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Azo compounds, polymers and their preparation methods and uses

A technology of azo compounds and polymers, applied in organic chemistry, eye implants, organic dyes, etc.

Active Publication Date: 2022-04-29
DONGGUAN HEC MEDICAL INTELLIGENT DEVICE R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the current ocular medical devices with blue light interception function and polymers for preparing ocular medical devices still need to be improved

Method used

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  • Azo compounds, polymers and their preparation methods and uses
  • Azo compounds, polymers and their preparation methods and uses
  • Azo compounds, polymers and their preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] 1-(4-((4-Hydroxyphenyl)diazenyl)phenoxy)-3-methoxypropan-2-ylmethacrylate

[0121]

[0122] Step 1: Synthesis of compound 1-(4-nitrophenoxy)-3-methoxypropan-2ol

[0123] Add 4-nitrophenol (41.7g, 0.3mol), potassium carbonate (56.5g, 0.1mol) and absolute ethanol (200mL) to the three-necked flask successively, and after stirring the mixture under reflux for 1h, slowly add 1- Chloro-3-methoxy-2-propanol (25.0 g, 0.2 mol), and stirring was continued for 24 h. The reaction solution was cooled to room temperature, filtered, and the filtrate was rotary evaporated to remove ethanol. The crude product was diluted with dichloromethane (250 mL), and washed with aqueous sodium hydroxide solution (5 wt%, 150 mL×2). The organic phase was dried overnight with anhydrous magnesium sulfate, filtered and evaporated to remove the solvent to obtain a light yellow viscous liquid (27 g, 59.1%). The mass spectrum and nuclear magnetic resonance H spectrum data of gained product are as foll...

Embodiment 2

[0146] Compound 1-(4-((4-Hydroxyphenyl)diazenyl)phenoxy)-3-methoxyprop-2-ylacrylate

[0147]

[0148] Step 1: Synthesis of compound 1-(4-tert-butoxycarbonylaminophenoxy)-3-methoxyprop-2-ylacrylate

[0149] 1-(4-tert-butoxycarbonylaminophenoxy)-3-methoxypropan-2-ol (8.00g, 26.94mmol), triethylamine (5.45g, 53.96mmol), 4-Dimethylaminopyridine (0.65 g, 2.50 mmol) and tetrahydrofuran (150 mL), after fully dissolving, slowly add acryloyl chloride (4.80 g, 46.12 mmol) dropwise to it, stir at 0 °C for 1 h, then return to room temperature and continue Stir for 24h. 50% aqueous sodium bicarbonate solution (10 mL) was added to the mixture to terminate the reaction, and after stirring for 10 minutes, the reaction solution was filtered, the tetrahydrofuran was removed by rotary evaporation, and the product was subjected to column chromatography (n-hexane / EtOAc (v / v) = 5 / 1 ) to obtain a pale red transparent viscous liquid (8.05 g, 81.9%). The mass spectrum and nuclear magnetic resona...

Embodiment 3

[0161] 1-(4-((2,4-Dihydroxyphenyl)diazenyl)phenoxy)-3-methoxyprop-2-ylacrylate

[0162]

[0163]The rest of the steps are the same as in Example 1, except that in step (6), 1-(4-aminophenoxy)-3-methoxypropan-2-yl methacrylate is successively added to the three-necked flask (3.00g, 11.30mmol), potassium bromide (1.35g, 11.30mmol) concentrated hydrochloric acid (5.70g, 56.50mmol) and acetone / water (v / v, 1 / 1) mixed solution (20mL), the mixed solution in Stir in a low-temperature bath at -5°C. When the internal temperature reaches below 0°C, dissolve sodium nitrite (0.93g, 13.60mmol) in water (20mL), slowly dropwise add to the above reaction solution, and continue stirring for 0.5h. Resorcinol (1.23g, 11.30mmol), sodium hydroxide (1.11g, 28.30mmol), sodium carbonate (1.50g, 14.10mmol) were dissolved in water (20mL), and added dropwise to the above diazonium salt solution, During the dropwise addition, keep the temperature of the solution not higher than 5°C. Stirring was cont...

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Abstract

The invention proposes an azo compound, a polymer, a preparation method and an application. The structural formula of this azo compound is shown in formula (I), wherein, R 1 , R 2 , R 3 and m have the meanings described in the specification. The azo compound has good performance of intercepting blue light, and the compound is a polymerizable azo compound, which is not easy to migrate and diffuse in the polymer.

Description

technical field [0001] The invention relates to the field of eye medical devices, in particular to an azo compound, a polymer polymerized from the azo compound, their preparation method and application. Background technique [0002] In recent years, with the popularization and development of electronic display devices, more and more attention has been paid to the damage of the blue light part of visible light to the human eye, especially the retina. Studies have shown that blue light in visible light can cause damage to the human eye, especially the retina, leading to vision loss or even blindness. Therefore, there are eye medical devices such as spectacle lenses that add films that can intercept blue light or components that can intercept blue light to prevent blue light from harming the human eye. [0003] However, current ocular medical devices with blue light interception function and polymers for preparing ocular medical devices still need to be improved. Contents of...

Claims

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Application Information

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IPC IPC(8): C07D249/18A61F2/16C09B69/10
CPCA61F2/16C07D249/18C09B69/10
Inventor 康小林李德珊刘敏曹立李建霖黄芳芳
Owner DONGGUAN HEC MEDICAL INTELLIGENT DEVICE R&D CO LTD
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