NO171068B - Fluorholdige organotinn-forbindelser som er anvendelige for fluorforsterkede tinnoksydbelegg - Google Patents
Fluorholdige organotinn-forbindelser som er anvendelige for fluorforsterkede tinnoksydbelegg Download PDFInfo
- Publication number
- NO171068B NO171068B NO881186A NO881186A NO171068B NO 171068 B NO171068 B NO 171068B NO 881186 A NO881186 A NO 881186A NO 881186 A NO881186 A NO 881186A NO 171068 B NO171068 B NO 171068B
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- Norway
- Prior art keywords
- trifluoroacetate
- tinnox
- fluorprefined
- fluorable
- coating
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 23
- 238000000576 coating method Methods 0.000 title abstract description 12
- 239000011248 coating agent Substances 0.000 title description 2
- GGBFOKTZTGOTFG-UHFFFAOYSA-K [butyl(dichloro)stannyl] 2,2,2-trifluoroacetate Chemical compound CCCC[Sn](Cl)(Cl)OC(=O)C(F)(F)F GGBFOKTZTGOTFG-UHFFFAOYSA-K 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QFACVQVCDZTJIT-UHFFFAOYSA-J [Cl-].[Cl-].[Sn+4].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F Chemical compound [Cl-].[Cl-].[Sn+4].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F QFACVQVCDZTJIT-UHFFFAOYSA-J 0.000 claims 1
- XAGGPHOSLFCFFC-UHFFFAOYSA-K butyl(chloro)tin(2+);2,2,2-trifluoroacetate Chemical compound CCCC[Sn+2]Cl.[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F XAGGPHOSLFCFFC-UHFFFAOYSA-K 0.000 claims 1
- BYUYXXGNGAGMJF-UHFFFAOYSA-K butyl(chloro)tin(2+);2,2,2-trifluoroacetate;acetate Chemical compound CC([O-])=O.CCCC[Sn+2]Cl.[O-]C(=O)C(F)(F)F BYUYXXGNGAGMJF-UHFFFAOYSA-K 0.000 claims 1
- YXPSLKXRUCMRIN-UHFFFAOYSA-L butyl(dichloro)stannanylium;2,2,2-trifluoroethanolate Chemical compound [O-]CC(F)(F)F.CCCC[Sn+](Cl)Cl YXPSLKXRUCMRIN-UHFFFAOYSA-L 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract description 20
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 abstract description 9
- 238000005229 chemical vapour deposition Methods 0.000 abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 abstract description 7
- 239000011737 fluorine Substances 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 6
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 abstract description 4
- 229910001887 tin oxide Inorganic materials 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- -1 chlorotin trifluoroacetates Chemical class 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- QLWWJOOITQGSQE-UHFFFAOYSA-K dichloro(phenyl)stannanylium;hydroxide Chemical compound [OH-].Cl[Sn+](Cl)C1=CC=CC=C1 QLWWJOOITQGSQE-UHFFFAOYSA-K 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- VBJIFLOSOQGDRZ-UHFFFAOYSA-N (2-chloro-2,2-difluoroacetyl) 2-chloro-2,2-difluoroacetate Chemical compound FC(F)(Cl)C(=O)OC(=O)C(F)(F)Cl VBJIFLOSOQGDRZ-UHFFFAOYSA-N 0.000 description 1
- QRRCTLYMABZQCS-IHWYPQMZSA-N (z)-4,4,4-trifluoro-3-methylbut-2-enoic acid Chemical compound FC(F)(F)C(/C)=C\C(O)=O QRRCTLYMABZQCS-IHWYPQMZSA-N 0.000 description 1
- QVXZSAWOXGFNIK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropan-2-ol Chemical compound FC(F)(F)C(F)(O)C(F)(F)F QVXZSAWOXGFNIK-UHFFFAOYSA-N 0.000 description 1
- XZNOAVNRSFURIR-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol Chemical compound FC(F)(F)C(O)(C(F)(F)F)C(F)(F)F XZNOAVNRSFURIR-UHFFFAOYSA-N 0.000 description 1
- FQDXJYBXPOMIBX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-methylpropan-2-ol Chemical compound FC(F)(F)C(O)(C)C(F)(F)F FQDXJYBXPOMIBX-UHFFFAOYSA-N 0.000 description 1
- OCGWWLDZAFOHGD-UHFFFAOYSA-N 1,1,1-trifluoro-2-methylpropan-2-ol Chemical compound CC(C)(O)C(F)(F)F OCGWWLDZAFOHGD-UHFFFAOYSA-N 0.000 description 1
- GILIYJDBJZWGBG-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-ol Chemical compound CC(O)C(F)(F)F GILIYJDBJZWGBG-UHFFFAOYSA-N 0.000 description 1
- NNZZMYIWZFZLHU-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanol Chemical compound OC(F)(F)C(F)(F)F NNZZMYIWZFZLHU-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- XETRHNFRKCNWAJ-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl 2,2,3,3,3-pentafluoropropanoate Chemical compound FC(F)(F)C(F)(F)C(=O)OC(=O)C(F)(F)C(F)(F)F XETRHNFRKCNWAJ-UHFFFAOYSA-N 0.000 description 1
- WXJFKAZDSQLPBX-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)F WXJFKAZDSQLPBX-UHFFFAOYSA-N 0.000 description 1
- AQQBRCXWZZAFOK-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(Cl)=O AQQBRCXWZZAFOK-UHFFFAOYSA-N 0.000 description 1
- JUGSKHLZINSXPQ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoropentan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)F JUGSKHLZINSXPQ-UHFFFAOYSA-N 0.000 description 1
- XAKMJUAGVWKMOB-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluoropentanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)=O XAKMJUAGVWKMOB-UHFFFAOYSA-N 0.000 description 1
- XCSFZFHJQXODPO-UHFFFAOYSA-N 2,2,3,3-tetrafluorobutanedioyl dichloride Chemical compound ClC(=O)C(F)(F)C(F)(F)C(Cl)=O XCSFZFHJQXODPO-UHFFFAOYSA-N 0.000 description 1
- OAWAZQITIZDJRB-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)Cl OAWAZQITIZDJRB-UHFFFAOYSA-N 0.000 description 1
- RBPHBIMHZSTIDT-UHFFFAOYSA-N 3,3,4,4,5,5,5-heptafluoropentan-2-ol Chemical compound CC(O)C(F)(F)C(F)(F)C(F)(F)F RBPHBIMHZSTIDT-UHFFFAOYSA-N 0.000 description 1
- IHYAGCYJVNHXCT-UHFFFAOYSA-N 3,3,4,4,5,5-hexafluorooxane-2,6-dione Chemical compound FC1(F)C(=O)OC(=O)C(F)(F)C1(F)F IHYAGCYJVNHXCT-UHFFFAOYSA-N 0.000 description 1
- ZLVLNNCBGQYRAB-UHFFFAOYSA-N 3,3,4,4-tetrafluorooxolane-2,5-dione Chemical compound FC1(F)C(=O)OC(=O)C1(F)F ZLVLNNCBGQYRAB-UHFFFAOYSA-N 0.000 description 1
- SZBKCQKJQAYJJN-UHFFFAOYSA-N 4-chloro-1,1,1,2,2,3,3-heptafluorobutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)CCl SZBKCQKJQAYJJN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- GJUGJUBXRVZKGT-UHFFFAOYSA-K [dichloro(phenyl)stannyl] 2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.Cl[Sn+](Cl)C1=CC=CC=C1 GJUGJUBXRVZKGT-UHFFFAOYSA-K 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AFOLZIVGFUUSMF-UHFFFAOYSA-K butyl(dichloro)stannanylium;acetate Chemical compound CCCC[Sn](Cl)(Cl)OC(C)=O AFOLZIVGFUUSMF-UHFFFAOYSA-K 0.000 description 1
- SSQZEQJKXRMDHR-UHFFFAOYSA-K butyltin(3+);2,2,2-trifluoroacetate Chemical compound CCCC[Sn+3].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F SSQZEQJKXRMDHR-UHFFFAOYSA-K 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- UFFSXJKVKBQEHC-UHFFFAOYSA-N heptafluorobutyric anhydride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(=O)OC(=O)C(F)(F)C(F)(F)C(F)(F)F UFFSXJKVKBQEHC-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- CXZGQIAOTKWCDB-UHFFFAOYSA-N perfluoropentanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CXZGQIAOTKWCDB-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical class F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- PDFNMVKYZSDSLJ-UHFFFAOYSA-K trichloro(2-methylpropyl)stannane Chemical compound CC(C)C[Sn](Cl)(Cl)Cl PDFNMVKYZSDSLJ-UHFFFAOYSA-K 0.000 description 1
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/40—Oxides
- C23C16/407—Oxides of zinc, germanium, cadmium, indium, tin, thallium or bismuth
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/004—Aftersun preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
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- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
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- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Chemically Coating (AREA)
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Description
BAKGRUNN FOR OPPFINNELSEN
1. Op<p>finnelsesfelt
Denne oppfinnelsen vedrører organotinn-forbindelser som inneholder fluor, hvilke er anvendelige ved dannelse av fluorbehandlede tinnoksyd-belegg.
2. Beskrivelse av teknikkens stand
Det følgende er henvisninger til teknikkens stand som beskriver forbindelser som er beslektet med dem i foreliggende oppfinnelse, men som imidlertid ikke har de egenskaper som kreves for å danne flytende belegg blandinger for kjemisk dampavsetning.
Menke beskriver i U.S. patent 3.759.743 fremstillingen av ikke-halogenerte organotinntrifluoracetater og blandinger derav i organiske løsningsmidler, så som metyletylketon, for fremstilling av fluorbehandlede tinnoksyd-belegg ved spføyteløsnings-metoden. Disse forstadier har imidlertid en lav flyktighet og er uegnet for den mer fordelaktige kjemiske dampavsetningprosess hvor ikke noe løsningsmiddel er tilsatt.
Wang og Shreeve, beskriver i Chemical Communications (1970) side 151, og J. Organomet. Chem. 38 (1972) side 287, fremstillingen av dialkylklortinn-tri-fluoracetater. Slike forbindelser er uheldigvis faststoffer som ikke kan brukes i kjemisk dampavsetningsprosess.
Plum, et al., beskriver i U.S. patent 4.374.778 fluororgano-tinn-forbindelser, hvori fluoratomet er direkte bundet til tinnatomet.
Franz, et al., omtaler i U.S. patent 4.254.046 dialkyltinn-difluorider for pulveravsetning av fluorbehandlede tinnoksyd-belegg.
Thompson beskriver i fransk patent 1.4 00.314 mono-, di- og trialkyltinn-tri-fluoracetater og deres fremstilling.
Liberte, Reiff og Davidsohn beskriver i Organic Preparation and Procedures 1 (3) 173-176 (1969) fremstillingen av dialkyltinn-polyfluorkarboksylater.
En artikkel i J. Organomet. Chem., (3) 151 (1970), beskriver et dialkylklortinn-trifluormetylacetat.
J. Inorg. Nucl. Chem. 1973, 35(6) 1827-31 beskriver fremstillingen av klortinnkarboksylater ved omsetning av SnCl4 med karboksylsyrer eller deres salter. SN(02CCF3)A ble oppnådd når CF3C02Ag ble anvendt.
J. Organomet. Chem. 49 (1973) 417-424 beskriver masse-spektroskopiske studier av noen faste dimetylklortinnkarboksy-later som viser at de er polymere i fast-fase og beholder en viss polymerkarakter i gass-fasen.
Disse henvisninger beskriver ikke et organotinn-forstadium som er anvendelig for kjemisk dampavsetning, spesielt fra en flytende belegg-blanding. Videre beskriver henvisningene ikke en organotinnforbindelse som har en monoalkyl eller beslektet substituent og minst et kloratom direkte knyttet til tinnatomet, og minst en trifluormetylholdig bestanddel.
Følgelig er et mål for denne oppfinnelsen å frembringe nye og forbedrede organotinn-forbindelser som kan brukes direkte til å danne fluorbehandlede tinnoksydbelegg med lav flateresistans.
Et annet mål er her å frembringe slike forbindelser som kan brukes til å fremstille fluorbehandlede tinnoksyd-belegg ved den kjemiske dampavsetningsmetoden.
Enda et annet mål er her å fremstille monoalkylklortinn-fluoracetater og beslektede forbindelser som med fordel kan brukes i flytende belegg-sammensetninger for kjemiske dampavsetT ning av fluorbehandlede tinnoksyd-belegg.
SAMMENFATNING AV OPPFINNELSEN
Organotinnforbindelsene ifølge oppfinnelsen som inneholder fluor har den generelle formel:
hvor R = alkyl, C1- C6; aryl; eller karbalkoksyalkyl
a = 1; b = 1 eller 2; c = 0 eller 1; d = 0 eller 1;
e = et heltall 0-2; f = 1 eller 2; og n = et heltall 1-6; a + b + c + f = 4.
Tabell I nedenunder sammenfatter forbindelser ifølge oppfinnelsen innenfor den generelle formel for hvert tilfelle av a,b,c,f,d,e og n i slike formler. Reaktantene som ble brukt ved fremstilling av slike forbindelser er også angitt deri.
Følgelig innbefatter de foretrukne forbindelser ifølge oppfinnelsen:
DETALJERT BESKRIVELSE AV OPPFINNELSEN
Forbindelsen ifølge oppfinnelsen kan fremstilles som beskrevet nedenunder.
Generelt reaksionsforløp
tilbakeløp
hvor M<*> er et kation.
Uttrykket "alkyl" slik det her brukes innbefatter rett-kjedede og forgrenede alkylgrupper som har fra 1-6 karbon-atomer.
Følgelig innbefatter representative organotinn-reaktanter som brukes ved fremstilling av forbindelsen ifølge oppfinnelsen monobutyltinn-triklorid, isobutyltinn-triklorid, metyltinn-triklorid, butyldiklortinnacetat og karbetoksyetyltinn-triklorid.
Fluoridreaktanten har en trifluormetyl-gruppe som befinner seg alfa eller beta til en funksjonell gruppe hvor karbon er bundet til oksygen valgt fra karboksylsyre, anhydrid, syrehalogenider eller alkohol.
Følgelig innbefatter egnede fluorreaktanter de følgende:
Karboksylsyrer
trifluoreddiksyre
klordi fluoreddiksyre
difluoreddiksyre
heptafluorsmørsyre
pentafluorpropionsyre
3-trifluormetylkrotonsyre
nonafluorpentansyre
Anhvdrider
trifluoreddiksyreanhydrid
heptafluorsmørsyreanhydrid
pentafluorpropionsyreanhydrid
klordifluoreddiksyreanhydrid
perfluorglutarsyreanhydrid
perfluorravsyreanhydrid
Syrehalogenider
heptafluorbutylklorid
perfluorglutarylfluorid
perfluoroktanoylklorid
perfluorsuccinylklorid
Alkoholer
2,2,2-trifluoretanol
1H,lH-heptafluorbutanol-1
3,3,4,4,5,5,5-heptafluorpentanol-2
heptafluorisopropanol
heksafluor-2-metylisopropanol
1H,1H,5H-oktafluor-l-pentanol
perfluor-t-butanol
2-trifluormetylepropanol-2
1,1,1-trifluorpropanol-2
perfluoretanol
I den foretrukne utførelsesform av oppfinnelsen omsettes monobutyltinn-triklorid med et salt av trifluoreddiksyre under dannelse av butyldiklortinn-trifluoracetat.
Oppfinnelsen skal illustreres med de følgende eksempler.
EKSEMPEL 1
Reaksjonsprodukt av monobutyltinn- triklorid og trifluoreddiksyre. Fremstilling av monobutvldiklortinn- trifluoracetat.
A. En reaksjonsblanding av monobutyltinn-triklorid (MBTC)
(8,46 g. 0,03 mol, 71,2 vekt%) og trifluoreddiksyre (TFA) (3,42 g. 0,03 mol, 28,8 vekt%), KOH (2,08 g. 0,03 mol), 15 ml H20, 50 ml eter, 50 ml metyletylketon (MEK) og 0,1 g
C16H3(CH3)3N<+>Br" som faseoverføringskatalysator (N+Br") ble fremstilt ved å oppløse KOH'et i vann og tilsette TFA; separat fylle inn MBTC'et, eter og MEK og tilsette N<+>Br'<1> deretter tilsette den andre løsning til den første løsning; oppvarme til tilbakeløp under røring under et nitrogenteppe, og tilbakeløpskoking ved 48°C i 2 timer.
Etter henstand natten over dannedes vann og organiske faser; vannfasen var et klart, fargeløst nedre skikt, og den organiske fasen var et klart gult øvre skikt. Det organiske skiktet ble konsentrert og resten plassert i en vakuum-eksikator natten over. Utbyttet var 9,60 gram brunt viskøst flytende monobutyldiklortinn-trifluoracetat (89 % utbytte). Analyse. Sn 33 %, 36 % faktisk; Cl. 20 %, 21 % faktisk.
B. En reaksjonsblanding av monobutyltinn-triklorid (200 g. , 0,7 mol) og natriumsaltet av trifluoreddiksyre (10 g., 0,07 mol) ble oppvarmet ved 70°C i 3 timer og fikk stå natten over ved romtemperatur. Natriumklorid biproduktet og ikke omsatt natriumsalt ble filtrert. En flytende overtrekks-blanding av ca. 12 vekt% monobutyldiklortinn-trifluoracetat og 88 vekt% monobutyltinn-triklorid.
EKSEMPEL 2
Reaksjonsprodukt av monofenvldiklortinnhydroksyd og trif luoreddiksyre. Fremstilling av monofenyldiklortinn-trifluoracetat
En reaksjonsblanding av monofenyldiklortinnhydroksyd (9,0 g, 0,03 mol) og trifluoreddiksyre (3,42 g, 0,03 mol) ble fremstilt som i eksempel 1 og tilbakeløpskokt i 2 timer og ga 81 % av det ønskede produkt.
EKSEMPEL 3
Eksperimentet fra eksempel 2 ble gjentatt ved å bruke ammoniumsaltet av trifluoreddiksyre med lignende resultater.
EKSEMPEL 4
Fremstilling av fluor- behandlede tinnoksvdbelegg
En flytende beleggblanding fra eksempel IB bile brukt for å fremstille fluorbehandlede tinnoksydbelegg på glass ved kjemisk dampavsetning. Gjennomsiktige, slørfrie belegg med en tykkelse på 200 nm erholdtes på 2 sekunders avsetningstid ved 650°C i en vannholdig luftatmosfaere. Flateresistansen var ca. 40 ohm pr. kvadrat; den infrarøde reflektivitet var mer enn 70 % ved 10 mikron, og den synlige transmisjon var større enn 70 %.
Claims (7)
1. Forbindelse med formelen
hvor:
R er alkyl; aryl eller karbalkoksyalkyl;
a = 1
b = 1 eller 2
c = 0 eller 1
d = 0 eller 1
e = et heltall 0-2 f = 1 eller 2
n = et heltall 1-6, oga + b + c+ f = 4
2. Forbindelse ifølge krav 1 hvor R er Cx - C6 alkyl.
3. Forbindelse ifølge krav 1 som er butyldiklortinn-trifluoracetat.
4. Forbindelse ifølge krav 1, som er butylklortinn-bis-trifluoracetat.
5. Forbindelse ifølge krav 1, som er butylklortinn-acetattrifluoracetat.
6. Forbindelse ifølge krav 1, som er karbetokysetyldiklor-tinntrifluoracetat.
7. Forbindelse ifølge krav 1, som er butyldiklortinn-trifluoretoksyd.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/888,298 US4731462A (en) | 1986-07-18 | 1986-07-18 | Organotin compounds containing fluorine useful for forming fluorine-doped tin oxide coating |
| PCT/US1987/001746 WO1988000588A1 (en) | 1986-07-18 | 1987-07-17 | Organotin compounds containing fluorine useful for forming fluorine-doped tin oxide coating |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO881186L NO881186L (no) | 1988-03-17 |
| NO881186D0 NO881186D0 (no) | 1988-03-17 |
| NO171068B true NO171068B (no) | 1992-10-12 |
| NO171068C NO171068C (no) | 1993-01-20 |
Family
ID=25392934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO881186A NO171068C (no) | 1986-07-18 | 1988-03-17 | Fluorholdige organotinn-forbindelser som er anvendelige for fluorforsterkede tinnoksydbelegg |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4731462A (no) |
| EP (1) | EP0318486B1 (no) |
| JP (1) | JPH02500974A (no) |
| KR (1) | KR900003453B1 (no) |
| CN (1) | CN1051088C (no) |
| AT (1) | ATE63918T1 (no) |
| AU (1) | AU609734B2 (no) |
| BR (1) | BR8707749A (no) |
| CA (1) | CA1276160C (no) |
| DE (1) | DE3770472D1 (no) |
| DK (1) | DK167875B1 (no) |
| EG (1) | EG19792A (no) |
| ES (1) | ES2007080A6 (no) |
| IL (1) | IL83178A (no) |
| IN (1) | IN168762B (no) |
| NO (1) | NO171068C (no) |
| TR (1) | TR24843A (no) |
| WO (1) | WO1988000588A1 (no) |
| ZA (1) | ZA875095B (no) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4325648C1 (de) * | 1993-07-30 | 1994-09-08 | Goldschmidt Ag Th | Alkylzinnverbindungen, deren Herstellung und diese enthaltende Mittel zur Bildung elektrisch leitfähiger und IR-reflektierender Schichten auf Oberflächen von Glas, Glaskeramik oder Email |
| DE4433206A1 (de) * | 1994-09-17 | 1996-03-21 | Goldschmidt Ag Th | Verfahren zur pyrolytischen Beschichtung von Glas-, Glaskeramik- und Emailprodukten |
| US5725904A (en) * | 1995-06-02 | 1998-03-10 | Elf Atochem North America, Inc. | Liquid methyltin halide compositions |
| US5698262A (en) * | 1996-05-06 | 1997-12-16 | Libbey-Owens-Ford Co. | Method for forming tin oxide coating on glass |
| FR2795745B1 (fr) * | 1999-06-30 | 2001-08-03 | Saint Gobain Vitrage | Procede de depot d'une couche a base de tungstene et/ou de molybdene sur un substrat verrier, ceramique ou vitroceramique, et substrat ainsi revetu |
| ATE492034T1 (de) | 2002-10-25 | 2011-01-15 | Nakajima Glass Co Inc | Herstellungsverfahren für solarbatteriemodule |
| JP4290194B2 (ja) * | 2004-04-27 | 2009-07-01 | 中島硝子工業株式会社 | 太陽電池モジュールの製造方法 |
| US7947374B2 (en) * | 2009-02-19 | 2011-05-24 | Guardian Industries Corp. | Coated article with sputter-deposited transparent conductive coating capable of surviving harsh environments, and method of making the same |
| US8097342B2 (en) * | 2009-02-19 | 2012-01-17 | Guardian Industries Corp. | Coated article with sputter-deposited transparent conductive coating capable of surviving harsh environments, and method of making the same |
| US20100209730A1 (en) * | 2009-02-19 | 2010-08-19 | Guardian Industries Corp., | Coated article with sputter-deposited transparent conductive coating for refrigeration/freezer units, and method of making the same |
| US10228561B2 (en) * | 2013-06-25 | 2019-03-12 | Microsoft Technology Licensing, Llc | Eye-tracking system using a freeform prism and gaze-detection light |
| US9625723B2 (en) * | 2013-06-25 | 2017-04-18 | Microsoft Technology Licensing, Llc | Eye-tracking system using a freeform prism |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1495783A1 (de) * | 1964-03-07 | 1969-04-03 | Hoechst Ag | Verfahren zur Herstellung von Polyaethylenterephthalat |
| US3836444A (en) * | 1968-10-01 | 1974-09-17 | Inst Francais Du Petrole | Process for polymerizing conjugated diolefins using organic compounds of the transition metals as catalysts |
| US3781315A (en) * | 1971-07-09 | 1973-12-25 | Prod Res & Chem Corp | Halo alkoxy metal compounds |
| US3775453A (en) * | 1972-03-14 | 1973-11-27 | Schaper | Preparation of hexafluoroisopropoxides of aluminum and group iv elements |
| DE3010077C2 (de) * | 1980-03-15 | 1981-07-30 | Vereinigte Glaswerke Gmbh, 5100 Aachen | Verfahren zum Aufbringen von mit einem Halogen, vorzugsweise mit Fluor dotierten Zinnoxidschichten auf Glasoberflächen durch Pyrolyse |
-
1986
- 1986-07-18 US US06/888,298 patent/US4731462A/en not_active Expired - Lifetime
-
1987
- 1987-07-13 ZA ZA875095A patent/ZA875095B/xx unknown
- 1987-07-13 IL IL83178A patent/IL83178A/xx unknown
- 1987-07-13 EG EG40987A patent/EG19792A/xx active
- 1987-07-16 IN IN550/CAL/87A patent/IN168762B/en unknown
- 1987-07-17 CA CA000542377A patent/CA1276160C/en not_active Expired - Lifetime
- 1987-07-17 JP JP62504611A patent/JPH02500974A/ja active Granted
- 1987-07-17 WO PCT/US1987/001746 patent/WO1988000588A1/en active IP Right Grant
- 1987-07-17 ES ES8702098A patent/ES2007080A6/es not_active Expired
- 1987-07-17 AT AT87905098T patent/ATE63918T1/de not_active IP Right Cessation
- 1987-07-17 DE DE8787905098T patent/DE3770472D1/de not_active Expired - Fee Related
- 1987-07-17 CN CN87104911A patent/CN1051088C/zh not_active Expired - Fee Related
- 1987-07-17 KR KR1019880700299A patent/KR900003453B1/ko not_active IP Right Cessation
- 1987-07-17 AU AU77837/87A patent/AU609734B2/en not_active Ceased
- 1987-07-17 EP EP87905098A patent/EP0318486B1/en not_active Expired - Lifetime
- 1987-07-17 TR TR87/0502A patent/TR24843A/xx unknown
- 1987-07-17 BR BR8707749A patent/BR8707749A/pt not_active IP Right Cessation
-
1988
- 1988-03-11 DK DK137088A patent/DK167875B1/da active
- 1988-03-17 NO NO881186A patent/NO171068C/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IN168762B (no) | 1991-06-01 |
| TR24843A (tr) | 1992-06-19 |
| DE3770472D1 (de) | 1991-07-04 |
| JPH0575756B2 (no) | 1993-10-21 |
| CA1276160C (en) | 1990-11-13 |
| DK137088D0 (da) | 1988-03-11 |
| CN87104911A (zh) | 1988-05-11 |
| NO881186L (no) | 1988-03-17 |
| ZA875095B (en) | 1988-01-13 |
| DK137088A (da) | 1988-03-11 |
| AU7783787A (en) | 1988-02-10 |
| NO171068C (no) | 1993-01-20 |
| DK167875B1 (da) | 1993-12-27 |
| AU609734B2 (en) | 1991-05-09 |
| CN1051088C (zh) | 2000-04-05 |
| KR880701724A (ko) | 1988-11-04 |
| JPH02500974A (ja) | 1990-04-05 |
| WO1988000588A1 (en) | 1988-01-28 |
| EG19792A (en) | 1996-02-29 |
| IL83178A0 (en) | 1987-12-31 |
| EP0318486B1 (en) | 1991-05-29 |
| ES2007080A6 (es) | 1989-06-01 |
| EP0318486A1 (en) | 1989-06-07 |
| NO881186D0 (no) | 1988-03-17 |
| IL83178A (en) | 1992-02-16 |
| US4731462A (en) | 1988-03-15 |
| KR900003453B1 (ko) | 1990-05-19 |
| BR8707749A (pt) | 1989-08-15 |
| ATE63918T1 (de) | 1991-06-15 |
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