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Organic bismuth compound, method for producing same, living radical polymerization initiator, method for producing polymer using same, and polymer

A technology of polymerization initiator and free radical, applied in the direction of bismuth organic compounds, etc., can solve the problems of undisclosed organic bismuth compounds and the like

Inactive Publication Date: 2007-12-19
OTSUKA CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although an organotellurium compound is used as an initiator, the organobismuth compound of the present invention is not disclosed

Method used

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  • Organic bismuth compound, method for producing same, living radical polymerization initiator, method for producing polymer using same, and polymer
  • Organic bismuth compound, method for producing same, living radical polymerization initiator, method for producing polymer using same, and polymer
  • Organic bismuth compound, method for producing same, living radical polymerization initiator, method for producing polymer using same, and polymer

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 4

[0184] Tetramethyldi (Synthesis Example 7)

[0185] Azo polymerization initiator:

[0186] 2,2'-Azobis(isobutyronitrile) (manufactured by Daisuke Chemical Co., Ltd., trade name: AIBN)

[0187] 1,1'-Azobis(1-cyclohexanenitrile) (manufactured by Daishin Chemical Co., Ltd., trade name: ACHN)

[0188] 2,2'-Azobis-2,4-dimethylvaleronitrile (manufactured by Daisen Chemical Co., Ltd., trade name: ADVN)

[0189] monomer:

[0190] Adamantane Monomer MADM

[0191]

[0192] Norbornane Monomer NBLM

[0193]

Synthetic example 1

[0195] Trimethyl Synthesis

[0196] Under an argon atmosphere, 25 g of bismuth tribromide dissolved in 40 ml of THF was added dropwise to 180 ml of a 1.0 M methyl lithium diethyl ether solution while maintaining reflux. It was then stirred at room temperature for 1.5 hours. After distilling off the solvent under normal pressure, distillation was performed under reduced pressure. By distilling the obtained distillate again, 8.1 g (54.8%) of a colorless oily substance was obtained.

[0197] pass 1 H-NMR confirmed the target object.

[0198] 1 H-NMR (300MHz, CDCl 3 )1.13(s, 9H)

Synthetic example 2

[0200] Dimethyl Synthesis of bromides

[0201] Under the atmosphere of argon gas, the trimethyl group synthesized in Synthesis Example 1 A liquid in which 7.2 g of bismuth tribromide was dissolved in 13 ml of THF was added dropwise to 8.0 g (31.5 mmol). It was then stirred at room temperature for 1.5 hours. After the reaction solution was filtered through a 0.2 µm membrane filter, THF was distilled off under reduced pressure to obtain 14.23 g (94.5%) of a light yellow amorphous substance.

[0202] pass 1 H-NMR confirmed the target object.

[0203] 1 H-NMR (300MHz, DMSO) 1.52(s, 6H)

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PUM

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Abstract

An organobismuth compound represented by the formula (1) wherein R 1 and R 2 are C 1 -C 8 alkyl, aryl, substituted aryl or an aromatic heterocyclic group, R 3 and R 4 are each a hydrogen atom or C 1 -C 8 alkyl, and R 5 is aryl, substituted aryl, an aromatic heterocyclic group, acyl, amido, oxycarbonyl or cyano.

Description

technical field [0001] The invention relates to an organic bismuth compound and a preparation method thereof. More specifically, it relates to an organic bismuth-based living radical polymerization initiator, a method for preparing a living radical polymer using the initiator, a method for preparing a living radical polymer, a random copolymer, a random copolymer, an embedded A preparation method of a block copolymer, a block copolymer, and these macromolecule living free radical polymerization initiators and polymers. [0002] In addition, the polymer of the present invention can be suitably used as a resist or the like used in the manufacture of a semiconductor device. Background technique [0003] Living radical polymerization is a polymerization method that not only maintains the simplicity and versatility of free radical polymerization, but also can precisely control the molecular structure. It has exerted great power in the synthesis of new polymer materials. As an e...

Claims

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Application Information

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IPC IPC(8): C07F9/94C08F4/42
CPCC07F9/94C08F297/02C08F257/02C08F4/42C08F291/06C08F212/08C08F226/10
Inventor 山子茂龟岛隆河野和浩伊东治大门惠美子周健菅生久仁彦
Owner OTSUKA CHEM CO LTD
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