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Trifluoromethyl substituted aromatic diamine compound containing aromatic ester structure and preparation method thereof

A technology of trifluoromethyl and aromatic diamine, applied in the field of trifluoromethyl substituted aromatic diamine compounds and their preparation, can solve the problems of reducing the heat resistance of materials, affecting the application range, etc., and achieves high heat resistance, excellent Effects of thermal stability and mechanical properties, good dissolution and film formation

Pending Publication Date: 2021-01-15
SHENZHEN DALTON ELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although polyaramid and polyimide can exhibit good solubility by introducing a flexible structure and large side groups into the molecular chain, the heat resistance of the material is reduced to a certain extent, which affects its application range.

Method used

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  • Trifluoromethyl substituted aromatic diamine compound containing aromatic ester structure and preparation method thereof
  • Trifluoromethyl substituted aromatic diamine compound containing aromatic ester structure and preparation method thereof
  • Trifluoromethyl substituted aromatic diamine compound containing aromatic ester structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060]Example 1 Synthesis of 4,4'-diamino-3'-trifluoromethyl phenyl benzoate

[0061](1) Dissolve phenol (37.6g) in acetonitrile (1000ml), add sodium trifluoromethanesulfinate (CF3SO2Na) (31.2g), dichlorodicyanobenzoquinone (22.7g), 800mW / cm-2Irradiated with visible light, reacted at 25°C for 24h to obtain 3-trifluoromethylphenol (8.42g) with a yield of 13%.

[0062](2) Dissolve 3-trifluoromethylphenol (4.2g) in tetrahydrofuran, add Cu(NO3)2·3H2O (20.42g), react at 25°C for 6h to obtain 3-trifluoromethyl-4-nitrophenol (3.65g) with a yield of 68%.

[0063](3) Add 4-nitrobenzoic acid (4.00g) and 3-trifluoromethyl-4-nitrophenol (4.96g) into 90ml dichloromethane, add dicyclohexylcarbodiimide (DCC) ( 4.94g) and 4-dimethylaminopyridine (DMAP) (0.03g), reacted at 30℃ for 6h, filtered, concentrated and recrystallized to obtain 4,4'-dinitro-3'-trifluoromethyl phenyl benzoate (8.53g), the yield is 85%.

[0064](4) Add 4,4'-dinitro-3'-trifluoromethyl phenyl benzoate (10.00g) into 100ml tetrahydrofuran, ad...

Embodiment 2

[0067]Example 2 Synthesis of 4,4'-diamino-3,3'-bis(trifluoromethyl)phenyl benzoate

[0068](1) Combine benzoic acid (18.3g), trifluoroacetic acid (600ml), sodium thiosulfate (7.14g), titanium dioxide (TiO2) (4.8g) was added to the flask under 365nm ultraviolet light irradiation, reacted at room temperature for 24h, column chromatography separated to obtain 3-trifluoromethyl-benzoic acid (5.43g), the yield was 18%.

[0069](2) Dissolve 3-trifluoromethyl-benzoic acid (5.2g) in tetrahydrofuran, add Cu(NO3)2·3H2O (21.55g), react at 25°C for 6h to obtain 3-trifluoromethyl-4-nitrobenzoic acid (3.86g) with a yield of 60%.

[0070](3) Dissolve phenol (37.6g) in acetonitrile (1000ml), add sodium trifluoromethanesulfinate (CF3SO2Na) (31.2g), dichlorodicyanobenzoquinone (22.7g), 800mW / cm-2Irradiated with visible light, reacted at 25°C for 24h to obtain 3-trifluoromethylphenol (7.78g) with a yield of 12%.

[0071](4) Dissolve 3-trifluoromethylphenol (4.2g) in tetrahydrofuran, add Cu(NO3)2·3H2O (20.42g), re...

Embodiment 3

[0076]Example 3 Synthesis of 4,4'-diamino-2,3',6'-tris(trifluoromethyl)phenyl benzoate

[0077](1) Combine benzoic acid (18.3g), trifluoroacetic acid (600ml), sodium thiosulfate (7.14g), titanium dioxide (TiO2) (4.8g) was added to the flask under 313nm ultraviolet light irradiation, reacted at room temperature for 24h, column chromatography separated to obtain 3-trifluoromethyl-benzoic acid (4.56g), the yield was 16%.

[0078](2) Dissolve 3-trifluoromethyl-benzoic acid (5.2g) in tetrahydrofuran, add Cu(NO3)2·3H2O, react at 25°C for 6h to obtain 3-trifluoromethyl-4-nitrobenzoic acid (3.86g) with a yield of 60%.

[0079](3) Dissolve phenol (37.6g) in acetonitrile (1000ml), add sodium trifluoromethanesulfinate (CF3SO2Na) (62.4g), dichlorodicyanobenzoquinone (22.7g), 800mW / cm-2Visible light irradiation, reaction at 25°C for 24h to obtain 3,5-bis(trifluoromethyl)phenol (7.78g), with a yield of 12%.

[0080](4) Dissolve 3,5-bis(trifluoromethyl)phenol (4.2g) in tetrahydrofuran, add Cu(NO3)2·3H2O (20.4...

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Abstract

The invention provides a trifluoromethyl substituted aromatic diamine compound containing an aromatic ester structure and a preparation method thereof, and relates to the field of organic synthesis. The trifluoromethyl substituted aromatic diamine compound has an aromatic ester structure and trifluoromethyl at the same time, and is stable in structure. Polyarylamide or polyimide prepared from thetrifluoromethyl substituted aromatic diamine compound is structurally characterized in that a main chain contains a polar aryl ester structure, and a high-heat-resistance trifluoromethyl large side group is suspended on the main chain, so that the prepared polyarylamide or polyimide has good solubility in a polar aprotic solvent while maintaining high heat resistance. That is to say, the polyarylamide and polyimide prepared from the aromatic diamine compound have good dissolving film-forming property, excellent thermal stability and excellent mechanical properties, and are expected to be applied to a new generation of microelectronic packaging materials and flexible display materials.

Description

Technical field[0001]This application relates to the field of organic synthesis, in particular to a trifluoromethyl substituted aromatic diamine compound containing an aromatic ester structure and a preparation method thereof.Background technique[0002]Both polyaramid and polyimide are heat-resistant polymer materials with excellent comprehensive properties. Since their industrialization began in the 1960s and 1970s, they have been used in various fields, especially as high-performance fibers, high-heat-resistant composite matrix and electronic packaging materials in aerospace, machinery, microelectronics, petrochemical and other industries Has a wide range of applications. Although this kind of high temperature resistant materials has excellent comprehensive performance, but because of their rigid main chain structure, as well as the strong interaction between molecules and the close packing of molecular chains, most of the polyaramids and polyimides have High melting temperature an...

Claims

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Application Information

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IPC IPC(8): C08G73/10C08G69/42C08G59/50
CPCC08G73/1039C08G73/1071C08G73/1007C08G69/42C08G59/504
Inventor 王胜林黎厚明王建新
Owner SHENZHEN DALTON ELECTRONICS MATERIAL CO LTD
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