AU741534B2 - Abrasion and stain resistant curable fluorinated coating - Google Patents
Abrasion and stain resistant curable fluorinated coating Download PDFInfo
- Publication number
- AU741534B2 AU741534B2 AU27629/99A AU2762999A AU741534B2 AU 741534 B2 AU741534 B2 AU 741534B2 AU 27629/99 A AU27629/99 A AU 27629/99A AU 2762999 A AU2762999 A AU 2762999A AU 741534 B2 AU741534 B2 AU 741534B2
- Authority
- AU
- Australia
- Prior art keywords
- fluorocopolymer
- group
- coating
- amino resin
- coating composition
- 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.)
- Ceased
Links
- 238000000576 coating method Methods 0.000 title claims description 70
- 239000011248 coating agent Substances 0.000 title claims description 55
- 238000005299 abrasion Methods 0.000 title description 15
- 239000000178 monomer Substances 0.000 claims description 87
- 229920003180 amino resin Polymers 0.000 claims description 75
- 239000008199 coating composition Substances 0.000 claims description 62
- 239000003795 chemical substances by application Substances 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 37
- 239000000758 substrate Substances 0.000 claims description 36
- -1 allyl glycolate Chemical compound 0.000 claims description 30
- 238000004132 cross linking Methods 0.000 claims description 30
- 229920001577 copolymer Polymers 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 17
- 229920002554 vinyl polymer Polymers 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 9
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 9
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 9
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003377 acid catalyst Substances 0.000 claims description 8
- 239000002184 metal Chemical class 0.000 claims description 8
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 230000000052 comparative effect Effects 0.000 claims description 6
- 125000006162 fluoroaliphatic group Chemical group 0.000 claims description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- 229920003986 novolac Polymers 0.000 claims description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims description 4
- 238000012546 transfer Methods 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical group OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 3
- 239000003822 epoxy resin Substances 0.000 claims description 3
- 229940015043 glyoxal Drugs 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 3
- POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 claims description 2
- DELJOESCKJGFML-DUXPYHPUSA-N (e)-3-aminobut-2-enenitrile Chemical compound C\C(N)=C/C#N DELJOESCKJGFML-DUXPYHPUSA-N 0.000 claims description 2
- BSSNZUFKXJJCBG-UPHRSURJSA-N (z)-but-2-enediamide Chemical compound NC(=O)\C=C/C(N)=O BSSNZUFKXJJCBG-UPHRSURJSA-N 0.000 claims description 2
- FCBZNZYQLJTCKR-UHFFFAOYSA-N 1-prop-2-enoxyethanol Chemical compound CC(O)OCC=C FCBZNZYQLJTCKR-UHFFFAOYSA-N 0.000 claims description 2
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 2
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 2
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 claims description 2
- RLLJBUZYAVNFOG-UHFFFAOYSA-N 2-methylprop-1-ene-1,1-diol Chemical compound CC(C)=C(O)O RLLJBUZYAVNFOG-UHFFFAOYSA-N 0.000 claims description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 claims description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
- HEDJXJIMHVAMEY-UHFFFAOYSA-N aziridin-1-yl prop-2-enoate Chemical compound C=CC(=O)ON1CC1 HEDJXJIMHVAMEY-UHFFFAOYSA-N 0.000 claims description 2
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 150000002689 maleic acids Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical class C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 2
- FTJXXXSSRCHQKC-UHFFFAOYSA-N n-(2-cyanoethyl)prop-2-enamide Chemical compound C=CC(=O)NCCC#N FTJXXXSSRCHQKC-UHFFFAOYSA-N 0.000 claims description 2
- ICMWSAALRSINTC-UHFFFAOYSA-N penta-1,4-dien-3-ol Chemical compound C=CC(O)C=C ICMWSAALRSINTC-UHFFFAOYSA-N 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 claims description 2
- 239000005050 vinyl trichlorosilane Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229920001774 Perfluoroether Chemical group 0.000 claims 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000005065 mining Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 26
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 229920000877 Melamine resin Polymers 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
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- 125000005842 heteroatom Chemical group 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
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- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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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
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
-
- 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
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/136185 | 1998-08-19 | ||
| US09/136,185 US6168866B1 (en) | 1998-08-19 | 1998-08-19 | Abrasion and stain resistant curable fluorinated coating |
| PCT/US1999/002979 WO2000011095A1 (en) | 1998-08-19 | 1999-02-11 | Abrasion and stain resistant curable fluorinated coating |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2762999A AU2762999A (en) | 2000-03-14 |
| AU741534B2 true AU741534B2 (en) | 2001-12-06 |
Family
ID=22471723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU27629/99A Ceased AU741534B2 (en) | 1998-08-19 | 1999-02-11 | Abrasion and stain resistant curable fluorinated coating |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6168866B1 (https=) |
| EP (1) | EP1114107B1 (https=) |
| JP (1) | JP2002523548A (https=) |
| KR (1) | KR100553925B1 (https=) |
| AR (1) | AR021760A1 (https=) |
| AU (1) | AU741534B2 (https=) |
| BR (1) | BR9914285A (https=) |
| CA (1) | CA2338789C (https=) |
| DE (1) | DE69908152T2 (https=) |
| ES (1) | ES2194443T3 (https=) |
| WO (1) | WO2000011095A1 (https=) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7320829B2 (en) | 1998-03-05 | 2008-01-22 | Omnova Solutions Inc. | Fluorinated polymer and amine resin compositions and products formed therefrom |
| US6686051B1 (en) | 1998-03-05 | 2004-02-03 | Omnova Solutions Inc. | Cured polyesters containing fluorinated side chains |
| JP2002505218A (ja) * | 1998-03-05 | 2002-02-19 | オムノヴア ソリユーシヨンズ インコーポレーテツド | 清掃容易なポリマーラミネート |
| US6383651B1 (en) | 1998-03-05 | 2002-05-07 | Omnova Solutions Inc. | Polyester with partially fluorinated side chains |
| US6673889B1 (en) * | 1999-06-28 | 2004-01-06 | Omnova Solutions Inc. | Radiation curable coating containing polyfuorooxetane |
| US6403760B1 (en) | 1999-12-28 | 2002-06-11 | Omnova Solutions Inc. | Monohydric polyfluorooxetane polymer and radiation curable coatings containing a monofunctional polyfluorooxetane polymer |
| US6962966B2 (en) | 1999-12-28 | 2005-11-08 | Omnova Solutions Inc. | Monohydric polyfluorooxetane oligomers, polymers, and copolymers and coatings containing the same |
| US6465566B2 (en) | 2000-07-06 | 2002-10-15 | Omnova Solutions Inc. | Anionic waterborne polyurethane dispersions containing polyfluorooxetanes |
| US6465565B1 (en) | 2000-07-06 | 2002-10-15 | Omnova Solutions, Inc. | Anionic waterborne polyurethane dispersions containing polyfluorooxetanes |
| JP4631137B2 (ja) * | 2000-08-01 | 2011-02-16 | 日東紡績株式会社 | 末端にメルカプト基を有するアリルアミン類重合体およびその製造方法 |
| US6689346B1 (en) * | 2000-10-25 | 2004-02-10 | L'oreal | Reshapable hair styling composition comprising acrylic copolymers |
| WO2002039148A1 (en) | 2000-11-09 | 2002-05-16 | Reflexite Corporation | Elastical optical structure |
| US6660828B2 (en) | 2001-05-14 | 2003-12-09 | Omnova Solutions Inc. | Fluorinated short carbon atom side chain and polar group containing polymer, and flow, or leveling, or wetting agents thereof |
| CA2447132C (en) * | 2001-05-14 | 2008-10-07 | Omnova Solutions Inc. | Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups |
| US20040146706A1 (en) * | 2001-06-19 | 2004-07-29 | Toshihiro Kasai | Protective film,adhesive sheet and floor surface protective structure |
| US6645478B2 (en) * | 2001-06-22 | 2003-11-11 | L'oreal S.A. | Reshapable hair styling composition comprising (meth)acrylic copolymers of four or more monomers |
| US6667378B2 (en) * | 2001-06-22 | 2003-12-23 | L'oreal, S.A. | Reshapable hair styling composition comprising heterogeneous (meth)acrylic copolymer particles |
| US20030147833A1 (en) * | 2001-12-20 | 2003-08-07 | L'oreal | Reshapable hair styling non-rinse composition comprising (meth)acrylic copolymers |
| CA2367898A1 (en) * | 2002-01-16 | 2003-07-16 | 3M Innovative Properties Company | Process for preparing improved abrasive article |
| US20030203980A1 (en) * | 2002-04-30 | 2003-10-30 | Valdes Reynaldo A. | Sol-gel composition, methods for manufacturing sol-gels, and applications for sol-gels |
| DE10252865A1 (de) * | 2002-11-12 | 2004-05-27 | Kronotec Ag | Verfahren zum Erzeugen eines strukturierten Dekors in einer Holzwerkstoffplatte |
| DE10252866B3 (de) | 2002-11-12 | 2004-04-29 | Kronotec Ag | Paneel und Verfahren zur Herstellung eines Paneels |
| US7617651B2 (en) * | 2002-11-12 | 2009-11-17 | Kronotec Ag | Floor panel |
| DE10252863B4 (de) * | 2002-11-12 | 2007-04-19 | Kronotec Ag | Holzfaserplatte, insbesondere Fussbodenpaneel |
| DE50309830D1 (de) * | 2002-11-15 | 2008-06-26 | Flooring Technologies Ltd | Einrichtung bestehend aus zwei miteinander verbindbaren Bauplatten und einem Einsatz zum Verriegeln dieser Bauplatten |
| US20040109947A1 (en) * | 2002-12-09 | 2004-06-10 | Weinert Raymond J. | Stain resistant coatings for flexible substrates, substrates coated therewith and related methods |
| DE10306118A1 (de) | 2003-02-14 | 2004-09-09 | Kronotec Ag | Bauplatte |
| US7678425B2 (en) | 2003-03-06 | 2010-03-16 | Flooring Technologies Ltd. | Process for finishing a wooden board and wooden board produced by the process |
| DE20304761U1 (de) * | 2003-03-24 | 2004-04-08 | Kronotec Ag | Einrichtung zum Verbinden von Bauplatten, insbesondere Bodenpaneele |
| DE10362218B4 (de) * | 2003-09-06 | 2010-09-16 | Kronotec Ag | Verfahren zum Versiegeln einer Bauplatte |
| DE20315676U1 (de) * | 2003-10-11 | 2003-12-11 | Kronotec Ag | Paneel, insbesondere Bodenpaneel |
| US7506481B2 (en) * | 2003-12-17 | 2009-03-24 | Kronotec Ag | Building board for use in subfloors |
| US6995222B2 (en) * | 2003-12-17 | 2006-02-07 | 3M Innovative Properties Company | Coating compositions with reactive fluorinated copolymers having pendant perfluoropolyether groups |
| DE102004005047B3 (de) * | 2004-01-30 | 2005-10-20 | Kronotec Ag | Verfahren und Einrichtung zum Einbringen eines die Feder einer Platte bildenden Streifens |
| DE102004011531C5 (de) * | 2004-03-08 | 2014-03-06 | Kronotec Ag | Holzwerkstoffplatte, insbesondere Fußbodenpaneel |
| DE102004011931B4 (de) * | 2004-03-11 | 2006-09-14 | Kronotec Ag | Dämmstoffplatte aus einem Holzwerkstoff-Bindemittelfaser-Gemisch |
| DE102005042658B3 (de) * | 2005-09-08 | 2007-03-01 | Kronotec Ag | Bauplatte, insbesondere Fußbodenpaneel |
| DE102005042657B4 (de) * | 2005-09-08 | 2010-12-30 | Kronotec Ag | Bauplatte und Verfahren zur Herstellung |
| US7854986B2 (en) * | 2005-09-08 | 2010-12-21 | Flooring Technologies Ltd. | Building board and method for production |
| DE102005063034B4 (de) | 2005-12-29 | 2007-10-31 | Flooring Technologies Ltd. | Paneel, insbesondere Bodenpaneel |
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- 1999-02-11 DE DE69908152T patent/DE69908152T2/de not_active Expired - Fee Related
- 1999-02-11 BR BR9914285-6A patent/BR9914285A/pt not_active IP Right Cessation
- 1999-02-11 AU AU27629/99A patent/AU741534B2/en not_active Ceased
- 1999-02-11 KR KR1020017002070A patent/KR100553925B1/ko not_active Expired - Fee Related
- 1999-02-11 JP JP2000566356A patent/JP2002523548A/ja active Pending
- 1999-02-11 CA CA002338789A patent/CA2338789C/en not_active Expired - Fee Related
- 1999-02-11 EP EP99908123A patent/EP1114107B1/en not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| KR100553925B1 (ko) | 2006-02-24 |
| US6168866B1 (en) | 2001-01-02 |
| AU2762999A (en) | 2000-03-14 |
| DE69908152T2 (de) | 2004-04-01 |
| CA2338789C (en) | 2009-01-27 |
| EP1114107B1 (en) | 2003-05-21 |
| WO2000011095A1 (en) | 2000-03-02 |
| DE69908152D1 (de) | 2003-06-26 |
| ES2194443T3 (es) | 2003-11-16 |
| CA2338789A1 (en) | 2000-03-02 |
| BR9914285A (pt) | 2001-06-19 |
| AR021760A1 (es) | 2002-08-07 |
| KR20010072747A (ko) | 2001-07-31 |
| JP2002523548A (ja) | 2002-07-30 |
| EP1114107A1 (en) | 2001-07-11 |
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