Triazine benzene compound, composition, condensate and preparation method and application thereof

Abstract

The invention discloses a triazine benzene compound, a composition, a cured product and a preparation method and application of the triazine benzene compound, the composition and the cured product. The compound is phenolic resin with a triazine benzene structure obtained through condensation polymerization of cyanophenol. Respectively reacting the phenolic resin with an epichlorohydrin compound and an acyl chloride compound to obtain epoxy resin with a triazine benzene structure and active ester; in the curing process, triazine ring (containing nitrogen) is introduced as a node, trifunctional epoxy resin with a rigid aromatic structure as an arm and an active ester curing agent (the same skeleton) are prepared into a thermosetting cross-linked network by adopting a non-polar cross-linking scheme, and a three-dimensional network intrinsic pore structure is formed through in-situ cross-linking regulation and control of a rigid long-arm branched unit. Further, the bottlenecks of low dielectric, high temperature resistance, flame retardance, low heat release and the like are broken through, and the cured material has the characteristics of excellent flame retardance, high temperature resistance, low dielectric, high bending modulus, low heat release rate and linear thermal expansion coefficient performance.

Description

Technical Field

[0001] The invention belongs to the field of thermosetting resin materials, and specifically relates to a triazine benzene compound, a composition, a cured product, and a preparation method and application thereof. Background Art

[0002] Thermosetting resin is a kind of high molecular polymer material, the molecular chain is chemically cross-linked together to form a rigid three-dimensional network structure, with excellent comprehensive performance. Commonly used thermosetting resins include epoxy resin, polyester resin, vinyl ester, bismaleimide, thermosetting polyimide, cyanate ester, etc. However, there are some performance deficiencies such as poor high temperature resistance, high dielectric constant and dielectric loss, high heat release, large thermal expansion coefficient, flammability, etc. These deficiencies limit its application field to a certain extent.

[0003] Epoxy resin refers to an organic polymer compound containing two or more epoxy groups in the molecule. Because its molecular structure contains active epoxy groups, it can undergo a cross-linking reaction with a curing agent to form an insoluble, infusible polymer with a three-dimensional network structure. This structure contains a large number of polar groups such as hydroxyl, ether, and amino groups, which give the material many excellent properties, such as excellent adhesion, high temperature resistance, insulation, corrosion resistance, and low shrinkage, and the cost is relatively low. However, a large number of polar groups will increase the dielectric loss and water absorption of the cured product, which cannot meet the requirements of the new generation of low-dielectric thermosetting resin materials. Summary of the invention

[0004] The purpose of the present invention is to provide a triazine benzene compound and a preparation method thereof. The triazine benzene compound is obtained by cyclotrimerization of a p-cyanophenol compound. A cured product prepared based on the compound has obvious improvements in high temperature resistance, low dielectric constant, high bending modulus, low heat release and low thermal expansion coefficient compared with traditional bisphenol A type and tetraglycidylamine type epoxy resins while ensuring flame retardancy.

[0005] The preparation method provided by the invention is simple, easy to implement and suitable for large-scale industrial production.

[0006] In order to achieve the above object, in the first aspect, the present invention provides a compound having the structure of the compound represented by the following general formula (I) or (II):

[0007]

[0008] In the general formula (I), R 1 -R 15 Each independently represents one of the following groups of general formula (I'),

[0009]

[0010] R 1 -R 15 At least three of them are not H; the A groups independently represent a linear or branched alkyl group having 0 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms;

[0011]

[0012] The multifunctional triazine benzene epoxy resin represented by the general formula (II) wherein R 1a -R 15a Each independently represents one of the following groups of general formula (II'), and there are at least three of them, and the rest are H,

[0013]

[0014] The multifunctional triazine benzene active ester represented by the general formula (II) wherein R 1a -R 15a Each independently represents one of the following groups of general formula (II"), and there are at least three of them, and the rest are H.

[0015]

[0016] In a second aspect, the present invention provides a method for preparing the above-mentioned compound, which comprises the following steps: dissolving a cyanophenol compound in a solvent, adding a catalyst, and preparing R of the compound represented by general formula (I) 1 , R 6 and R 11 The phenolic resin represents -OH; the p-cyanophenol compound is 4-hydroxybenzene-4-nitrile; the solvent is ethylene dichloride; the catalyst is trifluoromethanesulfonic acid or ZnCl 2 .

[0017] Optionally, the method for preparing the compound represented by the general formula (II) comprises the following steps: obtaining β-substituted epichlorohydrin or acyl chloride wherein the B or C group independently represents one of H, alkyl, alkenyl, alkynyl, and phenyl;

[0018] Under the action of a catalyst, a compound represented by the general formula (I) containing an active group undergoes a ring-opening and ring-closing reaction with β-substituted epichlorohydrin to obtain a multifunctional triazine benzene epoxy resin;

[0019] Alternatively, a compound represented by the general formula (I) containing an active group is subjected to a substitution reaction with an acyl chloride compound in the presence of a catalyst to obtain a polyfunctional triazine benzene active ester having the structure of the compound represented by the general formula (II).

[0020] In a fourth aspect, the present invention provides a method for preparing the compound as described above, comprising the following steps:

[0021] (1) dissolving a cyanophenol compound in a solvent, adding a catalyst, and preparing R of the compound represented by the general formula (I) 1 , R 6 and R 11 The phenolic resin represents -OH; the p-cyanophenol compound is 4-hydroxybenzene-4-nitrile; the solvent is ethylene dichloride; the catalyst is trifluoromethanesulfonic acid or ZnCl 2 .

[0022] (2) reacting the phenolic resin, epichlorohydrin compound and phase transfer catalyst described in step (1) to obtain R of the compound represented by general formula (II) 1a , R 6a and R 11a express The epoxy resin has an epoxy value of 0.400-0.514.

[0023] Optionally, the phase transfer catalyst is one or a combination of trioctylmethylammonium chloride, dodecyltrimethylammonium chloride, tetrabenzyltrimethylammonium chloride, tetramethylammonium bromide, benzyltriethylammonium chloride, tetrabutylammonium bromide and tetrabutylammonium hydrogen sulfate; and the epichlorohydrin compound is epichlorohydrin.

[0024] Optionally, the method for preparing the compound as described above comprises the following steps:

[0025] (1) dissolving a cyanophenol compound in a solvent, adding a catalyst, and preparing R of the compound represented by the general formula (I) 1 , R 6 and R 11 The phenolic resin represents -OH; the p-cyanophenol compound is 4-hydroxybenzene-4-nitrile; the solvent is ethylene dichloride; the catalyst is trifluoromethanesulfonic acid or ZnCl 2 .

[0026] (2) dissolving the phenolic resin in step (1) in a solvent, adding an acyl chloride compound and an amine compound in sequence, and reacting to obtain R of the compound represented by general formula (II) 1a , R 6a and R 11a express of active esters.

[0027] Optionally, in step (2), the solvent is tetrahydrofuran or ethyl acetate; the acyl chloride compound is acetyl chloride or benzoyl chloride; and the amine compound is triethylamine.

[0028] In a fifth aspect, the present invention provides a curable composition comprising the compound as described above or the compound obtained by the preparation method as described above.

[0029] In a sixth aspect, the present invention provides a cured product obtained by curing the curable composition as described above.

[0030] In the seventh aspect, the present invention provides a method for preparing the cured product as described above, which comprises the following steps: the multifunctional triazine benzene epoxy resin represented by the general formula (II) is melted by heating and cured by heating in sequence to obtain a triazine benzene epoxy cured product.

[0031] Optionally, the method for preparing the cured product as described above comprises the following steps: mixing the multifunctional triazine benzene epoxy resin represented by the general formula (II) and the multifunctional triazine benzene active ester represented by the general formula (II) according to a ratio, adding an accelerator, and obtaining a triazine benzene epoxy cured product after curing.

[0032] Optionally, the accelerator is an imidazole accelerator; the imidazole accelerator is preferably 2-methyl imidazoline (2MZL), 2-heptadecylimidazole (C17Z), 2-ethyl-4-methylimidazole (2E4MZ), 1-cyanoethyl-2-ethyl-4-methylimidazole (2E4MZ-CN), the imidazole accelerator is selected from 2-methylimidazole (2MZ), 1-dodecyl-2-methyl-3-benzylimidazole chloride (SFZ), 1-cyanoethyl-2-undecylimidazole (C11Z-CN), 1-cyanoethyl-2-phenylimidazole (2PZ-CN), 1,3-dibenzyl-2-methylimidazole chloride (FFZ), 2-ethyl-4-methylimidazole (2E4MZ), 1-cyanoethyl-2 -methylimidazole (2MZ-CN), 2-undecylimidazole (C11Z), 1-cyanoethyl-2-phenylimidazole trimellitate (2PZ-CNS), 1-benzyl-2-methylimidazole (1B2MZ), 2-phenyl-4-methylimidazole (2P4MZ), 1-cyanoethyl-2-methylimidazole trimellitate, 1-cyanoethyl-2-undecylimidazole trimellitate (C11Z-CNS), 2-phenylimidazole (2PZ), 1-cyanoethyl-2-ethyl-4-methylimidazole trimellitate (2E4MZ-CNS), trimellitate (2MZ-CNS) and 2,4-diamino-6[2'-methylimidazole-(1')]ethyl-S-triazine (2MZ-A) or a combination thereof.

[0033] In an eighth aspect, the present invention provides an application of a solidified material obtained by the preparation method as described above, which is applied in the fields of electronics, aerospace, automobile industry, construction or coatings.

[0034] Compared with the prior art, the present invention has the following beneficial effects:

[0035] (1) The present invention provides a triazine benzene compound and a preparation method thereof, wherein a phenolic resin having a triazine benzene structure is obtained by a polycondensation reaction of p-cyanophenol, and then the phenolic resin is reacted with an epichlorohydrin compound and an acyl chloride compound to obtain an epoxy resin and an active ester having a triazine benzene structure, and under the action of an imidazole accelerator, a triazine ring (containing nitrogen) is introduced as a node, and a triazine benzene epoxy resin with a rigid aromatic structure as an arm and a triazine benzene active ester curing agent (same skeleton) are prepared by a non-polar crosslinking scheme to obtain a thermosetting crosslinked network, and a three-dimensional network intrinsic structure is formed by in-situ crosslinking of rigid long-arm branching units, thereby breaking through the bottlenecks of low dielectric, high temperature resistance, flame retardancy, etc., and the cured material has excellent flame retardancy, high temperature resistance, low dielectric, high bending modulus, ultra-low heat release and low linear thermal expansion coefficient performance characteristics.

[0036] (2) The preparation method of the present invention introduces triazine rings and benzene structures into epoxy resin and active ester, and ensures the rigidity and high symmetry of the structure through "π-π" conjugation. The epoxy and active ester molecules are alternately ringed to form a porous structure; and the active ester and epoxy resin are cross-linked without generating hydroxyl groups, which further improves the dielectric properties of the epoxy resin.

[0037] (3) After the active ester reacts with the epoxy group, it does not form a hydroxyl group on the side chain, but instead produces an ester group with a smaller polarity and a larger volume, which is beneficial for reducing dielectric loss and water absorption, and reducing curing shrinkage and internal stress. Although the ester group as an epoxy curing agent will reduce Tg, the heat resistance of the cured product can be maintained to a certain extent by greatly improving the skeleton rigidity and functionality of the active ester curing agent.

[0038] (4) The present invention introduces a benzene structure into triazine epoxy. Compared with the biphenyl structure, the triazine benzene compound obtained has a higher degree of conjugation, a higher thermal decomposition temperature, and a more stable structure; a smaller molecular weight and a higher epoxy value, which further improves the flame retardancy, high temperature resistance and mechanical properties of the cured product.

[0039] (5) The preparation method of the present invention is simple and efficient, has good controllability, is easy to operate, and has high product purity, and is suitable for large-scale industrial production. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] Figure 1 The infrared spectra of the triazine benzene precursor, phenolic resin, epoxy resin and active ester in Examples 1 and 2 are shown.

[0041] Figure 2 This is the curing kinetics diagram of triazine benzene epoxy resin and active ester in Example 2.

[0042] Figure 3 This is the TGA diagram of the epoxy active ester cured product in Examples 1 and 2.

[0043] Figure 4 DMA diagram of epoxy active ester cured product in Examples 1 and 2.

[0044] Figure 5 1 and 2 are the relationship between the dielectric constant, dielectric loss and frequency of the epoxy active ester cured product.

[0045] Figure 6 This is the cone calorimeter diagram of the epoxy active ester cured product of Example 2.

[0046] Figure 7 This is the TMA diagram of the epoxy active ester cured product of Example 2.

[0047] Figure 8 This is a bending performance diagram of the cured epoxy active ester-Kevlar composite material of Example 2. DETAILED DESCRIPTION

[0048] In order to make the above-mentioned objects, features and advantages of the invention more obvious and easy to understand, the specific embodiments of the invention are described in detail below.

[0049] In the following description, many specific details are set forth to facilitate a full understanding of the present invention, but the present invention may also be implemented in other ways different from those described herein, and those skilled in the art may make similar generalizations without violating the connotation of the present invention. Therefore, the present invention is not limited to the specific embodiments disclosed below.

[0050] A method for preparing an epoxy resin containing a triazine benzene structure, comprising the following steps:

[0051] (1) Preparation of phenolic resin: dissolve a p-cyanophenol compound in a solvent to maintain its concentration at 15%-30% g / ml, stir and reflux at 0°C for 10 min, add a catalyst in a molar ratio of p-cyanophenol compound: catalyst = 1:3, stir for 30 min until the liquid phase is uniform, then slowly heat the system to room temperature (25°C) and react for 12 h, add ice water, add ammonia water dropwise to adjust the pH value to neutral, filter and wash with water 3-6 times, and vacuum dry to obtain a phenolic resin containing a triazine benzene structure, the structural formula of which is as follows:

[0052]

[0053] (2) Preparation of epoxy resin: The phenolic resin and epichlorohydrin compound prepared in step (1) are stirred under nitrogen reflux at 65° C. until they are homogeneous, a phase transfer catalyst is added, and the molar ratio of the phenolic resin: epichlorohydrin compound: phase transfer catalyst is 1:30:0.1565. After reacting for 10 minutes, sodium hydroxide is added, and the molar ratio of sodium hydroxide: phenolic resin is 3.6:1. The reaction is continued for 3 hours. After the reaction is completed, the filtrate is filtered, and the filtrate is washed with hot water for 3 times, and dehydrated with anhydrous sodium sulfate for more than 6 hours. The filtrate is filtered again and the solvent is removed by rotary evaporation. The product is placed in a vacuum oven and dried to obtain an epoxy resin containing a triazine benzene structure, and the epoxy value thereof is 0.400-0.514. The structural formula is as follows:

[0054]

[0055] (3) Preparation of active ester: The phenolic resin obtained in step (1) is stirred with a solvent under nitrogen reflux at 0°C until it becomes homogeneous, maintaining its concentration at 10%-35% g / ml, adding an acyl chloride compound, wherein the molar ratio is phenolic resin: acyl chloride compound = 1:1.5-2, keeping the temperature for 10 minutes, then slowly adding an amine compound dropwise, wherein the molar ratio is phenolic resin: amine compound = 1:1.5-2, reacting for 2 hours, then heating to 25°C to react for 2 hours, and then heating to 60°C to react for 2 hours, filtering to remove the generated amine compound salt, and rotary distilling the filtrate to remove the solvent, adding ethyl acetate to dissolve it again, washing with hot water until neutral, removing water with anhydrous sodium sulfate, and then rotary distilling to remove the solvent, and drying the product in a vacuum oven to obtain an active ester containing a triazine benzene structure, the structural formula of which is as follows:

[0056]

[0057] (4) Preparation of epoxy active ester curing material: After epoxy resin and active ester are uniformly mixed at 140°C according to the ratio, an accelerator is added and stirred rapidly. The molar ratio is epoxy resin: active ester: accelerator = 6:5:0.11. The mixture is poured into a mold and cured in three stages according to the curing process: 200°C / 2h, 225°C / 2h, and 250°C / 4h. After natural cooling, a triazine benzene epoxy active ester curing material is obtained.

[0058] In one embodiment of the present invention, the p-cyanophenol compound in step (1) is 4-hydroxybenzene-4-carbonitrile.

[0059] In one embodiment of the present invention, the solvent in step (1) is ethylene dichloride.

[0060] In one embodiment of the present invention, the catalyst in step (1) is trifluoromethanesulfonic acid or ZnCl 2 .

[0061] In one embodiment of the present invention, the phase transfer catalyst in step (2) is one or a combination of trioctylmethylammonium chloride, dodecyltrimethylammonium chloride, tetrabenzyltrimethylammonium chloride, tetramethylammonium bromide, benzyltriethylammonium chloride, tetrabutylammonium bromide or tetrabutylammonium hydrogen sulfate.

[0062] In one embodiment of the present invention, the epichlorohydrin compound in step (2) is epichlorohydrin.

[0063] In one embodiment of the present invention, the solvent in step (3) is tetrahydrofuran and ethyl acetate.

[0064] In one embodiment of the present invention, the acyl chloride compound in step (3) is acetyl chloride or benzoyl chloride.

[0065] In one embodiment of the present invention, the amine compound in step (3) is triethylamine

[0066] In one embodiment of the present invention, the accelerator of step (4) is 2-methyl imidazoline (2MZL), 2-heptadecylimidazole (C17Z), 2-ethyl-4-methylimidazole (2E4MZ), 1-cyanoethyl-2-ethyl-4-methylimidazole (2E4MZ-CN), the imidazole accelerator is selected from 2-methylimidazole (2MZ), 1-dodecyl-2-methyl-3-benzylimidazole chloride (SFZ), 1-cyanoethyl-2-undecylimidazole (C11Z-CN), 1-cyanoethyl-2-phenylimidazole (2PZ-CN), 1,3-dibenzyl-2-methylimidazole chloride (FFZ), 2-ethyl-4-methylimidazole (2E4MZ), 1-cyanoethyl -2-methylimidazole (2MZ-CN), 2-undecylimidazole (C11Z), 1-cyanoethyl-2-phenylimidazole trimellitate (2PZ-CNS), 1-benzyl-2-methylimidazole (1B2MZ), 2-phenyl-4-methylimidazole (2P4MZ), 1-cyanoethyl-2-methylimidazole trimellitate, 1-cyanoethyl-2-undecylimidazole trimellitate (C11Z-CNS), 2-phenylimidazole (2PZ), 1-cyanoethyl-2-ethyl-4-methylimidazole trimellitate (2E4MZ-CNS), trimellitate (2MZ-CNS) and 2,4-diamino-6[2'-methylimidazole-(1')]ethyl-S-triazine (2MZ-A).

[0067] The triazine benzene compound, composition, cured product and preparation method thereof of the present invention are specifically described below by way of examples. Main raw materials and equipment used: Unless otherwise specified, the raw materials and equipment of each embodiment and comparative example are the same; materials without specific models or types are purchased from the market or commonly available through common channels of the same model, and are not specifically limited.

[0068] Example 1

[0069] (1) Synthesis of phenolic resin (TZP): In a 250 ml four-necked flask equipped with a mechanical stirrer, condensation reflux, and nitrogen introduction device, 12.51 g of 4-hydroxybenzene-4-cyanide (HBZ) and 150 ml of ethylene dichloride were added, and the mixture was stirred and mixed in a water bath at 0°C under condensation reflux. After the temperature stabilized at 0°C, 141.9 g of trifluoromethanesulfonic acid was added, and the mixture was stirred for 30 min until the liquid phase was uniform and the temperature was stable. The system was then slowly heated to room temperature (25°C) and reacted for 12 h. Ice water was added, and aqueous ammonia was added dropwise to adjust the pH value to neutral. The mixture was filtered and washed with water for 2-4 times, and dried in vacuo to obtain phenolic resin with a yield of 93%.

[0070] (2) Synthesis of triazine benzene epoxy (TZP-EP): In a 250 ml four-necked flask equipped with mechanical stirring, condensation reflux, and nitrogen introduction device, add 10 g of phenolic resin (TZP) and 94.82 g of epichlorohydrin, and heat to 65°C under a nitrogen atmosphere. After the temperature stabilizes, add 0.618 g of benzyltriethylammonium chloride, react for 10 min, add 3.69 g of sodium hydroxide, and react for 3 h. After the reaction is completed, filter and wash the filtrate with hot water 3 times, remove water with anhydrous sodium sulfate for more than 6 h, filter again and remove the solvent by rotary evaporation. The product is placed in a vacuum oven to dry to obtain triazine benzene epoxy resin (TZP-EP) with a yield of 85%.

[0071] Example 2

[0072] (1) Synthesis of triazine benzene active ester (TZP-AE): In a 250 ml four-necked flask equipped with a mechanical stirrer, condensation reflux, and nitrogen introduction device, 10 g of phenolic resin (TZP, the synthesis steps are the same as in Example 1) and 100 g of tetrahydrofuran were added, and the mixture was stirred and mixed in a water bath at 0°C under condensation reflux until a homogeneous phase was obtained. After the temperature stabilized, 4.03 g of acetyl chloride was added and the mixture was stirred evenly. After the temperature stabilized, 3.78 g of triethylamine was added, and attention was paid to preventing temperature surge. The mixture was stirred for 2 h, and the temperature was raised to 25°C and the reaction was continued for 2 h. The temperature was then raised to 60°C and the reaction was continued for 2 h. After the reaction was completed, the generated amine compound salt was removed by suction filtration, the filtrate was evaporated to remove the solvent, ethyl acetate was added at 60°C to dissolve it again, and the mixture was washed with hot water for several times until it was neutral. The mixture was dehydrated with anhydrous sodium sulfate for more than 6 h, and the solvent was removed by evaporation. The product was dried in a vacuum oven to obtain triazine benzene active ester (TZP-AE) with a yield of 83%.

[0073] (2) Curing of TZP-EP and TZP-AE: After 5.36 g of TZP-EP and 6.675 g of TZP-AE were mixed evenly at 140°C, 0.12 g of 2-ethyl-4-methylimidazole was added and stirred rapidly. The mixture was poured into a mold and cured in three stages according to the curing process: 200°C / 2h, 225°C / 2h, and 250°C / 4h. After natural cooling, an epoxy active ester cured product (TZP-AE / EP) containing a triazine ring and a benzene structure was obtained.

[0074] The properties of the epoxy active ester cured product are as follows: the 5% thermal weight loss temperature under nitrogen atmosphere is 437°C, the carbon residue rate at 800°C is 68.6%, the glass transition temperature is 356°C, and the linear thermal expansion coefficient (a 1 <60ppm / ℃), dielectric constant (10 7 HZ) is 2.91, and has flame retardant and self-extinguishing properties, reaching UL-94 test V-0 level. Figure 6 The cone calorimeter test curve shows that TZP-EP and TZP-AE have ultra-low heat release after curing (rate: 111.3kW / m 2 ), and the flexural modulus of the composite material made with Kevlar fiber is 9.9GPa.

[0075] Comparative Example 1

[0076] E51 / DDM: Take 10g of epoxy resin E51 and 2.5g of diaminodiphenylmethane (DDM), mix them evenly at 120℃, pour them into the mold and cure them at 130℃ / 2h+160℃ / 2h+190℃ / 2h.

[0077] Performance Testing

[0078] Test method:

[0079] TGA: Select N 2 As the protective gas, the heating rate was 10°C / min, the test range was 25°C to 800°C, and the test was performed using a TA Instruments Q500 TGA instrument.

[0080] TMA: The coefficient of linear expansion (CTE) of the samples was measured using a TMA402 F1 / F3 Hyperion Thermomechanical Analyzer in compression mode at a heating rate of 5°C / min.

[0081] Determination of dielectric constant and loss: Dielectric tester Keysight E5071C and precision impedance analyzer Agilent4294A are used to test the dielectric constant and loss of epoxy resin at high and low frequencies respectively.

[0082] DMA: The test was performed using a TA Instruments Q800 DMA instrument in tensile mode with a frequency of 1 Hz and a heating rate of 5 °C / min.

[0083] Vertical burning test (UL-94): It is carried out on a M607B vertical burning test machine. The test is carried out according to the standard ASTM D3801-10, and the test sample size is 125×13X3mm.

[0084] Cone calorimeter: The test was conducted using an ISO 5660, 50 kW cone calorimeter.

[0085] The performance test results are shown in Table 1.

[0086] Table 1 Performance test results

[0087]

[0088] from Figure 1-8 It can be seen from the test data that, compared with the E51 / DDM epoxy resin cured product of the comparative example, the epoxy active ester cured product containing triazine ring and benzene structure (TZP-AE / EP) of the embodiment of the present invention has greatly improved in high temperature resistance (Tg), dimensional stability (TMA), dielectric properties, heat release, bending modulus, flame retardancy and other aspects.

[0089] Although some specific embodiments of the present invention have been described in detail by way of example, it will be appreciated by those skilled in the art that the above examples are for illustration only and are not intended to limit the scope of the present invention. It will be appreciated by those skilled in the art that the above embodiments may be modified without departing from the scope and spirit of the present invention. The scope of the present invention is defined by the appended claims.

Claims

1. A compound, characterized in that It has the structure of the compound represented by the following general formula (I) or (II), In the general formula (I), R1-R 15 Each independently represents the following general formula (I ’ ), R1-R 15 At least three of them are not H; the A groups independently represent a linear or branched alkyl group having 0 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms; The multifunctional triazine benzene epoxy resin represented by the general formula (II) wherein R 1a -R 15a Each independently represents the following general formula (II ’ ) and there are at least three of them, the rest are H, The multifunctional triazine benzene active ester represented by the general formula (II) wherein R 1a -R 15a Each independently represents one of the following groups of general formula (II"), and there are at least three of them, and the rest are H.

2. The method for preparing the compound according to claim 1, characterized in that: The preparation method of the compound represented by the general formula (I) comprises the following steps: dissolving a p-cyanophenol compound in a solvent, adding a catalyst, and preparing R1, R6 and R 11 The phenolic resin represents -OH; the p-cyanophenol compound is 4-hydroxybenzene-4-nitrile; the solvent is ethylene dichloride; and the catalyst is trifluoromethanesulfonic acid or ZnCl2.

3. The method for preparing the compound according to claim 1, characterized in that: The preparation method of the compound represented by the general formula (II) comprises the following steps: obtaining β-substituted epichlorohydrin or acyl chloride wherein the B or C group independently represents one of H, alkyl, alkenyl, alkynyl, and phenyl; Under the action of a catalyst, a compound represented by the general formula (I) containing an active group undergoes a ring-opening and ring-closing reaction with β-substituted epichlorohydrin to obtain a multifunctional triazine benzene epoxy resin; Alternatively, a compound represented by the general formula (I) containing an active group is subjected to a substitution reaction with an acyl chloride compound in the presence of a catalyst to obtain a polyfunctional triazine benzene active ester having the structure of the compound represented by the general formula (II).

4. The method for preparing the compound according to claim 1, characterized in that: The following steps are involved: (1) dissolving a cyanophenol compound in a solvent, adding a catalyst, and preparing R1, R6 and R 11 The phenolic resin represents -OH; the p-cyanophenol compound is 4-hydroxybenzene-4-nitrile; the solvent is ethylene dichloride; and the catalyst is trifluoromethanesulfonic acid or ZnCl2. (2) reacting the phenolic resin, epichlorohydrin compound and phase transfer catalyst described in step (1) to obtain R of the compound represented by general formula (II) 1a , R 6a and R 11a express The epoxy resin has an epoxy value of 0.400-0.

514.

5. The method for preparing the compound as claimed in claim 4, characterized in that: The phase transfer catalyst is one or a combination of trioctylmethylammonium chloride, dodecyltrimethylammonium chloride, tetrabenzyltrimethylammonium chloride, tetramethylammonium bromide, benzyltriethylammonium chloride, tetrabutylammonium bromide and tetrabutylammonium hydrogen sulfate; and the epichlorohydrin compound is epichlorohydrin.

6. The method for preparing the compound according to claim 1, characterized in that: The following steps are involved: (1) dissolving a cyanophenol compound in a solvent, adding a catalyst, and preparing R1, R6 and R 11 The phenolic resin represents -OH; the p-cyanophenol compound is 4-hydroxybenzene-4-nitrile; the solvent is ethylene dichloride; and the catalyst is trifluoromethanesulfonic acid or ZnCl2. (2) dissolving the phenolic resin in step (1) in a solvent, adding an acyl chloride compound and an amine compound in sequence, and reacting to obtain R of the compound represented by general formula (II) 1a , R 6a and R 11a express of active esters.

7. A curable composition, characterized in that The invention comprises the compound according to claim 1 or the compound obtained by the preparation method according to any one of claims 2 to 7.

8. A solidified product, characterized in that: The curable composition according to claim 8 is cured.

9. A method for preparing a solidified product as claimed in claim 9, characterized in that: The method comprises the following steps: the multifunctional triazine benzene epoxy resin represented by the general formula (II) is melted by heating and cured by heating in sequence to obtain a triazine benzene epoxy cured product.

10. Use of the solidified material obtained by the preparation method according to claim 8 or claim 9, characterized in that: Used in the fields of electronics, aerospace, automotive industry, construction or coatings.

Images