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Diamine monomer containing isoindigo structure and black polyimide synthesized by diamine monomer

A black polyimide and diamine monomer technology, applied in the direction of organic chemistry, can solve the problems of strict coating process requirements, high production conditions, complex preparation process, etc., achieve excellent shading performance, easy synthesis, and efficient reaction Effect

Active Publication Date: 2020-08-25
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, patent CN 108341950A discloses a method of adding amino-containing organosiloxane to modify polyamic acid, and then adding carbon black to prepare black polyimide film, but the production conditions required by this method are relatively high, and the preparation process Complex, and mainly use carbon black as a light-shielding substance, which will reduce the mechanical properties, heat resistance and other properties of the material
Another method is to coat a layer of light-shielding substance on the PI film. For example, patent CN102529262A discloses a kind of high-temperature-resistant coating type black polyimide film and its preparation method. This patent coats acrylic black matte ink on The upper and lower layers of polyimide film, but its black coating is easy to fade and uneven. In addition, the coating process is strict and the cost is higher

Method used

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  • Diamine monomer containing isoindigo structure and black polyimide synthesized by diamine monomer
  • Diamine monomer containing isoindigo structure and black polyimide synthesized by diamine monomer
  • Diamine monomer containing isoindigo structure and black polyimide synthesized by diamine monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] This example provides a (E) 6,6'-bis-(4-amino-phenyl)-1,1'-bis-(2-ethylhexyl)-[3,3'-dimethylene Synthesis method of ]-2,2'-diketone and black polyimide:

[0054] (1) (E) 6,6'-bis-(4-amino-phenyl)-1,1'-bis-(2-ethylhexyl)-[3,3'-dimethylhexyl]-2 , Synthesis of 2'-diketones:

[0055] ① Take a 250ml two-necked flask, weigh 6-bromo-indol-2-one (5g, 0.236mmol) and 6-bromoisatin (5.33g, 0.236mmol) with an analytical balance, add acetic acid (150mL) and Concentrated hydrochloric acid (37%) (1 mL) was refluxed at 120°C for 24 hours. After the reaction was completed, it was cooled to room temperature, the solvent was removed by suction filtration, the solid matter was washed with water, ethanol, and ethyl acetate in sequence, and dried in an oven overnight. After drying in vacuo, the reddish-brown product 1 was obtained.

[0056] ②Take a 250ml two-necked flask, weigh the product 1 (5g, 11.9mmol) and potassium carbonate (8.23g, 59.5mml) with an analytical balance, add DMF (80mL...

Embodiment 2

[0067] This example provides a (E) 6,6'-bis-(4-amino-phenyl)-1,1'-bis-(2-ethylhexyl)-[3,3'-dimethylene Synthesis method of ]-2,2'-diketone and black polyimide:

[0068] (1) (E) 6,6'-bis-(4-amino-phenyl)-1,1'-bis-(2-ethylhexyl)-[3,3'-dimethylhexyl]-2 , Synthesis of 2'-diketones:

[0069] ① Take a 250ml two-necked flask, weigh 6-bromo-indol-2-one (5g, 0.236mmol) and 6-bromoisatin (5.33g, 0.236mmol) with an analytical balance, add acetic acid (150mL) and Concentrated hydrochloric acid (37%) (1 mL) was refluxed at 120°C for 24 hours. After the reaction was completed, it was cooled to room temperature, the solvent was removed by suction filtration, the solid matter was washed with water, ethanol, and ethyl acetate in sequence, and dried in an oven overnight. After drying in vacuo, the reddish-brown product 1 was obtained.

[0070] ②Take a 250ml two-necked flask, weigh the product 1 (5g, 11.9mmol) and potassium carbonate (8.23g, 59.5mml) with an analytical balance, add DMF (80mL...

Embodiment 3

[0078] (1) (E) 6,6'-bis-(4-amino-phenyl)-1,1'-bis-(2-ethylhexyl)-[3,3'-dimethylhexyl]-2 , Synthesis of 2'-diketones:

[0079] ① Get a 250ml two-necked flask, weigh 6-bromo-indol-2-one (5g, 0.236mmol) and 6-bromoisatin (5.33g, 0.236mmol) with an analytical balance, add acetic acid (150mL) and Concentrated hydrochloric acid (37%) (1 mL) was refluxed at 120°C for 24 hours. After the reaction was completed, it was cooled to room temperature, the solvent was removed by suction filtration, the solid matter was washed with water, ethanol, and ethyl acetate in sequence, and dried in an oven overnight. After drying in vacuo, the reddish-brown product 1 was obtained.

[0080] ②Take a 250ml two-necked flask, weigh the product 1 (5g, 11.9mmol) and potassium carbonate (8.23g, 59.5mml) with an analytical balance, add DMF (80mL) to vacuumize, and pass nitrogen 3 times; stir at 80°C After 0.5-3h, 1-bromo-2-ethylhexane (4.7ml, 26.2mmol) was injected into the septum under the protection of nit...

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Abstract

The invention belongs to the technical field of organic polymer materials, and discloses a diamine monomer containing an isoindigo structure and black polyimide synthesized by the diamine monomer. According to the invention, halogenated indolone, halogenated isatin, alkyl halide (or acylating agent) and aminophenylboronic acid pinacol ester (or nitrophenylboronic acid pinacol ester) are used as raw materials to synthesize the dark red or black diamine monomer containing the isoindigo structure. Condensation polymerization is conducted on the synthesized diamine monomer (other diamines can be added) and aromatic dianhydride to obtain a polyamide acid solution, and thermal or chemical imidization is performed to prepare black polyimide. According to the invention, the intrinsic black polyimide is prepared from the diamine monomer containing the large-plane conjugated strong electron-withdrawing isoindigo structure, a method is simple to operate and efficient in reaction, and the black polyimide can be prepared without adding or coating any shading substance. The black polyimide prepared by the method is excellent in shading performance and has wide application value in the fields ofelectronic industry, aerospace, instrument communication and the like.

Description

technical field [0001] The invention belongs to the technical field of organic polymer materials, and in particular relates to a diamine monomer containing isoindigo structure and a black polyimide synthesized therefrom. Background technique [0002] Polyimide (PI) has excellent comprehensive properties because of its stable aromatic heterocyclic structure in its molecule, especially high and low temperature resistance, dimensional stability, mechanical properties, radiation resistance, etc., and is widely used in electronics , electrical appliances, aerospace and other fields. With the rapid development of the economy and the continuous improvement of people's living standards, people's requirements for the comprehensive performance of materials are getting higher and higher. However, the traditional PI film is mostly golden yellow due to the charge transfer complex generated between diamine and dianhydride, and the conjugated plane of the aromatic ring structure is small,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/34C08G73/10C08J5/18C08L79/08
CPCC07D209/34C08G73/1085C08J5/18C08J2379/08Y02E10/549
Inventor 叶强许江婷曹寮峰王以淋
Owner XIANGTAN UNIV
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