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EP0332247B1 - Lubricating compositions containing complexes endowed with anti-oxidant activity - Google Patents

Lubricating compositions containing complexes endowed with anti-oxidant activity Download PDF

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Publication number
EP0332247B1
EP0332247B1 EP89200481A EP89200481A EP0332247B1 EP 0332247 B1 EP0332247 B1 EP 0332247B1 EP 89200481 A EP89200481 A EP 89200481A EP 89200481 A EP89200481 A EP 89200481A EP 0332247 B1 EP0332247 B1 EP 0332247B1
Authority
EP
European Patent Office
Prior art keywords
composition according
lubricating composition
oil
alkyl
group
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
EP89200481A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0332247A1 (en
Inventor
Edilberto Colombo
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.)
Agip Petroli SpA
Original Assignee
Agip Petroli SpA
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 Agip Petroli SpA filed Critical Agip Petroli SpA
Priority to AT89200481T priority Critical patent/ATE67235T1/de
Publication of EP0332247A1 publication Critical patent/EP0332247A1/en
Application granted granted Critical
Publication of EP0332247B1 publication Critical patent/EP0332247B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C10M167/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound, a non-macromolecular compound and a compound of unknown or incompletely defined constitution, each of these compounds being essential
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
    • C10M129/92—Carboxylic acids
    • C10M129/93—Carboxylic acids having carboxyl groups 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
    • C10M129/95—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
    • 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
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    • 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
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
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    • 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
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
    • C10M135/30—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups; Derivatives thereof
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    • 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
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C—CHEMISTRY; METALLURGY
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    • C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/04—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing 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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/06—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing 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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/12—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing conjugated diene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—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
    • C10M145/12—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 monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/18—Complexes with metals
    • C—CHEMISTRY; METALLURGY
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    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C—CHEMISTRY; METALLURGY
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    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
    • C—CHEMISTRY; METALLURGY
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    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
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    • C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10N2010/04—Groups 2 or 12

Definitions

  • the present invention relates to lubricating compositions containing oil-soluble complexes constituted by salts of Cu-(I) with monovalent anions, and organic ligands based on phosphorus.
  • the present invention relates as well to concentrated blends, in oil, of commonly used additives for lubricant oils, additionally containing complexes formed by salts of Cu-(I) with monovalent anions, and organic ligands containing phosphorus.
  • concentrated blends which are incorporated into the mass of the lubricant, are used in order to supply said lubricant with the necessary additives.
  • Patent application EP-A-24,146 discloses lubricating compositions containing oil-soluble copper compounds, typically oil-soluble salts.
  • concentrations claimed for copper are of at least 5 ppm, but one can clearly see from the examples that, in order to attain acceptable results, the threshold value of 120 ppm results to be already critical.
  • the present Applicant has surprisingly found now that when in the lubricating composition and in the concentrates particular complexes are used which are formed by salts of Cu-(I) in which the anion is monovalent and the ligand is an organic, phosphorus-containing ligand, the antioxidant activity which is obtained persists even at extremely low values of concentration, values at which the compounds according to the prior art are no longer active.
  • Complexes of Cu-(I) which can be advantageously used in the lubricating compositions according to the present invention are those oil-soluble complexes of salts of Cu-(I) with monovalent anions, in which the ligands are organic, phosphorus-containing ligands.
  • the organic ligands can be phosphites and phosphines, in particular aryl and alkyl-aryl phosphites and phosphines, which are capable of endowing the complex with the salt of Cu-(I) with characteristics of oil-solubility.
  • phosphites and phosphines in particular aryl and alkyl-aryl phosphites and phosphines, which are capable of endowing the complex with the salt of Cu-(I) with characteristics of oil-solubility.
  • the ligands triphenylphosphite, trinonylphenylphosphite, tridodecylphenylphosphite, tri(2,4-ditert.-butylphenyl)phosphite, triphenylphosphines and alkylated triphenylphosphines can be used.
  • Counter-ions of the cuprous salt which can be advantageously used are, e.g.: Cl, Br, I, SCN, CN, BF4, BH4, NO2 and NO3.
  • This reaction can be carried out in the presence of the same lubricant oil, or in a suitable organic solvent.
  • the reaction is typically carried out under an inert atmosphere, at a temperature comprised within the range of from room temperature to 80°C, for a time comprised within the range of from 30 minutes to 5 hours.
  • the reaction is carried out in an inert, apolar solvent, e.g., benzene, under anhydrous conditions, at a temperature comprised within the range of from room temperature to the refluxing temperature, for about half an hour.
  • apolar solvent e.g., benzene
  • the lubricant oil can either be a mineral oil, or a synthesis oil (carboxy esters, polyolefins, carbonic acid esters, and so forth), as well as a mixture of both of them.
  • an ash-less dispersant is added, with the purpose of keeping dispersed any matter foreign to the oil, whether coming from the external environment, or deriving from thermal or oxidative alterations of the same oil.
  • the commonly used dispersants are in general nitrogen-containing derivatives, esters, anhydrides and salts of mono- and bi-carboxy acids bearing a long hydrocarbon chain of from 50 to 400 carbon atoms.
  • anhydrides of succinic acids with high-molecular weight aliphatic substituents, or esters of these acids with mono- and poly-alcohols, phenols, naphthols, or, still, amides or imides of these acids with polyethyleneamines are preferred.
  • alkenyl chains such as, e.g, in case of isobutenyl-succinic acids, are preferred.
  • a viscosity-index improver is then necessary, the purpose of which is of keeping the viscosity changes with temperature comprised within a narrower range than as obtained with the oil to which such an additive is not added.
  • Compounds displaying such an activity are oil-soluble polymers, among which the most representative are: ethylene-propylene copolymer, poly-iso-butenes, styrene-diene copolymers, poly-acrylates and poly-methacrylates.
  • a Zn dihydrocarbyldithiophosphate in which the substituents can be alkyl groups, alkenyl groups, aryl groups, alkylaryl groups, cycloalkyl groups, with such grops being either equal to, or different from, each other.
  • the presence of a detergent preventing impurities and residues from depositing on the metal surfaces can be necessary.
  • the most commonly used detergents are neutral calcium or magnesium sulphonate; the super-basic calcium or magnesium sulphonate; calcium, magnesium and barium phenolates and sulpho-phenolates; calcium and magnesium alkyl-salicylates and naphthenates.
  • the activity of the oil-soluble complexes constituted by salts of Cu-(I) and phosphorus-based organic ligands was compared to that of additives already known in the art, by means of a set of tests capable of evaluating the antioxidant and antiwear capabilities of them.
  • the antioxidant properties were evaluated on the lubricant, after that this latter was submitted to the IP 48-MOT oxidation test; with the changes being measured, which occurred in three typical parameters, viz.: viscosity, neutralization number and absorbance of the oxidation band measured on the I.R. spectrophotometer at 1,700 cm ⁇ 1.
  • the oxidation test consists in submitting a sample of lubricant oil to an air stream flowing at the rate of 0.3 litres/hour per sample gram at 165°C over 72 hours, in the presence of a homogeneous iron catalyst (50 ppm, as the metal).
  • the cuprous complex was prepared by reacting 160 g of trinonylphenylphosphite (0.24 mol) with 24 g of CuCl (0.24 mol) in 185 g of SN 450 oil under a blanketing nitrogen atmosphere.
  • the reaction mixture is kept with stirring at room temperature for 4 hours.
  • the lubricating composition used in this example is formed by SN 450 oil admixed with
  • Trinonylphenylphosphite CuCl was prepared as hereinabove seen, and tri(2,4-ditert.-butylphenyl)phosphite. CuCl was obtained according to the same route, by reacting 154 g of tri(2,4-ditert.-butylphenyl)phosphite (0.24 mol) with 24 g of CuCl (0.24 mol) in 178 g of SN 450 oil.
  • a “fail” oil an oil is understood which, when is submitted to the ASTM IIID test, showed a change in viscosity greater than 375%.
  • the ASTM IIID test developed by General Motors, uses a 1977 version of the 5.7-litre Oldsmobile V-8 engine, running at a high speed (3,000 rpm) at the temperature of 160°C, for 64 hours, under a constant load of 100 BHP.
  • an E7D47 composition was submitted to the "4-ball-wear" ASTM D4172 test, before and after undergoing the oxidation process.
  • a fourth ball is placed and made revolve under load, sliding on only three points of contact with the underlying balls.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP89200481A 1988-03-02 1989-02-27 Lubricating compositions containing complexes endowed with anti-oxidant activity Expired - Lifetime EP0332247B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT89200481T ATE67235T1 (de) 1988-03-02 1989-02-27 Schmiermittelzusammensetzungen, die komplexe mit antioxidationsakitivaet enthalten.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT8819609A IT1215961B (it) 1988-03-02 1988-03-02 Composizione lubrificanti contenenti complessi con attivita'antiossidante.
IT1960988 1988-03-02

Publications (2)

Publication Number Publication Date
EP0332247A1 EP0332247A1 (en) 1989-09-13
EP0332247B1 true EP0332247B1 (en) 1991-09-11

Family

ID=11159527

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Application Number Title Priority Date Filing Date
EP89200481A Expired - Lifetime EP0332247B1 (en) 1988-03-02 1989-02-27 Lubricating compositions containing complexes endowed with anti-oxidant activity

Country Status (6)

Country Link
EP (1) EP0332247B1 (it)
AT (1) ATE67235T1 (it)
DE (1) DE68900251D1 (it)
ES (1) ES2027441T3 (it)
GR (1) GR3002887T3 (it)
IT (1) IT1215961B (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10300097A1 (de) * 2003-01-07 2004-07-22 Bayer Ag Kupfer-Komplexe und ihre Verwendung

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL44792C (it) * 1935-04-11
US2199944A (en) * 1935-06-01 1940-05-07 Shell Dev Lubricant
US2645613A (en) * 1949-03-14 1953-07-14 Shell Dev Lubricating composition
US3933878A (en) * 1972-06-02 1976-01-20 Exxon Research And Engineering Company Ligand complexes of cu(1)salts
GB2056482A (en) * 1979-08-13 1981-03-18 Exxon Research Engineering Co Lubricating oil compositions

Also Published As

Publication number Publication date
DE68900251D1 (de) 1991-10-17
ES2027441T3 (es) 1992-06-01
IT1215961B (it) 1990-02-22
EP0332247A1 (en) 1989-09-13
GR3002887T3 (en) 1993-01-25
ATE67235T1 (de) 1991-09-15
IT8819609A0 (it) 1988-03-02

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