JP2018076500A - 安定な2,3,3,3−テトラフルオロプロペン組成物 - Google Patents
安定な2,3,3,3−テトラフルオロプロペン組成物 Download PDFInfo
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- JP2018076500A JP2018076500A JP2017212461A JP2017212461A JP2018076500A JP 2018076500 A JP2018076500 A JP 2018076500A JP 2017212461 A JP2017212461 A JP 2017212461A JP 2017212461 A JP2017212461 A JP 2017212461A JP 2018076500 A JP2018076500 A JP 2018076500A
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- tetrafluoropropene
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- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 claims abstract description 13
- DMUPYMORYHFFCT-UHFFFAOYSA-N 1,2,3,3,3-pentafluoroprop-1-ene Chemical compound FC=C(F)C(F)(F)F DMUPYMORYHFFCT-UHFFFAOYSA-N 0.000 claims abstract description 11
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000005057 refrigeration Methods 0.000 claims abstract description 9
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- -1 for example Chemical compound 0.000 claims abstract description 4
- 239000000314 lubricant Substances 0.000 claims description 17
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 claims description 10
- PRDFNJUWGIQQBW-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-yne Chemical compound FC(F)(F)C#C PRDFNJUWGIQQBW-UHFFFAOYSA-N 0.000 claims description 10
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 9
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 238000004378 air conditioning Methods 0.000 claims description 5
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 claims description 4
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 4
- WGZYQOSEVSXDNI-UHFFFAOYSA-N 1,1,2-trifluoroethane Chemical compound FCC(F)F WGZYQOSEVSXDNI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 229920001289 polyvinyl ether Polymers 0.000 claims description 4
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 claims description 2
- 239000006258 conductive agent Substances 0.000 claims description 2
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 claims 1
- 239000003507 refrigerant Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 7
- 239000012530 fluid Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- HMAHQANPHFVLPT-UHFFFAOYSA-N 1,3,3-trifluoroprop-1-yne Chemical compound FC#CC(F)F HMAHQANPHFVLPT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005796 dehydrofluorination reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 description 1
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- 238000006115 defluorination reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
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- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
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- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
- C10M2209/043—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical used as base material
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Abstract
Description
本発明のさらに他の対象は潤滑剤と組み合わせた上記組成物にある。
好ましいPOE潤滑剤は40℃で1〜1000センチストーク(cSt)の粘性、好ましくは10〜200cSt、有利には30〜80cStの粘度を有するものである。
熱安定性試験はASHRAE規格 97-2007:「冷媒システムで使用する材料の化学安定性をテストするための密封ガラス・チューブ法」に従って実行した。テスト条件は以下の通り:
流体の重量:2.2g
潤滑剤の重量:5g
温度:200℃
時間:14日間
(1)気相を回収し、ガスクロマトグラフィで分析する:主たる不純物をGC/MSで同定した(ガスクロマトグラフィをマススペクトロメトリに連結)。流体Fから来る不純物と潤滑剤から来る不純物とを含む。
(2)鋼を秤量(腐食速度の測定)し、顕微鏡で観察する。
(3)潤滑剤は色(分光測色法(Labomat DR Lange LICO220 Model MLG131)で)、含水率(カール・フィッシャー・クーロメトリ(Mettler DL37)で)および酸価(0.01N メタノール水酸化カリウムで定量分析)を分析した。
これらの試験で用いた流体は主としてHFO−1234yf(少なくとも99.9重量%)を含む。次いで、この流体にそれぞれ300ppmのHFO−1243zf、500ppmのE HFO−1234zeおよび300ppmのHFO−1243zf+500ppmのE HFO−1234zeを添加する。
Claims (11)
- 少なくともx重量%の2,3,3,3−テトラフルオロプロペン(99.8≦x<100)と、y重量%以下の3,3,3−トリフルオロプロペン(HFO−1243zf)および2,3,3,3−テトラフルオロプロペンの位置異性体、例えば1,3,3,3−テトラフルオロプロペン(Z異性体およびE異性体)および1,1,2,3−テトラフルオロプロペンの中から選択される不飽和化合物(Ia)(0<y≦0.2)と、任意成分としての500ppm以下の3,3,3−トリフルオロプロピンおよび/または200ppm以下の1,1,1,2,3−ペンタフルオロプロペン(HFO−1225ye)とを含む安定な組成物(SC)。
- 1,1,1,2−テトラフルオロプロパン(HFC−254eb)、1,1,1,2,3−ペンタフルオロプロパン(HFC−245eb)、1,1,1,2−テトラフルオロエタン(HFC−134a)、1,1,2−トリフルオロエタン(HFC−143)、1,1,1,2,3,3−ヘキサフルオロプロパン、ヘキサフルオロプロペン、シクロヘキサフルオロプロペンおよび1,1,1,3,3−ペンタフルオロプロペン(HFO−1225zc)の中から選択される少なくとも一種の化合物(Ib)をさらに含む請求項1に記載の組成物。
- 化合物(Ib)の量が組成物の500ppm以下である請求項2に記載の組成物。
- 少なくとも99.85重量%の2,3,3,3−テトラフルオロプロペンと、y重量%以下の3,3,3−トリフルオロプロペン(HFO−1243zf)および2,3,3,3−テトラフルオロプロペンの位置異性体、例えば1,3,3,3−テトラフルオロプロペン(Z異性体およびE異性体)および1,1,2,3−テトラフルオロプロペンの中から選択される不飽和化合物(Ia)(0<y≦0.15)と、任意成分としての250ppm以下の3,3,3−トリフルオロプロピンおよび/または50ppm以下の1,1,1,2,3−ペンタフルオロプロペン(HFO−1225ye)とを含む請求項1〜3のいずれか一項に記載の組成物。
- 少なくとも99.9重量%の2,3,3,3−テトラフルオロプロペンと、y重量%以下の3,3,3−トリフルオロプロペン(HFO−1243zf)および2,3,3,3−テトラフルオロプロペンの位置異性体、例えば1,3,3,3−テトラフルオロプロペン(Z異性体およびE異性体)および1,1,2,3−テトラフルオロプロペンの中から選択される不飽和化合物(Ia)(0<y≦0.1)と、任意成分として200ppm以下の3,3,3−トリフルオロプロピンおよび/または5ppm以下の1,1,1,2,3−ペンタフルオロプロペン(HFO−1225ye)とを含む請求項1〜4のいずれか一項に記載の組成物。
- 99.85〜99.98重量%の2,3,3,3−テトラフルオロプロペンと、0.02〜0.15重量%の3,3,3−トリフルオロプロペン(HFO−1243zf)および2,3,3,3−テトラフルオロプロペンの位置異性体、例えば1,3,3,3−テトラフルオロプロペン(Z異性体およびE異性体)および1,1,2,3−テトラフルオロプロペンの中から選択される不飽和化合物(Ia)と、任意成分として200ppm以下の3,3,3−トリフルオロプロピンおよび/または5ppm以下の1,1,1,2,3−ペンタフルオロプロペン(HFO−1225ye)および/または400ppm以下の化合物(Ib)とを含む請求項1〜5のいずれか一項に記載の組成物。
- 固定式または自動車の空調、冷蔵およびヒートポンプでの熱伝導剤として使用される請求項1〜6のいずれか一項に記載の組成物。
- 潤滑剤と一緒に使用される請求項1〜7のいずれか一項に記載の組成物。
- 潤滑剤がポリオールエステル(POE)、ポリアルキレングリコール(PAG)、ポリアルキレングリコールエステルおよびポリビニルエーテル(PVE)の中から選択される請求項1〜8のいずれか一項に記載の組成物。
- 純度が99.8重量%以上且つ100重量%未満で、0.2重量%以下の不飽和化合物(Ia)と、任意成分としての500ppm以下の3,3,3−トリフルオロプロピンおよび/または200ppm以下の1,1,1,2,3−ペンタフルオロプロペンおよび/または500ppm以下の化合物(Ib)とを含む2,3,3,3−テトラフルオロプロペン。
- 純度が99.9重量%以上且つ100重量%未満で、0.1重量%以下の不飽和化合物(Ia)と、任意成分として200ppm以下の3,3,3−トリフルオロプロピンおよび/または5ppm以下の1,1,1,2,3−ペンタフルオロプロペンおよび/または500ppm以下の化合物(Ib)とを含む請求項10に記載の2,3,3,3−テトラフルオロプロペン。
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2011
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- 2011-06-20 JP JP2013519130A patent/JP2013544896A/ja active Pending
- 2011-06-20 CN CN201180033620.XA patent/CN102985397B/zh active Active
- 2011-06-20 CN CN201710600480.9A patent/CN107254296B/zh active Active
- 2011-06-20 ES ES11737991.7T patent/ES2602747T3/es active Active
- 2011-06-20 PL PL11737991T patent/PL2590916T3/pl unknown
- 2011-06-20 WO PCT/FR2011/051406 patent/WO2012004487A2/fr active Application Filing
- 2011-06-20 EP EP11737991.7A patent/EP2590916B1/fr not_active Revoked
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Also Published As
Publication number | Publication date |
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US20180327645A1 (en) | 2018-11-15 |
CN102985397A (zh) | 2013-03-20 |
US10119055B2 (en) | 2018-11-06 |
JP6615846B2 (ja) | 2019-12-04 |
WO2012004487A3 (fr) | 2012-03-29 |
US10662357B2 (en) | 2020-05-26 |
FR2962442B1 (fr) | 2016-02-26 |
JP2020041147A (ja) | 2020-03-19 |
EP2590916A2 (fr) | 2013-05-15 |
CN107254296A (zh) | 2017-10-17 |
US20160115361A1 (en) | 2016-04-28 |
CN107254296B (zh) | 2021-04-20 |
ES2602747T3 (es) | 2017-02-22 |
CN102985397B (zh) | 2018-04-17 |
FR2962442A1 (fr) | 2012-01-13 |
WO2012004487A2 (fr) | 2012-01-12 |
JP2013544896A (ja) | 2013-12-19 |
US20130105724A1 (en) | 2013-05-02 |
PL2590916T3 (pl) | 2017-02-28 |
EP2590916B1 (fr) | 2016-10-12 |
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