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Thermosetting resin monomer containing fluorene and benzocyclobutene construction unit as well as preparation method and application thereof

A technology of benzocyclobutene and bromobenzocyclobutene, which is applied in the field of high-performance polymer manufacturing, can solve the problems of unstable heat resistance and dielectric properties of films, incomplete progress and the like, and achieves low moisture absorption, The effect of good temperature resistance and high chemical stability

Inactive Publication Date: 2013-05-08
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the incomplete [2+2] cycloaddition reaction of trifluorovinyl ether at high temperature, the heat resistance and dielectric properties of the film are unstable.

Method used

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  • Thermosetting resin monomer containing fluorene and benzocyclobutene construction unit as well as preparation method and application thereof
  • Thermosetting resin monomer containing fluorene and benzocyclobutene construction unit as well as preparation method and application thereof
  • Thermosetting resin monomer containing fluorene and benzocyclobutene construction unit as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 19

[0024] Synthesis of embodiment 19,9-bis(3-fluoro-4-hydroxyphenyl)fluorene

[0025] Under the protection of nitrogen, 36.2 grams of fluorenone, 90.1 grams of o-fluorophenol, 0.3 milliliters of β-mercaptopropionic acid and 100 milliliters of toluene were added to the reaction device, and after stirring for 0.5 hours at 30 ° C, 5 milliliters of concentrated After the addition of sulfuric acid, the temperature was raised to 55°C to react for 5 hours, cooled to room temperature, the product was poured into water, solids were precipitated, and recrystallized in toluene to obtain white crystals of fluorine-containing bisphenolfluorene with a yield of 92%. Melting point, 220-221°C (literature, USP5304688, 219-221°C). Mass spectrometry (EI-MS) characterized m / z: 386.11 (100.0%), 387.12 (27.3%), 388.12 (4.0%).

Embodiment 29

[0026] Synthesis of embodiment 29,9-bis(3-trifluoromethyl-4-hydroxyphenyl)fluorene

[0027] Under nitrogen protection, 18.2 grams of fluorenone, 64.8 grams of o-trifluoromethylphenol, 0.4 milliliters of β-mercaptopropionic acid and 80 milliliters of toluene were added to the reaction device, and after stirring for 0.5 hours at 30°C, slowly dropwise added 4 milliliters of concentrated sulfuric acid, after the dropwise addition, the temperature was raised to 55°C for 6 hours, cooled to room temperature, the product was neutralized with saturated sodium bicarbonate solution, washed with water until neutral, and the organic phase was rotary evaporated to obtain a solid crude product, which was passed through column chromatography ( Petroleum ether / ethyl acetate, 4:1) to obtain white crystals of fluorine-containing bisphenolfluorene with a yield of 85%. Mass spectrometry (EI-MS) characterization m / z: 486.11(100.0%), 487.11(29.5%), 488.11(4.5%)

Embodiment 32

[0028] Synthesis of Example 32,7-bis(trifluoromethyl)-9,9-bis(4-hydroxyphenyl)fluorene

[0029] Under the protection of argon, add 8.2 g of 2,7-dibromo-9,9-bis(4-hydroxyphenyl)fluorene to the reaction device (prepared according to the literature: R. Grisorio et al., Macromolecules 2011, 44, 7977-7986) , 2 grams of three (dibenzylideneacetone) dipalladium (i.e. Pd 2 (dba) 3 ), 4.23 grams of cuprous iodide, 32 milliliters of methyl fluorosulfonyl difluoroacetate and 100 milliliters of N,N-dimethylformamide, reacted at 100 ° C for 12 hours, cooled to room temperature, and the product was poured into water, with A solid precipitated out and was recrystallized in toluene to obtain 2,7-bis(trifluoromethyl)9,9-bis(4-hydroxyphenyl)fluorene as white crystals with a yield of 86%. Mass spectrometry (EI-MS) characterization m / z: 486.11(100.0%), 487.11(29.5%), 488.11(4.5%)

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Abstract

The invention belongs to the filed of high-performance polymer preparation, and particularly relates to a thermosetting resin monomer containing fluorene and benzocyclobutene construction unit as well as a preparation method and application thereof. The constitutional formula of the monomer is shown in the description; and the monomer is obtained through etherification reaction between bisphenol fluorine and 4-bromobenzocyclobutene in a solvent in the presence of cuprous salt, imidazole ligand and inorganic base. The monomer has very good film formation property, and a solid film with high heat resistance, low water absorbing capacity, low specific inductive capacity and high flatness can be obtained through thermal curing of the obtained organic film. In the atmosphere of nitrogen, 5% weight loss temperature (Td 5%) of the film is 468.5 DEG C, and the carbon yield at 1000 DEG C is up to 37.6%. The monomer is suitable for serving as a high-temperature resistant bonding agent in the fields of aerospace, national defense and the like and an encapsulating material of electronic devices and components in an electric industry.

Description

technical field [0001] The invention belongs to the technical field of high-performance polymer production, and specifically relates to a thermosetting resin monomer containing fluorene and benzocyclobutene structural units, a preparation method and an application. It is used to prepare thermosetting resins containing fluorene and benzocyclobutene structural units with high heat resistance, low water absorption and low dielectric constant. Background technique [0002] Due to their high quantum efficiency and modifiable molecular structure, π-conjugated fluorene-containing polymers have been widely used in the field of organic optoelectronic functional materials as organic electroluminescent materials, organic thin-film solar materials and biological detection materials. On the other hand, due to the large free volume of fluorene, the epoxy resin with bisphenol fluorene as the structural unit is favored by the aerospace field and the electrical and electronic industry becaus...

Claims

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Application Information

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IPC IPC(8): C07C43/275C07C43/29C07C41/16C08G61/02
Inventor 房强金凯凯李凯袁超童佳伟刁屾赖华
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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