US3929652A - Dual purpose cutting oil - Google Patents

Dual purpose cutting oil Download PDF

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Publication number
US3929652A
US3929652A US523301A US52330174A US3929652A US 3929652 A US3929652 A US 3929652A US 523301 A US523301 A US 523301A US 52330174 A US52330174 A US 52330174A US 3929652 A US3929652 A US 3929652A
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Prior art keywords
oil
lubricant
amount
weight percent
thiadiazole
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Expired - Lifetime
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US523301A
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English (en)
Inventor
Leonard S Seni
James E Davis
Henry R Harrison
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Texaco Inc
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Texaco Inc
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Priority to US523301A priority Critical patent/US3929652A/en
Priority to CA235,349A priority patent/CA1061320A/en
Priority to GB42119/75A priority patent/GB1523149A/en
Priority to SE7512091A priority patent/SE407074B/xx
Priority to FR7534063A priority patent/FR2291264A1/fr
Priority to DE19752549952 priority patent/DE2549952A1/de
Priority to BR7507394*A priority patent/BR7507394A/pt
Priority to DD189394A priority patent/DD121336A5/xx
Priority to IT29169/75A priority patent/IT1049057B/it
Priority to AT866475A priority patent/AT340029B/de
Application granted granted Critical
Publication of US3929652A publication Critical patent/US3929652A/en
Anticipated expiration legal-status Critical
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    • 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
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • 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
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • 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
    • C10M2207/08Aldehydes; Ketones
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    • 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
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    • 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
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    • 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
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • C10M2207/404Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106Thiadiazoles
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01Physico-chemical properties
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    • 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
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/24Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/241Manufacturing joint-less pipes
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/242Hot working
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/243Cold working
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/244Metal working of specific metals
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/244Metal working of specific metals
    • C10N2040/245Soft metals, e.g. aluminum
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
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    • C10N2040/244Metal working of specific metals
    • C10N2040/246Iron or steel
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    • C10N2040/20Metal working
    • C10N2040/244Metal working of specific metals
    • C10N2040/247Stainless steel

Definitions

  • ABSTRACT A dual purpose cutting oil is provided which serves as a heavy duty cutting oil and a machine lubricant.
  • the oil comprises a base oil, an extreme pressure agent comprising primarily Bis (,B-chlorophenethyl) disulfide and a copper corrosion inhibitor comprising an alkyl derivative of 2,5-di-mercapto 1, 3,4-thiadiazole.
  • Metal cutting and grinding have as their objective a progressive removal of metal from the work piece in the form of chips rather than by plastic reforming of the metal.
  • metal cutting lubricant In the field of metal cutting, the use of single and multiple point tools is well known and a great deal of metal working lubricant is used in the metal cutting process.
  • two types of lubricants are needed: a metal cutting lubricant and a machine oil.
  • the cutting oil serves to remove heat generated during machining of the metal and lubricates the cutting tool against the work and chips.
  • the machine oil lubricates the machine parts.
  • Cutting oils are generally paraffinic or intermediate base mineral oils. These are preferred because such products generally create less fog or smoke than naphthene oil. In severe conditions, which are more normal than not in heavy duty operations, it may be necessary to use an additive package in the cutting oil. These additives will comprise extreme pressure additives,
  • the invention is a lubricant which is useful as both a cutting oil and a machine lubricant which comprises a major amount of a base oil and minor amounts of Bis (B-chlorophenethyl) disulfide and minor amounts of an alkyl derivative of 2,5 di-mercapto-l,3,4-thiadiazole.
  • the dual purpose oil of our invention is comprised of a base oil and additive package.
  • the unique combination of additives in our oil was arrived at after many failures of so called equivalent additives in other combinations.
  • each component additive in our oil is used for a purpose for which it is generally known
  • the unique feature of our invention is the combination of additives which function collectively to give a single product, all the performance properties hereinafter enumerated without undesirable side effects such as malodor, corrosiveness, or instability. It was found in developing our invention that it was not enough to put together a list of additives wherein each was known in the art to impart a specific property.
  • our oil usually more of our oil consists of a base oil which may be paraffinic oil of from about to 170 SUS/100F viscosity and preferably to SUS/100F viscosity. It is also acceptable to use a combination of two or more oils as a base oil wherein one oil may range from about 80 to 120, and preferably from about 85 to 105 SUS/l00F viscosity and the other oil may range from to 220 and preferably from about to SUS/100F viscosity. Paraffinic or intermediate base mineral oils are generally preferred as a base oil in our invention since they generate less fog and smoke than a naphthene oil. However, any suitable base oil may be used.
  • the extreme pressure additives useful in our invention are halogenated aryl sulfides. These additives are, particularly, haloaryl polysulfides having one or more halogenated aromatic rings,which if desired can carry side chains containing halogen and/or other substituents.
  • the extreme pressure additives are chlorophenyl polysulfides.
  • a particularly preferred extreme pressure agent comprises primarily Bis (Ii-chlorophenyl) disulfide which is the reaction product of styrene and sulfur monochloride. This additive is present in amounts ranging from about 0.5 to 10 weight percent and preferably from about 1.0 to 5.0 weight percent of the total oil.
  • a copper corrosion inhibitor is needed for the oil of our invention.
  • the corrosion inhibitor which is useful for our invention is an alkyl derivative of 2,5di-mercapto-1,3,4-thiadiazole. This copper corrosion inhibitor should be present in amounts ranging from about 0.05 to 5.0 weight percent and preferably from about 0.05 to 0.5 weight percent in the oil of our invention.
  • a particularly preferred copper corrosion inhibitor is described in U.S. Pat. Nos. 2,714,125; 2,714,126 and 2,983,716.
  • the base oil and the two additives mentioned above will provide an acceptable dual purpose cutting oil, it is preferred that other additives be used to provide additional properties which enhance the desirability of the dual purpose cutting oil. It is particularly preferred that a rust inhibitor be used. It is particularly preferred for our invention that a combination of the extreme pressure agent and a copper corrosion inhibitor above be combined with a rust inhibitor comprising a mixture of alkylmaleic acid, phenol and lauryl acid phosphate. This three component additive system provides a particularly preferred cutting oil.
  • the alkylmaleic acid should be present in amounts ranging from about 0.01 to 1.0 weight percent and preferably from about 0.02 and 0.05 weight percent.
  • the lauryl acid phosphate should be present in amounts ranging from about 0.001 to 0.01 weight percent and preferably from about 0.002 to 0.005 weight percent.
  • the phenol should be present in amounts ranging from trace amounts to about 0.01 weight percent. The percentage of these components is only approximate and may be varied outside of the suggested ranges wihtout departing from the scope of our invention.
  • cutting oils have an oxidation inhibitor, an anti-mist additive, and an odorant.
  • the oxidation inhibitor may be selected from those known in the art. A great many oxidation inhibitors are available commercially on many are hindered phenols although other types may be acceptable. Several of these might work in the cutting oil and the dual purpose cutting oil of our invention. However, it is preferred that tertiary butyl phenol or 4-methyl-2,5-ditertiary butyl phenol may be used in amounts ranging from about 0.05 to 1.0 weight percent and preferably 0.1 to 0.5 weight percent.
  • An anti-mist additive is generally desirable and a few are known in the art. However, it is preferred in the cutting oil of our invention that a copolymer of ethylene and propylene be used.
  • a particular preferred copolymer of ethylene and propylene has a molecular weight ranging from about 70,000 to 100,000 and a propylene content of from about 35 to 50 percent. This copolymer is usually used diluted with a paraffinic mineral oil. About 0.1 to 10.0 arid preferably about 0.5 to 5.0 weight percent of an anti-mist additive is desirable.
  • the odorant in the oil of our invention may be any of those that are available in the commercial market. Generally, the choice of an odorant is important in that a specific odorant will normally mask only a few types important. In the oil of our invention, it was found that oil of citronella has performed adequately, although other odorants could have been used.
  • Table I following gives three formulations of our invention which have acceptable performance properties as listed.
  • Table II following, is an illustration of the problems encountered in putting together the formulation of our invention. We found that it was not enough simply to put together an additive package wherein each additive was known in the art to impart a specific property. The additives must be compatible with each other and the base oil, they must compliment each other and function together to give all the properties desired in the intended application.
  • Table ll,'following shows a comparison of an oil of our invention (A) and three unsuccessful oils, B, C and D.
  • the oils A, B, C and D all contain an additive package of ingredients known in the art to impart qualities which added together should result in a satisfactory dual purpose cutting oil. Yet only A was satisfactory in all respects.
  • oil B which contains sulfur and chlorine extreme pressure agents with zinc dialkyl dithiophosphate copper corrosion inhibitor had the desired performance characteristic but developed an unacceptable haziness in storage.
  • Oil C contained a non-corrosive extreme pressure additive and did not require a copper corrosion inhibitor. However, the odor of Oil B was considered objectionable to customers and could not be marketed. All attempts to mask the offensive odor failed.
  • Oil D was an attempt to develop a suitable product without malodorous or corrosive sulfurized extreme pressure additives. A high extreme pressure level was achieved by using a relatively high concentration of a chlorinated extreme pressure additive. Oil C appeared satisfactory in laboratory tests but gave unsatisfactory maching performance in shop test. Oil A proved satisof odor and thus the selection of an odorant becomes 40 factory in every respect.
  • a lubricant comprising polysulfide is present in an amount ranging from 1.0 to
  • a lubricant comprising:
  • I c. a minor amount of an alkyl derivative of 2,5-dimercapto-l ,3,4-thiadiazole and d. a minor amount of a mixture of alkylmaleic acid,
  • a lubricant comprising:

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US523301A 1974-11-13 1974-11-13 Dual purpose cutting oil Expired - Lifetime US3929652A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US523301A US3929652A (en) 1974-11-13 1974-11-13 Dual purpose cutting oil
CA235,349A CA1061320A (en) 1974-11-13 1975-09-12 Dual purpose cutting oil
GB42119/75A GB1523149A (en) 1974-11-13 1975-10-15 Dual purpose cutting oil
SE7512091A SE407074B (sv) 1974-11-13 1975-10-29 Smorjmedel for anvendning bade som skerolja och maskinsmorjolja
FR7534063A FR2291264A1 (fr) 1974-11-13 1975-11-07 Nouveaux lubrifiants comprenant un polysulfure d'aryle halogene et un derive alkyle de dimercapto-2,5 thiadiazole-1,3,4
DE19752549952 DE2549952A1 (de) 1974-11-13 1975-11-07 Als hochbelastbares schneidoel und als maschinenschmiermittel verwendbare mineralschmieroelformulierung
BR7507394*A BR7507394A (pt) 1974-11-13 1975-11-10 Lubrificante possuindo uma quantidade principal de oleo de base
DD189394A DD121336A5 (de) 1974-11-13 1975-11-11
IT29169/75A IT1049057B (it) 1974-11-13 1975-11-11 Lubrificanti per la lavorazione dei metalli
AT866475A AT340029B (de) 1974-11-13 1975-11-13 Als hochbelastbares schneidol und als maschinenschmiermittel verwendbare mineralschmierolformulierung

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US523301A US3929652A (en) 1974-11-13 1974-11-13 Dual purpose cutting oil

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US (1) US3929652A (de)
AT (1) AT340029B (de)
BR (1) BR7507394A (de)
CA (1) CA1061320A (de)
DD (1) DD121336A5 (de)
DE (1) DE2549952A1 (de)
FR (1) FR2291264A1 (de)
GB (1) GB1523149A (de)
IT (1) IT1049057B (de)
SE (1) SE407074B (de)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3980573A (en) * 1975-07-24 1976-09-14 Mobil Oil Corporation Substituted dimercapto thiadiazoles and lubricant compositions containing same
US4193882A (en) * 1973-07-06 1980-03-18 Mobil Oil Corporation Corrosion inhibited lubricant composition
US4210544A (en) * 1976-08-18 1980-07-01 Texaco Inc. Dual purpose cutting oil composition
US4216100A (en) * 1978-08-03 1980-08-05 Texaco Inc. Pentaerythritol-fatty acid ester lubricant composition
US4427560A (en) 1981-12-10 1984-01-24 Union Oil Company Of California Anti-oxidation and corrosion inhibitors for boron-containing lubricants
US4490265A (en) * 1981-12-10 1984-12-25 Union Oil Company Of California Lubricating compositions
US4595514A (en) * 1983-08-23 1986-06-17 Union Oil Company Of California Boron-containing heterocyclic compound and lubricating compositions containing same
US4623474A (en) * 1981-12-10 1986-11-18 Union Oil Company Of California Oxidation and corrosion inhibitors for boron-containing lubricants
US4627930A (en) * 1980-06-12 1986-12-09 Union Oil Company Of California Boron-containing heterocyclic compounds and lubricating oil containing same
US4629580A (en) * 1980-06-12 1986-12-16 Union Oil Company Of California Boron-containing heterocyclic compounds and lubricating oil containing same
US4629579A (en) * 1980-06-12 1986-12-16 Union Oil Company Of California Boron derivatives
US4657686A (en) * 1980-06-12 1987-04-14 Union Oil Company Of California Lubricating compositions
US4686056A (en) * 1980-06-12 1987-08-11 Union Oil Company Of California Metal-boron derivatives as lubricant additives
US4724099A (en) * 1980-06-12 1988-02-09 Union Oil Company Of California Lubricating compositions
US4756842A (en) * 1980-06-12 1988-07-12 Union Oil Company Of California Lubricating compositions
US4801729A (en) * 1980-06-12 1989-01-31 Union Oil Company Of California Lubricating compositions
US4846984A (en) * 1987-09-18 1989-07-11 Mobil Oil Corporation Lubricant additives derived from aminomercaptothiadiazole and lubricant compositions containing same
US4892670A (en) * 1985-01-29 1990-01-09 Union Oil Company Of California Lubricating compositions
US5227551A (en) * 1989-11-19 1993-07-13 Exxon Chemical Patents Inc. Method of suppressing mist formation from oil-containing functional fluids
US5318712A (en) * 1992-10-13 1994-06-07 The Lubrizol Corporation Lubricants, greases, aqueous fluids and concentrates containing additives derived from dimercaptothiadiazoles
US5368758A (en) * 1992-10-13 1994-11-29 The Lubrizol Corporation Lubricants, greases and aqueous fluids containing additives derived from dimercaptothiadiazoles
US5874390A (en) * 1997-12-22 1999-02-23 Cincinnati Milacron Inc. Aqueous machining fluid and method
US6204225B1 (en) 1999-12-13 2001-03-20 Midwest Biologicals, Inc. Water-dispersible metal working fluid
US6399548B1 (en) * 2000-09-22 2002-06-04 Chevron Oronite Company Llc Functional fluids
US10647939B2 (en) 2016-11-18 2020-05-12 International Petroleum Products & Additives Company, Inc. Thiadiazole components, compositions, and methods

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US3459663A (en) * 1967-04-06 1969-08-05 Sun Oil Co Aluminum rolling oil
US3816311A (en) * 1971-02-19 1974-06-11 Ethyl Corp Stable phosphate esters
US3853638A (en) * 1973-06-25 1974-12-10 Shell Oil Co Quenching oil composition

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
US3459663A (en) * 1967-04-06 1969-08-05 Sun Oil Co Aluminum rolling oil
US3816311A (en) * 1971-02-19 1974-06-11 Ethyl Corp Stable phosphate esters
US3853638A (en) * 1973-06-25 1974-12-10 Shell Oil Co Quenching oil composition

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4193882A (en) * 1973-07-06 1980-03-18 Mobil Oil Corporation Corrosion inhibited lubricant composition
US3980573A (en) * 1975-07-24 1976-09-14 Mobil Oil Corporation Substituted dimercapto thiadiazoles and lubricant compositions containing same
US4210544A (en) * 1976-08-18 1980-07-01 Texaco Inc. Dual purpose cutting oil composition
US4216100A (en) * 1978-08-03 1980-08-05 Texaco Inc. Pentaerythritol-fatty acid ester lubricant composition
US4801729A (en) * 1980-06-12 1989-01-31 Union Oil Company Of California Lubricating compositions
US4627930A (en) * 1980-06-12 1986-12-09 Union Oil Company Of California Boron-containing heterocyclic compounds and lubricating oil containing same
US4629580A (en) * 1980-06-12 1986-12-16 Union Oil Company Of California Boron-containing heterocyclic compounds and lubricating oil containing same
US4629579A (en) * 1980-06-12 1986-12-16 Union Oil Company Of California Boron derivatives
US4657686A (en) * 1980-06-12 1987-04-14 Union Oil Company Of California Lubricating compositions
US4686056A (en) * 1980-06-12 1987-08-11 Union Oil Company Of California Metal-boron derivatives as lubricant additives
US4724099A (en) * 1980-06-12 1988-02-09 Union Oil Company Of California Lubricating compositions
US4756842A (en) * 1980-06-12 1988-07-12 Union Oil Company Of California Lubricating compositions
US4427560A (en) 1981-12-10 1984-01-24 Union Oil Company Of California Anti-oxidation and corrosion inhibitors for boron-containing lubricants
US4490265A (en) * 1981-12-10 1984-12-25 Union Oil Company Of California Lubricating compositions
US4623474A (en) * 1981-12-10 1986-11-18 Union Oil Company Of California Oxidation and corrosion inhibitors for boron-containing lubricants
US4595514A (en) * 1983-08-23 1986-06-17 Union Oil Company Of California Boron-containing heterocyclic compound and lubricating compositions containing same
US4892670A (en) * 1985-01-29 1990-01-09 Union Oil Company Of California Lubricating compositions
US4846984A (en) * 1987-09-18 1989-07-11 Mobil Oil Corporation Lubricant additives derived from aminomercaptothiadiazole and lubricant compositions containing same
US5227551A (en) * 1989-11-19 1993-07-13 Exxon Chemical Patents Inc. Method of suppressing mist formation from oil-containing functional fluids
US5329055A (en) * 1991-06-19 1994-07-12 Exxon Chemical Patents Inc. Method of suppressing mist formation from oil-containing functional fluids
US5318712A (en) * 1992-10-13 1994-06-07 The Lubrizol Corporation Lubricants, greases, aqueous fluids and concentrates containing additives derived from dimercaptothiadiazoles
US5368758A (en) * 1992-10-13 1994-11-29 The Lubrizol Corporation Lubricants, greases and aqueous fluids containing additives derived from dimercaptothiadiazoles
AU669390B2 (en) * 1992-10-13 1996-06-06 Lubrizol Corporation, The Lubricants, greases, and aqueous fluids containing additives derived from dimercaptothiadiazoles
US5874390A (en) * 1997-12-22 1999-02-23 Cincinnati Milacron Inc. Aqueous machining fluid and method
US6204225B1 (en) 1999-12-13 2001-03-20 Midwest Biologicals, Inc. Water-dispersible metal working fluid
US6399548B1 (en) * 2000-09-22 2002-06-04 Chevron Oronite Company Llc Functional fluids
US10647939B2 (en) 2016-11-18 2020-05-12 International Petroleum Products & Additives Company, Inc. Thiadiazole components, compositions, and methods

Also Published As

Publication number Publication date
SE407074B (sv) 1979-03-12
DD121336A5 (de) 1976-07-20
DE2549952A1 (de) 1976-05-20
AT340029B (de) 1977-11-25
CA1061320A (en) 1979-08-28
IT1049057B (it) 1981-01-20
ATA866475A (de) 1977-03-15
GB1523149A (en) 1978-08-31
SE7512091L (sv) 1976-05-14
BR7507394A (pt) 1976-08-10
FR2291264A1 (fr) 1976-06-11

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