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Dianhydride monomer with side chains containing phenylacetylene and synthesis method and application of dianhydride monomer

A technology of acetylene dianhydride and ethynyl biphenyl dianhydride, which is applied in the field of polyimide synthesis and can solve the problems of low BET specific surface area, limited carbon dioxide adsorption performance, and further improvement of cross-linking degree

Active Publication Date: 2018-09-28
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Guan Shaowei, Yao Hongyan and others applied in 2014 for an invention patent (CN104478838A) titled a phenylethynyl-containing dianhydride monomer and its synthesis method and application, as well as the SCI article "Microporous polyimides networks constructed through a two -step polymerization approach, and their carbon dioxide adsorption performance” (Polym.Chem., 2017,8,1298-1305) and “From a flexible hyperbranched polyimide to a microporous polyimidenetwork: Microporous architecture and carbon dioxide adsorption, 2”( 115:176-183); show that the polyimide prepared after introducing the phenylethynyl group on the side chain of the dianhydride monomer can be used for the adsorption of carbon dioxide by cross-linking to form a network structure, but its BET ratio on the surface of the experimental data The surface is not high, which limits its carbon dioxide adsorption performance
The reason for this problem may be that there are fewer sites for cross-linking on its side chains, and the degree of cross-linking needs to be further improved.

Method used

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  • Dianhydride monomer with side chains containing phenylacetylene and synthesis method and application of dianhydride monomer
  • Dianhydride monomer with side chains containing phenylacetylene and synthesis method and application of dianhydride monomer
  • Dianhydride monomer with side chains containing phenylacetylene and synthesis method and application of dianhydride monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] This example illustrates the synthesis and preparation steps of 3,3'-bis(3,4-dicarboxyphenoxy)-4,4'-tolanyl biphenyl dianhydride, specifically as follows:

[0037] Step 1: Add 3,3'-dihydroxybenzidine (A) and hydrogen bromide solvent into a 500mL three-necked flask equipped with a nitrogen port and a constant pressure dropping funnel, and dissolve sodium nitrite in deionized water. Slowly add sodium nitrite solution dropwise into a three-necked flask at -5 ~ 0°C to prepare diazonium salt, and slowly add the obtained diazonium salt solution dropwise into a three-necked flask containing hydrogen bromide solution and cuprous bromide After that, the temperature was raised to 100°C to react for 10-12 hours, the material was discharged in deionized water, washed 3-4 times, and recrystallized with ethanol and water to obtain the product 4,4'-dibromo-3,3'-biphenol (Product B). In the reaction, the molar ratio of 3,3'-dihydroxybenzidine, sodium nitrite, and cuprous bromide is 1:...

Embodiment 2

[0046] This example takes the synthesis process of 3,3'-bis(3,4-dicarboxyphenoxy)-4,4'-diphenylethynyl biphenyl dianhydride and diamine to synthesize linear polyimide as an example Be explained.

[0047] Its synthetic route is as follows:

[0048]

[0049]

[0050] Taking 3,3'-bis(3,4-dicarboxyphenoxy)-4,4'-diphenylethynyl biphenyl dianhydride and biphenyldiamine copolymerization as an example, 3,3'-bis(3 ,4-dicarboxyphenoxy)-4,4'-diphenylethynyl biphenyl dianhydride, biphenyl diamine and m-cresol were added to the three-necked flask, reacted at 70-80°C for 10-12 hours, and heated to 170 React at ~180 ° C for 20 ~ 24 hours, discharge in absolute ethanol, wash with ethanol 4 to 5 times, and vacuum dry in a vacuum oven at 100 ° C.

[0051] The above-mentioned diamines include the following: biphenylenediamine, p-phenylenediamine, 3,3'-dihydroxybenzidine, 2,2'-bis(3-amino-4hydroxyphenyl)hexafluoropropane, 2,2 '-bis(3-amino-4-hydroxyphenyl)propane, 2,2'-bis(3-amino-4-hydr...

Embodiment 3

[0053] In the present invention, 3,3'-bis(3,4-dicarboxyphenoxy)-4,4'-diphenylethynyl biphenyl dianhydride and polyamines are prepared by adjusting the feeding ratio to obtain anhydride-blocked or amino-blocked terminal hyperbranched polyimide.

[0054] Its chemical reaction formula is as follows:

[0055]

[0056]In this example, 3,3'-bis(3,4-dicarboxyphenoxy)-4,4'-diphenylethynyl biphenyl dianhydride, 5,10,15,20-tetrakis(4-aminobenzene Base) porphyrin is an example for the synthesis of amino-terminated hyperbranched polyimide materials from raw materials, and its specific experimental steps are as follows:

[0057] (1) Add 5,10,15,20-tetrakis(4-aminophenyl)porphyrin dissolved in N-methylpyrrolidone (NMP) , slowly drop the solution of 3,3'-bis(3,4-dicarboxyphenoxy)-4,4'-diphenylethynyl biphenyl dianhydride dissolved in N-methylpyrrolidone (NMP) into the three-necked flask , react at room temperature for 10-12 hours, add 2-2.5mL isoquinoline into the there-necked flask, h...

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Abstract

The invention discloses a dianhydride monomer with side chains containing phenylacetylene and a synthesis method and application of the dianhydride monomer, and belongs to the technical field of synthesis and preparation of polyimide. The dianhydride monomer is called 3,3'-bi(3,4-dicarboxyphenoxy)-4,4'-diphenylethynylbiphenyl dianhydride, and the dianhydride monomer with the side chains containingphenylacetylene is based on a biphenyl structure, contains cross-linkable groups containing phenylacetylene, and can be applied to synthesis of linear and hyperbranched polyimide; and a polyimide material with better properties is prepared through post-crosslinking treatment, the structure of the material is regulated by controlling the content of cross-linking groups, so that the performance ofthe polyimide material is improved; the material has potential application in gas adsorbing materials.

Description

technical field [0001] The invention belongs to the field of polyimide synthesis. Background technique [0002] As a special engineering plastic, polyimide is widely used in aerospace, separation membrane, optoelectronic information and coatings and other fields. Hyperbranched polyimide has a three-dimensional network structure due to its high degree of branching, and has good solubility, mechanical properties, thermochemical stability and other properties. The present invention designs and synthesizes an acid anhydride, introduces a phenylacetylene group into the side chain, explores the synthesis of a polyimide material from a dianhydride monomer containing a phenylacetylene group in the side chain, and performs post-crosslinking treatment on the polymer precursor. It can significantly improve its performance, and at the same time broaden the processing temperature of polyimide polymer, making it more widely applicable. [0003] Guan Shaowei, Yao Hongyan and others appli...

Claims

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Application Information

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IPC IPC(8): C07D307/89C08G73/10B01J20/26B01J20/28B01J20/30B01D53/02
CPCB01D53/02B01J20/265B01J20/267B01J20/28014C07D307/89C08G73/1057C08G73/1064C08G73/1071Y02P20/50
Inventor 关绍巍石凯祥宋宁宁关尔佳祝世洋张博田野王天娇
Owner JILIN UNIV
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