WO2015073207A1 - Dispersants d'huile pour moteur à base d'époxyamine alcoxylate - Google Patents

Dispersants d'huile pour moteur à base d'époxyamine alcoxylate Download PDF

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Publication number
WO2015073207A1
WO2015073207A1 PCT/US2014/062822 US2014062822W WO2015073207A1 WO 2015073207 A1 WO2015073207 A1 WO 2015073207A1 US 2014062822 W US2014062822 W US 2014062822W WO 2015073207 A1 WO2015073207 A1 WO 2015073207A1
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Prior art keywords
dispersant
composition
base oil
oil
weight
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PCT/US2014/062822
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English (en)
Inventor
Cynthia Pierre
Cynthia L. Rand
Brian A. Jazdzewski
John B. Cuthbert
Daniel F. Zweifel
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Dow Global Technologies Llc
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Priority to EP14799609.4A priority Critical patent/EP3068852A1/fr
Priority to CN201480060907.5A priority patent/CN105722963A/zh
Priority to US15/034,348 priority patent/US20160289590A1/en
Publication of WO2015073207A1 publication Critical patent/WO2015073207A1/fr

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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
    • C10M169/00—Lubricating 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
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/04—Well-defined cycloaliphatic compounds
    • C10M2203/045—Well-defined cycloaliphatic compounds 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
    • C10M2205/223—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts 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
    • C10M2209/104—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
    • 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
    • C10M2209/107—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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property
    • C10N2030/041—Soot induced viscosity control
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/70—Soluble oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines

Definitions

  • the present invention relates to a dispersant for motor oil.
  • a dispersant for motor oil In particular, an epoxyamine alkoxylate that serves as an effective dispersant in polyalkylene glycol oil.
  • Soot detrimentally increases the viscosity of motor oil, thereby reducing engine fuel efficiency, while also increasing engine wear. Build-up of soot is especially problematic in diesel engines because their design tends to introduce greater oil contamination in return for reduced emissions.
  • Dispersant and detergents are included in fully formulated motor oils to control soot and other deposits.
  • a detergent functions to neutralize the precursors that lead to oil degradation whereas dispersants suspend soot and similar contaminants. The suspension of these particles prevents an increase in engine oil viscosity, soot induced wear, and filter blockage.
  • Polyalkylene glycol (PAG) motor oils are an attractive alternative to hydrocarbon motor oil.
  • PAG-based motor oils offer desirable advantages over hydrocarbon -based motor oils such as higher viscosity index, improved film formation, non-varnishing, improved heat transfer, excellent shear performance and stability. These inherent properties of PAGs allow them to be used as motor oils without need for added viscosity modifiers typical in many motor oils. Viscosity modifiers can break down during use and contribute to motor oil contaminates and diminished performance.
  • a challenge with PAG-based motor oils is identifying a suitable dispersant.
  • Many dispersants suitable for use in hydrocarbon-based motor oils are not effective in PAG-based motor oils.
  • PAGs are generally more polar than hydrocarbon based motor oil and, as a result, dispersants suitable for use in hydrocarbon based motor oils tend to not be soluble in PAG-based motor oil. Therefore, there is a need in the art to identify dispersants that are soluble in PAG-based motor oil, and that are effective soot dispersants especially in diesel motor oil applications.
  • the present invention provides a solution to the need for a dispersant that is soluble in PAG-based motor oil, even under the demanding application of diesel motor oil applications.
  • an epoxy amine alkoxylate has been found to be soluble in PAG-based motor oil and successfully disperses soot in the PAG-based motor oil even under stringent diesel motor testing.
  • the epoxy amine alkoxylate has the structure of Structure I:
  • A is a homopolymer of propylene oxide or a random copolymer of ethylene oxide (EO) and propylene oxide (PO) and where the concentration of EO moieties in A is from zero to 30 weight percent (wt ) based on total weight of EO and PO moieties.
  • the desirable molecular weight of the epoxy amine alkoxylate is in a range of 5,000 grams per mole (g/mol) to 7,500 g/mol, most preferably 6,000 g/mol to 7,000 g/mol.
  • the present invention is a composition comprising a base oil and a dispersant wherein the base oil comprises a polyalkylene glycol and the dispersant has the following structure:
  • A is homopolymer of propylene oxide or a random copolymer of ethylene oxide and propylene oxide and where the concentration of ethylene oxide moieties in A is from zero to 30 weight percent based on total weight of ethylene oxide and propylene oxide moieties and wherein the dispersant has a molecular weight in a range of 5,000 grams per mole and 7,500 grams per mole.
  • the present invention is process comprising the steps of providing the composition of the first aspect into a mechanical device where parts move with respect to one another such that the composition contacts at least a portion of the area between the parts that move with respect to one another.
  • composition of the present invention is useful as motor oil.
  • process of the present invention is useful for employing the composition as a lubricant.
  • Figure 1 shows an exemplary schematic for a two-step synthesis process for preparing a dispersant for use in the present invention.
  • Figures 2a and 2b illustrate shear stress sweep and time sweep curves for indicating formulation viscosities for formulations containing 5 wt dispersant and 5 wt carbon black.
  • Figures 3a and 3b illustrate shear stress sweep and time sweep curves for indicating formulation viscosities for formulations containing 5 wt dispersant and 5, 6, 7 and 8 wt loadings of carbon black.
  • Figures 4a and 4b illustrate shear stress sweep and time sweep for indicating formulation viscosities for formulations containing 6 wt dispersant and 5, 6, 7 and 8 wt loadings of carbon black.
  • Figures 5a and 5b illustrate shear stress sweep and time sweep curves for indicating formulation viscosities for formulations containing 7 wt dispersant and 5, 6, 7 and 8 wt loadings of carbon black.
  • Test methods refer to the most recent test method as of the priority date of this document unless a date is indicated with the test method number. References to test methods contain both a reference to the testing society and the test method number. Test method organizations are referenced by one of the following abbreviations: ASTM refers to ASTM International (formerly known as American Society for Testing and Materials); EN refers to European Norm; DIN refers to Deutsches Institute fiir Normung; and ISO refers to International Organization for Standards.
  • Polymer refers generally to both homopolymers and copolymers (that is, heteropolymers) without limitation unless otherwise indicated.
  • Copolymers that is, heteropolymers
  • Copolymer refers to a molecule containing multiple polymerized units of more than one monomeric species.
  • the composition of the present invention comprises a base oil that comprises a polyalkylene glycol (PAG).
  • the base oil desirably is composed primarily of (that is, contains more than 50 weight-percent based on total base oil weight) and can consist of one or a combination of more than one PAG.
  • Suitable PAGs normally have a viscosity at 40 degrees Celsius (°C) that is within a range of from 18 centiStokes, preferably 20 centiStokes (cSt)( 20 square millimeters per second (mm 2 /s)), to 10,000 cSt (10,000 mm 2 /s) and a viscosity at 100°C that is within a range of from 3 to 2,000 cSt (3 to 2,000 mm 2 /s).
  • °C degrees Celsius
  • Suitable PAGs include reaction products of a 1,2-oxide (vicinal epoxide) with one or more material selected from a group consisting of water, an alcohol, or an aliphatic polyhydric alcohol containing from 2 hydroxyl groups to 6 hydroxyl groups and two or more, preferably three or more, more preferably four or more while at the same time 22 or fewer, preferably 16 or fewer and more preferably 12 or fewer carbon atoms per molecule.
  • Suitable 1,2-oxides (alkylene oxides) include lower alkylene oxides (that is, alkylene oxides containing from two to eight carbon atoms).
  • suitable 1,2-oxides includes ethylene oxide, propylene oxide, butylene oxide, cyclohexene oxide and glycidol as well as any combination of more than one of these 1,2-oxides.
  • the PAG can 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 1,2- oxide.
  • the initiator can be first oxyalkylated with one type of 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 three weight percent (wt%) or more, preferably 5 wt or more and at the same time typically 60 wt or less, preferably 50 wt or less based on total mixture weight.
  • Aliphatic polyhydric alcohol reactants used in making the PAG include those containing from two hydroxyl (OH) groups to six OH groups and at the same time two or more, preferably three or more, more preferably four or more while at the same time 22 or fewer, preferably 16 or fewer and more preferably 12 or fewer carbon atoms carbon atoms per molecule.
  • Suitable aliphatic alcohol reactants include ethylene glycol, propylene glycol, 2,3-butylene glycol, 1,2-butylene glycol, 1,2-butanediol, 1,3-propanediol, 1,5-pentane diol, 1,6-hexene diol, glycerol, trimethylolpropanes, sorbitol, pentaerythritol, and mixtures thereof.
  • 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.
  • glycerol can be first oxyalkylated with PO and the resulting PAG oxyalkylated with EO.
  • glycerol can be reacted with EO and the resulting PAG 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 the aforesaid 1,2-oxides, in the same manner. Techniques for preparing suitable polyethers from mixed 1,2-oxides are shown in U.S. Patents 2,674,619; 2,733,272; 2,831,034; 2,948,575; and 3.036,118.
  • Monohydric alcohols typically used as initiators include the lower acyclic alcohols such as methanol, propylene glycol methyl ether (for example DOWANOLTM PM,
  • DOWANOL is a trademark of The Dow Chemical Company
  • ethanol propanol, butanol, pentanol, hexanol, neopentanol, isobutanol, and decanol as well as higher acyclic alcohols derived from both natural and petrochemical sources with 11 carbon atoms to 22 carbon atoms.
  • water can also be used an initiator.
  • the PAG for use in the present invention is selected from PAGs produced by the polymerization of PO or both EO and PO onto an initiator.
  • One desirable PAG is an alcohol initiated water-insoluble PO polymer.
  • the base oil can contain up to less than 50 wt based on total base oil weight of other lubricating oils such as vegetable oil, mineral oil, synthetic lubricants such as polyolesters, alkylaromatics, polyethers, hydrogenated or non-hydrogenated poly-alpha- olefins and similar substances of lubricating viscosity.
  • the base oil can also be free of any other lubricating oils.
  • PAGs are desirably selected from those having the following formula:
  • PAG products are currently available commercially, including but not limited to those products sold under the following brand names: PLURIOLTM A750E; PLURACOLTM WS55; WS100, WS170, B 11/25, B 11/50, B32/50; BREOXTM A299; BREOXTM 50A; PPG-33-series; UCONTM 50-HB series; SYNALOXTM 50-xxB series; SYNALOXTM 100-xxB series; D21/150; PLURONICTM 450PR, PLURONICTM 600PR; TERRALOX WA46; TERRALOX WA110; SYNALOXTM 40-D150; polygycol BO 1/20, BO 1/40, B01/50, B15, B35; UCONTM LB65, LB125, LB285, WI285, W1625, P41/200; PLURONIX GENAPOLTM; WAKO T01/15, T01/35, T01/60; LUPRAN
  • PLURIOL is a trademark of BASF SE Societas Europae. PLURACOL and
  • PLURONIC are a trademarks of BASF Corporation.
  • BREOX is a trademark of BP p.l.c.
  • UCON and SELEXOL are trademarks of Union Carbide Corporation.
  • SYNALOX is a trademark of The Dow Chemical Company.
  • GENAPOL is a trademark of Clariantstoff GMBH.
  • LUPRANOL is a trademark of BASF Aktiengesellschaft Corporation.
  • composition further comprises a dispersant that has the following structure:
  • A is propylene oxide or a random copolymer of ethylene oxide and propylene oxide and where the concentration of ethylene oxide moieties in A is from zero to 30 weight percent based on total weight of ethylene oxide and propylene oxide moieties and wherein the dispersant has a molecular weight in a range of 5,000 grams per mole and 7,500 grams per mole.
  • the dispersant is obtainable from a two-step synthesis process where an initial epoxy resin reacts with di-butyl- amine (DBA) in a first step and then the resulting product is alkoxylated in a second step, as shown schematically in Figure 1.
  • DBA di-butyl- amine
  • Each step can comprise any number of sub-steps.
  • the alkoxylation step can comprise any number of feed steps and digestion steps.
  • the final product shown in Figure 1 corresponds to Structure 1 where A of Structure 1 is indicated by the following structure:
  • n is either a PO moiety or an EO moiety as is indicated by the option of a pendant methyl or hydrogen group.
  • the initial epoxy resin is a liquid reaction product of epichlorohydrin and bisphenol A such as that which is commercially available as DERTM-331 Liquid Epoxy Resin (DER is a trademark of The Dow Chemical Company).
  • the epoxy resin reacts with two mole equivalents of DBA, with the DBA fed over 1.5 hours at 140°C and then allowed to digest at 140°C for three hours.
  • the second reaction step is the alkoxylation of the reaction product of the first reaction step (intermediate product).
  • Alkoxylation can be accomplished via multiple epoxide feeds.
  • Alkoxylation includes reacting with PO or EO and PO to create an alkoxy chain from the pendant hydroxyl (OH) groups of the intermediate product.
  • the alkoxy chain is either PO oxide or a random copolymer of EO and PO.
  • Conduct the alkoxylation by adding a base catalyst (for example, potassium hydroxide) and removing water by means of a vacuum. Slowly add alkylene oxide to the reactor as 125°C. Once all of the alkylene oxide has been added, keep the reactor at 125°C for five hours to allow the alkylene oxide to react. Remove the catalyst remains by absorption on a filter agent and filtration.
  • a base catalyst for example, potassium hydroxide
  • the alkoxylation step in preparing the dispersant is sufficient to achieve a concentration of EO moieties that is from zero to 30 weight percent based on the total weight of EO and PO moieties.
  • EO moieties correspond to the copolymerized components of ethylene oxide in the resulting polymer.
  • PO moieties correspond to the copolymerized components of propylene oxide in the resulting polymer.
  • the concentration of EO moieties is greater than zero, preferably three wt or more, more preferably five wt or more, and can be ten wt or more, 15 wt or more, 20 wt or more and even 25 wt or more but is 30 wt or less based on total weight of EO and PO moieties. If the concentration of EO exceeds 30 wt the material does not perform as a desirable soot dispersant.
  • the alkoxylation step in preparing the dispersant is further sufficient to achieve a dispersant molecule having a molecular weight that is in a range of 5,000 to 7,500 grams per mole.
  • the molecular weight of the dispersant is 5,500 g/mol or more, preferably 6,000 g/mol or more, still more preferably 6,500 g/mol or more and can be 7,000 g/mol or more while at the same time is 7,500 g/mol or less, preferably 7,000 g/mol or less.
  • the dispersant is of the structure of Structure I where A is a random copolymer of EO and PO with a PO moiety concentration that is 90 wt or more, preferably 93 wt or more, still more preferably 95 wt or more and less than 100 wt based on total combined weight of EO and PO moieties and where the dispersant has a molecular weight of 6,000 g/mol or more, preferably 6,500 g/mol or more and at the same time 7,000 g/mol or less.
  • the concentration of dispersant in the base oil is desirably one wt or more, preferably three wt or more, still more preferably four wt or more, even more preferably five wt or more and can be six wt or more, seven wt or more, eight wt or more , nine wt or more, ten wt or more and even 11 wt or more while at the same time is desirably 12 wt or less, preferably 11 wt or less and can be ten wt or less, nine wt or less, eight wt or less and even seven wt or less.
  • the dispersant At concentrations below one wt the dispersant is generally too dilute to effectively disperse soot particulates at a high enough concentration to be valuable in a motor oil. At concentrations above 12 wt the dispersant can cause an increase in the composition viscosity and that requires base oil modifications to compensate.
  • the dispersant of the present invention surprisingly has the necessary properties to act as a soot dispersant in PAG-based oils.
  • the dispersant is soluble in PAGs.
  • the dispersant demonstrates an ability to disperse soot in PAGs, even under motor oil use temperatures.
  • the dispersant is thermally stable in motor oil applications.
  • the dispersant proves to be a surprisingly effective dispersant in PAG-based motor oil.
  • composition of the present invention can further comprise other additives in addition to the dispersant and base oil.
  • suitable additives include extreme pressure (EP) and anti-wear (AW) additives.
  • Suitable additives include zinc
  • the process of the present invention provides a method for lubricating a mechanical device with the composition of the present invention.
  • the process of the present invention comprises providing the composition of the present invention into a mechanic device where parts move with respect to one another such that the composition contacts at least a portion of the area between the parts that move with respect to one another.
  • a particularly desirable mechanical device for this process is an engine where the parts that move with respect to one another are a piston and piston shaft of the engine.
  • the mechanical device is a diesel engine.
  • Diesel engines produce more soot in the motor oil lubricant than most engines so the dispersant serves a particularly demanding role in diesel engine motor oil compositions.
  • the composition of the present invention has proven to be successful in dispersing soot in diesel engine applications.
  • dispersant having the structure of Structure I and are further characterized by "A" being a random copolymer of EO and PO where the EO moiety concentration is five weight percent of the combined weight of EO and PO moieties and the average molecular weight of the dispersant is between 6,000 and 7,000 g/mol.
  • A being a random copolymer of EO and PO where the EO moiety concentration is five weight percent of the combined weight of EO and PO moieties and the average molecular weight of the dispersant is between 6,000 and 7,000 g/mol.
  • the base oils used are selected from those in Table 1.
  • SPECTRASYN and SYNESSTIC are trademarks of Exxon Mobil Corporation.
  • YUBASE is a trademark of SK Lubricants Co. Dispersant Solubility in Base Oils
  • the solubility of the dispersant in the base oils was characterized at concentrations up to 6 wt based on composition weight at 5°C and at 80°C. Characterize the solubility using Phase Identification and Characterization Apparatus (PICA) ⁇ in combination with Epoch software PICA II VI 0.0.5 -current version as of priority date of this document.
  • PICA Phase Identification and Characterization Apparatus
  • Tables 2 and 3 reveal clarity measurements for formulations of the dispersant with the various base oils at different concentrations.
  • Table 2 is an evaluation at 5°C and Table 3 is an evaluation at 80°C. The results reveal that the dispersant is soluble in the full variety of base oils at both temperatures.
  • Solubility was further characterized using a formulation that includes common oil additives to confirm solubility in the presence of the additives.
  • Table 4 contains the additive package used in the screening with concentration in wt% relative to total formulation weight.
  • Tables 5 and 6 present the clarity values for the additive-containing formulations with the dispersant at different concentrations.
  • Table 5 is at 5°C and Table 6 is at 80°C. Notably, results are only shown for the oils that the additive package itself was soluble in.
  • the data reveals that the dispersant is soluble in formulations where the additive package is soluble in the oil.
  • IRGANOX is a trademark of CIBA Specialty Chemicals Corporation.
  • Dispersing efficiency of the dispersant in a base oil was characterized using carbon black in an oil formulation containing a full set of additives. Carbon black was used to simulate soot. The ability to disperse carbon black, which represents soot, was
  • UCON LB- 165 is a PAG characterized as an alcohol-initiated base stock of oxypropylene groups with one terminal hydroxyl group. It is water insoluble and has an average molecular weight of 740 g/mole and a viscosity of 34 cSt at 40°C.
  • UCON LB-285 is a PAG characterized as an alcohol-initiated base stock of oxypropylene groups with one terminal hydroxyl group. It is water insoluble and has an average molecular weight of 1020 g/mole and a viscosity of 61 cSt at 40°C.
  • IRGAMET and IRGALUBE are trademarks of BASF SE Company.
  • Figures 2a and 2b illustrate shear stress sweep and time sweep curves for indicating formulation viscosities for formulations containing 5 wt dispersant and 5 wt carbon black.
  • the "aged" sample was heat aged at 150°C for 100 hours to simulate aged motor oil.
  • the figures reveal that a 5 wt loading of the dispersant effectively disperses a 5 wt loading of carbon black in the PAG formulation, even upon heat aging.
  • Figures 3a and 3b illustrate shear stress sweep and time sweep curves for indicating formulation viscosities for formulations containing 5 wt dispersant and 5, 6, 7 and 8 wt loadings of carbon black. The data reveals that 5 wt loading of the dispersant effectively dispersed up to 6 wt carbon black equally well but less well for 7 and 8 wt carbon black loadings.
  • Figures 4a and 4b illustrate shear stress sweep and time sweep for indicating formulation viscosities for formulations containing 6 wt dispersant and 5, 6, 7 and 8 wt loadings of carbon black.
  • the data in these figures reveals that increasing dispersant concentration to 6 wt improves dispersability of the carbon black over 5 wt loading of dispersant.
  • Figures 5a and 5b illustrate shear stress sweep and time sweep curves for indicating formulation viscosities for formulations containing 7 wt dispersant and 5, 6, 7 and 8 wt loadings of carbon black.
  • the data in these figures reveals that increasing dispersant concentration to 7 wt improves dispersability of the carbon black over 6 wt loading of dispersant.
  • Ford DV-4 Engine Test
  • the Peugeot DV-4 Engine Test (ACEA European Oil Sequences, Dec. 2010, 2.6 Medium temperature dispersivity test CEC L-093-04 (DV4TD)) evaluates the ability of an engine lubricant to disperse the combustion soot accrued during severe diesel engine operation.
  • the test consists of 240 thirty-minute cycles operated at 4000 revolutions per minute and 11.8 kilograms per hour of fuel flow and includes brief periods of operation at idle. The test is conducted at 120°C. Oil performance is evaluated by determining the viscosity increase of the oil at 100°C relative to the viscosity of fresh oil. Oil performance is evaluated once the oil achieves at least 6 wt soot as determined by thermogravimetric analysis (TGA). Piston merit is also assessed.
  • TGA thermogravimetric analysis
  • Piston merit is also assessed.
  • the test is included in the ACEA European Oil Sequences for the A, B and C categories for both viscosity increase and piston merit.
  • the Ober DV-4 Engine Test was performed by ISP,
  • Table 8 indicates the formulation tested in the Ford DV-4 Engine Test.
  • the base oil is the same as used in the carbon black dispersion evaluation as described above.
  • Figure 6 reveals that the test results showing viscosity of the formulation as a function of soot concentration. A maximum viscosity of 18.13 cSt is allowable to pass the test.
  • the data in Figure 6 reveals that the formulation of the present invention described in Table 8 passes the Peugeot DV-4 Engine Test with soot concentrations in excess of 6 wt .

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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)
  • Lubricants (AREA)

Abstract

L'invention concerne une composition comprenant une huile de base et un dispersant, l'huile de base comprenant un polyalkylène glycol et le dispersant étant un époxyamine alcoxylate de structure I utile dans un procédé dans lequel la composition est utilisée comme lubrifiant dans un dispositif mécanique.
PCT/US2014/062822 2013-11-14 2014-10-29 Dispersants d'huile pour moteur à base d'époxyamine alcoxylate WO2015073207A1 (fr)

Priority Applications (3)

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EP14799609.4A EP3068852A1 (fr) 2013-11-14 2014-10-29 Dispersants d'huile pour moteur à base d'époxyamine alcoxylate
CN201480060907.5A CN105722963A (zh) 2013-11-14 2014-10-29 烷氧基化环氧胺发动机油分散剂
US15/034,348 US20160289590A1 (en) 2013-11-14 2014-10-29 Epoxyamine alkoxylate motor oil dispersants

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US201361904168P 2013-11-14 2013-11-14
US61/904,168 2013-11-14

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JP7391962B2 (ja) 2018-12-11 2023-12-05 ダウ グローバル テクノロジーズ エルエルシー ポリアルコキシル化アミノアルコールを使用する難溶性有効成分の水溶液

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CN110724581A (zh) * 2018-07-17 2020-01-24 中国石油化工股份有限公司 一种食品级导热油组合物

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US2520733A (en) * 1946-08-26 1950-08-29 Shell Dev Polymers of trimethylene glycol
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
US20060089426A1 (en) * 2004-10-20 2006-04-27 Karlheinz Haubennestel Alkoxylated epoxide-amine adducts and their use
US20130157909A1 (en) * 2010-08-31 2013-06-20 Dow Global Technologies Llc Corrosion Inhibiting Polyalkylene Glycol-Based Lubricant Compositions
WO2012068099A1 (fr) * 2010-11-17 2012-05-24 Dow Global Technologies Llc Procédé faisant intervenir un dérivé alcoxylé et aminé de bisphénol a en tant que démulsifiant
WO2013066702A2 (fr) * 2011-11-01 2013-05-10 Dow Global Technologies Llc Compositions lubrifiantes de poly(alkylène glycol) solubles dans l'huile

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Publication number Priority date Publication date Assignee Title
JP7391962B2 (ja) 2018-12-11 2023-12-05 ダウ グローバル テクノロジーズ エルエルシー ポリアルコキシル化アミノアルコールを使用する難溶性有効成分の水溶液

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EP3068852A1 (fr) 2016-09-21
US20160289590A1 (en) 2016-10-06

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