US3928217A - Lubricating compositions - Google Patents

Lubricating compositions Download PDF

Info

Publication number
US3928217A
US3928217A US404887A US40488773A US3928217A US 3928217 A US3928217 A US 3928217A US 404887 A US404887 A US 404887A US 40488773 A US40488773 A US 40488773A US 3928217 A US3928217 A US 3928217A
Authority
US
United States
Prior art keywords
additive
composition
sulfur
oil
heterocyclic
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
Application number
US404887A
Other languages
English (en)
Inventor
Yves Labat
Yvon Mordelet
Jean Baptiste Signouret
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.)
ENTREPRISE DE RECHERCHES ET D'ACTIVITES PETROLIERES (ELF)
ERAP
Original Assignee
ERAP
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ERAP filed Critical ERAP
Application granted granted Critical
Publication of US3928217A publication Critical patent/US3928217A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • 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
    • C10N2040/02—Bearings
    • 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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
    • C10N2040/32—Wires, ropes or cables lubricants
    • 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
    • C10N2040/34—Lubricating-sealants
    • 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
    • C10N2040/36—Release agents or mold release agents
    • 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
    • C10N2040/38—Conveyors or chain belts
    • 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
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • 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
    • C10N2040/42—Flashing oils or marking oils
    • 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
    • C10N2040/44—Super vacuum or supercritical use
    • 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
    • C10N2040/50—Medical uses

Definitions

  • additives are chemical products in various quantities, incorporated in the lubricants to modify the physical, chemical or mechanical properties.
  • the composition of these additives differs according to the desired properties of the oil for the intended use.
  • additives for high pressure lubricants should improve the oil-metal contact by modifying the characteristics of the oil or chemical modification of the metallic surface.
  • These high pressure additives are used to formulate oils or greases for the lubrication, for example, of gears, hypoidal couples, machine tools, smooth bearings or highly charged rolling mechanisms.
  • the oil additives are essentially constituted by compounds containing sulfur, phosphorus or chlorine. Under the conditions of use, a film of metallic sulfur, phosphorus or chlorine is formed on the exposed surface of the machinery and these films allow avoidance of the mechanical deterioration mentioned above.
  • additives those which contain sulfur in the form of organic compounds are the most often used.
  • Basic studies relative to the possible use as additives for lubricating compositions of various linear organic polysulfides [R-(S-h-R'] have shown in actual usage tests that the high pressure qualities of the polysulfides improve with an increase in the x.
  • copper corrosion increases very rapidly as x of the polysulfide increases. It is difficult to avoid the corrosion using polysulfides where x is greater than 2.
  • additives possessing C-S bonds have an activity less than that of additives containing 8-8 bonds.
  • the compounds actually known as high pressure additives are linear compounds in which the sulfur is generally present in the 2 form of a disulfide. Further, as pointed out in British Pat. No. 1,215,174, only certain disulfides increase the load carrying capacity of lubricating oils to any marked degree.
  • a dimer be lieved to be is produced by reacting a non-conjugated olefin of at least 6 carbon atoms with a sulfur halide at a temperature of about 0-50 C. to form a di(haloalkyl) sulfide intermediate, and at once condensing the intermediate with a water-soluble inorganic higher polysulfide at a temperature of about 50-l00 C. in a mutual solvent.
  • the present invention resolves this sulfur content problem.
  • the invention is based on the concept of increasing the sulfur concentration by the presence of various kinds of disulfides and/or sulfides in the same organic molecule and not by increasing the sulfur chain, the solution looked to till now by those skilled in the art.
  • This invention relates to a new lubricating composition and more particularly to a new lubricating composition containing a heterocyclic sulfur additive which is a heterocyclic compound of disulfide and/or sulfide moieties and containing no more than 1 carbon atom between sulfur atoms in the heterocyclic ring.
  • a heterocyclic sulfur additive which is a heterocyclic compound of disulfide and/or sulfide moieties and containing no more than 1 carbon atom between sulfur atoms in the heterocyclic ring.
  • the principal constituents of the new lubricating compositions are the organic or synthetic mineral oil and one or more sulfur additives which are a heterocyclic compound of disulfide and/or sulfide moieties in which the heterocyclic sulfur atoms are separated by at most 1 carbon atom.
  • heterocyclic compounds used in the instant invention contain one or more (which need not be the same) disulfide moieties and one or more (which need not be the same) sulfide moieties
  • the disulfide and sulfide moieties can be arranged consecutively or alternately.
  • Preferred heterocyclic compounds are of the formula -C). CM. :1
  • R R R and R which can be the same or different, are hydrogen, alkyl or alkenyl radicals of 1-6 carbon atoms; R and R and also R and R,,, can respectively form with the carbon atom to which they are joined a saturated or unsaturated ring of 4-8 carbon atoms; n is l-4; m is 0-4; and the alkyl, alkenyl, cyclanic and cyclenic groups can contain hetero atoms such as sulfur.
  • suitable compounds are derived from tetrathiane heterocyclics such as 3,3,6,6-tetramethyl-l ,2,4,5-tetrathiane, 3,6-dicyciohexyl-l,2,4,5-tetrathiane, 3,3,6,6-tetravinyl-1,2,4,5-tetrathiane, as well as compounds derived from trithiolane heterocyclics such as 3,5-dicyclobexyl- 1,2,4-trithiolane and the like.
  • Products derived from 2,3,5,6,7-pentathiapanes are less suitable because they contain the trisulfide system and even though they have good high pressure properties, they are corrosive to copper metal.
  • the sulfur heterocyclic additives of the preceding formula can be-prepared according to known methods described in the literature.
  • oils used in the present compositions can be mineral oils obtained by different processes of refining, e. g., treatment with solvent or hydrorefining. These oils are not constituted by only one hydrocarbon but are said to be paraffms, naphthalenes or aromatics with one or another of these hydrocarbons in major proportion.
  • oils or synthetic oils such as alkylbenzene, esters and polyglycols.
  • the quantity of heterocyclic additive introduced into the oil for improving the lubricating properties can vary within quite large limits and varies according to the use to which the lubricant is destined.
  • the lubricant oils contain 0.5-15%, preferably 0.75-7.5%, by weight of heterocyclic additive and 99.5-%, preferably 99.25-92.5% of oil.
  • the lubricating oil compositions are prepared by mixing the oil and the heterocyclic additive at a temperature generally between 50-100 C. with agitation, preferably between 60-80 C.
  • Complementary adjuvants can be added under the same conditions in order to impart a particular quality or complementary property to the composition.
  • Such adjuvants can be, e.g., antioxidants, anticorrosives, viscosity controllers, antifoam additives, de-emulsifying agents, anti-usages, detergents and dispersants.
  • Lubricant compositions undergo a series of laboratory tests before industrialization which are designed to simulate the problems or conditions encountered in actual use. Being specially designed for high pressure oils, the additives of the present invention are studied in the following tests: high pressure 4 ball machine (norm ASTM D 2596 or norm FS 6503), machine FZG (norm DIN 51354), machine Timken (norm ASTM D 2509), and copper corrosion test (norm NF M 07-015).
  • EXAMPLE 1 parts of a synthetic alkylbenzene oil and 1 part of tetramethyl tetrathiane (TMTT) and 0.5 part of an amine anticorrosive agent were placed in a receptacle which was heated to 60 C. and strongly agitated. The resulting composition was subjected to a series of tests.
  • TMTT tetramethyl tetrathiane
  • composition possessed the qualities required by the French Navy for use in the lubrication of refrigera- TABLE I LUBRICANTS FOR COMPRESSORS (Norm Marine STM 7272) Characteristics Specifications Base Synthetic +1% Commercial Base Synthetic dibenzyl Base Synthetic 2% TMTT disulflde Alone 0.5% anti- 0.5% anti- (Alkyl Benzene) corrosive corrosive Copper Corrosion NF M 07-015 TABLE I-continued LUBRICANTS FOR COMPRESSORS (Norm Marine STM 7272) Base Synthetic +l% Commercial Base Synthetic dibenzyl Base Synthetic 2% TMTT disulfide Alone i- 0.5% anti- 0.5% anti Characteristics Specifications (Alkyl Benzene) corrosive corrosive 3 hours-100 C.
  • EXAMPLE 3 A lubricant composition was prepared as in Example 1 using a paraffin-type mineral oil and 5% of TMTT with and without 0.05% of a copper corrosion inhibitor. Test results are shown in Table III and compared with the same oils containing a sulfur-containing polybutene.
  • the compositions of the present invention give Base Mineral Base With 2% Mineral Commercial Specifi- With 2% Dibenzyl Characteristics cations Norm TM'I'I Disulfide Precipitation Index 0.1 AIR 165l/A pass pass charge Capacity 40 AIR 1650/A 55 Copper Corrosion (100 C 72 H) 2e NF M 07-015 2b 4b Storage 20 C. no sedimentation AIR 1651 [A pass fail lubricants which can advantageously be employed for industrial gears.
  • Lubricant compositions were prepared by mixing a paraffin-type base oil having the following characteristics: 200 NS (neutral solvent), viscosity 200 S/Saybolt Universal at 100 F., and 3% of an additive of the present invention or 3% of a prior art additive, as in Example 1. Each lubricant composition was tested on the 4-ball machine, norm FS 6503.
  • composition of claim 1 wherein said heterocyclic compound is of the formula comprises employing as the additive a heterocyclic compound consisting of 4 Ball Machine Norm FS 6 J 03 Additive L.N.S.L. (kg) W.L. (kg) L.W.l.
  • a high pressure lubricating oil composition comprising oil and as an additive therefor, a heterocyclic compound consisting of groups arranged consecutively or alternatively with groups to form the heterocyclic ring such that there is no more than one carbon atom between sulfur atoms in the heterocyclic ring so formed, wherein n is l-4 and m is 0-4, R R R and R are individually selected from the group consisting of hydrogen, alkyl of 1-6 carbon atoms, alkenyl of [-6 carbon atoms, sulfur-containing alkyl of l-6 carbon atoms, sulfur-containing alkenyl of l-6 carbon atoms, and wherein R and R and R and R respectively, can form with the carbon atom to which they are joined, a saturated, unsaturated or sulfur-containing ring of 4-8 carbon atoms, and wherein said additive is 05-15 weight percent of said composition.
  • R R R and R are individually selected from the group consisting of hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 1-6 carbon atoms, sulfur-containing alkyl of l-6 carbon atoms, sulfur-containing alkenyl of l-6 carbon atoms, and wherein R and R and R and R respectively, can form with the carbon atom to which they are joined, a saturated, unsaturated or sulfur-containing ring of 4-8 carbon atoms, said additive being 05-15 percent by weight of the resulting composition.
  • composition of claim 2 wherein said additive is l ,4-dicyclohexyl2,3,5-trithiolane.
  • composition of claim 2 wherein said additive is 3,6-dicyclohexyl-l ,2,4,5-tetrathiane.

Landscapes

  • 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)
US404887A 1972-10-19 1973-10-10 Lubricating compositions Expired - Lifetime US3928217A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7237129A FR2203873B1 (ja) 1972-10-19 1972-10-19

Publications (1)

Publication Number Publication Date
US3928217A true US3928217A (en) 1975-12-23

Family

ID=9105916

Family Applications (1)

Application Number Title Priority Date Filing Date
US404887A Expired - Lifetime US3928217A (en) 1972-10-19 1973-10-10 Lubricating compositions

Country Status (16)

Country Link
US (1) US3928217A (ja)
JP (1) JPS5415042B2 (ja)
BE (1) BE806238A (ja)
CA (1) CA1006498A (ja)
CH (1) CH587340A5 (ja)
DE (1) DE2352586C2 (ja)
ES (1) ES419753A1 (ja)
FR (1) FR2203873B1 (ja)
GB (1) GB1434980A (ja)
IT (1) IT995989B (ja)
LU (1) LU68636A1 (ja)
NL (1) NL181209C (ja)
PL (1) PL89474B1 (ja)
RO (1) RO72824A (ja)
SE (1) SE395281B (ja)
SU (1) SU475789A3 (ja)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012331A (en) * 1974-07-25 1977-03-15 Edwin Cooper And Company Limited Sulphur compounds
US4013571A (en) * 1975-01-24 1977-03-22 Phillips Petroleum Company Extreme pressure lubricating composition containing thiosulfinate extreme pressure agents

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1805052A (en) * 1927-10-21 1931-05-12 Goodyear Tire & Rubber Process for preventing the dissolution of metals in pickling baths
US2213804A (en) * 1938-02-23 1940-09-03 Continental Oil Co Lubricating oil
US2744070A (en) * 1952-12-22 1956-05-01 Continental Oil Co Soluble cutting oil
US2891072A (en) * 1955-12-07 1959-06-16 Pure Oil Co Preparation of dithianes
US2900392A (en) * 1955-12-20 1959-08-18 Pure Oil Co Preparation of dithianes
US2941945A (en) * 1956-06-28 1960-06-21 Standard Oil Co Extreme pressure lubricants
US2966521A (en) * 1958-05-19 1960-12-27 Union Oil Co Sulfurization of mercaptols

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2292456A (en) * 1938-02-23 1942-08-11 Continental Oil Co Lubricating oil
US2500672A (en) * 1949-06-08 1950-03-14 Socony Vacuum Oil Co Inc Synthetic lubricants
BE507418A (ja) * 1951-02-21
GB734412A (en) * 1951-07-19 1955-08-03 California Research Corp Improved lubricant compositions
US2722518A (en) * 1952-06-27 1955-11-01 Shell Dev Synthetic lubricants
US2985590A (en) * 1955-09-28 1961-05-23 Exxon Research Engineering Co Lubricating oil compositions comprising mercaptobenzothiazole ester derivatives
US2991251A (en) * 1957-09-27 1961-07-04 Exxon Research Engineering Co Corrosion inhibiting lubricating composition
BE586528A (ja) * 1959-01-14
US3069357A (en) * 1959-04-01 1962-12-18 Texaco Inc Synthetic lubricating composition
NL291191A (ja) * 1962-04-06
US3509051A (en) * 1964-08-07 1970-04-28 T R Vanderbilt Co Inc Lubricating compositions containing sulfurized oxymolybdenum dithiocarbamates
GB1215174A (en) * 1968-03-14 1970-12-09 British Petroleum Co Improvements in lubricating compositions
US3663438A (en) * 1969-06-23 1972-05-16 Shell Oil Co High temperature grease compositions

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1805052A (en) * 1927-10-21 1931-05-12 Goodyear Tire & Rubber Process for preventing the dissolution of metals in pickling baths
US2213804A (en) * 1938-02-23 1940-09-03 Continental Oil Co Lubricating oil
US2744070A (en) * 1952-12-22 1956-05-01 Continental Oil Co Soluble cutting oil
US2891072A (en) * 1955-12-07 1959-06-16 Pure Oil Co Preparation of dithianes
US2900392A (en) * 1955-12-20 1959-08-18 Pure Oil Co Preparation of dithianes
US2941945A (en) * 1956-06-28 1960-06-21 Standard Oil Co Extreme pressure lubricants
US2966521A (en) * 1958-05-19 1960-12-27 Union Oil Co Sulfurization of mercaptols

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012331A (en) * 1974-07-25 1977-03-15 Edwin Cooper And Company Limited Sulphur compounds
US4013571A (en) * 1975-01-24 1977-03-22 Phillips Petroleum Company Extreme pressure lubricating composition containing thiosulfinate extreme pressure agents

Also Published As

Publication number Publication date
PL89474B1 (ja) 1976-11-30
NL7314421A (ja) 1974-04-23
BE806238A (fr) 1974-02-15
RO72824A (ro) 1982-02-26
FR2203873B1 (ja) 1975-06-13
NL181209B (nl) 1987-02-02
IT995989B (it) 1975-11-20
ES419753A1 (es) 1976-03-01
JPS49134707A (ja) 1974-12-25
CA1006498A (fr) 1977-03-08
SE395281B (sv) 1977-08-08
CH587340A5 (ja) 1977-04-29
NL181209C (nl) 1987-07-01
DE2352586C2 (de) 1984-09-27
SU475789A3 (ru) 1975-06-30
GB1434980A (en) 1976-05-12
LU68636A1 (ja) 1973-12-27
JPS5415042B2 (ja) 1979-06-12
DE2352586A1 (de) 1974-05-02
FR2203873A1 (ja) 1974-05-17

Similar Documents

Publication Publication Date Title
US2268608A (en) Lubricants
US3533943A (en) Lubricant compositions
JPH032919B2 (ja)
GB1567144A (en) Lubricant additive
JPH029079B2 (ja)
US4517103A (en) Lubricating compositions containing 5,5'-dithiobis(1,3,4-thiadiazole-2-thiol)
US2756249A (en) Phenoxyalkyl dithiocarbamates
US2963433A (en) Lubricant composition
US2528782A (en) Lubricant
US2719827A (en) Lubricating oil compositions containing sulfur corrosive to silver
US2696473A (en) Halogen containing extreme pressure lubricant stabilized with a polyalkylene polyamine
US3928217A (en) Lubricating compositions
US2799651A (en) Corrosion inhibitors and compositions containing the same
US2363880A (en) Lubricants
US2902450A (en) Lubricating oil composition
US2491772A (en) Extreme pressure lubricants
US2614914A (en) Diesel fuel containing di-tertiary alkyl sulfides as ignition promoters
US2704745A (en) Stabilized extreme pressure lubricant
US3234129A (en) Lubricating compositions
US3030304A (en) Lubricating compositions
USRE22911E (en) Lubricant
US4137187A (en) Antiwear additive and lubricating oil composition containing same
US3277003A (en) Lubricating oils containing amine oxides
US2669544A (en) Benzothiazyl sulfenamides in lubricants
US2624707A (en) Lubricating composition