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Method for preparing multi-responsive block copolymer containing azopyridine

A technology of block copolymer and azopyridine, which is applied in the field of preparation of multi-responsive block copolymer, and achieves the effect of simple and easy synthesis method and wide sources.

Inactive Publication Date: 2012-08-15
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, there are many studies on the response of azobenzene polymers to ultraviolet light, but less research on azopyridine photoresponsive polymers.

Method used

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  • Method for preparing multi-responsive block copolymer containing azopyridine
  • Method for preparing multi-responsive block copolymer containing azopyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Dissolve 5 g of phenol and 4 g of sodium nitrite in 20 mL of 10% aqueous sodium hydroxide solution, and 6 g of 4-aminopyridine in 45 mL of 7.3 mol / L hydrochloric acid solution. At 0 °C, the former solution was added dropwise to the latter, after mixing, the pH value of the mixed solution was adjusted to 6 with 10% NaOH solution, filtered, and the precipitate was purified and dried to obtain product A. Then, 4 g of product A, 5.5 g of potassium carbonate, 3 g of 6-chloro-1-hexanol, and 5 g of potassium iodide were dissolved in an appropriate amount of solvent, reacted at 70 °C for 8 hours, purified and dried to obtain product B. Dissolve 3 g of product B in tetrahydrofuran, add 1.55 mL of triethylamine, then dropwise add 1 mL of methacryloyl chloride solution, react for 7 hours, pour the reaction solution into water to obtain a precipitate, and pass the dried precipitate through column chromatography After that, the photoresponsive monomer is obtained.

[0026] Dissolve...

Embodiment 2

[0028] Dissolve 5 g of phenol and 4 g of sodium nitrite in 25 mL of 10% aqueous sodium hydroxide solution, and 6 g of 2-aminopyridine in 55 mL of 7.3 mol / L hydrochloric acid solution. At -5 °C, the former solution was added dropwise to the latter, after mixing, the pH value of the mixed solution was adjusted to 7 with 10% NaOH solution, filtered, and the precipitate was purified and dried to obtain product A. Dissolve 4 g product A, 5.5 g potassium carbonate, 3 g 6-chloro-1-hexanol, and 6 g potassium iodide in an appropriate amount of dimethylformamide solvent, react at 85 °C for 10 hours, purify and dry to obtain Product B. Dissolve 3 g of product B in chloroform, add 2 mL of diethylamine, and then dropwise add it to a solution of 1.2 mL of methacryloyl chloride. After reacting for 9 hours, pour the reaction solution into water to obtain a precipitate. After drying, The photoresponsive monomer was obtained after the precipitate was subjected to column chromatography.

[002...

Embodiment 3

[0031] Dissolve 5 g of phenol and 4 g of sodium nitrite in 25 mL of 10% aqueous sodium hydroxide solution, and 6 g of 3-aminopyridine in 55 mL of 7.3 mol / L hydrochloric acid solution. At 5 °C, the former solution was added dropwise to the latter, after mixing, the pH of the mixed solution was adjusted to 6.5 with 10% NaOH solution, filtered, and the precipitate was purified and dried to obtain product A. Dissolve 4 g product A, 5.5 g potassium carbonate, 3.5 g 6-bromo-1-hexanol, and 6 g potassium iodide in an appropriate amount of dimethyl sulfoxide solvent, react at 95 °C for 12 hours, purify and dry to obtain Product B. Dissolve 3 g of product B in dichloromethane, add 2 mL of diethylamine, and then dropwise add it to a solution of 1.2 mL of methacryloyl chloride. After reacting for 8 hours, pour the reaction solution into water to obtain a precipitate. After drying, The photoresponsive monomer was obtained after the precipitate was subjected to column chromatography.

[0...

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Abstract

The invention belongs to the field of functional polymer materials and in particular relates to a method for preparing a multi-responsive block copolymer containing azopyridine. The preparation method is characterized by synthesizing azopyridine with photo-responsivity through a diazo coupling reaction and then reacting azopyridine with 6-chloro-1-hexanol and methacryloyl chloride in sequence to prepare a methacrylate monomer containing an azopyridine group; then synthesizing a methacrylic acid-N,N-(dimethylamino)ethyl monomer into a macroinitiator through atom transfer radial polymerization (ATRP) under the protection of an inert gas nitrogen or argon, wherein the block has temperature sensitivity and temperature responsivity; and finally synthesizing the macroinitiator with an azopyridine monomer to prepare the multi-responsive block copolymer containing azopyridine through ATRP. The method has the following advantages that the block copolymer simultaneously has photo-responsivity, pH sensitivity and temperature sensitivity and can be self-assembled into various aggregation morphologies such as stable nano micelle and vesicles in water, so the block copolymer is widely applied in the fields such as drug controlled release carriers, smart photo switches, photo sensors and nano devices; the synthesis method is simple and practical; the raw materials can be industrially produced; and the method has good popularization and application values.

Description

technical field [0001] The invention belongs to the field of polymer materials, and in particular relates to a preparation method of an azopyridine-containing multi-responsive block copolymer. Background technique [0002] Photoresponsive polymer is a smart polymer material that responds to changes in physical and chemical properties such as its shape, color, and hardness under the stimulation of external light signals such as ultraviolet light and infrared light. Among them, there are many studies on the responsiveness of azobenzene polymers to ultraviolet light, but few studies on azopyridine photoresponsive polymers. Such materials have broad applications in the fields of optical smart switching, optical sensors, and light-to-power conversion devices. Amphiphilic azopyridines can self-assemble into micelles or vesicles, and can also be applied to the field of biological drug delivery. [0003] The trans configuration of azopyridine is relatively stable under visible lig...

Claims

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Application Information

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IPC IPC(8): C08F293/00C08F220/36
Inventor 袁伟忠郭文
Owner TONGJI UNIV
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