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Method for catalyzing hybrid polymerization of alkene monomer and cyclic ester monomer by using imidazole ionic liquid

A technology of ionic liquids and polymerization methods, which is applied in the field of hybrid polymerization of imidazole ionic liquids to catalyze ethylenic monomers and cyclic ester monomers, can solve the problems of poor versatility of catalysts, harsh preparation conditions, and residual metal traces, etc., and can be designed Strong, stable, adjustable acidity, low vapor pressure

Pending Publication Date: 2022-03-08
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2012, Zhang Guangzhao's research group (Macromolecules, 2012, 45, 3312-3317) first discovered that in phosphazene base (t-BuP 4 ) catalysis, under the small molecular alcohol as initiator, caprolactone and methyl methacrylate undergo anionic hybrid copolymerization and form a random copolymer, but the catalyst used in this method has poor versatility and is expensive
In 2013, the Aoshima group (J.Am. Chem. Soc, 2013, 135,9330−9333) reported that Lewis acid tris(pentafluorophenyl)borane (B(C 6 f 5 ) 3 ) Cationic hybrid copolymerization of vinyl ether and isobutylene oxide under catalysis, but the preparation conditions of this method are harsh and the molecular weight is low, and the distribution is relatively wide
However, these hybrid polymerization methods in the prior art require multiple steps, involve different catalytic initiation systems, and have residual metal traces

Method used

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  • Method for catalyzing hybrid polymerization of alkene monomer and cyclic ester monomer by using imidazole ionic liquid
  • Method for catalyzing hybrid polymerization of alkene monomer and cyclic ester monomer by using imidazole ionic liquid
  • Method for catalyzing hybrid polymerization of alkene monomer and cyclic ester monomer by using imidazole ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The molar ratio is 1:25:25:50, respectively take 1-ethyl-3-methylimidazolium chloride salt, lactide, methyl methacrylate and propylene oxide, and 0.1 g of catalyst requires 5 mL of organic solvent Take tetrahydrofuran; add the above raw materials into the reaction flask, react at 80°C for 2 hours under vacuum atmosphere, cool to room temperature, dissolve the reaction system with chloroform, and obtain the crude product; use a large amount of hydrochloric acid acidified anhydrous methanol Settling treatment, pouring the supernatant, evaporating the solvent in a fume hood, and drying in a vacuum oven at 60° C. for 10 h to obtain the corresponding hybrid copolymer.

[0026] figure 1 For the proton nuclear magnetic spectrum of the poly(methyl methacrylate-co-lactide) that embodiment 1 prepares ( 1 H-NMR, CDCl 3 )picture.

[0027] figure 2 Infrared spectrum (FTIR) comparison chart of the poly(methyl methacrylate-co-lactide) prepared in Example 1 and the respective homo...

Embodiment 2

[0030] The molar ratio is 1:50:50:100, respectively take 1-ethyl-3-methylimidazolium chloride salt, caprolactone, methyl methacrylate and propylene oxide, and 0.05 g of catalyst requires 2.5 mL of organic solvent Take tetrahydrofuran; put the above raw materials into the reaction bottle, react at 100°C for 12h under vacuum atmosphere, cool to room temperature, dissolve the reaction system with chloroform, and obtain the crude product; use a large amount of hydrochloric acid acidified anhydrous methanol Settling treatment, pouring the supernatant, evaporating the solvent in a fume hood, and drying in a vacuum oven at 60° C. for 10 h to obtain the corresponding hybrid copolymer.

[0031] image 3 For the proton nuclear magnetic spectrum of the poly(methyl methacrylate-co-caprolactone) that embodiment 2 prepares ( 1 H-NMR, CDCl 3 )picture.

[0032] The polymer prepared in Example 2 is a copolymer of methyl methacrylate and caprolactone, rather than a mixture of both homopolyme...

Embodiment 3

[0034] The molar ratio is 1:50:50:100, respectively take 1-ethyl-3-methylimidazolium bromide, valerolactone, methyl methacrylate and propylene oxide, and 0.1 g of catalyst requires 5 mL of organic solvent Take 1,4-dioxane; put the above raw materials into the reaction flask, react at 80°C for 12h under vacuum atmosphere, cool to room temperature, dissolve the reaction system with chloroform, and obtain the crude product; acidify with a large amount of hydrochloric acid The crude product was settled with anhydrous methanol, the supernatant was poured, the solvent was evaporated in a fume hood, and dried in a vacuum oven at 60° C. for 10 h to obtain the corresponding hybrid copolymer.

[0035] Figure 4 For the proton nuclear magnetic spectrum of the poly(methyl methacrylate-co-valerolactone) prepared in embodiment 3 ( 1 H-NMR, CDCl 3 )picture.

[0036] The polymer prepared in Example 3 is a copolymer of methyl methacrylate and valerolactone, rather than a mixture of both hom...

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Abstract

The invention discloses a method for catalyzing hybrid polymerization of an alkene monomer and a cyclic ester monomer by using an imidazole ionic liquid, which comprises the following steps of: reacting the cyclic ester monomer, the alkene monomer, an epoxide, a catalyst and an organic solvent in a vacuum atmosphere at a certain temperature, cooling to room temperature, completely dissolving a product by using chloroform, and purifying by using a methanol solution acidified by hydrochloric acid to obtain the imidazole ionic liquid. And drying in vacuum to obtain the corresponding hybrid copolymer. A catalytic system used in the hybrid polymerization method is the ionic liquid, the method is green and environment-friendly, the applicable monomer range is wide, meanwhile, the preparation process is simple and convenient, additional cocatalysts and initiators do not need to be added, and a new thought is provided for synthesizing high-value polymer materials with new characteristics.

Description

technical field [0001] The invention relates to a hybrid polymerization method, in particular to a hybrid polymerization method of imidazole ionic liquid catalyzed alkene monomer and cyclic ester monomer. Background technique [0002] In the traditional copolymerization process, all monomers must have the same polymeric group (double bond, end group or ring), the polymerization mechanism is basically the same as the corresponding homopolymerization reaction, the only difference is that there is competition between different monomers . Different from traditional copolymerization, hybrid copolymerization is the copolymerization of two or more monomers with different polymerizable groups to form the same chain. Cyclic monomers and vinyl monomers are the most widely used monomers in the polymer industry and have broad application prospects. Due to structural differences, the polymerization reactions of cyclic monomers and vinyl monomers generally have very different polymeriza...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/08C08G63/87C08G63/84C08F120/14C08F120/58C08F120/54C08F120/18
CPCC08G63/08C08G63/823C08F120/14C08F120/58C08F120/54C08F120/18Y02P20/54
Inventor 宋鹏飞马菊萍李永莉马菁菁袁小龙席琦武雪
Owner NORTHWEST NORMAL UNIVERSITY
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