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Method for producing polypyridinium

外国特許コード F110005504
整理番号 N021-01WO
掲載日 2011年9月7日
出願国 アメリカ合衆国
出願番号 59317605
公報番号 20080132676
公報番号 7985829
出願日 平成17年3月23日(2005.3.23)
公報発行日 平成20年6月5日(2008.6.5)
公報発行日 平成23年7月26日(2011.7.26)
国際出願番号 JP2005005180
国際公開番号 WO2005090443
国際出願日 平成17年3月23日(2005.3.23)
国際公開日 平成17年9月29日(2005.9.29)
優先権データ
  • 特願2004-084518 (2004.3.23) JP
  • 2005WO-JP05180 (2005.3.23) WO
発明の名称 (英語) Method for producing polypyridinium
発明の概要(英語) (US7985829)
A production method for polypyridinium having a narrow molecular weight distribution and a desired molecular weight is provided.
Polypyridinium 3 having a narrow molecular weight distribution and a desired molecular weight is synthesized by allowing a pyridine derivative monomer 2 to polymerize on a polymerization initiator 1 such as a specially designed 4-halopyridinium and the like in the presence of a dissolution accelerating agent, such as tetrabutyl ammonium tetrafluoroborate, that dissolves the polymer formed in a solvent as in the chemical below. where Y represents an anion that dissolves in an organic solvent, X and Z represent halogen atoms, R represents hydrocarbon groups and the like and o is about 1 to 300.
特許請求の範囲(英語) [claim1]
1. A method for producing polypyridinium comprising reacting a polymerization initiator and a monomer represented by the chemical formula

in an organic solvent in the presence of a dissolution accelerating agent comprising hydrophobic anions, where R' represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, an ester group or an aromatic ring forming a condensed ring with the pyridine ring, m is an integer from 1 to 4 and Z represents a halogen atom,
wherein the polymerization initiator is 4-halopyridinium or its derivatives, 4-haloquinolinium or its derivatives, 9-haloacrydinium or its derivatives, 2- or 4-halopyrimidine or their derivatives, 3- or 4-halopyridazine or their derivatives, 2-halopyrazine or its derivatives, 2-, 4- or 5-haloimidazole or their derivatives, 3-, 4- or 5-halopyrazole or their derivatives, 3-, 4- or 5-haloisothiazole or their derivatives, 3-, 4- or 5-haloisooxazole or their derivatives, halotriazine, mononitro or polynitrohalobenzene or their derivatives, or polycyanohalobenzene or its derivatives.
[claim2]
2. The method of claim 1 wherein the polymerization initiator is a 4-halopyridinium represented by the chemical formula

or its derivatives, where R represents R''(CH2)n -- , wherein R'' represents a hydrocarbon group or a heterocyclic group and n represents an integer that is at least one, or an aryl group or a heterocyclic ring that may contain substituents, however, the heterocyclic group has its carbon atom bonded to the nitrogen atom in the pyridine ring, X represents a halogen atom, Y represents an anion soluble in the organic solvent, R' represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, an ester group or an aromatic ring forming a condensed ring with the pyridine ring and m is an integer from 1 to 4.
[claim3]
3. The method of claim 2 wherein Y is a halide ion, perchlorate ion, tetrafluoroborate ion, hexafluorophosphate ion or tetraphenyl borate ion, X and Y are chlorine atoms or bromine atoms, and the hydrophobic anion is a perchlorate ion, a tetrafluoroborate ion, a hexafluorophosphate ion, a tartarate ion, a citrate ion, a nicotinate ion, or a phosphate ion containing a binaphthyl group.
[claim4]
4. The method of claim 1 wherein the dissolution accelerating agent is tetrabutylammonium perchlorate, tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, sodium perchlorate, sodium tetrafluoroborate, sodium hexafluorophosphate, tetraethylammonium perchlorate, tetraethylammonium tetrafluoroborate, tetraethylammonium hexafluorophosphate, sodium tetraphenylborate, sodium p-toluenesulfonate, sodium alkylsulfonate having 6 to 24 carbon atoms, sodium alkylphosphate having 6 to 24 carbon atoms, or a phospholipid having 6 to 24 carbon atoms.
[claim5]
5. The method of claim 4 wherein the dissolution accelerating agent is tetrabutylammonium tetrafluoroborate.
[claim6]
6. The method of claim 5 wherein the polymerization initiator is N-(4'-tert-butylbenzyl)-4-chloropyridinium and the monomer is 4-chloropyridine.
[claim7]
7. The method of claim 1 further comprising reacting the reaction product with a polymerization terminating agent, wherein the polymerization terminating agent is pyridine, quinoline or acrydine substituted with amino groups, alkoxy groups or alkyl groups or their derivatives, triphenylphosphine or its derivatives, or amine derivatives substituted with alkyl groups or allyl groups.
[claim8]
8. The method of claim 7 wherein the polymerization terminating agent is added to the reaction solution to allow the reaction material to react with the polymerization terminating agent.
[claim9]
9. A polypyridinium produced by the method of claim 1.
[claim10]
10. The polypyridinium of claim 8 wherein the polypyridinium is represented by the chemical formula,

where R represents R''(CH2)n -- , wherein R'' represents a hydrocarbon group or a heterocyclic group and n represents an integer that is at least one, or an aryl -group or a heterocyclic ring that may contain substituents, however, the heterocyclic group has its carbon atom bonded to the nitrogen atom in the pyridine ring, Z represents a halogen atom, R' represents a hydrogen atom, an alkyl group, an alkoxv group, a halogen atom, a nitro group, an ester group or an aromatic ring forming a condensed ring with the pyridine ring, m is an integer from 1 to 4 and o is 1 to 300.
[claim11]
11. The method of claim 3 wherein the dissolution accelerating agent is tetrabutylammonium perchlorate, tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, sodium perchlorate, sodium tetrafluoroborate, sodium hexafluorophosphate, tetraethylammonium perchlorate, tetraethylammonium tetrafluoroborate, tetraethylammonium hexafluorophosphate, sodium tetraphenylborate, sodium p-toluenesulfonate, sodium alkylsulfonate having 6 to 24 carbon atoms, sodium alkylphosphate having 6 to 24 carbon atoms, or phospholipids having 6 to 24 carbon atoms.
[claim12]
12. The method of claim 11 wherein the dissolution accelerating agent is tetrabutylammonium tetrafluoroborate.
[claim13]
13. A polypyridinium produced by the method of claim 3.
[claim14]
14. The method of claim 6 further comprising reacting the reaction product with a polymerization terminating agent, wherein the polymerization terminating agent is pyridine, quinoline or acrydine substituted with amino groups, alkoxy groups or alkyl groups or their derivatives, triphenylphosphine or its derivatives, or amine derivatives substituted with alkyl groups or allyl groups.
[claim15]
15. The method of claim 14 wherein the polymerization terminating agent is added to the reaction solution to allow the reaction material to react with the polymerization terminating agent.
[claim16]
16. The method of claim 13 wherein the polymerization initiator is N-(4'-tert-butylbenzyl)-4-chloropyridinium and the monomer is 4-chloropyridine.
[claim17]
17. A polypyridinium produced by the method of claim 6.
[claim18]
18. The polypyridinium of claim 13 wherein the polypyridinium is represented by the chemical formula

where R represents R''(CH2)n -- , wherein R'' represents a hydrocarbon group or a heterocyclic group and n represents an integer that is at least one, or an aryl group or a heterocyclic ring that may contain substituents, however, the heterocyclic group has its carbon atom bonded to the nitrogen atom in the pyridine ring, Z represents a halogen atom, R' represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, an ester group or an aromatic ring forming a condensed ring with the pyridine ring, m is an integer from 1 to 4 and o is 1 to 300.
[claim19]
19. The polypyridinium of claim 17 wherein the polypyridinium is represented by the chemical formula

where R represents R''(CH2)n -- , wherein R'' represents a hydrocarbon group or a heterocyclic group and n represents an integer that is at least one, or an aryl group or a heterocyclic ring that may contain substituents, however, the heterocyclic group has its carbon atom bonded to the nitrogen atom in the pyridine ring, Z represents a halogen atom, R' represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, an ester group or an aromatic ring forming a condensed ring with the pyridine ring, m is an integer from 1 to 4 and o is 1 to 300.
  • 発明者/出願人(英語)
  • IYODA TOMOKAZU
  • KAMATA KAORI
  • SUZUKI YUKIMITSU
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
参考情報 (研究プロジェクト等) CREST Nano Factory and Process Monitoring for Advanced Information Processing and Communication AREA
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