Modified amino silane coupling agent, two-component silicone sealant and preparation method of two-component silicone sealant

Abstract

The invention relates to a modified amino silane coupling agent, a two-component silicone sealant and a preparation method of the two-component silicone sealant. The structural formula of the modified amino silane coupling agent is shown as a formula (I); the bi-component silicone sealant comprises a component A and a component B, wherein the component A comprises the following raw materials in parts by weight: 100 parts of alpha, omega-dihydroxy polydimethylsiloxane; 60 to 150 parts of a filler; 5 to 25 parts of dimethyl silicone oil; the component B is prepared from 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 a cross-linking agent; 16 to 75 parts of a coupling agent; 0.1 to 1.5 parts of a catalyst; the coupling agent comprises the modified amino silane coupling agent. According to the invention, by adding a proper amount of the modified amino silane coupling agent, the problems of performance degradation and poorer water immersion performance of the traditional two-component silicone sealant at high temperature can be effectively solved, and the heat resistance and water immersion cohesiveness of the two-component silicone sealant are improved.

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 vulcanized (RTV-2) silicone sealant can undergo a cross-linking reaction at room temperature to form an elastomer with a certain hardness. It has been widely used in the construction and industrial fields as the main product of sealing materials. Among them, silane coupling agent is an important component of sealant, which plays a connecting role between sealant and substrate. Its application in composite materials has been widely recognized and has a great influence on the bonding strength, water resistance and weather resistance of the substrate. Even a very small amount at the interface will have a significant impact on the performance of the composite material.

[0003] At present, the use of common two-component silicone sealants is relatively limited under certain conditions. For example, under long-term high temperature and water immersion conditions, its mechanical properties and tensile adhesion will be adversely affected. Patent CN202210877362.3 uses formula optimization to prepare a two-component high-temperature resistant and high-shear strength organic silicone adhesive, but its formula contains a large amount of organic silicone polysilazane, and the formula cost is high, which is not conducive to industrialization. Patent CN202410084455.X mixes organic siloxane / promoter dibutyltin dilaurate / cross-linking agent ethyl orthosilicate to react with each other to generate a new mixed adhesive, and then adds bamboo fiber to the mixed adhesive in a prescribed 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 conventional coupling agents obtained by reaction under specific conditions. Its synthesis process is relatively cumbersome and is an improvement on a single performance, and its use is limited under a variety of 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 of the embodiments, the molar ratio of 3-(diethylenetriamino)propyltrimethoxysilane to n-butyl benzoate is (0.8-1.2):1.

[0009] In some of the 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-dihydroxy polydimethylsiloxane;

[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 as 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-dihydroxy polydimethylsiloxane;

[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 coupling agent a;

[0030] The coupling agent a is selected from one or more of γ-glycidyloxypropyltrimethoxysilane, γ-glycidyloxypropyltrimethoxysilane, epoxycyclohexylmethyldimethoxysilane, chloropropyltrimethoxysilane, γ-(2,3-epoxypropoxy)propyltrimethoxysiloxane, γ-aminopropyltrimethoxysilane, γ-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, anilinomethyltrimethoxysilane, γ-isocyanatepropyltrimethoxysilane, epoxypropyltrimethoxysilane, and 3-(diethylenetriamine)propyltrimethoxysilane;

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

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

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

[0034] In some embodiments, the viscosity of the α,ω-dihydroxy polydimethylsiloxane at 25±0.5° C. is 5000 mPa·s to 80000 mPa·s, preferably 10000 mPa·s to 40000 mPa·s.

[0035] In some embodiments, the viscosity of the dimethyl silicone oil in component A at 25±0.5° C. is 300 mPa·s to 1000 mPa·s, preferably 300 mPa·s to 600 mPa·s.

[0036] In some embodiments, the crosslinking agent is selected from one or more of tetraethyl orthosilicate, propyl orthosilicate, polyethyl silicate, methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, polymethyltriethoxysilane oligomer, phenyltrimethoxysilane, phenyltriethoxysilane, methylphenyldimethoxysilane, methylphenyldiethoxysilane, diphenyldimethoxysilane, and 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 of the 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 adopts n-butyl benzoate to carry out structural modification on 3-(diethylenetriamino)propyltrimethoxysilane to obtain a modified aminosilane coupling agent, and further utilizes the modified aminosilane coupling agent to prepare a two-component silicone sealant. By adding an appropriate amount of the modified aminosilane coupling agent, the problems of performance attenuation and poor water immersion performance of the traditional two-component silicone sealant at high temperature can be effectively solved, the heat resistance and water immersion adhesion of the two-component silicone sealant can be improved, and the 80°C tensile bonding strength, 80°C tensile retention rate, and adhesion after water-ultraviolet light of the two-component silicone sealant can be improved. The two-component silicone sealant of the present invention is easy to construct and can meet the requirements of special buildings, automobiles, electronic appliances, etc.

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

[0047] In order to facilitate the 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 disclosure of the present invention more thorough and comprehensive.

[0048] The experimental methods in the following examples without specifying specific conditions are usually 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 in the present invention have the same meaning as those commonly understood by those skilled in the art to which the present invention belongs. The terms used in the specification of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The term "and / or" used in the present invention includes any and all combinations of one or more of the related listed items.

[0050] In addition, as used in the present invention, the term "or" is an inclusive "or" symbol and is 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. In addition, throughout the 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 involved, and the structural formula of the compound is 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 in 3-(diethylenetriamine)propyltrimethoxysilane. The synthesis route is as follows:

[0054]

[0055] Some embodiments of the present invention involve a method for preparing the above-mentioned compound, comprising the following steps: reacting n-butyl benzoate and 3-(diethylenetriamino)propyltrimethoxysilane to obtain.

[0056] In some preferred embodiments, the preparation method of the compound comprises the following steps: adding 3-(diethylenetriamino)propyltrimethoxysilane to a solvent, adding n-butyl benzoate after fully mixing, heating to 60°C to 100°C and reflux reaction for 4h to 12h, then distilling under reduced pressure to remove small molecules, separating, and obtaining 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 with a stirrer and a thermometer and filled with nitrogen for protection, 1 mol of n-butyl benzoate was added after fully mixing, the temperature was raised to 80°C and refluxed for 8 hours, then small molecules were removed by vacuum distillation, and the target 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 CN stretching vibration absorption peak appeared near 1077 cm -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) is 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 a kneader and stir and disperse. After 5 minutes, add 100 parts of 60 nm nano-active calcium carbonate during stirring to make the glue completely cover 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.

[0070] Component B (parts by weight): According to the proportion of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black are added into a planetary machine and stirred in vacuum, and the temperature is kept stable at 100°C for 30 minutes to obtain base material B, and then 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethoxy(ethyl)silane, 20 parts of γ-glycidyloxypropyltrimethoxy(ethyl)silane, 2 parts of modified aminosilane coupling agent and 1 part of dibutyltin dilaurate are added, stirred for 20 minutes under nitrogen protection to obtain the base material, and sealed for storage.

[0071] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum according to a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-type test piece for testing the tensile adhesion of the sample.

[0072] Example 2

[0073] This embodiment provides a two-component silicone sealant, including 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 a kneader and stir and disperse. After 5 minutes, add 100 parts of 60 nm nano-active calcium carbonate during stirring to make the glue completely cover 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.

[0076] Component B (parts by weight): According to the proportion of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black are added into a planetary machine for vacuum stirring, and the temperature is stabilized at 100°C for 30 minutes to obtain base material B. Then, 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethoxy(ethyl)silane, 20 parts of γ-glycidyloxypropyltrimethoxy(ethyl)silane, 5 parts of modified aminosilane coupling agent are added with 1 part of dibutyltin dilaurate, and the mixture is stirred for 20 minutes under nitrogen protection, and sealed for storage.

[0077] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum according to a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-type 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 nano-active calcium carbonate during stirring to make the glue completely cover 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 proportion of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black are added into a planetary machine and stirred in vacuum, and the temperature is kept stable at 100°C for 30 minutes to obtain base material B, and then 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethoxy(ethyl)silane, 20 parts of γ-glycidyloxypropyltrimethoxy(ethyl)silane, 10 parts of modified aminosilane coupling agent are added with 1 part of dibutyltin dilaurate, stirred for 20 minutes under nitrogen protection, and sealed for storage.

[0083] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum according to a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-type 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 20000 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 nano-active calcium carbonate during stirring to make the glue completely cover 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 proportion of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black are added into a planetary machine for vacuum stirring, and the temperature is stabilized at 100°C for 30 minutes to obtain base material B. Then, 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethoxy(ethyl)silane, 20 parts of γ-glycidyloxypropyltrimethoxy(ethyl)silane, 5 parts of modified aminosilane coupling agent are added with 1 part of dibutyltin dilaurate, and the mixture is stirred for 20 minutes under nitrogen protection, and sealed for storage.

[0089] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum according to a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-type 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 20000 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 nano-active calcium carbonate during stirring to make the glue completely cover 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 proportion of component B, 100 parts of 10000 mPa·s dimethyl silicone oil and 100 parts of carbon black are added into a planetary machine for vacuum stirring, and the temperature is stabilized at 100°C for 30 minutes to obtain base material B. Then, 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethoxy(ethyl)silane, 20 parts of γ-glycidyloxypropyltrimethoxy(ethyl)silane, 5 parts of modified aminosilane coupling agent are added with 1 part of dibutyltin dioctoate, and the mixture is stirred for 20 minutes under nitrogen protection, and sealed for storage.

[0095] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum according to a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-type 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, no 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 nano-active calcium carbonate during stirring to make the glue completely cover 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, add 100 parts of 10000mPa·s dimethyl silicone oil and 100 parts of carbon black into a planetary machine and stir under vacuum. Keep the temperature at 100°C for 30 minutes to obtain base material B. Add 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 30 parts of γ-aminopropyltrimethoxysilane, 20 parts of γ-glycidyloxypropyltrimethoxysilane and 1 part of dibutyltin dilaurate, stir for 20 minutes under nitrogen protection to obtain the base material B, and seal and store.

[0101] Component A and component B were then mixed uniformly in a planetary mixer in a vacuum according to a mixing volume ratio of 10:1 to obtain a two-component silicone sealant, which was then made into an H-type 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-aminopropyltrimethoxysilane, 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 nano-active calcium carbonate during stirring to make the glue completely cover 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, add 100 parts of 10000mPa·s dimethyl silicone oil and 100 parts of carbon black into a planetary machine and stir under vacuum. Keep the temperature at 100°C for 30 minutes to obtain base material B. Add 30 parts of propyltrimethoxysilane, 20 parts of methyltrimethoxysilane, 35 parts of γ-aminopropyltrimethoxysilane, 20 parts of γ-glycidyloxypropyltrimethoxysilane and 1 part of dibutyltin dilaurate, stir for 20 minutes under nitrogen protection, and seal for storage.

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

[0108] The raw materials for preparing 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 embodiments 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 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, and the 80°C tensile bonding strength and 80°C tensile retention rate 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. It 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 is better. Comparing Example 2 and Example 3, it can be seen that as the amount of the modified amino coupling agent continues to increase, the tensile strength of the prepared sealant gradually increases, and its 80°C tensile retention rate also gradually increases, but the maximum strength elongation of the sealant will decrease. This is because the increase in its amount promotes the crosslinking density of the two-component silicone sealant. The modified aminosilane coupling agent contains phenyl and multiple secondary amines at the same time, 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, wherein the comprehensive performance of the two-component silicone sealant is best when the addition amount of the modified aminosilane coupling agent is 5 parts.

[0123] By comparing Example 2, Example 4 and Example 5, it can be found that different viscosities of α, ω-dihydroxy polydimethylsiloxane and particle sizes of nano-active calcium carbonate will affect the mechanical properties of the prepared two-component silicone sealant. The viscosity of α, ω-dihydroxy polydimethylsiloxane, the particle size of nano-active calcium carbonate and the type of catalyst have no obvious effect on the 80°C tensile retention and water-ultraviolet light adhesion of the two-component silicone sealant containing the modified aminosilane coupling agent, indicating that the modified aminosilane coupling agent of the present invention is suitable for the above multiple two-component silicone sealant formulas.

[0124] Compared with Example 2, Comparative Example 1 does not add the modified aminosilane coupling agent of the present invention, and Comparative Example 2 uses coupling agent a to replace the modified aminosilane coupling agent of the present invention, both resulting in a significant decrease in the 80°C tensile bonding strength and 80°C tensile retention rate of the two-component silicone sealant, a significant increase in AF after water-ultraviolet light irradiation, and an increase in the degree of bond failure. By comparing Comparative Example 2 with Example 2, it can be obtained that the heat resistance and water-ultraviolet light resistance of the two-component silicone sealant cannot be improved by simply increasing the amount of coupling agent a without adding the modified aminosilane coupling agent of the present invention.

[0125] The above-mentioned embodiments only express several implementation methods of the present invention, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of the invention patent. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be subject to the attached claims.

Claims

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

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

3. The preparation method according to claim 2, characterized in that: 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 of the reaction is an alcohol solvent.

4. Use of the compound as claimed in 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-dihydroxy polydimethylsiloxane; 60 to 150 parts of filler; 5 to 25 parts of dimethyl silicone oil; The B component includes the following raw materials in parts by weight: The coupling agent comprises the compound as claimed in 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-dihydroxy polydimethylsiloxane; 90 to 110 parts of filler; 8 to 12 parts of dimethyl silicone oil; The B component includes the following raw materials in parts by weight:

7. The two-component silicone sealant according to claim 5 or 6, characterized in that: The volume ratio of the component A to the 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 one or more of γ-glycidyloxypropyltrimethoxysilane, γ-glycidyloxypropyltrimethoxysilane, epoxycyclohexylmethyldimethoxysilane, chloropropyltrimethoxysilane, Y-(2,3-epoxypropoxy)propyltrimethoxysiloxane, γ-aminopropyltrimethoxysilane, γ-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, anilinomethyltrimethoxysilane, γ-isocyanatepropyltrimethoxysilane, epoxypropyltrimethoxysilane, and 3-(diethylenetriamine)propyltrimethoxysilane; Preferably, the weight ratio of the compound to the coupling agent a is (1-15): (15-60); More preferably, the weight ratio of the compound to coupling agent a is (2-10):(45-55).

9. The two-component silicone sealant according to claim 5 or 6, characterized in that: The filler is nano-active calcium carbonate; preferably, the particle size of the nano-active calcium carbonate is 20nm to 200nm; 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 the component B is 5000mPa·s to 15000mPa·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.

10. The method for preparing a two-component silicone sealant according to any one of claims 5 to 9, characterized in that: The following steps are involved: (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; (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.

Images