High-temperature-resistant anaerobic adhesive and usage method therefor

Abstract

A high-temperature-resistant anaerobic adhesive and a usage method therefor. The high-temperature-resistant anaerobic adhesive comprises the following components in parts by weight: 40-70 parts of a protocatechuic-acid-modified acrylate, 5-20 parts of isobornyl methacrylate, 1-8 parts of hydroxyethyl methylacrylate, 1-5 parts of an initiator, 0.1-10 parts of an accelerator, 2-10 parts of filler, and 0.01-0.2 parts of a stabilizer. When treated at room temperature, at a high temperature of 150°C or at a high temperature of 85°C and a relative humidity of 85% for a long time, the high-temperature-resistant anaerobic adhesive exhibits good bonding strength; and the adhesive is suitable for automatic assembly of miniaturized high-precision assemblies.

Description

High temperature resistant anaerobic adhesive and its use method Technical Field

[0001] The present application relates to the technical field of adhesive sealants, and in particular to a high-temperature resistant anaerobic adhesive and a method for using the same. Background Art

[0002] Anaerobic adhesives are single-component adhesive sealants made by utilizing the principle of oxygen's inhibition of free radicals. They remain liquid in the presence of oxygen and rapidly solidify in the absence of oxygen, forming a strong bond. They offer advantages such as ease of use, room-temperature curing, solvent-free operation, and excellent acid and alkali resistance. Anaerobic adhesives are essential adhesives for sealing, fastening, and anti-loosening processes, and are widely used in machinery manufacturing and maintenance, aerospace, transportation, and electronics and electrical engineering.

[0003] The trend toward miniaturization of electronic devices such as microactuators and microsensors has created an urgent need for anaerobic adhesives with high bond strength, excellent high-temperature resistance, and applicability to planar structures. However, traditional anaerobic adhesives, primarily threadlockers, suffer from low bond strength and poor high-temperature resistance when used for bonding planar structures, making them difficult to meet the bonding requirements of miniaturized, high-precision components under high-temperature conditions.

[0004] Summary of the Invention

[0005] Based on this, it is necessary to provide a high-temperature resistant anaerobic adhesive and a method of using it to solve the shortcomings of traditional anaerobic adhesives when used for bonding planar structures, such as low bonding strength and poor high-temperature resistance, which makes it difficult to meet the bonding requirements of miniaturized and high-precision components under high-temperature conditions.

[0006] The above-mentioned purpose of this application is achieved through the following technical solutions:

[0007] In a first aspect of the present application, a high-temperature anaerobic adhesive is provided, comprising the following components in parts by weight:

[0008] Wherein, the protocatechuic acid modified acrylate has a structure as shown in the general formula (I):

[0009] Each occurrence of R is independently selected from one of H and an alkyl group containing 1 to 8 carbon atoms.

[0010] In one embodiment, each occurrence of R is independently selected from one of H and an alkyl group containing 1 to 6 carbon atoms.

[0011] In one embodiment, the preparation method of the protocatechuic acid modified acrylate comprises the following steps:

[0012] A mixed solution A containing protocatechuic acid, epichlorohydrin and a cosolvent is subjected to a substitution reaction under alkaline conditions to prepare a mixed solution B containing an intermediate;

[0013] Purifying the mixed solution B to prepare an intermediate;

[0014] Mixing the intermediate, catalyst, polymerization inhibitor and acrylic acid compound having a structure represented by general formula (III) to carry out a ring-opening addition reaction to prepare the protocatechuic acid-modified acrylate;

[0015] In one embodiment, R is selected from one of H, methyl, ethyl, 1-propyl and 2-propyl.

[0016] In one embodiment, a mixture A containing protocatechuic acid, epichlorohydrin, and a cosolvent is subjected to a substitution reaction under alkaline conditions, comprising the following steps:

[0017] Under the conditions of temperature of 30° C. to 65° C. and vacuum degree of -65 kPa to 0 kPa, alkali solution is added to the mixed solution A and reacted for 3 h to 6 h.

[0018] In one embodiment, in the mixed solution A, the mass ratio of the protocatechuic acid, the epichlorohydrin and the co-solvent is 1:(2-3):(0.5-1).

[0019] In one embodiment, the co-solvent includes one or more of water, butanol, propylene glycol methyl ether, toluene, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone.

[0020] In one embodiment, the alkali in the alkali solution includes one or more of NaOH, KOH, Na2CO3, NaHCO3, K2CO3 and KHCO3.

[0021] In one embodiment, the mass fraction of alkali in the alkali solution is 10% to 50%.

[0022] In one embodiment, the molar ratio of the protocatechuic acid to the alkali in the alkali solution is 1:(3.01-3.20).

[0023] In one embodiment, the intermediate, catalyst, polymerization inhibitor and acrylic acid compound are mixed to carry out a ring-opening addition reaction, comprising the following steps:

[0024] Mixing the intermediate, the catalyst and the polymerization inhibitor at 70° C. to 80° C. to prepare a mixed solution C;

[0025] The acrylic acid compound is added to the mixed solution C, and the mixture is reacted at 80° C. to 120° C. until the pH value of the system is ≤5.

[0026] In one embodiment, the molar ratio of protocatechuic acid to the acrylic acid compound in the mixed solution A is (1.01-1.10):3.

[0027] In one embodiment, the catalyst includes one or more of tetraphenylphosphine bromide, triphenylphosphine, tetrabutylphosphine chloride, ethyltriphenylphosphine bromide, tetraethylammonium bromide and tetrabutylammonium bromide.

[0028] In one embodiment, the molar ratio of the catalyst to the acrylic acid compound is (0.001-0.01):1.

[0029] In one embodiment, the polymerization inhibitor includes one or more of hydroquinone, p-benzoquinone, methylhydroquinone, p-hydroxyanisole and 2-tert-butylhydroquinone.

[0030] In one embodiment, the molar ratio of the polymerization inhibitor to the acrylic acid compound is (0.0001-0.001):1.

[0031] In one embodiment, the initiator includes one or more of dicumyl peroxide, tert-butyl perbenzoate, and cumene hydroperoxide.

[0032] In one embodiment, the accelerator includes one or more of saccharin, acetylphenylhydrazine, N,N-dimethyl-p-toluidine, 1,5-diphenylcarbazide, phthalimide, acrylic acid, methacrylic acid, maleic acid and ascorbic acid.

[0033] In one embodiment, the stabilizer includes one or more of 1,4-hydroquinone, 4-methoxyphenol, benzoquinone, oxalic acid and ethylenediaminetetraacetic acid.

[0034] In one embodiment, the filler includes one or more of fumed silica and bentonite.

[0035] In one embodiment, the high temperature resistant anaerobic adhesive further comprises the following components in parts by weight: 0 to 20 parts of a tackifier and 0.1 to 0.5 parts of a pigment.

[0036] In one embodiment, the tackifier includes one or more of polymethacrylic acid, dioctyl phthalate, unsaturated fumaric resin and methyl nylonate.

[0037] In one embodiment, the pigment includes one or more of phthalocyanine blue, phthalocyanine green, reactive red and lemon yellow.

[0038] In a second aspect of the present application, a method for using a high temperature resistant anaerobic adhesive is provided, comprising the following steps:

[0039] coating a surface promoter and the high-temperature resistant anaerobic adhesive as described above on a substrate to form a liquid film;

[0040] The components to be bonded are covered on the liquid film and cured under pressure.

[0041] In one embodiment, the surface promoter includes one or more of copper octoate, ferrocene and copper acetate.

[0042] This application has at least the following beneficial effects:

[0043] Protocatechuic acid is a trifunctional small molecule containing a benzene ring structure. The protocatechuic acid-modified acrylate prepared using it can introduce a highly rigid benzene ring structure and multiple acrylate functional groups into the molecular structure. Under curing conditions, a dense three-dimensional cured network structure can be formed, which is beneficial to increasing the crosslinking density, thereby improving the high temperature resistance of the cured product. In the high-temperature resistant anaerobic adhesive of the present application, the protocatechuic acid-modified acrylate has excellent high-temperature resistance, the isobornyl methacrylate has high bonding strength, and the hydroxyethyl methacrylate has good flexibility. By utilizing the synergistic cooperation of these three monomers, and in combination with initiators and promoters that accelerate the curing speed, fillers that adjust the viscosity and increase the bonding strength, and stabilizers that ensure storage stability, a high-temperature resistant anaerobic adhesive with excellent high-temperature resistance and high bonding strength can be obtained. It exhibits excellent bonding strength after long-term treatment at room temperature, at a high temperature of 150°C, and at a high temperature of 85°C and a relative humidity of 85%, and is suitable for miniaturized, high-precision component automated assembly. DETAILED DESCRIPTION

[0044] To make the above-mentioned objects, features, and advantages of the present application more clearly understood, the specific embodiments of the present application are described in detail below. The following description sets forth many specific details to facilitate a full understanding of the present application. However, the present application can be implemented in many other ways than those described herein, and those skilled in the art can make similar modifications without violating the scope of the present application. Therefore, the present application is not limited to the specific embodiments disclosed below.

[0045] Furthermore, the terms "first" and "second" are used for descriptive purposes only and should not be construed as indicating or implying relative importance or implicitly specifying the number of the technical features being referred to. Thus, a feature defined as "first" or "second" may explicitly or implicitly include at least one of such features. Throughout the description of this application, "plurality" means at least two, for example, two, three, etc., unless otherwise specifically defined.

[0046] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which this application pertains. The terms used herein in the specification of this application are for the purpose of describing specific embodiments only and are not intended to limit this application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0047] the term

[0048] Unless otherwise specified or incompatible therewith, terms and phrases used in this application shall have the following meanings:

[0049] Functionality: The number of functional groups in a monomer molecule that can participate in a condensation reaction is called functionality. For example, in the condensation reaction of acetic acid and ethanol, the functionality of both acetic acid and ethanol is 1; in the condensation reaction of octanol and phthalic anhydride, the functionality of octanol is 1, and the functionality of phthalic anhydride is 2. It can be understood that a monofunctional monomer is a monomer with one functional group that can participate in the reaction, a difunctional monomer is a monomer with two functional groups that can participate in the reaction, and a polyfunctional monomer is a monomer with at least three functional groups that can participate in the reaction.

[0050] In this application, when a substituent with the same symbol appears multiple times, each substituent may be the same or different. For example, when a general formula contains multiple R, each R may be the same or different.

[0051] "Alkyl" refers to a monovalent residue formed by the loss of a hydrogen atom from a saturated hydrocarbon containing a primary (normal) carbon atom, a secondary carbon atom, a tertiary carbon atom, a quaternary carbon atom, or a combination thereof. Alkyl can represent a straight chain, branched chain, and / or cyclic alkyl group. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, for example, "C1 to C9 alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Suitable examples include, but are not limited to, methyl (Me, -CH3), ethyl (Et, -CH2CH3), 1-propyl (n-Pr, n-propyl, -CH2CH2CH3), 2-propyl (i-Pr, i-propyl, -CH(CH3)2), 1-butyl (n-Bu, n-butyl, -CH2CH2CH2CH3), 2-methyl-1-propyl (i-Bu, i-butyl, -CH2CH(CH3)2), 2-butyl (s-Bu, s-butyl, -CH(C H3)CH2CH3), 2-methyl-2-propyl (t-Bu, t-butyl, -C(CH3)3), 1-pentyl (n-pentyl, -CH2CH2CH2CH2CH3), 2-pentyl (-CH(CH3)CH2CH2CH3), 3-pentyl (-CH(CH2CH3)2), 2-methyl-2-butyl (-C(CH3)2CH2CH3), 3-methyl-2-butyl (-CH(CH3)CH(CH3)2), 3-methyl-1-butyl (- CH2CH2CH(CH3)2), 2-methyl-1-butyl (-CH2CH(CH3)CH2CH3), 1-hexyl (-CH2CH2CH2CH2CH2CH3), 2-hexyl (-CH(CH3)CH2CH2CH2CH3), 3-hexyl (-CH(CH2CH3)(CH2CH2CH3)), 2-methyl-2-pentyl (-C(CH3)2CH2CH2CH3), 3-methyl-2-pentyl (-CH(CH3)CH( 2), 2-methyl-3-pentyl (-CH(CH2CH3)CH(CH3)2), 2,3-dimethyl-2-butyl (-C(CH3)2CH(CH3)2), 3,3-dimethyl-2-butyl (-CH(CH3)C(CH3)3, octyl (-(CH2)7CH3).

[0052] In this application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0053] In this application, when referring to numerical ranges, unless otherwise specified, the numerical ranges are considered continuous and include the minimum and maximum values ​​of the range, as well as every value between such minimum and maximum values. Further, when a range refers to an integer, every integer between the minimum and maximum values ​​of the range is included. In addition, when multiple ranges are provided to describe a feature or characteristic, the ranges can be combined. In other words, unless otherwise specified, all ranges disclosed herein should be understood to include any and all subranges subsumed therein.

[0054] The percentage contents involved in this application, unless otherwise specified, refer to mass percentage for solid-liquid mixture and solid-solid phase mixture, and refer to volume percentage for liquid-liquid phase mixture.

[0055] The temperature parameters in this application, unless otherwise specified, allow for both constant temperature treatment and treatment within a certain temperature range. The constant temperature treatment allows for temperature fluctuations within the precision range of instrument control.

[0056] In this application, room temperature refers to indoor temperature, normal temperature or general temperature. Generally speaking, the range of room temperature can be any one of the following temperature intervals: (1) 23℃±2℃; (2) 25℃±5℃; (3) 20℃±5℃.

[0057] In the first aspect of the present application, a high-temperature resistant anaerobic adhesive is provided to solve the problem that traditional anaerobic adhesives are mainly thread locking adhesives, which have disadvantages such as low bonding strength and poor high-temperature resistance when used for bonding planar structures, and are difficult to meet the bonding requirements of miniaturized and high-precision components under high-temperature conditions.

[0058] In some embodiments, the high temperature resistant anaerobic adhesive includes the following components in parts by weight:

[0059] Understandably, the chemical name of protocatechuic acid is 3,4-dihydroxybenzoic acid, and its molecular structure contains both a highly rigid benzene ring and highly chemically reactive hydroxyl and carboxyl groups.

[0060] It can be understood that multifunctional acrylate refers to an acrylate compound containing at least three acrylate functional groups in its molecular structure.

[0061] Protocatechuic acid is a trifunctional small molecule containing a benzene ring structure. The protocatechuic acid-modified acrylate prepared using it can introduce a highly rigid benzene ring structure and multiple acrylate functional groups into the molecular structure. Under curing conditions, a dense three-dimensional cured network structure can be formed, which is beneficial to increasing the crosslinking density, thereby improving the high temperature resistance of the cured product. In the high-temperature resistant anaerobic adhesive of the present application, the protocatechuic acid-modified acrylate has excellent high-temperature resistance, the isobornyl methacrylate has high bonding strength, and the hydroxyethyl methacrylate has good flexibility. By utilizing the synergistic cooperation of these three monomers, and in combination with initiators and promoters that accelerate the curing speed, fillers that adjust the viscosity and increase the bonding strength, and stabilizers that ensure storage stability, a high-temperature resistant anaerobic adhesive with excellent high-temperature resistance and high bonding strength can be obtained. It exhibits excellent bonding strength after long-term treatment at room temperature, at a high temperature of 150°C, and at a high temperature of 85°C and a relative humidity of 85%, and is suitable for miniaturized, high-precision component automated assembly.

[0062] In the present application, the weight of protocatechuic acid-modified acrylate is 40 to 70 parts, including but not limited to: 40 parts, 45 parts, 50 parts, 55 parts, 60 parts, 65 parts and 70 parts, preferably 45 to 65 parts. The weight of isobornyl methacrylate is 5 to 20 parts, including but not limited to: 5 parts, 10 parts, 12 parts, 14 parts, 16 parts, 18 parts and 20 parts, preferably 10 to 15 parts. The weight of hydroxyethyl methacrylate is 1 to 8 parts, including but not limited to: 1 part, 2 parts, 3 parts, 4 parts, 5 parts, 6 parts, 7 parts and 8 parts, preferably 4 to 8 parts. The weight of the initiator is 1 to 5 parts, including but not limited to: 1 part, 2 parts, 3 parts, 4 parts and 5 parts, preferably 2 to 3 parts. The weight portion of the accelerator is 0.1 to 10 parts, including but not limited to: 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10 parts, preferably 0.6 to 7 parts. The weight portion of the filler is 2 to 10 parts, including but not limited to: 2, 3, 4, 5, 6, 7, 8, 9 and 10 parts, preferably 3 to 6 parts. The weight portion of the stabilizer is 0.01 to 0.2 parts, including but not limited to: 0.01, 0.02, 0.05, 0.08, 0.1, 0.12, 0.15, 0.18 and 0.2 parts, preferably 0.01 to 0.1 parts.

[0063] In some embodiments, the protocatechuic acid-modified acrylate has a structure as shown in formula (I):

[0064] Each occurrence of R is independently selected from one of H and an alkyl group containing 1 to 8 carbon atoms.

[0065] In this application, each occurrence of R is independently selected from one of hydrogen and an alkyl group containing 1 to 8 carbon atoms. Preferably, each occurrence of R is independently selected from one of hydrogen and an alkyl group containing 1 to 6 carbon atoms. More preferably, each occurrence of R is independently selected from one of hydrogen and an alkyl group containing 1 to 4 carbon atoms. More preferably, R is each independently selected from H and an alkyl group containing 1 to 3 carbon atoms, that is, R is each independently selected from H, methyl (Me, -CH3), ethyl (Et, -CH2CH3), 1-propyl (n-Pr, n-propyl, -CH2CH2CH3), 2-propyl (i-Pr, i-propyl, -CH(CH3)2), 1-butyl (n-Bu, n-butyl, -CH2CH2CH2CH3), 2-methyl-1-propyl (i-Bu, i-butyl, -CH2CH(CH3)2), 2-butyl (s-Bu, s-butyl, -CH(CH3)CH2CH3) and 2-methyl-2-propyl (t-Bu, t-butyl, -C(CH3)3).

[0066] In some embodiments, R is selected from methyl (Me, -CH3), and the protocatechuic acid-modified acrylate has a structure as shown in the general formula (II):

[0067] In some embodiments, the preparation method of protocatechuic acid-modified acrylate comprises the following steps:

[0068] S1: subjecting a mixed solution A containing protocatechuic acid, epichlorohydrin and a co-solvent to a substitution reaction under alkaline conditions to prepare a mixed solution B containing an intermediate;

[0069] S2: Purify the mixed solution B to prepare an intermediate;

[0070] S3: mixing the intermediate, the catalyst, the polymerization inhibitor and the acrylic acid compound to carry out a ring-opening addition reaction to prepare protocatechuic acid-modified acrylate.

[0071] The preparation method of protocatechuic acid modified acrylate is described in detail below through step-by-step description.

[0072] S1: a mixed solution A containing protocatechuic acid, epichlorohydrin and a co-solvent is subjected to a substitution reaction under alkaline conditions to prepare a mixed solution B containing an intermediate.

[0073] Under alkaline conditions, epichlorohydrin will undergo a substitution reaction with the two hydroxyl groups and one carboxyl group in the molecular structure of protocatechuic acid to generate an intermediate containing three epoxy functional groups. The reaction formula is as follows:

[0074] In some embodiments, a mixed solution A containing protocatechuic acid, epichlorohydrin, and a co-solvent is subjected to a substitution reaction under alkaline conditions, comprising the following steps: adding alkaline solution to the mixed solution A at a temperature of 30° C. to 65° C. and a vacuum degree of -65 kPa to 0 kPa, and reacting for 3 h to 6 h.

[0075] Understandably, a vacuum degree of -65kPa to 0kPa represents the relative pressure of the system, meaning that the absolute pressure of the system is 65kPa to 0kPa lower than atmospheric pressure. A vacuum degree of 0kPa indicates normal pressure, while a negative vacuum value indicates negative pressure. Controlling the temperature and pressure during the addition of the alkali solution can promote the substitution reaction between the phenolic hydroxyl group of protocatechuic acid and epichlorohydrin, accelerating the reaction rate.

[0076] It can be understood that in the process of adding alkali solution to mixed solution A, the temperature can be 30°C, 35°C, 40°C, 45°C, 50°C, 55°C, 60°C and 65°C, preferably 40°C to 60°C; the pressure is normal pressure or negative pressure, preferably normal pressure; the reaction time after adding alkali solution to mixed solution A can be 3h, 3.5h, 4h, 4.5h, 5h, 5.5h and 6h, preferably 4h to 6h.

[0077] In some embodiments, the alkali solution is added to the mixed solution A dropwise, and the addition is done slowly in 3 to 6 times. This can avoid the problem of excessive reaction speed and insufficient reaction of the raw materials.

[0078] In some embodiments, the mass ratio of protocatechuic acid, epichlorohydrin, and cosolvent is 1:(2-3):(0.5-1). Specifically, the mass ratio of protocatechuic acid to epichlorohydrin is 1:(2-3), and can be 1:2, 1:2.2, 1:2.4, 1:2.6, 1:2.8, and 1:3. The mass ratio of protocatechuic acid to cosolvent is 1:(0.5-1), and can be 1:0.5, 1:0.6, 1:0.7, 1:0.8, 1:0.9, and 1:1. The mass ratio of epichlorohydrin to cosolvent is (2-3):(0.5-1), and can be 2:0.5, 2:0.8, 2:1, 2.5:0.5, 2.5:0.8, 2.5:1, 3:0.5, 3:0.8, and 3:1. Preferably, the mass ratio of protocatechuic acid, epichlorohydrin and co-solvent is 1:(2.5-2.8):(0.5-0.7).

[0079] In some embodiments, the cosolvent includes one or more of water, butanol, propylene glycol methyl ether, toluene, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, preferably methyl isobutyl ketone. It is understood that the cosolvent does not participate in the substitution reaction, but rather miscible with protocatechuic acid and epichlorohydrin, increasing the solubility of protocatechuic acid and epichlorohydrin in the system, thereby accelerating the reaction rate.

[0080] In some embodiments, the base in the alkali solution includes one or more of NaOH, KOH, Na2CO3, NaHCO3, K2CO3 and KHCO3, preferably NaOH.

[0081] In some embodiments, the mass fraction of the alkali in the alkali solution is 10% to 50%, for example, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% and 50%, preferably 30% to 50%, and more preferably 40% to 50%.

[0082] In some embodiments, the molar ratio of protocatechuic acid to the alkali in the alkali solution is 1:(3.01-3.20), specifically 1:3.01, 1:3.05, 1:3.10, 1:3.15 and 1:3.20, preferably 1:(3.02-3.1).

[0083] In some specific embodiments, step S1 includes the following steps: mixing protocatechuic acid, epichlorohydrin and a co-solvent uniformly to obtain a mixed solution A; heating the mixed solution A to 30°C to 65°C, and adding a 10% to 50% alkali solution by mass in 3 to 6 times under a vacuum degree of -65kPa to 0kPa, reacting for 3h to 6h to obtain a mixed solution B.

[0084] S2: Purify the mixed solution B to prepare an intermediate.

[0085] Through purification treatment, residual epichlorohydrin, cosolvent and alkali in mixed solution B can be removed, and by-products such as hydrochloride generated by the reaction can be removed to obtain a high-purity intermediate, reduce the adverse effects of various impurities on the subsequent ring-opening addition reaction, and improve the reaction rate and reaction selectivity of the ring-opening addition reaction.

[0086] In some embodiments, the purification process includes a neutralization process, a water washing process, and a nitrogen stripping process.

[0087] The neutralization treatment can neutralize the alkali in the mixed solution B and generate corresponding salt compounds. These salt compounds can be removed by multiple water washing treatments. The unreacted epichlorohydrin and the unreactive co-solvent can be removed by nitrogen stripping treatment, thereby obtaining a high-purity intermediate.

[0088] In some embodiments, the neutralizing agent used in the neutralization treatment includes one or more of hydrogen phosphate and dihydrogen phosphate, preferably dihydrogen phosphate, and more preferably sodium dihydrogen phosphate.

[0089] In some embodiments, the pH of the mixed solution B after neutralization is 6.9-7.1, preferably 6.95-7.05, and more preferably 7.

[0090] In some embodiments, the temperature of the nitrogen stripping treatment is 130°C to 150°C, such as 130°C, 135°C, 140°C, 145°C, and 150°C, preferably 130°C to 140°C.

[0091] In some embodiments, the vacuum degree of the nitrogen stripping treatment is -80 kPa to -95 kPa, for example, -80 kPa, -82 kPa, -84 kPa, -86 kPa, -88 kPa, -90 kPa, -92 kPa, and -95 kPa, preferably -80 kPa to -85 kPa. It can be understood that the vacuum degree of -80 kPa to -95 kPa is a relative pressure value of the system, which physically means that the absolute pressure value of the system is 80 kPa to 95 kPa lower than the atmospheric pressure.

[0092] In some embodiments, the nitrogen flow rate of the nitrogen stripping treatment is 0.2 mL / min to 15 mL / min, for example, 0.2 mL / min, 0.5 mL / min, 0.8 mL / min, 1 mL / min, 2 mL / min, 5 mL / min, 8 mL / min, 10 mL / min, 12 mL / min and 15 mL / min, preferably 0.5 mL / min to 5 mL / min.

[0093] In some specific embodiments, step S2 includes the following steps: neutralizing the mixed solution B with sodium dihydrogen phosphate to neutralize the alkali in the mixed solution B, and washing with water to remove the generated salt compounds; introducing nitrogen at a flow rate of 0.2 mL / min to 15 mL / min under the conditions of a temperature of 130° C. to 150° C. and a vacuum degree of -80 kPa to -95 kPa, and performing nitrogen stripping on the mixed solution B after the water washing to remove epichlorohydrin and co-solvent to obtain an intermediate.

[0094] S3: mixing the intermediate, the catalyst, the polymerization inhibitor and the acrylic acid compound to carry out a ring-opening addition reaction to prepare protocatechuic acid-modified acrylate.

[0095] In some embodiments, the acrylic acid compound has a structure as shown in formula (III):

[0096] In the acrylic acid compound, R is selected from one of hydrogen and an alkyl group containing 1 to 8 carbon atoms. Preferably, R is selected from one of hydrogen and an alkyl group containing 1 to 6 carbon atoms. More preferably, R is selected from one of hydrogen and an alkyl group containing 1 to 4 carbon atoms. More preferably, R is selected from one of H and an alkyl group containing 1 to 3 carbon atoms, that is, R is selected from one of H, methyl (Me, -CH3), ethyl (Et, -CH2CH3), 1-propyl (n-Pr, n-propyl, -CH2CH2CH3), 2-propyl (i-Pr, i-propyl, -CH(CH3)2), 1-butyl (n-Bu, n-butyl, -CH2CH2CH2CH3), 2-methyl-1-propyl (i-Bu, i-butyl, -CH2CH(CH3)2), 2-butyl (s-Bu, s-butyl, -CH(CH3)CH2CH3) and 2-methyl-2-propyl (t-Bu, t-butyl, -C(CH3)3).

[0097] In some embodiments, R is selected from one of H, methyl (Me, -CH3), ethyl (Et, -CH2CH3), 1-propyl (n-Pr, n-propyl, -CH2CH2CH3) and 2-propyl (i-Pr, i-propyl, -CH(CH3)2), that is, the acrylic acid compound includes one of acrylic acid, methacrylic acid, 2-ethylacrylic acid, 2-propylacrylic acid and 2-isopropylacrylic acid.

[0098] In this application, under the action of a catalyst, the carboxylic acid groups on the acrylic acid compound and the epoxy functional groups on the intermediate undergo a ring-opening addition reaction, thereby producing a protocatechuic acid-modified acrylic acid ester containing a benzene ring structure and multiple acrylate functional groups. At the same time, the polymerization inhibitor (Polymerization Inhibitor) is an industrial auxiliary agent that inhibits, slows down, or terminates the polymerization reaction, which can effectively inhibit the self-polymerization reaction of the acrylic acid compound and increase the grafting rate of the acrylic acid compound on the intermediate. The general reaction formula of the ring-opening addition reaction in step S3 is as follows:

[0099] In some embodiments, the intermediate, catalyst, polymerization inhibitor, and acrylic acid compound are mixed to perform a ring-opening addition reaction, comprising the following steps:

[0100] Mixing the intermediate, catalyst and polymerization inhibitor at 70°C to 80°C to prepare mixed solution C;

[0101] Add acrylic acid compound to mixed solution C and react at 80°C to 120°C until the pH of the system is ≤5.

[0102] It can be understood that when the reaction is carried out to a pH value of the system ≤ 5, the reaction product can be directly used in the preparation of high-temperature resistant anaerobic adhesive without any impurity removal or purification treatment.

[0103] In some embodiments, the molar ratio of protocatechuic acid to the acrylic acid compound in the mixed solution A is (1.01-1.10):3, specifically 1.01:3, 1.02:3, 1.04:3, 1.06:3, 1.08:3 and 1.10:3, preferably (1.03-1.05):3.

[0104] In some embodiments, the catalyst includes one or more of tetraphenylphosphine bromide, triphenylphosphine, tetrabutylphosphine chloride, ethyltriphenylphosphine bromide, tetraethylammonium bromide, and tetrabutylammonium bromide, preferably tetraethylammonium bromide.

[0105] In some embodiments, the mass ratio of the catalyst to the acrylic acid compound is (0.001-0.01):1, preferably (0.002-0.005):1.

[0106] The amount of the catalyst used is 0.1% to 1% of the reactants in step 4, and the amount of the inhibitor used is 0.01% to 0.1% of the reactants.

[0107] In some embodiments, the polymerization inhibitor includes one or more of hydroquinone, p-benzoquinone, methylhydroquinone, p-hydroxyanisole and 2-tert-butylhydroquinone, preferably p-hydroxyanisole.

[0108] In some embodiments, the mass ratio of the polymerization inhibitor to the acrylic acid compound is (0.0001-0.001):1, preferably (0.0002-0.0005):1.

[0109] In some embodiments, the acrylic acid compound is added to the mixed solution C by dropwise addition, and the dropwise addition time is 1 h to 3 h, including but not limited to: 1 h, 1.5 h, 2 h, 2.5 h and 3 h, preferably 1 h to 2 h.

[0110] In some embodiments, the reaction time after adding the acrylic acid compound to the mixed solution C is 1 h to 6 h, including but not limited to: 1 h, 2 h, 3 h, 4 h, 5 h and 6 h, preferably 2 h to 4 h.

[0111] In some embodiments, after the mixed solution C and the acrylic acid compound react at 80°C to 120°C for 1 hour to 6 hours, the system pH is ≤ 5, including but not limited to: 5, 4.5, 4, 3.5, 3, 2.5, 2, 1.5, 1 and 0.5, preferably 4 to 5.

[0112] In some specific embodiments, step S3 includes the following steps: mixing the intermediate, the catalyst and the inhibitor at 70°C to 80°C to prepare a mixed solution C; slowly adding the acrylic acid compound to the mixed solution C within a dropwise addition time of 1h to 3h, and reacting at 80°C to 120°C for 1h to 6h until the pH of the system is ≤5.

[0113] In summary, this application first undergoes a substitution reaction between protocatechuic acid and epichlorohydrin under alkaline conditions, and then purifies it through neutralization, water washing, and nitrogen stripping to obtain an intermediate containing three epoxy functional groups. Under the action of a catalyst and an inhibitor, the epoxy functional groups on the intermediate undergo a ring-opening addition reaction with the carboxyl groups of an acrylic acid compound, thereby producing a protocatechuic acid-modified acrylate with excellent high-temperature resistance.

[0114] In some embodiments, the initiator includes one or more of dicumyl peroxide, tert-butyl perbenzoate, and cumene hydroperoxide, preferably dicumyl peroxide and / or cumene hydroperoxide.

[0115] In some embodiments, the accelerator includes one or more of saccharin, acetylphenylhydrazine, N,N-dimethyl-p-toluidine, 1,5-diphenylcarbazide, phthalimide, acrylic acid, methacrylic acid, maleic acid and ascorbic acid, preferably one or more of saccharin, 1,5-diphenylcarbazide and maleic acid.

[0116] In some embodiments, the stabilizer includes one or more of 1,4-hydroquinone, 4-methoxyphenol, benzoquinone, oxalic acid, and ethylenediaminetetraacetic acid (EDTA), preferably one or more of 1,4-hydroquinone, oxalic acid, and EDTA.

[0117] In some embodiments, the filler comprises one or more of fumed silica and bentonite, preferably fumed silica.

[0118] In some embodiments, the high temperature resistant anaerobic adhesive further comprises the following components in parts by weight: 0 to 20 parts of a tackifier and 0.1 to 0.5 parts of a pigment.

[0119] In some embodiments, the tackifier includes one or more of polymethacrylic acid, dioctyl phthalate, unsaturated fumaric resin and methyl nylonate, preferably polymethacrylic acid, more preferably polymethacrylic acid with a weight average molecular weight of 40,000 to 50,000.

[0120] In some embodiments, the pigment includes one or more of phthalocyanine blue, phthalocyanine green, reactive red, and lemon yellow, preferably reactive red.

[0121] In a second aspect of the present application, a method for using a high-temperature resistant anaerobic adhesive is provided, which is the bonding application of the high-temperature resistant anaerobic adhesive as described above in a planar structure.

[0122] In some embodiments, the method of using a high temperature resistant anaerobic adhesive comprises the following steps:

[0123] coating a surface promoter and the high-temperature resistant anaerobic adhesive as described above on a substrate to form a liquid film;

[0124] The components to be bonded are covered on the liquid film and cured under pressure.

[0125] The present application combines a surface promoter with a high-temperature resistant anaerobic adhesive, which can shorten the curing time of the high-temperature resistant anaerobic adhesive and facilitate rapid positioning and automated assembly in the bonding of planar structures.

[0126] In some embodiments, the surface promoter includes one or more of copper isooctanoate, ferrocene, and copper acetate.

[0127] The above-mentioned surface promoters are all metal organic compounds. The presence of metal ions can cause the peroxide initiator in the anaerobic adhesive system to undergo free radical decomposition reaction, thereby accelerating the curing process.

[0128] Optionally, the surface promoter is provided in the form of a solution, which includes one or more of an ethanol solution of copper octoate, a dichloromethane solution containing ferrocene and trichloroacetic acid, and a methanol solution containing copper acetate and ascorbic acid, preferably an ethanol solution of copper octoate.

[0129] Optionally, in the ethanol solution of copper 2-octoate, the mass proportion of copper 2-octoate is 0.5% to 2%, specifically 0.5%, 0.8%, 1%, 1.2%, 1.5%, 1.8% and 2%, preferably 1%.

[0130] Optionally, the thickness of the liquid film is 0.05 μm to 0.5 μm, specifically 0.05 μm, 0.1 μm, 0.2 μm, 0.3 μm, 0.4 μm and 0.5 μm, preferably 0.1 μm to 0.2 μm.

[0131] Optionally, the pressure under the pressurization condition is 0.03 MPa to 0.1 MPa, including but not limited to 0.03 MPa, 0.04 MPa, 0.05 MPa, 0.06 MPa, 0.07 MPa, 0.08 MPa, 0.09 MPa, and 0.1 MPa, preferably 0.05 MPa to 0.08 MPa. The pressurization can isolate the liquid film between the component to be bonded and the substrate from oxygen, prompting the liquid film to quickly solidify and form a high-strength adhesive layer.

[0132] Optionally, the curing temperature is 20°C to 40°C, specifically 20°C, 25°C, 30°C, 35°C and 40°C, preferably 20°C to 30°C.

[0133] Optionally, the curing treatment time is 24h to 168h, specifically 24h, 36h, 48h, 60h, 72h, 84h, 96h, 108h, 120h, 132h, 144h, 156h and 168h, preferably 48h to 72h.

[0134] The present application is further described in detail below with reference to specific embodiments.

[0135] In the following specific examples and comparative examples, the raw materials used, unless otherwise specified, are all commercially available products; the instruments used, unless otherwise specified, are all commercially available products; and the processes used, unless otherwise specified, are all routinely selected by those skilled in the art.

[0136] Example 1

[0137] (1) Preparation of protocatechuic acid modified acrylate:

[0138] S1: Protocatechuic acid, epichlorohydrin, and methyl isobutyl ketone were uniformly mixed to obtain a mixed solution A. The mixed solution A was heated to 45°C and, under normal pressure, a NaOH solution was added dropwise in six portions. The mixture was reacted for 6 hours to obtain a mixed solution B. The mass ratio of protocatechuic acid, epichlorohydrin, and methyl isobutyl ketone was 100:220:50, the mass fraction of the NaOH solution was 45%, and the molar ratio of protocatechuic acid to NaOH was 1:3.02.

[0139] S2: The mixed solution B is neutralized with sodium dihydrogen phosphate to neutralize the alkali in the mixed solution B, and the resulting salt compounds are removed by washing with water; nitrogen is introduced at a flow rate of 1 mL / min under conditions of a temperature of 130° C. and a vacuum degree of -85 kPa, and the mixed solution B after the water washing is subjected to nitrogen stripping treatment to remove epichlorohydrin and co-solvent to obtain an intermediate.

[0140] S3: Lower the temperature to 80°C, add 2.1g of tetraethylammonium bromide and 0.35g of p-hydroxyanisole to the intermediate and mix well; slowly add 172g of methacrylic acid dropwise over a period of 1.5h at a reaction temperature of 100°C for 4h until the pH of the system is less than 5, which indicates the end of the reaction. Discharge the product to obtain protocatechuic acid-modified acrylate, which is recorded as PCA acrylate.

[0141] (2) Preparation of high temperature resistant anaerobic adhesive:

[0142] Please refer to Table 1. Weigh 45 parts of PCA acrylate, 15 parts of isobornyl methacrylate, 8 parts of hydroxyethyl methacrylate, 2.5 parts of initiator, 6.7 parts of accelerator, 0.082 parts of stabilizer, 15.6 parts of tackifier, 5.1 parts of filler and 0.2 parts of pigment, mix well to obtain high-temperature resistant anaerobic adhesive.

[0143] Among them, the initiator is dicumyl peroxide; the accelerator is composed of 0.9 parts of saccharin, 0.7 parts of 1,5-diphenylcarbazide and 5.1 parts of maleic acid; the stabilizer is composed of 0.07 parts of 1,4-hydroquinone, 0.01 parts of oxalic acid and 0.002 parts of EDTA; the thickener is polymethacrylic acid with a weight-average molecular weight of 40,000 to 50,000; the filler is fumed silica R202; and the pigment is reactive red.

[0144] Example 2

[0145] Referring to Table 1, 55 parts of PCA acrylate prepared in Example 1, 10 parts of isobornyl methacrylate, 4 parts of hydroxyethyl methacrylate, 3 parts of initiator, 1 part of accelerator, 0.082 parts of stabilizer, 10 parts of tackifier, 3 parts of filler and 0.2 parts of pigment were weighed and mixed uniformly to obtain a high-temperature resistant anaerobic adhesive.

[0146] Among them, the initiator is composed of 1.5 parts of dicumyl peroxide and 1.5 parts of isopropylbenzene hydroperoxide; the accelerator is composed of 0.5 parts of saccharin and 0.5 parts of 1,5-diphenylcarbazide; the stabilizer is composed of 0.07 parts of 1,4-hydroquinone, 0.01 parts of oxalic acid and 0.002 parts of EDTA; the thickener is polymethacrylic acid with a weight-average molecular weight of 40,000 to 50,000; the filler is fumed silica R202; and the pigment is reactive red.

[0147] Example 3

[0148] Referring to Table 1, 65 parts of PCA acrylate prepared in Example 1, 10 parts of isobornyl methacrylate, 5 parts of hydroxyethyl methacrylate, 3 parts of initiator, 0.6 parts of accelerator, 0.082 parts of stabilizer, 10 parts of tackifier, 3 parts of filler and 0.2 parts of pigment were weighed and mixed uniformly to obtain a high-temperature resistant anaerobic adhesive.

[0149] Among them, the initiator is dicumyl peroxide; the accelerator is composed of 0.5 parts of saccharin and 0.1 parts of 1,5-diphenylcarbazide; the stabilizer is composed of 0.07 parts of 1,4-hydroquinone, 0.01 parts of oxalic acid and 0.002 parts of EDTA; the thickener is polymethacrylic acid with a weight-average molecular weight of 40,000 to 50,000; the filler is fumed silica R202; and the pigment is reactive red.

[0150] Example 4

[0151] The difference between this embodiment and embodiment 1 is that no tackifier is added.

[0152] Comparative Example 1

[0153] Referring to Table 1, 35 parts of isobornyl methacrylate, 30 parts of hydroxyethyl methacrylate, 2.5 parts of initiator, 0.6 parts of accelerator, 0.082 parts of stabilizer, 3 parts of filler and 0.2 parts of pigment were weighed and mixed uniformly to obtain a high-temperature resistant anaerobic adhesive.

[0154] Among them, the initiator is dicumyl peroxide; the accelerator is composed of 0.5 parts of saccharin and 0.1 parts of 1,5-diphenylcarbazide; the stabilizer is composed of 0.07 parts of 1,4-hydroquinone, 0.01 parts of oxalic acid and 0.002 parts of EDTA; the filler is fumed silica R202; and the pigment is reactive red.

[0155] Comparative Example 2

[0156] Referring to Table 1, 40 parts of isobornyl methacrylate, 30 parts of hydroxyethyl methacrylate, 3 parts of initiator, 0.6 parts of accelerator, 0.082 parts of stabilizer, 10 parts of tackifier, 3 parts of filler and 0.2 parts of pigment were weighed and mixed uniformly to obtain a high-temperature resistant anaerobic adhesive.

[0157] Among them, the initiator is dicumyl peroxide; the accelerator is composed of 0.5 parts of saccharin and 0.1 parts of 1,5-diphenylcarbazide; the stabilizer is composed of 0.07 parts of 1,4-hydroquinone, 0.01 parts of oxalic acid and 0.002 parts of EDTA; the filler is fumed silica R202; and the pigment is reactive red.

[0158] Test Case

[0159] A 1% by mass copper octoate ethanol solution was applied to the clean steel surface, followed by application of the high-temperature resistant anaerobic adhesive prepared in the above examples and comparative examples to form a liquid film. The components to be bonded were covered on the liquid film, isolated from oxygen at a pressure of 0.05 MPa, and cured at room temperature for 24 hours.

[0160] After curing, the high-temperature anaerobic adhesive was tested for positioning time, room temperature bonding strength, 150°C bonding strength, and room temperature bonding strength after one week at 85°C and 85% relative humidity (RH) using the "HG / T 3737-2018 Anaerobic Adhesives" standard. The results are shown in Table 2.

[0161] As shown in Table 2, the high temperature resistant anaerobic adhesives of Examples 1 to 4 have a short positioning time, excellent bonding strength, and excellent high temperature resistance and heat and humidity aging resistance after curing.

[0162] Table 1. Formulas of high temperature resistant anaerobic adhesives of Examples 1 to 4 and Comparative Examples 1 to 2

[0163] Table 2. Performance comparison of high temperature resistant anaerobic adhesives of Examples 1 to 4 and Comparative Examples 1 to 2

[0164] The technical features of the above-mentioned embodiments can be combined arbitrarily. In order to make the description concise, not all possible combinations of the technical features in the above-mentioned 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.

[0165] The above-described embodiments merely represent several implementation methods of the present application. While the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the patented invention. It should be noted that a person skilled in the art could make various modifications and improvements without departing from the spirit of the present application, all of which fall within the scope of protection of the present application. Therefore, the scope of protection of the present application shall be determined by the appended claims, and the specification may be used to interpret the content of the claims.

Claims

1. A high temperature resistant anaerobic adhesive, characterized in that: The composition comprises the following components in parts by weight: Wherein, the protocatechuic acid modified acrylate has a structure as shown in the general formula (I): Each occurrence of R is independently selected from one of H and an alkyl group containing 1 to 8 carbon atoms.

2. The high temperature resistant anaerobic adhesive according to claim 1, characterized in that: Each occurrence of R is independently selected from one of H and an alkyl group containing 1 to 6 carbon atoms.

3. The high temperature resistant anaerobic adhesive according to claim 2, characterized in that: The preparation method of the protocatechuic acid modified acrylate comprises the following steps: A mixed solution A containing protocatechuic acid, epichlorohydrin and a cosolvent is subjected to a substitution reaction under alkaline conditions to prepare a mixed solution B containing an intermediate; Purifying the mixed solution B to prepare an intermediate; Mixing the intermediate, catalyst, polymerization inhibitor and acrylic acid compound having a structure represented by general formula (III) to carry out a ring-opening addition reaction to prepare the protocatechuic acid-modified acrylate; 4. The high temperature resistant anaerobic adhesive according to claim 3, characterized in that: R is selected from one of H, methyl, ethyl, 1-propyl and 2-propyl.

5. The high temperature resistant anaerobic adhesive according to claim 4, characterized in that: A mixed solution A containing protocatechuic acid, epichlorohydrin and a co-solvent is subjected to a substitution reaction under alkaline conditions, comprising the following steps: Under the conditions of temperature of 30° C. to 65° C. and vacuum degree of -65 kPa to 0 kPa, alkali solution is added to the mixed solution A and reacted for 3 h to 6 h.

6. The high temperature resistant anaerobic adhesive according to claim 5, characterized in that: One or more of the following conditions are met: (1) In the mixed solution A, the mass ratio of the protocatechuic acid, the epichlorohydrin and the co-solvent is 1:(2-3):(0.5-1); (2) the cosolvent comprises one or more of water, butanol, propylene glycol methyl ether, toluene, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; (3) the alkali in the alkali solution includes one or more of NaOH, KOH, Na2CO3, NaHCO3, K2CO3 and KHCO3; (4) The mass fraction of the alkali in the alkali solution is 10% to 50%; (5) The molar ratio of the protocatechuic acid to the alkali in the alkali solution is 1:(3.01-3.20).

7. The high temperature resistant anaerobic adhesive according to claim 4, characterized in that: The intermediate, catalyst, polymerization inhibitor and acrylic acid compound are mixed to carry out a ring-opening addition reaction, comprising the following steps: Mixing the intermediate, the catalyst and the polymerization inhibitor at 70° C. to 80° C. to prepare a mixed solution C; The acrylic acid compound is added to the mixed solution C, and the mixture is reacted at 80° C. to 120° C. until the pH value of the system is ≤5.

8. The high temperature resistant anaerobic adhesive according to claim 7, characterized in that: One or more of the following conditions are met: (1) The molar ratio of protocatechuic acid to the acrylic acid compound in the mixed solution A is (1.01-1.10):3; (2) The catalyst comprises one or more of tetraphenylphosphine bromide, triphenylphosphine, tetrabutylphosphine chloride, ethyltriphenylphosphine bromide, tetraethylammonium bromide and tetrabutylammonium bromide; (3) The molar ratio of the catalyst to the acrylic acid compound is (0.001-0.01):1; (4) the polymerization inhibitor comprises one or more of hydroquinone, p-benzoquinone, methylhydroquinone, p-hydroxyanisole and 2-tert-butylhydroquinone; (5) The molar ratio of the polymerization inhibitor to the acrylic acid compound is (0.0001-0.001):

1.

9. The high temperature resistant anaerobic adhesive according to any one of claims 1 to 8, characterized in that: One or more of the following conditions are met: (1) The initiator comprises one or more of dicumyl peroxide, tert-butyl perbenzoate and cumene hydroperoxide; (2) The accelerator includes one or more of saccharin, acetylphenylhydrazine, N,N-dimethyl-p-toluidine, 1,5-diphenylcarbazide, phthalimide, acrylic acid, methacrylic acid, maleic acid and ascorbic acid; (3) The stabilizer includes one or more of 1,4-hydroquinone, 4-methoxyphenol, benzoquinone, oxalic acid and ethylenediaminetetraacetic acid; (4) The filler includes one or more of fumed silica and bentonite.

10. The high temperature resistant anaerobic adhesive according to any one of claims 1 to 8, characterized in that: The high temperature resistant anaerobic adhesive further comprises the following components in parts by weight: 0 to 20 parts of a tackifier and 0.1 to 0.5 parts of a pigment.

11. The high temperature resistant anaerobic adhesive according to claim 10, characterized in that: One or more of the following conditions are met: (1) The tackifier comprises one or more of polymethacrylic acid, dioctyl phthalate, unsaturated fumaric resin and methyl nylonate; (2) The pigment includes one or more of phthalocyanine blue, phthalocyanine green, reactive red and lemon yellow.

12. A method for using a high temperature resistant anaerobic adhesive, characterized in that: The following steps are involved: Coating a surface promoter and the high-temperature resistant anaerobic adhesive according to any one of claims 1 to 11 on a substrate to form a liquid film; The components to be bonded are covered on the liquid film and cured under pressure.

13. The method for using the high temperature resistant anaerobic adhesive according to claim 12, wherein: The surface promoter includes one or more of copper isooctanoate, ferrocene and copper acetate.

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