EP2691498A1 - Compositions lubrifiantes comprenant un diéther de polyalkylène glycol à basse volatilité noack - Google Patents

Compositions lubrifiantes comprenant un diéther de polyalkylène glycol à basse volatilité noack

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Publication number
EP2691498A1
EP2691498A1 EP12710621.9A EP12710621A EP2691498A1 EP 2691498 A1 EP2691498 A1 EP 2691498A1 EP 12710621 A EP12710621 A EP 12710621A EP 2691498 A1 EP2691498 A1 EP 2691498A1
Authority
EP
European Patent Office
Prior art keywords
lubricant composition
composition according
formula
alkyl
percent
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Withdrawn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
EP12710621.9A
Other languages
German (de)
English (en)
Inventor
Daniel Zweifel
Ronald Van Voorst
Marinus Meertens
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.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
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 LLC filed Critical Dow Global Technologies LLC
Publication of EP2691498A1 publication Critical patent/EP2691498A1/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M129/16—Ethers
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
    • C—CHEMISTRY; METALLURGY
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/102—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only used as base material
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C10M2209/1065—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C10M2209/1075—Polyethers, 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • C10M2209/1085—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • C—CHEMISTRY; METALLURGY
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
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    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/74—Noack Volatility
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the invention relates to lubricant compositions comprising a polyalkylene glycol compound and an additive package containing an anti-oxidant.
  • the lubricant compositions exhibit favorable properties, including high viscosity index and low volatility.
  • Lubricant compositions such as engine lubricant oils are composed of base oils and additives.
  • Certain synthetic base oils such as polyalkylene glycols (PAGs), are
  • PAG-based lubricants possess a number of advantages compared to conventional mineral oil lubricants, and are increasingly being used by original equipment manufacturers (OEMs) because of their ability to address a growing number of new performance criteria requested by automotive engine design departments.
  • OEMs original equipment manufacturers
  • PAG based lubricants still exhibit some shortcomings.
  • PAGs may exhibit unfavorably high volatility, which can result in increased oil consumption.
  • the viscosity index of some PAGs may be too low to provide the desired lubrication and fuel efficiency properties.
  • some PAGs may not be oil soluble, resulting in increased costs associated with the process of switching mineral oil based engines to the PAG lubricants. Such costs result from the need to use additional flushing and disposal steps if the PAG is not soluble in the mineral oil.
  • Lubricant compositions that exhibit low volatility, high viscosity index or both low volatility and high viscosity index.
  • Lubricant compositions that are also oil soluble would be a further advantage.
  • a composition according to the invention comprises: (a) a polyalkylene glycol of formula I:
  • the lubricant composition has a Noack volatility of 13 percent or less and a viscosity index of at least 165.
  • the invention also provides a method for lubricating an internal combustion engine.
  • the method comprises providing to the engine a lubricant composition as described herein.
  • the invention provides lubricant compositions.
  • the inventors have discovered that the selection of PAGs with specific structural features, such as a short alkyl group at position R 1 in formula I, together with the use of an additive package that contains an anti-oxidant, certain highly desirable properties are achieved.
  • lubricant compositions are achieved that exhibit both high viscosity index and low volatility.
  • compositions of the invention are also oil soluble, thus facilitating the replacement in engines of conventional mineral oils with such the PAG based lubricants.
  • a lubricant composition according to the invention comprises: (a) a polyalkylene glycol of formula I:
  • R is C4-C22 alkyl
  • AO is independently ethyleneoxy, propyleneoxy, butyleneoxy, or mixtures of two or more thereof; n is 8- 16; and R 1 is C]_-C alkyl; and (b) an additive package comprising an anti-oxidant.
  • the lubricant composition has a Noack volatility of 13 percent or less and a viscosity index of at least 165.
  • Polyalkylene glycols of formula I may be readily prepared by those skilled in the art using well known synthetic techniques.
  • a PAG may be formed by known techniques in which an aliphatic alcohol (often called an "initiator") is reacted with a single 1,2-oxide (ethylene oxide, propylene oxide, or butylene 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 PO may, in some embodiments, be between 40 weight percent and 60 weight percent, and preferably between 45 weight percent and 55 weight percent, based on total mixture weight.
  • Aliphatic alcohol reactants used in making the PAG include those containing one hydroxyl (OH) group and from 4 carbon atoms to 22 carbon atoms per molecule. Specific examples include, but are not limited to, butanol, pentanol, hexanol, neopentanol, isobutanol, decanol, propylene glycol n-butyl ether (available from The Dow Chemical Company as DOWANOLTM PnB), dipropylene glycol n-butyl ether (available from Dow as DOWANOLTM DPnB), and dodecyl alcohol (available e.g., as NACOL® 12-99 from Sasol).
  • DOWANOLTM PnB dipropylene glycol n-butyl ether
  • dodecyl alcohol available e.g., as NACOL® 12-99 from Sasol.
  • PAGs of formula I contain a short alkyl group at the R 1 position. Such capping may be readily achieved by those skilled in the art, for instance by the Williamson Ether Synthesis.
  • the uncapped PAG is first reacted with a base, converting the end OH groups into the alcoholate ion form. This alcoholate is then reacted with an alkyl halide, resulting in the capped PAG.
  • the base that may be used are sodium hydroxide and sodium methanolate.
  • An example of an alkyl halide that may be used is methyl chloride.
  • Preferred PAGs of formula I include materials of formula 1-1, which are PAGs of formula I wherein R is linear C 4 -C 14 alkyl.
  • R is linear C 4 - 12 alkyl, alternatively it is C 4 alkyl, or alternatively C 12 alkyl.
  • Preferred PAGs of formula I and 1-1 include materials of formula 1-2, which are PAGs of formula I or 1-1 wherein R 1 Q-C3 alkyl, alternatively R 1 is methyl.
  • Preferred PAGs of formula 1, 1-1 and 1-2 include materials of formula 1-3, which are PAGs of formula 1, 1-1, or 1-2 wherein AO is a mixture of ethyleneoxy and propyleneoxy.
  • the proportion of propyleneoxy, based on the amount of PO used for making the PAG is about 50 weight percent based on total mixture weight of ethyleneoxy and propyleneoxy.
  • Preferred PAGs of formula 1, 1-1 and 1-2 include materials of formula 1-4, which are PAGs of formula 1, 1-1, or 1-2 wherein AO is a mixture of propyleneoxy and butyleneoxy.
  • the proportion of propyleneoxy, based on the amount of PO used for making the PAG is about 50 weight percent based on total mixture weight of butyleneoxy and propyleneoxy.
  • Preferred PAGs of formula 1, 1-1 and 1-2 include materials of formula 1-5, which are PAGs of formula 1, 1-1, or 1-2 wherein AO is butyleneoxy.
  • Preferred PAGs of formula 1, 1-1 and 1-2 include materials of formula 1-6, which are PAGs of formula 1, 1-1, or 1-2 wherein AO is propyleneoxy.
  • Preferred PAGs of formula 1, 1-1, 1-2, 1-3, 1-4, 1-5, and 1-6 include materials of formula 1-7, which are PAGs of formula 1, 1-1, 1-2, 1-3, 1-4, 1-5, or 1-6 wherein the number average molecular weight is from 500 to 1500 g/mol. In some embodiments, the number average molecular weight may be 700 to 1300 g/mol, alternatively 800 to 1200 g/mol.
  • compositions of the invention exhibit a favorable viscosity index (VI).
  • VI indicates how a lubricant viscosity changes with temperature. For example, a low VI (e.g. 100) suggests that fluid viscosity will vary considerably when it is used to lubricate a piece of equipment that operates over a wide range of temperatures, such as from 20 °C to 100 °C. As VI increases, lubricant performance also tends to improve. Based upon that recognition, skilled artisans prefer higher VI values (e.g. 150) over lower VI values (e.g. 100).
  • Compositions of the invention have a viscosity index (VI) of 165 or more. In some embodiments, VI may be 180 or more, alternatively 200 or more, or alternatively 220 or more.
  • VI may be 400 or less.
  • cSt centistokes
  • m2/sec square meters per second
  • ASTM American Society for Testing and Materials
  • compositions of the invention possess favorable volatility profiles, as illustrated by their Noack volatilities.
  • the compositions of the invention have a Noack volatility of 13 percent or less. In some embodiments, the Noack volatility is 10 percent or less, alternatively 8 percent or less, or alternatively 6 percent or less.
  • Noack volatility may be determined by ACEA's (European Automobile Manufacturers Association) test method CEC L-40, which determines the evaporation loss of lubricants in high-temperature service.
  • Some of the PAGs of formula I may be oil soluble in hydrocarbon oils. Such materials are particularly advantageous because they facilitate replacement of mineral oils in engines with the PAG based materials. In particular, because of the oil solubility of the PAGs in mineral oil, the replacement can be easily carried out without the need for multiple flushing operations and associated waste disposal.
  • oil soluble PAGs of the preceding embodiment are of the formula II:
  • R is C4-C22 alkyl; PO is propyleneoxy; n is 8-16; and R 1 is Q-C3 alkyl.
  • Preferred oil soluble PAGs of formula II include materials of formula II- 1, which are PAGs of formula II wherein R is linear C 4 -C 14 alkyl. In some embodiments, R is linear C 4 - 12 alkyl, alternatively C 4 alkyl, or alternatively C 12 alkyl.
  • Preferred oil soluble PAGs of formula II and II- 1 include materials of formula ⁇ -2, which are PAGs of formula ⁇ or II- 1 wherein R 1 is methyl.
  • Preferred oil soluble PAGs of formula II, II- 1, and II-2 include materials of formula ⁇ -3, which are PAGs of formula II, II- 1, or ⁇ -2 wherein the number average molecular weight is from 500 to 1500 g/mol. In some embodiments, the number average molecular weight may be 700 to 1300 g/mol, alternatively 800 to 1200 g/mol.
  • compositions of the invention also contain an additive package comprising an anti-oxidant.
  • the additive package may further contain additional additives commonly used in the industry, for instance, an extreme pressure anti-wear additive, or an anti-corrosion additive, or a friction modifier, or an acid scavenger, or any combination of the foregoing.
  • the additive package contains all of the foregoing components, i.e., an anti-oxidant, an extreme pressure anti-wear additive, an anti-corrosion additive, a friction modifier, and an acid scavenger.
  • the antioxidant may be any such conventional material.
  • the antioxidant may vary widely, including compounds from classes such as amines and phenolics.
  • the antioxidant may 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).
  • antioxidants also include, but are not limited to, IRGANOXTM L01, L06, L57, L93 (alkylated diphenyl amines and alkylated phenyl-naphtyl amines); IRGANOXTM L101, L107, L109, LI 15, LI 18, L135 (hindered phenolic
  • antioxidants include IRGANOXTM L64, L74, L94, L134, and L150 (antioxidant blends);
  • IRGAFOSTM 168 di-tert-butyl phenyl phosphate
  • IRGANOXTM E201 alpha-tocopherol
  • IRGANOXTM L93 sulfur-containing aromatic amine antioxidant
  • antioxidants include, but are not limited to, amine antioxidants such as N-phenyl-l-naphthalenamine, N-phenylbenzenamine reaction products with 2,4,4-trimethylpentenes; phenothiazine; dibenzo-l,4,thiazine; 1,2- dihydroquinoline; poly(2,2,4-trimethyl-l,2-dihydroquinoline); and 6,6'-di-tert-butyl-2,2'- methylendi-p-cresol.
  • amine antioxidants such as N-phenyl-l-naphthalenamine, N-phenylbenzenamine reaction products with 2,4,4-trimethylpentenes
  • phenothiazine dibenzo-l,4,thiazine
  • 1,2- dihydroquinoline poly(2,2,4-trimethyl-l,2-dihydroquinoline)
  • 6,6'-di-tert-butyl-2,2'- methylendi-p-cresol 6,6'-di
  • 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.
  • extreme pressure and anti-wear additives can be any such conventional material.
  • 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, ⁇ , ⁇ , ⁇ -triphenylphosphorothioate, Zn-di-n-butyldithiocarbamate, Mo- dibutyldithiocarbamate, and Zn-methylene-bis-dialkyldithiocarbamate, with dibenzyldisulfide being especially preferred.
  • anti-wear additives that can be employed in the practice of this invention include but are not limited to IRGALUBETM 63, 211, 232, and 353 (isopropylated triaryl phosphates); IRGALUBETM 211 and 232 (nonylated triphenyl phosphorothionates);
  • IRGALUBETM 349 (amine phosphate); IRGALUBETM 353 (dithiophosphate); IRGAFOSTM DDPP (iso-decyl diphenyl phosphite); and IRGAFOSTM OPH (di-n-octyl-phosphite).
  • the anti-corrosion additive may be any single compound or mixture of compounds that inhibits corrosion of metallic surfaces.
  • the corrosion inhibitor can be any such conventional material.
  • 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.
  • 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-lH-benzotriazol-l-yl-methyl-imino-bis and methyl- lH-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
  • IRGACORTM DC11 undecanedioic acid
  • IRGACORTM DC 12 dodecanedioic acid
  • IRGACORTM L 184 TEA neutralized polycarboxylic acid
  • IRGACORTM L 190 polycarboxylic 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 acid scavenger is a single compound or a mixture of compounds that has an ability to scavenge acids.
  • the acid scavenger can be any such conventional material.
  • 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 lubricant composition preferably contains from 0.1 wt percent to 1 wt percent of the acid scavenger, based upon total lubricant composition weight.
  • the friction (rheology) modifier can be any such conventional material.
  • 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 further provide the lubricant composition with a desired thickness or viscosity.
  • the compositions may also contain a dispersant system to stabilize products from the combustion process.
  • the lubricant composition contains less than 0.1 weight percent, alternatively less than 0.05 weight percent, of aspartic acid or an aspartic acid derivative (which may function as an acid scavenger). In some embodiments, the lubricant composition contains no aspartic acid or its derivatives.
  • the lubricant composition of the invention may comprise from 50 to 99.9 weight percent of the PAG based on the total weight of the composition. In some embodiments, the composition comprises from 0.10 to 10 weight percent of the additives package based on the total weight of the composition.
  • the lubricant compositions may be prepared by simple addition of the components and mixing. This can occur at room temperature (nominally 25 °C). Higher temperatures of up to, for example, 170 °C, may be employed to effect solubilization of the additives into the PAG base stock. One may effect mixing, for instance, ultrasonically or by using a high speed dispergator.
  • compositions have utility as lubricants for instance in internal combustion engines, such as automobile engines.
  • the lubricant has utility as lubricants for instance in internal combustion engines, such as automobile engines.
  • the lubricant has utility as lubricants for instance in internal combustion engines, such as automobile engines.
  • composition is a motor oil.
  • the motor oil is 0W-20 motor oil.
  • ethyleneoxy refers to -CH 2 -CH 2 -O-
  • propyleneoxy refers to -CH 2 -CH(CH 3 )-0- or -CH(CH 3 )-CH 2 -0-
  • butyleneoxy refers to -CH 2 - CH(CH 2 CH 3 )-0- or -CH(CH 2 CH 3 )-CH 2 -0-.
  • alkyl encompasses straight and branched chain aliphatic groups having the indicated number of carbon atoms.
  • PAGs may be prepared as described above.
  • the PAG of Sample A is dipropylene glycol n-butyl ether started EO-PO (1: 1) random copolymer with a molecular weight of 800g/mol, methyl capped.
  • DPnB is dipropylene glycol n-butyl ether
  • Nacol 12-99 is a 12 carbon linear fatty alcohol
  • PnB is propylene glycol n-butyl ether
  • PAG is formulated with an additive package containing 0.5 % of an antioxidant, such as N-phenyl-l-naphthalenamine , IRGANOX L57, 6,6'-di-tert-butyl-2,2' methylendi-p-cresol, or phenothiazine.
  • an antioxidant such as N-phenyl-l-naphthalenamine , IRGANOX L57, 6,6'-di-tert-butyl-2,2' methylendi-p-cresol, or phenothiazine.
  • Table 2 shows the viscosity index (VI) of various samples.
  • Table 3 compares Noack volatility between formulated and unformulated samples.
  • CEC-L-40-A93 test under limits A3 A3/B3 - A3/B4 - A5/B5. A pass under these limits requires an evaporative loss of 13 % or less under the tested conditions.

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

Abstract

Cette invention concerne des compositions lubrifiantes qui manifestent un indice élevé de viscosité et une basse volatilité Noack. La composition lubrifiante selon l'invention comprend : (a) un polyalkylène glycol de formule I : RO-(AO)n-R1 (I) où R, R1, et n sont tels que définis dans la présente ; et (b) un ensemble additifs comprenant un antioxydant.
EP12710621.9A 2011-03-29 2012-03-12 Compositions lubrifiantes comprenant un diéther de polyalkylène glycol à basse volatilité noack Withdrawn EP2691498A1 (fr)

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FR2990215B1 (fr) 2012-05-04 2015-05-01 Total Raffinage Marketing Composition lubrifiante pour moteur
FR2998303B1 (fr) 2012-11-16 2015-04-10 Total Raffinage Marketing Composition lubrifiante
FR3024461B1 (fr) * 2014-07-31 2017-12-29 Total Marketing Services Compositions lubrifiantes pour vehicule a moteur
KR102431118B1 (ko) * 2014-07-31 2022-08-11 다우 글로벌 테크놀로지스 엘엘씨 자동차 응용에서 베이스 오일을 위한 알킬 캡핑된 유용성 중합체 점도 지수 개선 첨가제
CN106661479B (zh) * 2014-07-31 2020-05-08 陶氏环球技术有限责任公司 具有低粘度和高粘度指数的封端的油溶性聚亚烷基二醇
CA2967475A1 (fr) * 2014-11-13 2016-05-19 Orica International Pte Ltd Acheminement d'explosif a emulsion
BR112018073649B1 (pt) * 2016-05-27 2022-03-15 Dow Global Technologies Llc Formulação agroquímica, e, processo para preparar uma formulação agroquímica
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CN103842488A (zh) 2014-06-04
WO2012134794A1 (fr) 2012-10-04

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