Preparation method of bisphenol monomer containing phthalazinone structure

A technology of phthalazinone and monomers, which is applied in the field of preparation of bisphenol monomers containing phthalazinone structures, can solve problems such as poor solubility, and achieve the effects of mild reaction, reduced synthesis cost, and low raw material cost

Active Publication Date: 2019-06-07
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional polyarylether materials, such as polyarylether ketone materials, are semi-crystalline polymers with excellent chemical stability and mechanical properties, but poor solubility, and are only soluble in concentrated sulfuric acid at room temperature

Method used

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  • Preparation method of bisphenol monomer containing phthalazinone structure
  • Preparation method of bisphenol monomer containing phthalazinone structure
  • Preparation method of bisphenol monomer containing phthalazinone structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: Add DHPZ and K in the there-necked flask that magnetic stirring, reflux condensation device are housed 2 CO 3 , Salt formation reaction at 135°C for 5-6 hours, after the completion of the salt formation reaction, the reaction solution was lowered to room temperature, then added Ullmann coupling ligand PNTM, catalyst CuI and reactant BPM, and reacted in the dark for 12 hours, the reaction The temperature was gradually raised from room temperature to 130°C. After the reaction, sink the reaction solution into hot water and drain it overnight, dissolve the brown solid in chloroform, add excess anhydrous sodium sulfate to the filtrate obtained by suction filtration, and obtain a brown powdery solid after rotary evaporation, and use acetone or ethanol Rinse 1-2 times to obtain a light yellow solid, which is placed in a vacuum drying oven at 100°C for 10-12 hours in vacuum. Refined by DMAc at a mass volume ratio of 1:2.5 to obtain a white solid powder.

Embodiment 2

[0019] Embodiment 2: Add DHPZ and K in the there-necked flask that magnetic stirring, reflux condensing device are housed 2 CO 3 , salt-forming reaction at 135°C for 5-6 hours. After the salt-forming reaction, the reaction liquid was lowered to room temperature, and then Ullmann coupling ligand PNTM, catalyst CuI and reactant BPM were added, and the reaction was protected from light for 18 hours. The temperature was gradually raised from room temperature to 130°C. After the reaction, sink the reaction solution into hot water and drain it overnight, dissolve the brown solid in chloroform, add excess anhydrous sodium sulfate to the filtrate obtained by suction filtration, and obtain a brown powdery solid after rotary evaporation, and use acetone or ethanol Rinse 1-2 times to obtain a light yellow solid, which is placed in a vacuum drying oven at 100°C for 10-12 hours in vacuum. Refined by DMAc at a mass volume ratio of 1:2.5 to obtain a white solid powder.

Embodiment 3

[0020] Embodiment 3: Add DHPZ and K in the there-necked flask that magnetic stirring, reflux condensing device are housed 2 CO 3 , salt-forming reaction at 135°C for 5-6 hours. After the salt-forming reaction, the reaction liquid was lowered to room temperature, and then Ullmann coupling ligand PNTM, catalyst CuI and reactant BPM were added, and the reaction was protected from light for 24 hours. The temperature was gradually raised from room temperature to 130°C. After the reaction, sink the reaction solution into hot water and drain it overnight, dissolve the brown solid in chloroform, add excess anhydrous sodium sulfate to the filtrate obtained by suction filtration, and obtain a brown powdery solid after rotary evaporation, and use acetone or ethanol Rinse 1-2 times to obtain a light yellow solid, which is placed in a vacuum drying oven at 100°C for 10-12 hours in vacuum. Refined by DMAc at a mass volume ratio of 1:2.5 to obtain a white solid powder.

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Abstract

The invention discloses a preparation method of a bisphenol monomer containing a phthalazinone structure, and belongs to the technical field of novel materials. The bisphenol monomer containing the phthalazinone structure is synthesized by a two-step reaction. The method comprises the following steps: a bisphenol-like monomer containing the phthalazinone structure and p-bromoanisole are used as raw materials, 1,10-phenanthroline hydrate is adopted as a N-N bidentate ligand, CuI is used as a catalyst, a C-O, C-N Ullmann coupling reaction is performed to obtain intermediate product DMPPZ, and Lewis acid reduction is performed to obtain the target monomer DHPPZ. The synthetic method provided by the invention has the advantages of a short synthetic period and mild conditions; and the purity ofthe target monomer tested by liquid chromatography-mass spectrometry is 98%, and the yield is 85%-90%.

Description

technical field [0001] The invention belongs to the technical field of new materials, and relates to a preparation method of a bisphenol monomer (DHPPZ) containing a phthalazinone structure. Background technique [0002] The bisphenol monomer prepared and synthesized in this patent can be widely used in the synthesis of polyarylether materials, and the ether bond in the bisphenol monomer can increase the ductility and flexibility of polyarylether materials. Traditional polyarylether materials, such as polyarylether ketone materials, are semi-crystalline polymers with excellent chemical stability and mechanical properties, but poor solubility, and are only soluble in concentrated sulfuric acid at room temperature. The bisphenol monomer has a novel all-aromatic ring, twisted, non-coplanar naphthyridine ring structure, which can endow the polymer with outstanding heat resistance and solubility. Bisphenol monomer has good reactivity, has various reaction possibilities, and has ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/32
Inventor 蹇锡高王锦艳翁志焕刘程宗立率李楠
Owner DALIAN UNIV OF TECH
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