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Cyano-containing polysubstituted aromatic diamine monomer and preparation method thereof

An aromatic diamine and monomer technology, applied in the field of diamine monomer and its preparation, can solve the problems of poor melt processability and solubility of polyimide, limited popularization and application, corrosion of mechanical equipment and the like, and achieves good solubility, The effect of low temperature and low cost

Active Publication Date: 2022-05-10
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003]However, common polyimide melt processability and solubility are very poor, which limits its popularization and application in civilian fields
In the process of synthesizing diamine monomers, most of them are synthesized by adding inorganic strong bases at present, but the addition of a large amount of inorganic bases in the industrial production process will lead to corrosion of mechanical equipment and release huge amounts of diamines during the reaction process. The heat is difficult to control, has certain dangers, and will also cause environmental pollution, and in industrial production, most of the prepared cyano-substituted diamine monomers are black or brown, and their purity is low

Method used

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  • Cyano-containing polysubstituted aromatic diamine monomer and preparation method thereof
  • Cyano-containing polysubstituted aromatic diamine monomer and preparation method thereof
  • Cyano-containing polysubstituted aromatic diamine monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] (1) Under the protection of nitrogen, in a three-necked flask equipped with mechanical stirring, add a molar ratio of 2:1 containing substituent R 1 The p-aminophenol A and dihalobenzonitrile compound B were further separated into ionic liquid catalysts, stirred at room temperature for half an hour, then heated to 65°C for 10 hours, and then ended the reaction;

[0065] (2) White diamine monomer can be obtained after settling, filtering, drying and recrystallization;

[0066] In above-mentioned reaction, described ionic liquid catalyst selects ionic liquid catalyst 1, and the structural formula of described ionic catalyst is: The dosage is containing substituent R 1 2 times the mass sum of p-aminophenol A and dihalobenzonitrile compound B, Ar 1 Choose as: Ar 2 Choose as: The chemical structural formula of gained target product is:

[0067]

[0068] The specific characterization data are as follows:

[0069] like figure 1 as shown, 13 C NMR (101MHz, DMSO-d...

Embodiment 2-7

[0073] The specific method is consistent with that of Example 1, except that the reaction temperature, reaction time, and molar ratio of raw materials will be somewhat different. The specific setting parameters and the purity of the target product are shown in Table 1.

Embodiment 8

[0075] Concrete method is consistent with embodiment 1, and difference is as shown in table 1, and ionic liquid catalyst selects ionic liquid catalyst 4 for use, and the structural formula of described ionic catalyst 4 is: The dosage is containing substituent R 1 2 times of the mass sum of p-aminophenol A and dihalobenzonitrile compound B, the chemical structural formula of the obtained target product is:

[0076]

[0077] The specific characterization data are as follows:

[0078] like image 3 as shown, 13 C NMR (101MHz, DMSO-d 6 )δ162.4, 144.5, 143.9, 135.2, 122.8, 122.1, 118.7, 114.7, 113.7, 107.8, 91.5, 17.4. The carbon spectrum is consistent with the structure of the expected product spectrum.

[0079] like Figure 4 as shown, 1 HNMR (400MHz, DMSO-d 6 )δ7.36(t, J=8.5Hz, 1H), 6.83–6.81(m, 2H), 6.78–6.75(m, 2H), 6.69–6.67(m, 2H), 6.31(d, J=8.5Hz ,2H), 4.89(s,4H). The hydrogen spectrum is consistent with the structure of the expected product.

[0080] The speci...

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Abstract

The invention provides a cyano-containing polysubstituted aromatic diamine monomer, the structural formula of the cyano-containing polysubstituted aromatic diamine monomer is shown in the specification, and R1 and R2 are one of-H,-CF3,-OCH3 or alkyl. The diamine monomer can be applied to the preparation of a high-performance polyimide film material, and can further improve the potential application values of dissolving film-forming property, optical transparency, tensile strength property, dielectric loss property and the like of the prepared polyimide film material.

Description

technical field [0001] The invention relates to the field of diamine monomer and its preparation, in particular to a cyano group-containing multi-substituted aromatic diamine monomer and its preparation method. Background technique [0002] Polyimide is a class of high-end polymer materials with excellent properties and is widely used in high-tech fields. It contains strong rigid benzene ring and imide ring, has excellent high temperature resistance, mechanical properties, corrosion resistance and electrical properties and is widely used in aerospace, electronic devices, precision machinery, high-performance packaging, microelectronics and other new products. technology field. In the future, the development of optoelectronic devices will gradually show the trend of light weight, large size, ultra-thin and flexible. Flexible polymer materials have become the first choice for flexible optoelectronic packaging substrate materials in the future due to their advantages such as l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/54C07C253/30C07C217/90C07C213/06C07D239/52C07D213/57C07D417/14C07D401/14C07D403/14C07D409/14C07D405/14C07D207/36
CPCC07C255/54C07C253/30C07C217/90C07C213/06C07D239/52C07D213/57C07D417/14C07D401/14C07D403/14C07D409/14C07D405/14C07D207/36
Inventor 谢劲夏嗣禹朱成建
Owner NANJING UNIV
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