WO2009134716A1 - Polyalkylene glycol lubricant composition - Google Patents

Polyalkylene glycol lubricant composition Download PDF

Info

Publication number
WO2009134716A1
WO2009134716A1 PCT/US2009/041800 US2009041800W WO2009134716A1 WO 2009134716 A1 WO2009134716 A1 WO 2009134716A1 US 2009041800 W US2009041800 W US 2009041800W WO 2009134716 A1 WO2009134716 A1 WO 2009134716A1
Authority
WO
WIPO (PCT)
Prior art keywords
lubricant composition
aspartic acid
lubricant
polyalkylene glycol
additive package
Prior art date
Application number
PCT/US2009/041800
Other languages
French (fr)
Inventor
Johan Thoen
Mathias Woydt
Daniel Zweifel
Original Assignee
Dow Global Technologies Inc.
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 Dow Global Technologies Inc. filed Critical Dow Global Technologies Inc.
Priority to EP09739518.0A priority Critical patent/EP2271732B1/en
Priority to MX2010011869A priority patent/MX324478B/en
Priority to CA2722431A priority patent/CA2722431C/en
Priority to US12/988,871 priority patent/US8357644B2/en
Publication of WO2009134716A1 publication Critical patent/WO2009134716A1/en
Priority to US13/715,078 priority patent/US8592357B2/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16Amides; Imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00Lubricating 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
    • C10M141/06Lubricating 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 nitrogen-containing compound
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04Mixtures of base-materials and additives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/1033Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C10M2209/1055Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C10M2209/1075Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106 used as base material
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • C10M2209/1085Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified used as base material
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
    • C10M2215/065Phenyl-Naphthyl amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08Amides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10Amides of carbonic or haloformic acids
    • C10M2215/102Ureas; Semicarbazides; Allophanates
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/223Five-membered rings containing nitrogen and carbon only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/083Dibenzyl sulfide
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108Phenothiazine
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/047Thioderivatives not containing metallic elements
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/10Groups 5 or 15
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01Physico-chemical properties
    • C10N2020/081Biodegradable compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10Inhibition of oxidation, e.g. anti-oxidants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64Environmental friendly compositions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/70Soluble oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines

Definitions

  • This invention pertains to a polyalkylene glycol (PAG) lubricant composition containing an amide or ester derivative of aspartic acid, or a Group V salt of an aspartic acid.
  • PAG polyalkylene glycol
  • Engine lubricant oils are composed of base oils and additives. Certain synthetic oils, such as PAGs, are characterized by inherent low friction properties and good low and high temperature viscosity properties which promote excellent hydrodynamic film formation between moving parts.
  • PAG-based engine lubricant oils find an increasing original equipment manufacturer (OEM) interest due to their intrinsic properties in relation to an increasing number of new performance criteria requested by automotive engine design departments.
  • OEM original equipment manufacturer
  • the criteria in directive EC/1999/45 are incorporated herein by reference as the criteria for determining whether an additive package is in accordance with this invention.
  • this invention is a lubricant composition useful for automotive engines, comprising: (A) at least one PAG suitable for use as a lubricant in an automotive engine, and (B) an additive package which comprises an acid scavenger, wherein the acid scavenger is an aspartic acid ester, an aspartic acid amide, a Group V salt of aspartic acid, or a combination thereof.
  • the lubricant composition may contain additional components and have certain properties including but not limited to compositions wherein: the additive package further comprises (i) at least ( ⁇ ) one extreme pressure anti-wear additive, (ii) ⁇ one anti-corrosion additive, (iii) ⁇ one antioxidant, (iv) ⁇ one friction modifier, (v) ⁇ one additional acid scavenger, or any combination of (i)-(v); the additive package is soluble at 25 degrees Centigrade ( 5 C) in the PAG; the additive package meets bio-no-tox criteria of EC/1999/45 and preferably does not deteriorate the bio-no- tox properties of the PAG (also known as "lubricant oil base stock) below (does not pass) the EC/1999/45 criteria; the composition excludes additives that do not meet the EC/1999/45 bio- no-tox criteria or will deteriorate the bio-no-tox properties of the lubricant oil base stock; the additive package includes ⁇ one thickening agent;
  • this invention is a method of lubricating an automobile engine, comprising: employing the above lubricant composition as a lubricant oil.
  • Lubricating oil base stocks used in formulating lubricant compositions of this invention are composed primarily or exclusively of PAGs of lubricating viscosity.
  • PAGs of lubricating viscosity.
  • a wide variety of such oleaginous liquids are available as articles of commerce.
  • the PAG has a viscosity at 40 5 C within a range of from 20 centistokes (cSt) (20 square millimeters per second (mm 2 /s)) to 10,000 cSt (10,000 mm 2 /s) and a viscosity within a range of from 3 cSt (3 mm 2 /s) to 2,000 cSt (2,000 mm 2 /s) at 100 5 C.
  • the base stocks preferably meet EC/1999/45 bio-no-tox criteria.
  • Suitable PAGs include, but are not limited to, a reaction product of a 1 ,2-oxide (vicinal epoxide) with water, or an alcohol, or an aliphatic polyhydric alcohol containing from 2 hydroxyl groups to 6 hydroxyl groups and between 2 carbon atoms (C 2 ) and 8 carbon atoms (C 8 ) per molecule.
  • Suitable compounds useful in preparing these PAGs include lower (C 2 to C 8 ) alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide, cyclohexene oxide, and glycidol. Mixtures of these 1 ,2-oxides are also useful in preparing PAGs.
  • a PAG may be formed by known techniques in which an aliphatic polyhydric alcohol or water or monohydric alcohol (often called an "initiator") is reacted with a single 1 ,2-oxide or a mixture of two or more of the 1 ,2- oxides.
  • the initiator may be first oxyalkylated with one 1 ,2-oxide, followed by oxyalkylation with a different 1 ,2-oxide or a mixture of 1 ,2-oxides.
  • the oxyalkylated initiator can be further oxyalkylated with a still different 1 ,2-oxide.
  • mixture when applied to a PAG containing a mixture of 1 ,2-oxides, includes both random and/or block polyethers such as those prepared by: (1 ) random addition obtained by simultaneously reacting two or more 1 ,2-oxides with the initiator; (2) block addition in which the initiator reacts first with one 1 ,2-oxide and then with a second 1 ,2-oxide, and (3) block addition in which the initiator first reacts with a first 1 ,2-oxide followed by random addition wherein the initiator reacts with a combination of the first 1 ,2-oxide and a second 1 ,2-oxide.
  • any suitable ratio of different 1 ,2-oxides may be employed.
  • the proportion of EO is generally between 3 weight percent (wt percent) and 60 wt percent, and preferably between 5 wt percent and 50 wt percent, based on total mixture weight.
  • Aliphatic polyhydric alcohol reactants used in making the PAG include those containing between from two hydroxyl (OH) groups to six OH groups and from two carbon atoms (C 2 ) to eight carbon atoms (C 8 ) per molecule, as illustrated by compounds such as: ethylene glycol, propylene glycol, 2,3-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butanediol, 1 ,3-propanediol, 1 ,5- pentane diol, 1 ,6-hexene diol, glycerol, trimethylolpropane, sorbitol, pentaerythritol, mixtures thereof and the like.
  • Cyclic aliphatic polyhydric compounds such as starch, glucose, sucrose, and methyl glucoside may also be employed in PAG preparation.
  • Each of the aforesaid polyhydric compounds and alcohols can be oxyalkylated with EO, PO, butylene oxide (BO), cyclohexene oxide, glycidol, or mixtures thereof.
  • EO oxyalkylated with PO
  • BO butylene oxide
  • cyclohexene oxide glycidol
  • glycerol is first oxyalkylated with PO and the resulting PAG is then oxyalkylated with EO.
  • glycerol is reacted with EO and the resulting PAG is reacted with PO and EO.
  • each of the above-mentioned polyhydric compounds can be reacted with mixtures of EO and PO or any two or more of any of the aforesaid 1 ,2-oxides, in the same manner.
  • Techniques for preparing suitable polyethers from mixed 1 ,2-oxides are shown in U.S. Pat. Nos. 2,674,619; 2,733,272; 2,831 ,034, 2,948,575; and 3,036,1 18.
  • the starting materials can be derived from naturally occurring materials, such as PO derived from monopropylene glycol (MPG) based on glycerin or EO derived from ethanol or tetrahydrofuran derived from hemicellulose.
  • MPG monopropylene glycol
  • polyglycolesters can be made from renewable esters, such as vegetable oils or oleic sunflower oils, canola oil, soy oil, their respective high oleic products, as well as castor oil, lesquerella oil, jathropa oil, and their derivatives.
  • renewable esters such as vegetable oils or oleic sunflower oils, canola oil, soy oil, their respective high oleic products, as well as castor oil, lesquerella oil, jathropa oil, and their derivatives.
  • Monohydric alcohols typically used as initiators include the lower acyclic alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, neopentanol, isobutanol, decanol, and the like, as well as higher acyclic alcohols derived from both natural and petrochemical sources with from 1 1 carbon atoms to 22 carbon atoms. As noted above, water can also be used as an initiator.
  • Preferred PAGs for use in this invention include PAGs produced by the polymerization of EO and PO onto an initiator.
  • the lubricant oil base stock may contain an amount, preferably a minor (less than 50 wt percent based upon total lubricant oil base stock weight) amount of other types of lubricating oils, such as vegetable oils, mineral oils, and synthetic lubricants such as polyesters, alkylaromatics, polyethers, hydrogenated or unhydrogenated poly-alpha-olefins and similar substances of lubricating viscosity.
  • lubricating oils such as vegetable oils, mineral oils, and synthetic lubricants such as polyesters, alkylaromatics, polyethers, hydrogenated or unhydrogenated poly-alpha-olefins and similar substances of lubricating viscosity.
  • one or more lubricant oil (preferably PAG) base stocks may be of formula:
  • R is H or an alkyl or an alkyl-phenyl group having from 1 carbon atom to 30 carbon atoms
  • X is O, S, or N
  • y is a single or combined integer from 3 to 30
  • Z is H or a hydrocarbyl or hydrocarboxyl group containing from 1 carbon atom to 30 carbon atoms
  • n+p is from 6 to 60 and the distribution of n and p can be random or in any specific sequence
  • m is 1 to 8
  • polyether molecular weight is from 350 Daltons to 3,500 Daltons.
  • PAGs used in compositions of this invention can include capped materials where existing OH functionality is converted to an ether group.
  • PAG products for engine and gear oil applications are currently available commercially, including but not limited to those products sold under the following brand names: PLURIOLTM A750E; PLURACOLTM WS55, WS100, WS170, B1 1/25, B1 1/50, B32/50; BREOXTM A299; BREOXTM 5OA; PPG-33- series; UCONTM 50-HB series; SYNALOXTM 50-xxB series; SYNALOXTM 100-xxB series; GLYGOYLETM HE460; D21/150; PLURONICTM 450PR, PLURONICTM 600PR; TERRALOXTM WA46, TERRALOXTM WA1 10; SYNALOXTM 40-D150; Polyglycol B01/20, B01/40, B01/50, B15, B35; UCON LB65, LB125, LB165, LB285, WI285, WI625; P41/200; PLURONICTM GENAPOL
  • the additive package and each of its components preferably meet EC/1999/45 bio-no-tox criteria and, more preferably, do not deteriorate performance lubricant oil base stocks below (that is, does not pass) the EC/1999/45 bio-no-tox criteria.
  • the additive package and each of its components more preferably are soluble in the lubricant oil base stock, either at room temperature (nominally 25 degrees centigrade ( 5 C) or at an elevated temperature.
  • Esters and amides, and Group V (of The Periodic Table of the Elements) salts, of aspartic acid are employed in the practice of this invention as a required lubricant composition component.
  • Compounds used to form the esters and amides may include from 1 carbon atom to 25 carbon atoms, more typically from 1 carbon atom to 6 carbon atoms.
  • the carboxylic acid groups can be converted to methyl or ethyl esters (or a mixture thereof).
  • One or both of the carboxylic acid groups of each aspartic acid functional group in the additive of this invention may be reacted to form such esters, amides, and Group V salts.
  • the carboxylic acid groups are reacted to form such esters, amides, and Group V salts for acid scavengers used in various aspects or embodiments of this invention.
  • the amount of such aspartic acid derivatives may vary. In general the amount is from 0.01 wt percent to 10 wt percent based on the total weight of the lubricant composition. More typically the amount is from 0.1 wt percent to 1 wt percent.
  • Materials used to react with aspartic acid to form aspartic acid derivatives include compounds such as ammonia and other Group V compounds including ammonium, phosphonium, arsonium, and antimonium based materials, amines such as C 1 -C 50 aliphatic amines such as methyl amine, ethyl amine, propyl amine, and butyl amine.
  • the Group V salts appear to be superior to Group 1 A cationic salts in terms of improved corrosion properties of the lubricant compositions.
  • the Group V salts have improved solubility, relative to Group 1 A salts, in PAG-based lubricant oil base stocks.
  • the aspartic acid additives used herein include mono-acids and poly-acids (for example, those containing two or more aspartic acid functional groups (“polyaspartic acids”)).
  • Aspartic acid and polyaspartic acid refer to compounds that contain one or more aspartic acid groups.
  • the additives used herein contain ⁇ two aspartic acid groups.
  • Aspartic acid esters, amides, and Group V salts include compositions based on the following formula.
  • carboxylic acid groups or moieties can be converted to any of esters, amides, and Group V salts.
  • Polyaspartic acid compounds can be based on any organic structure which includes multiple aspartic acid groups attached thereto such as compounds of the following formula:
  • A is aspartic acid ester, amide, or Group V salt
  • X is a divalent C 2 -C 25 hydrocarbon moiety.
  • X may include additional elements such as oxygen, nitrogen, and sulfur.
  • X can be a divalent alkane group, aliphatic group, or aromatic group, including alkane groups and aliphatic groups containing cyclic structures.
  • X can also be based on di-cyclohexyl methane.
  • a nitrogen atom of aspartic acid forms a bond with a divalent hydrocarbon moiety.
  • An exemplary polyaspartic acid compound has the following structure:
  • the extreme pressure and anti-wear additives can be any conventional material so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements.
  • Representative examples of extreme pressure and anti-wear additives include, but are not limited to, dialkyl-dithio-carbamates of metals and methylene, esters of polyaspartic acid, triphenyl-thio-phosphates, diaryldisulfides, dialkyldisulfides, alkylarylsulfides, dibenzyldisulphide, and combinations thereof.
  • preferred extreme pressure and anti- wear additives include, but are not limited to, dibenzyldisulfide (US FDA approved), 0,0,0- triphenylphosphorothioate, Zn-di-n-butyldithiocarbamate, Mo-dibutyldithiocarbamate, and Zn- methylene-bis-dialkyldithiocarbamate, with dibenzyldisulfide being especially preferred.
  • IRGALUBETM 63, 21 1 , 232, and 353 isopropylated triaryl phosphates
  • IRGALUBETM 21 1 and 232 nonylated triphenyl phosphorothionates
  • IRGALUBETM 349 amine phosphate
  • IRGALUBETM 353 dithiophosphate
  • IRGAFOSTM DDPP iso-decyl diphenyl phosphite
  • IRGAFOSTM OPH di- n-octyl-phosphite
  • the anti-corrosion additive (also known as a "metal deactivator”) may be any single compound or mixture of compounds that inhibits corrosion of metallic surfaces.
  • the corrosion inhibitor can be any conventional material so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements.
  • anti-corrosion additives include thiadiazoles and triazoles such as tolyltriazole; dimer and trimer acids such as those produced from tall oil fatty acids, oleic acid, and linoleic acid; alkenyl succinic acid and alkenyl succinic anhydride corrosion inhibitors such as tetrapropenylsuccinic acid, tetrapropenylsuccinic anhydride, dodecenylsuccinic acid, dodecenylsuccinic anhydride, hexadecenylsuccinic acid, and similar compounds; and half esters of C 8 -C 24 alkenyl succinic acids with alcohols such as diols and polyglycols.
  • thiadiazoles and triazoles such as tolyltriazole
  • dimer and trimer acids such as those produced from tall oil fatty acids, oleic acid, and linoleic acid
  • Preferred anti-corrosion additives include, but are not limited to, morpholine, N-methyl morpholine, N-ethyl morpholine, amino ethyl piperazine, monoethanol amine, 2 amino-2-methylpropanol (AMP), liquid tolutriazol derivatives such as 2,2'-methyl-1 H-benzotriazol-1 -yl-methyl-imino-bis and methyl-1 H- benzotriazol, isopropyl hydroxylamine, IRGAMETTM 30 (liquid tolutriazol derivative), IRGAMETTM 30 (liquid triazol derivative), IRGAMETTM SBT 75 (tetrahydrobenzotriazole), IRGAMETTM 42 (tolutirazole derivative), IRGAMETTM BTZ (benzotriazole), IRGAMETTM TTZ (tolutriazole), imidazoline and its derivatives, IRGACORTM DC1 1 (undecaned
  • the lubricant composition preferably contains from 0.005 wt percent to 0.5 wt percent, and more preferably from 0.01 wt percent to 0.2 wt percent, of anti-corrosion additive, each wt percent being based upon total lubricant composition weight.
  • the antioxidant(s) can be any conventional antioxidant so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements.
  • the antioxidant can vary widely, including compounds from classes such as amines and phenolics.
  • the antioxidant can include a sterically hindered phenolic antioxidant (for example, an ortho-alkylated phenolic compound such as 2,6-di-tert-butylphenol, 4-methyl-2,6-di-tert-butylphenol, 2,4,6-tri-tert- butylphenol, 2-tert-butylphenol, 2,6-di-isopropylphenol, 2-methyl-6-tert-butylphenol, 2,4- dimethyl-6-tert-butylphenol, 4-(N,N-dimethylaminomethyl)-2,6-di-tert-butylphenol, 4-ethyl-2,6-di- tert-butylphenol, 2-methyl-6-styrylphenol, 2,6-di
  • antioxidants include, but are not limited to, amine antioxidants such as N-phenyl-1 -naphthylamine N-phenylbenzenamine reaction products with 2,4,4-trimethylpentenes; phenothizines such as dibenzo-1 ,4,thiazine, 1 ,2-dihydroquinoline and poly(2,2,4-trimethyl-1 ,2-dihydroquinoline).
  • amine antioxidants such as N-phenyl-1 -naphthylamine N-phenylbenzenamine reaction products with 2,4,4-trimethylpentenes
  • phenothizines such as dibenzo-1 ,4,thiazine, 1 ,2-dihydroquinoline and poly(2,2,4-trimethyl-1 ,2-dihydroquinoline).
  • antioxidants include, but are not limited to, IRGANOXTM L01 , L06, L57, L93 (alkylated diphenyl amines and alkylated phenyl-naphtyl amines); IRGANOXTM L101 , L107, L109, L1 15, L1 18, L135 (hindered phenolic antioxidants); IRGANOXTM L64, L74, L94, L134, and L150 (antioxidant blends); IRGFOSTM 168 (di-tert-butyl phenyl phosphate); IRGANOXTM E201 (alpha-tocopherol), and IRGANOXTM L93 (sulfur-containing aromatic amine antioxidant).
  • IRGANOXTM L01 , L06, L57, L93 alkylated diphenyl amines and alkylated phenyl-naphtyl amines
  • the lubricant composition preferably contains from 0.01 wt percent to 1.0 wt percent, more preferably from 0.05 wt percent to 0.7 wt percent, of such antioxidant(s), each wt percent being based on total lubricant composition weight.
  • the additional acid scavenger is a single compound or a mixture of compounds that has an ability to scavenge acids.
  • the acid scavenger can be any conventional material so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements.
  • Representative acid scavengers include, but are not limited to, sterically hindered carbo- diimides, such as those disclosed in FR 2,792,326, incorporated herein by reference.
  • the friction (rheology) modifier can be any conventional material so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements.
  • a representative non-limiting example of such a material is a copolymer of diphenylmethane-diisocyanate hexamethylene diamine and sterarylamine (for example, LUVODURTM PVU-A).
  • the lubricating compositions preferably contain from 0.01 wt percent to 1.0 wt percent, more preferably from 0.05 wt percent to 0.7 wt percent, of such friction modifiers, each wt percent being based on total lubricant composition weight.
  • the lubricant compositions optionally contain small amounts of a demulsifier and/or an antifoam agent.
  • demulsifiers include organic sulphonates and oxyalkylated phenolic resins.
  • antifoam agents are well known in the art, such as stearylamine, silicones and organic polymers such as acrylate polymers. If present, such additives typically comprise, on an individual basis, no more than 1 wt percent based on total lubricant composition weight.
  • the lubricant compositions also optionally contain a thickening agent such as a polyethylene oxide, a polyacrylate, a styrene-acrylate latex, a styrene butadiene latex, and a polyurethane prepolymer.
  • a thickening agent such as a polyethylene oxide, a polyacrylate, a styrene-acrylate latex, a styrene butadiene latex, and a polyurethane prepolymer.
  • the thickening agent when present, is used in an amount sufficient to provide the lubricant composition with a desired thickness or viscosity.
  • lubricant compositions by simple addition of the components and mixing. This can occur at room temperature (nominally 25 5 C). Higher temperatures of up to, for example, 170 5 C, may be employed to effect solubilization of the additives into the lubricant oil (preferably PAG) base stock. One may effect mixing ultrasonically or by using a high speed dispergator.
  • the lubricant compositions have utility as lubricants for automobile engines.
  • Table 1 provides compositions prepared according to this invention. These lubricant compositions display excellent lubricity, are solutions (all material is solubilized), and meet or exceed EC/1999/45 bio-no-tox criteria. SYNALOXTM 100-30B and SYNALOXTM 100-20B are commercially available PAGs for the engine lubricant market.
  • compositions when tested for their lubricant properties, possess excellent lubricity.
  • the additive packages are soluble in the PAGs, meet EC/1999/45 bio-no-tox criteria and do not deteriorate the bio-no-tox properties of the lubricant oil base stock (PAG) below the EC/1999/45 bio-no-tox criteria.
  • PAG lubricant oil base stock
  • Example 2 when subjected to EC/1999/45 bio-no-tox testing, has a Daphnia (EL 50 ) rating of 138 milligrams per liter (mg/L), an Alga (EL 50 ) rating of greater than 100 mg/L and a biodegradability (per Organization for Economic Co-operation and Development (OECD 301 F)) of more than 60 percent.
  • EL 50 Daphnia
  • EL 50 Alga
  • biodegradability per Organization for Economic Co-operation and Development
  • Table 2 shows viscosity information and Schwingungs-Reibverschlei ⁇ -Prafgerat (SRV) tribology data using an Optimal Instruments device and amplitude of oscillation (x) of 1 millimeter (mm) and 2 mm in terms of Newtons (N) and megapascals (MPs) for Examples 2 and 3 as well as for a commercial (Castrol) 5W-30 motor oil prior to any engine testing.
  • x millimeter
  • N Newtons
  • MPs megapascals
  • the lubricant compositions of Examples 2 and 3 are expected to perform at least as well as the commercial 5W-30 motor oil in extended engine testing
  • Table 3 shows additional PAG compositions (Examples 4-12, Example 5 being a comparative example (CEx)) containing an additive package as described above. Table 3 also shows the results of a polyglycol ICOT test (in hours) for each of Examples (Ex) 4-12.
  • WA D46-4 is a PAG made available by The Dow Chemical Company under the Tradename TERRALOXTM WA-46 (1 ,4-butanediol initiated (18 wt percent) extended with 64 wt percent ethylene oxide (EO) and 18 wt percent propylene oxide (PO) in mixed feed) to a number average molecular weight (Mn) of 664 Daltons
  • PPG 32-2 is a PAG made available by Clariant under the Tradename B01/20 (Butanol initiated and extended with PO to Mn of 900 Daltons).
  • CEx 5 a comparative example, uses no polyaspartic acid salt and shows the least stabilization from among the additives used in Table 3.
  • Ex 10 surprisingly provides stabilization of the lubricant composition sufficient to enable approximately a 40,000 kilometer driving cycle before an oil change would be needed.
  • the polyaspartic acid derivatives appear to serve as acid scavengers, but do not appear to alter extreme pressure/anti-wear properties of the PAGs.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

A lubricant composition useful for automotive engines, comprising: (A) at least one polyalkylene glycol suitable for use as a lubricant in an automotive engine, (B) an additive package which comprises an acid scavenger, wherein the acid scavenger is an aspartic acid ester, aspartic acid amide, a Group V aspartic acid salt, or a combination thereof.

Description

POLYALKYLENE GLYCOL LUBRICANT COMPOSITION
By: Johan A. Thoen, Mathias Woydt, Daniel F. Zweifel
This application is a non-provisional application claiming priority from the U.S. Provisional Patent Application No. 61/125,701 , filed on April 28, 2008, entitled "POLYALKYLENE GLYCOL LUBRICANT COMPOSITION," the teachings of which are incorporated by reference herein, as if reproduced in full hereinbelow.
This invention pertains to a polyalkylene glycol (PAG) lubricant composition containing an amide or ester derivative of aspartic acid, or a Group V salt of an aspartic acid.
Engine lubricant oils are composed of base oils and additives. Certain synthetic oils, such as PAGs, are characterized by inherent low friction properties and good low and high temperature viscosity properties which promote excellent hydrodynamic film formation between moving parts.
PAG-based engine lubricant oils find an increasing original equipment manufacturer (OEM) interest due to their intrinsic properties in relation to an increasing number of new performance criteria requested by automotive engine design departments.
A need exists for additive packages which are soluble in PAGs, preferably where the package itself meets certain bio-no-tox criteria or will not deteriorate biological and toxicological ("bio-no- tox") properties of a base oil below criteria set forth in, for example, European Community directive EC/1999/45, and which are adapted to the specific chemistry and oxidation kinetics of PAGs in order to meet critical application performance requirements for use in internal combustion engine oils and exceed those known from hydrocarbons. The criteria in directive EC/1999/45 are incorporated herein by reference as the criteria for determining whether an additive package is in accordance with this invention.
In one aspect or embodiment, this invention is a lubricant composition useful for automotive engines, comprising: (A) at least one PAG suitable for use as a lubricant in an automotive engine, and (B) an additive package which comprises an acid scavenger, wherein the acid scavenger is an aspartic acid ester, an aspartic acid amide, a Group V salt of aspartic acid, or a combination thereof.
The lubricant composition may contain additional components and have certain properties including but not limited to compositions wherein: the additive package further comprises (i) at least (≥) one extreme pressure anti-wear additive, (ii) ≥ one anti-corrosion additive, (iii) ≥ one antioxidant, (iv) ≥ one friction modifier, (v) ≥ one additional acid scavenger, or any combination of (i)-(v); the additive package is soluble at 25 degrees Centigrade (5C) in the PAG; the additive package meets bio-no-tox criteria of EC/1999/45 and preferably does not deteriorate the bio-no- tox properties of the PAG (also known as "lubricant oil base stock) below (does not pass) the EC/1999/45 criteria; the composition excludes additives that do not meet the EC/1999/45 bio- no-tox criteria or will deteriorate the bio-no-tox properties of the lubricant oil base stock; the additive package includes ≥ one thickening agent; the additive package includes ≥ one detergent is included; and combinations thereof.
In another aspect, this invention is a method of lubricating an automobile engine, comprising: employing the above lubricant composition as a lubricant oil.
Lubricating oil base stocks used in formulating lubricant compositions of this invention are composed primarily or exclusively of PAGs of lubricating viscosity. A wide variety of such oleaginous liquids are available as articles of commerce. Normally the PAG has a viscosity at 40 5C within a range of from 20 centistokes (cSt) (20 square millimeters per second (mm2/s)) to 10,000 cSt (10,000 mm2/s) and a viscosity within a range of from 3 cSt (3 mm2/s) to 2,000 cSt (2,000 mm2/s) at 100 5C. The base stocks preferably meet EC/1999/45 bio-no-tox criteria.
Suitable PAGs include, but are not limited to, a reaction product of a 1 ,2-oxide (vicinal epoxide) with water, or an alcohol, or an aliphatic polyhydric alcohol containing from 2 hydroxyl groups to 6 hydroxyl groups and between 2 carbon atoms (C2) and 8 carbon atoms (C8) per molecule. Suitable compounds useful in preparing these PAGs include lower (C2 to C8) alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide, cyclohexene oxide, and glycidol. Mixtures of these 1 ,2-oxides are also useful in preparing PAGs. A PAG may be formed by known techniques in which an aliphatic polyhydric alcohol or water or monohydric alcohol (often called an "initiator") is reacted with a single 1 ,2-oxide or a mixture of two or more of the 1 ,2- oxides. If desired, the initiator may be first oxyalkylated with one 1 ,2-oxide, followed by oxyalkylation with a different 1 ,2-oxide or a mixture of 1 ,2-oxides. The oxyalkylated initiator can be further oxyalkylated with a still different 1 ,2-oxide.
For convenience, "mixture," when applied to a PAG containing a mixture of 1 ,2-oxides, includes both random and/or block polyethers such as those prepared by: (1 ) random addition obtained by simultaneously reacting two or more 1 ,2-oxides with the initiator; (2) block addition in which the initiator reacts first with one 1 ,2-oxide and then with a second 1 ,2-oxide, and (3) block addition in which the initiator first reacts with a first 1 ,2-oxide followed by random addition wherein the initiator reacts with a combination of the first 1 ,2-oxide and a second 1 ,2-oxide.
Any suitable ratio of different 1 ,2-oxides may be employed. When a mixture of ethylene oxide (EO) and propylene oxide (PO) is utilized to form polyethers by random and/or block addition, the proportion of EO is generally between 3 weight percent (wt percent) and 60 wt percent, and preferably between 5 wt percent and 50 wt percent, based on total mixture weight.
Aliphatic polyhydric alcohol reactants used in making the PAG include those containing between from two hydroxyl (OH) groups to six OH groups and from two carbon atoms (C2) to eight carbon atoms (C8) per molecule, as illustrated by compounds such as: ethylene glycol, propylene glycol, 2,3-butylene glycol, 1 ,3-butylene glycol, 1 ,4-butanediol, 1 ,3-propanediol, 1 ,5- pentane diol, 1 ,6-hexene diol, glycerol, trimethylolpropane, sorbitol, pentaerythritol, mixtures thereof and the like. Cyclic aliphatic polyhydric compounds such as starch, glucose, sucrose, and methyl glucoside may also be employed in PAG preparation. Each of the aforesaid polyhydric compounds and alcohols can be oxyalkylated with EO, PO, butylene oxide (BO), cyclohexene oxide, glycidol, or mixtures thereof. For example, glycerol is first oxyalkylated with PO and the resulting PAG is then oxyalkylated with EO. Alternatively, glycerol is reacted with EO and the resulting PAG is reacted with PO and EO. Each of the above-mentioned polyhydric compounds can be reacted with mixtures of EO and PO or any two or more of any of the aforesaid 1 ,2-oxides, in the same manner. Techniques for preparing suitable polyethers from mixed 1 ,2-oxides are shown in U.S. Pat. Nos. 2,674,619; 2,733,272; 2,831 ,034, 2,948,575; and 3,036,1 18. The starting materials can be derived from naturally occurring materials, such as PO derived from monopropylene glycol (MPG) based on glycerin or EO derived from ethanol or tetrahydrofuran derived from hemicellulose. Likewise, polyglycolesters can be made from renewable esters, such as vegetable oils or oleic sunflower oils, canola oil, soy oil, their respective high oleic products, as well as castor oil, lesquerella oil, jathropa oil, and their derivatives.
Monohydric alcohols typically used as initiators include the lower acyclic alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, neopentanol, isobutanol, decanol, and the like, as well as higher acyclic alcohols derived from both natural and petrochemical sources with from 1 1 carbon atoms to 22 carbon atoms. As noted above, water can also be used as an initiator.
Preferred PAGs for use in this invention include PAGs produced by the polymerization of EO and PO onto an initiator.
The lubricant oil base stock may contain an amount, preferably a minor (less than 50 wt percent based upon total lubricant oil base stock weight) amount of other types of lubricating oils, such as vegetable oils, mineral oils, and synthetic lubricants such as polyesters, alkylaromatics, polyethers, hydrogenated or unhydrogenated poly-alpha-olefins and similar substances of lubricating viscosity.
In an embodiment, one or more lubricant oil (preferably PAG) base stocks may be of formula:
R-[X-(CH2CH2O)n(CyH2yO)p-Z]m
where R is H or an alkyl or an alkyl-phenyl group having from 1 carbon atom to 30 carbon atoms; X is O, S, or N; y is a single or combined integer from 3 to 30; Z is H or a hydrocarbyl or hydrocarboxyl group containing from 1 carbon atom to 30 carbon atoms; n+p is from 6 to 60 and the distribution of n and p can be random or in any specific sequence; m is 1 to 8; and polyether molecular weight is from 350 Daltons to 3,500 Daltons. PAGs used in compositions of this invention can include capped materials where existing OH functionality is converted to an ether group.
A variety of PAG products for engine and gear oil applications are currently available commercially, including but not limited to those products sold under the following brand names: PLURIOL™ A750E; PLURACOL™ WS55, WS100, WS170, B1 1/25, B1 1/50, B32/50; BREOX™ A299; BREOX™ 5OA; PPG-33- series; UCON™ 50-HB series; SYNALOX™ 50-xxB series; SYNALOX™ 100-xxB series; GLYGOYLE™ HE460; D21/150; PLURONIC™ 450PR, PLURONIC™ 600PR; TERRALOX™ WA46, TERRALOX™ WA1 10; SYNALOX™ 40-D150; Polyglycol B01/20, B01/40, B01/50, B15, B35; UCON LB65, LB125, LB165, LB285, WI285, WI625; P41/200; PLURONIC™ GENAPOL™; WAKO T01/15, T01/35, T01/60; LUPRANOL™ 9209 and 3300; and SELEXOL™. The additive package and each of its components preferably meet EC/1999/45 bio-no-tox criteria and, more preferably, do not deteriorate performance lubricant oil base stocks below (that is, does not pass) the EC/1999/45 bio-no-tox criteria. The additive package and each of its components more preferably are soluble in the lubricant oil base stock, either at room temperature (nominally 25 degrees centigrade (5C) or at an elevated temperature.
Esters and amides, and Group V (of The Periodic Table of the Elements) salts, of aspartic acid (collectively "aspartic acid derivatives") are employed in the practice of this invention as a required lubricant composition component. Compounds used to form the esters and amides may include from 1 carbon atom to 25 carbon atoms, more typically from 1 carbon atom to 6 carbon atoms. For example, the carboxylic acid groups can be converted to methyl or ethyl esters (or a mixture thereof). One or both of the carboxylic acid groups of each aspartic acid functional group in the additive of this invention may be reacted to form such esters, amides, and Group V salts. Typically all the carboxylic acid groups are reacted to form such esters, amides, and Group V salts for acid scavengers used in various aspects or embodiments of this invention. The amount of such aspartic acid derivatives may vary. In general the amount is from 0.01 wt percent to 10 wt percent based on the total weight of the lubricant composition. More typically the amount is from 0.1 wt percent to 1 wt percent. Materials used to react with aspartic acid to form aspartic acid derivatives include compounds such as ammonia and other Group V compounds including ammonium, phosphonium, arsonium, and antimonium based materials, amines such as C1-C50 aliphatic amines such as methyl amine, ethyl amine, propyl amine, and butyl amine. The Group V salts appear to be superior to Group 1 A cationic salts in terms of improved corrosion properties of the lubricant compositions. In addition, the Group V salts have improved solubility, relative to Group 1 A salts, in PAG-based lubricant oil base stocks. The aspartic acid additives used herein include mono-acids and poly-acids (for example, those containing two or more aspartic acid functional groups ("polyaspartic acids")). Aspartic acid and polyaspartic acid refer to compounds that contain one or more aspartic acid groups. Typically the additives used herein contain ≥ two aspartic acid groups. Aspartic acid esters, amides, and Group V salts include compositions based on the following formula.
Figure imgf000007_0001
In the formula above, which describes a homo-polymer of aspartic acid, carboxylic acid groups or moieties can be converted to any of esters, amides, and Group V salts.
Polyaspartic acid compounds can be based on any organic structure which includes multiple aspartic acid groups attached thereto such as compounds of the following formula:
A-X-A
wherein A is aspartic acid ester, amide, or Group V salt, and X is a divalent C2-C25 hydrocarbon moiety. X may include additional elements such as oxygen, nitrogen, and sulfur. X can be a divalent alkane group, aliphatic group, or aromatic group, including alkane groups and aliphatic groups containing cyclic structures. X can also be based on di-cyclohexyl methane. Typically a nitrogen atom of aspartic acid forms a bond with a divalent hydrocarbon moiety. An exemplary polyaspartic acid compound has the following structure:
Figure imgf000008_0001
which is aspartic acid N,N'-(methylene-d-4,1 ,-cyclohexanediyl)bis-tetraethyl ester. This polyaspartic acid ester appears to correspond to DESMOPHEN™ NH1420 polyaspartic polyamino co-reactant (Bayer MaterialScience) and K-CORR™ 100 (King Industries).
The extreme pressure and anti-wear additives can be any conventional material so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements. Representative examples of extreme pressure and anti-wear additives include, but are not limited to, dialkyl-dithio-carbamates of metals and methylene, esters of polyaspartic acid, triphenyl-thio-phosphates, diaryldisulfides, dialkyldisulfides, alkylarylsulfides, dibenzyldisulphide, and combinations thereof. Representative examples of preferred extreme pressure and anti- wear additives include, but are not limited to, dibenzyldisulfide (US FDA approved), 0,0,0- triphenylphosphorothioate, Zn-di-n-butyldithiocarbamate, Mo-dibutyldithiocarbamate, and Zn- methylene-bis-dialkyldithiocarbamate, with dibenzyldisulfide being especially preferred. Representative examples of commercially available anti-wear additives that can be employed in the practice of this invention include but are not limited to IRGALUBE™ 63, 21 1 , 232, and 353 (isopropylated triaryl phosphates); IRGALUBE™ 21 1 and 232 (nonylated triphenyl phosphorothionates); IRGALUBE™ 349 (amine phosphate); IRGALUBE™ 353 (dithiophosphate); IRGAFOS™ DDPP (iso-decyl diphenyl phosphite); and IRGAFOS™ OPH (di- n-octyl-phosphite).
The anti-corrosion additive (also known as a "metal deactivator") may be any single compound or mixture of compounds that inhibits corrosion of metallic surfaces. The corrosion inhibitor can be any conventional material so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements. Representative anti-corrosion additives include thiadiazoles and triazoles such as tolyltriazole; dimer and trimer acids such as those produced from tall oil fatty acids, oleic acid, and linoleic acid; alkenyl succinic acid and alkenyl succinic anhydride corrosion inhibitors such as tetrapropenylsuccinic acid, tetrapropenylsuccinic anhydride, dodecenylsuccinic acid, dodecenylsuccinic anhydride, hexadecenylsuccinic acid, and similar compounds; and half esters of C8-C24 alkenyl succinic acids with alcohols such as diols and polyglycols. Also useful are aminosuccinic acids or derivatives thereof. Preferred anti-corrosion additives include, but are not limited to, morpholine, N-methyl morpholine, N-ethyl morpholine, amino ethyl piperazine, monoethanol amine, 2 amino-2-methylpropanol (AMP), liquid tolutriazol derivatives such as 2,2'-methyl-1 H-benzotriazol-1 -yl-methyl-imino-bis and methyl-1 H- benzotriazol, isopropyl hydroxylamine, IRGAMET™ 30 (liquid tolutriazol derivative), IRGAMET™ 30 (liquid triazol derivative), IRGAMET™ SBT 75 (tetrahydrobenzotriazole), IRGAMET™ 42 (tolutirazole derivative), IRGAMET™ BTZ (benzotriazole), IRGAMET™ TTZ (tolutriazole), imidazoline and its derivatives, IRGACOR™ DC1 1 (undecanedioic acid), IRGACOR™ DC 12 (dodecanedioic acid), IRGACOR™ L 184 (TEA neutralized polycarboxylic acid), IRGACOR™ L 190 (polycarboxylic acid), IRGACOR™ L12 (succinic acid ester), IRGACOR™ DSS G (n-oleyl sarcosine), and IRGACOR™ NPA (iso-nonyl phenoxy acetic acid). The lubricant composition preferably contains from 0.005 wt percent to 0.5 wt percent, and more preferably from 0.01 wt percent to 0.2 wt percent, of anti-corrosion additive, each wt percent being based upon total lubricant composition weight.
The antioxidant(s) can be any conventional antioxidant so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements. The antioxidant can vary widely, including compounds from classes such as amines and phenolics. The antioxidant can include a sterically hindered phenolic antioxidant (for example, an ortho-alkylated phenolic compound such as 2,6-di-tert-butylphenol, 4-methyl-2,6-di-tert-butylphenol, 2,4,6-tri-tert- butylphenol, 2-tert-butylphenol, 2,6-di-isopropylphenol, 2-methyl-6-tert-butylphenol, 2,4- dimethyl-6-tert-butylphenol, 4-(N,N-dimethylaminomethyl)-2,6-di-tert-butylphenol, 4-ethyl-2,6-di- tert-butylphenol, 2-methyl-6-styrylphenol, 2,6-di-styryl-4-nonylphenol, and their analogs and homologs). Representative examples of preferred antioxidants include, but are not limited to, amine antioxidants such as N-phenyl-1 -naphthylamine N-phenylbenzenamine reaction products with 2,4,4-trimethylpentenes; phenothizines such as dibenzo-1 ,4,thiazine, 1 ,2-dihydroquinoline and poly(2,2,4-trimethyl-1 ,2-dihydroquinoline). Representative examples of commercially available and suitable antioxidants include, but are not limited to, IRGANOX™ L01 , L06, L57, L93 (alkylated diphenyl amines and alkylated phenyl-naphtyl amines); IRGANOX™ L101 , L107, L109, L1 15, L1 18, L135 (hindered phenolic antioxidants); IRGANOX™ L64, L74, L94, L134, and L150 (antioxidant blends); IRGFOS™ 168 (di-tert-butyl phenyl phosphate); IRGANOX™ E201 (alpha-tocopherol), and IRGANOX™ L93 (sulfur-containing aromatic amine antioxidant). The lubricant composition preferably contains from 0.01 wt percent to 1.0 wt percent, more preferably from 0.05 wt percent to 0.7 wt percent, of such antioxidant(s), each wt percent being based on total lubricant composition weight.
The additional acid scavenger is a single compound or a mixture of compounds that has an ability to scavenge acids. The acid scavenger can be any conventional material so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements. Representative acid scavengers include, but are not limited to, sterically hindered carbo- diimides, such as those disclosed in FR 2,792,326, incorporated herein by reference.
The friction (rheology) modifier can be any conventional material so long as it meets the above EC/1999/45 bio-no-tox and solubility performance requirements. A representative non-limiting example of such a material is a copolymer of diphenylmethane-diisocyanate hexamethylene diamine and sterarylamine (for example, LUVODUR™ PVU-A). The lubricating compositions preferably contain from 0.01 wt percent to 1.0 wt percent, more preferably from 0.05 wt percent to 0.7 wt percent, of such friction modifiers, each wt percent being based on total lubricant composition weight.
The lubricant compositions optionally contain small amounts of a demulsifier and/or an antifoam agent. Such demulsifiers include organic sulphonates and oxyalkylated phenolic resins. Various antifoam agents are well known in the art, such as stearylamine, silicones and organic polymers such as acrylate polymers. If present, such additives typically comprise, on an individual basis, no more than 1 wt percent based on total lubricant composition weight. The lubricant compositions also optionally contain a thickening agent such as a polyethylene oxide, a polyacrylate, a styrene-acrylate latex, a styrene butadiene latex, and a polyurethane prepolymer. The thickening agent when present, is used in an amount sufficient to provide the lubricant composition with a desired thickness or viscosity.
Prepare the lubricant compositions by simple addition of the components and mixing. This can occur at room temperature (nominally 25 5C). Higher temperatures of up to, for example, 170 5C, may be employed to effect solubilization of the additives into the lubricant oil (preferably PAG) base stock. One may effect mixing ultrasonically or by using a high speed dispergator. The lubricant compositions have utility as lubricants for automobile engines.
Examples that follow illustrate the invention, but do not limit its scope or that of any claims appended hereto. Unless otherwise noted, all percentages are by weight.
Table 1 provides compositions prepared according to this invention. These lubricant compositions display excellent lubricity, are solutions (all material is solubilized), and meet or exceed EC/1999/45 bio-no-tox criteria. SYNALOX™ 100-30B and SYNALOX™ 100-20B are commercially available PAGs for the engine lubricant market.
Table 1
Figure imgf000012_0001
These compositions, when tested for their lubricant properties, possess excellent lubricity. The additive packages are soluble in the PAGs, meet EC/1999/45 bio-no-tox criteria and do not deteriorate the bio-no-tox properties of the lubricant oil base stock (PAG) below the EC/1999/45 bio-no-tox criteria. Example 2, when subjected to EC/1999/45 bio-no-tox testing, has a Daphnia (EL50) rating of 138 milligrams per liter (mg/L), an Alga (EL50) rating of greater than 100 mg/L and a biodegradability (per Organization for Economic Co-operation and Development (OECD 301 F)) of more than 60 percent. Per EC/1999/45 EL50 ratings in excess of 100 mg/L are rated as "low toxicity" and > 60 percent biodegradability equates to "readily biodegradable".
Table 2 below shows viscosity information and Schwingungs-Reibverschleiβ-Prafgerat (SRV) tribology data using an Optimal Instruments device and amplitude of oscillation (x) of 1 millimeter (mm) and 2 mm in terms of Newtons (N) and megapascals (MPs) for Examples 2 and 3 as well as for a commercial (Castrol) 5W-30 motor oil prior to any engine testing.
Figure imgf000013_0001
The lubricant compositions of Examples 2 and 3 are expected to perform at least as well as the commercial 5W-30 motor oil in extended engine testing
Table 3 below shows additional PAG compositions (Examples 4-12, Example 5 being a comparative example (CEx)) containing an additive package as described above. Table 3 also shows the results of a polyglycol ICOT test (in hours) for each of Examples (Ex) 4-12. In Table 3, WA D46-4 is a PAG made available by The Dow Chemical Company under the Tradename TERRALOX™ WA-46 (1 ,4-butanediol initiated (18 wt percent) extended with 64 wt percent ethylene oxide (EO) and 18 wt percent propylene oxide (PO) in mixed feed) to a number average molecular weight (Mn) of 664 Daltons, and PPG 32-2 is a PAG made available by Clariant under the Tradename B01/20 (Butanol initiated and extended with PO to Mn of 900 Daltons). The ICOT test is described in "Test d'oxydation catalyse par I'acetyle acetonate de fer (ICOT), Groupe Frangais de Coordination (GFC), Le Consulat, 147, av. Paul Doumer, F- 92852 Rueil-Malmaison, gfc@gfc-tests.org; see also IP48/97 (2004), Determination of oxidation characteristics of lubricating oil." Table 3
Figure imgf000014_0001
CEx 5, a comparative example, uses no polyaspartic acid salt and shows the least stabilization from among the additives used in Table 3. Ex 10 surprisingly provides stabilization of the lubricant composition sufficient to enable approximately a 40,000 kilometer driving cycle before an oil change would be needed. The polyaspartic acid derivatives appear to serve as acid scavengers, but do not appear to alter extreme pressure/anti-wear properties of the PAGs.
Further modifications and alternative embodiments of this invention will be apparent to those skilled in the art in view of this description. Equivalent elements or materials may be substituted for those illustrated and described herein

Claims

What is claimed is:
1 . A lubricant composition useful for automotive engines, comprising: (A) at least one polyalkylene glycol suitable for use as a lubricant in an automotive engine, and (B) an additive package which comprises an acid scavenger, wherein the acid scavenger is an aspartic acid ester, aspartic acid amide, a Group V aspartic acid salt, their derivatives, or a combination thereof.
2. The lubricant composition of claim 1 , wherein the additive package further comprises (i) at least one extreme pressure anti-wear additive, or (ii) at least one anti-corrosion additive, or (iii) at least one antioxidant, or (iv) at least one friction modifier, or (v) at least one additional acid scavenger, or (vi) any combination of (i)-(v).
3. The lubricant composition of claim 1 , wherein the wherein the additive package is soluble at 25 degrees Centigrade in the polyalkylene glycol.
4. The lubricant composition of claim 1 , wherein the additive package meets bio-no-tox criteria of European Community directive EC/1999/45 and does not deteriorate the bio-no-tox properties of the polyalkylene glycol to a point where the composition does not meet such criteria.
5. The lubricant composition of Claim 1 , wherein the Group V aspartic acid salt is an amine salt.
6. A process for manufacturing the lubricant composition of any of Claims 1 through 5, which method comprises admixing the at least one polyalkylene glycol and the additive package.
7. A method of lubricating an automobile engine, which method comprises using the lubricant composition of any of Claims 1 through 5 to lubricate the engine.
PCT/US2009/041800 2008-04-28 2009-04-27 Polyalkylene glycol lubricant composition WO2009134716A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP09739518.0A EP2271732B1 (en) 2008-04-28 2009-04-27 Polyalkylene glycol lubricant composition
MX2010011869A MX324478B (en) 2008-04-28 2009-04-27 Polyalkylene glycol lubricant composition.
CA2722431A CA2722431C (en) 2008-04-28 2009-04-27 Polyalkylene glycol lubricant composition
US12/988,871 US8357644B2 (en) 2008-04-28 2009-04-27 Polyalkylene glycol lubricant composition
US13/715,078 US8592357B2 (en) 2008-04-28 2012-12-14 Polyalkylene glycol lubricant composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12570108P 2008-04-28 2008-04-28
US61/125,701 2008-04-28

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/988,871 A-371-Of-International US8357644B2 (en) 2008-04-28 2009-04-27 Polyalkylene glycol lubricant composition
US13/715,078 Continuation US8592357B2 (en) 2008-04-28 2012-12-14 Polyalkylene glycol lubricant composition

Publications (1)

Publication Number Publication Date
WO2009134716A1 true WO2009134716A1 (en) 2009-11-05

Family

ID=40863749

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/041800 WO2009134716A1 (en) 2008-04-28 2009-04-27 Polyalkylene glycol lubricant composition

Country Status (7)

Country Link
US (2) US8357644B2 (en)
EP (1) EP2271732B1 (en)
KR (1) KR101628406B1 (en)
CA (1) CA2722431C (en)
MX (1) MX324478B (en)
TW (1) TWI493027B (en)
WO (1) WO2009134716A1 (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012033668A1 (en) * 2010-09-07 2012-03-15 The Lubrizol Corporation Hydroxychroman derivatives as engine oil antioxidants
WO2012070007A1 (en) 2010-11-26 2012-05-31 Total Raffinage Marketing Engine lubricant composition
US8236204B1 (en) 2011-03-11 2012-08-07 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
US8236205B1 (en) 2011-03-11 2012-08-07 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles and methods for using same
WO2012129056A1 (en) 2011-03-23 2012-09-27 Dow Global Technologies Llc Polyalkylene glycol based heat transfer fluids and monofluid engine oils
CN103087811A (en) * 2011-11-07 2013-05-08 3M创新有限公司 Rustproof lubricating agent
WO2013164459A1 (en) 2012-05-04 2013-11-07 Total Marketing Services Engine lubricant for vehicles having a hybrid or micro-hybrid engine
WO2013164449A1 (en) 2012-05-04 2013-11-07 Total Marketing Services Engine lubricant composition
WO2013164457A1 (en) 2012-05-04 2013-11-07 Total Marketing Services Lubricant composition for an engine
WO2013066702A3 (en) * 2011-11-01 2013-11-07 Dow Global Technologies Llc Oil soluble polyalkylene glycol lubricant compositions
US9309205B2 (en) 2013-10-28 2016-04-12 Wincom, Inc. Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures
WO2018078290A1 (en) 2016-10-27 2018-05-03 Total Marketing Services Composition for an electric vehicle
US20180245017A1 (en) * 2015-02-26 2018-08-30 Dow Global Technologies Llc Lubricant formulations with enhanced anti-wear and extreme pressure performance
US10752858B2 (en) 2012-11-16 2020-08-25 Total Marketing Services Lubricant composition

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009134716A1 (en) * 2008-04-28 2009-11-05 Dow Global Technologies Inc. Polyalkylene glycol lubricant composition
US9057038B2 (en) * 2010-08-31 2015-06-16 Dow Global Technologies Llc Corrosion inhibiting polyalkylene glycol-based lubricant compositions
US20140018273A1 (en) * 2011-03-29 2014-01-16 Dow Global Technologies Llc Lubricant compositions
FR2977895B1 (en) 2011-07-12 2015-04-10 Total Raffinage Marketing ADDITIVE COMPOSITIONS ENHANCING STABILITY AND MOTOR PERFORMANCE OF NON-ROAD GASES
WO2014066076A1 (en) * 2012-10-25 2014-05-01 Dow Global Technologies Llc Lubricant composition
WO2014150663A1 (en) 2013-03-15 2014-09-25 Cytec Industries Inc. Corrosion inhibitors and methods of using same
US8822392B1 (en) * 2013-07-18 2014-09-02 Afton Chemical Corporation Friction modifiers for lubricating oils
US9296971B2 (en) * 2013-07-18 2016-03-29 Afton Chemical Corporation Friction modifiers for lubricating oils
JP6422565B2 (en) * 2014-07-31 2018-11-14 ダウ グローバル テクノロジーズ エルエルシー Capped oil-soluble polyalkylene glycol with low viscosity and high viscosity index
CN107001969B (en) 2014-09-19 2019-11-05 范德比尔特化学品有限责任公司 Industrial lubricants composition based on polyalkylene glycol
EP3262145B1 (en) 2015-02-26 2018-12-26 Dow Global Technologies LLC Enhanced extreme pressure lubricant formulations
EP3337884B1 (en) * 2015-08-20 2019-09-25 Dow Global Technologies LLC Fluid with polyalkylene glycol and unsaturated ester
JP6882343B2 (en) * 2016-06-02 2021-06-02 ビーエイエスエフ・ソシエタス・エウロパエアBasf Se Lubricant composition
CA3037868A1 (en) * 2016-09-23 2018-03-29 Basf Se Lubricant composition
JP2022513654A (en) * 2018-11-28 2022-02-09 ビーエーエスエフ ソシエタス・ヨーロピア Antioxidant Mixture for Low Viscosity Polyalkylene Glycol Base Stock

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0578449A1 (en) 1992-07-10 1994-01-12 Rohm And Haas Company Process for preparing polysuccinimides from aspartic acid
WO1996003644A1 (en) 1994-07-27 1996-02-08 The Dow Chemical Company Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereof
FR2792326A1 (en) 1999-04-19 2000-10-20 Renault NON-TOXIC AND BIODEGRADABLE FUNCTIONAL FLUIDS BASED ON COPOLYMERS OF ETHYLENE OXIDE AND PROPYLENE OXIDE FOR MOTOR VEHICLES
US20040094743A1 (en) 2000-09-22 2004-05-20 Mathias Woydt Biodegradable functional fluid for mechanic drives
DE102005041909A1 (en) 2005-09-03 2007-03-08 Tea Gmbh Technologiezentrum Emissionsfreie Antriebe Use of a glycol based lubricant for steam power machines, motors operated with hydrogen and water impact machine

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2733272A (en) 1950-10-27 1956-01-31 Trihydroxy polyoxyalkylene ethers
US2674619A (en) 1953-10-19 1954-04-06 Wyandotte Chemicals Corp Polyoxyalkylene compounds
US2831034A (en) 1953-12-07 1958-04-15 Dow Chemical Co Polyoxyalkylene glycol ethers of glycerine
US2948575A (en) 1956-04-19 1960-08-09 Dow Chemical Co Dispensing container for sheet wrapping material
US3036118A (en) 1957-09-11 1962-05-22 Wyandotte Chemicals Corp Mixtures of novel conjugated polyoxyethylene-polyoxypropylene compounds
US4218328A (en) * 1978-12-28 1980-08-19 Chevron Research Company Lubricating oil additive
US4855070A (en) 1986-12-30 1989-08-08 Union Carbide Corporation Energy transmitting fluid
EP0355977B1 (en) 1988-07-21 1994-01-19 BP Chemicals Limited Polyether lubricants
EP0460317B1 (en) 1990-06-08 1993-10-20 Ethyl Petroleum Additives Limited Polyalkylene glycol lubricant compositions
US5219892A (en) 1992-06-16 1993-06-15 R. T. Vanderbilt Company, Inc. Liquid stabilizer compositions for polyols and polyurethane foam
US5275749A (en) * 1992-11-06 1994-01-04 King Industries, Inc. N-acyl-N-hydrocarbonoxyalkyl aspartic acid esters as corrosion inhibitors
DE69508185T2 (en) 1994-11-08 1999-07-08 Betzdearborn Europe, Inc., Trevose, Pa. Process using a water-soluble corrosion inhibitor based on salt from dicarboxylic acids, cyclic amines and alkanolamines.
DE19605162C1 (en) 1996-02-13 1997-09-18 Elf Oil Deutschland Gmbh Synthetic lubricating oil and its use
DE19647554A1 (en) 1996-11-16 1998-05-28 Daimler Benz Ag Functional fluid for lifetime lubricated internal combustion engines
ES2199558T3 (en) * 1998-02-27 2004-02-16 Shell Internationale Research Maatschappij B.V. LUBRICATING COMPOSITION.
DE19820883A1 (en) 1998-05-09 1999-11-18 Daimler Chrysler Ag Functional fluid containing polyalkylene glycol(s) for use as lubricant for tribo-systems in racing car engines
JP3555844B2 (en) 1999-04-09 2004-08-18 三宅 正二郎 Sliding member and manufacturing method thereof
FR2792325B1 (en) 1999-06-30 2006-07-14 Renault NON-TOXIC AND BIODEGRADABLE FUNCTIONAL FLUIDS BASED ON NEOPOLYOL FAT CHAIN ESTERS FOR MOTOR VEHICLES
JP2001214186A (en) * 2000-01-31 2001-08-07 Asahi Denka Kogyo Kk Lubricating composition
FR2817874B1 (en) 2000-12-08 2005-02-11 Renault FUNCTIONAL FLUID FOR MOTOR VEHICLES COMPRISING UREA
US6436883B1 (en) * 2001-04-06 2002-08-20 Huntsman Petrochemical Corporation Hydraulic and gear lubricants
US7179769B2 (en) 2003-07-17 2007-02-20 E. I. Du Pont De Nemours And Company Poly (trimethylene-ethylene ether) glycol lube oils
EP1661971A4 (en) 2003-08-06 2008-12-03 Nippon Oil Corp System having dlc contacting faces, method for lubricating the system and lubricating oil for the system
US7790660B2 (en) * 2004-02-13 2010-09-07 Exxonmobil Research And Engineering Company High efficiency polyalkylene glycol lubricants for use in worm gears
MX221601B (en) 2004-05-14 2004-07-22 Basf Ag Functional fluids containing alkylene oxide copolymers having low pulmonary toxicity
WO2006019548A1 (en) * 2004-07-16 2006-02-23 Dow Global Technologies Inc. Food grade lubricant compositions
DE102005011776A1 (en) 2005-03-11 2006-09-14 Daimlerchrysler Ag Polyalkylene glycol based synthetic lubricant with an additive composition, useful in motor tribology system for steel, light metal and/or colored metal, comprises an antioxidant, anti-wear additive and a colored metal activator
US20100204075A1 (en) * 2005-07-01 2010-08-12 Enbio Industries, Inc. Environmentally compatible hydraulic fluid
US7741259B2 (en) * 2005-07-01 2010-06-22 Enbio Industries, Inc. Environmentally compatible hydraulic fluid
WO2009134716A1 (en) * 2008-04-28 2009-11-05 Dow Global Technologies Inc. Polyalkylene glycol lubricant composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0578449A1 (en) 1992-07-10 1994-01-12 Rohm And Haas Company Process for preparing polysuccinimides from aspartic acid
WO1996003644A1 (en) 1994-07-27 1996-02-08 The Dow Chemical Company Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereof
FR2792326A1 (en) 1999-04-19 2000-10-20 Renault NON-TOXIC AND BIODEGRADABLE FUNCTIONAL FLUIDS BASED ON COPOLYMERS OF ETHYLENE OXIDE AND PROPYLENE OXIDE FOR MOTOR VEHICLES
EP1046699A1 (en) 1999-04-19 2000-10-25 Renault Non-toxic, biodegradable functional fluids for motor vehicles
US20040094743A1 (en) 2000-09-22 2004-05-20 Mathias Woydt Biodegradable functional fluid for mechanic drives
DE102005041909A1 (en) 2005-09-03 2007-03-08 Tea Gmbh Technologiezentrum Emissionsfreie Antriebe Use of a glycol based lubricant for steam power machines, motors operated with hydrogen and water impact machine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
VAN VOORST R: "Polyglycols as Base Fluids for Environmentally- Friendly Lubricants", JOURNAL OF SYNTHETIC LUBRICATION, LEAF COPPIN PUBLISHING LTD., DEAL, KENT, GB, vol. 16, no. 4, 1 January 2000 (2000-01-01), pages 313 - 322, XP007909273, ISSN: 0265-6582 *

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012033668A1 (en) * 2010-09-07 2012-03-15 The Lubrizol Corporation Hydroxychroman derivatives as engine oil antioxidants
EP3070153A1 (en) * 2010-09-07 2016-09-21 The Lubrizol Corporation Hydroxychroman derivatives as antioxidants
WO2012070007A1 (en) 2010-11-26 2012-05-31 Total Raffinage Marketing Engine lubricant composition
US9546335B2 (en) 2010-11-26 2017-01-17 Dow Global Technologies Llc Engine lubricant composition
US8535567B2 (en) 2011-03-11 2013-09-17 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
US9447322B2 (en) 2011-03-11 2016-09-20 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
US8535569B2 (en) 2011-03-11 2013-09-17 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles and methods for using same
US8535568B2 (en) 2011-03-11 2013-09-17 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
US8236204B1 (en) 2011-03-11 2012-08-07 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
US8236205B1 (en) 2011-03-11 2012-08-07 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles and methods for using same
WO2012129056A1 (en) 2011-03-23 2012-09-27 Dow Global Technologies Llc Polyalkylene glycol based heat transfer fluids and monofluid engine oils
CN103459546A (en) * 2011-03-23 2013-12-18 陶氏环球技术有限责任公司 Polyalkylene glycol based heat transfer fluids and monofluid engine oils
US20140018272A1 (en) * 2011-03-23 2014-01-16 Dow Global Technologies Llc Polyalkylene Glycol Based Heat Transfer Fluids and Monofluid Engine Oils
JP2014511913A (en) * 2011-03-23 2014-05-19 ダウ グローバル テクノロジーズ エルエルシー Polyalkylene glycol heat transfer fluid and single fluid engine oil
WO2013066702A3 (en) * 2011-11-01 2013-11-07 Dow Global Technologies Llc Oil soluble polyalkylene glycol lubricant compositions
CN103087811A (en) * 2011-11-07 2013-05-08 3M创新有限公司 Rustproof lubricating agent
WO2013164449A1 (en) 2012-05-04 2013-11-07 Total Marketing Services Engine lubricant composition
WO2013164457A1 (en) 2012-05-04 2013-11-07 Total Marketing Services Lubricant composition for an engine
WO2013164459A1 (en) 2012-05-04 2013-11-07 Total Marketing Services Engine lubricant for vehicles having a hybrid or micro-hybrid engine
US9957462B2 (en) 2012-05-04 2018-05-01 Total Marketing Services Engine lubricant composition
US10604717B2 (en) 2012-05-04 2020-03-31 Total Marketing Services Lubricant composition for an engine
US10752858B2 (en) 2012-11-16 2020-08-25 Total Marketing Services Lubricant composition
US9309205B2 (en) 2013-10-28 2016-04-12 Wincom, Inc. Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures
US9802905B2 (en) 2013-10-28 2017-10-31 Wincom, Inc. Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures
US20180245017A1 (en) * 2015-02-26 2018-08-30 Dow Global Technologies Llc Lubricant formulations with enhanced anti-wear and extreme pressure performance
WO2018078290A1 (en) 2016-10-27 2018-05-03 Total Marketing Services Composition for an electric vehicle
US11473029B2 (en) 2016-10-27 2022-10-18 Total Marketing Services Composition for an electric vehicle

Also Published As

Publication number Publication date
EP2271732A1 (en) 2011-01-12
CA2722431C (en) 2016-08-02
TWI493027B (en) 2015-07-21
MX2010011869A (en) 2010-11-30
CA2722431A1 (en) 2009-11-05
US20130102507A1 (en) 2013-04-25
US20110039741A1 (en) 2011-02-17
KR20110018327A (en) 2011-02-23
KR101628406B1 (en) 2016-06-08
US8357644B2 (en) 2013-01-22
MX324478B (en) 2014-10-14
US8592357B2 (en) 2013-11-26
TW201000623A (en) 2010-01-01
EP2271732B1 (en) 2013-04-17

Similar Documents

Publication Publication Date Title
US8592357B2 (en) Polyalkylene glycol lubricant composition
WO2012134794A1 (en) Lubricant compositions comprising polylkylene glycol diether with low noack volatility
US20140018272A1 (en) Polyalkylene Glycol Based Heat Transfer Fluids and Monofluid Engine Oils
AU2002367745A1 (en) Biodegradable non-toxic gear oil
CA1280402C (en) Lubricants for reciprocating air compressors
CN109312253B (en) Lubricating oil composition
EP3732228B1 (en) Modified oil soluble polyalkylene glycols
KR102589022B1 (en) Modified oil-soluble polyalkylene glycol
AU2021416533A1 (en) Process to produce low shear strength base oils
EP3601502B1 (en) Synthetic lubricant compositions having improved oxidation stability
WO2023074424A1 (en) Lubricant composition
JP2022531533A (en) Polyalkylene glycol lubricant composition

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09739518

Country of ref document: EP

Kind code of ref document: A1

DPE2 Request for preliminary examination filed before expiration of 19th month from priority date (pct application filed from 20040101)
WWE Wipo information: entry into national phase

Ref document number: 12988871

Country of ref document: US

Ref document number: 2009739518

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2722431

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: MX/A/2010/011869

Country of ref document: MX

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20107026515

Country of ref document: KR

Kind code of ref document: A