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Diamine monomer containing spiro pyran structure, preparation method and application thereof, polyimide and preparation and application thereof

A technology of diamine monomer and polyimide, which is applied in the field of gas membrane separation, can solve the problems of low chain spacing and specific surface area of ​​polymer films, low gas permeability of films, and compact molecular chains, and achieve excellent thermal performance. , Improve the effect of poor solubility and good solubility

Active Publication Date: 2020-07-03
JILIN UNIV
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Problems solved by technology

[0004] At present, the main problem of polyimide gas separation membrane is that although it has good gas pair selectivity, the molecular chains are tightly packed, and the chain spacing and specific surface area of ​​the polymer film are low, resulting in low gas permeability of the film. Low, solubility, poor selectivity

Method used

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  • Diamine monomer containing spiro pyran structure, preparation method and application thereof, polyimide and preparation and application thereof
  • Diamine monomer containing spiro pyran structure, preparation method and application thereof, polyimide and preparation and application thereof
  • Diamine monomer containing spiro pyran structure, preparation method and application thereof, polyimide and preparation and application thereof

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preparation example Construction

[0050] The present invention provides a preparation method for a diamine monomer containing a spiropyran structure described in the above technical scheme, comprising the following steps:

[0051] Mix mesityl oxide, hydroxy compound, first catalyst and first reaction solvent to perform isomerization reaction to obtain pyran spiro diphenol compound; the hydroxy compound is 2,5-dihydroxytoluene or m- Hydroquinone;

[0052] Mixing the pyran spiro diphenol compound, the mononitro compound, the second catalyst and the second reaction solvent, and performing a nucleophilic substitution reaction to obtain a dinitro compound;

[0053] mixing the dinitro compound, an organic solvent, a reducing agent and a third catalyst, and performing a reduction reaction to obtain a diamine monomer;

[0054] The mononitro compound is X-R', wherein X is F, Cl or Br, and R' includes

[0055] In the present invention, unless otherwise specified, the required preparation materials are commercially...

Embodiment 1

[0101] Preparation of methylpyran spirodiphenol:

[0102] Add 74.4840g (0.6mol) 2,5-dihydroxytoluene, 6.2578g (0.039mol) ferric chloride and 200mL (1.88mol) toluene to the 250mL reactor equipped with mechanical stirring device, under the protection of nitrogen, Raise the temperature to 100°C at a heating rate of 10°C / min, slowly add 11.3687g (0.12mol) mesityl oxide into the system dropwise with a constant pressure dropping funnel, continue stirring, and the reaction is when the raw material point disappears as detected by TLC End, stop the reaction; filter while it is hot, cool the filtrate to precipitate crude crystals, place the obtained crude crystals in a vacuum tube furnace, heat to a temperature of 150°C to sublime the crude product, collect the sublimated product, and obtain 12.0987g (0.033mol) methylpyridine Furan spiro ring diphenol compound, the product structure that obtains is as follows formula:

[0103]

[0104] Preparation of methylpyran spiromethoxypyridine...

Embodiment 2

[0109] The preparation process of methylpyran spirocyclic diphenol is with embodiment 1;

[0110] Preparation of methylpyran spirocyclic pyridine diamine:

[0111] The first step of reaction: In a 250mL three-necked flask equipped with a mechanical stirring device, add 5.5271g (0.015mol) of methylpyrandiol compound, 46mL (0.59mol) of N,N-dimethylformamide, The catalyst potassium carbonate of 4.6991g (0.034mol) is the reaction raw material, make the system ultrasonic in the ultrasonic wave of 20KHz for half an hour, fully mix, add the 2-chloro-5-nitropyridine of 5.9453g (0.0375mol), make the reaction The solid content of the system is 21%. Stir and heat the system to 120°C. When the raw material point disappears as detected by TLC, the reaction is completed. After the reaction is completed, the system is cooled and discharged into a mixed solvent of methanol: water = 1:1, pumped Filtrate and dry to obtain a crude product. Dissolve the obtained crude product in N,N-dimethylform...

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Abstract

The invention provides a diamine monomer containing a spiro pyran structure, a preparation method and application thereof, polyimide and preparation and application thereof, and belongs to the technical field of gas membrane separation. The diamine monomer has a micro-pore structure and contains a flexible group (ether bond) and a pyridine structure, a polyimide film prepared from the diamine monomer has a micro-pore structure, a flexible group (ether bond) and a pyridine structure, due to the micro-pore structure, gas micromolecules can easily permeate, the selective permeability of the filmis improved; due to the existence of a flexible group (ether bond), the free volume and flexibility of a polyimide molecular chain can be increased, a solvent is easy to permeate, the problem of poorsolubility of a traditional gas separation membrane caused by a rigid chain is solved, the gas separation membrane has good solubility in a common organic solvent; the introduction of a basic group pyridine structure can increase the permeability of acidic greenhouse gas carbon dioxide and increase the separation efficiency of other gases and carbon dioxide.

Description

technical field [0001] The invention relates to the technical field of gas membrane separation, in particular to a diamine monomer containing a spirocyclic pyran structure and its preparation method and application, polyimide and its preparation and application. Background technique [0002] Gas membrane separation technology is a new type of green separation technology, which has the advantages of high separation efficiency, simple operation, low energy consumption, green, and little environmental pollution. It has been widely used in the fields of medicine, food, biochemistry, energy and environmental protection. Polymer membrane has good separation performance, excellent mechanical properties and physical and chemical properties, so it has become a commonly used gas separation membrane material. Gas separation membrane technology is an important part of many applications in membrane separation technology, and it is the third generation of gas separation technology after c...

Claims

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Application Information

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IPC IPC(8): C07D493/10C08G73/10B01D71/64
CPCB01D71/64C07D493/10C08G73/1039C08G73/105C08G73/1071
Inventor 陈春海王书丽李莉姚佳楠周宏伟赵晓刚
Owner JILIN UNIV
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