EP0566956A1 - Inhibiteur de corrosion - Google Patents
Inhibiteur de corrosion Download PDFInfo
- Publication number
- EP0566956A1 EP0566956A1 EP93105957A EP93105957A EP0566956A1 EP 0566956 A1 EP0566956 A1 EP 0566956A1 EP 93105957 A EP93105957 A EP 93105957A EP 93105957 A EP93105957 A EP 93105957A EP 0566956 A1 EP0566956 A1 EP 0566956A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- weight
- alkenyl
- ester
- succinic acid
- 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
Links
- 238000005260 corrosion Methods 0.000 title claims abstract description 23
- 230000007797 corrosion Effects 0.000 title claims abstract description 17
- 239000003112 inhibitor Substances 0.000 title abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- -1 alkenyl succinic acid, Chemical compound 0.000 claims description 30
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000002480 mineral oil Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000011814 protection agent Substances 0.000 claims description 7
- 239000001384 succinic acid Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 238000005555 metalworking Methods 0.000 claims description 5
- 235000010446 mineral oil Nutrition 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- VRMUTGLITCWVPW-UHFFFAOYSA-N 3-prop-1-enoxycarbonyl-2,2,3-tris(prop-1-enyl)hex-4-enoic acid Chemical compound CC=COC(=O)C(C=CC)(C=CC)C(C=CC)(C=CC)C(O)=O VRMUTGLITCWVPW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000005068 cooling lubricant Substances 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 235000011044 succinic acid Nutrition 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000004005 nitrosamines Chemical class 0.000 description 3
- RYNKSPIWLXKJHG-ZJUUUORDSA-N (3s)-3-[(3s)-oct-1-en-3-yl]oxolane-2,5-dione Chemical compound CCCCC[C@@H](C=C)[C@@H]1CC(=O)OC1=O RYNKSPIWLXKJHG-ZJUUUORDSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- UMXHTMOMWDGZKZ-UHFFFAOYSA-M sodium;4-(2-methylpropoxy)-4-oxobutanoate Chemical compound [Na+].CC(C)COC(=O)CCC([O-])=O UMXHTMOMWDGZKZ-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C10M173/00—Lubricating compositions containing more than 10% 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
- 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
- C10M129/16—Ethers
-
- 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
- C10M129/68—Esters
- C10M129/76—Esters containing free hydroxy or carboxyl groups
-
- 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
-
- 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
- C23F11/128—Esters of carboxylic 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
- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
-
- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/046—Hydroxy ethers
-
- 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
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/288—Partial esters containing free carboxyl groups
-
- 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
- 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
- C10N2040/20—Metal working
-
- 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
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/01—Emulsions, colloids, or micelles
Definitions
- Corrosion protection agents are used in many areas of metalworking when it comes to protecting the metal parts used from rust.
- the previously used corrosion protection agents contain constituents such as petroleum sulfonates, salts of alkylsulfonamidocarboxylic acids and amine salts of a partial ester of an alkyl or alkenyl succinic acid.
- DE-A-26 40 854 discloses lubricant compositions with anti-rust properties based on amine salts of a partial ester of an alkyl or alkenyl succinic acid.
- Corrosion protection agents based on alkylarylsulfonic acids, alkanolamine and partial esters of an alkyl or alkenyl succinic acid are known from EP-A-336 467.
- sulfur-containing compounds such as alkylarylsulfonic acids, petroleum sulfonates, salts of alkylsulfonamidocarboxylic acids
- sulfur-containing compounds can easily be broken down by microorganisms, such as sulfur-reducing bacteria.
- Nitrogen-containing corrosion protection agents, especially secondary amines, can e.g. are chemically converted into health-endangering nitrosamines.
- the object of the invention is to provide anti-corrosion agents which are free of amines and which, when used, preclude the formation of substances which are hazardous to health, such as nitrosamines.
- salts in particular alkali metal and alkaline earth metal salts of alkyl or alkenylsuccinic acid semiesters, can be used as corrosion inhibitors, and a risk from nitrosamines can thus be excluded.
- the invention relates to corrosion protection agents, characterized by a content of amine-free salt of a half ester of an alkyl or alkenyl succinic acid, the alkyl or alkenyl substituents of which contain 8 to 30 carbon atoms, preferably 9 to 15 carbon atoms.
- the amine-free salts are obtained by esterification of alkyl- or alkenylsuccinic anhydride with alcohol, preferably in equimolar amounts, optionally with the addition of a catalyst, such as alcoholate solution, at temperatures up to the boiling point of the solution, preferably 20 ° C. to boiling point, particularly preferably 40-80 ° C.
- a catalyst such as alcoholate solution
- the reaction is preferably carried out with nitrogen gas.
- the solution is advantageously stirred at a temperature up to the boiling point of the solution, preferably from 60 ° C. to the boiling point of the solution.
- the half-esters obtained are mixed with dilute alkali to a pH above 7, preferably up to a pH in the range of 9.
- the half ester is derived from an alkyl or alkenyl succinic acid in which the alkenyl or alkyl substituent contains 8 to 30 carbon atoms, preferably 9 to 15 carbon atoms.
- succinic acids are octenyl, dodecenyl, hexadecenyl, isooctadecenyl or triacontenyl succinic acid.
- the substituent group can also consist of a polyolefinic group, such as a tri, tetra or pentapropenyl group.
- the alcohol used to form the half ester preferably has 1 to 15 carbon atoms and preferably contains an alkyl alcohol (alkanol) such as methanol, ethanol, propanol or butanol.
- alkyl alcohol alkanol
- the lye, which is reacted with the half ester of the substituted succinic acid is preferably an aqueous hydroxide solution, such as sodium hydroxide solution or potassium hydroxide solution.
- aqueous solutions of polyvalent metal hydroxides, such as alkaline earth metal hydroxides, are also suitable.
- the aqueous solution of the amine-free salts thus obtained can be used directly as an anti-corrosion agent without further purification of the alkyl or alkenylsuccinic acid.
- These amine-free salts can be used in the case of aqueous corrosion protection agents, and are preferably used in a concentration of 0.5 to 65% by weight, particularly preferably 1 to 10% by weight, based on the aqueous solution.
- the pH of the aqueous anticorrosive agent is above pH 7, preferably at a pH of approximately 9.
- the amine-free salts can also be used in a mixture with other compounds as corrosion inhibitors.
- Such an anti-corrosion agent consists of, for example 40-80% by weight of a salt of a half ester of an alkyl or alkenyl succinic acid, 30-1% by weight of an oxyethylate of the formula R1 - O - (CH2CH2O) n H, where R1 is C10-C22-alkyl, C10-C22-alkenyl or alkaryl and n is 1 to 10, preferably 1 to 5, 30 - 1 wt .-% fatty acid of the formula R2 - COOH wherein R2 is C10-C20 alkyl or C10-C30 alkenyl and 30-0% by weight of ether carboxylic acid of the formula R3 - O - (CH2CH2O) n - CH2 - COOH, wherein R3 is C10-C22-alkyl, C10-C22-alkenyl or al
- Such anti-corrosion agents are characterized by complete “solubility" in combination with water. When mixed with water, they form finely divided emulsions that can be clear (transparent) opal or milky.
- Mixtures of the above-mentioned amine-free salts of the half esters of alkyl or alkenylsuccinic acid with oxethylates, fatty acids and optionally ether carboxylic acids are preferably used with mineral oils, in an amount of up to 70% by weight of mineral oil, based on the total weight, and show good properties as corrosion inhibitors.
- Suitable mineral oils are mineral oils which consist of paraffins, naphthenes and partly of aromatics and usually have viscosities of 25 to 30 mm2 / s, measured at 20 ° C.
- aqueous solutions of the amine-free salts of the half esters of alkyl or alkenylsuccinic acid, with oxethylates, fatty acids and optionally ether carboxylic acids and mineral oil are preferably used as corrosion inhibitors, where they show good results especially with regard to good hard water stability.
- test results listed below show that the amine-free salts according to the invention are effective as anti-corrosion agents.
- Table 1 shows the corrosion-inhibiting effect of an aqueous alkaline solution of the amine-free salt.
- Table 2 shows the corrosion-inhibiting effect of a mixture.
- the corrosion-inhibiting effect was determined using the Herbert test (DIN 51360/1) and the filter paper test (DIN 51360/2).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Lubricants (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4213150 | 1992-04-22 | ||
DE4213150 | 1992-04-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0566956A1 true EP0566956A1 (fr) | 1993-10-27 |
EP0566956B1 EP0566956B1 (fr) | 1996-07-31 |
Family
ID=6457193
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP93105957A Expired - Lifetime EP0566956B1 (fr) | 1992-04-22 | 1993-04-13 | Inhibiteur de corrosion |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0566956B1 (fr) |
JP (1) | JPH0617268A (fr) |
AT (1) | ATE140982T1 (fr) |
BR (1) | BR9301612A (fr) |
CA (1) | CA2094556A1 (fr) |
CZ (1) | CZ287586B6 (fr) |
DE (1) | DE59303348D1 (fr) |
ES (1) | ES2092715T3 (fr) |
RU (1) | RU2110613C1 (fr) |
SK (1) | SK36493A3 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0657410A1 (fr) * | 1993-12-07 | 1995-06-14 | Hoechst Aktiengesellschaft | Procédé pour la préparation d'alkoxylates utilisant des esters comme catalyseurs |
WO1996012054A1 (fr) * | 1994-10-14 | 1996-04-25 | Henkel Kommanditgesellschaft Auf Aktien | Utilisation de sels de guanidine d'acides gras insatures comme principes actifs anticorrosifs |
GB2325238A (en) * | 1997-03-21 | 1998-11-18 | Castrol Ltd | Metalworking fluid containing an alkyl (alk(en)yl) succinate monoester |
EP1354905A2 (fr) * | 2002-04-18 | 2003-10-22 | Clariant GmbH | Procédé de fabrication d'acides ether-carboxyliques à bas point d'écoulement |
US8802605B2 (en) | 2009-08-07 | 2014-08-12 | Basf Se | Lubricant composition |
US8802606B2 (en) | 2010-08-06 | 2014-08-12 | Basf Se | Lubricant composition having improved antiwear properties |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2483099C2 (ru) * | 2006-05-23 | 2013-05-27 | Циба Холдинг Инк. | Замедляющая коррозию композиция для цветных металлов |
MD1025Z (ro) * | 2015-09-30 | 2016-11-30 | Институт Химии Академии Наук Молдовы | Inhibitor de coroziune a oţelului în apă |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4053426A (en) * | 1975-03-17 | 1977-10-11 | Mobil Oil Corporation | Lubricant compositions |
EP0216280A2 (fr) * | 1985-09-27 | 1987-04-01 | Hoechst Aktiengesellschaft | Utilisation de mono-amides d'acides alcénylsucciniques comme inhibiteurs de corrosion |
-
1993
- 1993-04-13 EP EP93105957A patent/EP0566956B1/fr not_active Expired - Lifetime
- 1993-04-13 DE DE59303348T patent/DE59303348D1/de not_active Expired - Fee Related
- 1993-04-13 ES ES93105957T patent/ES2092715T3/es not_active Expired - Lifetime
- 1993-04-13 AT AT93105957T patent/ATE140982T1/de not_active IP Right Cessation
- 1993-04-19 SK SK364-93A patent/SK36493A3/sk unknown
- 1993-04-20 BR BR9301612A patent/BR9301612A/pt not_active Application Discontinuation
- 1993-04-21 JP JP5094551A patent/JPH0617268A/ja active Pending
- 1993-04-21 CZ CZ1993691A patent/CZ287586B6/cs not_active IP Right Cessation
- 1993-04-21 CA CA002094556A patent/CA2094556A1/fr not_active Abandoned
- 1993-04-21 RU RU93004634A patent/RU2110613C1/ru active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4053426A (en) * | 1975-03-17 | 1977-10-11 | Mobil Oil Corporation | Lubricant compositions |
EP0216280A2 (fr) * | 1985-09-27 | 1987-04-01 | Hoechst Aktiengesellschaft | Utilisation de mono-amides d'acides alcénylsucciniques comme inhibiteurs de corrosion |
Non-Patent Citations (1)
Title |
---|
PATENT ABSTRACTS OF JAPAN vol. 10, no. 219 (C-363)(2275) 31. Juli 1986 & JP-A-61 056 287 ( CHIYODA KAGAKU KENKYUSHO K.K ) 20. März 1986 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0657410A1 (fr) * | 1993-12-07 | 1995-06-14 | Hoechst Aktiengesellschaft | Procédé pour la préparation d'alkoxylates utilisant des esters comme catalyseurs |
US5600020A (en) * | 1993-12-07 | 1997-02-04 | Hoechst Aktiengesellschaft | Process for the preparation of alkoxylates using ester compounds as catalyst |
WO1996012054A1 (fr) * | 1994-10-14 | 1996-04-25 | Henkel Kommanditgesellschaft Auf Aktien | Utilisation de sels de guanidine d'acides gras insatures comme principes actifs anticorrosifs |
US5749947A (en) * | 1994-10-14 | 1998-05-12 | Henkel Kommanditgesellschaft Auf Aktien | Use of guanidinium salts of unsaturated fatty acids as corrosion inhibitors |
GB2325238A (en) * | 1997-03-21 | 1998-11-18 | Castrol Ltd | Metalworking fluid containing an alkyl (alk(en)yl) succinate monoester |
EP1354905A2 (fr) * | 2002-04-18 | 2003-10-22 | Clariant GmbH | Procédé de fabrication d'acides ether-carboxyliques à bas point d'écoulement |
EP1354905B1 (fr) * | 2002-04-18 | 2006-01-11 | Clariant GmbH | Utilisation des acides ether-carboxyliques à bas point d'écoulement |
US8802605B2 (en) | 2009-08-07 | 2014-08-12 | Basf Se | Lubricant composition |
US9340745B2 (en) | 2009-08-07 | 2016-05-17 | Basf Se | Lubricant composition |
US8802606B2 (en) | 2010-08-06 | 2014-08-12 | Basf Se | Lubricant composition having improved antiwear properties |
Also Published As
Publication number | Publication date |
---|---|
ATE140982T1 (de) | 1996-08-15 |
RU2110613C1 (ru) | 1998-05-10 |
ES2092715T3 (es) | 1996-12-01 |
DE59303348D1 (de) | 1996-09-05 |
SK36493A3 (en) | 1993-11-10 |
JPH0617268A (ja) | 1994-01-25 |
CZ69193A3 (en) | 1994-01-19 |
BR9301612A (pt) | 1993-10-26 |
EP0566956B1 (fr) | 1996-07-31 |
CA2094556A1 (fr) | 1993-10-23 |
CZ287586B6 (en) | 2000-12-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0222311B1 (fr) | Utilisation d'acides gras alcoyloxy hydroxy substitués comme inhibiteurs de corrosion dans des huiles et des émulsions contenant de l'huile | |
EP0088724B1 (fr) | Mélanges de benzotriazoles, leur procédé de préparation, et leur application comme inhibiteurs de corrosion de métaux | |
EP0127132B1 (fr) | Utilisation de monoamides d'acides alcénylsucciniques comme inhibiteurs de corrosion | |
DE2736408A1 (de) | Verfahren zur herstellung von sulfobetainen | |
EP0566956B1 (fr) | Inhibiteur de corrosion | |
DE2840112C2 (de) | Wassermischbare Korrosionsschutzmittel und Verfahren zur Verhinderung der Korrosion von Eisenmetallen | |
DE2342685A1 (de) | Organische massen mit korrosionsinhibierenden eigenschaften | |
DE3888569T2 (de) | Schmierölzusammensetzungen, die Antiverschleiss- oder Extremdruckadditive enthalten. | |
EP0144738B1 (fr) | Mono-dialkylamides d'acides succiniques comme inhibiteurs de corrosion solubles dans l'eau | |
DE69208288T2 (de) | Korrosioninhibierung in stark sauren Umgebungen | |
EP0231524B1 (fr) | Application d'acides alkylbenzoylacryliques comme inhibiteurs de corrosion | |
EP0216280B1 (fr) | Utilisation de mono-amides d'acides alcénylsucciniques comme inhibiteurs de corrosion | |
DE3300874A1 (de) | Bernsteinsaeurederivate als korrosionsschutzmittel | |
DE69024225T2 (de) | Aminocarboxylate als korrosionsinhibitoren bei der beschichtung | |
EP0098809A2 (fr) | Sels d'acides phosphoryl-mercapto carboxyliques | |
EP0060456B1 (fr) | Inhibiteurs contre la corrosion par acide sulfhydrique et dioxyde de carbone dans des émulsions huileuses | |
EP0726335A1 (fr) | Compositions inhibitrices de la corrosion contenant un amide de l'acide lactobionique | |
DE3501180A1 (de) | Salze von alkenylbernsteinsaeurehalbamiden, verfahren zu deren herstellung und deren verwendung als korrosionsinhibitoren | |
DE2433478C3 (de) | Alkylammoniumcarboxylatsalzäthoxylierte Alkylphenolester einer trimeren oder dinieren Säure und Zusammensetzung davon | |
DE3341633C2 (fr) | ||
EP0106234A1 (fr) | Utilisation de sels d'amines d'amide de l'acide maléique comme inhibiteur de corrosion de C02 et H2S dans des émulsions eau dans l'huile | |
DE1176445B (de) | Verwendung von Salzen des Triaethanolamins enthaltenden Mischungen als Inhibitor in auf Eisen und Kupfer korrodierend wirkenden Fluessigkeiten | |
EP0015442B1 (fr) | Inhibiteurs de corrosion peu moussants et à propriétés microbiocides, contenant comme composé actif un produit de réaction d'acide borique et d'une alcanolamine | |
EP0823494A1 (fr) | Compositions inhibiteurs ou protectrices de la corrosion contenant des amides d'acide lactobionique | |
EP4381032A1 (fr) | Nouveau mélange d'additifs |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE ES FR GB IT LI NL SE |
|
17P | Request for examination filed |
Effective date: 19940228 |
|
17Q | First examination report despatched |
Effective date: 19941207 |
|
GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AT BE CH DE ES FR GB IT LI NL SE |
|
REF | Corresponds to: |
Ref document number: 140982 Country of ref document: AT Date of ref document: 19960815 Kind code of ref document: T |
|
GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
REF | Corresponds to: |
Ref document number: 59303348 Country of ref document: DE Date of ref document: 19960905 |
|
ITF | It: translation for a ep patent filed | ||
GBT | Gb: translation of ep patent filed (gb section 77(6)(a)/1977) |
Effective date: 19961003 |
|
ET | Fr: translation filed | ||
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2092715 Country of ref document: ES Kind code of ref document: T3 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed | ||
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: AT Payment date: 19980401 Year of fee payment: 6 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 19990318 Year of fee payment: 7 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990413 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PUE Owner name: HOECHST AKTIENGESELLSCHAFT TRANSFER- CLARIANT GMBH |
|
BECA | Be: change of holder's address |
Free format text: 19991028 *CLARIANT G.M.B.H.:BRUENINGSTRASSE 50, 65929 FRANKFURT AM MAIN |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: TP |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20000414 |
|
NLS | Nl: assignments of ep-patents |
Owner name: CLARIANT GMBH |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: PC2A |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: 732E |
|
EUG | Se: european patent has lapsed |
Ref document number: 93105957.0 |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: IF02 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 20030218 Year of fee payment: 11 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20030220 Year of fee payment: 11 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 20030221 Year of fee payment: 11 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20030224 Year of fee payment: 11 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 20030226 Year of fee payment: 11 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: ES Payment date: 20030227 Year of fee payment: 11 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 20030311 Year of fee payment: 11 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20040413 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: ES Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20040414 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20040430 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20040430 Ref country code: BE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20040430 |
|
BERE | Be: lapsed |
Owner name: *CLARIANT G.M.B.H. Effective date: 20040430 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20041101 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20041103 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20040413 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20041231 |
|
NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee |
Effective date: 20041101 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20050413 |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FD2A Effective date: 20040414 |