Aromatic diamines monomer with double miscellaneous naphthalenone structures and trifluoromethyl substituted and preparation thereof

A technology of trifluoromethyl and aromatic diamines, which is applied in the field of aromatic diamines and its preparation, can solve the problems of polyimide insolubility, loss, and reduction of high temperature resistance of polyimide, and achieve good film formation properties, excellent mechanical properties, and excellent heat resistance

Inactive Publication Date: 2009-06-03
DONGHUA UNIV
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  • 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

Method used

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  • Aromatic diamines monomer with double miscellaneous naphthalenone structures and trifluoromethyl substituted and preparation thereof
  • Aromatic diamines monomer with double miscellaneous naphthalenone structures and trifluoromethyl substituted and preparation thereof
  • Aromatic diamines monomer with double miscellaneous naphthalenone structures and trifluoromethyl substituted and preparation thereof

Examples

Experimental program
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Embodiment 1

[0023] 2-(4-amino-2-trifluoromethylphenyl)-4-[4-(4-amino-2-trifluoromethylphenoxy)-naphthyl]-naphthyridine-1 - Preparation of ketones:

[0024] ①Under nitrogen protection, mix 22.9g (0.05mol) 4,4'-oxo-bis[(4-(1,4-phenyl)-phthalazin-1-one] and 22.6g (0.1mol) 2-Chloro-5-nitrobenzotrifluoride was added to a 500ml three-necked flask, and then 14.5g (0.105mol) of potassium carbonate and 150ml of N,N-dimethylformamide were added respectively, and the reaction was carried out at 100-150°C for 10- After 20 hours, the product was poured into 1000ml of methanol / water (1:1), fully stirred, precipitated and filtered, and the product was repeatedly washed with hot water, and further separated and purified by column chromatography to obtain a white fluorine-containing dinitro compound: 4,4'- Bis[2-(4-nitro-2-trifluoromethylphenyl)-phthalazin-1-one-yl]-diphenyl ether, the yield is about 70-80%, and the melting point is 159-161 ° C. FT -IR(KBr)v / cm -1 : 1677 (C=O), 1537, 1355 (-NO 2 ), 12...

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Abstract

The invention relates to an aromatic diamines monomer with double miscellaneous naphthalenone structures and trifluoromethyl substituted and a preparation method thereof. A diamine structure is prepared according to the following steps: (1), 4,4'-oxygen-bis(4-(1,4-phenyl)-phthalazine-1-ketone) reacts with 2-chlorine-5-nitro benzotrifluoride under an alkaline condition according to a molar ratio of 1 to 2, and then a dinitro compound is acquired; and (2), the dinitro compound is reduced in organic solvent by palladium-charcoal and hydrazine hydrate, and then the monomer is acquired; and the monomer can be used to prepare polyimide and aromatic polyamides. The prepared aromatic diamines with double miscellaneous naphthalenone structures and trifluoromethyl substituted has high purity, and is steady at normal temperature; and the polyimide and the aromatic polyamides prepared by the aromatic diamines monomer have excellent comprehensive properties such as good solubility and film forming capability, strong high temperature resistance and excellent mechanical properties, high optical transparency, low dielectric constant and the like.

Description

technical field [0001] The invention belongs to the field of aromatic diamine monomers and their preparation, and in particular relates to aromatic diamine monomers containing bis-naphthalene structures and trifluoromethyl-substituted aromatic diamines and their preparation. Background technique [0002] Both polyimide and polyaramid are heat-resistant polymer materials with excellent comprehensive properties. Since the industrialization began in the 1960s and 1970s, they have been applied in various fields. Especially as a high-performance fiber, a high heat-resistant composite material matrix and an electronic packaging material, it has been widely used in aerospace, machinery, microelectronics, petrochemical and other industries. Although such high-temperature resistant materials have excellent comprehensive properties, due to their rigid main chain structure, strong interaction between molecules and close packing of molecular chains, most polyimides and polyarylamides ...

Claims

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Application Information

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IPC IPC(8): C07D237/30C08G73/10C08G69/32
Inventor 汪称意李光李鹏辉杨胜林金俊弘江建明
Owner DONGHUA UNIV
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