Anionic ring-opening polymerization of n-sulfonylaziridine derivatives in air atmosphere

A heterocyclopropane, ring-opening polymerization technology, applied in the field of polymer chemistry, can solve the problems of unclear polymer structure and wide molecular weight distribution, and achieve the effects of easy availability, strong nucleophilicity, and wide variety

Active Publication Date: 2022-01-11
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the commercialized polyethyleneimine mainly has a branched structure, and there are problems such as unclear polymer structure and wide molecular weight distribution.

Method used

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  • Anionic ring-opening polymerization of n-sulfonylaziridine derivatives in air atmosphere
  • Anionic ring-opening polymerization of n-sulfonylaziridine derivatives in air atmosphere
  • Anionic ring-opening polymerization of n-sulfonylaziridine derivatives in air atmosphere

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1, Potassium ethyl xanthate initiates the air atmosphere polymerization of 2-methyl-N-tosyl aziridine

[0037] In an air atmosphere (relative humidity 70%), weigh 8.0 mg of potassium ethyl xanthate, 530 mg of 2-methyl-N-tosyl aziridine, add to the reaction tube, and then add dimethylformamide 2.5mL, stirred and mixed evenly, and reacted at 25°C for 4h (the synthetic route is as follows figure 1 shown). Precipitation in methanol yielded poly(2-methyl-N-tosylaziridine). GPC test molecular weight is 9500Da, PDI is 1.05.

[0038] figure 2 It is the NMR spectrum of the poly(2-methyl-N-tosylaziridine) prepared in Example 1.

[0039] image 3 It is the GPC elution curve of the poly(2-methyl-N-tosylaziridine) prepared in Example 1.

Embodiment 2

[0040] Embodiment 2, Potassium ethyl xanthate initiates the air atmosphere polymerization of 2-methyl-N-4-bromobenzenesulfonyl aziridine

[0041] In an air atmosphere (relative humidity 70%), weigh 8.0 mg of potassium ethyl xanthate and 690 mg of 2-methyl-N-4-bromobenzenesulfonyl aziridine, add them to the reaction tube, and then add dimethyl 2.5mL of methyl formamide, stirred and mixed evenly, and reacted at 25°C for 4h. Precipitate in methanol to obtain poly(2-methyl-N-4-bromobenzenesulfonylaziridine). GPC test molecular weight is 8500Da, PDI is 1.06.

[0042] Figure 4 It is the NMR spectrum of the poly(2-methyl-N-4-bromobenzenesulfonyl aziridine) prepared in Example 2.

[0043] Figure 5 GPC elution curve for the poly(2-methyl-N-4-bromobenzenesulfonylaziridine) prepared in Example 2.

Embodiment 3

[0044] Embodiment 3, Potassium ethyl xanthate initiates the air atmosphere polymerization of 2-methyl-N-4-nitrobenzenesulfonyl aziridine

[0045] In an air atmosphere (relative humidity 70%), weigh 4.0 mg of potassium ethyl xanthate and 305 mg of 2-methyl-N-4-nitrobenzenesulfonyl aziridine, add them to the reaction tube, and then add two Methylformamide 1.25mL, stirred and mixed evenly, reacted at 25°C for 4h. Precipitate in methanol to obtain poly(2-methyl-N-4-nitrobenzenesulfonylaziridine). GPC test molecular weight is 7800Da, PDI is 1.35.

[0046] Figure 6 It is the NMR spectrum of the poly(2-methyl-N-4-nitrobenzenesulfonyl aziridine) prepared in Example 2.

[0047] Figure 7 GPC elution curve for the poly(2-methyl-N-4-nitrobenzenesulfonylaziridine) prepared in Example 2.

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Abstract

The invention relates to an air atmosphere anion ring-opening polymerization method of N-sulfonyl aziridine derivatives. The invention uses air-stable sulfide anion as an initiator, adds sulfide anion, N-sulfonyl aziridine derivative monomer and solvent in an air atmosphere according to a metered ratio to carry out active anion ring-opening polymerization to obtain a corresponding polymer. Both the initiator and monomer of the polymerization system are insensitive to air and water, and can realize active anionic polymerization in the air atmosphere. There are many types of initiators and are easy to obtain, and a wide range of applicable monomers can realize N-sulfonyl aziridine derivatives Large-scale controllable preparation of homopolymers and copolymers. Since it does not require high-vacuum technology and inert atmosphere, the method is suitable for industrial scale-up production.

Description

technical field [0001] The invention belongs to the field of macromolecular chemistry, in particular to a series of air atmosphere anion ring-opening polymerization methods of N-sulfonyl aziridine derivatives; in particular to a kind of N-sulfonyl nitrogen that can be polymerized in an open system containing water and oxygen Air atmosphere anionic ring-opening polymerization method of heterocyclopropane derivatives. Background technique [0002] Polyethyleneimine and its derivatives have important applications in many fields such as gene delivery, antibacterial materials, and carbon dioxide fixation. [0003] Currently commercialized polyethyleneimines are mainly branched, and there are problems such as unclear polymer structure and wide molecular weight distribution. The current methods for preparing linear polyethyleneimine and its derivatives mainly include living cationic ring-opening polymerization of 2-oxazoline and living anion ring-opening polymerization of N-sulfon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/02
CPCC08G73/02
Inventor 朱新远霍猛童刚生卞雅文
Owner SHANGHAI JIAO TONG UNIV
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