JP2004514768A - 高分子量パーフルオロシクロブタンポリマーおよびその製造方法 - Google Patents
高分子量パーフルオロシクロブタンポリマーおよびその製造方法 Download PDFInfo
- Publication number
- JP2004514768A JP2004514768A JP2002546592A JP2002546592A JP2004514768A JP 2004514768 A JP2004514768 A JP 2004514768A JP 2002546592 A JP2002546592 A JP 2002546592A JP 2002546592 A JP2002546592 A JP 2002546592A JP 2004514768 A JP2004514768 A JP 2004514768A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- catalyst
- polymerization initiator
- alkyl
- molecular weight
- 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.)
- Withdrawn
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- 229920000642 polymer Polymers 0.000 title claims abstract description 45
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 235000019407 octafluorocyclobutane Nutrition 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000000178 monomer Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 21
- -1 trifluorovinyl Chemical group 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 5
- 239000002685 polymerization catalyst Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- IERHLVCPSMICTF-XVFCMESISA-N cytidine 5'-monophosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(O)=O)O1 IERHLVCPSMICTF-XVFCMESISA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002524 organometallic group Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- QNDHDIXRBUDLFJ-UHFFFAOYSA-N 1-(1,2,2-trifluoroethenoxy)-4-[4-(1,2,2-trifluoroethenoxy)phenyl]benzene Chemical group C1=CC(OC(F)=C(F)F)=CC=C1C1=CC=C(OC(F)=C(F)F)C=C1 QNDHDIXRBUDLFJ-UHFFFAOYSA-N 0.000 claims 1
- 125000005410 aryl sulfonium group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 19
- 150000008378 aryl ethers Chemical class 0.000 description 9
- 238000009826 distribution Methods 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000006085 branching agent Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- XAUHHCMRFFGRMF-UHFFFAOYSA-N 1-[1,1-bis[4-(1,2,2-trifluoroethenoxy)phenyl]ethyl]-4-(1,2,2-trifluoroethenoxy)benzene Chemical compound C=1C=C(OC(F)=C(F)F)C=CC=1C(C=1C=CC(OC(F)=C(F)F)=CC=1)(C)C1=CC=C(OC(F)=C(F)F)C=C1 XAUHHCMRFFGRMF-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
Classifications
-
- 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
- C08F114/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F114/18—Monomers containing fluorine
-
- 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
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F16/32—Monomers containing two or more unsaturated aliphatic radicals
-
- 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
- C08F114/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F114/18—Monomers containing fluorine
- C08F114/185—Monomers containing fluorine not covered by the groups C08F114/20 - C08F114/28
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/726,837 US6646075B2 (en) | 1999-12-23 | 2000-11-30 | High molecular weight perfluorocyclobutane polymers and method of making |
| PCT/US2001/019523 WO2002044223A1 (en) | 2000-11-30 | 2001-06-19 | High molecular weight perfluorocyclobutane polymers and method of making |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004514768A true JP2004514768A (ja) | 2004-05-20 |
| JP2004514768A5 JP2004514768A5 (enExample) | 2008-08-07 |
Family
ID=24920211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002546592A Withdrawn JP2004514768A (ja) | 2000-11-30 | 2001-06-19 | 高分子量パーフルオロシクロブタンポリマーおよびその製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6646075B2 (enExample) |
| EP (1) | EP1341827B1 (enExample) |
| JP (1) | JP2004514768A (enExample) |
| KR (1) | KR100807898B1 (enExample) |
| AT (1) | ATE274536T1 (enExample) |
| AU (1) | AU2001268553A1 (enExample) |
| DE (1) | DE60105190T2 (enExample) |
| WO (1) | WO2002044223A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7582704B2 (en) * | 2005-07-01 | 2009-09-01 | Bausch & Lomb Incorporated | Biomedical devices |
| US7538160B2 (en) * | 2005-07-01 | 2009-05-26 | Bausch & Lomb Incorporated | Trifluorovinyl aromatic containing poly(alkyl ether) prepolymers |
| US7402634B2 (en) * | 2005-07-01 | 2008-07-22 | Bausch And Lamb Incorporated | Perfluorocyclobutane copolymers |
| US7425600B2 (en) * | 2005-07-01 | 2008-09-16 | Bausch & Lomb Incorporated | Polymerization products and biomedical devices containing same |
| US7534836B2 (en) * | 2005-07-01 | 2009-05-19 | Bausch & Lomb Incorporated | Biomedical devices |
| KR100868450B1 (ko) * | 2006-11-20 | 2008-11-11 | 광주과학기술원 | 퍼플루오로싸이클로부탄 기능기를 포함하는 전기변색화합물 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3418302A (en) * | 1963-08-30 | 1968-12-24 | Du Pont | Perfluorocyclic ether polymers |
| US4358412A (en) | 1980-06-11 | 1982-11-09 | The Dow Chemical Company | Preparation of vinyl ethers |
| US4337211A (en) | 1980-06-11 | 1982-06-29 | The Dow Chemical Company | Fluorocarbon ethers having substituted halogen site(s) and process to prepare |
| US4812352A (en) | 1986-08-25 | 1989-03-14 | Minnesota Mining And Manufacturing Company | Article having surface layer of uniformly oriented, crystalline, organic microstructures |
| US5039561A (en) | 1986-08-25 | 1991-08-13 | Minnesota Mining And Manufacturing Company | Method for preparing an article having surface layer of uniformly oriented, crystalline, organic microstructures |
| US5037918A (en) | 1989-12-15 | 1991-08-06 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers with crosslinking |
| US5021602A (en) | 1989-06-09 | 1991-06-04 | The Dow Chemical Company | Reactive compounds containing perfluorocyclobutane rings |
| 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 |
| US5037917A (en) | 1989-06-09 | 1991-08-06 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| JP3022921B2 (ja) | 1989-06-09 | 2000-03-21 | ザ ダウ ケミカル カンパニー | ペルフルオロシクロブタン環を有するポリマーの製造方法及びペルフルオロシクロブタン環を含むポリマー |
| US5066746A (en) | 1989-06-09 | 1991-11-19 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| US5159038A (en) | 1989-06-09 | 1992-10-27 | Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| US5023380A (en) | 1989-06-09 | 1991-06-11 | The Dow Chemical Company | Perfluorovinyl compounds |
| US5364547A (en) | 1989-06-09 | 1994-11-15 | The Dow Chemical Company | Lubricants containing perfluorocyclobutane rings |
| US5246782A (en) | 1990-12-10 | 1993-09-21 | The Dow Chemical Company | Laminates of polymers having perfluorocyclobutane rings and polymers containing perfluorocyclobutane rings |
| US5159037A (en) | 1989-06-09 | 1992-10-27 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| 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 |
| US5037919A (en) | 1989-06-09 | 1991-08-06 | 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 |
| US5264508A (en) | 1992-06-25 | 1993-11-23 | The Dow Chemical Company | Polymers of haloperfluoro and perfluoro ethers |
| US5449825A (en) | 1992-06-25 | 1995-09-12 | The Dow Chemical Company | Preparation of haloperfluoro and perfluoro ethers |
| US5338430A (en) | 1992-12-23 | 1994-08-16 | Minnesota Mining And Manufacturing Company | Nanostructured electrode membranes |
| US5426164A (en) | 1992-12-24 | 1995-06-20 | The Dow Chemical Company | Photodefinable polymers containing perfluorocyclobutane groups |
| US5834523A (en) | 1993-09-21 | 1998-11-10 | Ballard Power Systems, Inc. | Substituted α,β,β-trifluorostyrene-based composite membranes |
| US5620807A (en) | 1995-08-31 | 1997-04-15 | The Dow Chemical Company | Flow field assembly for electrochemical fuel cells |
| JP4657390B2 (ja) | 1997-07-25 | 2011-03-23 | アセップ・インク | ペルフルオロビニルイオン化合物および重合体型のイオン電導体の成分、選択膜の成分または触媒の成分としてのそれらの使用 |
| US5910378A (en) | 1997-10-10 | 1999-06-08 | Minnesota Mining And Manufacturing Company | Membrane electrode assemblies |
| US5879828A (en) | 1997-10-10 | 1999-03-09 | Minnesota Mining And Manufacturing Company | Membrane electrode assembly |
| WO1999038842A1 (fr) | 1998-01-30 | 1999-08-05 | Hydro-Quebec | Derives bis-sulfonyles polymerisables et leur utilisation dans la preparation de membranes echangeuses d'ions |
-
2000
- 2000-11-30 US US09/726,837 patent/US6646075B2/en not_active Expired - Lifetime
-
2001
- 2001-06-19 JP JP2002546592A patent/JP2004514768A/ja not_active Withdrawn
- 2001-06-19 KR KR1020037007228A patent/KR100807898B1/ko not_active Expired - Fee Related
- 2001-06-19 AU AU2001268553A patent/AU2001268553A1/en not_active Abandoned
- 2001-06-19 WO PCT/US2001/019523 patent/WO2002044223A1/en not_active Ceased
- 2001-06-19 AT AT01946511T patent/ATE274536T1/de not_active IP Right Cessation
- 2001-06-19 DE DE60105190T patent/DE60105190T2/de not_active Expired - Fee Related
- 2001-06-19 EP EP01946511A patent/EP1341827B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1341827B1 (en) | 2004-08-25 |
| ATE274536T1 (de) | 2004-09-15 |
| AU2001268553A1 (en) | 2002-06-11 |
| KR20030061413A (ko) | 2003-07-18 |
| US6646075B2 (en) | 2003-11-11 |
| DE60105190D1 (de) | 2004-09-30 |
| DE60105190T2 (de) | 2005-09-08 |
| US20020065382A1 (en) | 2002-05-30 |
| EP1341827A1 (en) | 2003-09-10 |
| KR100807898B1 (ko) | 2008-02-27 |
| WO2002044223A1 (en) | 2002-06-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080617 |
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| A621 | Written request for application examination |
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| A977 | Report on retrieval |
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