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

Info

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
Authority
WO
WIPO (PCT)
Prior art keywords
formula
membrane
fluorinated
polymer
benzoate
Prior art date
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
Original Assignee
Korea Research Institute Of Chemical Technology
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 filed Critical Korea Research Institute Of Chemical Technology
Publication of WO2007114652A1 publication Critical patent/WO2007114652A1/fr

Links

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 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 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

Similar Documents

Publication Publication Date Title
KR101845108B1 (ko) 4차화된 폴리벤즈이미다졸
CN101270059A (zh) 含氟不对称芳香二胺、其制备及在合成聚酰亚胺中的应用
US11932729B2 (en) Polybenzimidazole, precursor polyamide thereof, and method for producing same
US20230099704A1 (en) Fluorinated amide compound, compound containing fluorinated nitrogen-containing heterocyclic ring, and fluorinated compound
JP4051955B2 (ja) ポリフェニレンスルホン酸類の製造方法
CN101274914B (zh) 含杂萘酮联萘结构不对称芳香二胺及其制备方法和应用
JP2013221086A (ja) ポリアリーレン及びその製造方法
WO2007114652A1 (fr) Nouveaux monomères benzimidazole terminés par des groupes trifluorovinyloxy et membrane de polybenzimidazoles préparée au moyen de ces monomères
US6054554A (en) Soluble polyimide resin comprising polyalicyclic structure
KR101816188B1 (ko) 폴리에테르에테르케톤 계열의 공중합체, 이를 포함하는 연료전지용 음이온교환막 및 이의 제조방법
US4599388A (en) Process for modifying polybenzimidazole polymers with ethylene carbonates
US20220251300A1 (en) Bio-based polysulfones and uses thereof
KR20190026132A (ko) 폴리에테르에테르케톤 계열의 공중합체를 포함하는 연료전지용 음이온교환막 및 이의 제조방법
CN111909377B (zh) 一种含有2,5-呋喃二甲醇残基的二酐单体及其制备方法、聚酰亚胺薄膜及其制备方法
JP2010058073A (ja) 親水化ポリエーテルスルホン分離膜及びその製造方法
US4734466A (en) Modified polybenzimidazole polymer membranes
KR102041379B1 (ko) 폴리에테르에테르케톤 계열의 공중합체를 포함하는 기체분리막 및 이의 제조방법
CN108997580B (zh) 一种含蒽酮和三氟甲基结构的聚醚酰亚胺及其制备方法
US5300625A (en) Heteroaromatic polyether
US7282553B2 (en) Flexible isopropylidene and tetramethyl-containing fluoropolyamide and fluoropolymide and preparation method thereof
KR20230142277A (ko) 폴리벤즈이미다졸계 화합물, 이의 제조 방법, 이를 포함하는 고분자 전해질 막, 막-전극 어셈블리, 및 전지
US8299202B2 (en) Phenol compounds and (co)polymers thereof
KR101559959B1 (ko) 다수의 기능기를 가지는 방향족 단량체와 이 단량체를 이용하여 제조된 중합체
WO2023219085A1 (fr) Composé polyamide fluoré, composé polyimide fluoré, matériau faiblement diélectrique, composant électronique haute fréquence
JP2020019854A (ja) セルロース誘導体とその成形体

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07745813

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 07745813

Country of ref document: EP

Kind code of ref document: A1