EP0735128A2 - Des huiles de corrosion et d'oxidation à vie prolongée - Google Patents

Des huiles de corrosion et d'oxidation à vie prolongée Download PDF

Info

Publication number
EP0735128A2
EP0735128A2 EP96302164A EP96302164A EP0735128A2 EP 0735128 A2 EP0735128 A2 EP 0735128A2 EP 96302164 A EP96302164 A EP 96302164A EP 96302164 A EP96302164 A EP 96302164A EP 0735128 A2 EP0735128 A2 EP 0735128A2
Authority
EP
European Patent Office
Prior art keywords
formula
weight percent
oxidation
carbon atoms
dithiocarbamate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP96302164A
Other languages
German (de)
English (en)
Other versions
EP0735128A3 (fr
EP0735128B1 (fr
Inventor
Ramnath Iyer
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.)
Ethyl Corp
Original Assignee
Ethyl Corp
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 Ethyl Corp filed Critical Ethyl Corp
Publication of EP0735128A2 publication Critical patent/EP0735128A2/fr
Publication of EP0735128A3 publication Critical patent/EP0735128A3/fr
Application granted granted Critical
Publication of EP0735128B1 publication Critical patent/EP0735128B1/fr
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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/08—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066—Arylene diamines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/067—Polyaryl amine alkanes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/30—Heterocyclic 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; 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
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal 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
    • C10M2219/10—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
    • 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
    • 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
    • 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
    • C10M2223/049—Phosphite
    • 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
    • C10M2223/10—Phosphatides, e.g. lecithin, cephalin

Definitions

  • This invention relates to the field of improved thermal and oxidative stability of lubricating fluids.
  • Lubricating oils such as circulating oils, turbine oils, hydraulic fluids and transformer oils as well as others require good oxidation stability and good rust inhibition properties. Extended life for such fluids where desired rust and oxidation (R&O) inhibition properties are maintained for extended periods of use is demanded by industrial users and provides important economic benefit.
  • R&O oils are widely used in turbine and compressor circulating systems. Their thermal and oxidative stability are of particular importance.
  • R&O oils provide rust protection, corrosion protection and metal passivation. Antiwear protection is sometimes needed.
  • U. S. Patent 4,125,479 to Chesluk et al. discloses an oxidation inhibited lubricating oil with a combination of additives comprising methylenebis(di-n-butyldithiocarbamate) and 4-methyl-2,6-ditertiary butyl phenol, said to provide enhanced oxidation inhibition.
  • U. S. Patent 4,125,479 to Chesluk et al. discloses an oxidation inhibited lubricating oil with a combination of additives comprising methylenebis(di-n-butyldithiocarbamate) and 4-methyl-2,6-ditertiary butyl phenol, said to provide enhanced oxidation inhibition.
  • U. S. Patent 4,125,479 to Chesluk et al. discloses an oxidation inhibited lubricating oil with a combination of additives comprising methylenebis(di-n-butyldithiocarbamate) and 4-methyl-2
  • Patent 4,880,551 to Doe discloses an antioxidant composition consisting of a 1-(di(4-octylphenyl) aminomethyl)tolutriazole and at least one antioxidant selected from the group consisting essentially of methylenebis(di-n-butyldithiocarbamate); 2,6-di-t-butyl-4-sec-butylphenol; 2,6-di-t-butyl-4-methylphenol and butylated phenol mixture.
  • R&O lubricant concentrate packages typically contain phenolic, amino and other antioxidants, rust inhibitor(s), a metal deactivator, and a demulsifying agent. They may include additional components such as an antiwear agent depending on the final performance properties desired.
  • the principle function of the antioxidants is the inhibition of oxidative degradation of R&O oils that are obtained by blending the R&O lubricant concentrate package in a particular basestock oil of choice. Basestock oils have varying degrees of thermal and oxidative stability.
  • This invention will serve to improve the thermal and oxidative properties of even those basestock oils that are known to have less than satisfactory stability.
  • the current invention relates to the use of certain components. that contribute directly to prolonging the life of R&O oils.
  • a rust and oxidation (R&O) inhibited lubricant composition comprising a base oil and rust and oxidation inhibitors
  • said lubricant composition comprises (a) a dithiocarbamate compound represented by the formula wherein R 4 is a hydrocarbylene group having 1 to 10 carbon atoms, each R 5 is a hydrogen or a hydrocarbyl group having 1 to 18 carbon atoms, and each R 3 is a hydrocarbyl group having 1 to 18 carbon atoms; and (b) an alkylphenyl- ⁇ -naphthylamine.
  • the lubricant composition further optionally comprises (c) a hydrocarbyl phosphite represented by the formula (R 6 O) 3 P where each R 6 is independently C 1 to C 18 alkyl, C 2 to C 18 alkenyl, or C 6 to C 18 aryl.
  • Each component (a) and (b), or (a), (b) and (c) is present in an amount sufficient to provide improved inhibition of oxidation to the R&O lubricant composition.
  • the additive combinations of this invention may be used in any lubricating oil where oxidation inhibition is required.
  • This may include circulating oils used in compressor and turbine circulating systems, transformer oils, engine oils and other oils which are subjected to conditions where oxidation is a problem. It has been found that a dithiocarbamate compound in combination with an alkylphenyl- ⁇ -naphthylamine, in effective amounts, and that combination in further combination with an effective amount of hydrocarbyl phosphite, provide important and unexpected enhancement of thermal and oxidation stability, with resulting improvement in the life of the R&O oil.
  • the additive combinations of this invention can be incorporated in a wide variety of lubricants and functional fluids in effective amounts to provide suitable active ingredient concentrations.
  • the base oils useful herein can be hydrocarbon oils of suitable viscosities; synthetic oils such as hydrogenated polyolefin oils; poly- ⁇ -olefin oligomers (such as hydrogenated poly-1-decene) ; alkyl esters of dicarboxylic acids; complex esters of dicarboxylic acid, polyglycol and alcohol; alkyl esters of carbonic or phosphoric acids; polysilicones; fluorohydrocarbon oils; and mixtures of mineral, natural and/or synthetic oils in any proportion, etc.
  • base oil for this disclosure includes all the foregoing and mixtures thereof.
  • the dithiocarbamate compound to be included in the combination of the invention is represented by the formula wherein R 4 is a hydrocarbylene group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms.
  • R 4 is an alkylene group, most preferably a methylene or ethylene group.
  • Each R 5 is a hydrogen or a hydrocarbyl group having 1 to 18 carbon atoms, preferably 2 to 10, more preferably 2 to 6.
  • Each R 3 is a hydrocarbyl group having 1 to 18 carbon atoms, preferably 2 to 10, more preferably 2 to 6.
  • a commercially available dithiocarbamate compound appropriate for use in the invention is VANLUBE° 7723, methylenebis(di-n-butyldithiocarbamate).
  • dithiocarbamate compound may start hurting or interfering with relevent bench tests other than R&O tests. Higher levels of dithiocarbamate compound may result in deterioration of thermal stability, causing undesired sludge in thermal stability tests. Also rust problems may occur at higher dithiocarbamate compound levels, which may result in failure of specified rust tests.
  • An effective amount of dithiocarbamate compound is up to 1.0 weight percent of the finished lubricant composition, for example 0.01 to 1.0 weight percent, 0.02 to 0.5 preferred, 0.03-0.2 most preferred.
  • alkylphenyl- ⁇ -naphthylamine for use in the invention is represented by the formula wherein R 1 and R 2 are independently hydrogen or C 1 to C 18 alkyl.
  • alkylphenyl- ⁇ -naphthylamine includes phenyl- ⁇ -naphthylamine (PANA), where both R 1 and R 2 are hydrogen.
  • An effective amount of alkylphenyl- ⁇ -naphthylamine for use in the invention is up to 0.15 weight percent of the finished lubricant composition, for example 0.025 to 0.15 weight percent, 0.03 to 0.125 weight percent preferred.
  • the hydrocarbyl phosphite compound for use in the invention is represented by the formula: (R 6 O) 3 P where each R 6 is independently C 1 to C 18 alkyl, C 2 to C 18 alkenyl, or C 6 to C 18 aryl. In preferred compounds, each R 6 is independently C 3 to C 12 alkyl or C 6 to C 18 aryl. In most preferred compounds, R 6 is C 6 to C 18 aryl, including triphenylphosphite, tricresylphos-phite, trinonylphenylphosphite (C15), tridodecylphenylphosphite, and mixtures thereof.
  • An effective amount of the hydrocarbyl phosphite compound for use in the invention is up to 0.075 weight percent of the finished lubricant composition, for example 0.005 to 0.075 weight percent, 0.01 to 0.06 preferred.
  • R&O oils will typically contain a conventional quantity of one or more antioxidants in order to protect the composition from premature degradation in the presence of air, especially at elevated temperatures.
  • Typical antioxidants include various alkylated phenols, hindered phenols and phenol derivatives such as t-butyl hydroquinone, butylated hydroxyanisole, polybutylated bisphenol A, butylated hydroxy toluene, alkylated hydroquinone, 2,5-ditertaryl hydroquinone; 2,6-ditert-butyl-para-cresol; 2,2'-methylenebis(6-tert-butyl-p-cresol); 1,5-naphthalenediol; 4,4'-thiobis(t-tert-butyl-m-cresol); p,p-biphenol; 4,4'-butylidenebis(6-tert-butyl-m-cresol); 4-methoxy-2,6-di-tert-butylphenol; and the
  • Phenolic antioxidants are known and may be represented by the general formula: where R 7 is hydrogen or an alkyl group with 1 to 4 carbons, R 8 is an alkyl group with 1 to 4 carbons or a benzylic group, and R 9 is hydrogen, an alkyl group with 1 to 6 carbons, or an alkoxy group with 1 to 6 carbons.
  • R 7 is hydrogen
  • R 8 is an alkyl group with 1 to 4 carbons
  • R 9 is an alkyl group with 1 to 6 carbons; most preferably both R 8 and R 9 are t-butyl.
  • R 9 is hydrogen, R 7 is an alkyl group with 1 to 4 carbons, and R 8 is an alkyl group with 1 to 4 carbons; most preferably both R 7 and R 8 are t-butyl.
  • the R&O oil compositions useful herein will also typically comprise a rust inhibitor and a metal deactivator. These are commonly selected from alkenyl succinic acid esters and from triazoles and triazole derivatives, known for these purposes.
  • a corrosion inhibitor This may be a single compound or a mixture of compounds having the property of inhibiting corrosion of metallic surfaces.
  • One type of such additives are inhibitors of copper corrosion.
  • Such compounds include thiazoles, triazoles and thiadizoles.
  • Examples of such compounds include benzotriazole, tolytriazole, octyltriazole, decyltriazole, dodecyltriazole, 2-mercaptobenzothiazole, 2, 5-dimercapto-1, 3, 4-thiadiazole, 2-mercapto-5-hydrocarbylthio-1,3,4-thiadiazoles, 2-mercapto-5-hydrocarbyldithio-1, 3, 4-thiadiazoles, 2, 5-bis(hydrocarbylthio)-1, 3, 4-thiadiazoles, and 2, 5-(bis)hydrocarbyldithio), 1, 3, 4-thiadiazoles.
  • the preferred compounds are the 1, 3, 4-thiadiazoles, a number of which are available as articles of commerce.
  • Such compounds are generally synthesized from hydrazine and carbon disulfide by known procedures. See for example U.S. Pat. Nos. 2,765,289; 2,749, 311; 2,760,933; 2,850,453; 2,910,439; 3,663,561; 3,862,798; and 3,840,549.
  • Other types of corrosion inhibitors are known and suitable for use in the compositions of this invention. Suitable corrosion inhibitors include ether amines; acid phosphates; amines; polyethoxylated compounds such as ethoxylated amines, ethoxylated and/or propoxylated phenols, and ethoxylated alcohols; imidazolines; and the like. Materials of these types are well known to those skilled in the art and a number of such materials are available as articles of commerce.
  • the lubricating composition of the present invention may further contain other additives such as extreme pressure agents and/or antiwear agents.
  • the additives of the present invention can be incorporated into a lubricating oil in any convenient way.
  • the compounds, or mixtures thereof, can be added directly to the oil at the desired level or by adding concentrates of the additive to the oil.
  • the additive compounds can be blended with a suitable oil soluble solvent such as mineral spirits and/or base oil to form a concentrate and then the concentrate may be blended with lubricating oil to obtain a final formulation.
  • a complete R&O lubricant concentrate package can be prepared containing antioxidants, rust inhibitor, metal, deactivator, demulsifier, additional desired components as well as the components of the invention, i.e.
  • the components are present in the lubricant concentrate package at a level sufficient to provide an effective level in the finished composition to provide the enhanced oxidation inhibition properties.
  • HiTec 575® Ashless Rust & Oxidation Inhibitor is a lubricant additive concentrate package commercially available from Ethyl Corporation. This is fully formulated for high-performance, turbine-quality hydraulic fluids. It provides extended oxidation life, excellent rust control, demulsibility and filterability, and is compatible with other additives commonly used in hydraulic fluids.
  • HiTec 575 lubricant additive represents a typical R&O package and has been used in the studies reported herein to demonstrate the improved oxidation properties obtained with the present invention.
  • Texaco ISO 46 basestock oil was used in preparing the formulation of the examples below. In Example 1, HiTec 575 lubricant additive was blended with the basestock oil at its recommended dosage, 0.80 weight percent.
  • HiTec 575 lubricant additive contains PANA in an amount that provides 0.10 weight percent to the blended lubricant composition at this recommended dosage.
  • the PANA was removed from the HiTec 575 lubricant additive.
  • the HiTec 575 lubricant additive without PANA was blended with the Texaco ISO 46 basestock oil at 0.80 weight percent dosage, and the dithiocarbamate compound and triphenylphosphite were added in the amounts indicated.
  • commercially available HiTec 575 lubricant additive was blended with the basestock at 0.80 weight percent dosage, and the dithiocarbamate compound and triphenylphosphite were added in the amounts indicated.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP96302164A 1995-03-28 1996-03-28 Des huiles de corrosion et d'oxidation à vie prolongée Expired - Lifetime EP0735128B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US41303895A 1995-03-28 1995-03-28
US413038 1995-03-28

Publications (3)

Publication Number Publication Date
EP0735128A2 true EP0735128A2 (fr) 1996-10-02
EP0735128A3 EP0735128A3 (fr) 1997-06-11
EP0735128B1 EP0735128B1 (fr) 2000-08-23

Family

ID=23635549

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96302164A Expired - Lifetime EP0735128B1 (fr) 1995-03-28 1996-03-28 Des huiles de corrosion et d'oxidation à vie prolongée

Country Status (2)

Country Link
EP (1) EP0735128B1 (fr)
CA (1) CA2171924C (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0994175A2 (fr) * 1998-10-16 2000-04-19 Ethyl Corporation Des huiles pour turbomoteurs ayant une excellente stabilité à l'oxydation à température élevée
US6207623B1 (en) 2000-01-14 2001-03-27 Exxonmobil Research And Engineering Company Industrial oils of enhanced resistance to oxidation
EP1104800A2 (fr) * 1999-12-02 2001-06-06 Oronite Japan Limited Composition d'huile lubrificante pour moteurs à gaz
CN1067714C (zh) * 1998-08-27 2001-06-27 中国石油化工集团公司 用于透平油的复合添加剂
WO2011153178A2 (fr) 2010-06-02 2011-12-08 The Lubrizol Corporation Composition lubrifiante contenant un polymère à fonction carboxylique
RU2493243C2 (ru) * 2009-02-02 2013-09-20 Ар.Ти. ВАНДЕРБИЛТ КОМПАНИ, ИНК. Беззольная смазывающая композиция
CN103517972A (zh) * 2011-05-16 2014-01-15 卢布里佐尔公司 用于涡轮机和水力系统的具有改进抗氧化性的润滑组合物
CN107573987A (zh) * 2017-09-29 2018-01-12 中国石油化工股份有限公司 涡轮机油添加剂组合物及其用途
EP3189125A4 (fr) * 2014-09-04 2018-01-24 Vanderbilt Chemicals, LLC Additif antioxydant liquide sans cendre pour compositions lubrifiantes
CN107653025A (zh) * 2017-09-29 2018-02-02 中国石油化工股份有限公司 涡轮机油组合物及其用途

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2679663C1 (ru) * 2018-04-06 2019-02-12 Федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский государственный энергетический университет" (ФГБОУ ВО "КГЭУ") Способ замедления окисления трансформаторного масла

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB810741A (en) * 1956-05-28 1959-03-25 Wakefield & Co Ltd C C Improvements in or relating to lubricating oil compositions
US3230168A (en) * 1964-12-08 1966-01-18 Shell Oil Co Lubricant compositions
US4119551A (en) * 1977-06-28 1978-10-10 Texaco Inc. Synthetic aircraft turbine lubricating oil compositions
US4125479A (en) * 1975-12-22 1978-11-14 Texaco Inc. Oxidation inhibited lubricating oil
US4226732A (en) * 1978-06-30 1980-10-07 Texaco Inc. Synthetic aircraft turbine oil
EP0528610A1 (fr) * 1991-08-09 1993-02-24 Oronite Japan Limited Composition d'huile moteur à faible teneur en phosphore et compositions d'additifs
US5236610A (en) * 1992-02-03 1993-08-17 The United States Of America As Represented By The Secretary Of The Commerce Stable high temperature liquid lubricant blends and antioxidant additives for use therewith

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB810741A (en) * 1956-05-28 1959-03-25 Wakefield & Co Ltd C C Improvements in or relating to lubricating oil compositions
US3230168A (en) * 1964-12-08 1966-01-18 Shell Oil Co Lubricant compositions
US4125479A (en) * 1975-12-22 1978-11-14 Texaco Inc. Oxidation inhibited lubricating oil
US4119551A (en) * 1977-06-28 1978-10-10 Texaco Inc. Synthetic aircraft turbine lubricating oil compositions
US4226732A (en) * 1978-06-30 1980-10-07 Texaco Inc. Synthetic aircraft turbine oil
EP0528610A1 (fr) * 1991-08-09 1993-02-24 Oronite Japan Limited Composition d'huile moteur à faible teneur en phosphore et compositions d'additifs
US5236610A (en) * 1992-02-03 1993-08-17 The United States Of America As Represented By The Secretary Of The Commerce Stable high temperature liquid lubricant blends and antioxidant additives for use therewith

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1067714C (zh) * 1998-08-27 2001-06-27 中国石油化工集团公司 用于透平油的复合添加剂
EP0994175A3 (fr) * 1998-10-16 2001-10-31 Ethyl Corporation Des huiles pour turbomoteurs ayant une excellente stabilité à l'oxydation à température élevée
CN1100859C (zh) * 1998-10-16 2003-02-05 乙基公司 具有优异的高温氧化稳定性的汽轮机油
US6326336B1 (en) 1998-10-16 2001-12-04 Ethyl Corporation Turbine oils with excellent high temperature oxidative stability
EP0994175A2 (fr) * 1998-10-16 2000-04-19 Ethyl Corporation Des huiles pour turbomoteurs ayant une excellente stabilité à l'oxydation à température élevée
EP1104800A3 (fr) * 1999-12-02 2001-06-20 Oronite Japan Limited Composition d'huile lubrificante pour moteurs à gaz
EP1104800A2 (fr) * 1999-12-02 2001-06-06 Oronite Japan Limited Composition d'huile lubrificante pour moteurs à gaz
US6207623B1 (en) 2000-01-14 2001-03-27 Exxonmobil Research And Engineering Company Industrial oils of enhanced resistance to oxidation
RU2493243C2 (ru) * 2009-02-02 2013-09-20 Ар.Ти. ВАНДЕРБИЛТ КОМПАНИ, ИНК. Беззольная смазывающая композиция
WO2011153178A2 (fr) 2010-06-02 2011-12-08 The Lubrizol Corporation Composition lubrifiante contenant un polymère à fonction carboxylique
US8969266B2 (en) 2010-06-02 2015-03-03 The Lubrizol Corporation Lubricating composition containing a carboxylic functionalised polymer
CN103517972A (zh) * 2011-05-16 2014-01-15 卢布里佐尔公司 用于涡轮机和水力系统的具有改进抗氧化性的润滑组合物
EP3189125A4 (fr) * 2014-09-04 2018-01-24 Vanderbilt Chemicals, LLC Additif antioxydant liquide sans cendre pour compositions lubrifiantes
CN107573987A (zh) * 2017-09-29 2018-01-12 中国石油化工股份有限公司 涡轮机油添加剂组合物及其用途
CN107653025A (zh) * 2017-09-29 2018-02-02 中国石油化工股份有限公司 涡轮机油组合物及其用途

Also Published As

Publication number Publication date
EP0735128A3 (fr) 1997-06-11
CA2171924C (fr) 2007-03-13
EP0735128B1 (fr) 2000-08-23
CA2171924A1 (fr) 1996-09-29

Similar Documents

Publication Publication Date Title
EP0644922B2 (fr) Liquide fonctionnel
US7829511B2 (en) Stabilized lubricant compositions
US7928045B2 (en) Stabilizing compositions for lubricants
EP1833952B1 (fr) Compositions lubrifiantes stabilisees au moyen de plusieurs antioxydants
US5895778A (en) Poly(neopentyl polyol) ester based coolants and improved additive package
EP0160620B1 (fr) Désactivateurs de métaux
EP1733010B2 (fr) Lubrifiants de haute performance à base de polyalkyleneglycol utilisés dans des vis sans fin
EP3189125B1 (fr) Compositions lubrifiantes comprenant additif antioxydant liquide sans cendre
US4880551A (en) Antioxidant synergists for lubricating compositions
EP0735128B1 (fr) Des huiles de corrosion et d'oxidation à vie prolongée
JP2007520618A (ja) 酸化防止剤ブレンドを含む潤滑剤組成物
US4965006A (en) N-substituted tetrahydroquinolines for use as antioxidants in lubricants
US4919833A (en) Functional fluids
CA1284987C (fr) Compositions lubrifiantes
US6143702A (en) Lubricating oils of enhanced oxidation stability containing n-phenyl-naphthyl amines, or substituted derivatives of n-phenyl naphthyl amine and carbodiimide acid scavengers
US6750182B1 (en) Polar oil based industrial oils with enhanced sludge performance
EP0205398A1 (fr) Additif pour fluides fonctionnels
JPS60156788A (ja) 安定剤およびそれを含有するポリアルキレングリコール組成物
EP0322362B1 (fr) Dérivés de thiadiazoles comme additifs pour lubrifiants
RU2680133C1 (ru) Улучшенные антиоксидантные композиции и содержащие их смазочные композиции
EP0682022B1 (fr) Produits de condensation de mélamine, de benzotriazoles et d'aldéhydes
EP0089023A1 (fr) Système de stabilisation pour des huiles lubrifiantes et méthode pour stabiliser des huiles lubrifiantes
EP0014547B1 (fr) Fluides résistant au feu
US4919832A (en) N-substituted tetrahydroquinolines for use as antioxidants in lubricants

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): BE GB

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): BE GB

17P Request for examination filed

Effective date: 19970827

17Q First examination report despatched

Effective date: 19971030

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

17Q First examination report despatched

Effective date: 19971030

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE GB

EN Fr: translation not filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20150327

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20150327

Year of fee payment: 20

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20160327

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20160327