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A kind of photoresponsive maleopimaric acid-based azobenzene amphiphilic polymer, preparation method and application thereof

A technology of pimaric acid-based azobenzene and amphiphilic polymer, which is applied in the field of maleopimaric acid-based azobenzene amphiphilic polymer, can solve the problem of low profit in rosin industry, insufficient international competitiveness, low deep processing rate, etc. problem, to achieve the effect of excellent photoresponse performance, good aggregation ability, good reversibility

Active Publication Date: 2022-07-08
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Rosin is a characteristic forestry biomass resource in my country. Although the output is huge, the deep processing rate is not high and the added value of the product is low, which directly leads to the low profit of my country's rosin industry and the lack of international competitiveness.

Method used

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  • A kind of photoresponsive maleopimaric acid-based azobenzene amphiphilic polymer, preparation method and application thereof
  • A kind of photoresponsive maleopimaric acid-based azobenzene amphiphilic polymer, preparation method and application thereof
  • A kind of photoresponsive maleopimaric acid-based azobenzene amphiphilic polymer, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Polyethylene glycol monomethyl ether (Mn=1000) (4g, 0.004mol) and triethylamine (0.2g, 0.02mol) were placed in a 100mL round bottom flask, dissolved in 30mL of dry dichloromethane, the reaction mixture was Cool to 0°C; then add 4-toluenesulfonyl chloride (3.80g, 0.02mol), react at 0°C for 2h, then heat up to 25°C, react for 12h, the reaction is terminated, precipitate with ether and recrystallize with ethanol to obtain p-toluene Sulfopolyethylene glycol monomethyl ether.

[0041] p-Toluenesulfopolyethylene glycol monomethyl ether (1.5 g, 1.3 mmol) and MPA-AZO-OH (0.77 g, 1.3 mmol) were placed in a round-bottomed flask, respectively, with 50 mL of DMF and K 2 CO 3 (0.2 g, 1.3 mmol) dissolved. The reaction mixture was stirred in a preheated oil bath at 50°C for 24 hours, then the reaction was stopped. The product was precipitated in excess cold ether, recrystallized in ethanol, dried for 48 hours, dialyzed in water for 3 days, and freeze-dried to obtain the maleopimari...

Embodiment 2

[0045] Put polyethylene glycol monomethyl ether (Mn=2000) (4g, 0.002mol) and triethylamine (0.1g, 0.01mol) into a 100mL round bottom flask, dissolve in 30mL of dry dichloromethane, the reaction mixture Cool to 0°C; then add 4-toluenesulfonyl chloride (1.90g, 0.01mol), react at 0°C for 2h, then heat up to 25°C, react for 12h, the reaction is terminated, precipitate with ether and recrystallize with ethanol to obtain p-toluene Sulfopolyethylene glycol monomethyl ether.

[0046] p-Toluenesulfopolyethylene glycol monomethyl ether (1.5 g, 0.7 mmol) and MPA-AZO-OH (0.42 g, 0.7 mmol) were placed in a round-bottomed flask, respectively, with 50 mL of DMF and K 2 CO 3 (0.1 g, 0.7 mmol) dissolved. The reaction mixture was stirred in a preheated oil bath at 50°C for 24 hours, then the reaction was stopped. The product was precipitated in excess cold ether and recrystallized in ethanol, dried for 48 hours, dialyzed in water for 3 days, and freeze-dried to obtain the maleopimaric acid-b...

Embodiment 3

[0050] Polyethylene glycol monomethyl ether (Mn=4000) (4g, 0.001mol) and triethylamine (0.05g, 0.005mol) were put into a 250mL round bottom flask, dissolved in 100mL of dry dichloromethane, the reaction mixture was Cool to 0°C; then add 4-toluenesulfonyl chloride (0.90g, 0.005mol), react at 0°C for 2h, then heat up to 25°C, react for 12h, the reaction is terminated, precipitate with ether and recrystallize with ethanol to obtain Tosyl sulfopolyethylene glycol monomethyl ether.

[0051] p-Toluenesulfopolyethylene glycol monomethyl ether (1.5 g, 0.375 mmol) and MPA-AZO-OH (0.11 g, 0.19 mmol) were placed in a round-bottomed flask, respectively, with 50 mL of DMF and K 2 CO 3 (0.05 g, 0.375 mmol) dissolved. The reaction mixture was stirred in a preheated oil bath at 50°C for 24 hours, then the reaction was stopped. The product was precipitated in excess cold ether, recrystallized in ethanol, dried for 48 hours, dialyzed in water for 3 days, and freeze-dried to obtain the maleop...

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PUM

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Abstract

The invention discloses a photoresponsive maleopimaric acid-based azobenzene amphiphilic polymer, a preparation method and application thereof, and a photoresponsive maleopimaric acid-based azobenzene amphiphilic polymer , characterized in that: its structural formula is: wherein, n=17~69 The above-mentioned photoresponsive maleopimaric acid-based azobenzene amphiphilic polymer self-assembles in an aqueous solution to form spherical micelles, and after 1min of ultraviolet light irradiation , the initial spherical micelles tend to become larger, and can be completely destroyed after 10min of ultraviolet light irradiation, and the initial spherical micelles can be basically restored after being placed in the dark for 24h. It has good reversibility and can be used as polymer nanocarriers , for drug controlled release.

Description

technical field [0001] The invention relates to a photoresponsive maleopimaric acid-based azobenzene amphiphilic polymer, a preparation method and application thereof, and belongs to the technical field of polymer self-assembly. Background technique [0002] Amphiphilic polymers refer to high molecular polymers that contain both hydrophilic and hydrophobic segments in the same molecular chain. The incompatibility of hydrophilic and hydrophobic segments leads to microphase separation, which enables amphiphilic polymers to self-assemble in selective solvents to form aggregates including micelles and vesicles. [0003] Rosin is a characteristic forestry biomass resource in my country. Although the output is huge, the deep processing rate is not high and the added value of the product is low, which directly leads to the low profit of my country's rosin industry and the lack of international competitiveness. Therefore, the development of high value-added rosin products is the pr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/337C08G65/333A61K47/22
CPCC08G65/337C08G65/33396A61K47/22
Inventor 张海波李婉冰商士斌翟兆兰
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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