CA2010969C - Organosilane coating compositions - Google Patents
Organosilane coating compositionsInfo
- Publication number
- CA2010969C CA2010969C CA002010969A CA2010969A CA2010969C CA 2010969 C CA2010969 C CA 2010969C CA 002010969 A CA002010969 A CA 002010969A CA 2010969 A CA2010969 A CA 2010969A CA 2010969 C CA2010969 C CA 2010969C
- Authority
- CA
- Canada
- Prior art keywords
- epoxycyclohexyl
- coating composition
- group
- glycidoxypropyl
- antistatic coating
- 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.)
- Expired - Fee Related
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 59
- 150000001282 organosilanes Chemical class 0.000 title description 5
- -1 organosilane compound Chemical class 0.000 claims abstract description 69
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
- 239000011248 coating agent Substances 0.000 claims abstract description 21
- 238000000576 coating method Methods 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 21
- RGPUVZXXZFNFBF-UHFFFAOYSA-K diphosphonooxyalumanyl dihydrogen phosphate Chemical compound [Al+3].OP(O)([O-])=O.OP(O)([O-])=O.OP(O)([O-])=O RGPUVZXXZFNFBF-UHFFFAOYSA-K 0.000 claims abstract description 18
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 13
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 11
- 150000001399 aluminium compounds Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 27
- 230000007062 hydrolysis Effects 0.000 claims description 24
- 238000006460 hydrolysis reaction Methods 0.000 claims description 24
- 238000006068 polycondensation reaction Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 15
- 239000002798 polar solvent Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000012454 non-polar solvent Substances 0.000 claims description 6
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- UWGJCHRFALXDAR-UHFFFAOYSA-N diethoxy-ethyl-methylsilane Chemical compound CCO[Si](C)(CC)OCC UWGJCHRFALXDAR-UHFFFAOYSA-N 0.000 claims description 5
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 claims description 5
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 claims description 5
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 claims description 5
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 claims description 5
- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-UHFFFAOYSA-N 0.000 claims description 5
- FKDLBUPSJQZYFZ-UHFFFAOYSA-N ethoxy-ethyl-dimethylsilane Chemical compound CCO[Si](C)(C)CC FKDLBUPSJQZYFZ-UHFFFAOYSA-N 0.000 claims description 5
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 claims description 5
- HTSRFYSEWIPFNI-UHFFFAOYSA-N ethyl-dimethoxy-methylsilane Chemical compound CC[Si](C)(OC)OC HTSRFYSEWIPFNI-UHFFFAOYSA-N 0.000 claims description 5
- SUHRFYWSDBWMFS-UHFFFAOYSA-N ethyl-methoxy-dimethylsilane Chemical compound CC[Si](C)(C)OC SUHRFYWSDBWMFS-UHFFFAOYSA-N 0.000 claims description 5
- MDLRQEHNDJOFQN-UHFFFAOYSA-N methoxy(dimethyl)silicon Chemical compound CO[Si](C)C MDLRQEHNDJOFQN-UHFFFAOYSA-N 0.000 claims description 5
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 5
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 claims description 5
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 claims description 5
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 claims description 4
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 229940072049 amyl acetate Drugs 0.000 claims description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 3
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 3
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
- 229940011051 isopropyl acetate Drugs 0.000 claims description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 3
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- RPUZVWKKWXPKIP-UHFFFAOYSA-H dialuminum;hydrogen phosphate Chemical group [Al+3].[Al+3].OP([O-])([O-])=O.OP([O-])([O-])=O.OP([O-])([O-])=O RPUZVWKKWXPKIP-UHFFFAOYSA-H 0.000 claims 4
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 claims 4
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 claims 3
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 239000011147 inorganic material Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000007769 metal material Substances 0.000 abstract description 2
- 239000011368 organic material Substances 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910008051 Si-OH Inorganic materials 0.000 description 4
- 229910006358 Si—OH Inorganic materials 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000011083 cement mortar Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- WHGNXNCOTZPEEK-VIFPVBQESA-N dimethoxy-methyl-[3-[[(2r)-oxiran-2-yl]methoxy]propyl]silane Chemical compound CO[Si](C)(OC)CCCOC[C@H]1CO1 WHGNXNCOTZPEEK-VIFPVBQESA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LBDROUOCQSGOFI-UHFFFAOYSA-N methanol;phosphoric acid Chemical compound OC.OP(O)(O)=O LBDROUOCQSGOFI-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- 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
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/91—Antistatic compositions
- Y10S524/912—Contains metal, boron, phosphorus, or silicon
Abstract
An antistatic coating composition comprising:
(a) a reaction product of phosphoric acid and an aluminium compound, particularly preferably aluminium dihydrogenphosphate;
(b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(c) a second organosilane compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent.
The coating compoisition has a long pot life to be stably stored for a long period of time, and may be coated on any of usual materials including metallic, inorganic and organic materials to form a cured coating film which is excellent in resistance to heat, durability, water-proof property and resistance to chemicals by heating at a relatively low temerature for a short time.
Also provided is an improved process for preparing such a coating composition.
(a) a reaction product of phosphoric acid and an aluminium compound, particularly preferably aluminium dihydrogenphosphate;
(b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(c) a second organosilane compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent.
The coating compoisition has a long pot life to be stably stored for a long period of time, and may be coated on any of usual materials including metallic, inorganic and organic materials to form a cured coating film which is excellent in resistance to heat, durability, water-proof property and resistance to chemicals by heating at a relatively low temerature for a short time.
Also provided is an improved process for preparing such a coating composition.
Description
TITLE OF THE INVENTION:
Organosilane coating Composition BACKGROUND OF THE INVENTION:
Field of the Invention;
The present invention relates generally to a coating composition.
More particularly, it relates to a novel organosilane coating composition which is adapted to be coated on a metallic materials, such as iron, stainless steel and aluminium or alloys thereof, and other inorganic and organic materials including cement mortar, glass, wood and synthetic resins to form a cured coating film which is excellent in resistance to heat, durability, water-proof property and resistance to chemicals by heating at a relatively low temerature for a short time.
Statement of Related Prior Art:
A process has hitherto been known for preparing a coating composition containing the products of hydrolysis and subsequent partial condensation of silane compounds, wherein the silane compound is dissolved in a solvent miscible with water, such as ethanol, and then subjected to hydrolysis and partial condensation by the catalytic action of an acid in the presence of water.
The known acids generally used as the catalyst in the known process include hydrochloric acid, sulfuric acid and phosphoric acid. However, the use of such mineral acids 2C ~ 969 is detrimental to the properties of the resultant coating composition. For example, when hydrochloric acid is used as the catalyst, hydrochloric ions are not incorporated in the condensation product of silane to be left in the form of free ions to cause electrolytic corrosion. On the other hand, when phosphoric acid is used, although phosphoric ions are incorporated in the condensation product of silane, adhesiveness of the resultant coating composition is becomes inferior or the storage stability thereof becomes poor to shorten the pot life of the coating composition.
There is a demand for an improved antistatic coating composition which can be stored stably for a long period of time and forms a cured coating film having excellent properties, particularly satisfactory antistatic property and high adhesive strength to protect the material coated therewith reliably.
OBJECTS AND SUMMARY OF THE INVENTION: -Accordingly, the primary object of this invention is to provide an antistatic coating composition for forming a cured coating film which is improved in resistance to heat, durability, water-proof property and resistance to chemicals.
Another object of this invention is to provide an antistatic coating composition which is improved in adhesiveness to form a tough coating on a variety of materials including metals and synthetic resins.
~201 0969 A further object of this invention is to provide an antistatic coating composition which can be stored stably for a prolonged period of time and forms an electrically insulating and antistatic coating film by heating at a relatively low temperature.
A still further object of this invention is to provide a process for preparing such a coating composition.
After eager pursuits for preparing an antistatic coating composition, it has been found that an organosilane coating composition having a long pot life and forming a tough coating can be prepared by combining particular hydrolyzable organosilane compounds and then co-polycondensing the products of hydrolysis in the presence of a reaction product of phosphoric acid and an aluminium compound, preferably in the presence of aluminium dihydrogenphosphate. The hydrolysis and subsequent co-polycondensation take place on the material coated with the coating composition of this invention by heating at a relatively low temperature.
More specifically, this invention provides an antistatic coating composition comprising:
(a) a reaction product of phosphoric acid and an aluminium compound:
(b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(c) a second organosilane compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent.
In the most preferred embodiment, the reaction product of phosphoric acid and an aluminium compound is aluminium dihydrogenphosphate.
According to a further aspect of this invention, provided is a process for the preparation of an antistatic coating composition containing products of hydrolysis and subsequent polycondensation of first and second organosilane compounds, said first organosilane compound having at least one epoxy group and a hydrolyzable alkoxy group and said second organosilane compound having two or more hydrolyzable alkoxy groups, and said partial hydrolysis and subsequent polycondensation being carried out in the presence of at least water, an organic solvent and a catalyst which is a reaction product of phosphoric acid and an aluminium compound, most preferably aluminium dihydrogenphosphate.
In yet another aspect, the present invention provides an antistatic coating composition comprising:
(a) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(b) a second organosilane compound having no epoxy group and two or more hydrolyzable alkoxy groups; (c) 2 to 20 wt%, based on the total weight of said first and second organosilane compounds, of aluminum dihydrogenphosphate;
and (d) 50 to 500 parts by weight, based on the total weight of said first and second organosilane compounds, of an organic solvent for said first and second organosilane compounds, wherein said first organosilane compound and said second organosilane compound are present in an amount effective to provide an antistatic coating.
In yet another aspect, the present invention provides, in a process for the preparation of an antistatic coating composition containing products of hydrolysis and subsequent polycondensation of first and second organosilane compounds, said first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group and said second organosilane compound having no epoxy group and two or more hydrolyzable alkoxy groups, and said hydrolysis and subsequent polycondensation being carried out in the presence of water, an organic solvent and a catalyst, the improvement which comprises said catalyst is aluminum dihydrogenphosphate, wherein said first organosilane compound and said second organosilane compound are present in an amount effective to provide an antistatic coating.
DESCRIPTION OF PREFERRED EMBODIMENT:
The present invention will now be described in detail.
As aforementioned, the antistatic coating composition of this invention comprises the four components of (a) a reaction product of phosphoric acid and an aluminium compound (b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group: (c) a second organosilane 4a , .
.
compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent. The most important feature of the invention is the use of a reaction product of phosphoric acid and an aluminium compound, most preferably aluminium dihydrogenphosphate, which acts as a catalyst for hydrolysis and subsequent co-polycondensation and is incorporated into the molecules of the resultant co-polycondensation product.
Although details of the partial hydrolysis and subsequent co-polycondensation reactions of the first and second organosilane compounds, which take place in the presence of aluminium ~ihydrogenphosphate, have not been fully clarified, it is estimated that the following reactions take place during the heating step effected after the coating composition is coated on a sheet or surface to be coated with the protective coating film.
OR' OR' OH
R-Si(OR')2 > R-Si-OH + R-Si-oH + R-Si-OH
H OR' OH OH
OH R R R
R-Si-OH ~ -Si-O-Si-O-Si-OH OH OH OH
OR' f O \ ~ OR' O \
R-Si-OR' + HO-P-O Al ~ R-Si-o-P-O Al OR' \ 1H ~ 3 \ OR~ OH 3 R R R OH OH
-Si-O-Si-O-Si-O- + HO-P-O-Al-O-P-OH
OH OH OH O O O
HO-P=O
OH
R
--si--o--O O O O
> R-Si-O-P-O-Al-O-P-O-Si-R
Il l I I
1 0 ~ ~ O ~
HO-P=O Si OH R
In the reaction formulae set forth above, R and R' each stands for an alkyl group.
When aluminium dihydrogenphosphate (Al(H2PO4)3) is used as the catalyst, a commercially available 20 to 50%
aqueous solution thereof may be used. The quantity o~
aluminium dihydrogenphosphate added in the composition of this invention ranges, preferably, from 2 to 20~ by weight, based on the total weight of the first and second organo-silane compound contained in the composition. If the added quantity of aluminium dihydrogenphosphate is less than 2~ by weight, the rates of hydrolysis and subsequent co-polycondensation become too low to increase the period of time required for setting or curing the coating composition;
whereas if the added quantity of aluminium dihydrogen-2 0 1 0 9 6 ~
phosphate is more than 20~ by weight, the rates ofhydrolysis and subsequent co-polycondensation become too high to make it impossible to control the reactions and there arises adverse tendency of gelation of the coating composition.
The first organosilane compound, which may be used in the present invention, include those represented by the following formula of:
CH2-CH-CH2-O(CH2)3Si(OR)3;
wherein R is an straight-chain alkyl group having 1 to 2 carbon atoms.
Specific examples of the first organosilane compound are as follows:
~ -glycidoxypropyl trimethoxysilane;
\2 / 2 2 2 2 ( 3)3 r-glycidoxypropyl methyldimethoxysilane;
CH2-CHCH2OCH2CH2CH2Si(OCH3)2 ~-glycidoxypropyl dimethylmethoxysilane;
CH2 -CHCH20CH2CH2CH2SiOCH3 ~-glycidoxypropyl triethoxysilane;
CH -cHcH2ocH2cH2cH2si(oc2 5)3 ~-glycidoxypropyl methyldiethoxysilane;
CH2-CHCH2OCH2CH2CH2Si(OCH3)2 ~-glycidoxypropyl dimethylethoxysilane;
CH2-CHCH2OCH2CH2CH2Si(OCH3)3 ~-(3,4-epoxycyclohexyl)ethyltrimethoxysilane;
O- C - CH
HC CHCH2CH2Si(OCH3)3 H C - CH
~-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane;
H
O- C - CH CH
I / \2 1 3 HC / 2 2 ( 3)2 H C - CH
~-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane;
H
HC CHCH2CH2SiOCH3 r ~-(3,4-epoxycyclohexyl)ethyltriethoxysilane;
H
O- C - CH
HC CHcH2cH2si(oc2H5)3 ~-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane:
H
HC CHcH2cH2si(oc2H5)2 ~-(3,4-epoxycyclohexyl)ethyldimethylethoxysilane:
H
and mixtures thereof.
It is possible to use co-polycondensation products prepared by hydrolysis of any one or more of the first organosilane compounds set forth above and subsequent partial co-polycondensation of the products of the hydrolysis.
The second organosilane compounds, which may be preferably used in the composition of this invention include those represented by the following formula of:
CH3Si(OR)3:
wherein R is a straight-chain alkyl group having 2Q~9~i9 1 to 2 carbon atoms.
Specific examples of the second organosilane compounds are methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, orthomethyl silicate, orthoethyl silicate and mixtures thereof.
It is possible to use co-polycondensation products prepared by hydrolysis of any one or more of the second organosilane compounds set forth above and subsequent partial co-polycondensation of the products of hydrolysis.
The organic solvent used in the composition of this invention is a solvent for the organosilane compounds, the solvent being miscible with water. The organic solvent serves to dissolve and disperse the used catalyst, preferably aluminium dihydrogenphosphate, and to properly control the hydrolysis and subsequent polycondensation reactions. Although it is preferred to use a polar solvent, a mixture of a polar solvent with a non-polar solvent may also be used.
Specific examples of the polar solvent, which may be used in the composition of this invention, are alcohols such as methanol, ethanol, isopropanol, n-butanol and _ 2 0 1 0 9 6 g isobutanol; ether alcohols such as ethyleneglycol monomethyl ether, ethyleneglycol monoethyl ether and ethyleneglycol monobutyl ether; esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, amyl acetate, ethyleneglycol monomethyl ether acetate and ethyleneglycol monoethyl ether acetate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and diacetone alcohol;
and mixtures thereof. The most preferable polar solvent is methanol, since it is inexpensive and perfectly miscible with water.
Specific examples of preferable non-polar solvent, which may be added to the polar solvent, are hexane, heptane, octane and mixtures thereof. Although an aromatic compound such as toluene and xylene may be added to the polar solvent, it is desirable that the aromatic compound be used as little as possible since the coating composition becomes cloudy when a large amount thereof is added.
The content of the organic solvent ranges preferably from 50 to 500 parts by weight, based on the total weight of the first and second organosilane compounds.
If the content of the organic solvent is less than 50 parts by weight, the viscosity of the resultant coating composition becomes too high and the pot life of the composition is shortened. On the contrary, although the pot life of the resultant coating composition can be prolonged 20 t 0 9 6 9 by adding 500 parts by weight or more of the organic solvent, the viscosity of the composition becomes too low and makes it difficult to form a coating film having a sufficient thickness.
Water contained in the coating composition of this invention is normally supplied as water used for dissolving aluminium dihydrogenphosphate. However, water may be added as desired to prepare a coating composition having a proper VlS COS 1 ty.
EXAMPLE
The present invention will now be described more specifically with reference to an example thereof. However, it is to be noted hereby that the following example is given by way of example only and thus the invention should not be limited thereby, the scope of the invention being defined by the appended claims.
A coating composition was prepared by mixing the components, as will be set forth below, and the mixture was allowed to stand at room temperature for 24 hours:
Methyltrimethoxysilane 25g ~-Glycidoxypropyltrimethoxysilane 25g 50 wt% Aqueous Solution of Aluminium lOg Dihydrogenphosphate Methanol 50g The following are the properties of the thus pre-pared coating composition and the coating film after curing.
~ 20 1 0 9 6 9 Properties of the Coating Composition:
Specific Gravity: 0.939 (at 25~C) Viscosity: 3.5 cp. (at 25~C) Properties of the Cured Coating Film:
Condition for Curing Pencil Hardness 25~C, 1 hr. 3H
25~C, 24 hrs. 6H
70~C, 2 hrs. 5H
100~C, 2 hrs. 9H
Surface Resistivity:
The surface resistivity of a cured coating film applied on an acrylic resin plate was measured by the method stipulated in JIS K 6911 to find that the surface resistivity was 1.0 x 10 ohm.cm.
The coating composition was applied on plates, respectively, made of an ABS resin, PZ, Teflon (Trade Mark) and PVC, and the surface resistivities of the cured coating films were measured. The results were substantially equivalent to that of the coating film applied on the acrylic resin plate.
Antistatic Property:
The coating composition was applied on an acrylic resin plate and then cured. The antistatic property of the cured coating film was measured by the JIS L-1094 method to obtain the following results (the results being expressed by the half-value periods of the 20 ~ 0969 initial values when an electric potential of 10 KV was applied). The results revealed that the cured coating films formed by the use of the coating composition of the invention exhibited superior antistatic effects.
Equivalent results were obtained when the coating composition was applied, respectively, on different substrates made of PVC, PZ, Teflon (Trade Mark) and ABS.
Normal Condition (25~C, 55% RH*) 1.0 sec.
25~C, 30% RH* 5.0 sec.
After being treated at 70~C for 100 hrs. 11.9 sec.
*Note: RH = Relative Humidity As will be seen from the data given above, the coating composition of the invention forms a cured coating film superior over that obtainable by the conventional technology.
Although the invention has been described with reference to a presently preferred embodiment, many modifications and alternations may be conceived by a person having ordinary skill in the art without departing from the spirit and scope of the invention which is defined in the appended claims.
Organosilane coating Composition BACKGROUND OF THE INVENTION:
Field of the Invention;
The present invention relates generally to a coating composition.
More particularly, it relates to a novel organosilane coating composition which is adapted to be coated on a metallic materials, such as iron, stainless steel and aluminium or alloys thereof, and other inorganic and organic materials including cement mortar, glass, wood and synthetic resins to form a cured coating film which is excellent in resistance to heat, durability, water-proof property and resistance to chemicals by heating at a relatively low temerature for a short time.
Statement of Related Prior Art:
A process has hitherto been known for preparing a coating composition containing the products of hydrolysis and subsequent partial condensation of silane compounds, wherein the silane compound is dissolved in a solvent miscible with water, such as ethanol, and then subjected to hydrolysis and partial condensation by the catalytic action of an acid in the presence of water.
The known acids generally used as the catalyst in the known process include hydrochloric acid, sulfuric acid and phosphoric acid. However, the use of such mineral acids 2C ~ 969 is detrimental to the properties of the resultant coating composition. For example, when hydrochloric acid is used as the catalyst, hydrochloric ions are not incorporated in the condensation product of silane to be left in the form of free ions to cause electrolytic corrosion. On the other hand, when phosphoric acid is used, although phosphoric ions are incorporated in the condensation product of silane, adhesiveness of the resultant coating composition is becomes inferior or the storage stability thereof becomes poor to shorten the pot life of the coating composition.
There is a demand for an improved antistatic coating composition which can be stored stably for a long period of time and forms a cured coating film having excellent properties, particularly satisfactory antistatic property and high adhesive strength to protect the material coated therewith reliably.
OBJECTS AND SUMMARY OF THE INVENTION: -Accordingly, the primary object of this invention is to provide an antistatic coating composition for forming a cured coating film which is improved in resistance to heat, durability, water-proof property and resistance to chemicals.
Another object of this invention is to provide an antistatic coating composition which is improved in adhesiveness to form a tough coating on a variety of materials including metals and synthetic resins.
~201 0969 A further object of this invention is to provide an antistatic coating composition which can be stored stably for a prolonged period of time and forms an electrically insulating and antistatic coating film by heating at a relatively low temperature.
A still further object of this invention is to provide a process for preparing such a coating composition.
After eager pursuits for preparing an antistatic coating composition, it has been found that an organosilane coating composition having a long pot life and forming a tough coating can be prepared by combining particular hydrolyzable organosilane compounds and then co-polycondensing the products of hydrolysis in the presence of a reaction product of phosphoric acid and an aluminium compound, preferably in the presence of aluminium dihydrogenphosphate. The hydrolysis and subsequent co-polycondensation take place on the material coated with the coating composition of this invention by heating at a relatively low temperature.
More specifically, this invention provides an antistatic coating composition comprising:
(a) a reaction product of phosphoric acid and an aluminium compound:
(b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(c) a second organosilane compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent.
In the most preferred embodiment, the reaction product of phosphoric acid and an aluminium compound is aluminium dihydrogenphosphate.
According to a further aspect of this invention, provided is a process for the preparation of an antistatic coating composition containing products of hydrolysis and subsequent polycondensation of first and second organosilane compounds, said first organosilane compound having at least one epoxy group and a hydrolyzable alkoxy group and said second organosilane compound having two or more hydrolyzable alkoxy groups, and said partial hydrolysis and subsequent polycondensation being carried out in the presence of at least water, an organic solvent and a catalyst which is a reaction product of phosphoric acid and an aluminium compound, most preferably aluminium dihydrogenphosphate.
In yet another aspect, the present invention provides an antistatic coating composition comprising:
(a) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(b) a second organosilane compound having no epoxy group and two or more hydrolyzable alkoxy groups; (c) 2 to 20 wt%, based on the total weight of said first and second organosilane compounds, of aluminum dihydrogenphosphate;
and (d) 50 to 500 parts by weight, based on the total weight of said first and second organosilane compounds, of an organic solvent for said first and second organosilane compounds, wherein said first organosilane compound and said second organosilane compound are present in an amount effective to provide an antistatic coating.
In yet another aspect, the present invention provides, in a process for the preparation of an antistatic coating composition containing products of hydrolysis and subsequent polycondensation of first and second organosilane compounds, said first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group and said second organosilane compound having no epoxy group and two or more hydrolyzable alkoxy groups, and said hydrolysis and subsequent polycondensation being carried out in the presence of water, an organic solvent and a catalyst, the improvement which comprises said catalyst is aluminum dihydrogenphosphate, wherein said first organosilane compound and said second organosilane compound are present in an amount effective to provide an antistatic coating.
DESCRIPTION OF PREFERRED EMBODIMENT:
The present invention will now be described in detail.
As aforementioned, the antistatic coating composition of this invention comprises the four components of (a) a reaction product of phosphoric acid and an aluminium compound (b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group: (c) a second organosilane 4a , .
.
compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent. The most important feature of the invention is the use of a reaction product of phosphoric acid and an aluminium compound, most preferably aluminium dihydrogenphosphate, which acts as a catalyst for hydrolysis and subsequent co-polycondensation and is incorporated into the molecules of the resultant co-polycondensation product.
Although details of the partial hydrolysis and subsequent co-polycondensation reactions of the first and second organosilane compounds, which take place in the presence of aluminium ~ihydrogenphosphate, have not been fully clarified, it is estimated that the following reactions take place during the heating step effected after the coating composition is coated on a sheet or surface to be coated with the protective coating film.
OR' OR' OH
R-Si(OR')2 > R-Si-OH + R-Si-oH + R-Si-OH
H OR' OH OH
OH R R R
R-Si-OH ~ -Si-O-Si-O-Si-OH OH OH OH
OR' f O \ ~ OR' O \
R-Si-OR' + HO-P-O Al ~ R-Si-o-P-O Al OR' \ 1H ~ 3 \ OR~ OH 3 R R R OH OH
-Si-O-Si-O-Si-O- + HO-P-O-Al-O-P-OH
OH OH OH O O O
HO-P=O
OH
R
--si--o--O O O O
> R-Si-O-P-O-Al-O-P-O-Si-R
Il l I I
1 0 ~ ~ O ~
HO-P=O Si OH R
In the reaction formulae set forth above, R and R' each stands for an alkyl group.
When aluminium dihydrogenphosphate (Al(H2PO4)3) is used as the catalyst, a commercially available 20 to 50%
aqueous solution thereof may be used. The quantity o~
aluminium dihydrogenphosphate added in the composition of this invention ranges, preferably, from 2 to 20~ by weight, based on the total weight of the first and second organo-silane compound contained in the composition. If the added quantity of aluminium dihydrogenphosphate is less than 2~ by weight, the rates of hydrolysis and subsequent co-polycondensation become too low to increase the period of time required for setting or curing the coating composition;
whereas if the added quantity of aluminium dihydrogen-2 0 1 0 9 6 ~
phosphate is more than 20~ by weight, the rates ofhydrolysis and subsequent co-polycondensation become too high to make it impossible to control the reactions and there arises adverse tendency of gelation of the coating composition.
The first organosilane compound, which may be used in the present invention, include those represented by the following formula of:
CH2-CH-CH2-O(CH2)3Si(OR)3;
wherein R is an straight-chain alkyl group having 1 to 2 carbon atoms.
Specific examples of the first organosilane compound are as follows:
~ -glycidoxypropyl trimethoxysilane;
\2 / 2 2 2 2 ( 3)3 r-glycidoxypropyl methyldimethoxysilane;
CH2-CHCH2OCH2CH2CH2Si(OCH3)2 ~-glycidoxypropyl dimethylmethoxysilane;
CH2 -CHCH20CH2CH2CH2SiOCH3 ~-glycidoxypropyl triethoxysilane;
CH -cHcH2ocH2cH2cH2si(oc2 5)3 ~-glycidoxypropyl methyldiethoxysilane;
CH2-CHCH2OCH2CH2CH2Si(OCH3)2 ~-glycidoxypropyl dimethylethoxysilane;
CH2-CHCH2OCH2CH2CH2Si(OCH3)3 ~-(3,4-epoxycyclohexyl)ethyltrimethoxysilane;
O- C - CH
HC CHCH2CH2Si(OCH3)3 H C - CH
~-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane;
H
O- C - CH CH
I / \2 1 3 HC / 2 2 ( 3)2 H C - CH
~-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane;
H
HC CHCH2CH2SiOCH3 r ~-(3,4-epoxycyclohexyl)ethyltriethoxysilane;
H
O- C - CH
HC CHcH2cH2si(oc2H5)3 ~-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane:
H
HC CHcH2cH2si(oc2H5)2 ~-(3,4-epoxycyclohexyl)ethyldimethylethoxysilane:
H
and mixtures thereof.
It is possible to use co-polycondensation products prepared by hydrolysis of any one or more of the first organosilane compounds set forth above and subsequent partial co-polycondensation of the products of the hydrolysis.
The second organosilane compounds, which may be preferably used in the composition of this invention include those represented by the following formula of:
CH3Si(OR)3:
wherein R is a straight-chain alkyl group having 2Q~9~i9 1 to 2 carbon atoms.
Specific examples of the second organosilane compounds are methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, orthomethyl silicate, orthoethyl silicate and mixtures thereof.
It is possible to use co-polycondensation products prepared by hydrolysis of any one or more of the second organosilane compounds set forth above and subsequent partial co-polycondensation of the products of hydrolysis.
The organic solvent used in the composition of this invention is a solvent for the organosilane compounds, the solvent being miscible with water. The organic solvent serves to dissolve and disperse the used catalyst, preferably aluminium dihydrogenphosphate, and to properly control the hydrolysis and subsequent polycondensation reactions. Although it is preferred to use a polar solvent, a mixture of a polar solvent with a non-polar solvent may also be used.
Specific examples of the polar solvent, which may be used in the composition of this invention, are alcohols such as methanol, ethanol, isopropanol, n-butanol and _ 2 0 1 0 9 6 g isobutanol; ether alcohols such as ethyleneglycol monomethyl ether, ethyleneglycol monoethyl ether and ethyleneglycol monobutyl ether; esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, amyl acetate, ethyleneglycol monomethyl ether acetate and ethyleneglycol monoethyl ether acetate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and diacetone alcohol;
and mixtures thereof. The most preferable polar solvent is methanol, since it is inexpensive and perfectly miscible with water.
Specific examples of preferable non-polar solvent, which may be added to the polar solvent, are hexane, heptane, octane and mixtures thereof. Although an aromatic compound such as toluene and xylene may be added to the polar solvent, it is desirable that the aromatic compound be used as little as possible since the coating composition becomes cloudy when a large amount thereof is added.
The content of the organic solvent ranges preferably from 50 to 500 parts by weight, based on the total weight of the first and second organosilane compounds.
If the content of the organic solvent is less than 50 parts by weight, the viscosity of the resultant coating composition becomes too high and the pot life of the composition is shortened. On the contrary, although the pot life of the resultant coating composition can be prolonged 20 t 0 9 6 9 by adding 500 parts by weight or more of the organic solvent, the viscosity of the composition becomes too low and makes it difficult to form a coating film having a sufficient thickness.
Water contained in the coating composition of this invention is normally supplied as water used for dissolving aluminium dihydrogenphosphate. However, water may be added as desired to prepare a coating composition having a proper VlS COS 1 ty.
EXAMPLE
The present invention will now be described more specifically with reference to an example thereof. However, it is to be noted hereby that the following example is given by way of example only and thus the invention should not be limited thereby, the scope of the invention being defined by the appended claims.
A coating composition was prepared by mixing the components, as will be set forth below, and the mixture was allowed to stand at room temperature for 24 hours:
Methyltrimethoxysilane 25g ~-Glycidoxypropyltrimethoxysilane 25g 50 wt% Aqueous Solution of Aluminium lOg Dihydrogenphosphate Methanol 50g The following are the properties of the thus pre-pared coating composition and the coating film after curing.
~ 20 1 0 9 6 9 Properties of the Coating Composition:
Specific Gravity: 0.939 (at 25~C) Viscosity: 3.5 cp. (at 25~C) Properties of the Cured Coating Film:
Condition for Curing Pencil Hardness 25~C, 1 hr. 3H
25~C, 24 hrs. 6H
70~C, 2 hrs. 5H
100~C, 2 hrs. 9H
Surface Resistivity:
The surface resistivity of a cured coating film applied on an acrylic resin plate was measured by the method stipulated in JIS K 6911 to find that the surface resistivity was 1.0 x 10 ohm.cm.
The coating composition was applied on plates, respectively, made of an ABS resin, PZ, Teflon (Trade Mark) and PVC, and the surface resistivities of the cured coating films were measured. The results were substantially equivalent to that of the coating film applied on the acrylic resin plate.
Antistatic Property:
The coating composition was applied on an acrylic resin plate and then cured. The antistatic property of the cured coating film was measured by the JIS L-1094 method to obtain the following results (the results being expressed by the half-value periods of the 20 ~ 0969 initial values when an electric potential of 10 KV was applied). The results revealed that the cured coating films formed by the use of the coating composition of the invention exhibited superior antistatic effects.
Equivalent results were obtained when the coating composition was applied, respectively, on different substrates made of PVC, PZ, Teflon (Trade Mark) and ABS.
Normal Condition (25~C, 55% RH*) 1.0 sec.
25~C, 30% RH* 5.0 sec.
After being treated at 70~C for 100 hrs. 11.9 sec.
*Note: RH = Relative Humidity As will be seen from the data given above, the coating composition of the invention forms a cured coating film superior over that obtainable by the conventional technology.
Although the invention has been described with reference to a presently preferred embodiment, many modifications and alternations may be conceived by a person having ordinary skill in the art without departing from the spirit and scope of the invention which is defined in the appended claims.
Claims (27)
1. An antistatic coating composition comprising:
(a) a reaction product of phosphoric acid and an aluminium compound;
(b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(c) a second organosilane compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent.
(a) a reaction product of phosphoric acid and an aluminium compound;
(b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(c) a second organosilane compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent.
2. The antistatic coating composition according to claim 1, wherein said reaction product of phosphoric acid and an aluminum compound is aluminum dihydrogenphosphate.
3. The antistatic coating composition according to claim 1, wherein said first organosilane compound is selected from the group consisting of:
.gamma.-glycidoxypropyl trimethoxysilane;
.gamma.-glycidoxypropyl methyldimethoxysilane;
.gamma.-glycidoxypropyl dimethylmethoxysilane;
.gamma.-glycidoxypropyl triethoxysilane;
.gamma.-glycidoxypropyl methyldiethoxysilane;
.gamma.-glycidoxypropyl dimethylethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyltrimethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyltriethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyldimethylethoxysilane;
and mixtures thereof.
.gamma.-glycidoxypropyl trimethoxysilane;
.gamma.-glycidoxypropyl methyldimethoxysilane;
.gamma.-glycidoxypropyl dimethylmethoxysilane;
.gamma.-glycidoxypropyl triethoxysilane;
.gamma.-glycidoxypropyl methyldiethoxysilane;
.gamma.-glycidoxypropyl dimethylethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyltrimethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyltriethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyldimethylethoxysilane;
and mixtures thereof.
4. An antistatic coating composition comprising:
(a) a reaction product of phosphoric acid and an aluminium compound;
(b) a co-polycondensation product prepared by hydrolysis of any one or more of the first organosilane compounds set forth in claim 3 and subsequent partial polycondensation of the products of said hydrolysis, (c) a second organosilane compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent.
(a) a reaction product of phosphoric acid and an aluminium compound;
(b) a co-polycondensation product prepared by hydrolysis of any one or more of the first organosilane compounds set forth in claim 3 and subsequent partial polycondensation of the products of said hydrolysis, (c) a second organosilane compound having two or more hydrolyzable alkoxy groups; and (d) an organic solvent.
5. The antistatic coating composition according to claim 1, wherein said second organosilane compound is selected from the group consisting of methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, orthomethyl silicate, orthoethyl silicate and mixtures thereof.
6. An antistatic coating composition comprising:
(a) a reaction product of phosphoric acid and an aluminium compound;
(b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(c) a co-polycondensation product prepared by hydrolysis of any one or more of the second organosilane compounds set forth in claim 5 and subsequent partial polycondensation of the products of said hydrolysis; and (d) an organic solvent.
(a) a reaction product of phosphoric acid and an aluminium compound;
(b) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(c) a co-polycondensation product prepared by hydrolysis of any one or more of the second organosilane compounds set forth in claim 5 and subsequent partial polycondensation of the products of said hydrolysis; and (d) an organic solvent.
7. The antistatic coating composition according to claim 1, wherein said organic solvent is a polar solvent.
8. The antistatic coating composition according to claim 7, wherein said polar solvent is selected from the group consisting of alcohols selected from the group comprising methanol, ethanol, isopropanol, n-butanol and isobutanol; ether alcohols selected from the group consisting of ethyleneglycol monomethyl ether, ethyleneglycol monoethyl ether and ethyleneglycol monobutyl ether; esters selected from the group consisting of methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, amyl acetate, ethyleneglycol monomethyl ether acetate and ethyleneglycol monoethyl ether acetate;
ketones selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone and diacetone alcohol; and mixtures thereof.
ketones selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone and diacetone alcohol; and mixtures thereof.
9. The antistatic coating composition according to claim l, wherein said organic solvent is a mixture of a polar solvent and a non-polar solvent.
10. The antistatic coating composition according to claim 9, wherein said non-polar solvent is selected from the group consisting of hexane, heptane, octane and mixtures thereof.
11. In a process for the preparation of an antistatic coating composition containing products of hydrolysis and subsequent polycondensation of first and second organosilane compounds, said first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group and said second organosilane compound having two or more hydrolyzable alkoxy groups, and said hydrolysis and subsequent polycondensation being carried out in the presence of at least water, an organic solvent and a catalyst, an improvement which comprises said catalyst is aluminium hydrogenphosphate.
12. The improved process according to claim 11, wherein said aluminium hydrogen phosphate is aluminium dihydrogenphosphate.
13. The improved process according to claim 11, wherein said first organosilane compound is selected from the group consisting of:
.gamma.-glycidoxypropyl trimethoxysilane;
.gamma.-glycidoxypropyl methyldimethoxysilane;
.gamma.-glycidoxypropyl dimethylmethoxysilane;
.gamma.-glycidoxypropyl triethoxysilane;
.gamma.-glycidoxypropyl methyldiethoxysilane;
.gamma.-glycidoxypropyl dimethylethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyltrimethoxysilane:
.beta.-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane::
.beta.-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane::
.beta.-(3,4-epoxycyclohexyl)ethyltriethoxysilane:
.beta.-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane:
.beta.-(3,4-epoxycyclohexyl)ethyldimethylethoxysilane:
and mixtures thereof: and wherein said second organosilane compound is selected from the group consisting of methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, orthomethyl silicate, orthoethyl silicate and mixtures thereof.
.gamma.-glycidoxypropyl trimethoxysilane;
.gamma.-glycidoxypropyl methyldimethoxysilane;
.gamma.-glycidoxypropyl dimethylmethoxysilane;
.gamma.-glycidoxypropyl triethoxysilane;
.gamma.-glycidoxypropyl methyldiethoxysilane;
.gamma.-glycidoxypropyl dimethylethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyltrimethoxysilane:
.beta.-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane::
.beta.-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane::
.beta.-(3,4-epoxycyclohexyl)ethyltriethoxysilane:
.beta.-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane:
.beta.-(3,4-epoxycyclohexyl)ethyldimethylethoxysilane:
and mixtures thereof: and wherein said second organosilane compound is selected from the group consisting of methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, orthomethyl silicate, orthoethyl silicate and mixtures thereof.
14. The improved process according to any of claims 11 to 13, wherein said catalyst is added in an amount of from 2 to 20 parts by weight based on the total weight of said first and second organosilane compounds.
15. The improved process according to any of claims 11 to 13, wherein said catalyst is added in the form of an aqueous solution containing 20 to 50% of aluminium hydrogenphosphate.
16. The improved process according to claim 14, wherein said catalyst is added in the form of an aqueous solution containing 20 to 50 % of aluminium hydrogenphosphate.
17. An antistatic coating composition comprising:
(a) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(b) a second organosilane compound having no epoxy group and two or more hydrolyzable alkoxy groups;
(c) 2 to 20 wt%, based on the total weight of said first and second organosilane compounds, of aluminum dihydrogenphosphate; and (d) 50 to 500 parts by weight, based on the total weight of said first and second organosilane compounds, of an organic solvent for said first and second organosilane compounds, wherein said first organosilane compound and said second organosilane compound are present in an amount effective to provide an antistatic coating.
(a) a first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group;
(b) a second organosilane compound having no epoxy group and two or more hydrolyzable alkoxy groups;
(c) 2 to 20 wt%, based on the total weight of said first and second organosilane compounds, of aluminum dihydrogenphosphate; and (d) 50 to 500 parts by weight, based on the total weight of said first and second organosilane compounds, of an organic solvent for said first and second organosilane compounds, wherein said first organosilane compound and said second organosilane compound are present in an amount effective to provide an antistatic coating.
18. The antistatic coating composition according to claim 17, wherein said first organosilane compound is selected from the group consisting of:
.gamma.-glycidoxypropyl trimethoxysilane;
.gamma.-glycidoxypropyl methyldimethoxysilane;
.gamma.-glycidoxypropyl dimethylmethoxysilane;
.gamma.-glycidoxypropyl triethoxysilane;
.gamma.-glycidoxypropyl methyldiethoxysilane;
.gamma.-glycidoxypropyl dimethylethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyltrimethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane;
.beta.(3,4-epoxycyclohexyl)ethyltriethoxysilane;
.beta.(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane;
.beta.(3,4-epoxycyclohexyl)ethyldimethylethoxysilane;
and mixtures thereof.
.gamma.-glycidoxypropyl trimethoxysilane;
.gamma.-glycidoxypropyl methyldimethoxysilane;
.gamma.-glycidoxypropyl dimethylmethoxysilane;
.gamma.-glycidoxypropyl triethoxysilane;
.gamma.-glycidoxypropyl methyldiethoxysilane;
.gamma.-glycidoxypropyl dimethylethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyltrimethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane;
.beta.-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane;
.beta.(3,4-epoxycyclohexyl)ethyltriethoxysilane;
.beta.(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane;
.beta.(3,4-epoxycyclohexyl)ethyldimethylethoxysilane;
and mixtures thereof.
19. The antistatic coating composition according to claim 17, wherein said second organosilane compound is selected from the group consisting of:
methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, orthomethyl silicate, orthoethyl silicate, and mixtures thereof.
methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, orthomethyl silicate, orthoethyl silicate, and mixtures thereof.
20. The antistatic coating composition according to claim 17, wherein said organic solvent is a polar solvent.
21. The antistatic coating composition according to claim 20, wherein said polar solvent is selected from the group consisting of alcohols, ether alcohols, esters, ketones and mixtures thereof.
22. The antistatic coating composition according to claim 20, wherein said polar solvent is selected from the group consisting of methanol, ethanol, isopropanol, n-butanol, isobutanol, ethyleneglycol monomethyl ether, ethyleneglycol monoethyl ether, ethyleneglycol monobutyl ether, methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, amyl acetate, ethyleneglycol monomethyl ether acetate, ethyleneglycol monoethyl ether acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, diacetone alcohol and mixtures thereof.
23. The antistatic coating composition according to claim 17, wherein said organic solvent is a mixture of a polar solvent and a non-polar solvent.
24. The antistatic coating composition according to claim 23, wherein said non-polar solvent is selected from the group consisting of hexane, heptane, octane, and mixtures thereof.
25. In a process for the preparation of an antistatic coating composition containing products of hydrolysis and subsequent polycondensation of first and second organosilane compounds, said first organosilane compound having at least one epoxy group and at least one hydrolyzable alkoxy group and said second organosilane compound having no epoxy group and two or more hydrolyzable alkoxy groups, and said hydrolysis and subsequent polycondensation being carried out in the presence of water, an organic solvent and a catalyst, the improvement which comprises said catalyst is aluminum dihydrogenphosphate, wherein said first organosilane compound and said second organosilane compound are present in an amount effective to provide an antistatic coating.
26. The improved process according to claim 25, wherein said first organosilane compound is selected from the group consisting of:
-glycidoxypropyl trimethoxysilane;
-glycidoxypropyl methyldimethoxysilane;
-glycidoxypropyl dimethylmethoxysilane;
-glycidoxypropyl triethoxysilane;
-glycidoxypropyl methyldiethoxysilane;
-glycidoxypropyl dimethylethoxysilane;
-(3,4-epoxycyclohexyl)ethyltrimethoxysilane;
-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane;
-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane;
-(3,4-epoxycyclohexyl)ethyltriethoxysilane;
-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane;
-(3,4-epoxycyclohexyl)ethyldimethylethoxysilane;
and mixtures thereof; and wherein said second organosilane compound is selected from the group consisting of:
methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane.
-glycidoxypropyl trimethoxysilane;
-glycidoxypropyl methyldimethoxysilane;
-glycidoxypropyl dimethylmethoxysilane;
-glycidoxypropyl triethoxysilane;
-glycidoxypropyl methyldiethoxysilane;
-glycidoxypropyl dimethylethoxysilane;
-(3,4-epoxycyclohexyl)ethyltrimethoxysilane;
-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane;
-(3,4-epoxycyclohexyl)ethyldimethylmethoxysilane;
-(3,4-epoxycyclohexyl)ethyltriethoxysilane;
-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane;
-(3,4-epoxycyclohexyl)ethyldimethylethoxysilane;
and mixtures thereof; and wherein said second organosilane compound is selected from the group consisting of:
methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, phenyltriethoxysilane, dimethyldiethoxysilane.
27. The improved process according to claim 25, wherein aluminum dihydrogenphosphate is added in the form of an aqueous solution containing 20 to 50% of aluminum dihydrogenphosphate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1169793A JPH0335073A (en) | 1989-07-03 | 1989-07-03 | Production of inorganic coating composition |
| JP169793/1989 | 1989-07-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2010969A1 CA2010969A1 (en) | 1991-01-03 |
| CA2010969C true CA2010969C (en) | 1999-05-11 |
Family
ID=15892989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002010969A Expired - Fee Related CA2010969C (en) | 1989-07-03 | 1990-02-27 | Organosilane coating compositions |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US5091468A (en) |
| JP (1) | JPH0335073A (en) |
| CA (1) | CA2010969C (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5567235A (en) * | 1990-08-30 | 1996-10-22 | Elf Atochem North America, Inc. | Method for strengthening a brittle oxide substrate, silane-based compositions, and a polymerized cross-linked siloxane coated brittle oxide substrate |
| US6013333A (en) * | 1990-08-30 | 2000-01-11 | Elf Atochem North America, Inc. | Method for strengthening a brittle oxide substrate |
| JP2791253B2 (en) * | 1992-08-31 | 1998-08-27 | 松下電器産業株式会社 | Antistatic film and method for producing the same |
| PE56294A1 (en) * | 1993-06-21 | 1995-01-17 | Atochem North America Elf | A METHOD FOR STRENGTHENING A CRISPABLE OXIDE SUBSTRATE, SILANO BASED COMPOSITIONS, AND A SILOXANE COATED CROSS-LINED CROSS-CROSSED OXIDE SUBSTRATE |
| US5728203A (en) * | 1995-10-26 | 1998-03-17 | Lord Corporation | Aqueous protective and adhesion promoting composition |
| JP2000505143A (en) * | 1996-11-22 | 2000-04-25 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | Lacquer composition |
| DE19649183A1 (en) * | 1996-11-27 | 1998-06-04 | Fraunhofer Ges Forschung | Antistatic agent, process for its preparation and its use for the production of antistatic coatings |
| US6037008A (en) * | 1998-09-08 | 2000-03-14 | Ck Witco Corporation | Use of emulsified silane coupling agents as primers to improve adhesion of sealants, adhesives and coatings |
| US6461419B1 (en) | 1999-11-01 | 2002-10-08 | 3M Innovative Properties Company | Curable inkjet printable ink compositions |
| KR100521889B1 (en) * | 2001-01-19 | 2005-10-17 | 바이오시스텍 주식회사 | Container having functions of removing ethylene and suppressing generation of ethylene |
| EP1381331B1 (en) | 2001-03-16 | 2009-03-11 | Novartis AG | Method for making a colored contact lens |
| US6793971B2 (en) | 2001-12-03 | 2004-09-21 | Cardinal Ig Company | Methods and devices for manufacturing insulating glass units |
| JP4680611B2 (en) * | 2004-01-20 | 2011-05-11 | 株式会社砺波商店 | Tableware |
| US7530683B2 (en) * | 2004-07-29 | 2009-05-12 | E.I. Du Pont De Nemours And Company | Fixing fluid and inkjet ink sets comprising same |
| DE102005001616A1 (en) * | 2005-01-12 | 2006-07-20 | Huhtamaki Forchheim Zweigniederlassung Der Huhtamaki Deutschland Gmbh & Co. Kg | Antistatic surface finish |
| US20090264316A1 (en) * | 2008-04-17 | 2009-10-22 | Marshall University Research Corporation | Ultraviolet/Ozone Patterned Organosilane Surfaces |
| EP4206272A1 (en) * | 2021-12-28 | 2023-07-05 | Kyushu High Tech. Co., Ltd | Inorganic glass coating agent |
| CN115260899A (en) * | 2022-07-28 | 2022-11-01 | 广东美的白色家电技术创新中心有限公司 | Hydrophobic coating and preparation method and application thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56103224A (en) * | 1980-01-22 | 1981-08-18 | Toshiba Silicone Co Ltd | Preparation of epoxy-modified silicone resin |
| JPS6243468A (en) * | 1985-08-21 | 1987-02-25 | Kansai Paint Co Ltd | Water-based organic silicone resin coating composition |
-
1989
- 1989-07-03 JP JP1169793A patent/JPH0335073A/en active Granted
-
1990
- 1990-01-29 US US07/471,349 patent/US5091468A/en not_active Expired - Fee Related
- 1990-02-27 CA CA002010969A patent/CA2010969C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2010969A1 (en) | 1991-01-03 |
| US5091468A (en) | 1992-02-25 |
| JPH0335073A (en) | 1991-02-15 |
| JPH0545612B2 (en) | 1993-07-09 |
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