JP2008539312A - ３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびフルオロエーテルを含む伝熱および冷媒組成物 - Google Patents
３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびフルオロエーテルを含む伝熱および冷媒組成物 Download PDFInfo
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- JP2008539312A JP2008539312A JP2008509030A JP2008509030A JP2008539312A JP 2008539312 A JP2008539312 A JP 2008539312A JP 2008509030 A JP2008509030 A JP 2008509030A JP 2008509030 A JP2008509030 A JP 2008509030A JP 2008539312 A JP2008539312 A JP 2008539312A
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- JP
- Japan
- Prior art keywords
- weight percent
- nonafluoro
- hexene
- difluoromethoxy
- methoxypropane
- 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.)
- Withdrawn
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- 239000000203 mixture Substances 0.000 title claims abstract description 172
- GVEUEBXMTMZVSD-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohex-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C GVEUEBXMTMZVSD-UHFFFAOYSA-N 0.000 title claims abstract description 125
- 229920001774 Perfluoroether Polymers 0.000 title claims abstract description 23
- 239000003507 refrigerant Substances 0.000 title claims description 77
- 238000012546 transfer Methods 0.000 title claims description 14
- 238000005057 refrigeration Methods 0.000 claims abstract description 51
- -1 aliphatic hydrocarbylene radical Chemical class 0.000 claims description 85
- 239000002904 solvent Substances 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 44
- 229930195733 hydrocarbon Natural products 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 239000004215 Carbon black (E152) Substances 0.000 claims description 40
- 239000013529 heat transfer fluid Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000007850 fluorescent dye Substances 0.000 claims description 24
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 239000000975 dye Substances 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000002596 lactones Chemical class 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 14
- 238000001704 evaporation Methods 0.000 claims description 14
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- XDFJJLSCPQLSBD-UHFFFAOYSA-N 1,1,1,2-tetrafluoro-2-(fluoromethoxy)ethane Chemical compound FCOC(F)C(F)(F)F XDFJJLSCPQLSBD-UHFFFAOYSA-N 0.000 claims description 10
- BEPCUGVFWAYLBF-UHFFFAOYSA-N 1,1,1,2-tetrafluoro-2-methoxyethane Chemical compound COC(F)C(F)(F)F BEPCUGVFWAYLBF-UHFFFAOYSA-N 0.000 claims description 10
- KVRDTYTVCCKIMF-UHFFFAOYSA-N 1,1,1-trifluoro-2-methoxypropane Chemical compound COC(C)C(F)(F)F KVRDTYTVCCKIMF-UHFFFAOYSA-N 0.000 claims description 10
- YUOXYWMLEGWQLB-UHFFFAOYSA-N 1,1,1-trifluoro-3-methoxypropane Chemical compound COCCC(F)(F)F YUOXYWMLEGWQLB-UHFFFAOYSA-N 0.000 claims description 10
- YQQHEHMVPLLOKE-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-methoxyethane Chemical compound COC(F)(F)C(F)F YQQHEHMVPLLOKE-UHFFFAOYSA-N 0.000 claims description 10
- PYSBCYQDWOCAHY-UHFFFAOYSA-N 1,1,2-trifluoro-1-methoxy-2-(trifluoromethoxy)ethane Chemical compound COC(F)(F)C(F)OC(F)(F)F PYSBCYQDWOCAHY-UHFFFAOYSA-N 0.000 claims description 10
- YKICUSOQECKQRR-UHFFFAOYSA-N 1,1,2-trifluoro-2-methoxyethane Chemical compound COC(F)C(F)F YKICUSOQECKQRR-UHFFFAOYSA-N 0.000 claims description 10
- CRGZRXUKXVTRNO-UHFFFAOYSA-N 1,1-difluoro-2-methoxyethane Chemical compound COCC(F)F CRGZRXUKXVTRNO-UHFFFAOYSA-N 0.000 claims description 10
- KQUULKREOKHZAM-UHFFFAOYSA-N 1-(difluoromethoxy)-1,2,2-trifluoroethane Chemical compound FC(F)OC(F)C(F)F KQUULKREOKHZAM-UHFFFAOYSA-N 0.000 claims description 10
- HBRLMDFVVMYNFH-UHFFFAOYSA-N 1-ethoxy-1,1,2,2-tetrafluoroethane Chemical compound CCOC(F)(F)C(F)F HBRLMDFVVMYNFH-UHFFFAOYSA-N 0.000 claims description 10
- UUXWSQGUZUAECB-UHFFFAOYSA-N 1-ethoxy-1,2,2-trifluoroethane Chemical compound CCOC(F)C(F)F UUXWSQGUZUAECB-UHFFFAOYSA-N 0.000 claims description 10
- RPVUQXHGCXIWHO-UHFFFAOYSA-N 2-(difluoromethoxy)-1,1-difluoroethane Chemical compound FC(F)COC(F)F RPVUQXHGCXIWHO-UHFFFAOYSA-N 0.000 claims description 10
- ISSHBUUZSURRBQ-UHFFFAOYSA-N 2-ethoxy-1,1,1,2-tetrafluoroethane Chemical compound CCOC(F)C(F)(F)F ISSHBUUZSURRBQ-UHFFFAOYSA-N 0.000 claims description 10
- ZKNHDJMXIUOHLX-UHFFFAOYSA-N 2-ethoxy-1,1,1-trifluoroethane Chemical compound CCOCC(F)(F)F ZKNHDJMXIUOHLX-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- 230000006835 compression Effects 0.000 claims description 10
- 238000007906 compression Methods 0.000 claims description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- ZYAMKYAPIQPWQR-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-3-methoxypropane Chemical compound COCC(F)(F)C(F)(F)F ZYAMKYAPIQPWQR-UHFFFAOYSA-N 0.000 claims description 9
- MZCHBFQEZMHILC-UHFFFAOYSA-N 1,1,1,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethane Chemical compound FC(F)C(F)(F)OC(F)C(F)(F)F MZCHBFQEZMHILC-UHFFFAOYSA-N 0.000 claims description 9
- XLJTWSJIJSUZLQ-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-3-(trifluoromethoxy)propane Chemical compound FC(F)C(F)(F)COC(F)(F)F XLJTWSJIJSUZLQ-UHFFFAOYSA-N 0.000 claims description 9
- DEYAWNMYIUDQER-UHFFFAOYSA-N 1-(1,1,2,2-tetrafluoroethoxy)propane Chemical compound CCCOC(F)(F)C(F)F DEYAWNMYIUDQER-UHFFFAOYSA-N 0.000 claims description 9
- BFPGPHGEDKDBCN-UHFFFAOYSA-N 1-(2,2-difluoroethoxy)-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)COC(F)(F)C(F)(F)F BFPGPHGEDKDBCN-UHFFFAOYSA-N 0.000 claims description 9
- HNQMKNFMSPECFD-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,3-heptafluoropropane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)F HNQMKNFMSPECFD-UHFFFAOYSA-N 0.000 claims description 9
- UQGJBCKUPBIEDQ-UHFFFAOYSA-N 2-(difluoromethoxy)-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(C)OC(F)F UQGJBCKUPBIEDQ-UHFFFAOYSA-N 0.000 claims description 9
- RMFXYVDVYHFRRQ-UHFFFAOYSA-N 2-ethoxy-1,1,1,2,3,3,3-heptafluoropropane Chemical compound CCOC(F)(C(F)(F)F)C(F)(F)F RMFXYVDVYHFRRQ-UHFFFAOYSA-N 0.000 claims description 9
- PCTQNZRJAGLDPD-UHFFFAOYSA-N 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane Chemical compound FC(F)OCC(F)(F)C(F)F PCTQNZRJAGLDPD-UHFFFAOYSA-N 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- PKMXTDVNDDDCSY-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-3-methoxypropane Chemical compound COC(F)(F)C(F)C(F)(F)F PKMXTDVNDDDCSY-UHFFFAOYSA-N 0.000 claims description 8
- VNXYDFNVQBICRO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-methoxypropane Chemical compound COC(C(F)(F)F)C(F)(F)F VNXYDFNVQBICRO-UHFFFAOYSA-N 0.000 claims description 8
- CMRJNALMNDBXQC-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-1-methoxypropane Chemical compound COC(F)(F)C(F)(F)C(F)F CMRJNALMNDBXQC-UHFFFAOYSA-N 0.000 claims description 8
- OMGXRQKWXWMTFU-UHFFFAOYSA-N 2,3-difluoro-4-(trifluoromethyl)oxetane Chemical compound FC1OC(C(F)(F)F)C1F OMGXRQKWXWMTFU-UHFFFAOYSA-N 0.000 claims description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052731 fluorine Chemical group 0.000 claims description 8
- 239000011737 fluorine Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- DFEYYRMXOJXZRJ-UHFFFAOYSA-N sevoflurane Chemical compound FCOC(C(F)(F)F)C(F)(F)F DFEYYRMXOJXZRJ-UHFFFAOYSA-N 0.000 claims description 8
- UNIYHTKWMKXESF-UHFFFAOYSA-N 2-(difluoromethoxy)-1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)OC(C(F)(F)F)C(F)(F)F UNIYHTKWMKXESF-UHFFFAOYSA-N 0.000 claims description 7
- LTRUYHVIVWXQMY-UHFFFAOYSA-N 3-(difluoromethoxy)-1,1,1,2,2,3-hexafluoropropane Chemical compound FC(F)OC(F)C(F)(F)C(F)(F)F LTRUYHVIVWXQMY-UHFFFAOYSA-N 0.000 claims description 7
- NKEBKUGEYSHGKA-UHFFFAOYSA-N 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)OCC(F)(F)C(F)(F)F NKEBKUGEYSHGKA-UHFFFAOYSA-N 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 7
- 150000008378 aryl ethers Chemical class 0.000 claims description 6
- 239000002516 radical scavenger Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 5
- 230000000873 masking effect Effects 0.000 claims description 5
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 5
- VWCLQNINSPFHFV-UHFFFAOYSA-N 10-oxapentacyclo[12.8.0.02,11.04,9.015,20]docosa-1(14),2(11),4,6,8,12,15,17,19,21-decaene Chemical compound C1=CC=C2C3=CC=C4OC5=CC=CC=C5CC4=C3C=CC2=C1 VWCLQNINSPFHFV-UHFFFAOYSA-N 0.000 claims description 4
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims description 4
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 claims description 4
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 4
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 4
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 4
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 230000004907 flux Effects 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002905 orthoesters Chemical group 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 claims 1
- 238000004378 air conditioning Methods 0.000 abstract description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 150000003254 radicals Chemical class 0.000 description 18
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229940052303 ethers for general anesthesia Drugs 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 3
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- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ULIAPOFMBCCSPE-UHFFFAOYSA-N tridecan-7-one Chemical compound CCCCCCC(=O)CCCCCC ULIAPOFMBCCSPE-UHFFFAOYSA-N 0.000 description 1
- WKJHMKQSIBMURP-UHFFFAOYSA-N tridecanenitrile Chemical compound CCCCCCCCCCCCC#N WKJHMKQSIBMURP-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical group CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical group COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- SZKKNEOUHLFYNA-UHFFFAOYSA-N undecanenitrile Chemical compound CCCCCCCCCCC#N SZKKNEOUHLFYNA-UHFFFAOYSA-N 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
- C11D7/5063—Halogenated hydrocarbons containing heteroatoms, e.g. fluoro alcohols
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
- C23G5/02803—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/032—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/11—Ethers
- C09K2205/112—Halogenated ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
- C09K2205/126—Unsaturated fluorinated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/32—The mixture being azeotropic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
- C11D2111/22—Electronic devices, e.g. PCBs or semiconductors
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Metallurgy (AREA)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67492905P | 2005-04-26 | 2005-04-26 | |
| PCT/US2006/015581 WO2006116372A1 (en) | 2005-04-26 | 2006-04-25 | Heat transfer and refrigerant compositions comprising 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and a fluoroether |
| US11/410,491 US7413676B2 (en) | 2005-04-26 | 2006-04-25 | Heat transfer and refrigerant compositions comprising 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and a fluoroether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008539312A true JP2008539312A (ja) | 2008-11-13 |
| JP2008539312A5 JP2008539312A5 (https=) | 2009-05-07 |
Family
ID=37185912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008509030A Withdrawn JP2008539312A (ja) | 2005-04-26 | 2006-04-25 | ３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびフルオロエーテルを含む伝熱および冷媒組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7413676B2 (https=) |
| EP (1) | EP1874888B1 (https=) |
| JP (1) | JP2008539312A (https=) |
| CN (1) | CN101166804B (https=) |
| AR (1) | AR055055A1 (https=) |
| ES (1) | ES2378243T3 (https=) |
| WO (1) | WO2006116372A1 (https=) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008539311A (ja) * | 2005-04-26 | 2008-11-13 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびヒドロフルオロカーボンを含む伝熱および冷媒組成物 |
| JP2014005419A (ja) * | 2012-06-27 | 2014-01-16 | Central Glass Co Ltd | フッ素化エーテルを含む熱伝達作動媒体 |
| JP2019523752A (ja) * | 2016-05-09 | 2019-08-29 | スリーエム イノベイティブ プロパティズ カンパニー | ハイドロフルオロオレフィン及びその使用方法 |
| WO2022045115A1 (ja) * | 2020-08-31 | 2022-03-03 | ダイキン工業株式会社 | フッ素オイルを含む組成物 |
| JP2024515551A (ja) * | 2021-04-05 | 2024-04-10 | ザイノン・テクノロジーズ・エルエルシー | 光ファイバコネクタおよび端面の非接触クリーニングのための方法 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2642570T3 (es) * | 2006-02-28 | 2017-11-16 | The Chemours Company Fc, Llc | Composiciones azeotrópicas que comprenden compuestos fluorados para aplicaciones de limpieza |
| JP5109556B2 (ja) * | 2006-11-01 | 2012-12-26 | セントラル硝子株式会社 | １，１，２，２−テトラフルオロ−１−メトキシエタンを含む共沸及び共沸様組成物 |
| JP4855305B2 (ja) * | 2007-03-06 | 2012-01-18 | 三菱電機株式会社 | 空気調和装置 |
| CN102066852B (zh) * | 2008-06-16 | 2014-03-05 | 三菱电机株式会社 | 非共沸混合制冷剂及冷冻循环装置 |
| CN102227395A (zh) * | 2008-11-13 | 2011-10-26 | 苏威氟有限公司 | 氢氟烯烃、氢氟烯烃的制造以及使用氢氟烯烃的方法 |
| US8846754B2 (en) * | 2009-12-16 | 2014-09-30 | Honeywell International Inc. | Azeotrope-like compositions of cis-1,1,1,4,4,4-hexafluoro-2-butene |
| JP5903998B2 (ja) * | 2012-04-19 | 2016-04-13 | セントラル硝子株式会社 | 沸騰冷却器用媒体及びその使用方法 |
| CN103666839A (zh) * | 2013-11-11 | 2014-03-26 | 青岛佰众化工技术有限公司 | 清洁剂 |
| FR3083800B1 (fr) * | 2018-07-13 | 2020-12-25 | Total Marketing Services | Composition refroidissante et ignifugeante pour systeme de propulsion d'un vehicule electrique ou hybride |
| FR3083802B1 (fr) | 2018-07-13 | 2021-02-12 | Total Marketing Services | Composition refroidissante et ignifugeante pour systeme de propulsion d'un vehicule electrique ou hybride |
| US10836983B2 (en) * | 2018-07-17 | 2020-11-17 | Illinois Tool Works Inc. | Azeotropic composition containing 1,1,1,3,3,3-hexafluoro-2-methoxypropane |
| WO2020115602A1 (en) * | 2018-12-03 | 2020-06-11 | 3M Innovative Properties Company | Visually distinguishable working fluids |
| GB202014635D0 (en) * | 2020-09-17 | 2020-11-04 | Mexichem Fluor Sa De Cv | Composition |
| CN115572579B (zh) * | 2022-10-12 | 2023-10-13 | 澳江(无锡)网络能源有限公司 | 一种液冷用全氟化合物组合物及其在浸没式冷却中的应用 |
| US20240279520A1 (en) * | 2022-10-13 | 2024-08-22 | Honeywell International Inc. | Fluorine substituted ethers and compositions, methods and uses including same |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5458800A (en) * | 1990-02-20 | 1995-10-17 | Societe Atochem | Use of (perfluoroalkyl) ethylenes as cleaning or drying agents, and compositions which can be used for this purpose |
| US5039445A (en) * | 1990-10-03 | 1991-08-13 | E. I. Du Pont De Nemours And Company | Ternary azeotropic compositions of N-perfluorobutylethylene and cis-1,2-dichloroethylene with methanol or ethanol or isopropanol |
| US5037573A (en) * | 1990-10-03 | 1991-08-06 | E. I. Du Pont De Nemours And Company | Binary azeotropic compositions of 1,1-dichloro-1-fluoroethane and n-perfluorobutylethylene |
| US5827446A (en) * | 1996-01-31 | 1998-10-27 | E. I. Du Pont De Nemours And Company | Nonafluoromethoxybutane compositions |
| US5730894A (en) * | 1996-04-16 | 1998-03-24 | E. I. Du Pont De Nemours And Company | 1,1,2,2,3,3,4,4-octafluorobutane azeotropic (like) compositions |
| US5851436A (en) * | 1996-06-13 | 1998-12-22 | E. I. Du Pont De Nemours And Company | Nonafluoromethoxybutane compositions |
| US6183663B1 (en) * | 1998-10-09 | 2001-02-06 | Bright Solutions, Inc. | Leak detection dye delivery system |
| US6793840B2 (en) * | 2000-12-22 | 2004-09-21 | E. I. Du Pont De Nemours And Company | Azeotrope mixtures with perfluorobutylethylene |
| CN100465204C (zh) * | 2001-11-13 | 2009-03-04 | 大金工业株式会社 | 合成树脂发泡体的制造方法 |
| KR20060123531A (ko) | 2004-01-14 | 2006-12-01 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 1-에톡시-1,1,2,2,3,3,4,4-노나플루오로부탄 및수소화플루오르화탄소를 포함하는 냉매 조성물 및 그의용도 |
| US7276177B2 (en) * | 2004-01-14 | 2007-10-02 | E.I. Dupont De Nemours And Company | Hydrofluorocarbon refrigerant compositions and uses thereof |
-
2006
- 2006-04-25 AR ARP060101656A patent/AR055055A1/es not_active Application Discontinuation
- 2006-04-25 JP JP2008509030A patent/JP2008539312A/ja not_active Withdrawn
- 2006-04-25 WO PCT/US2006/015581 patent/WO2006116372A1/en not_active Ceased
- 2006-04-25 ES ES06751343T patent/ES2378243T3/es not_active Expired - Lifetime
- 2006-04-25 US US11/410,491 patent/US7413676B2/en not_active Expired - Fee Related
- 2006-04-25 CN CN200680014316XA patent/CN101166804B/zh not_active Expired - Fee Related
- 2006-04-25 EP EP06751343A patent/EP1874888B1/en not_active Expired - Lifetime
-
2008
- 2008-07-15 US US12/173,470 patent/US20080283794A1/en not_active Abandoned
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008539311A (ja) * | 2005-04-26 | 2008-11-13 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびヒドロフルオロカーボンを含む伝熱および冷媒組成物 |
| JP2014005419A (ja) * | 2012-06-27 | 2014-01-16 | Central Glass Co Ltd | フッ素化エーテルを含む熱伝達作動媒体 |
| JP2019523752A (ja) * | 2016-05-09 | 2019-08-29 | スリーエム イノベイティブ プロパティズ カンパニー | ハイドロフルオロオレフィン及びその使用方法 |
| WO2022045115A1 (ja) * | 2020-08-31 | 2022-03-03 | ダイキン工業株式会社 | フッ素オイルを含む組成物 |
| JP2022041936A (ja) * | 2020-08-31 | 2022-03-11 | ダイキン工業株式会社 | フッ素オイルを含む組成物 |
| JP7068598B2 (ja) | 2020-08-31 | 2022-05-17 | ダイキン工業株式会社 | フッ素オイルを含む組成物 |
| JP2024515551A (ja) * | 2021-04-05 | 2024-04-10 | ザイノン・テクノロジーズ・エルエルシー | 光ファイバコネクタおよび端面の非接触クリーニングのための方法 |
| JP7828366B2 (ja) | 2021-04-05 | 2026-03-11 | ザイノン・テクノロジーズ・エルエルシー | 光ファイバコネクタおよび端面の非接触クリーニングのための方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1874888A1 (en) | 2008-01-09 |
| US20060237683A1 (en) | 2006-10-26 |
| WO2006116372A1 (en) | 2006-11-02 |
| AR055055A1 (es) | 2007-08-01 |
| CN101166804B (zh) | 2011-06-08 |
| US7413676B2 (en) | 2008-08-19 |
| CN101166804A (zh) | 2008-04-23 |
| EP1874888B1 (en) | 2011-12-14 |
| ES2378243T3 (es) | 2012-04-10 |
| US20080283794A1 (en) | 2008-11-20 |
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