can be assigned. 6.1 ppm (Ha, 1H) is the characteristic signal peak of the vinylic hydrogen at the end of the R group, and this hydrogen atom is on the opposite side of the methyl group. 5.6 ppm (Hb, 1H) is the characteristic signal peak of the vinylic hydrogen at the end of the R group, but this hydrogen atom is on the same side of the methyl group. 4.2 ppm (Hd, 2H) is the characteristic signal peak of the hydrogen on the first methylene group connected to the ester group. 1.9 ppm (Hc, 3H) is the characteristic absorption peak of the methyl group on the R group. 1.7 ppm (He, 2H) is the characteristic signal peak of the hydrogen atom on the second methylene group connected to the ester group. 0.7 ppm (Hf, 2H) is the characteristic signal peak of the hydrogen atom on the third methylene group connected to the ester group. Based on the above test results, a single γ-methacryloxypropylcaged silsesquioxane was successfully synthesized.

[0039] Figure 3 The thermogravimetric curve of c shows that γ-methacryloxypropylcaged silsesquioxane has good heat resistance, which is the theoretical basis for improving the heat resistance of anaerobic adhesives.

[0040] Example 2

[0041] The components and their mass fractions of a high-temperature resistant anaerobic adhesive with a functionalized caged silsesquioxane structure are as follows:

[0042]

[0043]

[0044] During preparation, according to the above weight fractions, the methacrylate monomer was added to a three-necked flask and stirred evenly at 80 °C. Then, γ-methacryloxypropylcaged silsesquioxane was added and stirred evenly. Then, sodium ethylenediaminetetraacetate, hydroquinone, maleic acid, saccharin, and acetylphenylhydrazine were added in proportion and stirred for one hour. Then, the temperature was lowered to 50 °C, and glycerol, deionized water, and diisopropylbenzene hydroperoxide were added, and stirring was continued for one hour. After stirring evenly, the finished product could be obtained.

[0045] Example 3

[0046]

[0047]

[0048] During preparation, according to the above weight parts, add the methacrylate monomer into a three-necked flask, stir evenly at 80 °C, then add γ-methacryloxypropylcage silsesquioxane, stir evenly, and then add sodium ethylenediaminetetraacetate, hydroquinone, maleic acid, saccharin and acetylphenylhydrazine in proportion, stir for one hour, then cool down to 50 °C, add glycerol, deionized water and diisopropylbenzene hydroperoxide, continue to stir for one hour, and the finished product can be obtained after stirring evenly.

[0049] Example 4

[0050]

[0051] During preparation, according to the above weight parts, add the methacrylate monomer into a three-necked flask, stir evenly at 80 °C, then add γ-methacryloxypropylcage silsesquioxane, stir evenly, and then add sodium ethylenediaminetetraacetate, hydroquinone, maleic acid, saccharin and acetylphenylhydrazine in proportion, stir for one hour, then cool down to 50 °C, add glycerol, deionized water and diisopropylbenzene hydroperoxide, continue to stir for one hour, and the finished product can be obtained after stirring evenly.

[0052] Example 5

[0053]

[0054] During preparation, according to the above weight parts, add the methacrylate monomer into a three-necked flask, stir evenly at 80 °C, then add γ-methacryloxypropylcage silsesquioxane, stir evenly, and then add sodium ethylenediaminetetraacetate, hydroquinone, maleic acid, saccharin and acetylphenylhydrazine in proportion, stir for one hour, then cool down to 50 °C, add glycerol, deionized water and diisopropylbenzene hydroperoxide, continue to stir for one hour, and the finished product can be obtained after stirring evenly.

[0055] Example 6

[0056]

[0057]

[0058] During preparation, according to the above weight parts, add the methacrylate monomer into a three-necked flask, stir evenly at 80 °C, then add γ-methacryloxypropylcage silsesquioxane, stir evenly, and then add sodium ethylenediaminetetraacetate, hydroquinone, maleic acid, saccharin and acetylphenylhydrazine in proportion, stir for one hour, then cool down to 50 °C, add glycerol, deionized water and diisopropylbenzene hydroperoxide, continue to stir for one hour, and the finished product can be obtained after stirring evenly.

[0059] Comparative Example 1

[0060]

[0061]

[0062] During preparation, according to the above weight parts, the methacrylate monomer was added to a three-necked flask, stirred evenly at 80 °C, and then sodium ethylenediaminetetraacetate, hydroquinone, maleic acid, saccharin, and acetylphenylhydrazine were added in proportion, and stirred for one hour. Then the temperature was lowered to 50 °C, and glycerol, deionized water, and cumene hydroperoxide were added, and stirring was continued for one hour. After stirring evenly, the finished product could be obtained.

[0063] The anaerobic adhesives obtained in Example 2, Example 3, Example 4, Example 5, Example 6, and Comparative Example 1 were numbered 1#, 2#, 3#, 4#, 5#, and 6 respectively. The 1#, 2#, 3#, 4#, 5#, and 6 anaerobic adhesives were cured for 24 hours, and the torque strength and shear strength of the 1#, 2#, 3#, 4#, 5#, and 6 anaerobic adhesives at different temperatures were tested. The test results are shown in Table 2, Table 3, and Table 4. The thermogravimetric data of 1#, 2#, 3#, 4#, 5#, and 6 are as Figure 1 , Figure 2 shown.

[0064] Test method for torque of anaerobic adhesive: The torque test was carried out using a special torque wrench provided by Shaanxi Dongfang Aeronautical Instrument Co., Ltd. The torque test was carried out using a special torque wrench provided by the company. The torque was tested according to the "HB5315-1993 Test Method for Tightening Torque of Anaerobic Adhesives for Aeronautical Use". The torque value when relative displacement occurred between the nut and the bolt for the first time was defined as the failure torque (Tb) of the specimen, and the average disassembly torque (Tp) of the specimen was defined as the average value of the torques continuously read when the nut was unscrewed 1 / 4, 2 / 4, 3 / 4, and one turn;

[0065] Test method for shear strength (MPa) of anaerobic adhesive: The shear strength was tested by the static shear strength of the socket joints bonded by the adhesive using a tensile testing machine. The shear was tested according to the "HB 5314-1993 Test Method for Static Shear Strength of Anaerobic Adhesives for Aeronautical Use". The tested bonded part was placed in a hollow support cylinder, and pressure was applied to the steel shaft to make the steel shaft and the collar displace relative to each other at a speed of 2 mm / min. The maximum failure load value (N) at the relative displacement was recorded, and then divided by the bonding area to obtain the shear strength (MPa).

[0066] Test method for thermogravimetry of anaerobic adhesive: Thermogravimetric analysis was carried out using a TGA550 thermogravimetric analyzer from the United States. In a nitrogen atmosphere, the heating rate was 10 °C / min, and the heating range was 25 °C - 800 °C.

[0067] Table 2 Test results of breaking torque Tp (Nm) of 1#~6# anaerobic adhesives

[0068] 25℃ 150℃ 200℃ 300℃ 350℃ 1# 29 29 26 25 23 2# 32 31 31 28 26 3# 35 34 32 29 28 4# 48 46 45 43 36 5# 37 35 35 26 25 6# 21 14 3 0 0

[0069] Table 3 Test results of disassembly torque Tb (Nm) of 1#~6# anaerobic adhesives

[0070] 25℃ 150℃ 200℃ 300℃ 350℃ 1# 31 30 26 26 22 2# 33 31 30 27 24 3# 34 32 32 30 25 4# 50 44 42 40 37 5# 39 32 32 28 23 6# 19 11 2 0 0

[0071] Table 4 Test results of shear strength (MPa) of 1# to 6# anaerobic adhesives

[0072] 25℃ 150℃ 200℃ 300℃ 350℃ 1# 24 24 23 21 16 2# 27 26 26 18 17 3# 31 31 28 24 19 4# 34 32 32 29 26 5# 27 25 24 19 15 6# 19 16 2 0 0

[0073] According to the test data results in Table 2, Table 3, and Table 4, it can be seen that the prepared high-temperature resistant anaerobic adhesive with a functionalized cage-type silsesquioxane structure not only has better torque strength and shear strength at room temperature than the comparative example, but also still has good bonding strength in a high temperature environment. Figure 1 and Figure 2 It is also proved that the prepared high temperature resistant anaerobic adhesive with functionalized cage-type silsesquioxane structure has better heat resistance than the anaerobic adhesive prepared in the comparative example.

[0074] Comparative Example 2

[0075] The preparation method of γ-methacryloxypropyl cage-type silsesquioxane is as follows:

[0076] In a four-necked flask equipped with a stirring device, 60 grams of anhydrous ethanol and 100g of deionized water are added. Start the stirring device and stir the anhydrous ethanol and deionized water evenly. Then add hydrochloric acid solution dropwise until the pH of the solution environment in the reaction bottle is 3. Finally, 16.5g KH570 is slowly added dropwise using a peristaltic pump. After the addition of KH570 is complete, the temperature of the reaction device is set to 40°C and the reaction is carried out at a constant temperature for 72h. After obtaining a uniform and transparent solution, sodium hydroxide is added to adjust the pH of the solution to 7. The neutral solution is subjected to a liquid vacuum distillation operation to remove soluble impurities, and finally γ-methacryloxypropyl cage-type silsesquioxane (γMA-POSS) is obtained. Table 4 is the GPC data of the synthetic product of Example 2, which is quite different from the theoretical molecular weight 1434, indicating that the synthetic product is impure.

[0077] Table 5

[0078]

[0079] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any other changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the present invention shall be equivalent replacement methods and are all included in the protection scope of the present invention.

Claims

1. A high-temperature resistant anaerobic adhesive with a functionalized cage-type silsesquioxane structure, characterized in that, The high-temperature resistant anaerobic adhesive is composed of the following components in parts by weight: 4 - 18 parts of methacryloxypropylcage silsesquioxane 80 - 100 parts of methacrylate monomer 0.5 - 1 part of inhibitor 0.1 - 0.5 part of metal chelating agent 1 - 12 parts of initiator 0.5 - 3 parts of accelerator 1 - 2 parts of auxiliary materials; The methacryloxypropylcage silsesquioxane is γ-methacryloxypropylcage silsesquioxane, and the preparation method of the γ-methacryloxypropylcage silsesquioxane is as follows: Drop the mixed acid solution into the ethanol aqueous solution until the pH is 4 - 5, drop γ-methacryloxypropyltrimethoxysilane, adjust the temperature to 35 - 40 °C, react at a constant temperature for 72 - 90 h. After obtaining a homogeneous transparent solution, adjust the pH of the solution to 7 and distill to obtain γ-methacryloxypropylcage silsesquioxane; In the ethanol aqueous solution, the mass ratio of absolute ethanol to water is 6 - 7:10, and the mixed acid solution is prepared by mixing nitric acid and trifluoromethanesulfonic acid in a volume ratio of 1:1 - 3; The mass ratio of γ-methacryloxypropyltrimethoxysilane to the ethanol aqueous solution is 1:8 - 10.

2. The high-temperature resistant anaerobic adhesive with a functionalized cage-type silsesquioxane structure according to claim 1, characterized in that, The methacrylate monomer is one or a mixture of two of triethylene glycol dimethacrylate and bisphenol A epoxy dimethacrylate; The inhibitor is one or a mixture of several of hydroquinone, maleic acid, p-methoxyphenol, and p-tert-butylphenol.

3. The high-temperature resistant anaerobic adhesive with a functionalized cage-type silsesquioxane structure according to claim 1, characterized in that, The metal chelating agent is at least one of sodium ethylenediaminetetraacetate and disodium ethylenediaminetetraacetate; The initiator is one or a mixture of several of cumene hydroperoxide, diisopropylbenzene hydroperoxide, and tert-butyl hydroperoxide; The accelerator is one or a mixture of several of phthalimide, acetylphenylhydrazine, and triethylamine; The auxiliary materials are one or a mixture of two of glycerol and water.

4. A method for preparing the high-temperature resistant anaerobic adhesive according to any one of claims 1 to 3, characterized in that, It includes the following steps: (1) Under the stirring condition of 80 °C - 90 °C, stir the methacrylate monomer and methacryloxypropylcage silsesquioxane evenly in proportion, then add the metal chelating agent, inhibitor, and accelerator in proportion, stir for 1 - 2 h, cool down to 50 °C - 55 °C, add the auxiliary materials and initiator, and continue to stir for 1 - 2 h. After stirring evenly, a high-temperature resistant anaerobic adhesive with a functionalized cage silsesquioxane structure is obtained.

5. Application of the high-temperature resistant anaerobic adhesive according to any one of claims 1 - 3 in chemical pipelines, automobile assembly, locking, sealing, and holding of metal parts.

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