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Asymmetric aromatic diamine having naphthalenone binaphthyl structure, preparation and use thereof

A technology of xinthaphthylone binaphthyl and aromatic diamine, which is applied in the field of aromatic diamine compound and its preparation and application, can solve the loss of polyimide, only between 200-300°C, polyimide is insoluble, etc. problems, to achieve good film-forming properties, excellent mechanical properties, and high light transmittance

Inactive Publication Date: 2008-10-01
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the introduction of fluorine-containing side groups and ether bonds solves the problem of polyimide insolubility, due to the introduction of a relatively large density of flexible structural unit ether bonds in the main chain of the polymer molecule, the glass of this type of polyimide The melting temperature is generally only between 200 and 300 ° C, which has a greater loss compared with commercial polyimides.

Method used

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  • Asymmetric aromatic diamine having naphthalenone binaphthyl structure, preparation and use thereof
  • Asymmetric aromatic diamine having naphthalenone binaphthyl structure, preparation and use thereof
  • Asymmetric aromatic diamine having naphthalenone binaphthyl structure, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 2-(4-aminophenyl)-4-[4-(4-aminophenoxy)-naphthyl]-phthalazin-1-one:

[0037] ①Under nitrogen protection, add 14.4g (0.05mol) 4-(4-hydroxynaphthyl)-2,3-naphthyridine-1-one and 15.8g (0.1mol) p-chloronitrobenzene to 500ml Add 14.5g (0.105mol) of potassium carbonate, 100ml of N,N-dimethylacetamide and 40ml of toluene to a three-necked flask, dehydrate using a water separator, and react azeotropically at 140-150°C for 3-6 hours until dehydration Completely, then the toluene was evaporated by heating up and the reaction was completed after reflux reaction at about 168°C for 3 hours. Crystallization gave a dark green dinitro compound: 2-(4-nitrophenyl)-4-[4-(4-nitrophenoxy)-naphthyl]-phthalazin-1-one, yield About 80-90%, melting point 239-241 ℃. FT-IR(KBr)v / cm -1 : 1675 (C=O), 1519, 1345 (-NO 2 ), 1245(C-O-C). 1H NMR (DMSO-d 6 , 400MHz) δ: 8.51(d, 1H), 8.38(d, 2H), 8.29(d, 2H), 8.06~8.10(m, 3H), 7.98(t, 1H), 7.89(m, 2H), 7.82 (d, 2H), 7.64 (t, 1H), 7.57 ...

Embodiment 2

[0040] 2-(4-amino-2-trifluoromethylphenyl)-4-[4-(4-amino-2-trifluoromethylphenoxy)-naphthyl]-naphthyridine-1 - Preparation of ketones:

[0041] ①Under nitrogen protection, mix 14.4g (0.05mol) 4-(4-hydroxynaphthyl)-2,3-naphthyridine-1-one and 22.6g (0.1mol) 2-chloro-5-nitro Add benzotrifluoride to a 500ml three-necked flask, then add 14.5g (0.105mol) potassium carbonate and 120ml N,N-dimethylformamide respectively, react at 100-150°C for 10-20h, and pour the product into 1000ml methanol In / water (1:1), fully stir the precipitate and filter, and wash the product repeatedly with hot water, and further separate and purify it by column chromatography to obtain a white fluorine-containing dinitro compound: 2-(4-nitro-2-trifluoroform phenyl)-4-[4-(4-nitro-2-trifluoromethylphenoxy)-naphthyl]-phthalazin-1-one, the yield is about 80-90%, and the melting point is 112 ~114°C. 1681 (C=O), 1536, 1333 (-NO 2 ), 1264(C-O-C), 1152(CF 3 ). 1 H NMR (DMSO-d 6 , 400MHz) δ: 8.75(d, 1H), 8.65...

Embodiment 3

[0044] Preparation of polyimide:

[0045] Add 1.5mmol asymmetric diamine and 1.5mmol pyromellitic dianhydride monomer containing xinhone-binaphthyl structure respectively in the 50ml three-necked round-bottomed flask that is dried and ventilated with nitrogen, then add 15ml m-cresol solvent (system solid The content is 5-20%), then add about 0.3ml of isoquinoline as a catalyst, raise the temperature of the reaction system to 100-120°C for 2-3 hours, then raise the temperature to 190-200°C for about 15 hours, cool to 120°C Pour the polymer solution into methanol, collect the precipitate by filtration, wash it twice with boiling water, and dry it in vacuum at 150°C to obtain polyimide.

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Abstract

The invention relates to asymmetric aromatic diamine containing the structure of phenodiazine ketone binaphthyl and a preparation method and application thereof. The general structure is as the right formula and the preparation is as follows: 1) 4-(4-hydroxy naphthyl)-2, 3-naphthyridine-1-ketone and parachloronitrobenzene or 2-chlorine-5-nitro benzotrifluoride with molar ratio of 1:2 react under alkaline condition to obtain a binitro compound; 2) the binitro compound is reduced by palladium-charcoal and hydrazine hydrate with the existence of an organic solvent and the diamine is obtained. The application is to prepare polyimide. The asymmetric aromatic diamine containing the structure of phenodiazine ketone binaphthyl prepared by the invention has high purity and is stable under room temperature; polyimide prepared hereby has excellent solubility, high temperature resistance, mechanical property, film forming ability, optical property and other excellent comprehensive performances.

Description

technical field [0001] The invention belongs to the field of aromatic diamine compounds and their preparation and application, and in particular relates to an asymmetric aromatic diamine containing a xinhone-binaphthyl structure and a preparation method and application thereof. Background technique [0002] Polyimide is a kind of heat-resistant polymer material with excellent comprehensive performance. Since the development and industrialization of DuPont in the United States in the 1960s, it has been applied in various fields. Especially as a heat-resistant material and electronic packaging material, it is widely used in aerospace and microelectronics industries. Although polyimides have excellent comprehensive properties, due to their rigid benzene rings and imide rings, as well as the strong interaction between molecules and the close packing of molecular chains, most polyimides have High melting temperature, generally insoluble in organic solvents, which limits their f...

Claims

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Application Information

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IPC IPC(8): C07D237/32C08G73/10
Inventor 汪称意李光谭甲辉杨胜林金俊弘江建明
Owner DONGHUA UNIV
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