GB2182030A - Corrosion inhibition - Google Patents
Corrosion inhibition Download PDFInfo
- Publication number
- GB2182030A GB2182030A GB08625208A GB8625208A GB2182030A GB 2182030 A GB2182030 A GB 2182030A GB 08625208 A GB08625208 A GB 08625208A GB 8625208 A GB8625208 A GB 8625208A GB 2182030 A GB2182030 A GB 2182030A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- triazole
- composition according
- copper
- corrosion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000005260 corrosion Methods 0.000 title claims abstract description 34
- 230000007797 corrosion Effects 0.000 title claims abstract description 34
- 230000005764 inhibitory process Effects 0.000 title description 2
- -1 triazole compound Chemical class 0.000 claims abstract description 53
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229910052802 copper Inorganic materials 0.000 claims abstract description 42
- 239000010949 copper Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 19
- 229910052751 metal Inorganic materials 0.000 claims abstract description 16
- 239000002184 metal Substances 0.000 claims abstract description 16
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 24
- 239000012530 fluid Substances 0.000 claims description 23
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 239000003112 inhibitor Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 13
- 239000003921 oil Substances 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000002480 mineral oil Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 239000007866 anti-wear additive Substances 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000314 lubricant Substances 0.000 claims description 5
- RZYDLVDZJFHULI-UHFFFAOYSA-N 5-[2-(1h-1,2,4-triazol-5-yl)ethyl]-1h-1,2,4-triazole Chemical compound N=1C=NNC=1CCC1=NC=NN1 RZYDLVDZJFHULI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003139 biocide Substances 0.000 claims description 4
- 239000006078 metal deactivator Substances 0.000 claims description 4
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- 239000002270 dispersing agent Substances 0.000 claims description 3
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- 230000002706 hydrostatic effect Effects 0.000 claims description 3
- 239000003507 refrigerant Substances 0.000 claims description 3
- 239000013535 sea water Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- YBEQMBOBWUJWTB-UHFFFAOYSA-N 5-[4-(1h-1,2,4-triazol-5-yl)butyl]-1h-1,2,4-triazole Chemical compound N1=CNN=C1CCCCC=1N=CNN=1 YBEQMBOBWUJWTB-UHFFFAOYSA-N 0.000 claims description 2
- 239000005069 Extreme pressure additive Substances 0.000 claims description 2
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- 229910052760 oxygen Inorganic materials 0.000 claims 1
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- 239000002253 acid Substances 0.000 description 13
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- 150000003839 salts Chemical class 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 2
- AFHLFBRAUWBAFJ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol hexane-1,6-diol 2-(2-hydroxyethoxy)ethanol 2-[2-(2-hydroxyethoxy)ethoxy]ethanol methanol octadecan-1-ol Chemical compound OCC(CO)(CO)CO.C(CCCCCO)O.C(COCCOCCO)O.C(CCCCCCCCCCCCCCCCC)O.C(COCCO)O.CO AFHLFBRAUWBAFJ-UHFFFAOYSA-N 0.000 description 2
- IQEKRNXJPCBUAT-UHFFFAOYSA-N 2-[hydroperoxy(hydroxy)phosphoryl]acetic acid Chemical compound OOP(O)(=O)CC(O)=O IQEKRNXJPCBUAT-UHFFFAOYSA-N 0.000 description 2
- YZYJTQZIVRRSKM-UHFFFAOYSA-N 5-cyclohexyl-1h-1,2,4-triazole Chemical compound C1CCCCC1C1=NC=NN1 YZYJTQZIVRRSKM-UHFFFAOYSA-N 0.000 description 2
- HIRMAUHNLQGSGK-UHFFFAOYSA-N 5-hexyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CCCCCCC1=NN=C(S)N1 HIRMAUHNLQGSGK-UHFFFAOYSA-N 0.000 description 2
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
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- 239000012670 alkaline solution Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- IXHMTDIIQNIVBN-UHFFFAOYSA-N n'-(2,2-dihydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCC(O)O IXHMTDIIQNIVBN-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229940117969 neopentyl glycol Drugs 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
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- 150000003440 styrenes Chemical class 0.000 description 2
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- 239000011701 zinc Substances 0.000 description 2
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- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical class O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- PWNBRRGFUVBTQG-UHFFFAOYSA-N 1-n,4-n-di(propan-2-yl)benzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(NC(C)C)C=C1 PWNBRRGFUVBTQG-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- 150000000215 1-octanols Chemical class 0.000 description 1
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical class SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
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- HFWHTGSLDKKCMD-UHFFFAOYSA-N 2,2-bis(octanoyloxymethyl)butyl octanoate Chemical compound CCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC HFWHTGSLDKKCMD-UHFFFAOYSA-N 0.000 description 1
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- ITSTUNVMBZXJOF-UHFFFAOYSA-N 5-(1H-1,2,4-triazol-5-ylmethyl)-1H-1,2,4-triazole Chemical compound C(C1=NNC=N1)C1=NNC=N1 ITSTUNVMBZXJOF-UHFFFAOYSA-N 0.000 description 1
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- LVWSUQFUFQINOO-UHFFFAOYSA-N 5-(2-ethylhexyl)-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound C(C)C(CC1=NNC(=N1)S)CCCC LVWSUQFUFQINOO-UHFFFAOYSA-N 0.000 description 1
- GEDAJUCYLSNXIN-UHFFFAOYSA-N 5-(2-ethylhexyl)-1H-1,2,4-triazole Chemical compound C(C)C(CC1=NNC=N1)CCCC GEDAJUCYLSNXIN-UHFFFAOYSA-N 0.000 description 1
- ZTOVUOVWUQVXIM-UHFFFAOYSA-N 5-[3-(1H-1,2,4-triazol-5-yl)propyl]-1H-1,2,4-triazole Chemical compound C(CCC1=NNC=N1)C1=NNC=N1 ZTOVUOVWUQVXIM-UHFFFAOYSA-N 0.000 description 1
- MAGFPLALYSZUTR-UHFFFAOYSA-N 5-benzyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1C(S)=NN=C1CC1=CC=CC=C1 MAGFPLALYSZUTR-UHFFFAOYSA-N 0.000 description 1
- VZEAUAKJULSHNO-UHFFFAOYSA-N 5-benzyl-1h-1,2,4-triazole Chemical compound C=1C=CC=CC=1CC1=NC=NN1 VZEAUAKJULSHNO-UHFFFAOYSA-N 0.000 description 1
- ILHGXDYIVFQLIO-UHFFFAOYSA-N 5-butyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CCCCC1=NNC(S)=N1 ILHGXDYIVFQLIO-UHFFFAOYSA-N 0.000 description 1
- QGLIDFZDUPNYOI-UHFFFAOYSA-N 5-butyl-1h-1,2,4-triazole Chemical compound CCCCC1=NC=NN1 QGLIDFZDUPNYOI-UHFFFAOYSA-N 0.000 description 1
- PJOIGPQNQXRMAJ-UHFFFAOYSA-N 5-cyclododecyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1NC(=S)N=C1C1CCCCCCCCCCC1 PJOIGPQNQXRMAJ-UHFFFAOYSA-N 0.000 description 1
- HGDXTQPSTSDWCC-UHFFFAOYSA-N 5-cyclopentyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1C(S)=NN=C1C1CCCC1 HGDXTQPSTSDWCC-UHFFFAOYSA-N 0.000 description 1
- GOPHOSNTVPDHSS-UHFFFAOYSA-N 5-decyl-1h-1,2,4-triazole Chemical compound CCCCCCCCCCC1=NC=NN1 GOPHOSNTVPDHSS-UHFFFAOYSA-N 0.000 description 1
- IVDCOMSOZYWRHU-UHFFFAOYSA-N 5-dodecyl-1h-1,2,4-triazole Chemical compound CCCCCCCCCCCCC1=NC=NN1 IVDCOMSOZYWRHU-UHFFFAOYSA-N 0.000 description 1
- QKCNMYZGZIKYHA-UHFFFAOYSA-N 5-ethyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CCC1=NC(=S)NN1 QKCNMYZGZIKYHA-UHFFFAOYSA-N 0.000 description 1
- XTWRQARBVPMUPP-UHFFFAOYSA-N 5-heptyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CCCCCCCC1=NC(=S)NN1 XTWRQARBVPMUPP-UHFFFAOYSA-N 0.000 description 1
- SBESMWZBVQPWTQ-UHFFFAOYSA-N 5-heptyl-1h-1,2,4-triazole Chemical compound CCCCCCCC1=NC=NN1 SBESMWZBVQPWTQ-UHFFFAOYSA-N 0.000 description 1
- ZFBUMSNXMBBNCT-UHFFFAOYSA-N 5-naphthalen-1-yl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1C(S)=NC(C=2C3=CC=CC=C3C=CC=2)=N1 ZFBUMSNXMBBNCT-UHFFFAOYSA-N 0.000 description 1
- YKKGFDQJKLAEFR-UHFFFAOYSA-N 5-naphthalen-1-yl-1h-1,2,4-triazole Chemical compound N1C=NC(C=2C3=CC=CC=C3C=CC=2)=N1 YKKGFDQJKLAEFR-UHFFFAOYSA-N 0.000 description 1
- QEBIATYMRXSORI-UHFFFAOYSA-N 5-nonyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CCCCCCCCCC1=NC(=S)NN1 QEBIATYMRXSORI-UHFFFAOYSA-N 0.000 description 1
- KFXWHISVVLPQHQ-UHFFFAOYSA-N 5-octadecyl-1h-1,2,4-triazole Chemical compound CCCCCCCCCCCCCCCCCCC1=NC=NN1 KFXWHISVVLPQHQ-UHFFFAOYSA-N 0.000 description 1
- OTAAOINHVFMIDG-UHFFFAOYSA-N 5-octyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CCCCCCCCC1=NC(=S)NN1 OTAAOINHVFMIDG-UHFFFAOYSA-N 0.000 description 1
- SRNLWDPWTHXUEW-UHFFFAOYSA-N 5-pentyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CCCCCC1=NC(S)=NN1 SRNLWDPWTHXUEW-UHFFFAOYSA-N 0.000 description 1
- JRLMMJNORORYPO-UHFFFAOYSA-N 5-phenyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1C(S)=NC(C=2C=CC=CC=2)=N1 JRLMMJNORORYPO-UHFFFAOYSA-N 0.000 description 1
- AJNQPSCMOSUVKK-UHFFFAOYSA-N 5-propan-2-yl-1h-1,2,4-triazole Chemical compound CC(C)C=1N=CNN=1 AJNQPSCMOSUVKK-UHFFFAOYSA-N 0.000 description 1
- ZAHAMKQVODCJTO-UHFFFAOYSA-N 5-propyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CCCC1=NC(=S)NN1 ZAHAMKQVODCJTO-UHFFFAOYSA-N 0.000 description 1
- ZFWJVKLPEZPKNL-UHFFFAOYSA-N 5-propyl-1h-1,2,4-triazole Chemical compound CCCC1=NC=NN1 ZFWJVKLPEZPKNL-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
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- WFSUUZRZYJBATE-UHFFFAOYSA-N CC(CCCCCC)NC1=CC=C(C=C1)NC(CCCCCC)C.CC(CCCCCC)NC1=CC=C(C=C1)NC(CCCCCC)C.C(C)C(CC(CC)C)NC1=CC=C(C=C1)NC(CC(CC)C)CC.CC(CCC(C)C)NC1=CC=C(C=C1)NC(CCC(C)C)C Chemical compound CC(CCCCCC)NC1=CC=C(C=C1)NC(CCCCCC)C.CC(CCCCCC)NC1=CC=C(C=C1)NC(CCCCCC)C.C(C)C(CC(CC)C)NC1=CC=C(C=C1)NC(CC(CC)C)CC.CC(CCC(C)C)NC1=CC=C(C=C1)NC(CCC(C)C)C WFSUUZRZYJBATE-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- MAFYIFJGJVQPFH-UHFFFAOYSA-N N,N'-bis(2-methylphenyl)ethane-1,2-diamine 1-(diaminomethylidene)-2-(2-methylphenyl)guanidine N,N'-diphenylethane-1,2-diamine N,N'-diphenylpropane-1,3-diamine Chemical compound C1(=C(C=CC=C1)NC(=N)NC(=N)N)C.C1(=CC=CC=C1)NCCCNC1=CC=CC=C1.CC1=C(C=CC=C1)NCCNC1=C(C=CC=C1)C.C1(=CC=CC=C1)NCCNC1=CC=CC=C1 MAFYIFJGJVQPFH-UHFFFAOYSA-N 0.000 description 1
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- DIOYAVUHUXAUPX-KHPPLWFESA-N Oleoyl sarcosine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CC(O)=O DIOYAVUHUXAUPX-KHPPLWFESA-N 0.000 description 1
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- 239000004115 Sodium Silicate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- CFRNDJFRRKMHTL-UHFFFAOYSA-N [3-octanoyloxy-2,2-bis(octanoyloxymethyl)propyl] octanoate Chemical compound CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC CFRNDJFRRKMHTL-UHFFFAOYSA-N 0.000 description 1
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- 238000005273 aeration Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 238000004140 cleaning Methods 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- WIYAGHSNPUBKDT-UHFFFAOYSA-N dinonyl hexanedioate Chemical compound CCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCC WIYAGHSNPUBKDT-UHFFFAOYSA-N 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical class N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- KEZPMZSDLBJCHH-UHFFFAOYSA-N n-(4-anilinophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 KEZPMZSDLBJCHH-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000141 poly(maleic anhydride) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011684 sodium molybdate Substances 0.000 description 1
- 235000015393 sodium molybdate Nutrition 0.000 description 1
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/16—Sulfur-containing compounds
- C23F11/161—Mercaptans
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- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
A method of inhibiting the corrosion of paper or of a metal containing copper, comprising contacting the surface of the copper, or metal containing copper, with a corrosion-inhibiting amount of a triazole compound having the formula I: <IMAGE> wherein R1 is H or SH; and R2 is C2-C20 straight- or branched-chain alkyl, C5-C12 cycloalkyl, C7-C13 aralkyl, optionally substituted C6 or C10 aryl, pyridyl or a residue of formula II: <IMAGE> or, when R1 is H, (a) R2 may be a C6 or C10 arylene residue having the formula X-arylene- in which X is a residue of formula III: <IMAGE> or (b) R2 may be a residue X in which X has its previous significance, or (c) R2 may be a C1-C8 alkylene residue optionally substituted by a heteroatom and having the formula X-alkylene in which X has its previous significance.
Description
SPECIFICATION
Corrosion inhibition
The present invention relates to a method of inhibiting the corrosion of copper; and to compositions in contact with copper, and containing specified triazole corrosion inhibitors for copper.
It is well established that surfaces of copper are susceptible to corrosion when such surfaces come into contact with aqueous or non-aqueous media. Furthermore, the products of such copper corrosion may catalyse the decomposition of any organic media in contact with the corroded copper surface and may also induce corrosion of other metals, eg iron or aluminium, which may be present.
Many compounds of widely different structures have been proposed as copper corrosion inhibitors for use in media such as aqueous systems of functional fluids.
Amongst many others, one type of compound which has been found to be effective is that derived from 1,2,4-triazole. For example, in EP 25863, 3-amino-5-alkyl-1,2,4-triazoles are described and are said to be useful as corrosion inhibitors for non-ferrous metals in aqueous systems.
In earlier publications, totally different 1,2,4-triazole structures viz.. 3,5-di-substituted 1,2,4triazoles have been described as metal corrosion inhibitors in a wide range of systems. Thus in
JP 51-10186 3,5-di-aryl-1,2,4-triazole corrosion inhibitors are disclosed; in JP 51-10187, 3,5di-alkyl (or benzyl)-1,2,4-triazole inhibitors are shown; in JP Kokai 48-62634, 3,5-di-hydrocarbyl (or heterncyclyl)-1,2,4-triazole corrosion inhibitors are described.
In corrosion Science 1980, Vol. 20, 1195 to 1200, 3-mercapto-5-aryl-1,2,4-triazoles are described as useful corrosion inhibitors not for copper, rather for mild steel.
Against this varied background art, suggesting many detergent metal corrosion-inhibiting 1,2,4triazole structures for different metals, we have now found, surprisingly, certain specific 1,2,4triazole derivatives which provide outstanding copper corrosion-inhibition in various media eg functional fluids and aqueous systems.
Accordingly, the present invention provides a method of inhibiting the corrosion of copper or of a metal containing copper, comprising contacting the surface of the copper, or metal containing copper, with a corrosion-inhibiting amount of a compound having the formula I:
wherein R1 is H or SH; and R2 is C2-C20 straight- or branched chain alkyl, C5-C,2 cycloalkyl,
C7-C13 aralkyl, optionally substituted C6 or C10 aryl, pyridyl or a residue of formula ll:
or, when R1 is H, (a) R2 may be a C6 or C10 arylene residue having the formula X-arylene- in which X is a residue of formula Ill:
or (b) R2 may be a residue X wherein X has its previous significance, or (c) R2 may be a C1-C8 alkylene residue, optionally interrupted by a heteroatom and having the formula X-alkylene in which X has its previous significance.
When R2 is a C2-C20 alkyl group, it may be of straight- or branched chain eg ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl or n-eicosyl.
C5-Cl2-Cycloalkyl groups R2 may be cyclopentyl, cyclohexyl, cyclooctyl, cyclodecyi, adamantyl or cyclododecyl.
C7-C13-Aralkyl groups R2 may be benzyl, 2-phenylethyl, benzhydryl or naphthylmethyl.
C6- or C10 Aryl groups R2 are phenyl or naphthyl. Optional substituents in these aryl groups are eg nitro and hydroxyl groups.
C1-C8 alkylene groups R2 include methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene, 1 ,7-heptylene and 1,8-octylene, each optionally interrupted by a heteroatom eg an oxygen-, nitrogen- or sulfur atom.
C6- or C10 Arylene groups which are a component of the group X-arylene- are eg 1,2-, 1,3- or 1,4-phenylene and 1,4-naphthalene.
Preferred compounds of formula I are those having the formula IA:
in which R2, C2-C20 alkyl, phenyl, benzyl or X-alkylene (Cl-C8)-in which X is a residue of formula
III. In the compounds of formula IA, R2, is preferably C4-C10 alkyl, phenyl, benzyl or X-alkylene
(C,-C2) in which X is a residue of formula Ill.
Other preferred compounds of formula IB:
in which R2" is C2-C20 alkyl, especially C4-C1O alkyl.
Specific examples of compounds of formula I for use in the compositions of the inventions include: 3-Ethyl- 2,4-triazole, 3-n-Propyl- 1 ,2,4-triazole, 3-Iso-Propyl- 1 ,2,4-triazole, 3-n-Butyl- 1 2,4-triazole, 3-Sec. butyl -1,2,4-triazole, 3-n-Pentyl- 1 2,4-triazole, 3-n-Hexyl-1 2,4-triazole, 3-n-Heptyl- 1 ,2,4-triazole, 3-n-Octyl- 1 2,4-triazole, 3-(2-Ethylhexyl)- 1 ,2,4-triazole, 3-n-Nonyl-1 2,4-triazole, 3-n-Decyl- 1 ,2,4-triazole, 3-n-Dodecyl -1 ,2,4-triazole, 3-n-Tetradecyl- 1 ,2,4-triazole, 3-n-Hexadecyl-1 2,4-triazole, 3-n-Octadecyl- 1 ,2,4-triazole, 3-n-Eicosyl- 1 ,2,4-triazole, 3-Cyclopentyl-1 2,4-triazole, 3-Cyclohexyl-1 ,2,4-triazole, 3-Cyclododecyl-1 ,2,4-triazole, 3-Benzyl-1 ,2,4-triazole, 3-Phenyl- 1 2,4-triazole, 3-(4-Nitrophenyl)-1 2,4-triazole 3-Naphthyl-1 ,2,4-triazole, 3-(2-Pyridyl)- 1 ,2,4-triazole 3-(3-Pyridyl)- 1 ,2,4-triazole 3-(4-Pyridyl)- 1 2,4-triazole 3-(4H- 1 ,2,4-Triazolyl)- 1 ,2,4-triazole, 3 ,3'-( 1 ,2-Phenylene)-bis-( 1 2,4-triazole), 3,3'-(1 ,3-Phenylene)-bis-( 1,2,4-triazole), 3,3'-Bis-(1 2,4-triazole) 3,3'-Methylene-bis(1,2,4-triazole), 3 ,3'-Ethylene-bis( 1 ,2,4-triazole), 3,3'- [ 1 ,3-propylene ] -bis( 1 ,2,4-triazole) 3 ,3'- [ 1 ,4-butylene ] -bis( 1 2,4-triazole) 3,3'-1 ,8-Octylene-bis(1 ,2,4-triazole), 3-Ethyl-5-mercapto- 1,2,4-triazole, 3-n-Propyl-5-mercapto- 1,2,4-triazole, 3-lsopropyl-5-mercapto- 1 ,2,4-triazole, 3-n-Butyl-5-mercapto- 1,2,4-triazole, 3-Mercapto-5-n-pentyl- 1,2,4-triazole, 3-n-Hexyl-5-mercapto- 1,2,4-triazole, 3-n-Heptyl-5-mercapto- 1 ,2,4-triazole, 3-n-Octyl-5-mercapto- 1,2,4-triazole, 3-(2-Ethylhexyl)-5-mercapto- 1,2,4-triazole, 3-n-Nonyl-5-mercapto- 1,2,4-triazole, 3-n-Decyl-5-mercapto- 1,2,4-triazole, 3-n-Dodecyl-5-mercapto- 1,2,4-triazole, 3-n-Tetradecyl-5-mercapto- 1,2,4-triazole, 3-n-Hexadecyl-5-mercapto- 1 ,2,4-triazole, 3-n-Octadecyl-5-mercapto- 1,2,4-triazole, 1 2,4-triazole, 3-n-Eicosyl-5-mercapto- 1,2,4-triazole, 3-Cyclopentyl-5-mercapto- 1 ,2,4-triazole, 3-Cyclohexyl-5-mercapto- 1 2,4-triazole, 3-Cyclododecyl-5-mercapto- 1,2,4-triazole, 3-Benzyl-5-mercapto- 1 ,2,4-triazole, 3-Phenyl-5-mercapto- 1,2,4-triazole, 3-Naphthyl-5-mercapto- 1,2,4-triazole.
Particularly preferred compounds of formula I are: 3-Phenyl-1 2,4-triazole, 3-n-Hexyl-1 2,4-triazole, 3-n-Hexyl-5-mercapto- 1,2,4-triazole, 3,3'-Methylene-bis(1 2,4-triazole), 3,3'-Ethylene-bis(l,2,4-triazole).
3-Benzyl-1 ,2,4-triazole 3-Cyclohexyl-5-mercapto- 1,2,4-triazole and 3-Cyclohexyl-1 ,2,4-triazole.
Many of the compounds of formula I are known but some specific compounds viz. those having the formula:
wherein n is 2, 3 or 4 are new and, as such, form a further aspect of the present invention.
The compounds of formula I whether known or new may be produced by methods which are well known per se.
For example, the compounds of formula I in which Rl is hydrogen may be prepared by (a) cyclisation of the corresponding acylamidrazones using the method described by Heinz, Hilgetag and Jahnchen in Chem.Ber. 1968, 101, 2033; (b) by deamination of the corresponding 3-amino1,2,4-triazoles using the process described by Bachman and Heisey in J.Amer.Chem.Soc. 1949, 71, 1985; or (c) by de-sulfurisation of the corresponding 3-mercapto-1,2,4-triazoles using the method of Hoggarth in J.Chem.Soc. 1949, 1160.
Compounds of formula I in which Rl is a mercapto group may be synthesized by (a) cyclising the corresponding acylthiosemicarbazides using the method of Dutta et al. J.lndian Chem.Soc.
1968, 45, 338; or (b) condensing the appropriate carboxylic acid ester with thiosemicarbazide using the method of Willems and Vandenberghe, Bull.Soc.Chim.Belges. 1966, 75, 358).
The compounds of formula IV may be produced by desulphurisation of the corresponding, known 3,3'-alkylene-bis-1 ,2,4-triazole-5-thiones (Willems and Vandenberghe, supra), using the method of Jones and Ainsworth in J. Amer. Chem. Soc. 1953, 75, 4915.
The compound of formula I may be contacted with the copper surface to be protected by any of a variety of techniques. For example, the copper surface may be wrapped in a film impregnated with the compound of formula I or the copper surface may be dipped into a solution eg an aqueous solution containing a compound of formula I. More usually however, the copper surface will be permanently in contact with a substrate which causes corrosion of the copper surface. In such cases, the copper surface can be effectively inhibited against corrosion by adding a corrosion-inhibiting amount of a compound of formula I to the substrate.
The present invention therefore also provides a composition comprising a substrate in contact with copper, or a metal containing copper and a copper corrosion-inhibiting amount, preferably 0.0001% to 5% by weight, based on total weight of the substrate, of a compound of formula I as hereinbefore defined.
Examples of substrates which may be treated according to the present invention include functional fluids such as lubricants eg those having a mineral oil, poly-alpha olefin or synthetic carboxylic acid ester base; hydraulic fluids eg those based on mineral oils, phosphate esters, aqueous polyglycol/polyglycol ether mixtures or glycol systems; oil-in-water or water-in-oil systems; metal-working fluids having, as their base, mineral oil or aqueous systems; water- or aqueous glycol- or ethylene- or propylene glycol/methanol based engine coolant systems; transformer- or switch oils; as well as aqueous systems eg industrial cooling water; aqueous airconditioning systems; steam-generating systems; sea-water evaporator systems; hydrostatic cookers; and aqueous closed circuit heating or refrigerant systems.
For use in oil-based functional fluids, those compounds of formula I are preferred in which R1 is H and R2 is an oleophilic group, especially a C2-C10 straight- or branched-chain alkyl group, a
C6 or C10 aryl group, a C7-C,3 aralkyl group or a C6-C12 cycloalkyl group.
On the other hand, for use in aqueous, glycol or water/glycol functional fluids, those compounds of formula I are preferred in which R1 is H or SH and R2 is C4-C7 straight- or branchedchain alkyl, C6 or C10 aryl, C7-C13 aralkyl or a residue of formula X-(CH2)n- in which X has its previous significance and n is O or 1 to 8, but in which n is preferably 0 or 1 to 4.
Those compounds of formula I in which R1 is SH are preferably incorporated into a functional fluid as pre-formed alkali metal (preferably sodium) or organic amine salts, or they may be dissolved in an aqueous functional fluid by adding to the latter an appropriate amount of an alkali (preferably sodium hydroxide).
Those compounds of formula I in which R1 is H may be incorporated into a functional fluid as the neutral species and, indeed, this technique is very much preferred when such compounds are incorporated into oil-based functional fluids.
Alternatively, for use in non-oil based functional fluids, the compounds of formula I may be used in either alkaline or acidic solution. In alkaline solution, sodium hydroxide is the preferred base used and, in acidic solution, the use of a mineral acid such as hydrochloric, sulfuric or phosphoric acid is preferred.
When a functional fluid substrate is a synthetic lubricant, examples thereof include lubricants based on a diester of a dibasic acid and a monohydric alcohol, for instance dioctyl sebacate or dinonyladipate; on a triester of trimethylolpropane and a monobasic acid or mixture of such acids, for instance trimethylol propane tripelargonate, trimethylolpropane tricaprylate or mixtures thereof; on a tetraester of pentaerythritol and a monobasic acid or mixture of such acids, for instance pentaerythritol tetracaprylate; or on complex esters derived from monobasic acids, dibasic acids and polyhydric alcohols, for instance a complex ester derived from trimethylol propane, caprylic acid and sebacic acid; or of mixtures thereof.
Other synthetic lubricants are those known to the art-skilled and described eg in "Schmiermittel-Taschenbuch" (Huethig Verlag, Heidelberg 1974). Especially suitable, apart from the preferred mineral oils are eg phosphates, glycols, polyglycols, polyalkylene glycols and poly-alpha olefins.
In order to improve various applicational properties, a functional fluid composition of the invention may also contain other additives such as, for oil-based systems, one or more of antioxidants, metal deactivators, further corrosion or rust inhibitors, viscosity-index improvers, pour-point depressants, dispersants/surfactants or anti-wear additives; and for aqueous-based systems, one or more of antioxidants, other corrosion- and rust inhibitors, metal deactivators, extreme pressure- or anti-wear additives, complexing agents, precipitation inhibitors, biocides, buffering agents and anti-foams.
For oil-based systems, examples of other additives are:
Examples of phenolic antioxidants
1. Alkylated Monophenols 2,6-Di-tert.-butylphenol 2-tert.-butyl-4,6-dimethylphenol 2,6-Di-tert.-butyl-4-ethylphenol 2,6-Di-tert.-butyl-4-n-butylphenol 2,6-Di-tert.-butyl-4-i-butylphenol 2,6-Di-cyclopentyl-4-methylphenol 2-(ss-Methylcyclohexyl)-4,6-dimethylphenol 2,6-Di-octadecyl-4-methylphenol 2,4,6-Tri-cyclohexylphenol 2,6-Di-tert.-butyl-4-methoxymethylphenol 2. Alkylated Hydroquinones 2,6-Di-tert.-butyl-4-methoxyphenol 2,5-Di-tert.-butyl-hydroquinone 2,5-Di-tert.-amyl-hydroquinone 2,6-diphenyl-4-octadecyloxyphenol 3.Hydroxylated Thiodiphenylethers 2,2'-Thio-bis-(6-tert.butyl-4-methylphenol) 2,2'-Thio-bis-(4-octylphenol) 4,4'-Thio-bis-(6-tert.butyl-3-methylphenol) 4,4'-Thio-bis-(6-tert. butyl-2-methylphenol) 4. Alkylidene-Bisphenols 2,2'-Methylene-bis-(6-tert.-butyl-4-methylphenol) 2, 2'-Methylene-bis-(6-tert.-butyl-4-ethylphenol) 2,2'-Methylene-bis-(4-methyl-6-(a-methylcycloheXyl)-phenol) 2,2'-Methylene-bis-(4-methyl-6-cyclohexylphenol) 2,2'-Methylene-bis-(6-nonyl-4-methylphenol) 2,2'-Methylene-bis-(4,6-di-tert.-butylphenol) 2,2'-Ethylidene-bis-(4, 6-di-tert.-butylphenol) 2,2'-Ethylidene-bis-(6-tert.-butyl-4-isobutylphenol) 2,2'-Methylene-bis-(6-(a-methylbenzyl-4-nonylphenol) 2,2'-Methylene-bis-(6-(a, -dimethylbenzyl)-4-nonylphenol) 4,4'-Methylene-bis-(6-tert.-butyl-2-methylphenol) 1,1 '-Bis-(5-tert.-butyl-4-hydroxy-2-methylphenol)-butane 2,6'-Di-(3-tert. butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol 1,1 ,3-Tris-(5-tert.butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane Ethyleneglycol-bis- [ 3 ,3-bis-(3'-tert.-butyl-4'-hydroxyphenyl)-butyrate ] Di-(3-tert.-butyl-4-hydroxy-5-methylphenyl)-dicyclopentadiene Di-[3'-tert.-butyl-2'-hydroxy-5'-methyl-benzyl)-6-tert.-butyl-4-methyl-phenyl]-terephthalate 5.Benzyl Compounds 1,3 ,5-Tri-(3 ,5-di-tert.-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene Di-(3 ,5-di-tert.-butyl-4-hydroxybenzyl)-sulfide Bis-(4-tert.-butyl-3-hydroxy-2,6-dimethylbenzyl)dithiolterephthalate 1 ,3,5-Tris-(3,5-di-tert.-butyl-4-hydroxybenzyl)-isocyanurate 1.3. 5-Tris-(4-tert.-butyl-3-hydroxy-2 ,6-dimethylbenzyl)-isocyanurate 3,5-Di-Tert.-butyl-4-hydroxybenzyl-phosphonic acid-dioctadecylester 3,5-Di-tert.-butyl-4-hydroxybenzyl-phosphonic acid-monoethylester Calcium-salt 6.Acylaminophenols 4-Hydroxy-lauric acid anilide 4-Hydroxy-stearic acid anilide 2,4-Bis-octylmercapto-6-(3 , 5-di-tert.-butyl-4-hydroxyanilino)-s-triazine N-(3 ,5-di-tert.-butyl-4-hydroxyphenyl)-carbamic acid octyl ester 7. Esters of fi-(3, 5-Di-tert. -buty!-4-hydroxypheno!)-propionic acid with mono- or polyhydric alcohols eg with
Methanol Diethyleneglycol
Octadecanol Triethyleneglycol 1,6-Hexandiol Pentaerythritol
Neopentylglycol Tris-hydroxyethyl-isocyanurate
Thiodiethyleneglycol Di-hydroxyethyl-oxalic acid diamide 8.Esters of fl-(5-tert.-butyl-4-hydroxy-3-methylphenyl)-propionic acid with mono- or polyhydric alcohols eg with
Methanol Diethyleneglycol
Octadecanol Triethyleneglycol 1,6-Hexandiol Pentaerythritol
Neopentylglycol Tris-hydroxyethyl-isocyanurate
Thiodiethyleneglycol Di-hydroxyethyl-oxalic acid diamide 9.Amides of fi-(3,5-Di-tert.-butyl-4-hydroxyphenyl)-propionic acid eg N,N'-Di-(3,5-di-tert.-butyl-4-hydroxyphenylpropionyi)-hexamethylene-diamine N,N'-Di-(3,5-di-tert.-butyl-4-hydroxyphenylpropionyl)-trimethylene-diamine N,N'-Di-(3,5-di-tert.-butyl-4-hydroxyphenylpropionyl)-hydrazine Examples of amine antioxidants::
N,N'-Di-isopropyl-p-phenylenediamine
N,N'-Di-sec.-butyl-p-phenylenediamine N,N'-Bis( 1 ,4-dimethyl-pentyl)-p-phenylenediamine N,N'-Bis( 1 -ethyl-3-methyl-pentyl)-p-phenylenediamine N,N'-Bis( 1 -methyl-heptyl)-p-phenylenediamine N,N'-Bis( 1 -methyl-heptyl)-p-phenylenediamine N,N'-Dicycldhexyl-p-phenylenediamine N,N'-Diphenyl-p-phenylenediamine N,N'-Di-(naphthyl-2-)-p-phenylenediamine N-lsopropyl-N'-phenyl-p-phenylenediamine N-( 1 ,3-dimethyl-butyl)-N'-phenyl-p-phenylenediamine N-( 1 -Methyl-heptyl)-N'-phenyl-p-phenylenediamine
N-Cyclohexyl-N'-phenyl-p-phenylenediamine 4-(p-Toluene-sulfonamido)-diphenylamine N,N'-dimethyl-N,N'-di-sec.-butyl-p-phenylenediamine Diphenylamine 4-lsopropoxy-diphenylamine
N-Phenyl- 1 -naphthylamine
N-Phenyl-2-naphthylamine octylated Diphenylamine octylated N-phenyl- (or) naphthylamine 4-n-Butylaminophenol 4-Butyrylamino-phenol 4-Nonanoylamino-phenol 4-lsodecanoylamino-phenol 4-Octadecanoylamino-phenol
Di-(4-methoxy-phenyl)-amine 2,6-Di-tert.-butyl-4-dimethylamino-methyl-phenol 2,4'-diamino-diphenylmethane 4,4'-Diamino-diphenylmethane N,N,N',N'-Tetramethyl-4,4'-diamino-diphenylmethane 1,2-Di-(phenylamino)-ethane 1,2-Di- [ (2-methyl-phenyl)-amino ] -ethane 1,3-Di-(phenylamino)-propane (o-tolyl)-biguanide Di- [ 4-(1 ',3'-dimethyl-butyl)-phenyl ] amine Examples of further metal passivators are: for copper eg
Benzotriazole, tolutriazole and derivatives thereof, tetrahydrobenzotriazole,2-mercaptobenzthiazole, 2,5-dimercaptothiadiazole, salicylidene-propylenediamine and salts of salicylaminoguanidine.
Examples of rust inhibitors are: (a) Organic acids, their esters, metal salt and anhydrides eg N-oleoyl-sarcosine, sorbitan-monooleate, lead-naphthenate, dodecenyl-succinic acid (and its partial esters and amides), 4-nonyl-phenoxy-acetic acid.
(b) nitrogen-containing compounds eg.
I. Primary, secondary or tertiary aliphatic or cycloaliphatic amines and amine-salts of organic and inorganic acids eg oil-soluble alkylammonium carboxylates
II. Heterocyclic compounds eg substituted imidazolines and oxalines (c) Phosphorus-containing compounds eg
Amine salts of phosphonic acid partial esters, zinc dialkyldithio phosphates (d) Sulfur-containing compounds eg
Barium-dinonylnaphthalene-n-sulfonates, calcium petroleum sulfonates
Examples of viscosity-index improvers are eg
Polymethacrylates, vinylpyrrolidone/methacrylate-copolymers, polybutenes, olefin-copolymers styrene/acrylate-copolymers.
Examples of pour-point depressants are eg
Polymethacrylates, or alkylated naphthalene derivatives
Examples of dispersants/surfactants are eg
Polybutenylsuccinic acid-amides, polybutenylphosphonic acid derivatives, basic magnesium-, calcium-, and bariumsulfonates and -phenolates.
Examples of anti-wear additives are eg
Sulfur- and/or phosphorus- and/or halogen-containing compounds eg sulfurised vegetable oils, zinc dialkyldithiophosphates, tritolylphosphate, chlorinated paraffins, alkyl- and aryldisulfides.
In the treatment of substrates which are completely aqueous, such as cooling water systems, air-conditioning system, steam-generating systems, sea-water evaporator systems, hydrostatic cookers, and closed circuit heating or refrigerant systems, further corrosion inhibitors may be used such as, for example, water soluble zinc salts; phosphates; polyphosphates; phosphonic acids and their salts, for example, acetodiphosphonic acid, nitrilotris methylene phosphonic acid and methylamino dimethylene phosphonocarboxylic acids and their salts, for example, those described in German Offenlegungsschrift 2632774, hydroxyphosphonoacetic acid, 2-phosphonobutane-1,2,4-tricarboxylic acid and those disclosed in GB 1572406; nitrates, for example sodium nitrate; nitrites eg sodium nitrite; molybdates eg sodium molybdate; tungstates; silicates eg sodium silicate; benzotriazole, bis-benzotriazole or copper deactivating benzotriazole or tolutriazole derivatives or their Mannich base derivatives; N-acyl sarcosines; N-acylimino diacetic acids; ethanolamines; fatty amines; and polycarboxylic acids, for example, polymaleic acid and polyacrylic acid, as well as their respective alkali metal salts, copolymers of maleic anhydride, eg copolymers of maleic anhydride and sulfonated styrene, copolymers of acrylic acid eg copolymers of acrylic acid and hydroxyalkylated acrylic acid, and substituted derivatives of polymaleic and polyacrylic acids and their copolymers.Moreover, in such completely aqueous systems, the triazole copper corrosion inhibitor used according to the invention may be used in conjunction with dispersing and/or threshold agents eg polymerised acrylic acid (or its salts), phosphinopolycarboxylic acids (as described and claimed in British Patent 1458235), the cotelomeric compounds described in European Patent Application No. 0150706, hydrolysed polyacrylonitrile, polymerised methacrylic acid and its salts, polyacrylamide and co-polymers thereof from acrylic and methacrylic acids, lignin sulphonic acid and its salts, tannin, naphthalene sulphonic acid/formaldehyde condensation products, starch and its derivatives, cellulose, acrylic acid/lower alkyl hydroxyacrylate copolymers eg those described in US Patent Specification No. 4029577, styrene/maleic anhydride copolymers and sulfonated styrene homopolymers eg those described in US
Patent Specification No. 4374733 and combinations thereof. Specific threshold agents, such as for example, 2-phosphonobutane-1,2,4-tri-carboxylic acid, acetodiphosphonic acid, hydrolysed polymaleic anhydride and its salts, alkyl phosphonic acid, hydroxyphosphonoacetic acid 1-aminoalkyl-1, 1-diphosphonic acids and their salts, and alkali metal poly-phosphates, may also be used.
Precipitating agents such as alkali metal orthophosphates, carbonates; oxygen scavengers such as alkali metal sulphites and hydrazines; sequestering agents such as nitrilotriacetic acid and its salts; antifoaming agents such as silicones eg polydimethylsiloxanes, distearylsebacamides, distearyl adipamide and related products derived from ethylene oxide and/or propylene oxide condensations, in addition to fatty alcohols, such as capryl alcohols and their ethylene oxide condensates; and biocides eg amines, quaternary ammonium compounds, chlorophenols, sulphurcontaining compounds such as sulphones, methylene bis thiocyanates and carbamates, isothiazolones, brominated propionamides, triazines, phosphonium compounds, chlorine and chlorine-release agents and organometallic compounds such as tributyl tin oxide, may be used.
The compounds of formula I combine excellent copper deactivation properties with good solubility in aqueous- and oil-based substrates.
The following Examples further illustrate the present invention. All parts and percentages given therein are by weight. Examples 1 and 2 are included for the purposes of comparison only.
Examples 1 to 17
A 0.006% solution of a test compound of formula (I) is prepared in water containing 0.132 g/l MgS04.7H2O and 0.68 g/l CaCl2.6H2O (water as used in DIN 51360 test), and the pH of the solution is adjusted to 8.5 with sodium hydroxide.
A piece of copper foil (20 x 50 x 0.1 mm) is cleaned by rubbing it with cotton wool soaked with water and powdered pumice, dried and weighed. It is then fully immersed in 50 ml of the solution so prepared contained in a 60 ml bottle fitted with a screw cap. The bottle is then placed for 24 hours in an oven maintained at 70 C. At the end of this time, the strip is removed, washed and dried and its colour is recorded (using the ASTM D130 colour ranking). It is then immersed for 15 seconds in 5N hydrochloric acid at 20 C, washed, dried and reweighed.
The results are summarised in Table l: Table I
I Exatiple I Ccmpourxi of formula I I Test Results I Example ~~~~~~~~~~~~~~~~~~~~~~~~~ I I I I Weight loss I Metal Appearance I Solution I I I R1 i R2 I (mg) I and rating I AFçearance I I I----- ------------- I I - I - ~l~~~~~~ I------------------ l~ I - I | CONTROL I 4.6 1 4D I Colourless I I 1 I H I | H I 1.0 1 10% surface I Colourless I I i I II pale green I I 2 I SH I | H | H | 0.3 I purple stains I 1 3 I H I C2H5 1 0.2 1 1B I Colourless I 1 4 I H I n-C4H9 1 0.3 1 1B I colourless I I 5 I H I | i-C4Hg I 0.1 I 1B I 1 6 I H n-C6H13 1 0.4 1 1B I Colourless I 1 7 I H I nC7H13 n- q 0.3 I 0.3| 1B I Colourless I 1 8 |I H I Ph 1 0.2 1 1A I Colourless I 1 9 t H I CH2Ph I 0.2 1 1B I Colourless I 1 10 1 H C-C6H11 I 0.1 I 1B I Colourless I I I I I I I 11 I H I 1 I 0.3 1 1B I Colourless I I I1 -N I I I I I I I I I I I I I 1 12 I H I HN-N I 1 0.5 |1 1B I Colourless I I I I 1 I I l I NN CH2CH2- I i I I I I I 1 13 I SH t C2H5 I 0.1 I 1B I Colourless I 1 14 I SH |n-C4Hg 1 0.2 1 1B I Colourless I I 15 I SH I i-C4Hg I 0.1 I IB I | Colourless I 1 16 1 SH I n-C6H13 1 0.4 1 1B I Colourless I I 17 I H I 4-N02C#% 1 0.2 I iB I Colourless I I I 17 I I I 4-N02C6H4 ~~~~~~~~0.2 1 1B |ColourlessI ~~~~~~~ On the ASTM D130 rating, 1 represents zero to slight tarnish, 2 represents moderate tarnish, 3 represents dark tarnish and 4 represents corrosion. The designations A,B and D indicate shadings within the numerical gradings.
Examples 18 to 23
A 0.2% solution of a test compound of formula I is prepared in an antifreeze formulation comprising:
Component wt%
Borax 3% triethanolamine 2.9%
Phosphoric acid 1.1% Glycol 93%
The 0.2% test formulation is then diluted to 33% v/v with ASTM D1384 water, thus giving a test compound concentration of 666ppm.
A 3"x0.5" (7.62cmx 1.27cm) cleaned, preweighed copper foil strip is placed in the solution, through which air is passed at a rate of Il/hour whilst the temperature of the solution is maintained at 78-82 C for 48 hours.
On completion, the copper strip is taken from the solution, washed with deionised water, then immersed in a 5N hydrochloric acid solution at 200C for 15 seconds. The copper strip is then washed and reweighed.
The appearance of both the test solution and copper strip is recorded and the weight loss is expressed in mg.
The results are set out in Table II.
Table II
I Example I Compound of formula I I Test Results I I I I I I-I IE2 I Weight loss I Metal Appearance Solution I I I R1 I I (mg) I and rating I Appearance I I- I----II-------------------I ---------- I---------------I-I I- I I - |I #NTTOL 1 33 1 Green deposit I Green I I I I I I I 18 |I |n-C6H13 I 1.8 I 2B I Colourless I 1 19 I H I Ph I I I I 1 20 |I H I CH2Ph 1 1.6 1 1B I Colourless I I I I I I I 1 21 |H |HIN I 1.1 I 1B g Colourless I I I l#' I I I I N N cH2CH2- I I I I I I I I I I I 1 22 I SH I n#H9 SH |n-C4Hg|1.3 1 1B I Colourless I I 23 I SH I n#H13 I 0.1 I iB I Colourless I 1 23| I | nC6H13 I 0.1 1 1BI Colourless Examples 24 to 28
Two clean, pre-weighed copper coupons (50mm x 25mm x 1 mm) are suspended in 200ml of a 500ppm sodium chloride solution in distilled water at pH 7 containing the desired amount of compound of formula (I).
The test is then run for 65 hr+ 1 hr at 400C with aeration rate of 500 ml/min air, any evaporative loss being made up with distilled water.
After cleaning the weight losses of the two metal coupons are determined and the corrosion rate calculated in mg/dm2/day (mdd).
The results are set out in Table Ill.
Table III
I Example I Compound of formula I I Test Results I l I IConcentrationlCorrosion Rate I IR1 1 R2 g (ppm) I (mdd) 1---------1-----1----------------------- I I I I I I - I CONTROL |I 1 13.48 1 24 I H I -Ph I 10 1 0.22 1 25 1 SH I n-C4H9 1 10 1 0.87 1 26 |I H I n-C6H13 1 10 1 0.22 1 27 |H H I -CH2Ph 1 10 1 0.51 1 28 |H |H I RN----N 1 10 1 1.88 I I N I CH2CH2
Examples 29 to 32
A 0.05% solution of the test compound of formula (I) is prepared in a turbine quality mineral oil containing 50ppm of- added, dissolved sulphur.
A copper strip (60x lOx lmm) is polished with 100 grade silicon carbide grit which has been picked up on cotton wool wetted with petroleum ether. The polished strip is then immediately totally immersed in the prepared solution, which is maintained at 1000C for 2 hours. After this time, the strip is removed, washed with petroleum ether, dried and its colour is compared with those of the ASTM D130 Copper Strip Corrosion Standard Chart.
The results are summarised in Table IV.
Table IV
I i Compound of formula I I I Example I~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ g I Rating I R1 I R2 I I - I Blank (Control) I I 3B I I 2q I H I | phenyl I 1A l 30 1 H I cyclohexyl I 1B I I I i 31 H I | benzyl I 1B l Examples 32 to 34 3,3'-ethylene-bis(1,2,4-triazoline-5-thione) (1 1.4g; 0.05 mole) is added in small portions to a stirred mixture of conc. nitric acid (10 ml) and water (20 ml) containing sodium nitrite (0.05g) at 45-50 C. After complete addition, the mixture is cooled on ice and neutralised with 50% NaOH solution. Upon neutralisation, a white solid, 3,3'-ethylene-bis-1,2,4-triazole precipitated and is filtered off, washed with a small quantity of water and then dried in vacuo.
Yield=4.2g; mp=241-3 C 'H nmr (d6-Me2SO) : b3.15 (s,4H); 8.1 (s,2H); 10-11 (broadened peak, 2H) 13C nmr (d6-Me2SO) : d26.2, 148.8, 159.1
Using analogous procedures, 3,3'- [ 1,3-propylene ] -bis(1,2,4-triazole m. point 135-400C and 3,3'- [ 1,4-butylene ] -bis(1,2,4-triazole) m. point 236-9 C are prepared.
Claims (21)
1. A method of inhibiting the corrosion of copper or of a metal containing copper, comprising contacting the surface of the copper, or metal containing copper, with a corrosion-inhibiting amount of a triazole compound having the formula l:
wherein R1 is H or SH; and R2 is C2-C20 straight- or branched-chain alkyl, C5-C12 cycloalkyl,
C7-C13 aralkyl, optionally substituted C6 or C10 aryl, pyridyl or a residue of formula ll:
or, when R1 is H, (a) R2 may be a C6 or C10 arylene residue having the formula X-arylene- in which X is a residue of formula Ill:
or (b) (R2) may be a residue X in which X has its previous significance or (c) R2 may be a C1-C8 alkylene residue optionally substituted by a heteroatom and having the formula X-alkylene in which X has its previous significance.
2;: A method according to claim 1 wherein the triazole compound has the formula IA:
in which R2' is C2-C20 alkyl, phenyl, benzyl or X-alkylene (C1-C8)- wherein X is as defined in claim 1.
3. A method according to claim 2 wherein R2, is C4-C10 alkyl, phenyl, benzyl or X-alkylene (C1-C2)- in which X is as defined in claim 1.
4. A method according to claim 1 wherein the triazole compound has the formula IB:
in which R2" is C2-C20 alkyl.
5. A method according to claim 4 wherein R2" is C4-Cro alkyl.
6. A composition comprising a substrate, in contact with copper, or a metal containing copper, and a copper corrosion-inhibiting amount of a compound of formula I, as defined in claim 1.
7. A composition according to claim 6 wherein the amount of the compound of formula I is from 0.0001% to 5% by weight, based on the total weight of the substrate.
8. A composition according to claim 6 or 7 wherein the substrate is a functional fluid.
9. A composition according to claim 8 wherein the functional fluid is a lubricant, a hydraulic fluid; an oil-in-water or water-in-oil system; metal working fluids with a mineral oil or aqueous base; an engine coolant system based on water, aqueous glycol, or ethylene glycol (or propylene glycol)/methanol; or a transformer or switch oil.
10. A composition according to claim 8 or 9 wherein the functional fluid is oil-based and, in the compound of formula I, R1 is H and R2 is an oleophilic group.
11. A composition according to claim 10 wherein R2 is a C2-C,O alkyl group, a C7-C,3 aralkyl group or a C5-C12 cycloalkyl group.
12. A composition according to claim 8 or 9 wherein the functional fluid is an aqueous, glycol or water/glycol fluid and, in the compound of formula I, R1 is H or SH and R2 is C4-C7 alkyl, C6 or C10 aryl, C7-C13 aralkyl or a residue of formula X-(CH2)n- in which X is as defined in claim 1 and n is O or 1 to 8.
13. A composition according to any of claims 8 to 12 wherein the functional fluid is oilbased and contains one or more antioxidants, metal deactivators, further corrosion or rust inhibitors, viscosity-index improvers, pour-point depressants, dispersants/surfactants or anti-wear additives.
14. A composition according to any of claims 8 to 12 wherein the functional fluid is aqueous-based and contains one or more antioxidants, other corrosion- or rust inhibitors, metal deactivators, extreme-pressure or anti-wear additives, complexing agents, precipation inhibitors, biocides, buffering agents or anti-foams.
15. A composition according to claim 6 or 7 wherein the substrate is industrial cooling water, an aqueous air-conditioning system, a steam-generating system, a sea-water evaporator system, a hydrostatic cooker, or an aqueous closed-circuit heating or refrigerant system.
16. A composition according to claim 16 wherein the substrate contains one or more further corrosion inhibitors; dispersing and/or threshold agents; precipitating agents; oxygen scavengers; antifoaming agents; or biocides.
17. A method according to claim 1 substantially as described with reference to any of
Examples 3 to 31.
18. Composition according to claim 6 substantially as described with reference to any of
Examples 3 to 31.
19. 3,3'-Ethylene-bis(1 ,2,4-triazole).
20. 3,3'- [ 1 ,3-Propylene ] -bis-(1 2,4-triazole).
21. 3,3'- [ 1 ,4-Butylene ] -bis-( 1 ,2,4-triazole).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB858526160A GB8526160D0 (en) | 1985-10-23 | 1985-10-23 | Corrosion inhibition |
Publications (2)
Publication Number | Publication Date |
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GB8625208D0 GB8625208D0 (en) | 1986-11-26 |
GB2182030A true GB2182030A (en) | 1987-05-07 |
Family
ID=10587134
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB858526160A Pending GB8526160D0 (en) | 1985-10-23 | 1985-10-23 | Corrosion inhibition |
GB08625208A Withdrawn GB2182030A (en) | 1985-10-23 | 1986-10-21 | Corrosion inhibition |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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GB858526160A Pending GB8526160D0 (en) | 1985-10-23 | 1985-10-23 | Corrosion inhibition |
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JP (1) | JPS6299484A (en) |
DE (1) | DE3635636A1 (en) |
FR (1) | FR2588883A1 (en) |
GB (2) | GB8526160D0 (en) |
IT (1) | IT8622087A0 (en) |
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US10737280B2 (en) | 2016-09-23 | 2020-08-11 | Central South University | Method of using flotation collector containing azolethione structure |
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JPH02122060A (en) * | 1988-10-28 | 1990-05-09 | Technol Res Assoc Super Heat Pump Energ Accum Syst | Chemical heat accumulator and its surface treatment |
GB9013142D0 (en) * | 1990-06-13 | 1990-08-01 | Ciba Geigy Ag | Chemical compounds useful as metal deactivators |
CN103086988B (en) * | 2013-02-21 | 2014-10-29 | 天津师范大学 | Phenyl bistriazole compound, and preparation method and application thereof |
DE102014105823A1 (en) * | 2014-04-25 | 2015-10-29 | Harting Kgaa | Post-cleaning process of metallic contact elements |
WO2023190264A1 (en) * | 2022-03-29 | 2023-10-05 | 四国化成工業株式会社 | Triazole compound, method for synthesizing said triazole compound, coupling agent and uses thereof |
TW202411469A (en) * | 2022-06-30 | 2024-03-16 | 日商四國化成工業股份有限公司 | Surface treatment agent for metal cord and use of said surface treatment agent |
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US3408307A (en) * | 1966-02-10 | 1968-10-29 | Nalco Chemical Co | Inhibiting corrosion of copper with tetrazoles |
US4178253A (en) * | 1977-04-05 | 1979-12-11 | Ciba-Geigy Corporation | Corrosion inhibited lubricant compositions |
JPS55164263A (en) * | 1979-06-09 | 1980-12-20 | Toshiba Chem Corp | Electrical insulating varnish for cloth pipe |
US4357396A (en) * | 1981-01-26 | 1982-11-02 | Ppg Industries, Inc. | Silver and copper coated articles protected by treatment with mercapto and/or amino substituted thiadiazoles or mercapto substituted triazoles |
DE3129193A1 (en) * | 1981-07-24 | 1983-02-03 | Hoechst Ag, 6000 Frankfurt | Azole derivatives, processes for their preparation, and their use as agents for combating pests |
-
1985
- 1985-10-23 GB GB858526160A patent/GB8526160D0/en active Pending
-
1986
- 1986-10-20 DE DE19863635636 patent/DE3635636A1/en not_active Withdrawn
- 1986-10-21 GB GB08625208A patent/GB2182030A/en not_active Withdrawn
- 1986-10-22 IT IT8622087A patent/IT8622087A0/en unknown
- 1986-10-22 FR FR8614642A patent/FR2588883A1/en not_active Withdrawn
- 1986-10-23 JP JP61252779A patent/JPS6299484A/en active Pending
Non-Patent Citations (2)
Title |
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CORROSION SCIENCE VOL 20, 1980 PP 1195-1200 * |
WO-8501964 * |
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US10737280B2 (en) | 2016-09-23 | 2020-08-11 | Central South University | Method of using flotation collector containing azolethione structure |
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JPS6299484A (en) | 1987-05-08 |
IT8622087A0 (en) | 1986-10-22 |
GB8526160D0 (en) | 1985-11-27 |
FR2588883A1 (en) | 1987-04-24 |
GB8625208D0 (en) | 1986-11-26 |
DE3635636A1 (en) | 1987-04-23 |
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