TWI718152B - 氫氟烯烴及其使用方法 - Google Patents
氫氟烯烴及其使用方法 Download PDFInfo
- Publication number
- TWI718152B TWI718152B TW105117671A TW105117671A TWI718152B TW I718152 B TWI718152 B TW I718152B TW 105117671 A TW105117671 A TW 105117671A TW 105117671 A TW105117671 A TW 105117671A TW I718152 B TWI718152 B TW I718152B
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- TW
- Taiwan
- Prior art keywords
- carbon atoms
- hydrofluoroolefin
- working fluid
- heteroatoms
- heat transfer
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 53
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 51
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 239000012530 fluid Substances 0.000 claims description 107
- 238000012546 transfer Methods 0.000 claims description 24
- 230000007246 mechanism Effects 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000013529 heat transfer fluid Substances 0.000 claims description 10
- 239000004065 semiconductor Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000446 fuel Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 description 154
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
- 239000000047 product Substances 0.000 description 58
- 239000002904 solvent Substances 0.000 description 42
- 238000003756 stirring Methods 0.000 description 42
- -1 perfluorinated vinyl amine Chemical class 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000000463 material Substances 0.000 description 37
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- 238000004140 cleaning Methods 0.000 description 26
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- 239000004094 surface-active agent Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 150000004678 hydrides Chemical class 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 20
- 239000012071 phase Substances 0.000 description 19
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- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000003638 chemical reducing agent Substances 0.000 description 17
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 17
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 16
- 239000011737 fluorine Substances 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 15
- 239000002243 precursor Substances 0.000 description 15
- 150000001336 alkenes Chemical class 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 14
- AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical class CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 239000004215 Carbon black (E152) Substances 0.000 description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 13
- 239000012279 sodium borohydride Substances 0.000 description 13
- 229910000033 sodium borohydride Inorganic materials 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000008199 coating composition Substances 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 239000006260 foam Substances 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000002667 nucleating agent Substances 0.000 description 10
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 150000003839 salts Chemical class 0.000 description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
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- 239000006184 cosolvent Substances 0.000 description 8
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- 239000000314 lubricant Substances 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- 238000005481 NMR spectroscopy Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
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- 238000004508 fractional distillation Methods 0.000 description 7
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- 239000002918 waste heat Substances 0.000 description 7
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- 239000004744 fabric Substances 0.000 description 6
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- 150000002891 organic anions Chemical class 0.000 description 6
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000004088 foaming agent Substances 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 230000008016 vaporization Effects 0.000 description 5
- 238000004293 19F NMR spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 241000208340 Araliaceae Species 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 4
- 235000003140 Panax quinquefolius Nutrition 0.000 description 4
- 229920001774 Perfluoroether Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 4
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- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 4
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- 239000002808 molecular sieve Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-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
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 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
- 238000010998 test method Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/24—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton the carbon skeleton being 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0019—Use of organic additives halogenated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/143—Halogen containing compounds
- C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
- H01L21/67005—Apparatus not specifically provided for elsewhere
- H01L21/67011—Apparatus for manufacture or treatment
- H01L21/67098—Apparatus for thermal treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/16—Unsaturated hydrocarbons
- C08J2203/162—Halogenated unsaturated hydrocarbons, e.g. H2C=CF2
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
- C08J2325/02—Homopolymers or copolymers of hydrocarbons
- C08J2325/04—Homopolymers or copolymers of styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
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| US201562171446P | 2015-06-05 | 2015-06-05 | |
| US62/171,446 | 2015-06-05 |
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| 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 |
| JP6868623B2 (ja) | 2015-12-02 | 2021-05-12 | スリーエム イノベイティブ プロパティズ カンパニー | アリル末端不飽和ヒドロフルオロアミン及びアリル末端不飽和ヒドロフルオロエーテル化合物並びにこれらの使用方法 |
| JP6949023B2 (ja) | 2015-12-17 | 2021-10-13 | スリーエム イノベイティブ プロパティズ カンパニー | アミン含有ポリマー、その分散液並びにこれらの製造方法及び使用方法 |
| EP3455322B1 (en) * | 2016-05-09 | 2021-03-03 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| US11479525B2 (en) * | 2016-08-22 | 2022-10-25 | 3M Innovative Properties Company | Propenylamines and methods of making and using same |
| 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 |
| EP3558915A4 (en) | 2016-12-21 | 2020-07-29 | 3M Innovative Properties Company | HYDROFLUOROLEFINS AND ASSOCIATED PROCESSES FOR USE |
| EP3601470B1 (en) * | 2017-03-21 | 2024-04-24 | 3M Innovative Properties Company | A method for selectively making hfp-trimer |
| US11452238B2 (en) | 2017-06-07 | 2022-09-20 | 3M Innovative Properties Company | Fluids for immersion cooling |
| WO2019220293A1 (en) * | 2018-05-15 | 2019-11-21 | 3M Innovative Properties Company | Perfluoroaminoolefins and methods of making and using the same |
| CN113195674B (zh) * | 2018-12-20 | 2023-09-01 | 3M创新有限公司 | 氢氟烯烃及其使用方法 |
| WO2020132309A1 (en) | 2018-12-21 | 2020-06-25 | Honeywell International Inc. | Solvent compositions containing 1,2,2-trifluoro-1-trifluoromethylcyclobutane (tfmcb) |
| US11773352B2 (en) * | 2018-12-26 | 2023-10-03 | 3M Innovative Properties Company | Hydrochlorofluoroolefins and methods of using same |
| WO2020170080A1 (en) * | 2019-02-19 | 2020-08-27 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| WO2020187839A1 (en) * | 2019-03-18 | 2020-09-24 | Solvay Specialty Polymers Italy S.P.A. | Heat exchange method using fluorinated compounds having a low gwp |
| US12414267B2 (en) * | 2019-06-12 | 2025-09-09 | 3M Innovative Properties Company | Fluorinated aromatics and methods of using same |
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| US4782148A (en) | 1985-07-23 | 1988-11-01 | Agency Of Industrial Science & Technology | Method for production of perfluoro N-(vinyl)amines |
| JPS6470444A (en) | 1987-09-10 | 1989-03-15 | Agency Ind Science Techn | Novel perfluoroalkenylamine and production thereof |
| JPS6470445A (en) | 1988-07-23 | 1989-03-15 | Agency Ind Science Techn | Novel perfluoroalkenylamine and production thereof |
| US5396000A (en) | 1993-05-24 | 1995-03-07 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,2,3,-pentafluoropropane |
| DE69812901T2 (de) | 1997-01-31 | 2003-11-06 | E.I. Du Pont De Nemours And Co., Wilmington | Katalytische herstellung von pentafluorpropenen |
| US5986151A (en) | 1997-02-05 | 1999-11-16 | Alliedsignal Inc. | Fluorinated propenes from pentafluoropropane |
| US6203944B1 (en) | 1998-03-26 | 2001-03-20 | 3M Innovative Properties Company | Electrode for a lithium battery |
| WO2001003444A2 (en) | 1999-07-07 | 2001-01-11 | Rossides Michael T | Expected value methods and systems for paying and qualifying |
| US7279451B2 (en) * | 2002-10-25 | 2007-10-09 | Honeywell International Inc. | Compositions containing fluorine substituted olefins |
| US7833433B2 (en) * | 2002-10-25 | 2010-11-16 | Honeywell International Inc. | Heat transfer methods using heat transfer compositions containing trifluoromonochloropropene |
| US9994750B2 (en) * | 2002-10-25 | 2018-06-12 | Honeywell International Inc. | Compositions containing fluorine substituted olefins and methods and systems using same |
| US8530708B2 (en) | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
| US9499729B2 (en) * | 2006-06-26 | 2016-11-22 | Honeywell International Inc. | Compositions and methods containing fluorine substituted olefins |
| US7560602B2 (en) | 2005-11-03 | 2009-07-14 | Honeywell International Inc. | Process for manufacture of fluorinated olefins |
| US8193397B2 (en) * | 2006-12-06 | 2012-06-05 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| WO2009019219A2 (en) | 2007-08-03 | 2009-02-12 | Solvay (Société Anonyme) | Methods of using a solvent or a foam blowing agent |
| US8820079B2 (en) | 2008-12-05 | 2014-09-02 | Honeywell International Inc. | Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids |
| US8261560B2 (en) * | 2009-11-02 | 2012-09-11 | 3M Innovative Properties Company | Methods of using hydrofluoroethers as heat transfer fluids |
| 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 |
| JP6773326B2 (ja) * | 2013-12-20 | 2020-10-21 | スリーエム イノベイティブ プロパティズ カンパニー | 作動流体としてのフッ素化オレフィン及びその使用方法 |
| 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 |
| WO2016064585A1 (en) * | 2014-10-24 | 2016-04-28 | 3M Innovative Properties Company | Segregated fluorinated esters |
| US20160262490A1 (en) * | 2015-03-13 | 2016-09-15 | Honeywell International Inc. | Foams, foamable compositions and methods of making integral skin foams |
| 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 |
| JP6868623B2 (ja) * | 2015-12-02 | 2021-05-12 | スリーエム イノベイティブ プロパティズ カンパニー | アリル末端不飽和ヒドロフルオロアミン及びアリル末端不飽和ヒドロフルオロエーテル化合物並びにこれらの使用方法 |
| JP6949023B2 (ja) * | 2015-12-17 | 2021-10-13 | スリーエム イノベイティブ プロパティズ カンパニー | アミン含有ポリマー、その分散液並びにこれらの製造方法及び使用方法 |
| 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 |
| EP3455322B1 (en) * | 2016-05-09 | 2021-03-03 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| 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 |
-
2016
- 2016-05-27 CN CN201680032493.4A patent/CN107614560A/zh active Pending
- 2016-05-27 JP JP2017562981A patent/JP6749347B2/ja active Active
- 2016-05-27 KR KR1020187000130A patent/KR102580755B1/ko active Active
- 2016-05-27 WO PCT/US2016/034514 patent/WO2016196240A1/en not_active Ceased
- 2016-05-27 US US15/578,280 patent/US10738001B2/en active Active
- 2016-05-27 EP EP16804087.1A patent/EP3303435B1/en active Active
- 2016-06-03 TW TW105117671A patent/TWI718152B/zh active
Non-Patent Citations (1)
| Title |
|---|
| Hanna Wójtowicz‐Rajchel et al.,"A Convenient Method for the Synthesis of Stable α-Fluoro Enamines of NucleobasesA Convenient Method for the Synthesis of Stable α-Fluoro Enamines of Nucleobases", Eur. J. Org. Chem., Vol.2, 2008, pages 368-376. * |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20180015719A (ko) | 2018-02-13 |
| EP3303435B1 (en) | 2020-11-25 |
| US10738001B2 (en) | 2020-08-11 |
| CN107614560A (zh) | 2018-01-19 |
| JP6749347B2 (ja) | 2020-09-02 |
| EP3303435A1 (en) | 2018-04-11 |
| WO2016196240A1 (en) | 2016-12-08 |
| JP2018525327A (ja) | 2018-09-06 |
| US20180141893A1 (en) | 2018-05-24 |
| KR102580755B1 (ko) | 2023-09-19 |
| TW201714879A (zh) | 2017-05-01 |
| EP3303435A4 (en) | 2019-02-20 |
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