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- Withdrawn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 (cg-RX-API-DMAC7.html) | 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 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1341827B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2004514768A (cg-RX-API-DMAC7.html) |
| KR (1) | KR100807898B1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE274536T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2001268553A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60105190T2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002044223A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7538160B2 (en) | 2005-07-01 | 2009-05-26 | Bausch & Lomb Incorporated | Trifluorovinyl aromatic containing poly(alkyl ether) prepolymers |
| 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 |
| 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 |
| 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 |
| US4337211A (en) | 1980-06-11 | 1982-06-29 | The Dow Chemical Company | Fluorocarbon ethers having substituted halogen site(s) and process to prepare |
| US4358412A (en) | 1980-06-11 | 1982-11-09 | The Dow Chemical Company | Preparation of vinyl ethers |
| 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 |
| US5159037A (en) | 1989-06-09 | 1992-10-27 | 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 |
| US5023380A (en) | 1989-06-09 | 1991-06-11 | The Dow Chemical Company | Perfluorovinyl compounds |
| US5037917A (en) | 1989-06-09 | 1991-08-06 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| US5159038A (en) | 1989-06-09 | 1992-10-27 | Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| US5364917A (en) | 1989-06-09 | 1994-11-15 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| US5021602A (en) * | 1989-06-09 | 1991-06-04 | The Dow Chemical Company | Reactive compounds containing perfluorocyclobutane rings |
| US5162468A (en) | 1989-06-09 | 1992-11-10 | The Dow Chemical Company | Perfluorovinyl compounds |
| US5066746A (en) | 1989-06-09 | 1991-11-19 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| US5198513A (en) | 1989-06-09 | 1993-03-30 | The Dow Chemical Company | Reactive compounds containing perfluorovinyl groups |
| 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 |
| US5246782A (en) | 1990-12-10 | 1993-09-21 | The Dow Chemical Company | Laminates of polymers having perfluorocyclobutane rings and polymers containing perfluorocyclobutane rings |
| US5037919A (en) | 1989-06-09 | 1991-08-06 | The Dow Chemical Company | Reactive compounds containing perfluorovinyl groups |
| US5364547A (en) | 1989-06-09 | 1994-11-15 | The Dow Chemical Company | Lubricants containing perfluorocyclobutane rings |
| US5159036A (en) | 1989-12-15 | 1992-10-27 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers with crosslinking |
| US5449825A (en) | 1992-06-25 | 1995-09-12 | The Dow Chemical Company | Preparation of haloperfluoro and perfluoro ethers |
| US5264508A (en) | 1992-06-25 | 1993-11-23 | The Dow Chemical Company | Polymers 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 |
| US6288187B1 (en) | 1997-07-25 | 2001-09-11 | Acep Inc. | Perfluorovinyl ionic compounds and their use in conductive materials |
| 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 |
| EP1312603A1 (fr) | 1998-01-30 | 2003-05-21 | Hydro-Quebec | Dérivés bis-sulfonyles polymérisables et leur utilisation dans la préparation de membranes échangeuses 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 AT AT01946511T patent/ATE274536T1/de not_active IP Right Cessation
- 2001-06-19 EP EP01946511A patent/EP1341827B1/en not_active Expired - Lifetime
- 2001-06-19 KR KR1020037007228A patent/KR100807898B1/ko not_active Expired - Fee Related
- 2001-06-19 WO PCT/US2001/019523 patent/WO2002044223A1/en not_active Ceased
- 2001-06-19 DE DE60105190T patent/DE60105190T2/de not_active Expired - Fee Related
- 2001-06-19 AU AU2001268553A patent/AU2001268553A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE274536T1 (de) | 2004-09-15 |
| US20020065382A1 (en) | 2002-05-30 |
| DE60105190T2 (de) | 2005-09-08 |
| US6646075B2 (en) | 2003-11-11 |
| EP1341827A1 (en) | 2003-09-10 |
| KR20030061413A (ko) | 2003-07-18 |
| EP1341827B1 (en) | 2004-08-25 |
| DE60105190D1 (de) | 2004-09-30 |
| WO2002044223A1 (en) | 2002-06-06 |
| AU2001268553A1 (en) | 2002-06-11 |
| KR100807898B1 (ko) | 2008-02-27 |
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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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| A761 | Written withdrawal of application |
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