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1,4-bis(4-amino-benzene oxymethylene) cyclohexyl and preparation and application thereof

A technology of aminophenoxymethylene and nitrophenoxymethylene, applied in 1 field, can solve problems such as unfavorable polymerization reactions

Inactive Publication Date: 2007-12-05
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the amino group of this diamine monomer is directly connected to the alicyclic ring. During the polymerization process, the amino group is easy to form a salt due to its high alkalinity, which is not conducive to the polymerization reaction under normal conditions. Only by improving the reaction conditions can the polymerization proceed smoothly.

Method used

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  • 1,4-bis(4-amino-benzene oxymethylene) cyclohexyl and preparation and application thereof
  • 1,4-bis(4-amino-benzene oxymethylene) cyclohexyl and preparation and application thereof
  • 1,4-bis(4-amino-benzene oxymethylene) cyclohexyl and preparation and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0022] (a) In a 150mL three-neck flask equipped with a stirrer, a reflux condenser, a thermometer, and a nitrogen conduit, add 1.5 grams (60%) of sodium hydride, and add 1,4-cyclohexane dropwise under ice-water bath cooling and nitrogen protection. Alkanedimethanol solution (2.0 g of 1,4-cyclohexanedimethanol dissolved in 20 mL of N,N-dimethylformamide), kept slightly boiling. Stir for 2 hours after dropping, then slowly add p-chloronitrobenzene solution (4.8 grams of p-chloronitrobenzene is dissolved in 30mL N, N-dimethylformamide), then rise to room temperature and continue to stir for 20 hours. The reaction solution was poured into 400 mL of water, filtered, and dried to obtain 4.5 g of yellow solid powder: 1,4-bis(4-nitrophenoxymethylene)cyclohexane, with a yield of 84%. The product was heated to 100°C in N,N-dimethylformamide to dissolve, filtered while hot, and the filtrate was cooled to precipitate light yellow crystals, dried under vacuum at 80°C for 12 hours to obtain...

Embodiment 2

[0025] (a) In a 150mL three-neck flask equipped with a stirrer, a reflux condenser, a thermometer, and a nitrogen conduit, add 1.5 grams (60%) of sodium hydride, and add 1,4-cyclohexane dropwise under ice-water bath cooling and nitrogen protection. Alkanedimethanol solution (2.0 g of 1,4-cyclohexanedimethanol dissolved in 20 mL of N,N-dimethylformamide), kept slightly boiling. Stir for 2 hours after dropping, then slowly add p-fluoronitrobenzene solution (4.3 grams of p-fluoronitrobenzene is dissolved in 30mL N, N-dimethylformamide) dropwise, then rise to room temperature and continue stirring for 15 hours. The reaction solution was poured into 400 mL of water, filtered, and dried to obtain 4.0 g of yellow solid powder: 1,4-bis(4-nitrophenoxymethylene)cyclohexane, with a yield of 75%. After the product was heated to 100°C in N,N-dimethylformamide to dissolve, it was filtered while it was hot, and the filtrate was cooled to precipitate light yellow crystals, which were dried un...

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Abstract

The present invention relates to 1, 4-bis(4-aminophenoxylmethylene)cyclohexane, which is white or light red crystal and has smelting point of 150-152 deg.c and chemical structure as shown. Its preparation process includes the reaction of 1, 4-cyclohexane dimethanol and p-halo nitrobenzene to obtain 1, 4-bis(4-nitrophenoxylmethylene)cyclohexane, and the further reaction with active carbon, ferric trichloride hexahydrate, anhydrous alcohol and hydrazine hydrate to obtain 1, 4-bis(4-aminophenoxylmethylene)cyclohexane. The compound 1, 4-bis(4-aminophenoxylmethylene)cyclohexane may be polymerized to form polyimide material with alicyclic ring structure, and the polyimide material may find its wide application in liquid crystal display, optical fiber communication and other hi-tech fields.

Description

technical field [0001] The invention relates to an organic compound and its preparation and application, in particular to 1,4-bis(4-aminophenoxymethylene)cyclohexane, its preparation method and application. Background technique [0002] As a modified polyimide, alicyclic polyimide has high thermal stability, low dielectric constant, corrosion resistance and other properties, and can improve the insoluble / melting and opaque properties of traditional aromatic polyimides. However, it has a wide range of application values ​​in many fields. Polyimide is mainly prepared by polycondensation reaction of diamine monomer and dianhydride monomer. To obtain alicyclic polyimide, the first task is to prepare diamine monomer or dianhydride monomer containing alicyclic structure. , and then undergo polycondensation. Compared with dianhydride monomers, diamine monomers have the advantage of being easier to prepare. Therefore, diamine monomers containing alicyclic structures play an extre...

Claims

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Application Information

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IPC IPC(8): C07C217/86C07C213/06C08G69/36
Inventor 陈超峰黄象安钦维民
Owner DONGHUA UNIV
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