Controllable free radical polymerization method based on C-N bond cleavage

A polymerization method and free-radical technology are applied in the field of reversible deactivation free-radical polymerization catalysis to achieve the effects of simple and convenient polymer post-processing, simple and easy-to-operate equipment, and easy-to-obtain raw materials.

Active Publication Date: 2021-07-02
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, based on the reversible breakage of the C-N bond, the regulation and control of free radical polymerization has not been reported at home and abroad.

Method used

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  • Controllable free radical polymerization method based on C-N bond cleavage
  • Controllable free radical polymerization method based on C-N bond cleavage
  • Controllable free radical polymerization method based on C-N bond cleavage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: synthetic quaternary ammonium salt catalyst

[0037] The present embodiment provides a kind of synthetic method of quaternary ammonium salt catalyst, specifically comprises the following steps:

[0038] 1) Mix methyl α-bromophenylacetate (MBP) and pentamethyldiethylenetriamine (PMDETA) evenly at a molar ratio of 1:1, and react at room temperature to form a quaternary ammonium salt.

[0039] 2) After all the liquids are converted into solids, wash the synthesized quaternary ammonium salt with n-hexane, centrifuge in a centrifuge, pour off the upper layer liquid, wash with n-hexane, wash and centrifuge repeatedly for three times, then dry in a vacuum oven to obtain the quaternary ammonium salt. salt solids.

Embodiment 2

[0040] Embodiment 2: verification of quaternary ammonium salt catalyst

[0041] 1) Take appropriate amount of black silver oxide (Ag 2 O) The powder is placed in two identical vials 1 and 2, and 1 ml of deionized water is added to each of the vials 1 and 2.

[0042]2) Add an appropriate amount of the solid obtained in Example 1 to No. 2 vials, and after storing Vials 1 and 2 in the dark for a period of time, find the black Ag in No. 2 vials. 2 O turned into a light yellow substance, and No. 1 vial had no obvious change.

[0043] 3) Put the vials 1 and 2 under the light again, and after a period of time, it was found that the light yellow substance in the No. 2 bottle turned black while the No. 1 bottle had no obvious change.

Embodiment 3

[0044] Embodiment 3: MMA active polymerization catalyzed by quaternary ammonium salt catalyst

[0045] This embodiment provides a controllable free radical polymerization quaternary ammonium salt catalyst based on C-N bond breaking to catalyze the active polymerization of methyl methacrylate (MMA), specifically comprising the following steps:

[0046] 1) Add MMA (0.472g, 4.71mmol), MBP (0.00108g, 0.00471mmol), Me6TREN (0.00109g, 0.00471mmol) into a 5ml ampoule, and then add 0.5ml DMSO as a reaction solvent.

[0047] 2) Pass the argon gas through the ampoule containing the solution for 15 minutes to remove oxygen, and then seal the tube.

[0048] 3) Put the sealed tube under LED lamp (14W) to react.

[0049] 4) After the reaction reaches the set time, open the tube, and add an appropriate amount of tetrahydrofuran (THF) to dilute the polymerization solution. The diluted polymer solution was dropped into 250ml of refrigerated anhydrous methanol, precipitated, and suction filte...

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PUM

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Abstract

The invention discloses a controllable free radical polymerization method based on C-N bond cleavage, wherein the method comprises the following steps: dissolving a polymeric monomer, halogenated hydrocarbon and tertiary amine in an organic solvent, and reacting the obtained solution under an illumination condition in a protective atmosphere to obtain a polymer, wherein the polymeric monomer is a methacrylate monomer or an acrylamide monomer, the halogenated hydrocarbon is selected from one of methyl alpha-bromophenylacetate, hydroxyethyl isobromobutyrate and methyl 2-bromoisobutyrate, and the tertiary amine is selected from one of triethylamine, pentamethyldiethylenetriamine and tris(2-dimethylaminoethyl). The invention provides the brand new reversible inactivation free radical polymerization method; the catalytic system has the advantages of no metal ion participation, mild catalytic conditions, high catalytic activity and the like.

Description

technical field [0001] The invention relates to the technical field of reversible deactivation radical polymerization catalysis, in particular to a controllable radical polymerization method based on C-N bond breaking. Background technique [0002] Reversible deactivating radical polymerization (RDRP) has revolutionized modern polymer chemistry, thereby laying the foundation for the synthesis of complex macromolecules and enabling the preparation of previously unavailable materials. Many advanced polymer materials have been developed, and these materials are widely used in the fields of coatings and adhesives, electronics, medicine, cosmetics, environment, etc. At present, the main methods of reversible inactivated radical polymerization are: reversible addition-fragmentation transfer (RAFT), atom transfer radical polymerization (ATRP), nitroxide stabilized radical polymerization (NMRP), iniferter terminator (Iniferter ). Although the catalytic systems, mechanisms and adva...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/14C08F265/06C08F220/14C08F4/00
CPCC08F120/14C08F265/06C08F4/00C08F2438/00C08F220/14
Inventor 张卫东黄燕孙悦
Owner SUZHOU UNIV
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