Preparation method of monoamino-terminated polyethylene glycol-polyester amphiphilic block copolymer and obtained product

An amphiphilic block, polyethylene glycol technology, applied in the field of chemical synthesis, can solve the problem of difficult control of the ratio of polyethylene glycol and poly-e-caprolactone, the decrease of polymer molecular weight controllability, temperature conditions Large changes and other issues, to achieve the effect of easy implementation, mild conditions, and easy conditions

Inactive Publication Date: 2013-07-10
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first step reaction is a one-spoon stew, the temperature conditions change greatly and frequently, it is difficult to detect and control the molecular weight of polyethylene glycol intermediates, and the adjustability of the ratio of polyethylene glycol and poly-e-caprolactone is difficult to control
In the second step reaction, cysteamine hydrochloride will carry out nucleophilic addition to the ester carbonyl of the poly-e-caprolactone segment at high temperature, causing the poly-e-caprolactone segment to break, and the molecular weight of the polymer can vary. Control is further reduced

Method used

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  • Preparation method of monoamino-terminated polyethylene glycol-polyester amphiphilic block copolymer and obtained product
  • Preparation method of monoamino-terminated polyethylene glycol-polyester amphiphilic block copolymer and obtained product
  • Preparation method of monoamino-terminated polyethylene glycol-polyester amphiphilic block copolymer and obtained product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of Monoamino Polyethylene Glycol

[0041] In a dry reaction flask, add N, N-dimethylformamide (20 ml), then add polyethylene glycol-2400 monoallyl ether (2.4 g, 1 mmol), mercaptoethylamine hydrochloride ( 2.27 g, 20 mmol) and azobisisobutyronitrile (3.17 g, 12 mmol), heated to 60-65°C, and reacted for 24 h. Remove most of the solvent by distillation under reduced pressure, add 10 ml of distilled water, control the temperature at 25-30 °C, add 1 mol / L potassium carbonate aqueous solution (20 ml) dropwise, evaporate the water under reduced pressure, cool down to room temperature, add 30 ml of dichloro Methane, stirred for 0.5 h, filtered, and the filtrate was dried overnight with anhydrous sodium sulfate, evaporated under reduced pressure until about 3 ml of solvent remained, added 30 ml of anhydrous ether to precipitate, and filtered with suction. The resulting white solid was dissolved in as little dichloromethane as possible, and precipitated with 10 times...

Embodiment 2

[0047] Preparation of Monoamino Polyethylene Glycol

[0048] In a dry reaction flask, add 1,4-dioxane (20 ml), then add polyethylene glycol-2400 monoallyl ether (2.4 g, 1 mmol), mercaptoethylamine hydrochloride (1.14 g, 10 mmol) and azobisisobutyronitrile (0.264 g, 1 mmol), heated to 60-65°C, and reacted for 24 h. Remove most of the solvent by distillation under reduced pressure, add 10 ml of distilled water, control the temperature at 25-30 °C, add dropwise 1 mol / L potassium carbonate aqueous solution (20 ml), evaporate the water under reduced pressure, cool down to room temperature, add 30 ml of dichloro Methane, stirred for 0.5 h, filtered, and the filtrate was dried overnight with anhydrous sodium sulfate, evaporated under reduced pressure until about 3 ml of solvent remained, added 30 ml of anhydrous ether to precipitate, and filtered with suction. The resulting white solid was dissolved in as little dichloromethane as possible, and precipitated with 10 times the amount ...

Embodiment 3

[0050] Preparation of monoaminopolyethylene glycol-poly-d-valerolactone

[0051] In a dry reaction flask, mix and dissolve the monoaminopolyethylene glycol-2400 (2.48 g, 1 mmol) obtained in Example 1, 1 mol / L diethyl ether hydrochloride (2 ml) and chloroform (100 ml), then add d-valerolactone (4.96 g, 49.6 mmol) was reacted at room temperature for 24 h, washed three times with saturated aqueous sodium carbonate solution, dried over anhydrous sodium sulfate, and the organic solvent was distilled off under reduced pressure. A small amount of dichloromethane was added to dissolve the resulting glassy solid, and it was precipitated with 10 times the amount of anhydrous ether. Repeated twice to obtain 6.55 g of powdery white solid with a yield of 89%, and the number of repeating units of polyester in the obtained polymer was 57. 1 H-NMR spectrum such as image 3 . Explanation: This compound is the target compound, poly d-valerolactone is introduced, and the polyester structure i...

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Abstract

The invention discloses a preparation method of a monoamino-terminated polyethylene glycol-polyester amphiphilic block copolymer and an obtained product. The preparation method comprises the following steps: carrying out free radical addition on polyethylene glycol monoallyl ether as a starting raw material and a sulfydryl amine salt under the action of an azo catalyst, thereby obtaining monoamino-terminated polyethylene glycol; and carrying out a ring-opening polymerization reaction on monoamino-terminated polyethylene glycol and a polyester monomer under the catalysis of ether hydrochloride, thereby obtaining monoamino-terminated polyethylene glycol-polyester. The method is simple to operate, easy in condition realization, moderate in condition, easy to implement and easy in regulation and control of the molecular weight and the proportion of each chain segment of the obtained copolymer, so that the monoamino-terminated polyethylene glycol-polyester amphiphilic block copolymer can be prepared simply. The amino is led into the obtained copolymer at the other side of a PEG (polyethylene glycol) segment, thereby being more favorable for leading into various targeted tumor molecules to realize the targeting transportation of medicines to tumor cells or tissues. As a result, a more convenient way is provided for application of the copolymer in the field of medicines.

Description

technical field [0001] The invention relates to a preparation method of a monoamino-terminated polyethylene glycol-polyester amphiphilic block copolymer and the obtained copolymer, belonging to the technical field of chemical synthesis. Background technique [0002] Poly(ethylene glycol), PEG) amphiphilic block copolymers are a kind of copolymers with hydrophilic-lipophilic properties, which can form core-shell aggregated micelles, nano Granules etc. The hydrophilic shell and water can interact to improve the water solubility of this type of copolymer, while the lipophilic core interacts with lipophilic compounds (especially drugs) intermolecular force, causing the aggregation and entrapment of lipophilic drugs in the core , providing a good platform for improving the water solubility of lipophilic drugs. At the same time, polyethylene glycol can reduce the endocytosis of the phagocytic system in the body, thereby prolonging the circulation time of the contained compound i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/664C08G63/78
Inventor 冯润良宋智梅朱文霞杨凤英刘娜
Owner UNIV OF JINAN
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