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Acrylic star polymer

a star polymer and acrylic acid technology, applied in the field of acrylic acid-based star polymer, can solve the problems of not being able to achieve satisfactory properties and cannot be said to control molecular weight, and achieve the effect of excellent acid decomposability and great industrial utility valu

Inactive Publication Date: 2009-08-20
NIPPON SODA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0014]As described above, the star polymer of the present invention has a narrow molecular weight distribution and is also excellent in acid decomposability, and is therefore useful as a resist material and its industrial utility value is great.

Problems solved by technology

However, the molecular weight distribution of the compound is mostly 1.5 or more and it cannot be said that the molecular weight is controlled.
Although a trial of applying the compound as a resist material was made by making use of acid decomposability, satisfactory properties were not obtained necessarily.

Method used

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Examples

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Effect test

example 1

[0051]Under a nitrogen atmosphere, 331 g of tetrahydrofuran (THF) containing 13 mmol of lithium chloride was maintained at −40° C. and 26 mmol of sec-butyllithium (SBL) was added while stirring, and then 88 g of a THF solution containing 97 mmol of 2-methyl-2-adamanthyl methacrylate (2MAdMA), 78 mmol of a mixture (TLMA) of (±)-octahydro-3-oxo-4,7-methanoisobenzofuran-5-ylmethacrylate and a (±)-octahydro-1-oxo-4,7-methanoisobenzofuran-5-ylmethacrylate as a positional isomer and 19 mmol of tert-butyl methacrylate (tBMA) was added dropwise and the reaction was continued for 30 minutes. A small amount of the reaction solution was taken out from the reaction system and gas chromatography (hereinafter, abbreviated as GC) analysis revealed that the monomer was completely consumed.

[0052]Then, 12 g of a THF solution containing 22 mmol of 2,5-dimethyl-2,5-hexanediol dimethacrylate (MDMA) was added dropwise and the reaction was continued for 30 minutes. A small amount of the reaction solution ...

example 2

[0053]Under a nitrogen atmosphere, 233 g of THF containing 15 mmol of lithium chloride was maintained at −40° C. and 31 mmol of SBL was added while stirring, and then 171 g of a THF solution containing 88 mmol of 2MAdMA, 88 mmol of methacrylic acid-5-oxo-4-oxatricyclo[4.2.1.03,7]nonan-2-yl (NLMA) and 19 mmol of tBMA was added dropwise and the reaction was continued for 30 minutes. A small amount of the reaction solution was taken out from the reaction system and GC analysis revealed that the monomer was completely consumed.

[0054]Then, 12 g of a THF solution containing 22 mmol of MDMA was added dropwise and the reaction was continued for 30 minutes. A small amount of the reaction solution was taken out from the reaction system and GC analysis revealed that the MDMA monomer was completely consumed, and then the reaction was terminated by the THF solution containing hydrochloric acid. The reaction-terminated solution was poured into a large amount of water thereby to precipitate a poly...

example 3

[0055]Under a nitrogen atmosphere, 341 g of THF containing 7 mmol of lithium chloride was maintained at −40° C. and 14 mmol of SBL was added while stirring, and then 10 g of a THF solution containing 22 mmol of 2MAdMA was added dropwise and the reaction was continued for 30 minutes. A small amount of the reaction solution was taken out from the reaction system and GC analysis revealed that the 2MAdMA monomer was completely consumed. Then, 78 g of a THF solution containing 66 mmol of 2MAdMA, 88 mmol of TLMA and 19 mmol of tBMA was added dropwise and the reaction was continued for 30 minutes. A small amount of the reaction solution was taken out from the reaction system and GC analysis revealed that the monomer was completely consumed.

[0056]Then, 12 g of a THF solution containing 22 mmol of MDMA was added dropwise and the reaction was continued for 30 minutes. A small amount of the reaction solution was taken out from the reaction system and GC analysis revealed that the MDMA monomer ...

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Abstract

An object of the present invention is to provide an acrylic acid-based star polymer which has a controlled structure with a narrow molecular weight distribution and acid decomposability. The star polymer contains, as a core portion, a polymer chain having a repeating unit derived from a polyacrylate which has at least two partial structures represented by formula (I):(wherein R1, represents a hydrogen atom or a methyl group, R2 and R3 each independently represents an organic group which is combined via a carbon atom, and a Cl carbon represents a carbon atom which is combined with a moiety via a carbon atom) and, as an arm portion, a polymer chain having a repeating unit derived from a (meth)acrylic ester represented by formula (II):(wherein R4 represents a hydrogen atom or a methyl group, and represents an organic group), excluding a homopolymer chain having a repeating unit derived from a (meth)acrylic ester in which R5 is a C1-C4 alkyl group when R1 in formula (I) is a methyl group.

Description

TECHNICAL FIELD[0001]The present invention relates to an acrylic acid-based star polymer and, more particularly, to a star polymer containing a repeating unit derived from a polyacrylate as a core portion and a repeating unit derived from an acrylic ester as an arm portion.[0002]This application claims priority on Japanese Patent Application No. 2004-162081 filed on May 31, 2004 and Japanese Patent Application No. 2005-132073 filed on Apr. 28, 2005, the disclosure of which is incorporated by reference herein.BACKGROUND ART[0003]It has been known that a star polymer is obtained by polymerizing methyl methacrylate, isobutyl methacrylate and t-butyl methacrylate using, as an initiator, diphenylhexyllithium obtained by reacting 1,1-diphenylethylene with s-butyllithium, and reacting with dicumyl alcohol dimethacrylate or 2,5-dimethyl-2,5-hexanediol dimethacrylate (see, for example, Nonpatent Document 1).[0004][Nonpatent Document 1] L. Kilian, et. al., J. Polymer Science, Part A, 2003, 30...

Claims

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Application Information

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IPC IPC(8): C08G63/08C08F293/00C08F297/02
CPCC08F293/00C08F297/02C08F297/026C08L53/00C08L2666/02
Inventor MATSUMOTO, HITOSHINAKAMURA, MITSUHIRO
Owner NIPPON SODA CO LTD
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