CN115558099A - Hyperbranched polyphenyl ether epoxy plastic packaging material - Google Patents
Hyperbranched polyphenyl ether epoxy plastic packaging material Download PDFInfo
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- CN115558099A CN115558099A CN202211307650.1A CN202211307650A CN115558099A CN 115558099 A CN115558099 A CN 115558099A CN 202211307650 A CN202211307650 A CN 202211307650A CN 115558099 A CN115558099 A CN 115558099A
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- CN
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- Prior art keywords
- epoxy resin
- hyperbranched
- ether epoxy
- polyphenyl ether
- epoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 229920013636 polyphenyl ether polymer Polymers 0.000 title claims abstract description 6
- 239000004593 Epoxy Substances 0.000 title claims description 9
- 239000004033 plastic Substances 0.000 title claims description 8
- 229920003023 plastic Polymers 0.000 title claims description 8
- 239000005022 packaging material Substances 0.000 title description 5
- 239000003822 epoxy resin Substances 0.000 claims abstract description 33
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 14
- 229920000587 hyperbranched polymer Polymers 0.000 claims description 4
- -1 cyano, triphenyl triazine Chemical compound 0.000 claims description 2
- 229920001955 polyphenylene ether Polymers 0.000 claims description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
- 239000012965 benzophenone Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 11
- 238000004806 packaging method and process Methods 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000009477 glass transition Effects 0.000 abstract 1
- 230000015654 memory Effects 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000005979 thermal decomposition reaction Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 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 8
- 239000000047 product Substances 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YXWJGZQOGXGSSC-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(F)=C1F YXWJGZQOGXGSSC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 229920006336 epoxy molding compound Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
Classifications
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
- C08G65/485—Polyphenylene oxides
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4006—(I) or (II) containing elements other than carbon, oxygen, hydrogen or halogen as leaving group (X)
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
Abstract
The hyperbranched polyphenyl ether epoxy resin material can realize high dispersibility, improve internal stress and packaging stability, and has a good packaging effect on electronic devices such as LED chips and the like. Meanwhile, the synthesis method is disclosed, the process is simple, the raw materials are easy to obtain, and the method is suitable for large-scale popularization. The material has high glass transition temperature and high thermal decomposition temperature, and can be used in the field of packaging of chips, memories, circuit boards and the like.
Description
Technical Field
The invention belongs to the technical field of structural adhesives, and particularly relates to a hyperbranched polyphenyl ether epoxy plastic packaging material.
Background
In 1938, epoxy resins were cured by Pierre Castan, switzerland and s.o.greenlee using amine curing agents, showing good mechanical properties. After the second war, developed countries including the united states have vigorously studied new technologies for epoxy resins. Nowadays, epoxy resins have hundreds of different structures, more than 100 curing agents and modifiers are matched with the epoxy resins, and the epoxy resins have been developed into one of essential basic raw materials for the economic development of the world.
Epoxy resins are generally a class of high molecular polymers with two epoxy groups in organic molecules, and can be classified into viscous state and solid state according to molecular weight. The cured resin has good mechanical property and higher weather resistance compared with other resins. The epoxy resin is not only widely applied to high-end fields of aerospace, chip packaging and the like, but also plays an important role in daily necessities of people such as coatings, adhesives and the like. Because of low price, simple curing and forming process and good weather resistance, the research on synthesis and modification of the modified polycarbonate is more and more important. Since the application of epoxy resin in a large quantity, new varieties and corresponding curing agents thereof emerge endlessly, and the processing technology is continuously innovated, so that the epoxy resin is developed rapidly. The epoxy resin and different curing agents can present different properties after curing, the curing temperature is divided into low, medium and high, and the curing time can be instant or slow. Thus, epoxy resins provide strong coverage for applications. The epoxy resin with excellent performance has the advantages of small epoxy value change, concentrated molecular weight distribution, light color, low impurity content and low organic chlorine content.
Epoxy resins have been developed to date, and their types are still on the verge. The classification method has a room temperature state and a molecular structure. The state of room temperature can be divided into viscous state and solid state. According to the molecular structure, the epoxy resin is divided into glycidyl ether, glycidyl ester, glycidyl amine, linear aliphatic and alicyclic epoxy resin.
As electronic devices are developed to have high integration and small volume, the requirements for packaging are higher and higher. The epoxy resin material has good water resistance and heat resistance, but the internal stress formed by the shrinkage of the epoxy resin material cannot be solved well all the time, so that the toughness of the epoxy resin material is improved in the modification process, and the enhancement of the toughness can reduce the internal stress caused by the shrinkage of the epoxy resin after the epoxy resin is cured and reduce the probability of damage of the encapsulated material.
In view of the above, there is a need for an improved epoxy resin in the prior art to solve the above problems.
Disclosure of Invention
The invention aims to disclose a preparation method of a bisphenol A type epoxy resin modified material, so that a product has excellent mechanical property and low stress property. The main body resin of the general electronic plastic packaging material is mainly epoxy resin, can be applied to civil electronic products, and has the defects of large internal stress and poor heat resistance in the packaging of high-performance circuit boards. The unique molecular structure of the hyperbranched polymer can increase the compatibility with the epoxy resin when the molecular weight is not large. Based on the point, the project designs the micromolecular hyperbranched material as the internal stress modifier to be added into the epoxy resin. The epoxy resin is crosslinked with an epoxy resin system, so that the high thermal stability and low stress of an epoxy resin condensate are realized, and the epoxy molding compound is effectively modified.
The invention designs reasonable hyperbranched modifier molecules from a synthesis angle based on the existing medicines in a laboratory. And a factory-type process is tried to be synthesized and optimized, a purer product is finally obtained, and the mechanical, thermal and optical properties of the material and the influence on the device after packaging are tested. The main technical breakthrough of the project is that the hyperbranched polymer end group has a plurality of epoxy structures, the unique molecular structure of the hyperbranched polymer can be utilized to improve the thermal stability and the stress shrinkage performance of the epoxy plastic package material after being copolymerized with the epoxy resin, and other excellent performances of the epoxy resin are reserved.
The invention leads the polyhydric alcohol and ECH to be in the same system and catalyzed by phase transfer catalyst, the ring opening addition is an intermediate with hydroxyl and chlorine at the end group, and then the dehydrochlorination is carried out under the alkaline aqueous solution to form epoxy group by ring closure. The method has less by-products, but has complex flow and high cost. The molecular design is carried out by adopting common medicines, and a finished product is prepared after two-step synthesis. The molecules designed in the method contain ether bonds, the flexibility of the chains can assist in reducing internal stress, the rigidity of the benzene rings provides high hardness for the packaging material, and the hyperbranched structure can increase the degree of crosslinking of the molecules to form a latticed structure so as to increase the free volume of the molecules and reduce the internal stress of the molecules. The first step is as follows: pentafluorobenzonitrile and BPA are subjected to 5 substitution under an alkaline condition at 60 ℃ to obtain a one-step product. The second step is that: the method comprises the steps of using a two-step method, firstly adding ECH as a solvent into a phase transfer catalyst for reaction for 6 hours to obtain chlorohydrin ether, adding 30 wt% of NaOH solution into a mixture of BPA and ECH, heating to 90 ℃, installing a water division reflux device, enabling a mixed solution to reach azeotropy at 112 ℃, keeping boiling, carrying out condensation and reflux on water, continuously reacting the evaporated ECH through condensation and reflux, and controlling the water content in the whole system to be 0.2-1%. And finally, washing the resin with water, and distilling the obtained organic phase under reduced pressure to remove redundant ECH and moisture to obtain a product. Adding 30% sodium hydroxide solution into BPA, heating to 80 ℃, adding ECH once, continuously heating to 90 ℃ for dehydration under normal pressure, then decompressing to 86 kPa, heating to 140 ℃ for polymerization, removing alkali liquor, extracting resin by using a solvent, and washing by using water to obtain the product, wherein the transparency of the extracted resin is higher.
Detailed Description
In the following, embodiments of the present invention will be described clearly and completely, and it is obvious that the described embodiments are only a part of the present invention, not all embodiments. All other examples, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments of the present invention, belong to the protection scope of the present invention.
The branched polyphenyl ether modified epoxy plastic packaging material has the advantages of common use of synthetic drugs, small molecular internal stress, few byproducts and the like, and is a material which has great development prospect and can toughen and modify epoxy resin.
The branched polyphenylene ether C1 is a compound having the following structure:
examples synthesis of molecule C1:
reacting pentafluorophenylnitrile and BPA with K under nitrogen atmosphere 2 CO 3 Dissolved in acetone, N 2 The gas was vented for 15 min and reacted at 60 ℃ for 36 h. After cooling to room temperature, adopting a two-step method, adding excess ECH, taking the ECH as a solvent, adding a phase transfer catalyst, and reacting for 6 hours to obtain chlorohydrin ether, wherein the solution is semitransparent. After 6 h of reaction, 30 wt% NaOH solution was added dropwise, and the system rapidly turned yellow and white crystals appeared. And after the dropwise addition is finished, the aqueous solution becomes small droplets under the action of shearing force and is dispersed in the solution, the reaction is carried out for 3 hours, and the final modifier is obtained through a ring-closure reaction.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (2)
1. A hyperbranched polyphenyl ether epoxy plastic package material is characterized in that: the hyperbranched polymer is modified, cannot be separated under the condition of small molecular weight, can obviously improve the toughness and Tg of the epoxy resin, and has the structural general formula:
wherein, R is an electron acceptor, including cyano, triphenyl triazine, benzophenone, and diphenyl sulfone.
2. The hyperbranched polyphenylene ether epoxy plastic package material of claim 1, wherein: the independent structure of R is any one of the following:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211307650.1A CN115558099A (en) | 2022-10-25 | 2022-10-25 | Hyperbranched polyphenyl ether epoxy plastic packaging material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211307650.1A CN115558099A (en) | 2022-10-25 | 2022-10-25 | Hyperbranched polyphenyl ether epoxy plastic packaging material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115558099A true CN115558099A (en) | 2023-01-03 |
Family
ID=84767574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211307650.1A Pending CN115558099A (en) | 2022-10-25 | 2022-10-25 | Hyperbranched polyphenyl ether epoxy plastic packaging material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115558099A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060116492A1 (en) * | 2004-12-01 | 2006-06-01 | 3M Innovative Properties Company | Branched polymer |
| CN101570592A (en) * | 2008-04-30 | 2009-11-04 | 北京化工大学 | Polyether type hyperbranched epoxy resin and preparation method thereof |
| CN102924690A (en) * | 2012-11-07 | 2013-02-13 | 北京化工大学 | Epoxy resin material used for toughening and reinforcing of hyperbranched polyether type epoxy resin and preparation method thereof |
| CN105600773A (en) * | 2015-12-18 | 2016-05-25 | 上海交通大学 | Preparation method of graphene quantum point by using graphite nanoparticle liquid phase stripping |
-
2022
- 2022-10-25 CN CN202211307650.1A patent/CN115558099A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060116492A1 (en) * | 2004-12-01 | 2006-06-01 | 3M Innovative Properties Company | Branched polymer |
| CN101570592A (en) * | 2008-04-30 | 2009-11-04 | 北京化工大学 | Polyether type hyperbranched epoxy resin and preparation method thereof |
| CN102924690A (en) * | 2012-11-07 | 2013-02-13 | 北京化工大学 | Epoxy resin material used for toughening and reinforcing of hyperbranched polyether type epoxy resin and preparation method thereof |
| CN105600773A (en) * | 2015-12-18 | 2016-05-25 | 上海交通大学 | Preparation method of graphene quantum point by using graphite nanoparticle liquid phase stripping |
Non-Patent Citations (2)
| Title |
|---|
| LAIHUI XIAO等: "Diphenolic Acid-Derived Hyperbranched Epoxy Thermosets with High Mechanical Strength and Toughness", 《ACS OMEGA》, vol. 6, pages 34142 * |
| 吕健勇等: "超支化聚苯醚对双酚A 型环氧树脂的低介电改性", 《北京化工大学学报(自然科学版)》, vol. 40, no. 4, pages 41 - 45 * |
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