CN112898927B - Epoxy resin composition and preparation method and application thereof - Google Patents

Epoxy resin composition and preparation method and application thereof Download PDF

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CN112898927B
CN112898927B CN202110088117.XA CN202110088117A CN112898927B CN 112898927 B CN112898927 B CN 112898927B CN 202110088117 A CN202110088117 A CN 202110088117A CN 112898927 B CN112898927 B CN 112898927B
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epoxy resin
sealant according
parts
curing agent
glycidyl
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CN112898927A (en
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段伟森
张亚平
舒小辉
刘兆辉
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Dongguan Powerbond New Materials Technology Development Co ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/44Amides
    • C08G59/446Phosphoramides
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02Non-macromolecular additives
    • C09J11/06Non-macromolecular additives organic
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1339Gaskets; Spacers; Sealing of cells

Abstract

The invention provides an epoxy resin composition and a preparation method and application thereof, wherein the epoxy resin composition comprises 50-100 parts by weight of epoxy resin, 20-40 parts by weight of hardener and 5-20 parts by weight of curing agent; the curing agent is any one or the combination of at least two of compounds with the structure shown in the formula I. According to the epoxy resin composition, the curing agent with the hydrophobic chain segment is introduced into the epoxy resin matrix, and the curing agent in a specific part is matched, so that the prepared epoxy resin composition has high temperature resistance and excellent water vapor barrier property, can be applied to a display device as a sealant, and has important research significance.

Description

Epoxy resin composition and preparation method and application thereof
Technical Field
The invention belongs to the technical field of adhesives, and particularly relates to an epoxy resin composition, and a preparation method and application thereof.
Background
The technologies of LCD, electronic ink, OLED, etc. have become the main display technologies in the display market, and the application fields thereof are also increasingly wide, and the technologies are widely applied in the fields of portable terminals, automobiles, computers, liquid crystal displays, etc. with the continuous innovation, development and popularization of the display technologies, the requirements on the quality of the liquid crystal display units are also increasingly high, and especially, some liquid crystal display units need to work for a long time under different conditions of high temperature, high humidity, etc. and are required to have higher humidity-resistant reliability; the sealant is used as a structural protection component, and the barrier property of the sealant to water vapor is the key of the humidity resistance reliability of the whole display unit; therefore, the demand for high moisture resistance of the sealant is also increasing.
There are many reports that epoxy resin compositions are used as a commonly used sealant for protecting a structure in a liquid crystal display device. CN104159968A discloses a method of curing a composite material useful for radio frequency filter applications, said method comprising the steps of: a curable thermoset epoxy resin composition comprising at least one epoxy resin; at least one toughening agent; at least one hardener; and at least one filler; curing the curable thermoset epoxy resin composition to form a cured composite; wherein the curable thermoset epoxy resin composition upon curing provides a cured composite product having a balance of properties including Tg, coefficient of thermal expansion, tensile strength, thermal conductivity, and having a density of less than 2.7 g/cc. CN103589111A discloses a resin composition comprising an epoxy resin, zinc oxide powder and a hardener, wherein the mohs hardness of the zinc oxide powder is about 4 to 5 and the particle size is about 0.1 micrometer to about 50 micrometers, and the content of the zinc oxide powder is greater than about 0.5 parts by weight and less than 10 parts by weight based on 100 parts by weight of the epoxy resin. By means of the composition, the prepared laminated plate has excellent size stability, heat resistance, electric property, dissipation factor and the like, and can effectively inhibit the crack phenomenon between layers of the laminated plate. CN101676315 discloses a sealant which is used for a liquid crystal dropping process with high precision, durability and reliability, and does not adversely affect liquid crystals. The present invention provides a sealant for manufacturing a liquid crystal display by a liquid crystal dropping process, which comprises a maleimide compound, an epoxy resin and a latent epoxy hardener, and does not contain a photoinitiator, is temporarily curable by light irradiation, and is curable to a final cured state by heating after the light irradiation. However, the moisture barrier properties of the epoxy resin composition for a sealant disclosed in the above patent, particularly the moisture barrier properties at high temperature, still do not satisfy our requirements and need to be improved.
Therefore, the development of an epoxy resin composition having excellent water vapor barrier properties at high temperatures has important research value.
Disclosure of Invention
In view of the deficiencies of the prior art, the present invention aims to provide an epoxy resin composition, a preparation method and an application thereof, wherein the epoxy resin composition comprises a combination of an epoxy resin, a hardener and a curing agent; by introducing the curing agent with the hydrophobic chain segment and matching with the hardening agent in a specific part, the prepared epoxy resin composition has high temperature resistance and excellent water vapor barrier property, and can be applied to a display device as a sealant.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an epoxy resin composition, comprising the following components in parts by weight: 50-100 parts of epoxy resin, 20-40 parts of hardener and 5-20 parts of curing agent;
the curing agent is any one or the combination of at least two of compounds with the structure shown in the formula I:
Figure GDA0003012283620000031
wherein R is selected from
Figure GDA0003012283620000032
Figure GDA0003012283620000033
Any one of them;
n 1 、n 2 and n 3 Each independently is an integer from 1 to 7 (e.g., 2, 3, 4, 5, or 6);
* Indicates the attachment site.
According to the epoxy resin composition provided by the invention, a compound containing a hydrophobic chain segment in a specific part is introduced into the epoxy resin composition, and the blocking performance of the epoxy resin composition on water vapor can be improved while the high-temperature resistance of the epoxy resin composition is not influenced by matching with a hardening agent in a specific part; and the curing agent and the hardening agent have good compatibility with an epoxy resin matrix, so that the obtained epoxy resin composition has good mechanical properties, meets the use requirement of the epoxy resin composition as a sealant in a display device, and has important research significance.
The epoxy resin may be 55 parts by weight, 60 parts by weight, 65 parts by weight, 70 parts by weight, 75 parts by weight, 80 parts by weight, 85 parts by weight, 90 parts by weight, or 95 parts by weight, and specific points therebetween, are not exhaustive for the invention and are included for brevity.
The hardener may be 22 parts by weight, 24 parts by weight, 26 parts by weight, 28 parts by weight, 30 parts by weight, 32 parts by weight, 34 parts by weight, 36 parts by weight, or 38 parts by weight, and specific points therebetween are not exhaustive, and for brevity and clarity, the invention is not intended to be limited to the specific points included in the ranges.
The curing agent may be 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight, 10 parts by weight, 12 parts by weight, 14 parts by weight, 16 parts by weight, or 18 parts by weight, and specific points therebetween are not exhaustive for the invention and are included for brevity.
Preferably, said n 1 、n 2 And n 3 Each independently selected from 1 or 2.
Preferably, the epoxy resin includes a glycidyl-based epoxy resin and/or a non-glycidyl-based epoxy resin.
Preferably, the glycidyl epoxy resin comprises any one of glycidyl ether epoxy resin, glycidyl ester epoxy resin or glycidyl amine epoxy resin or a combination of at least two of the glycidyl ether epoxy resin, the glycidyl ester epoxy resin or the glycidyl amine epoxy resin.
Preferably, the glycidyl ether type epoxy resin includes any one of or a combination of at least two of bisphenol a type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, or hydrogenated bisphenol a type epoxy resin.
Preferably, the glycidyl ester type epoxy resin includes diglycidyl phthalate.
Preferably, the non-glycidyl epoxy resin comprises a cycloaliphatic epoxy resin.
Preferably, the hardener includes any one of imidazole type hardener, organic urea type hardener, dicyandiamide type hardener, hydrazide type hardener or amine type hardener or a combination of at least two of them.
Preferably, the curing agent is selected from any one of or a combination of at least two of the compounds having the following structures:
Figure GDA0003012283620000041
Figure GDA0003012283620000051
preferably, the curing agent is prepared by a method comprising: phenyl phosphoryl dichloride and R-NH 2 Carrying out reaction to obtain the curing agent; r has the same limits as in formula I.
Preferably, the phenyl phosphoryl dichloride and R-NH 2 The molar ratio of (1), (2-2.5), for example 1.
Preferably, the reaction is carried out in a solvent.
Preferably, the solvent includes any one of toluene, xylene, 1, 6-dioxane, n-hexane, or furan.
Preferably, a catalyst is also added to the reaction.
Preferably, the molar ratio of the phenylphosphoryl dichloride to the catalyst is 1 (0.5 to 0.75), such as 1.
Preferably, the catalyst is triethylamine.
Preferably, the reaction temperature is in the range of 40 to 80 ℃, such as 45 ℃, 50 ℃, 55 ℃, 60 ℃, 65 ℃, 70 ℃ or 75 ℃, and the specific values therebetween, are not exhaustive for the invention and for the sake of brevity.
Preferably, the reaction time is 10 to 15 hours, such as 10.5 hours, 11 hours, 11.5 hours, 12 hours, 12.5 hours, 13 hours, 13.5 hours, 14 hours or 14.5 hours, and specific values therebetween, not exhaustive list of the specific values included in the range is provided for brevity and conciseness.
The process for the preparation of the curing agents of the present invention can also be synthesized with reference to the prior art ("image of halogen-free flame retardant with varied phosphor chemical coating on the properties of a biochemical-A type epoxy resin: synthesis, flame retardant mechanical and mechanical properties", RSC Advances.2016,6, 59226-59236).
Preferably, other additives are also included in the epoxy resin composition.
Preferably, the epoxy resin contains the other additives in an amount of 5 to 40 parts by weight, for example, 7 parts by weight, 9 parts by weight, 13 parts by weight, 15 parts by weight, 19 parts by weight, 23 parts by weight, 25 parts by weight, 29 parts by weight, 33 parts by weight, 36 parts by weight, or 39 parts by weight, and specific points therebetween, which are included in the range are not exhaustive for the invention in the interests of brevity and conciseness.
Preferably, the other additives include any one of a coupling agent, a filler, a thixotropic agent, or an antifoaming agent, or a combination of at least two thereof.
Preferably, the coupling agent comprises any one of a silane coupling agent, a titanate coupling agent, or an aluminate coupling agent, or a combination of at least two thereof.
Preferably, the filler comprises any one of carbonate type filler, sulfate type filler, metal oxide or metal powder or a combination of at least two of the above.
Preferably, the thixotropic agent comprises a natural thixotropic agent.
Preferably, the thixotropic agent further comprises a cellulosic thixotropic agent and/or bentonite.
Preferably, the defoaming agent comprises any one of alcohol defoaming agent, ester defoaming agent, ether defoaming agent or organic silicon or the combination of at least two of the above.
In a second aspect, the present invention provides a process for preparing an epoxy resin composition according to the first aspect, the process comprising: mixing an epoxy resin, a hardener, a curing agent, and optionally other additives to obtain the epoxy resin composition.
Preferably, the mixing time is 4 to 6 hours, such as 4.2 hours, 4.4 hours, 4.6 hours, 4.8 hours, 5 hours, 5.2 hours, 5.4 hours, 5.6 hours, or 5.8 hours, and specific values therebetween, not to be limited by space and for the sake of brevity, the invention is not exhaustive of the specific values included in the ranges.
In a third aspect, the present invention provides a use of the epoxy resin composition according to the first aspect in a liquid crystal display device.
Preferably, the application is as a sealant.
Compared with the prior art, the invention has the following beneficial effects:
(1) According to the epoxy resin composition provided by the invention, the curing agent with the hydrophobic chain segment is added into the epoxy resin matrix in a specific part, so that the epoxy resin composition with excellent high-temperature resistance and water vapor barrier property is obtained; the curing agent epoxy resin matrix has good compatibility, and the curing agent epoxy resin matrix is matched with the hardener in a specific part, so that the prepared epoxy resin composition has excellent mechanical properties, completely meets the requirement of the curing agent epoxy resin composition in a display device, and is suitable for large-scale batch production and use.
(2) Specifically, the epoxy resin composition provided by the invention has the viscosity of 28000-32000 mPa & s, the Shore hardness of 80-88, the glass transition temperature of 115-125 ℃, the bonding strength of 33-38 MPa, the shrinkage rate of 1.6-1.8%, the water absorption of 0.1-0.3%, the dielectric strength of 19-20 kV/mm, the water mist generation time of a boiling-resistant test of 72-96 h and the volume resistivity of 1.5 x 10 15 ~2×10 15 Ω·cm。
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Preparation example 1
A curing agent, the structural formula of which is shown as follows:
Figure GDA0003012283620000081
the preparation process comprises slowly introducing 194.98g (1 mol) of phenylphosphoryl dichloride into a reactor containing 142g (2 mol)
Figure GDA0003012283620000082
101.19g (2 mol) of triethylamine and 1000g of toluene were reacted at 40 ℃ for 2 hours, at 80 ℃ for 8 hours, and then filtered to obtain a compound M01.
Preparation example 2
A curing agent has the following structural formula:
Figure GDA0003012283620000083
the preparation method comprises the following steps: 194.98g (1 mol) of phenylphosphoryl dichloride were added to a solution containing 146g (2 mol)
Figure GDA0003012283620000084
101.19g (2 mol) of triethylamine and 1000g of toluene were reacted at 40 ℃ for 2 hours, at 80 ℃ for 6 hours, and then filtered to obtain a compound M02.
Preparation example 3
Figure GDA0003012283620000091
The preparation process comprises adding 194.98g (1 mol) of phenylphosphoryl dichloride to a mixture containing 270.2g (2 mol)
Figure GDA0003012283620000092
101.19g (2 mol) of triethylamine and 1000g of toluene were reacted at 40 ℃ for 2 hours, at 80 ℃ for 10 hours, and then filtered to obtain a compound M03.
Examples 1 to 3
An epoxy resin composition comprises the following specific components in parts by weight as shown in Table 1;
TABLE 1
Name (R) Example 1 Example 2 Example 3
Epoxy resin 75 50 100
Imidazole hardener 30 20 40
Curing agent 15 5 20
Silane coupling agent 1 1 1
Metal oxides 20 3.5 38.5
Defoaming agent 0.5 0.5 0.5
The preparation method of the epoxy resin composition provided in example 1 includes: epoxy resin (Mitsubishi, YX8000, japan), imidazole hardener (Ajinomoto Fine-techno Co. Inc, PN-40), curing agent (preparation example 1), silane coupling agent KH550, metal oxide (DAM series, PLV-6) and defoaming agent BYK051 were mixed for 2 hours to obtain the epoxy resin composition.
The preparation method of the epoxy resin composition provided in example 2 includes: epoxy resin (Mitsubishi, YX 8000), imidazole hardener (Ajinomoto Fine-techno Co. Inc, PN-40), curing agent (preparation example 2), silane coupling agent KH550, metal oxide (DAM series, PLV-6) and defoaming agent BYK051 were mixed for 2 hours to obtain the epoxy resin composition.
The preparation method of the epoxy resin composition provided in example 3 includes: epoxy resin (Mitsubishi, YX 8000), imidazole hardener (Ajinomoto Fine-techno Co. Inc, PN-40), curing agent (preparation example 3), silane coupling agent KH550, metal oxide (DAM series, PLV-6) and defoaming agent BYK051 were mixed for 2 hours to obtain the epoxy resin composition.
Example 4
An epoxy resin composition was distinguished from example 1 only in that a curing agent was added in an amount of 5 parts by weight, an imidazole-based curing agent was added in an amount of 40 parts by weight, and other components, amounts and preparation methods were the same as in example 1.
Example 5
An epoxy resin composition was distinguished from example 1 only in that a curing agent was added in an amount of 20 parts by weight, an epoxy resin was added in an amount of 25 parts by weight, and other components, amounts and preparation methods were the same as in example 1.
Comparative example 1
An epoxy resin composition was distinguished from example 1 only in that, without adding a curing agent, an imidazole-based hardener (AJinomoto Fine-techno co. Inc, PN-40) was added in an amount of 45 parts by weight, and other components, amounts and preparation methods were the same as example 1.
Comparative example 2
An epoxy resin composition was distinguished from example 1 only in that a curing agent and an imidazole-based curing agent were not added, and that an azelaic acid dihydrazide curing agent was added in an amount of 45 parts by weight, and other components, amounts and preparation methods were the same as those of example 1.
And (3) performance testing:
(1) Viscosity: testing by adopting a Bohler fly DVS + rotary viscometer-Brookfield viscometer;
(2) Shore hardness: testing was performed according to standard ASTM-D-2240;
(3) Glass transition temperature: testing was performed according to standard ASTM-D-3418;
(4) Bonding strength: testing according to the standard ASTM-D-638;
(6) Shrinkage rate: testing according to ASTM D792 test standard;
(7) Water absorption: testing according to ASTM D570 test standard;
(8) Dielectric strength: testing was performed according to ASTM-D-149 test Standard;
(9) Boiling resistance test: taking 10g of the epoxy resin composition to be tested, adding 0.05g of the gap particles into a mold, uniformly stirring, transferring the epoxy resin composition to a glass slide by a screen printing device, pre-fixing at 90 ℃ for 10min, taking out, adhering by using the glass slide, and pressurizing at 160 ℃ (0.1 MPa) for curing for 60min. Sealing with sealing glue after curing, putting the sealed test piece into a pressure cooker, boiling with water, and recording the time of water mist generation;
(10) Volume resistivity: testing was performed according to ASTM-D-257 test standard.
The epoxy resin compositions obtained in examples 1 to 5 and comparative examples 1 to 2 were tested according to the above test methods, and the test results are shown in tables 2 and 3:
TABLE 2
Figure GDA0003012283620000111
Figure GDA0003012283620000121
TABLE 3
Figure GDA0003012283620000122
As can be seen from the data in tables 3 and 2: the epoxy resin composition provided by the embodiments 1 to 5 has obviously improved reliability by introducing the reactive heat-resistant curing agent, and fully meets the requirements of high-requirement application fields.
The epoxy resin compositions obtained in examples 1 to 5 had a viscosity of 28000 to 32000mPa s, a Shore hardness of 80 to 88, a glass transition temperature of 115 to 125 ℃, a cohesive strength of 33 to 38MPa, a shrinkage of 1.6 to 1.8%, a water absorption of 0.1 to 0.3%, a dielectric strength of 19 to 20kV/mm, a boiling-resistant test in which the time for generating water mist was 72 to 96 hours, and a volume resistivity of 1.5X 10 15 ~2×10 15 Ω·cm。
Comparing the epoxy resin compositions obtained in example 1, comparative example 1 and comparative example 2, it can be found that the epoxy resin composition obtained in example 1 has a higher adhesive strength, indicating a better adhesive property; the time for water mist to appear in a boiling test is longer, which shows that the reliability is more excellent.
The applicant states that the present invention is illustrated by the above examples to an epoxy resin composition and a preparation method and application thereof, but the present invention is not limited to the above examples, i.e. it does not mean that the present invention must be implemented by relying on the above examples. It should be understood by those skilled in the art that any modifications of the present invention, equivalent substitutions of the raw materials of the product of the present invention, and the addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (25)

1. A sealant for a liquid crystal display device is characterized by comprising the following components in parts by weight: 50-100 parts of epoxy resin, 20-40 parts of hardener and 5-20 parts of curing agent;
the hardener is an imidazole hardener;
the curing agent is any one or the combination of at least two of the following compounds:
Figure FDA0003909651440000011
2. the encapsulant of claim 1, wherein the epoxy resin comprises a glycidyl-based epoxy resin and/or a non-glycidyl-based epoxy resin.
3. The sealant according to claim 2, wherein the glycidyl-based epoxy resin comprises any one of or a combination of at least two of glycidyl ether-based epoxy resin, glycidyl ester-based epoxy resin, or glycidyl amine-based epoxy resin.
4. The sealant according to claim 3, wherein the glycidyl ether type epoxy resin comprises any one of bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin or hydrogenated bisphenol A type epoxy resin or a combination of at least two thereof.
5. The sealant according to claim 3, wherein the glycidyl ester based epoxy resin comprises diglycidyl phthalate.
6. The encapsulant of claim 2, wherein the non-glycidyl-based epoxy resin comprises a cycloaliphatic epoxy resin.
7. The sealant according to claim 1, wherein the curing agent is prepared by a method comprising: reacting phenyl phosphoryl dichloride with an amine compound to obtain the curing agent;
the amine compound is selected from
Figure FDA0003909651440000021
Figure FDA0003909651440000022
Any one of them.
8. The sealant according to claim 7, wherein the molar ratio of the phenylphosphoryl dichloride to the amine compound is 1 (2-2.5).
9. The sealant according to claim 7, wherein the reaction is carried out in a solvent.
10. The sealant according to claim 9, wherein the solvent comprises any one of toluene, xylene, 1, 6-dioxane, n-hexane, or furan.
11. The sealant according to claim 7, wherein a catalyst is further added to the reaction.
12. The sealant according to claim 11, wherein the molar ratio of the phenylphosphoryl dichloride and the catalyst is 1 (0.5-0.75).
13. The sealant according to claim 11, wherein the catalyst is triethylamine.
14. The sealant according to claim 7, wherein the temperature of the reaction is 40 to 80 ℃.
15. The sealant according to claim 7, wherein the reaction time is 10 to 15 hours.
16. The sealant according to claim 1, further comprising other additives.
17. The sealant according to claim 16, wherein the content of the other additive is 5 to 40 parts by weight.
18. The sealant according to claim 16, wherein the other additive comprises any one of a coupling agent, a filler, a thixotropic agent, or an antifoaming agent, or a combination of at least two thereof.
19. The sealant according to claim 18, wherein the coupling agent comprises any one of a silane coupling agent, a titanate coupling agent, or an aluminate coupling agent, or a combination of at least two thereof.
20. The sealant according to claim 18, wherein the filler comprises any one of a carbonate-based filler, a sulfate-based filler, a metal oxide or a metal powder or a combination of at least two thereof.
21. The sealant according to claim 18, wherein the thixotropic agent further comprises a cellulose-based thixotropic agent and/or bentonite.
22. The sealant according to claim 18, wherein the defoamer comprises any one of or a combination of at least two of an alcohol defoamer, an ester defoamer, an ether defoamer or a silicone.
23. A method of preparing a sealant according to any one of claims 1 to 22, comprising: mixing an epoxy resin, a hardener, a curing agent, and optionally other additives to obtain the sealant.
24. The method of claim 23, wherein the mixing time is 4 to 6 hours.
25. Use of the sealant according to any one of claims 1 to 22 in a liquid crystal display device.
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CN106854219A (en) * 2016-12-06 2017-06-16 沈阳化工大学 A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent and preparation method thereof
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