DE2817366C2 - - Google Patents
Info
- Publication number
- DE2817366C2 DE2817366C2 DE2817366A DE2817366A DE2817366C2 DE 2817366 C2 DE2817366 C2 DE 2817366C2 DE 2817366 A DE2817366 A DE 2817366A DE 2817366 A DE2817366 A DE 2817366A DE 2817366 C2 DE2817366 C2 DE 2817366C2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compounds
- fluoride
- compound
- reaction
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 34
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 14
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 10
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 9
- NHJFHUKLZMQIHN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl 2,2,3,3,3-pentafluoropropaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)F NHJFHUKLZMQIHN-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- -1 alkoxy ester compound Chemical class 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- UOGPGUXIITWAJH-UHFFFAOYSA-N OC(C(C(OC(C(OCC(F)(F)F)(F)F)(C(F)(F)F)F)(F)F)(F)F)=O Chemical compound OC(C(C(OC(C(OCC(F)(F)F)(F)F)(C(F)(F)F)F)(F)F)(F)F)=O UOGPGUXIITWAJH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 2
- 229920001198 elastomeric copolymer Polymers 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 235000011008 sodium phosphates Nutrition 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LIHVFFFGWFBSAT-UHFFFAOYSA-N 2,2-difluoropropanedioic acid Chemical class OC(=O)C(F)(F)C(O)=O LIHVFFFGWFBSAT-UHFFFAOYSA-N 0.000 description 1
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXRROZVNOOEPPZ-UHFFFAOYSA-N Flupropanate Chemical compound OC(=O)C(F)(F)C(F)F PXRROZVNOOEPPZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical group FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229940096017 silver fluoride Drugs 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- XCXLEIPEAAEYTF-UHFFFAOYSA-M sodium fluorosulfate Chemical compound [Na+].[O-]S(F)(=O)=O XCXLEIPEAAEYTF-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- MIECFAZUSQCOEL-UHFFFAOYSA-N sulfane;hydrofluoride Chemical class [F-].[SH3+] MIECFAZUSQCOEL-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 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
- 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
- C08F16/14—Monomers containing only one unsaturated aliphatic radical
- C08F16/26—Monomers containing oxygen atoms in addition to the ether oxygen
-
- 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
- C07C59/60—Unsaturated compounds containing ether groups, groups, groups, or groups the non-carboxylic part of the ether being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/789,724 US4131740A (en) | 1977-04-20 | 1977-04-20 | Alkyl perfluoro-ω-fluoroformyl esters and their preparation |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2817366A1 DE2817366A1 (de) | 1978-10-26 |
DE2817366C2 true DE2817366C2 (en, 2012) | 1989-01-26 |
Family
ID=25148499
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19782817366 Granted DE2817366A1 (de) | 1977-04-20 | 1978-04-20 | Alkylperfluor-omega-fluorformylester und verfahren zu ihrer herstellung |
Country Status (15)
Country | Link |
---|---|
US (2) | US4131740A (en, 2012) |
JP (1) | JPS6049176B2 (en, 2012) |
AU (1) | AU515564B2 (en, 2012) |
BE (1) | BE866123A (en, 2012) |
BR (1) | BR7802432A (en, 2012) |
DE (1) | DE2817366A1 (en, 2012) |
FR (1) | FR2387938A1 (en, 2012) |
GB (1) | GB1593222A (en, 2012) |
IT (1) | IT1094423B (en, 2012) |
MX (2) | MX149082A (en, 2012) |
NL (1) | NL187435C (en, 2012) |
NZ (1) | NZ187025A (en, 2012) |
SE (1) | SE436869B (en, 2012) |
SU (1) | SU869555A3 (en, 2012) |
ZA (1) | ZA782223B (en, 2012) |
Families Citing this family (82)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4267364A (en) * | 1977-04-20 | 1981-05-12 | E. I. Dupont De Nemours And Company | Fluorinated ion exchange polymer containing carboxylic groups, process for making same, and film and membrane thereof |
US4209635A (en) * | 1979-03-02 | 1980-06-24 | Asahi Glass Company Limited | Process for producing perfluorinated vinyl ether having ester group |
US4292449A (en) * | 1979-03-14 | 1981-09-29 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
US4273728A (en) * | 1979-03-14 | 1981-06-16 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
US4273729A (en) * | 1979-03-14 | 1981-06-16 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
US4275225A (en) * | 1979-03-14 | 1981-06-23 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
US4349650A (en) * | 1979-03-14 | 1982-09-14 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
US4608206A (en) * | 1979-11-16 | 1986-08-26 | E. I. Du Pont De Nemours And Company | Fluorinated 3-ketoglutaroyl halides |
US5023362A (en) * | 1980-04-03 | 1991-06-11 | E. I. Du Pont De Nemours And Company | Alkyl perfluoro(2-methyl-5-oxo-3-oxahexanoate) |
US4335255A (en) * | 1980-04-03 | 1982-06-15 | E. I. Du Pont De Nemours And Company | Alkyl perfluoro (2-methyl-5-oxo-3-oxahexanoate) |
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 |
US4515989A (en) * | 1980-06-11 | 1985-05-07 | The Dow Chemical Company | Preparation decarboxylation and polymerization of novel acid flourides and resulting monomers |
US4578512A (en) * | 1980-06-11 | 1986-03-25 | The Dow Chemical Company | Process to produce novel fluorocarbon vinyl ethers and resulting polymers |
US4337137A (en) * | 1980-06-11 | 1982-06-29 | The Dow Chemical Company | Composite ion exchange membranes |
US4804727A (en) * | 1980-06-11 | 1989-02-14 | The Dow Chemical Company | Process to produce novel fluorocarbon vinyl ethers and resulting polymers |
US4330654A (en) * | 1980-06-11 | 1982-05-18 | The Dow Chemical Company | Novel polymers having acid functionality |
US4470889A (en) * | 1980-06-11 | 1984-09-11 | The Dow Chemical Company | Electrolytic cell having an improved ion exchange membrane and process for operating |
US4345092A (en) * | 1980-08-04 | 1982-08-17 | E. I. Du Pont De Nemours And Company | Process for alkyl perfluoro(4,7-dioxa-5-methyl-8-fluoroformylnonanoate |
US4316986A (en) * | 1980-09-23 | 1982-02-23 | E. I. Dupont De Nemours & Company | Preparation of difluoromalonyl fluoride |
US4414159A (en) * | 1980-09-26 | 1983-11-08 | E. I. Du Pont De Nemours & Co. | Vinyl ether monomers and polymers therefrom |
US4334082A (en) * | 1980-09-26 | 1982-06-08 | E. I. Du Pont De Nemours And Company | Dialkyl perfluoro-ω-fluoroformyl diesters and monomers and polymers therefrom |
US4360601A (en) * | 1980-12-10 | 1982-11-23 | E. I. Du Pont De Nemours And Company | Process for extraction of fluorinated copolymers with fluorocarbons |
US4401711A (en) * | 1981-01-16 | 1983-08-30 | E. I. Du Pont De Nemours And Company | Cation exchange membrane with high equivalent weight component |
US4385187A (en) * | 1981-06-30 | 1983-05-24 | E. I. Du Pont De Nemours And Company | Perfluoroketovinyl ethers and copolymers therefrom |
US4434273A (en) | 1981-06-30 | 1984-02-28 | E. I. Du Pont De Nemours And Company | Perfluoroketovinyl ethers and copolymers therefrom |
US4474700A (en) * | 1981-07-02 | 1984-10-02 | E. I. Du Pont DeNemours and Company | β-Substituted polyfluoropropionate salts and derivatives |
US4390720A (en) * | 1981-10-14 | 1983-06-28 | E. I. Du Pont De Nemours And Company | Alkyl-ω-fluoroformyl ester and process |
US4454247A (en) * | 1981-12-14 | 1984-06-12 | E. I. Du Pont De Nemours & Company | Ion exchange membranes |
US4440917A (en) * | 1981-12-14 | 1984-04-03 | E. I. Du Pont De Nemours & Company | Vinyl ethers monomers and polymers therefrom |
US4420638A (en) * | 1982-03-02 | 1983-12-13 | E. I. Du Pont De Nemours And Company | Fluorinated ether-ketones |
US4686300A (en) * | 1983-03-07 | 1987-08-11 | E. I. Du Pont De Nemours And Company | Polyfluoro gamma-ketoesters and 5-hydroxy gamma lactone analogues thereof |
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 |
JPS60147415A (ja) * | 1984-01-10 | 1985-08-03 | Daikin Ind Ltd | 含フッ素共重合体および硬化用被覆組成物 |
US4591439A (en) * | 1984-05-08 | 1986-05-27 | E. I. Du Pont De Nemours And Company | Ion exchange process and apparatus |
US4859745A (en) * | 1987-12-22 | 1989-08-22 | The Dow Chemical Company | Stratified fibrous fluoropolymer compositions and process for forming such fluoropolymers |
US5006259A (en) * | 1988-03-21 | 1991-04-09 | E. I. Du Pont De Nemours And Company | Process and means for use of anaphylatoxin adsorbents |
US4970295A (en) * | 1989-02-27 | 1990-11-13 | Arco Chemical Technology, Inc. | Preparation of oxetane polyether polyols using a bleaching earth catalyst |
US5134211A (en) * | 1990-01-31 | 1992-07-28 | E. I. Du Pont De Nemours And Company | Hydroxy containing fluorovinyl compounds and polymers thereof |
US5128014A (en) * | 1991-03-01 | 1992-07-07 | E. I. Du Pont De Nemours And Company | Irradiation of cation exchange membranes |
US5252193A (en) * | 1991-11-04 | 1993-10-12 | E. I. Du Pont De Nemours And Company | Controlled roughening of reinforced cation exchange membrane |
EP0545068A3 (en) * | 1991-11-08 | 1993-12-22 | Du Pont | Wetting of diaphragms |
US5264093A (en) * | 1992-04-30 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Irradiation of cation exchange membranes to increse current efficiency and reduce power consumption |
EP0606883B1 (en) | 1993-01-14 | 1998-10-14 | Nippon Mektron, Ltd. | Fluorine-containing elastomer composition |
US5330626A (en) * | 1993-02-16 | 1994-07-19 | E. I. Du Pont De Nemours And Company | Irradiation of polymeric ion exchange membranes to increase water absorption |
US5824749A (en) * | 1994-10-04 | 1998-10-20 | Nippon Mektron, Limited | Fluorine-containing elastomer composition |
JP3398492B2 (ja) * | 1994-10-21 | 2003-04-21 | 日本メクトロン株式会社 | 含フッ素エラストマー組成物 |
JP3599390B2 (ja) * | 1994-11-04 | 2004-12-08 | 日本メクトロン株式会社 | パーフルオロ不飽和ニトリル化合物およびその製造法 |
US5637748A (en) * | 1995-03-01 | 1997-06-10 | E. I. Du Pont De Nemours And Company | Process for synthesizing fluorinated nitrile compounds |
JP3223776B2 (ja) * | 1995-03-31 | 2001-10-29 | 日本メクトロン株式会社 | 含フッ素エラストマー組成物 |
US5919878A (en) * | 1996-09-13 | 1999-07-06 | E. I. Du Pont De Nemours And Company | Amorphous fluoropolymer containing perfluoro(ethyl vinyl ether) |
US5969067A (en) * | 1996-09-13 | 1999-10-19 | E.I. Dupont De Nemours And Company | Phosphorus-containing fluoromonomers and polymers thereof |
JP3292072B2 (ja) * | 1996-12-02 | 2002-06-17 | 信越化学工業株式会社 | ヘキサフロロプロペンオキシドの重合方法 |
JP3533889B2 (ja) | 1997-07-15 | 2004-05-31 | ダイキン工業株式会社 | 末端に酸素官能基をもつフルオロビニルエーテルおよびその製法 |
US6248469B1 (en) | 1997-08-29 | 2001-06-19 | Foster-Miller, Inc. | Composite solid polymer electrolyte membranes |
US7049380B1 (en) * | 1999-01-19 | 2006-05-23 | Gore Enterprise Holdings, Inc. | Thermoplastic copolymer of tetrafluoroethylene and perfluoromethyl vinyl ether and medical devices employing the copolymer |
US7550216B2 (en) * | 1999-03-03 | 2009-06-23 | Foster-Miller, Inc. | Composite solid polymer electrolyte membranes |
US6407282B1 (en) * | 1999-11-04 | 2002-06-18 | Nippon Mektron, Limited | Process for producing monoester from dicarboxylic acid fluoride |
JP4802438B2 (ja) * | 2000-06-02 | 2011-10-26 | 旭硝子株式会社 | 熱分解反応による不飽和化合物の製造方法 |
US7019163B2 (en) * | 2001-06-29 | 2006-03-28 | Asahi Kasei Kabushiki Kaisha | Process for producing perfluorovinylcarboxylic acid ester |
WO2003002506A1 (fr) * | 2001-06-29 | 2003-01-09 | Asahi Kasei Kabushiki Kaisha | Procédé de production d'éther vinylique fluoré |
US7276624B2 (en) * | 2002-05-14 | 2007-10-02 | E. I. Du Pont De Nemours And Company | Fluorosulfates of hexafluoroisobutylene and its higher homologs |
US6747110B2 (en) | 2002-06-13 | 2004-06-08 | Acushnet Company | Golf balls comprising non-ionomeric fluoropolymer |
US7009002B2 (en) * | 2002-06-13 | 2006-03-07 | Acushnet Company | Impact resistant non-ionic fluoropolymer blends for golf ball inner layers |
US20040024448A1 (en) | 2002-08-05 | 2004-02-05 | Chang James W. | Thermoplastic fluoropolymer-coated medical devices |
EP1587784B1 (en) | 2003-01-29 | 2014-10-15 | Greene, Tweed Of Delaware, Inc. | Bisaminophenyl-based curatives and amidine-based curatives and cure accelerators for perfluoroelastomeric compositions |
CN100410278C (zh) * | 2003-01-29 | 2008-08-13 | 特拉华特威德·格林公司 | 用于全氟弹性体组合物的基于双氨基苯基的固化剂和基于脒的固化剂以及固化促进剂 |
DE10336796B4 (de) * | 2003-08-08 | 2005-05-19 | Henkel Kgaa | Wasch- oder Reinigungsmittel |
US7514506B2 (en) * | 2004-03-31 | 2009-04-07 | Greene, Tweed Of Delaware, Inc. | Fast curing fluoroelastomeric compositions, adhesive fluoroelastomeric compositions and methods for bonding fluoroelastomeric compositions |
WO2006057203A1 (ja) * | 2004-11-25 | 2006-06-01 | Unimatec Co., Ltd. | 含フッ素共重合体 |
US7834209B2 (en) * | 2005-06-07 | 2010-11-16 | E.I. Du Pont De Nemours And Company | Hydrofluoroalkanesulfonic acids from fluorovinyl ethers |
US20070036926A1 (en) | 2005-08-12 | 2007-02-15 | Fish Robert B Jr | Multilayered pipes |
US20070231588A1 (en) * | 2006-03-31 | 2007-10-04 | Karthikeyan Kanakarajan | Capacitive polyimide laminate |
US20070232734A1 (en) * | 2006-03-31 | 2007-10-04 | Karthikeyan Kanakarajan | Polyimide based compositions useful in high frequency circuitry applications and methods relating thereto |
JP5228913B2 (ja) * | 2006-10-03 | 2013-07-03 | ユニマテック株式会社 | 含フッ素エラストマー組成物 |
US20100185007A1 (en) * | 2007-06-25 | 2010-07-22 | Akiyoshi Yamauchi | Process for preparing fluoroamide and fluoronitrile |
US20140255703A1 (en) | 2013-03-05 | 2014-09-11 | E I Du Pont De Nemours And Company | Adhesion of Fluoropolymer to Metal |
JP6104382B2 (ja) * | 2013-06-19 | 2017-03-29 | 旭化成株式会社 | 含フッ素系重合体、陽イオン交換膜及び電解槽 |
EP3093281B1 (en) | 2014-01-10 | 2018-11-21 | Unimatec Co., Ltd. | Alkali metal salt of perfluoro(vinyloxy polyether) carboxylic acid, and method for producing same |
CN113056492B (zh) | 2018-11-14 | 2023-01-06 | 3M创新有限公司 | 全氟脂环族甲基乙烯基醚的共聚物 |
JP6888698B2 (ja) * | 2019-09-13 | 2021-06-16 | ダイキン工業株式会社 | フルオロポリエーテル基含有化合物およびその製造方法 |
EP4029898B1 (en) * | 2019-09-13 | 2025-08-06 | Daikin Industries, Ltd. | Fluoropolyether group containing compound and method for producing same |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3114778A (en) * | 1963-12-17 | Fluorinated vinyl ethers and their | ||
US3250808A (en) * | 1963-10-31 | 1966-05-10 | Du Pont | Fluorocarbon ethers derived from hexafluoropropylene epoxide |
US3248419A (en) * | 1964-01-03 | 1966-04-26 | Pennsalt Chemicals Corp | Preparation of halogenated esters from halogenated chlorosulfate |
US3706773A (en) * | 1967-04-25 | 1972-12-19 | Allied Chem | Fluorocarbon compounds |
US3852326A (en) * | 1972-06-14 | 1974-12-03 | Du Pont | Cyanoperfluoro(vinyl ethers), their preparation and copolymers thereof |
GB1529514A (en) * | 1975-04-02 | 1978-10-25 | Du Pont | Catalytic reaction of hexafluoropropylene epoxide with a ketone or acid fluoride |
-
1977
- 1977-04-20 US US05/789,724 patent/US4131740A/en not_active Expired - Lifetime
-
1978
- 1978-01-11 US US05/868,615 patent/US4138426A/en not_active Expired - Lifetime
- 1978-03-16 SE SE7803062A patent/SE436869B/sv not_active IP Right Cessation
- 1978-04-17 AU AU35165/78A patent/AU515564B2/en not_active Expired
- 1978-04-18 JP JP53044909A patent/JPS6049176B2/ja not_active Expired
- 1978-04-19 MX MX173174A patent/MX149082A/es unknown
- 1978-04-19 GB GB15526/78A patent/GB1593222A/en not_active Expired
- 1978-04-19 ZA ZA00782223A patent/ZA782223B/xx unknown
- 1978-04-19 IT IT22497/78A patent/IT1094423B/it active
- 1978-04-19 NZ NZ187025A patent/NZ187025A/xx unknown
- 1978-04-19 BE BE186900A patent/BE866123A/xx not_active IP Right Cessation
- 1978-04-19 FR FR7811504A patent/FR2387938A1/fr active Granted
- 1978-04-19 MX MX197260A patent/MX172538B/es unknown
- 1978-04-19 SU SU782604925A patent/SU869555A3/ru active
- 1978-04-19 BR BR7802432A patent/BR7802432A/pt unknown
- 1978-04-20 DE DE19782817366 patent/DE2817366A1/de active Granted
- 1978-04-20 NL NLAANVRAGE7804228,A patent/NL187435C/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
FR2387938A1 (fr) | 1978-11-17 |
NL187435B (nl) | 1991-05-01 |
SE7803062L (sv) | 1978-10-21 |
US4131740A (en) | 1978-12-26 |
ZA782223B (en) | 1979-04-25 |
JPS53132519A (en) | 1978-11-18 |
GB1593222A (en) | 1981-07-15 |
AU3516578A (en) | 1979-10-25 |
FR2387938B1 (en, 2012) | 1984-08-10 |
DE2817366A1 (de) | 1978-10-26 |
MX149082A (es) | 1983-08-19 |
IT1094423B (it) | 1985-08-02 |
IT7822497A0 (it) | 1978-04-19 |
SU869555A3 (ru) | 1981-09-30 |
NL7804228A (nl) | 1978-10-24 |
NZ187025A (en) | 1979-06-19 |
BE866123A (fr) | 1978-10-19 |
AU515564B2 (en) | 1981-04-09 |
BR7802432A (pt) | 1979-01-02 |
MX172538B (es) | 1993-12-17 |
JPS6049176B2 (ja) | 1985-10-31 |
NL187435C (nl) | 1991-10-01 |
SE436869B (sv) | 1985-01-28 |
US4138426A (en) | 1979-02-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE2817366C2 (en, 2012) | ||
DE69402473T2 (de) | Perfluorodioxole, ihre Herstellung und deren Homopolymere und Copolymere | |
DE1645126C3 (de) | Homopolymerisate und Mischpolymerisate von Perfluor-(2-methylen-4-methyl-1,3-dioxolan) und Verfahren zu deren Herstellung | |
DE3486428T2 (de) | Halogen enthaltendes Polyether | |
US4515989A (en) | Preparation decarboxylation and polymerization of novel acid flourides and resulting monomers | |
DE2147102C3 (de) | Verfahren zur Herstellung von difunktionellen fluorhaltigen Polymeren | |
DE69315593T2 (de) | Fluorinierte monomere und polymere | |
DE3032471C2 (en, 2012) | ||
DE69316012T2 (de) | Verfahren zur produktion fluorinierter vinylether | |
US4687821A (en) | Preparation, decarboxylation and polymerization of novel acid fluorides and resulting monomers | |
DE69011337T2 (de) | Polyhalodihydrodioxine und polyhalodioxole. | |
DE69202764T2 (de) | Perfluorierte cyclische polyether, verwendbar als schmiermittel und wärmeübertragungsflüssigkeiten. | |
DE4219764A1 (de) | Cyclopolymerisierbare Fluorverbindungen, Verfahren zu deren Herstellung und daraus erhältliche thermoplastische Fluorpolymere | |
DE69300047T2 (de) | Oligoetherderivate von Hexafluorpropylenoxid und Verfahren zu ihrer Herstellung. | |
EP0087737A1 (de) | Perfluorierte Vinylether mit einem sekundären Wasserstoffatom, Polymere daraus, sowie Verfahren zur Herstellung der Monomeren | |
DE2261108C3 (de) | Verfahren zur Herstellung fluorhaltiger Carbonyldihalogenide | |
DE69706014T2 (de) | Verfahren zur Polymerisation von Hexafluoropropenoxid | |
US4247713A (en) | Alkyl perfluoro-ω-fluoroformyl esters and their preparation | |
DE2708677C3 (de) | Verfahren zur Herstellung von Alkoxycarbonylperfluoralkylperfluorvinyläthern | |
DE2517357C3 (de) | Perfluorierte Vinylether und Verfahren zu deren Herstellung | |
JPS627898B2 (en, 2012) | ||
DE2411170A1 (de) | Perfluormethylencyclopropanpolymerisate | |
JP2792983B2 (ja) | α―ブロモ‐アシル‐フルオリドの製造法 | |
US4531011A (en) | Alkyl perfluoro-omega-(2-iodoethoxy) compounds and vinyl ethers therefrom | |
CA1144566A (en) | Alkyl perfluoro-w-fluoroformyl esters, their preparation and monomers therefrom |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
8110 | Request for examination paragraph 44 | ||
D2 | Grant after examination | ||
8364 | No opposition during term of opposition | ||
8339 | Ceased/non-payment of the annual fee |