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Epoxide-carbon dioxide stereoselective alternating copolymer

A technology of epoxy and carbon dioxide, which is applied in the field of preparing polycarbonate with high stereoregularity, can solve the problem of high price and achieve the effect of high enantioselectivity

Inactive Publication Date: 2010-05-26
THE UNIV OF TOKYO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] It is believed that the above-mentioned optically active polycarbonates can be prepared by using one of the optical isomers of chiral epoxides, but since chiral epoxides are usually obtained in the form of racemic mixtures, the preparation method must prepare very expensive One of the high optical isomers

Method used

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  • Epoxide-carbon dioxide stereoselective alternating copolymer
  • Epoxide-carbon dioxide stereoselective alternating copolymer
  • Epoxide-carbon dioxide stereoselective alternating copolymer

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0035] The epoxide compound that can be used as a monomer raw material in the production method of the present invention includes any of chiral epoxides and meso epoxides. Specifically, an epoxide represented by the following formula may be included.

[0036]

[0037] (In the above formula, R 1 and R 2 Under the condition that they are not hydrogen atoms at the same time, they can be the same or different, and R 1 and R 2 independently hydrogen atom, halogen atom, substituted amino (-NR 3 R 4 ), cyano, linear or branched C 1 ~C 20 Alkyl, C 2 ~C 20 Alkenyl or C 2 ~C 20 Alkynyl, C 4 ~C 10 Cycloalkyl, C 6 ~C 40 Aryl or C 7 ~C 40 Arylalkyl, or, R 1 and R 2 can also together form saturated or unsaturated C 4 ~C 10 Alicyclic group; the aryl part in the above-mentioned aryl and arylalkyl and the above-mentioned alicyclic group can also be selected from halogen atoms, straight chain or branched C 1 ~C 20 Alkyl, C 2 ~C 20 Alkenyl or C 2 ~C 20 Alkynyl, C 4 ...

Embodiment

[0052] The present invention will be described more specifically by the following examples, but the present invention is not limited to these examples.

[0053] The compounds obtained in this example 1 The measurement of the H NMR spectrum was performed with JNM-ECP500 (500 MHz) manufactured by JEOL Corporation.

[0054] Molecular weight determination of optically active polycarbonate, using a high-performance liquid chromatography system (DG660B·PU713·UV702·RI704·C0631A) manufactured by GL Sciences and 2 KF-804F columns manufactured by SHODEX, using tetrahydrofuran as the eluent (40° C., 1.0 mL / min), measured in terms of polystyrene standard as a standard, processed and obtained by analysis software (EZChrom Elite, manufactured by Scientific Software Co., Ltd.).

[0055] In addition, in this example, the optical purity of the unreacted optically active epoxide was determined based on the enantiomeric excess (%ee) calculated by converting the epoxide into the corresponding cy...

Synthetic example A

[0065] Synthesis Example A: Synthesis of Novel Schiff Base Compounds

[0066] A-1. Synthesis of salcy ligand 1b

[0067]

[0068] Under argon atmosphere, in a Schlenk tube with a capacity of 20 mL, add salicylaldehyde derivative 3 (248 mg, 0.91 mmol) and tetrahydrofuran (10 mL), slowly add (S)-2- (Diphenylmethoxymethyl)pyrrolidine [(S)-4, 450 mg, 1.7 mmol]. After stirring at 25°C for 2 hours, the resulting precipitate was filtered, and the filtrate was concentrated to obtain a salicylaldehyde derivative (S)-5 (384 mg, yield 84%). 1 HNMR (CDCl 3 , 500MHz)d10.29(s, 1H), 7.56-7.50(m, 5H), 7.40-7.29(m, 8H), 4.36(d, J=13.5Hz, 1H), 3.99(dd, J=9.9, 4.1Hz, 1H), 3.68(d, J=13.7Hz, 1H), 2.96(s, 3H), 2.38-2.34(m, 1H), 2.20-2.15(m, 1H), 2.10-2.02(m, 1H ), 1.86-1.80 (m, 1H), 1.46-1.40 (m, 1H), 1.30 (s, 9H), 0.72-0.62 (m, 1H).

[0069]

[0070] The obtained salicylaldehyde derivative (S)-5 (178 mg, 0.39 mmol) was dissolved in ethanol (1.0 mL), dichloromethane (3.0 mL), and (1R,...

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Abstract

The present invention provides a method for manufacturing polycarbonate, which has a high conversion rate of a propylene oxide material into a polymer and can control stereoregularity of the macromolecular structure, and a catalytic compound for the manufacturing method. The manufacturing method of the present invention is a method for manufacturing a polycarbonate copolymer by copolymerizing an epoxide compound as a monomer with carbon dioxide in the presence of a planar tetracoordinate-type cobalt-Schiff base complex, wherein a ligand of the Schiff base is N,N'-bis(2-hydroxybenzylidene) ethylenediamine, N,N'-bis(2-hydroxybenzylidene) phenylenediamine, or a derivative thereof, and a methyl group substituted with an amino group having an asymmetrical carbon atom or an asymmetrical axis is introduced to the 3- and / or 3'-position of the benzene ring derived from the salicyl group. In addition, the catalytic compound of the present invention is a cobalt-Schiff base complex, wherein a methyl group substituted with an amino group having an asymmetrical carbon atom or an asymmetrical axis is introduced to the 3- and / or 3'-position of the salicyl group.

Description

technical field [0001] The present invention relates to a process for the preparation of polycarbonate by alternating copolymerization of epoxides and carbon dioxide and a catalyst for the preparation. In particular, the present invention relates to a method for producing polycarbonate having high stereoregularity and a catalyst used for the production method. Background technique [0002] In recent years, as a technique for effectively utilizing carbon dioxide, a production method of polycarbonate utilizing copolymerization of epoxide and carbon dioxide has attracted attention. In addition, by controlling the stereoregularity of polycarbonate, development and research aiming at the presentation of new physical properties and functions, and the expansion of applications are ongoing. [0003] For example, control of stereoregularity of polycarbonate by regularly introducing optically active centers into the polycarbonate polymer chain has been studied. An optically active p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G64/34
CPCC08G64/34
Inventor 野崎京子中野幸司
Owner THE UNIV OF TOKYO
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