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Metal free catalyst system for synergistic catalysis of lactone ring opening polymerization in organic solvent

A technology of metal-free catalysis and synergistic catalysis, applied in the field of polymer synthetic materials, can solve the problems of poor catalytic activity and low conversion rate, and achieve the effects of fast reaction, high conversion rate, and simple and easy-to-operate polymerization process.

Active Publication Date: 2019-06-07
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problems of poor catalytic activity and low conversion rate in the ring-opening polymerization of polyester materials, the invention provides a metal-free catalytic system for organic synergistic catalysis of lactone ring-opening polymerization, i.e. N-heterocyclic exoolefin ( NHOs) and thiourea (TUs) / urea (Us) synergistic catalytic system, using benzyl alcohol, butanediol and other alcohols as initiators, realized an efficient, fast and controllable active ring-opening polymerization catalytic system, and obtained molecular weight Narrow distribution, metal-free polyester material

Method used

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  • Metal free catalyst system for synergistic catalysis of lactone ring opening polymerization in organic solvent
  • Metal free catalyst system for synergistic catalysis of lactone ring opening polymerization in organic solvent
  • Metal free catalyst system for synergistic catalysis of lactone ring opening polymerization in organic solvent

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: Synthesis of N-heterocyclic exoolefin NHO 1

[0047] The reaction formula of synthetic N-heterocyclic exoolefin NHO 1 is as follows:

[0048]

[0049] Under argon or nitrogen atmosphere, 50mL Schlenk reaction tube is pumped and baked three times, dry compound Pre 1 (2.38g, 10mmol), 5mL newly steamed anhydrous tetrahydrofuran is added in the 50mL Schlenk reaction tube, the tetrahydrofuran solution (THF) of injection KHMDS ( 10 mL, 1M in THF), stirred at room temperature for 6 h, filtered, and vacuum-dried to constant weight to obtain yellow solid NHO 1 (0.73 g, yield=66%). 1 H NMR (400MHz, d 8 -Toluene)δ(ppm)5.32(s,2H,N-CH=CH-N),2.55(s,2H,-C=CH 2 ),2.41(s,6H,N-CH 3 ). 13 C NMR (400MHz, d 8 -Toluene) δ (ppm) 112.54, 39.92, 32.07.

Embodiment 2

[0050] Embodiment 2: Synthesis of N-heterocyclic exoolefin NHO 2

[0051] Synthetic N-heterocyclic exoolefin NHO The reaction formula is as follows:

[0052]

[0053] Under argon or nitrogen atmosphere, the 10mL Schlenk reaction tube was pumped and baked three times, the dry compound Pre 2 (0.53g, 2mmol), 3mL freshly steamed anhydrous tetrahydrofuran was added in the 10mL Schlenk reaction tube, and the THF solution of KHMDS ( 2mL, 1M in THF), stirred at room temperature for 6h, filtered, and vacuum-dried to constant weight to obtain yellow solid NHO 2 (0.26g, yield=19%). 1 H NMR (400MHz, d 8 -Toluene)δ(ppm)2.67(s,2H,-C=CH 2 ),2.53(s,6H,N-CH 3 ),1.42(s,6H,C-CH 3 ). 13 C NMR (400MHz, d 8 -Toluene) δ (ppm) 153.11, 113.83, 40.12, 28.81, 8.16.

Embodiment 3

[0054] Embodiment 3: Synthesis of N-heterocyclic exoolefin NHO 3

[0055] The reaction formula of synthetic N-heterocyclic exoolefin NHO is as follows:

[0056]

[0057] Under argon or nitrogen atmosphere, the 25mL Schlenk reaction tube was pumped and baked three times, the dry compound Pre 3 (1.47g, 5mmol), 5mL of newly steamed anhydrous THF were added in the 25mL Schlenk reaction tube, and the THF solution of KHMDS ( 5mL, 1M in THF), stirred at room temperature for 6h, filtered, and vacuum-dried to constant weight to obtain yellow solid NHO 3 (0.64g, yield=77%). 1 H NMR (400MHz, d 8 -Toluene)δ(ppm)2.59(s,6H,N-CH 3 ),1.86(s,6H,C-CH 3 ), 1.47(s,6H,-C=CCH 3 ).

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Abstract

The invention discloses a metal free catalyst system for synergistic catalysis of lactone ring opening polymerization in an organic solvent, and belongs to the field of polymer synthesis. The providedsystem is used to efficiently catalyze controllable active ring opening polymerization of lactone. Under the protection of inert gas, lactone is taken as the monomer, in an organic solvent, N-heterocyclic alkene and thiourea (or urea) co-catalyze the alcohol triggered ring opening polymerization of lactone. The synthesis method is carried out in an organic solvent, obtained aliphatic hydrocarbonpolyester does not contain any metal; the reaction conditions are mild, the reactions are fast, the polymerization process is easy and is easy to operate; the using amount of catalysts is very little,the conversion rate is high, and the obtained polyester has narrow molecular weight distribution.

Description

technical field [0001] The invention relates to a metal-free catalytic system for organic synergistic catalysis of lactone ring-opening polymerization, which belongs to the technical field of polymer synthetic materials. Background technique [0002] In recent years, small molecular organic compounds have been widely used as catalysts or initiators in the ring-opening polymerization of lactones. Through different catalytic reaction mechanisms, a metal-free biocompatible and biodegradable aliphatic polyester / polyether / polyamine material is obtained. Because aliphatic hydrocarbon polyester materials have good mechanical properties, they are widely used in chemical, food packaging, medical polymer and other fields. [0003] At present, catalytic ring-opening polymerization is the most important method for preparing synthetic aliphatic polyesters, and its catalytic system includes metal-ligand or metal alkane compound catalysis, enzyme catalysis and organic small molecule catal...

Claims

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Application Information

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IPC IPC(8): C08G63/87C08G63/08
Inventor 王庆刚周丽徐广强咸漠吕承东孙西同
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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