An acrylate resin and a preparation method thereof, an adhesive and a preparation method thereof

Abstract

The application belongs to the technical field of resin synthesis, and specifically discloses an acrylate resin, a preparation method thereof, an adhesive and a preparation method thereof. The main chain of the acrylate resin provided by the application introduces a long carbon chain alkane structure, enhances the movement ability of molecular chain segments, and endows the acrylate resin with higher flexibility and lower glass transition temperature; thus, the elastic modulus of the adhesive is improved, and the adhesive has higher bonding strength. Meanwhile, after the acrylate resin is added into the adhesive and subjected to light-heat double curing, the acrylate groups will quickly react and crosslink to form a compact three-dimensional network structure. In addition, the material of an alignment film in a liquid crystal display element is usually polyimide, the acrylate resin provided by the application has a soft skeleton, has high similarity with the chain segments of polyimide, and has good bonding stability because the bonding force after curing is not prone to failure under the action of thermal expansion and contraction or mechanical stress.

Description

Technical Field

[0001] This invention belongs to the field of resin synthesis technology, and particularly relates to an acrylate resin and its preparation method, and an adhesive and its preparation method. Background Technology

[0002] In recent years, with the development of information technology and the increasing demand for portable devices, display technology has continued to advance. Liquid crystal displays (LCDs) and organic light-emitting diodes (OLEDs) occupy an important position in the consumer electronics market due to their thinness, lightness, and low power consumption. In the production process of LCDs, to ensure the reliability and lifespan of the display panel, adhesives made of curable resin compositions are typically used to seal gaps and prevent external contaminants from entering and affecting display quality and lifespan. These adhesives must not only possess good mechanical stability but also maintain consistent performance under various environmental conditions.

[0003] Traditional adhesives tend to be quite rigid after curing. This isn't a problem for glass substrates with minimal shape changes, but it's no longer suitable for flexible display technology. When the substrate bends or deforms, the rigid adhesive may peel off or break because it cannot adapt to the deformation. This is especially true for LCD components with narrow bezels. The narrower the bezel, the less space is available for the adhesive. Not only must the adhesive form good adhesion to the substrate surface, but it also needs to maintain its bonding performance in extreme environments with high temperature and humidity. Furthermore, to ensure the long-term reliable operation of the display device, the adhesive also needs excellent moisture resistance to prevent moisture intrusion that could cause corrosion or other damage to internal components. Summary of the Invention

[0004] The purpose of this invention is to overcome the above-mentioned problems existing in the prior art and to provide an acrylic resin and its preparation method, as well as an adhesive and its preparation method.

[0005] To achieve the above-mentioned technical objectives, the present invention is implemented through the following technical solution:

[0006] In a first aspect, the present invention provides an acrylate resin, the chemical structure of which is shown in formula (Ⅰ):

[0007]

[0008] In formula (Ⅰ), X represents a hydrocarbon group with 1-20 C atoms.

[0009] Secondly, the present invention provides a method for preparing an acrylate resin, the method comprising the following steps:

[0010] S1. Dibromoalkane was dissolved in tetrahydrofuran, and 1,3-dihydroxyacetone, triethylamine and potassium iodide were added. The mixture was stirred and reacted in a water bath at 60-70°C for 10-12 hours. After the reaction, the pH was adjusted to neutral. The crude product was obtained by drying, filtering and concentrating. The crude product was purified by silica gel column chromatography to obtain compound A.

[0011] S2. Compound A and 4-[2-(4-chlorophenyl)prop-2-yl]benzoic acid were dissolved in N,N-dimethylformamide, pyridine was added, and the mixture was stirred at 65-75℃ for 8-12 h. After the reaction, the product was dried, filtered, and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain compound B.

[0012] S3. Dissolve compound B in methanol, add sodium borohydride, stir the reaction at 0℃ for 6-9 h, adjust the pH to 2, dry, filter and concentrate to obtain crude product, and purify by silica gel column chromatography to obtain compound C.

[0013] S4. Mix compound C, 2-hydroxyethyl methacrylate, and concentrated sulfuric acid, stir until homogeneous, and stir at room temperature for 8-10 hours. After reaction, dry, filter, and concentrate to obtain crude product, which is then purified by silica gel column chromatography to obtain acrylate resin.

[0014] Further, in step S1, the dibromoalkane is any one of 1,8-dibromooctane, 1,9-dibromononane, 1,10-dibromodecane, 1,13-dibromotridecane, 1,15-dibromopentadecane, 1,16-dibromohexadecane, 1,17-dibromoheptadecane, 1,18-dibromooctadecane, 1,19-dibromononadecane, and 1,20-dibromoeicosane.

[0015] Further, in step S1, the ratio of the amounts of dibromoalkane, 1,3-dihydroxyacetone, triethylamine, potassium iodide, and tetrahydrofuran is (21-31)g:(14.2-14.5)g:9.7g:(1.35-1.5)g:200mL.

[0016] Further, in step S2, the ratio of compound A, 4-[2-(4-chlorophenyl)prop-2-yl]benzoic acid, pyridine, and N,N-dimethylformamide is (22-30)g:(25-28)g:3mg:270mL.

[0017] Furthermore, in step S3, the ratio of compound B, sodium borohydride, and methanol is (20-30) g: 3.5 g: 150 mL.

[0018] Further, in step S4, the ratio of compound C, 2-hydroxyethyl methacrylate, and concentrated sulfuric acid is (45-48)g:(3.1-3.2)g:3mg.

[0019] Thirdly, the present invention provides an adhesive comprising the following raw materials in parts by weight: 20-40 parts of acrylate resin, 40-60 parts of bisphenol A type epoxy acrylate, 20-25 parts of bisphenol A type epoxy resin, 1-5 parts of photoradical initiator, 1-5 parts of thermal radical initiator, 2-4 parts of curing agent, 1-5 parts of silane coupling agent, and 25-32 parts of filler;

[0020] The acrylate resin is the acrylate resin provided in the first aspect of the present invention or the acrylate resin prepared by the preparation method provided in the second aspect of the present invention.

[0021] Further, the photoradical initiator is any one or more of 2,2-dimethoxy-phenylacetophenone, 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 2-(dimethylamino)-2-((4-methylphenyl)methyl)-1-(4-(4-morpholino)phenyl)-1-butanone, and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, mixed in any proportion;

[0022] The thermal free radical initiator is any one or more of 4-cyanopentanoic acid, 2,2'-azo(2-methyl-N-(2-hydroxyethyl)propionamide), and 2,2-azobisisobutyronitrile, mixed in any proportion;

[0023] The hardener is any one or more of malondihydrazide, sebacic dihydrazide, isophthalic dihydrazide, and adipic dihydrazide, mixed in any proportion;

[0024] The silane coupling agent is any one or more of 3-epoxypropoxypropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, and 3-isocyanate-propyltrimethoxysilane, mixed in any proportion;

[0025] The filler is any one or more of the following in any proportion: silicon dioxide, aluminum oxide, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate, talc, glass beads, asbestos, gypsum, diatomaceous earth, green clay, bentonite, montmorillonite, sericite, and activated clay.

[0026] Fourthly, the present invention provides a method for preparing an adhesive, the method comprising the following steps: according to the formula, mixing acrylate resin, bisphenol A type epoxy acrylate, bisphenol A type epoxy resin, photoradical initiator, thermal radical initiator, curing agent, silane coupling agent and filler evenly, grinding, filtering, to obtain the adhesive.

[0027] Compared with the prior art, the beneficial effects of the present invention are:

[0028] 1. The acrylic resin of this invention incorporates a long-chain alkane structure into its main chain, enhancing the mobility of molecular chain segments and endowing the acrylic resin with higher flexibility and a lower glass transition temperature; thereby increasing the elastic modulus of the adhesive and giving it higher bonding strength. Simultaneously, when this acrylic resin is added to the adhesive and undergoes photothermal dual curing, the acrylate groups rapidly react and crosslink, forming a tight three-dimensional network structure. Furthermore, the alignment film material in liquid crystal display elements is typically polyimide. The acrylic resin of this invention has a flexible backbone and a high degree of chain segment similarity to polyimide, resulting in better bonding stability as the cured adhesive is less prone to failure under thermal expansion and contraction or mechanical stress.

[0029] 2. The adhesive of the present invention has soft responsive properties. When applied to flexible or semi-flexible display elements, it can change with the curvature of the substrate and will not crack or fail due to bending or deformation of the substrate.

[0030] 3. The adhesive of the present invention has strong adhesion to the alignment film, can establish a firm bond with the alignment film, ensure that there are no display defects caused by poor adhesion, maintain its bonding strength under high temperature and high humidity conditions, and effectively block moisture penetration to avoid damage to internal components. Attached Figure Description

[0031] The accompanying drawings, which are included to provide a further understanding of the invention and form part of this application, illustrate exemplary embodiments of the invention and, together with their description, serve to explain the invention and do not constitute an undue limitation thereof. In the drawings:

[0032] Figure 1 These are the adhesion force curves of the adhesives provided in Examples 3-8 and Comparative Examples 1-2 of the present invention as a function of displacement. Detailed Implementation

[0033] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0034] Example 1 and Example 2 respectively provide a method for preparing acrylate resin M and a method for preparing acrylate resin N.

[0035] Example 1

[0036] Example 1 provides a method for preparing acrylate resin M, comprising the following steps:

[0037] S1. Dissolve 30.45 g of 1,20-dibromoeicosane in 200 mL of tetrahydrofuran, add 14.28 g of 1,3-dihydroxyacetone, 9.7 g of triethylamine and 1.35 g of potassium iodide, and stir the reaction in a water bath at 70 °C for 12 h. After the reaction, adjust the pH to neutral, dry, filter and concentrate to obtain the crude product, and purify it by silica gel column chromatography to obtain compound A1.

[0038] S2. 28.94g of compound A1 and 27.71g of 4-[2-(4-chlorophenyl)prop-2-yl]benzoic acid were dissolved in 270mL of N,N-dimethylformamide, 3mg of pyridine was added, and the mixture was stirred at 70℃ for 8h. After the reaction, the product was dried, filtered, and concentrated to obtain the crude product, which was purified by silica gel column chromatography to obtain compound B1.

[0039] S3. Dissolve 25.23g of compound B1 in 150mL of methanol, add 3.50g of sodium borohydride, stir and react at 0℃ for 6h, adjust pH to 2, dry, filter and concentrate to obtain crude product, and purify by silica gel column chromatography to obtain compound C1.

[0040] S4. Mix 47.56g of compound C1, 3.19g of 2-hydroxyethyl methacrylate, and 3mg of concentrated sulfuric acid, stir until homogeneous, and stir at room temperature for 8 hours. After reaction, dry, filter, and concentrate to obtain crude product, which is then purified by silica gel column chromatography to obtain acrylate resin M.

[0041] The preparation process described above is as follows:

[0042]

[0043] Example 2

[0044] Example 2 provides a method for preparing acrylate resin N, comprising the following steps:

[0045] S1. Dissolve 24.5 g of 1,10-dibromodecane in 200 mL of tetrahydrofuran, add 14.28 g of 1,3-dihydroxyacetone, 9.7 g of triethylamine and 1.35 g of potassium iodide, and stir the reaction in a water bath at 60 °C for 10 h. After the reaction, adjust the pH to neutral, dry, filter and concentrate to obtain the crude product, and purify it by silica gel column chromatography to obtain compound A2.

[0046] S2. 22.47g of compound A2 and 27.70g of 4-[2-(4-chlorophenyl)prop-2-yl]benzoic acid were dissolved in 270mL of N,N-dimethylformamide, and 3mg of pyridine was added. The mixture was stirred at 65℃ for 12h. After the reaction, the product was dried, filtered, and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain compound B2.

[0047] S3. Dissolve 20.15g of compound B2 in 150mL of methanol, add 3.50g of sodium borohydride, stir and react at 0℃ for 9h, adjust pH to 2, dry, filter and concentrate to obtain crude product, and purify by silica gel column chromatography to obtain compound C2.

[0048] S4. Mix 45.05g of compound C2, 3.19g of 2-hydroxyethyl methacrylate, and 3mg of concentrated sulfuric acid, stir until homogeneous, and stir at room temperature for 10h. After reaction, dry, filter, and concentrate to obtain crude product, which is then purified by silica gel column chromatography to obtain acrylate resin N.

[0049] The preparation process described above is as follows:

[0050]

[0051] Examples 3-8 and Comparative Examples 1 and 2 provide an adhesive and its preparation method.

[0052] Example 3

[0053] Example 3 provides an adhesive and its preparation method, as detailed below:

[0054] An adhesive comprises the following raw materials in parts by weight: 20 parts of acrylate resin M, 60 parts of bisphenol A type epoxy acrylate, 20 parts of bisphenol A type epoxy resin, 1 part of photoradical initiator, 1 part of thermal radical initiator, 4 parts of curing agent, 1 part of silane coupling agent, and 32 parts of filler.

[0055] The bisphenol A type epoxy acrylate is model EA-1010LC (Shinnakamura Chemical Industry Co., Ltd.); the bisphenol A type epoxy resin is model EXA-830CRP (DIC Corporation); the photoradical initiator is 2,2-dimethoxy-phenylacetophenone; the thermal radical initiator is 4-cyanopentanoic acid; the curing agent is malonyl diazid; the silane coupling agent is 3-epoxypropoxypropyltrimethoxysilane; and the filler is silica.

[0056] A method for preparing an adhesive includes the following steps:

[0057] According to the formula, acrylate resin M, bisphenol A type epoxy acrylate, bisphenol A type epoxy resin, photoradical initiator, thermal radical initiator, hardener, silane coupling agent, and filler are mixed evenly, ground, and filtered to obtain the adhesive.

[0058] Example 4

[0059] Example 4 provides an adhesive and its preparation method, as detailed below:

[0060] An adhesive comprises the following raw materials in parts by weight: 30 parts of acrylate resin M, 50 parts of bisphenol A type epoxy acrylate, 23 parts of bisphenol A type epoxy resin, 2 parts of photoradical initiator, 3 parts of thermal radical initiator, 2 parts of curing agent, 3 parts of silane coupling agent, and 28 parts of filler.

[0061] The bisphenol A type epoxy acrylate is model EA-1010LC (Shinnakamura Chemical Industry Co., Ltd.); the bisphenol A type epoxy resin is model EXA-830CRP (DIC Corporation); the photoradical initiator is 1-hydroxycyclohexylphenyl ketone; the thermal radical initiator is 2,2-azobisisobutyronitrile; the curing agent is sebacic acid dihydrazide; the silane coupling agent is 3-mercaptopropyltrimethoxysilane; and the filler is montmorillonite.

[0062] A method for preparing an adhesive includes the following steps:

[0063] According to the formula, acrylate resin M, bisphenol A type epoxy acrylate, bisphenol A type epoxy resin, photoradical initiator, thermal radical initiator, hardener, silane coupling agent, and filler are mixed evenly, ground, and filtered to obtain the adhesive.

[0064] Example 5

[0065] Example 5 provides an adhesive and its preparation method, as detailed below:

[0066] An adhesive comprises the following raw materials in parts by weight: 40 parts of acrylate resin M, 40 parts of bisphenol A type epoxy acrylate, 25 parts of bisphenol A type epoxy resin, 5 parts of photoradical initiator, 5 parts of thermal radical initiator, 3 parts of curing agent, 5 parts of silane coupling agent, and 25 parts of filler.

[0067] The bisphenol A type epoxy acrylate is model EA-1010LC (Shinnakamura Chemical Industry Co., Ltd.); the bisphenol A type epoxy resin is model EXA-830CRP (DIC Corporation); the photoradical initiator is 2,2-dimethoxy-phenylacetophenone; the thermal radical initiator is 2,2'-azo (2-methyl-N-(2-hydroxyethyl)propionamide); the curing agent is isophthalic acid dihydrazide; the silane coupling agent is 3-aminopropyltrimethoxysilane; and the filler is alumina.

[0068] A method for preparing an adhesive includes the following steps:

[0069] According to the formula, acrylate resin M, bisphenol A type epoxy acrylate, bisphenol A type epoxy resin, photoradical initiator, thermal radical initiator, hardener, silane coupling agent, and filler are mixed evenly, ground, and filtered to obtain the adhesive.

[0070] Example 6

[0071] Example 6 provides an adhesive and its preparation method, as detailed below:

[0072] An adhesive comprises the following raw materials in parts by weight: 20 parts of acrylate resin N, 60 parts of bisphenol A type epoxy acrylate, 20 parts of bisphenol A type epoxy resin, 1 part of photoradical initiator, 1 part of thermal radical initiator, 4 parts of curing agent, 1 part of silane coupling agent, and 32 parts of filler.

[0073] The bisphenol A type epoxy acrylate is model EA-1010LC (Shinnakamura Chemical Industry Co., Ltd.); the bisphenol A type epoxy resin is model EXA-830CRP (DIC Corporation); the photoradical initiator is 2,2-dimethoxy-phenylacetophenone; the thermal radical initiator is 4-cyanopentanoic acid; the curing agent is malonyl diazid; the silane coupling agent is 3-epoxypropoxypropyltrimethoxysilane; and the filler is silica.

[0074] A method for preparing an adhesive includes the following steps:

[0075] According to the formula, acrylate resin N, bisphenol A type epoxy acrylate, bisphenol A type epoxy resin, photoradical initiator, thermal radical initiator, hardener, silane coupling agent, and filler are mixed evenly, ground, and filtered to obtain the adhesive.

[0076] Example 7

[0077] Example 7 provides an adhesive and its preparation method, as detailed below:

[0078] An adhesive comprises the following raw materials in parts by weight: 30 parts of acrylate resin N, 50 parts of bisphenol A type epoxy acrylate, 23 parts of bisphenol A type epoxy resin, 2 parts of photoradical initiator, 3 parts of thermal radical initiator, 2 parts of curing agent, 3 parts of silane coupling agent, and 28 parts of filler.

[0079] The bisphenol A type epoxy acrylate is model EA-1010LC (Shinnakamura Chemical Industry Co., Ltd.); the bisphenol A type epoxy resin is model EXA-830CRP (DIC Corporation); the photoradical initiator is 1-hydroxycyclohexylphenyl ketone; the thermal radical initiator is 2,2-azobisisobutyronitrile; the curing agent is sebacic acid dihydrazide; the silane coupling agent is 3-mercaptopropyltrimethoxysilane; and the filler is montmorillonite.

[0080] A method for preparing an adhesive includes the following steps:

[0081] According to the formula, acrylate resin N, bisphenol A type epoxy acrylate, bisphenol A type epoxy resin, photoradical initiator, thermal radical initiator, hardener, silane coupling agent, and filler are mixed evenly, ground, and filtered to obtain the adhesive.

[0082] Example 8

[0083] Example 8 provides an adhesive and its preparation method, as detailed below:

[0084] An adhesive comprising the following raw materials in parts by weight: 40 parts of acrylate resin N, 40 parts of bisphenol A type epoxy acrylate, 25 parts of bisphenol A type epoxy resin, 5 parts of photoradical initiator, 5 parts of thermal radical initiator, 3 parts of curing agent, 5 parts of silane coupling agent, and 25 parts of filler.

[0085] The bisphenol A type epoxy acrylate is model EA-1010LC (Shinnakamura Chemical Industry Co., Ltd.); the bisphenol A type epoxy resin is model EXA-830CRP (DIC Corporation); the photoradical initiator is 2,2-dimethoxy-phenylacetophenone; the thermal radical initiator is 2,2'-azo (2-methyl-N-(2-hydroxyethyl)propionamide); the curing agent is isophthalic acid dihydrazide; the silane coupling agent is 3-aminopropyltrimethoxysilane; and the filler is alumina.

[0086] A method for preparing an adhesive includes the following steps:

[0087] According to the formula, acrylate resin N, bisphenol A type epoxy acrylate, bisphenol A type epoxy resin, photoradical initiator, thermal radical initiator, hardener, silane coupling agent, and filler are mixed evenly, ground, and filtered to obtain the adhesive.

[0088] Comparative Example 1

[0089] Comparative Example 1 provides an adhesive and its preparation method, as detailed below:

[0090] An adhesive comprises the following raw materials in parts by weight: 20 parts of bisphenol A glycerol dimethacrylate, 60 parts of bisphenol A type epoxy acrylate, 20 parts of bisphenol A type epoxy resin, 1 part of photoradical initiator, 1 part of thermal radical initiator, 4 parts of curing agent, 1 part of silane coupling agent, and 32 parts of filler.

[0091] The bisphenol A type epoxy acrylate is model EA-1010LC (Shinnakamura Chemical Industry Co., Ltd.); the bisphenol A type epoxy resin is model EXA-830CRP (DIC Corporation); the photoradical initiator is 2,2-dimethoxy-phenylacetophenone; the thermal radical initiator is 4-cyanopentanoic acid; the curing agent is malonyl diazid; the silane coupling agent is 3-epoxypropoxypropyltrimethoxysilane; and the filler is silica.

[0092] A method for preparing an adhesive includes the following steps:

[0093] According to the formula, bisphenol A glycerol dimethacrylate, bisphenol A type epoxy acrylate, bisphenol A type epoxy resin, photoradical initiator, thermal radical initiator, hardener, silane coupling agent, and filler are mixed evenly, ground, and filtered to obtain the adhesive.

[0094] Comparative Example 2

[0095] Comparative Example 2 provides an adhesive and its preparation method, as follows:

[0096] An adhesive comprises the following raw materials in parts by weight: 20 parts modified epoxy acrylate, 60 parts bisphenol A type epoxy acrylate, 20 parts bisphenol A type epoxy resin, 1 part photoradioinitiator, 1 part thermal free radical initiator, 4 parts curing agent, 1 part silane coupling agent, and 32 parts filler.

[0097] The modified epoxy acrylate is model EBECRYL3708 (Zhenxin Company, USA); the bisphenol A type epoxy acrylate is model EA-1010LC (Shinnakamura Chemical Industry Co., Ltd.); the bisphenol A type epoxy resin is model EXA-830CRP (DIC Corporation); the photoradical initiator is 2,2-dimethoxy-phenylacetophenone; the thermal radical initiator is 4-cyanopentanoic acid; the curing agent is malonyl hydrazide; the silane coupling agent is 3-epoxypropoxypropyltrimethoxysilane; and the filler is silica.

[0098] A method for preparing an adhesive includes the following steps:

[0099] According to the formula, the modified epoxy acrylate, bisphenol A epoxy acrylate, bisphenol A epoxy resin, photoradical initiator, thermal radical initiator, hardener, silane coupling agent, and filler are mixed evenly, ground, and filtered to obtain the adhesive.

[0100] Performance testing

[0101] The properties of the adhesives prepared in Examples 3-8 and Comparative Examples 1-2 were tested. The relevant test items and test procedures are as follows:

[0102] 1. Adhesion

[0103] The following tests were conducted using a universal testing machine: (1) Sample preparation: Glass was cut to 4.5*2.5cm, and adhesive strength test samples were prepared using a dispensing machine (cross dispensing method) and a vacuum bonding machine (pressure: 0.5Pa, delay 5s). The glass thickness was 0.5mm, the dispensing diameter was 3mm, and the dispensing thickness was 4μm; (2) UV (3000mj, 25cm) + heat (120℃, 50min) curing; (3) Testing: Adhesion strength was tested using a universal testing machine with a pressure head diameter of 5mm and a push speed of 5mm / s; (4) Data processing: Data was processed using Origin, and the results are shown in Table 1 and Figure 1 As shown.

[0104] 2. Thixotropy

[0105] The viscometer was used for testing: (1) A total of 4g was stored in a sample bottle under the conditions of 25℃ and 60% humidity; (2) 0.1ml was taken for each test, and the rotor was No. 7 with a rotation speed of 1rpm / 5rpm / 10rpm; (3) Results analysis: Thixotropy (Ti value) is expressed as the ratio of 1rpm to 10rpm, and the results are shown in Table 1.

[0106] 3. Adhesion after PCT

[0107] The PCT conditions were 121℃, 100% humidity, and 2 atmospheres. The adhesion test method after PCT was the same as the adhesion test method, and the results are shown in Table 1.

[0108] 4. Moisture permeability

[0109] (1) Prepare a 300µm thick film; (2) After UV (3000mj, 25cm) + heat (120℃, 50min) curing, cut it into a ring shape to meet the requirements of the moisture permeation cup; (3) Test the quality change of the film for 10 days under the conditions of temperature 85℃ / humidity 85%, and the results are shown in Table 1.

[0110] Table 1

[0111]

[0112] As shown in Table 1, the adhesives obtained in Examples 3-8 have better bonding performance than those in Comparative Examples 1 and 2, and can still maintain good bonding strength under high temperature and high humidity conditions, which fully demonstrates that the acrylate resin of the present invention can improve the bonding performance of the adhesive.

[0113] Specifically, compared with Example 1, in Comparative Examples 1 and 2, 20 parts of acrylate resin M in the raw material composition of the adhesive were replaced with bisphenol A glycerol dimethacrylate and modified epoxy acrylate, respectively. As can be seen from the test data of Example 3 and Comparative Examples 1 and 2 in Table 1, the acrylate resin provided by the present invention, when added to the adhesive, produces an adhesive with better bonding performance.

[0114] In the description of this specification, references to terms such as "an embodiment," "example," "specific example," etc., indicate that a specific feature, structure, material, or characteristic described in connection with that embodiment or example is included in at least one embodiment or example of the invention. In this specification, illustrative expressions of the above terms do not necessarily refer to the same embodiment or example. Furthermore, the specific features, structures, materials, or characteristics described may be combined in any suitable manner in one or more embodiments or examples.

[0115] The foregoing has shown and described the basic principles, main features, and advantages of the present invention. Those skilled in the art should understand that the present invention is not limited to the above embodiments. The embodiments and descriptions in the specification are merely illustrative of the principles of the invention. Various changes and modifications can be made to the invention without departing from its spirit and scope, and all such changes and modifications fall within the scope of the claimed invention.

Claims

1. An acrylic resin, characterized in that, The chemical structure of the acrylate resin is shown in formula (Ⅰ): In formula (Ⅰ), X represents a hydrocarbon group with 1-20 C atoms.

2. A method for preparing the acrylate resin according to claim 1, characterized in that, The method includes the following steps: S1. Dibromoalkane was dissolved in tetrahydrofuran, and 1,3-dihydroxyacetone, triethylamine and potassium iodide were added. The mixture was stirred and reacted in a water bath at 60-70°C for 10-12 hours. After the reaction, the pH was adjusted to neutral. The crude product was obtained by drying, filtering and concentrating. The crude product was purified by silica gel column chromatography to obtain compound A. S2. Compound A and 4-[2-(4-chlorophenyl)prop-2-yl]benzoic acid were dissolved in N,N-dimethylformamide, pyridine was added, and the mixture was stirred at 65-75℃ for 8-12 h. After the reaction, the product was dried, filtered, and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain compound B. S3. Dissolve compound B in methanol, add sodium borohydride, stir the reaction at 0℃ for 6-9 h, adjust the pH to 2, dry, filter and concentrate to obtain crude product, and purify by silica gel column chromatography to obtain compound C. S4. Mix compound C, 2-hydroxyethyl methacrylate, and concentrated sulfuric acid, stir until homogeneous, and stir at room temperature for 8-10 hours. After reaction, dry, filter, and concentrate to obtain crude product, which is then purified by silica gel column chromatography to obtain acrylate resin.

3. The method for preparing an acrylate resin according to claim 2, characterized in that, In step S1, the dibromoalkane is any one of 1,8-dibromooctane, 1,9-dibromononane, 1,10-dibromodecane, 1,13-dibromotridecane, 1,15-dibromopentadecanane, 1,16-dibromohexadecane, 1,17-dibromoheptadecane, 1,18-dibromooctadecane, 1,19-dibromononadecanane, and 1,20-dibromoeicosane.

4. The method for preparing an acrylate resin according to claim 2, characterized in that, In step S1, the ratio of the amounts of dibromoalkane, 1,3-dihydroxyacetone, triethylamine, potassium iodide, and tetrahydrofuran is (21-31)g:(14.2-14.5)g:9.7g:(1.35-1.5)g:200mL.

5. The method for preparing an acrylate resin according to claim 2, characterized in that, In step S2, the ratio of compound A, 4-[2-(4-chlorophenyl)prop-2-yl]benzoic acid, pyridine, and N,N-dimethylformamide is (22-30)g:(25-28)g:3mg:270mL.

6. The method for preparing an acrylate resin according to claim 2, characterized in that, In step S3, the ratio of compound B, sodium borohydride, and methanol is (20-30)g:3.5g:150mL.

7. The method for preparing an acrylate resin according to claim 2, characterized in that, In step S4, the ratio of compound C, 2-hydroxyethyl methacrylate, and concentrated sulfuric acid is (45-48)g:(3.1-3.2)g:3mg.

8. An adhesive, characterized in that, The raw materials include the following parts by weight: 20-40 parts of acrylate resin, 40-60 parts of bisphenol A type epoxy acrylate, 20-25 parts of bisphenol A type epoxy resin, 1-5 parts of photoradical initiator, 1-5 parts of thermal radical initiator, 2-4 parts of curing agent, 1-5 parts of silane coupling agent, and 25-32 parts of filler. The acrylate resin is the acrylate resin according to claim 1 or the acrylate resin according to any one of claims 2-7 prepared by the method of preparation.

9. An adhesive according to claim 8, characterized in that, The photoradical initiator is any one or more of 2,2-dimethoxy-phenylacetophenone, 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 2-(dimethylamino)-2-((4-methylphenyl)methyl)-1-(4-(4-morpholino)phenyl)-1-butanone, and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, mixed in any proportion; The thermal free radical initiator is any one or more of 4-cyanopenic acid, 2,2'-azo(2-methyl-N-(2-hydroxyethyl)propionamide), and 2,2-azobisisobutyronitrile, mixed in any proportion; The hardener is any one or more of malondihydrazide, sebacic dihydrazide, isophthalic dihydrazide, and adipic dihydrazide, mixed in any proportion; The silane coupling agent is any one or more of 3-epoxypropoxypropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, and 3-isocyanate-propyltrimethoxysilane, mixed in any proportion; The filler is any one or more of the following in any proportion: silicon dioxide, aluminum oxide, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate, talc, glass beads, asbestos, gypsum, diatomaceous earth, green clay, bentonite, montmorillonite, sericite, and activated clay.

10. A method for preparing the adhesive according to any one of claims 8-9, characterized in that, The method includes the following steps: according to the formula, acrylate resin, bisphenol A type epoxy acrylate, bisphenol A type epoxy resin, photoradical initiator, thermal radical initiator, curing agent, silane coupling agent and filler are mixed evenly, then ground and filtered to obtain adhesive.

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