KR920700182A - 퍼플루오로사이클로부탄 환을 함유하는 반응성 화합물 - Google Patents

퍼플루오로사이클로부탄 환을 함유하는 반응성 화합물

Info

Publication number
KR920700182A
KR920700182A KR1019910700158A KR910700158A KR920700182A KR 920700182 A KR920700182 A KR 920700182A KR 1019910700158 A KR1019910700158 A KR 1019910700158A KR 910700158 A KR910700158 A KR 910700158A KR 920700182 A KR920700182 A KR 920700182A
Authority
KR
South Korea
Prior art keywords
groups
compound
group
independently
formula
Prior art date
Application number
KR1019910700158A
Other languages
English (en)
Inventor
에스. 클레멘트 케더린
에이. 밥 데이비드
알. 이젤 바비
Original Assignee
리챠드 지.워터맨
더 다우 케미칼 캄파니
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 리챠드 지.워터맨, 더 다우 케미칼 캄파니 filed Critical 리챠드 지.워터맨
Publication of KR920700182A publication Critical patent/KR920700182A/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/235—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/247—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/88—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/235—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/253—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
    • C07C65/26—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F38/00—Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

Abstract

내용 없음

Description

퍼플루오로사이클로부탄 환을 함유하는 반응성 화합물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (9)

  1. 적어도 하나의 퍼플루오로사이클로부탄 환 및 적어도 두개의 반응성 작용 그룹을 갖는 화합물.
  2. 제1항에 있어서, 2 내지 50개의 퍼플루오로사이클로부탄 그룹을 갖는 화합물.
  3. 제1항에 있어서, 하기 일반식(Ⅱ)의 구조를 갖는 화합물.
    상기식에서, R 및 R´는 독립적으로 임의의 불활성적으로 치환된 그룹이고; X 및 X´는 R 및 R´와 퍼플루오로사이클로부탄 환율 연결하는 분자 구조이며; n 및 n´는 각각 적어도 1의 독립적 정수이고; G 및 G´는 독립적으로 반응성 작용 그룹 또는 반응성 작용 그룹으로 전환가능한 그룹이다.
  4. 제3항에 있어서, n은 n´각각 1 내지 4의 정수인 화합물.
  5. 제4항에 있어서, X 및 X´가 독립적으로 결합, 산소원자, 황원자, 카복실산 에스테르 그룹 및 티오카복실산 에스테르 그룹, 설파이드, 설폰, 퍼플루오로알킬렌, 퍼플루오로알킬렌 에테르, 알킬렌, 아세틸렌, 포스핀, 카보닐 및 티오카보닐 그룹; 셀레노; 텔루로; 티트리도(NO), 실란디일, 트리실란디일, 테트라실란테트라일, 실옥산디일, 디실옥산디일, 트리실옥실, 트리실라지닐, 또는 실릴티오그룹; 보란디일 또는 메틸보란디일 그룹; 및 이들의 혼합물과 같은 연결구조로부터 선택되고; R 및 R´는 독립적으로 분자량이 14 내지 20,000인 비치환되거나 또는 불활성적으로 치환된 하이드로카빌 그룹이며; G 및 G´는 독립적으로 하이드록실 그룹(알콜성 및 페놀성 모두) 및 이의 에스테르, 티오카복실산 그룹 및 카복실산 그룹, 아실 할라이드(예: 클로라이드), 이소시아네이트, 아실 이자이드, 아세틸 그룹, 트리할로이세틸 그룹, 1급 또는 2급 아민, 설파이드 그룹, 설폰산 그룹, 설폰아미드 그룹, 케톤, 알데하이드, 에폭시 그룹, 1급 또는 2급 아미드, 할로 그룹, 니트로 그룹, 시아노 그룹, 무수물, 이미드, 시이네이트 그룹, 비닐, 알릴, 아세틸렌 -;실리콘 그룹－함유 치환체, 인－함유 그룹, 붕소－함유 그룹, 에스테르(예 : 티오카복실산 에스테르 및 카복실산 에스테르); 트리할로메틸 그룹(예 : 트리클로로메틸 그룹), 알콕시 그룹 및 알킬 그룹(R이 방향족인 경우)으로 구성된 그룹중에서 선택되는 화합물.
  6. 적어도 하나의 퍼플루오로사이클로부탄 환 및 적어도 두개의 작용성 그룹을 갖는 제1화합물과 제1화합물의 작용성 그룹에 반응성인 적어도 2개의 작용성 그룹을 갖는 적어도 하나의 제2화합물의 반응 생성물인 중합체.
  7. 적어도 하나의 퍼플루오로사이클로부탄 환 및 적어도 두개의 작용성 그룹을 갖는 제1화합물과 제1화합물의 작용성 그룹에 반응성인 적어도 두개의 작용성 그룹을 갖는 적어도 하나의 제2화합물을 반응시킴을 포함하는 중합체의 제조방법.
  8. 하기 일반식(Ⅰ)의 트리플루오로비닐 화합물을 열적으로 이량체화하여 하기 일반식(Ⅱ)의 화합물을 형성함을 포함하는, 적어도 하나의 퍼플루오로사이클로부탄 환 및 적어도 두개의 반응성 작용그룹을 갖는 일반식(Ⅱ)의 화합물을 제조하는 방법.
    상기식에서, R및 R´는 독립적으로 임의의 불활성적으로 치환된 하이드로카빌 그룹이고; X 및 X´는 R 및 R´와 퍼플루오로사이클로탄 환을 연결하는 그룹이며; n 및 n´는 독립적으로 각각 적어도 1의 정수이고; G 및 G´, 는 독립적으로 반응성 작용 그룹 또는 반응성 작용그룹으로 전환가능한 그룹이며, 단, 일반식(I)에서의 G, X 및 n은 각각 일반식(Ⅱ)에서의 G 또는 G´, X 또는 X´ 및 n 또는 n´이다.
  9. (a) 하기 일반식(Ⅲ)의 2－할로테트라플루오로 화합물을 제조하고, (b) G´가 G 또는 G´로 전환시키기에 적합한 작용성 그룹인 경우, 그룹 G´를 화학적으로 변형시켜 작용성 그룹 G 또는 G´를 생성하며; (c) 2－할로테트라플루오로 화합물을 탈할로겐화시켜 상응하는 트리플루오로비닐 화합물을 형성한 다음; (d) 하기 일반식(Ⅰ)의 트리플루오로 비닐 화합물을 열적으로 이량체화하여 일반식(Ⅱ)의 화합물을 형성하는 단계를 포함하는, 적어도 하나의 퍼플루오로사이클로부탄환 및 적어도 두개의 반응성 작용그룹을 갖는 하기 일반식(Ⅱ)의 화합물을 제조하는 방법.
    상기식에서, R 및 R´는 독립적으로 임의의 불활성적으로 치환된 하이드로카빌 그룹이고; X 및 X´는 R 및 R´와 퍼플루오로사이클로탄 환을 연결하는 그룹이며; n 및 n´는 독립적으로 각각 적어도 1의 정수이고; G 및 G´는 독립적으로 반응성 작용그룹 또는 반응성 작용그룹으로 전환가능한 그룹이며, Q는 브롬, 염소 또는 요오드이고, G˝는 상기에서 정의한 바와 같은 작용성 그룹 G, 또는 G 또는 G´로 전환시키기에 적합한 작용성 그룹이며, 단, 일반식(Ⅲ)에서의 X 및 R은 일반식(Ⅱ)에서의 X, X´, R 및 R´에 대해 정의한 바와 같고, 일반식(Ⅲ)에서의 n은 G˝그룹의 수이며, 일반식(Ⅰ)에서의 G, X 및 n은 각각 일반식(Ⅱ)에서의 G 또는 G´, X 또는 X´, 및 n 또는 n´이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910700158A 1989-06-09 1990-06-04 퍼플루오로사이클로부탄 환을 함유하는 반응성 화합물 KR920700182A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US07/364,686 US5021602A (en) 1989-06-09 1989-06-09 Reactive compounds containing perfluorocyclobutane rings
US364686 1989-06-09
PCT/US1990/003152 WO1990015044A2 (en) 1989-06-09 1990-06-04 Reactive compounds containing perfluorocyclobutane rings

Publications (1)

Publication Number Publication Date
KR920700182A true KR920700182A (ko) 1992-02-19

Family

ID=23435619

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019910700158A KR920700182A (ko) 1989-06-09 1990-06-04 퍼플루오로사이클로부탄 환을 함유하는 반응성 화합물

Country Status (8)

Country Link
US (1) US5021602A (ko)
EP (1) EP0429618A1 (ko)
JP (1) JPH04500364A (ko)
KR (1) KR920700182A (ko)
AU (1) AU5834290A (ko)
CA (1) CA2030800A1 (ko)
FI (1) FI910629A0 (ko)
WO (1) WO1990015044A2 (ko)

Families Citing this family (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5159038A (en) * 1989-06-09 1992-10-27 Dow Chemical Company Perfluorocyclobutane ring-containing polymers
US5159037A (en) * 1989-06-09 1992-10-27 The Dow Chemical Company Perfluorocyclobutane ring-containing polymers
US5246782A (en) * 1990-12-10 1993-09-21 The Dow Chemical Company Laminates of polymers having perfluorocyclobutane rings and polymers containing perfluorocyclobutane rings
US5364547A (en) * 1989-06-09 1994-11-15 The Dow Chemical Company Lubricants containing perfluorocyclobutane rings
US5162468A (en) * 1989-06-09 1992-11-10 The Dow Chemical Company Perfluorovinyl compounds
US5364917A (en) * 1989-06-09 1994-11-15 The Dow Chemical Company Perfluorocyclobutane ring-containing polymers
US5210265A (en) * 1989-06-09 1993-05-11 The Dow Chemical Company Reactive compounds containing perfluorocyclobutane rings
US5198513A (en) * 1989-06-09 1993-03-30 The Dow Chemical Company Reactive compounds containing perfluorovinyl groups
US5159036A (en) * 1989-12-15 1992-10-27 The Dow Chemical Company Perfluorocyclobutane ring-containing polymers with crosslinking
DE69111699T2 (de) * 1990-06-01 1996-04-18 Asahi Glass Co Ltd Fluoropolymer-Überzugszusammensetzung und damit beschichteter Gegenstand.
US5730922A (en) * 1990-12-10 1998-03-24 The Dow Chemical Company Resin transfer molding process for composites
US5225515A (en) * 1991-04-17 1993-07-06 The Dow Chemical Company Poly(aryl ether) polymers containing perfluorocyclobutane rings
US5426164A (en) * 1992-12-24 1995-06-20 The Dow Chemical Company Photodefinable polymers containing perfluorocyclobutane groups
JP3267452B2 (ja) * 1993-08-31 2002-03-18 キヤノン株式会社 光電変換装置及び太陽電池モジュール
US5540997A (en) * 1995-03-13 1996-07-30 The Dow Chemical Company Alignment layer for a liquid crystal in a liquid crystal display device
JPH09143420A (ja) * 1995-09-21 1997-06-03 Asahi Glass Co Ltd 低誘電率樹脂組成物
JP2002530505A (ja) 1998-11-24 2002-09-17 ザ ダウ ケミカル カンパニー 架橋性マトリックス前駆体および気孔発生体を含有する組成物、並びにそれから製造された多孔質マトリックス
US6646075B2 (en) * 1999-12-23 2003-11-11 3M Innovative Properties Company High molecular weight perfluorocyclobutane polymers and method of making
US6361583B1 (en) 2000-05-19 2002-03-26 Membrane Technology And Research, Inc. Gas separation using organic-vapor-resistant membranes
US6361582B1 (en) 2000-05-19 2002-03-26 Membrane Technology And Research, Inc. Gas separation using C3+ hydrocarbon-resistant membranes
US6592650B2 (en) 2000-05-19 2003-07-15 Membrane Technology And Research, Inc. Gas separation using organic-vapor-resistant membranes and PSA
US6572679B2 (en) 2000-05-19 2003-06-03 Membrane Technology And Research, Inc. Gas separation using organic-vapor-resistant membranes in conjunction with organic-vapor-selective membranes
US6544316B2 (en) 2000-05-19 2003-04-08 Membrane Technology And Research, Inc. Hydrogen gas separation using organic-vapor-resistant membranes
US6579341B2 (en) 2000-05-19 2003-06-17 Membrane Technology And Research, Inc. Nitrogen gas separation using organic-vapor-resistant membranes
US6572680B2 (en) 2000-05-19 2003-06-03 Membrane Technology And Research, Inc. Carbon dioxide gas separation using organic-vapor-resistant membranes
US6559237B1 (en) 2000-06-05 2003-05-06 3M Innovative Properties Company Sulfonated perfluorocyclobutane ion-conducting membranes
US6268532B1 (en) 2000-06-05 2001-07-31 3M Innovative Properties Company Sulfonated perfluorovinyl functional monomers
US6649715B1 (en) 2000-06-27 2003-11-18 Clemson University Fluoropolymers and methods of applying fluoropolymers in molding processes
US7265174B2 (en) * 2001-03-22 2007-09-04 Clemson University Halogen containing-polymer nanocomposite compositions, methods, and products employing such compositions
US6953653B2 (en) 2001-08-30 2005-10-11 Clemson University Fluoropolymer compositions, optical devices, and methods for fabricating optical devices
US6896717B2 (en) * 2002-07-05 2005-05-24 Membrane Technology And Research, Inc. Gas separation using coated membranes
US7538160B2 (en) 2005-07-01 2009-05-26 Bausch & Lomb Incorporated Trifluorovinyl aromatic containing poly(alkyl ether) prepolymers
US7582704B2 (en) * 2005-07-01 2009-09-01 Bausch & Lomb Incorporated Biomedical devices
US7534836B2 (en) * 2005-07-01 2009-05-19 Bausch & Lomb Incorporated Biomedical devices
US7425600B2 (en) * 2005-07-01 2008-09-16 Bausch & Lomb Incorporated Polymerization products and biomedical devices containing same
US7402634B2 (en) * 2005-07-01 2008-07-22 Bausch And Lamb Incorporated Perfluorocyclobutane copolymers
CA2669279C (en) * 2006-10-27 2017-01-03 Cms Technologies Holdings, Inc. Removal of water and methanol from fluids
EP2203498B1 (en) 2007-10-05 2017-12-06 Interface Biologics Inc. Oligofluorinated cross-linked polymers and uses thereof
US7897692B2 (en) * 2008-05-09 2011-03-01 Gm Global Technology Operations, Inc. Sulfonated perfluorocyclobutane block copolymers and proton conductive polymer membranes
US8030405B2 (en) * 2008-05-09 2011-10-04 GM Global Technology Operations LLC Blended PEM's with elastomers for improved mechanical durability
US7897691B2 (en) * 2008-05-09 2011-03-01 Gm Global Technology Operations, Inc. Proton exchange membranes for fuel cell applications
US7985805B2 (en) * 2008-05-09 2011-07-26 GM Global Technology Operations LLC Polyelectrolyte membranes comprised of blends of PFSA and sulfonated PFCB polymers
US7897693B2 (en) * 2008-05-09 2011-03-01 Gm Global Technology Operations, Inc. Proton conductive polymer electrolytes and fuel cells
US8008404B2 (en) * 2008-05-09 2011-08-30 GM Global Technology Operations LLC Composite membrane
US7888433B2 (en) * 2008-05-09 2011-02-15 Gm Global Technology Operations, Inc. Sulfonated-polyperfluoro-cyclobutane-polyphenylene polymers for PEM fuel cell applications
US7976730B2 (en) * 2008-08-25 2011-07-12 GM Global Technology Operations LLC Blends of low equivalent molecular weight PFSA ionomers with Kynar 2751
US8003732B2 (en) * 2008-08-25 2011-08-23 GM Global Technology Operations LLC Gradient reinforced proton exchange membrane
US20110045381A1 (en) * 2009-08-18 2011-02-24 Gm Global Technology Operations, Inc. Hydrocarbon PEM Membranes with Perfluorosulfonic Acid Groups for Automotive Fuel Cells
US8852823B2 (en) * 2009-08-26 2014-10-07 GM Global Technology Operations LLC Sodium stannate additive to improve the durability of PEMS for H2/air fuel cells
US8053530B2 (en) * 2009-08-26 2011-11-08 GM Global Technology Operations LLC Polyelectrolyte membranes made of poly(perfluorocyclobutanes) with pendant perfluorosulfonic acid groups and blends with poly(vinylidene fluoride)
US20110053008A1 (en) * 2009-08-28 2011-03-03 Gm Global Technology Operations, Inc. Water vapor transfer membrane and paper integrated assembly
US7972732B2 (en) * 2009-08-28 2011-07-05 GM Global Technology Operations LLC Perfluorocyclobutane based water vapor transfer membranes with side chain perfluorosulfonic acid moieties
US8354201B2 (en) * 2009-08-28 2013-01-15 GM Global Technology Operations LLC Fuel cell with spatially non-homogeneous ionic membrane
US20110053009A1 (en) * 2009-08-28 2011-03-03 Gm Global Technology Operations, Inc. Customized water vapor transfer membrane layered structure
US8058352B2 (en) * 2009-08-28 2011-11-15 GM Global Technology Operations LLC Perfluorocyclobutane based water vapor transfer membranes
US8048963B2 (en) * 2009-08-31 2011-11-01 GM Global Technology Operations LLC Ion exchange membrane having lamellar morphology and process of making the same
US8409765B2 (en) 2009-08-31 2013-04-02 GM Global Technology Operations LLC Co(II)tetramethoxyphenylporphyrin additive to PFSA PEMS for improved fuel cell durability
US8252712B2 (en) * 2009-11-13 2012-08-28 GM Global Technology Operations LLC Polymer dispersant addition to fuel cell electrode inks for improved manufacturability
US20110159404A1 (en) * 2009-12-29 2011-06-30 Gm Global Technology Operations, Inc. Polyolefin Support to Prevent Dielectric Breakdown in PEMS
US20110159405A1 (en) * 2009-12-30 2011-06-30 Gm Global Technology Operations, Inc. Hydrophilic Polyelectrolyte Membranes Containing Poly(Vinyl Acetate) and Poly(Vinyl Alcohol)
US20110165497A1 (en) * 2010-01-06 2011-07-07 Gm Global Technology Operations, Inc. Method for Mitigating Fuel Cell Chemical Degradation
US7989512B1 (en) 2010-03-17 2011-08-02 GM Global Technology Operations LLC Polyelectrolyte membranes derived from soluble perfluorocyclobutane polymers with sulfonyl chloride groups
US8044146B1 (en) 2010-04-16 2011-10-25 GM Global Technology Operations LLC Combination of main-chain and side-chain sulfonation of PFCB-6F high-temperature fuel cell membranes
US8735021B2 (en) 2010-04-16 2014-05-27 GM Global Technology Operations LLC Cobalt(II) tetramethoxyphenylporphyrin (CoTMPP) ionomer stabilization to prevent electrode degradation
US8609739B2 (en) 2011-02-17 2013-12-17 GM Global Technology Operations LLC Poly(perfluorocyclobutane) ionomer with phosphonic acid groups for high temperature fuel cells
CN107986989B (zh) * 2017-11-28 2020-07-14 湖北鼎龙控股股份有限公司 一种异氰酸酯
JPWO2020162371A1 (ja) 2019-02-08 2021-12-09 Ａｇｃ株式会社 含フッ素エーテル化合物、含フッ素エーテル組成物、コーティング液、物品、物品の製造方法、及び含フッ素化合物の製造方法
WO2020229227A1 (en) 2019-05-10 2020-11-19 Solvay Specialty Polymers Italy S.P.A. Method of making perfluorocyclobutane-containing monomer

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3114778A (en) * 1963-12-17 Fluorinated vinyl ethers and their
US2404374A (en) * 1943-04-23 1946-07-23 Du Pont Polyfluorinated cycloparaffins and process for producing them
US2671799A (en) * 1950-08-30 1954-03-09 William T Miller Perhalocarbon compounds and method of preparing them
US2848504A (en) * 1954-07-21 1958-08-19 Du Pont Alkyl hexafluorocyclobutanes and process for preparing them
US2958685A (en) * 1957-08-09 1960-11-01 Du Pont Polymers of perfluoropropylene
US2982786A (en) * 1958-07-09 1961-05-02 Du Pont Novel cyclic dimers of perfluorovinyl ethers
US2922823A (en) * 1958-07-16 1960-01-26 Dow Corning 2-vinylchlorohexafluorocyclobutane
US3022356A (en) * 1958-10-16 1962-02-20 Du Pont Process for preparing bis (omega-hydroperfluoroalkyl) carbinols
US3316312A (en) * 1959-04-10 1967-04-25 Du Pont Perfluorinated dialkyl cyclobutanes
US3111509A (en) * 1961-10-05 1963-11-19 Goodrich Co B F Stable, high softening, vinyl cyclobutane homopolymers and method for preparing same
US3277068A (en) * 1962-07-31 1966-10-04 Leo A Wall Perfluorovinylphenylethers and their polymers
US3303145A (en) * 1963-01-11 1967-02-07 Du Pont Fluorocarbon polyethers
US3310606A (en) * 1963-08-28 1967-03-21 Du Pont Thermosetting perfluorinated divinyl ether resins
US3397191A (en) * 1965-06-02 1968-08-13 Du Pont Fluorocarbon ethers
US3549606A (en) * 1966-01-10 1970-12-22 Monsanto Co Fluoroalkyl ethers of alicyclic fluoroolefins
US4154753A (en) * 1966-01-12 1979-05-15 Imperial Chemical Industries Limited Fluorinated compounds containing functional groups
US3505411A (en) * 1966-10-11 1970-04-07 Minnesota Mining & Mfg Perfluoroalkylene oxide polymers
GB1185564A (en) * 1968-03-06 1970-03-25 Du Pont Improvements relating to Perfluorinated Ethers
US3682876A (en) * 1969-10-24 1972-08-08 Dow Chemical Co Polyperfluorocyclobutadiene
US3696154A (en) * 1970-06-12 1972-10-03 Dow Chemical Co Perfluorinated ether sulfides
DE2029556A1 (de) * 1970-06-16 1971-12-23 Farbwerke Hoechst AG, vormals Meister Lucius & Brumng, 6000 Frankfurt Verfahren zur Herstellung von Aryl 1,1,2,2 tetrafluorathylathern
US3900380A (en) * 1972-03-02 1975-08-19 Dow Chemical Co Preparation of fluorinated cyclobutenyl alkyl ether copolymers
US3840603A (en) * 1972-03-02 1974-10-08 Dow Chemical Co Fluorinated cyclobutenyl alkyl ether copolymers
US4423249A (en) * 1981-08-26 1983-12-27 The Dow Chemical Company Preparation of halofluoroalkyl ethers
US4377711A (en) * 1981-11-04 1983-03-22 Rhone-Poulenc Industries Novel aromatic bromopolyfluoroalkyl ethers and method for the preparation thereof
HUT41398A (en) * 1984-10-04 1987-04-28 Ici Plc Insecticidal compositions comprising tetrazolyl derivatives as active substance and process for preparing the active substances
US4897457A (en) * 1987-08-14 1990-01-30 Asahi Glass Company Ltd. Novel fluorine-containing cyclic polymer

Also Published As

Publication number Publication date
JPH04500364A (ja) 1992-01-23
US5021602A (en) 1991-06-04
AU5834290A (en) 1991-01-07
FI910629A0 (fi) 1991-02-08
WO1990015044A2 (en) 1990-12-13
EP0429618A1 (en) 1991-06-05
CA2030800A1 (en) 1990-12-10
WO1990015044A3 (en) 1991-04-04

Similar Documents

Publication Publication Date Title
KR920700182A (ko) 퍼플루오로사이클로부탄 환을 함유하는 반응성 화합물
KR920700181A (ko) 퍼플루오로비닐 그룹을 함유하는 반응성 조성물
US4107216A (en) 2-Decarboxy-2-hydroxy-methyl-ω-phenyl-PGD analogs
NO993981D0 (no) Sammensetning og fremgangsmÕte for fremstilling av brenselsbestandig flytende polytioeterpolymerer med god lav-temperatur-fleksibilitet
KR900701741A (ko) 0-(3-아미노-2-히드록시프로필)히드록심산 할라이드 및 그의 제조방법
KR840006476A (ko) 3-페녹시벤질 2-(4-알콕시페닐)-2-메틸프로필 에테르의 제조방법
US4097537A (en) 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-PGF1α compounds
KR840006206A (ko) 이소퀴놀린 유도체의 제조방법
JPS57125257A (en) Stabilized synthetic resin composition
GB1444855A (en) Organo copper compounds and their production
KR910008027A (ko) 폴리티오카보네이트와 그 제조방법
JPS5661380A (en) Preparation of haloalkyl-dialkylxanthine
US4208538A (en) 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-ω-phenyl-PGF2 compounds
US5861540A (en) Substituted 1,1,1-triaryl-2,2,2-trifuoroethanes and processes for their synthesis
US4204057A (en) 9-Deoxy-6,9α-epoxymethano-PG C-1 amines
JPS5584340A (en) Stabilizer for chlorine-containing resin
US3985787A (en) 4,5-Cis-didehydro-PGA1 analogs
US4206303A (en) 9-Deoxy-6,9α-epoxymethano-PG C-1 alcohols
JPH04282336A (ja) ポリアリル化合物
ES464901A1 (es) Procedimiento mejorado para la obtencion de nuevos poli (carbonatos-uretanos) alifaticos o cicloalifaticos trioles.
US3989735A (en) 4.5-Cis-didehydro-PGB1 analogs
US4164501A (en) 2-Decarboxy-2-hydroxymethyl-trans-4,5,13,14-tetradehydro-PGI1 compounds
JPS56108757A (en) Preparation of dioximate compound
JPS559059A (en) Preparation of dicyclohexyl neophyltin halide
Yankee et al. 8β, 12α-17-Phenyl-18, 19, 20-trinor-PGF 2 α compounds

Legal Events

Date Code Title Description
WITN Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid