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Synthesis of diamine monomer with azo and polyimide prepared from diamine monomer

A technology of polyimide and diamine monomers, applied in the direction of azo dyes, diaryl/triarylmethane dyes, diaryl/triarylmethane dyes, etc., to achieve the effect of simple process operation and wide application

Inactive Publication Date: 2016-01-20
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of transition metal complexes and azobenzene derivatives with Schiff base structure by this technology belongs to the category of small molecules. In liquid crystal display devices, they can only be used as liquid crystal filling units.

Method used

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  • Synthesis of diamine monomer with azo and polyimide prepared from diamine monomer
  • Synthesis of diamine monomer with azo and polyimide prepared from diamine monomer
  • Synthesis of diamine monomer with azo and polyimide prepared from diamine monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] This example is to prepare 4,4`-diamino-4``azotriphenylmethane, that is, diamine monomer, whose structural formula is:

[0051]

[0052] This embodiment specifically includes the following steps:

[0053] Step 1, synthetic 4-hydroxyl-4 `-methoxy azobenzene, its structural formula is:

[0054] Specifically:

[0055] 1.1) 4-Methoxyaniline (6.1625g, 50mmol) was dissolved in 50mL concentrated HCl / H 2 O(V HCl :V H2O =1:4) in the beaker of the mixed solution, after it was completely dissolved, it was placed in an ice-water bath and cooled to below 5°C.

[0056] 1.2) Under vigorous stirring environment, 10mL of cold sodium nitrite (3.5237g, 50mmol) aqueous solution was added dropwise to this solution to obtain the diazonium salt solution of 4-methoxyaniline, and this solution was maintained at 5 below ℃.

[0057] 1.3) In another beaker, phenol (4.7012g, 50mmol) was dissolved in 25mL of 10% aqueous sodium hydroxide solution, cooled to below 5°C in an ice-water bath, ...

Embodiment 2

[0068] This embodiment is a polyimide prepared from the azodiamine-containing monomer described in Example 1, and its structural formula is:

[0069]

[0070] This embodiment specifically includes the following steps:

[0071] Step 1, feed nitrogen into the reactor equipped with mechanical stirring, nitrogen import and export and thermometer, the diamine monomer (3.0015g, 5mmol) of azo structure and diphenyl ether tetra-acid dianhydride (ODPA) single The polyamic acid solution (1.6263g, 5mmol) was dissolved in 10.8975g N,N-dimethylacetamide (DMAc), and reacted at 10°C for 8h to obtain a polyamic acid solution, the structural formula of which was:

[0072]

[0073] Step 2: Coating the polyamic acid solution at a speed of 3 cm / s, pre-baking at 50°C for 2 hours, then keeping the pre-baked film at 90°C for 2 hours, 120°C for 2 hours, and 200°C for 2 hours. 250 ° C for 2 hours, and finally obtained polyimide, the infrared spectrum of polyimide is as follows figure 2 shown....

Embodiment 3

[0075] This embodiment is a polyimide prepared from the azodiamine-containing monomer described in Example 1, and its structural formula is:

[0076]

[0077] This embodiment specifically includes the following steps:

[0078] Step 1, feed nitrogen into the reactor equipped with mechanical stirring, nitrogen inlet and outlet and thermometer, the diamine monomer (3.0056g, 5mmol) of azo structure and biphenyltetraacid dianhydride (BPDA) monomer ( 1.4705g, 5mmol) was dissolved in 10.9556g N,N-dimethylacetamide (DMAc), and reacted at 12°C for 10h to obtain a polyamic acid solution, whose structural formula is:

[0079]

[0080] Step 2: Coating the polyamic acid solution at a speed of 3.5cm / s, pre-baking at 50°C for 2.5h, then keeping the pre-baked film at 90°C for 2.5h, 120°C for 2.5h, 200°C ℃ for 2.5 hours, 250 ℃ for 2.5 hours, and finally polyimide is obtained. The thermal weight loss curve of polyimide is as follows image 3 shown.

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Abstract

The invention discloses synthesis of a diamine monomer with azo and polyimide prepared from the diamine monomer. The structural formula of the polyimide is shown in the specification. The polyimide is synthesized through polycondensation of the diamine monomer and a dianhydride monomer. The polyimide has the good heat stability, mechanical property and photoinduced orientation performance, and is beneficial to being used as a liquid crystal display device.

Description

technical field [0001] The invention relates to a new material in the field of liquid crystal devices, in particular to the synthesis of an azodiamine-containing monomer and the polyimide prepared therefrom. Background technique [0002] The quality of liquid crystal display devices depends on the orientation of liquid crystal molecules. So far, polyimide is the most widely used liquid crystal orientation material in industry. However, most of the currently used liquid crystal alignment agents use rubbing alignment. Rubbing alignment has high requirements for rubbing materials and equipment, and dust, static electricity and scratches will be generated during the rubbing alignment process, which will have a relatively large negative effect on the quality of liquid crystal devices. impact, which further limits their application in related fields. In order to avoid problems in the process of rubbing alignment, and to prepare polyimide materials with excellent comprehensive pro...

Claims

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Application Information

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IPC IPC(8): C07C245/08C08G73/10
CPCC09B56/00C09B11/12C09B69/106
Inventor 路庆华童发钦
Owner SHANGHAI JIAO TONG UNIV
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