EP0222311A2 - Utilisation d'acides gras alcoyloxy hydroxy substitués comme inhibiteurs de corrosion dans des huiles et des émulsions contenant de l'huile - Google Patents
Utilisation d'acides gras alcoyloxy hydroxy substitués comme inhibiteurs de corrosion dans des huiles et des émulsions contenant de l'huile Download PDFInfo
- Publication number
- EP0222311A2 EP0222311A2 EP86115325A EP86115325A EP0222311A2 EP 0222311 A2 EP0222311 A2 EP 0222311A2 EP 86115325 A EP86115325 A EP 86115325A EP 86115325 A EP86115325 A EP 86115325A EP 0222311 A2 EP0222311 A2 EP 0222311A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- general formula
- radicals
- compounds
- oils
- use according
- 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.)
- Granted
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- 230000007797 corrosion Effects 0.000 title claims description 36
- 238000005260 corrosion Methods 0.000 title claims description 36
- 239000000839 emulsion Substances 0.000 title claims description 28
- 239000003921 oil Substances 0.000 title claims description 26
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 16
- 239000000194 fatty acid Substances 0.000 title claims description 16
- 229930195729 fatty acid Natural products 0.000 title claims description 16
- 239000003112 inhibitor Substances 0.000 title claims description 16
- 150000004665 fatty acids Chemical class 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002480 mineral oil Substances 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000010687 lubricating oil Substances 0.000 claims description 3
- 238000005555 metalworking Methods 0.000 claims description 3
- 230000005540 biological transmission Effects 0.000 claims description 2
- 230000001050 lubricating effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 18
- 239000002253 acid Substances 0.000 abstract description 11
- 239000002184 metal Substances 0.000 abstract description 9
- 229910052751 metal Inorganic materials 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 9
- 150000007513 acids Chemical class 0.000 abstract description 7
- 238000004140 cleaning Methods 0.000 abstract description 4
- 229920000642 polymer Polymers 0.000 abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 238000005554 pickling Methods 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 235000018553 tannin Nutrition 0.000 abstract 1
- 229920001864 tannin Polymers 0.000 abstract 1
- 239000001648 tannin Substances 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- 235000010446 mineral oil Nutrition 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910000831 Steel Inorganic materials 0.000 description 7
- 239000010959 steel Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- -1 amine salts Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 101000614439 Homo sapiens Keratin, type I cytoskeletal 15 Proteins 0.000 description 1
- 102100040443 Keratin, type I cytoskeletal 15 Human genes 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
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- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
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- 238000005553 drilling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003443 succinic acid derivatives Chemical class 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
- C10M129/40—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms monocarboxylic
-
- 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
- C23F11/12—Oxygen-containing compounds
- C23F11/124—Carboxylic acids
- C23F11/126—Aliphatic acids
-
- 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
- C23F11/141—Amines; Quaternary ammonium compounds
- C23F11/143—Salts of amines
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/128—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
Definitions
- oils and oil-containing emulsions come into contact with metal surfaces at high temperatures, the liquid media containing more or less large amounts of water. These result in part from the particular process taking place, as is the case, for example, with steam turbines, but can also be a desired component of the respective liquid media. In all such cases, protecting the metal surfaces coming into contact with the liquid media against corrosion poses a significant problem. Iron or iron-containing alloys in particular are corroded by water or moisture in the process liquids. The result in the ongoing process is a reduction in the service life of the respective system or, in the case of further processing of the metal surfaces, the need for complex cleaning of the metal surfaces in preparation for subsequent process steps, for example by phosphating, electroplating, painting, etc.
- a corrosion inhibitor is added to the process, cleaning or cooling liquids in such cases, which should inhibit, if not completely suppress, the corrosion.
- DE-AS 11 49 843 and EP-PS 0 002 780 describe amine salts of amic acids which are obtained by reacting succinic or maleic anhydride with primary alkylamines, and alkanolamine salts of maleic acids as corrosion inhibitors for fuel and lubricating oils and also water containing systems called.
- such compounds have the disadvantage that they tend to foam very strongly or - with a low tendency to foam - lose a large part of their corrosion-inhibiting effect.
- DE-AS 12 98 672 also discloses alkali or amine salts of sulfonaminocarboxylic acids, which likewise have a good corrosion protection effect in known metalworking fluids or oil-containing oil emulsions.
- a disadvantage of these compounds is that they are to be regarded as relatively toxic and their use is therefore subject to severe restrictions.
- alkanolamine salts of certain alkenylsuccinic acids are also known which, in aqueous systems without foam formation, show good corrosion protection on metal surfaces made of iron or iron-containing alloys.
- EP-A 0 127 132 also discloses alkenylsuccinic acid halamides as corrosion inhibitors, which are also described in aqueous process fluids for drilling, cutting or rolling metals. In aqueous media in particular, however, hydrolysis of the succinic acid derivatives mentioned is observed, which drastically reduces the corrosion-inhibiting effect of such compounds.
- the invention relates to the use of alkoxyhydroxy fatty acids and their salts of the general formula (I) in the R for unbranched alkyl radicals or alkenyl radicals with 6 to 8 C atoms, R 2 for unbranched or branched alkyl radicals with 1 to 18 C atoms or for unbranched or branched alkenyl radicals with 2 to 18 C atoms, M for hydrogen or organic ammonium radicals with one or more alkyl radicals or hydroxyalkyl radicals on the nitrogen atom and m are integers in the range from 3 to 13, in quantities of 0.01 to 10% by weight, based on oil, as corrosion inhibitors in oils and oil-containing emulsions.
- the compounds of the general formula (I) which are used according to the invention for corrosion inhibition are known as such.
- the process for their preparation is described in the relevant literature, for example in DE-OS 33 18 596.
- Alkoxyhydroxy fatty acids and their salts of the general formula (I) are formed, for example, by the fact that fatty acids or their esters of the general formula (II) in which R1 and m have the meanings given above and M can represent hydrogen or an alkyl group, preferably alcohols occurring in natural fats or oils, are epoxidized by methods known per se. Such an epoxidation reaction can take place, for example, by reacting the fatty acids or their esters of the general formula (II) with organic peroxo acids under suitable conditions.
- the epoxides obtained in this way which carry the oxirane ring at the position in the molecule at which the olefinic double bond was found in the starting materials, are then, according to processes which are also known per se, by acid-catalyzed ring opening with alcohols of the general formula in which R 2 can have the meanings given above, converted into the corresponding alkoxyhydroxyfatty acid derivatives in which the alkoxy group R 2 0 and the H y -droxy group each on the two carbon atoms connected in the starting material by the olefinic double bond are connected.
- the terminal ester grouping of the epoxides can also be transesterified.
- esters resulting from this reaction sequence are then subjected to alkaline hydrolysis by methods which are also known per se, giving the salts of the general formula (I) in which M represents organic ammonium radicals having one or more alkyl or hydroxyalkyl radicals on the nitrogen atom. If appropriate, the corresponding salts can be converted into the corresponding acids (I) in which M represents hydrogen by adjusting an acidic pH in the reaction medium.
- fats and oils of the general formula (II) are preferably used, which are inexpensively available in large quantities from native sources.
- Soybean oil which has a high content of oleic acid and linoleic acid, sunflower oil, sesame oil, corn oil, cottonseed oil, palm oil or coconut oil are preferred.
- Such natural fats and oils contain high proportions of esters of unsaturated fatty acids of the general formula (I), in which R represents unbranched alkyl radicals or alkenyl radicals, for example with 8 carbon atoms.
- esters of different chain lengths can also be found in such oils of native origin; for example, in soybean oil one can find mixtures of fatty acid esters of the general formula (II) in which R represents alkyl and alkenyl radicals with 8 carbon atoms, the saturated and unsaturated ones Shares to each other in the weight ratio of Stand 1: 2.
- Such compounds are to be regarded as preferably usable in the sense of the present invention.
- the alcohols of the general formula (III) used for the alcoholysis of the oxirane ring contain unbranched or branched alkyl radicals with 1 to 18 carbon atoms or unbranched or branched alkenyl radicals with 2 to 18 carbon atoms.
- Unbranched alkyl radicals or alkenyl radicals with 8 to 18 carbon atoms are to be regarded as preferred, which can also be provided inexpensively in large quantities from native sources.
- alcohol mixtures of natural origin are used which have unbranched alkyl radicals with 16 carbon atoms and alkenyl radicals with 18 carbon atoms.
- the free alkoxyhydroxy fatty acids (I) in which M represents hydrogen can be used as corrosion inhibitors.
- Preferred cations of such salts are ammonium cations which carry two or three alkyl radicals or hydroxyalkyl radicals on the nitrogen atom.
- the salt (I) in which M stands for a diethanolammonium radical is particularly preferably used.
- the alkoxyhydroxy fatty acids mentioned and their salts of the general formula (I) given are in Lubricating oils, greases, power transmission oils and metalworking emulsions based on mineral oils are used as corrosion inhibitors. They are used in a wide range of quantities in oils or oil-containing emulsions. The amounts can vary in the range from 0.01 to 10% by weight, based on the oil base, and are preferably from 0.05 to 0.5%. Oils and oil-containing emulsions which contain alkoxyhydroxyfatty acids or their salts of the general formula (I) in these amounts show a corrosion protection on iron and iron-containing metal surfaces which is at least equivalent to the previously known compounds.
- the alkoxyhydroxy fatty acids mentioned or their salts are superior to the previously known compounds in that they can be made inexpensively accessible in large quantities from natural raw materials.
- test specimens were stored in solutions without inhibitor (cf. 1) or in the corresponding mixtures, which contained a commercially available alkenylsuccinic acid half-ester, the concentration of which corresponded to the concentration of the alkoxyhydroxy fatty acids used according to the invention (cf. 2).
- concentration of which corresponded to the concentration of the alkoxyhydroxy fatty acids used according to the invention cf. 2.
- the emulsions were prepared from the corresponding concentrates by customary methods using water with a total hardness of 3.58 mmol CaCl 2 . 6H 2 0 and MgSO 4 . 7H 2 O manufactured.
- the emulsions were prepared by stirring 8 to 25% by weight of the stated concentrates (formulations 1 and 2) in water with the stated total hardness. This corresponds to DIN 51360 / Part 2.
- the corrosion protection S was then calculated in% according to the following equation from the comparison of the results with the averaged removals in the case of a blank sample made from inhibitor-free emulsion:
- steel sheets (quality ST 1405, degreased and sanded, dimensions: 25 x 50 mm) were immersed in mineral oil emulsions which had been produced using the substances used according to the invention. Different amounts of inhibitor were used in the mineral oil emulsions. After a certain draining and drying time, the sheets were stored in a humidity chamber at 100% relative atmospheric humidity. After the test period (1 to 7 days), the steel sheets were checked for signs of corrosion. The evaluation was carried out on the evaluation scale given in Example 1 from 0 to 4.
- Example 4 identical steel sheets of the same size were stored in mineral oil emulsions which did not contain an inhibitor.
- the comparison emulsions contained naphthenic mineral oil and emulsifier (adduct of 6.5 EO with nonylphenol) in a weight ratio of 4: 1.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Mechanical Engineering (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Lubricants (AREA)
- Colloid Chemistry (AREA)
- Detergent Compositions (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT86115325T ATE60083T1 (de) | 1985-11-13 | 1986-11-05 | Verwendung von alkoxyhydroxyfettsaeuren als korrosionsinhibitoren in oelen und oelhaltigen emulsionen. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3540246 | 1985-11-13 | ||
DE19853540246 DE3540246A1 (de) | 1985-11-13 | 1985-11-13 | Verwendung von alkoxyhydroxyfettsaeuren als korrosionsinhibitoren in oelen und oelhaltigen emulsionen |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0222311A2 true EP0222311A2 (fr) | 1987-05-20 |
EP0222311A3 EP0222311A3 (en) | 1989-05-03 |
EP0222311B1 EP0222311B1 (fr) | 1991-01-16 |
Family
ID=6285879
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86115325A Expired - Lifetime EP0222311B1 (fr) | 1985-11-13 | 1986-11-05 | Utilisation d'acides gras alcoyloxy hydroxy substitués comme inhibiteurs de corrosion dans des huiles et des émulsions contenant de l'huile |
Country Status (8)
Country | Link |
---|---|
US (2) | US4957641A (fr) |
EP (1) | EP0222311B1 (fr) |
JP (1) | JPS62115093A (fr) |
AT (1) | ATE60083T1 (fr) |
AU (1) | AU577715B2 (fr) |
DE (2) | DE3540246A1 (fr) |
ES (1) | ES2003505A6 (fr) |
ZA (1) | ZA868592B (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0302007A1 (fr) * | 1987-07-14 | 1989-02-01 | Ciba-Geigy Ag | Acides hydroxy-éther-carboxyliques et leur lactones, procédé pour les produire et leur utilisation comme inhibiteurs de corrosion |
EP0318429A2 (fr) * | 1987-11-21 | 1989-05-31 | Ciba-Geigy Ag | Inhibiteur de la corrosion |
WO1991005033A1 (fr) * | 1989-10-04 | 1991-04-18 | Henkel Kommanditgesellschaft Auf Aktien | Procede pour la fabrication d'emulsions aqueuses antirouille stables et faiblement visqueuses |
US5091113A (en) * | 1987-05-15 | 1992-02-25 | Ciba-Geigy Corporation | Corrosion inhibiting composition |
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US5411677A (en) * | 1993-04-26 | 1995-05-02 | The Penn State Research Foundation | Method and composition for preventing copper corrosion |
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AU3144497A (en) * | 1996-05-30 | 1998-01-05 | Salient Science, Inc. | Foaming acidic detergent/cleansing gel |
US5707955A (en) * | 1996-07-15 | 1998-01-13 | Colgate-Palmolive Co. | High foaming nonionic surfactant based liquid detergent |
EP0960170A1 (fr) * | 1997-01-31 | 1999-12-01 | Elisha Technologies Co. L.L.C. | Revetements anti-corrosion |
US5895763A (en) * | 1997-04-16 | 1999-04-20 | H.E.R.C. Products Incorporated | Controlled carbonate removal from water conduit systems |
US5873944A (en) * | 1997-05-13 | 1999-02-23 | H.E.R.C. Products Incorporated | Vacuum waste pipe cleaning |
US6197451B1 (en) | 1998-04-07 | 2001-03-06 | Henkel Corporation | Corrosion inhibiting electrolytic solutions |
ZA991306B (en) * | 1998-07-23 | 1999-08-20 | Magdelena Christiana Cor Stols | "A cleaning composition". |
DE19842054A1 (de) * | 1998-09-15 | 2000-03-16 | Bayer Ag | Verwendung von wasserlöslichen polymeren Polycarboxylaten in Reinigerformulierungen mit abrasiver Wirkung |
US6165952A (en) * | 1999-04-05 | 2000-12-26 | King Industries, Inc. | Ashless rust inhibitor lubricant compositions |
US6346217B1 (en) * | 1999-06-02 | 2002-02-12 | Water Whole International, Inc. | Composition and method for cleaning drink water tanks |
DE10005113A1 (de) * | 2000-02-07 | 2001-08-09 | Henkel Kgaa | Korrosionsschutzmittel und Korrosionsschutzverfahren für Metalloberflächen |
DK1274883T3 (da) | 2000-04-13 | 2006-10-23 | Baker Hughes Inc | Korrosionsinhibitor |
US6964275B2 (en) * | 2001-12-26 | 2005-11-15 | H.E.R.C. Products Incorporated | Countermeasure washdown system cleaning |
US20040235680A1 (en) * | 2002-09-18 | 2004-11-25 | Ecolab Inc. | Conveyor lubricant with corrosion inhibition |
US20040074847A1 (en) * | 2002-10-16 | 2004-04-22 | Jaquess Percy A. | Stable N-bromo-2-pyrrolidone and methods to make the same |
US7964044B1 (en) * | 2003-10-29 | 2011-06-21 | Birchwood Laboratories, Inc. | Ferrous metal magnetite coating processes and reagents |
US20060180795A1 (en) * | 2005-02-17 | 2006-08-17 | Mccormick David R | Stable acid inhibitor formulations with improved performance, lower toxicity and minimal environmental issues |
US7828908B1 (en) | 2010-03-31 | 2010-11-09 | Ecolab USA, Inc. | Acid cleaning and corrosion inhibiting compositions comprising gluconic acid |
WO2012087773A1 (fr) * | 2010-12-21 | 2012-06-28 | The Lubrizol Corporation | Composition lubrifiante contenant un agent anti-usure |
US8795589B1 (en) | 2011-04-29 | 2014-08-05 | Cortec Corporation | Bio-based volatile corrosion inhibitors |
NL2011852C2 (en) | 2013-11-28 | 2015-06-01 | Univ Delft Tech | Biobased membrane. |
US9567554B2 (en) | 2014-01-10 | 2017-02-14 | General Electric Company | Apparatus, method, and solvent for cleaning turbine components |
CN115323385A (zh) * | 2022-08-30 | 2022-11-11 | 重庆广仁铁塔制造有限公司 | 一种高效环保镀锌酸洗缓蚀剂的制备方法、缓蚀剂及其应用 |
CN115433945B (zh) * | 2022-10-19 | 2023-09-05 | 中国大唐集团科学技术研究院有限公司中南电力试验研究院 | 一种用于燃煤锅炉化学清洗的四元复合缓蚀剂及应用 |
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-
1985
- 1985-11-13 DE DE19853540246 patent/DE3540246A1/de not_active Withdrawn
-
1986
- 1986-10-15 US US06/919,098 patent/US4957641A/en not_active Expired - Fee Related
- 1986-11-05 EP EP86115325A patent/EP0222311B1/fr not_active Expired - Lifetime
- 1986-11-05 AT AT86115325T patent/ATE60083T1/de active
- 1986-11-05 DE DE8686115325T patent/DE3676950D1/de not_active Expired - Fee Related
- 1986-11-12 ZA ZA868592A patent/ZA868592B/xx unknown
- 1986-11-12 AU AU65064/86A patent/AU577715B2/en not_active Ceased
- 1986-11-12 ES ES8603000A patent/ES2003505A6/es not_active Expired
- 1986-11-13 JP JP61270814A patent/JPS62115093A/ja active Pending
-
1987
- 1987-09-21 US US07/098,712 patent/US4851149A/en not_active Expired - Lifetime
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DE1149843B (de) * | 1958-01-07 | 1963-06-06 | Socony Mobil Oil Co Inc | Zusatzmittel fuer Brennstoff- und Schmieroele |
EP0002780A1 (fr) * | 1977-12-24 | 1979-07-11 | BASF Aktiengesellschaft | Utilisation d'inhibiteurs de corrosion dans des systèmes aqueux |
EP0127810A1 (fr) * | 1983-05-21 | 1984-12-12 | Henkel Kommanditgesellschaft auf Aktien | Acides hydroxyalkoxycarboxyliques et leurs sels, leurs procédés de préparation ainsi que leur utilisation |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5091113A (en) * | 1987-05-15 | 1992-02-25 | Ciba-Geigy Corporation | Corrosion inhibiting composition |
EP0302007A1 (fr) * | 1987-07-14 | 1989-02-01 | Ciba-Geigy Ag | Acides hydroxy-éther-carboxyliques et leur lactones, procédé pour les produire et leur utilisation comme inhibiteurs de corrosion |
US5055230A (en) * | 1987-07-14 | 1991-10-08 | Ciba-Geigy Corporation | Corrosion inhibiting compositions |
EP0318429A2 (fr) * | 1987-11-21 | 1989-05-31 | Ciba-Geigy Ag | Inhibiteur de la corrosion |
EP0318429A3 (en) * | 1987-11-21 | 1990-03-14 | Ciba-Geigy Ag | Corrosion inhibitor |
WO1991005033A1 (fr) * | 1989-10-04 | 1991-04-18 | Henkel Kommanditgesellschaft Auf Aktien | Procede pour la fabrication d'emulsions aqueuses antirouille stables et faiblement visqueuses |
Also Published As
Publication number | Publication date |
---|---|
EP0222311B1 (fr) | 1991-01-16 |
ZA868592B (en) | 1987-06-24 |
ATE60083T1 (de) | 1991-02-15 |
US4957641A (en) | 1990-09-18 |
ES2003505A6 (es) | 1988-11-01 |
AU6506486A (en) | 1987-05-21 |
AU577715B2 (en) | 1988-09-29 |
JPS62115093A (ja) | 1987-05-26 |
US4851149A (en) | 1989-07-25 |
DE3540246A1 (de) | 1987-05-14 |
EP0222311A3 (en) | 1989-05-03 |
DE3676950D1 (de) | 1991-02-21 |
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