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WO2024218169A1 - Composition lubrifiante comprenant un sel d'amine d'ester de phosphate - Google Patents

Composition lubrifiante comprenant un sel d'amine d'ester de phosphate Download PDF

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Publication number
WO2024218169A1
WO2024218169A1 PCT/EP2024/060452 EP2024060452W WO2024218169A1 WO 2024218169 A1 WO2024218169 A1 WO 2024218169A1 EP 2024060452 W EP2024060452 W EP 2024060452W WO 2024218169 A1 WO2024218169 A1 WO 2024218169A1
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WO
WIPO (PCT)
Prior art keywords
group
lubricant composition
amine
phosphate
phosphate ester
Prior art date
Application number
PCT/EP2024/060452
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English (en)
Inventor
Michael HEERAN
John Thomas Dixon
Ezio AMERIO
Rudolf Anthonius Maria Venderbosch
Original Assignee
Nouryon Chemicals International B.V.
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Filing date
Publication date
Application filed by Nouryon Chemicals International B.V. filed Critical Nouryon Chemicals International B.V.
Publication of WO2024218169A1 publication Critical patent/WO2024218169A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/08—Ammonium or amine salts
    • 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
    • C10M153/00—Lubricating compositions characterised by the additive being a macromolecular compound containing phosphorus
    • C10M153/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/043—Ammonium or amine salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • 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
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/43—Sulfur free or low sulfur content compositions
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/45—Ash-less or low ash content

Definitions

  • the present disclosure generally relates to lubricant compositions that include phosphate ester amine salts. More specifically, the phosphate ester amine salts include naturally derived C8-C18 groups, e.g. cocoyl and tallowyl groups. BACKGROUND [0002] Amine neutralized phosphate esters are a type of lubricant additive that combines the properties of both phosphate esters and amine salts.
  • phosphate esters are known to be produced by reacting a phosphate ester with an amine, such as an alkanolamine or an alkyleneamine, to form an amine salt.
  • the resulting amine neutralized phosphate ester combines the anti-wear and anti- oxidant properties of phosphate esters with the friction reduction, detergency and dispersancy properties of amine salts. This can provide enhanced performance in a variety of lubricant applications, particularly in high-temperature, high-load applications where conventional anti- wear additives may not be effective.
  • Amine neutralized phosphate esters are typically used in lubricants for gearboxes, hydraulic systems, and other heavy-duty industrial applications. They can help to reduce friction, prevent wear, and protect against rust and corrosion.
  • amine neutralized phosphate esters can also help to prevent the formation of deposits and sludge, which can improve the overall performance and lifespan of the lubricant.
  • amine neutralized phosphate esters can also act as emulsifiers, allowing them to be used in applications where water contamination may be a concern, such as in marine or off-shore equipment. [0004] Overall, amine neutralized phosphate esters offer a unique combination of properties that can provide enhanced performance in a variety of lubricant applications. Nevertheless, there remains a need for a significant reduction in friction with concurrent reduction in wear. This enables improvement in the energy efficiency of many mechanical systems, while simultaneously extending the lifetime of mechanical equipment.
  • This disclosure provides a lubricant composition that is ashless, metal free, and sulfur free and that comprises: (1) an oil of lubricating viscosity; and (2) about 0.05 to about 3 wt% actives of a phosphate ester amine salt based on a total weight of the composition, wherein the phosphate ester amine salt is the reaction product of: a phosphate ester; and an amine; wherein the phosphate ester has the following structure (I) (I) wherein R’ has the formula R-O-[(CH 2 CH 2 O) m (CH 2 CH 2 CH 2 O) n ]; R is a naturally derived C8-C18 group; m+n is from 3 to 15; and R” is H or independently a second R’; wherein the amine has the following structure (II) ; wherein at least two of R 1 , R 2 , and R 3 are independently a naturally derived C 8 - C18 group and R 2
  • R 1 , R 2 , and R 3 is independently a naturally derived C 8 -C 18 group and one or two of R 1 , R 2 , and R 3 is CH3 or 2-ethylhexyl, or R 1 a naturally derived C8-C18 group and R 3 is H or CH3 or (CH2CH2O)xH, wherein x is from 1 to 3 and R 2 is CH 2 CH 2 CH 2 NR 4 2 wherein R 4 is H or CH 3 or (CH2CH2O)yH, wherein y is from 1 to 3; or R 1 is a naturally derived C8-C18 group and each of R 2 and R 3 is (CH 2 CH 2 O) x H, wherein x is from 1 to 3.
  • the compositions of this disclosure provide exhibit excellent wear performance, provide good wear protection at comparatively low treat rates, exhibit good oil solubility (e.g. high carbon content), have comparatively low phosphorous content as compared to comparative compositions, exhibit both good wear performance and low friction coefficients simultaneously, have customizable TBN values, detergency properties, and friction modification properties, and can include phosphate ester amine salts that have comparatively low conductivity properties. Combinations of these attributes allow for the formation of excellent engine oils, hydraulic fluids, transmission oils, EV fluids, greases, etc.
  • compositions are formed that are ashless, halogen-, sulphur- and metal-free (which can be important in several applications e.g. engine oils, transmission fluids for EVs and hydraulic fluids), that exhibit improved wear performance when compared to compositions that include sulfur, and optionally include or exclude, for example, ZDDP (industry standard) and/or MoDTC (molybdenum containing friction modifier) and/or DTC (dithiocarbamate), that exhibit excellent wear performance at comparatively low treat rates, that exhibit low P-content which allows for use in engine oil applications, that exhibit both low friction coefficients and low wear performance (contrary to ZDDPs), that exhibit variable friction performance at the same low wear performance (which can be desirable for transmission fluids), and that have multifunctionality e.g.
  • FIG.1 is a plot of coefficient of friction versus wear scar diameter showing the superior combined coefficient of friction and wear prevention performance of various embodiments of this disclosure as described in the Examples.
  • DETAILED DESCRIPTION [0009] The following detailed description is merely exemplary in nature and is not intended to limit the current lubricant composition. Furthermore, there is no intention to be bound by any theory presented in the preceding background or the following detailed description.
  • Embodiments of the present disclosure are generally directed to lubricant compositions and methods for forming the same.
  • conventional techniques related to lubricant compositions may not be described in detail herein.
  • the various tasks and process steps described herein may be incorporated into a more comprehensive procedure or process having additional steps or functionality not described in detail herein.
  • steps in the manufacture of lubricant compositions are well- known and so, in the interest of brevity, many conventional steps will only be mentioned briefly herein or will be omitted entirely without providing the well-known process details.
  • the terminology “about” can describe values ⁇ 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10%, in various embodiments.
  • the terminology “free of” describes embodiments that include less than about 5, 4, 3, 2, 1, 0.5, or 0.1, weight percent (or weight percent actives) of the compound or element at issue using an appropriate weight basis as would be understood by PCT PATENT APPLICATION ATTORNEY DOCKET NO. 364.1480PC one of skill in the art. In other embodiments, the terminology “free of” describes embodiments that have zero weight percent of the compound or element at issue.
  • Lubricant Composition This disclosure provides a lubricant composition which may be described herein as the “lubricating composition” or the “composition.”
  • the composition is typically ashless, metal free, and sulfur free. However, these are not strictly independent requirements that must each be met in all circumstances, as will be understood. Moreover, it is contemplated that not all embodiments are ashless and may include some ash content. Having ashless components allow for the preparation of low ash containing lubricants that still provide effective lubrications benefits.
  • the terminology “ashless” describes that the composition does not include metallic additives or other materials that leave behind a residue, known as "ash,” when burned.
  • the composition includes less than 5, 4, 3, 2, 1, 0.5, 0.1, 0.05, or 0.01, weight percent of a metallic additive or other material that would leave behind a residue when burned, based on a total weight of the composition.
  • the composition can be metal free. Typically, this means that the composition is free of any metals.
  • the term “metal free” may be used to describe that the composition is substantially free from metals. However, it is contemplated that the terminology “metal free” may describe embodiments that the composition includes less than 5, 4, 3, 2, 1, 0.5, 0.1, 0.05, or 0.01, weight percent of a metal, based on a total weight of the composition.
  • the composition includes an oil of lubricating viscosity and a phosphate amine ester salt. In other embodiments, the composition consists essentially of the oil and the phosphate amine ester salt. In other embodiments, the composition consists of the oil and the phosphate amine ester salt.
  • the oil of lubricating viscosity i.e., an oil exhibiting a viscosity suitable for use in lubricating applications such as those described here, may be alternatively described as a “base stock” or “base oil” or simply “oil” herein.
  • This oil is typically the primary liquid constituent of the composition and may be any known in the art.
  • the oil is described as a base oil and is chosen from natural (vegetable, animal or mineral) and synthetic lubricating oils and combinations thereof.
  • the type of oil is not particularly limited and may be any type of oil of lubricating viscosity known in the art.
  • the oil is a Group III base stock as defined in the American Petroleum Institute (API) publication “Engine Oil Licensing and Certification System”, Industry Services Department, Fourteenth Edition, December 1996, Addendum 1, December 1998.
  • the Group III base stock typically has a viscosity of about 3 to about 12, about 4 to about 10, or about 4.5 to about 8, mm 2 /s (cSt) at 100° C.
  • cSt mm 2 /s
  • the oil may be as described in the American Petroleum Institute (API) publication “Engine Oil Licensing and Certification System”, Industry Services Department, Fourteenth Edition, December 1996, Addendum 1, December 1998.
  • the oil may be a Group I base stock that includes less than about 90 percent saturates and/or greater than about 0.03 percent sulphur and has a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in Table E-1.
  • the oil may be a Group II base stock that includes greater than or equal to about 90 percent saturates and less than or equal to about 0.03 percent sulphur and has a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in PCT PATENT APPLICATION ATTORNEY DOCKET NO. 364.1480PC Table E-1.
  • the oil may be a Group III base stock that includes greater than or equal to about 90 percent saturates and less than or equal to about 0.03 percent sulphur and has a viscosity index greater than or equal to 120 using the test methods specified in Table E-1.
  • the oil may be a Group IV base stock such as an polyalphaolefins (PAO).
  • PAO polyalphaolefins
  • the oil may be a Group V base stock that includes all other base stocks not included in Group I, II, III, or IV.
  • saturates may be determined using ASTM D 2007, viscosity index may be determined using ASTM D 2270, sulphur may be determined using ASTM D 2622, ASTM D 4294, ASTM D 4927, ASTM D 3120, or combinations thereof.
  • the oil includes greater than or equal to about 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, or 95, mass %, of a Group III base stock, based on the total mass of the oil itself.
  • the oil consists of, or consists essentially of, a Group III base stock.
  • Additives included in the oil may comprise a carrier oil which is not a Group III base stock.
  • all values and ranges of values, both whole and fractional, including and between those described above, are hereby expressly contemplated for use herein.
  • the oil is or includes a natural oil which may be chosen from animal and vegetable oils (e.g. castor and lard oil), liquid petroleum oils and hydro-refined, solvent-treated mineral lubricating oils of the paraffinic, naphthenic and mixed paraffinic- naphthenic types, and combinations thereof.
  • the oil may be derived from coal or shale.
  • the oil is or includes a synthetic lubricating oil which may be chosen from hydrocarbon oils such as polymerized and interpolymerized olefins (e.g. polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1-octenes), poly(1-decenes)); alkylbenzenes (e.g. dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes); polyphenols (e.g.
  • hydrocarbon oils such as polymerized and interpolymerized olefins (e.g. polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1-octenes), poly
  • the oil is or includes an ester of a dicarboxylic acid (e.g. phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, PCT PATENT APPLICATION ATTORNEY DOCKET NO.
  • a dicarboxylic acid e.g. phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, PCT PATENT APPLICATION ATTORNEY DOCKET NO.
  • 364.1480PC alkylmalonic acids, alkenyl malonic acids) with a variety of alcohols e.g. butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, and combinations thereof.
  • alcohols e.g. butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol
  • esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
  • esters include those made from C5 to C12 monocarboxylic acids and polyols, and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol. Still others include esters made from mono carboxylic acids and mono- alcohols e.g. methanol, ethanol, etc. Methyl esters often have low viscosities. These mono- esters can also be based on alkoxylated alcohols wherein alkoxylate groups are ethylene oxide and/or propylene oxide. Other examples include polyalkylene glycol (PAG) based base stocks.
  • PAG polyalkylene glycol
  • the oil is or includes an unrefined, refined or re-refined oil.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment. For example, a shale oil obtained directly from retorting operations, a petroleum oil obtained directly from distillation or ester oil obtained directly from an esterification process and used without further treatment would be unrefined oil.
  • Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties.
  • the oil is or includes a gas-to-liquid (“GTL”) base oil, i.e. the oil may be an oil derived from Fischer-Tropsch synthesized hydrocarbons made from synthesis gas containing H 2 and CO using a Fischer-Tropsch catalyst.
  • GTL gas-to-liquid
  • hydrocarbons typically require further processing in order to be useful as a base oil.
  • they may, by methods PCT PATENT APPLICATION ATTORNEY DOCKET NO. 364.1480PC known in the art, be hydroisomerized; hydrocracked and hydroisomerized; dewaxed; or hydroisomerized and dewaxed.
  • the oil is or includes a Group I, Group II, Group IV or Group V base stocks or base oil blends of the aforementioned base stocks.
  • the volatility of the oil as measured by the NOACK test (ASTM D5880), is less than or equal to 16%, 13.5%, 12%, 10%, or 8%.
  • the viscosity index (VI) of the oil is at least 95, 110, 120, or 125, or from about 130 to 140. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those described above, are hereby expressly contemplated for use herein. [0031] In various embodiments, the oil is present in an amount of greater than 55, 60, 65, 70, 75, 80, 85, or 90, mass %, based on the total mass of the composition. In other embodiments, the oil is present in an amount of less than about 99, 98, 97, 96, 95, 94, 93, 92, 91, or 90, mass %, based on the total mass of the composition.
  • the oil may be present in an amount to balance the amount of the phosphate ester amine salt (e.g. as described below), such that the total is about 100%.
  • the amount of the oil may be such that the amount of the oil, plus the amount of the phosphate ester amine salt, plus the amount of any one or more additives described herein, is about 100%.
  • all values and ranges of values, both whole and fractional, including and between those described above, are hereby expressly contemplated for use herein.
  • the composition may be alternatively described as a physical mixture of the oil and the phosphate ester amine salt and any optional additives, e.g. those described herein.
  • the phosphate ester amine salt is present in the composition in an amount of from about 0.05 to about 3, about 0.1 to about 3, about 0.5 to about 2.5, about 1 to about 2, about 1.5 to about 2, about 1 to about 1.5, about 0.5 to about 1, about 0.5 to about 1.5, about 0.5 to about 2, about 0.1 to about 1.5, about 0.2 to about 1.4, about 0.3 to about 1.3, about 0.4 to about 1.2, about 0.5 to about 1.1, about 0.6 to about 1, about 0.7 to about 0.9, or about 0.8 to about 0.9, weight percent actives based on a total weight of the composition.
  • the phosphate ester amine salt is the reaction product of a phosphate ester and an amine, each of which is described in greater detail below. It is contemplated that a single phosphate ester or more than one phosphate ester may be utilized. Similarly, a single amine or more than one amine may be utilized. Typically, a combination of phosphate esters are utilized.
  • the phosphate ester typically has the following structure (I) (I) In this structure, R’ has the n]. Moreover, R” is H or independently a second R’. If ester is a phosphate monoester. If R” is independently a second R’, then the phosphate ester is a phosphate diester. Typically, a mixture of monoesters and diesters are used. [0036] Referring back to R’ in Formula (I), R is a naturally derived C8-C18 group. The terminology “naturally derived” means that the group is not a synthetic group and is derived from a natural source such as a plant or animal source, e.g. from animal fat.
  • the C8-C18 group may be alternatively described as a naturally sourced group or as a group derived from a natural source. Alternatively, the group may be described as a plant based group or as an animal fat based group.
  • the naturally derived C8-C18 group may be linear or branched having 8 to 18 carbon atoms so long as it is naturally derived.
  • the group may be saturated or unsaturated or partially unsaturated. In various embodiments, the group has 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms. In other embodiments, the group has 8 to 18, 9 to 17, 10 to 16, 11 to 15, 12 to 14, 10 to 18, 12 to 18, 14 to 18, 16 to 18, 12 to 18, 12 to 16, or 14 to 16 carbon atoms.
  • Non- limiting examples of naturally derived C 8 -C 18 groups include tallowyl groups, oleyl groups, cocoyl groups, etc.
  • plant or animal esters e.g. palm oil, rape seed oil, palm kernel oil, coconut oil, babassu oil, soybean oil, castor oil, tallow, tall oil, whale or fish oils, grease, lard, and mixtures thereof.
  • 364.1480PC groups include cocoyl, oleyl, tallowyl, tallyl, soyayl, rapeseedyl, palmyl groups and the like.
  • the naturally derived C8-C18 group is chosen from groups such as C8 – Caprylic, C10 – Capric, C12 – Lauric, C14 – Myristic, C15 – Pentadecylic, C16 – Palmitic, C17 – Margaric, C18 – Stearic, C14 – Myristoleic, C16’ – Palmitoleic, C18’ – Oleic, C18“ – Linoleic, and combinations thereof. Any one or more of these may be utilized herein.
  • a tallowyl group can be described as a C16-C18 group since about 95 mol% of its carbon chains fall within this range, whereas a cocoyl group includes a mixture of C 8 -C 18 chains wherein about 70 mol% are C12-C14 chains. Therefore, it is contemplated that any one or more naturally derived C8-C18 groups may include a distribution of compounds of varying chain lengths, as is understood by the skilled person. It is to be understood that anywhere “co” and/or “tallow” is used herein, it is contemplated that such a group may alternatively be an oleyl group or any other naturally derived C8-C18 group in other embodiments.
  • cocoyl refers to a hydrocarbyl chain that was obtained from coconut oil whereas the terminology coco is generally used in the art to relate to the source of the material, e.g. an oil or an acid or an alcohol.
  • m and n describe an average number of ethylene oxide and propylene oxide units/moles, respectively.
  • m+n is from 3 to 15, 4 to 14, 5 to 13, 6 to 12, 7 to 11, 8 to 10, or 9 to 10.
  • m+n may be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15.
  • m itself is any one of the values above such that n may be zero.
  • n itself is any one of the values above such that m may be zero.
  • m is from 3 to 8, 3 to 7, 3 to 6, 3 to 5, or 3 to 4, and n may be zero or any value above.
  • n is from 3 to 8, 3 to 7, 3 to 6, 3 to 5, or 3 to 4, and m may be zero or any value above.
  • all values and ranges of values, both whole and fractional, including and between those described above, are hereby expressly contemplated for use herein.
  • PCT PATENT APPLICATION ATTORNEY DOCKET NO. 364.1480PC [0041]
  • the phosphate ester includes or is a mixture or combination of phosphate monoester and a phosphate diester wherein the phosphate monoester has the following structure (Ia) and the phosphate diester has the following structure (Ib) (Ib) wherein each R’ has the , to 6.
  • the phosphate ester can be formed using a vegetable based C16- C18 and/or C18-unsaturated alcohol, e.g. a palm oil derivative.
  • an oleic chain e.g. an 9Z)-9-octadecen-1-yl chain can be utilized.
  • the phosphate ester comprises a mixture of a phosphate monoester and a phosphate diester such that the monoester is present in a mole ratio of greater than 1:1 to the diester. In other words, the phosphate monoester is present in a number of moles that is greater than the number of moles of the phosphate diester.
  • this ratio is of from about 0.6:1 to about 20:1 such that the phosphate monoester may be present in an amount less than, equal to, or more than the phosphate diester.
  • all values and ranges of values, both whole and fractional, including and between those described above, are hereby expressly contemplated for use herein. It is contemplated that each of the aforementioned ratios need not be limited to the particular chemistry set forth above and may be used in other embodiments with different R group chemistry.
  • at least one R of the phosphate ester is a C 16 -C 18 group.
  • At least one R of the phosphate ester is a cocoyl group or an oleyl group or a tallowyl group.
  • m+n is 3 to 6.
  • m is 3 to 6 and n is zero.
  • n is 3 to 6 and m is zero.
  • Amine Referring back to the amine, the amine has the following structure (II) PCT PATENT APPLICATION ATTORNEY DOCKET NO. 364.1480PC . [0046] Typically, the amine is either a amine, depending on substituents.
  • each of (or at least one of) R 1 , R 2 , and R 3 may be independently a naturally derived C 8 -C 18 group.
  • each of R 1 and R 3 may be independently a naturally derived C8-C18 group and R 2 may be H.
  • each of R 1 and R 3 may be independently a naturally derived C8-C18 group and R 2 may be CH 2 CH 2 CH 2 NH 2 .
  • R 1 may be a naturally derived C 8 -C 18 group and each of R 2 and R 3 may be (CH 2 CH 2 O) x H, wherein x is from 1 to 3.
  • the amine may be described as an unsymmetric amine and/or a functionalized amine.
  • the amine can be described as follows wherein: at least two of R 1 , R 2 , and R 3 are independently a naturally derived C 8 -C 18 group and R 2 is optionally H; or at least one of R 1 , R 2 , and R 3 is independently a naturally derived C 8 -C 18 group and one or two of R 1 , R 2 , and R 3 is CH 3 or 2-ethylhexyl, or R 1 a naturally derived C8-C18 group and R 3 is H or CH3 or (CH2CH2O)xH, wherein x is from 1 to 3 and R 2 is CH2CH2CH2NR 4 2 wherein R 4 is H or CH3 or (CH2CH2O)yH, wherein y is from 1 to 3; or R 1 is a naturally derived C 8 -C 18 group and each of R 2 and R 3 is (CH 2 CH 2 O) x H, wherein x is from 1 to 3.
  • each of R 1 , R 2 , and R 3 is independently a naturally derived C 8 - C18 group. This group may be any of those described above.
  • each of (or one or more of) R 1 , R 2 , and R 3 is a C 16 -C 18 group.
  • at least one of (or one or more of) R 1 , R 2 , and R 3 is an cocoyl group or a tallowyl group.
  • one or more may be cocoyl, one or more may be tallowyl, or one two may be tallowyl and the other cocoyl or one or two may be cocoyl and the other tallowyl.
  • R 1 , R 2 , and R 3 are independently a naturally derived C8-C18 group and R 2 is optionally H. Relative to a tertiary amine, R 2 is not H and may be any group described above or herein.
  • the amine is chosen from dimethyl cocoamine (C 8 - C18N(CH3)2), methyl di-cocoamine ((C8-C18)2NCH3), and combinations thereof.
  • the amine is dimethyl cocoamine (C8-C18N(CH3)2). In another embodiment, the amine is methyl di-cocoamine ((C 8 -C 18 ) 2 NCH 3 ). [0051] In another embodiment, at least one of R 1 , R 2 , and R 3 is independently a naturally derived C8-C18 group and one or two of R 1 , R 2 , and R 3 is 2-ethylhexyl. In another embodiment, the amine is 2-ethylhexyl(tallowyl)methylamine wherein R 1 is the naturally derived C 8 -C 18 group, R 2 is CH 3 , and R 3 is 2-ethylhexyl.
  • each of R 1 and R 3 is independently a naturally derived C8-C18 group, which may be any as described above, and R 2 is H.
  • each of R 1 and R 3 is a C16-C18 group.
  • at least one of R 1 and R 3 is an cocoyl group or a tallowyl group.
  • one or both may be cocoyl, one or both may be tallowyl, or one may be tallowyl and the other cocoyl.
  • at least two of R 1 , R 2 , and R 3 are independently a naturally derived C8-C18 group and R 2 is optionally H.
  • each of R 1 and R 3 is independently a naturally derived C 8 - C18 group, which may be any as described above, and R 2 is CH2CH2CH2NH2.
  • each of R 1 and R 3 is a C16-C18 group.
  • at least one of R 1 and R 3 is an cocoyl group or a tallowyl group. Alternatively, one or both may be cocoyl, one or both may be tallowyl, or one may be tallowyl and the other cocoyl.
  • R 1 is a naturally derived C 8 -C 18 group, which may be any as described above, and each of R 2 and R 3 is (CH2CH2O)xH, wherein x is from 1 to 3. Alternatively, x may be 1, 2, or 3 or may be 1 to 2 or 2 to 3. In one embodiment, R 1 is a C16- C 18 group. In another embodiment, R 1 is an cocoyl group or a tallowyl group. Additional Amines PCT PATENT APPLICATION ATTORNEY DOCKET NO.
  • R 1 , R 2 , and R 3 is independently a naturally derived C8-C18 group and one or two of R 1 , R 2 , and R 3 is CH3 or 2-ethylhexyl. Any one or more of the aforementioned naturally derived groups may be utilized.
  • one of R 1 , R 2 , and R 3 is CH 3 and the other two of R 1 , R 2 , and R 3 is the naturally derived C 8 -C 18 group.
  • two of R 1 , R 2 , and R 3 is CH3 and the other one of R 1 , R 2 , and R 3 is the naturally derived C8-C18 group.
  • R 1 is a naturally derived C 8 -C 18 group and R 3 is H or CH 3 or (CH2CH2O)xH, wherein x is from 1 to 3 and R 2 is CH2CH2CH2NR 4 2 wherein R 4 is H or CH3 or (CH2CH2O)yH, wherein y is from 1 to 3.
  • R 1 is a naturally derived C 8 -C 18 group and R 3 is H.
  • R 1 is a naturally derived C 8 -C 18 group and R 3 is CH 3.
  • R 1 is a naturally derived C8-C18 group and R 3 (CH2CH2O)xH, wherein x is from 1 to 3, e.g. 1, 2, or 3 or any range thereof.
  • R 2 is CH 2 CH 2 CH 2 NR 4 2 wherein R 4 is H.
  • R 2 is CH3.
  • R 2 is (CH2CH2O)yH, wherein y is from 1 to 3, e.g. 1, 2, or 3 or any range thereof.
  • R 1 is a naturally derived C8-C18 group and each of R 2 and R 3 is (CH2CH2O)xH, wherein x is from 1 to 3, e.g. 1, 2, or 3 or any range thereof.
  • one of R 1 , R 2 , and R 3 is a naturally derived C 12 -C 14 group and another of R 1 , R 2 , and R 3 is a naturally derived C 16 -C 18 group.
  • at least one of R 1 , R 2 , and R 3 is a cocoyl group or a tallowyl group.
  • each of R 1 and R 3 is independently a cocoyl group or a tallowyl group and R 2 is H.
  • the amine is chosen from: N-tallow-1,3-diaminopropane (C8- C18N(H)(CH2CH2CH2NH2), N.N.N'-trimethyl-N'-tallow-1,3-diaminopropane (C8- C 18 N(CH 3 )(CH 2 CH 2 CH 2 N(CH 3 ) 2 , tris(2-hydroxyethyl)-N-tallowalkyl-1,3-diaminopropane ((C8-C18N(CH2CH2OH) (CH2CH2CH2N(CH2CH2OH)2); and combinations thereof.
  • the amine is N.N.N'-trimethyl-N'-tallow-1,3-diaminopropane (C8- C 18 N(CH 3 )(CH 2 CH 2 CH 2 N(CH 3 ) 2 .
  • the amine is tris(2-hydroxyethyl)-N-tallowalkyl-1,3-diaminopropane ((C8-C18N(CH2CH2OH)(CH2CH2CH2N (CH2CH2OH)2).
  • R 1 is a cocoyl group or a tallowyl group and each of R 2 and R 3 is (CH 2 CH 2 O) x , wherein x is from 1 to 3.
  • R 1 is a naturally derived C8-C18 group and R 3 is H.
  • R 1 is a naturally derived C8-C18 group and R 3 is CH3.
  • R 1 is a naturally derived C 8 -C 18 group and R 3 is (CH 2 CH 2 O) x H, wherein x is from 1 to 3.
  • R 2 is CH2CH2CH2NR 4 2 wherein R 4 is H.
  • R 2 is CH 2 CH 2 CH 2 NR 4 2 , wherein R 4 is CH 3
  • R 2 is CH 2 CH 2 CH 2 NR 4 2 , wherein R 4 is (CH 2 CH 2 O) y H, wherein y is from 1 to 3.
  • R 1 is a cocoyl group or a tallowyl group.
  • at least one of R 1 , R 2 , and R 3 is independently a naturally derived C 8 -C 18 group and one or two of R 1 , R 2 , and R 3 is 2-ethylhexyl.
  • the amine may be 2- ethylhexyl(tallowyl)methylamine.
  • any one or more of the aforementioned embodiments may be combined together relative to one or more of R 1 , R 2 , and R 3 independently.
  • other amines may be used, for example, fatty esters of triethanolamine.
  • a non-limiting example of such an ester compound is fatty acids, tallow, compounded with triethanolamine, e.g. a mixture of tallow esters of triethanol amine (i.e. mono-, di- and triesters). This can also be described as mono-, di- and triesters of a tertiary hydroxyl amine and a fatty acid.
  • the composition may include, or be free of, one or more additives that is not the phosphate ester salt described above.
  • the composition may include, or be free of, one or more additives such as, but not limited to, metal deactivators, viscosity modifiers, detergents, friction modifiers, antiwear agents, corrosion inhibitors, dispersants, dispersant viscosity modifiers, extreme pressure agents, antioxidants, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents, and any combination or mixture thereof.
  • the composition includes from about 5 to about 25, about 5 to about 18, or about PCT PATENT APPLICATION ATTORNEY DOCKET NO.
  • the composition includes an ashless dispersant in an amount of from about 0.1 to about 20, e.g. about 1 to about 8, mass %.
  • the composition includes a metal detergent in an amount of from about 0.1 to about 15, e.g. about 0.2 to about 9, mass %.
  • the composition includes a friction modifier in an amount of about 0.1 to about 5, e.g.
  • the composition includes an antioxidant in an amount of from about 0.01 to about 5, e.g. about 0.01 to about 3, mass %. In other embodiments, the composition includes a pour point depressant in an amount of from about 0.01 to about 5, e.g. about 0.01 to about 1.5, mass %. In other embodiments, the composition includes an anti-foaming agent in an amount of from about 0.001 to about 5, e.g. about 0.001 to about 0.15, mass %. In other embodiments, the composition includes an antiwear agent in an amount of from about 0.01 to about 5, e.g. about 0.1 to about 2, mass %.
  • the composition includes a viscosity modifier in an amount of from about 0.01 to about 6, e.g. about 0.01 to about 4, mass %.
  • a viscosity modifier in an amount of from about 0.01 to about 6, e.g. about 0.01 to about 4, mass %.
  • dispersants include, for example, derivatives of long chain hydrocarbon-substituted carboxylic acids, examples being derivatives of high molecular weight hydrocarbyl-substituted succinic acid.
  • a noteworthy group of dispersants is constituted by hydrocarbon-substituted succinimides, made, for example, by reacting acids (or derivatives) with a nitrogen-containing compound, advantageously a polyalkylene polyamine, such as a polyethylene polyamine. Particularly typical are the reaction products of polyalkylene polyamines with alkenyl succinic anhydrides.
  • the composition includes, or is free of, one or more anti-wear agents that is not the phosphate ester amine salt of this disclosure.
  • anti-wear agents may include sulfur or phosphorous or both and may be capable of depositing polysulfide films on the surfaces involved.
  • dihydrocarbyl dithiophosphate metal salts wherein the metal may be an alkali or alkaline earth metal, or aluminum, lead, tin, molybdenum, manganese, nickel or copper.
  • zinc dihydrocarbyl dithiophosphate metal salts may be prepared in accordance with known techniques by first forming a dihydrocarbyl dithiophosphoric acid (DDPA), usually by reaction of one or more alcohols or a phenol with P2S5 and then neutralizing the formed DDPA with a metal compound.
  • DDPA dihydrocarbyl dithiophosphoric acid
  • a dithiophosphoric acid may be made by reacting mixtures of primary and secondary alcohols.
  • multiple dithiophosphoric acids can be prepared where the hydrocarbyl groups on one are entirely secondary in character and the hydrocarbyl groups on the others are entirely primary in character.
  • any basic or neutral metal compound could be used but the oxides, hydroxides and carbonates are most generally employed.
  • Commercial additives frequently include an excess of metal due to the use of an excess of the basic metal compound in the neutralization reaction.
  • the typical dihydrocarbyl dithiophosphate metal salts are zinc dihydrocarbyl dithiophosphates (ZDDP) which are oil-soluble salts of dihydrocarbyl dithiophosphoric acids.
  • the zinc dihydrocarbyl dithiophosphate comprises a zinc dialkyl dithiophosphate.
  • the composition includes an amount of dihydrocarbyl dithiophosphate metal salt that introduces from zero to about 0.10 mass % of phosphorus into the composition.
  • the composition is free of ZDDP.
  • PCT PATENT APPLICATION ATTORNEY DOCKET NO. 364.1480PC various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those described above, are hereby expressly contemplated for use herein.
  • the composition has a coefficient of friction as determined using ASTM D4172 that is at least about 20, 25, 30, 35, 40, 45, or greater, % less than that of a comparative composition that comprises zinc dialkyl dithiophosphate (ZDDP) in a comparative amount but is free of the phosphate ester amine salt.
  • ZDDP zinc dialkyl dithiophosphate
  • the instant composition has an improved coefficient of friction as described above.
  • the terminology “in a comparative amount” means that the ZDDP is included in an amount that may or may not be the same weight or molar amount as the phosphate ester amine salt but is an amount that would be known to be comparative by the skilled person.
  • such an amount is about ⁇ 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 mole or weight % different. It is contemplated that the above values may change depending on a content and type of base oil (e.g. oil of lubricating viscosity) that is used for the test. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those described above, are hereby expressly contemplated for use herein.
  • base oil e.g. oil of lubricating viscosity
  • the composition has a 4-ball wear preventative performance as determined using ASTM D4172 that has an average wear scar diameter that is at least about 10, 15, 20, 25, 30, 35, 40, 45, or greater % smaller than that of a comparative composition that comprises zinc dialkyl dithiophosphate (ZDDP) in a comparative amount, but is free of the phosphate ester amine salt.
  • ZDDP zinc dialkyl dithiophosphate
  • a comparative amount means that the ZDDP is included in an amount that may or may not be the same weight or molar amount as the phosphate ester amine salt but is an amount that would be known to be comparative by the skilled person. In various embodiments, such an amount is about ⁇ 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 mole or weight % different. It is contemplated that the above values may change depending on a content and type of base oil (e.g. oil of lubricating viscosity) that is used for the test. In various non-limiting embodiments, all values and ranges PCT PATENT APPLICATION ATTORNEY DOCKET NO.
  • composition is not limited to any particular total base number (TBN). However, in various embodiments, the composition has a TBN of from about 4 to about 15, about 5 to about 14, about 6 to about 13, about 7 to about 12, about 8 to about 11, or about 9 to about 10. In various non-limiting embodiments, all values and ranges of values, both whole and fractional, including and between those described above, are hereby expressly contemplated for use herein.
  • TBN total base number
  • the composition is also not limited relative to viscometric description.
  • the composition may be described as SAE 20WX, SAE 15WX, SAE 10WX, SAE 5WX or SAE 0WX, where X represents any one of 20, 30, 40 and 50 wherein the characteristics of the different viscometric grades can be found in the SAE J300 classification.
  • the composition is in the form of an SAE 10WX, SAE 5WX or SAE 0WX, In various embodiments in the form of an SAE 5WX or SAE 0WX, wherein X represents any one of 20, 30, 40 and 50.
  • X is 20 or 30.
  • the composition may be described as a transmission/gear oils.
  • Typical transmission oil grades are SAE 80W, 75W-90, 80W-90 and SAE 90.
  • the composition may be described as a hydraulic oil which has ISO viscosity grades and typical ISO grades such as ISO VG 32, ISO VG 46, ISO VHG 68, and ISO VG 100.
  • the composition is not limited in its use and may be used to lubricate mechanical engine components, particularly in internal combustion engines, e.g. spark-ignited or compression-ignited two- or four-stroke reciprocating engines.
  • the engines may be conventional gasoline or diesel engines designed to be powered by gasoline or petroleum diesel, respectively; alternatively, the engines may be specifically modified to be powered by an alcohol-based fuel or biodiesel fuel.
  • the composition is a crankcase lubricant.
  • the composition is used in the lubrication of a compression- ignited internal combustion engine (diesel engine), especially a compression-ignited internal combustion engine which is fueled at least in part with a biodiesel fuel.
  • diesel engine a compression- ignited internal combustion engine
  • Such engines include passenger car diesel engines and heavy duty diesel engines, for example engines found in road PCT PATENT APPLICATION ATTORNEY DOCKET NO. 364.1480PC trucks.
  • the composition is used in the lubrication of a passenger car compression-ignited internal combustion engine (e.g. a light duty diesel engine), which is fueled at least in part with a biodiesel fuel, e.g.
  • the composition is used in the lubrication of a crankcase of the aforementioned engines.
  • Method of Forming the Composition may be formed by any method known in the art.
  • the method includes the step of providing the oil of lubricating viscosity, providing the phosphate ester amine salt, and combining the oil and the salt to form the composition.
  • the method may include the step of providing one or more additives and the step of combining the one or more additives with the oil, the salt, and/or with the combination of the oil and the salt, to form the composition.
  • the method may include batch or continuous steps.
  • the method of forming the phosphate ester amine salt is not particularly limited and may be any known in the art.
  • the method of forming the composition itself may include one or more steps of the synthesis of the phosphate ester amine salt.
  • the phosphate ester amine salt may be formed entirely independently from the method of forming the composition.
  • the phosphate ester amine salt may be provided in an already formed state.
  • the reaction to form the phosphate ester amine salt may generally proceed as follows wherein ultimate charge balance is understood by those of skill in the art: [0096] Typically, the skilled person determines the base number (BN) of the amine and the acid number (AN) of the phosphate ester independently.
  • the amine can have two base numbers if it is a diamine.
  • the phosphate ester For example, the phosphate PCT PATENT APPLICATION ATTORNEY DOCKET NO. 364.1480PC monoester has a certain acid number while the phosphate diester has a different acid number.
  • the skilled person can neutralize about 95 mol% of the phosphate monoester with the amine based on the measured BN and AN values, wherein the extent of the reaction is determined potentiometrically.
  • the skilled person may choose to not neutralize the phosphate diester because it is typically more difficult.
  • the skilled person can choose to react one or both of the amine moieties with the phosphate monoester. Therefore, the terminology “salt” has a broad definition and neutralization can mean different things, each as understood by the skilled person.
  • the terminology “phosphate ester amine salt” may include compounds generated by any one or more of the aforementioned methods, again as is understood by the skilled person.
  • the phosphate ester amine salt may be formed as described in WO 2018/017449, which is expressly incorporated herein by reference in its entirety in various non-limiting embodiments.
  • EXAMPLES [0097] The following examples, illustrating embodiments of this disclosure, are intended to illustrate and not to limit the scope of the embodiments described herein. Unless otherwise noted, all solvents, substrates, and reagents are purchased or otherwise obtained from various commercial suppliers and utilized as received (i.e., without further purification) or as in a form used conventionally in the art.
  • General Procedure For Formation Of Salts [0098] Various phosphate ester amine salts were synthesized using the same or similar procedure as described hereafter.
  • the temperature of the reaction mixture was raised to 75°C, after which, under a stream of nitrogen, 0.95 equivalents (247.47 grams) of amine AM1 (amine value 4.276 mmole/g) was dosed over a period of 1 hour. During dosing, the temperature was kept between 75 and 80°C.
  • the PCT PATENT APPLICATION ATTORNEY DOCKET NO. 364.1480PC temperature was brought to 100°C, and the mixture was allowed to react for an additional 4 hours. Under a reduced pressure of 100 mbar, for 1 hour, water from the phosphate ester was distilled off. The product was collected as an oil. [0099] The procedure described above is common to all of the phosphate ester amine salts in the Examples below.
  • Phosphate Esters Phosphatized naturally derived C 16 -C 18 fatty alkoxylated alcohol, source of P1 alkoxylation is ethylene oxide, with average alkoxylation degree of 4, with a pyrophosphate content less than 1%, mono to diester ratio in the range of 1-1.5, and a phosphorous content of 4.8%
  • Phosphatized naturally derived C 16 -C 18 fatty alkoxylated alcohol, source of alkoxylation is ethylene oxide, with average alkoxylation degree of 4, with a P2 pyrophosphate content from 25% to 35%, mono to diester ratio in the range of 0.5-1, and a phosphorous content of 5.6%
  • Phosphatized naturally derived C16-C18 fatty alkoxylated alcohol, source of alkoxylation is propylene oxide, with average alkoxylation degree of 4, with a P3 pyrophosphate content less than 1%, mono to diester ratio in the range of 1-1.5, and a phosphorous content of
  • the antiwear and friction-reducing performances were benchmarked against a commercial amine phosphate derived from C 11 -C 14 branched alkylamines and mono- of dihexyl phosphates, with a phosphorus content of 4.8% (referred to as 'AP' hereinafter), and a primary zinc dialkyldithiophosphate with a phosphorus content of 9.5% (referred to as 'ZDDP' hereinafter).
  • 'AP' a commercial amine phosphate derived from C 11 -C 14 branched alkylamines and mono- of dihexyl phosphates, with a phosphorus content of 4.8%
  • 'ZDDP' primary zinc dialkyldithiophosphate with a phosphorus content of 9.5%

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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

Une composition lubrifiante est sans cendre, exempte de métal et exempte de soufre et comprend une huile de viscosité lubrifiante et environ 0,05 à environ 3 % en poids d'agents actifs d'un sel d'amine d'ester de phosphate sur la base d'un poids total de la composition. Le sel d'amine d'ester de phosphate est le produit de réaction d'un ester de phosphate particulier et d'une amine particulière.
PCT/EP2024/060452 2023-04-18 2024-04-17 Composition lubrifiante comprenant un sel d'amine d'ester de phosphate WO2024218169A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3169923A (en) * 1962-03-22 1965-02-16 Universal Oil Prod Co Oil of lubricating viscosity
JP2002060773A (ja) * 2000-08-18 2002-02-26 Asahi Denka Kogyo Kk 潤滑剤
WO2015116233A1 (fr) * 2014-02-03 2015-08-06 Fuchs Petrolub Se Compositions d'additifs et fluides de traitement industriels
WO2018017449A1 (fr) 2016-07-20 2018-01-25 The Lubrizol Corporation Sels d'amines de phosphate d'alkyle utilisables dans des lubrifiants
JP6472721B2 (ja) * 2015-06-24 2019-02-20 竹本油脂株式会社 摺動面用潤滑油組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3169923A (en) * 1962-03-22 1965-02-16 Universal Oil Prod Co Oil of lubricating viscosity
JP2002060773A (ja) * 2000-08-18 2002-02-26 Asahi Denka Kogyo Kk 潤滑剤
WO2015116233A1 (fr) * 2014-02-03 2015-08-06 Fuchs Petrolub Se Compositions d'additifs et fluides de traitement industriels
JP6472721B2 (ja) * 2015-06-24 2019-02-20 竹本油脂株式会社 摺動面用潤滑油組成物
WO2018017449A1 (fr) 2016-07-20 2018-01-25 The Lubrizol Corporation Sels d'amines de phosphate d'alkyle utilisables dans des lubrifiants

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Engine Oil Licensing and Certification System", INDUSTRY SERVICES DEPARTMENT, December 1996 (1996-12-01)

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