US3764535A - Tetra-t-dodecylamarcapto-p-benzoquinone - Google Patents

Tetra-t-dodecylamarcapto-p-benzoquinone Download PDF

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US3764535A
US3764535A US00256855A US3764535DA US3764535A US 3764535 A US3764535 A US 3764535A US 00256855 A US00256855 A US 00256855A US 3764535D A US3764535D A US 3764535DA US 3764535 A US3764535 A US 3764535A
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percent
lubricating oil
benzoquinone
tetra
wear
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R Schlicht
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Texaco Inc
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Texaco Inc
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    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • 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
    • C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024—Propene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/17—Fisher Tropsch reaction products
    • C10M2205/173—Fisher Tropsch reaction products used as base 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • 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
    • C10M2219/046—Overbased sulfonic acid 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
    • 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
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • C10M2225/041—Hydrocarbon polymers
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • ABSTRACT A lubricating oil composition of improved corrosion, wear and oxidation inhibiting properties consisting of a hydrocarbon lubricating oil composition comprising a major amount of hydrocarbon lubricating oil and between about 0.1 and 10 wt. percent of tetra-tdodecylmercapto-p-benzoquinone and optionally including additional automative lubricating oil additives such as VI improvers, detergent-dispersants, antifoamants and supplementary corrosion, wear and oxidation inhibitors.
  • Lubricating oils employed in the lubrication of internal combustion engines normally contain additives imparting desired properties thereto such as detergentdispersancy, oxidation resistance, corrosion resistance, wear resistance, antifoaming, etc. Since the demands on the automative lubricating oil compositions have been becoming increasingly severe, a greater number and a greater quantity of additives in the lube oil for.- mulations have been required. Many of the additives employed are metal containing, and therefore, the increased requirements result in undesirably increased metal deposits in the engines which in turn result in decreased engine efficiency.
  • ashless lube oil additives are the tetraalkylmercapto-p-benzoquinones which are broadly known as dopes and extreme pressure agents in lubricating oils (Dutch Pat. No. 76,835).
  • the tetra-alkylmercapto-p-benzoquinones specifically described in the art such as tetra-n-dodecylmercapto-pbenzoquinone are in many respects undesirable additives for lube oils in that they increased wear and substantially contributed to the undesirable thickening of the lubricating oil during use.
  • R, R and R are alkyl groups such that R R R equal 11 carbon atoms. Specific examples are where R and R are methyl and R is a trimethylhexyl group and where R and R are ethyl and R is heptyl.
  • t-dodecyl denotes a single isomeric form as well as isomeric mixtures.
  • the tetra-t-dodecylmercapto-p-benzoquinone additive is incorporated in the lubricating oil base by standard means such as by direct addition to the base accompanied with agitation, e.g., stirring, to insure uniform distribution throughout or may be incorporated as a lube oil concentrate, e.g., 50-50 50 weight mixture of the benzoquinone and a light lubricating oil (100 SUS at 100 F.) with the concentrate being added to the lubricating oil base accompanied by agitation.
  • a lube oil concentrate e.g., 50-50 50 weight mixture of the benzoquinone and a light lubricating oil (100 SUS at 100 F.) with the concentrate being added to the lubricating oil base accompanied by agitation.
  • Suitable base oils useful in the compositions of the invention as well as diluent to form the tetra-tdodecylmercapto-p-benzoquinone lube oil concentrate include a wide variety of hydrocarbon lubricating oil such as naphthenic base, paraffinic base mineral oils or other hydrocarbon lubricants, e.g., lubricating oils derived from coal products and synthetic hydrocarbons, e. g., polyalkylene such as polypropylene and polybutylene of a molecular weight between about 250 and 2,500.
  • the base oils have an SUS'viscosity at 100 F. between about 50 and 2,000 and constitute between about and 99.9 wt. percent of the lube oil composition.
  • additives in addition to supplementary wear, oxidation and corrosion additives, may be any of the standard suitable additives such as detergent-dispersants, e.g., calcium carbonate overbased calcium petroleum sulfonates having a total base number of about 200 to 500 or more as set forth in U. S. Pat. No. 3,537,996 utilized in an amount of between about 1 and 6 wt. percent and/or ethoxylated inorganic phosphorus acid free, steam hydrolyzed polybutene (1,000-5,000 m.w.)-P S reaction product as set forth in U. S. Pat. No. 3,087,956 utilized in an amount between about 2 and 6 wt.
  • detergent-dispersants e.g., calcium carbonate overbased calcium petroleum sulfonates having a total base number of about 200 to 500 or more as set forth in U. S. Pat. No. 3,537,996 utilized in an amount of between about 1 and 6 wt. percent and/or ethoxylated inorganic
  • VI improvers such as the polymethacrylates, e.g., the copolymers of dodecyl and octadecyl methacrylates having an intrinsic viscosity in benzene at 77 F. of between about 0.1 and l and utilized in an amount of between about 0.05 and 1 wt. percent and antifoamants such as the polysilicones in amounts of 10 to 1,000 ppm.
  • the polymethacrylates e.g., the copolymers of dodecyl and octadecyl methacrylates having an intrinsic viscosity in benzene at 77 F. of between about 0.1 and l and utilized in an amount of between about 0.05 and 1 wt. percent
  • antifoamants such as the polysilicones in amounts of 10 to 1,000 ppm.
  • Exactly what other additives are included in the finished oil compositions and the particular amounts employed depends on the particular use and severity to which the finished oil product is to be subject
  • EXAMPLE I This example illustrates a method of preparing the tetra-t-dodecylmercapto-p-benzoquinone additive.
  • Comparative Composition C was identical to Compositions A and B but contained no benzoquinone ingredient.
  • the formulation was as follows: 89.67 wt. percent paraffinic lube oil of an SUS viscosity of about 130 at 100 F., 0.93 wt. percent of the benzoquinone, 6 wt. percent of lube oil concentrate containing 44 wt. percent of ethoxylated, inorganic phosphorus acid free, steam hydrolyzed polybutene (1,200 m.w.)-P S reaction product, 2.9 wt. percent lube oil concentrate containing about 50 wt.
  • Composition C consisted of 90.6 wt. percent of the lube oil, 6 wt. percent of the ethoxylated concentrate, 2.9 wt. percent of the sulfonate concentrate and 0.5 wt. percent of the polyacrylate concentrate.
  • compositions A, B and C were subjected to three lubrication tests:
  • the MacCoull Corrosion Test outlined in U. S. Pat. No. 3,549,534 which measures the corrosion in terms of bearing weight loss, the greater the weight loss the greater the degree of corrosion.
  • the MacCoull test further measures the degree of oxidative thickening under the MacCoull test conditions, the greater the kinematic viscosity the greater the thickening.
  • the second test employed was the Four Ball Wear Test described in U. S. Pat. No. 3,384,588 which is the measure of the amount of wear the lubricating oil permits under engine test conditions. The greater amount of wear, the poorer the ability of the test oil composition to prevent such wear. This wear is measured in terms of millimeter wear.
  • the final test was the Oxygen Absorption Test. It measures the number of hours that it takes for a 25 gram test sample at 340 F. to absorb 500 mls. of oxy gen. The longer the time that is required for oxygen absorption, the greater the resistance of the test composition to oxidation.
  • a lubricating oil composition comprising a major amount of a hydrocarbon lubricating oil containing between about 0.1 and 10 wt. percent of tetra-tdodecylmercaptan-p-benzoquinone 2.
  • a lubricant composition comprising between about 2 and 6 wt. percent of an ethoxylated, inorganic phosphorus acid free, steam hydrolyzed polybutene (l,000-5,000 m.w.)-P S reaction product, between about 1 and 6 wt. percent of a calcium carbonate overbased calcium petroleum sulfonate of a total base number between about 200 and 500, between about 0.05 and 1 wt.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00256855A 1972-05-25 1972-05-25 Tetra-t-dodecylamarcapto-p-benzoquinone Expired - Lifetime US3764535A (en)

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US25685572A 1972-05-25 1972-05-25

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US (1) US3764535A (fr)
JP (1) JPS5034603A (fr)
AU (1) AU471439B2 (fr)
BE (1) BE802631A (fr)
CA (1) CA991629A (fr)
DE (1) DE2334337A1 (fr)
FR (1) FR2238749B1 (fr)
GB (1) GB1404567A (fr)
NL (1) NL7310096A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5460642A (en) * 1994-03-21 1995-10-24 Teledyne Industries, Inc. Aerosol reduction process for metal halides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6034801A (ja) * 1983-12-29 1985-02-22 ウロコ製作所 剥削板の搬出装置
WO1994010269A1 (fr) * 1992-11-02 1994-05-11 Exxon Chemical Limited Nouveaux additifs anti-usure-antioxydant pour huiles lubrifiantes

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB566055A (en) * 1941-01-08 1944-12-12 Elliott Alfred Evans Improvements in or relating to lubricants
US3328301A (en) * 1965-09-23 1967-06-27 Eastman Kodak Co Antioxidants for lubricating oils

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB566055A (en) * 1941-01-08 1944-12-12 Elliott Alfred Evans Improvements in or relating to lubricants
US3328301A (en) * 1965-09-23 1967-06-27 Eastman Kodak Co Antioxidants for lubricating oils

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5460642A (en) * 1994-03-21 1995-10-24 Teledyne Industries, Inc. Aerosol reduction process for metal halides

Also Published As

Publication number Publication date
FR2238749B1 (fr) 1979-01-26
BE802631A (fr) 1974-01-21
GB1404567A (en) 1975-09-03
AU5797773A (en) 1975-01-16
CA991629A (en) 1976-06-22
DE2334337A1 (de) 1975-01-30
AU471439B2 (en) 1976-04-29
JPS5034603A (fr) 1975-04-03
NL7310096A (nl) 1975-01-22
FR2238749A1 (fr) 1975-02-21

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