Unlock instant, AI-driven research and patent intelligence for your innovation.

Sulfonated aromatic diamine monomer containing tetramethyl fluorene structure and preparation method thereof

A technology for sulfonating aromatic diamine and tetramethylfluorene, which is applied in the field of sulfonated aromatic diamine monomers, can solve the problems of low yield of fluorene-containing monomers, achieve improved hydrolysis stability, simple synthesis route, and high yield high effect

Active Publication Date: 2014-04-16
大连新阳光材料科技有限公司
View PDF2 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, there are few studies on fluorene-containing sulfonated aromatic diamine monomers, because the yield of fluorene-containing monomers is low

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
  • Sulfonated aromatic diamine monomer containing tetramethyl fluorene structure and preparation method thereof
  • Sulfonated aromatic diamine monomer containing tetramethyl fluorene structure and preparation method thereof
  • Sulfonated aromatic diamine monomer containing tetramethyl fluorene structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of 9,9-bis(3,5-dimethyl-4-aminophenyl)fluorene (BAFL)

[0025] Add 9.01g (0.05mol) of 9-fluorenone and 12.12g (0.10mol) of 2,6-dimethylaniline to a 100ml three-necked flask equipped with nitrogen conduit, thermometer, condenser and mechanical stirring, and stir at room temperature After 10 minutes, 2ml of trifluoromethanesulfonic acid was slowly added dropwise, and after 0.5 hours of reaction, the temperature was raised to 160°C, and the reaction was refluxed for 8 hours to end the reaction. After the reaction system dropped to room temperature, the product was transferred to an appropriate amount of ethanol and neutralized with 10% sodium hydroxide solution. After standing for several hours, filter with suction, wash and dry the product with ethanol, and further recrystallize with toluene to obtain a yellow powdery diamine monomer, and obtain an intermediate product after vacuum drying: 9,9-bis(3,5-di Methyl-4-aminophenyl) fluorene (BAFL), the yield can re...

Embodiment 2

[0032] Preparation of 9,9-bis(3,5-dimethyl-4-aminophenyl)fluorene (BAFL)

[0033] Add 9.01g (0.05mol) of 9-fluorenone and 18.17g (0.15mol) of 2,6-dimethylaniline to a 100ml three-necked flask equipped with nitrogen conduit, thermometer, condenser and mechanical stirring, and stir at room temperature After 10 minutes, 5ml of trifluoromethanesulfonic acid was slowly added dropwise, and after 0.5 hours of reaction, the temperature was raised to 160°C, and the reaction was refluxed for 12 hours to end the reaction. After the reaction system dropped to room temperature, the product was transferred to an appropriate amount of ethanol and neutralized with 10% sodium hydroxide solution. After standing for several hours, filter with suction, wash and dry the product with ethanol, and further recrystallize with toluene to obtain a white powdery diamine monomer, and obtain an intermediate product after vacuum drying: 9,9-bis(3,5-di Methyl-4-aminophenyl)fluorene (BAFL), the yield is abou...

Embodiment 3

[0037] Preparation of 9,9-bis(3,5-dimethyl-4-aminophenyl)fluorene (BAFL)

[0038] Add 9.01g (0.05mol) of 9-fluorenone and 15.13g (0.125mol) of 2,6-dimethylaniline to a 100ml three-necked flask equipped with nitrogen conduit, thermometer, condenser and mechanical stirring, and stir at room temperature After 10 min, 3.5 ml of trifluoromethanesulfonic acid was slowly added dropwise, and after 0.5 h of reaction, the temperature was raised to 160° C., and the reaction was refluxed for 10 h to end the reaction. After the reaction system dropped to room temperature, the product was transferred to an appropriate amount of ethanol and neutralized with 10% sodium hydroxide solution. After standing for several hours, filter with suction, wash and dry the product with ethanol, and further recrystallize with toluene to obtain a white powdery diamine monomer, and obtain an intermediate product after vacuum drying: 9,9-bis(3,5-di Methyl-4-aminophenyl)fluorene (BAFL), the yield is about 86%;...

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
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a sulfonated aromatic diamine monomer containing a tetramethyl fluorene structure (img file='DDA0000455994210000011. TIF' wi='624' he='408' / ). A preparation method of the sulfonated aromatic diamine monomer comprises the following steps: mixing 9-fluorenone and 2,6-dimethylaniline; dropwise adding a catalyst under stirring; reacting and then heating for refluxing reaction; after the reaction is completed, cooling a reaction system to room temperature; then moving a product to a proper amount of ethanol; neutralizing; after suction filtration and drying, recrystallizing a crude product with toluene to obtain an intermediate product; placing the intermediate product in an ice bath; then dropwise adding concentrated sulfuric acid; reacting and then heating slowly for reaction; after the reaction is completed, pouring mixed liquid into crushed ices for sedimentation to obtain a precipitate; adjusting pH to be about 4-5; filtering out the sedimentation; and drying in vacuum to obtain a reddish powder product. The sulfonated aromatic diamine monomer is simple in synthesis route and high in yield, and can be directly obtained through sulfonation of sulfuric acid under relatively mild reaction conditions without adding additional fuming sulphuric acid; and as a hydrophobic tetramethyl structure is introduced to a sulfonic acid lateral group, the hydrolytic stability of sulfonated polyimide can be further improved.

Description

technical field [0001] The invention relates to the field of sulfonated aromatic diamine monomers, in particular to a sulfonated aromatic diamine monomer containing a tetramethylfluorene structure and a preparation method thereof. Background technique [0002] The proton exchange membrane is one of the core components of the proton exchange membrane fuel cell (PEMFC). It plays the role of transferring protons and blocking fuel in the fuel cell. Its performance directly affects the performance of the cell. At present, the perfluorinated sulfonated polymers represented by DuPont's Nafion are in practical application. This kind of commercial Nafion proton exchange membrane has high proton conductivity, excellent mechanical properties and chemical stability. However, this kind of material also has disadvantages such as high price, low operating temperature, and strong methanol permeability. Therefore, the development of new proton exchange membrane materials with low price, hig...

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): C07C309/47C07C303/06
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