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One-step synthesis method of terminal amino functionalized polyether

A technology of amino functionalization and synthesis method is applied in the field of one-step synthesis of terminal amino functionalized polyether, which can solve the problems of cumbersome deprotection process and limitations, and achieve the effects of product purity and yield improvement, high reaction efficiency and huge stock.

Active Publication Date: 2021-08-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method does not introduce additional functional groups, but these initiators are uncommon compounds and require additional small molecule synthesis steps to obtain, and the deprotection process is cumbersome
The difficulty of synthesizing diheterofunctionalized PEG with a single amino group can be seen from this. On this basis, the further synthesis of amino-functionalized polyethers with special end groups, substituents and topological structures will be more limited.

Method used

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  • One-step synthesis method of terminal amino functionalized polyether
  • One-step synthesis method of terminal amino functionalized polyether
  • One-step synthesis method of terminal amino functionalized polyether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In this example, alkanolamine is used as the initiator, and the non-covalent bond formed with alkyl boron is used to protect the amino group, and the hydroxyl group activated by the organic base initiates the ring-opening polymerization of ethylene oxide to prepare α-amino-ω-hydroxyl Polyethylene oxide (two-terminal heterofunctionalized PEG, NH 2 -PEG-OH). The specific operation is as follows:

[0035] In an inert atmosphere, add 1 part (mole parts) of ethanolamine into a dry glass reactor, continue to add 1.2 parts of a tetrahydrofuran solution containing triethylborane, stir and mix well. After the white mist generated during the in-situ formation of non-covalent bonds between amino groups and triethylboron dissipated, continue to add 0.005 parts of phosphazene base t-BuP 1 solution in tetrahydrofuran. In this embodiment, the molar ratio of alkylboron to amino group is 1.2, and excess alkylboron forms Lewis acid-base pair with organic base, and the molar ratio is 4...

Embodiment 2

[0038] In this embodiment, the organic base is replaced by the tertiary amine DABCO, and the others are the same as in Embodiment 1. Reaction at room temperature for 10h, that is. Theoretical number average molecular weight M of polyethylene oxide n,th It is 3.1kg / mol. The molecular weight measured by SEC was 3.4 kg / mol, and the degree of dispersion was 1.09.

Embodiment 3

[0040] In this embodiment, the organic base is replaced by triaminophosphine HMTP, and the others are the same as in Embodiment 1. Reaction at room temperature for 24h, that is. Theoretical number average molecular weight M of polyethylene oxide n,th It is 3.1kg / mol. The molecular weight measured by SEC was 3.4 kg / mol, and the degree of dispersion was 1.10.

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a one-step synthesis method of terminal amino functionalized polyether. Under an inert atmosphere, the epoxy monomer is added to a non-covalently protected amino alcohol type catalyst / initiator system to react to obtain a terminal amino functionalized polyether; the non-covalently protected amino alcohol type catalyst / initiator system includes amino Alcohols, organic bases and boron alkyls. The present invention utilizes the advantage that the non-covalent bond formed in situ between the amino group and the alkyl boron can exist stably during the ring-opening polymerization of epoxy monomers, and realizes the effective protection of the amino group: at the same time, the excess alkyl boron and the organic base Composition of Lewis acid-base pair catalyst, chemoselective implementation of ring-opening polymerization of epoxy monomers. This system can realize complete protection of amino groups and quantitative initiation of hydroxyl groups at room temperature, and further synthesize terminal amino-functionalized polyethers with definite structures in one step.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a one-step synthesis method of terminal amino functionalized polyether. Background technique [0002] Polyethylene oxide (also known as polyethylene glycol, PEO / PEG) has excellent water solubility, biocompatibility and anti-protein adsorption performance, and is a kind of polyether material with a wide range of uses. In recent years, the diverse functional requirements in different fields have prompted the continuous innovation and development of PEG structures. The PEG backbone consists of repeating ether linkages (-CH 2 -CH 2 -O-) chain link structure, so the abundant terminal functional groups become the decisive factor for PEG to meet various application requirements. The common method is to add polyethylene glycol monomethyl ether (mPEG, CH 3 O-PEG-OH) terminal hydroxyl groups are transformed into carboxyl, amino, mercapto, (saturated / unsaturated) a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/28
CPCC08G65/2624C08G65/2627
Inventor 赵俊鹏陈烨张广照
Owner SOUTH CHINA UNIV OF TECH
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