CA2263307C - Aqueous dehydrofluorination method - Google Patents
Aqueous dehydrofluorination method Download PDFInfo
- Publication number
- CA2263307C CA2263307C CA002263307A CA2263307A CA2263307C CA 2263307 C CA2263307 C CA 2263307C CA 002263307 A CA002263307 A CA 002263307A CA 2263307 A CA2263307 A CA 2263307A CA 2263307 C CA2263307 C CA 2263307C
- Authority
- CA
- Canada
- Prior art keywords
- fluoropolymer
- emulsion
- base compound
- dehydrofluorination
- reaction solution
- 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
- 238000000034 method Methods 0.000 title claims abstract description 46
- 238000005796 dehydrofluorination reaction Methods 0.000 title claims abstract description 43
- 229920002313 fluoropolymer Polymers 0.000 claims abstract description 159
- 239000004811 fluoropolymer Substances 0.000 claims abstract description 158
- 239000000839 emulsion Substances 0.000 claims abstract description 78
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 239000003960 organic solvent Substances 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 239000002585 base Substances 0.000 claims description 54
- 230000015271 coagulation Effects 0.000 claims description 18
- 238000005345 coagulation Methods 0.000 claims description 18
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 10
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 9
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 9
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000005323 carbonate salts Chemical class 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 150000007514 bases Chemical class 0.000 abstract 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 68
- 239000000243 solution Substances 0.000 description 34
- 239000003637 basic solution Substances 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 12
- 239000000178 monomer Substances 0.000 description 9
- 229910017974 NH40H Inorganic materials 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 238000004448 titration Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 230000001804 emulsifying effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000003444 phase transfer catalyst Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- -1 tetraalkylammonium hydroxide compound Chemical class 0.000 description 4
- 238000004293 19F NMR spectroscopy Methods 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 229920001973 fluoroelastomer Polymers 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 1
- VUWKDMFLTIEFLA-UHFFFAOYSA-N 2-chloro-1,3,4,4,5,6,6,6-octafluorohex-1-ene Chemical compound ClC(=CF)C(C(C(C(F)(F)F)F)(F)F)F VUWKDMFLTIEFLA-UHFFFAOYSA-N 0.000 description 1
- LVRCEUVOXCJYSV-UHFFFAOYSA-N CN(C)S(=O)=O Chemical compound CN(C)S(=O)=O LVRCEUVOXCJYSV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- DZGPDEKNLIGJNH-UHFFFAOYSA-N FC(=C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)F)OC(=C(F)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)F Chemical compound FC(=C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)F)OC(=C(F)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)F DZGPDEKNLIGJNH-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004673 fluoride salts Chemical group 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical group C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000010626 work up procedure 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/26—Removing halogen atoms or halogen-containing groups from the molecule
Landscapes
- Chemical & Material Sciences (AREA)
- General 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/703422 | 1996-08-26 | ||
| US08/703,422 US5733981A (en) | 1996-08-26 | 1996-08-26 | Aqueous dehydrofluorination method |
| PCT/US1996/020651 WO1998008880A1 (en) | 1996-08-26 | 1996-12-23 | Aqueous dehydrofluorination method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2263307A1 CA2263307A1 (en) | 1998-03-05 |
| CA2263307C true CA2263307C (en) | 2005-12-20 |
Family
ID=24825324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002263307A Expired - Fee Related CA2263307C (en) | 1996-08-26 | 1996-12-23 | Aqueous dehydrofluorination method |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5733981A (enExample) |
| EP (1) | EP0920457B1 (enExample) |
| JP (1) | JP3975249B2 (enExample) |
| AU (1) | AU1350397A (enExample) |
| CA (1) | CA2263307C (enExample) |
| DE (1) | DE69621840T2 (enExample) |
| WO (1) | WO1998008880A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6197393B1 (en) | 1997-06-27 | 2001-03-06 | 3M Innovative Properties Company | Multi-layer compositions comprising a fluoropolymer |
| DK173613B1 (da) | 1998-10-02 | 2001-04-30 | Stigsnaes Industrimiljoe As | Fremgangsmåde til behandling af halogenholdigt organisk affaldsmateriale |
| US6166156A (en) * | 1998-11-12 | 2000-12-26 | Wu; Chengjiu | Method for making photocurable halofluorinated acrylates |
| WO2000052084A1 (en) | 1999-03-02 | 2000-09-08 | 3M Innovative Properties Company | Compositions for fluoropolymer bonding to non-fluorinated polymers |
| AU1383701A (en) | 1999-09-16 | 2001-04-17 | Merck Patent Gmbh | Optical compensator and liquid crystal display i |
| IT1318683B1 (it) | 2000-08-22 | 2003-08-27 | Ausimont Spa | Miscele di elastomeri fluorurati ed acrilici. |
| US7351471B2 (en) * | 2000-12-06 | 2008-04-01 | 3M Innovative Properties Company | Fluoropolymer coating compositions with multifunctional fluoroalkyl crosslinkers for anti-reflective polymer films |
| US7141303B2 (en) | 2001-03-06 | 2006-11-28 | 3M Innovative Properties Company | Protective articles |
| US20030198770A1 (en) * | 2002-04-18 | 2003-10-23 | 3M Innovative Properties Company | Composite fluoropolymer-perfluoropolymer assembly |
| US6849314B2 (en) * | 2002-04-18 | 2005-02-01 | 3M Innovative Properties Company | Fluoropolymer blends and multilayer articles |
| US7569275B2 (en) | 2002-04-18 | 2009-08-04 | 3M Innovative Properties Company | Fluoropolymer articles |
| US6759129B2 (en) | 2002-04-18 | 2004-07-06 | 3M Innovative Properties Company | Adhesion and bonding of multi-layer articles including a fluoropolymer layer |
| US6956085B2 (en) * | 2003-02-14 | 2005-10-18 | 3M Innovative Properties Company | Fluoroelastomer compositions |
| US20060147177A1 (en) * | 2004-12-30 | 2006-07-06 | Naiyong Jing | Fluoropolymer coating compositions with olefinic silanes for anti-reflective polymer films |
| US7297810B2 (en) * | 2004-12-30 | 2007-11-20 | 3M Innovative Properties Company | High refractive index monomers for optical applications |
| US20060148996A1 (en) * | 2004-12-30 | 2006-07-06 | Coggio William D | Low refractive index fluoropolymer compositions having improved coating and durability properties |
| US7323514B2 (en) * | 2004-12-30 | 2008-01-29 | 3M Innovative Properties Company | Low refractive index fluoropolymer coating compositions for use in antireflective polymer films |
| JP4952968B2 (ja) * | 2005-04-06 | 2012-06-13 | ソニー株式会社 | 二次電池用負極および二次電池 |
| US7589140B2 (en) * | 2005-09-29 | 2009-09-15 | 3M Innovative Properties Company | Fluoropolymer bonding compositions |
| US7981986B2 (en) * | 2008-04-29 | 2011-07-19 | 3M Innovative Properties Company | Optical films comprising fluorenol (meth)acrylate monomer |
| US20090275720A1 (en) * | 2008-04-30 | 2009-11-05 | 3M Innovative Properties Company | Ortho-benzylphenol mono(meth)acrylate monomers suitable for microstructured optical films |
| US8552227B2 (en) * | 2009-01-05 | 2013-10-08 | E I Du Pont De Nemours And Company | Preparation of hydrofluoroolefins by dehydrofluorination |
| DE102013008998A1 (de) | 2013-05-25 | 2014-11-27 | Manfred Eschwey | Verfahren und Intermediate zur Herstellung von Kohlenstoffstrukturen |
| US10584189B2 (en) * | 2017-02-16 | 2020-03-10 | The Regents Of The University Of Michigan | Ferroelectric polymers from dehydrofluorinated PVDF |
| EP3663321B1 (en) * | 2017-09-12 | 2022-01-19 | Daikin Industries, Ltd. | Polydifluoroacetylene, method for producing polydifluoroacetylene, precursor polymer, molded article and powder |
| FR3142189A1 (fr) * | 2022-11-23 | 2024-05-24 | Arkema France | Procédé de préparation d’un polymère halogéné par déshydro halogénation |
| CN115746180B (zh) * | 2022-11-24 | 2024-01-26 | 上海赛恩孚聚合物有限公司 | 一种具有高透明度的含氟聚合物的生产方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507844A (en) * | 1965-08-03 | 1970-04-21 | Aviat Uk | Fluoroelastomer sealants |
| US3752789A (en) * | 1971-08-20 | 1973-08-14 | Du Pont | Isolation of a fluoropolymer from a latex |
| JPS6197347A (ja) * | 1984-10-18 | 1986-05-15 | Asahi Glass Co Ltd | 加硫可能な組成物 |
| US4678842A (en) * | 1984-11-29 | 1987-07-07 | Pennwalt Corporation | Poly(fluoroacetylene) containing polymers |
| IT1212111B (it) * | 1985-03-06 | 1989-11-08 | Montefluos Spa | Procedimento per preparare fluoroelastomeri insaturi. |
| JPS6275431A (ja) * | 1985-09-28 | 1987-04-07 | Fuji Photo Film Co Ltd | フイルムの給送方法 |
| JPS6286044A (ja) * | 1985-10-11 | 1987-04-20 | Asahi Glass Co Ltd | 加硫可能な組成物 |
| US4946902A (en) * | 1988-05-27 | 1990-08-07 | E. I. Du Pont De Nemours And Company | Process for the setabilization of fluoropolymers |
| GB9017156D0 (en) * | 1990-08-03 | 1990-09-19 | Ici Plc | Stabilisation of fluoropolymers |
| TW222650B (enExample) * | 1991-04-01 | 1994-04-21 | Dow Corning | |
| US5285002A (en) * | 1993-03-23 | 1994-02-08 | Minnesota Mining And Manufacturing Company | Fluorine-containing polymers and preparation and use thereof |
-
1996
- 1996-08-26 US US08/703,422 patent/US5733981A/en not_active Expired - Fee Related
- 1996-12-23 CA CA002263307A patent/CA2263307C/en not_active Expired - Fee Related
- 1996-12-23 EP EP96945045A patent/EP0920457B1/en not_active Expired - Lifetime
- 1996-12-23 DE DE69621840T patent/DE69621840T2/de not_active Expired - Fee Related
- 1996-12-23 JP JP51159998A patent/JP3975249B2/ja not_active Expired - Lifetime
- 1996-12-23 WO PCT/US1996/020651 patent/WO1998008880A1/en not_active Ceased
- 1996-12-23 AU AU13503/97A patent/AU1350397A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2263307A1 (en) | 1998-03-05 |
| US5733981A (en) | 1998-03-31 |
| EP0920457A1 (en) | 1999-06-09 |
| DE69621840D1 (de) | 2002-07-18 |
| WO1998008880A1 (en) | 1998-03-05 |
| EP0920457B1 (en) | 2002-06-12 |
| AU1350397A (en) | 1998-03-19 |
| JP3975249B2 (ja) | 2007-09-12 |
| DE69621840T2 (de) | 2003-01-30 |
| JP2000516982A (ja) | 2000-12-19 |
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