JP6971249B2 - アミン含有非環状ハイドロフルオロエーテル及びその使用方法 - Google Patents
アミン含有非環状ハイドロフルオロエーテル及びその使用方法 Download PDFInfo
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- JP6971249B2 JP6971249B2 JP2018547944A JP2018547944A JP6971249B2 JP 6971249 B2 JP6971249 B2 JP 6971249B2 JP 2018547944 A JP2018547944 A JP 2018547944A JP 2018547944 A JP2018547944 A JP 2018547944A JP 6971249 B2 JP6971249 B2 JP 6971249B2
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- Prior art keywords
- acyclic
- fluorocompound
- atom
- present disclosure
- carbon atoms
- Prior art date
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- 125000002015 acyclic group Chemical group 0.000 title claims description 65
- 150000001412 amines Chemical class 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 65
- 239000012530 fluid Substances 0.000 claims description 57
- -1 Acyclic fluoro compound Chemical class 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000003792 electrolyte Substances 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 23
- 238000004140 cleaning Methods 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000013529 heat transfer fluid Substances 0.000 claims description 11
- 238000005476 soldering Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 238000012546 transfer Methods 0.000 description 28
- 238000000034 method Methods 0.000 description 27
- 239000011248 coating agent Substances 0.000 description 20
- 238000000576 coating method Methods 0.000 description 20
- 239000000758 substrate Substances 0.000 description 20
- 230000008569 process Effects 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 17
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- 238000003756 stirring Methods 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 238000010792 warming Methods 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001450 anions Chemical class 0.000 description 9
- 239000008199 coating composition Substances 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 150000003254 radicals Chemical group 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000008016 vaporization Effects 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
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- 150000002891 organic anions Chemical class 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
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- 239000000314 lubricant Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012808 vapor phase Substances 0.000 description 5
- 239000002918 waste heat Substances 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical class FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 231100000053 low toxicity Toxicity 0.000 description 4
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 4
- 239000010702 perfluoropolyether Substances 0.000 description 4
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 230000035939 shock Effects 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- XHVKFIIHYDDMQB-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-4-methoxybutane Chemical compound COCC(F)(F)C(F)C(F)(F)F XHVKFIIHYDDMQB-UHFFFAOYSA-N 0.000 description 3
- YSJPWKICFXZRAH-UHFFFAOYSA-N 4-ethoxy-1,1,1,2,3,3-hexafluoropentane Chemical compound CCOC(C)C(F)(F)C(F)C(F)(F)F YSJPWKICFXZRAH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- 235000012431 wafers Nutrition 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- WZAAPMFOOIVWCZ-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-[1,2,2-trifluoro-3-[2,2,3-trifluoro-3-(2,2,3,3,5,5,6,6-octafluoromorpholin-4-yl)propoxy]propyl]morpholine Chemical compound FC(N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F)C(F)(F)COCC(F)(F)C(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F WZAAPMFOOIVWCZ-UHFFFAOYSA-N 0.000 description 2
- WIDURIOYTWKSHX-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoromorpholine Chemical compound FC1(F)NC(F)(F)C(F)(F)OC1(F)F WIDURIOYTWKSHX-UHFFFAOYSA-N 0.000 description 2
- DXNIRXJFXRBTSX-UHFFFAOYSA-N 4-[3-ethoxy-1,2-difluoro-2-(trifluoromethyl)butyl]-2,2,3,3,5,5,6,6-octafluoromorpholine Chemical compound CCOC(C)C(F)(C(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F)C(F)(F)F DXNIRXJFXRBTSX-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical class NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910017008 AsF 6 Inorganic materials 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ZHXYBQYDAXYKLU-UHFFFAOYSA-N FC1(C(N(C(C(O1)(F)F)(F)F)C(C(COC)(F)F)F)(F)F)F Chemical compound FC1(C(N(C(C(O1)(F)F)(F)F)C(C(COC)(F)F)F)(F)F)F ZHXYBQYDAXYKLU-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
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- 229920001577 copolymer Polymers 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229910001412 inorganic anion Inorganic materials 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 description 2
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
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- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical class CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- 230000003134 recirculating effect Effects 0.000 description 2
- 238000007655 standard test method Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- HBZVXKDQRIQMCW-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoroheptane Chemical compound FC(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F HBZVXKDQRIQMCW-UHFFFAOYSA-N 0.000 description 1
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 description 1
- KSUHRWWSNHJRMY-UHFFFAOYSA-N 1,1,1,2,2,4-hexafluorobutane Chemical compound FCCC(F)(F)C(F)(F)F KSUHRWWSNHJRMY-UHFFFAOYSA-N 0.000 description 1
- GAJMTULQAJVYMD-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-1-(1,1,2,3,3-pentafluoroprop-2-enoxy)-3-(trifluoromethoxy)propane Chemical compound FC(F)=C(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)F GAJMTULQAJVYMD-UHFFFAOYSA-N 0.000 description 1
- UERAGWQPCSLYTB-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-3-methylcyclobutane Chemical compound CC1CC(F)(F)C1(F)F UERAGWQPCSLYTB-UHFFFAOYSA-N 0.000 description 1
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical class FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 1
- DHZPVNGMSDDSQX-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(F)CCC1(F)F DHZPVNGMSDDSQX-UHFFFAOYSA-N 0.000 description 1
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
- XXZOEDQFGXTEAD-UHFFFAOYSA-N 1,2-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1C(F)(F)F XXZOEDQFGXTEAD-UHFFFAOYSA-N 0.000 description 1
- UJIGKESMIPTWJH-UHFFFAOYSA-N 1,3-dichloro-1,1,2,2,3-pentafluoropropane Chemical compound FC(Cl)C(F)(F)C(F)(F)Cl UJIGKESMIPTWJH-UHFFFAOYSA-N 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical group O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- WFJINAXLTGKWLB-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC=C WFJINAXLTGKWLB-UHFFFAOYSA-N 0.000 description 1
- ZLFSOCVJMGQPTE-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)OC=C ZLFSOCVJMGQPTE-UHFFFAOYSA-N 0.000 description 1
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- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
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- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/26—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/38—Halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- 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
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- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
- C11D3/245—Organic compounds containing halogen containing fluorine
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- 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
- C11D7/22—Organic compounds
- C11D7/28—Organic compounds containing 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
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
- C11D9/22—Organic compounds, e.g. vitamins
- C11D9/28—Organic compounds, e.g. vitamins containing halogen
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- Wood Science & Technology (AREA)
- Combustion & Propulsion (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
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| US201662306947P | 2016-03-11 | 2016-03-11 | |
| US62/306,947 | 2016-03-11 | ||
| PCT/US2017/018780 WO2017155686A1 (en) | 2016-03-11 | 2017-02-22 | Amine-containing acyclic hydrofluoroethers and methods of using the same |
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| JP2019510760A5 JP2019510760A5 (enExample) | 2020-04-02 |
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| CN107614560A (zh) * | 2015-06-05 | 2018-01-19 | 3M创新有限公司 | 氢氟烯烃及其使用方法 |
| JP6738837B2 (ja) * | 2015-06-05 | 2020-08-12 | 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 |
| JP6971249B2 (ja) | 2016-03-11 | 2021-11-24 | スリーエム イノベイティブ プロパティズ カンパニー | アミン含有非環状ハイドロフルオロエーテル及びその使用方法 |
| US10301293B2 (en) | 2016-03-11 | 2019-05-28 | 3M Innovative Properties Company | Amine-containing cyclic hydrofluoroethers and methods of using the same |
| CN109689637B (zh) * | 2016-08-29 | 2022-07-08 | 3M创新有限公司 | 含氮和二氧戊环的氢氟醚及其使用方法 |
| JP7043489B2 (ja) * | 2016-09-26 | 2022-03-29 | スリーエム イノベイティブ プロパティズ カンパニー | 窒素及び/又は酸素含有ヒドロフルオロオレフィン、並びにその製造方法及び使用方法 |
| US20190233321A1 (en) | 2018-01-26 | 2019-08-01 | Corning Incorporated | Liquid-assisted laser micromachining of transparent dielectrics |
| WO2021127346A1 (en) * | 2019-12-20 | 2021-06-24 | 3M Innovative Properties Company | Fluorinated copolymer and compositions and articles including the same |
| CN117821020B (zh) * | 2023-12-25 | 2024-08-16 | 润威新材料科技(上海)有限公司 | 一种复合冷却介质组合物及其制备方法和用途 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700695A (en) | 1969-10-16 | 1972-10-24 | Hooker Chemical Corp | Fluorinated tetrahydro-pyrans |
| GB8301506D0 (en) | 1983-01-20 | 1983-02-23 | Electricity Council | Fluorinated ethers |
| US4782148A (en) | 1985-07-23 | 1988-11-01 | Agency Of Industrial Science & Technology | Method for production of perfluoro N-(vinyl)amines |
| US4929725A (en) | 1985-09-06 | 1990-05-29 | Moore George G I | Perfluoroaminoethers |
| US4788339A (en) * | 1985-09-06 | 1988-11-29 | Minnesota Mining And Manufacturing Company | Perfluoroaminoethers |
| US4985556A (en) | 1987-09-10 | 1991-01-15 | Agency Of Industrial Science & Technology | Perfluoro(dialkylaminopropene) derivatives |
| JPH0170445U (enExample) | 1987-10-28 | 1989-05-10 | ||
| JPS6470445A (en) | 1988-07-23 | 1989-03-15 | Agency Ind Science Techn | Novel perfluoroalkenylamine and production thereof |
| US5658962A (en) * | 1994-05-20 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application |
| US6548471B2 (en) * | 1995-01-20 | 2003-04-15 | 3M Innovative Properties Company | Alkoxy-substituted perfluorocompounds |
| US5925611A (en) * | 1995-01-20 | 1999-07-20 | Minnesota Mining And Manufacturing Company | Cleaning process and composition |
| US6552090B1 (en) * | 1997-09-15 | 2003-04-22 | 3M Innovative Properties Company | Perfluoroalkyl haloalkyl ethers and compositions and applications thereof |
| US7691282B2 (en) * | 2005-09-08 | 2010-04-06 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| US8193397B2 (en) * | 2006-12-06 | 2012-06-05 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| CN101657931B (zh) | 2006-12-20 | 2013-03-20 | 3M创新有限公司 | 用于锂电池电解液的氟化化合物 |
| CN101778835B (zh) | 2007-08-17 | 2013-03-20 | 旭硝子株式会社 | 经精制的含氟二磺酰亚胺的铵盐的制造方法 |
| JP2011528659A (ja) * | 2008-07-18 | 2011-11-24 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化エーテル化合物及びその使用方法 |
| US7988877B2 (en) * | 2008-11-03 | 2011-08-02 | 3M Innovative Properties Company | Methods of making fluorinated ethers, fluorinated ethers, and uses thereof |
| JP5212350B2 (ja) | 2008-12-24 | 2013-06-19 | 住友化学株式会社 | 含ハロゲン有機硫黄化合物およびその用途 |
| US8323524B2 (en) * | 2009-10-01 | 2012-12-04 | 3M Innovative Properties Company | Apparatus including hydrofluoroether with high temperature stability and uses thereof |
| US8261560B2 (en) * | 2009-11-02 | 2012-09-11 | 3M Innovative Properties Company | Methods of using hydrofluoroethers as heat transfer fluids |
| US8535559B2 (en) * | 2010-03-26 | 2013-09-17 | 3M Innovative Properties Company | Nitrogen-containing fluoroketones for high temperature heat transfer |
| JP5959632B2 (ja) * | 2011-06-10 | 2016-08-02 | スリーエム イノベイティブ プロパティズ カンパニー | 部分フッ素化ケトン並びにその製造方法及びその使用方法 |
| US9540316B2 (en) * | 2013-07-25 | 2017-01-10 | 3M Innovative Properties Company | Nitrogen containing hydrofluoroethers and methods of making same |
| EP3169745B1 (en) * | 2014-07-16 | 2020-04-29 | 3M Innovative Properties Company | Hydrofluoroether olefins and methods of using same |
| JP6621469B2 (ja) * | 2014-09-23 | 2019-12-18 | スリーエム イノベイティブ プロパティズ カンパニー | 窒素含有ハイドロフルオロエーテルを含む作動流体 |
| US20170369755A1 (en) | 2014-12-08 | 2017-12-28 | 3M Innovative Properties Company | Hydrofluoroolefins and methods for using same |
| CN104577200A (zh) | 2015-02-06 | 2015-04-29 | 宁德新能源科技有限公司 | 一种电解液添加剂及其应用 |
| US10301293B2 (en) | 2016-03-11 | 2019-05-28 | 3M Innovative Properties Company | Amine-containing cyclic hydrofluoroethers and methods of using the same |
| JP6971249B2 (ja) | 2016-03-11 | 2021-11-24 | スリーエム イノベイティブ プロパティズ カンパニー | アミン含有非環状ハイドロフルオロエーテル及びその使用方法 |
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2017
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- 2017-02-22 EP EP17763731.1A patent/EP3426643A4/en not_active Withdrawn
- 2017-02-22 CN CN201780016040.7A patent/CN108713014A/zh active Pending
- 2017-02-22 US US16/073,854 patent/US10344006B2/en not_active Expired - Fee Related
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| EP3426643A4 (en) | 2019-08-21 |
| JP2019510760A (ja) | 2019-04-18 |
| EP3426643A1 (en) | 2019-01-16 |
| US10344006B2 (en) | 2019-07-09 |
| WO2017155686A1 (en) | 2017-09-14 |
| US20190040024A1 (en) | 2019-02-07 |
| CN108713014A (zh) | 2018-10-26 |
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