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Phosphine-containing aromatic diamine compound, preparation method and application thereof

A technology of aromatic diacids and compounds, which is applied in the field of phosphine-containing aromatic diamine compounds and their preparation and application, can solve the problems of poor film transparency and low heat resistance of polyimide, and achieve improved heat resistance, The effect of high glass transition temperature and good visible light transparency

Active Publication Date: 2009-09-16
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the aryl phosphine group of 2,4-BADPO is located at the ortho or para position of the ether bond (-O-), which has an asymmetric molecular structure and high steric hindrance effect, and is compatible with the aromatic tetraacid bis Polyimide formed by polycondensation reaction of anhydride has low heat resistance and poor film transparency

Method used

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  • Phosphine-containing aromatic diamine compound, preparation method and application thereof
  • Phosphine-containing aromatic diamine compound, preparation method and application thereof
  • Phosphine-containing aromatic diamine compound, preparation method and application thereof

Examples

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Embodiment 1、3

[0029] Embodiment 1,3, the synthesis of 5-BADPO

[0030] Add 0.165mol (4.0095g) of magnesium powder and 27ml of tetrahydrofuran into a 500ml three-neck flask, and use an ice-water bath to control the temperature of the reactants in the reaction flask at 0-5°C. Mix 0.15mol (28.9485g) of 3,5-difluorobromobenzene and 68ml of tetrahydrofuran in a constant pressure funnel, and slowly drop them into the system under nitrogen protection. After all the drops were completed, the temperature of the reaction system was slowly returned to room temperature, and stirring was continued for 3 h to obtain a gray-black solution.

[0031]Cool the temperature of the reaction system to 0-5°C with an ice-water bath; add 0.1254mol (29.6863g) of diphenylphosphoryl chloride and 41ml of tetrahydrofuran into a constant pressure funnel, and then slowly drop them into the reaction system. After the drop, the temperature of the reaction system was slowly returned to room temperature, and the stirring was ...

Embodiment 2、3

[0044] Embodiment 2,3, the synthesis of 5-BADPO

[0045] The synthesis of 3,5-difluorophenyldiphenylphosphine oxide is the same as in Example 1.

[0046] In a 250ml three-necked flask, add 0.02mol (6.2854g) 3,5-difluorophenyl diphenylphosphine oxide, 0.042mol (4.5835g) 3-aminophenol, 0.052mol (7.1869g) anhydrous potassium carbonate, 35ml 1 , 3-dimethylimidazolinone (DMI) and 18.4ml toluene. Heated to 135°C under nitrogen protection, and maintained constant temperature for 12h. Part of the toluene was distilled off, the temperature of the system was raised to 190° C., and the stirring was continued for 3 h to obtain a black solution. Cool to room temperature, filter to obtain a brown solution, pour into 5% acetic acid aqueous solution, and mechanically stir to obtain a brown precipitate. The precipitate was filtered out, dried under vacuum at 65°C, recrystallized with ethanol, and decolorized with activated carbon. A light brown solid was obtained, and the yield of the seco...

Embodiment 3、3

[0052] Embodiment 3, 3, the synthesis of 5-BADPO

[0053] The synthesis of 3,5-difluorophenyldiphenylphosphine oxide is the same as in Example 1.

[0054] Add 0.02mol (6.2854g) 3,5-difluorophenyldiphenylphosphine oxide, 0.042mol (4.5835g) 3-aminophenol, 0.052mol (7.1869g) anhydrous potassium carbonate, 35ml in a 250ml three-necked flask, N,N-Dimethylacetamide (DMAc), and 18.4 ml toluene. Heated to 135°C under the protection of nitrogen, and maintained constant temperature reaction for 15h. Part of the toluene was distilled off, the temperature of the system was raised to 160°C, and the stirring was continued for 4 hours to obtain a black solution. Cool to room temperature, filter to obtain a brown solution, pour into 5% acetic acid aqueous solution, and mechanically stir to obtain a brown precipitate. The precipitate was filtered out, dried under vacuum at 65°C, recrystallized with ethanol, and decolorized with activated carbon. A light brown solid was obtained with a seco...

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Abstract

The invention discloses an aromatic diamine compound containing aryl phosphine groups, a prepration method and an application thereof. The structural general formula of the compound is shown in a formula I. The compound takes 3,5-difluoro-bromobenzene and diphenylphosphinic chloride as raw materials, firstly prepares 3,5-difluorophenyl diphenyl phosphine oxide by Grignard reaction and then continuously reacts with 3-aminophenol for preparation. The compound has smaller steric effect and has great value for improving the heat resistance performance of atomic oxygen resistant polyimide thin film materials and improving the visible light transparency. In addition, polyimide phosphine-containing polymer materials prepared by utilizing the phosphine-containing aromatic diamine compound have good atomic oxygen resistance performance, higher glass transition temperature and better visible light transparency, thereby being capable of being applied in the manufacturing of satellites and other aircraft parts in the LEO environment.

Description

technical field [0001] The invention relates to a phosphine-containing aromatic diamine compound, a preparation method and application thereof. Background technique [0002] Phosphine-containing polymer materials have excellent heat resistance, flame resistance, anti-atomic oxygen ablation performance, and excellent adhesion to different substrates, so they are widely used in high-tech fields such as aviation, aerospace, and microelectronics. application background. In recent years, the anti-atomic oxygen ablation performance of phosphine-containing polymers has made its application in low earth orbit (LEO) vehicles receive great attention (J.W.Connell, K.A.Watson, High Perform.Polym., 2001, 13: 23 -34). Atomic oxygen (AO) in the space environment of LEO (200-800Km) is an extremely active substance, which will generate high energy when it collides with the surface of the aircraft, and then trigger the physical, mechanical and optical properties of organic materials on the ...

Claims

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Application Information

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IPC IPC(8): C07F9/53C08G73/10
Inventor 杨士勇李卓刘金刚
Owner INST OF CHEM CHINESE ACAD OF SCI
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