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Method for catalyzing ring-opening polymerization of cyclic ester by aza-aromatic ring

An aromatic ring-catalyzed cyclic ester and ring-opening polymerization technology, which is applied in the field of nitrogen-heteroaromatic catalyzed ring-opening polymerization of cyclic esters, and can solve problems such as poor catalytic activity

Active Publication Date: 2020-07-03
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the PDI of the generated polymer is in a relatively narrow range of about 1.1, the catalytic reaction time is above 10h, indicating that the catalytic activity is poor under this condition

Method used

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  • Method for catalyzing ring-opening polymerization of cyclic ester by aza-aromatic ring
  • Method for catalyzing ring-opening polymerization of cyclic ester by aza-aromatic ring
  • Method for catalyzing ring-opening polymerization of cyclic ester by aza-aromatic ring

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0015] Example 1-10: Catalyst 1-3 Catalyzed performance research of ε-caprolactone ring-opening polymerization reaction

[0016] Among them, in Example 1-2, Catalyst 1 was used to carry out ring-opening polymerization of ε-caprolactone at the same temperature, different solvents, and the ratio of monomer, catalyst, and initiator being 100:1:1.

Embodiment 1

[0018] Under the condition of anhydrous and oxygen-free nitrogen atmosphere, absorb 5.8 mg (50 μmol) of the catalyst 1 liquid and dissolve it in 5 mL tetrahydrofuran solvent, and then add 0.02 mL n-butyllithium (2.5mol / L, 50 μmol) to it As an initiator, stir the reaction for 30 min; control the temperature at 25 °C and add 0.55 mL (5 mmol) ε-caprolactone monomer at a ratio of monomer:catalyst:initiator molar ratio of 100:1:1, control Stirring was continued for 4 min at 25 °C. During the reaction, by absorbing the reaction liquid, using 1 H NMR analysis monitors monomer conversion and makes calculations and records. Then 3.0 mL of benzoic acid (quencher) was added to terminate the reaction, and then 80 mL of methanol was added to completely precipitate the white polymer. The white polymer was filtered and washed, and finally the polycaprolactone product was obtained by drying. The results of the polymerization reaction are shown in Table 1 No. 1.

Embodiment 2

[0020] The solvent was toluene, and the stirring reaction was continued for 3 minutes, and the rest of the operations were the same as in Example 1. The results of the polymerization reaction are shown in Table 1 No. 2.

[0021] It can be seen that when the polymerization reaction is carried out in tetrahydrofuran and toluene solvent, the monomer conversion rate of 100% can be achieved in a short period of time, but the reaction rate carried out in tetrahydrofuran solvent is faster, and the relative molecular weight of the generated polymer product is The smaller the distribution value, the better the performance.

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Abstract

The invention discloses a method for catalyzing ring-opening polymerization of cyclic ester by an aza-aromatic ring, belongs to the technical field of polymer polymerization, and aims to provide a method for catalyzing ring-opening polymerization of cyclic ester by an aza-aromatic ring. According to the method, an aza-aromatic ring compound (indole), quinoline and pyridine are taken as catalysts,under the action of a strong base initiator, ring-opening polymerization reaction research is carried out on monomers: epsilon-caprolactone and rac-lactide respectively, and MALDI-TOF mass spectrometry analysis is carried out on the generated polymer. The method has the characteristics that the aza-aromatic ring compound (indole), quinoline and pyridine are used as catalysts, have stable chemicalproperties, are easy to purchase and are convenient to purify and store. The organic compound is used as a catalyst, has very high catalytic activity in ring-opening polymerization reaction of lactonemonomers epsilon-caprolactone and rac-lactide at the normal temperature under the initiation of a strong alkali, and can be used for preparing polycaprolactone and polylactide products with a high molecular weight and narrow relative molecular weight distribution.

Description

technical field [0001] The invention belongs to the technical field of polymer polymerization methods, and in particular relates to a ring-opening polymerization method of cyclic esters catalyzed by nitrogen heteroaromatic rings. Background technique [0002] The use of organic base catalysts in the ring-opening polymerization of cyclic lactones has become a system. There are many kinds of organic bases, such as basic organic substances such as phosphazene, amidine, and guanidine, which can be used as catalysts for ring-opening polymerization, and the ring-opening polymerization can be carried out through the activation of the hydroxyl group of the cyclic lactone by the initiator. Organic bases include not only amine compounds, but also other fused-ring aromatic organic compounds that can donate electron pairs, among which pyridine is a common organic base. Hedrick was the first to use 4-dimethylaminopyridine as an organic catalyst to catalyze the ring-opening polymerizatio...

Claims

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Application Information

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IPC IPC(8): C08G63/08C08G63/87
CPCC08G63/08C08G63/823C08G63/87
Inventor 陈霞范子垚吴晨
Owner SHANXI UNIV
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