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Aromatic diamine monomer containing cyano structure, preparation method of aromatic diamine monomer, polyimide, polyimide film, and preparation method and application of polyimide film

A technology of polyimide film and aromatic diamine, which is applied in the field of polyimide, can solve the problem of reducing the dielectric constant of polyimide, the complex synthesis route of new diamine monomer, the thermal stability of polyimide and the Problems such as mechanical properties need to be improved to achieve good thermal stability and mechanical properties, suitable for large-scale production, and improve processing performance

Pending Publication Date: 2021-10-08
UNIV OF SCI & TECH BEIJING
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  • Description
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Problems solved by technology

However, the synthesis route of the novel diamine monomer containing large substituted side groups or fluorine-containing structure is complex, and the technical problem produced at the same time is to reduce the dielectric constant of the polyimide prepared by it, and to use it as a raw material. The thermal stability and mechanical properties of polyimide still need to be improved

Method used

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  • Aromatic diamine monomer containing cyano structure, preparation method of aromatic diamine monomer, polyimide, polyimide film, and preparation method and application of polyimide film
  • Aromatic diamine monomer containing cyano structure, preparation method of aromatic diamine monomer, polyimide, polyimide film, and preparation method and application of polyimide film
  • Aromatic diamine monomer containing cyano structure, preparation method of aromatic diamine monomer, polyimide, polyimide film, and preparation method and application of polyimide film

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preparation example Construction

[0045] The present invention also provides a preparation method for the cyano-containing aromatic diamine monomer described in the technical solution, comprising the following steps:

[0046] (1) mixing a compound having a structure shown in formula I with a compound having a structure shown in formula II, a basic compound and a polar solvent, and performing a nucleophilic substitution reaction to obtain an intermediate having a structure shown in formula III;

[0047]

[0048] R in the formulas I, II and III 1 , R 2 is independently cyano;

[0049] (2) performing a reduction reaction on an intermediate having a structure shown in formula III to obtain an aromatic diamine monomer having a cyano group structure having a structure shown in formula IV;

[0050]

[0051] R in the formula IV 1 , R 2 is independently cyano.

[0052] In the present invention, unless otherwise specified, the raw materials used are conventional commercially available products in this field. ...

Embodiment 1

[0125] Preparation of aromatic diamine monomer bis(2-cyano-4-aminophenyl)amine containing cyano group structure

[0126] (1) 2.447g of 2-cyano-4-nitroaniline, 2.738g of 2-chloro-5-nitrobenzonitrile and 2.073g of anhydrous potassium carbonate and 30mL of DMAC polar solvent were added to the container Mix in a 250mL round-bottomed three-necked flask with a nitrogen inlet, magnetic stirring and condenser, stir and heat to 160°C for 24 hours, after the reaction, cool the system to 110°C, mix it with 200mL deionized water, and filter to obtain The reddish-brown solid was washed successively with deionized water and ethanol for 2 to 3 times, and dried in a vacuum oven at 80° C. for 12 hours to obtain 3.063 g of reddish-brown solid powder, which was then recrystallized with acetonitrile to obtain 2.389 g of brown solid powder (2 -cyano-4-nitrophenyl)amine intermediate, the productive rate is 75~80%; wherein said 2-cyano-4-nitroaniline, 2-chloro-5-nitrobenzonitrile and carbonic acid ...

Embodiment 2

[0136] The bis(2-cyano-4-aminophenyl)amine prepared in Example 1 was used as a diamine monomer to prepare a cyano-containing polyimide film PI-1.

[0137] (1) Di(2-cyano-4-aminophenyl)amine (0.1245g, 0.5mmol) and pyromellitic dianhydride (0.1091g, 0.5mmol) were dissolved in 2.1024mL of N,N-dimethyl Add acetamide (DMAC) into the reactor equipped with mechanical stirring, nitrogen gas inlet and outlet and thermometer, feed nitrogen gas, carry out polycondensation reaction for 5-8 hours under the condition of stirring at room temperature, put it in a vacuum drying oven to remove air bubbles for 3 minutes, and obtain A homogeneous viscous polyamic acid solution with a mass concentration of 10%; wherein, the cyano-containing aromatic diamine monomer (two (2-cyano-4-aminophenyl) amine) and the dianhydride monomer (Pyromellitic dianhydride) The ratio of the amount of substance is 1:1;

[0138] (2) Cast the polyamic acid solution obtained in the step (1) onto a clean and dry glass pl...

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Abstract

The invention provides an aromatic diamine monomer containing a cyano structure, a preparation method of the aromatic diamine monomer, a polyimide, a polyimide film, and a preparation method and application of the polyimide film, and belongs to the field of polyimide materials. A cyano group is introduced to the main chain of a polymer, and the cyano group has relatively large dipole moment, so that the cyano group is easy to form hydrogen bonds or intermolecular acting force, the polarity of the polymer can be increased, the intermolecular acting force between the main chains is remarkably improved, the dielectric constant of the polyimide material prepared from the polymer is improved, and the polyimide material has good thermal stability and mechanical properties; the regularity of a chain of polyimide prepared from the aromatic diamine monomer is broken and a non-coplanar structure is formed by adjusting the site of the cyano group on a benzene ring of the aromatic diamine monomer, the processability of the polyimide prepared from the aromatic diamine monomer is remarkably improved, and the aromatic diamine monomer is to prepare the polyimide film with the highest dielectric constant of 5.5 and the glass-transition temperature of 400 DEG C at the frequency of 102 Hz.

Description

technical field [0001] The invention relates to the field of polyimide materials, in particular to an aromatic diamine monomer containing a cyano group structure and a preparation method thereof, polyimide, a polyimide film, a preparation method and application thereof. Background technique [0002] Polyimide (Polyimide, PI) is a class of high-performance polymer materials containing imide rings in the molecular chain. It has excellent mechanical properties and reasonable breakdown strength. It can be used as membrane materials and high-performance fibers in modern high tech. Polyimide is generally prepared from diamine and dianhydride monomers by a one-step or two-step method. Due to the diversity of monomer types, the molecular structure of polyimide can be adjusted by selecting a combination of monomers with different structures. relationship with performance. The synthesis of diamine monomers with new structures has become one of the primary methods for preparing good ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/58C07C253/30C08G73/10C08J5/18C08L79/08
CPCC07C255/58C08G73/1067C08G73/1071C08J5/18C08J2379/08
Inventor 查俊伟田娅娅郑明胜
Owner UNIV OF SCI & TECH BEIJING
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