Application of a condensation product of a pillar aromatic hydrocarbon and a crown ether hybrid macrocycle as an adhesive

A technology of pillar aromatic hydrocarbons and condensates, which is applied in the application field of condensates as adhesives, which can solve problems such as failure and viscosity reduction, and achieve the effects of fast hardening speed, no change in adhesion ability, and simple adhesion process

Active Publication Date: 2021-08-17
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is because most supramolecular adhesives are temperature-sensitive materials, and their viscosity will be greatly reduced or even invalidated as the temperature increases or decreases.
Especially at extremely low temperatures, no successful adhesion has been reported

Method used

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  • Application of a condensation product of a pillar aromatic hydrocarbon and a crown ether hybrid macrocycle as an adhesive
  • Application of a condensation product of a pillar aromatic hydrocarbon and a crown ether hybrid macrocycle as an adhesive
  • Application of a condensation product of a pillar aromatic hydrocarbon and a crown ether hybrid macrocycle as an adhesive

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The compound provided by this embodiment has the molecular structural formula as follows:

[0037]

[0038] In a 100-ml round-bottomed flask, drop 2.36 g of benzo-21-crown-7-carboxylic acid, 0.52 g of decaamine[5]arene and 1.44 g of 4-dimethylaminopyridine, dissolve in 50 ml of dichloromethane, After stirring in an ice bath for ten minutes, 4.54 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added and reacted at room temperature for 6 days. After adding 2 ml of 10% hydrochloric acid and stirring for 5 minutes, the layers were separated. The lower organic layer was washed with water and spin-dried to obtain a crude product. The crude product was separated and purified by a silica gel column to obtain 1.28 g of the product with a yield of 45%.

[0039] The hydrogen spectrum and carbon spectrum data are as follows:

[0040] 1 H NMR (400MHz, CDCl 3 ,room temperature)δ7.40(d,J=16.0Hz,20H),6.73(d,J=12.0Hz,20H),4.10(s,20H),3.97(s,20H),3.92(s,16H) ,...

Embodiment 2

[0043] The compound provided by this embodiment has the molecular structural formula as follows:

[0044]

[0045] In a 100-ml round-bottom flask, put 2.59 g of bisbenzo-24-crown-8-carboxylic acid, 0.48 g of decaamine[5]arene and 1.32 g of 4-dimethylaminopyridine, and dissolve with 50 ml of dichloromethane After stirring in an ice bath for ten minutes, 4.17 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added and reacted at room temperature for 6 days. After the reaction was completed, 2 ml of 10% hydrochloric acid was added and stirred for 5 minutes before separation. The lower organic layer was washed with water and spin-dried to obtain a crude product, which was separated and purified by a silica gel column to obtain 1.72 g of product with a yield of 55%.

[0046] The hydrogen spectrum and carbon spectrum data are as follows:

[0047] 1 H NMR (400MHz, CDCl 3,room temperature)δ7.43(s,16H),6.85(s,40H),6.71(s,6H),6.67(d,J=8.0Hz,8H),4.14–4.09(m,44H),...

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Abstract

The invention discloses the application of a condensate of pillar aromatic hydrocarbons and crown ether compounds as an adhesive, which can not only adhere to a series of materials such as glass, metal, and marble in daily environments, but also adhere to ultra-low temperature resistant metal materials, and can Used in the temperature range of -196°C ~ 60°C, even if it is taken out from an extremely low temperature (liquid nitrogen, -196°C) environment, it can still maintain its strong adhesion performance. It is a new type of green, environmentally friendly and recyclable adhesive. .

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to the application of a condensate of a pillar aromatic hydrocarbon and a crown ether hybrid macrocycle as an adhesive. Background technique [0002] Adhesive is a kind of material that can bond the surfaces of two materials together and prevent it from falling off. It is mostly composed of polymer compounds and various auxiliary materials. With the development of supramolecular adhesives, a group of adhesives with reversible properties have emerged, which can be reused many times due to the dynamic non-covalent bonds. Although traditional adhesives or biomimetic adhesives containing dihydroxyphenylalanine (DOPA) can firmly adhere to various surfaces, it is difficult to separate the adhered surfaces without destroying the bonded parts. Although the reported supramolecular adhesives have been able to easily separate the bonded parts without damaging the adhesiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09J187/00C09J5/06C09J5/00
CPCC09J5/00C09J5/06C09J187/00
Inventor 董盛谊李兴邓燕
Owner HUNAN UNIV
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