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Method for preparing 2-furancarboxylic acid ester-terminated polybutadiene

A technology of ester-based polybutadiene and hydroxyl-terminated polybutadiene, which is applied in the field of preparing terminal 2-furanoate-based polybutadiene, can solve problems such as contact toxicity and skin rashes, and achieve low cost and avoid Easy and safe use, reaction operation and post-processing

Active Publication Date: 2021-04-09
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, dicyclohexylcarbodiimide has significant contact toxicity and can cause allergic reactions such as skin rashes

Method used

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  • Method for preparing 2-furancarboxylic acid ester-terminated polybutadiene
  • Method for preparing 2-furancarboxylic acid ester-terminated polybutadiene
  • Method for preparing 2-furancarboxylic acid ester-terminated polybutadiene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Take 10 g of hydroxyl-terminated polybutadiene, and dissolve 1.19 g (1.3 equivalents) of 4-dimethylaminopyridine in 40 mL of dry dichloromethane. Stir at room temperature for 10 minutes to completely dissolve 4-dimethylaminopyridine and hydroxyl-terminated polybutadiene, slowly add 0.88 mL (1.2 equivalents) of 2-furoyl chloride in an ice bath, remove the ice bath, and stir at room temperature for 5 hours. The reaction system was washed 2 to 3 times with saturated ammonium chloride solution, most of the solvent in the organic phase was removed under reduced pressure, the sample was applied by dry method, and the column chromatography separated to obtain a light yellow transparent viscous liquid terminal 2-furanoate-based polybutylene Alkene 4.2g, yield 39%.

[0027] figure 1 Among them, 1.9-2.2ppm corresponds to the hydrogen atom on the methylene group connected to the olefin in the polybutadiene chain; 4.9-5.0ppm and 5.3-5.5ppm respectively correspond to the two types ...

Embodiment 2

[0032] Take 10 g of hydroxyl-terminated polybutadiene, and dissolve 1.37 g (1.5 equivalents) of 4-dimethylaminopyridine in 40 mL of dry dichloromethane. Stir at room temperature for 10 minutes to completely dissolve 4-dimethylaminopyridine and hydroxyl-terminated polybutadiene, slowly add 0.89ml (1.2 equivalents) of 2-furoyl chloride in an ice bath, remove the ice bath, and stir for 5 hours at room temperature. The reaction system was washed 2 to 3 times with saturated ammonium chloride solution, most of the solvent in the organic phase was removed under reduced pressure, the sample was applied by dry method, and the column chromatography separated to obtain a light yellow transparent viscous liquid terminal 2-furanoate-based polybutylene Alkene 7.6g, yield 71%.

Embodiment 3

[0034] Take 10 g of hydroxyl-terminated polybutadiene, and dissolve 1.83 g (2.0 equivalents) of 4-dimethylaminopyridine in 40 mL of dry dichloromethane. Stir at room temperature for 10 minutes to completely dissolve 4-dimethylaminopyridine and hydroxyl-terminated polybutadiene, slowly add 1.11 mL (1.5 equivalents) of 2-furoyl chloride in an ice bath, remove the ice bath, and stir at room temperature for 5 hours. The reaction system was washed 2 to 3 times with saturated ammonium chloride solution, most of the solvent in the organic phase was removed under reduced pressure, the sample was applied by dry method, and the column chromatography separated to obtain a light yellow transparent viscous liquid terminal 2-furanoate-based polybutylene Alkene 6.2g, yield 58%.

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Abstract

The invention provides a method for preparing 2-furancarboxylic acid ester-terminated polybutadiene. The method comprises the following steps: adding hydroxyl-terminated polybutadiene, 4-dimethylaminopyridine and an organic solvent into a reactor, and conducting sufficient stirring at room temperature to realize uniform mixing; cooling a mixture to 0 DEG C, slowly adding 2-furoyl chloride, and then conducting stirring for a reaction at a reaction temperature of 0 to room temperature for 1-48 hours; and washing the mixture, conducting drying, concentrating an organic phase, and carrying out column chromatography separation and purification to obtain the product, namely 2-furancarboxylic acid ester-terminated polybutadiene. According to the invention, while 4-dimethylaminopyridine is used as an acid-binding agent, esterification reaction efficiency can be effectively improved; the reaction activity of 2-furoyl chloride is high, the cost of 2-furoyl chloride is low, and the use of dicyclohexylcarbodiimide is avoided; and reaction operation and post-treatment are simple, convenient and safe, yield is stable in an amplified preparation process, and the method has great industrial application potential.

Description

technical field [0001] The invention relates to a method for preparing terminal 2-furanoate group polybutadiene, which belongs to the technical field of new materials. Background technique [0002] Hydroxyl-terminated polybutadiene (HTPB) is butyl hydroxy, with its low viscosity, good process performance, high solid addition, relatively complete curing reaction and good storage performance, and its cost-reduced advantages, It is widely used in adhesives, coatings, rubber materials, insulating materials, sealing materials, national defense technology and other fields. With the continuous improvement of material stability requirements, the development of new self-healing material systems based on hydroxyl-terminated polybutadiene framework structures is a feasible solution. [0003] The research on intrinsic self-healing materials based on covalent reversible reactions has attracted extensive attention in recent years, and the Diels-Alder reversible cycloaddition reaction is ...

Claims

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Application Information

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IPC IPC(8): C08F8/14C08F136/06
CPCC08F8/14C08F136/06
Inventor 杨帆致刘宁宁夏敏罗运军
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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