Polyimide with main chain containing benzo norbornene structure and preparation method thereof

A technology of benzonorbornene and polyimide, which is applied in the field of polyimide materials and preparation, can solve the problems of high glass transition temperature or melting temperature, processing difficulties, etc., and achieves reduction of close packing and excellent mechanical properties. , the effect of improving heat resistance

Active Publication Date: 2021-09-14
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such materials have extremely high glass transition temperature or melting temperature, are insoluble and insoluble, and are difficult to process.

Method used

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  • Polyimide with main chain containing benzo norbornene structure and preparation method thereof
  • Polyimide with main chain containing benzo norbornene structure and preparation method thereof
  • Polyimide with main chain containing benzo norbornene structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] (1) Preparation of diketone compound.

[0051] Under the conditions of nitrogen, ice bath and mechanical stirring, take benzoquinone compound 21.62g (200mmol) and 250mL acetone in a 500mL three-necked flask, dissolve 14.85mL (220mmol) cyclopentadiene compound in 60mL acetone in a constant pressure dropping funnel , under vigorous mechanical stirring, the cyclopentadiene solution was added dropwise to the 1,4-benzoquinone solution, kept for 1.5 hours, slowly raised to room temperature (25°C), and reacted at room temperature for 6 hours to obtain a brown solution. The acetone was removed by a rotary evaporator, and the remaining tan solid was recrystallized from n-hexane to precipitate 30.92 g of a yellow diketone compound.

[0052] (2) Preparation of a diphenol compound containing a benzonorbornene structure.

[0053] Under the condition of room temperature and magnetic stirring, get 10g (57mmol) diketone compound, 20g basic aluminum oxide and 200mL ethyl acetate in 250...

Embodiment 2

[0061] 1) Preparation of diketone compounds.

[0062] Under the conditions of nitrogen, ice bath and mechanical stirring, take 21.62g (200mmol) of benzoquinone compound and 350mL methanol in a 500mL three-necked flask, dissolve 14.2mL (210mmol) cyclopentadiene compound in 60mL methanol in a constant pressure dropping funnel , under vigorous mechanical stirring, the cyclopentadiene solution was added dropwise to the 1,4-benzoquinone solution, kept for 1.5 hours, slowly raised to room temperature (25°C), and reacted at room temperature for 6 hours to obtain a brown-yellow solution. Methanol was removed by a rotary evaporator, and the remaining tan solid was recrystallized from n-hexane to precipitate 30.12 g of a yellow diketone compound.

[0063] (2) Preparation of a diphenol compound containing a benzonorbornene structure.

[0064] Under the condition of room temperature and magnetic stirring, get 10g (57mmol) diketone compound, 15g basic aluminum oxide and 230mL ethyl acetat...

Embodiment 3

[0072] (1) Preparation of diketone compound.

[0073] Under the conditions of nitrogen, ice bath and mechanical stirring, take 21.62g (200mmol) of benzoquinone compound and 300mL methanol in a 500mL three-necked flask, dissolve 13.5mL (200mmol) cyclopentadiene compound in 50mL methanol in a constant pressure dropping funnel , under vigorous mechanical stirring, the cyclopentadiene solution was added dropwise to the 1,4-benzoquinone solution, kept for 1.5 hours, slowly raised to room temperature (25°C), and reacted at room temperature for 6 hours to obtain a brown solution. Methanol was removed by a rotary evaporator, and the remaining tan solid was recrystallized from n-hexane to precipitate 32.56 g of a yellow diketone compound.

[0074] (2) Preparation of a diphenol compound containing a benzonorbornene structure.

[0075] Under the condition of room temperature and magnetic stirring, get 10g (57mmol) diketone compound, 20g basic aluminum oxide and 200mL ethyl acetate in 25...

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Abstract

The invention discloses polyimide with a main chain containing a benzo norbornene structure and a preparation method thereof, and belongs to the technical field of high polymer materials. Starting from p-benzoquinone and cyclopentadiene, the dianhydride monomer containing the benzo norbornene structure and the polyimide with the main chain containing the benzo norbornene structure are efficiently synthesized through D-A reaction, isomerization, nucleophilic substitution, a two-step method and other reactions. Starting from p-benzoquinone and cyclopentadiene, the dianhydride monomer containing the benzo norbornene structure and the polyimide with the main chain containing the benzo norbornene structure are efficiently synthesized through D-A reaction, isomerization, nucleophilic substitution, a two-step method and other reactions. Norbornene bicyclic ring is used as a side group, so that regular stacking among polyimide molecular chains is destroyed, the free volume is increased, and the dielectric constant can be reduced. And double bonds of bornene are further crosslinked under high heat, so that the thermal properties, mechanical properties and solvent resistance of the material are improved. The prepared polyimide material has the advantages of excellent thermal properties and mechanical properties, simple synthesis process, low cost, good solubility, excellent solvent resistance and low dielectric constant.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and relates to a polyimide material and a preparation method. Background technique [0002] Polyimide refers to a class of high-performance polymers containing imide rings on the main chain, mainly formed by condensation of diamines and dianhydrides. Polyimide material has excellent thermal and mechanical properties and is widely used in engineering fields. However, such materials have extremely high glass transition temperature or melting temperature, are insoluble and insoluble, and are difficult to process. Therefore, it is very important to modify polyimide. Generally, the performance of polyimide can be improved by designing molecular structure or blending. Literature (European Polymer Journal, 2013,49 (11): 3657-3672.) designed and synthesized dianhydride monomers TA-TFMB and TA-TFBP with trifluoromethyl as side groups, and combined it with commercial diamine monomers TFMB con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/12C08J5/18C08L79/08
CPCC08G73/126C08G73/127C08J5/18C08J2379/08Y02E10/549
Inventor 贺晓慧温宇飞邹建华武斌
Owner NANCHANG UNIV
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