Latent curing agent based on dynamic crosslinking-controllable dissolution mechanism

Abstract

The invention provides a latent curing agent based on a dynamic crosslinking-controllable dissolution mechanism. The latent curing agent at least comprises a reaction product of a component with a maleimide structure, a component with a furan ring structure and an amine component with at least two amino groups or imino groups, and the reaction product has a dynamic cross-linked network structure containing a Diels-Alder addition structure. Compared with the prior art, the latent curing agent provided by the invention can be used for realizing long-term storage and medium and low temperature curing of a single-component thermosetting material, and especially when the latent curing agent is applied to an epoxy-anhydride system, an epoxy-phenolic aldehyde system and an epoxy-dicyandiamide system, not only is the curing temperature reduced, but also the storage life is longer, and the curing effect is better. Meanwhile, the preparation process of the latent curing agent is simple, easy and convenient to operate, good in controllability, easy to implement and suitable for large-scale industrial production.

Description

Technical Field

[0001] The present application specifically relates to a latent curing agent based on a dynamic cross-linking-controllable dissolution mechanism and a preparation method thereof, and belongs to the technical field of polymer materials. Background Art

[0002] Thermosetting plastics are widely used in electronic packaging materials, coatings, adhesives, composite materials and other fields due to their excellent thermal properties, mechanical properties, chemical stability, dimensional stability, etc. In order to achieve high performance, thermosetting materials (including epoxy resins, unsaturated polyesters, phenolic resins, polyurethanes, rubbers, etc.) are usually used with crosslinkers (also called hardeners and curing agents) to obtain a permanently crosslinked network. In order to avoid the crosslinking reaction before use, the thermosetting material and the crosslinker need to be freshly mixed (called two-component thermosetting materials), which leads to time waste, unstable quality, inflexible processing time and waste of residual products. In contrast, single-component thermosetting materials containing thermosetting resin monomers and crosslinkers in one pot can solve these problems. In order to achieve single-component thermosetting materials, latent crosslinkers (or accelerators) play a vital role. So far, there are three methods to obtain latent crosslinkers (or accelerators): high melting point, chemical modification, and microencapsulation to reduce or reversibly block the reactivity of highly active crosslinkers (or accelerators). However, single-component thermosetting materials often require very low storage temperatures (e.g. -18°C) for long-term storage; high temperatures are required to complete crosslinking due to decreased activity. Therefore, single-component thermosetting materials that combine long storage life with rapid crosslinking at medium and low temperatures remain a huge challenge. Summary of the invention

[0003] The main purpose of the present application is to provide a class of latent curing agents based on a dynamic cross-linking-controllable dissolution mechanism and a preparation method thereof, so as to overcome the deficiencies in the prior art.

[0004] In order to achieve the above-mentioned invention objectives, the technical solutions adopted in this application are as follows.

[0005] The first aspect of the present application provides a latent curing agent based on a dynamic cross-linking-controlled dissolution mechanism, the chemical structure of which is a dynamic cross-linking network, and the dynamic chemical structure in the cross-linking network includes a Diels-Alder addition structure.

[0006] The second aspect of the present application provides a latent curing agent based on a dynamic crosslinking-controlled dissolution mechanism, which at least comprises a reaction product of the following components:

[0007] Component A, including a component having a maleimide structure,

[0008] Component B, including a component having a furan ring structure,

[0009] Component C, comprising an amine component having at least two amino groups or imino groups;

[0010] Wherein, the reaction product has a dynamic cross-linked network structure including a Diels-Alder addition structure.

[0011] In one embodiment, the mass ratio of the component having a maleimide structure to the component having a furan ring structure is 5:1-20, preferably 5:1-10, and more preferably 5:2-6, so as to obtain a cross-linked polymer compound and make the product easier to break.

[0012] In one embodiment, the mass ratio of the amine component having at least two amino or imino groups to the component having a maleimide structure is 25:3-5. If the mass ratio is too large or too small, some structures of the two cannot be cross-linked or the product is not easily broken.

[0013] In one embodiment, the component having a maleimide structure includes 1,5-bis(maleimide maleimide)-2-methyl-pentane, 1,5-bis(maleimide) pentane, 1,5-bis(maleimide) hexane, N',N-1,3-phenylene bismaleimide, N',N-1,4-phenylene bismaleimide, N,N-(4-methyl-1,3-phenylene) bismaleimide, 4,4'-bismaleimide diphenylmethane, 1,2-bis(maleimide) ethane and N',N- Any one or a combination of two or more of isophorone bismaleimide, 1,1′-[methylenebis(2-methyl-4,1-cyclohexanediyl)]bismaleimide, 1,1′-methylenebis(cyclohexylidene)bismaleimide, 1,1′-[1,4-cyclohexanediylbis(methylene)]bismaleimide, tris(2-maleimidoethyl)amine, 6-maleimidocaproic acid, 11-maleimidodecanoic acid, 3-maleimidopropionic acid, and 4-(maleimido)phenylisocyanate, and is not limited thereto.

[0014] In one embodiment, the component having a furan ring structure includes any one or a combination of two or more of furfuryl alcohol glycidyl ether, furan dimethanol diglycidyl ether, furfurylamine diglycidyl amine, furfural, furan acrylic acid, 2-furanacetic acid, tri(2-furanyl)phosphine, and 5-piperidin-1-yl-2-furanaldehyde, and is not limited thereto.

[0015] In one embodiment, the amine component having at least two amino groups or imino groups includes diethylenetriamine, pentamethyldiethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, 4,4′-diaminodiphenylmethane, ethylenediamine, hexamethylenediamine, adipic acid diamine, 1,5-diamino-2-methylpentane, 1,7-diaminoheptane, pentamethylenediamine, diethylaminopropylamine, menthanediamine, isophoronediamine, N-aminoethylpiperazine, 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiroundecane adduct, bis(4 -amino-3-methylcyclohexyl)methane, 4,4′-diaminodicyclohexylmethane, polyamide, tris(2-aminoethyl)amine, polyetheramine, histamine, propylenediamine, N,N-dimethyldipropylenetriamine, diethylenetriaminopropyltrimethoxysilane, bis(hexamethylene)triamine, N-(6-aminohexyl)-1,6-hexanediamine, trientine impurity, metaphenylenediamine, polyethylene polyamine, N-(3-aminopropyl)cyclohexylamine, N'-(3-aminopropyl)-N,N-dimethyl-1,3-propylenediamine, one or a combination of more than two thereof, and is not limited thereto.

[0016] In one embodiment, to obtain the reaction product, a first reaction and a second reaction can be carried out in sequence, wherein the first reaction mainly occurs between a component having a maleimide structure and a component having a furan ring structure, including a Diels-A1der addition reaction; the second reaction mainly occurs between the product of the first reaction and an amine component having at least two amino groups or imino groups, including one or more of an addition reaction of epoxy and amine, an organic acid and amine ionization reaction, a Schiff base reaction, and an addition reaction of isocyanate and amine. The temperature of the first reaction can be 40 to 90°C. The temperature of the second reaction can be 0 to 90°C, preferably 20 to 80°C, to promote reaction efficiency.

[0017] The third aspect of the present application provides a method for preparing the latent curing agent based on the dynamic crosslinking-controlled dissolution mechanism, which comprises:

[0018] Allowing a first uniformly mixed reaction system comprising component A, component B and a solvent to undergo a first reaction to obtain a first reaction mixture;

[0019] allowing a second uniformly mixed reaction system comprising the first reaction mixture and component C to undergo a second reaction to obtain the latent curing agent;

[0020] Wherein, the component A includes a component having a maleimide structure, the component B includes a component having a furan ring structure, the component C includes an amine component having at least two amino groups or imino groups, the first reaction includes a Diels-Alder addition reaction, and the second reaction includes one or more of an addition reaction of epoxy and amine, an ionization reaction of an organic acid and amine, a Schiff base reaction, and an addition reaction of an isocyanate and amine.

[0021] In one embodiment, the mass ratio of the component having a maleimide structure to the component having a furan ring structure is 5:1-20, preferably 5:1-10, and more preferably 5:2-6.

[0022] In one embodiment, the mass ratio of the amine component having at least two amino groups or imino groups to the component having a maleimide structure is 25:3-5.

[0023] In one embodiment, the mass ratio of the solvent to the component having a maleimide structure is 0 to 50:10, preferably 0 to 30:10, and more preferably 0 to 20:10, so that the target product is easier to obtain.

[0024] In one embodiment, the component having a maleimide structure includes 1,5-bis(maleimide maleimide)-2-methyl-pentane, 1,5-bis(maleimide) pentane, 1,5-bis(maleimide) hexane, N',N-1,3-phenylene bismaleimide, N',N-1,4-phenylene bismaleimide, N,N-(4-methyl-1,3-phenylene) bismaleimide, 4,4'-bismaleimide diphenylmethane, 1,2-bis(maleimide) ethane and N',N- Any one or a combination of two or more of isophorone bismaleimide, 1,1′-[methylenebis(2-methyl-4,1-cyclohexanediyl)]bismaleimide, 1,1′-methylenebis(cyclohexylidene)bismaleimide, 1,1′-[1,4-cyclohexanediylbis(methylene)]bismaleimide, tris(2-maleimidoethyl)amine, 6-maleimidocaproic acid, 11-maleimidodecanoic acid, 3-maleimidopropionic acid, and 4-(maleimido)phenylisocyanate, and is not limited thereto.

[0025] In one embodiment, the component having a furan ring structure includes any one or a combination of two or more of furfuryl alcohol glycidyl ether, furan dimethanol diglycidyl ether, furfurylamine diglycidyl amine, furfural, furan acrylic acid, 2-furanacetic acid, tri(2-furanyl)phosphine, and 5-piperidin-1-yl-2-furanaldehyde, and is not limited thereto.

[0026] In one embodiment, the amine component having at least two amino groups or imino groups includes diethylenetriamine, pentamethyldiethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, 4,4′-diaminodiphenylmethane, ethylenediamine, hexamethylenediamine, adipic acid diamine, 1,5-diamino-2-methylpentane, 1,7-diaminoheptane, pentamethylenediamine, diethylaminopropylamine, menthanediamine, isophoronediamine, N-aminoethylpiperazine, 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiroundecane adduct, bis(4 -amino-3-methylcyclohexyl)methane, 4,4′-diaminodicyclohexylmethane, polyamide, tris(2-aminoethyl)amine, polyetheramine, histamine, propylenediamine, N,N-dimethyldipropylenetriamine, diethylenetriaminopropyltrimethoxysilane, bis(hexamethylene)triamine, N-(6-aminohexyl)-1,6-hexanediamine, trientine impurity, metaphenylenediamine, polyethylene polyamine, N-(3-aminopropyl)cyclohexylamine, N'-(3-aminopropyl)-N,N-dimethyl-1,3-propylenediamine, one or a combination of more than two thereof, and is not limited thereto.

[0027] In one embodiment, the solvent includes any one or a combination of two or more of toluene, xylene, N',N-dimethylformamide, 1,4-dioxane, dimethyl sulfoxide, chloroform, water, tetrahydrofuran, ethanol, propanol, isopropanol, n-butanol, isobutanol, and N-methylpyrrolidone, and is not limited thereto.

[0028] In one embodiment, the temperature of the first reaction is 40-90°C, preferably 60-80°C, to obtain higher reaction efficiency and make the reaction more thorough. If the temperature of the first reaction is too high or too low, the Diels-Alder addition structure will be more reversible than the forward reaction or will not form.

[0029] In one embodiment, the first reaction time is 2 to 72 hours, preferably 6 to 24 hours.

[0030] In one embodiment, the temperature of the second reaction is 0-90°C, preferably 20-80°C, to obtain higher reaction efficiency and make the reaction more thorough. If the temperature of the second reaction is too high or too low, the Diels-Alder bond will dissociate or cross-linking will fail.

[0031] In one embodiment, the second reaction time is 0.5 to 36 hours, preferably 0.5 to 10 hours.

[0032] In one embodiment, after the second reaction is completed, the target product, namely the latent curing agent, can be separated from the formed second reaction mixture by post-treatment. The post-treatment may include operations such as removing solvent, washing, and drying.

[0033] The fourth aspect of the present application provides the use of the latent curing agent based on the dynamic crosslinking-controlled dissolution mechanism in the preparation of epoxy resin latent curing agent, latent epoxy resin curing accelerator, single-component coating, adhesive, electronic packaging material or composite material prepreg. In addition, the latent curing agent can also be used in the aerospace field.

[0034] The fifth aspect of the present application provides a resin composition comprising an epoxy resin and the latent curing agent based on the dynamic cross-linking-controlled dissolution mechanism.

[0035] In one embodiment, the mass ratio of the latent curing agent to the epoxy resin is 0.5-150:100, preferably 3-80:100.

[0036] In one embodiment, the resin composition includes an epoxy system. Further, the epoxy system includes any one or a combination of two or more of an epoxy-anhydride system, an epoxy-phenolic system, and an epoxy-dicyandiamide system, but is not limited thereto.

[0037] The sixth aspect of the present application provides a one-component thermosetting material, which can be formed by an epoxy resin and the latent curing agent based on the dynamic cross-linking-controlled dissolution mechanism.

[0038] In one embodiment, the mass ratio of the latent curing agent to the epoxy resin is 0.5-150:100, preferably 3-80:100.

[0039] Compared with the prior art, this application has at least the following beneficial effects:

[0040] First, a latent curing agent based on a dynamic cross-linked network structure is constructed, wherein a dynamic cross-linking-controlled dissolution mechanism is introduced, that is, at low temperatures (such as room temperature), the curing agent is a cross-linked network structure, insoluble in epoxy resin and exhibits no curing activity; under heating, the dynamic cross-linked structure in the curing agent is de-cross-linked, dissolved in epoxy resin and exhibits high curing activity, providing a new, simple and efficient strategy for the development of single-component thermosetting resins. Using the latent curing agent as a latent curing agent or curing accelerator for thermosetting resins can effectively hide and control the release of the reaction activity of the highly active cross-linking agent, achieve long storage and rapid cross-linking of single-component thermosetting materials, especially taking into account long-term storage at room temperature and rapid curing at medium and low temperatures, and has broad application prospects in the fields of single-component coatings, adhesives, electronic packaging materials, composite prepregs, etc.

[0041] Secondly, the process for preparing the latent curing agent based on the dynamic cross-linked network structure is simple, easy to operate, well controlled, easy to implement, and suitable for large-scale industrial production. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments recorded in the present application. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0043] Figure 1 is a photograph of a latent curing agent in Example 1 of the present application;

[0044] Figure 2 This is a temperature-dependent infrared spectrum of a latent curing agent in Example 1 of the present application;

[0045] Figure 3 It is a latent curing agent in Example 1 of the present application after heating 1 H NMR spectrum. DETAILED DESCRIPTION

[0046] In order to further understand the application, the application is further described below in conjunction with some embodiments. It should be understood that these embodiments are only used to illustrate the application and are not used to limit the scope of the application. The non-essential improvements and adjustments made by this field technician under the core guiding ideology of the application still belong to the protection scope of the application. The experimental methods without specifying specific conditions in the following examples are usually according to conventional conditions or according to the conditions recommended by the manufacturer. The experimental materials adopted in the following examples, if not otherwise specified, can all be purchased by conventional biochemical reagent stores.

[0047] Some of the test methods used in the following examples are as follows:

[0048] Rheological experiments: The viscosity of the samples was measured by isothermal rheological experiments with a rheometer (MCR) 302e (Anton Paar, Austria) in a 25 mm sample tray under parallel plate geometry at a shear strain of 0.01% to 10% (the specific shear strain value was determined by the test value in the linear elastic region), a frequency of 1 Hz, a temperature of 25 °C, and a time of 10 min.

[0049] Differential scanning calorimetry (DSC): Mettler-Toledo Star3 DSC (Mettler-Toledo, USA) was used in a nitrogen atmosphere at 50 mL min -1 The heating rate from 25 to 180 °C was 10 °C min -1 DSC curves were recorded to measure the glass transition temperature.

[0050] Tensile test: A universal testing machine UTM4000 (Shenzhen Sansi Zongheng Technology Co., Ltd., China) was used. The specimen gauge length was 40 mm, and the size was 80 mm (length) × 6 mm (width) × 0.3 mm (thickness). -1 Test at speed.

[0051] Example 1

[0052] 100 parts (all parts by mass unless otherwise specified below) of 1,5-bis(maleimide maleimide)-2-methyl-pentane, 110 parts of furfuryl alcohol glycidyl ether and 200 parts of toluene were placed in a round-bottom flask, stirred with a stirrer and subjected to a first reaction at 70°C for 8 hours. After cooling to room temperature, 80 parts of tetraethylenepentamine were added. After a second reaction at 70°C for 36 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain the target product, i.e., a latent curing agent, which was in powder form, such as Figure 1 The temperature-dependent infrared spectrum of the latent curing agent is shown in Figure 2 As shown, at 1650cm- 1 It is the infrared characteristic absorption peak of Diels-Alder addition structure. Figure 3 The latent curing agent is dissolved in DMSO-d6 at 130°C. 1 From the H NMR spectrum, we can see the peaks of the furan ring after the reverse Diels-Alder reaction of the Diels-Alder addition structure and the hydrogen atoms on the maleimide structure.

[0053] Comparative Example 1

[0054] 100 parts of 1,5-bis(maleimide maleimide)-2-methyl-pentane, 110 parts of furfuryl alcohol glycidyl ether and 200 parts of toluene were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 8 hours, then cooled to room temperature, the solvent was removed, crushed into fine powder, washed with petroleum ether and dried to obtain the final product.

[0055] Comparative Example 2

[0056] 100 parts of 1,5-bis(maleimide maleimide)-2-methyl-pentane, 110 parts of furfuryl alcohol glycidyl ether, 80 parts of tetraethylene pentamine and 200 parts of toluene are placed together in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 44 hours, then the solvent is removed, the mixture is crushed into fine powder, washed with petroleum ether and dried to obtain the final product.

[0057] Comparative Example 3 The preparation method of a latent curing agent provided in this comparative example is basically the same as that of Example 1, except that 500 parts of tetraethylenepentamine are used.

[0058] Comparative Example 4 The preparation method of a latent curing agent provided in this comparative example is basically the same as that of Example 1, except that 60 parts of tetraethylenepentamine are used.

[0059] Comparative Example 5 The preparation method of a latent curing agent provided in this comparative example is basically the same as that in Example 1, except that the temperature of the first reaction is set to 35°C.

[0060] Comparative Example 6 The preparation method of a latent curing agent provided in this comparative example is basically the same as that in Example 1, with the only difference being that the temperature of the first reaction is set to 95°C.

[0061] Comparative Example 7 The preparation method of a latent curing agent provided in this comparative example is basically the same as that in Example 1, except that the temperature of the first reaction is set to -1°C.

[0062] Example 2

[0063] 100 parts of N', N-isophorone bismaleimide and 120 parts of furfuryl alcohol glycidyl ether were placed in a round-bottom flask, stirred with a stirrer and reacted at 90°C for 2 hours. After cooling to room temperature, 80 parts of tetraethylenepentamine were added. After reacting at 0°C for 36 hours, the mixture was crushed into fine powder, washed with ethanol, and dried to obtain the target product in powder form.

[0064] Example 3

[0065] 358 parts of 4,4'-bismaleimidodiphenylmethane, 240 parts of furandimethanol diglycidyl ether and 1790 parts of ethanol were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 5 hours. After cooling to room temperature, 750 parts of 4,4'-diaminodiphenylmethane were added. After reacting at 90°C for 1 hour, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain the target product in powder form.

[0066] Example 4

[0067] 358 parts of N', N-1, 3-phenylene bismaleimide, 240 parts of furandimethanol diglycidyl ether and 380 parts of 1, 4-dioxane were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 5 hours. After cooling to room temperature, 750 parts of N-aminoethylpiperazine were added. After reacting at 70°C for 0.5 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain the target product in powder form.

[0068] Example 5

[0069] 100 parts of 4,4'-bismaleimidodiphenylmethane, 150 parts of furfuryl alcohol glycidyl ether and 280 parts of 1,4-dioxane were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 3 hours. After cooling to room temperature, 100 parts of trientine impurity were added. After 36 hours of reaction at 70°C, the solvent was removed, crushed into fine powder, washed with petroleum ether and dried to obtain a powdery target product.

[0070] Example 6

[0071] 100 parts of 1,5-bis(maleimide maleimide)-2-methyl-pentane and 120 parts of furfurylamine diglycidyl ether were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 72 hours. After cooling to room temperature, 60 parts of polyetheramine D230 were added. After reacting at 70°C for 6 hours, a gel product was obtained, which was crushed and vacuum dried at 70°C for 24 hours, the solvent was removed, crushed into fine powder, and dried to obtain a powdery target product.

[0072] Example 7

[0073] 80 parts of tris(2-maleimidoethyl)amine, 64 parts of furfuryl alcohol glycidyl ether and 400 parts of 1,4-dioxane were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 10 hours. After cooling to room temperature, 400 parts of tris(2-aminoethyl)amine were added. After reacting at 0°C for 36 hours, the solvent was removed, crushed into fine powder, washed with water and dried to obtain a powdery target product.

[0074] Example 8

[0075] 20 parts of 4-(maleimido)phenyl isocyanate, 15 parts of furfuryl alcohol glycidyl ether and 100 parts of N-methylpyrrolidone were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 5 hours. After cooling to room temperature, 100 parts of 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiroundecane were added, reacted at 70°C for 0.5 hours, the solvent was removed, crushed into fine powder, washed with water and dried to obtain a powdery target product.

[0076] Example 9

[0077] 100 parts of 1,5-bis(maleimide maleimide)-2-methyl-pentane, 110 parts of furfuryl alcohol glycidyl ether and 80 parts of N',N-dimethylformamide were placed in a round-bottom flask, stirred with a stirrer and reacted at 50°C for 12 hours. After cooling to room temperature, 80 parts of 4,4'-diaminodiphenylmethane were added. The mixture was reacted at 90°C for 0.5 hours, the solvent was removed, the mixture was crushed into fine powder, washed with propanol and dried to obtain the target product in powder form.

[0078] Example 10

[0079] 20 parts of 1,1′-[methylenebis(2-methyl-4,1-cyclohexanediyl)]bismaleimide, 60 parts of furfuryl alcohol glycidyl ether and 100 parts of xylene were placed in a round-bottom flask, stirred with a stirrer and reacted at 90°C for 5 hours. After cooling to room temperature, 80 parts of triethylenetetramine were added. After reacting at 90°C for 0.5 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain a powdery target product.

[0080] Embodiment 11

[0081] 100 parts of 1,1′-[1,4-cyclohexanediylbis(methylene)]bismaleimide, 150 parts of furfurylamine diglycidylamine and 500 parts of toluene were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 22 hours. After cooling to room temperature, 160 parts of triethylenetetramine were added. After reacting at 0°C for 20 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain a powdery target product.

[0082] Example 12

[0083] 100 parts of 1,1′-[1,4-cyclohexanediyl-bis(methylene)]bismaleimide, 100 parts of 5-phenyl-2-furancarboxylic acid and 280 parts of anisole were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 22 hours. After cooling to room temperature, 160 parts of triethylenetetramine were added. After reacting at 80°C for 5 hours, the solvent was removed, the mixture was crushed into fine powder, washed with ethanol and dried to obtain a powdery target product.

[0084] Example 13

[0085] 50 parts of N', N-1, 3-phenylene bismaleimide, 50 parts of 5-piperidin-1-yl-2-furanaldehyde and 180 parts of tetrahydrofuran were placed in a round-bottom flask, stirred with a stirrer and reacted at 65°C for 8 hours. After cooling to room temperature, 60 parts of propylene diamine were added. After reacting at 60°C for 5 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain the target product in powder form.

[0086] Embodiment 14

[0087] 70 parts of 3-maleimidopropionic acid, 60 parts of furan acrylic acid and 80 parts of chloroform were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 72 hours. After cooling to room temperature, 80 parts of m-phenylenediamine were added. The mixture was reacted at 90°C for 15 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain the target product in powder form.

[0088] Embodiment 15

[0089] 70 parts of 4,4'-bismaleimidodiphenylmethane, 130 parts of furfural and 140 parts of 1,4-dioxane were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 12 hours. After cooling to room temperature, 80 parts of tetraethylenepentamine were added. The mixture was reacted at 70°C for 3 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain the target product in powder form.

[0090] Example 16

[0091] 100 parts of 6-maleimidocaproic acid, 220 parts of furfural and 300 parts of ethylene glycol monomethyl ether were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 5 hours. After cooling to room temperature, 80 parts of tetraethylenepentamine were added. The mixture was reacted at 70°C for 36 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain the target product in powder form.

[0092] Embodiment 17

[0093] 100 parts of 11-maleimidodecanoic acid, 300 parts of furfural and 300 parts of dimethyl sulfoxide were placed in a round-bottom flask, stirred with a stirrer and reacted at 60°C for 5 hours. After cooling to room temperature, 500 parts of diethylenetriamine-propyltrimethoxysilane were added. The mixture was reacted at 0°C for 20 hours, the solvent was removed, the mixture was crushed into fine powder, washed with water and dried to obtain a powdery target product.

[0094] Embodiment 18

[0095] 200 parts of tris(2-maleimidoethyl)amine, 40 parts of furfural and 400 parts of chloroform were placed in a round-bottom flask, stirred with a stirrer and reacted at 60°C for 22 hours. After cooling to room temperature, 120 parts of pentamethylenediamine were added. The mixture was reacted at 70°C for 36 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain the target product in powder form.

[0096] Embodiment 19

[0097] 100 parts of tris(2-maleimidoethyl)amine, 400 parts of furfural and 200 parts of 1,4-dioxane were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 12 hours. After cooling to room temperature, 100 parts of pentamethylenediamine were added. The mixture was reacted at 50°C for 18 hours, the solvent was removed, the mixture was crushed into fine powder, washed with petroleum ether and dried to obtain the target product in powder form.

[0098] Embodiment 20

[0099] 500 parts of tri(2-maleimidoethyl)amine, 100 parts of tri(2-furyl)phosphine, 300 parts of 1,4-dioxane and 200 parts of acetonitrile were placed in a round-bottom flask, stirred with a stirrer and reacted at 70°C for 10 hours. After cooling to room temperature, 300 parts of polyetheramine D230 were added. The mixture was reacted at 60°C for 3 hours, the solvent was removed, the mixture was crushed into fine powder, washed with water and dried to obtain the target product in powder form.

[0100] Application Example 1

[0101] 60 parts of the final product of Example 1 were added to 100 parts of bisphenol A epoxy resin (E-51) and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After 6 months, the viscosity was 1.05 times the initial viscosity. The single-component mixture was heated at 130°C for 2.5 hours, with a glass transition temperature of 75°C and a tensile strength of 85 MPa.

[0102] Comparative Application Example 1-1

[0103] 60 parts of the final product of Comparative Example 1 were added to 100 parts of bisphenol A epoxy resin (E-51) and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After 6 months, the viscosity was 1.01 times the initial viscosity. The mixture was heated at 130°C for 2.5 hours and remained liquid without solidification.

[0104] Comparative Application Example 1-2

[0105] 60 parts of the final product of Comparative Example 2 were added to 100 parts of bisphenol A epoxy resin (E-51) and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After 6 months, the viscosity was 3.2 times the initial viscosity. The single-component mixture was heated at 130°C for 2.5 hours, with a glass transition temperature of 60°C and a tensile strength of 40 MPa.

[0106] Comparative Application Examples 1-3

[0107] 60 parts of the final product of Comparative Example 3 were added to 100 parts of bisphenol A epoxy resin (E-51) and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After one day, the viscosity was 6 times the initial viscosity. After half a month, the single-component mixture was heated at 130°C for 2.5 hours, with a glass transition temperature of 45°C and a tensile strength of 35 MPa.

[0108] Comparative Application Examples 1-4

[0109] 60 parts of the final product of Comparative Example 4 were added to 100 parts of bisphenol A epoxy resin (E-51) and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After 6 months, the viscosity was 1.01 times the initial viscosity. The single-component mixture was heated at 130°C for 2.5 hours, with a glass transition temperature of 67°C and a tensile strength of 50 MPa.

[0110] Comparative Application Examples 1-5

[0111] 60 parts of the final product of Comparative Example 5 were added to 100 parts of bisphenol A epoxy resin (E-51) and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After one day, the solid was formed. The single-component mixture was heated at 130°C for 2.5 hours. The glass transition temperature was 68°C and the tensile strength was 74 MPa.

[0112] Comparative Application Examples 1-6

[0113] 60 parts of the final product of Comparative Example 6 were added to 100 parts of bisphenol A epoxy resin (E-51) and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After 2 months, the viscosity was 2.1 times the initial viscosity. The single-component mixture was heated at 130°C for 2.5 hours, with a glass transition temperature of 65°C and a tensile strength of 70 MPa.

[0114] Comparative Application Examples 1-7

[0115] 60 parts of the final product of Comparative Example 6 were added to 100 parts of bisphenol A epoxy resin (E-51) and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After 0.5 month, the viscosity was 2.3 times the initial viscosity. The single-component mixture was heated at 130°C for 2.5 hours, with a glass transition temperature of 63°C and a tensile strength of 65 MPa.

[0116] Application Example 2

[0117] Three parts of the final product of Example 1 were added to 100 parts of bisphenol A epoxy resin (AG-80) and 140 parts of polyazelaic anhydride and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After four months, the viscosity remained essentially unchanged. The single-component mixture was heated at 130°C for 2 hours, with a glass transition temperature of 125°C and a tensile strength of 110 MPa.

[0118] Comparative Application Example 2-1

[0119] Three parts of the final product of Comparative Example 1 were added to 100 parts of bisphenol A epoxy resin (AG-80) and 140 parts of polyazelaic anhydride and mixed evenly. The viscosity was then monitored using a rheometer at room temperature. Four months later, the viscosity was 1.01 times the initial viscosity. The single-component mixture was heated at 130°C for 2 hours and remained liquid and could not be cured.

[0120] Comparative Application Example 2-2

[0121] 3 parts of the final product of Comparative Example 2 were added to 100 parts of bisphenol A epoxy resin (AG-80) and 140 parts of polyazelaic anhydride and mixed evenly. The viscosity was then monitored using a rheometer at room temperature. Half a month later, the viscosity was 2.6 times the initial viscosity. The single-component mixture was heated at 130°C for 2 hours, with a glass transition temperature of 104°C and a tensile strength of 95 MPa.

[0122] Comparative Application Example 2-3

[0123] 3 parts of the final product of Comparative Example 3 were added to 100 parts of bisphenol A epoxy resin (AG-80) and 140 parts of polyazelaic anhydride and mixed evenly. The viscosity was then monitored using a rheometer at room temperature. After one day, the viscosity was 2.4 times the initial viscosity. After half a month, it had become a solid. The single-component mixture was heated at 130°C for 2 hours, with a glass transition temperature of 106°C and a tensile strength of 98 MPa.

[0124] Comparative Application Example 2-4

[0125] Three parts of the final product of Comparative Example 4 were added to 100 parts of bisphenol A epoxy resin (AG-80) and 140 parts of polyazelaic anhydride and mixed evenly. The viscosity was then monitored using a rheometer at room temperature. After four months, the viscosity was 1.01 times the initial viscosity. The single-component mixture was heated at 130°C for 2 hours, with a glass transition temperature of 92°C and a tensile strength of 89 MPa.

[0126] Comparative Application Example 2-5

[0127] Three parts of the final product of Comparative Example 5 were added to 100 parts of bisphenol A epoxy resin (AG-80) and 140 parts of polyazelaic anhydride and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. After two days, the viscosity was 2.3 times the initial viscosity. The single-component mixture was heated at 130°C for two hours, with a glass transition temperature of 95°C and a tensile strength of 92 MPa.

[0128] Comparative Application Example 2-6

[0129] Three parts of the final product of Comparative Example 6 were added to 100 parts of bisphenol A epoxy resin (AG-80) and 140 parts of polyazelaic anhydride and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. One month later, the viscosity was 2.2 times the initial viscosity. The single-component mixture was heated at 130°C for 2 hours, with a glass transition temperature of 100°C and a tensile strength of 91 MPa.

[0130] Comparative Application Example 2-7

[0131] Three parts of the final product of Comparative Example 7 were added to 100 parts of bisphenol A epoxy resin (AG-80) and 140 parts of polyazelaic anhydride and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. One month later, the viscosity was 2.1 times the initial viscosity. The single-component mixture was heated at 130°C for 2 hours, with a glass transition temperature of 98°C and a tensile strength of 92 MPa.

[0132] Application Example 3

[0133] 3 parts of the final product of Example 1 were added to 100 parts of bisphenol A epoxy resin (E-51) and 7 parts of dicyandiamide and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. The viscosity was 1.2 times the initial viscosity after 6 months. The single-component mixture was cured at 130°C for 1 hour and at 150°C for 3 hours. The glass transition temperature was 110°C and the tensile strength was 60 MPa.

[0134] Application Example 4

[0135] 0.5 parts of the final product of Example 2 was added to 100 parts of bisphenol A epoxy resin (DER-331) and 70 parts of tetrahydrophthalic anhydride and mixed uniformly. The viscosity was then monitored by a rheometer at room temperature. The viscosity was 1.01 times the initial viscosity after 6 months. The single component was cured at 120° C. for 0.5 hours and then at 150° C. for 2.5 hours. The glass transition temperature was 100° C. and the tensile strength was 75 MPa.

[0136] Application Example 5

[0137] 40 parts of the final product of Example 3 were added to 100 parts of bisphenol A epoxy resin (DER-331) and uniformly mixed, and then stored at room temperature for 5 months. The viscosity was 1.01 times the initial viscosity after 6 months. The single-component mixture was cured at 110° C. for 1 hour and then at 160° C. for 3 hours. The glass transition temperature was 165° C. and the tensile strength was 80 MPa.

[0138] Application Example 6

[0139] 50 parts of the final products of Examples 4 to 10 were added to 100 parts of bisphenol A epoxy resin (DER-331) and mixed uniformly. The viscosity was then monitored by a rheometer at room temperature. The viscosity was 1.02, 1.03, 1.01, 1.12, 1.01 and 1.02 times the initial viscosity after 6 months. The single component was cured at 140° C. for 2 hours. The glass transition temperatures were 121° C., 90° C., 78° C., 95° C., 110° C., 157° C. and 135° C., and the tensile strengths were 105 MPa, 80 MPa, 70 MPa, 83 MPa, 120 MPa, 95 MPa and 125 MPa, respectively.

[0140] Application Example 7

[0141] 50 parts of the final products of Examples 19 and 20 were added to 100 parts of bisphenol A epoxy resin (E-54) and mixed evenly. The viscosity was then monitored by a rheometer at room temperature. The viscosities were 1.01, 1.19 and 1.03 times the initial values ​​after 6 months. The three single-component mixtures were cured at 150°C for 5 hours to successfully prepare cured products with glass transition temperatures of 123°C, 130°C and 125°C, respectively, and tensile strengths of 126 MPa, 115 MPa and 130 MPa, respectively.

[0142] Application Example 8

[0143] 40 parts of the final product of the product of Examples 12, 14, and 18 were added to 100 parts of bisphenol A epoxy resin (E-54) and mixed uniformly. Then, the viscosity was monitored by a rheometer at room temperature. The viscosity was 1.3 times, 1.4 times, and 1.03 times the initial viscosity after 6 months. The three single-component mixtures were placed at 130° C. for 5 hours, and then 150° C. for 2.5 hours to successfully prepare a cured product. The glass transition temperatures were 81° C., 175° C., and 95° C., respectively, and the tensile strengths were 100 MPa, 85 MPa, and 65 MPa, respectively.

[0144] Application Example 9

[0145] 50 parts of the final products of Examples 12, 14 and 18 were respectively added to 100 parts of bisphenol A epoxy resin (E-54) and mixed evenly, and then the viscosity was monitored by a rheometer at room temperature. The viscosity was 1.3 times, 1.4 times and 1.05 times the initial viscosity after 6 months. The three single-component mixtures were cured at 120°C for 5 hours and then cured at 160°C for 2.5 hours to successfully prepare a cured product. The glass transition temperatures were 90°C, 180°C and 100°C, respectively, and the tensile strengths were 105 MPa, 90 MPa and 70 MPa, respectively.

[0146] Application Example 10

[0147] Three parts of the final products of Examples 13, 15, and 16 were added to 100 parts of bisphenol F epoxy resin (S-170) and 60 parts of phenolic resin and mixed uniformly. The viscosity was then monitored by a rheometer at room temperature. The viscosity was 1.4 times, 1.5 times, and 1.05 times the initial viscosity after 6 months. The three single-component mixtures were cured at 130° C. for 5 hours. Then, the cured product was successfully prepared by curing at 140° C. for 2.5 hours. The glass transition temperatures were 115° C., 120° C., and 98° C., respectively, and the tensile strengths were 75 MPa, 80 MPa, and 93 MPa, respectively.

[0148] In addition, the applicant also referred to the above embodiments and conducted experiments with other raw materials, process operations, and process conditions described in this specification, and obtained relatively ideal results.

[0149] Based on the above embodiments, it can be seen that the epoxy resin latent curing agent (or accelerator) developed by the present application based on the dynamic cross-linking-controlled dissolution mechanism has a simple preparation process, simple operation, good controllability, easy implementation, and is suitable for large-scale industrial production. Moreover, based on this type of epoxy resin latent curing agent (or accelerator), long-term storage and medium and low temperature curing of single-component thermosetting materials can be achieved, especially when applied to epoxy-anhydride systems, epoxy-phenolic systems, and epoxy-dicyandiamide systems, which not only reduces the curing temperature, but also greatly prolongs the storage period, and provides a new, simple and efficient strategy for the development of single-component thermosetting resins.

[0150] Although the present application has been described with reference to illustrative embodiments, it will be appreciated by those skilled in the art that various other changes, omissions, and / or additions may be made and that elements of the described embodiments may be substituted with substantial equivalents without departing from the spirit and scope of the present application. In addition, many modifications may be made to adapt a particular situation or material to the teachings of the present application without departing from the scope of the present application. Therefore, it is not intended herein to limit the present application to the disclosed specific embodiments for carrying out the present application, but rather it is intended that the present application will include all embodiments within the scope of the appended claims.

Claims

1. A latent curing agent based on dynamic crosslinking-controlled dissolution mechanism, characterized in that: The reaction product comprising at least the following components: Component A, including a component having a maleimide structure, Component B, including a component having a furan ring structure, Component C, comprising an amine component having at least two amino groups or imino groups; Wherein, the reaction product has a dynamic cross-linked network structure including a Diels-Alder addition structure.

2. The latent curing agent based on dynamic crosslinking-controlled dissolution mechanism according to claim 1, characterized in that: The mass ratio of the component having a maleimide structure to the component having a furan ring structure is 5:1-20, and the mass ratio of the amine component having at least two amino or imino groups to the component having a maleimide structure is 25-3:

5.

3. The latent curing agent based on dynamic crosslinking-controlled dissolution mechanism according to any one of claims 1-2, characterized in that: The components having maleimide structures include 1,5-bis(maleimide maleimide)-2-methyl-pentane, 1,5-di(maleimide)pentane, 1,5-di(maleimide)hexane, N',N-1,3-phenylene bismaleimide, N',N-1,4-phenylene bismaleimide, N,N-(4-methyl-1,3-phenylene)bismaleimide, 4,4'-bismaleimide diphenylmethane, 1,2-di(maleimide)ethane and N',N-isopropylamine. Any one of phorone bismaleimide, 1,1′-[methylenebis(2-methyl-4,1-cyclohexanediyl)]bismaleimide, 1,1′-methylenebis(cyclohexylidene)bismaleimide, 1,1′-[1,4-cyclohexanediylbis(methylene)]bismaleimide, tris(2-maleimidoethyl)amine, 6-maleimidocaproic acid, 11-maleimidodecanoic acid, 3-maleimidopropionic acid, and 4-(maleimido)phenylisocyanate, or a combination of two or more thereof; And / or, the component having a furan ring structure includes any one or a combination of two or more of furfuryl alcohol glycidyl ether, furan dimethanol diglycidyl ether, furfurylamine diglycidyl amine, furfural, furan acrylic acid, 2-furanacetic acid, tri(2-furanyl)phosphine, and 5-piperidin-1-yl-2-furanaldehyde; And / or, the amine component having at least two amino groups or imino groups includes diethylenetriamine, pentamethyldiethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, 4,4′-diaminodiphenylmethane, ethylenediamine, hexamethylenediamine, adipic acid diamine, 1,5-diamino-2-methylpentane, 1,7-diaminoheptane, pentamethylenediamine, diethylaminopropylamine, menthanediamine, isophoronediamine, N-aminoethylpiperazine, 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiroundecane adduct, bis( 4-amino-3-methylcyclohexyl)methane, 4,4'-diaminodicyclohexylmethane, polyamide, tris(2-aminoethyl)amine, polyetheramine, histamine, propylenediamine, N,N-dimethyldipropylenetriamine, diethylenetriaminopropyltrimethoxysilane, bis(hexamethylene)triamine, N-(6-aminohexyl)-1,6-hexanediamine, trientine impurity, metaphenylenediamine, polyethylene polyamine, N-(3-aminopropyl)cyclohexylamine, N'-(3-aminopropyl)-N,N-dimethyl-1,3-propylenediamine, one or a combination of two or more thereof.

4. A method for preparing a latent curing agent based on a dynamic crosslinking-controlled dissolution mechanism, characterized in that: include: Allowing a first uniformly mixed reaction system comprising component A, component B and a solvent to undergo a first reaction to obtain a first reaction mixture; allowing a second uniformly mixed reaction system comprising the first reaction mixture and component C to undergo a second reaction to obtain the latent curing agent; Wherein, the component A includes a component having a maleimide structure, the component B includes a component having a furan ring structure, the component C includes an amine component having at least two amino groups or imino groups, the first reaction includes a Diels-Alder addition reaction, and the second reaction includes one or more of an addition reaction of epoxy and amine, an ionization reaction of an organic acid and amine, a Schiff base reaction, and an addition reaction of an isocyanate and amine.

5. The preparation method according to claim 4, characterized in that: The mass ratio of the component having a maleimide structure to the component having a furan ring structure is 5:1 to 20, the mass ratio of the amine component having two or more amino or imino groups to the component having a maleimide structure is 25 to 3:5; and / or the mass ratio of the solvent to the component having a maleimide structure is 0 to 50:

10.

6. The preparation method according to any one of claims 4-5, characterized in that: The components having maleimide structures include 1,5-bis(maleimide maleimide)-2-methyl-pentane, 1,5-di(maleimide)pentane, 1,5-di(maleimide)hexane, N',N-1,3-phenylene bismaleimide, N',N-1,4-phenylene bismaleimide, N,N-(4-methyl-1,3-phenylene)bismaleimide, 4,4'-bismaleimide diphenylmethane, 1,2-di(maleimide)ethane and N',N-isopropylamine. Any one of phorone bismaleimide, 1,1′-[methylenebis(2-methyl-4,1-cyclohexanediyl)]bismaleimide, 1,1v-methylenebis(cyclohexylidene)bismaleimide, 1,1′-[1,4-cyclohexanediylbis(methylene)]bismaleimide, tris(2-maleimidoethyl)amine, 6-maleimidocaproic acid, 11-maleimidodecanoic acid, 3-maleimidopropionic acid, and 4-(maleimido)phenylisocyanate, or a combination of two or more thereof. And / or, the component having a furan ring structure includes any one or a combination of two or more of furfuryl alcohol glycidyl ether, furandimethanol diglycidyl ether, furfurylamine diglycidyl amine, furfural, furan acrylic acid, 2-furanacetic acid, tri(2-furanyl)phosphine, and 5-piperidin-1-yl-2-furanaldehyde. and / or, the amine component having at least two amino groups or imino groups includes diethylenetriamine, pentamethyldiethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, 4,4′-diaminodiphenylmethane, ethylenediamine, hexamethylenediamine, adipic acid diamine, 1,5-diamino-2-methylpentane, 1,7-diaminoheptane, pentamethylenediamine, diethylaminopropylamine, menthanediamine, isophoronediamine, N-aminoethylpiperazine, 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiroundecane adduct, bis(3-aminopropyl)-2,4,8,10-tetraoxaspiroundecane adduct, (4-amino-3-methylcyclohexyl) methane, bis(4-aminocyclohexyl) methane, polyamide, tris(2-aminoethyl) amine, polyether amine, histamine, propylene diamine, N,N-dimethyldipropylene triamine, diethylenetriaminopropyl trimethoxysilane, bis(hexamethylene) triamine, N-(6-aminohexyl)-1,6-hexanediamine, trientine impurity, metaphenylenediamine, polyethylene polyamine, N-(3-aminopropyl) cyclohexylamine, N'-(3-aminopropyl)-N,N-dimethyl-1,3-propylene diamine, one or a combination of two or more thereof; And / or, the solvent includes any one or a combination of two or more of toluene, xylene, N',N-dimethylformamide, 1,4-dioxane, dimethyl sulfoxide, chloroform, water, tetrahydrofuran, ethanol, propanol, isopropanol, n-butanol, isobutanol, N-methylpyrrolidone, acetonitrile, anisole or ethylene glycol monomethyl ether.

7. The preparation method according to claim 4, characterized in that: The temperature of the first reaction is 40-90° C., and the time is 2-72 hours; and / or, the temperature of the second reaction is 0-90° C., and the time is 0.5-36 hours.

8. Use of the latent curing agent based on dynamic crosslinking-controlled dissolution mechanism according to any one of claims 1 to 3 in the preparation of epoxy resin latent curing agent, epoxy resin latent curing accelerator, single-component coating, adhesive, electronic packaging material or composite material prepreg.

9. A resin composition comprising an epoxy resin, characterized in that: The resin composition further comprises a latent curing agent based on a dynamic cross-linking-controlled dissolution mechanism as described in any one of claims 1 to 3.

10. The resin composition according to claim 9, characterized in that: The mass ratio of the latent curing agent to the epoxy resin is 0.5 to 150:100; and / or the resin composition includes an epoxy system, and the epoxy system includes any one of an epoxy-anhydride system, an epoxy-phenolic system, and an epoxy-dicyandiamide system, or a combination of two or more thereof.

Images