DE19649954A1 - Fluoralkyl-funktionelle Organosiloxan-haltige Zusammensetzungen auf Alkoholbasis, Verfahren zu deren Herstellung sowie deren Verwendung - Google Patents
Fluoralkyl-funktionelle Organosiloxan-haltige Zusammensetzungen auf Alkoholbasis, Verfahren zu deren Herstellung sowie deren VerwendungInfo
- Publication number
- DE19649954A1 DE19649954A1 DE19649954A DE19649954A DE19649954A1 DE 19649954 A1 DE19649954 A1 DE 19649954A1 DE 19649954 A DE19649954 A DE 19649954A DE 19649954 A DE19649954 A DE 19649954A DE 19649954 A1 DE19649954 A1 DE 19649954A1
- Authority
- DE
- Germany
- Prior art keywords
- fluoroalkyl
- mono
- group
- branched
- alkyl group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 27
- 230000008569 process Effects 0.000 title claims abstract description 15
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000007519 polyprotic acids Polymers 0.000 claims abstract description 13
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000008043 acidic salts Chemical class 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 6
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 230000007062 hydrolysis Effects 0.000 claims abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000002585 base Substances 0.000 claims description 16
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 14
- 150000001282 organosilanes Chemical class 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 7
- 239000005871 repellent Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- -1 basic salt magnesium hydroxide Chemical class 0.000 claims description 3
- 239000004566 building material Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000003365 glass fiber Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 230000002940 repellent Effects 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 239000002966 varnish Substances 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000004971 Cross linker Substances 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 229940009827 aluminum acetate Drugs 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 230000006872 improvement Effects 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000002444 silanisation Methods 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 238000003756 stirring Methods 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000003980 solgel method Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940089951 perfluorooctyl triethoxysilane Drugs 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- AVYKQOAMZCAHRG-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AVYKQOAMZCAHRG-UHFFFAOYSA-N 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- 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
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/24—Coatings containing organic materials
- C03C25/40—Organo-silicon compounds
-
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
-
- 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
-
- 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
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
- D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
- D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H19/32—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming a linkage containing silicon in the main chain of the macromolecule
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/16—Sizing or water-repelling agents
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Textile Engineering (AREA)
- Inorganic Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Wood Science & Technology (AREA)
- General Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Paints Or Removers (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19649954A DE19649954A1 (de) | 1996-12-03 | 1996-12-03 | Fluoralkyl-funktionelle Organosiloxan-haltige Zusammensetzungen auf Alkoholbasis, Verfahren zu deren Herstellung sowie deren Verwendung |
| JP9229241A JPH10158521A (ja) | 1996-12-03 | 1997-08-26 | アルコールを基礎とするオルガノポリシロキサン含有組成物、該組成物の製造法並びに該組成物の使用法 |
| DE59701107T DE59701107D1 (de) | 1996-12-03 | 1997-10-11 | Fluororgano-funktionelle Siloxan-haltige Zusammensetzungen auf Alkoholbasis, Verfahren zu deren Herstellung sowie deren Verwendung |
| EP97117643A EP0846715B2 (de) | 1996-12-03 | 1997-10-11 | Verfahren zur Herstellung fluoralkyl-funktioneller Organopoly-siloxan-haltiger Zusammensetzungen auf Alkolholbasis und Verwendung des Verfahrensproduktes |
| DK97117643T DK0846715T4 (da) | 1996-12-03 | 1997-10-11 | Fluororgano-funktionelle, siloxanholdige sammensætninger på alkoholbasis, fremgangsmåde til deres fremstilling samt deres anvendelse |
| AT97117643T ATE189688T1 (de) | 1996-12-03 | 1997-10-11 | Fluororgano-funktionelle siloxan-haltige zusammensetzungen auf alkoholbasis, verfahren zu deren herstellung sowie deren verwendung |
| ES97117643T ES2143827T5 (es) | 1996-12-03 | 1997-10-11 | Procedimiento para la fabricacion de composiciones basadas en alcohol, con funciones fluoroalquilo y contenido en organosiloxano y uso del producto del procedimiento. |
| KR1019970065124A KR100548658B1 (ko) | 1996-12-03 | 1997-12-02 | 알콜을기재로하는플루오로알킬관능성오가노실록산함유조성물및이의제조방법 |
| US08/984,162 US6177582B1 (en) | 1996-12-03 | 1997-12-03 | Fluoroalkyl-functional organosiloxane-containing compositions based on alcohol, a process for their preparation and their use |
| US09/685,341 US6713186B1 (en) | 1996-12-03 | 2000-10-11 | Fluoroalkyl-functional organosiloxane-containing compositions based on alcohol, a process for their preparation and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19649954A DE19649954A1 (de) | 1996-12-03 | 1996-12-03 | Fluoralkyl-funktionelle Organosiloxan-haltige Zusammensetzungen auf Alkoholbasis, Verfahren zu deren Herstellung sowie deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19649954A1 true DE19649954A1 (de) | 1998-06-04 |
Family
ID=7813404
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19649954A Withdrawn DE19649954A1 (de) | 1996-12-03 | 1996-12-03 | Fluoralkyl-funktionelle Organosiloxan-haltige Zusammensetzungen auf Alkoholbasis, Verfahren zu deren Herstellung sowie deren Verwendung |
| DE59701107T Expired - Lifetime DE59701107D1 (de) | 1996-12-03 | 1997-10-11 | Fluororgano-funktionelle Siloxan-haltige Zusammensetzungen auf Alkoholbasis, Verfahren zu deren Herstellung sowie deren Verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59701107T Expired - Lifetime DE59701107D1 (de) | 1996-12-03 | 1997-10-11 | Fluororgano-funktionelle Siloxan-haltige Zusammensetzungen auf Alkoholbasis, Verfahren zu deren Herstellung sowie deren Verwendung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6177582B1 (enExample) |
| EP (1) | EP0846715B2 (enExample) |
| JP (1) | JPH10158521A (enExample) |
| KR (1) | KR100548658B1 (enExample) |
| AT (1) | ATE189688T1 (enExample) |
| DE (2) | DE19649954A1 (enExample) |
| DK (1) | DK0846715T4 (enExample) |
| ES (1) | ES2143827T5 (enExample) |
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| DE10104394A1 (de) * | 2001-01-19 | 2002-08-01 | Salzenbrodt Gmbh & Co Kg | Imprägniermittel |
| DE10258352A1 (de) * | 2001-12-14 | 2003-07-17 | Schott Glas | Verfahren zum Beschichten von Glasfasern |
| DE102008047306A1 (de) | 2008-09-16 | 2010-04-15 | JODLAUK, Jörg | Zusammensetzung temper- und sinterbarer Überzugsmassen |
| DE102009023497A1 (de) | 2009-06-02 | 2010-12-09 | Nanogate Ag | Glasurzusammensetzung mit Glasplättchen verschiedener Größe |
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| US6541671B1 (en) | 2002-02-13 | 2003-04-01 | The Regents Of The University Of California | Synthesis of 2H- and 13C-substituted dithanes |
| US6564935B1 (en) | 1999-11-04 | 2003-05-20 | Nippon Sheet Glass Co., Ltd. | Coating solution, method and kit for preparing the same, and method for water-repellent treatment using the same |
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| DE102008041920A1 (de) | 2008-09-09 | 2010-03-11 | Evonik Degussa Gmbh | Neue Katalysatoren für die Vernetzung von funktionellen Silanen oder funktionellen Siloxanen, insbesondere mit Substraten |
| ATE555172T1 (de) * | 2008-10-16 | 2012-05-15 | Nanogate Ag | Silangemisch |
| DE102009017822A1 (de) | 2009-04-20 | 2010-10-21 | Evonik Degussa Gmbh | Wässrige Silansysteme basierend auf Tris(alkoxysilylalkyl)aminen und deren Verwendung |
| KR101500327B1 (ko) * | 2013-04-11 | 2015-03-10 | 주식회사 오앤에스 | 콘 구조의 형태를 갖는 폴리실록산, 초소수성 표면을 갖는 적층체 및 상기 적층체의 제조방법 |
| EP3445737A1 (en) | 2016-04-20 | 2019-02-27 | Dow Silicones Corporation | Lithium alkylsiliconate composition, coating, and method of making same |
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| US20210032498A1 (en) * | 2019-08-01 | 2021-02-04 | The Boeing Company | Hydrophobic-icephobic organosilane compositions, coatings, and methods |
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| GR20220100627A (el) | 2022-08-01 | 2024-03-12 | Παπαδοπουλος Νικολαος-Ξαφακης Σωτηριος Ομορρυθμη Εταιρεια, | Μεθοδος αναπτυξης προστατευτικων και ευκολα καθαριζομενων νανοεπικαλυπτικων συστηματων υψηλης αντοχης για πολλαπλα υποστρωματα |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5266222A (en) * | 1990-05-23 | 1993-11-30 | California Institute Of Technology | Durable low surface-energy surfaces |
| EP0629673B1 (en) * | 1991-01-23 | 2002-05-02 | Matsushita Electric Industrial Co., Ltd. | Water- and oil-repelling adsorbed film |
| JPH05170486A (ja) * | 1991-12-25 | 1993-07-09 | Central Glass Co Ltd | ガラス表面用撥水処理剤およびその撥水処理ガラス |
| JP3367572B2 (ja) * | 1993-12-08 | 2003-01-14 | 日本板硝子株式会社 | 撥水被膜の形成方法 |
| JP3269314B2 (ja) * | 1994-01-31 | 2002-03-25 | 信越化学工業株式会社 | 撥水処理剤 |
| SG83635A1 (en) * | 1994-08-30 | 2001-10-16 | Xaar Ltd | Coating, coating composition and method of forming coating |
| DE4443825A1 (de) * | 1994-12-09 | 1996-06-13 | Huels Chemische Werke Ag | Wasserbasierende Organopolysiloxan-haltige Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
| JP3196621B2 (ja) * | 1995-04-20 | 2001-08-06 | 信越化学工業株式会社 | 水溶性表面処理剤 |
| JPH09176622A (ja) * | 1995-12-25 | 1997-07-08 | Toshiba Silicone Co Ltd | 撥水剤組成物 |
| FR2746811B1 (fr) * | 1996-04-02 | 1998-04-30 | Saint Gobain Vitrage | Composition pour un revetement non-mouillable, procede de traitement d'un vitrage a l'aide de la composition et produits obtenue |
-
1996
- 1996-12-03 DE DE19649954A patent/DE19649954A1/de not_active Withdrawn
-
1997
- 1997-08-26 JP JP9229241A patent/JPH10158521A/ja active Pending
- 1997-10-11 ES ES97117643T patent/ES2143827T5/es not_active Expired - Lifetime
- 1997-10-11 DK DK97117643T patent/DK0846715T4/da active
- 1997-10-11 DE DE59701107T patent/DE59701107D1/de not_active Expired - Lifetime
- 1997-10-11 AT AT97117643T patent/ATE189688T1/de not_active IP Right Cessation
- 1997-10-11 EP EP97117643A patent/EP0846715B2/de not_active Expired - Lifetime
- 1997-12-02 KR KR1019970065124A patent/KR100548658B1/ko not_active Expired - Fee Related
- 1997-12-03 US US08/984,162 patent/US6177582B1/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6251989B1 (en) | 1998-05-26 | 2001-06-26 | Degussa-Huels Aktiengesellschaft | Oligomerized organopolysiloxane cocondensate, its production and its use for treatment of surfaces |
| DE10104394A1 (de) * | 2001-01-19 | 2002-08-01 | Salzenbrodt Gmbh & Co Kg | Imprägniermittel |
| DE10258352A1 (de) * | 2001-12-14 | 2003-07-17 | Schott Glas | Verfahren zum Beschichten von Glasfasern |
| DE10258352B4 (de) * | 2001-12-14 | 2004-01-29 | Schott Glas | Verfahren zum Beschichten von Glasfasern sowie Verwendung der beschichteten Glasfasern |
| DE102008047306A1 (de) | 2008-09-16 | 2010-04-15 | JODLAUK, Jörg | Zusammensetzung temper- und sinterbarer Überzugsmassen |
| DE102009023497A1 (de) | 2009-06-02 | 2010-12-09 | Nanogate Ag | Glasurzusammensetzung mit Glasplättchen verschiedener Größe |
| DE102009023497B4 (de) * | 2009-06-02 | 2012-04-19 | Nanogate Ag | Glasurzusammensetzung mit Glasplättchen verschiedener Größe, Verfahren zu deren Herstellung, Verfahren zur Herstellung von glasierter Sanitärkeramik sowie Verwendung der Glasurzusammensetzung |
Also Published As
| Publication number | Publication date |
|---|---|
| DK0846715T3 (da) | 2000-06-26 |
| ES2143827T5 (es) | 2004-06-16 |
| US6177582B1 (en) | 2001-01-23 |
| EP0846715B2 (de) | 2003-12-03 |
| DK0846715T4 (da) | 2004-04-13 |
| JPH10158521A (ja) | 1998-06-16 |
| ES2143827T3 (es) | 2000-05-16 |
| EP0846715A2 (de) | 1998-06-10 |
| EP0846715B1 (de) | 2000-02-09 |
| ATE189688T1 (de) | 2000-02-15 |
| KR19980063670A (ko) | 1998-10-07 |
| KR100548658B1 (ko) | 2006-06-28 |
| DE59701107D1 (de) | 2000-03-16 |
| EP0846715A3 (de) | 1998-08-05 |
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