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Preparation method of photo-repair azobenzene polymer

An azobenzene and light repair technology, applied in organic chemistry and other directions, can solve the problems of expensive Grubb catalyst, high price, complicated preparation process, etc., and achieve excellent photo-crosslinking and de-crosslinking characteristics, excellent characteristics under photoisomerization Effect

Active Publication Date: 2019-10-18
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This repair method is simple and has high repair efficiency, but its biggest defect is that it can only be repaired once, and the Grubb catalyst is expensive and has the possibility of deactivation
Subsequently, White et al. developed a microvascular self-repair system with a three-dimensional network structure. This system can achieve multiple cycle repairs, but its preparation process is cumbersome and expensive.

Method used

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  • Preparation method of photo-repair azobenzene polymer
  • Preparation method of photo-repair azobenzene polymer
  • Preparation method of photo-repair azobenzene polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The synthesis of p-nitrophenoxyhexanol is prepared by reacting 6-chlorohexanol with p-nitrophenol.

[0043] 6-chlorohexanol (37.0mmol, 5.05g), 4-nitrophenol (44.4mmol, 6.18g), K 2 CO 3 (55.4mmol, 7.65g), KI (5mg), and DMF (50mL) were added to a three-necked flask, refluxed at 120 ° C, and the reaction was stopped after 6 hours of reaction. After drying, p-nitrophenoxyhexanol was obtained with a yield of about 87% and a purity of 95% by HPLC analysis.

[0044] figure 1 It is the H NMR spectrum (CDCl) of purified p-nitrophenoxyhexanol 3 as a solvent). The peaks with chemical shifts of 8.08ppm and 6.99ppm correspond to the proton peaks (a, b) on the carbon of the benzene ring, and the peak with a chemical shift of 4.08ppm corresponds to the proton peak (c) on the methylene connected to oxygen, and the chemical shift is 3.72 The ppm peak corresponds to the proton peak (g) of the methylene group connected to the hydroxyl group, and the peaks with chemical shifts of 1.89...

Embodiment 2

[0046] Synthesis of p-nitrophenoxyhexanol

[0047] 6-chlorohexanol (22.2mmol, 3.03g), 4-nitrophenol (44.4mmol, 6.18g), K 2 CO 3 (55.4mmol, 7.65g), KI (5mg), and DMF (50mL) were added to a three-necked flask, refluxed at 120 ° C, and the reaction was stopped after 6 hours of reaction. After drying, p-nitrophenoxyhexanol was obtained with a yield of about 89% and a purity of 95% by HPLC analysis.

Embodiment 3

[0049] Synthesis of p-nitrophenoxyhexanol

[0050] 6-chlorohexanol (88.8mmol, 12.12g), 4-nitrophenol (44.4mmol, 6.18g), K 2 CO 3 (55.4mmol, 7.65g), KI (5mg), and DMF (50mL) were added to a three-necked flask, refluxed at 120 ° C, and the reaction was stopped after 6 hours of reaction. After drying, p-nitrophenoxyhexanol was obtained with a yield of about 85% and a purity of 96% by HPLC analysis.

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Abstract

The invention belongs to the technical field of polymer materials and specifically relates to a photo-repair azobenzene polymer and a preparation method thereof. The preparation method comprises the steps: firstly, carrying out multi-step reactions such as etherification, nitro-reduction, diazo coupling and esterification on p-nitrophenol to obtain monomers containing anthracene and azobenzene groups, namely 4'-(hexyl methacrylate-oxyl)-4-(anthracene-2-methylacetate)azobenzene(MMA-AZO-AN); and then, carrying out free radical polymerization on MMA-AZO-AN serving as a monomer under the conditionthat an initiator exists to prepare the 4'-(hexyl methacrylate-oxyl)-4-(anthracene-2-methylacetate)azobenzene(MMA-AZO-AN). The novel photo-repair azobenzene polymer is prepared by applying the cooperation of two photo-responsive structures in combination with a reversible Diels-Alder addition reaction generated by the anthracene group under the condition of light excitation and a reversible cis-trans isomerism behavior generated by azobenzene under the conditions of ultraviolet light and visible light excitation.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a preparation method of a light-restorable azobenzene polymer. Background technique [0002] During long-term use, polymers and their composites will be subjected to chemical erosion, mechanical abrasion or impact, and thermal decomposition and other environmental influences, resulting in micro-cracks, resulting in final destruction of the material and shortening its life. This is also the direct cause of the performance degradation of the material in use. Traditional repair methods such as welding, bonding, and stitching are only part of the macro-level reunification of polymeric materials or reinforcement of damage. Introducing the self-healing function into polymer materials allows the materials to self-repair after internal damage, which helps to obtain structural materials with longer service life, more reliable performance and more economical performa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/36C07C245/08
CPCC07C245/08C08F120/36
Inventor 薛小强梁康蒋必彪黄文艳杨宏军蒋其民江力
Owner CHANGZHOU UNIV
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