Aryl bridged silsesquioxane monomer and preparation method thereof

A technology of sesquisiloxane and triethoxychlorosilane is applied in the field of aryl bridged silsesquioxane monomer and its preparation, which can solve the problems of high cost, difficulty in mass production, and reduced rigidity of bridge chain.

Inactive Publication Date: 2013-12-18
HEFEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] One: it is realized by the hydrosilylation reaction between divinylarene and trialkoxysilane. Although this method has strong specificity, it needs expensive platinum catalyst in the production process, and The bridging group contains two ethyl groups in addition to the aryl group, which reduces the rigidity of the bridge chain
[0007] The second: it is realized by using an affinity substitution reaction between a trialkoxychlorosilane with an electrophilic group and an aromatic hydrocarbon with a double nucleophilic end group. Although the method is simple and the yield is relatively high, but Raw materials are not easy to obtain, and the synthesis of precursors is difficult, so it is difficult to realize industrial mass production
[0008] The third is to use the metallation of dihaloarenes (using Grignard reagent or organolithium), and then nucleophilic substitution reaction with silane reagents. Preparation, but the currently used silane reagent is tetraalkoxysilane, it is not easy to achieve monosubstitution of alkoxy group, the product is often a mixture of monosubstitution and double substitution, it is not easy to separate the target product, and the yield is low

Method used

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  • Aryl bridged silsesquioxane monomer and preparation method thereof
  • Aryl bridged silsesquioxane monomer and preparation method thereof
  • Aryl bridged silsesquioxane monomer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1: the preparation of 1,4-two (triethoxysilyl) benzene

[0035] Add 5g magnesium powder, 100mL TECS and two grains of iodine into the three-neck flask, vacuumize for 10min with double-pipe system, fill with nitrogen for 3min, and repeat this three times. Dissolve 16g of 1,4-dibromobenzene in 200mL of tetrahydrofuran, suck it up with a syringe, inject it dropwise into a sealed three-necked flask, protect it with nitrogen, stir it magnetically, heat it in an oil bath at 65°C, and reflux for 3 hours. When a gray-green suspension appeared, the reaction was stopped, cooled to room temperature, and tetrahydrofuran was distilled off under reduced pressure. Add anhydrous n-hexane under continuous stirring to precipitate magnesium and magnesium salts, and filter quickly to obtain a clear filtrate. Distill under reduced pressure to remove n-hexane and excess TECS in turn to obtain a brown oil. Raise the temperature and distill under reduced pressure to obtain a color...

Embodiment 2

[0038] Embodiment 2: the preparation of 1,4-two (triethoxysilyl) benzene

[0039] Add 8g of magnesium powder, 180mL of TECS and two grains of iodine into the three-neck flask, vacuumize for 15min with double-pipe system, and fill with nitrogen for 3min, and repeat this three times. Dissolve 22g of 1,4-dichlorobenzene in 400mL of dioxane, suck it up with a syringe, pour it dropwise into a sealed three-necked flask, protect it with nitrogen, stir it with a magnetic force, heat it in an oil bath at 100°C, and reflux it for 5 hours. When a gray-green suspension appeared, the reaction was stopped, cooled to room temperature, and tetrahydrofuran was distilled off under reduced pressure. Add anhydrous n-hexane under continuous stirring to precipitate magnesium and magnesium salts, and filter quickly to obtain a clear filtrate. Distill under reduced pressure to remove n-hexane and excess TECS in turn to obtain a brown oil. Raise the temperature and distill under reduced pressure to ...

Embodiment 3

[0042] Example 3: Preparation of 4,4'-bis(triethoxysilyl)biphenyl

[0043]Add 6g of magnesium powder, 100mL of TECS and two grains of iodine into the three-neck flask, vacuumize for 15min with double-pipe system, and fill with nitrogen for 5min, and repeat this three times. Dissolve 20g of 4,4′-dibromobiphenyl in 300mL of tetrahydrofuran, absorb it with a syringe, and inject it dropwise into a sealed three-necked flask, under nitrogen protection, magnetic stirring, heating in an oil bath at 80°C, and reflux for 5 hours. When a gray-green suspension appeared, the reaction was stopped, cooled to room temperature, and tetrahydrofuran was distilled off under reduced pressure. Add anhydrous n-hexane under continuous stirring to precipitate magnesium and magnesium salts, and filter quickly to obtain a clear filtrate. Distill under reduced pressure to remove n-hexane and excess TECS in turn to obtain a brown oil. Raise the temperature and distill under reduced pressure to obtain a ...

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Abstract

The invention discloses a preparation method of an aryl bridged silsesquioxane monomer. The preparation method comprises the following steps: performing Grignard reaction on dihalogenated arene and metal magnesium to prepare a Grignard reagent; performing nucleophilic substitution reaction on the Grignard reagent and triethoxychlorosilane to produce the aryl bridged silsesquioxane monomer. In the reaction, triethoxychlorosilane serves as a reaction raw material, so the reaction has low activation energy and strong specificity, the yield of the aryl bridged silsesquioxane monomer is high, and aryl bridged polysilsesquioxanes prepared from the prepared aryl bridged silsesquioxane monomer through hydrolysis-polycondensation has excellent pore-forming property and high-temperature resistance.

Description

technical field [0001] The invention relates to the field of bridging silsesquioxane production, in particular to an aryl bridging silsesquioxane monomer and a preparation method thereof. Background technique [0002] Bridged silsesquioxanes are a class of Y 3 Si-X-SiY 3 Structure molecule, wherein Y is a reactive substituent, such as methoxy, ethoxy, etc., and X can be a chemically stable substituent, such as alkyl, aryl, or a reactive group, Such as amino, ester, carboxyl, hydroxyl, etc. Bridged polysilsesquioxane can be obtained by hydrolysis-polycondensation of bridged silsesquioxane monomers. It is an inorganic-organic hybrid material with excellent comprehensive performance. It not only has the advantages of both inorganic and organic substances, Moreover, due to the wide adjustability in material composition, it also has unique properties that cannot be compared with single inorganic and organic substances. Bridged polysilsesquioxane has heat resistance, oxidation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18
Inventor 杨本宏杨宪孙改行
Owner HEFEI UNIV
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