JP5144523B2 - α，α−ジヒドロフルオロビニルエーテル、そのホモポリマーおよびコポリマー - Google Patents
α，α−ジヒドロフルオロビニルエーテル、そのホモポリマーおよびコポリマー Download PDFInfo
- Publication number
- JP5144523B2 JP5144523B2 JP2008536782A JP2008536782A JP5144523B2 JP 5144523 B2 JP5144523 B2 JP 5144523B2 JP 2008536782 A JP2008536782 A JP 2008536782A JP 2008536782 A JP2008536782 A JP 2008536782A JP 5144523 B2 JP5144523 B2 JP 5144523B2
- Authority
- JP
- Japan
- Prior art keywords
- ocf
- ether
- dihydrofluorovinyl
- group
- tfe
- 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.)
- Expired - Fee Related
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 56
- 229920001519 homopolymer Polymers 0.000 title claims description 12
- 229920001577 copolymer Polymers 0.000 title description 18
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 124
- 229920001774 Perfluoroether Chemical group 0.000 claims description 13
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 12
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 11
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 9
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 39
- 229920001973 fluoroelastomer Polymers 0.000 description 36
- 239000000178 monomer Substances 0.000 description 34
- 229920000642 polymer Polymers 0.000 description 25
- 239000000203 mixture Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 150000002170 ethers Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- PYLIXCKOHOHGKQ-UHFFFAOYSA-L disodium;hydrogen phosphate;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O PYLIXCKOHOHGKQ-UHFFFAOYSA-L 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- 229940052354 dibasic sodium phosphate heptahydrate Drugs 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 238000007720 emulsion polymerization reaction Methods 0.000 description 9
- 230000009477 glass transition Effects 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- -1 perfluoro Chemical group 0.000 description 9
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 7
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 7
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000806 elastomer Substances 0.000 description 6
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 6
- 239000004816 latex Substances 0.000 description 6
- 229920000126 latex Polymers 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- JQHYTVDCWJSRGU-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-methoxy-3-(1,2,2-trifluoroethenoxy)propane Chemical compound COC(F)(F)C(F)(F)COC(F)=C(F)F JQHYTVDCWJSRGU-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- YOALFLHFSFEMLP-UHFFFAOYSA-N azane;2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YOALFLHFSFEMLP-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000010702 perfluoropolyether Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 3
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 3
- ILUHDFNNECCMJZ-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-methoxypropan-1-ol Chemical compound COC(F)(F)C(F)(F)CO ILUHDFNNECCMJZ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229920002313 fluoropolymer Polymers 0.000 description 3
- 239000004811 fluoropolymer Substances 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- UZUFPBIDKMEQEQ-UHFFFAOYSA-N perfluorononanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UZUFPBIDKMEQEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- ISPLDXGHYASNMO-UHFFFAOYSA-N 1-[[difluoro(trifluoromethoxy)methoxy]-difluoromethoxy]-1,1-difluoro-2-(1,2,2-trifluoroethenoxy)ethane Chemical compound FC(F)=C(F)OCC(F)(F)OC(F)(F)OC(F)(F)OC(F)(F)F ISPLDXGHYASNMO-UHFFFAOYSA-N 0.000 description 1
- PJRIQFXPYMVWOU-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,5-nonafluoropentan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F PJRIQFXPYMVWOU-UHFFFAOYSA-N 0.000 description 1
- AKQIUIMGAPTSMT-UHFFFAOYSA-N 2-chloro-1,1,3,4,4,5,6,6,6-nonafluoro-3-(trifluoromethyl)hex-1-ene Chemical compound FC(C(F)(F)F)C(C(C(F)(F)F)(C(=C(F)F)Cl)F)(F)F AKQIUIMGAPTSMT-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
- OUJSWWHXKJQNMJ-UHFFFAOYSA-N 3,3,4,4-tetrafluoro-4-iodobut-1-ene Chemical compound FC(F)(I)C(F)(F)C=C OUJSWWHXKJQNMJ-UHFFFAOYSA-N 0.000 description 1
- FDKVJQSCOYNONR-UHFFFAOYSA-N FC=COCC(OCCC#N)C Chemical compound FC=COCC(OCCC#N)C FDKVJQSCOYNONR-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- KURZCZMGELAPSV-UHFFFAOYSA-N [Br].[I] Chemical compound [Br].[I] KURZCZMGELAPSV-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- NDNOUXQCMAHOSA-UHFFFAOYSA-N methyl 2,2,3,3-tetrafluoro-3-methoxypropanoate Chemical compound COC(=O)C(F)(F)C(F)(F)OC NDNOUXQCMAHOSA-UHFFFAOYSA-N 0.000 description 1
- MHAIQPNJLRLFLO-UHFFFAOYSA-N methyl 2-fluoropropanoate Chemical compound COC(=O)C(C)F MHAIQPNJLRLFLO-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CBHOWTTXCQAOID-UHFFFAOYSA-L sodium ethane formaldehyde mercury(2+) molecular iodine 2-sulfidobenzoate Chemical compound [Na+].[Hg++].C[CH2-].II.C=O.[O-]C(=O)c1ccccc1[S-] CBHOWTTXCQAOID-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
-
- 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
- C08F14/00—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 a halogen
- C08F14/18—Monomers containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72816905P | 2005-10-19 | 2005-10-19 | |
| US60/728,169 | 2005-10-19 | ||
| US11/498,907 US20070088143A1 (en) | 2005-10-19 | 2006-08-03 | Alpha, alpha-dihydrofluorovinyl ethers, homopolymers and copolymers thereof |
| US11/498,907 | 2006-08-03 | ||
| PCT/US2006/040764 WO2007047788A1 (en) | 2005-10-19 | 2006-10-19 | α,α-DIHYDROFLUOROVINYL ETHERS, HOMOPOLYMERS AND COPOLYMERS THEREOF |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009512759A JP2009512759A (ja) | 2009-03-26 |
| JP2009512759A5 JP2009512759A5 (enExample) | 2009-12-03 |
| JP5144523B2 true JP5144523B2 (ja) | 2013-02-13 |
Family
ID=37714679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008536782A Expired - Fee Related JP5144523B2 (ja) | 2005-10-19 | 2006-10-19 | α，α−ジヒドロフルオロビニルエーテル、そのホモポリマーおよびコポリマー |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20070088143A1 (enExample) |
| EP (1) | EP1940762A1 (enExample) |
| JP (1) | JP5144523B2 (enExample) |
| WO (1) | WO2007047788A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3280379B2 (ja) | 1992-07-09 | 2002-05-13 | シー． ブリグズ，オーブリー | 工業プロセス等のための汚染制御装置 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159609A (en) * | 1956-10-26 | 1964-12-01 | Du Pont | Copolymers of perfluorovinyl ethers |
| CA950923A (en) * | 1971-03-29 | 1974-07-09 | E. I. Du Pont De Nemours And Company | Polymers of perfluorovinyl ethers |
| US4513128A (en) * | 1983-06-23 | 1985-04-23 | E. I. Du Pont De Nemours And Company | Fluorinated vinyl ether copolymers having low glass transition temperatures |
| US4948844A (en) * | 1988-04-16 | 1990-08-14 | Tokuyama Soda Kabushiki Kaisha | Process for preparation of perfluorinated copolymer |
| JPH072815B2 (ja) * | 1988-04-16 | 1995-01-18 | 株式会社トクヤマ | パーフルオロ化共重合体の製造方法 |
| JP2953564B2 (ja) * | 1988-12-29 | 1999-09-27 | 株式会社トクヤマ | 含フッ素ランダム共重合体 |
| JP3040378B2 (ja) * | 1988-12-29 | 2000-05-15 | 株式会社トクヤマ | 含フッ素ランダム共重合体の製造方法 |
| DE4040471A1 (de) * | 1990-08-01 | 1992-02-06 | Bayer Ag | Haertbare mischungen zur herstellung von epoxidnetzwerken, verfahren zu deren herstellung und verwendung |
| JP3080121B2 (ja) * | 1993-01-08 | 2000-08-21 | 株式会社トクヤマ | 電 線 |
| JP2878070B2 (ja) * | 1993-06-01 | 1999-04-05 | 株式会社トクヤマ | パーフルオロ共重合体の製造方法 |
| JP3334959B2 (ja) * | 1993-09-27 | 2002-10-15 | 株式会社トクヤマ | 含フッ素ビニルエーテル共重合体 |
| JPH09302188A (ja) * | 1996-05-17 | 1997-11-25 | Tokuyama Corp | 含フッ素共重合体の製造方法 |
| JPH09309919A (ja) * | 1996-05-23 | 1997-12-02 | Tokuyama Corp | フッ素化重合体の製造方法 |
| CA2252298A1 (en) * | 1998-03-31 | 1999-09-30 | Molly S. Shoichet | New fluoromonomers and methods of production, and new fluoropolymers produced therefrom |
| US6294627B1 (en) * | 1998-08-31 | 2001-09-25 | Dyneon Llc | Low temperature fluorocarbon elastomers |
| JP2001089531A (ja) * | 1999-07-19 | 2001-04-03 | Tokuyama Corp | 含フッ素共重合体 |
| JP2002097230A (ja) * | 2000-09-22 | 2002-04-02 | Nippon Mektron Ltd | 含フッ素共重合体の製造方法 |
| US6730760B2 (en) * | 2001-01-31 | 2004-05-04 | 3M Innovative Properties Company | Perfluoroelastomers having a low glass transition temperature and method of making them |
| JP4272867B2 (ja) * | 2002-10-08 | 2009-06-03 | 富士フイルム株式会社 | 反射防止膜、反射防止フィルム、画像表示装置、および反射防止膜の製造方法 |
| JP2005070213A (ja) * | 2003-08-21 | 2005-03-17 | Mitsubishi Rayon Co Ltd | マルチコアプラスチック光ファイバおよびマルチコアプラスチック光ファイバケーブル |
-
2006
- 2006-08-03 US US11/498,907 patent/US20070088143A1/en not_active Abandoned
- 2006-10-19 WO PCT/US2006/040764 patent/WO2007047788A1/en not_active Ceased
- 2006-10-19 EP EP06817138A patent/EP1940762A1/en not_active Withdrawn
- 2006-10-19 JP JP2008536782A patent/JP5144523B2/ja not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3280379B2 (ja) | 1992-07-09 | 2002-05-13 | シー． ブリグズ，オーブリー | 工業プロセス等のための汚染制御装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009512759A (ja) | 2009-03-26 |
| US20070088143A1 (en) | 2007-04-19 |
| WO2007047788A1 (en) | 2007-04-26 |
| EP1940762A1 (en) | 2008-07-09 |
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