NL1000709C2 - Titaan- en zirkoniumcomplexen van carbonzuren als corrosieremmers. - Google Patents
Titaan- en zirkoniumcomplexen van carbonzuren als corrosieremmers. Download PDFInfo
- Publication number
- NL1000709C2 NL1000709C2 NL1000709A NL1000709A NL1000709C2 NL 1000709 C2 NL1000709 C2 NL 1000709C2 NL 1000709 A NL1000709 A NL 1000709A NL 1000709 A NL1000709 A NL 1000709A NL 1000709 C2 NL1000709 C2 NL 1000709C2
- Authority
- NL
- Netherlands
- Prior art keywords
- alkyl
- formula
- oxygen
- alkoxy
- interrupted
- Prior art date
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- 239000010936 titanium Substances 0.000 title claims description 76
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 title claims description 72
- 229910052719 titanium Inorganic materials 0.000 title claims description 72
- 230000007797 corrosion Effects 0.000 title claims description 39
- 238000005260 corrosion Methods 0.000 title claims description 39
- 239000003112 inhibitor Substances 0.000 title claims description 33
- 150000003754 zirconium Chemical class 0.000 title claims description 32
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 217
- -1 C 1 -C 2 Chemical group 0.000 claims description 150
- 229910052739 hydrogen Inorganic materials 0.000 claims description 134
- 239000001257 hydrogen Substances 0.000 claims description 128
- 150000001875 compounds Chemical class 0.000 claims description 116
- 229910052726 zirconium Inorganic materials 0.000 claims description 114
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 113
- 229910052760 oxygen Inorganic materials 0.000 claims description 106
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 105
- 239000001301 oxygen Substances 0.000 claims description 105
- 229910052717 sulfur Inorganic materials 0.000 claims description 100
- 239000011593 sulfur Substances 0.000 claims description 100
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 98
- 150000002431 hydrogen Chemical class 0.000 claims description 98
- 125000003545 alkoxy group Chemical group 0.000 claims description 80
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 239000008199 coating composition Substances 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 125000001624 naphthyl group Chemical class 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 239000000460 chlorine Substances 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 21
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 150000003755 zirconium compounds Chemical class 0.000 claims description 19
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims description 16
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 16
- 239000011230 binding agent Substances 0.000 claims description 15
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 14
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 14
- 239000003973 paint Substances 0.000 claims description 14
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000005605 benzo group Chemical group 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004450 alkenylene group Chemical group 0.000 claims description 11
- 239000000049 pigment Substances 0.000 claims description 11
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 9
- 125000001118 alkylidene group Chemical group 0.000 claims description 9
- 125000004419 alkynylene group Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000001326 naphthylalkyl group Chemical group 0.000 claims description 9
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 239000003822 epoxy resin Substances 0.000 claims description 7
- 229920000647 polyepoxide Polymers 0.000 claims description 7
- 229920000178 Acrylic resin Polymers 0.000 claims description 6
- 239000004925 Acrylic resin Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- 239000005011 phenolic resin Substances 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 229920000180 alkyd Polymers 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229920005749 polyurethane resin Polymers 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 229920001225 polyester resin Polymers 0.000 claims description 3
- 239000004645 polyester resin Substances 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- 239000013008 thixotropic agent Substances 0.000 claims description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- 241001331845 Equus asinus x caballus Species 0.000 claims description 2
- 229920006243 acrylic copolymer Polymers 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims 1
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 150000003609 titanium compounds Chemical class 0.000 claims 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 68
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
- 229910001868 water Inorganic materials 0.000 description 59
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 0.000 description 51
- 238000002360 preparation method Methods 0.000 description 50
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 40
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 38
- 239000000843 powder Substances 0.000 description 35
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 27
- 239000005711 Benzoic acid Substances 0.000 description 20
- 235000010233 benzoic acid Nutrition 0.000 description 20
- 235000019260 propionic acid Nutrition 0.000 description 19
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 19
- 238000012360 testing method Methods 0.000 description 17
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 16
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical class [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 15
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 12
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 229910000831 Steel Inorganic materials 0.000 description 7
- 230000032798 delamination Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000010959 steel Substances 0.000 description 7
- LEXSFKZESQMHJD-UHFFFAOYSA-N 2-(1,3-benzothiazole-2-carbothioyl)butanedioic acid Chemical compound C1=CC=C2SC(C(=S)C(C(O)=O)CC(=O)O)=NC2=C1 LEXSFKZESQMHJD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 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 description 6
- 239000004922 lacquer Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 229960002510 mandelic acid Drugs 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- RPXQLBYEQLJBTB-UHFFFAOYSA-N 3-(4-methylanilino)propanoic acid Chemical compound CC1=CC=C(NCCC(O)=O)C=C1 RPXQLBYEQLJBTB-UHFFFAOYSA-N 0.000 description 4
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 235000019502 Orange oil Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000010502 orange oil Substances 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000001384 succinic acid Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 description 4
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 3
- BTQZPXFENISXER-UHFFFAOYSA-N 2-(4-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(C)C=C1 BTQZPXFENISXER-UHFFFAOYSA-N 0.000 description 3
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 3
- GNPISAHACGIXLZ-UHFFFAOYSA-N 3-(4-methylphenoxy)propanoic acid Chemical compound CC1=CC=C(OCCC(O)=O)C=C1 GNPISAHACGIXLZ-UHFFFAOYSA-N 0.000 description 3
- IXWOVMRDYFFXGI-UHFFFAOYSA-N 4-(4-methylphenyl)butanoic acid Chemical compound CC1=CC=C(CCCC(O)=O)C=C1 IXWOVMRDYFFXGI-UHFFFAOYSA-N 0.000 description 3
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KSPPWGQIGVSIRK-UHFFFAOYSA-N 1-nitrocyclohexa-3,5-diene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)(C(O)=O)C1 KSPPWGQIGVSIRK-UHFFFAOYSA-N 0.000 description 2
- JNIHETDSIZRHLI-UHFFFAOYSA-N 2-(2-sulfanylidene-3h-1,3-benzothiazol-4-yl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)C1=CC=CC2=C1NC(=S)S2 JNIHETDSIZRHLI-UHFFFAOYSA-N 0.000 description 2
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 2
- CAHWDGJDQYAFHM-UHFFFAOYSA-N 2-nitroisophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1[N+]([O-])=O CAHWDGJDQYAFHM-UHFFFAOYSA-N 0.000 description 2
- ZRYGVBRPRKRFHJ-UHFFFAOYSA-N 3-(4-methylphenyl)sulfanylpropanoic acid Chemical compound CC1=CC=C(SCCC(O)=O)C=C1 ZRYGVBRPRKRFHJ-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
- MFFVROSEPLMJAP-UHFFFAOYSA-J zirconium(4+);tetraacetate Chemical class [Zr+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O MFFVROSEPLMJAP-UHFFFAOYSA-J 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
- C09D5/082—Anti-corrosive paints characterised by the anti-corrosive pigment
- C09D5/086—Organic or non-macromolecular compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211894 | 1994-07-01 | ||
| CH211894 | 1994-07-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NL1000709A1 NL1000709A1 (nl) | 1996-01-02 |
| NL1000709C2 true NL1000709C2 (nl) | 1998-07-27 |
Family
ID=4226296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1000709A NL1000709C2 (nl) | 1994-07-01 | 1995-06-30 | Titaan- en zirkoniumcomplexen van carbonzuren als corrosieremmers. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5612093A (ja) |
| JP (1) | JPH0848916A (ja) |
| KR (1) | KR100353564B1 (ja) |
| AT (1) | AT402297B (ja) |
| CA (1) | CA2152975A1 (ja) |
| DE (1) | DE19523539A1 (ja) |
| DK (1) | DK70295A (ja) |
| FR (1) | FR2721938B1 (ja) |
| GB (1) | GB2290789B (ja) |
| NL (1) | NL1000709C2 (ja) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998048075A1 (fr) | 1997-04-24 | 1998-10-29 | Nippon Steel Corporation | Tole enduite et fluide de traitement de surface pour metaux |
| WO2000043459A1 (de) * | 1999-01-21 | 2000-07-27 | Ciba Specialty Chemicals Holding Inc. | Korrosionsinhibierende überzugszusammensetzung für metalle |
| US6503305B1 (en) | 2000-05-18 | 2003-01-07 | Hammond Group, Inc. | Non-toxic corrosion inhibitor |
| DE10202545A1 (de) * | 2002-01-24 | 2003-08-07 | Basf Coatings Ag | Korrosionshemmende Mischung und Beschichtungsstoffe, enthaltend die korrosionshemmende Mischung |
| DE10202543A1 (de) * | 2002-01-24 | 2003-08-07 | Basf Coatings Ag | Beschichtungsstoffe und ihre Verwendung zur Herstellung schweißbarer Beschichtungen |
| US20050031873A1 (en) * | 2003-08-04 | 2005-02-10 | Guenter Berschel | Method for multi-coat refinishing of substrates |
| JP4850525B2 (ja) * | 2006-01-31 | 2012-01-11 | 富士通株式会社 | 多層回路基板およびその製造方法 |
| WO2009061208A1 (en) | 2007-11-09 | 2009-05-14 | Pronova Biopharma Norge As | Lipid compounds for use in cosmetic products, as food supplement or as a medicament |
| EP2147910A1 (en) * | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
| MY159778A (en) * | 2008-12-31 | 2017-01-31 | Memc Singapore Pte Ltd | Methods to recover and purify silicon paricles from saw kerf |
| TWI558395B (zh) | 2009-05-08 | 2016-11-21 | 普諾華生物製藥諾治股份有限公司 | 新穎的脂質化合物 |
| EA028535B1 (ru) | 2010-11-05 | 2017-11-30 | Пронова Биофарма Норге Ас | Способы лечения с применением липидных соединений |
| EP3578170A1 (en) | 2013-02-28 | 2019-12-11 | Basf As | A composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same |
| ES2980790T3 (es) | 2015-04-28 | 2024-10-03 | Basf As | Acidos grasos estructuralmente mejorados que contienen azufre para su uso en el tratamiento de la esteatohepatitis no alcohólica |
| GB201709767D0 (en) * | 2017-06-19 | 2017-08-02 | Ecolab Usa Inc | Naphthenate inhibition |
| CN111712240A (zh) | 2017-12-06 | 2020-09-25 | 巴斯夫股份公司 | 用于治疗非酒精性脂肪性肝炎的脂肪酸衍生物 |
| TWI811888B (zh) * | 2021-12-14 | 2023-08-11 | 國立清華大學 | 新型鈦觸媒之用途以及聚酯樹酯之製備方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1257873A (fr) * | 1960-03-22 | 1961-04-07 | Magnesium Elektron Ltd | Procédé pour la préparation de sels de zirconium d'acides organiques |
| EP0234649A1 (en) * | 1986-02-18 | 1987-09-02 | Akzo N.V. | A process for the preparation of zirconium carboxylate |
| GB2258464A (en) * | 1991-08-08 | 1993-02-10 | Tioxide Specialties Ltd | Preparation of titanium derivatives of carboxylic acids |
| EP0554023A1 (en) * | 1992-01-25 | 1993-08-04 | Ciba-Geigy Ag | Corrosion inhibitors |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1295432A (ja) * | 1968-09-19 | 1972-11-08 | ||
| US4243416A (en) * | 1975-10-08 | 1981-01-06 | Rohm And Haas Company | Corrosion-inhibiting method using latex paints and article |
| US4243417A (en) * | 1975-11-17 | 1981-01-06 | Rohm And Haas Company | Corrosion-inhibiting latex paints |
| GB1514361A (en) * | 1976-03-13 | 1978-06-14 | Tioxide Group Ltd | Titanium chelates |
| GB8313321D0 (en) * | 1983-05-14 | 1983-06-22 | Ciba Geigy Ag | Preparation of mercaptan substituted carboxylic acids |
| DE3338953A1 (de) * | 1983-10-27 | 1985-05-09 | Henkel KGaA, 4000 Düsseldorf | Verwendung von korrosionsinhibitoren in waessrigen systemen |
| JPS6195044A (ja) * | 1984-10-16 | 1986-05-13 | Nippon Soda Co Ltd | 表面処理剤 |
| GB8918086D0 (en) * | 1989-08-08 | 1989-09-20 | Ciba Geigy | Coating compositions |
| DE4120344A1 (de) * | 1990-06-26 | 1992-01-02 | Kali Chemie Ag | Verfahren zur abscheidung von titan, zirkonium oder hafnium enthaltenden schichten |
| DE4031817A1 (de) * | 1990-10-08 | 1992-04-09 | Henkel Kgaa | Verfahren zur passivierenden nachbehandlung von phosphatierten metalloberflaechen |
| GB9101468D0 (en) * | 1991-01-23 | 1991-03-06 | Ciba Geigy | Coating compositions |
| ES2095143T3 (es) * | 1993-04-07 | 1997-02-01 | Ciba Geigy Ag | Sales de metales alcalinoterreos, de metales de transicion y complejos de metales de transicion de acidos cetocarboxilicos como inhibidores de la corrosion. |
-
1995
- 1995-06-20 GB GB9512542A patent/GB2290789B/en not_active Expired - Fee Related
- 1995-06-20 DK DK070295A patent/DK70295A/da not_active Application Discontinuation
- 1995-06-28 DE DE19523539A patent/DE19523539A1/de not_active Ceased
- 1995-06-29 FR FR9507820A patent/FR2721938B1/fr not_active Expired - Fee Related
- 1995-06-29 CA CA002152975A patent/CA2152975A1/en not_active Abandoned
- 1995-06-29 AT AT0111095A patent/AT402297B/de not_active IP Right Cessation
- 1995-06-29 KR KR1019950018009A patent/KR100353564B1/ko not_active IP Right Cessation
- 1995-06-30 US US08/491,333 patent/US5612093A/en not_active Expired - Fee Related
- 1995-06-30 NL NL1000709A patent/NL1000709C2/nl not_active IP Right Cessation
- 1995-07-03 JP JP7189793A patent/JPH0848916A/ja not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1257873A (fr) * | 1960-03-22 | 1961-04-07 | Magnesium Elektron Ltd | Procédé pour la préparation de sels de zirconium d'acides organiques |
| EP0234649A1 (en) * | 1986-02-18 | 1987-09-02 | Akzo N.V. | A process for the preparation of zirconium carboxylate |
| GB2258464A (en) * | 1991-08-08 | 1993-02-10 | Tioxide Specialties Ltd | Preparation of titanium derivatives of carboxylic acids |
| EP0554023A1 (en) * | 1992-01-25 | 1993-08-04 | Ciba-Geigy Ag | Corrosion inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2152975A1 (en) | 1996-01-02 |
| FR2721938B1 (fr) | 1999-07-23 |
| US5612093A (en) | 1997-03-18 |
| AT402297B (de) | 1997-03-25 |
| KR100353564B1 (ko) | 2005-04-06 |
| GB2290789B (en) | 1998-09-16 |
| NL1000709A1 (nl) | 1996-01-02 |
| GB2290789A (en) | 1996-01-10 |
| JPH0848916A (ja) | 1996-02-20 |
| FR2721938A1 (fr) | 1996-01-05 |
| ATA111095A (de) | 1996-08-15 |
| KR960004466A (ko) | 1996-02-23 |
| DK70295A (da) | 1996-01-02 |
| DE19523539A1 (de) | 1996-01-04 |
| GB9512542D0 (en) | 1995-08-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AD1A | A request for search or an international type search has been filed | ||
| CD | Transfer of rights (laid open patent application) |
Free format text: CIBA SC HOLDING AG |
|
| DD | Changes of names of applicants of laid open patent applications |
Free format text: CIBA SPECIALTY CHEMICALS HOLDING INC. |
|
| RD2N | Patents in respect of which a decision has been taken or a report has been made (novelty report) |
Effective date: 19980519 |
|
| PD2B | A search report has been drawn up | ||
| VD1 | Lapsed due to non-payment of the annual fee |
Effective date: 20050101 |