CN111574482A - Method for efficiently catalyzing and synthesizing epoxy bisphenol fluorene - Google Patents
Method for efficiently catalyzing and synthesizing epoxy bisphenol fluorene Download PDFInfo
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Abstract
The invention relates to the technical field of chemical chemistry, in particular to a method for efficiently catalyzing and synthesizing epoxy bisphenol fluorene, which can effectively shorten the reaction time, simplify the reaction steps, conveniently control the reaction temperature, effectively improve the product yield, and has the advantages of easy purification and good chromaticity of the product; the method comprises the following steps: s1, mixing and dissolving; s2, catalytic reaction: adding a catalyst into the reaction liquid obtained in the step S1, adjusting the temperature of the reaction liquid to 50-100 ℃, and reacting for 3-6 hours; s3, adding alkali for reaction: adjusting the temperature of the reaction liquid to be 30-70 ℃, adding alkali into the reaction liquid, adjusting the temperature of the reaction liquid to be 50-80 ℃, and continuing to react for 1-3 hours; s4, filtering and separating; s5, washing with water; s6, distilling; s7, recrystallization: adding a recrystallization solvent into the white solid product obtained in the step S6, fully dissolving to obtain a recrystallization mixed solution, regulating the temperature of the mixed solution to-5 ℃, and cooling and separating out; s8, centrifugal separation; and S9, drying.
Description
Technical Field
The invention relates to the technical field of chemical engineering chemistry, in particular to a method for efficiently catalyzing and synthesizing epoxy bisphenol fluorene.
Background
Epoxybisphenol fluorene, namely epoxy bisphenol fluorene, is a white crystal or white powder, can be used as a solvent, a catalyst for alkylation esterification and polymerization reaction, and is mainly applied to the field of medicine and the electroplating industry. The epoxy bisphenol fluorene copolymer is widely used in the fields of composite material substrates, insulating materials, adhesives, optical coating materials and the like, and has attracted much attention in recent years from domestic and abroad, so that the production of the epoxy bisphenol fluorene is also important.
The prior patent No. CN106519187A discloses a preparation method of epoxy resin, which comprises the steps of injecting epoxy chloropropane and bisphenol A into a reaction kettle with a stirrer and a reflux condenser tube, starting the stirrer, and heating the reaction kettle by water bath; dissolving sodium hydroxide with distilled water, slowly adding into a reaction kettle, continuously stirring, reacting for 60 minutes until the liquid is completely creamy yellow, stopping the reaction, and naturally cooling to normal temperature; adding distilled water and benzene into a reaction kettle, fully stirring, placing into a liquid separating device, standing, heating a separated organic layer by using a water bath to distill off the benzene, recovering the distilled benzene by using a reflux condensing device, then distilling under reduced pressure to remove water and unreacted epoxy chloropropane, wherein the residual faint yellow viscous liquid is the bisphenol A epoxy resin.
In the document thermosetting resin (volume 27, phase 3, 2012, 23-26), it is reported that a preparation method of epoxy bisphenol fluorene resin is disclosed, bisphenol fluorene and epichlorohydrin are uniformly mixed, and a stepwise catalytic reaction is carried out in a cetyl trimethyl ammonium bromide and sodium hydroxide solution, but the process has the problems of high reaction temperature in the later period, more high polymers and the like in the operation process, and the yield of epoxy bisphenol fluorene resin is not reported in the document.
Disclosure of Invention
In order to solve the technical problems, the invention provides a method for efficiently catalyzing and synthesizing epoxy bisphenol fluorene, which can effectively shorten the reaction time, simplify the reaction steps, conveniently control the reaction temperature, effectively improve the product yield, and has the advantages of easy product purification and good chromaticity.
The invention relates to a method for synthesizing epoxy bisphenol fluorene by high-efficiency catalysis, which comprises the following steps:
s1, mixing and dissolving: respectively measuring epoxy chloropropane and bisphenol fluorene with the mass ratio of 10: 1-25: 1, and adding the bisphenol fluorene into the epoxy chloropropane for dissolving;
s2, catalytic reaction: adding a catalyst into the reaction liquid obtained in the step S1, adjusting the temperature of the reaction liquid to 50-100 ℃, adding the reaction liquid into a container containing a stirrer, reacting for 3-6 hours, and stirring during the reaction;
s3, adding alkali for reaction: adjusting the temperature of the reaction liquid to be 30-70 ℃, adding alkali into the reaction liquid, adjusting the temperature of the reaction liquid to be 50-80 ℃, and continuing to react for 1-3 hours to obtain a suspension reaction liquid containing epoxy bisphenol fluorene;
s4, filtering and separating: filtering the suspended reaction solution obtained in S3 to remove salts formed therein, and recovering the salts;
s5, water washing treatment: washing the reaction solution obtained after filtration with water to obtain a neutral solution containing epoxy bisphenol fluorene;
s6, distillation treatment: distilling the washed solution, condensing and distilling to recover epoxy chloropropane which does not participate in the reaction, concentrating the recovered epoxy chloropropane for reuse, and distilling to obtain white solid product containing epoxy bisphenol fluorene;
s7, recrystallization: adding a recrystallization solvent into the white solid product obtained in the step S6, fully dissolving to obtain a recrystallization mixed solution, regulating the temperature of the mixed solution to-5 ℃, and cooling and separating out;
s8, centrifugal separation: carrying out centrifugal separation on the solid-liquid mixture obtained after recrystallization, and filtering to obtain a wet product of the epoxy resin;
s9, drying: and drying the wet epoxy resin product to obtain a white solid containing epoxy bisphenol fluorene, wherein the Hazen chromaticity of the white solid is less than 15.
Preferably, the addition ratio of the substances of the epichlorohydrin and the bisphenol fluorene is 13: 1-21: 1.
Further, the catalyst used in S2 is any one of triethylamine, tributylamine, tetrabutylammonium bromide, hexadecyltrimethylammonium bromide, tetrabutylammonium hydrogen sulfate, trioctylmethylammonium chloride, dodecyltrimethylammonium chloride, and tetradecyltrimethylammonium chloride.
Furthermore, the mass ratio of the catalyst to the bisphenol fluorene in the S2 is 1: 25-1: 40.
Further, the base used in S3 is one of an organic base or an inorganic base, the inorganic base is selected from sodium hydroxide, potassium hydroxide, calcium hydroxide, potassium hydride or sodium hydride, and the organic base is selected from the bases of potassium tert-butoxide, sodium ethoxide, sodium methoxide, tetramethylammonium hydroxide, tetramethylethylenediamine, methylimidazole or pyridine.
Further, the recrystallization solvent used in S7 is a mixed solution of one or more solvents selected from toluene, xylene, methanol, ethanol, ethylene glycol dimethyl ether, N-dimethylformamide, dichloromethane, dichloroethane, and acetonitrile.
Furthermore, the addition mass ratio of the recrystallization solvent to the white solid product in the S7 is 1: 1-1: 10.
Compared with the prior art, the invention has the beneficial effects that: when the epoxy bisphenol fluorene is produced by the method, the synthesis steps are simple, epoxy chloropropane and bisphenol fluorene are reacted at the mass ratio of 10: 1-25: 1 at the temperature of 30-100 ℃ in the presence of alkali under the action of a catalyst, and the method mainly comprises the following two steps: firstly, etherification reaction is carried out, under the action of a catalyst, ring opening of epoxy chloropropane is carried out to carry out etherification reaction; secondly, ring-closure reaction, namely adding alkali such as sodium hydroxide and the like to carry out ring-closure reaction; the method has the advantages of simple and convenient operation, easily controlled reaction temperature, 4-10 hours of total reaction time, effectively shortened reaction time required by production, no water participation in the whole reaction process, effective avoidance of side reaction, great increase of product yield, more than 90 percent, high purity and easy purification of the obtained product, recycling of residual epoxy chloropropane by distillation in the reaction process, easy recycling of recrystallization, relatively saved production cost, green and environment-friendly product preparation process, adoption of the solid base catalytic synthesis reaction process in the reaction process, no generation of waste gas and waste residue in the reaction process, less organic waste liquid, environmental pollution reduction, mild synthesis process conditions, good controllability and high safety factor, and suitability for green sustainable development of industrial production, the obtained product has good chromaticity, and the epoxy bisphenol fluorene prepared by the method has the same property as epoxy bisphenol fluorene produced by other processes, and also has the characteristics of good mechanical property, good heat resistance, chemical resistance, wear resistance, strong adhesive force and the like; meanwhile, due to the introduction of the fluorene structure, the crosslinking density of the resin after curing can be reduced, and the increase of the number of benzene rings can improve the rigidity of a molecular chain, improve the glass transition temperature of the resin, increase the non-polarity of molecules and reduce the water absorption of the resin, so that the moisture and heat resistance of the resin is greatly improved.
Detailed Description
FIG. 1 is a flow chart of a method for efficiently catalytically synthesizing epoxybisphenol fluorene provided by the invention.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The reactants and the reaction products used in the following comparative examples and examples were analyzed and examined by a high performance liquid chromatography analyzer.
Comparative example
The preparation method reported in the literature thermosetting resin is adopted, and the test is carried out after optimization:
adding 180g of bisphenol fluorene, 6g of triethylamine and 620.3g of epichlorohydrin into a 1000ml three-neck flask provided with a mechanical stirring device, a thermometer and a reflux condenser, adding the three-neck flask into a water bath kettle at 60 ℃, completely dissolving and clarifying the system, controlling the temperature in the kettle to be 60 ℃, reacting for 6 hours, cooling to room temperature to be 30 ℃, slowly dropwise adding 116.1g of 42% sodium hydroxide solution, controlling the temperature to be 25-30 ℃, dropwise adding for about 3 hours, maintaining the kettle at 30 ℃ after adding alkali, reacting for 6 hours again, washing with water, removing the solvent of the reaction liquid after washing with water, and adding 540g of acetone: recrystallizing a mixed solvent with the mass ratio of methanol being 1:3, cooling, carrying out suction filtration to obtain a crude product, carrying out secondary crystallization on the crude product by butanone to obtain a qualified product, drying a wet product to obtain a white solid which is an epoxy bisphenol fluorene product, wherein the actual yield is 60.5%, the liquid chromatogram indicates that the product purity is 97.10%, and the Hazen chroma is less than 15.
Example 1
The preparation method comprises the following steps:
putting 180g of bisphenol fluorene, 6g of tetrabutylammonium bromide and 620.3g of epoxy chloropropane into a 1000ml three-neck flask provided with a mechanical stirring device, a thermometer and a reflux condenser tube, adding the three-neck flask into a water bath kettle at 55 ℃, completely dissolving and clarifying the system, controlling the temperature in the kettle to be 60-90 ℃, carrying out gradient temperature rise, reacting for 4 hours, cooling to control the kettle temperature to be 65-70 ℃, adding 45g of sodium hydroxide, maintaining the kettle temperature to be 65-70 ℃ after adding alkali, reacting for 1 hour, cooling, washing with water, removing a solvent from a reaction solution after washing with water, pulping with 195g of acetonitrile, cooling, carrying out suction filtration to obtain a wet product, drying to obtain a white solid, wherein the actual yield is 90.15%, the liquid chromatogram represents that the product purity is 96.75%, and the Hazen chromaticity is less than 15.
Example 2
The preparation method comprises the following steps:
putting 180g of bisphenol fluorene, 6g of tetrabutylammonium bromide and 620.3g of epichlorohydrin into a 1000ml three-neck flask provided with a mechanical stirring pipe, a thermometer and a reflux condenser pipe, adding the three-neck flask into a water bath kettle at 55 ℃, completely dissolving and clarifying the system, controlling the temperature in the kettle to be 60-90 ℃, carrying out gradient temperature rise, reacting for 4 hours, cooling to control the kettle temperature to be 65-70 ℃, adding 50g of sodium hydroxide, maintaining the kettle temperature to be 65-70 ℃ after adding alkali, reacting for 1 hour, cooling, washing with water, removing a solvent from a reaction solution after washing with water, pulping with 195g of acetonitrile, cooling, carrying out suction filtration to obtain a wet product, drying to obtain a white solid, wherein the actual yield is 91.03%, the purity of a liquid chromatogram characterization product is 97.12%, and the Hazen chromaticity is less than 15.
Example 3
The preparation method comprises the following steps:
putting 180g of bisphenol fluorene, 6g of tetrabutylammonium bromide and 763g of epoxy chloropropane into a 1000ml three-neck flask provided with a mechanical stirring device, a thermometer and a reflux condenser, adding the three-neck flask into a water bath kettle at 55 ℃, completely dissolving and clarifying the system, controlling the temperature in the kettle to be 60-90 ℃, carrying out gradient temperature rise, reacting for 4 hours, cooling to control the kettle temperature to be 65-70 ℃, adding 45g of sodium hydroxide, maintaining the kettle temperature to be 65-70 ℃ after adding alkali, reacting for 1 hour, cooling, washing with water, removing a solvent from a reaction solution after washing with water, pulping with 195g of acetonitrile, cooling, carrying out suction filtration to obtain a wet product, drying to obtain a white solid, wherein the actual yield is 91.75%, the purity of a liquid chromatogram characterization product is 97.25%, and the Hazen chromaticity is less than 15.
Example 4
The preparation method comprises the following steps:
putting 180g of bisphenol fluorene, 6g of tetrabutylammonium bromide and 763g of epoxy chloropropane into a 1000ml three-neck flask provided with a mechanical stirring pipe, a thermometer and a reflux condenser pipe, adding the three-neck flask into a water bath kettle at 55 ℃, completely dissolving and clarifying the system, controlling the temperature in the kettle to be 60-90 ℃, carrying out gradient temperature rise, reacting for 4 hours, cooling to control the kettle temperature to be 65-70 ℃, adding 50g of sodium hydroxide, maintaining the kettle temperature to be 65-70 ℃ after adding alkali, reacting for 1 hour, cooling, washing with water, removing a solvent from a reaction solution after washing with water, pulping with 195g of acetonitrile, cooling, carrying out suction filtration to obtain a wet product, drying to obtain a white solid, wherein the actual yield is 92.15%, the purity of a liquid chromatogram characterization product is 97.73%, and the Hazen chromaticity is less than 15.
Example 5
The preparation method comprises the following steps:
putting 180g of bisphenol fluorene, 6g of tetrabutylammonium bromide and 859g of epichlorohydrin into a 1000ml three-neck flask provided with a mechanical stirring pipe, a thermometer and a reflux condenser pipe, adding the three-neck flask into a water bath kettle at 55 ℃, completely dissolving and clarifying the system, controlling the temperature in the kettle to be 60-90 ℃, carrying out gradient temperature rise, reacting for 4 hours, reducing the temperature to be 65-70 ℃, adding 45g of sodium hydroxide, maintaining the kettle temperature to be 65-70 ℃ after adding alkali, reacting for 1 hour, cooling, washing with water, removing a solvent from a reaction solution after washing with water, pulping with 195g of acetonitrile, cooling, carrying out suction filtration to obtain a wet product, drying to obtain a white solid, wherein the actual yield is 92.35%, the purity of a liquid chromatogram characterization product is 97.89%, and the Hazen chromaticity is less than 15.
Example 6
The preparation method comprises the following steps:
putting 180g of bisphenol fluorene, 6g of tetrabutylammonium bromide and 859g of epichlorohydrin into a 1000ml three-neck flask provided with a mechanical stirring pipe, a thermometer and a reflux condenser pipe, adding the three-neck flask into a water bath kettle at 55 ℃, completely dissolving and clarifying the system, controlling the temperature in the kettle to be 60-90 ℃, carrying out gradient heating, reacting for 4 hours, cooling to control the kettle temperature to be 65-70 ℃, adding 50g of sodium hydroxide, maintaining the kettle temperature to be 65-70 ℃ after adding alkali, reacting for 1 hour, cooling, washing with water, removing a solvent from a reaction solution after washing with water, pulping with 195g of acetonitrile, cooling, carrying out suction filtration to obtain a wet product, drying to obtain a white solid, wherein the actual yield is 93.15%, the liquid chromatogram represents that the product purity is 98.21%, and the Hazen chromaticity is less than 15.
Example 7
The preparation method comprises the following steps:
putting 180g of bisphenol fluorene, 6g of tetrabutylammonium bromide and 954g of epichlorohydrin into a 1000ml three-neck flask provided with a mechanical stirring device, a thermometer and a reflux condenser, adding the three-neck flask into a water bath kettle at 55 ℃, completely dissolving and clarifying the system, controlling the temperature in the kettle to be 60-90 ℃, carrying out gradient heating, reacting for 4 hours, cooling to control the kettle temperature to be 65-70 ℃, adding 45g of sodium hydroxide, after adding alkali, maintaining the kettle temperature to be 65-70 ℃, reacting for 1 hour, cooling, washing with water, removing a solvent from a reaction solution after washing with water, pulping with 195g of acetonitrile, cooling, carrying out suction filtration to obtain a wet product, drying to obtain a white solid, wherein the actual yield is 92.26%, the purity of a liquid chromatogram characteristic product is 98.12%, and the Hazen chromaticity is less than 15.
Example 8
The preparation method comprises the following steps:
putting 180g of bisphenol fluorene, 6g of tetrabutylammonium bromide and 954g of epichlorohydrin into a 1000ml three-neck flask provided with a mechanical stirring device, a thermometer and a reflux condenser, adding the three-neck flask into a water bath kettle at 55 ℃, completely dissolving and clarifying the system, controlling the temperature in the kettle to be 60-90 ℃, carrying out gradient heating, reacting for 4 hours, cooling to control the kettle temperature to be 65-70 ℃, adding 50g of sodium hydroxide, after adding alkali, maintaining the kettle temperature to be 65-70 ℃, reacting for 1 hour, cooling, washing with water, removing a solvent from a reaction solution after washing with water, pulping with 195g of acetonitrile, cooling, carrying out suction filtration to obtain a wet product, drying to obtain a white solid, wherein the actual yield is 93.73%, the purity of a liquid chromatogram characterization product is 97.99%, and the Hazen chromaticity is less than 15.
Comparing the comparative example with examples 1 to 8, the following conclusions can be drawn:
in the preparation process of epoxy bisphenol fluorene, after alkaline solution is added, the local temperature is too high, the high polymer byproducts are more, the reaction time is as long as 10-12 hours, a large amount of sewage is generated along with the water washing and solvent removal post-treatment, the product yield is lower and is generally about 60-65%, and therefore, the defects of long reaction time, low product yield, high production cost and the like exist in the preparation of the conventional process.
The comparative process is optimized by adopting the preparation method of the embodiment 1-8, and the alkali liquor is changed into the solid alkali, so that the reaction is promoted more quickly, the byproduct of the high polymer is reduced, the reaction time is obviously shortened, the wastewater is less, the product yield can reach more than 90 percent through the post-treatment of water washing and solvent removal, the process reaction time is short, the product yield is high, and the production cost is low.
The above description is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, several modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (7)
1. A method for efficiently catalyzing and synthesizing epoxy bisphenol fluorene is characterized by comprising the following steps:
s1, mixing and dissolving: respectively measuring epoxy chloropropane and bisphenol fluorene with the mass ratio of 10: 1-25: 1, and adding the bisphenol fluorene into the epoxy chloropropane for dissolving;
s2, catalytic reaction: adding a catalyst into the reaction liquid obtained in the step S1, adjusting the temperature of the reaction liquid to 50-100 ℃, adding the reaction liquid into a container containing a stirrer, reacting for 3-6 hours, and stirring during the reaction;
s3, adding alkali for reaction: adjusting the temperature of the reaction liquid to be 30-70 ℃, adding alkali into the reaction liquid, adjusting the temperature of the reaction liquid to be 50-80 ℃, and continuing to react for 1-3 hours to obtain a suspension reaction liquid containing epoxy bisphenol fluorene;
s4, filtering and separating: filtering the suspended reaction solution obtained in S3 to remove salts formed therein, and recovering the salts;
s5, water washing treatment: washing the reaction solution obtained after filtration with water to obtain a neutral solution containing epoxy bisphenol fluorene;
s6, distillation treatment: distilling the washed solution, condensing and distilling to recover epoxy chloropropane which does not participate in the reaction, concentrating the recovered epoxy chloropropane for reuse, and distilling to obtain white solid product containing epoxy bisphenol fluorene;
s7, recrystallization: adding a recrystallization solvent into the white solid product obtained in the step S6, fully dissolving to obtain a recrystallization mixed solution, regulating the temperature of the mixed solution to-5 ℃, and cooling and separating out;
s8, centrifugal separation: carrying out centrifugal separation on the solid-liquid mixture obtained after recrystallization, and filtering to obtain a wet product of the epoxy resin;
s9, drying: drying the wet epoxy resin product to obtain white solid containing epoxy bisphenol fluorene with Hazen chroma less than 15;
s10, index detection: and (4) analyzing and detecting the obtained white solid by using a high performance liquid chromatography analyzer, directly exporting qualified white solid to obtain a finished product, and repeating the steps S7-S10 on the unqualified white solid.
2. The method for efficiently catalytically synthesizing epoxybisphenol fluorene according to claim 1, wherein the addition ratio of the substances of epichlorohydrin to bisphenol fluorene is 13: 1-21: 1.
3. The method for efficiently catalytically synthesizing epoxybisphenol fluorene according to claim 1, wherein the catalyst used in S2 is any one of triethylamine, tributylamine, tetrabutylammonium bromide, hexadecyltrimethylammonium bromide, tetrabutylammonium hydrogen sulfate, trioctylmethylammonium chloride, dodecyltrimethylammonium chloride and tetradecyltrimethylammonium chloride.
4. The method for efficiently catalytically synthesizing epoxybisphenol fluorene as claimed in claim 1, wherein the mass ratio of the catalyst in S2 to bisphenol fluorene is 1: 25-1: 40.
5. The method according to claim 1, wherein the base used in S3 is one of an organic base or an inorganic base, the inorganic base is selected from sodium hydroxide, potassium hydroxide, calcium hydroxide, potassium hydride or sodium hydride, and the organic base is selected from potassium tert-butoxide, sodium ethoxide, sodium methoxide, tetramethylammonium hydroxide, tetramethylethylenediamine, methylimidazole or pyridine.
6. The method for efficiently catalytically synthesizing epoxybisphenol fluorene as claimed in claim 1, wherein the recrystallization solvent used in S7 is a mixture of one or more solvents selected from toluene, xylene, methanol, ethanol, ethylene glycol dimethyl ether, N-dimethylformamide, dichloromethane, dichloroethane and acetonitrile.
7. The method for efficiently catalytically synthesizing epoxybisphenol fluorene as claimed in claim 1, wherein the addition mass ratio of the recrystallization solvent to the white solid product in S7 is 1: 1-1: 10.
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| CN112745201A (en) * | 2020-12-25 | 2021-05-04 | 长春长光宇航复合材料有限公司 | Bio-based bisphenol monomer containing fluorene ring structure, bio-based epoxy resin monomer, bio-based epoxy resin material and preparation method thereof |
| CN113024377A (en) * | 2021-03-15 | 2021-06-25 | 沧州临港丰亚化工有限公司 | Novel method for synthesizing multi-ethoxy acrylate with fluorenyl structure by using supported catalyst |
| CN113024358A (en) * | 2021-03-15 | 2021-06-25 | 沧州临港丰亚化工有限公司 | Method for catalytically synthesizing phenyl diether fluorene by ethylene oxide |
| CN113548947A (en) * | 2021-07-01 | 2021-10-26 | 万华化学集团股份有限公司 | Method for preparing phenyl diether fluorene |
| CN115595089A (en) * | 2022-10-09 | 2023-01-13 | 北京康美特科技股份有限公司（Cn） | Conductive silver adhesive and preparation method and application thereof |
| CN116573989A (en) * | 2023-05-12 | 2023-08-11 | 湖南大学 | Preparation method of tetraphenol fluorene and preparation method of tetraphenol fluorenyl epoxy resin |
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| CN112745201A (en) * | 2020-12-25 | 2021-05-04 | 长春长光宇航复合材料有限公司 | Bio-based bisphenol monomer containing fluorene ring structure, bio-based epoxy resin monomer, bio-based epoxy resin material and preparation method thereof |
| CN113024377A (en) * | 2021-03-15 | 2021-06-25 | 沧州临港丰亚化工有限公司 | Novel method for synthesizing multi-ethoxy acrylate with fluorenyl structure by using supported catalyst |
| CN113024358A (en) * | 2021-03-15 | 2021-06-25 | 沧州临港丰亚化工有限公司 | Method for catalytically synthesizing phenyl diether fluorene by ethylene oxide |
| CN113548947A (en) * | 2021-07-01 | 2021-10-26 | 万华化学集团股份有限公司 | Method for preparing phenyl diether fluorene |
| CN113548947B (en) * | 2021-07-01 | 2022-09-20 | 万华化学集团股份有限公司 | Method for preparing phenyl diether fluorene |
| CN115595089A (en) * | 2022-10-09 | 2023-01-13 | 北京康美特科技股份有限公司（Cn） | Conductive silver adhesive and preparation method and application thereof |
| CN116573989A (en) * | 2023-05-12 | 2023-08-11 | 湖南大学 | Preparation method of tetraphenol fluorene and preparation method of tetraphenol fluorenyl epoxy resin |
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Application publication date: 20200825 |