CA2045205A1 - Salts of alkenylsuccinic monoamides and their use as anticorrosive agents and emulsifiers for metal-working oils - Google Patents
Salts of alkenylsuccinic monoamides and their use as anticorrosive agents and emulsifiers for metal-working oilsInfo
- Publication number
- CA2045205A1 CA2045205A1 CA002045205A CA2045205A CA2045205A1 CA 2045205 A1 CA2045205 A1 CA 2045205A1 CA 002045205 A CA002045205 A CA 002045205A CA 2045205 A CA2045205 A CA 2045205A CA 2045205 A1 CA2045205 A1 CA 2045205A1
- Authority
- CA
- Canada
- Prior art keywords
- alkenylsuccinic
- monoamides
- water
- alkenyl
- mineral oil
- 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.)
- Abandoned
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 14
- 150000003839 salts Chemical class 0.000 title abstract description 7
- 238000005555 metalworking Methods 0.000 title abstract description 4
- 239000003921 oil Substances 0.000 title abstract description 4
- 239000003995 emulsifying agent Substances 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 239000002480 mineral oil Substances 0.000 claims abstract description 11
- 235000010446 mineral oil Nutrition 0.000 claims abstract description 9
- -1 2-hydroxypropyl Chemical group 0.000 claims abstract description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 6
- 239000000194 fatty acid Substances 0.000 claims abstract description 6
- 229930195729 fatty acid Natural products 0.000 claims abstract description 6
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 3
- 238000009472 formulation Methods 0.000 claims abstract 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229960004418 trolamine Drugs 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- 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 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003784 tall oil Substances 0.000 description 3
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000005068 cooling lubricant Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FOACHEGMCPHDMJ-UHFFFAOYSA-N 2,2,3-tris(prop-1-enyl)-3-(prop-1-enylcarbamoyl)hex-4-enoic acid Chemical compound C(=CC)NC(C(C(C(=O)O)(C=CC)C=CC)(C=CC)C=CC)=O FOACHEGMCPHDMJ-UHFFFAOYSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 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
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical class CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000010494 opalescence Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 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
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
-
- 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
- C10M133/16—Amides; Imides
-
- 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
- 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
- C23F11/145—Amides; N-substituted amides
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
-
- 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
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
-
- 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
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
Abstract of the Disclosure Salts of alkenylsuccinic monoamides and their use as anticorrosive agents and emulsifiers for metal-working oils The invention relates to alkenylsuccinic monoamides of the formulae or in which R is C13-C30-alkenyl and Me+ is an alkali metal ion, a proton or an ammonium ion of the formula +NHR1R2R3 and R1, R2 and R3 are identical or different and are hydrogen, 2-hydroxyethyl or 2-hydroxypropyl.
The invention further relates to the use of these alkenyl-succinic monoamides as anticorrosive agents in water-and/or mineral oil-containing formulations, if appro-priate together with ethoxylates and/or fatty acid alkanolamides, and water- and/or mineral oil-containing anticorrosive agents, containing alkenylsuccinic mono-amides of this type.
The invention further relates to the use of these alkenyl-succinic monoamides as anticorrosive agents in water-and/or mineral oil-containing formulations, if appro-priate together with ethoxylates and/or fatty acid alkanolamides, and water- and/or mineral oil-containing anticorrosive agents, containing alkenylsuccinic mono-amides of this type.
Description
2~ ~ ?~5 HOECHST ARTIENGESELLSCHAFT HOE 90/F 182 Dr.GT/fe Description Salts of alkenylsuccinic monoamides and their uffe as anticorrosive agents and emulsifier~ for metal-working oils Anticorrosive agents and emul6ifiers in emulsifiable metal-working oils containing between 20 - 50% of these products and 80 - 20% of naphthene-base, paraffin-base or mixed-base mineral oils should meet the following requirements:
Distinct anticorrosive properties towards iron metals, emulsifying power towards mineral oils, possibly also in combination with selected nonionic compounds, low ten-dency to foaming or rapid foam breakdown, growth inhibi-tion of microorganisms.
Only some of these requirements are met by the compoundslisted in EP 0,127,132. This document has already dis-closed alkenylsuccinic monoamides of the formula R ~ J ~ CH2 ~ CONH2 COO~ K~
where R is C6-Cl2-alkenyl and their use as anticorrosive agents.
However, these compounds show insufficient emulsifying power, which leads to unsatisfactory shelf lives of the emulsions to be used. Furthermore, emulsions containing these compounds have a tendency to foaming, which is a particular disadvantage in working processes, such as grinding, where the emulsions are exposed to high mechanical influences.
The disadvantages described can be overcome by using the - 2 _ 2 ~ ~ ~ 2 ~ ~
longer-chain alkenylsuccinic monoamides according to the invention which are described below. The opalescence of the emulsions achieved with these longer-chain alkenyl-succinic monoamides indicates finer dispersion of the emulsions compared with the shorter-chain ones and thus long shelf lives, i.e. the emulsion can be used longer.
The longer-chain alkenylsuccinic monoamides according to the inventio~ also fulfil the requirement of low tendency to foaming or rapid foam breakdown, which is not the case in the shorter-chain compounds.
Accordingly, the invention relates to alkenylsuccinic monoamides of the formulae R - CH - CH2 - CONH2 or R - CH - CH2 - coda Me~
COOe Me~ CONH2 in which R is Cl3-C30-alkenyl, preferably C15-C21-alkenyl, where R can be straight-chain or branched, and Ne~ is an alkali metal ion (Na', R+), a proton or an ammonium ion of the formula ~NHRlR2R3 and Rl, R2 and R3 are identical or different and are hydrogen, 2-hydroxyethyl or 2-hydroxy-propyl and to their use as anticorrosive agents.
The preparation of the alkenylsuccinic anhydrides used as starting materials from olefin and maleic anhydride is known. The alkenylsuccinic monoamides are obtained by reaction of 1 mol of an alkenylsuccinic anhydride with at least 2 mol of ammonia, which gives the alkenylsuccinic monoamide in the form of the ammonium salt. If aqueous ammonia solution is used, the ammonium salt of the alkenylsuccinic monoamide is formed in an aqueous solu-tion. By displacing the ammonia by means of other bases, other salts of the monoamides can be prepared. Salts which are particularly preferably used as anticorrosive agents are the alkanolamine salts, such as triethanol-amine or triisopropanolamine salts, which are prepared by reacting ~the initially formed ammonium salts with an aqueous splution of alkanolamine at elevated temperature.
2~ 32~ -The ammonia liberated can be xemoved completely by heating the aqueous solution of the alkanolammonium salt and passing a vigorous nitrogen stream through the solution. The removal of ammonia can be 6upported by additionally distilling off a certain amount of water, which makes it possible to obtain at the same time a certain concentration of the active substance.
The alkenylsuccinic monoamides described above are clearly water-soluble or give easily emulsifiable pro-ducts with mineral oil. These products can be used asanticorrosive agents in aqueous cooling lubricants, in particular drilling, cutting and rolling fluids. These aqueous cooling lubricants are prepared by stirring the reaction products into the required amount of water or mixing them with mineral oil and emulsifying the con-centrates obtained in water. The concentration used in the drilling, cutting and rolling fluids is in general about 0.1 to 10% by weight, preferably 2-10% by weight.
The concentrations mentioned refer to the use of the products by themselves and also to the combinations mentioned with mineral oil.
These emulsion concentrates contain additional auxilia-ries for optimizing the emulsifying behavior and the corrosion protection. Examples which are used for this are ethoxylates of the formula R4 - 0 - (CH2 - CHz - O)~H
in which R4 is C,0-C20-alkyl, alkenyl or alkylphenyl and n represents numbers from 2to 10 and/or fatty acid alkanol-amides of the formula 3 o R5 - C0 - NR6R~
in which R5 is C10-C20-alkyl or C,0-C20-alkenyl and R6 and R7 are identical or different and are hydrogen, 2-hydroxy-ethyl or 2-hydroxypropyl. These products can be present h ~ ~
in the emulsion concentrate~ in amount6 of in each case about 20 to 40%.
Examples Example 1 Triethanolamine/sodium ~alt of pentapropenylsuccinic monoamide 300 g of purified water and 300 g (4.4 mol) of 25%
strength aqueous ammonia solution are initially intro-duced into a 4-neck flask equipped with distillation head, dropping funnel, thermometer and stirrer, and the mixture is cooled to 0C. 696 g (2.0 mol) of penta-propenylsuccinic anhydride are then added over a period of 30 minutes, while maintaining the temperature at 10-20DC with cooling. After the dropwise addition i8 completed, the mixture is stirred for another 3 hours at 298 g (2.0 mol) of triethanolamine are added to this ammonium salt solution, the mixture i8 stirred for 5 minutes, 96 g (1.2 mol) of NaOH (50% strength) are then added. The mixture is slowly (about 2 hours) heated to 110C with stirring, during which ammonia escapes and water and olefin distil off. The distillation is con-tinued for another 2 hours at 110C, during which about 500 g of ammoniacal water and about 50 g of olefin distil over. About 1090 g of a dark liquid having an active compound content of about 80% are obtained. The crude pentapropenylsuccinic anhydride used in this example has the following main componentss Pentapropenylsuccinic anhydride about 57%
Hexapropenyl~uccinic anhydride about 10%
Heptapropenylsuccinic anhydride about 3%
Pentapropylene about 22%
.
:~
5 2 ~ L,~ 2 ~ n~
Example 2 370 g of the product prepared in Example 1, 310 g of a tall oil fatty acid diethanolamide, 160 g of oleyl alcohol polyglycol ether (2 mol of ethylene oxide) and 160 g of nonylphenol polyglycol ether (2 mol of ethylene oxide) are mixed at room temperature and stirred until a clear solution has been formed.
Comparative sub~tance A
Triethanolamine/sodium salt of tripropenylsuccinic monoamide 150 g of water and 150 g (2.2 mol) of 25~ strength aqueous ammonia solution are initially introduced into a 4-necked flask equipped with distillation head, dropping funnel, thermometer and stirrer, and the m$xture is cooled to 5C. 224 g (1.0 mol) of tripropenylsuccinic anhydride are then added dropwise over a period of 15 minutes, while maintaining the temperature at 10-20C
with cooling. After the dropwise addition is completed, the mixture is stirred for another 3 hours at 30C.
149 g (1.0 mol) of triethanolamine are added, the mixture is stirred for 5 minutes, and 48 g (0.6 mol) of NaOH (50~
strength) are then added. The mixture is heated to 110C
over a period of 1-2 hours, while passing nitrogen through the solution. 299 g of ammoniacal water is distilled off at 110C over a period of 2 hours. The solids content is brought to 79% with 83 g of water.
469 g of product having a water content of about 18~ are obtained.
Comparative substance B 2 ~ 2 ~ ~
Triethanolamine/sodium salt of tetrapropenylsuccinic monoamide 150 g of water and 150 g (2.2 mol) of 25% strength aqueous ammonia solution are initially introduced into a 4-neck flask equipped with distillation head, dropping funnel, thermometer and stirrer, and the mixture is cooled to 0-5C. 266 g (1.0 mol) of tetrapropenylsuccinic anhydride are then added dropwise over a period of 15 minutes, while maintaining the temperature at 10-20C
with cooling. After the dropwise addition is completed, the mixture is stirred for another 3 hours at 30C.
149 g (1.0 mol) of triethanolamine are added, the mixture is stirred for 5 minutes, and 48 g (0.6 mol) of NaOH (50%
strength) are then added. The mixture is heated to 110C
over a period of 1-2 hours, while passing nitrogen through the solution. 270 g of ammoniacal water is distilled off at 110C over a period of 2 hours. The solids content is brought to 80.8% with 48.8 g of water.
Weight: 494 g Comparative substance C
370 g of comparative substance A, 310 g of tall oil fatty acid diethanolamide 160 g of oleyl alcohol polyglycol ether (2 mol of ethylene oxide) and 160 g of nonylphenol polyglycol ether (2 mol of ethylene oxide) are mixed at room temperature and stirred until a clear solution has been formed.
Comparative substance D
370 g of comparative substance B, 310 g of tall oil fatty acid diethanolamide 160 g of oleyl alcohol polyglycol ether (2 mol of 2 ~ 1 3 2 ~ ~
ethylene oxide) and 160 g of nonylphenol polyglycol ether (2 mol of ethylene oxide) are mixed at room temperature ancl stirred until a clear solution has been formed.
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Distinct anticorrosive properties towards iron metals, emulsifying power towards mineral oils, possibly also in combination with selected nonionic compounds, low ten-dency to foaming or rapid foam breakdown, growth inhibi-tion of microorganisms.
Only some of these requirements are met by the compoundslisted in EP 0,127,132. This document has already dis-closed alkenylsuccinic monoamides of the formula R ~ J ~ CH2 ~ CONH2 COO~ K~
where R is C6-Cl2-alkenyl and their use as anticorrosive agents.
However, these compounds show insufficient emulsifying power, which leads to unsatisfactory shelf lives of the emulsions to be used. Furthermore, emulsions containing these compounds have a tendency to foaming, which is a particular disadvantage in working processes, such as grinding, where the emulsions are exposed to high mechanical influences.
The disadvantages described can be overcome by using the - 2 _ 2 ~ ~ ~ 2 ~ ~
longer-chain alkenylsuccinic monoamides according to the invention which are described below. The opalescence of the emulsions achieved with these longer-chain alkenyl-succinic monoamides indicates finer dispersion of the emulsions compared with the shorter-chain ones and thus long shelf lives, i.e. the emulsion can be used longer.
The longer-chain alkenylsuccinic monoamides according to the inventio~ also fulfil the requirement of low tendency to foaming or rapid foam breakdown, which is not the case in the shorter-chain compounds.
Accordingly, the invention relates to alkenylsuccinic monoamides of the formulae R - CH - CH2 - CONH2 or R - CH - CH2 - coda Me~
COOe Me~ CONH2 in which R is Cl3-C30-alkenyl, preferably C15-C21-alkenyl, where R can be straight-chain or branched, and Ne~ is an alkali metal ion (Na', R+), a proton or an ammonium ion of the formula ~NHRlR2R3 and Rl, R2 and R3 are identical or different and are hydrogen, 2-hydroxyethyl or 2-hydroxy-propyl and to their use as anticorrosive agents.
The preparation of the alkenylsuccinic anhydrides used as starting materials from olefin and maleic anhydride is known. The alkenylsuccinic monoamides are obtained by reaction of 1 mol of an alkenylsuccinic anhydride with at least 2 mol of ammonia, which gives the alkenylsuccinic monoamide in the form of the ammonium salt. If aqueous ammonia solution is used, the ammonium salt of the alkenylsuccinic monoamide is formed in an aqueous solu-tion. By displacing the ammonia by means of other bases, other salts of the monoamides can be prepared. Salts which are particularly preferably used as anticorrosive agents are the alkanolamine salts, such as triethanol-amine or triisopropanolamine salts, which are prepared by reacting ~the initially formed ammonium salts with an aqueous splution of alkanolamine at elevated temperature.
2~ 32~ -The ammonia liberated can be xemoved completely by heating the aqueous solution of the alkanolammonium salt and passing a vigorous nitrogen stream through the solution. The removal of ammonia can be 6upported by additionally distilling off a certain amount of water, which makes it possible to obtain at the same time a certain concentration of the active substance.
The alkenylsuccinic monoamides described above are clearly water-soluble or give easily emulsifiable pro-ducts with mineral oil. These products can be used asanticorrosive agents in aqueous cooling lubricants, in particular drilling, cutting and rolling fluids. These aqueous cooling lubricants are prepared by stirring the reaction products into the required amount of water or mixing them with mineral oil and emulsifying the con-centrates obtained in water. The concentration used in the drilling, cutting and rolling fluids is in general about 0.1 to 10% by weight, preferably 2-10% by weight.
The concentrations mentioned refer to the use of the products by themselves and also to the combinations mentioned with mineral oil.
These emulsion concentrates contain additional auxilia-ries for optimizing the emulsifying behavior and the corrosion protection. Examples which are used for this are ethoxylates of the formula R4 - 0 - (CH2 - CHz - O)~H
in which R4 is C,0-C20-alkyl, alkenyl or alkylphenyl and n represents numbers from 2to 10 and/or fatty acid alkanol-amides of the formula 3 o R5 - C0 - NR6R~
in which R5 is C10-C20-alkyl or C,0-C20-alkenyl and R6 and R7 are identical or different and are hydrogen, 2-hydroxy-ethyl or 2-hydroxypropyl. These products can be present h ~ ~
in the emulsion concentrate~ in amount6 of in each case about 20 to 40%.
Examples Example 1 Triethanolamine/sodium ~alt of pentapropenylsuccinic monoamide 300 g of purified water and 300 g (4.4 mol) of 25%
strength aqueous ammonia solution are initially intro-duced into a 4-neck flask equipped with distillation head, dropping funnel, thermometer and stirrer, and the mixture is cooled to 0C. 696 g (2.0 mol) of penta-propenylsuccinic anhydride are then added over a period of 30 minutes, while maintaining the temperature at 10-20DC with cooling. After the dropwise addition i8 completed, the mixture is stirred for another 3 hours at 298 g (2.0 mol) of triethanolamine are added to this ammonium salt solution, the mixture i8 stirred for 5 minutes, 96 g (1.2 mol) of NaOH (50% strength) are then added. The mixture is slowly (about 2 hours) heated to 110C with stirring, during which ammonia escapes and water and olefin distil off. The distillation is con-tinued for another 2 hours at 110C, during which about 500 g of ammoniacal water and about 50 g of olefin distil over. About 1090 g of a dark liquid having an active compound content of about 80% are obtained. The crude pentapropenylsuccinic anhydride used in this example has the following main componentss Pentapropenylsuccinic anhydride about 57%
Hexapropenyl~uccinic anhydride about 10%
Heptapropenylsuccinic anhydride about 3%
Pentapropylene about 22%
.
:~
5 2 ~ L,~ 2 ~ n~
Example 2 370 g of the product prepared in Example 1, 310 g of a tall oil fatty acid diethanolamide, 160 g of oleyl alcohol polyglycol ether (2 mol of ethylene oxide) and 160 g of nonylphenol polyglycol ether (2 mol of ethylene oxide) are mixed at room temperature and stirred until a clear solution has been formed.
Comparative sub~tance A
Triethanolamine/sodium salt of tripropenylsuccinic monoamide 150 g of water and 150 g (2.2 mol) of 25~ strength aqueous ammonia solution are initially introduced into a 4-necked flask equipped with distillation head, dropping funnel, thermometer and stirrer, and the m$xture is cooled to 5C. 224 g (1.0 mol) of tripropenylsuccinic anhydride are then added dropwise over a period of 15 minutes, while maintaining the temperature at 10-20C
with cooling. After the dropwise addition is completed, the mixture is stirred for another 3 hours at 30C.
149 g (1.0 mol) of triethanolamine are added, the mixture is stirred for 5 minutes, and 48 g (0.6 mol) of NaOH (50~
strength) are then added. The mixture is heated to 110C
over a period of 1-2 hours, while passing nitrogen through the solution. 299 g of ammoniacal water is distilled off at 110C over a period of 2 hours. The solids content is brought to 79% with 83 g of water.
469 g of product having a water content of about 18~ are obtained.
Comparative substance B 2 ~ 2 ~ ~
Triethanolamine/sodium salt of tetrapropenylsuccinic monoamide 150 g of water and 150 g (2.2 mol) of 25% strength aqueous ammonia solution are initially introduced into a 4-neck flask equipped with distillation head, dropping funnel, thermometer and stirrer, and the mixture is cooled to 0-5C. 266 g (1.0 mol) of tetrapropenylsuccinic anhydride are then added dropwise over a period of 15 minutes, while maintaining the temperature at 10-20C
with cooling. After the dropwise addition is completed, the mixture is stirred for another 3 hours at 30C.
149 g (1.0 mol) of triethanolamine are added, the mixture is stirred for 5 minutes, and 48 g (0.6 mol) of NaOH (50%
strength) are then added. The mixture is heated to 110C
over a period of 1-2 hours, while passing nitrogen through the solution. 270 g of ammoniacal water is distilled off at 110C over a period of 2 hours. The solids content is brought to 80.8% with 48.8 g of water.
Weight: 494 g Comparative substance C
370 g of comparative substance A, 310 g of tall oil fatty acid diethanolamide 160 g of oleyl alcohol polyglycol ether (2 mol of ethylene oxide) and 160 g of nonylphenol polyglycol ether (2 mol of ethylene oxide) are mixed at room temperature and stirred until a clear solution has been formed.
Comparative substance D
370 g of comparative substance B, 310 g of tall oil fatty acid diethanolamide 160 g of oleyl alcohol polyglycol ether (2 mol of 2 ~ 1 3 2 ~ ~
ethylene oxide) and 160 g of nonylphenol polyglycol ether (2 mol of ethylene oxide) are mixed at room temperature ancl stirred until a clear solution has been formed.
-- 8 -- 2 i~
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I~ I
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~ ~ 3 e ~ u , æ~ ~
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c ~ 0 OD
~ ~ ~ .~ ~ æ~ q O n~ ~q O O
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a ~ " ~ ~ ~ ~ ~ ~ x ~ ~ 0 ,î~ ô
Claims (5)
1. An alkenylsuccinic monoamide of the formula or in which R is C13-C30-alkenyl, preferably C15-C21-alkenyl, where R can be branched or straight-chain, and Me+ is an alkali metal ion, a proton or an ammonium ion of the formula +NHR1R2R3 and R1, R2 and R3 are identical or dif-ferent and are hydrogen, 2-hydroxyethyl or 2-hydroxy-propyl.
2. Use of an alkenylsuccinic monoamide as claimed in claim 1 as anticorrosive agent in water- and/or mineral oil-containing formulations.
3. Use of an alkenylsuccinic monoamide as claimed in claim 1 as anticorrosive agent in water- and/or mineral oil-containing formulations together with ethoxylates of the formula R4 - O - (CH2 - CH2 - O)nH
in which R4 is C10-C20-alkyl, alkenyl or alkylphenyl and n represents numbers from 2 to 10 and/or fatty acid alkanolamides of the formula in which R5 is C10-C20-alkyl or C10-C20-alkenyl and R6 and R7 are identical or different and are hydrogen, 2-hydroxy-ethyl or 2-hydroxypropyl.
in which R4 is C10-C20-alkyl, alkenyl or alkylphenyl and n represents numbers from 2 to 10 and/or fatty acid alkanolamides of the formula in which R5 is C10-C20-alkyl or C10-C20-alkenyl and R6 and R7 are identical or different and are hydrogen, 2-hydroxy-ethyl or 2-hydroxypropyl.
4. A water- and/or mineral oil-containing anticorrosive agent, containing an alkenylsuccinic monoamide as claimed in claim 1.
5. A water- and/or mineral oil-containing anticorrosive agent, containing 0.1 to 10% by weight of an alkenyl-succinic monoamide as claimed in claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4020061 | 1990-06-23 | ||
| DEP4020061.2 | 1990-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2045205A1 true CA2045205A1 (en) | 1991-12-24 |
Family
ID=6408950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002045205A Abandoned CA2045205A1 (en) | 1990-06-23 | 1991-06-21 | Salts of alkenylsuccinic monoamides and their use as anticorrosive agents and emulsifiers for metal-working oils |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0464473B1 (en) |
| JP (1) | JPH04230251A (en) |
| AT (1) | ATE109455T1 (en) |
| CA (1) | CA2045205A1 (en) |
| CS (1) | CS191091A2 (en) |
| DE (1) | DE59102414D1 (en) |
| ES (1) | ES2061115T3 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59308091D1 (en) * | 1992-08-22 | 1998-03-12 | Clariant Gmbh | Alkenyl succinic acid derivatives as metalworking aids |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2982634A (en) * | 1959-01-27 | 1961-05-02 | Socony Mobil Oil Co Inc | Alkenyl succinamic acid deicer |
| US3256196A (en) * | 1963-11-13 | 1966-06-14 | Sinclair Research Inc | Amide load carrying agent |
| DE3319183A1 (en) * | 1983-05-27 | 1984-11-29 | Hoechst Ag, 6230 Frankfurt | USE OF ALKENYLSBERSTALIC ACID HALBAMIDES AS AN ANTI-CORROSIVE AGENT |
| US4579922A (en) * | 1983-08-02 | 1986-04-01 | Arakawa Kagaku Kogyo Kabushiki Kaisha | Emulsifier for emulsion polymerization |
| DE3501180A1 (en) * | 1985-01-16 | 1986-07-17 | Hoechst Ag, 6230 Frankfurt | SALTS OF ALKENYLSBERSTALIC ACID HALBAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS CORROSION INHIBITORS |
| DE3534439A1 (en) * | 1985-09-27 | 1987-04-02 | Hoechst Ag | USE OF ALKENYLSBERSTALIC ACID HALBAMIDES AS AN ANTI-CORROSIVE AGENT |
-
1991
- 1991-06-19 AT AT91110057T patent/ATE109455T1/en not_active IP Right Cessation
- 1991-06-19 EP EP91110057A patent/EP0464473B1/en not_active Expired - Lifetime
- 1991-06-19 DE DE59102414T patent/DE59102414D1/en not_active Expired - Fee Related
- 1991-06-19 ES ES91110057T patent/ES2061115T3/en not_active Expired - Lifetime
- 1991-06-20 JP JP3148962A patent/JPH04230251A/en not_active Withdrawn
- 1991-06-21 CS CS911910A patent/CS191091A2/en unknown
- 1991-06-21 CA CA002045205A patent/CA2045205A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04230251A (en) | 1992-08-19 |
| EP0464473A1 (en) | 1992-01-08 |
| ES2061115T3 (en) | 1994-12-01 |
| ATE109455T1 (en) | 1994-08-15 |
| CS191091A2 (en) | 1991-12-17 |
| EP0464473B1 (en) | 1994-08-03 |
| DE59102414D1 (en) | 1994-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |