WO2021260557A1 - Epoxy adhesive composition, epoxy adhesive, and method for preparing epoxy adhesive - Google Patents

Epoxy adhesive composition, epoxy adhesive, and method for preparing epoxy adhesive Download PDF

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Publication number
WO2021260557A1
WO2021260557A1 PCT/IB2021/055516 IB2021055516W WO2021260557A1 WO 2021260557 A1 WO2021260557 A1 WO 2021260557A1 IB 2021055516 W IB2021055516 W IB 2021055516W WO 2021260557 A1 WO2021260557 A1 WO 2021260557A1
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WIPO (PCT)
Prior art keywords
epoxy
adhesive composition
weight
epoxy adhesive
epoxy resin
Prior art date
Application number
PCT/IB2021/055516
Other languages
French (fr)
Inventor
Shuanghul DENG
Michael A. Kropp
Matthew J. Kryger
Original Assignee
3M Innovative Properties Company
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Publication date
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Publication of WO2021260557A1 publication Critical patent/WO2021260557A1/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates 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
    • C08G59/18—Macromolecules 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
    • C08G59/40—Macromolecules 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
    • C08G59/50—Amines
    • C08G59/5006—Amines aliphatic
    • C08G59/5013—Amines aliphatic containing more than seven carbon atoms, e.g. fatty amines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates 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
    • C08G59/18—Macromolecules 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
    • C08G59/20—Macromolecules 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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/223—Di-epoxy compounds together with monoepoxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates 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
    • C08G59/18—Macromolecules 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
    • C08G59/20—Macromolecules 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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates 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
    • C08G59/18—Macromolecules 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
    • C08G59/68—Macromolecules 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 catalysts used
    • C08G59/686—Macromolecules 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 catalysts used containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend

Definitions

  • plastics are widely used to replace traditional glass and metal substrates so as to achieve lightweight electronic products.
  • Many small plastic components such as protective boards for printed circuit boards, magnets, and electronic shelf labels, need to be adhered to specific locations of electronic products by suitable adhesives.
  • some special applications such as encapsulation and caulking of electronic products, also require the use of suitable adhesives.
  • one-part adhesives that can be cured at a low temperature are typically used to achieve precise dispensing of electronic products.
  • suitable adhesives mainly include epoxy mercaptan-based epoxy adhesives.
  • epoxy adhesives typically have poor resistance to water vapor permeation and often fail to meet the requirements of practical application.
  • One object of the present invention is to provide an epoxy adhesive composition and an epoxy adhesive prepared from the epoxy adhesive composition.
  • the epoxy adhesive composition has a good workability and curing process operability.
  • the epoxy adhesive has a good T-peel strength on a plastic surface (especially a polyethylene terephthalate (PET) surface) and good resistance to water vapor permeation.
  • PET polyethylene terephthalate
  • the present invention provides an epoxy adhesive composition, comprising: a) 10-50 parts by weight of a bisphenol A epoxy resin, a bisphenol F epoxy resin, or a combination of a bisphenol A epoxy resin and a bisphenol F epoxy resin, wherein the bisphenol A epoxy resin and the bisphenol F epoxy resin have an epoxy equivalent weight of 150-250 g/Eq; b) 20-50 parts by weight of a dihydroxy phenol glycidyl ether epoxy resin having an epoxy equivalent weight of 100-150 g/Eq; c) 1-5 parts by weight of a silane coupling agent; d) 20-60 parts by weight of a polyetheramine curing agent; e) 10-40 parts by weight of a filler; and f) 0-10 parts by weight of an imidazole accelerator.
  • the content of the bisphenol A epoxy resin, the bisphenol F epoxy resin, or the combination of the bisphenol A epoxy resin and the bisphenol F epoxy resin is 10-50 parts by weight, preferably 15-40 parts by weight.
  • the content of the dihydroxy phenol glycidyl ether epoxy resin is 20-50 parts by weight, preferably 30-45 parts by weight.
  • the silane coupling agent is one or more selected from the group of: an epoxy-terminated silane coupling agent, an amino-terminated silane coupling agent, and a thiol-terminated silane coupling agent.
  • the content of the silane coupling agent is 1-5 parts by weight, preferably 2-4 parts by weight.
  • the polyetheramine curing agent is one or more selected from the group of: bifunctional polypropylene glycol polyetheramine, trifunctional polypropylene glycol polyetheramine, and bifunctional polybutylene glycol polyetheramine.
  • the content of the polyetheramine curing agent is 20-60 parts by weight, preferably 40-60 parts by weight.
  • the filler is one or more selected from the group of: talcum powder, polyolefin powder, wollastonite, quartz powder, and mica powder.
  • the content of the filler is 10-40 parts by weight, preferably 15-30 parts by weight.
  • the present invention provides an epoxy adhesive, comprising: a cured product of the epoxy adhesive composition provided according to the present invention.
  • the present invention provides a method for preparing an epoxy adhesive, comprising the step of: curing the epoxy adhesive composition provided according to the present invention to obtain the epoxy adhesive.
  • the epoxy adhesive composition provided by the present invention has a good workability and curing process operability; and an epoxy adhesive prepared from the epoxy adhesive composition has a good peel strength on a plastic surface (especially on a PET surface) and a good water vapor permeability.
  • the epoxy adhesive composition provided by the present invention comprises: a) 10- 50 parts by weight of a bisphenol A epoxy resin, a bisphenol F epoxy resin, or a combination of a bisphenol A epoxy resin and a bisphenol F epoxy resin, wherein the epoxy equivalent weight thereof is 150-250 g/Eq; b) 20-50 parts by weight of a dihydroxy phenol glycidyl ether epoxy resin having an epoxy equivalent weight of 100- 150 g/Eq; c) 1 -5 parts by weight of a silane coupling agent; d) 20-60 parts by weight of a polyetheramine curing agent; e) 10-40 parts by weight of a filler; and f) 0-10 parts by weight of an imidazole accelerator.
  • the bisphenol A epoxy resin and the bisphenol F epoxy resin have an epoxy equivalent weight of 150-250 g/Eq.
  • the bisphenol A epoxy resin and the bisphenol F epoxy resin can adjust the water vapor permeability of the epoxy adhesive.
  • the bisphenol A epoxy resin may be selected from EPON 826 available from Hexion Specialty Chemicals Co., Ltd. (Columbus, USA).
  • the bisphenol F epoxy resin may be selected from Araldite GY 285 available from Huntsman Co., Ltd. (Houston, USA).
  • the dihydroxy phenol glycidyl ether epoxy resin can adjust not only the viscosity of the epoxy adhesive but also the peel strength thereof on a plastic surface (especially a PET surface).
  • the dihydroxy phenol glycidyl ether epoxy resin is one or more selected from the group of: a phenyl diphenol glycidyl ether epoxy resin and a naphthyl diphenol glycidyl ether epoxy resin.
  • the content of the dihydroxy phenol glycidyl ether epoxy resin is 20-50 parts by weight, preferably 30-45 parts by weight.
  • the phenyl diphenol glycidyl ether epoxy resin may be selected from Denacol EX-201 IM available from Nagase America Corporation (New York City, USA); and the naphthyl diphenol glycidyl ether epoxy resin may be selected from HP4032D available from DIC Co., Ltd. (Tokyo, Japan).
  • the content of the silane coupling agent is 1-5 parts by weight, preferably 2-4 parts by weight.
  • the silane coupling agent may be selected from Z6040 available from Dowcoming Co., Ltd. (Midland, USA).
  • the content of the polyetheramine curing agent is 20-60 parts by weight, preferably 30-50 parts by weight.
  • the bifunctional polypropylene glycol polyetheramine curing agent may be selected from D230 and D400 available from Huntsman Co., Ltd. (Houston, USA); and the trifunctional polypropylene glycol polyetheramine curing agent may be selected from T403 available from Huntsman Co., Ltd. (Houston, USA).
  • the filler can adjust the water vapor permeability of the epoxy adhesive.
  • the filler is one or more selected from the group of: talcum powder, polyolefin powder, wollastonite, quartz powder, and mica powder.
  • the talcum powder may be selected from AH51210 available from Quartz Industry Materials (Shanghai) Co., Ltd. (Shanghai, China); and the polyolefin powder may be selected from MICROTHENE F FA 700-00 available from LyondellBassell Chemical Company (Houston, USA).
  • an imidazole accelerator may be optionally added to the epoxy adhesive composition to shorten the curing time thereof, thereby improving the curing process operability.
  • the imidazole accelerator is one or more selected from the group of: N-methylimidazole, 1,2-dimethylimidazole, and 2- ethyl-4-methylimidazole.
  • the content of the imidazole accelerator is 0-10 parts by weight, preferably 2-5 parts by weight.
  • N-methylimidazole and 2- ethyl-4-methylimidazole are commercially available from Shikoku Chemicals Corporation (Chiba City, Japan); and 1,2-dimethylimidazole is commercially available from Ningxia Joie Material Co., Ltd. (Ningxia, China).
  • the epoxy adhesive composition has a viscosity less than or equal to 2000 mPa s at 25°C and a working window greater than or equal to 6 hours at 25°C.
  • the epoxy adhesive composition may be stored at a condition less than or equal to -20°C.
  • the epoxy adhesive provided by the present invention comprises: a cured product of the epoxy adhesive composition provided according to the present invention.
  • a cured product of the epoxy adhesive composition provided according to the present invention.
  • the preparation method may comprise the following steps:
  • Step 1 mixing the bisphenol A epoxy resin and/or the bisphenol F epoxy resin, the dihydroxy phenol glycidyl ether epoxy resin, and the silane coupling agent of the epoxy adhesive composition provided by the present invention under a condition of room temperature (25 °C) to obtain a first mixture;
  • Step 2 adding the filler of the epoxy adhesive composition provided by the present invention to the first mixture to obtain a second mixture;
  • the filler of the epoxy adhesive composition provided by the present invention may be added to the first mixture after high-speed dispersion mixing, which is subjected to at least three times of three-roll milling to obtain the second mixture.
  • the mixture in Step 3, after adding the polyetheramine curing agent and the imidazole accelerator of the epoxy adhesive composition provided by the present invention to the second mixture, the mixture may be mixed thoroughly at a low temperature ( ⁇ 10°C) and then subjected to sufficient vacuum defoaming to obtain the epoxy adhesive.
  • EPON 826 a bisphenol A epoxy resin having an epoxy equivalent weight of 178-186 g/Eq, commercially available from Hexion Specialty Chemicals Co., Ltd. (Columbus, USA).
  • Araldite GY 285, a bisphenol F epoxy resin having an epoxy equivalent weight of 164-173 g/Eq, commercially available from Huntsman Co., Ltd. (Houston, USA).
  • HP4032D a naphthyl diphenol glycidyl ether epoxy resin having an epoxy equivalent weight of 140 g/Eq, commercially available from DIC Co., Ltd. (Tokyo, Japan).
  • AFG-90 an aminophenol trifunctional epoxy resin having an epoxy equivalent weight of 105-115 g/Eq, commercially available from ShangHai HuaYi Resins Co., Ltd. (Shanghai, China).
  • DY-D a butanediol di glycidyl ether epoxy resin having an epoxy equivalent weight of 118-125 g/Eq, commercially available from Huntsman Co., Ltd. (Houston, USA).
  • Z6040 an epoxy-terminated silane coupling agent, commercially available from Dowcoming Co., Ltd. (Midland, USA).
  • Polyetheramine curing agent D230 a bifunctional polypropylene glycol polyetheramine curing agent having an active hydrogen equivalent weight of 60 g/Eq, commercially available from Huntsman Co., Ltd. (Houston, USA).
  • T403 a trifunctional polypropylene glycol polyetheramine curing agent having an active hydrogen equivalent weight of 80 g/Eq, commercially available from Huntsman Co., Ltd. (Houston, USA).
  • WSE600 wollastonite, commercially available from Quartz Industry Materials (Shanghai) Co., Ltd. (Shanghai, China);
  • N-methylimidazole commercially available from Shikoku Chemicals Corporation (Chiba City, Japan);
  • 1,2-dimethylimidazole commercially available from Ningxia Joie Material Co., Ltd. (Ningxia, China);
  • Step 1 The adhesive composition is removed from a freezer, and the time at which is recorded as To, and then the adhesive composition is warmed naturally to 25°C and is in a liquid state.
  • Step 2 The warmed adhesive composition is charged into a material cup, and the viscometer is zeroed and calibrated.
  • the adhesive has a good T-peel strength; and when the measured T-peel strength is greater than or equal to 1.5 N/mm, it indicates that the adhesive has an excellent T-peel strength.
  • This test is in accordance with ASTM F-1249 to measure the water vapor permeability of the adhesives (1 mm thick) provided in the examples and the comparative examples of the present invention at 60°C, the test conditions were “60°C, 100% humidity”, and the unit of test results is g mm/m 2 -24hr.
  • ASTM F-1249 to measure the water vapor permeability of the adhesives (1 mm thick) provided in the examples and the comparative examples of the present invention at 60°C, the test conditions were “60°C, 100% humidity”, and the unit of test results is g mm/m 2 -24hr.
  • Step 1 The adhesive composition is removed from a freezer, and then the adhesive composition is warmed naturally to 25°C and is in a liquid state.
  • Step 3 The adhesive composition warmed to 25°C is used as a test sample and placed on the test aluminum plate.
  • the height of the aluminum plate is lower to 0.5 mm (that is, the thickness of the test sample is 0.5 mm).
  • the holding furnace is turned off, followed by measuring the curing time of the sample (at 70°C). The time corresponding to the position where the storage modulus and loss modulus curves of the test sample intersect is the curing time.
  • the epoxy adhesive composition was heated to 70°C, cured for 1 hours, and left at room temperature (25°C) for 3 days to ully cure, thereby obtaining an epoxy adhesive.
  • the epoxy adhesive composition was subjected to the workability test according to the test method described herein, and the epoxy adhesive was subjected to the T-peel strength test and resistance to water vapor permeation test.
  • the test results are listed in Table 1
  • the epoxy adhesives of comparative examples C1-C5 were prepared in the same manner as example El with the exception that the components and amounts of the epoxy adhesive compositions used to prepare the epoxy adhesives were different. The components and amounts thereof are specifically listed in Table 2.
  • the epoxy adhesives of examples E8-E11 is prepared in the same manner as example El with the exception that as the polyetheramine curing agent was added, an imidazole accelerator was also added, and the components and amounts of the epoxy adhesive compositions used to prepare the epoxy adhesives were different. The components and amounts thereof are specifically listed in Table 3.
  • epoxy adhesive compositions provided by examples E8-E11 were subjected to the workability test according to the test method described herein, and the epoxy adhesives were subjected to the T-peel strength test and resistance to water vapor permeation test.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The present invention relates to an epoxy adhesive composition, comprising: a) 10-50 parts by weight of a bisphenol A epoxy resin, a bisphenol F epoxy resin, or a combination of a bisphenol A epoxy resin and a bisphenol F epoxy resin, wherein the epoxy equivalent weight thereof is 150-250 g/Eq; b) 20-50 parts by weight of a dihydroxy phenol glycidyl ether epoxy resin having an epoxy equivalent weight of 100-150 g/Eq; c) 1-5 parts by weight of a silane coupling agent; d) 20-60 parts by weight of a polyetheramine curing agent; e) 10-40 parts by weight of a filler; and f) 0-10 parts by weight of an imidazole accelerator. The epoxy adhesive composition provided by the present invention has a good workability and curing process operability. In addition, an epoxy adhesive prepared from the epoxy adhesive composition has a good peel strength on a plastic surface and good resistance to water vapor permeation.

Description

EPOXY ADHESIVE COMPOSITION, EPOXY ADHESIVE, AND METHOD FOR
PREPARING EPOXY ADHESIVE
Technical Field
The present invention relates to the field of adhesives. In particular, the present invention relates to an epoxy adhesive composition, an epoxy adhesive, and a method for preparing the epoxy adhesive.
Background
With the rapid development of electronic products, the precision, integration, artistry, and efficiency thereof are increasing. Meanwhile, plastics are widely used to replace traditional glass and metal substrates so as to achieve lightweight electronic products. Many small plastic components, such as protective boards for printed circuit boards, magnets, and electronic shelf labels, need to be adhered to specific locations of electronic products by suitable adhesives. In addition, some special applications, such as encapsulation and caulking of electronic products, also require the use of suitable adhesives.
Because electronic components generally need to be temperature resistant, one-part adhesives that can be cured at a low temperature are typically used to achieve precise dispensing of electronic products. Currently, suitable adhesives mainly include epoxy mercaptan-based epoxy adhesives. However, such epoxy adhesives typically have poor resistance to water vapor permeation and often fail to meet the requirements of practical application.
Therefore, in order to solve the aforementioned technical problem, it is necessary to develop a novel adhesive having good resistance to water vapor permeation.
Summary
One object of the present invention is to provide an epoxy adhesive composition and an epoxy adhesive prepared from the epoxy adhesive composition. The epoxy adhesive composition has a good workability and curing process operability. In addition, the epoxy adhesive has a good T-peel strength on a plastic surface (especially a polyethylene terephthalate (PET) surface) and good resistance to water vapor permeation.
Another object of the present invention is to provide a method for preparing an epoxy adhesive. To this end, in one aspect, the present invention provides an epoxy adhesive composition, comprising: a) 10-50 parts by weight of a bisphenol A epoxy resin, a bisphenol F epoxy resin, or a combination of a bisphenol A epoxy resin and a bisphenol F epoxy resin, wherein the bisphenol A epoxy resin and the bisphenol F epoxy resin have an epoxy equivalent weight of 150-250 g/Eq; b) 20-50 parts by weight of a dihydroxy phenol glycidyl ether epoxy resin having an epoxy equivalent weight of 100-150 g/Eq; c) 1-5 parts by weight of a silane coupling agent; d) 20-60 parts by weight of a polyetheramine curing agent; e) 10-40 parts by weight of a filler; and f) 0-10 parts by weight of an imidazole accelerator.
According to certain technical solutions of the present invention, the content of the bisphenol A epoxy resin, the bisphenol F epoxy resin, or the combination of the bisphenol A epoxy resin and the bisphenol F epoxy resin is 10-50 parts by weight, preferably 15-40 parts by weight.
According to certain technical solutions of the present invention, the dihydroxy phenol glycidyl ether epoxy resin is one or more selected from the group of: a phenyl diphenol glycidyl ether epoxy resin and a naphthyl diphenol glycidyl ether epoxy resin.
According to certain technical solutions of the present invention, the content of the dihydroxy phenol glycidyl ether epoxy resin is 20-50 parts by weight, preferably 30-45 parts by weight.
According to certain technical solutions of the present invention, the silane coupling agent is one or more selected from the group of: an epoxy-terminated silane coupling agent, an amino-terminated silane coupling agent, and a thiol-terminated silane coupling agent.
According to certain technical solutions of the present invention, the content of the silane coupling agent is 1-5 parts by weight, preferably 2-4 parts by weight.
According to certain technical solutions of the present invention, the polyetheramine curing agent is one or more selected from the group of: bifunctional polypropylene glycol polyetheramine, trifunctional polypropylene glycol polyetheramine, and bifunctional polybutylene glycol polyetheramine.
According to certain technical solutions of the present invention, the content of the polyetheramine curing agent is 20-60 parts by weight, preferably 40-60 parts by weight. According to certain technical solutions of the present invention, the filler is one or more selected from the group of: talcum powder, polyolefin powder, wollastonite, quartz powder, and mica powder.
According to certain technical solutions of the present invention, the content of the filler is 10-40 parts by weight, preferably 15-30 parts by weight.
According to certain technical solutions of the present invention, the epoxy adhesive composition has a viscosity less than or equal to 2000 mPa· s at 25°C and a working window greater than or equal to 6 hours at 25°C.
According to certain technical solutions of the present invention, the imidazole accelerator is one or more selected from the group of: N-methylimidazole, 1,2- dimethylimidazole, and 2-ethyl-4-methylimidazole.
According to certain technical solutions of the present invention, the content of the imidazole accelerator is 2-5 parts by weight.
According to certain technical solutions of the present invention, the epoxy adhesive composition has a curing time less than or equal to 30 minutes.
In another aspect, the present invention provides an epoxy adhesive, comprising: a cured product of the epoxy adhesive composition provided according to the present invention.
According to certain technical solutions of the present invention, the epoxy adhesive has a T-peel strength greater than or equal to 1.0 N/mm on a polyethylene terephthalate (PET) surface and a water vapor permeability less than or equal to 6.0 g mm/m2-24hr at 60°C.
In yet another aspect, the present invention provides a method for preparing an epoxy adhesive, comprising the step of: curing the epoxy adhesive composition provided according to the present invention to obtain the epoxy adhesive.
According to one embodiment of the present invention, the epoxy adhesive composition provided by the present invention has a good workability and curing process operability; and an epoxy adhesive prepared from the epoxy adhesive composition has a good peel strength on a plastic surface (especially on a PET surface) and a good water vapor permeability.
Hereinafter, the present invention will be described in more detail in combination with the detailed description of the present invention. Detailed Description
Hereinafter, in order to describe the present invention more clearly, several technical solutions of the present invention and several technical solutions for comparison are described. However, this section only exemplifies some specific embodiments claimed, in which the technical features recited in one or more technical solutions can be combined with any one or more technical solutions, and these technical solutions obtained by combination also fall within the protection scope of the present application as long as they do not depart from the spirit of the present invention.
Epoxy adhesive composition
The epoxy adhesive composition provided by the present invention comprises: a) 10- 50 parts by weight of a bisphenol A epoxy resin, a bisphenol F epoxy resin, or a combination of a bisphenol A epoxy resin and a bisphenol F epoxy resin, wherein the epoxy equivalent weight thereof is 150-250 g/Eq; b) 20-50 parts by weight of a dihydroxy phenol glycidyl ether epoxy resin having an epoxy equivalent weight of 100- 150 g/Eq; c) 1 -5 parts by weight of a silane coupling agent; d) 20-60 parts by weight of a polyetheramine curing agent; e) 10-40 parts by weight of a filler; and f) 0-10 parts by weight of an imidazole accelerator.
In the present invention, the bisphenol A epoxy resin and the bisphenol F epoxy resin have an epoxy equivalent weight of 150-250 g/Eq. The bisphenol A epoxy resin and the bisphenol F epoxy resin can adjust the water vapor permeability of the epoxy adhesive.
According to one embodiment of the present invention, the content of the bisphenol A epoxy resin, the bisphenol F epoxy resin, or the combination of the bisphenol A epoxy resin and the bisphenol F epoxy resin is 10-50 parts by weight, preferably 15-40 parts by weight.
According to one embodiment of the present invention, the bisphenol A epoxy resin may be selected from EPON 826 available from Hexion Specialty Chemicals Co., Ltd. (Columbus, USA).
According to one embodiment of the present invention, the bisphenol F epoxy resin may be selected from Araldite GY 285 available from Huntsman Co., Ltd. (Houston, USA).
In the present invention, the dihydroxy phenol glycidyl ether epoxy resin can adjust not only the viscosity of the epoxy adhesive but also the peel strength thereof on a plastic surface (especially a PET surface). According to one embodiment of the present invention, the dihydroxy phenol glycidyl ether epoxy resin is one or more selected from the group of: a phenyl diphenol glycidyl ether epoxy resin and a naphthyl diphenol glycidyl ether epoxy resin.
According to one embodiment of the present invention, the content of the dihydroxy phenol glycidyl ether epoxy resin is 20-50 parts by weight, preferably 30-45 parts by weight.
According to one embodiment of the present invention, the phenyl diphenol glycidyl ether epoxy resin may be selected from Denacol EX-201 IM available from Nagase America Corporation (New York City, USA); and the naphthyl diphenol glycidyl ether epoxy resin may be selected from HP4032D available from DIC Co., Ltd. (Tokyo, Japan).
In the present invention, the silane coupling agent can adjust the peel strength of the epoxy adhesive on a plastic surface (especially a PET surface).
According to one embodiment of the present invention, the silane coupling agent is one or more selected from the group of: an epoxy -terminated silane coupling agent, an amino-terminated silane coupling agent, and a thiol-terminated silane coupling agent.
According to one embodiment of the present invention, the content of the silane coupling agent is 1-5 parts by weight, preferably 2-4 parts by weight.
According to one embodiment of the present invention, the silane coupling agent may be selected from Z6040 available from Dowcoming Co., Ltd. (Midland, USA).
In the present invention, the polyetheramine curing agent can not only promote the curing of the epoxy adhesive composition, but also adjust the viscosity of the epoxy adhesive and the peel strength on a plastic surface (especially a polyethylene terephthalate (PET) surface).
According to one embodiment of the present invention, the polyetheramine curing agent is one or more selected from the group of: bifunctional polypropylene glycol polyetheramine, trifunctional polypropylene glycol polyetheramine, and bifunctional polybutylene glycol polyetheramine.
According to one embodiment of the present invention, the content of the polyetheramine curing agent is 20-60 parts by weight, preferably 30-50 parts by weight.
According to one embodiment of the present invention, the bifunctional polypropylene glycol polyetheramine curing agent may be selected from D230 and D400 available from Huntsman Co., Ltd. (Houston, USA); and the trifunctional polypropylene glycol polyetheramine curing agent may be selected from T403 available from Huntsman Co., Ltd. (Houston, USA).
In the present invention, the filler can adjust the water vapor permeability of the epoxy adhesive. According to one embodiment of the present invention, the filler is one or more selected from the group of: talcum powder, polyolefin powder, wollastonite, quartz powder, and mica powder.
According to one embodiment of the present invention, the content of the filler is 10- 40 parts by weight, preferably 15-30 parts by weight.
According to one embodiment of the present invention, the talcum powder may be selected from AH51210 available from Quartz Industry Materials (Shanghai) Co., Ltd. (Shanghai, China); and the polyolefin powder may be selected from MICROTHENE F FA 700-00 available from LyondellBassell Chemical Company (Houston, USA).
In the present invention, an imidazole accelerator may be optionally added to the epoxy adhesive composition to shorten the curing time thereof, thereby improving the curing process operability.
According to one embodiment of the present invention, the imidazole accelerator is one or more selected from the group of: N-methylimidazole, 1,2-dimethylimidazole, and 2- ethyl-4-methylimidazole.
According to one embodiment of the present invention, the content of the imidazole accelerator is 0-10 parts by weight, preferably 2-5 parts by weight.
According to one embodiment of the present invention, N-methylimidazole and 2- ethyl-4-methylimidazole are commercially available from Shikoku Chemicals Corporation (Chiba City, Japan); and 1,2-dimethylimidazole is commercially available from Ningxia Joie Material Co., Ltd. (Ningxia, China). According to one embodiment of the present invention, the epoxy adhesive composition has a viscosity less than or equal to 2000 mPa s at 25°C and a working window greater than or equal to 6 hours at 25°C.
According to one embodiment of the present invention, the epoxy adhesive composition may be stored at a condition less than or equal to -20°C.
Epoxy adhesive
The epoxy adhesive provided by the present invention comprises: a cured product of the epoxy adhesive composition provided according to the present invention. For details of each component included in the epoxy adhesive composition, see the “Epoxy adhesive composition” section of the present specification, which will not be described herein again.
According to one embodiment of the present invention, the epoxy adhesive has a T- peel strength greater than or equal to 1.0 N/mm on a polyethylene terephthalate (PET) surface and a water vapor permeability less than or equal to 6.0 g mm/m2-24hr at 60°C.
Method for preparing epoxy adhesive
The method for preparing an epoxy adhesive provided by the present invention comprises the step of: curing the epoxy adhesive composition provided according to the present invention to obtain the epoxy adhesive. For details of each component included in the epoxy adhesive composition, see the “Epoxy adhesive composition” section of the present specification, which will not be described herein again.
According to one embodiment of the present invention, in particular, the preparation method may comprise the following steps:
Step 1, mixing the bisphenol A epoxy resin and/or the bisphenol F epoxy resin, the dihydroxy phenol glycidyl ether epoxy resin, and the silane coupling agent of the epoxy adhesive composition provided by the present invention under a condition of room temperature (25 °C) to obtain a first mixture;
Step 2, adding the filler of the epoxy adhesive composition provided by the present invention to the first mixture to obtain a second mixture; and
Step 3 : adding the polyetheramine curing agent and the imidazole accelerator of the epoxy adhesive composition provided by the present invention to the second mixture, followed by curing to obtain the epoxy adhesive.
According to one embodiment of the present invention, in Step 2, the filler of the epoxy adhesive composition provided by the present invention may be added to the first mixture after high-speed dispersion mixing, which is subjected to at least three times of three-roll milling to obtain the second mixture.
According to one embodiment of the present invention, in Step 3, the second mixture may be cooled to 10°C or below before adding the polyetheramine curing agent and the imidazole accelerator of the epoxy adhesive composition provided by the present invention to the second mixture.
According to one embodiment of the present invention, in Step 3, after adding the polyetheramine curing agent and the imidazole accelerator of the epoxy adhesive composition provided by the present invention to the second mixture, the mixture may be mixed thoroughly at a low temperature (<10°C) and then subjected to sufficient vacuum defoaming to obtain the epoxy adhesive.
Examples
Hereinafter, preferred examples will be provided to better understand the present invention. However, the following examples are only for illustrative purposes and for a person skilled in the art to better understand the present invention, and the present invention should not be limited by these examples.
1. Raw Materials
(1) Bisphenol A epoxy
EPON 826, a bisphenol A epoxy resin having an epoxy equivalent weight of 178-186 g/Eq, commercially available from Hexion Specialty Chemicals Co., Ltd. (Columbus, USA).
(2) Bisphenol F epoxy resin
Araldite GY 285, a bisphenol F epoxy resin having an epoxy equivalent weight of 164-173 g/Eq, commercially available from Huntsman Co., Ltd. (Houston, USA).
(3) Dihydroxy phenol glycidyl ether epoxy
Denacol EX-201 IM, a phenyl diphenol glycidyl ether epoxy resin having an epoxy equivalent weight of 120-135 g/Eq, commercially available from Nagase America Corporation (New York City, USA).
HP4032D, a naphthyl diphenol glycidyl ether epoxy resin having an epoxy equivalent weight of 140 g/Eq, commercially available from DIC Co., Ltd. (Tokyo, Japan).
(4) Other epoxy resin
AFG-90, an aminophenol trifunctional epoxy resin having an epoxy equivalent weight of 105-115 g/Eq, commercially available from ShangHai HuaYi Resins Co., Ltd. (Shanghai, China).
DY-D, a butanediol di glycidyl ether epoxy resin having an epoxy equivalent weight of 118-125 g/Eq, commercially available from Huntsman Co., Ltd. (Houston, USA).
(5) Silane coupling agent
Z6040, an epoxy-terminated silane coupling agent, commercially available from Dowcoming Co., Ltd. (Midland, USA).
(6) Polyetheramine curing agent D230, a bifunctional polypropylene glycol polyetheramine curing agent having an active hydrogen equivalent weight of 60 g/Eq, commercially available from Huntsman Co., Ltd. (Houston, USA).
D400, a bifunctional polypropylene glycol polyetheramine curing agent having an active hydrogen equivalent weight of 115 g/Eq, commercially available from Huntsman Co., Ltd. (Houston, USA).
T403, a trifunctional polypropylene glycol polyetheramine curing agent having an active hydrogen equivalent weight of 80 g/Eq, commercially available from Huntsman Co., Ltd. (Houston, USA).
(7) Filler
AH51105, talcum powder, commercially available from Quartz Industry Materials (Shanghai) Co., Ltd. (Shanghai, China);
WSE600, wollastonite, commercially available from Quartz Industry Materials (Shanghai) Co., Ltd. (Shanghai, China);
MICROTHENE F FA 700-00, polyolefin powder, commercially available from Lyondell Bassell Chemical Company (Houston, USA).
(8) Substrate
A PET substrate, commercially available from REIKO Company (Tokyo, Japan).
(9) Imidazole accelerator
N-methylimidazole, commercially available from Shikoku Chemicals Corporation (Chiba City, Japan);
1,2-dimethylimidazole, commercially available from Ningxia Joie Material Co., Ltd. (Ningxia, China);
2-ethyl-4-methylimidazole, commercially available from Shikoku Chemicals Corporation (Chiba City, Japan).
2. Test method (1) Workability test
This test uses a viscometer (model DV2TLV, commercially available from Brookfield Company, Middleboro, USA) to test the viscosity of the adhesive composition provided in the examples and comparative examples of the present invention. The specific test steps are as follows: Step 1 : The adhesive composition is removed from a freezer, and the time at which is recorded as To, and then the adhesive composition is warmed naturally to 25°C and is in a liquid state.
Step 2: The warmed adhesive composition is charged into a material cup, and the viscometer is zeroed and calibrated.
Step 3 : A suitable rotor is selected, which corresponding viscosity value is tested with a viscometer and recorded, and the torque is ensured within 10% to 90%.
Step 4: After a certain time interval, the viscosity value of the adhesive composition is tested, and the time when the viscosity of the adhesive composition reaches 10000 mPa s is recorded as Ti. Assuming that the working window of the adhesive composition is T, then T=Ti-To.
When the measured viscosity of the epoxy adhesive composition is less than or equal to 2000 mPa s, and the working window T of the epoxy adhesive composition at 25°C is greater than or equal to 6 hours, it indicates that the epoxy adhesive composition has a good workability. When the measured viscosity of the epoxy adhesive composition is less than or equal to 1000 mPa· s, and the working window T of the epoxy adhesive composition at 25°C is greater than or equal to 8 hours, it indicates that the epoxy adhesive composition has an excellent workability.
(2) T-peel strength test
This test is in accordance with Test Standard ASTM D1876 and performed on a polyethylene terephthalate (PET) substrate surface at a stretching rate of 100 mm/minute to measure the T-peel strengths on the PET surface of the adhesives provided in the examples and the comparative examples of the present invention.
When the measured T-peel strength is greater than or equal to 1.0 N/mm, it indicates that the adhesive has a good T-peel strength; and when the measured T-peel strength is greater than or equal to 1.5 N/mm, it indicates that the adhesive has an excellent T-peel strength.
(3) Resistance to water vapor permeation test
This test is in accordance with ASTM F-1249 to measure the water vapor permeability of the adhesives (1 mm thick) provided in the examples and the comparative examples of the present invention at 60°C, the test conditions were “60°C, 100% humidity”, and the unit of test results is g mm/m2-24hr. When the measured water vapor permeability is less than or equal to 6.0 g mm/m2-24hr, it indicates that the adhesive has good resistance to water vapor permeation; and when the measured water vapor permeability is less than or equal to 5.5 g mm/m2-24hr, it indicates that the adhesive has excellent resistance to water vapor permeation.
(4) Cure speed test
This test uses a rheometer (model ARES G2, commercially available from TA Instruments, USA) to test the cure speed of the adhesive composition provided in the examples and comparative examples of the present invention. The test steps are as follows:
Step 1: The adhesive composition is removed from a freezer, and then the adhesive composition is warmed naturally to 25°C and is in a liquid state.
Step 2: A 25 mm test aluminum pan is selected and mounted on the rheometer, followed by zeroing, and the operate program is set with a test temperature of 70°C, a shear rate of 5.0 1/s, and total test duration of 5400 s.
Step 3 : The adhesive composition warmed to 25°C is used as a test sample and placed on the test aluminum plate. The height of the aluminum plate is lower to 0.5 mm (that is, the thickness of the test sample is 0.5 mm). The holding furnace is turned off, followed by measuring the curing time of the sample (at 70°C). The time corresponding to the position where the storage modulus and loss modulus curves of the test sample intersect is the curing time.
When the measured curing time is less than or equal to 30 min, it indicates that the test sample has a good curing process operability.
Example El
21 g EPON 826, 9 g Araldite GY 285, 30 g Denacol EX-201 IM, 15 g HP4032D, and 2 g Z6040 were added to a 250 ml reaction vessel. Then, under the condition of 25°C, the above was stirred at a rotation speed of 1000 revolutions per minute until a homogeneous first mixture was obtained.
20 g of a filler (WSE600) was added to the first solution. Then, the above was mechanically stirred until well dispersed and resulting in a second mixture.
The second mixture was milled three times with a three-roll miller, model 50, commercially available from EXAKT Advanced Technology Company, Norderstedt, Germany, to ensure that the average particle diameter of the second mixture was controlled at 50 microns or less. The second mixture was cooled to 10°C or below, and 20 g D230 and 40 g D400 were added thereto. Then, under the condition of vacuum, the above was stirred at a rotation speed of 1000 revolutions per minute until a uniform epoxy adhesive composition was obtained. Preferably, the epoxy adhesive composition may be sealed and stored at less than or equal to -20°C.
The epoxy adhesive composition was heated to 70°C, cured for 1 hours, and left at room temperature (25°C) for 3 days to ully cure, thereby obtaining an epoxy adhesive.
The epoxy adhesive composition was subjected to the workability test according to the test method described herein, and the epoxy adhesive was subjected to the T-peel strength test and resistance to water vapor permeation test. The test results are listed in Table 1
Examples E2-E7
The epoxy adhesives of examples E2-E7 were prepared in the same manner as example El with the exception that the components and amounts of the epoxy adhesive compositions used to prepare the epoxy adhesives were different. The components and amounts thereof are specifically listed in Table 1.
The epoxy adhesive compositions provided by examples E2-E7 were subjected to the workability test according to the test method described herein, and the epoxy adhesives were subjected to the T-peel strength test and resistance to water vapor permeation test. The test results are listed in Table 1.
Comparative examples C1-C5
The epoxy adhesives of comparative examples C1-C5 were prepared in the same manner as example El with the exception that the components and amounts of the epoxy adhesive compositions used to prepare the epoxy adhesives were different. The components and amounts thereof are specifically listed in Table 2.
The epoxy adhesive compositions provided by comparative examples C1-C5 were subjected to the workability test according to the test method described herein, and the epoxy adhesives were subjected to the T-peel strength test and resistance to water vapor permeation test. The test results are listed in Table 2.
Examples E8-E11
The epoxy adhesives of examples E8-E11 is prepared in the same manner as example El with the exception that as the polyetheramine curing agent was added, an imidazole accelerator was also added, and the components and amounts of the epoxy adhesive compositions used to prepare the epoxy adhesives were different. The components and amounts thereof are specifically listed in Table 3.
The epoxy adhesive compositions provided by examples E8-E11 were subjected to the workability test according to the test method described herein, and the epoxy adhesives were subjected to the T-peel strength test and resistance to water vapor permeation test.
The test results are listed in Table 3.
Table 1. Examples E1-E7
Figure imgf000015_0001
Table 2. Comparative examples C1-C5
Figure imgf000016_0001
Table 3. Example E8-E11
Figure imgf000017_0001

Claims

What is claimed is:
1. An epoxy adhesive composition, comprising: a) 10-50 parts by weight of a bisphenol A epoxy resin, a bisphenol F epoxy resin, or a combination of a bisphenol A epoxy resin and a bisphenol F epoxy resin, wherein the bisphenol A epoxy resin and the bisphenol F epoxy resin have an epoxy equivalent weight of 150-250 g/Eq; b) 20-50 parts by weight of a dihydroxy phenol glycidyl ether epoxy resin having an epoxy equivalent weight of 100-150 g/Eq; c) 1-5 parts by weight of a silane coupling agent; d) 20-60 parts by weight of a polyetheramine curing agent; e) 10-40 parts by weight of a filler; and f) 0-10 parts by weight of an imidazole accelerator.
2. The epoxy adhesive composition according to claim 1, wherein the content of the bisphenol A epoxy resin, the bisphenol F epoxy resin, or the combination of the bisphenol A epoxy resin and the bisphenol F epoxy resin is 15-40 parts by weight.
3. The epoxy adhesive composition according to claim 1, wherein the dihydroxy phenol glycidyl ether epoxy resin is one or more selected from the group of: a phenyl diphenol glycidyl ether epoxy resin and a naphthyl diphenol glycidyl ether epoxy resin.
4. The epoxy adhesive composition according to claim 1, wherein the content of the dihydroxy phenol glycidyl ether epoxy resin is 30-45 parts by weight.
5. The epoxy adhesive composition according to claim 1, wherein the silane coupling agent is one or more selected from the group of: an epoxy -terminated silane coupling agent, an amino- terminated silane coupling agent, and a thiol-terminated silane coupling agent.
6. The epoxy adhesive composition according to claim 1, wherein the content of the silane coupling agent is 2-4 parts by weight.
7. The epoxy adhesive composition according to claim 1, wherein the polyetheramine curing agent is one or more selected from the group of: bifunctional polypropylene glycol polyetheramine, trifunctional polypropylene glycol polyetheramine, and bifunctional polybutylene glycol polyetheramine.
8. The epoxy adhesive composition according to claim 1 or 4, wherein the content of the polyetheramine curing agent is 40-60 parts by weight.
9. The epoxy adhesive composition according to claim 1, wherein the filler is one or more selected from the group of: talcum powder, polyolefin powder, wollastonite, quartz powder, and mica powder.
10. The epoxy adhesive composition according to claim 1, wherein the content of the filler is 15-30 parts by weight.
11. The epoxy adhesive composition according to claim 1, wherein the epoxy adhesive composition has a viscosity less than or equal to 2000 mPa· s at 25°C and a working window greater than or equal to 6 hours at 25 °C.
12. The epoxy adhesive composition according to claim 1, wherein the imidazole accelerator is one or more selected from the group of: N-methylimidazole, 1,2-dimethylimidazole, and 2-ethyl- 4-methylimidazole.
13. The epoxy adhesive composition according to claim 1, wherein the content of the imidazole accelerator is 2-5 parts by weight.
14. The epoxy adhesive composition according to any one of claims 1, 12, and 13, wherein the epoxy adhesive composition has a curing time less than or equal to 30 minutes.
15. An epoxy adhesive, comprising: a cured product of the epoxy adhesive composition according to any one of claims 1-14.
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