Rigid aromatic diamine monomer as well as preparation method and application thereof

A technology for aromatic diamines and monomers, which is applied in the field of rigid aromatic diamine monomers. It can solve the problems of being in the initial stage and few types of monomers, and achieve excellent film-forming properties, easy separation and purification, and simple synthesis routes.

Active Publication Date: 2014-01-08
大连新阳光材料科技有限公司
View PDF6 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Aromatic diamine monomers containing fluorene structures are important monomers for the preparation of polyarylamides. However, there are few such monomers that have been reported so far, and various technical researches are still in their infancy.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Rigid aromatic diamine monomer as well as preparation method and application thereof
  • Rigid aromatic diamine monomer as well as preparation method and application thereof
  • Rigid aromatic diamine monomer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A preparation method of rigid aromatic diamine monomer 9,9-bis(4-amino-3-isopropylphenyl) fluorene has the following preparation steps:

[0022] (1) Under the protection of nitrogen, add 18.02g (0.10mol) of 9-fluorenone and 40.56g (0.3mol) of 2-isopropylaniline into a 250ml three-necked flask, stir at room temperature until 9-fluorenone is dissolved , And then slowly add 4.5g (0.03mol) of trifluoromethanesulfonic acid, continue to stir and react for 5h under reflux state, and end the reaction;

[0023] (2) After the reaction product of step (1) is brought to room temperature, it is neutralized to neutrality with 10% sodium hydroxide solution, and the reaction product is transferred to a mixed solvent of ethanol and water (the volume ratio of ethanol and water is 5: 1) Fully agitate, precipitate, filter with suction, and further recrystallize with toluene to obtain a white powdery solid, which is a rigid aromatic diamine monomer containing a fluorenyl structure and a diisopro...

Embodiment 2

[0028] A preparation method of rigid aromatic diamine monomer 9,9-bis(4-amino-3-isopropylphenyl) fluorene has the following preparation steps:

[0029] (1) Under the protection of nitrogen, add 18.02g (0.10mol) of 9-fluorenone and 28.97g (0.214mol) of 2-isopropylaniline into a 250ml three-necked flask, stir at room temperature and wait until 9-fluorenone is dissolved , And then slowly add 3.0g (0.02mol) of trifluoromethanesulfonic acid, continue to stir and react under reflux for 10h, and end the reaction;

[0030] (2) After the reaction product of step (1) is brought to room temperature, it is neutralized with a 10% sodium carbonate solution, and the reaction product is transferred to a mixed solvent of ethanol and water (the volume ratio of ethanol and water is 3:1 ), fully agitate, precipitate, filter with suction, and further recrystallize with ethanol to obtain a white powdery solid, that is, a rigid aromatic diamine monomer containing a fluorenyl structure and a diisopropyl g...

Embodiment 3

[0033] A preparation method of 9,9-bis(4-amino-3-isopropylphenyl) fluorene-based polyaramid has the following steps:

[0034] Under the protection of nitrogen, 3mmol 9,9-bis(4-amino-3-isopropylphenyl) fluorene and 3mmol aromatic diacid (terephthalic acid, isophthalic acid, diphenyl ether acid or hexafluoroiso One of propyl diacid) was added to a 50ml three-necked flask, and then 6-9mmol triphenyl phosphite, 6-9mmol pyridine, 0.3-0.6g anhydrous calcium chloride and 12-16ml N- Methylpyrrolidone, stir at room temperature until the reactants are completely dissolved, then heat to 100~120℃, stir and react for 4~8h, when the system becomes viscous, stop the reaction, pour the reaction solution into ethanol, and obtain a white fibrous shape The polymer was further washed twice with hot water and dried under vacuum at 120°C to obtain polyaramid polymer.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to view more

Abstract

The invention relates to the field of technical research of rigid aromatic diamine monomers and in particular relates to a biisopropyl substituted rigid aromatic diamine 9,9-bis(4-amido-3-isopropyl phenyl)fluorene monomer containing a fluorenyl structure. The rigid aromatic diamine monomer is obtained by reacting reactants including 2-isopropylaniline and 9-fluorenone under the condition of an acid catalyst, neutralizing the product with defined amount of aqueous alkali and then transferring the product to a mixed solvent of ethanol and water and carrying out leaching, drying and further recrystallization. The monomer has a simpler synthetic method and high yield, is easy to purify and is stable under room temperature. The obtained biisopropyl substituted rigid aromatic diamine monomer containing the fluorenyl structure can be applied to preparation of soluble aromatic polyamides and the prepared aromatic polyamides have good solubility and excellent film-forming properties.

Description

Technical field [0001] The invention relates to the technical research field of rigid aromatic diamine monomers, in particular to a rigid aromatic diamine monomer containing a fluorenyl structure and a diisopropyl group substitution and its preparation and application. Background technique [0002] Aramids are an important class of high-performance polymers. Since their successful development in the 1960s and 1970s, they have played an important role in many fields. For example, polyaramid high-performance fiber used in body armor and composite material reinforcement, polyaramid insulation paper used as a high-temperature dielectric material in the electronic and electrical field, polyaramid separation membrane used in the field of seawater desalination, gas separation Aramid separation membrane that plays an important role in the field. Although polyaramid high-performance polymers have excellent comprehensive performance and high use value, due to their rigid backbone structur...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/50C07C209/78C08G69/32
Inventor 汪称意陈云云陈文涛赵晓燕李坚任强
Owner 大连新阳光材料科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap