JPWO2019141568A5 - - Google Patents
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- Publication number
- JPWO2019141568A5 JPWO2019141568A5 JP2020539813A JP2020539813A JPWO2019141568A5 JP WO2019141568 A5 JPWO2019141568 A5 JP WO2019141568A5 JP 2020539813 A JP2020539813 A JP 2020539813A JP 2020539813 A JP2020539813 A JP 2020539813A JP WO2019141568 A5 JPWO2019141568 A5 JP WO2019141568A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- bis
- methylimidazolium
- melting composition
- ice melting
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 claims description 110
- 238000002844 melting Methods 0.000 claims description 83
- -1 Tributyl Octyl Chemical group 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 30
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L MgCl2 Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 24
- 239000002608 ionic liquid Substances 0.000 claims description 21
- 230000005496 eutectics Effects 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 239000010426 asphalt Substances 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 14
- 230000000996 additive Effects 0.000 claims description 14
- XIYUIMLQTKODPS-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CC[N+]=1C=CN(C)C=1 XIYUIMLQTKODPS-UHFFFAOYSA-M 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 150000003949 imides Chemical class 0.000 claims description 12
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 12
- 239000002270 dispersing agent Substances 0.000 claims description 11
- AKDNDOBRFDICST-UHFFFAOYSA-N methylazanium;methyl sulfate Chemical compound [NH3+]C.COS([O-])(=O)=O AKDNDOBRFDICST-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000005755 formation reaction Methods 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- ODGCEQLVLXJUCC-UHFFFAOYSA-N tetrafluoroborate Chemical compound F[B-](F)(F)F ODGCEQLVLXJUCC-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- PXELHGDYRQLRQO-UHFFFAOYSA-N 1-butyl-1-methylpyrrolidin-1-ium Chemical compound CCCC[N+]1(C)CCCC1 PXELHGDYRQLRQO-UHFFFAOYSA-N 0.000 claims description 4
- LSBXQLQATZTAPE-UHFFFAOYSA-N 1-butyl-3-methylimidazol-3-ium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCCC[N+]=1C=CN(C)C=1 LSBXQLQATZTAPE-UHFFFAOYSA-N 0.000 claims description 4
- GXZCAMSPWNHTAE-UHFFFAOYSA-N 1-methyl-3-octylimidazol-1-ium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCCCCCCCN1C=C[N+](C)=C1 GXZCAMSPWNHTAE-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 4
- UEGPKNKPLBYCNK-UHFFFAOYSA-L Magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011449 brick Substances 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011654 magnesium acetate Substances 0.000 claims description 4
- 235000011285 magnesium acetate Nutrition 0.000 claims description 4
- 229940069446 magnesium acetate Drugs 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 4
- GCRCSLNXFKCFHB-UHFFFAOYSA-N triethyl(hexyl)azanium Chemical compound CCCCCC[N+](CC)(CC)CC GCRCSLNXFKCFHB-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- GSGLHYXFTXGIAQ-UHFFFAOYSA-M 1,3-dimethylimidazol-1-ium;dimethyl phosphate Chemical compound COP([O-])(=O)OC.CN1C=C[N+](C)=C1 GSGLHYXFTXGIAQ-UHFFFAOYSA-M 0.000 claims description 2
- FBPIPPWLOCMHGR-UHFFFAOYSA-N 1,3-dimethylimidazol-1-ium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CN1C=C[N+](C)=C1 FBPIPPWLOCMHGR-UHFFFAOYSA-N 0.000 claims description 2
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 claims description 2
- ARSMIBSHEYKMJT-UHFFFAOYSA-M 1,3-dimethylimidazolium iodide Chemical compound [I-].CN1C=C[N+](C)=C1 ARSMIBSHEYKMJT-UHFFFAOYSA-M 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- IXQYBUDWDLYNMA-UHFFFAOYSA-N 1-Butyl-3-methylimidazolium hexafluorophosphate Chemical compound F[P-](F)(F)(F)(F)F.CCCCN1C=C[N+](C)=C1 IXQYBUDWDLYNMA-UHFFFAOYSA-N 0.000 claims description 2
- BMQZYMYBQZGEEY-UHFFFAOYSA-M 1-Ethyl-3-methylimidazolium chloride Chemical compound [Cl-].CCN1C=C[N+](C)=C1 BMQZYMYBQZGEEY-UHFFFAOYSA-M 0.000 claims description 2
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2H-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 claims description 2
- KYCQOKLOSUBEJK-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;bromide Chemical compound [Br-].CCCCN1C=C[N+](C)=C1 KYCQOKLOSUBEJK-UHFFFAOYSA-M 0.000 claims description 2
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 claims description 2
- ICIVTHOGIQHZRY-UHFFFAOYSA-N 1-butyl-3-methylimidazol-3-ium;cyanoiminomethylideneazanide Chemical compound [N-]=C=NC#N.CCCCN1C=C[N+](C)=C1 ICIVTHOGIQHZRY-UHFFFAOYSA-N 0.000 claims description 2
- KIDIBVPFLKLKAH-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;octyl sulfate Chemical compound CCCCN1C=C[N+](C)=C1.CCCCCCCCOS([O-])(=O)=O KIDIBVPFLKLKAH-UHFFFAOYSA-M 0.000 claims description 2
- XREPTGNZZKNFQZ-UHFFFAOYSA-M 1-butyl-3-methylimidazolium iodide Chemical compound [I-].CCCCN1C=C[N+](C)=C1 XREPTGNZZKNFQZ-UHFFFAOYSA-M 0.000 claims description 2
- DADKKHHMGSWSPH-UHFFFAOYSA-N 1-butyl-3-methylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC(C)=C1 DADKKHHMGSWSPH-UHFFFAOYSA-N 0.000 claims description 2
- XUZKQHMUEBPODI-UHFFFAOYSA-N 1-butyl-3-methylpyridin-1-ium;hexafluorophosphate Chemical compound F[P-](F)(F)(F)(F)F.CCCC[N+]1=CC=CC(C)=C1 XUZKQHMUEBPODI-UHFFFAOYSA-N 0.000 claims description 2
- UQEAMJVKASNOMA-UHFFFAOYSA-N 1-butyl-3-methylpyridin-1-ium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCCC[N+]1=CC=CC(C)=C1 UQEAMJVKASNOMA-UHFFFAOYSA-N 0.000 claims description 2
- NNLHWTTWXYBJBQ-UHFFFAOYSA-N 1-butyl-4-methylpyridin-1-ium Chemical compound CCCC[N+]1=CC=C(C)C=C1 NNLHWTTWXYBJBQ-UHFFFAOYSA-N 0.000 claims description 2
- XBSZSSGZQFAUPF-UHFFFAOYSA-N 1-butyl-4-methylpyridin-1-ium;hexafluorophosphate Chemical compound F[P-](F)(F)(F)(F)F.CCCC[N+]1=CC=C(C)C=C1 XBSZSSGZQFAUPF-UHFFFAOYSA-N 0.000 claims description 2
- VISYYHYJMCAKAF-UHFFFAOYSA-N 1-butyl-4-methylpyridin-1-ium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCCC[N+]1=CC=C(C)C=C1 VISYYHYJMCAKAF-UHFFFAOYSA-N 0.000 claims description 2
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 claims description 2
- CTMFVASPBJWPFC-UHFFFAOYSA-N 1-butylpyridin-1-ium;hexafluorophosphate Chemical compound F[P-](F)(F)(F)(F)F.CCCC[N+]1=CC=CC=C1 CTMFVASPBJWPFC-UHFFFAOYSA-N 0.000 claims description 2
- XLWDQAHXRCBPEE-UHFFFAOYSA-N 1-butylpyridin-1-ium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCCC[N+]1=CC=CC=C1 XLWDQAHXRCBPEE-UHFFFAOYSA-N 0.000 claims description 2
- FQWUDBZGMGXIAR-UHFFFAOYSA-N 1-dodecylimidazole;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[O-].CCCCCCCCCCCC[NH+]1C=CN=C1 FQWUDBZGMGXIAR-UHFFFAOYSA-N 0.000 claims description 2
- GWQYPLXGJIXMMV-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;bromide Chemical compound [Br-].CCN1C=C[N+](C)=C1 GWQYPLXGJIXMMV-UHFFFAOYSA-M 0.000 claims description 2
- VRFOKYHDLYBVAL-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCN1C=C[N+](C)=C1 VRFOKYHDLYBVAL-UHFFFAOYSA-M 0.000 claims description 2
- HZKDSQCZNUUQIF-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CCN1C=C[N+](C)=C1 HZKDSQCZNUUQIF-UHFFFAOYSA-M 0.000 claims description 2
- IKQCDTXBZKMPBB-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;iodide Chemical compound [I-].CCN1C=C[N+](C)=C1 IKQCDTXBZKMPBB-UHFFFAOYSA-M 0.000 claims description 2
- CAVPTISELCJZGX-UHFFFAOYSA-N 1-ethyl-3-methylimidazol-3-ium;methanetricarbonitrile Chemical compound N#CC(C#N)C#N.CCN1C=C[N+](C)=C1 CAVPTISELCJZGX-UHFFFAOYSA-N 0.000 claims description 2
- CUNYTRQQXKCRTJ-UHFFFAOYSA-N 1-ethyl-3-methylimidazol-3-ium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CC[N+]=1C=CN(C)C=1 CUNYTRQQXKCRTJ-UHFFFAOYSA-N 0.000 claims description 2
- VASPYXGQVWPGAB-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;thiocyanate Chemical compound [S-]C#N.CCN1C=C[N+](C)=C1 VASPYXGQVWPGAB-UHFFFAOYSA-M 0.000 claims description 2
- YPWSSSRXUOQNMQ-UHFFFAOYSA-N 1-hexyl-3-methylimidazol-3-ium;hexafluorophosphate Chemical compound F[P-](F)(F)(F)(F)F.CCCCCCN1C=C[N+](C)=C1 YPWSSSRXUOQNMQ-UHFFFAOYSA-N 0.000 claims description 2
- CZIUVCSYOGFUPH-UHFFFAOYSA-M 1-hexyl-3-methylimidazol-3-ium;iodide Chemical compound [I-].CCCCCC[N+]=1C=CN(C)C=1 CZIUVCSYOGFUPH-UHFFFAOYSA-M 0.000 claims description 2
- MFXLOVLEQJRXFP-UHFFFAOYSA-N 1-hexyl-3-methylimidazol-3-ium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCCCCCN1C=C[N+](C)=C1 MFXLOVLEQJRXFP-UHFFFAOYSA-N 0.000 claims description 2
- NKRASMXHSQKLHA-UHFFFAOYSA-M 1-hexyl-3-methylimidazolium chloride Chemical compound [Cl-].CCCCCCN1C=C[N+](C)=C1 NKRASMXHSQKLHA-UHFFFAOYSA-M 0.000 claims description 2
- YQFWGCSKGJMGHE-UHFFFAOYSA-N 1-methyl-1-propylpyrrolidin-1-ium Chemical compound CCC[N+]1(C)CCCC1 YQFWGCSKGJMGHE-UHFFFAOYSA-N 0.000 claims description 2
- LSFWFJFDPRFPBK-UHFFFAOYSA-N 1-methyl-3-pentylimidazol-1-ium Chemical compound CCCCCN1C=C[N+](C)=C1 LSFWFJFDPRFPBK-UHFFFAOYSA-N 0.000 claims description 2
- QVRCRKLLQYOIKY-UHFFFAOYSA-M 1-methyl-3-prop-2-enylimidazol-1-ium;chloride Chemical compound [Cl-].C[N+]=1C=CN(CC=C)C=1 QVRCRKLLQYOIKY-UHFFFAOYSA-M 0.000 claims description 2
- IPVXEUXSWNLULC-UHFFFAOYSA-M 1-methyl-3-prop-2-enylimidazol-1-ium;iodide Chemical compound [I-].C[N+]=1C=CN(CC=C)C=1 IPVXEUXSWNLULC-UHFFFAOYSA-M 0.000 claims description 2
- WVDDUSFOSWWJJH-UHFFFAOYSA-N 1-methyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1 WVDDUSFOSWWJJH-UHFFFAOYSA-N 0.000 claims description 2
- IVCMUVGRRDWTDK-UHFFFAOYSA-M 1-methyl-3-propylimidazol-1-ium;iodide Chemical compound [I-].CCCN1C=C[N+](C)=C1 IVCMUVGRRDWTDK-UHFFFAOYSA-M 0.000 claims description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-Butanol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 2
- OXFHNKYFIVWAAT-UHFFFAOYSA-N 2-ethyl-1,3-dimethylimidazol-1-ium Chemical compound CCC=1N(C)C=C[N+]=1C OXFHNKYFIVWAAT-UHFFFAOYSA-N 0.000 claims description 2
- FLVCCOBLYCNTDS-UHFFFAOYSA-N 2-hydroxybenzoic acid;1-nonylimidazole Chemical compound OC(=O)C1=CC=CC=C1[O-].CCCCCCCCC[NH+]1C=CN=C1 FLVCCOBLYCNTDS-UHFFFAOYSA-N 0.000 claims description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 2
- WXMVWUBWIHZLMQ-UHFFFAOYSA-N 3-methyl-1-octylimidazolium Chemical compound CCCCCCCCN1C=C[N+](C)=C1 WXMVWUBWIHZLMQ-UHFFFAOYSA-N 0.000 claims description 2
- OXFBEEDAZHXDHB-UHFFFAOYSA-M 3-methyl-1-octylimidazolium chloride Chemical compound [Cl-].CCCCCCCCN1C=C[N+](C)=C1 OXFBEEDAZHXDHB-UHFFFAOYSA-M 0.000 claims description 2
- YMGJQBWOTAGHGX-UHFFFAOYSA-M 4-methylbenzenesulfonate;methyl(tripropyl)phosphanium Chemical compound CCC[P+](C)(CCC)CCC.CC1=CC=C(S([O-])(=O)=O)C=C1 YMGJQBWOTAGHGX-UHFFFAOYSA-M 0.000 claims description 2
- FOZHLSIBKHFJBR-UHFFFAOYSA-M 4-methylbenzenesulfonate;methyl-bis(2-methylpropyl)-octylphosphanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCC[P+](C)(CC(C)C)CC(C)C FOZHLSIBKHFJBR-UHFFFAOYSA-M 0.000 claims description 2
- SNXTZFCNWIVLKZ-UHFFFAOYSA-M 4-methylbenzenesulfonate;methyl-tris(2-methylpropyl)phosphanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CC(C)C[P+](C)(CC(C)C)CC(C)C SNXTZFCNWIVLKZ-UHFFFAOYSA-M 0.000 claims description 2
- ZZAZFRIZOXHKGA-UHFFFAOYSA-M 4-methylbenzenesulfonate;tritert-butyl(methyl)phosphanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CC(C)(C)[P+](C)(C(C)(C)C)C(C)(C)C ZZAZFRIZOXHKGA-UHFFFAOYSA-M 0.000 claims description 2
- DVARTQFDIMZBAA-UHFFFAOYSA-O Ammonium nitrate Chemical compound [NH4+].[O-][N+]([O-])=O DVARTQFDIMZBAA-UHFFFAOYSA-O 0.000 claims description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
- IQQRAVYLUAZUGX-UHFFFAOYSA-N C4mim Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 2
- 229940044172 CALCIUM FORMATE Drugs 0.000 claims description 2
- KVFJTXHIACIBEQ-UHFFFAOYSA-O CCCCOC[n+]1cc[nH]c1 Chemical compound CCCCOC[n+]1cc[nH]c1 KVFJTXHIACIBEQ-UHFFFAOYSA-O 0.000 claims description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L Calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 2
- CBOCVOKPQGJKKJ-UHFFFAOYSA-L Calcium formate Chemical compound [Ca+2].[O-]C=O.[O-]C=O CBOCVOKPQGJKKJ-UHFFFAOYSA-L 0.000 claims description 2
- 229960003178 Choline Chloride Drugs 0.000 claims description 2
- SGMZJAMFUVOLNK-UHFFFAOYSA-M Choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 2
- 235000019743 Choline chloride Nutrition 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N Diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- FKSGWCHYJXNQIO-UHFFFAOYSA-N F[P-](F)(F)(F)(F)F.CC(O)CC1C=[N+](C)C=N1 Chemical compound F[P-](F)(F)(F)(F)F.CC(O)CC1C=[N+](C)C=N1 FKSGWCHYJXNQIO-UHFFFAOYSA-N 0.000 claims description 2
- BKACLUZRLYZOAV-UHFFFAOYSA-N F[P-](F)(F)(F)(F)F.CCOCCOn1cc[n+](C)c1 Chemical compound F[P-](F)(F)(F)(F)F.CCOCCOn1cc[n+](C)c1 BKACLUZRLYZOAV-UHFFFAOYSA-N 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N Hexamethylphosphoramide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N M-Xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N MeOtBu Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N Nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- WFIZEGIEIOHZCP-UHFFFAOYSA-M Potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N Propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M Sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 2
- 239000004280 Sodium formate Substances 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N Sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N Tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 2
- LAGQNGWYNLUQRI-UHFFFAOYSA-N Trioctylmethylammonium bis(trifluoromethylsulfonyl)imide Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC LAGQNGWYNLUQRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 2
- OMMLVGFDYVJZPD-UHFFFAOYSA-M bis(dioctylamino)methylidene-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCN(CCCCCCCC)C(=[N+](C)C)N(CCCCCCCC)CCCCCCCC OMMLVGFDYVJZPD-UHFFFAOYSA-M 0.000 claims description 2
- XOZHIVUWCICHSQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XOZHIVUWCICHSQ-UHFFFAOYSA-N 0.000 claims description 2
- UCCKRVYTJPMHRO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-2,3-dimethylimidazol-3-ium Chemical compound CCCC[N+]=1C=CN(C)C=1C.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F UCCKRVYTJPMHRO-UHFFFAOYSA-N 0.000 claims description 2
- INDFXCHYORWHLQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-3-methylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F INDFXCHYORWHLQ-UHFFFAOYSA-N 0.000 claims description 2
- LRESCJAINPKJTO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-ethyl-3-methylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F LRESCJAINPKJTO-UHFFFAOYSA-N 0.000 claims description 2
- IEKPEVWFUIKZFI-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-hexadecyl-3-methylimidazol-3-ium Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 IEKPEVWFUIKZFI-UHFFFAOYSA-N 0.000 claims description 2
- RCNFOZUBFOFJKZ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-hexyl-3-methylimidazol-3-ium Chemical compound CCCCCC[N+]=1C=CN(C)C=1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F RCNFOZUBFOFJKZ-UHFFFAOYSA-N 0.000 claims description 2
- IEFUHGXOQSVRDQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-methyl-1-propylpiperidin-1-ium Chemical compound CCC[N+]1(C)CCCCC1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F IEFUHGXOQSVRDQ-UHFFFAOYSA-N 0.000 claims description 2
- DHMWATGUEVQTIY-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-methyl-3-prop-2-enylimidazol-1-ium Chemical compound C[N+]=1C=CN(CC=C)C=1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F DHMWATGUEVQTIY-UHFFFAOYSA-N 0.000 claims description 2
- CDWUIWLQQDTHRA-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-methyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F CDWUIWLQQDTHRA-UHFFFAOYSA-N 0.000 claims description 2
- CHJFYGKCKZENPL-UHFFFAOYSA-N bis[butyl(ethyl)amino]methylidene-dimethylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCCCN(CC)C(=[N+](C)C)N(CC)CCCC CHJFYGKCKZENPL-UHFFFAOYSA-N 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 239000001639 calcium acetate Substances 0.000 claims description 2
- 235000011092 calcium acetate Nutrition 0.000 claims description 2
- 229960005147 calcium acetate Drugs 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 235000011148 calcium chloride Nutrition 0.000 claims description 2
- 239000004281 calcium formate Substances 0.000 claims description 2
- 235000019255 calcium formate Nutrition 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- MKHFCTXNDRMIDR-UHFFFAOYSA-N cyanoiminomethylideneazanide;1-ethyl-3-methylimidazol-3-ium Chemical compound [N-]=C=NC#N.CCN1C=C[N+](C)=C1 MKHFCTXNDRMIDR-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- HQWOEDCLDNFWEV-UHFFFAOYSA-M diethyl phosphate;1-ethyl-3-methylimidazol-3-ium Chemical compound CC[N+]=1C=CN(C)C=1.CCOP([O-])(=O)OCC HQWOEDCLDNFWEV-UHFFFAOYSA-M 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
- AHRQMWOXLCFNAV-UHFFFAOYSA-O ethylammonium nitrate Chemical compound CC[NH3+].[O-][N+]([O-])=O AHRQMWOXLCFNAV-UHFFFAOYSA-O 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000008079 hexane Substances 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- LPPJNZJBKFSQGA-UHFFFAOYSA-M hydron;2-hydroxyethyl(trimethyl)azanium;phosphate Chemical compound OP(O)([O-])=O.C[N+](C)(C)CCO LPPJNZJBKFSQGA-UHFFFAOYSA-M 0.000 claims description 2
- 235000011147 magnesium chloride Nutrition 0.000 claims description 2
- GMDNUWQNDQDBNQ-UHFFFAOYSA-L magnesium;diformate Chemical compound [Mg+2].[O-]C=O.[O-]C=O GMDNUWQNDQDBNQ-UHFFFAOYSA-L 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 229940078552 o-xylene Drugs 0.000 claims description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 2
- WVGZZTIINNFUQS-UHFFFAOYSA-N pentamethylphosphoranuidylmethane Chemical compound C[P-](C)(C)(C)(C)C WVGZZTIINNFUQS-UHFFFAOYSA-N 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 229920001484 poly(alkylene) Polymers 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004576 sand Substances 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 235000002639 sodium chloride Nutrition 0.000 claims description 2
- 235000019254 sodium formate Nutrition 0.000 claims description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
- GTCDARUMAMVCRO-UHFFFAOYSA-M tetraethylazanium;acetate Chemical compound CC([O-])=O.CC[N+](CC)(CC)CC GTCDARUMAMVCRO-UHFFFAOYSA-M 0.000 claims description 2
- DTIFFPXSSXFQCJ-UHFFFAOYSA-N tetrahexylazanium Chemical compound CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC DTIFFPXSSXFQCJ-UHFFFAOYSA-N 0.000 claims description 2
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 claims description 2
- AQQOUVLRCMEMHI-UHFFFAOYSA-N tributyl(heptyl)azanium Chemical compound CCCCCCC[N+](CCCC)(CCCC)CCCC AQQOUVLRCMEMHI-UHFFFAOYSA-N 0.000 claims description 2
- FJAPXHMQWAFWMW-UHFFFAOYSA-N tributyl(hexyl)azanium Chemical compound CCCCCC[N+](CCCC)(CCCC)CCCC FJAPXHMQWAFWMW-UHFFFAOYSA-N 0.000 claims description 2
- YWRSPDSZBLLBPN-UHFFFAOYSA-M tributyl(octyl)azanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCCCCCC[N+](CCCC)(CCCC)CCCC YWRSPDSZBLLBPN-UHFFFAOYSA-M 0.000 claims description 2
- WCZKTXKOKMXREO-UHFFFAOYSA-N triethylsulfanium Chemical compound CC[S+](CC)CC WCZKTXKOKMXREO-UHFFFAOYSA-N 0.000 claims description 2
- RJELOMHXBLDMDB-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC RJELOMHXBLDMDB-UHFFFAOYSA-M 0.000 claims description 2
- JCQGIZYNVAZYOH-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC JCQGIZYNVAZYOH-UHFFFAOYSA-M 0.000 claims description 2
- WCKLETBLOAOZDE-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium;hexafluorophosphate Chemical compound F[P-](F)(F)(F)(F)F.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC WCKLETBLOAOZDE-UHFFFAOYSA-N 0.000 claims description 2
- SIKCPMYZUKIFIB-UHFFFAOYSA-N bis(dioctylamino)methylidene-dimethylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCCCCCCCN(CCCCCCCC)C(=[N+](C)C)N(CCCCCCCC)CCCCCCCC SIKCPMYZUKIFIB-UHFFFAOYSA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
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| US201862618877P | 2018-01-18 | 2018-01-18 | |
| US62/618,877 | 2018-01-18 | ||
| PCT/EP2019/050473 WO2019141568A1 (fr) | 2018-01-18 | 2019-01-10 | Saturation accrue de compositions de fonte de glace et procédés d'utilisation |
Publications (2)
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| JP2021510760A JP2021510760A (ja) | 2021-04-30 |
| JPWO2019141568A5 true JPWO2019141568A5 (fr) | 2022-02-07 |
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| US (1) | US11584874B2 (fr) |
| EP (1) | EP3740543A1 (fr) |
| JP (1) | JP2021510760A (fr) |
| KR (1) | KR20200108449A (fr) |
| CN (1) | CN111511871A (fr) |
| AU (1) | AU2019209219A1 (fr) |
| CA (1) | CA3086816A1 (fr) |
| WO (1) | WO2019141568A1 (fr) |
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| CN113046026B (zh) * | 2021-04-07 | 2023-03-24 | 山西大同大学 | 一种无氯低腐蚀性煤炭防冻液 |
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| JPS63117089A (ja) * | 1986-11-05 | 1988-05-21 | Mototada Matsushima | 液状融雪・融氷剤 |
| JP2013506753A (ja) * | 2009-10-05 | 2013-02-28 | カーギル・インコーポレイテッド | 改善された凍結防止剤組成物 |
| US8187489B1 (en) * | 2011-03-23 | 2012-05-29 | The United States Of America As Represented By The Secretary Of The Navy | Biodegradable ionic liquids for aircraft deicing |
| CN103709995B (zh) * | 2013-12-04 | 2015-01-14 | 宁波保税区安德利斯机械有限公司 | 一种环境友好的跑道融雪除冰剂 |
| CN104862709A (zh) | 2015-04-28 | 2015-08-26 | 安徽不二越精工轴承有限公司 | 一种钢材防腐处理液 |
| CN105062421A (zh) * | 2015-09-06 | 2015-11-18 | 温州泓呈祥科技有限公司 | 环保型融雪剂及其制备方法 |
| CN107129874A (zh) * | 2017-05-23 | 2017-09-05 | 句容耀皮节能玻璃科技发展有限公司 | 一种汽车玻璃水及其制备方法 |
| CN107083234A (zh) * | 2017-05-23 | 2017-08-22 | 句容耀皮节能玻璃科技发展有限公司 | 一种汽车玻璃防雾防冻剂及其制备方法 |
-
2019
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- 2019-01-10 WO PCT/EP2019/050473 patent/WO2019141568A1/fr unknown
- 2019-01-10 US US16/961,960 patent/US11584874B2/en active Active
- 2019-01-10 KR KR1020207023089A patent/KR20200108449A/ko unknown
- 2019-01-10 EP EP19700656.2A patent/EP3740543A1/fr not_active Withdrawn
- 2019-01-10 AU AU2019209219A patent/AU2019209219A1/en active Pending
- 2019-01-10 CA CA3086816A patent/CA3086816A1/fr active Pending
- 2019-01-10 CN CN201980006693.6A patent/CN111511871A/zh active Pending
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