EP0192358A2 - Composition lubrifiante pour le traitement de métal - Google Patents

Composition lubrifiante pour le traitement de métal Download PDF

Info

Publication number
EP0192358A2
EP0192358A2 EP86300562A EP86300562A EP0192358A2 EP 0192358 A2 EP0192358 A2 EP 0192358A2 EP 86300562 A EP86300562 A EP 86300562A EP 86300562 A EP86300562 A EP 86300562A EP 0192358 A2 EP0192358 A2 EP 0192358A2
Authority
EP
European Patent Office
Prior art keywords
composition according
alkoxy
acid
amine
composition
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
Application number
EP86300562A
Other languages
German (de)
English (en)
Other versions
EP0192358B1 (fr
EP0192358A3 (en
Inventor
Yuval Halpern
Lee Cherney
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GE Chemicals Inc
Original Assignee
GE Chemicals Inc
Borg Warner Chemicals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by GE Chemicals Inc, Borg Warner Chemicals Inc filed Critical GE Chemicals Inc
Publication of EP0192358A2 publication Critical patent/EP0192358A2/fr
Publication of EP0192358A3 publication Critical patent/EP0192358A3/en
Application granted granted Critical
Publication of EP0192358B1 publication Critical patent/EP0192358B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00Lubricating compositions containing more than 10% water
    • C10M173/02Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00Lubricating compositions characterised by the additive being an inorganic material
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26Carboxylic acids; Salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00Lubricating compositions containing more than 10% water
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02Water
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06Metal compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08Inorganic acids or salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08Inorganic acids or salts thereof
    • C10M2201/081Inorganic acids or salts thereof containing halogen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08Inorganic acids or salts thereof
    • C10M2201/082Inorganic acids or salts thereof containing nitrogen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08Inorganic acids or salts thereof
    • C10M2201/084Inorganic acids or salts thereof containing sulfur, selenium or tellurium
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/085Phosphorus oxides, acids or salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/18Ammonia
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/122Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/141Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/22Acids obtained from polymerised unsaturated acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/22Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01Emulsions, colloids, or micelles

Definitions

  • the present invention relates to water soluble metal-working compositions in general, and to water soluble lubricants and coolants in particular.
  • Metal-working compositions of the present invention may be used in commercial applications, such as steel drilling, milling, tapping, grinding, boring, turning and cutting.
  • U.S. Patent No. 2,917,160 to Turinsky relates to a water-soluble lubricating composition of an ethoxylated amine and a salt-forming acid, such as phosphoric acid or lactic acid. According to Turinsky, this lubricant composition should have a pH below 8, and is useful in water emulsions in a ratio of 1 part amine to 3 parts water.
  • a similar aqueous cutting fluid is disclosed by U.S. Patent No. 3,186,946 to Sluhan. This cutting fluid consists of a tertiary ethoxylated amine in aqueous solution with boric acid to form an amine salt.
  • U.S. Patent No. 3,195,332 to Ranauto discloses an aqueous lubricant composition which includes a polyoxyethylene imidazoline.
  • a corrosion inhibitor such as sodium nitrite, triethanol amine or morpholine may also be included.
  • U.S. Patent No. 2,990,369 to Shapiro discloses a metal-working lubricant specifically adapted for the cutting and grinding of titanium.
  • This water-based lubricant composition comprises sodium fluoride, a high molecular weight imidazoline, a silicofluoride and a rosin amine ethylene oxide adduct.
  • U.S. Patent No. 3,265,620 to Heiman discloses an aqueous metal-working coolant comprising an ethanol amine, an alkali metal nitrite, and an aryl triazole which is at least one of benzotriazole and 4-nitrobenzotriazole.
  • a chelating agent such as an amino polycarboxylic acid.
  • compositions which may be emulsified in water, is disclosed by U.S. Patent No. 4,185,485 to Schick et al.
  • This composition includes an ester formed by reacting an alkenylsuccinic anhydride or acid with a hydroxy containing tertiary alkylamine, such as triethanol amine, or a hydroxy polyether amine.
  • This composition may also contain a C 2 -C 10 monocarboxylic acid.
  • the reaction product' is formed from an alkenylsuccinic anhydride or acid reacted with a hydroxy polyether amine
  • the composition may contain a rosin soap in addition to or instead of the monocarboxylic acid.
  • U.S. Patent No. 3,280,029 to Waldmann relates to a composition for improved lubricating oils and water-in- oil emulsions comprising alkyl amino monoalkanols, such as monoethyl aminoethanol, diethyl amino ethanol and diethyl amino ethoxy ethanol.
  • U.S. Patent No. 4,043,925 to Felton relates to a water-based metal-forming composition comprising a block copolymer with a central portion of polypropylene oxide with polyethylehe oxide at each end, a sulfochlorinated fatty acid, an alkoxylated 1,5-aza pentane, and potassium hydroxide.
  • 4,329,249 to Forsberg relates to the formation of nitrogen-containing phosphorous-free carboxylic acid derivatives.
  • These derivatives may be formed by reacting a carboxylic acid acylating agent with an alkylmonoalkoxy tertiary amine, and are useful for the incorporation of oil-soluble, water-insoluble functional additives into water-based functional fluids, such as water-based hydraulic fluids.
  • metal-working fluids related in certain aspects to the metal-working fluid of the present invention, are disclosed by U.S. Patent Nos. 4,172,802 to Rieder, 4,177,154 to Chakrabarti, and 3,933,658 to Beiswanger et al.
  • a phosphoral tris(diethanolamide) additive is disclosed for water-based and ethylene-glycol based hydraulic fluids and lubricants in Wear, 50 (1978) 365-369, Ludomir, Tokarzewski, Zakrzew- ski, Wachowicz and Szczepaniak.
  • Another phosphorus based metal-working composition is disclosed in Polish Patent Document No. 116,962 to Szczepaniak et al.
  • metal working fluids may have some disadvantages which are obviated or minimized by the metal working fluid of the present invention.
  • the metal working composition of the present invention may be synthesized by merely mixing the components together.
  • metal working fluids do not require that the components chemically react with each other, many compositions require a high proportion of relatively more expensive active ingredients to relatively less expensive ingredients, thereby increasing the cost of the metal-working composition.
  • Some metal working compositions may have the further disadvantage of requiring components which pose a potential health hazard to persons using them.
  • many metal working fluids used in the past contained nitrites, which have recently been recognized as participating in the conversion of certain chemical substances into carcinogens.
  • the United States Environmental Protection Agency recently promulgated a rule prohibiting the addition of nitrosating agents, such as nitrites, to triethanolamine salts of substituted organic acids when the mixture is to be used in metal working fluids due to the carcenogenic propensity of such materials demonstrated in animal studies (Federal Register, Vol. 49 No. 116, June 14, 1984, Rules and Regulations). This difficulty is avoided by the present invention, which exhibits good metal working properties without containing nitrosating agents.
  • the present invention is a water-soluble, metal-working composition which includes a relatively large alkoxylated amine, an alkanol amine and an acid-derived compound, wherein the large alkoxylated amine is generally described by the formula: Consistent with this formula, R 1 is selected from the group consisting of hydrogen, hydrocarbyl moieties, alkoxy moieties and polyalkoxy moieties, R 2 is selected from the group consisting of C 7 and larger hydrocarbyl moieties, and R 3 is selected from the group consisting of alkoxy moieties and polyalkoxy moieties.
  • the alkanol amine may generally be described by the formula:
  • R 4 is selected from the group consistent of hydrogen, C 1 -C 6 hydrocarbyl moieties, and monomeric and polymeric alkoxy moieties consisting essentially of alkoxy units selected from the group consisting of ethoxy, 2-propoxy, 2-butoxy and mixtures thereof.
  • R 5 is selected from the group consisting of C 1 -C 6 hydrocarbyl moieties, and monomeric and polymeric alkoxy moieties consisting essentially of alkoxy units selected from the group consisting of ethoxy, 2-propoxy, 2-butoxy and mixtures thereof.
  • R 6 is selected from the group consisting of monomeric and polymeric alkoxy moieties consisting essentially of alkoxy units selected from the group consisting of ethoxy, 2-propoxy, 2-butoxy and mixtures thereof.
  • R 4 , R 5 and R 6 are additionally selected so that the alkanol amine contains a total of 6 or fewer alkoxy units.
  • the acid-derived compound included in the present invention is selected from the group consisting of inorganic acids, organic acids, and salts thereof.
  • the present invention is a water-soluble, metal-working composition
  • a relatively large alkoxylated amine is a relatively large amine which may be generally described by the formula:
  • R 2 is a relatively large hydrocarbon group selected from the group consisting C 7 and larger hydrocarbyl moieties.
  • hydrocarbyl moieties are generally alkyl or alkenyl in character, but may be an aryl moiety such as benzyl, methyl benzyl or dimethoxy benzyl, and alkyl phenyls such as nonyl phenyl.
  • alkyl and alkenyl moieties are preferred.
  • Polyalkoxy groups are not included.
  • Stearyl, oleyl, soya, coco and tallow moieties are most preferred.
  • R 1 is selected from the group consisting of hydrogen, hydrocarbyl moieties, alkoxy moieties and polyalkoxy moieties.
  • the hydrocarbyl moieties may be aryl, alkyl or alkenyl in character, such as phenyl, stearyl, oleyl, soya, coco and tallow. Alkyl or alkenyl groups are preferred.
  • R 1 may be selected independent of R 2 , when R 1 is hydrocarbyl it is preferred that R 1 be the same as R 2 due to the relative cost efficiency of preparing the alkoxylated amine when, instead of being different hydrocarbyl moieties, both R1 and R2 are the same.
  • R1 is an alkoxy or a polyalkoxy moiety, consistent with those defined for R 3 .
  • R 3 may only be selected from the group consisting of alkoxy and polyalkoxy moieties.
  • these alkoxy and polyalkoxy moieties consist essentially of alkoxy units generally described by the following formula.
  • the oxygen of alkoxy moieties and the terminal oxygen of polyalkoxy moieties is bonded to hydrogen, not shown in the above formula, to form a terminal hydroxy group.
  • R 7 is selected from the group consisting of hydrogen and C 1 -C 28 hydrocarbyl moieties, such as alkyl groups like methyl, ethyl and propyl. More preferably, R 7 is hydrogen, methyl or ethyl, so that the alkoxy unit is an ethoxy, 2-propoxy or 2-butoxy unit, respectively. Ethoxy and propoxy units, wherein R 7 is hydrogen or methyl, respectively, are even more preferred.
  • R 3 may be a polyalkoxy moiety consisting of a mixture of different alkoxy units, such as a mixture of ethoxy units and propoxy units, it is more preferred that R 3 be homogenous. Hydroxy ethyl and homogenous polyethoxy moieties are most preferred.
  • R 1 may be selected independently from R 3 , when R 1 is an alkoxy or polyalkoxy moiety, it is preferred that R 1 consist essentially of at least some of the same alkoxy units as R 3 in order to simplify preparation of the tertiary alkoxylated amine.
  • R 3 when R 3 is a polyalkoxy moiety of mixed ethoxy and propoxy units, it is preferred that R be hydroxy ethyl, hydroxy propyl, polyethoxy, polypropoxy or a polyalkoxy moiety of mixed ethoxy and propoxy units.
  • R 1 when R 3 is a polyethoxy moiety, it is preferred that R 1 be hydroxy ethyl, polyethoxy or a mixed polyalkoxy moiety of ethoxy units and other alkoxy units. Most preferably, however, both R 1 and R 3 consist essentially of the same kind of alkoxy units.
  • R 1 and R 3 are chosen such that the total number of alkoxy units in the large alkoxylated amine is equal to 2 to about 35.
  • the total number of alkoxy groups may be equal to 2 when each of R 1 and R 3 is hydroxy ethyl, or when R 3 is a polyethoxy moiety consisting of 2 ethoxy units and R 1 is hydrogen or a hydrocarbyl moiety such as tallow.
  • the total number of alkoxy units in said large alkoxylated amine is equal to about 5 to about 20, such as where R 3 is a polyethoxy moiety consisting of three ethoxy units, and R 1 is a polyethoxy moiety consisting of two ethoxy units.
  • Relatively large alkoxylated amines consistent with the preferred embodiment of the invention are commercially available from the Borg - Warner Corporation under the trademark "PEGAMEEN".
  • the alkanol amine of the present invention is a relatively small amine, and may be generally described by the formula:
  • R 4 is selected from the group consisting of hydrogen, C 1 -C 6 hydrocarbyl moieties such as methyl, phenyl, ethyl, propyl and butyl, and monomeric and polymeric alkoxy moieties.
  • R 4 is a monomeric or polymeric alkoxy moiety, the alkoxy moiety consists essentially of alkoxy units selected from the group consisting of ethoxy, 2-propoxy, 2-butoxy and mixtures thereof.
  • R 4 when R 4 is a monomeric alkoxy moiety, R 4 is selected from the group consisting of hydroxy ethyl(HO-CH 2 CH 2 -), 2-hydroxy propyl(CH 3 CH(OH) CH 2 ), and 2-hydroxy butyl(CH 3 CH 2 CH(OH)CH Z -) moieties.
  • R 4 may be a polymeric alkoxy moiety, such as polyethoxy(HOCH2CH2OCH2-CH2-) or polypropoxy (CH 3 CH(OH)-CH 2 OCH(CH 3 )CH 2 -),
  • R 4 preferably is a simple alkoxy moiety, such as hydroxy ethyl or 2-hydroxy propyl, a simple hydrocarbyl such as methyl, ethyl, or hydrogen, such as in dimethyl ethanol amine, N-phenyl ethanol amine, and N,N-diethyl ethanol amine. Hydroxy ethyl and hydrogen are most preferred, such as when the alkanol amine is triethanol amine, diethanol amine or N-methyl ethanol amine.
  • R S may be selected from the group consisting of C 1 -C 6 hydrocarbyl moieties, as discussed above for R 4 , and monomeric and polymeric alkoxy moieties which consist essentially of alkoxy units selected from the group consisting of ethoxy, 2-propoxy, 2-butoxy and mixtures thereof, as discussed above for R 4 .
  • R 5 may not be hydrogen. Consequently, although the alkanol amine may be a secondary or tertiary amine, the alkanol amine may not be a primary amine.
  • R is methyl, as in N-methyl ethanol amine or dimethyl ethanol amine, or hydroxy ethyl, as in diethanol amine or triethanol amine.
  • R 6 may be a monomeric or polymeric alkoxy moiety consisting essentially of alkoxy units selected from the group consisting of ethoxy, 2-propoxy, 2-butoxy, and mixtures thereof, as discussed above for R 4 .
  • R 6 is hydroxy ethyl or 2-hydroxy propyl. Hydroxy ethyl is more preferred. Triethanol amine, N-methyl ethanol amine and mixtures thereof are most preferred.
  • each of R 41 R 5 and R 6 may be a polymeric alkoxy group
  • the alkanol amine may contain no more than a total of 6 alkoxy units. However, fewer than 6 alkoxy units are preferred, such as in triethanol amine, diethanol amine and N-methyl ethanol amine, wherein the total number of alkoxy units is equal to or less than 3.
  • the composition of the present invention also contains an acid-derived compound.
  • This acid-derived compound may be an organic acid, an inorganic acid or a salt derived from an organic or inorganic acid by the replacement of an acidic hydrogen by another appropriate cation.
  • Preferred organic acid-derived compounds include acetic acid, propionic acid, butyric acid, formic acid, oxalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, benzoic acid, suberic acid, azelaic acid, para-toluene sulfonic acid, sebacic acid, and amino acids such as alanine, leucine, phenylalanine, glycine, tyrosine, serine, aspartic acid and glutamic acid.
  • the acid-derived compound is an inorganic acid, with phosphoric acid, nitric acid and sulfuric acid being preferred. Boric acid is not preferred. Phosphoric acid is most preferred.
  • the acid-derived compound may be a salt of an organic or inorganic acid, and preferably is a salt of the preferred acids discussed above.
  • the acid-derived compound is a salt, it is preferred that the acid-derived compound be a Group VIII metal, alkaline metal, alkaline earth metal or amine salt.
  • salts consistent with this embodiment include iron phosphates, ammonium sulfates and sodium nitrates.
  • the composition of the present invention provides a metal-working composition in which time-consuming and costly component preparation may be avoided, and yet achieve excellent cooling, high lubricity, and extreme-pressure properties. Further, the composition of the present invention may exhibit high thermal and hydrolytic stability, while inhibiting the development of rust on the workpiece and equipment. Some formulations, such as those containing N-methyl ethanol amine as some or all of the alkanol amine component, may also exhibit a lowered susceptibility to the growth of mold and bacteria.
  • the ratio of the ingredients for optimum performance in a particular application, such as extreme-pressure properties, can be adjusted as needed. It is preferred, however, that the ratio by weight of the alkanol amine to the relatively large alkoxylated amine be about 20:1 to about 0.0.5:1. More preferably, however, the ratio by weight of the alkanol amine to the large alkoxylated amine is about 10:1 to about 0.1:1, with a ratio of about 7:1 to about 0.5:1 being most preferred.
  • the ratio of the alkanol amine to the relatively large alkoxylated amine is about 20:1 to about 0.05:1, it is preferred that the ratio by weight of the acid-derived compound to the large alkoxylated amine be about 3:1 to about 0.01:1. Ratios of acid-derived compound to large alkoxylated amine of about 1.5:1 to about 0.1:1, however, are more preferred.
  • the composition of the present invention usually will be stored and shipped in a relatively concentrated form. Although this concentrate may contain no significant quantities of water, the composition usually will be shipped and stored as an aqueous solution which contains 10-60% by weight, and preferably 20-50% by weight, of the relatively large alkoxylated amine, the alkanol amine and the acid-derived compound combined.
  • composition of the present invention may be used in a concentrated form, due to the fact that a significant portion of the cost of a lubricating composition generally is for the "active" components rather than the carrier medium, e.g. water or oil, it is generally preferred that the amount of metal-working composition in a lubricant or coolant be as low as practically possible.
  • the composition of the present invention may be used in the form of highly dilute aqueous solutions without adversely affecting the lubricity, extreme-pressure or anti-wear properties of the invention.
  • the composition is an aqueous solution which includes at least 85% by weight water, based on the total weight of the solution, and about 0.1 1 to 15% by weight of the combined large alkoxylated amine, alkanol amine and the acid-derived compound, although, as is known to those skilled in the art, the appropriate concentration will vary depending on the application. More preferably, however, the large alkoxylated amine, the alkanol amine and the acid-derived compound together constitute about 0.5 to about 10% by weight of the solution, with about 0.5 to 5% being most preferred.
  • the pH of the composition be equal to about 7.5 to about 10.5 in order to minimize the corrosive effects of the composition on the workpiece; pH's in the range of about 8 to about 9.5 are more preferred. Consistent with the invention, pH's in the preferred ranges may be attained by adjusting the proportions of the various components to each other, and/or by adding other components, such as acids or bases, to maintain the proper pH balance. Other components may also be added to assist in solubilizing the composition in water, although these are not usually necessary. Other known additives, such as biocides, dyes, perfumes, antifoam compounds, crystal growth modifiers, scale inhibitors and chelating agents for hard water use may also be included.
  • Examples 1-28 illustrate the testing of various fluids to determine their load carrying properties by determining their maximum load to failure. Testing reported in Tables I and II was performed according to ASTM No. D 3233-73, "Standard Methods for Measurement of Extreme Pressure Properties of Fluid Lubricants (Falex Methods)".
  • the lubricating fluids in these examples are fluids formed by placing the components indicated in deionized water. Amounts indicated are weight percent, based upon the total weight of the fluid.
  • the term DEA indicates diethanol amine and TEA indicates triethanol amine.
  • Examples 1-7 represent various formulations of the preferred embodiment of the invention, wherein the solubilizing component is the inorganic acid, H 3 P0 4 .
  • the composition of the present invention is not limited to inorganic acids or H 3 PO 4 in particular may be seen from Examples 21-28.
  • Comparative Examples C8-C12 represent testing of various commercially available metal-working compositions as a basis for comparing the composition of the present invention.
  • Cim Cool 400 is a proprietary metal-working concentrate, for heavy machinery and grinding, of Cincinnati Milacron; Do-All is #470 soluble oil of Do-All Finishing Company; Antara HR-719 is a proprietary metal-working lubricant of GAF Corp.; E-Cool is a proprietary fluid from Henry E. Sanson & Sons, Inc., and Clear Mint is a concentrated, synthetic cutting lubricant, coolant and rust inhibitor from Amitron Products, Inc.
  • Comparative Examples C13-C20 represent testing of various components useful in making the composition of the present invention.
  • H 3 P0 4 is 85 wt% phosphoric acid aqueous solution.
  • PEGAMEEN is a Trademark of Borg-Warner Chemicals, Inc. used in conjunction with amine compounds corresponding to relatively large alkoxylated amines useful in the present invention, according to the general formula discussed above, wherein R 1 is an alkoxy or polyalkoxy moiety.
  • the numerical portion of the PEGAMEEN designation, such as T-7, T-15 and T-25, indicates the average value of the total number of alkoxy units in the large amine compound.
  • T-7 indicates an average value of 7
  • T-15 indicates an average value of 15
  • T-25 indicates an average value of 25.
  • R 2 of the alkoxylated amine is a tallow moiety.
  • Examples 21-28 illustrate the effect of various inorganic acids, such as H 2 SO 4 and boric oxide, which hydrolyzes to boric acid in the presence of water, carboxylic acids, and salts on the extreme-pressure test results conducted as described above.
  • a series of compositions were prepared containing 0.4% by weight of Pegameen T-7, 2.0% by weight triethanol amine and various concentrations of different acids or salts. The acids or salts, their concentration and the extreme-pressure test results are indicated in Table II.
  • alkanol amine may be N-methyl ethanol amine without degrading the metal working properties of the composition of the present invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP86300562A 1985-02-04 1986-01-28 Composition lubrifiante pour le traitement de métal Expired - Lifetime EP0192358B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US69781085A 1985-02-04 1985-02-04
US697810 1985-02-04

Publications (3)

Publication Number Publication Date
EP0192358A2 true EP0192358A2 (fr) 1986-08-27
EP0192358A3 EP0192358A3 (en) 1987-10-14
EP0192358B1 EP0192358B1 (fr) 1991-01-02

Family

ID=24802646

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86300562A Expired - Lifetime EP0192358B1 (fr) 1985-02-04 1986-01-28 Composition lubrifiante pour le traitement de métal

Country Status (5)

Country Link
EP (1) EP0192358B1 (fr)
JP (1) JPS61235499A (fr)
KR (1) KR930007896B1 (fr)
DE (1) DE3676315D1 (fr)
MX (1) MX168689B (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0252533A1 (fr) * 1986-05-13 1988-01-13 Berol (Suisse) S.A. Procédé de formage mécanique d'aluminium et des alliages de l'aluminium, en présence d'un agent réfrigérant et lubrifiant, et produit concentré de la composition refrigérante et lubrifiante
WO1989009254A1 (fr) * 1988-03-30 1989-10-05 Berol Nobel Stenungsund Ab Fluide a base d'eau pour le travail des metaux, renfermant au moins un compose d'alcanolamine comme agent antimicrobien, et procede de travail des metaux mis en oeuvre en presence dudit fluide
US5633222A (en) * 1992-12-17 1997-05-27 Berol Nobel Ab Use of a secondary amine as a corrosion inhibiting and antimicrobial agent and an aqueous alkaline industrial fluid containing said amine
WO2000014191A1 (fr) * 1998-09-07 2000-03-16 Skoeld Rolf Travail mecanique d'un metal contenant du cuivre ou de l'aluminium
CN101597540B (zh) * 2009-07-03 2012-05-23 华南理工大学 一种适用于气门加工的防锈切削液
US8372336B2 (en) 2009-07-03 2013-02-12 Akzo Nobel Chemicals International B.V. Polymeric corrosion inhibitors
US8940227B2 (en) 2010-08-30 2015-01-27 Akzo Nobel Chemical International B.V. Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors
CN111500352A (zh) * 2020-04-13 2020-08-07 南通科星化工有限公司 一种金属切削液及制备方法
CN113462458A (zh) * 2021-07-15 2021-10-01 江苏捷捷半导体新材料有限公司 一种高效金刚线硅片切割液
CN113736550A (zh) * 2021-09-02 2021-12-03 江苏捷捷半导体新材料有限公司 一种用于切片设备循环系统的金刚线切割液及其制备方法
CN111925858B (zh) * 2020-08-05 2023-01-06 沂盟材料科技(上海)有限公司 用于金属件加工的水性全合成搓丝液及其制备方法和应用

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0269508A (ja) * 1988-09-03 1990-03-08 Fuji Kobunshi Kk 熱圧成形化粧板用樹脂組成物
CN111040827B (zh) * 2019-12-11 2022-11-29 富兰克润滑科技(太仓)有限公司 一种有机羧酸复配剂、制备方法及钢板水基加工液

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2917160A (en) * 1951-04-12 1959-12-15 Armour & Co Metal working method and lubricant therefor
US3799876A (en) * 1970-12-11 1974-03-26 Texaco Inc Corrosion inhibiting lubrication method
FR2231739A1 (fr) * 1973-05-29 1974-12-27 Exxon Research Engineering Co
US4420414A (en) * 1983-04-11 1983-12-13 Texaco Inc. Corrosion inhibition system

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6043394B2 (ja) * 1983-02-07 1985-09-27 出光興産株式会社 金属加工油
JPS6025080B2 (ja) * 1982-12-03 1985-06-15 出光興産株式会社 金属加工油

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2917160A (en) * 1951-04-12 1959-12-15 Armour & Co Metal working method and lubricant therefor
US3799876A (en) * 1970-12-11 1974-03-26 Texaco Inc Corrosion inhibiting lubrication method
FR2231739A1 (fr) * 1973-05-29 1974-12-27 Exxon Research Engineering Co
US4420414A (en) * 1983-04-11 1983-12-13 Texaco Inc. Corrosion inhibition system

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0252533A1 (fr) * 1986-05-13 1988-01-13 Berol (Suisse) S.A. Procédé de formage mécanique d'aluminium et des alliages de l'aluminium, en présence d'un agent réfrigérant et lubrifiant, et produit concentré de la composition refrigérante et lubrifiante
EP0252534A1 (fr) * 1986-05-13 1988-01-13 Berol (Suisse) S.A. Procédé de formage mécanique d'aluminium et des alliages de l'aluminium, en présence d'un agent réfrigérant et lubrifiant, et produit concentré de la composition réfrigérante et lubrifiante
WO1989009254A1 (fr) * 1988-03-30 1989-10-05 Berol Nobel Stenungsund Ab Fluide a base d'eau pour le travail des metaux, renfermant au moins un compose d'alcanolamine comme agent antimicrobien, et procede de travail des metaux mis en oeuvre en presence dudit fluide
US5132046A (en) * 1988-03-30 1992-07-21 Berol Nobel Stenungsund Ab Water-based metal working fluid containing at least one alkanolamine compound as antimicrobial agent and a metal working process performed in the presence of said fluid
US5633222A (en) * 1992-12-17 1997-05-27 Berol Nobel Ab Use of a secondary amine as a corrosion inhibiting and antimicrobial agent and an aqueous alkaline industrial fluid containing said amine
US6602833B1 (en) 1998-09-07 2003-08-05 Ab Chem Dimension Mechanical working in the presence of a metal containing copper or aluminum
WO2000014191A1 (fr) * 1998-09-07 2000-03-16 Skoeld Rolf Travail mecanique d'un metal contenant du cuivre ou de l'aluminium
CN101597540B (zh) * 2009-07-03 2012-05-23 华南理工大学 一种适用于气门加工的防锈切削液
US8372336B2 (en) 2009-07-03 2013-02-12 Akzo Nobel Chemicals International B.V. Polymeric corrosion inhibitors
US8940227B2 (en) 2010-08-30 2015-01-27 Akzo Nobel Chemical International B.V. Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors
CN111500352A (zh) * 2020-04-13 2020-08-07 南通科星化工有限公司 一种金属切削液及制备方法
CN111925858B (zh) * 2020-08-05 2023-01-06 沂盟材料科技(上海)有限公司 用于金属件加工的水性全合成搓丝液及其制备方法和应用
CN113462458A (zh) * 2021-07-15 2021-10-01 江苏捷捷半导体新材料有限公司 一种高效金刚线硅片切割液
CN113736550A (zh) * 2021-09-02 2021-12-03 江苏捷捷半导体新材料有限公司 一种用于切片设备循环系统的金刚线切割液及其制备方法

Also Published As

Publication number Publication date
JPS61235499A (ja) 1986-10-20
KR860006535A (ko) 1986-09-11
KR930007896B1 (ko) 1993-08-21
EP0192358B1 (fr) 1991-01-02
EP0192358A3 (en) 1987-10-14
DE3676315D1 (de) 1991-02-07
MX168689B (es) 1993-06-04

Similar Documents

Publication Publication Date Title
US4151099A (en) Water-based hydraulic fluid and metalworking lubricant
EP0152677B1 (fr) Systèmes aqueux contenant des composés organo-borate
AU703374B2 (en) Alkyl ether amine conveyor lubricants containing corrosion inhibitors
EP0192358B1 (fr) Composition lubrifiante pour le traitement de métal
EP0061693B1 (fr) Fluides hydrauliques à base d'eau ayant des proportions lubrifiantes et d'inhibition de corrosion améliorées
CA1197371A (fr) Alcools composites anticorrosion
US6511946B1 (en) Water-miscible cooling lubricant concentrate
US4661275A (en) Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products
US4452758A (en) Compositions and process for inhibiting corrosion of aluminum
US4927550A (en) Corrosion preventive composition
CA1203527A (fr) Fluide de coupe ou de commande hydraulique
EP0183050A1 (fr) Additif pour lubrifiant
US4313836A (en) Water-based hydraulic fluid and metalworking lubricant
US4218329A (en) Cooling and lubricating fluid for metal working
JP2530633B2 (ja) ヒドロカルビル置換こはく酸及び/又は無水物とアミン末端付ポリ(オキシアルキレン)との反応生成物並びに同上を含む水性システム
CA1190541A (fr) Fluide fonctionnel aqueux
US4670172A (en) Process and kit for working metals
US3798164A (en) Polyoxyalkylene bis-thiourea extreme pressure agents and methods of use
CA1294511C (fr) Fluides aqueux
US6238621B1 (en) Corrosion inhibiting compositions
US4414125A (en) Alkali metal or amine salts of a mixture of 2- and 3-alkyladipic acids as corrosion inhibitors
US4683081A (en) Aqueous corrosion inhibitor compositions of a half-amide and a dicarboxylic acid amine salt
US5668093A (en) Use of alkenylsuccinic acid half-amides
EP1115816A1 (fr) Procede de travail mecanique d'un metal contenant du cobalt
JP3148395B2 (ja) 潤滑剤組成物

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: A2

Designated state(s): DE FR GB IT NL

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

RHK1 Main classification (correction)

Ipc: C10M173/02

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): DE FR GB IT NL

17P Request for examination filed

Effective date: 19871116

17Q First examination report despatched

Effective date: 19890306

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: GE CHEMICALS, INC.

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE FR GB IT NL

REF Corresponds to:

Ref document number: 3676315

Country of ref document: DE

Date of ref document: 19910207

ET Fr: translation filed
ITF It: translation for a ep patent filed
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: FR

Payment date: 19931214

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19931217

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19931222

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19940131

Year of fee payment: 9

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19950128

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19950801

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19950128

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19950929

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 19950801

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19951003

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;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050128