EP0192358A2 - Metallbearbeitungsflüssigkeitzusammensetzung - Google Patents
Metallbearbeitungsflüssigkeitzusammensetzung Download PDFInfo
- 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
Links
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
- 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
- C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
-
- 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
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/06—Metal compounds
-
- 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
- C10M2201/08—Inorganic acids or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/08—Inorganic acids or salts thereof
- C10M2201/081—Inorganic acids or salts thereof containing halogen
-
- 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
- C10M2201/08—Inorganic acids or salts thereof
- C10M2201/082—Inorganic acids or salts thereof containing nitrogen
-
- 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
- C10M2201/08—Inorganic acids or salts thereof
- C10M2201/084—Inorganic acids or salts thereof containing sulfur, selenium or tellurium
-
- 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
- C10M2201/085—Phosphorus oxides, acids or salts
-
- 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
- C10M2201/18—Ammonia
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- 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
- 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)
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 (de) | 1986-08-27 |
EP0192358A3 EP0192358A3 (en) | 1987-10-14 |
EP0192358B1 EP0192358B1 (de) | 1991-01-02 |
Family
ID=24802646
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86300562A Expired - Lifetime EP0192358B1 (de) | 1985-02-04 | 1986-01-28 | Metallbearbeitungsflüssigkeitzusammensetzung |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0192358B1 (de) |
JP (1) | JPS61235499A (de) |
KR (1) | KR930007896B1 (de) |
DE (1) | DE3676315D1 (de) |
MX (1) | MX168689B (de) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0252534A1 (de) * | 1986-05-13 | 1988-01-13 | Berol (Suisse) S.A. | Verfahren in der mechanischen Bearbeitung von Aluminium und Aluminiumlegierungen in Gegenwart eines kühlenden Schmiermittels, und ein Konzentrat des kühlenden Schmiermittels |
WO1989009254A1 (en) * | 1988-03-30 | 1989-10-05 | 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 |
WO2000014191A1 (en) * | 1998-09-07 | 2000-03-16 | Skoeld Rolf | Mechanical working in the presence of a metal containing copper or aluminum |
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)
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)
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 (de) * | 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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6025080B2 (ja) * | 1982-12-03 | 1985-06-15 | 出光興産株式会社 | 金属加工油 |
JPS6043394B2 (ja) * | 1983-02-07 | 1985-09-27 | 出光興産株式会社 | 金属加工油 |
-
1986
- 1986-01-28 EP EP86300562A patent/EP0192358B1/de not_active Expired - Lifetime
- 1986-01-28 DE DE8686300562T patent/DE3676315D1/de not_active Expired - Fee Related
- 1986-01-30 MX MX001430A patent/MX168689B/es unknown
- 1986-02-03 KR KR1019860000705A patent/KR930007896B1/ko not_active IP Right Cessation
- 1986-02-04 JP JP61022823A patent/JPS61235499A/ja active Pending
Patent Citations (4)
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 (de) * | 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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0252534A1 (de) * | 1986-05-13 | 1988-01-13 | Berol (Suisse) S.A. | Verfahren in der mechanischen Bearbeitung von Aluminium und Aluminiumlegierungen in Gegenwart eines kühlenden Schmiermittels, und ein Konzentrat des kühlenden Schmiermittels |
EP0252533A1 (de) * | 1986-05-13 | 1988-01-13 | Berol (Suisse) S.A. | Verfahren in der mechanischen Bearbeitung von Aluminium und Aluminiumlegierungen in Gegenwart eines kühlenden Schmiermittels und ein Konzentrat des kühlenden Schmiermittels |
WO1989009254A1 (en) * | 1988-03-30 | 1989-10-05 | 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 |
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 (en) * | 1998-09-07 | 2000-03-16 | Skoeld Rolf | Mechanical working in the presence of a metal containing copper or aluminum |
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 |
---|---|
DE3676315D1 (de) | 1991-02-07 |
JPS61235499A (ja) | 1986-10-20 |
KR930007896B1 (ko) | 1993-08-21 |
MX168689B (es) | 1993-06-04 |
KR860006535A (ko) | 1986-09-11 |
EP0192358A3 (en) | 1987-10-14 |
EP0192358B1 (de) | 1991-01-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4151099A (en) | Water-based hydraulic fluid and metalworking lubricant | |
EP0152677B1 (de) | Organo-Borat-Verbindungen enthaltende wässrige Anlagen | |
US4389371A (en) | Process for inhibiting the corrosion of aluminum | |
EP0192358B1 (de) | Metallbearbeitungsflüssigkeitzusammensetzung | |
EP0061693B1 (de) | Hydraulikflüssigkeiten auf Wasserbasis mit verbesserten schmierenden und korrosionshemmenden Eigenschaften | |
US6511946B1 (en) | Water-miscible cooling lubricant concentrate | |
US4450088A (en) | Corrosion inhibited alcohol compositions | |
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 (en) | Functional fluid | |
EP0183050A1 (de) | Schmiermittelzusatz | |
US4218329A (en) | Cooling and lubricating fluid for metal working | |
US4313836A (en) | Water-based hydraulic fluid and metalworking lubricant | |
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 (en) | Aqueous functional fluid composition | |
US4670172A (en) | Process and kit for working metals | |
US3798164A (en) | Polyoxyalkylene bis-thiourea extreme pressure agents and methods of use | |
JP2510233B2 (ja) | 水溶性金属加工油剤 | |
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 | |
JP3148395B2 (ja) | 潤滑剤組成物 | |
JPS63168493A (ja) | 難燃性切削油剤 |
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 |
Owner name: SAIC BREVETTI S.R.L. |
|
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 |