Diamine monomer containing pyrazine structure and preparation method thereof, polyimide containing pyrazine structure and preparation method thereof

A technology of diamine monomer and polyimide, which is applied in the field of polyimide containing pyrazine structure and its preparation, can solve the problems such as difficulty in applying transparent optical materials, and achieves improved electron transport properties, good thermal conductivity and the like. The effect of stability and high light transmittance

Active Publication Date: 2018-12-07
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Polyimide containing pyrazine structure is one of pyrazine-based polymers, which are widely used in locomotives, ships, aerospace and other fields due to their high mechanical strength, high glas...

Method used

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  • Diamine monomer containing pyrazine structure and preparation method thereof, polyimide containing pyrazine structure and preparation method thereof
  • Diamine monomer containing pyrazine structure and preparation method thereof, polyimide containing pyrazine structure and preparation method thereof
  • Diamine monomer containing pyrazine structure and preparation method thereof, polyimide containing pyrazine structure and preparation method thereof

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preparation example Construction

[0049] The present invention also provides the preparation method of the diamine monomer containing pyrazine structure, comprising the following steps:

[0050] Mix chloropyrazine, nitrophenol and alkaline ionic liquid to undergo nucleophilic substitution reaction to obtain dinitro compound;

[0051] Mixing the dinitro compound, phosphotungstic acid, zinc powder and an organic solvent for a reduction reaction to obtain a diamine monomer containing a pyrazine structure;

[0052] Wherein, the chloropyrazine is

[0053] The nitrophenol is Ar 1 is

[0054]

[0055] In the present invention, unless otherwise specified, all raw materials are commercially available products well known to those skilled in the art.

[0056] The invention mixes chloropyrazine, nitrophenol and alkaline ionic liquid to undergo nucleophilic substitution reaction to obtain dinitro compounds. In the present invention, the chloropyrazine is preferably 2,6-dichloropyrazine, 2,2'-dichlorobipyrazine,...

Embodiment 1

[0102] The preparation of 2,6-bis (4-aminophenoxy) pyrazine, its structural formula is as follows:

[0103]

[0104] At normal temperature and pressure, transfer 100mmol 2,6-dichloropyrazine, 210mmol p-nitrophenol, and 2200mmol basic ionic liquid [bmin]OH to a three-necked flask, and react for 5 hours under stirring and nitrogen protection , to obtain the product system;

[0105] Pour the obtained product system into deionized water, recover the basic ionic liquid [bmin]OH, filter the precipitated solid with suction, wash 3 times with deionized water, dry at 80°C for 12 hours, and recrystallize with methanol. 2,6-bis(4-nitrophenoxy)pyrazine was obtained with a yield of 85%.

[0106] Dissolve 50mmol of 2,6-bis(4-nitrophenoxy)pyrazine in 100mmol of absolute ethanol, add 1.25mmol of phosphotungstic acid and 250mmol of zinc powder under nitrogen protection, and transfer the mixed solution to a high-pressure reactor. React for 3 hours under the conditions of 0.3Mpa and 180°C; ...

Embodiment 2

[0110] The preparation of 2,2'-bis(2-methyl-4-aminophenoxy)bipyrazine, its structural formula is as follows:

[0111]

[0112] At normal temperature and pressure, 100mmol 2,2'-dichlorobipyrazine, 220mmol 2-hydroxy-5-nitrotoluene, and 2400mmol basic ionic liquid [bmin]OH were transferred to a three-necked flask, under stirring and nitrogen protection Under the condition of reaction 8 hours, obtain product system;

[0113] Pour the obtained product system into deionized water, recover the basic ionic liquid [bmin]OH, filter the precipitated solid with suction, wash 5 times with deionized water, dry at 80°C for 12 hours, and recrystallize with methanol. 2,2'-bis(2-methyl-4-nitrophenoxy)bipyrazine was obtained with a yield of 85%.

[0114] Dissolve 50mmol 2,2'-bis(2-methyl-4-nitrophenoxy)bipyrazine in 200mmol anhydrous methanol, add 1.25mmol phosphotungstic acid and 500mmol zinc powder under nitrogen protection, and mix The solution was transferred to a high-pressure reactor,...

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Abstract

The invention provides a diamine monomer containing a pyrazine structure as shown in formula I. In polyimide prepared from the diamine monomer, the electron affinity can be enhanced due to the existence of nitrogenous aromatic rings, so that the electron transmission property is improved, the intermolecular and intra-molecular charge transfer interaction of polyimide is weakened and the ultraviolet visible light transmittance of polyimide is enhanced; a lateral group is introduced into the diamine monomer containing the pyrazine structure, so that the mechanical properties and thermal properties of polyimide are not damaged while dense accumulation of molecular chains of polyimide is effectively reduced and solubility of polyimide in an organic solvent is enhanced; according to the disclosure of embodiments, the polyimide prepared from the diamine monomer containing the pyrazine structure provided by the invention has high heat stability, high mechanical strength, higher photo-permeability, excellent solubility and wide application value in the photoelectric field.

Description

technical field [0001] The invention relates to the technical field of polymer synthesis, in particular to a diamine monomer containing a pyrazine structure and a preparation method thereof, and a polyimide containing a pyrazine structure and a preparation method thereof. Background technique [0002] Aromatic heterocyclic polymers such as pyridine, pyrazine, pyrimidine, etc. are widely used in the synthesis of drugs and the preparation of aggregation-induced luminescent materials due to their special properties. Pyrazine-based polymers not only have relatively stable thermal properties and high mechanical strength, but also have special optical properties, so that they have better applications in charge-coupled devices and direct digital frequency synthesizers. However, there are few reports on the pyrazine-based polymers as transparent optical materials. [0003] Polyimide containing pyrazine structure is one of pyrazine-based polymers, which are widely used in locomotive...

Claims

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Application Information

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IPC IPC(8): C07D241/18C07D241/44C08G73/10C08J5/18C08L79/08
CPCC07D241/18C07D241/44C08G73/1007C08G73/1039C08G73/1064C08G73/1085C08J5/18C08J2379/08
Inventor 陈春海米智明周宏伟王小问赵晓刚王大明
Owner JILIN UNIV
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