DK2954015T3 - Oxidativt hærdbar coatingsammensætning - Google Patents
Oxidativt hærdbar coatingsammensætning Download PDFInfo
- Publication number
- DK2954015T3 DK2954015T3 DK14710945.8T DK14710945T DK2954015T3 DK 2954015 T3 DK2954015 T3 DK 2954015T3 DK 14710945 T DK14710945 T DK 14710945T DK 2954015 T3 DK2954015 T3 DK 2954015T3
- Authority
- DK
- Denmark
- Prior art keywords
- formulation
- manganese
- alkyd
- chelant
- formula
- Prior art date
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- 239000008199 coating composition Substances 0.000 title claims abstract description 51
- 230000001590 oxidative effect Effects 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 claims abstract description 251
- 238000009472 formulation Methods 0.000 claims abstract description 155
- 229920000180 alkyd Polymers 0.000 claims abstract description 113
- 239000011572 manganese Substances 0.000 claims abstract description 102
- 229920005989 resin Polymers 0.000 claims abstract description 86
- 239000011347 resin Substances 0.000 claims abstract description 86
- 229910001428 transition metal ion Inorganic materials 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 39
- 239000003973 paint Substances 0.000 claims abstract description 33
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 84
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 40
- 239000010941 cobalt Substances 0.000 claims description 39
- 229910052742 iron Inorganic materials 0.000 claims description 36
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 34
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 28
- -1 pyridin-2-yl-methyl Chemical group 0.000 claims description 25
- 229910017052 cobalt Inorganic materials 0.000 claims description 22
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 18
- 229910001429 cobalt ion Inorganic materials 0.000 claims description 18
- 239000010949 copper Substances 0.000 claims description 18
- 229910001431 copper ion Inorganic materials 0.000 claims description 18
- 229910001456 vanadium ion Inorganic materials 0.000 claims description 18
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 16
- 229910052720 vanadium Inorganic materials 0.000 claims description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 15
- 229910052802 copper Inorganic materials 0.000 claims description 15
- 150000002500 ions Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- 239000002738 chelating agent Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 7
- YPIFGDQKSSMYHQ-UHFFFAOYSA-M 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC([O-])=O YPIFGDQKSSMYHQ-UHFFFAOYSA-M 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 229910021568 Manganese(II) bromide Inorganic materials 0.000 claims description 4
- RJYMRRJVDRJMJW-UHFFFAOYSA-L dibromomanganese Chemical compound Br[Mn]Br RJYMRRJVDRJMJW-UHFFFAOYSA-L 0.000 claims description 4
- 229910000357 manganese(II) sulfate Inorganic materials 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000005609 naphthenate group Chemical group 0.000 claims description 3
- 229910021380 Manganese Chloride Inorganic materials 0.000 claims description 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011565 manganese chloride Substances 0.000 claims description 2
- 235000002867 manganese chloride Nutrition 0.000 claims description 2
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000013522 chelant Substances 0.000 abstract description 82
- 229910052748 manganese Inorganic materials 0.000 abstract description 33
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract description 31
- 238000001035 drying Methods 0.000 description 48
- 229910052751 metal Inorganic materials 0.000 description 40
- 239000002184 metal Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 36
- 238000002474 experimental method Methods 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000011230 binding agent Substances 0.000 description 24
- 239000003446 ligand Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 18
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexanol Substances CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000005755 formation reaction Methods 0.000 description 17
- 239000000344 soap Substances 0.000 description 16
- 229910021645 metal ion Inorganic materials 0.000 description 13
- 229910052723 transition metal Inorganic materials 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000002696 manganese Chemical class 0.000 description 9
- 229910001437 manganese ion Inorganic materials 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 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 group 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000000976 ink Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 150000002431 hydrogen Chemical group 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 5
- DJTZIDSZSYWGKR-UHFFFAOYSA-N acetic acid tetrahydrate Chemical compound O.O.O.O.CC(O)=O DJTZIDSZSYWGKR-UHFFFAOYSA-N 0.000 description 5
- NLTSCOZQKALPGZ-UHFFFAOYSA-N acetic acid;dihydrate Chemical compound O.O.CC(O)=O NLTSCOZQKALPGZ-UHFFFAOYSA-N 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011133 lead Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- KGGVGTQEGGOZRN-PLNGDYQASA-N (nz)-n-butylidenehydroxylamine Chemical compound CCC\C=N/O KGGVGTQEGGOZRN-PLNGDYQASA-N 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 3
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 229910052684 Cerium Inorganic materials 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 239000012972 dimethylethanolamine Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- CNFDGXZLMLFIJV-UHFFFAOYSA-L manganese(II) chloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Mn+2] CNFDGXZLMLFIJV-UHFFFAOYSA-L 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 description 2
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(III) nitrate Inorganic materials [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
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- 235000010755 mineral Nutrition 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000010773 plant oil Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 235000015096 spirit Nutrition 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZUUZGQPEQORUEV-UHFFFAOYSA-N tetrahydrate;hydrochloride Chemical compound O.O.O.O.Cl ZUUZGQPEQORUEV-UHFFFAOYSA-N 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- DTRGDWOPRCXRET-UHFFFAOYSA-N (9Z,11E,13E)-4-Oxo-9,11,13-octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCC(=O)CCC(O)=O DTRGDWOPRCXRET-UHFFFAOYSA-N 0.000 description 1
- DTRGDWOPRCXRET-SUTYWZMXSA-N (9e,11e,13e)-4-oxooctadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCC(=O)CCC(O)=O DTRGDWOPRCXRET-SUTYWZMXSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- ZKALVNREMFLWAN-VOTSOKGWSA-N (ne)-n-(4-methylpentan-2-ylidene)hydroxylamine Chemical compound CC(C)C\C(C)=N\O ZKALVNREMFLWAN-VOTSOKGWSA-N 0.000 description 1
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- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
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- 230000003247 decreasing effect Effects 0.000 description 1
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- 239000000539 dimer Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
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- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(II) nitrate Inorganic materials [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- SWTHFGISIJYNAE-UHFFFAOYSA-N manganese;2-pyridin-2-ylpyridine Chemical class [Mn].N1=CC=CC=C1C1=CC=CC=N1 SWTHFGISIJYNAE-UHFFFAOYSA-N 0.000 description 1
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- 125000005474 octanoate group Chemical class 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
- C08K13/02—Organic and inorganic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/08—Polyesters modified with higher fatty oils or their acids, or with resins or resin acids
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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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F9/00—Compounds to be used as driers, i.e. siccatives
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
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- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
Claims (13)
- OXIDATIVT HÆRDBAR COATINGSAMMENSÆTNING1. Formulering, der omfatter en oxidativt hærdbar alkyd-baseret hærdbar harpiks og et kompleks af et chalateringsmiddel med formlen (I): (hvor:hver R er uafhængigt udvalgt fra hydrogen, Ci-C24-alkyl, CH2CH2OH, CH2COOH og pyridin-2-yl- methyl; Q er en C2-C6-alkylenbro, en Q-Cio -arylenbro eller en bro, der omfatter en eller to Ci-C3-alkylenenheder og en C6-Ci0-arylenenhed, hvilken bro eventuelt kan være substitueret én eller flere gange med uafhængigt udvalgte CrC24-alkylgrupper; og hver Ri, R2, R3 og R4 er uafhængigt udvalgt fra H, Ci-C4-alkyl og Ci-C4-alkylhydroxy) og en overgangsmetalion, der er udvalgt fra gruppen bestående af mangan-, jern-, cobalt-, vanadium- og kobberioner, hvor komplekset ikke er veldefineret.
- 2. Formulering ifølge krav 1, hvor Q er ethylen, n-propylen, n-butylen, n-pentylen eller n-hexylen.
- 3. Formulering ifølge krav 1, hvor chelateringsmidlet er l,2-bis-(4,7-dimethyl-l,4,7,-triazacyclonon-l-yl)-ethan.
- 4. Fremgangsmåde til fremstilling af en formulering som defineret i et hvilket som helst af kravene 1 til 3, hvilken fremgangsmåde omfatter etablering af kontakt mellem en sammensætning, der omfatter en alkyd-baseret harpiks, og en sammensætning, der omfatter et chelateringsmiddel med formlen (I).
- 5. Fremgangsmåde ifølge krav 4 hvor fremgangsmåden omfatter etablering af kontakt mellem en formulering, der omfatter en oxidativt hærdbar alkyd-baseret hærdbar harpiks og et chelateringsmiddel med formlen (I), som defineret i krav 1, hvilken formulering omfatter mindre end 0,001 vægt-% ioner af hver af mangan, jern, cobalt, vanadium og kobber og en kilde af mangan-, jern-, cobalt-, vanadium- eller kobberioner.
- 6. Fremgangsmåde ifølge krav 5, hvor formuleringen bringes i kontakt med et eventuelt hydreret salt, der er udvalgt fra gruppen bestående af MnS04, MnCl2, MnBr2, Mn(N03)2, Mn(CH3COO)3, Mn(CH3COO)2, Mn(acetylacetonat)2, Mn(acetylacetonat)3, Mn(octanonat)2, Mn(2-ethylhexanoat)2, Mn(naphthenat)2 og Mn(neodecanoat)2.
- 7. Fremgangsmåde ifølge krav 4, hvor sammensætningen, der omfatter chelateringsmidlet med formlen (I), omfatter et kompleks som defineret i et hvilket som helst af kravene 1 til 3.
- 8. Fremgangsmåde ifølge krav 7, hvor sammensætningen, der omfatter komplekset, omfatter en blanding af chelateringsmidlet med formlen (I) og et salt af overgangsmetalionen.
- 9. Formulering ifølge et hvilket som helst af kravene 1 til 3, der kan opnås ved hjælp af en fremgangsmåde som defineret i et hvilket som helst af kravene 5 til 8.
- 10. Sammensætning, der er resultatet af hærdning af en formulering som defineret i et hvilket som helst af kravene 1 til 3 og 9.
- 11. Kit, der omfatter påføring til et substrat af en formulering som defineret i et hvilket som helst af kravene 1 til 3 og 9.
- 12. Kit, der omfatter en formulering, der omfatter en oxidativt hærdbar alkyd-baseret hærdbar harpiks og et chelateringsmiddel med formlen (I), som defineret i krav 1, hvilken formulering omfatter mindre end 0,001 vægt-% ioner af hver af mangan, jem, cobalt, vanadium og kobber, og separat en sammensætning, der omfatter overgangsmetalioner, der er udvalgt fra gruppen bestående af mangan-, jem-, cobalt, vanadium- og kobberioner.
- 13. Kit ifølge krav 12, hvor Q er ethylen, n-propylen, n-butylen, n-pentylen eller n-hexylen eller chelateringsmidlet er l,2-bis-(4,7-dimethyl-l,4,7,-triazacyclonon-l-yl)-ethan. REFERENCES CITED IN THE DESCRIPTION This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard. Patent documents cited in the description • WO 0011090 A1 [0010] · WO 2011098584 A1 [0016] [0020] • WO 2007024592 A1 [0010] · WO 2011098587 A1 [0016] [0020] • WO 2008127739 A1 [0010] · WO 2012092034 A2 [0017] [0020] • WO 03093384 A1 [0012] · WO 2012093250 A1 [0019] • WO 03029371 A1 [0013] · US 20010008932 A1, Bakkeren [0089] • EP 1382648 A1 [0014] [0018] · US 20050245639 A1, Oostveen [0089] • WO 2008003652 A1 [0015] [0020] · WO 2012003712 A [0094] • WO 2011098583 A1 [0016] [0020] · WO 2011106906 A [0094] Non-patent literature cited in the description • J H BIELEMAN. Additives in Plastics and Paints, · ZOOYMANetal. Surface Coating International Part Chimia, 2002, vol. 56, 184 [0009] B - Coatings Transaction, 2005, vol. 88, 269 [0016] • J H BIELEMAN. Additives in Plastics and Paints. · W H CANTY ; G K WHEELER ; R R MYERS. Ind. Chimia [0011] Eng. Chem., 1960, vol. 52, 67 [0018] • J H BIELEMAN. Marcomol. Symp., 2002, vol. 187, · P K WEISSENBORN ; A MOTIEJAUSKAITE. Prog. 811 [0011] Org. Coat., 2000, vol. 40, 253 [0018] • R E VAN GORKUM ; E BOUWMAN. Coord. Chem. · R VAN GORKUM et al. Inorg. Chem., 2004, vol. 43, Rev., 2005, vol. 249, 1709 [0011] 2456 [0018] • Surface Coatings. Chapman & Hall, 1993, 55 [0040]
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|---|---|---|---|
| EP13154852 | 2013-02-11 | ||
| PCT/GB2014/050270 WO2014122432A1 (en) | 2013-02-11 | 2014-01-31 | Oxidatively curable coating composition |
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| DK2954015T3 true DK2954015T3 (da) | 2018-04-30 |
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| KR (1) | KR102208428B1 (da) |
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| RU (1) | RU2665570C2 (da) |
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| AR107070A1 (es) | 2015-12-18 | 2018-03-14 | Catexel Ltd | Composición de recubrimiento oxidativamente curable |
| AR107530A1 (es) * | 2016-02-05 | 2018-05-09 | Catexel Ltd | Método para preparar una formulación para un recubrimiento curable por oxidación |
| CA3104688A1 (en) * | 2018-07-05 | 2020-01-09 | Borchers Catalyst (UK) Limited | Oxidatively curable coating composition |
| WO2022194298A1 (en) * | 2021-03-19 | 2022-09-22 | The Hong Kong Polytechnic University | Chiral TACN/NOTA compounds/derivatives with and without metals for application |
| WO2024126770A1 (en) | 2022-12-16 | 2024-06-20 | Borchers Gmbh | Vanadium complexes with nitrogen and oxygen donor atoms |
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| EP1115800A1 (en) | 1998-08-24 | 2001-07-18 | Akzo Nobel N.V. | Anti-skinning agent for coating compositions |
| WO2000020498A1 (fr) * | 1998-10-08 | 2000-04-13 | Kaneka Corporation | Compositions durcissables |
| AU2358901A (en) | 1999-12-22 | 2001-07-03 | Akzo Nobel N.V. | Coating composition comprising an oxidatively drying polyunsaturated condensation product, a polythiol, and siccative |
| EP1440130A1 (en) | 2001-09-28 | 2004-07-28 | Akzo Nobel Coatings International B.V. | Oxidatively drying coating composition |
| EP1501906A1 (en) | 2002-05-03 | 2005-02-02 | Ato B.V. | Drier for air-drying coatings |
| EP1382648A1 (en) | 2002-07-17 | 2004-01-21 | Universiteit Leiden | Drier for alkyd based coating |
| RU2261880C2 (ru) * | 2003-03-24 | 2005-10-10 | Открытое акционерное общество "Концерн Стирол" | Способ стабилизации лакокрасочных материалов на алкидной основе |
| US20070049657A1 (en) | 2005-08-23 | 2007-03-01 | Martyak Nicholas M | Antiskinning compound and compositions containing them |
| ZA200900038B (en) | 2006-07-07 | 2010-04-28 | Unilever Plc | Liquid hardening |
| US20080250977A1 (en) | 2007-04-16 | 2008-10-16 | Andrew Mason | Oxime free anti-skinning combination |
| UA99468C2 (uk) * | 2007-07-20 | 2012-08-27 | Сікпа Холдінг Са | Композиція фарби для глибокого друку, спосіб її одержання, застосування, спосіб глибокого друку із застосуванням фарби та захищений документ або цінний документ |
| EP2343336A1 (en) * | 2010-01-06 | 2011-07-13 | Unilever Plc, A Company Registered In England And Wales under company no. 41424 of Unilever House | Curing liquids |
| WO2011098587A1 (en) * | 2010-02-11 | 2011-08-18 | Dsm Ip Assets B.V. | Manganese complex as drier for coating compositions |
| PT2550283T (pt) | 2010-03-03 | 2016-08-16 | Catexel Ltd | Preparação de catalisadores de branqueamento |
| CN102947375B (zh) * | 2010-06-16 | 2014-02-26 | 阿克佐诺贝尔化学国际公司 | 促进剂溶液和固化可固化树脂的方法 |
| BR112013000236B1 (pt) * | 2010-07-06 | 2018-11-13 | Catexel Limited | método de produzir um composto, e, sal protonado |
| AU2010365740B2 (en) * | 2010-12-15 | 2015-12-24 | Ppg Europe Bv | Drier composition and use thereof |
| CA2823515C (en) | 2010-12-28 | 2019-06-04 | Dura Chemicals, Inc. | Additives for curable liquid compositions |
| EP2474578A1 (en) * | 2011-01-06 | 2012-07-11 | Rahu Catalytics Limited | Antiskinning compositions |
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| EP2954015A1 (en) | 2015-12-16 |
| NZ710668A (en) | 2020-02-28 |
| EP2954015B1 (en) | 2018-01-10 |
| AU2014213759B2 (en) | 2017-03-09 |
| CN104981521A (zh) | 2015-10-14 |
| CA2900891A1 (en) | 2014-08-14 |
| KR20150118589A (ko) | 2015-10-22 |
| WO2014122432A1 (en) | 2014-08-14 |
| ES2665118T3 (es) | 2018-04-24 |
| AU2014213759A1 (en) | 2015-08-20 |
| RU2015138729A (ru) | 2017-03-16 |
| AR094743A1 (es) | 2015-08-26 |
| MA38343A1 (fr) | 2016-03-31 |
| US9890297B2 (en) | 2018-02-13 |
| US20150337162A1 (en) | 2015-11-26 |
| CN104981521B (zh) | 2018-08-24 |
| RU2665570C2 (ru) | 2018-08-31 |
| TN2015000318A1 (en) | 2017-01-03 |
| AU2014213759C1 (en) | 2017-08-03 |
| CA2900891C (en) | 2021-04-20 |
| MA38343B1 (fr) | 2018-03-30 |
| BR112015018937A2 (pt) | 2020-02-04 |
| KR102208428B1 (ko) | 2021-01-28 |
| BR112015018937B1 (pt) | 2022-11-29 |
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