A dianhydride monomer containing a pyrazine structure and a preparation method thereof, and a polyimide containing a pyrazine structure and a preparation method thereof

A dianhydride monomer and polyimide technology, which is applied in the field of polyimide containing pyrazine structure and its preparation, can solve the problems that it is difficult to apply transparent optical materials, achieve good solubility, reduce molecular chain The effect of dense packing and good thermal stability

Active Publication Date: 2020-05-08
浙江中科亚安新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 glass transition temperature and corrosion resistance. , but it is difficult to apply it in transparent optical materials due to the limitation of strong UV-visible light absorption of the pyrazine-based polymer

Method used

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  • A dianhydride monomer containing a pyrazine structure and a preparation method thereof, and a polyimide containing a pyrazine structure and a preparation method thereof
  • A dianhydride monomer containing a pyrazine structure and a preparation method thereof, and a polyimide containing a pyrazine structure and a preparation method thereof
  • A dianhydride monomer containing a pyrazine structure and a preparation method thereof, and a polyimide containing a pyrazine structure and a preparation method thereof

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preparation example Construction

[0047] The present invention also provides a preparation method of the dianhydride monomer containing pyrazine structure, including the following steps:

[0048] Mixing the pyrazine derivative, the dicyano compound, the base I and the ionic liquid to undergo a nucleophilic substitution reaction to obtain a tetracyano compound;

[0049] Mixing the tetracyano compound, organic solvent, water, base II, and a catalyst to undergo a hydrolysis reaction to obtain a tetraacid containing a pyrazine structure;

[0050] Mixing the tetraacid containing a pyrazine structure and acetic anhydride to undergo a dehydration cyclization reaction to obtain a dianhydride monomer containing a pyrazine structure;

[0051] The pyrazine derivative is

[0052]

[0053]

[0054] In the present invention, unless otherwise specified, all raw materials are commercially available products well known to those skilled in the art.

[0055] In the present invention, a pyrazine derivative, a dicyano compound, a base I and...

Embodiment 1

[0107] The preparation of 2,6-bis(3,3',4,4'-diphthalic anhydride oxy)pyrazine, its structural formula is as follows:

[0108]

[0109] Put 100mmol of 2,6-dichloropyrazine, 205mmol of 3,4-dicyanophenol, 210mol of sodium hydride and 700mmol of 1-methyl-3-ethylimidazole formate into a stainless steel reactor at a pressure of 0.3Mpa and Under stirring conditions, control the temperature of the system at 70℃ and react for 30 minutes. After the system returns to normal temperature and pressure, pour the solution into deionized water to separate the solids, recover the ionic liquid and filter the solids, and wash them with deionized water After 3 times, it was dried at 80°C for 12 hours, and recrystallized with acetonitrile to obtain 2,6-bis(3,3`,4,4`-tetracyanophenoxy)pyrazine 96mmol;

[0110] Put 50mmol 2,6-bis(3,3`,4,4`-tetracyanophenoxy)pyrazine, 500mmol 18-crown-6, 1000mmol water, and 600mmol calcium hydroxide into a three-necked flask and heat up To reflux, keep the reflux rate for...

Embodiment 2

[0115] The preparation of 27-bis(33`44`-diphthalic anhydride oxy)quinoxaline, its structural formula is as follows:

[0116]

[0117] Put 100mmol 2,7-dichloroquinoxaline, 210mmol 3,4-dicyanophenol, 220mol calcium hydride and 850mmol 1,3-dimethylimidazole iodide into the stainless steel reaction kettle, and stir under 0.5Mpa pressure. Conditions: control the temperature of the system at 70℃, react for 30 minutes, after the system returns to normal temperature and pressure, pour the solution into deionized water to precipitate solids, recover the ionic liquid and filter the resulting solids, and wash them with deionized water 5 times Dry at 80°C for 12 hours and recrystallize with acetonitrile to obtain 2,7-bis(3,3`,4,4`-tetracyanophenoxy)quinoxaline 93mmol;

[0118] Put 50mmol 2,7-bis(3,3`,4,4`-tetracyanophenoxy)quinoxaline, 800mmol 18-crown-6, 1100mmol water, and 800mmol potassium hydroxide into a three-necked flask, Raise the temperature to reflux and keep the reflux rate at 2 se...

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Abstract

The invention provides a dianhydride monomer containing pyrazine structure, which is represented as the formula (I); polyimide, prepared with the dianhydride monomer as a monomer, is enhanced in constraining force on electrons since the pyrazine structure is an important electron-deficient unit, so that intermolecular and intramolecular charge transfer interactions are effectively reduced, and ultraviolet-visible light transmittance of the polyimide is improved; meanwhile, by introducing side groups into the dianhydride monomer containing pyrazine structure, close packing of molecular chains of the polyimide is effectively reduced without damage on mechanical and thermal properties of the polyimide, thereby increasing dissolubility of the polyimide in organic solvents. According to embodiments, the polyimide, prepared from the dianhydride monomer containing pyrazine structure, has excellent thermal stability, mechanical strength, light transmittance and dissolubility. Furthermore, thepolyimide has extensive application value in the field of photoelectricity.

Description

Technical field [0001] The invention relates to the technical field of polymer synthesis, in particular to a dianhydride 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 drug synthesis, preparation of aggregation-induced luminescent materials, etc. due to their special properties. Pyrazine-based polymers have relatively stable thermal properties and high mechanical strength, as well as special optical properties, which make them suitable for use in charge-coupled devices and direct digital frequency synthesizers; but The pyrazine-based polymers are rarely reported as transparent optical materials. [0003] Polyimide containing pyrazine structure is one of the pyrazine-based polymers. It is widely used in locomotives, ships, aerospace and other fields du...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C08G73/10
CPCC07D405/14C08G73/1085
Inventor 周宏伟王小问陈春海米智明王大明赵晓刚
Owner 浙江中科亚安新材料有限公司
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