NL1000709C2 - Titaan- en zirkoniumcomplexen van carbonzuren als corrosieremmers. - Google Patents

Titaan- en zirkoniumcomplexen van carbonzuren als corrosieremmers. Download PDF

Info

Publication number: NL1000709C2
Authority: NL; Netherlands
Prior art keywords: alkyl; formula; oxygen; alkoxy; interrupted
Prior art date: 1994-07-01

Application number

NL1000709A

Other languages

English (en)

Dutch (nl)

Other versions

NL1000709A1 (nl

Inventor

Andreas Kramer

Adalbert Braig

Markus Frey

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1994-07-01

Filing date

1995-06-30

Publication date

1998-07-27

1995-06-30 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1996-01-02 Publication of NL1000709A1 publication Critical patent/NL1000709A1/xx

1998-07-27 Application granted granted Critical

1998-07-27 Publication of NL1000709C2 publication Critical patent/NL1000709C2/nl

Links

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
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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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)

NL1000709A 1994-07-01 1995-06-30 Titaan- en zirkoniumcomplexen van carbonzuren als corrosieremmers. NL1000709C2 (nl)

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 (da)
JP (1)	JPH0848916A (da)
KR (1)	KR100353564B1 (da)
AT (1)	AT402297B (da)
CA (1)	CA2152975A1 (da)
DE (1)	DE19523539A1 (da)
DK (1)	DK70295A (da)
FR (1)	FR2721938B1 (da)
GB (1)	GB2290789B (da)
NL (1)	NL1000709C2 (da)

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KR20010012101A (ko)	1997-04-24	2001-02-15	아사무라 타카싯	표면처리 금속판 및 금속 표면처리액
AU2106600A (en) *	1999-01-21	2000-08-07	Ciba Specialty Chemicals Holding Inc.	Corrosion-inhibiting coating compositions for metals
US6503305B1 (en)	2000-05-18	2003-01-07	Hammond Group, Inc.	Non-toxic corrosion inhibitor
DE10202543A1 (de) *	2002-01-24	2003-08-07	Basf Coatings Ag	Beschichtungsstoffe und ihre Verwendung zur Herstellung schweißbarer Beschichtungen
DE10202545A1 (de) *	2002-01-24	2003-08-07	Basf Coatings Ag	Korrosionshemmende Mischung und Beschichtungsstoffe, enthaltend die korrosionshemmende Mischung
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
EP2217224B1 (en)	2007-11-09	2019-05-08	Basf 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
EP2662432A1 (en) *	2008-12-31	2013-11-13	MEMC Singapore Pte. Ltd.	Methods to recover and purify silicon particles from saw kerf
AU2010244136B2 (en)	2009-05-08	2016-05-12	Pronova Biopharma Norge As	Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas
WO2012059818A1 (en)	2010-11-05	2012-05-10	Pronova Biopharma Norge As	Methods of treatment using lipid compounds
AU2014222389B2 (en)	2013-02-28	2018-11-29	Pronova Biopharma Norge As	A composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same
KR102644400B1 (ko)	2015-04-28	2024-03-06	바스프 에이에스	비알코올성 지방간염의 예방 및/또는 치료를 위한 구조적으로 강화된 함황 지방산의 용도
GB201709767D0 (en) *	2017-06-19	2017-08-02	Ecolab Usa Inc	Naphthenate inhibition
CA3084728A1 (en)	2017-12-06	2019-06-13	Basf As	Fatty acid derivatives for treating non-alcoholic steatohepatitis
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

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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

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GB1295432A (da) *	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
DE59400788D1 (de) *	1993-04-07	1996-11-14	Ciba Geigy Ag	Erdalkalimetallsalze, Uebergangsmetallsalze und Uebergangsmetallkomplexe von Ketocarbonsäuren als Korrosionsinhibitoren

1995
- 1995-06-20 DK DK070295A patent/DK70295A/da not_active Application Discontinuation
- 1995-06-20 GB GB9512542A patent/GB2290789B/en not_active Expired - Fee Related
- 1995-06-28 DE DE19523539A patent/DE19523539A1/de not_active Ceased
- 1995-06-29 AT AT0111095A patent/AT402297B/de not_active IP Right Cessation
- 1995-06-29 CA CA002152975A patent/CA2152975A1/en not_active Abandoned
- 1995-06-29 KR KR1019950018009A patent/KR100353564B1/ko not_active Expired - Fee Related
- 1995-06-29 FR FR9507820A patent/FR2721938B1/fr not_active Expired - Fee Related
- 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

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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
GB9512542D0 (en)	1995-08-23
US5612093A (en)	1997-03-18
GB2290789A (en)	1996-01-10
KR960004466A (ko)	1996-02-23
JPH0848916A (ja)	1996-02-20
GB2290789B (en)	1998-09-16
CA2152975A1 (en)	1996-01-02
AT402297B (de)	1997-03-25
DK70295A (da)	1996-01-02
ATA111095A (de)	1996-08-15
NL1000709A1 (nl)	1996-01-02
FR2721938A1 (fr)	1996-01-05
KR100353564B1 (ko)	2005-04-06
DE19523539A1 (de)	1996-01-04
FR2721938B1 (fr)	1999-07-23

Publication	Publication Date	Title
NL1000709C2 (nl)	1998-07-27	Titaan- en zirkoniumcomplexen van carbonzuren als corrosieremmers.
AU699265B2 (en)	1998-11-26	Aminosilane salts and silanamides of carboxylic acids as corosion inhibitors
NL1005253C2 (nl)	2000-04-20	Corrosie-remmende bekledingssamenstelling voor metalen.
KR100239142B1 (ko)	2000-01-15	부식 억제제를 함유하는 코팅 조성물
DE69223164T2 (de)	1998-03-19	Korrosionshemmende Überzugsmassen
CN103289007B (zh)	2015-09-30	一种改进的丙烯酸锌/铜树脂制备方法
US5128396A (en)	1992-07-07	Coating compositions containing water-insoluble salts of keto-acids
AU670359B2 (en)	1996-07-11	Alkaline earth metal salts, transition metal salts and transition metal complexes of ketocarboxylic acids as corrosion inhibitors
Lamprakou et al.	2022	Tannin-based inhibitive pigment for sustainable epoxy coatings formulation
EP0669328B1 (de)	1998-09-30	Komplexe von Morpholinderivaten mit Ketocarbonsäuren als Korrosionsinhibitoren
CA2261586A1 (en)	1998-11-26	Anti-corrosion coating material
GB2279344A (en)	1995-01-04	Carrier-bound ketocarboxylic acids as corrosion inhibitors
AU2020442769A1 (en)	2022-12-15	Anti-blackening coating composition
WO2000043459A1 (de)	2000-07-27	Korrosionsinhibierende überzugszusammensetzung für metalle
KR910003848B1 (ko)	1991-06-12	방청 도료
CA2056755A1 (en)	1992-06-14	Compound, preparation and use
CH692344A5 (de)	2002-05-15	Korrosionsinhibierende Ueberzugszusammensetzung für Metalle.

Legal Events

Date	Code	Title	Description
1996-03-01	AD1A	A request for search or an international type search has been filed
1997-03-03	CD	Transfer of rights (laid open patent application)	Free format text: CIBA SC HOLDING AG
1997-06-02	DD	Changes of names of applicants of laid open patent applications	Free format text: CIBA SPECIALTY CHEMICALS HOLDING INC.
1998-08-03	RD2N	Patents in respect of which a decision has been taken or a report has been made (novelty report)	Effective date: 19980519
1998-10-01	PD2B	A search report has been drawn up
2005-03-01	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20050101