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Diamine monomer, synthetic method thereof, and polyimide prepared from diamine monomer

A diamine monomer and synthesis method technology, applied in the field of fluorine-containing polyimide, can solve the problems of limited application, high melting point or softening temperature, poor solubility, etc., and achieve reduced water absorption, good moisture-sensitive performance, and reduced crystallization The effect of strength and rigidity

Inactive Publication Date: 2012-06-13
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most aromatic polyimides have a rigid skeleton and strong interchain interactions, resulting in a high melting point or softening temperature and poor solubility in most organic solvents
These limit its application in many frontier fields

Method used

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  • Diamine monomer, synthetic method thereof, and polyimide prepared from diamine monomer
  • Diamine monomer, synthetic method thereof, and polyimide prepared from diamine monomer
  • Diamine monomer, synthetic method thereof, and polyimide prepared from diamine monomer

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specific Embodiment approach 1

[0026] Specific embodiment 1: This embodiment is a diamine monomer, the chemical name of the diamine monomer is 4-(4-aminophenoxy)-3-fluoroaniline, and the structural formula is as follows:

[0027]

[0028] The 4-(4-aminophenoxy)-3-fluoroaniline diamine monomer of this embodiment is a diamine monomer with a fluorine-containing asymmetric aromatic ether structure. It is a white to light yellow solid and is a good synthetic polyamide. The raw material of imine.

specific Embodiment approach 2

[0029] Embodiment 2: This embodiment is the method for synthesizing the diamine monomer described in Embodiment 1, which is obtained through the following steps: 1. Synthesis of 2-fluoro-4-nitro-1-(4-nitro (Phenoxy) benzene: Add 2-fluoro-4-nitrophenol, 4-nitrochlorobenzene, anhydrous potassium carbonate and N,N-dihydrogen to a reactor equipped with a magnet, a thermometer and a condenser. Methylformamide (DMF), then place the reactor in an oil bath at 120°C to 160°C, keep it warm and stir and reflux for 10 to 15 hours to obtain the reaction system, then filter the reaction system while it is hot, and then add the filtrate Add distilled water at 5℃~15℃ until no solid matter is precipitated, and then recrystallize with absolute ethanol to obtain 2-fluoro-4-nitro-1-(4-nitrophenoxy)benzene (light yellow needles) Crystal), wherein the molar ratio of 2-fluoro-4-nitrophenol and 4-nitrochlorobenzene is 1:1, and the molar ratio of anhydrous potassium carbonate and 4-nitrochlorobenzene i...

specific Embodiment approach 3

[0042] Specific embodiment three: This embodiment is different from the specific embodiment two in that the molar ratio of anhydrous potassium carbonate and 4-nitrochlorobenzene in step one is 1.1:1. Other steps and parameters are the same as in the second embodiment.

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Abstract

The invention relates to a fluorine-containing diamine monomer with an asymmetric aromatic ether structure, a synthetic method thereof and fluorine-containing polyimide prepared from the diamine monomer. The diamine monomer has a structural formula as described in the specification; polyimide has a structural formula as described in the specification, and n in the structural formula of polyimide is in a range of 100 to 500. The synthetic method is as follows: 2-fluoro-4-nitrophenol and 4-nitrochlorobenzene undergo nucleophilic substitution so as to prepare FNNB; the diamine monomer is prepared from FNNB with Pd / C as a catalyst and hydrazine hydrate as a reducing agent; and the diamine monomer and 6FDA undergo polycondensation so as to prepare polyimide. According to the invention, ether groups and fluorine-containing strong hydrophobic groups are introduced into the diamine monomer, so the diamine monomer has weak polarity, thereby enabling the polarity of polyimide prepared from the diamine monomer to be reduced; thus, crystallinity and rigidity of polyimide are reduced, and solubility and the water absorption rate of polyimide are improved. Since polyimide has an aromatic structure, good mechanical properties and thermal stability are provided, which is favorable for development of a humidity sensing device.

Description

Technical field [0001] The invention relates to a diamine monomer with a fluorine-containing asymmetric aromatic ether structure, its synthesis method and a fluorine-containing polyimide prepared therefrom. Background technique [0002] Polyimide (English name Polyimide, PI for short) is a new type of polymer moisture-sensitive material. Among them, aromatic polyimide (English name Aromatic heterocyclic polyimide), with its superior thermal stability, good chemical stability, mechanical strength, and lower dielectric constant, has been widely used in many fields. However, most aromatic polyimides have a rigid framework and strong interactions between molecular chains, which makes them have a high melting point or softening temperature, and have poor solubility in most organic solvents. These have restricted its application in many frontier fields. [0003] At present, in order to make up for these shortcomings, when designing and synthesizing new monomers for polymerization react...

Claims

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Application Information

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IPC IPC(8): C07C217/90C07C213/02C08G73/10
Inventor 唐冬雁梁桃魏菁娴毛义武
Owner HARBIN INST OF TECH
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