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Pyrrolyl aromatic diamine containing phthalonitrile structure and its preparation method and application

A technology of pyrrolyl aromatic diamine and phthalonitrile, which is applied in the field of polymer preparation to achieve the effects of improving flame retardancy and organic solubility

Inactive Publication Date: 2016-08-17
四川启科新材料有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, among the monomer raw materials used to prepare polyimides, diamine monomers containing phthalonitrile side groups are rarely reported, and there are no pyrrolyl aromatic diamines containing phthalonitrile structures. reported that a monomer belonging to a new class of structure

Method used

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  • Pyrrolyl aromatic diamine containing phthalonitrile structure and its preparation method and application
  • Pyrrolyl aromatic diamine containing phthalonitrile structure and its preparation method and application
  • Pyrrolyl aromatic diamine containing phthalonitrile structure and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1: Preparation of 1,4-diphenyl-1,4-diketone (compound 1)

[0051] 30.0g anhydrous tetrahydrofuran and 3.0g (15mmol) 2-bromoacetophenone were successively added to the reaction kettle with stirrer, thermometer and nitrogen replacement device, and 1.0g (15mmol) zinc powder and 0.1 g iodine. React at 66°C for 17 hours; after the reaction, filter the insoluble matter, slowly pour the filtrate into water, extract the organic phase with chloroform and wash with water, extract the chloroform by rotary evaporation and dry it with anhydrous magnesium sulfate, and use chloroform / n-hexane with a volume ratio of 8:2 The white needle-like solid is 1,4-diphenyl-1,4-dione after separation by eluent column chromatography, the yield is about 65-80%, and the melting point is 143-145°C. Infrared spectrum FT-IR (KBr tablet): 3081, 3071, 1677, 1577, 989, 761. H NMR spectrum test 1 H NMR (CDCl 3 , 200Hz) δ: 3.46 (s, 4H), 7.50 (m, 6H), 8.04 (m, 4H).

Embodiment 2

[0052] Example 2: Preparation of 4-(2,5-diphenyl-1H-pyrrolyl)phthalonitrile (compound 2)

[0053] 800mL dry toluene, 23.8g (100mmol) 1,4-diphenyl-1,4-dione (compound 1), 17.2g (120mmol) 4-aminophthalonitrile and 2.1g (12mmol) Add p-toluenesulfonic acid into a reaction kettle equipped with a stirrer, thermometer and nitrogen replacement device, raise the temperature to reflux under normal pressure; react at reflux temperature for 120h; after the reaction, evaporate toluene, wash with water and dry over anhydrous magnesium sulfate , using dichloroethane / n-hexane with a volume ratio of 1:1 as eluent column chromatography to obtain a gray solid that is 4-(2,5-diphenyl-1H-pyrrolyl)phthalonitrile, producing The rate is about 78-86%; H NMR spectrum test 1 H NMR (400MHz, CD 3 Cl) δ: 6.53 (s, 2H), 7.40 (m, 2H), 7.56 (m, 4H), 7.72 (m, 5H), 7.81 (d, 1H), 8.09 (d, 1H). C 24 h 15 N 3 (345) Elemental analysis theoretical value: C, 83.46; H, 4.38; N, 12.17; measured value: C, 83.51; H,...

Embodiment 3

[0054] Example 3: Preparation of 4-(2,5-bis(4-nitrophenyl)-1H-pyrrolyl)phthalonitrile (compound 3)

[0055] Mix 10mL of concentrated nitric acid with a mass concentration of 70% and 12mL of concentrated sulfuric acid with a mass concentration of 98% to form a mixed acid solution, add it to a reaction kettle equipped with a stirrer, a thermometer and a nitrogen replacement device, and cool it to 0°C; then add dropwise 22 mL of a nitromethane solution of 2M 4-(2,5-diphenyl-1H-pyrrolyl)phthalonitrile to this mixed acid solution, and keep the system temperature at 0°C; after the dropwise addition, react at 0°C for 2h and 35°C for 2h; after the reaction, slowly pour the reaction solution into crushed ice to obtain a light yellow solid, which is washed with water until neutral and collected by filtration; 1:1 methanol / toluene mixed solvent recrystallization, vacuum drying to obtain 4-(2,5-bis(4-nitrophenyl)-1H-pyrrolyl)phthalonitrile with a yield of about 72-74 %; H NMR spectrum te...

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Abstract

The invention discloses a pyrrole aromatic diamine containing a phthalic nitrile structure and a preparation method thereof. 2-bromoacetophenone is taken as a raw material to prepare 4-(2,5-bi(4-aminophenyl)-pyrryl) phthalonitrile by reaction of four steps, namely condensation, closed loop, nitration and reduction. The aromatic diamine disclosed by the invention is high in purity, and stable at room temperature, and is an important monomer component for preparing a plurality of polyimides, and an application of the polyimides in the fields such as a high-performance fiber, organic luminescent materials, a functional coating, a special adhesive and the like is expanded.

Description

technical field [0001] The invention belongs to the field of polymer preparation, in particular to pyrrolyl aromatic diamine containing phthalonitrile structure and its preparation method and application. Background technique [0002] Polyimide is a class of high-performance polymers containing imide rings in its chemical structure. Its products include films, molding compounds, composite matrix resins, fibers, coatings, adhesives, etc., because of its good heat resistance It is difficult to be replaced as a special material in high-tech industries such as aerospace and microelectronics due to its special physical properties such as high resistance, radiation resistance, low dielectric constant, high strength and high modulus. Although polyimide has many excellent properties, its application fields are greatly limited due to its rigid main chain and strong intermolecular forces, which make it difficult to dissolve and melt process. In order to overcome these shortcomings, r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/335C08G73/10
CPCC07D207/335C08G73/1007C08G73/1082
Inventor 武迪蒙江时喜唐文睿
Owner 四川启科新材料有限责任公司
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