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Multi-functional-group polyethylene oxide-b-aliphatic polyester block copolymers, preparing method thereof and applications thereof

A technology of aliphatic polyester and ethylene oxide, which is applied in pharmaceutical formulations, medical preparations of inactive ingredients, etc., can solve the problems of functional groups affecting polymerization, restricting promotion and application, and difficulty in monomer synthesis, and achieves the reaction conditions. Controllable, easy-to-operate, and easy-to-quantify effects

Active Publication Date: 2014-07-23
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthesis route is simple, there are many problems in the actual reaction process, such as difficulty in monomer synthesis, low yield of copolymer, functional groups affecting polymerization and other factors, which limit the promotion and application of this method.

Method used

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  • Multi-functional-group polyethylene oxide-b-aliphatic polyester block copolymers, preparing method thereof and applications thereof
  • Multi-functional-group polyethylene oxide-b-aliphatic polyester block copolymers, preparing method thereof and applications thereof
  • Multi-functional-group polyethylene oxide-b-aliphatic polyester block copolymers, preparing method thereof and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthesis of poly(ethylene oxide-co-epichlorohydrin) random copolymer P(EO-co-ECH)

[0052] Add 3.0g of ethylene oxide and 0.7g of epichlorohydrin into the reaction flask at about 0°C, add 25mL of dichloromethane, and then add 0.75mL of 1.0M tetrahydrofuran solution of potassium triisobutyloxide, triisobutylaluminum Catalyst 1.5 mL. After 4 hours of reaction, the temperature was raised to room temperature and the reaction was continued for 24 hours. All the above operations ensure that the reaction system is anhydrous and oxygen-free. Add 200 μL of ethanol to stop the reaction. After most of the solvent was removed by rotary evaporation, it was precipitated in 200 mL of ice methanol to obtain 3.2 g of the product poly(ethylene oxide-co-epichlorohydrin) with a yield of 86%. Its molecular weight was measured by gel permeation chromatography (see Figure 7 ), the chemical structure was confirmed by proton NMR spectroscopy. The number average molecula...

Embodiment 2

[0053] Embodiment 2: Synthesis of P(EO-co-Glycidyl Azide)

[0054] Dissolve 2.0 g of poly(ethylene oxide-co-epichlorohydrin) random copolymer with a number average molecular weight of 5000 (where the molar ratio of ethylene oxide to epichlorohydrin is 9 / 1) in 15 mL of nitrogen , nitrogen-dimethylformamide (DMF), adding sodium azide (NaN 3 ) 2.0g, refluxed at 100°C for 48 hours under the protection of argon. After cooling to room temperature, the precipitate was removed by centrifugation, and the supernatant was precipitated in 200 mL of ice ether. The product was vacuum-dried to remove the organic solvent, dissolved in 10 mL of deionized water, transferred into a dialysis bag with a molecular weight cut-off of 3500 Da, and dialyzed for 48 hours, changing the water every 8 hours. After the dialysis was completed, the moisture was removed by freeze-drying to obtain 1.6 g of P(EO-co-Glycidyl Azide) product with a yield of 80%. Its molecular weight was measured by gel permeatio...

Embodiment 3

[0055] Embodiment 3: the synthesis of the amphiphilic block copolymer containing P (EO-co-Glycidyl Azide) block

[0056] (1) Synthesis of PCL-b-P (EO-co-Glycidyl Azide)

[0057] 2.0 g of P (EO-co-Glycidyl Azide) prepared in Example 2 (wherein the ratio of ethylene oxide to azidopropylene oxide is 9 / 1) was placed in the reaction flask, and the reaction system was repeatedly pumped out to remove the Sn(Oct) with a concentration of 0.982mol / L was sequentially added after oxygen 2 Toluene solution 5.0μL, caprolactone 2.0g, toluene 12mL. The closed reaction system was reacted at 110°C for 48 hours, cooled to room temperature, and precipitated in 300 mL of glacial ether to obtain 3.6 g of PCL-b-P (EO-co-Glycidyl Azide) block copolymer with a yield of 90%. Its molecular weight was measured by gel permeation chromatography (see Figure 9 ), the chemical structure was confirmed by proton NMR spectroscopy (see Figure 10 ).

[0058] After measurement, the number average molecular w...

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Abstract

The invention discloses aliphatic polyester-b-poly(ethylene oxide-co-propylene epoxide) amphipathy block copolymers side hydrophilic chains of which are provided with different functional groups, and a preparing method of the copolymers. The functional groups comprise halogen, azido, amino, carboxyl, and other groups. P(EO-co-ECH) is synthesized under mild reaction conditions through a controllable anionic coordinate polymerization method. A random copolymer (P(EO-co-Glycidyl Azide)) side chains of which is provided with the azido is obtained by azidation of the halogen on the P(EO-co-ECH). An amphipathy block copolymer the side hydrophilic chains of which are functionalized is obtained by subjecting the P(EO-co-Glycidyl Azide) and an aliphatic ester monomer to ring opening polymerization. Through reduction and click chemistry reactions, the azido of the block copolymer is converted, so as to obtain a series of amphipathy block copolymers the side hydrophilic chains of which are provided with the different functional groups such as amino and carboxyl are obtained.

Description

technical field [0001] The invention relates to a multifunctional polyethylene oxide-b-aliphatic polyester block copolymer and its preparation method and application. Background technique [0002] In the field of drug controlled release, the micellar drug-loading system formed by amphiphilic polymers has unique advantages due to its core-shell structure: 1) The hydrophobic core of the micelles can increase the solubility of the drug while protecting the activity of the drug; 2) The core-shell structure of the micelles can be regulated by controlling the chemical structure of the polymer, so as to achieve the purpose of controlling drug release; 3) The nanometer size of the micelles enables them to stay at the tumor site and thus have a passive targeting effect. (Xiao, L. et a1. Role of cellular uptake in the reversal of multidrug resistance by PEG-b-PLA polymeric micelles. Biomaterials2011, 32, 5148.) [0003] Aliphatic polyester-b-polyethylene oxide amphiphilic block copol...

Claims

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Application Information

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IPC IPC(8): C08G63/08C08G65/325C08G65/24C08G65/333C08G65/332A61K47/34
Inventor 刘俊杰喻青松甘志华
Owner INST OF CHEM CHINESE ACAD OF SCI
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