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Synthesizing method of linear polyethyleneimine block copolymer

A polyethyleneimine block and synthesis method technology, applied in the field of polymer materials, can solve the problems that nitrogen heterocyclic carbene is not suitable for industrial scale-up and limits the application of polyethyleneimine

Active Publication Date: 2018-09-28
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the initiators they use are all metal salts of bis(trimethylsilyl)amide, and the metal residue problem of this type of initiator greatly limits the application of polyethyleneimine in biomedicine
Recently, it has also been reported that aziridine ring-opening polymerization was initiated using azacyclic carbene, but azacyclic carbene is not suitable for industrial scale-up, and the reaction time exceeds 24 hours

Method used

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  • Synthesizing method of linear polyethyleneimine block copolymer
  • Synthesizing method of linear polyethyleneimine block copolymer
  • Synthesizing method of linear polyethyleneimine block copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Under nitrogen flow purging, add THF solution (0.06mmol, lequiv) of tetrabutylammonium fluoride to the reaction bottle equipped with magnetic stirring bar, add phenylglycidyl ether (Z) after removing THF under reduced pressure (1.2 mmol, 20 equiv). Then the system was placed in an oil bath at 50° C. for 3-4 hours, and the consumption of GPE was monitored by 1H NMR. The monomers were completely consumed and did not stir. Add dimethyl sulfoxide (1 mL) to the system to dissolve the system, and wait until it is completely dissolved. 2-Methyl-1-(p-tolylsulfonyl)aziridine (H) (1.2 mmol, 20 equiv) was added to continue the reaction for 2 h. Finally, the reaction solution was dropped into excess methanol to precipitate a white polymer. After removing the upper layer of methanol by centrifugation, the crude product was washed with cold methanol for 3-4 times to obtain a pure product. After drying it in a vacuum oven for 2 days, it was analyzed by hydrogen spectrometry. The co...

Embodiment 2

[0098]Under nitrogen flow purging, add THF solution (0.06mmol, lequiv) of tetrabutylammonium chloride to the reaction bottle equipped with magnetic stirring bar, add phenylglycidyl ether (Z) after removing THF under reduced pressure (1.8 mmol, 30 equiv). Then the system was placed in an oil bath at 50° C. for 3-4 hours, and the consumption of GPE was monitored by 1H NMR. The monomers were completely consumed and did not stir. Add dimethyl sulfoxide (1 mL) to the system to dissolve the system, and wait until it is completely dissolved. 2-Methyl-1-(p-tolylsulfonyl)aziridine (H) (1.8 mmol, 30 equiv) was added to continue the reaction for 2 h. Finally, the reaction solution was dropped into excess methanol to precipitate a white polymer. After removing the upper layer of methanol by centrifugation, the crude product was washed with cold methanol for 3-4 times to obtain a pure product. After drying it in a vacuum oven for 2 days, it was analyzed by hydrogen spectrometry. The con...

Embodiment 3

[0100] Under nitrogen flow purging, add THF solution (0.06mmol, lequiv) of tetrabutylammonium bromide to the reaction flask equipped with magnetic stirring bar, add phenyl glycidyl ether (Z) after removing THF under reduced pressure (1.8 mmol, 30 equiv). Then the system was placed in an oil bath at 50° C. for 3-4 hours, and the consumption of GPE was monitored by 1H NMR. The monomers were completely consumed and did not stir. Add dimethyl sulfoxide (1 mL) to the system to dissolve the system, and wait until it is completely dissolved. 2-Methyl-1-(p-tolylsulfonyl)aziridine (H) (1.8 mmol, 30 equiv) was added to continue the reaction for 2 h. Finally, the reaction solution was dropped into excess methanol to precipitate a white polymer. After removing the upper layer of methanol by centrifugation, the crude product was washed with cold methanol for 3-4 times to obtain a pure product. After drying it in a vacuum oven for 2 days, it was analyzed by hydrogen spectrometry. The con...

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Abstract

The invention discloses a synthesizing method of a linear polyethyleneimine block copolymer, and belongs to the technical field of macromolecule materials. The synthesizing method comprises the following steps of initiating a cyclic monomer to generate block polymerization by a one-pot two-step method, namely that organic salt is used as an initiator; firstly, initializing an epoxy oxygen-containing ring to generate ring-opening polymerization, so as to form epoxy macromolecule chains; then, initiating an aziridine derivative monomer, and performing block polymerization; after the polymerization is completed, enabling methyl alcohol to terminate reaction; finally, synthesizing the polyethyleneimine block copolymer. The synthesizing method has the advantages that the initiator is organic and environmentally friendly, any metal residue is avoided, and the initiating effect is mild, efficient and quick; the one-pot two-step method is used for block polymerization, so that the operation issimple and convenient, and the synthesizing method is suitable for industrialization amplifying; the feature of activity controllability is realized in the whole polymerizing process, the molecular weight distribution of the product is narrow, and the molecular weight is controllable.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a method for synthesizing a linear polyethyleneimine block copolymer. technical background [0002] Polyethylenimine has received more and more attention as the cationic polymer with the highest charge density known so far. Polyethyleneimine has high cationicity, high reactivity, high adhesion and high adsorption. These unique properties determine its wide application in many fields. It can not only be used as a moisturizing agent for unsized absorbent paper, a fixing agent for dyed paper with acid dyes, a transfection agent that can replace viruses, but also be used for fiber modification, printing and dyeing auxiliaries, ion exchange resins and in certain absorbs carbon dioxide from moist air. Polyamides are precursors of polyethyleneimines. [0003] Early synthesis of polyethyleneimine was prepared by cationic polymerization of aziridine and hydrolysis...

Claims

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Application Information

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IPC IPC(8): C08G73/04C08G65/333C08G65/22C08G65/08
CPCC08G65/08C08G65/22C08G65/33303C08G73/0206
Inventor 郭凯王海鑫李振江罗子堃刘亚亚王鑫刘博周方园
Owner NANJING UNIV OF TECH
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