Pyridazine-group-containing diamine monomer and preparation method and application thereof

A technology of diamine monomer and pyridazineoxy group, which is applied in the field of diamine monomer containing pyridazine structure and its preparation, can solve the problems of poor optical transmission of polyimide materials, and avoid the difficulty of post-reduction treatment , reasonable design, reduce the effect of conjugation

Active Publication Date: 2017-08-18
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention i

Method used

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  • Pyridazine-group-containing diamine monomer and preparation method and application thereof
  • Pyridazine-group-containing diamine monomer and preparation method and application thereof
  • Pyridazine-group-containing diamine monomer and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0032] (1) Under room temperature and nitrogen protection conditions, 54.40mmol (11.99g) 4,4'-dihydroxydiphenylmethane, 130.56mmol (20.83g) 3-chloro-2-nitropyridazine and 130.56mmol (18.04 g) Potassium carbonate was dissolved in 1935mmol (180ml) N,N'-dimethylacetamide, the total mass fraction of solids in the system was 10% to 50%, then heated to 60°C, and reacted for 6 hours; after cooling down to room temperature, The reactant is poured into a sodium hydroxide solution with a mass fraction of 5%, filtered, and the resulting solid is repeatedly washed with deionized water until the washing liquid is neutral to obtain 15 g of dinitro crude product; Dissolve 6g of activated carbon in 861mmol (80ml) of N,N'-dimethylacetamide, heat to 70-90°C, filter after 30 minutes, add water dropwise to the filtrate until the solution is saturated, filter, and place the obtained solid in vacuum at 80°C Treated for 8 hours to obtain 4,4'-bis(6-nitro-3-pyridazinyloxy)diphenylmethane containing a...

Embodiment 2

[0038] (1) Under room temperature and nitrogen protection conditions, 54.40mmol (11.99g) 3,3'-dihydroxydiphenylmethane, 146.88mmol (23.43g) 3-chloro-2-nitropyridazine and 146.88mmol (20.71 g) Potassium carbonate was dissolved in 1613mmol (150ml) N,N'-dimethylacetamide, the total mass fraction of solids in the system was 10% to 50%, then heated to 60°C, and reacted for 6 hours; after cooling down to room temperature, The reactant was poured into a sodium hydroxide solution with a mass fraction of 5%, filtered, and the obtained solid was repeatedly washed with deionized water until the washing liquid was neutral, and 12 g of dinitro crude product was obtained; the dinitro crude product was Dissolve 6g of activated carbon in 964mmol (90ml) N,N'-dimethylacetamide, heat to 70-90°C, filter after 30 minutes, add water dropwise to the filtrate until the solution is saturated, filter, and vacuum the obtained solid at 80°C Treated for 8 hours to obtain 3,3'-bis(6-nitro-3-pyridazinyloxy)...

Embodiment 3

[0043] (1) Under room temperature and nitrogen protection conditions, 54.40mmol (15.14g) 3-hydroxy-6-(4-hydroxyphenoxy)biphenyl, 163.20mmol (26.03g) 3-chloro-2-nitropyridine Dissolve oxazine and 163.20mmol (23.01g) of potassium carbonate in 1720mmol (160ml) of N,N'-dimethylacetamide, the total mass fraction of solids in the system is 10% to 50%, then heat to 60°C and react for 6 hours After being down to room temperature, the reactant is poured into a mass fraction of 5% sodium hydroxide solution, filtered, and the gained solid is repeatedly washed with deionized water until the washing liquid is neutral, and 14 g of dinitro crude product is obtained; The dinitro crude product and 8.4g of activated carbon were dissolved in 1286mmol (120ml) N,N'-dimethylacetamide, heated to 70-90°C, filtered after 30 minutes, added water dropwise to the filtrate until the solution was saturated, and filtered , the resulting solid was vacuum-treated at 80°C for 8 hours to obtain 3-(6-nitro-3-pyr...

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Abstract

The invention provides pyridazine-group-containing diamine monomer and a preparation method and application thereof and belongs to the technical field of organic synthesis. The preparation method includes: adopting a nucleophilic substitution method to enable a dihydroxyl compound containing flexible group or asymmetric structure or bulky side group to react with chlorine-containing nitro pyridazine to obtain a dinitro intermediate containing a pyridazine structure, and reducing the dinitro intermediate to obtain diamine monomer containing a pyridazine structure; enabling the diamine monomer to react with dianhydride, and performing thermal imidization to obtain a high-performance heterocyclic polyimide film. The high-performance heterocyclic polyimide film maintains excellent thermal performance and mechanical performance that polyimide has originally, has solubility and photopermeability improved remarkably and has wide application prospect.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a diamine monomer containing a pyridazine structure and a preparation method and application thereof. Background technique [0002] Polyimide is a kind of macromolecule material with imide ring repeating unit aromatic heterocyclic ring on the molecular main chain. The unique aromatic structure endows polyimide with excellent high temperature resistance, outstanding mechanical properties, optical properties, aging resistance, radiation resistance and solvent resistance, and makes polyimide have longer service life and higher safety Coefficient, widely used in coatings, adhesives, aerospace, automotive and electrical and electronic fields, especially in high-end technical fields, such as aerospace and microelectronics, is one of the indispensable materials. [0003] Although the unique structure of polyimide endows it with various excellent properties, there are still so...

Claims

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Application Information

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IPC IPC(8): C07D237/22C08G73/10C08J5/18
CPCC07D237/22C08G73/1057C08G73/1067C08J5/18
Inventor 周宏伟张昭姚佳楠赵晓刚王大明陈春海
Owner JILIN UNIV
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