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

Side-chain-type difluoro monomer and synthesis method thereof

A synthesis method and technology of fluorine monomers, applied in the field of materials, can solve the problems of difficult synthesis, few types of side chain monomers, and high solubility

Active Publication Date: 2015-02-04
SHAANXI NORMAL UNIV
View PDF4 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with the main chain functional polymer, the side chain functional polymer has the advantages of low melting point and high solubility, and the functional group is far away from the main chain structure, which helps to form a phase separation structure, but there are relatively few types of side chain monomers. more difficult to synthesize

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
  • Side-chain-type difluoro monomer and synthesis method thereof
  • Side-chain-type difluoro monomer and synthesis method thereof
  • Side-chain-type difluoro monomer and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Taking the side chain difluoromonomer with the following structural formula as an example, the specific preparation method is as follows:

[0032]

[0033] 1. Preparation of compound a

[0034] Under the protection of nitrogen, add 0.79g (32.42mmol) of magnesium powder and 5mL of dry tetrahydrofuran to a 100mL three-necked flask, turn on magnetic stirring, increase the temperature to 65℃, and slowly add 5.00g (27.02mmol) of 3,5-dimethyl A mixed solution of bromobenzene and 40mL dry tetrahydrofuran was stirred at 65°C for 3 hours to prepare a Grignard reagent, and then slowly dropwise added 3.76g (27.02mmol) 2,6-difluorobenzonitrile and 40mL dry tetrahydrofuran mixed solution, Continue to stir at 65°C for 6 hours. After the reaction is complete, add 80 mL of 0.1mol / L hydrochloric acid aqueous solution, stir and reflux for 12 hours at 80°C, wash the reaction solution to neutrality, concentrate the organic phase to prepare compound a, The yield is 65.2%, and the structural cha...

Embodiment 2

[0042] Taking the side chain difluoromonomer with the following structural formula as an example, the specific preparation method is as follows:

[0043]

[0044] In step 3 of Example 1, the 3,5-dimethylphenylboronic acid used was replaced with equimolar 2,4-dimethylphenylboronic acid, and the other steps were the same as in Example 1, to prepare side chain difluoro The yield of the monomer is 66.1%, and the structure characterization data are as follows:

[0045] 1 H-NMR(DMSO-d 6 Is the solvent, TMS is the internal standard, 300MHz, ppm): 7.66 (m, 1H), 7.49 (s, 1H), 7.40 (d, 2H), 7.26 (t, 2H), 6.99 (s, 1H), 6.98 ( s, 1H), 6.92 (s, 1H), 3.87 (s, 2H), 2.29 (s, 3H), 2.19 (s, 6H).

Embodiment 3

[0047] Taking the side chain difluoromonomer with the following structural formula as an example, the specific preparation method is as follows:

[0048]

[0049] In step 3 of Example 1, the 3,5-dimethylphenylboronic acid used was replaced with equimolar 4-methylphenylboronic acid, and the other steps were the same as in Example 1, to prepare a side chain difluoromonomer, The yield is 67.2%, and the structural characterization data are as follows:

[0050] 1 H-NMR (DMSO-d6 is solvent, TMS is internal standard, 300MHz, ppm): 7.67 (m, 1H), 7.46 (s, 1H), 7.30 (d, 2H), 7.22 (t, 2H), 6.98 ( s, 4H), 3.88 (s, 2H), 2.29 (s, 3H), 2.19 (s, 3H).

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

No PUM Login to View More

Abstract

The invention discloses a side-chain-type difluoro monomer and a synthesis method thereof. A structure formula of the monomer is described as follows, wherein X is represented as CH3 or OCH3 and n is an integer between 1 and 3. The monomer is prepared with 3,5-dimethylbromobenzene as a raw material and through a Grignard reaction, a nucleophilic addition addition, a bromination reaction and a coupled reaction. The side-chain-type difluoro monomer contains a polymerizable difluoro group and functionalizable methyl or methoxy. Through a polycondensation reaction and functional group transition, a quaternized or sulfonated polymer can be prepared from the side-chain-type difluoro monomer. A functional polymer can be employed as a polymer electrolyte membrane material of a fuel cell.

Description

Technical field [0001] The invention belongs to the technical field of materials, and specifically relates to a side chain type difluoromonomer and a preparation method thereof. Background technique [0002] With the continuous development of science and technology, ordinary polymer materials can no longer meet the needs of specific functions, and functional polymer materials have emerged at the historic moment. At present, the functionalized polymer materials can be used in many fields, such as fuel cells, photovoltaic cells, separation membranes and other fields. For polymers containing specific functional groups, for example, polymers containing methyl functional groups are brominated and ammoniumized to form quaternized polymer materials, which can be used in anion exchange membranes for fuel cells. The methoxy functional group-containing polymer reacts with the sulfonated lactone after demethylation to obtain a sulfonated polymer, and this sulfonated polymer material can be...

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): C07C49/813C07C49/84C07C45/68
Inventor 陈新兵石倩陈沛安忠维
Owner SHAANXI NORMAL UNIV