CN112409972A - Low-temperature fast-curing single-component epoxy electronic adhesive with benzoquinone as stabilizer - Google Patents
Low-temperature fast-curing single-component epoxy electronic adhesive with benzoquinone as stabilizer Download PDFInfo
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- CN112409972A CN112409972A CN202011368479.6A CN202011368479A CN112409972A CN 112409972 A CN112409972 A CN 112409972A CN 202011368479 A CN202011368479 A CN 202011368479A CN 112409972 A CN112409972 A CN 112409972A
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- benzoquinone
- low
- curing
- component epoxy
- stabilizer
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 239000004593 Epoxy Substances 0.000 title claims abstract description 42
- 239000000853 adhesive Substances 0.000 title claims abstract description 32
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 32
- 239000003381 stabilizer Substances 0.000 title claims abstract description 23
- 239000003822 epoxy resin Substances 0.000 claims abstract description 17
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 17
- 239000003292 glue Substances 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims abstract description 12
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 9
- 239000013008 thixotropic agent Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 4
- JJSYPAGPNHFLML-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-sulfanylpropanoic acid Chemical compound OC(=O)CCS.OC(=O)CCS.OC(=O)CCS.CCC(CO)(CO)CO JJSYPAGPNHFLML-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910021485 fumed silica Inorganic materials 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 229920005692 JONCRYL® Polymers 0.000 claims description 3
- 239000004844 aliphatic epoxy resin Substances 0.000 claims description 2
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims description 2
- 235000013923 monosodium glutamate Nutrition 0.000 claims description 2
- 239000004223 monosodium glutamate Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 abstract description 7
- 238000007323 disproportionation reaction Methods 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000013035 low temperature curing Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 3
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000007240 daidzein Nutrition 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 229920006335 epoxy glue Polymers 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012205 single-component adhesive Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- 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
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention relates to a low-temperature fast-curing single-component epoxy electronic adhesive taking benzoquinone as a stabilizer, which comprises the following components in part by weight: epoxy resin monomer, benzoquinone, a cross-linking agent, a curing accelerator and a thixotropic agent. The beneficial effects are as follows: the benzoquinone is innovatively used as a stabilizer to prepare the low-temperature fast-curing single-component epoxy electronic glue, the benzoquinone can perform disproportionation reaction with free radicals formed by epoxy resin monomers in the storage process to generate benzoquinone type free radicals, and the benzoquinone type free radicals can be combined with active free radicals to obtain inactive products, so that the benzoquinone type free radicals play a role of the stabilizer. The addition of benzoquinone can prolong the storage time of the single-component epoxy electronic adhesive at room temperature to more than one month. Meanwhile, benzoquinone can be sublimated rapidly when being heated, so that the curing speed of the single-component epoxy electronic adhesive is accelerated (8 min at 60 ℃ and 2min at 80 ℃).
Description
Technical Field
The invention relates to the field of high-molecular bonding materials, in particular to a single-component epoxy electronic adhesive capable of realizing rapid curing at a low temperature.
Background
With the advancement of technology and the increase of consumer level, people have more and more demands on electronic products, so that consumer electronics have been rapidly developed in recent years. New electronic products such as smart phones, sports watches, sweeping robots and unmanned aerial vehicles are in a large number, and new requirements for structural bonding are provided in the new products. Because most electronic components are sensitive to temperature and cannot resist high temperature, a bonding material capable of being cured at low temperature is urgently needed in the field of electronic glue to meet the use requirement. The double-component adhesive needs to be prepared on site, has higher use requirement, is easy to have quality problems of disordered matching, no solidification/incomplete solidification and the like, so the single-component adhesive has obvious advantages. However, the low-temperature curing one-component epoxy resins currently available on the market generally have the problems of slow curing speed at low temperature or short operable time at room temperature.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a low-temperature fast-curing single-component epoxy electronic adhesive taking benzoquinone as a stabilizer. Acid substances are mostly used as a stabilizer in common low-temperature curing single-component epoxy glue, the patent application publication No. CN 106554740A and the invention patent with the application publication date of 2017, 04, month and 5 disclose a low-temperature fast curing single-component epoxy adhesive glue and a preparation method thereof, and the invention uses acid substances such as salicylic acid, lactic acid, benzoic acid and the like as the stabilizer. The prepared glue can be placed for 2 weeks at room temperature and can be cured at 60 ℃ for 20 minutes. Although the invention meets the requirements of low-temperature curing and room-temperature storage to a certain extent, the curing speed and room-temperature storage time have further room for improvement. The invention discloses a low-temperature curing type single-component epoxy disclosed in patent application publication No. CN 107400490A, which is an invention patent with publication date of 2017, 11 and 28, wherein an accelerator with low activity is selected, and although the prepared single-component epoxy can be stored for three months at room temperature, the curing time in use needs about 2 hours, and the requirement on the production efficiency of electronic products cannot be met.
The invention provides a low-temperature fast curing single-component epoxy electronic adhesive with benzoquinone as a stabilizer, which comprises the following technical scheme:
a low-temperature fast-curing single-component epoxy electronic adhesive taking benzoquinone as a stabilizer comprises an epoxy resin monomer, benzoquinone, a cross-linking agent, a curing accelerator and a thixotropic agent.
The weight percentage of the epoxy resin monomer in the single-component epoxy electronic adhesive is 30-70%, the weight percentage of benzoquinone in the epoxy electronic adhesive is 0.2-3%, the weight percentage of the cross-linking agent in the epoxy electronic adhesive is 20-60%, the weight percentage of the curing accelerator in the epoxy electronic adhesive is 1-9%, and the weight percentage of the thixotropic agent in the epoxy electronic adhesive is 0.3-6%.
The epoxy resin monomer is low-viscosity aliphatic epoxy resin and is selected from one or a mixture of any two of DER755, DER732 and JONCRYL 61 of Dow chemical.
The cross-linking agent is one or a mixture of any more of pentaerythritol tetra-3-mercaptopropionate (PETMP), trimethylolpropane tri (3-mercaptopropionate) (TMPMP), pentaerythritol tetra-mercaptoacetate (PETMMA) and trimethylolpropane tri (3-mercaptopropionate) (TMPMA).
The curing accelerator is one or a mixture of any more of PN-23J, MY-24 of Japanese monosodium glutamate and Asahi electrochemical EH 4070S.
The thixotropic agent is one or a mixture of any more of fumed silica R974, A200 and A300.
The implementation of the invention comprises the following technical effects:
the invention provides a low-temperature fast curing single-component epoxy electronic adhesive taking benzoquinone as a stabilizer. The benzoquinone is innovatively used as a stabilizer to prepare the low-temperature fast-curing single-component epoxy electronic glue, the benzoquinone can perform disproportionation reaction with free radicals formed by epoxy resin monomers in the storage process to generate benzoquinone type free radicals, and the benzoquinone type free radicals can be combined with active free radicals to obtain inactive products, so that the benzoquinone type free radicals play a role of the stabilizer. The addition of benzoquinone can prolong the storage time of the single-component epoxy electronic adhesive at room temperature to more than one month. Meanwhile, benzoquinone can be sublimated rapidly when heated, so that the curing speed of the single-component epoxy electronic adhesive is increased, the single-component epoxy electronic adhesive can be cured within 8 minutes at 60 ℃ and can be cured within 2 minutes at 80 ℃, and the production efficiency of electronic products can be greatly improved.
Drawings
FIG. 1 shows the results of DSC measurement in example 2.
Detailed Description
The present invention will be described in detail with reference to the following examples, which are intended to facilitate the understanding of the present invention and should not be construed as limiting in any way.
The low-temperature fast-curing single-component epoxy electronic glue with benzoquinone as a stabilizer provided by the embodiment comprises an epoxy resin monomer, benzoquinone, a cross-linking agent, a curing accelerator and a thixotropic agent. The specific processing process flow is as follows: accurately weighing an epoxy resin monomer and benzoquinone, stirring and mixing the epoxy resin monomer and the benzoquinone for 20 minutes in a double-planet way at the temperature of 0-30 ℃, adding a corresponding amount of a cross-linking agent and a curing accelerator, continuously stirring for 30 minutes, then adding a thixotropic agent according to the amount, stirring for 20 minutes, defoaming and filling in vacuum to obtain the low-temperature fast-curing single-component epoxy electronic adhesive.
The preparation method of the low-temperature fast curing one-component epoxy electronic glue using benzoquinone as a stabilizer is described in the following examples.
Example 1
The preparation method of the low-temperature fast curing single-component epoxy electronic adhesive using benzoquinone as the stabilizer in the embodiment is that 5000 g of Dow chemical DER755 epoxy resin and 20 g of benzoquinone are precisely weighed and stirred and mixed in a double planetary way for 20 minutes at 0-30 ℃, then 3800 g of pentaerythritol tetra-3-mercaptopropionate (PETMP) and 200 g of Nizhisu PN-23J are added to continue stirring for 30 minutes to ensure that the accelerator is uniformly dispersed in the resin, 180 g of winning R974 fumed silica is added to stir for 20 minutes, and the low-temperature fast curing single-component epoxy electronic adhesive is obtained by vacuum deaeration.
Example 2
In the preparation method of the low-temperature fast curing single-component epoxy electronic adhesive using benzoquinone as a stabilizer, 8000 g of Dow chemical DER732 epoxy resin and 60 g of benzoquinone are precisely weighed and stirred and mixed for 20 minutes in a double planetary way at 0-30 ℃, 5200 g of trimethylolpropane tris (3-mercaptopropionate) (TMPMP) and 300 g of Ribes MY-24 are added and stirred for 30 minutes to ensure that the accelerator is uniformly dispersed in the resin, 260 g of Windaway A200 fumed silica is added and stirred for 20 minutes, and the low-temperature fast curing single-component epoxy electronic adhesive is obtained by vacuum defoaming.
Example 3
The preparation method of the low-temperature fast curing single-component epoxy electronic adhesive using benzoquinone as the stabilizer in this example is that 6000 g of basf JONCRYL 61 epoxy resin and 40 g of benzoquinone are precisely weighed and stirred and mixed with each other in a double planetary way at 0-30 ℃ for 20 minutes, 3200 g of pentaerythritol tetra-mercapto acetate (PETMA) and 260 g of Asahi electrochemical EH4070S are added and stirred for 30 minutes to ensure that the accelerator is dispersed evenly in the resin, 150 g of creative A300 fumed silica is added and stirred for 20 minutes, and the low-temperature fast curing single-component epoxy electronic adhesive is obtained by vacuum deaeration.
Example 4
In this embodiment, 10000 g of dow chemical DER755 epoxy resin and 480 g of benzoquinone are precisely weighed and stirred and mixed with each other in a double planetary way at 0-30 ℃ for 20 minutes, then 7800 g of trimethylolpropane tris (3-mercaptopropionate) (TMPMA) and 850 g of MYs-24 of daidzein are added and stirred for 30 minutes to ensure that the accelerator is uniformly dispersed in the resin, 420 g of won R974 fumed silica is added and stirred for 20 minutes, and the low-temperature fast curing single-component epoxy electronic adhesive is obtained by vacuum deaeration.
Table 1 examples 1-4 test results
Example 1 | Example 2 | Example 3 | Example 4 | |
Setting time (60 ℃ C.) | 5 minutes | 6 minutes | 6 minutes | 7 minutes |
Setting time (80 ℃ C.) | 1.5 minutes | 2 minutes | 2 minutes | 2 minutes |
Storage time at room temperature | More than or equal to 30 days | More than or equal to 30 days | More than or equal to 30 days | More than or equal to 45 days |
Adhesion (aluminium/aluminium) | 12Mpa | 11Mpa | 12Mpa | 9Mpa |
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention, and not for limiting the protection scope of the present invention, although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (5)
1. A low-temperature fast-curing single-component epoxy electronic glue taking benzoquinone as a stabilizer comprises an epoxy resin monomer, benzoquinone, a cross-linking agent, a curing accelerator and a thixotropic agent; the method is characterized in that: the weight percentage of the epoxy resin monomer in the single-component epoxy electronic adhesive is 30-70%, the weight percentage of benzoquinone in the epoxy electronic adhesive is 0.2-3%, the weight percentage of the cross-linking agent in the epoxy electronic adhesive is 20-60%, the weight percentage of the curing accelerator in the epoxy electronic adhesive is 1-9%, and the weight percentage of the thixotropic agent in the epoxy electronic adhesive is 0.3-6%.
2. The low-temperature fast curing one-component epoxy electronic glue with benzoquinone as a stabilizer according to claim 1, wherein: the epoxy resin monomer is low-viscosity aliphatic epoxy resin and is selected from one or a mixture of any two of DER755, DER732 and JONCRYL 61 of Dow chemical.
3. The low-temperature fast curing one-component epoxy electronic glue with benzoquinone as a stabilizer according to claim 1, wherein: the cross-linking agent is one or a mixture of any more of pentaerythritol tetra-3-mercaptopropionate (PETMP), trimethylolpropane tri (3-mercaptopropionate) (TMPMP), pentaerythritol tetra-mercaptoacetate (PETMMA) and trimethylolpropane tri (3-mercaptopropionate) (TMPMA).
4. The low-temperature fast curing one-component epoxy electronic glue with benzoquinone as a stabilizer according to claim 1, wherein: the curing accelerator is one or a mixture of any more of PN-23J, MY-24 of Japanese monosodium glutamate and EH4070S of Asahi electrification.
5. The low-temperature fast curing one-component epoxy electronic glue with benzoquinone as a stabilizer according to claim 1, wherein: the thixotropic agent is one or a mixture of any more of fumed silica R974, A200 and A300.
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CN202011368479.6A CN112409972A (en) | 2020-12-02 | 2020-12-02 | Low-temperature fast-curing single-component epoxy electronic adhesive with benzoquinone as stabilizer |
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CN202011368479.6A CN112409972A (en) | 2020-12-02 | 2020-12-02 | Low-temperature fast-curing single-component epoxy electronic adhesive with benzoquinone as stabilizer |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113999637A (en) * | 2021-11-08 | 2022-02-01 | 韦尔通(厦门)科技股份有限公司 | Single-component low-temperature epoxy adhesive and preparation method thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1288481A (en) * | 1998-01-16 | 2001-03-21 | 洛克泰特(R&D)有限公司 | Curable epoxy-based compositions |
JP2005047997A (en) * | 2003-07-30 | 2005-02-24 | Sumitomo Bakelite Co Ltd | Epoxy resin composition and semiconductor device |
CN109762496A (en) * | 2018-12-24 | 2019-05-17 | 惠州市杜科新材料有限公司 | A kind of transparent single-component epoxy adhesive and preparation method thereof |
-
2020
- 2020-12-02 CN CN202011368479.6A patent/CN112409972A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1288481A (en) * | 1998-01-16 | 2001-03-21 | 洛克泰特(R&D)有限公司 | Curable epoxy-based compositions |
JP2005047997A (en) * | 2003-07-30 | 2005-02-24 | Sumitomo Bakelite Co Ltd | Epoxy resin composition and semiconductor device |
CN109762496A (en) * | 2018-12-24 | 2019-05-17 | 惠州市杜科新材料有限公司 | A kind of transparent single-component epoxy adhesive and preparation method thereof |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113999637A (en) * | 2021-11-08 | 2022-02-01 | 韦尔通(厦门)科技股份有限公司 | Single-component low-temperature epoxy adhesive and preparation method thereof |
CN113999637B (en) * | 2021-11-08 | 2023-08-04 | 韦尔通科技股份有限公司 | Single-component low-temperature epoxy adhesive and preparation method thereof |
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