JP2022553440A - フッ素化アイオノマーの熱分解によるフルオロオレフィンの製造方法 - Google Patents
フッ素化アイオノマーの熱分解によるフルオロオレフィンの製造方法 Download PDFInfo
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- JP2022553440A JP2022553440A JP2022538714A JP2022538714A JP2022553440A JP 2022553440 A JP2022553440 A JP 2022553440A JP 2022538714 A JP2022538714 A JP 2022538714A JP 2022538714 A JP2022538714 A JP 2022538714A JP 2022553440 A JP2022553440 A JP 2022553440A
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- WUMVZXWBOFOYAW-UHFFFAOYSA-N 1,2,3,3,4,4,4-heptafluoro-1-(1,2,3,3,4,4,4-heptafluorobut-1-enoxy)but-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)F WUMVZXWBOFOYAW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YUCJJNOEOYQJQO-UHFFFAOYSA-N 1,2,3,4,4,4-hexafluoro-1-[1,2,3,4,4,4-hexafluoro-3-(trifluoromethyl)but-1-enoxy]-3-(trifluoromethyl)but-1-ene Chemical compound FC(OC(F)=C(F)C(F)(C(F)(F)F)C(F)(F)F)=C(F)C(F)(C(F)(F)F)C(F)(F)F YUCJJNOEOYQJQO-UHFFFAOYSA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- ZXABMDQSAABDMG-UHFFFAOYSA-N 3-ethenoxyprop-1-ene Chemical compound C=CCOC=C ZXABMDQSAABDMG-UHFFFAOYSA-N 0.000 description 1
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- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
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- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
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- GZKHDVAKKLTJPO-UHFFFAOYSA-N ethyl 2,2-difluoroacetate Chemical compound CCOC(=O)C(F)F GZKHDVAKKLTJPO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
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- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 229910001540 lithium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- ACFSQHQYDZIPRL-UHFFFAOYSA-N lithium;bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F ACFSQHQYDZIPRL-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
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- 239000007769 metal material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- CSSYKHYGURSRAZ-UHFFFAOYSA-N methyl 2,2-difluoroacetate Chemical compound COC(=O)C(F)F CSSYKHYGURSRAZ-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
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- 229910052754 neon Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- CDXZRBLOGJXGTN-UHFFFAOYSA-N prop-2-enoxycyclohexane Chemical compound C=CCOC1CCCCC1 CDXZRBLOGJXGTN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000002352 steam pyrolysis Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- RCYJPSGNXVLIBO-UHFFFAOYSA-N sulfanylidenetitanium Chemical compound [S].[Ti] RCYJPSGNXVLIBO-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- RBYFNZOIUUXJQD-UHFFFAOYSA-J tetralithium oxalate Chemical compound [Li+].[Li+].[Li+].[Li+].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O RBYFNZOIUUXJQD-UHFFFAOYSA-J 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C07C17/367—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by depolymerisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本出願は、2019年12月23日に出願された米国特許仮出願第62/952,582号の優先権を主張し、その開示は、参照によりその全体が本明細書に組み込まれる。
フッ素化オレフィン、特にテトラフルオロエチレン(tetrafluoroethylene、TFE)は、フルオロポリマーの調製に重要な原材料である。TFEは一般に、例えば大気中のオゾン層破壊への潜在的影響のために環境上懸念があるフッ素及び塩素含有出発物質(例えば、R-22=CHClF2)から調製される。したがって、TFEを生成する代替的な方法が必要とされる。
「1つの(a)」、「1つの(an)」及び「その(the)」などの用語は、単数の実体のみを指すことを意図するものではなく、具体例を例示するために用いることができる一般的な種類を含む。「a」、「an」及び「the」の用語は、「少なくとも1つ」という用語と互換可能に使用される。
[式中、Rd fは、F又は1個~10個(いくつかの実施形態では1個~5個)の炭素原子を有するペルフルオロアルキル基を表す]に対応するオレフィンを含む。いくつかの実施形態では、プロセスによって作製されるフッ素化オレフィンは、テトラフルオロエチレン(TFE)又はヘキサフルオロプロピレン(HFP)のうちの少なくとも1つを含む。いくつかの実施形態では、TFE及びHFPの両方が作製される。
850μmの平均粒径を有する自由流動性焼結PTFE材料を、垂直流動床反応器(高さ58mm、直径35mm)に連続的に供給した(2グラム/分)。反応器は、SiC粒子を含み、流動床は、過熱蒸気を反応器に供給することによって生成された。反応器内の温度を620℃に維持した。高温の熱分解ガスをNaOH水溶液でクエンチした。熱分解収率は90%であり、94%のTFE、5%のHFP及び1%のC4F8-シクロブタンが生成された。
Na形態で1100の当量及び1mmの粒径を有する乾燥アイオノマー(TFE及びCF2=CF-O-(CF2)4-SO3Naを基準とする)を、実施例1に記載されるように熱分解した。TFE/HFP収率は21%であり、TFE及びHFPの比は、67%のTFE及び33%のHFPだった。GC分析によって観察されたように、多くの不特定ガスが生成された。
SO3H形態のEW1100を有する比較例2に類似のアイオノマー(500グラム)を、395℃で1時間、連続蒸気流下、4Lの撹拌式床反応器中で処理した。アイオノマー材料は、12%の重量損失を示し、SO3H基が除去されたことを示した。
Claims (18)
- スルホン酸基、カルボン酸基、又はこれらの塩のうちの少なくとも1つを含むフッ素化コポリマーからフッ素化オレフィンを生成するためのプロセスであって、
前記フッ素化コポリマーを450℃以下の第1の温度で加熱して、スルホン酸基、カルボン酸基、又はこれらの塩のうちの少なくとも1つを分解して、部分的に熱分解された中間体を形成することと、
続いて、前記部分的に熱分解された中間体を少なくとも550℃の第2の温度で加熱して、前記フッ素化オレフィンを生成することと、を含む、プロセス。 - 前記第1の温度が、300℃~450℃の範囲であり、前記第2の温度が、600℃~700℃の範囲である、請求項1に記載のプロセス。
- 前記フッ素化コポリマーが、スルホン酸基又はカルボン酸基のうちの少なくとも1つを含む、請求項1又は2に記載のプロセス。
- Z及びZ’が、それぞれ水素である、請求項4に記載のプロセス。
- 前記フッ素化コポリマーを無機酸と組み合わせることを更に含む、請求項5に記載のプロセス。
- 前記コポリマーが、500~2000の範囲の-SO3Z又は-CO2Z’当量を有する、請求項1~8のいずれか一項に記載のプロセス。
- 前記フッ素化オレフィンが、テトラフルオロエチレン又はヘキサフルオロプロピレンのうちの少なくとも1つを含む、請求項1~9のいずれか一項に記載のプロセス。
- 加熱又は後続の加熱のうちの少なくとも1つが、少なくとも部分的にマイクロ波照射で実施される、請求項1~10のいずれか一項に記載のプロセス。
- 前記フッ素化コポリマー又は前記部分的に熱分解された中間体のうちの少なくとも1つを、マイクロ波活性粒子と接触させる、請求項11に記載のプロセス。
- 前記フッ素化コポリマーが、触媒インク、ポリマー電解質膜、触媒層、ガス拡散層、バイポーラプレート、又は電解セルのうちの少なくとも1つを含むデバイスの構成要素である、請求項1~12のいずれか一項に記載のプロセス。
- 前記デバイスを粉砕すること又は細断することと、前記フッ素化コポリマーを同時に加熱しながら前記デバイスを加熱することとの少なくとも1つを更に含む、請求項13に記載のプロセス。
- 前記フッ素化オレフィンを生成した後に金属を回収することを更に含む、請求項13又は14に記載のプロセス。
- 前記金属が、金、銀、白金、又はパラジウムのうちの少なくとも1つを含む、請求項15に記載のプロセス。
- 加熱又は後続の加熱のうちの少なくとも1つが、流動床反応器、撹拌反応器、又はロータリーキルン中で実施される、請求項1~16のいずれか一項に記載のプロセス。
- 加熱又は後続の加熱のうちの少なくとも1つが、窒素、水蒸気、又は希ガスのうちの少なくとも1つを含むキャリアガスの存在下で実施される、請求項1~17のいずれか一項に記載のプロセス。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09501458A (ja) * | 1993-08-11 | 1997-02-10 | ザ ユニバーシティ オブ アクロン | 解重合法 |
JP2012504633A (ja) * | 2008-10-01 | 2012-02-23 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化材料の熱分解によるフルオロオレフィンの製造プロセス |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3832411A (en) | 1971-02-02 | 1974-08-27 | Liquid Nitrogen Processing | Method for the depolymerization of polytetrafluoroethylene |
US4349650A (en) | 1979-03-14 | 1982-09-14 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
JPH1167274A (ja) | 1997-08-22 | 1999-03-09 | Daikin Ind Ltd | リチウム二次電池及び高分子ゲル電解質並びにリチウム二次電池用結着剤 |
US6294627B1 (en) | 1998-08-31 | 2001-09-25 | Dyneon Llc | Low temperature fluorocarbon elastomers |
US6255536B1 (en) | 1999-12-22 | 2001-07-03 | Dyneon Llc | Fluorine containing vinyl ethers |
JP5178980B2 (ja) | 2000-02-10 | 2013-04-10 | サウス アフリカン ニュークリア エナージィ コーポレイション リミテッド | 炭化フッ素供給原料の処理方法 |
WO2001058840A2 (en) | 2000-02-10 | 2001-08-16 | South African Nuclear Energy Corporation Limited | Treatment of fluorocarbon feedstocks |
KR100337889B1 (ko) | 2000-06-22 | 2002-05-24 | 김순택 | 리튬 2차전지 |
EP1481957B1 (en) | 2002-03-01 | 2008-01-16 | Daikin Industries, Ltd. | Process for producing fluoromonomer |
US20040107869A1 (en) | 2002-12-10 | 2004-06-10 | 3M Innovative Properties Company | Catalyst ink |
US8367267B2 (en) | 2005-10-28 | 2013-02-05 | 3M Innovative Properties Company | High durability fuel cell components with cerium oxide additives |
US8628871B2 (en) | 2005-10-28 | 2014-01-14 | 3M Innovative Properties Company | High durability fuel cell components with cerium salt additives |
CN101341202B (zh) | 2005-11-30 | 2011-11-30 | 南非原子能股份有限公司 | 含氟聚合物的解聚 |
US7575534B2 (en) | 2006-12-22 | 2009-08-18 | Torvec, Inc. | Transmission with resistance torque control |
GB0801194D0 (en) | 2008-01-23 | 2008-02-27 | 3M Innovative Properties Co | Processing aid compositions comprising fluoropolymers having long-chain branches |
US20190027769A1 (en) * | 2016-03-07 | 2019-01-24 | 3M Innovative Properties Company | Fluorinated copolymer having sulfonyl pendant groups and method of making an ionomer |
EP3896052A1 (en) | 2017-05-19 | 2021-10-20 | 3M Innovative Properties Co. | Methods of making a polyfluorinated allyl ether and compounds relating to the methods |
-
2020
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09501458A (ja) * | 1993-08-11 | 1997-02-10 | ザ ユニバーシティ オブ アクロン | 解重合法 |
JP2012504633A (ja) * | 2008-10-01 | 2012-02-23 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化材料の熱分解によるフルオロオレフィンの製造プロセス |
Non-Patent Citations (2)
Title |
---|
FENG, M., ET AL.: "Characterization of the thermolysis products of Nafion membrane: A potential source of perfluorinate", SCIEMTIFIC REPORTS, vol. 5, no. 9859, JPN6022054908, 7 May 2015 (2015-05-07), pages 1 - 8, ISSN: 0004961882 * |
SUROWIEC. J. AND BOGOCZEK, R.: "STUDIES ON THE THERMAL STABILITY OF THE PERFLUORINATED CATION-EXCHANGE MEMBRANE NAFION-417", JOURNAL OF THERMAL ANALYSIS, vol. 33, JPN6022054909, December 1998 (1998-12-01), pages 1097 - 1102, ISSN: 0004961881 * |
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