Modified aminosilane coupling agent, two-component silicone sealant and preparation method thereof

Abstract

The application relates to a modified amino silane coupling agent, a two-component silicone sealant and a preparation method thereof; the structural formula of the modified amino silane coupling agent is shown as formula (I); the two-component silicone sealant comprises an A component and a B component; the A component comprises the following raw materials in parts by weight: alpha, omega-dihydroxypolydimethylsiloxane 100 parts; fillers 60-150 parts; dimethyl silicone oil 5-25 parts; the B component comprises the following raw materials in parts by weight: dimethyl silicone oil 100 parts; carbon black 50-150 parts; a crosslinking agent 15-60 parts; a coupling agent 16-75 parts; a catalyst 0.1-1.5 parts; and the coupling agent contains the modified amino silane coupling agent. Through the addition of the modified amino silane coupling agent in an appropriate amount, the application can effectively solve the problems of performance attenuation of a traditional two-component silicone sealant at high temperatures and poor water immersion performance, and improve the heat resistance and water immersion adhesion of the two-component silicone sealant.

Description

Technical Field

[0001] The invention belongs to the technical field of sealants, and in particular relates to a modified aminosilane coupling agent, a two-component silicone sealant and a preparation method thereof. Background Art

[0002] Condensation-type, two-component, room-temperature vulcanizing (RTV-2) silicone sealants rapidly crosslink at room temperature to form an elastomer with a certain hardness. Currently, they are a staple sealing material, widely used in the construction and industrial sectors. Silane coupling agents are a crucial component of sealants, serving as a bridge between the sealant and the substrate. Their application in composite materials has been widely recognized, significantly influencing the substrate's bond strength, water resistance, and weather resistance. Even a minimal amount at the interface can significantly impact the composite's performance.

[0003] Currently, the use of common two-component silicone sealants is relatively limited under specific conditions. For example, under long-term high temperature and water immersion conditions, their mechanical properties and tensile adhesion will be adversely affected. Patent CN202210877362.3 uses formula optimization to produce a two-component high-temperature resistant and high-shear strength organic silicone adhesive, but its formula contains a large amount of organic silicone polysilazane, the formula cost is high, and it is not conducive to industrialization. Patent CN202410084455.X mixes organic siloxane / promoter dibutyltin dilaurate / crosslinking agent ethyl orthosilicate, allowing the three to react with each other to form a new mixed adhesive, and then adds bamboo fiber to the mixed adhesive in a specified proportion, thereby improving the high-temperature resistance of the two-component. Patent CN202310785475.5 improves the sealant's resistance to water immersion and water UV aging by using specially treated calcium carbonate and a conventional coupling agent obtained by reaction under specific conditions. Its synthesis process is relatively cumbersome and only improves a single property, which limits its use under various special conditions. Summary of the Invention

[0004] Based on this, the object of the present invention is to provide a modified aminosilane coupling agent and a two-component silicone sealant, wherein the heat resistance and water immersion adhesion of the two-component silicone sealant can be effectively improved by adding the modified aminosilane coupling agent.

[0005] The first aspect of the present invention is to provide a compound, the structural formula of the compound is shown in the following formula (I):

[0006]

[0007] The second aspect of the present invention is to provide a method for preparing the above-mentioned compound, comprising the following steps: reacting n-butyl benzoate and 3-(diethylenetriamino)propyltrimethoxysilane to obtain.

[0008] In some embodiments, the molar ratio of 3-(diethylenetriamino)propyltrimethoxysilane to n-butyl benzoate is (0.8-1.2):1.

[0009] In some embodiments, the reaction temperature is 60° C. to 100° C., and the reaction time is 4 h to 12 h.

[0010] In some embodiments, the solvent of the reaction is an alcohol solvent.

[0011] The third aspect of the present invention is to provide the use of the compound as described above as a coupling agent in the preparation of a sealant.

[0012] A fourth aspect of the present invention is to provide a two-component silicone sealant comprising component A and component B:

[0013] The A component includes the following raw materials in parts by weight:

[0014] 100 parts of α,ω-dihydroxypolydimethylsiloxane;

[0015] 60 to 150 parts of filler;

[0016] 5 to 25 parts of dimethyl silicone oil;

[0017] The B component includes the following raw materials in parts by weight:

[0018]

[0019]

[0020] The coupling agent comprises the compound described above.

[0021] In some embodiments, the two-component silicone sealant includes component A and component B:

[0022] The A component includes the following raw materials in parts by weight:

[0023] 100 parts of α,ω-dihydroxypolydimethylsiloxane;

[0024] 90 to 110 parts of filler;

[0025] 8 to 12 parts of dimethyl silicone oil;

[0026] The B component includes the following raw materials in parts by weight:

[0027]

[0028] In some embodiments, the volume ratio of component A to component B is (8-12):1, preferably (9-11):1.

[0029] In some embodiments, the coupling agent comprises the compound and a coupling agent a;

[0030] The coupling agent a is selected from one or more of γ-glycidoxypropyltrimeth(eth)oxy silane, γ-glycidoxypropyltrimeth(eth)oxy silane, epoxycyclohexylmethyl dimeth(eth)oxy silane, chloropropyltrimeth(eth)oxy silane, γ-(2,3-epoxypropoxy)propyltrimethoxysiloxane, γ-aminopropyltrimeth(eth)oxy silane, γ-aminopropylmethyl dimeth(eth)oxy silane, N-(2-aminoethyl)-3-aminopropyltrimeth(eth)oxy silane, N-(2-aminoethyl)-3-aminopropylmethyl dimeth(eth)oxy silane, phenylaminomethyltrimeth(eth)oxy silane, γ-isocyanatopropyltrimethoxysilane, epoxylpropyltrimethoxysilane, 3-(diethylenetriaminyl)propyltrimethoxysilane.

[0031] Preferably, the weight ratio of the compound and the coupling agent a is (1-15):(15-60).

[0032] More preferably, the weight ratio of the compound and the coupling agent a is (2-10):(45-55).

[0033] In some embodiments, the filler is nano-active calcium carbonate; preferably, the nano-active calcium carbonate has a particle size of 20-200 nm, more preferably 40-150 nm.

[0034] In some embodiments, the α,ω-dihydroxypolydimethylsiloxane has a viscosity of 5000-80000 mPa·s, preferably 10000-40000 mPa·s at 25±0.5℃.

[0035] In some embodiments, the dimethyl silicone oil in the A component has a viscosity of 300-1000 mPa·s, preferably 300-600 mPa·s at 25±0.5℃.

[0036] In some embodiments, the cross-linking agent is selected from one or more of tetraethyl orthosilicate, tetrapropyl orthosilicate, polyethyl orthosilicate, methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, polymethyltriethoxysilane oligomer, phenyltrimethoxysilane, phenyltriethoxysilane, methylphenyldimethoxysilane, methylphenyldiethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane.

[0037] In some embodiments, the viscosity of the dimethyl silicone oil in component B at 25±0.5° C. is 5000 mPa·s to 15000 mPa·s, preferably 8000 mPa·s to 12000 mPa·s.

[0038] In some embodiments, the catalyst is selected from one or more of dibutyltin dilaurate, dibutyltin diacetate, dibutyltin dioctoate or tin octoate, isopropyl titanate, and n-butyl titanate.

[0039] A fifth aspect of the present invention is to provide a method for preparing the two-component silicone sealant as described above, comprising the following steps:

[0040] (1) adding the filler, α,ω-dihydroxy polydimethylsiloxane, and dimethyl silicone oil into a planetary mixer and mixing them uniformly at 60° C. to 120° C. to obtain component A;

[0041] (2) Add the dimethyl silicone oil, carbon black, crosslinking agent, coupling agent, and catalyst into a planetary mixer, stir and mix them evenly to obtain component B.

[0042] In some embodiments, the mixing time in step (1) is 10 min to 200 min.

[0043] In some embodiments, the mixing time in step (2) is 10 min to 100 min.

[0044] When in use, take the component A and the component B, mix them evenly, and then obtain the two-component silicone sealant.

[0045] The present invention utilizes n-butyl benzoate to structurally modify 3-(diethylenetriamino)propyltrimethoxysilane to obtain a modified aminosilane coupling agent, which is then used to prepare a two-component silicone sealant. Adding an appropriate amount of the modified aminosilane coupling agent effectively addresses the performance degradation and poor water immersion resistance of conventional two-component silicone sealants at high temperatures, improving the heat resistance and water-immersion adhesion of the two-component silicone sealant, and increasing the 80°C tensile bond strength, 80°C tensile retention, and adhesion after water-UV irradiation. The two-component silicone sealant of the present invention is easy to construct and can meet the requirements of various applications, such as special construction, automobiles, and electronic appliances.

[0046] The modified aminosilane coupling agent of the invention has simple synthesis process and high yield. DETAILED DESCRIPTION

[0047] To facilitate understanding of the present invention, the present invention will be described more fully below. The present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the present disclosure more thorough and comprehensive.

[0048] In the following examples, the experimental methods without specific conditions are generally carried out under conventional conditions or conditions recommended by the manufacturers. The various commonly used chemical reagents used in the examples are all commercially available products.

[0049] Unless otherwise defined, all technical and scientific terms used herein have the same meanings as commonly understood by those skilled in the art to which this invention pertains. The terms used in this specification are for the purpose of describing specific embodiments only and are not intended to limit the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0050] Furthermore, as used herein, the term "or" is inclusive and equivalent to the term "and / or," unless the context clearly dictates otherwise. The term "based on" is not exclusive and allows for being based on other factors not described, unless the context clearly dictates otherwise. Furthermore, throughout this specification, the meanings of "a," "an," and "the" include plural referents. The meaning of "in" includes "in" and "on."

[0051] In some embodiments of the present invention, a compound is provided, the structural formula of the compound being shown in the following formula (I):

[0052]

[0053] The compound is generated by the reaction of the ester group of n-butyl benzoate with the primary amine group of 3-(diethylenetriamino)propyltrimethoxysilane. The synthesis route is as follows:

[0054]

[0055] In some embodiments of the present invention, a method for preparing the compound as described above is provided, comprising the following steps: reacting n-butyl benzoate and 3-(diethylenetriamino)propyltrimethoxysilane to obtain the compound.

[0056] In some preferred embodiments, the preparation method of the compound comprises the following steps: adding 3-(diethylenetriamino)propyltrimethoxysilane to a solvent, mixing thoroughly and evenly, adding n-butyl benzoate, heating to 60°C to 100°C and reflux reaction for 4h to 12h, then distilling under reduced pressure to remove small molecules, and separating to obtain the compound.

[0057] In some preferred embodiments, the molar ratio of 3-(diethylenetriamino)propyltrimethoxysilane to n-butyl benzoate is (0.8-1.2):1, preferably (0.9-1.1):1.

[0058] In some preferred embodiments, the temperature is raised to 70° C. to 90° C. and refluxed for 4 h to 12 h.

[0059] In some preferred embodiments, the separation method is column chromatography.

[0060] In some preferred embodiments, the solvent is an alcohol solvent, for example, including but not limited to n-butanol, propanol, n-propanol, and isopropanol.

[0061] The present invention is further described in detail below with reference to specific embodiments.

[0062] In the following examples, the compound is named as modified aminosilane coupling agent.

[0063] The modified aminosilane coupling agent used in the following examples was prepared by the following method: 1 mol of 3-(diethylenetriamino)propyltrimethoxysilane and 0.5 mol of n-butanol were added to a four-necked flask equipped with a stirrer and thermometer and filled with nitrogen. After thorough mixing, 1 mol of n-butyl benzoate was added. The temperature was raised to 80°C and refluxed for 8 hours. Small molecules were then removed by distillation under reduced pressure, and the desired product was obtained by column chromatography. The yield was 92.32%.

[0064] Through infrared detection, at 3370cm -1 No primary amine (-NH2) group stretching vibration absorption peak was found nearby. -1 The oxygen-containing amino vibration absorption peak of -C=ONH- appears near 2837cm -1 and 2938cm -1 The stretching vibration absorption peak of CH appeared near 1457 cm -1 and 1465cm -1 The stretching vibration absorption peak of CN appears near 1077cm -1 and 1085cm -1 The stretching vibration absorption peak of Si-OC appears nearby, indicating that the modified aminosilane coupling agent shown in the following formula (I) has been successfully prepared:

[0065]

[0066] Example 1

[0067] This embodiment provides a two-component silicone sealant, including component A and component B:

[0068] Component A (parts by weight):

[0069] Take 100 parts of α, ω-dihydroxy polydimethylsiloxane with a viscosity of 10000 mPa s, then add 10 parts of 400 mPa s dimethyl silicone oil into the kneader for stirring and dispersion, after 5 minutes, add 100 parts of 60 nm particle size nano active calcium carbonate into it during stirring to make the glue completely cover the powder to form a self-leveling base, control the reaction temperature to be 90°C, mix for 1 h to obtain component A, and grind for standby use.

[0070] Component B (parts by weight): According to the mixing ratio of component B, 100 parts of 10000 mPa s dimethyl silicone oil and 100 parts of carbon black are added into a planetary mixer for stirring under vacuum, and the temperature is kept stable at 100°C for 30 min to obtain B base, then 30 parts of propyl trimethoxysilane, 20 parts of methyl trimethoxysilane, 30 parts of γ-aminopropyl trimeth(eth)oxysilane, 20 parts of γ-glycidyl ether propyl trimeth(eth)oxysilane, 2 parts of modified amino silane coupling agent, and 1 part of dibutyltin dilaurate are added, stirred for 20 min under nitrogen protection, sealed and stored.

[0071] Then, component A and component B are mixed uniformly in a planetary stirrer under vacuum according to the mixing volume ratio of 10:1 to obtain a two-component silicone sealant, and then an H-shaped test piece is prepared for standby to test the tensile bonding of the sample.

[0072] Example 2

[0073] The embodiment provides a two-component silicone sealant, which comprises component A and component B:

[0074] Component A (parts by weight):

[0075] Take 100 parts of α, ω-dihydroxy polydimethylsiloxane with a viscosity of 10000 mPa s, then add 10 parts of 400 mPa s dimethyl silicone oil into the kneader for stirring and dispersion, after 5 minutes, add 100 parts of 60 nm particle size nano active calcium carbonate into it during stirring to make the glue completely cover the powder to form a self-leveling base, control the reaction temperature to be 90°C, mix for 1 h to obtain component A, and grind for standby use.

[0076] Component B (parts by weight): According to the ratio of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black were added to a planetary machine and stirred under vacuum. After the temperature was stabilized at 100°C and maintained for 30 minutes, base material B was obtained. Then, 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethyl(ethyl)oxysilane, 20 parts of γ-glycidyloxypropyltrimethyl(ethyl)oxysilane, 5 parts of modified aminosilane coupling agent were added with 1 part of dibutyltin dilaurate, stirred under nitrogen protection for 20 minutes, and sealed for storage.

[0077] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum at a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-shaped test piece for testing the tensile adhesion of the sample.

[0078] Example 3

[0079] This embodiment provides a two-component silicone sealant, including component A and component B:

[0080] Component A (parts by weight):

[0081] Take 100 parts of α, ω-dihydroxy polydimethylsiloxane with a viscosity of 10000 mPa·s, then add 10 parts of 400 mPa·s dimethyl silicone oil into a kneader and stir and disperse. After 5 minutes, add 100 parts of 60 nm particle size nano-activated calcium carbonate during stirring so that the glue completely covers the powder to form a self-leveling base material. Control the reaction temperature to 90°C and mix for 1 hour to obtain component A, which is ground and set aside.

[0082] Component B (parts by weight): According to the ratio of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black are added to a planetary machine and stirred in vacuum. After the temperature is stabilized at 100°C and maintained for 30 minutes, base material B is obtained. Then, 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethyl(ethyl)oxysilane, 20 parts of γ-glycidyloxypropyltrimethyl(ethyl)oxysilane, 10 parts of modified aminosilane coupling agent are added with 1 part of dibutyltin dilaurate, stirred under nitrogen protection for 20 minutes, and sealed for storage.

[0083] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum at a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-shaped test piece for testing the tensile adhesion of the sample.

[0084] Example 4

[0085] This embodiment provides a two-component silicone sealant, including component A and component B:

[0086] Component A (parts by weight):

[0087] Take 100 parts of α, ω-dihydroxy polydimethylsiloxane with a viscosity of 20,000 mPa·s, then add 10 parts of 400 mPa·s dimethyl silicone oil into a kneader and stir and disperse. After 5 minutes, add 100 parts of 40 nm particle size nano-activated calcium carbonate during stirring so that the glue completely covers the powder to form a self-leveling base material. Control the reaction temperature to 90°C and mix for 1 hour to obtain component A, which is ground and set aside.

[0088] Component B (parts by weight): According to the ratio of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black were added to a planetary machine and stirred under vacuum. After the temperature was stabilized at 100°C and maintained for 30 minutes, base material B was obtained. Then, 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethyl(ethyl)oxysilane, 20 parts of γ-glycidyloxypropyltrimethyl(ethyl)oxysilane, 5 parts of modified aminosilane coupling agent were added with 1 part of dibutyltin dilaurate, stirred under nitrogen protection for 20 minutes, and sealed for storage.

[0089] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum at a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-shaped test piece for testing the tensile adhesion of the sample.

[0090] Example 5

[0091] This embodiment provides a two-component silicone sealant, including component A and component B:

[0092] Component A (parts by weight):

[0093] Take 100 parts of α, ω-dihydroxy polydimethylsiloxane with a viscosity of 20,000 mPa·s, then add 10 parts of 400 mPa·s dimethyl silicone oil into a kneader and stir and disperse. After 5 minutes, add 100 parts of 40 nm particle size nano-activated calcium carbonate during stirring so that the glue completely covers the powder to form a self-leveling base material. Control the reaction temperature to 90°C and mix for 1 hour to obtain component A, which is ground and set aside.

[0094] Component B (parts by weight): According to the ratio of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black are added to a planetary machine and stirred in vacuum. After the temperature is stabilized at 100°C and maintained for 30 minutes, base material B is obtained. Then, 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethyl(ethyl)oxysilane, 20 parts of γ-glycidyloxypropyltrimethyl(ethyl)oxysilane, 5 parts of modified aminosilane coupling agent are added with 1 part of dibutyltin dioctoate, stirred under nitrogen protection for 20 minutes, and sealed for storage.

[0095] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum at a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-shaped test piece for testing the tensile adhesion of the sample.

[0096] Comparative Example 1

[0097] This comparative example provides a two-component silicone sealant, including component A and component B. Except for the B component, Except for the modified aminosilane coupling agent, the others are the same as those in Example 2. , as follows:

[0098] Component A (parts by weight):

[0099] Take 100 parts of α, ω-dihydroxy polydimethylsiloxane with a viscosity of 10000 mPa·s, then add 10 parts of 400 mPa·s dimethyl silicone oil into a kneader and stir and disperse. After 5 minutes, add 100 parts of 60 nm particle size nano-activated calcium carbonate during stirring so that the glue completely covers the powder to form a self-leveling base material. Control the reaction temperature to 90°C and mix for 1 hour to obtain component A, which is ground and set aside.

[0100] Component B (parts by weight): According to the ratio of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black are added to a planetary machine and stirred in vacuum. After the temperature is stabilized at 100°C and maintained for 30 minutes, base material B is obtained. Then, 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethyl(ethyl)oxysilane, 20 parts of γ-glycidyloxypropyltrimethyl(ethyl)oxysilane, and 1 part of dibutyltin dilaurate are added and stirred under nitrogen protection for 20 minutes to obtain the base material B. The base material is sealed and stored.

[0101] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum at a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-shaped test piece for testing the tensile adhesion of the sample.

[0102] Comparative Example 2

[0103] This comparative example provides a two-component silicone sealant, including component A and component B. In addition to the B component Except that the modified aminosilane coupling agent is replaced by γ-aminopropyltrimethyl(ethyl)oxysilane, the other steps are the same as those in Example 2. :

[0104] Component A (parts by weight):

[0105] Take 100 parts of α, ω-dihydroxy polydimethylsiloxane with a viscosity of 10000 mPa·s, then add 10 parts of 400 mPa·s dimethyl silicone oil into a kneader and stir and disperse. After 5 minutes, add 100 parts of 60 nm particle size nano-activated calcium carbonate during stirring so that the glue completely covers the powder to form a self-leveling base material. Control the reaction temperature to 90°C and mix for 1 hour to obtain component A, which is ground and set aside.

[0106] Component B (parts by weight): According to the ratio of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black are added to a planetary machine and stirred in vacuum. After the temperature is stabilized at 100°C and maintained for 30 minutes, base material B is obtained. Then, 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 35 parts of γ-aminopropyltrimethyl(ethyl)oxysilane, 20 parts of γ-glycidyloxypropyltrimethyl(ethyl)oxysilane and 1 part of dibutyltin dilaurate are added and stirred under nitrogen protection for 20 minutes to obtain the base material B. The base material is sealed and stored.

[0107] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum at a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-shaped test piece for testing the tensile adhesion of the sample.

[0108] The raw materials for the above examples and comparative examples are shown in Table 1.

[0109] Table 1 List of raw material ingredients for Examples and Comparative Examples

[0110]

[0111]

[0112] The following properties of the two-component silicone sealants prepared in the above examples and comparative examples were tested:

[0113] 23℃ tensile adhesion: tested according to 5.9 of JG / T 475-2015.

[0114] 80℃ tensile adhesion: Test according to 5.9.2 of JG / T 475-2015 and calculate the retention rate according to 5.1.3.

[0115] Tensile adhesion test after water-UV irradiation: Test according to 5.9.4 of JG / T 475-2015 and calculate the bond failure area according to 5.1.3.

[0116] Fill in the results in Table 2.

[0117] Table 2 Performance test results of examples and comparative examples

[0118]

[0119]

[0120] In the table, *CF represents cohesive failure, and AF represents adhesive failure.

[0121] By comparing these experimental results, it can be seen that the strength, 80°C tensile bonding strength, 80°C tensile retention rate, and adhesion after water-ultraviolet irradiation of the two-component silicone sealant to which the modified aminosilane coupling agent is added are significantly improved.

[0122] By comparing Examples 1 to 3, it can be seen that the amount of modified aminosilane coupling agent added will affect the improvement effect of the heat resistance and water immersion adhesion of the two-component silicone sealant. In Example 1, the amount of modified aminosilane coupling agent added is 2 parts. The 80°C tensile bonding strength and 80°C tensile retention of the obtained two-component silicone sealant are lower than those of Example 2 (5 parts) and Example 3 (10 parts), and the AF after water-ultraviolet irradiation is 8%, and there is adhesion failure. This shows that when the amount of modified aminosilane coupling agent added is small, the improvement effect on heat resistance and water immersion performance is general. When the amount of modified aminosilane coupling agent added exceeds 5 parts (Examples 2 to 3), the comprehensive performance of the two-component silicone sealant reaches a better level. Comparing Examples 2 and 3, it can be seen that as the amount of the modified amino coupling agent increases, the tensile strength of the prepared sealant gradually increases, and its 80°C tensile retention also gradually increases, but the maximum strength elongation of the sealant decreases. This is because the increase in its amount promotes the crosslinking density of the two-component silicone sealant. The modified aminosilane coupling agent contains both phenyl and multiple secondary amines, which improves the heat resistance and water immersion performance of the two-component silicone sealant. In the present invention, the addition amount of the modified aminosilane coupling agent is preferably 2 to 10 parts, more preferably 5 to 10 parts. Among them, the comprehensive performance of the two-component silicone sealant is best when the modified aminosilane coupling agent is added in an amount of 5 parts.

[0123] Comparison of Examples 2, 4, and 5 reveals that varying α,ω-dihydroxypolydimethylsiloxane viscosities and nano-activated calcium carbonate particle sizes affect the mechanical properties of the resulting two-component silicone sealants. The viscosity of the α,ω-dihydroxypolydimethylsiloxane, the particle size of the nano-activated calcium carbonate, and the type of catalyst have no significant effect on the 80°C tensile retention and adhesion after water-UV irradiation of the two-component silicone sealants containing the modified aminosilane coupling agent, demonstrating that the modified aminosilane coupling agent of the present invention is suitable for use in various two-component silicone sealant formulations.

[0124] Compared with Example 2, Comparative Example 1 does not add the modified amino silane coupling agent according to the present application, and Comparative Example 2 uses coupling agent a to replace the modified amino silane coupling agent according to the present application, both of which result in significant decrease of the 80℃ tensile adhesive strength and 80℃ tensile retention rate of the two-component silicone sealant, obvious increase of AF after water-UV irradiation, and increase of the degree of adhesive failure. Through comparison between Comparative Example 2 and Example 2, it can be obtained that without adding the modified amino silane coupling agent according to the present application, only increasing the amount of coupling agent a cannot improve the heat resistance and water-UV irradiation resistance of the two-component silicone sealant.

[0125] The above examples only express several embodiments of the present application, and the description is more specific and detailed, but it should not be understood as limiting the scope of the patent. It should be pointed out that for ordinary skilled in the art, several modifications and improvements can be made without departing from the concept of the present application, which are all within the protection scope of the present application. Therefore, the protection scope of the present patent should be subject to the appended claims.

Claims

1. A compound, characterized in that The structural formula of the compound is shown in the following formula (I): Formula (I).

2. The method for preparing the compound according to claim 1, wherein The following steps are involved: The product is obtained by reacting n-butyl benzoate and 3-(diethylenetriamino)propyltrimethoxysilane.

3. The preparation method according to claim 2, wherein The molar ratio of 3-(diethylenetriamino)propyltrimethoxysilane to n-butyl benzoate is (0.8-1.2):1; and / or, The reaction temperature is 60°C to 100°C and the reaction time is 4h to 12h; and / or, The solvent for the reaction is an alcohol solvent.

4. Use of the compound according to claim 1 as a coupling agent in the preparation of sealants.

5. A two-component silicone sealant, characterized in that: Including component A and component B: The A component includes the following raw materials in parts by weight: 100 parts of α,ω-dihydroxypolydimethylsiloxane; 60~150 parts of filler; 5 to 25 parts of dimethyl silicone oil; The B component includes the following raw materials in parts by weight: 100 parts of dimethyl silicone oil; 50 to 150 parts of carbon black; 15 to 60 parts of cross-linking agent; 16 to 75 parts of coupling agent; 0.1 to 1.5 parts of catalyst; The coupling agent comprises the compound according to claim 1.

6. The two-component silicone sealant according to claim 5, characterized in that: Including component A and component B: The A component includes the following raw materials in parts by weight: 100 parts of α,ω-dihydroxypolydimethylsiloxane; 90~110 parts of filler; 8 to 12 parts of dimethyl silicone oil; The B component includes the following raw materials in parts by weight: 100 parts of dimethyl silicone oil; 90 to 110 parts of carbon black; 45 to 55 parts of cross-linking agent; 47 to 65 parts of coupling agent; 0.8 to 1.2 parts of catalyst.

7. The two-component silicone sealant according to claim 5 or 6, characterized in that: The volume ratio of component A to component B is (8~12):

1.

8. The two-component silicone sealant according to claim 5 or 6, characterized in that: The coupling agent comprises the compound and coupling agent a; The coupling agent a is selected from γ-glycidyloxypropyltrimethoxysilane, γ-glycidyloxypropyltriethoxysilane, epoxycyclohexylmethyldimethoxysilane, epoxycyclohexylmethyldiethoxysilane, chloropropyltrimethoxysilane, chloropropyltriethoxysilane, γ-(2,3-epoxypropoxy)propyltrimethoxysiloxane, γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropylmethyldimethoxysilane, γ-aminopropylmethyldiethoxysilane, N- One or more of (2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldiethoxysilane, anilinomethyltrimethoxysilane, anilinomethyltriethoxysilane, γ-isocyanatepropyltrimethoxysilane, epoxypropyltrimethoxysilane, and 3-(diethylenetriamino)propyltrimethoxysilane.

9. The two-component silicone sealant according to claim 8, characterized in that: The weight ratio of the compound to coupling agent a is (1-15): (15-60).

10. The two-component silicone sealant according to claim 9, characterized in that: The weight ratio of the compound to coupling agent a is (2-10): (45-55).

11. The two-component silicone sealant according to claim 5 or 6, characterized in that: The filler is nano-active calcium carbonate; and / or, The viscosity of the α,ω-dihydroxy polydimethylsiloxane at 25±0.5° C. is 5000 mPa·s to 80000 mPa·s; and / or, The viscosity of the dimethyl silicone oil in component A at 25±0.5° C. is 300 mPa·s to 1000 mPa·s; and / or, The crosslinking agent is selected from one or more of ethyl orthosilicate, propyl orthosilicate, polyethyl silicate, methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, polymethyltriethoxysilane oligomer, phenyltrimethoxysilane, phenyltriethoxysilane, methylphenyldimethoxysilane, methylphenyldiethoxysilane, diphenyldimethoxysilane, and diphenyldiethoxysilane; and / or, The viscosity of the dimethyl silicone oil in component B is 5000 mPa·s to 15000 mPa·s at 25±0.5°C; and / or, The catalyst is selected from one or more of dibutyltin dilaurate, dibutyltin diacetate, dibutyltin dioctoate or tin octoate, isopropyl titanate, and n-butyl titanate.

12. The two-component silicone sealant according to claim 11, characterized in that: The particle size of the nano-active calcium carbonate is 20nm~200nm.

13. The method for preparing a two-component silicone sealant according to any one of claims 5 to 12, characterized in that: The following steps are involved: (1) Add the filler, α,ω-dihydroxy polydimethylsiloxane, and dimethyl silicone oil into a planetary mixer and mix them uniformly at 60°C to 120°C to obtain component A; (2) Add the dimethyl silicone oil, carbon black, crosslinking agent, coupling agent, and catalyst into a planetary mixer, stir and mix them evenly to obtain component B.

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