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Diamine monomer, polyimide film and preparation method and application thereof

A technology of polyimide film and diamine monomer, which is used in the preparation of amino compounds from amines, organic chemistry, chemical recycling, etc. Low problems such as high temperature resistance and transparency, excellent light transmittance and heat resistance, and simple procedures

Active Publication Date: 2022-08-05
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Diamine monomers currently used to prepare polyamides mainly realize the transparency of polyimides by introducing strong electron-withdrawing groups such as -CF3, alicyclic structures, large side groups, and building asymmetric non-coplanar structures. Improvements in both transparency and thermal performance, but difficult to achieve simultaneous improvements in transparency and thermal performance
Moreover, the existing diamine monomers have complex preparation procedures, low overall yield, and require steps such as hydrogenation reduction, which is not conducive to its industrial application
At the same time, the transparent polyimide prepared from it often has the problem of poor thermal performance and it is difficult to exceed 400 °C.

Method used

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  • Diamine monomer, polyimide film and preparation method and application thereof
  • Diamine monomer, polyimide film and preparation method and application thereof
  • Diamine monomer, polyimide film and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] An embodiment of the diamine monomer of the present invention, the chemical name of the diamine monomer in this embodiment is: 2,2"-dimethyl-[1,1':4',1"-terphenyl] -4,4"-diamine (DMTD), the structural formula is as follows:

[0049]

[0050] In this embodiment, the preparation method of the diamine monomer comprises the following steps:

[0051] (1) In a 250ml Shrek bottle, add 4-bromo-3-methylaniline (3.71g, 19.95mmol, 2.1eq) and 1,4-phenylenediboronic acid (1.57g, 9.50mmol, 1.0eq) in turn , then add 60ml ultra-dry tetrahydrofuran and 2mol / L K 2 CO 3 solution (28.5ml, 57mmol, 6eq);

[0052] (2) Degas the system in step (1) for 20 minutes in an argon atmosphere, and then quickly add Pd (PPh) in an argon atmosphere 3 ) 4 (329mg, 0.285mmol, 0.03eq) to give a reaction mixture;

[0053] (3) the reaction mixture was refluxed at 85°C for 24 hours under vigorous stirring, and the degree of completion of the reaction was tracked by thin layer chromatography;

[0054] ...

Embodiment 2

[0060] An example of the diamine monomer of the present invention, the chemical name of the diamine monomer in this example is: 2,2",5,5"-tetramethyl-[1,1':4',1 "-terphenyl]-4,4"-diamine (TMTD), the structural formula is as follows:

[0061]

[0062] In this example, the diamine monomer is composed of 4-bromo-2,5-dimethylaniline (2.90g, 14.50mmol, 2.2eq) and 1,4-benzenediboronic acid (1.09g, 6.58mmol, 1.0 eq) synthesis, the remaining reagent selection, step sequence, process parameters, etc. are the same as in Example 1.

[0063] In the preparation method of the diamine monomer described in this example, the crude product was further purified by a rapid preparative liquid chromatograph (EA:PE=1:3) to obtain a white product (1.4g, 67%), which is the present implementation Example of the diamine monomer.

[0064] The chemical reaction formula of the diamine monomer described in this example is as follows image 3 shown.

[0065] The hydrogen spectrum and carbon spectrum o...

Embodiment 3

[0069] An example of the diamine monomer of the present invention, the chemical name of the diamine monomer in this example is: 2,2",3,3"-tetramethyl-[1,1':4',1 "-terphenyl]-4,4"-diamine (23TMTD), the structural formula is as follows:

[0070]

[0071] In this example, the diamine monomer was composed of 4-bromo-2,3-dimethylaniline (1.01g, 5.04mmol, 2.1eq) and 1,4-benzenediboronic acid (0.40g, 2.40mmol, 1.0g) eq) synthesis, the remaining reagent selection, step sequence, process parameters, etc. are the same as in Example 1.

[0072] In the preparation method of the diamine monomer described in this example, the crude product was further purified by a rapid preparative liquid chromatograph (EA:PE=1:3) to obtain a whitish product (700 mg, 92%), which is the present implementation Example of the diamine monomer.

[0073] The chemical reaction formula of the diamine monomer described in this example is as follows Figure 4 shown.

[0074] The hydrogen spectrum and carbon s...

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Abstract

The invention discloses a terphenyl diamine monomer containing methyl, the structural formula of the diamine monomer is shown as a general formula M, R1-R12 are respectively and independently selected from methyl and hydrogen atoms, and at least one of R1-R12 is methyl. The diamine monomer has unique structural characteristics, and polyimide prepared from the diamine monomer has excellent light transmittance and heat resistance at the same time. Meanwhile, the invention also discloses a preparation method of the diamine monomer, which is simple in preparation procedure and relatively high in yield, and discloses polyimide which is prepared from the diamine monomer and has excellent light transmittance and heat resistance.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a methyl group-containing diamine monomer, a polyimide film, a preparation method thereof and the application of the diamine monomer in the preparation of a polyimide film. Background technique [0002] Polyimide is widely used as a substrate material for flexible devices due to its excellent heat resistance and good optical properties. Diamine monomer is one of the main raw materials for preparing polyimide, and the structure and properties of diamine monomer have a direct impact on the structure and properties of the obtained polyimide. Currently, common wholly aromatic polyimides exhibit darker colors in the visible light region due to intermolecular and intramolecular generated charge transfer complexes (CTCs), which affect their optical properties and limit their further applications. The thermal resistance and optical properties of polyimide are closely related t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/50C07C209/68C08G73/10C08J5/18C08L79/08
CPCC07C211/50C07C209/68C08G73/1007C08G73/1039C08G73/1082C08G73/1067C08J5/18C08J2379/08Y02P20/584Y02E10/549
Inventor 路庆华方云志张书宇
Owner SHANGHAI JIAO TONG UNIV
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