CA2393460A1 - Fluorine containing allylethers and higher homologs - Google Patents
Fluorine containing allylethers and higher homologs Download PDFInfo
- Publication number
- CA2393460A1 CA2393460A1 CA002393460A CA2393460A CA2393460A1 CA 2393460 A1 CA2393460 A1 CA 2393460A1 CA 002393460 A CA002393460 A CA 002393460A CA 2393460 A CA2393460 A CA 2393460A CA 2393460 A1 CA2393460 A1 CA 2393460A1
- Authority
- CA
- Canada
- Prior art keywords
- perfluorinated
- ether
- perfluoro
- allyl
- hydrogen
- 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.)
- Abandoned
Links
- 229910052731 fluorine Inorganic materials 0.000 title description 7
- 239000011737 fluorine Substances 0.000 title description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title description 5
- -1 perfluoro allyl ethers Chemical class 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000002243 precursor Substances 0.000 claims abstract description 20
- 150000002170 ethers Chemical class 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 150000001336 alkenes Chemical class 0.000 claims abstract description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000000382 dechlorinating effect Effects 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- MHNPWFZIRJMRKC-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound F[C]=C(F)F MHNPWFZIRJMRKC-UHFFFAOYSA-N 0.000 claims description 2
- 238000006298 dechlorination reaction Methods 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 abstract description 14
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 229920001774 Perfluoroether Polymers 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- PQMAKJUXOOVROI-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-(trifluoromethyl)morpholine Chemical compound FC(F)(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F PQMAKJUXOOVROI-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 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 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229920001973 fluoroelastomer Polymers 0.000 description 3
- 239000011701 zinc Substances 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
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-UHFFFAOYSA-N 0.000 description 2
- ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 2,3-dichloropropan-1-ol Chemical compound OCC(Cl)CCl ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001348 alkyl chlorides Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UKBFZYZBLPXEIL-UHFFFAOYSA-N 1,3-dichloro-1-(1,3-dichloro-1,2,2,3,3-pentafluoropropoxy)-1,2,2,3,3-pentafluoropropane Chemical compound FC(F)(Cl)C(F)(F)C(F)(Cl)OC(F)(Cl)C(F)(F)C(F)(F)Cl UKBFZYZBLPXEIL-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IBTLFDCPAJLATQ-UHFFFAOYSA-N 1-prop-2-enoxybutane Chemical compound CCCCOCC=C IBTLFDCPAJLATQ-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- VNJOEUSYAMPBAK-UHFFFAOYSA-N 2-methylbenzenesulfonic acid;hydrate Chemical compound O.CC1=CC=CC=C1S(O)(=O)=O VNJOEUSYAMPBAK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical class OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005459 perfluorocyclohexyl group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/24—Preparation of ethers by reactions not forming ether-oxygen bonds by elimination of halogens, e.g. elimination of HCl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/470,034 | 1999-12-22 | ||
| US09/470,034 US6255535B1 (en) | 1999-12-22 | 1999-12-22 | Fluorine containing allylethers and higher homologs |
| PCT/US2000/013116 WO2001046108A1 (en) | 1999-12-22 | 2000-05-12 | Fluorine containing allylethers and higher homologs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2393460A1 true CA2393460A1 (en) | 2001-05-28 |
Family
ID=23866006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002393460A Abandoned CA2393460A1 (en) | 1999-12-22 | 2000-05-12 | Fluorine containing allylethers and higher homologs |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6255535B1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1240126B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2003518052A (cg-RX-API-DMAC7.html) |
| AU (1) | AU4712800A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2393460A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60026022T2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2001046108A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200204981B (cg-RX-API-DMAC7.html) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4626118B2 (ja) | 1999-08-31 | 2011-02-02 | 旭硝子株式会社 | ｖｉｃ−ジクロロ酸フルオリド化合物の製造方法 |
| US6794457B2 (en) * | 2001-04-30 | 2004-09-21 | 3M Innovative Properties Company | Fluoropolymer curing system containing a nitrogen cure site monomer |
| US20050113609A1 (en) * | 2002-07-03 | 2005-05-26 | Asahi Glass Company Limited | Fluorine-containing unsaturated compound and method for its production |
| EP1535892A4 (en) * | 2002-07-03 | 2006-08-02 | Asahi Glass Co Ltd | Fluorinated unsaturated compound and method of making same |
| JP5021317B2 (ja) | 2003-12-30 | 2012-09-05 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマーの凝集方法および組成物 |
| US7402630B2 (en) * | 2004-12-16 | 2008-07-22 | 3M Innovative Properties Company | Curing compositions for fluoropolymers |
| GB0427913D0 (en) * | 2004-12-21 | 2005-01-19 | 3M Innovative Properties Co | Fluoropolymer for making a fluoroelastomer |
| JP2006232704A (ja) * | 2005-02-23 | 2006-09-07 | Asahi Glass Co Ltd | 新規なフルオロスルホニル基含有化合物 |
| US7294677B2 (en) * | 2005-08-25 | 2007-11-13 | 3M Innovative Properties Company | Catalyst for making fluoroelastomer compositions and methods of using the same |
| US7531701B2 (en) * | 2006-09-12 | 2009-05-12 | Honeywell International Inc. | Allyloxytrifluoropropenes |
| GB2459672A (en) * | 2008-04-30 | 2009-11-04 | 3M Innovative Properties Co | Linear short-chained perfluorinated alkoxy allyl ethers and their preparation |
| EP2445939B1 (en) | 2009-06-25 | 2020-09-23 | 3M Innovative Properties Company | Curing compositions for fluoropolymers |
| CN103619811B (zh) * | 2011-06-27 | 2016-08-17 | 索尔维特殊聚合物意大利有限公司 | 新颖的氟化的不饱和化合物及自其可获得的聚合物 |
| KR101976232B1 (ko) | 2011-11-09 | 2019-05-07 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 플루오로중합체용 경화 조성물 |
| KR102497892B1 (ko) * | 2014-12-19 | 2023-02-08 | 메르크 파텐트 게엠베하 | 불소 화합물 |
| US20200255646A1 (en) | 2015-11-13 | 2020-08-13 | 3M Innovative Properties Company | Compositions including amorphous fluoropolymers and methods of using the same |
| US11179886B2 (en) | 2016-01-21 | 2021-11-23 | 3M Innovative Properties Company | Additive processing of fluoropolymers |
| CN105503548A (zh) * | 2016-01-26 | 2016-04-20 | 巨化集团技术中心 | 一种氟卤代烯醚的合成方法 |
| TW201815845A (zh) | 2016-05-17 | 2018-05-01 | ３Ｍ新設資產公司 | 包括二氟亞乙烯與四氟乙烯的共聚物之組成物及其使用方法 |
| US20190344496A1 (en) | 2016-12-20 | 2019-11-14 | 3M Innovative Properties Company | Composition including fluoropolymer and inorganic filler and method of making a three-dimensional article |
| US11292763B2 (en) | 2017-05-19 | 2022-04-05 | 3M Innovative Properties Company | Methods of making a polyfluorinated allyl ether and compounds relating to the methods |
| WO2019123342A1 (en) | 2017-12-21 | 2019-06-27 | 3M Innovative Properties Company | Methods of making polyfunctional polyfluorinated compounds |
| WO2020068409A1 (en) | 2018-09-24 | 2020-04-02 | Exxonmobil Chemical Patents Inc. | Crosslinked elastomer-polymer blends |
| RU2018141773A (ru) | 2018-11-27 | 2020-05-27 | 3М Инновейтив Пропертиз Компани | Композиции полимерных процессинговых добавок и изделия, полученные с использованием указанных композиций |
| US12312426B2 (en) | 2018-12-17 | 2025-05-27 | 3M Innovative Properties Company | Composition including curable fluoropolymer and curative and methods of making and using them |
| WO2020175674A1 (ja) | 2019-02-28 | 2020-09-03 | Ａｇｃ株式会社 | スルホン酸基含有ポリマー、フルオロスルホニル基含有ポリマーおよび液状組成物 |
| JP2022535815A (ja) | 2019-06-04 | 2022-08-10 | スリーエム イノベイティブ プロパティズ カンパニー | 多官能性フッ素化化合物、その化合物から製造されるフッ素化ポリマー、及び関連方法 |
| WO2021046266A1 (en) | 2019-09-05 | 2021-03-11 | 3M Innovative Properties Company | Composition and article including fluoropolymer and branched silsesquioxane polymer |
| CN114846066A (zh) | 2019-12-30 | 2022-08-02 | 3M创新有限公司 | 包括含氟聚合物、过氧化苯甲酰和交联剂的组合物及相关制品和方法 |
| WO2021214664A1 (en) | 2020-04-21 | 2021-10-28 | 3M Innovative Properties Company | Particles including polytetrafluoroethylene and process for making a three-dimensional article |
| US20240132643A1 (en) | 2021-02-26 | 2024-04-25 | 3M Innovative Properties Company | Process for Making a Fluoropolymer and Fluoropolymer Made Therefrom |
| WO2022189938A1 (en) | 2021-03-10 | 2022-09-15 | 3M Innovative Properties Company | Branched silsesquioxane polymer and compositions and articles including the same |
| EP4526284A1 (en) | 2022-05-17 | 2025-03-26 | DuPont Specialty Products USA, LLC | Method of making halo (alkyl vinyl) ether monomers and fluorinated polymers made with the halo (alkyl vinyl) ether monomer |
| CN120584153A (zh) | 2023-01-27 | 2025-09-02 | 杜邦特种产品美国有限责任公司 | 氟聚合物组合物以及由其制成的制品 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2713593A (en) | 1953-12-21 | 1955-07-19 | Minnesota Mining & Mfg | Fluorocarbon acids and derivatives |
| US4273728A (en) | 1979-03-14 | 1981-06-16 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
| JPS5759850A (en) | 1980-09-30 | 1982-04-10 | Daikin Ind Ltd | Polyfluoroallyl ether and its preparation and use |
| DE3045473A1 (de) | 1980-12-03 | 1982-07-01 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 2-alkenyl-1,1,2-trifluor-2-halogenethyl-ethern |
| US4522995A (en) * | 1983-05-02 | 1985-06-11 | E. I. Du Pont De Nemours And Company | Fluorinated alkyl ether-containing ethylenes, precursors thereto, and copolymers thereof with tetrafluoroethylene |
| DE3863965D1 (de) | 1987-04-25 | 1991-09-05 | Daikin Ind Ltd | Fluorierte vinylaether. |
| DE3718726A1 (de) | 1987-06-04 | 1988-12-22 | Hoechst Ag | Verfahren zur herstellung fluorierter vinylether |
| DE58904307D1 (de) | 1988-03-19 | 1993-06-17 | Hoechst Ag | Verfahren zur herstellung von ungesaettigten halogenierten kohlenwasserstoffen. |
| US5326917A (en) | 1992-12-21 | 1994-07-05 | E. I. Du Pont De Nemours And Company | Fluorinated monomers and polymers |
| US5350497A (en) | 1993-05-21 | 1994-09-27 | E. I. Du Pont De Nemours And Company | Production of perfluoro(alkyl vinyl ethers) |
| US5488142A (en) | 1993-10-04 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Fluorination in tubular reactor system |
| IT1282378B1 (it) * | 1996-04-24 | 1998-03-20 | Ausimont Spa | Perfluoroelastomeri a base di diossoli |
| US5891965A (en) | 1997-01-06 | 1999-04-06 | Dyneon Llc | Low temperature perfluoroether-containing fluoroelastomers |
| JP4078412B2 (ja) | 1997-05-02 | 2008-04-23 | スリーエム カンパニー | 断続電流を用いた電気化学的フッ素処理 |
-
1999
- 1999-12-22 US US09/470,034 patent/US6255535B1/en not_active Expired - Lifetime
-
2000
- 2000-05-12 EP EP00928975A patent/EP1240126B1/en not_active Expired - Lifetime
- 2000-05-12 CA CA002393460A patent/CA2393460A1/en not_active Abandoned
- 2000-05-12 JP JP2001546622A patent/JP2003518052A/ja active Pending
- 2000-05-12 AU AU47128/00A patent/AU4712800A/en not_active Abandoned
- 2000-05-12 DE DE60026022T patent/DE60026022T2/de not_active Expired - Lifetime
- 2000-05-12 WO PCT/US2000/013116 patent/WO2001046108A1/en not_active Ceased
-
2002
- 2002-06-20 ZA ZA200204981A patent/ZA200204981B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE60026022T2 (de) | 2006-10-26 |
| US6255535B1 (en) | 2001-07-03 |
| WO2001046108A1 (en) | 2001-06-28 |
| ZA200204981B (en) | 2003-11-27 |
| EP1240126A1 (en) | 2002-09-18 |
| AU4712800A (en) | 2001-07-03 |
| JP2003518052A (ja) | 2003-06-03 |
| DE60026022D1 (de) | 2006-04-20 |
| EP1240126B1 (en) | 2006-02-15 |
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