TW506972B - Process for preparing fluoroalkyl-containing organosilicon compounds - Google Patents
Process for preparing fluoroalkyl-containing organosilicon compounds Download PDFInfo
- Publication number
- TW506972B TW506972B TW086110794A TW86110794A TW506972B TW 506972 B TW506972 B TW 506972B TW 086110794 A TW086110794 A TW 086110794A TW 86110794 A TW86110794 A TW 86110794A TW 506972 B TW506972 B TW 506972B
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- Taiwan
- Prior art keywords
- group
- patent application
- platinum
- general formula
- alkyl
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- 150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 32
- 125000003709 fluoroalkyl group Chemical group 0.000 title abstract description 19
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 14
- 239000011737 fluorine Substances 0.000 claims abstract description 14
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 13
- 239000011541 reaction mixture Substances 0.000 claims abstract description 9
- 150000001336 alkenes Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 16
- -1 alkyl organosilicon compounds Chemical class 0.000 claims description 13
- 150000003377 silicon compounds Chemical class 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000002131 composite material Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- DPYXSRCCHQQIGT-UHFFFAOYSA-N O1CCCCC1.[Pt] Chemical compound O1CCCCC1.[Pt] DPYXSRCCHQQIGT-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 238000011049 filling Methods 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000001165 gas chromatography-thermal conductivity detection Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DTDFWYZVBJYVPL-UHFFFAOYSA-N 3-(1,1,2,2-tetrafluoroethoxy)prop-1-ene Chemical compound FC(F)C(F)(F)OCC=C DTDFWYZVBJYVPL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910004721 HSiCl3 Inorganic materials 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000002079 cooperative effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000003058 platinum compounds Chemical class 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- ICSWLKDKQBNKAY-UHFFFAOYSA-N 1,1,3,3,5,5-hexamethyl-1,3,5-trisilinane Chemical compound C[Si]1(C)C[Si](C)(C)C[Si](C)(C)C1 ICSWLKDKQBNKAY-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- FYQFWFHDPNXORA-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C FYQFWFHDPNXORA-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- DAYVBIXMFTUYIG-UHFFFAOYSA-N C(=C)[SiH](N([Si](C)(C)C)C)C=C.[Pt] Chemical compound C(=C)[SiH](N([Si](C)(C)C)C)C=C.[Pt] DAYVBIXMFTUYIG-UHFFFAOYSA-N 0.000 description 1
- 229910002621 H2PtCl6 Inorganic materials 0.000 description 1
- 102100030500 Heparin cofactor 2 Human genes 0.000 description 1
- 101001082432 Homo sapiens Heparin cofactor 2 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- PIZSEPSUZMIOQF-UHFFFAOYSA-N platinum;2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound [Pt].C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 PIZSEPSUZMIOQF-UHFFFAOYSA-N 0.000 description 1
- 229920001709 polysilazane Polymers 0.000 description 1
- 239000005053 propyltrichlorosilane Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- WPPVEXTUHHUEIV-UHFFFAOYSA-N trifluorosilane Chemical compound F[SiH](F)F WPPVEXTUHHUEIV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
- D06M13/517—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond containing silicon-halogen bonds
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/4922—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as monomers, i.e. as organosilanes RnSiX4-n, e.g. alkyltrialkoxysilane, dialkyldialkoxysilane
- C04B41/4933—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as monomers, i.e. as organosilanes RnSiX4-n, e.g. alkyltrialkoxysilane, dialkyldialkoxysilane containing halogens, i.e. organohalogen silanes
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
-
- 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
- C23C30/00—Coating with metallic material characterised only by the composition of the metallic material, i.e. not characterised by the coating process
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/657—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing fluorine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Ceramic Engineering (AREA)
- Structural Engineering (AREA)
- Inorganic Chemistry (AREA)
- Metallurgy (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Description
經濟部中央標準局員工消費合作社印製 506972 A7 ______ B7 五、發明説明(,) 本發明是關於一種在鉑觭媒存在的情況下使含氟烯煙 與含至少一値H-Si基之有機矽化合物反應以製備含氟烷 基之有機矽化合物之方法。 本發明同時也提出此類含氟烷基之有機矽化合物之應 用。 近年來,基於氟烷基氣矽烷及氟烷基院氣矽烷之待殊 性質,其已經大量的出現在各類嶄新的應用場合當中。 這些化合物偽做為界面活性劑使用,例如為強化透鏡及 光纖表面所用之潤滑劑,氟樹脂之底塗層,化妝品製劑 之成分,氟橡膠及矽_橡謬之改質劑,及用以製造防油 -,防污及防水表面之添加劑。 大家都知道,鉑化合物可做為含氟烯烴與上述矽烷的 氫矽烷化反應之觸媒使用。其中所使用的化合物為氧化 態( + 4)鉑。然而,這些觸媒糸統在反應過程中卻出現若 干缺點。 在很多情況下,上述反應只可能在密閉条統中操作。 JP 021 78292 A2 中提出 F3 C(CF2 ) C (CF 3 ) 2 CH 2 CH : CH2與HSiCl3之反應僳在H2 PtCl6觸媒存在的情況下 於吹製玻璃管中進行,該反應以1 〇〇 C之溫度進行3小時之 後得到的産率為83%。EP 0538061 A2中提出 CF 3 CF2 CF2 0CF(CF3 )CF2 〇CF2 CF2 CH: CH 2 1¾ CH3SiHCl2之反應傺在h2 PtCl6觸媒存在的情況下於鋼 製高壓釜中進行,該反應以1 2 0 1C之溫度進行2 0小時之 後得到的産率為67%。 本纸張尺度適用中國國家標準(CNS ) Α4規格(210 X 297公釐) j 碰—I (請先閲讀背面之注意事項再填寫本頁)
、1T 舞 A7 B7 五、發明説明C>) … 在大氣壓下,此類反應的反應時間是相當長的。例如 J P 0 6 , 2 3 9 , 8 7 2號中提出在H2 PtCl6觸媒存在的情況下 C 3 F 7 0[CF(CF 3 )0] 3 CF(CF 3 )CH:CH 2 與(CH2)3_nSiHCln U=1,2)之反應•該反應以150*0之®度進行48 小時之後得到的産率為89%。W0 94/ 20442提出一種氣 矽烷化反應,該反應在Η 2 PtCl 6 «媒存在的情況下以 100¾之溫度進行50小時之後得到的産率為88%。此外 ,W0 94/20442 中也指出,p-CF3 C6 H4 CH: CH2 與 CH3SiHCl2之反應可能會發生異構化,而導致在氫矽 烷化反應過程中選擇率的降低;在情況下,産率為89% ,/3-矽烷化氟烯烴α-矽烷化氟烯烴之比約為87: 13。 為提高選擇率及反應性,在很多情況下是添加複合劑 到鉑觸媒中,有時候這樣做同時也能夠提高铂化合物之 溶解度。例如,在JP 03,1 06,889 Α2中是添加丙酮,ΕΡ 0 466 958 Α1是添加異丙醇,ΕΡ 0 573 282 Α1則提出 在2 -乙基己醛中H2PtCl6之用法,其中另外還提出添 加間二甲苯六氟化物到鉑觸媒之方法。以上所舉各例, 製造費用及複雜度都相當高。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 上述觸媒条統的反應性及選擇率都不盡令人滿意, 因此,從經濟的觀點來看,要以此類方法來製備含氟烷 基之有機矽化合物很難引起人家的興趣。 DE-A 19 41 411, FR-A2 474和 US 3 775 452中提出 ICARSTEDT型鈉觸媒。此類觸媒與磺框架結構者相比較, 很明顯的具備較高之穩定性(在氧化基質中尤其穩定), 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 506972 B7 五、發明説明(今) 較高及較少的異構化效果。此類觸媒的應用例子為矽酮 類之製備及改質。 本發明的目的是提供一種簡單經濟的製備含氟烷基之 有機矽化合物之方法,本發明特別考慮到要如何提高含 氟烯烴與含H-Si基之有機矽化合物之催化反應之産率。 我們出乎意料的發現能夠利用含氟烯煙與含至少一値 H-Si基之有機矽化合物之催化反應簡單經濟的製備含氟 烷基之有機矽化合物,該反應偽在鉑(0)複合觸媒存在的 情況下進行,並且能夠從反應混合物中回收含氣烷基之 有機矽化合物。因此根據本發明方法,其傑出的回收含 氟烷基之有機矽化合物之方法使得産率能夠高達99%。 因此,本發明傜提供一種利用含氣烯烴與含至少一個 H-Si基之有機矽化合物之反應製備含氟烷基之有機矽化 合物之方法,該反應僳在鉑(0)複合觸媒存在的情況下 進行,並且能夠從反應混合物中回收含氟烷基之有機矽 化合物。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 在本發明新穎方法中,較佳的觸媒是KARSTEDT型鉑(0) 複合觸媒。此類觸媒中鉑之含量一般是在0.01-20重量% 之間,而以0*1-1腫量%為較佳,又以0.5-5重量%為特 佳。關於觸媒,較佳的例子包括:雙〔1,3-雙(η -2-乙 烯基)-1,1,3,3,-四甲基二矽氣烷〕鉑(0),三苯基膝_ 〔1,3 -雙U -2 -乙烯基)-1,1,3,3,-四甲基二矽氧烷〕 鉑(0), 2,4,6,8-四乙烯基-2,4,6,8-四甲基環四矽氧烷 鉑(0),在本發明方法中,觸媒条統可溶在溶劑中,該 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 506972
A7 B7 五、發明説明(4 ) 溶劑在反應過程中實質上是惰性的,此類溶劑的例子包 括甲苯和二甲苯。 在本發明方法中,偽使用至少一値如通式(I)、所示之 含氟烯烴進行反應: R1YmCH=CH2 (I) 其中,R1為單寡-或金氟化芳基或含1-9個磺原子之單-, 寡-或全氟化院基,Y為-CH2 -0 -或基,m為0或1。 例如 CF3 (C F 2 ) π CH : CH 2 ,其中 n=3, 5, 7 和 9; HCF2 CF2 〇CH2 CH: CH 2 , R f CH 2 CH 2 〇(C : 0) (C (CH 3 )) :C H 2 ,其中 R eCn F,丄,,n = 2 - 1 8 〇 2n+l 關於含至少一個Η-Si基之有機矽化合物,最好是使用 如通式(I I)所示之氫矽院進行反應: H(“.b>SiR2aXb (II) 其中,R2相同與否均可,並且像代表芳基(以苯基為 較佳)或含卜20個碩原子之烷基(以甲基或乙基為較佳), X為C 1或Br , a = 0,1,2 或 3,1) = 0,1,2 或 3,並且 IS (a + b)S3, 或如通式(III)所示之二矽氣烷: 經濟部中央標準局員工消費合作社印装 (請先閱讀背面之注意事項再填寫本頁) R'AH^SiOSi Hp^b)R2A (III) 其中,R2相同與否均可,並且像代表芳基(以苯基為 較佳)或含1-20個碩原子之烷基(以甲基或乙基為較佳), X為C 1或Br , a = 0,1或 2 ,b=0,l 或 2 ,並且 lS(a + b)S2, 或如通式(IV)所示之環矽氣烷: 本紙張尺度適用中國國家標準(CNS ) A4規格(21〇X:297公釐) 506972 A7 B7 五、發明説明(r ) (R2ASi?)抓㈣ Si0)y (1 v ) 其中,R2相同與否均可,並且偽代表芳基(以苯基為 較佳)或含1-20個磺原子之烷基(以甲基或乙基為較佳), X為C 1或B r , a = 0,1 或 2 b=0,l 或 2 ,並且 a + b = 2, X代表0-5之數字, s = 0 或 1 , t = 0 或 1,並且 OS (s + t)Sl, y代表1-5之數字,並且3S(x + y)蠤5, 或如通式(V)所示之線性聚矽氣烷混合物: RV^SiCHRV^SiO^RV^HSiO)rSiR2,Xb (V ) 其中,R2相同與否均可,並且僳代表芳基(以苯基為 較佳)或含1-20個碩原子之烷基(以甲基或乙基為較佳), X為C 1或Br , a = 0,1,2 或 3,b=0,l,2 或 3,並且 a + b=3, f=0,l 或2 ,而i=0,l或2,並且f + i= 2, q ^ 0 , s=0或 1, t=0 或 1,並且 0S(s + t)Sl, r ^ 1 , 並且 505(9 4)5 50,000,而以 5,000-10,000 為較佳。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 如此,在本發明中使用含至少一個H-Si基之有機矽化 合物是可行的,例如HSiCl3,HSiCH3Cl2或 HS i (CH 3 ) 2 C1〇 一般而言,在本發明方法中,偽將含氟烯烴裝入一可 加熱或冷卻之攪拌槽中,槽中具備攪拌設備及回流冷凝 器,並且可在氮氣氛中操作,加入此槽中的鉑(0)觸媒 最好是溶在溶劑中。 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 506972 經濟部中央標準局員工消費合作社印製 Α7 Β7 五、發明説明(b ) 在本發明方法中,鉑觸媒用量對如通式I所示起始材 料之重量比是以1 : 1 0 0 - 1 : 1 0 0 , 0 0 0為較佳,而以1 : 1 , 0 〇 〇 -1: 30,000 為更佳,又以 1: 5,000-1: 2 0,000 為特佳。 接著即可利用計量裝置將含至少一値H-Si基之有機矽 化合物饋入反應槽中。 含至少一値H-Si基之有機矽化合物一般是在室溫下添 加。在添加過程中所放出的熱可用來建立本發明反應之 反應溫度。因此本發明方法即使在大氣壓下也不霈要熱 源,而設備的投資相對的就比較低。而且由於一般都不 霈用到過量的含至少一個H-Si基之有機矽化合物,因此 原來在反應之後必須另外處理的副産物及殘留化合物之 比率也跟著能夠降到最少程度。 在本發明方法中(500ml實驗室規模),含至少一個H-Si 基之有機矽化合物之添加時間一般是在20 - 1 20分鐘之間 ,而以30 -60分鐘之間為較佳。而攪拌通常會再繼鑛1 -5 小時。 在本發明方法中,反應溫度是以1〇-20〇υ為較佳,而 以20-1 50 1為特佳。反應壓力是以1-50巴(絶對壓力)為 較佳,而以1-10巴為更佳。 接著卽對在本發明方法中製得之反應混合物進行回收 含氟烷基之有機矽化合物之步驟。例如利用蒸餾方法。 如此,根據本發明方法即可簡單而經濟的製得例如3, 3,4,4,5,5,6,6,7,7,8,8,9,9,10 ,10,10-十七氟辛基三 氣矽烷,3,3,4,4 ,5,5,6,6,7,7,8,8,8-十三氟辛基甲基 本紙張尺度適用中國國家標準(CNS ) Α4規格(210 X 297公釐) (請先閲讀背面之注意事項再填寫本頁) 訂 506972 . . A7 . B7 五、發明説明(7 ) 、 二氣矽烷及3-(1,1,2,2 -四氣乙氧基)丙基三氯矽烷。 本發明方法的優點是可在溫和的反應條件下進行含氣 烷基之有機矽化合物之合成反應,並且,還具備高産率及 高選擇性,而且使甩的是低濃度的觸媒。在本發明方法 中,例如與三氛矽烷,烷基氛矽烷,或芳基氯矽烷之加 成反應之過程中雙鍵的異構化反應,或氟烷基自由基之 異構化反應一般而言是不可能發生的。另外,反應時間 短及反應能夠均勻的進行也可算本發明之優點。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 在上述氫矽烷化反應中於鉑(0)複合觸媒(尤其是 KARSTEDT型)存在的情況下所製得的含氟烷基之有機矽 化合物,其中包括額外再含至少一値C卜Si基或Br-Si基 者,可利用醇類(例如甲醇,乙醇,正丙醇,異丙醇,正 丁醇,異丁醇,第三丁醇或2 -甲氣乙醇予以酯化而得到 對應的烷氣基矽化合物。在此情況下,上述製備含氟烷 基之有機矽化合物之程序中製得之反應混合物不必預先 蒸餾純化即可直接做為Cl-Si基或Br-Si基與醇類之傳統 酯化反應之起始材料使用。一般而言酯化步驟是沒有任 何問題存在的。利用簡單的蒸餾方法即可分離出任何殘 留的高揮發性成分,以面積GC-TCD方法(利用熱導率偵 測器偵測所得在層析圖中積分尖峰面積之百分比)測知 可獲得純度98.5-99,9%之含氟烷基或含氧烷基之有機 砂化合物,例如3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛 基甲基二氣矽烷。本發明不僅效率高而且成本甚低。 因此,本發明也提供如通式(VI)所示含氟烷基之有機 本紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) 經濟邰t夹樣隼局貝工消費合作杜印¾ 506972 . &年•—r A7..... __ Ί ., i B7____ 五、發明説明(《) 矽化合物之製法: R1-Ym-(CH2)2SiHaR2b(〇R3)(3.a.b) (VI) 其中,R1為單寡-或全氟化芳基或含1-9值磺原子 之單寡-或全氣化烷基,且以CF3 (CF2)7 -, CF 3 (C 6 Η 4 ) - , C 6 F ^ , R f CH 2 CH 2 (C:0)-(其中 IU =CnF 2n+1,n = 2 - 1 8 )為佳; Y為CH 2 , 0或S基。 R2為芳基或含1-8値碩原子之烷基, R3為芳基或含1-8傾磺原子之烷基, a=0, 1 或 2, b=0,1 或 2,並且 a + bS2, 此製法之步驟包括使含至少一個C卜Si基或B「- Si基之 含氟烷基之有機矽化合物與一元醇反應,然後從反應混 合物中回收如通式(VI)所示含氟烷基之有機矽化合物。 本發明另外還提供使用KARSTEDT型觸媒製備如申請專 利範圍第1-15項中任何一項之含氟烷基之有機矽化合物 之方法。 本發明另外還提供以如申請專利範圍第1-15項中任何 一項之含氣烷基之有機矽化合物做為織物用肋劑或織物 用助劑之製劑之應用,以如申請專利範圍第1-15項中任 何一項之含氟烷基之有機矽化合物來強化塑膠,玻璃, 金颶,陶瓷及石頭表面或做為這些強化表面之製劑,以 如申請專利範圍第1-15項中任何一項之含氟烷基之有機 矽化合物做為建築防腐劑或建築防腐劑之製劑。 以下將藉肋各實施例對本發明做更詳盡之說明。 -10- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) (請先閲讀背面之注意事項再填寫本頁) ί® 裝. 、11 506972 ' A7 B7 五、發明説明(?) 實施例 實施例1 於氮氣氣氛中將126克(0.8莫耳)1,1,2,2 -四氟乙基烯 丙基醚裝入一具有頂部水冷凝器,磁攪拌器,溫度計及 滴液漏斗之5 00ml三頸玻璃燒瓶中,然後加入0.4克CPC 〇72(溶於二甲苯中之鉑(0)-二乙烯基四甲基二矽氣烷; 濃Pt : 1 , 1 , 2 , 2-四氟乙基烯丙基醚=1 : 20 , 000 ) 〇接箸 於室溫下滴入108克(0.8莫耳)三氣矽烷之後予以攪拌80 分鐘。此時立卽發生放熱反應,而使得溫度升高到11 〇 υ 。當各反應物都添加完成之後,反應混合物再繼缠攪拌1 小時,然後進行氣相層析(GC)分析。經一短管柱蒸餾塔 純化之後獲得225(0, 77莫耳)3-(1, 1,2,2-四氟乙氧基) 丙基三氣矽烷(産率:96%,純度:>98面積%GC-TCD)。 實施例2 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 於氮氣氣氛中將192克(0.55莫耳)3,3,4,4,5,5,6,6,7,7 ,8,8,8-十三氟辛烯裝入一具有頂部水冷凝器,磁攪拌 器,溫度計及滴液漏斗之500ml三頸玻璃燒瓶中,然後 加入0.3克CPC 072(溶於二甲苯中之鉑(0)_二乙烯基四 甲基二矽氧烷;濃Pt: 1,1,2,2-四氟乙基烯丙基醚= 1: 20,000)。接著於室溫下滴入80克(0.59莫耳)三氣矽 烷之後予以攪拌85分鐘。此時立即發生放熱反應,而使 得溫度升高到1151C。當各反應物都添加完成之後,反 應混合物再繼缠攪拌1 . 5小時,然後進行GC分析。經一 短管柱蒸餾塔純化之後獲得262克(0.54莫耳)3,4,4,5,5 -11- 本紙張尺度適用中國國家標準(CNS ) A4規格(210 X 297公釐) 506972 A7 B7 五、發明説明(1。) ,6,6,7,7, 8,8,8 -十三氟辛基三氛矽烷(産率:99%,純 度:>97面積 %GC-TCD)。 實施例3 同時將1 2 3克(0 · 5莫耳)3,3 , 4,4,5,5,6,6,6 -九氟B烯 7 6克(〇.5莫耳)三氛矽烷及〇.34克0?(: 0 7 2 (溶於二甲苯中 之鉑(〇)-二乙烯基四甲基二矽氧烷;濃Pt: I,1,2,2-四 氟乙基烯丙基醚=1:20, 〇〇〇)裝入一 250nl實驗室级銷高 壓釜中β關閉高壓釜之後隨即在一油浴中以70分鐘的時 間加熱姪140 W。約8分鐘之後開始發生放熱反應,而使 得混合物溫度升高到165 °C。然後冷卻,將反應器排空, 進行短管柱蒸餾之後獲得17 6克(0·46莫耳)3, 4,4, 5, 5,6, 6,6-九氟己基三氯矽院(産率:90%,純度:>98面積% GC-TCD) 〇 實施例4 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 將544克(1·83莫耳)3"*(1,1,2,2-四氣乙氣基)丙基二 氣矽烷裝入一具有頂部水冷凝器,磁搜拌器,溫度計及 滴液漏斗之三頸玻璃燒中,然&以6·5小時的 時間摄拌滴入256克(5.57莫耳)乙醇。此時立即發生放 熱反應,而使得溫度升高到110 °C。然後再以90分鐘的 時間加入165克^0£1溶液(21%,溶於乙醇中)。冷卻之 後濾掉所形成的NaC1,涌胃一 $管柱蒸蒸、 後獲得519克(1·61莫耳)3-(1,1,2,2 -四氟乙氣基)丙基 三乙氣基矽烷(産率:90%,純度:>97面積%GC-TCD)〇 -12- 本紙張纽適财關_ ( CNS ) A4驗(21G X297公釐)
Claims (1)
- 506972 公告本 91. 8. 1修正 子月曰六、申請專利範圍 第861 10794號「製備含氟烷基有機矽化合物之方法」專利案 (91年8月14日修正) 六申請專利範圍: 1. 一種製備具有通式(VI)之含氟烷基有機矽化合物之方 法,其係在鉑觸媒存在下,使含氟烯烴與具有至少含 有一個H-Si基之有機矽化合物反應,其包括在鉑含 量在0.01-20重量%間之鉑(〇)複合觸媒存在之下,於 10〜200°C間之反應溫度、1〜50巴(絕對壓力)間之壓力 下來進行該反應,以及從反應合物中收取具有通式 (VI)之含氟烷基有機矽化合物; R1-Ym-(CH2)2SiHaR2b(OR3)(3.a.b) (VI) 其中,Ri爲單_,寡-或全氟化芳基或含1-9個碳原 子之單-,寡-或全氟化烷基,且 γ爲CH2,0或S基。 R2相同與否均可,爲芳基或含1-8個碳原子之烷基, R3爲芳基或含1-8個碳原子之烷基,且 m爲0或1,a=0,l或或2,並且 a + b S 2, 其中含氟烯烴係具有通式(I) R'YmCH^ CH2 ( I ) 其中,R1爲單-,寡-或全氟化芳基或含1-9個碳原 子之單-,寡-或全氟化烷基,γ爲_CH2-,-0-,-〇-CH2-或基,m爲〇或1;或具有如下通式之含氟506972 六、申請專利範圍 烯烴, CF3(CF2)nCH = CH2 其中n = 3、5、7及9 ; 其中使用的鉑(0)複合觸媒爲KARSTEDT型之自雙 〔1,3 -雙(;/ -2·乙烯基)-1,1,3,3,-四甲基二矽氧 烷〕鉑(0)、三苯基膦-〔1,3-雙(7? -2 -乙烯基)一 1,1,3,3,-四甲基二矽氧烷〕鉑(〇)、及2,4,6,8-四乙 烯基- 2,4,6,8 -四甲基環四矽氧烷鉑(〇)中選取的觸 媒,並且鉑觸媒用量對如通式(I )所示起始材料之重 量比是在1 : 100-1 : 100,000之間。 2 .如申請專利範圍第1項之方法,其中有機矽化合物係 如以下通式(11 )所示之氫矽烷進: H(4.a-b)SiR2aXb (Π) 其中,R2相同與否均可,並且係代表芳基或含丨-20 個碳原子之院基, X爲C1或Br, a =0,1,2 或 3,b=〇,l,2 或 3,並且 l$(a + b)S 3 ° 3 .如申請專利範圍第1項之方法,其中有機矽化合物係 如通式(Π I )所示之二矽氧烷: R2aXbH(3.a.b)SiOSiH(3.a.b)R2aXb (III) 其中,R2相同與否均可,並且在係代表芳基或含^ 20個碳原子之烷基, 506972 六、申請專利範圍 X爲C1或Br, a·二 〇,1 或 2 ,b二 0,1 或 2,並且 l$(a + b)S2。 4 .如申請專利範圍第1項之方法,其中有機矽化合物係 如通式(I v )所示之環砂氧院: (R2aXbSi〇)x(R2sXtH(2-s-t)SiO)y (IV) 其中,R2相同與否均可,並且係代表芳基或含1-20 個碳原子之烷基, X爲C1或Br, a =0,1 或 2,b=〇,l 或 2,並且 a + b=2, X代表0-5之數字, s =0 或 1 ,t =〇 或 1,並且 〇^(s + t)Sl, y代表1-5之數字,並且3$(x + y)S5。 5 ·如申請專利範圍第1項之方法,其中有機矽化合物係 如通式(V )所示之線性聚矽氧烷混合物: R2aXbSiO(R2fX1SiO)q(R2sXtH(2.s.t)SiO)rSiR2aXb (V) 其中,R2相同與否均可,並且係代表芳基或含1-20 個碳原子之烷基, X爲C1或Br, a =0,1,2 或 3,b二 〇,1,2 或 3,並且 a + b=3, ί^Ο,Ι 或 2 ,而 i=0,l 或 2,並且 qg〇,s=0 或 1,1:=0 或 1,並且 〇S(s + t)$l, r- 1,並且 50S U+r) $ 50,〇〇〇。 6 ·如申請專利範圍第1至5項中任一項之方法,其中反 506972 、申請專利範圍 應溫度是在20 - 1 50°C之間。 7.如申1靑專利$0圍弟1項之方法’其中反應壓力是在1· 1 0巴(絕對壓力)之間。 8 ·如申請專利範圍第1項之方法,其包括含氟烷基有 機矽化合物與醇類反應以產製對應的含烷氧有機矽化 合物,該含氟垸基有機矽化合物係爲至少含有一個 Cl-Si或Br-Si基含氟烷基有機矽化合物,以及在 P t ( 0 )複合觸媒存在之下,依照申請專利範圍第1至 7項中任一項之方法之羥矽烷化反應所產製之含氟烷 基有機矽化合物。
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-
1996
- 1996-10-26 DE DE19644561A patent/DE19644561C2/de not_active Expired - Fee Related
-
1997
- 1997-07-29 TW TW086110794A patent/TW506972B/zh not_active IP Right Cessation
- 1997-08-27 JP JP23075397A patent/JP4217283B2/ja not_active Expired - Fee Related
- 1997-08-30 DE DE59709679T patent/DE59709679D1/de not_active Expired - Lifetime
- 1997-08-30 ES ES97115056T patent/ES2191796T3/es not_active Expired - Lifetime
- 1997-08-30 EP EP97115056A patent/EP0838467B1/de not_active Expired - Lifetime
- 1997-08-30 AT AT97115056T patent/ATE236170T1/de not_active IP Right Cessation
- 1997-10-21 US US08/955,290 patent/US5869728A/en not_active Expired - Lifetime
- 1997-10-23 CN CN97121473A patent/CN1180706A/zh active Pending
- 1997-10-24 CA CA002219606A patent/CA2219606A1/en not_active Abandoned
- 1997-10-24 KR KR1019970054586A patent/KR100581155B1/ko not_active IP Right Cessation
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1998
- 1998-12-09 US US09/207,988 patent/US6255516B1/en not_active Expired - Lifetime
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DE59709679D1 (de) | 2003-05-08 |
DE19644561A1 (de) | 1998-04-30 |
US6255516B1 (en) | 2001-07-03 |
KR100581155B1 (ko) | 2006-09-06 |
EP0838467A1 (de) | 1998-04-29 |
JPH10130278A (ja) | 1998-05-19 |
ES2191796T3 (es) | 2003-09-16 |
DE19644561C2 (de) | 2003-10-16 |
CN1180706A (zh) | 1998-05-06 |
JP4217283B2 (ja) | 2009-01-28 |
US5869728A (en) | 1999-02-09 |
CA2219606A1 (en) | 1998-04-26 |
EP0838467B1 (de) | 2003-04-02 |
KR19980033125A (ko) | 1998-07-25 |
ATE236170T1 (de) | 2003-04-15 |
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