US3256187A - Cutting fluid - Google Patents

Cutting fluid Download PDF

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Publication number
US3256187A
US3256187A US281351A US28135163A US3256187A US 3256187 A US3256187 A US 3256187A US 281351 A US281351 A US 281351A US 28135163 A US28135163 A US 28135163A US 3256187 A US3256187 A US 3256187A
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United States
Prior art keywords
succinic acid
percent
acid anhydride
alkanolamine
salt
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.)
Expired - Lifetime
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US281351A
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English (en)
Inventor
Robert H Davis
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.)
ExxonMobil Oil Corp
Original Assignee
Socony Mobil Oil Co Inc
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Filing date
Publication date
Application filed by Socony Mobil Oil Co Inc filed Critical Socony Mobil Oil Co Inc
Priority to US281351A priority Critical patent/US3256187A/en
Priority to DES91029A priority patent/DE1257331B/de
Priority to FR974118A priority patent/FR1392444A/fr
Priority to FR974633A priority patent/FR1393172A/fr
Priority to GB20349/64A priority patent/GB1028458A/en
Priority to GB20350/64A priority patent/GB1021004A/en
Priority to CH636564A priority patent/CH482825A/de
Priority to DE1964S0091111 priority patent/DE1284018B/de
Priority to AT435964A priority patent/AT249839B/de
Application granted granted Critical
Publication of US3256187A publication Critical patent/US3256187A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C10M129/26—Carboxylic acids; Salts thereof
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    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; 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
    • C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/09—Complexes with metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles

Definitions

  • This invention relates to cutting fluids, and, more particularly, to aqueous compositions adapted for use as lubricants and coolants in metal machining operations.
  • Another object of the invention is to provide an improved cutting fluid having corrosion and rust inhibiting properties, and which does not leave hard or insoluble deposits'on metal surfaces during machining operations.
  • Still another object of the invention is to provide an improved cutting fluid which does not cause excessive foam formation during the machining operation.
  • Still further objects of the invention are to provide improved cutting fluids which are resistant to rancidity, maintain their transparency, do not precipitate in hard water solutions, and avoid the formation of tacky waterinsoluble residues during their machining operations.
  • aqueous compositions comprising a balanced formulation and containing as essential components the combination of an alkanolamine and an organic acid of intermediate molecular weight, viz., an organic acid having from about 6 to about 12 carbon atoms per molecule, and an alkenyl succinic anhydride.
  • the alkanolamine component in addition to functioning as a corrosion inhibiting agent in which the aforemenioned organic acids are soluble, also functions as a plasticizer, in that in the course of use, evaporation of water from the cutting fluid leaves a residue upon machinery parts which is desirably soft or semi-liquid.
  • the function of the organic acid component, in combination with the alkanolamine is primarily that of a corrosion inhibitor, in the form of the amine acid salt.
  • the alkanolamine employed in the novel formulation may be of any molecular weight but should preferably be liquid at room temperature.
  • the lower molecular weight compounds are generally preferred, and, for this purpose, it has been found that such alkanolamines as mono-, di-, or tri-ethanolamine, are most effective.
  • Other alkanolamines include isopropanolamines and methyl diethanolamine.
  • the alkanolamine may be employed as either a specific compound or as a combination of such compounds, if so desired.
  • the organic acid component is of the type commonly known as the intermediate molecular weight acids, namely those having from about 6 to about 12 carbon atoms per molecule, and may comprise either staturated or unsaturated acids, or mixtures thereof.
  • the relatively lower molecular Weight organic acids i.e., acids having from 1 to about 5 carbon atoms per molecule, do not satisfactorily function as rust-inhibitors and are also objectionable because of their strong odor.
  • alkenyl succinic anhydrides to function as rust-inhibitors, by reason of their synergistic effects with the aforementioned organic acids, as more fully hereinafter described.
  • Any alkenyl succinic acid anhydride or the corresponding acid is utilizable in the improved formulation of the present invention.
  • the general structural formulae of these compounds are:
  • R is an alkenyl radical.
  • the alkenyl radical can be straight-chain or branched-chain; and it can be saturated at the point of unsaturation by the addition of a substance which adds to olefinic double bonds, such as hydrogen, sulfur, bromine, chlorine, or iodine. It is obvious, of course, that there must be at least two carbon atoms in the alkenyl radical, but there is no real upper limit to the number of carbon atoms therein.
  • the alkenyl succinic acid anhydrides and the alkenyl succinic acids are interchangeable for the purposes of the present invention.
  • alkenyl succinic acid anhydride when used herein, it must be clearly understood that it embraces the alkenyl succinic acids as well as their anhydrides, and the derivatives thereof in which the olefinic double bond has been saturated, as set forth hereinbefore.
  • alkenyl succinic acid anhydride component is Ethenyl succinic acid anhydride Ethenyl succinic acid Ethyl succinic acid anhydride Propenyl succinic acid anhydride Sulfurized propeny'l succinic acid anhydride Butenyl succinic acid I Z-methylbutenyl succinic acid anhydride 1,2-dichloropentyl succinic acid anhydride Hexenyl succinic acid anhydride Hexyl succinic acid Sulfurized 3-methylpenetenyl succinic acid anhydride 2,3-dimet-hylbutenyl succinic acid anhydride 3,3-dimethylb-utenyl succinic acid 1,2-dibromo-2-ethylbutyl succinic acid Heptenyl succinic acid anhydride 1,2-diiodooctyl succinic acid Oetenyl succinic acid anhydride Diisobutyl succinic
  • alkenyl succinic anhydrides suitable for use in the above formulations and their preparation is disclosed in Patent No. 2,638,450, issued May 12, 1953. Particularly preferred are alkenyl succinic anhydrides having from 8 to 12 carbon atoms per molecule.
  • an alkali metal nitrite may also be employed in the formulation in order to impart increased anti-rust properties to the lubricant composition.
  • more specific increased resistance to copper corrosion may be obtained by the use of the sodium salt of mercapto-benzothiazole.
  • the overall performance properties of the lubricant composition may be enhanced by the addition of germicidal agents, particularly phenolic materials such as phenol, sodium salts of orthophenylphenol, chlorinated phenols, such as hexachlorophene, tetrachlorophenol and p-ch'loro-m-xylenol, and also boric acid or oxides of boron.
  • germicidal agents particularly phenolic materials such as phenol, sodium salts of orthophenylphenol, chlorinated phenols, such as hexachlorophene, tetrachlorophenol and p-ch'loro-m-xylenol, and also boric acid or oxides of boron.
  • an alkali metal hydroxide serving to raise the pH of the system, may be employed. These may include, for example, sodium, lithium or potassium hydroxide.
  • various watersoluble chelating agents may be employed to soften the water vehicle.
  • the sodium salt of diethylene .triamine pentaacetic acid or salts of ethylenediamine tetraacetic acid or nitri-lo-triacetic acid can'be used.
  • the novel cutting and lubricant compositions of the present invention are formulated with certain balanced proportions, expressed in weight percent.
  • the alkanolamine is employed in an amount from about 5 to about 40 percent, and preferably in an amount from about 20 to about 35 percent, by weight.
  • the organic acid component is employed in an amount from about 0.1 to about 9 percent, and preferably in an amount from about 1 to about 4 percent, by weight.
  • the alkenyl succinic anhydride is employed in an amount from about 0.1 to about 9 percent, and preferably in an amount from about 0.1 to about 4 percent, by weight.
  • alkali metal nitrite when included in the formulation, is.
  • the watersoluble boron additive e.g., boric acid, when present, is
  • the novel lubricant and. cutting compositions con-' templated in accordance with the present invention are preferably prepared by a blending procedure which comprises reacting alkaline components with acids and/or anhydrides and about 10 to 20 parts of water, which is to be present in the finished formulation. This blending procedure may be satisfactorily carried out at room temperature. When the resulting solution has become clear,
  • the compounding of the novel compositions of the present invention may be illustrated by the preparation of lubricant and cutting fluids from the formulations shown in the following tables and examples, and which also include comparative data and the observations noted when compositions are prepared which do not include the essential components of the present improved formulations.
  • the outstanding properties of the improved lubricant compositions of the present invention are their rust-inhibiting properties and high machining efficiency. Accordingly, these improved compositions were subjected, for the purpose of evaluation, to the following corrosion and machining efficiency tests.
  • CORROSION TEST Malleable iron chips are placed in a 50 ml. beaker together with the fluid composition which is to be evaluated. All excess liquid is then drained off, and the beaker is stored in an atmosphere of approximately 90 percent relative humidity and at a temperature between about 70 and about 75 F. The sample is then checked, after a period of 48 hours storage, for the appearance of rust. This test, and a more detailed method for carrying it out, is fully dsecribed in Patent No. 3,071,545, issued January 1, 1963.
  • Anhydride is converted to the amine salt in presence of methano amine and water.
  • Example 3 there is a definite F TABLE II.-AQ,UEOUS EXTREME PRESSURE LUBRICANTS CONTAINING AN ALKANOLAMINE SALT OF AN INTER- MEDIA'IE MOLECULAR WEIGHT ORGANIC ACID ANCI AN ALKENYL SUCCINIC ACID Base Formula, Percent Wt. Tapping Efficiency 1-5 EX. Dil. Base N0. Tri- Caprylic Noneuyl Dist. Formula-Dist.
  • triethanolamine when used alone (Example 4), nor the combination of triethanolamine and caprylic acid (EX- ample 5) are effective load-support agents, as indicated by the respective tapping efliciency in each case, which is below 82 percent. It will be noted, however, that the combination of the aforementioned triethanolamine, caprylic acid and nonenyl succinic anhydride produces a tapping efficiency of 94.7 percent (Example 6). It will, therefore, be apparent that there is a synergistic extreme pressure effect between the succinic acid anhydride and the triethanolamine and caprylic acid components.
  • An aqueous lubricant composition consisting essentially of a salt of a water-soluble alkanolamine selected from the group consisting of monoethanolamine, diethanolamine, and triethanolamine and a fatty organic acid having from about 6 to about 12 carbon atoms per molecule and a salt of said alkanolamine and an alkenyl succinic acid anhydride, obtained from an aqueous mixture consisting essentially of, by weight, from about 5 to about 40 percent of said alkanolamine, from about-0.1 to about 9 percent of said organic acid, and from about 0.1 to about 9 percent of said alkenyl succinic acid anhydride.
  • An aqueous lubricant composition consisting essentially of a salt of a water-soluble alkanolamine selected from the group consisting of monoethanolamine, diethanolarnine, and-triethanolamine and a fatty organic acid having from about 6 to about 12 carbon atoms per molecule, a salt of said alkanolamine and an alkenyl succinic acid anhydride, and an alkali metal nitrite, obtained from an aqueous mixture consisting essentially of, by weight, from about 5 to about 40 percent of said alkanolamine, from about 0.1 to about 9 percent of said organic acid, from about 0.1 to about 9 percent of said alkenyl succinic acid anhydride, and from about 0.1 to about 10 percen of said alkali metal nitrite.
  • An aqueous lubricant composition consisting essentially of a salt of a water-soluble alkanolamine selected from the group consisting of monoethanolamine, diethanolamine, and triethanolamine and a fatty organic acid having from abopt 6 to about 12 carbon atoms per molecule, a salt of said alkanolamine and an alkenyl succinic acid anhydride, an alkali metal nitrite, and sodium mercapto benzothiazole, obtained from an aqueous mixture consisting essentially of, by weight, from about 5 to about 40 percent of said alkanolamine, from about 0.1 to about 9 percent of said organic acid, from about 0.1 to about 9 percent of said alkenyl succinic acid anhydride, from about 0.1 to about 10 percent'of said alkali 7 metal nitrite, and from about 0.1 to about 6 percent of sodium mercapto-benzothiazole.
  • An aqueous lubricant composition consisting essentially of a salt of a water-soluble alkanolamine selected from the group consisting of monoethanolamine, diethanolamine, and triethanolamine and a fatty organic acid having from about 6 to about 12 carbon atoms per molecule and a salt of said alkanolamine and an alkenyl succinic acid anhydride, obtained from an aqueous mixture consisting essentially of, by weight, from'about 20 to about 35 percent of said alkanolamine, from about 1 to about 4 percent of said organic acid, and from about 0.1 to about 4 percent of said alkenyl succinic acid anhydride.
  • An aqueous lubricant composition consisting essentially of a salt of a water-soluble alkanolamine selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine and a fatty organic acid having from about 6 to about 12 carbon atoms per molecule, a salt of said alkanolamine and an alkenyl succinic acid anhydride, and an alkali metal nitrite, obtained from an aqueous mixture consisting essentially of, by weight, from about 20 to about 35 percent of said alkanolamine, from about 1 to about 4 percent of said organic acid, from about 0.1 to about 4 percent of said alkenyl succinic acid anhydride, and from about 0.1 to about 5 percent of said alkali metal nitrite.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US281351A 1963-05-17 1963-05-17 Cutting fluid Expired - Lifetime US3256187A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US281351A US3256187A (en) 1963-05-17 1963-05-17 Cutting fluid
FR974118A FR1392444A (fr) 1963-05-17 1964-05-12 Liquides de coupe et plus particulièrement compositions lubrifiantes aqueuses
DES91029A DE1257331B (de) 1963-05-17 1964-05-12 Waessrige Metallbearbeitungsfluessigkeit
GB20349/64A GB1028458A (en) 1963-05-17 1964-05-15 Cutting fluid
FR974633A FR1393172A (fr) 1963-05-17 1964-05-15 Nouveaux liquides de coupe aqueux perfectionnés
GB20350/64A GB1021004A (en) 1963-05-17 1964-05-15 Cutting fluid
CH636564A CH482825A (de) 1963-05-17 1964-05-15 Bei der mechanischen Bearbeitung von Metallen anwendbares wässriges Mittel
DE1964S0091111 DE1284018B (de) 1963-05-17 1964-05-15 Waessrige Metallbearbeitungsfluessigkeit
AT435964A AT249839B (de) 1963-05-17 1964-05-19 Wässerige Schmiermittelzusammensetzung

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CH (1) CH482825A (fr)
DE (2) DE1257331B (fr)
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GB (2) GB1028458A (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3897351A (en) * 1973-10-04 1975-07-29 Mobil Oil Corp Lubricant compositions
US4129510A (en) * 1976-04-28 1978-12-12 The Lubrizol Corporation Sulfur-containing compounds and lubricants and fuels containing them
US4239636A (en) * 1978-10-23 1980-12-16 Exxon Research & Engineering Co. Thio-bis-(alkyl lactone acid esters) and thio-bis-(hydrocarbyl diacid esters) are useful additives for lubricating compositions
US4289636A (en) * 1979-10-01 1981-09-15 Mobil Oil Corporation Aqueous lubricant compositions
US4425248A (en) 1981-12-18 1984-01-10 Mobil Oil Corporation Water soluble lubricant compositions
US4519925A (en) * 1976-04-28 1985-05-28 The Lubrizol Corporation Sulfur-containing compounds and lubricants containing them
US4670168A (en) * 1986-05-01 1987-06-02 Aluminum Company Of America Aqueous metal removal fluid
US4725373A (en) * 1986-02-24 1988-02-16 The Dow Chemical Company Novel compositions prepared from alkyl substituted nitrogen-containing aromatic heterocyclic compounds and dicarboxylic acid monoanhydrides
US4900358A (en) * 1988-03-30 1990-02-13 King Industries, Inc. Water soluble corrosion inhibiting compositions and protective coatings prepared therefrom

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2364266A1 (fr) * 1976-09-13 1978-04-07 Mobil Oil Compositions lubrifiantes perfectionnees contenant des sels d'esters partiels d'acides alkyl- ou alcenylsucciniques
US4146488A (en) * 1978-01-24 1979-03-27 Union Carbide Corporation Metal lubricants
DE10046265A1 (de) * 2000-09-19 2002-03-28 Bayer Ag Wirkstoffkombination zum Schutz von tierischen Häuten
DE102007033430A1 (de) * 2007-07-18 2009-01-22 Evonik Goldschmidt Gmbh Siliconfreies Schneidöl und seine Verwendung

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2638449A (en) * 1949-12-30 1953-05-12 Socony Vacuum Oil Co Inc Reaction products of fatty acids, dialkanolamines, and alkenyl succinic acid anhydrides
US2741597A (en) * 1952-03-08 1956-04-10 Texas Co Manufacture of alkenyl succinic acid
US2825693A (en) * 1955-02-03 1958-03-04 Shell Dev Metal working lubricant
US3071545A (en) * 1960-02-08 1963-01-01 Socony Mobil Oil Co Inc Cutting fluid

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1033825B (de) * 1957-01-31 1958-07-10 Hamker & Rieth Verfahren zur Herstellung von transparentwasserloeslichen Metallbearbeitungs- und Kuehlkonzentraten

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2638449A (en) * 1949-12-30 1953-05-12 Socony Vacuum Oil Co Inc Reaction products of fatty acids, dialkanolamines, and alkenyl succinic acid anhydrides
US2741597A (en) * 1952-03-08 1956-04-10 Texas Co Manufacture of alkenyl succinic acid
US2825693A (en) * 1955-02-03 1958-03-04 Shell Dev Metal working lubricant
US3071545A (en) * 1960-02-08 1963-01-01 Socony Mobil Oil Co Inc Cutting fluid

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3897351A (en) * 1973-10-04 1975-07-29 Mobil Oil Corp Lubricant compositions
US4129510A (en) * 1976-04-28 1978-12-12 The Lubrizol Corporation Sulfur-containing compounds and lubricants and fuels containing them
US4519925A (en) * 1976-04-28 1985-05-28 The Lubrizol Corporation Sulfur-containing compounds and lubricants containing them
US4239636A (en) * 1978-10-23 1980-12-16 Exxon Research & Engineering Co. Thio-bis-(alkyl lactone acid esters) and thio-bis-(hydrocarbyl diacid esters) are useful additives for lubricating compositions
US4289636A (en) * 1979-10-01 1981-09-15 Mobil Oil Corporation Aqueous lubricant compositions
US4425248A (en) 1981-12-18 1984-01-10 Mobil Oil Corporation Water soluble lubricant compositions
US4725373A (en) * 1986-02-24 1988-02-16 The Dow Chemical Company Novel compositions prepared from alkyl substituted nitrogen-containing aromatic heterocyclic compounds and dicarboxylic acid monoanhydrides
US4670168A (en) * 1986-05-01 1987-06-02 Aluminum Company Of America Aqueous metal removal fluid
US4900358A (en) * 1988-03-30 1990-02-13 King Industries, Inc. Water soluble corrosion inhibiting compositions and protective coatings prepared therefrom

Also Published As

Publication number Publication date
DE1284018B (de) 1968-11-28
FR1392444A (fr) 1965-03-12
DE1257331B (de) 1967-12-28
AT249839B (de) 1966-10-10
GB1028458A (en) 1966-05-04
CH482825A (de) 1969-12-15
FR1393172A (fr) 1965-03-19
GB1021004A (en) 1966-02-23

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