EP1280872A2 - Stabilising compositions for lubricating oils - Google Patents

Stabilising compositions for lubricating oils

Info

Publication number
EP1280872A2
EP1280872A2 EP01925763A EP01925763A EP1280872A2 EP 1280872 A2 EP1280872 A2 EP 1280872A2 EP 01925763 A EP01925763 A EP 01925763A EP 01925763 A EP01925763 A EP 01925763A EP 1280872 A2 EP1280872 A2 EP 1280872A2
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
alkyl
phosphite
neutral
phosphate
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.)
Withdrawn
Application number
EP01925763A
Other languages
German (de)
French (fr)
Inventor
Alan Holt
Gerard Mulqueen
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.)
Lanxess Switzerland GmbH
Original Assignee
Great Lakes Chemical Europe GmbH
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 Great Lakes Chemical Europe GmbH filed Critical Great Lakes Chemical Europe GmbH
Publication of EP1280872A2 publication Critical patent/EP1280872A2/en
Withdrawn legal-status Critical Current

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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
    • 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
    • C10M129/12—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring with 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
    • 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
    • C10M129/76—Esters containing free hydroxy or carboxyl 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
    • 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
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M135/24—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; 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
    • 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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    • 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
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    • 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
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    • 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
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    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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    • 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
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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    • C10M2207/28—Esters
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    • C10M2207/289—Partial esters containing free hydroxy 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • 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
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    • 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
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    • C10M2215/066—Arylene diamines
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    • C10M2215/067—Polyaryl amine alkanes
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    • 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
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    • 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
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    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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    • C10M2219/088—Neutral salts
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    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention relates to stabilising compositions for lubricant base stocks and lubricant formulations ⁇
  • lubricant base stocks such as mineral and synthetic base oils chosen from Group I, Group II, Group III, Group IV and Group V base stocks as classified by the American Petroleum Institute, as well as natural and synthetic esters including polyol esters, more particularly, but not limited to automotive oils, circulatory oils, gear oils, greases, hydraulic fluids, turbine fluids and metal working fluids.
  • lubricant formulations is meant a lubricant base stock as described above, plus additional additives including but not limited to antioxidants, rust inhibitors, metal passivators, ashless dispersants, antiwear additives, extreme pressure additives and detergents, viscosity index improvers and antifoam agents.
  • a stabilising composition for lubricant base stocks and lubricant compositions comprises :
  • R ⁇ and R 2 are the same or different and may be H, an alkyl group with 4 to 9 carbon atoms or an aralkyl group with 8 carbon atoms and m and n are 0 to 2 but m + n is not greater than 3, either alone or optionally blended with at least one hindered phenolic antioxidant selected from those corresponding to one of the following general formulae:
  • R 3 , R ⁇ R 5 and 5 are the same or different and may be an alkyl group with 1 to 4 carbon atoms and X is -S- or -CH 2 - or - CH 2 CH 2 -S-CH 2 CH 2 - or - -CH 2 -S-CH 2 - or -CH 2 CH 2 CO 2 CH 2 CH 2 -S-CH 2 CH CO 2 CH 2 CH 2 -
  • R 7 is an alkyl group with 6 to 20 carbon atoms
  • R 9 and Rw are the same or different and may be H, CH 3 , isopropyl or tertiary butyl and m is 0 to 2;
  • R ⁇ , R 12 and R 13 are all the same and are alkyl groups with 4 to 12 carbon atoms; (iii) neutral alkyl aryl phosphates:
  • R 1 is different from R 15 and R 16 and R 14 is an alkyl group with 4 to 12 carbon atoms and R 15 is phenyl or substituted phenyl with 7 to 10 carbon atoms and R 16 may be an alkyl group with 4 to 12 carbon atoms or phenyl or substituted phenyl with 7 to 10 carbon atoms;
  • R 1 is an alkyl group with 5 to 12 carbon atoms and m is 1 or 2 and n is 1 or 2 but m+n is not greater than 3; (v) neutral triaryl phosphites :
  • R 18 , R 1 , R20 are the same or different and are H or alkyl with 1 to 9 carbon atoms;
  • R 21 , R 2 2 and R 23 are the same or different and are alkyl groups with 1 to 18 carbon atoms.
  • R 24 and R 2 are the same or different and are alkyl groups with 1 to 12 carbon atoms or R 24 is phenyl or substituted phenyl where R 26 is alkyl with 1 to 9 carbon atoms.
  • R 2 may be an alkyl group with 4 to 18 carbon atoms, phenyl or substituted phenyl with 7 to 10 carbon atoms and m is 1 or 2, n is 1 or 2 but m + n is not greater than 3, and wherein the antioxidants and the phosphate(s) and/or phosphite(s) are utilised in a weight ratio from 10:1 to 1:10, preferably 1:1 to 1:5.
  • the stabilising composition is prepared by heating the antioxidant(s) and the phosphate(s) and/or phosphite(s) for 0.2 to 6 hours at a temperature range of 40°C to 150°C.
  • the treat rates of the antioxidant(s) and the phosphate(s) and/or phosphite(s) in the lubricant base stocks and lubricant compositions preferably are within the following weight ranges:
  • the amine and hindered phenol antioxidants are used at 0.5 to 2.0% each.
  • the neutral alkyl, aryl and alkyl aryl phosphates and phosphites are used at 0.5 to 4%.
  • the acid phosphates and phosphites at 0.025 to 0.05% (when used together with the neutral phosphates).
  • formula I compounds are 4-tert-butyl, 4'-tert-octyl diphenylamine; 4,4'- di-tert-octyl diphenyl amine and 4,4'-di-iso-nonyl diphenylamine.
  • formula II compounds are 4,4'-methylene bis (2,6 ditertiary butyl phenol); 2,2' thiodiethylene bis [3-(3,5-di-tert-butyl-4-hydroxy-phenyl) propionate]; 4,4'-thiobis (2-t-butyl-5-methyl phenol); 6,6'-thiobis (2-methyl-4-t-butylphenol).
  • Examples of formula III compounds are C 7 . alkyl ester of 3,5-di-tert-butyl-4-hydroxy benzene-3-propionic acid; C ⁇ e alkyl ester of 3,5-di-tert-butyl-4-hydroxybenzene-3- propionic acid.
  • An Example of formula IN compounds is pentaerythritol tetra ester of 3,5 di-tert-butyl- 4-hydroxy benzene-3-propionic acid.
  • Examples of formula N compounds are tri-dimethyl phenyl phosphate; tri-isopropyl phenyl phosphate; mono-phenyl-di (-tert-butyl phenyl) phosphate.
  • Examples of formula NI compounds are tributyl phosphate; trioctyl phosphate.
  • Examples of formula VII compounds are octyldiphenyl phosphate; dibutyl-mono-phenyl phosphate.
  • N ⁇ i compounds dipentyl hydrogen phosphate; di C 10 - 12 alkyl- hydrogen phosphate; C 10-1 2 alkyl-dihydrogen phosphate.
  • An Example of formula LX is tris nonyl phenyl phosphite.
  • Examples of formula X are trilauryl phosphite; trioctyl phosphite.
  • Examples of formula XI are decyl diphenyl phosphite; didecyl monophenyl phosphite.
  • Examples of formula XII are dibutyl hydrogen phosphite; dioctyl hydrogen phosphite; cetyl stearyl hydrogen phosphite.
  • lubricant base stocks and lubricant formulations can have varying levels of stability dependent on:
  • the Table shows the relative oxidation stability results obtained by adding certain antioxidant(s) and phosphate(s) and/or phosphite(s) mixtures to Group III base stocks.
  • the relative oxidation stabilities of the lubricant base stock is determined by the rotating bomb oxidation stability test (RBOT), IP test method number 229.
  • the oxidation stability is defined as the number of minutes required to effect a reduction in oxygen pressure of 25.4 PSI or 1.75 bar when the oil and additives are heated at 150°C in an oxygen pressurised vessel.

Abstract

Stabilising compositions for lubricant base stocks and lubricant formulations are composed of a mixture of (a) at least one aromatic aminic amine antioxidant optionally blended with at least one hindered phenolic antioxidant and (b) at least one neutral organo phosphate or phosphite, optionally blended with at least one acid organo phosphate or phosphite. These stabilising composition mixtures are characterised by their stabilising capacity which is considerably higher than that of either the single antioxidants or the single phosphate or phosphite additives. These stabilising compositions can be used in all fields where the single components of the mixtures are generally used and where deterioration due to oxidation processes takes place.

Description

STAB1 ISING COMPOSITIONS FOR LUBRICATING OILS
This invention relates to stabilising compositions for lubricant base stocks and lubricant formulations^
We have unexpectedly found that mixtures of certain aromatic aminic antioxidants, optionally in admixture with certain hindered phenol antioxidants, when mixed with certain organo phosphate esters and organo phosphite esters offer unique synergy and improved performance in terms of stability when used within lubricant base stocks and lubricant formulations.
By lubricant base stocks is meant lubricants such as mineral and synthetic base oils chosen from Group I, Group II, Group III, Group IV and Group V base stocks as classified by the American Petroleum Institute, as well as natural and synthetic esters including polyol esters, more particularly, but not limited to automotive oils, circulatory oils, gear oils, greases, hydraulic fluids, turbine fluids and metal working fluids.
By lubricant formulations, is meant a lubricant base stock as described above, plus additional additives including but not limited to antioxidants, rust inhibitors, metal passivators, ashless dispersants, antiwear additives, extreme pressure additives and detergents, viscosity index improvers and antifoam agents.
According to the present invention a stabilising composition for lubricant base stocks and lubricant compositions comprises :
(a) at least one aromatic aminic antioxidant having the general formula:
wherein RΪ and R2 are the same or different and may be H, an alkyl group with 4 to 9 carbon atoms or an aralkyl group with 8 carbon atoms and m and n are 0 to 2 but m + n is not greater than 3, either alone or optionally blended with at least one hindered phenolic antioxidant selected from those corresponding to one of the following general formulae:
II
wherein R3, R^ R5 and 5 are the same or different and may be an alkyl group with 1 to 4 carbon atoms and X is -S- or -CH2- or - CH2CH2-S-CH2CH2 - or - -CH2-S-CH2 - or -CH2CH2CO2CH2CH2-S-CH2CH CO2CH2CH2-
III wherein R7 is an alkyl group with 6 to 20 carbon atoms; and
IN with (b) at least one neutral organo phosphate or phosphite optionally mixed with at least one acid organo phosphate or phosphite selected from those corresponding to the following general formulae:
(i) neutral triaryl phosphates :
N
wherein s, R9 and Rw are the same or different and may be H, CH3, isopropyl or tertiary butyl and m is 0 to 2;
(ii) neutral trialkyl phosphates:
R11-(T I "0- R13 0
R12
NI
wherein Rπ, R12 and R13 are all the same and are alkyl groups with 4 to 12 carbon atoms; (iii) neutral alkyl aryl phosphates:
Nil
wherein R1 is different from R15 and R16 and R14 is an alkyl group with 4 to 12 carbon atoms and R15 is phenyl or substituted phenyl with 7 to 10 carbon atoms and R16 may be an alkyl group with 4 to 12 carbon atoms or phenyl or substituted phenyl with 7 to 10 carbon atoms;
(iv) alkyl acid phosphates:
( HOJ -( 0R17 ) n
Niπ
wherein R1 is an alkyl group with 5 to 12 carbon atoms and m is 1 or 2 and n is 1 or 2 but m+n is not greater than 3; (v) neutral triaryl phosphites :
LX
wherein R18, R1 , R20 are the same or different and are H or alkyl with 1 to 9 carbon atoms;
(vi) neutral trialkyl phosphites:
R21— 0 P— 0— R23
I 0
R22
X
wherein R21, R22 and R23 are the same or different and are alkyl groups with 1 to 18 carbon atoms. (vii) neutral alkyl aryl phosphites:
XI
wherein R24 and R2 are the same or different and are alkyl groups with 1 to 12 carbon atoms or R24 is phenyl or substituted phenyl where R26 is alkyl with 1 to 9 carbon atoms.
(viii) alkyl acid phosphites:
( HOJ -(0R27)n
XII
wherein R2 may be an alkyl group with 4 to 18 carbon atoms, phenyl or substituted phenyl with 7 to 10 carbon atoms and m is 1 or 2, n is 1 or 2 but m + n is not greater than 3, and wherein the antioxidants and the phosphate(s) and/or phosphite(s) are utilised in a weight ratio from 10:1 to 1:10, preferably 1:1 to 1:5.
In one embodiment of the invention, the stabilising composition is prepared by heating the antioxidant(s) and the phosphate(s) and/or phosphite(s) for 0.2 to 6 hours at a temperature range of 40°C to 150°C. The treat rates of the antioxidant(s) and the phosphate(s) and/or phosphite(s) in the lubricant base stocks and lubricant compositions preferably are within the following weight ranges:
(a) aromatic amine antioxidants - 0.1 to 5%;
(b) hindered phenol antioxidants - 0.1 to 5%;
(c) neutral aryl phosphates - 0.2 to 10%;
(d) neutral alkyl phosphates - 0.2 to 10%;
(e) neutral alkyl aryl phosphates - 0.2 to 10%;
(f) alkyl acid phosphates - 0.01 to 5%;
(g) neutral aryl phosphites - 0.2 to 10%; (h) neutral alkyl phosphites - 0.2 to 10%; (i) neutral alkyl aryl phosphites - 0.2 to 10%; (j) alkyl acid phosphites - 0.01 to 5%;
Preferably, the amine and hindered phenol antioxidants are used at 0.5 to 2.0% each. The neutral alkyl, aryl and alkyl aryl phosphates and phosphites are used at 0.5 to 4%. The acid phosphates and phosphites at 0.025 to 0.05% (when used together with the neutral phosphates).
Examples of formula I compounds are 4-tert-butyl, 4'-tert-octyl diphenylamine; 4,4'- di-tert-octyl diphenyl amine and 4,4'-di-iso-nonyl diphenylamine.
Examples of formula II compounds are 4,4'-methylene bis (2,6 ditertiary butyl phenol); 2,2' thiodiethylene bis [3-(3,5-di-tert-butyl-4-hydroxy-phenyl) propionate]; 4,4'-thiobis (2-t-butyl-5-methyl phenol); 6,6'-thiobis (2-methyl-4-t-butylphenol).
Examples of formula III compounds are C7. alkyl ester of 3,5-di-tert-butyl-4-hydroxy benzene-3-propionic acid; C^e alkyl ester of 3,5-di-tert-butyl-4-hydroxybenzene-3- propionic acid.
An Example of formula IN compounds is pentaerythritol tetra ester of 3,5 di-tert-butyl- 4-hydroxy benzene-3-propionic acid. Examples of formula N compounds are tri-dimethyl phenyl phosphate; tri-isopropyl phenyl phosphate; mono-phenyl-di (-tert-butyl phenyl) phosphate.
Examples of formula NI compounds are tributyl phosphate; trioctyl phosphate.
Examples of formula VII compounds are octyldiphenyl phosphate; dibutyl-mono-phenyl phosphate.
Examples of formula Nπi compounds are dipentyl hydrogen phosphate; di C10-12 alkyl- hydrogen phosphate; C 10-12 alkyl-dihydrogen phosphate.
An Example of formula LX is tris nonyl phenyl phosphite.
Examples of formula X are trilauryl phosphite; trioctyl phosphite.
Examples of formula XI are decyl diphenyl phosphite; didecyl monophenyl phosphite.
Examples of formula XII are dibutyl hydrogen phosphite; dioctyl hydrogen phosphite; cetyl stearyl hydrogen phosphite.
Using stabilising compositions of the invention, lubricant base stocks and lubricant formulations can have varying levels of stability dependent on:
(i) proper choice of the antioxidant(s) and phosphate(s) and/or phosphite(s) to provide for the best performance, in terms of stability, within particular lubricant base stocks or particular lubricant formulations; or
(ii) by changing the ratio of the antioxidant to the phosphate(s) and/or phosphite(s); or
(iii) keeping the ratio of the antioxidant(s) to the phosphate(s) and/or phosphite(s) constant while altering or decreasing the treat rate of the antioxidant(s) and phosphate(s) and/or phosphite(s).
(iv) changing the ratio of neutral phosphate to acid phosphate and neutral phosphite to acid phosphite. In other words, the components of the mixtures of the invention, either individually or in combination, can be tailored to provide the required performance characteristics in terms of stability, in a particular base stock and/or lubricant formulation.
Embodiments of the invention will now be described by way of example with reference to the Table set out below.
The Table shows the relative oxidation stability results obtained by adding certain antioxidant(s) and phosphate(s) and/or phosphite(s) mixtures to Group III base stocks. The relative oxidation stabilities of the lubricant base stock is determined by the rotating bomb oxidation stability test (RBOT), IP test method number 229. The oxidation stability is defined as the number of minutes required to effect a reduction in oxygen pressure of 25.4 PSI or 1.75 bar when the oil and additives are heated at 150°C in an oxygen pressurised vessel.
The results in the Table show that there is a synergistic effect (in terms of stability) when a blend of additives according to the invention is added to Group III lubricant base stocks.
ASTM IP 229 ROTARY BOMB OXIDATION TEST DATA

Claims

C AIMS
1. A stabilising composition comprising a mixture of:
(a) at least one aromatic aminic antioxidant having the general formula:
wherein Ri and R2 are the same or different and may be H, an alkyl group with 4 to 9 carbon atoms or an aralkyl group with 8 carbon atoms and m and n are 0 to 2 but m + n is not greater than 3, either alone or optionally blended with at least one hindered phenolic antioxidant selected from those corresponding to one of the following general formulae:
π
wherein R3, R_%, R5 and R5 are the same or different and may be an alkyl group with 1 to 4 carbon atoms and X is -S- or -CH2- or - CH2CH2-S-CH2CH2 - or - -CH2-S-CH2 -or -CH2CH2Cθ2CH2CH2-S-CH2CH2Cθ2CH2CH2-
wherein R7 is an alkyl group with 6 to 20 carbon atoms; and
IN
with (b) at least one neutral organo phosphate or phosphite optionally mixed with at least one acid organo phosphate or phosphite selected from those corresponding to the following general formulae
(i) neutral triaryl phosphates :
N
wherein Rg, R9 and Rio are the same or different and may be H, CH3, isopropyl or tertiary butyl and m is 0 to 2; (ii) neutral trialkyl phosphates:
R11— 0 I -R13 0
R12
NI
wherein Rπ, R12 and Rι3 are all the same and are alkyl groups with 4 to 12 carbon atoms:
(iii) neutral alkyl aryl phosphates:
VII
wherein Rι4 is different from Rι5 and Rie and Rι4 is an alkyl group with 4 to 12 carbon atoms and Rι5 is phenyl or substituted phenyl with 7 to 10 carbon atoms and R16 may be an alkyl group with 4 to 12 carbon atoms or phenyl or substituted phenyl with 7 to 10 carbon atoms; (iv) alkyl acid phosphates:
Niπ
wherein Rπ is an alkyl group with 5 to 12 carbon atoms and m is 1 or 2 and n is 1 or 2 but m + n is not greater than 3;
(v) neutral triaryl phosphites:
LX
wherein R]8, Rι9, R2o are the same or different and are H or alkyl with 1 to 9 carbon atoms. (vi) neutral trialkyl phosphites
R21— 0 P— -0— R23
I 0
R22
X
wherein R21, R22, and R23 are the same or different and are alkyl groups with 1 to 18 carbon atoms.
(viϊ) neutral alkyl aryl phosphites:
XI
wherein ^ and R25 are the same or different and are alkyl groups with 1 to 12 carbon atoms or ∑4 is phenyl or substituted phenyl where R26 is alkyl with 1 to 9 carbon atoms. (viii) alkyl acid phosphites:
( HO)- — P ( 0R27)n
XII
wherein R2 may be an alkyl group with 4 to 18 carbon atoms, phenyl or substituted phenyl with 7 to 10 carbon atoms and m is 1 or 2, n is 1 or 2 but m + n is not greater than 3, and wherein the antioxidants and the phosphate(s) andor phosphite(s) are utilised in a weight ratio from 10:1 to 1:10.
2. The stabilising composition in accordance with claim 1 wherein the antioxidant(s) and the phosphate(s) and/or phosphite(s) are utilised in a weight ratio from 1:1 to 1:5.
3. The stabilising composition in accordance with claim 1 or claim 2 which has been prepared by heating the antioxidant(s) and the phosphate(s) and/or phosphite(s) for 0.2 to 6 hours at a temperature between 40°C and 150°C.
4. A lubricant base stock or lubricant composition stabilised by the stabilised composition of any one of claims 1 to 3.
EP01925763A 2000-05-10 2001-05-10 Stabilising compositions for lubricating oils Withdrawn EP1280872A2 (en)

Applications Claiming Priority (3)

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GBGB0011189.8A GB0011189D0 (en) 2000-05-10 2000-05-10 Anti-oxidant additives
PCT/GB2001/002058 WO2001085878A2 (en) 2000-05-10 2001-05-10 Stabilising compositions for lubricating oils

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JP2004501234A (en) 2004-01-15
WO2001085878A2 (en) 2001-11-15

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