Method for cyclic compound ring opening polymerization

A ring-opening polymerization technology for cyclic compounds, which is applied in the field of organic catalysis and polymer materials, can solve the problems of few catalyst preparation methods, and achieve the effects of large commercial application potential, narrow molecular weight distribution, and wide sources

Active Publication Date: 2017-12-01
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation method of the catalyst is rarely reported (J.C.S.CHEM.COMM., 1980)

Method used

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  • Method for cyclic compound ring opening polymerization
  • Method for cyclic compound ring opening polymerization
  • Method for cyclic compound ring opening polymerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Add organic salt (1) (33.3mg, 0.1mmol, 1.0equiv), benzyl alcohol (10.3μL, 0.1mmol, 1.0equiv) and δ-valerolactone (0.27ml, 3.0mmol, 30equiv) into the reaction flask, and use 1 mL of dichloromethane was dissolved, and under the protection of Ar, the reaction was stirred at room temperature for 12 hours. The reactant was concentrated and poured into methanol, the precipitate was filtered and dried to constant weight, the conversion rate was 96% (proton nuclear magnetic resonance spectrum, 400MHz, CDCl 3 ), the number average molecular weight M of polyvalerolactone n 2850g mol -1 , the dispersion PDI is 1.08 (molecular exclusion chromatography, Waters column: 5mm, 300 7.8mm, tetrahydrofuran mobile phase, 0.7mL min-1, polystyrene as standard), 1 H NMR (400MHz, CDCl 3 ):δ(ppm)1.68(m,2H×n,(–CH2CH2CH2O–)n),1.70(m,2H×n,(–COCH2–CH2CH2–)n),2.34(t,2H×n,J= 6.8Hz, (–OCOCH2CH2–)n), 3.65(t, 2H, J=6.1Hz, –CH2CH2OH), 4.08(t, 2H×n, J=5.5Hz, (–CH2CH2O-)n), 5.12(s , 2H, ArCH2O), 7.32...

Embodiment 2

[0045] Organic salt (2) (22.1 mg, 0.05 mmol, 0.5 equiv), 5-hexen-1-ol (12.0 μL, 0.1 mmol, 1.0 equiv) and ε-caprolactone (5.5 ml, 50 mmol, 500 equiv) were added In the reaction flask, the temperature was raised to 180° C., and the reaction was stirred for 20 hours under the protection of Ar. The reaction solution was poured into ethanol, the precipitate was filtered and dried to constant weight, the conversion rate was 92% (proton nuclear magnetic resonance spectrum, 400MHz, CDCl 3 ), the number average molecular weight M of polycaprolactone n 41300g mol -1 , the dispersion PDI is 1.27 (molecular exclusion chromatography, Waters column: 5mm, 300 7.8mm, tetrahydrofuran mobile phase, 0.7mL min-1, polystyrene as the standard sample); 1 H NMR (400MHz, CDCl 3 ):δ(ppm),1.39(m,2H×n,(–CH2CH2CH2CH2CH2–)n),1.63(m,2H×n,(–CH2CH2CH2O–)n),1.68(m,2H×n,(–COCH2CH2CH2 –)n), 2.31(t, 2H×n, J=7.3Hz, (–OCOCH2CH2–)n), 3.65(t, 2H, J=6.6Hz, CH2CH2OH), 4.06(t, 2H×n, J= 6.6Hz, (–CH2CH2O–)n), 5.12(s,...

Embodiment 3

[0048] Add organic salt (4) (1955mg, 3mmol, 30equiv), propynyl alcohol (5.8μL, 0.1mmol, 1.0equiv) and carbonate (0.3mg, 3.0mmol, 30equiv) into the reaction flask, dissolve with 5mL of chloroform, Under the protection of Ar, the reaction was stirred at room temperature for 24 hours. The reactant was concentrated and poured into n-hexane, the precipitate was filtered and dried to constant weight, the conversion rate was 92% (proton nuclear magnetic resonance spectrum, 400MHz, CDCl 3 ), the number average molecular weight M of polycarbonate n 2820g mol -1 ;, the dispersion PDI is 1.10 (size exclusion chromatography, Waters column: 5mm, 300 7.8mm, tetrahydrofuran mobile phase, 0.7mL min-1, polystyrene as standard); 1 H NMR (400MHz, CDCl 3 ):δ(ppm)1.91(q,2H,J=6.1Hz,–CH2CH2OH),2.02–2.07(m,2H×n-1,(–OCH2CH2–)n-1),3.73(t,2H,J =6.0Hz, –CH2OH), 4.22–4.30(m, 4H×n-1, (–OCH2CH2CH2O–)n-1; m, 2H, –OCH2CH2CH2OH), 5.15(s, 2H, ArCH2O), 7.25–7.37( m, 5H, aromatic).

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Abstract

The invention discloses a method for cyclic compound ring opening polymerization and belongs to the technical field of organic catalytic and high polymer materials. According to the method disclosed by the invention, a cyclopropene salt is utilized to catalyze cyclic compound ring opening polymerization in the presence of an initiator to obtain polyester compounds. By means of the method disclosed by the invention, a macromolecular biodegradable material with large molecular weight, narrow dispersity and no metallic impurities can be obtained. A novel catalyst system is stable and general and is effective for a long time in a storage aspect. The macromolecular material prepared by the method can be applied to aspects of medicine carriers, nano reactors, films, material connectors and the like, further has biodegradability and is an environment-friendly material.

Description

technical field [0001] The invention belongs to the technical field of organic catalysis and polymer materials, and in particular relates to a method for catalyzing ring-opening polymerization of cyclic compounds. Background technique [0002] Among many synthetic polymer materials, aliphatic polyester is a biodegradable and bioabsorbable polymer material, which is easy to blend with other polymer materials and can improve the degradability of polymer materials. As a fully degradable and environmentally friendly material derived from renewable resource crops, it has attracted widespread attention and research from people all over the world. [0003] The traditional method of preparing polyester is mainly polycondensation method. This method usually requires high temperature, consumes a lot of energy, and the obtained product has a low molecular weight and a wide molecular weight distribution. The reaction process is uncontrollable, which is not conducive to the stability of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/82C08G63/08C08G63/84C08G63/87C08G64/30
CPCC08G63/08C08G63/823C08G63/84C08G63/87C08G64/30
Inventor 郭凯徐嘉熙李振江刘晶晶徐松泉王海鑫王鑫
Owner NANJING UNIV OF TECH
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