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Azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction and preparation method thereof and application of azobenzene derivative as photoswitch adhesive

An azobenzene derivative, solid-liquid conversion technology, applied in the direction of organic chemistry, etc., can solve the problems of difficult recovery, difficult to wash off, and become solid, and achieve the effect of good solubility and easy removal

Active Publication Date: 2018-11-09
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Adhesives are ubiquitous in life. For example, you must have encountered such a thing: sticking things with tape or hooks is convenient and simple to use, but if used improperly, the tape or hooks are easy to fall off and fall off. If you stick it again, it will not stick; if you accidentally drop the super glue on your hands or clothes, it will quickly become solid and difficult to wash off, and it cannot be reused
Adhesive materials are faced with difficult recycling and non-reusable problems, which also bring huge challenges to the environment and resources

Method used

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  • Azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction and preparation method thereof and application of azobenzene derivative as photoswitch adhesive
  • Azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction and preparation method thereof and application of azobenzene derivative as photoswitch adhesive
  • Azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction and preparation method thereof and application of azobenzene derivative as photoswitch adhesive

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Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0037] 1. Add 3.68g (20mmol) methyl gallate and 9.365g (62.0mmol) bromopentane into two reaction tubes, then add 5.52g (40.0mmol) of K 2 CO 3, catalyst equivalent (20 mg) of TBAB, then add 100ml of acetone solvent, stir evenly under a nitrogen atmosphere and react at 70°C for 48h; after the reaction is complete, cool to room temperature, remove the acetone solvent by rotary evaporation, and extract with dichloromethane and water , concentrate the organic phase, and then purify on a silica gel column, and the product obtained is denoted as a1-COOCH 3 ;

[0038] 1 H NMR (400MHz, CDCl 3 )δ7.28(s, 2H), 4.04(dt, J=10.4, 5.2Hz, 6H), 3.90(s, 3H), 1.81(ddd, J=19.5, 13.9, 6.9Hz, 6H), 1.44(ddt ,J=35.4, 14.5,7.3Hz,12H),0.94(td,J=7.1,3.3Hz,9H);

[0039]

[0040] 2. Add 2.96g (7.5mmol) a1-COOCH 3 and 815 mg (15 mmol) of potassium hydroxide were added to the reaction tube, then 50 ml of ethanol solvent was added, stirred evenly under a nitrogen atmosphere, and then reacted at 80°C ...

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Abstract

The invention discloses an azobenzene derivative for realizing solid-liquid conversion based on photo-thermal induction and a preparation method thereof and application of the azobenzene derivative asa photoswitch adhesive. Through two-step esterification reaction between two hydroxyl groups of bis-naphthol and carboxyl azobenzene and gallic acid derivative respectively, the final product is obtained. Based on the characteristics of low melting point and long absorption band of a solid azobenzene compound, under irradiation of green ray, luminous energy absorbed will be converted to heat, andrising of temperature leads to melting of the azobenzene derivative. Being placed at room temperature, a liquid-state azobenzene derivative will exist in the solid form when the temperature drops below the melting point, and has strong bonding performance. Under irradiation of green ray once again, the derivative will be molten again and lose bonding performance, and the liquid-state azobenzene derivative will become solid again when being cooled to room temperature and then adhesive force will be displayed. The photoswitch adhesive is extremely easy to dissolve in common organic solvents, iseasy to clean and recover, can be reused, and is a green, environment-friendly and resource-saving adhesive.

Description

technical field [0001] The invention belongs to the technical field of adhesive materials, and in particular relates to an azobenzene derivative that realizes solid-liquid transition based on photothermal induction, a preparation method thereof, and an application as an optical switch adhesive. Background technique [0002] As a bridge connecting two materials, adhesive plays a very important role in production and life. Adhesive is an indispensable material in the field of national economy. Compared with other polymer materials, it has a wide range of uses and varieties. Therefore, it is also called industrial seasoning and has become an indispensable material in many modern industries. Adhesives are ubiquitous in life. For example, you must have encountered such a thing: sticking things with tape or hooks is convenient and simple to use, but if used improperly, the tape or hooks are easy to fall off and fall off. If you stick it again, it will not stick; if you accidental...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08
CPCC07C245/08
Inventor 尹梅贞吴振赵绪杰
Owner BEIJING UNIV OF CHEM TECH
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