WO2007114652A1 - Nouveaux monomères benzimidazole terminés par des groupes trifluorovinyloxy et membrane de polybenzimidazoles préparée au moyen de ces monomères - Google Patents

Nouveaux monomères benzimidazole terminés par des groupes trifluorovinyloxy et membrane de polybenzimidazoles préparée au moyen de ces monomères Download PDF

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Publication number
WO2007114652A1
WO2007114652A1 PCT/KR2007/001650 KR2007001650W WO2007114652A1 WO 2007114652 A1 WO2007114652 A1 WO 2007114652A1 KR 2007001650 W KR2007001650 W KR 2007001650W WO 2007114652 A1 WO2007114652 A1 WO 2007114652A1
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WO
WIPO (PCT)
Prior art keywords
formula
membrane
fluorinated
polymer
benzoate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2007/001650
Other languages
English (en)
Inventor
Jeong-Hoon Kim
Soo Bok Lee
Bong-Jun Chang
In Jun Park
Dong-Kwon Kim
Jong-Wook Ha
Kwang-Won Lee
Kwang-Han Kim
Dong Jin Kim
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Korea Research Institute of Chemical Technology KRICT
Original Assignee
Korea Research Institute of Chemical Technology KRICT
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Korea Research Institute of Chemical Technology KRICT filed Critical Korea Research Institute of Chemical Technology KRICT
Publication of WO2007114652A1 publication Critical patent/WO2007114652A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a fluorinated benzimidazole monomer
  • this polymer shows improved processability, gas
  • membrane to be useful as a material for fuel cell, gas permeation as an optical or
  • Polybenzimidazole has superior properties in various aspects such as
  • polybenzimidazole shows
  • polybenzimidazole to increase solubility in an organic solvent and gas permeability
  • polybenzimidazole with improved solubility, gas permeability and low dielectric
  • trifluorovinyloxy groups shows improvements in properties such as staining
  • the preset invention aims to provide a fluorinated benzimidazole
  • the present invention also aims to provide a polymer membrane prepared
  • J Ai T is I l] or I Ij I Il
  • X is a direct bond, -O-, -S-, -
  • step (a) methyl(bromotetrafluoroethoxy)benzoate of
  • formula (4) is prepared by reacting hydroxybenzoate of formula (2) and
  • the water or aprotic polar solvent is used as a reaction solvent, and any combination thereof.
  • aprotic polar solvent such as dimethylsulfoxide (DMSO), N-methyl-DMSO
  • aprotic solvent may be used as the aprotic solvent.
  • This reaction solvent is preferably used in such an amount as to maintain the concentration of total monomers of formulas 2 and 3 within 1-40 wt%. If the
  • alkaline earth metal or the precursor compound thereof is used
  • NaOH or KOH is preferred when water is used as the
  • This alkaline earth metal or precursor compound thereof is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-oxide
  • the reaction is preferred to be performed at 0-50 0 C for 1-48 hours.
  • step (c) fluorinated benzimidazole monomer of
  • formula (1) is prepared by oxidizing the imidazole benzoate compounds of formula
  • THF tetrahydrofuran
  • dioxane dioxane
  • solvent is preferred to be used in an amount of 5-40 wt% relative to the weight o f
  • reaction efficiency may be lowered when the amount is below 5
  • imidazole benzoate compound of formula 6 is oxidized to introduce
  • I Ar I is I Ij or I IJ I Ij ;
  • X is a direct bond, -O-, -S-, -CO-,
  • n is an integer of from 50 to 1,000.
  • This polymer is prepared by introducing perfluorocyclobutane group with superiority in chemical resistance and thermal stability into conventional
  • the present invention also relates to a polymer membrane
  • the polymer of formula 7 is dissolved in an organic solvent to prepared
  • the coating may be performed
  • the organic solvent may be selected among those which are not involved in
  • DMSO dimethylsulfoxide
  • DMAc dimethylacetate
  • DMF dimethylformamide
  • NMP N-methyl-2-pyrrolidone
  • invention e.g. glass, metal, ceramic and polymer such as polysulfone or
  • the step of drying was performed at 50-200 0 C under normal pressure or vacuum for from 10 minutes to 24 hours, which is a common condition in a
  • This polymer membrane may be prepared into any form including a film, a
  • Figure 1 is a hydrogen nuclear magnetic resonance ( 1 H NMR) spectrum of a
  • Figure 2 is a fluorine nuclear magnetic resonance ( 19 F NMR) spectrum of a
  • Figure 3 is a hydrogen nuclear magnetic resonance ( 1 H NMR) spectrum of a
  • Example 2 is a fluorine nuclear magnetic resonance ( 19 F NMR) spectrum of a
  • the polymer membrane herein comprising fluorinated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

La présente invention concerne un monomère benzimidazole fluoré comprenant des groupes trifluorovinyloxy et une membrane polymère préparée au moyen de ce monomère benzimidazole fluoré, et en particulier un nouveau monomère benzimidazole fluoré terminé par des groupes trifluorovinyloxy et un polymère benzimidazole fluoré comprenant un groupe perfluorocyclobutane. Du fait d'une faible énergie de surface du groupe perfluorocyclobutane, ce polymère présente une aptitude au traitement, une perméation gazeuse et un pouvoir d'adhérence améliorés, une faible énergie de surface et une constante diélectrique faible, ce qui permet d'utiliser cette membrane de polymère comme matériau pour une pile à combustible, pour la perméation gazeuse ou comme matériau optique, électrique ou électronique.
PCT/KR2007/001650 2006-04-05 2007-04-04 Nouveaux monomères benzimidazole terminés par des groupes trifluorovinyloxy et membrane de polybenzimidazoles préparée au moyen de ces monomères Ceased WO2007114652A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2006-0031052 2006-04-05
KR1020060031052A KR100744827B1 (ko) 2006-04-05 2006-04-05 트리플루오로비닐옥시기를 포함하는 불소계 벤즈이미다졸 단량체 및 이의 제조방법

Publications (1)

Publication Number Publication Date
WO2007114652A1 true WO2007114652A1 (fr) 2007-10-11

Family

ID=38563875

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2007/001650 Ceased WO2007114652A1 (fr) 2006-04-05 2007-04-04 Nouveaux monomères benzimidazole terminés par des groupes trifluorovinyloxy et membrane de polybenzimidazoles préparée au moyen de ces monomères

Country Status (2)

Country Link
KR (1) KR100744827B1 (fr)
WO (1) WO2007114652A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012510458A (ja) * 2008-12-02 2012-05-10 サミット コーポレイション ピーエルシー 抗細菌化合物
US8987308B2 (en) 2010-06-01 2015-03-24 Summit Corporation Plc Compounds for the treatment of Clostridium difficile-associated disease

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HUTZLER R.F. ET AL.: "Synthesis and characterization of polybenzazoles containing hexafluoroisopropylidene", HIGH PERFORMANCE POLYMERS, vol. 4, no. 3, 1992, pages 161 - 171 *
JIN J. ET AL.: "Polybenzimidazoles(PBI) from perfluorocyclobutyl(PFCB) monomers", PMSE PREPRINTS, vol. 91, 2004, pages 504 - 505 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012510458A (ja) * 2008-12-02 2012-05-10 サミット コーポレイション ピーエルシー 抗細菌化合物
US8975416B2 (en) 2008-12-02 2015-03-10 Summit Corporation Plc Antibacterial compounds
US9314456B2 (en) 2008-12-02 2016-04-19 Summit Therapeutics Plc Antibacterial compounds
US9763925B2 (en) 2008-12-02 2017-09-19 Summit Therapeutics Plc Antibacterial compounds
US8987308B2 (en) 2010-06-01 2015-03-24 Summit Corporation Plc Compounds for the treatment of Clostridium difficile-associated disease
US9278091B2 (en) 2010-06-01 2016-03-08 Summit Therapeutics Plc Compounds for the treatment of Clostridium difficile associated disease

Also Published As

Publication number Publication date
KR100744827B1 (ko) 2007-08-01

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