Aromatic polyimide with main chain containing benzo norbornene structure and preparation method

A technology of benzonorbornene and polyimide, which is applied in the field of polymer materials and preparation, and can solve the problems that the glass transition temperature of aromatic polyimide needs to be improved, it is not suitable for industrial production, and the number of modification methods is increased. , to achieve the effects of reducing close packing and crystallization tendency, increasing glass transition temperature, and improving solubility

Active Publication Date: 2021-10-19
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Literature (Journal of Polymer Research2004,11,9) reported a side chain coupling norbornane aromatic diamine monomer and its aromatic polyimide synthesized with a series of commercially available dianhydride monomers. The introduction of heterocycles retains certain dielectric properties and solubility properties, but its glass transition temperature needs to be improved compared with aromatic polyimides, and its raw material 3,6-dihydroxybenzonorbornane is not easily available and The cost is high, it is not suitable for industrial production, and the means of modification need to be increased

Method used

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  • Aromatic polyimide with main chain containing benzo norbornene structure and preparation method
  • Aromatic polyimide with main chain containing benzo norbornene structure and preparation method
  • Aromatic polyimide with main chain containing benzo norbornene structure and preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] (1) Preparation of diketone compound.

[0059] 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 methanol solution of cyclopentadiene was added dropwise to the methanol solution of 1,4-benzoquinone, kept for 1.5 hours, slowly raised to room temperature (25°C), and reacted at room temperature for 6 hours to obtain Tan solution. Methanol was removed by a rotary evaporator, and the remaining tan solid was recrystallized with n-hexane, and 32.56 g of a yellow needle-like crystal product, namely norbornenecyclohexenedione compound, was precipitated.

[0060] (2) Preparation of dinitro compounds containing benzonorbornene structure.

[0061] Under the conditions of nitrogen and magnetic stirring, take 1.74g (10mmol...

Embodiment 2

[0069] 1) Preparation of diketone compounds.

[0070] Under the conditions of nitrogen, ice bath and mechanical stirring, take 21.62g (200mmol) of benzoquinone compound and 250mL of acetone in a 500mL three-necked flask, and dissolve 14.85mL (220mmol) of cyclopentadiene compound in 40mL of acetone in a constant pressure dropping funnel , under vigorous mechanical stirring, the acetone solution of cyclopentadiene was added dropwise to the acetone solution of 1,4-benzoquinone, kept for 1.5 hours, slowly raised to room temperature (25°C), and reacted at room temperature for 6 hours to obtain Tan solution. The acetone was removed by a rotary evaporator, and the remaining tan solid was recrystallized with n-hexane, and 30.92 g of a yellow needle-like crystal product, namely norbornene and cyclohexenedione compound, was precipitated.

[0071] (2) Preparation of dinitro compounds containing benzonorbornene structure.

[0072]Under the conditions of nitrogen and magnetic stirring, t...

Embodiment 3

[0080] 1) Preparation of diketone compounds.

[0081] Under the conditions of nitrogen, ice bath and mechanical stirring, take 21.62g (200mmol) of benzoquinone compound and 350mL of acetonitrile in a 500mL three-necked flask, and dissolve 16.2mL (240mmol) of cyclopentadiene compound in 60mL of acetonitrile in a constant pressure dropping funnel In , under vigorous mechanical stirring, the acetonitrile solution of cyclopentadiene was added dropwise to the acetonitrile solution of 1,4-benzoquinone, kept for 1.5 hours, slowly raised to room temperature (25°C), and reacted at room temperature for 6 hours to obtain Brown-yellow solution. The acetonitrile was removed by a rotary evaporator, and the remaining tan solid was recrystallized with n-hexane, and 29.48 g of a yellow needle-like crystal product, namely norbornene and cyclohexenedione compound, was precipitated.

[0082] (2) Preparation of dinitro compounds containing benzonorbornene structure.

[0083] Under the conditions...

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Abstract

The invention relates to aromatic polyimide with a main chain containing a benzo norbornene structure and a preparation method. The aromatic polyimide is characterized in that p-benzoquinone and cyclopentadiene are used as starting materials, and a diamine monomer containing a benzo norbornene structure and aromatic polyimide with a main chain containing a benzo norbornene structure are efficiently synthesized through a D-A reaction, nucleophilic substitution, reduction and a two-step method, so that the flexibility of a molecular chain is ensured, and the thermal performance is not obviously reduced. According to the invention, a norbornene bicyclic ring is used as a side group, so that the free volume between chain segments is increased, the solubility of the polymer is retained, and the dielectric constant of the material is reduced; the double ring has the sp2-configuration cis-double bond with the large polarity, such that the accumulation between macromolecules is ensured, the glass-transition temperature of the polymer is improved, and the double bond of the bornene can be subjected to cross-linking under the high heat so as to improve the thermal property and the mechanical property of the material; through copolymerization modification, the performance of the material is further widened, and the cost is reduced; and the aromatic polyimide has the advantages of low cost, simple synthesis process, low dielectric constant and excellent thermal and mechanical properties.

Description

technical field [0001] The invention belongs to the technical field of polymer materials and preparation, and relates to an aromatic polyimide material and a preparation method. Background technique [0002] Aromatic polyimide materials have excellent thermal and mechanical properties and are 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. Generally, the processing performance can be improved by changing the monomer structure, among which the introduction of diamine monomers with steric hindrance groups is a very effective method. Foreign companies including Mitsui Chemicals and SABIC have successively developed thermoplastic Formed and Polyimide engineering resin. However, the introduction of diamine monomers with complex structures increases the process steps and production costs, and reduces the thermal and mechanical propert...

Claims

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Application Information

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IPC IPC(8): C07C217/90C07C217/80C07C213/02C07C213/10C07D213/73C08G73/12C08J5/18C08L79/08
CPCC07C217/90C07C217/80C07D213/73C08G73/126C08G73/127C08J5/18C07C2603/66C08J2379/08Y02E10/549
Inventor 贺晓慧武斌邹建华温宇飞
Owner NANCHANG UNIV
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