A kind of method for preparing terminal 2-furanoate group polybutadiene

A technology for ester-based polybutadiene and hydroxyl-terminated polybutadiene is applied in the field of preparing 2-furocarboxylate-terminated polybutadiene, which can solve the problems of contact toxicity, rash and the like, and achieves low cost and high reaction efficiency. High activity and the effect of improving the efficiency of esterification reaction

Active Publication Date: 2022-03-25
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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  • A kind of method for preparing terminal 2-furanoate group polybutadiene
  • A kind of method for preparing terminal 2-furanoate group polybutadiene
  • A kind of method for preparing terminal 2-furanoate group 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 polybutadiene with 2-furanoic acid ester group, comprising the following steps: adding hydroxyl-terminated polybutadiene, 4-dimethylaminopyridine and an organic solvent into a reactor, stirring at room temperature fully Mix well; cool the mixture to 0°C, slowly add 2-furoyl chloride, then stir the reaction, the reaction temperature is 0°C~room temperature, and the reaction time is 1h~48h; the mixture is washed, dried, concentrated organic phase, and separated and purified by column chromatography Obtain product terminal 2-furanoate group polybutadiene. In the present invention, while using 4-dimethylaminopyridine as an acid-binding agent, the efficiency of the esterification reaction can be effectively improved, and the 2-furoyl chloride has high reactivity and low cost, and avoids the use of dicyclohexylcarbodiimide. The reaction operation and post-treatment in the invention are simple and safe, the yield is stable in the scale-up preparation process, and 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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Patent Type & Authority Patents(China)
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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