Amine-terminated polyether and continuous preparation method thereof

A technology for amino-terminated polyether and polyether, which is applied in the field of amino-terminated polyether and its preparation, can solve the problems of reduced amino group conversion rate, deactivation, long preparation period, etc., and achieves the effect of high efficiency and high purity of amino-terminated polyether.

Inactive Publication Date: 2011-10-12
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CDI activators are often unstable and particularly sensitive to water, which can easily cause deactivation and lead to a decrease in the conversion rate of amino groups
The preparation cycle of the traditional discontinuous method is also relatively long

Method used

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  • Amine-terminated polyether and continuous preparation method thereof
  • Amine-terminated polyether and continuous preparation method thereof
  • Amine-terminated polyether and continuous preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1. Polyethylene glycol-polypropylene glycol-polyethylene glycol (PEO-PPO-PEO, molecular weight 5800, code P123) was vacuumed at 120 o C for four hours to remove water in a three-necked bottle. After cooling with argon protection, add 50mL of anhydrous acetonitrile with a syringe to form a solution. After repeated three times of vacuum-replacing argon, add CDI in the flask in an amount 4 times molar to the P123 hydroxyl group in an argon atmosphere, add 60 mL of acetonitrile, and stir to dissolve. Slowly add the P123 acetonitrile solution to the CDI solution dropwise, and the dropwise addition lasts for more than 4 hours. After the dropwise addition was completed, stirring was continued overnight. A P123-CDI solution was obtained. Vacuumize the three-necked bottle - replace argon three times, add 50 mL of ethylenediamine under argon atmosphere, slowly add P123-CDI solution into ethylenediamine dropwise for about 4 hours, and continue stirring for 4 hours after ...

Embodiment 2

[0025] Example 2 Dihydroxypolyethylene glycol (PEG, molecular weight 1500) was vacuumed to remove water at 120 o C for four hours in a three-necked bottle. After cooling with argon protection, add 50mL of anhydrous acetonitrile with a syringe to form a solution. Under an argon atmosphere, add CDI in a dry flask in an amount 4 times the molar amount relative to the PEG hydroxyl group, add 60 mL of acetonitrile, and stir to dissolve. The polyethylene glycol acetonitrile solution is slowly added dropwise to the CDI solution, and the dropwise addition lasts for more than 4 hours. After the dropwise addition was completed, stirring was continued overnight. Obtain PEG-CDI solution. Add 50 mL of ethylenediamine under an argon atmosphere, slowly drop the PEG-CDI stock solution into the ethylenediamine for about 4 hours, and continue stirring for 4 hours after the addition is complete. PEG-NH 2 solution.

[0026] PEG-NH 2 The solution was rotary steamed at 70-80 degrees Celsius. ...

Embodiment 3

[0027] Example 3 Dihydroxypolyethylene glycol (PEG, molecular weight 5000) was vacuumed to remove water at 120 o C for four hours in a three-necked bottle. After cooling with argon protection, add 50mL of anhydrous acetonitrile with a syringe to form a solution. Under an argon atmosphere, add CDI in a dry flask in an amount 4 times the molar amount relative to the PEG hydroxyl group, add 60 mL of acetonitrile, and stir to dissolve. The polyethylene glycol acetonitrile solution is slowly added dropwise to the CDI solution, and the dropwise addition lasts for more than 4 hours. After the dropwise addition was completed, stirring was continued overnight. Obtain PEG-CDI solution. Add 100 mL of ethylenediamine under an argon atmosphere, slowly add the PEG-CDI solution slurry into the ethylenediamine dropwise, add dropwise for about 4 hours, and continue stirring for 4 hours after the dropwise addition. PEG-NH 2 solution.

[0028] PEG-NH 2 The solution was rotary steamed at 70...

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Abstract

The invention belongs to the technical field of polymer synthesis and biomaterial preparation, and particularly discloses amine-terminated polyether and a continuous preparation method thereof. The preparation method comprises the following steps of: activating terminal hydroxyl of polyether by using N,N-carbonyl diimidazole (CDI), directly performing next reaction with ethanediamine without separating and purifying an activation product, performing rotary steaming on a product, dialyzing, and freeze-drying to obtain a product with high terminal amino group efficiency and high terminal amino group purity. The amine-terminated polyether can be used as a polymer synthesis intermediate or a biomaterial modified intermediate.

Description

technical field [0001] The invention belongs to the technical field of polymer synthesis and biological material preparation, and specifically relates to an amino-terminated polyether and a preparation method thereof. Background technique [0002] Polyethers have important application value in the modification of proteins, peptides and other biochemical drugs and biomaterials. The terminal group of polyether is usually a hydroxyl group, which has low activity and is difficult to react directly. It often needs to be converted into other active groups first. Amino-terminated polyether is one of the important derivatives, which has important applications in the fields of polymer synthesis and biomaterials. For example, amino-terminated polyethylene glycol is used to make polyethylene glycol-polyamino acid block polymers, and amino-terminated polyethylene glycol-polypropylene glycol-polyethylene glycol is used as a drug carrier material. There are many ways to convert hydroxyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/48C07K1/107A61K47/34
Inventor 丁建东常广涛
Owner FUDAN UNIV
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