AU2004248127B2 - Coating compositions containing reactive diluents and methods - Google Patents
Coating compositions containing reactive diluents and methods Download PDFInfo
- Publication number
- AU2004248127B2 AU2004248127B2 AU2004248127A AU2004248127A AU2004248127B2 AU 2004248127 B2 AU2004248127 B2 AU 2004248127B2 AU 2004248127 A AU2004248127 A AU 2004248127A AU 2004248127 A AU2004248127 A AU 2004248127A AU 2004248127 B2 AU2004248127 B2 AU 2004248127B2
- Authority
- AU
- Australia
- Prior art keywords
- reactive diluent
- water
- oil
- coating composition
- pentaerythritol
- 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
- 239000003085 diluting agent Substances 0.000 title claims description 110
- 239000008199 coating composition Substances 0.000 title claims description 79
- 238000000034 method Methods 0.000 title claims description 34
- 229920000642 polymer Polymers 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 239000004814 polyurethane Substances 0.000 claims description 33
- 229920002635 polyurethane Polymers 0.000 claims description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 26
- 231100000344 non-irritating Toxicity 0.000 claims description 23
- 238000000576 coating method Methods 0.000 claims description 21
- 229920000180 alkyd Polymers 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 14
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 14
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 13
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 13
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 9
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 7
- 239000004952 Polyamide Substances 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- 229920002647 polyamide Polymers 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 238000012545 processing Methods 0.000 claims description 5
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 4
- XDWRKTULOHXYGN-UHFFFAOYSA-N 1,3-bis(ethenoxy)-2,2-bis(ethenoxymethyl)propane Chemical compound C=COCC(COC=C)(COC=C)COC=C XDWRKTULOHXYGN-UHFFFAOYSA-N 0.000 claims description 3
- TYMYJUHDFROXOO-UHFFFAOYSA-N 1,3-bis(prop-2-enoxy)-2,2-bis(prop-2-enoxymethyl)propane Chemical compound C=CCOCC(COCC=C)(COCC=C)COCC=C TYMYJUHDFROXOO-UHFFFAOYSA-N 0.000 claims description 3
- 229920006397 acrylic thermoplastic Polymers 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- IQQVCMQJDJSRFU-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO IQQVCMQJDJSRFU-UHFFFAOYSA-N 0.000 claims 2
- WKMJYOVHEKZRTD-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol 2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO WKMJYOVHEKZRTD-UHFFFAOYSA-N 0.000 claims 1
- GXMLTDBPAGDQIQ-UHFFFAOYSA-N CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(CO)(CO)CO Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(CO)(CO)CO GXMLTDBPAGDQIQ-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- -1 tile Substances 0.000 description 30
- 235000019198 oils Nutrition 0.000 description 22
- 239000003921 oil Substances 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 229920005862 polyol Polymers 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- 239000012855 volatile organic compound Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 238000001723 curing Methods 0.000 description 11
- 239000002253 acid Chemical group 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
- 150000001412 amines Chemical group 0.000 description 10
- 150000003077 polyols Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 150000007519 polyprotic acids Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- 229940035437 1,3-propanediol Drugs 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 235000019437 butane-1,3-diol Nutrition 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 210000004905 finger nail Anatomy 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229940060367 inert ingredients Drugs 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000056139 Brassica cretica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
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- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- WSNJGKKVNMLQPC-UHFFFAOYSA-N 1-(6-hydroxy-6-methyl-4-prop-1-en-2-ylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC(C(C)=C)=CC1(C)O WSNJGKKVNMLQPC-UHFFFAOYSA-N 0.000 description 1
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 1
- DUKJZYZDOKKAMU-UHFFFAOYSA-N 1-chloronaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(Cl)=C(C=O)C=CC2=C1 DUKJZYZDOKKAMU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08J3/246—Intercrosslinking of at least two polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- General Chemical & Material Sciences (AREA)
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- Application Of Or Painting With Fluid Materials (AREA)
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| US7728068B2 (en) | 2003-06-12 | 2010-06-01 | Valspar Sourcing, Inc. | Coating compositions containing reactive diluents and methods |
| CN1805989A (zh) * | 2003-06-12 | 2006-07-19 | 瓦尔斯帕供应公司 | 含有反应性稀释剂的涂料组合物和方法 |
| WO2006047746A1 (en) * | 2004-10-26 | 2006-05-04 | Noveon, Inc. | Water-borne dispersions of oil modified urethane polymers |
| AU2005309870B2 (en) * | 2004-11-22 | 2011-03-03 | Valspar Sourcing, Inc. | Coating composition and methods |
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| US20080305349A1 (en) * | 2007-06-05 | 2008-12-11 | Sun Chemical Corporation | Energy-curing breathable coatings (combined) |
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| CA3040096C (en) | 2010-12-28 | 2021-04-06 | Dura Chemicals, Inc. | Additives for curable liquid compositions |
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| BR112017020720B1 (pt) | 2015-04-01 | 2022-12-06 | Swimc Llc | Concentrado, colorante fluido, composição de revestimento de látex colorida, e, métodos para produção de um concentrado intermediário, para produção de colorantes fluidos e para produção de composições de revestimento fluidas de látex coloridas |
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| KR101989277B1 (ko) * | 2018-04-25 | 2019-06-13 | 주식회사 비전씨앤디 | 폐식용유를 활용한 접착 바인더를 포함하는 도로용 포장재 조성물 및 이를 이용한 도로 포장방법 |
| IT202000001963A1 (it) | 2020-01-31 | 2021-07-31 | Lamberti Spa | Metodo per rivestire un substrato mediante polimerizzazione a fascio di elettroni |
| KR102367820B1 (ko) * | 2020-05-19 | 2022-02-25 | 주식회사 케이씨씨 | 에폭시 내화도료 조성물 |
| CN114870413B (zh) * | 2022-04-14 | 2023-08-01 | 杭州特种纸业有限公司 | 一种钢纸用氯化锌溶液循环利用方法 |
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2004
- 2004-05-27 CN CNA2004800163732A patent/CN1805989A/zh active Pending
- 2004-05-27 CN CN2012101885963A patent/CN102690595A/zh active Pending
- 2004-05-27 JP JP2006533463A patent/JP2007502905A/ja active Pending
- 2004-05-27 MX MXPA05013238 patent/MX276236B/es active IP Right Grant
- 2004-05-27 CA CA2526970A patent/CA2526970C/en not_active Expired - Fee Related
- 2004-05-27 AU AU2004248127A patent/AU2004248127B2/en not_active Ceased
- 2004-05-27 KR KR1020107003143A patent/KR20100022127A/ko not_active Ceased
- 2004-05-27 BR BRPI0411101-0A patent/BRPI0411101A/pt not_active IP Right Cessation
- 2004-05-27 US US10/854,890 patent/US7605209B2/en active Active
- 2004-05-27 WO PCT/US2004/016755 patent/WO2004111143A2/en not_active Ceased
- 2004-05-27 EP EP04753568A patent/EP1631610B1/en not_active Revoked
- 2004-05-27 KR KR1020057023588A patent/KR101088274B1/ko not_active Expired - Fee Related
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2009
- 2009-09-11 US US12/557,683 patent/US9469780B2/en active Active
-
2016
- 2016-10-17 US US15/295,101 patent/US20170029662A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| US20170029662A1 (en) | 2017-02-02 |
| CN102690595A (zh) | 2012-09-26 |
| US7605209B2 (en) | 2009-10-20 |
| AU2004248127A1 (en) | 2004-12-23 |
| CA2526970C (en) | 2013-07-09 |
| KR20060026041A (ko) | 2006-03-22 |
| MX276236B (es) | 2010-05-28 |
| US9469780B2 (en) | 2016-10-18 |
| MXPA05013238A (es) | 2006-03-09 |
| JP2007502905A (ja) | 2007-02-15 |
| EP1631610B1 (en) | 2013-03-13 |
| EP1631610A2 (en) | 2006-03-08 |
| BRPI0411101A (pt) | 2006-07-18 |
| US20040254293A1 (en) | 2004-12-16 |
| KR20100022127A (ko) | 2010-02-26 |
| WO2004111143A3 (en) | 2005-10-06 |
| CN1805989A (zh) | 2006-07-19 |
| WO2004111143A2 (en) | 2004-12-23 |
| US20100004376A1 (en) | 2010-01-07 |
| CA2526970A1 (en) | 2004-12-23 |
| KR101088274B1 (ko) | 2011-11-30 |
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