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WO2025221891A1 - Nouveaux modificateurs de frottement - Google Patents

Nouveaux modificateurs de frottement

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Publication number
WO2025221891A1
WO2025221891A1 PCT/US2025/024968 US2025024968W WO2025221891A1 WO 2025221891 A1 WO2025221891 A1 WO 2025221891A1 US 2025024968 W US2025024968 W US 2025024968W WO 2025221891 A1 WO2025221891 A1 WO 2025221891A1
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WO
WIPO (PCT)
Prior art keywords
compounds
formula
composition
base oil
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/024968
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English (en)
Inventor
Christopher John CLAYSON
Kevin John DUNCAN
Jonathan David Townend
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cargill Inc
Original Assignee
Cargill Inc
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Filing date
Publication date
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Publication of WO2025221891A1 publication Critical patent/WO2025221891A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/76—Esters containing free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/22—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/102—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the present disclosure relates to biobased friction modifiers for lubricants that can be used in a variety of industrial applications including gear, engine, and transmission applications. Use of biobased ingredients is increasingly preferred to lower the carbon footprint of industrial products.
  • Lubricants and process fluids industries are increasingly searching for materials that are biobased and biodegradable.
  • One of the largest losses of energy in any mechanical system is friction. When mechanical energy is converted to heat through friction it is lost to the environment and the efficiency of the mechanical system suffers.
  • Lubricants and process fluids are complex systems and vary depending on the particular needs of the application. Often these lubricant systems contain a minor component distinct from the lubricant specifically tailored to reduce friction and accordingly increase the efficiency of the system. These materials are often referred to as friction modifiers or traction control additives.
  • the present disclosure describes novel biobased friction modifiers for use in mechanical systems.
  • Biobased means that the materials described herein are derived from sustainable plant sources as opposed to non-regenerable or sustainable sources such as petroleum.
  • Biodegradability means that the lubricants and process fluids (hereinafter “fluids”) have the ability in a natural environment to degrade over a period of time, which may be measured by tests such as those promulgated by the Organization of Economic Co-Operation and Development (OECD).
  • Fluids lubricants and process fluids
  • OECD Organization of Economic Co-Operation and Development
  • Renewable biobased products contain, by definition, high levels of renewable carbons, and standards are being set to encourage increasingly greater levels of renewability.
  • the European Ecolabel now stresses that hydraulic fluids should be biodegradable and preferably contain at least 50 percent by weight renewable carbons.
  • Traction additive packages can be expensive and consumed during the lifetime of their use. Therefore, novel biobased additives to improve the traction performance of base oils is highly desired.
  • compositions described herein exhibit the surprising ability to reduce the traction, or friction, in lubricant formulations even if utilized in modest quantities in the overall formulation.
  • Compounds of this type are commonly referred to as “friction modifiers”.
  • the compounds disclosed herein are utilized at less than 10% of the final formulation and even more typically at between 2% and 6%. They can be utilized in low or high viscosity formulations and can be tailored to a variety of end applications. This level of stability for biobased material is unique and highly valuable to the end user.
  • the compounds of Formula 1 are cheaper and easier to produce than currently utilized alternatives.
  • compositions comprising a base oil wherein the base oil comprises 0.5% to 9.9% of one or more compounds of the Formula 1 :
  • n is an integer from 2-6; R is C1-C12 alkyl; R2 is C5-C11 alkyl; R3 is C4-C10 alkyl.
  • lubricating compositions comprising 0.5% to 9.9% of one or more compounds of the Formula 1 : wherein n is an integer from 2-6; R is C1-C12 alkyl; R2 is C5-C11 alkyl; R3 is C4-C10 alkyl.
  • the lubricating composition may contain 10%-100% of a base oil.
  • the lubricating composition may comprise 50%-100% of the base oil.
  • Figure 1 shows the GPC data for an Example of the present disclosure (Example 1 IB) where the polymeric distribution of the material is represented.
  • Figures 2-7 show the traction curve data for Examples of the present disclosure (as mentioned below) where the traction of a lubricant formulations are compared with and without the compounds of the present disclosure.
  • values expressed in a range format should be interpreted in a flexible manner to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range is explicitly recited.
  • a range of “0.1% to 5%” or “0.1% to 5%” should be interpreted to include not just 0.1% to 5%, but also the individual values (e.g., 1%, 2%, 3%, and 4%) and the sub-ranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the indicated range.
  • the term “less than” means a value lower than the reference value stated.
  • the term “less than” is intended to include situations where presence of the measured variable may be non-detectable but is not intended to mean the absolute absence of a measured variable is possible or desirable.
  • an Acid Value (AV) of less than 0.3 is intended to include the range from 0.3 to an AV that is non-detected but is not intended to mean an absolute value of zero is possible or desired.
  • the acts can be carried out in any order without departing from the principles of the disclosure, except when a temporal or operational sequence is explicitly recited. Furthermore, specified acts can be carried out concurrently unless explicit claim language recites that they be carried out separately. For example, a claimed act of doing X and a claimed act of doing Y can be conducted simultaneously within a single operation, and the resulting process will fall within the literal scope of the claimed process.
  • substantially refers to a majority of, or mostly, as in at least about 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98%, 99%, 99.5%, 99.9%, 99.99%, or at least about 99.999% or more, or 100%. In some aspects, substantially means greater than 90%. In some aspects, substantially means greater than 75%.
  • alkyl as used herein means a saturated or unsaturated, branched, or straight-chain monovalent, or divalent, hydrocarbon radical derived by the removal of one, or two, hydrogen atoms from the carbon atoms of a parent alkane, alkene, or alkyne. In some aspects, one or more of the alkyl groups are substantially saturated. In some aspects, one or more of the alkyl groups are fully or partially saturated.
  • C1-C22 alkyl; C2-C12, C3-C12; and C1-C10 alkyl means alkyl groups containing 1-22, 2-12, 3-12 and 1-10 carbons. Any similar numerical ranges should be considered likewise.
  • alkyl groups may be branched.
  • alkyl groups may be unbranched or straight.
  • the alkyl groups may be a mixture of branched or unbranched.
  • One or more of the alkyl groups may be saturated, unsaturated, or a mixture there of.
  • the alkyl groups may substituted, unsubstituted, or a mixture thereof.
  • substituted means that one of the hydrogen atoms of the alkyl chain is replaced by another substituent.
  • the alkyl groups are substituted in one more places by hydroxyl, amino, dialkyl amino, alkyl acetylated hydroxyl, an alkyl ester, or an alkyl ether substituent.
  • the alkyl group is substituted with a hydroxyl or alkylacetylated hydroxyl group.
  • Base Oil as used herein means the primary lubricating components of a lubricant formulation not including additional performance additives.
  • the base oil may be a single lubricating components or a mixture of multiple lubricating components depending on the particular needs of the intended application.
  • Each viscosity grade is designated by the nearest whole number to its midpoint kinematic viscosity in mm2/s at 40°C (104°F), and a range of +/- 10 percent of this value is permitted.
  • the 20 viscosity grades with the limits appropriate to each are listed below.
  • the classification is based on the principle that the midpoint (nominal) kinematic viscosity of each grade should be approximately 50 percent greater than that of the preceding one.
  • an ISOIOO oil would define an oil with a kinematic viscosity between 90 cSt and 110 cSt at 40°C and an ISO 320 oil would define an oil with a kinematic viscosity between 288 cSt and 352 cSt at 40°C.
  • n is an integer from 2-6; R is C1-C22 alkyl; R2 is C3-C12 alkyl; 3 is hydrogen or C1-C10 alkyl.
  • the compounds of Formula 1 are those wherein R is a C3-C12 alkyl.
  • R is a branched Ce-Cio alkyl.
  • R is 2-ethylhexyl.
  • the compounds of Formula 1 are those where R2is a C5-C11 alkyl.
  • R2 is a straight chain saturated or unsaturated C7-C11 alkyl.
  • R2 is a straight chain C11 alkyl.
  • the compounds of Formula 1 are those where R3 is a branched C4-C12 alkyl. In other aspects, is a straight chain C4-C8 alkyl. In other aspects, R3 is a straight chain Ce alkyl.
  • the compounds of Formula 1 are those where R is 2-ethylhexyl, R2 is a straight chain C9 alkyl, and 3 is a straight chain Ce alkyl.
  • a subset of the compounds of Formula 1 can be represented as compounds of Formula 3. wherein n is an integer from 2-6 and R is C1-C22 alkyl.
  • the compounds of Formula 1 or the compounds of Formula 3 can be present as a mixture of oligomers wherein with the majority of the oligomers contain between 2 and 6 units and greater than 50% of the oligomers contain 3 or more units.
  • Compounds of Formulas land 3 can be prepared through the oligomerization of a hydroxy substituted fatty acid (or mixture of hydroxy substituted fatty acids) and subsequent esterification of the remaining acid groups with an alcohol.
  • Hydroxy substituted fatty acids are known in the art, commercially available, and may be prepared by one of skill in the art. As shown in the Examples 12-hydroxy stearic acid and 10-hydroxy stearic acid maybe used to prepare compounds of Formula 1. Either enantiomer, or a mixture thereof, of the hydroxystearic acid is functional in the present disclosure.
  • hydroxy substituted fatty acids are known in the art and may be prepared by example through epoxidation of an unsaturated fatty acid followed by reductive ring opening can yield a variety of monohydroxy fatty acid residues.
  • 10-hydroxy stearic acid (CAS: 638-26-6) is known in the art and can be purchased or prepared by enzymatic treatment of oleic acid.
  • 12-Hydroxy stearic acid (CAS: 106-14-9) can be directly derived from castor oil and is commercially available from a variety of companies such as Gokul Overseas, Jay ant Agro-Organics Ltd, De Monchy UK Ltd; Acme Hardesty, or Hampshire Commodities Ltd. Because commercially available 12-hydroxy stearic acid is derived from castor oil, it typically contains a quantity of stearic acid as an impurity. A representative example of commercially available 12-hydroxystearic acid is shown in the examples.
  • a hydroxy substituted fatty acid, or mixture of acids can be oligomerized at elevated temperature using a tin, titanium, or nitrogen containing catalyst where the formed water is removed.
  • the reaction is typically performed in the absence of a solvent, but some a small amount of solvent could optionally be used.
  • the water removal may be accomplished by means of an entrainer, reduced pressure, and/or nitrogen sparging.
  • the result of this step is an oligomerized acid which includes a distribution of compounds of Formula 2 as follows:
  • n is an integer from 2-6; R2 is C3-C12 alkyl; R3 is hydrogen or C1-C10 alkyl.
  • the progress of the oligomerization may be tracked by the reduction in acid value of the reactants.
  • the degree of oligomerization may be limited by the presence of other fatty acids in the starting materials that effectively endcap the reactive hydroxyl group. For example, typically, a distribution is achieved with the majority of the oligomers containing between 2 and 6 units and greater than 50% containing 3 or more units.
  • Figure 1 shows the GPC distribution of an Example 1 IB of the present disclosure.
  • pre-oligomerized hydroxyfatty acids are also commercially available such a Hyperm er LP1 from Croda.
  • the Compounds of Formula 2 can then be esterified by reaction with a straight or branched alcohol having from 1 to 22 carbon atoms.
  • the alcohol may be selected from methanol, ethanol, isopropanol, butanol, 2-ethylhexanol, 2-(2-butoxypropoxy)propan-l-ol (DPnB), 1-decanol, 1-octanol, 2-octanol, and Isofol 18 (2-Octyl decyl). Additional tin, titanium, nitrogen, or acid containing catalyst may be employed at this point, and formed water is removed, yielding an esterified product of Formula 1 with an AV of less than 1.0 KOH/g or less than 0.2mg KOH/g.
  • compounds of Formula 1 can be prepared in a single pot by reacting a hydroxy fatty acid with an alcohol directly.
  • the hydroxy fatty acid is heated in the presence of an excess of alcohol under nitrogen.
  • Catalyst such as TNBT is typically added part way though the reaction to reach an AV of less than 0.2mg KOH/g.
  • Base oils may further comprise one more compounds of Formula 4:
  • n is an integer from 2-6; R is C1-C22 alkyl; R2 is C3-C12 alkyl; R3 is hydrogen or C1-C10 alkyl, and R4 is C1-C22 acyl.
  • compounds of Formula 4 are those wherein R is 2-ethylhexyl, R4 is a Cl 8 acyl, R2 is a straight chain C9 alkyl, and R3 is a straight chain Ce alkyl.
  • the compounds of Formulas 1, 3, and 4, or mixtures thereof may be formulated into lubricating compositions by combination with base oils and/or additives. Preparation of lubricating compositions is known in the art and any effective method may be utilized. Typically, ingredients in the formulation are mixed at ambient or elevated temperatures. Mixing can be performed batchwise or continuously as desired. In certain embodiments, the lubricating composition further comprises one or more additives known to those in the art such as friction modifiers, viscosity modifiers, antioxidants, anti-wear additives, extreme pressure additives, defoamers, demulsifers, and corrosion inhibitors. Additives are typically included in the final formulations at a level between 1 and 20% depending on the particular application and needs of the user.
  • Additives may be included separately or as part of what is known in the art as an add pack.
  • An add pack is a commercially available mixture of additives formulated by a supplier for inclusion in particular base oils and for particular applications.
  • the lubricating composition comprises l%-10% additives by weight. In some aspects, the lubricating composition comprises 2%-6% additives by weight.
  • Base oils in which the compositions of this disclosure are employed can be based on natural or synthetic oils, or blends thereof can be formulated into final gear oil formulations, provided the lubricant has a suitable viscosity for use in desired applications.
  • the base oils for such use can be mineral oil base stocks such as for example conventional and solvent-refined paraffinic neutrals and bright stocks, hydrotreated paraffinic neutrals and bright stocks, naphthenic oils, cylinder oils, etc., including straight run and blended oils.
  • base oil is selected from the group consisting of polyalphaolefins (PAOs), synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, long chain alkyl esters such as those described and disclosed in WO2022/258664, and mixtures thereof.
  • PAOs polyalphaolefins
  • synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, long chain alkyl esters such as those described and disclosed in WO2022/258664, and mixtures thereof.
  • Synthetic base stocks can also be used in the practice of this invention, such as for example PAO, alkylated aromatics, polybutenes, diesters, polyol esters, polyglycols, polyphenyl ethers, etc., and blends thereof.
  • Polyalphaolefins are typically manufactured from C8 to Cl 4 olefins, and the result is generally combinations of dimers, trimers, tetramers, pentamers, and so forth. It is also known for PAOs and esters to be blended with mineral oils to form semi synthetics. Synthetic base oils are preferred, especially base oils having PAO or mixtures of PAOs as a major component.
  • PAOs are well known and readily available such as Chevron - Synfluid, Exxon - Spectrasyn, INEOS - Durasyn, and the like. Synthetic esters are also well known such as Oleon - Radialube, NYCO - NYCOBASE, Lanxess - Hatcol, and Exxon - Esterex. The skilled artisan is well aware of the technical properties of these materials and how to blend them to a desired outcome.
  • the compounds of Formula 1 may be used in base oils in the preparation of a final lubricating formulation.
  • the base oil comprises 0.5% to 9.9% of one or more of the compounds of Formula 1.
  • compounds of Formula 1 comprise between 2 and 9.9%; between 2% and 8%, between 4% and 8%, or between 4% and 10% of the lubricating composition.
  • the compounds of Formula 3 may be used in base oils in the preparation of a final lubricating formulation.
  • the base oil comprises 0.5% to 9.9% of one or more of the compounds of Formula 3.
  • compounds of Formula 3 comprise between 2 and 9.9%; between 2% and 8%, between 4% and 8%, or between 4% and 9.9% of the lubricating composition.
  • the compounds of Formula 1 may be used in base oils in the preparation of a final lubricating composition.
  • the lubricating composition comprises 0.5% to 9.9% of one or more of the compounds of Formula 3.
  • compounds of Formula 1 comprise between 2 and 9.9%; between 2% and 8%, between 2% and 6%, or between 4% and 9.9% of the lubricating composition.
  • the compounds of Formula 3 may be used in base oils in the preparation of a final lubricating composition.
  • lubricating composition comprises 0.5% to 9.9% of one or more of the compounds of Formula 3.
  • compounds of Formula 3 comprise between 2 and 9.9%; between 2% and 8%, between 2% and 6%, or between 4% and 9.9% of the lubricating composition.
  • the base oil comprises 0.5% to 9.9% of one or more of the compounds of Formula 1 and further comprises one more compounds of Formula 4.
  • the base oil comprises 0.5% to 9.9% of one or more of the compounds of Formula 3 and further comprises one more compounds of Formula 4.
  • the reaction was heated to 190°C and vacuum applied with caution to achieve a steady reflux of 2-EH into the trap. Reflux was maintained during the reaction by lowering the pressure as necessary. After 8h under reaction conditions (l lh total reaction time) the AV was measured to be 7.0mg KOH/g. Catalyst (TNBT, 0.2 ml) was added and the reaction allowed to progress for a further 5.5 h (16.5h total reaction time), after which the AV of the reaction had reached ⁇ 0.2mg KOH/g. The reaction temperature was adjusted to 125°C and full vacuum applied to remove the excess 2-EH through the trap.
  • Example IB was a repeat experiment with the same stoichiometry as 1 A, however, the hydroxystearic acid oligomerization was run for 4 hours to an AV of 65.3mg KOH/g prior to the introduction of the 2-EH.
  • Example 1C was a repeat experiment with the same stoichiometry as 1 A, however, the hydroxystearic acid oligomerization was run for 3.5 hours to an AV of 70 mg KOH/g prior to the introduction of the 2-EH.
  • Example ID is a repeat of 1C.
  • Example IE is repeat of Example 1A with a 10% stoichiometric increase in 2-EH.
  • Example 1 The material from Example 1 was returned to a reaction vessel.
  • a second 250ml 3- necked flask was charged with 50ml distilled water and a sizable quantity of anti-bumping granules, and fitted with a sintered gas distribution tube via a length of PTFE tubing.
  • the gas distribution tube was introduced into the sample reaction vessel so that the sintered end was as low as possible without fouling the stirred blade.
  • the steam vessel was placed in a water bath on a hot-plate stirrer with a set point of 30°C.
  • the reaction vessel contents were heated to 115°C under a separate nitrogen purge. At the set temperature the nitrogen purge was shut off and vacuum applied, causing low temperature steam to be drawn through the gas distribution tube and sparge through the reaction bulk. After approximately 3 hours the heat was removed and the vacuum tap closed. Once at room temperature the vacuum was released though the steam sparge by repressurising the steam generator flask.
  • Example 3 After 2.5h the temperature was reduced to 180°C, 0.2 ml TNBT was added and the reaction allowed to progress for a further 16h, after which time the AV had fallen to 1.36mg KOH/g. An additional 0.2ml TNBT was added and the reaction continued for a further 24h after which time the AV had fallen to O.lmg KOH/g. The temperature was reduced to 120°C and vacuum applied with a nitrogen sparge for 3h and the product filtered through SW-10 cellulose filter aid overnight to yield the material of Example 3.
  • the reaction was initially heated to 180°C before gradually increasing the temperature to 200°C, rate of heating controlled by rate of water evolution, ⁇ 2 hours.
  • TnBT catalyst ( ⁇ 0.2g) and 2-octanol ( ⁇ 10mls) were added to the reaction vessel, Acid Value ⁇ 20mgKOH/g.
  • the reaction was maintained at 200°C until the reaction was complete (AV ⁇ 0.2mgKOH/g).
  • An additional dose of TnBT catalyst (0.2g) and 2-octanol ( ⁇ 10mls) were added after 16 hours.
  • the product was cooled to 110°C, then activated carbon ( ⁇ 1 wt%) was added to the reaction vessel and vacuum was applied ( ⁇ 5 mbar). Reaction conditions were maintained for 5 hours before the product was discharged and filtered. The material was vacuum filtered using Fibra-cel SW-10 as the filter aid.
  • the reaction was initially heated to 160°C before gradually increasing the temperature to 200°C, rate of heating controlled by rate of water evolution, ⁇ 3 hours.
  • Tyzor TnBT catalyst ⁇ 0.4g
  • 1-decanol ⁇ 25mls
  • the reaction was maintained at 200°C until the reaction was complete (AV ⁇ 0.2mgKOH/g), approximately 24 hours.
  • the product was cooled to 145°C, then activated carbon ( ⁇ 1 wt%) was added to the reaction vessel and vacuum was applied ( ⁇ 5 mbar). Reaction conditions were maintained for 5 hours before the product was discharged and filtered. The material was vacuum filtered using Fibra-cel SW-10 as the filter aid.
  • the product, 1 -decyl poly( 12-hydroxy stearate) was an off white, paste like solid.
  • the reaction was maintained at 190°C as TnBT catalyst was added ( ⁇ 1.7g).
  • the reaction was maintained at 190°C until the reaction was complete (AV ⁇ 0.2mgKOH/g), approximately 38 hours.
  • the reaction was cooled to 120°C.
  • the reaction was reconfigured for steam stripping: a subsurface nitrogen sparge was connected to a 1 liter, 3 necked round bottomed flask filled with water, ⁇ 500g, and anti-bumping granules.
  • the nitrogen / steam exhaust tube from the 3 necked flask was connected to a sub-surface sparge in the reactor vessel.
  • the reaction was heated to 110°C and vacuum applied ( ⁇ 20 mbar), the nitrogen flow to the vessel was reduced to a minimal amount.
  • the water in the flask was heated gently with a heat gun to allow the water to remain at room temperature and a vigorous bubbling of gas (nitrogen + steam) in the reaction vessel observed: for a constant vacuum, the temperature of the water will dictate the vigor of the steam strip process.
  • the product was discharged, filtered (filter aid: Celite® 512) and subject to full analytical work up.
  • the product 2-ethylhexyl poly 12-hydroxy stearate, a clear, amber, viscous liquid.
  • Example 6 Material prepared according to Example 6 (550.0g), activated carbon ( ⁇ 1 wt%) and Tonsil Optium 210-ff ( ⁇ 1 wt%) were charged to a 5-necked round bottomed flask equipped with a sub-surface nitrogen sparge ( ⁇ 30ml /min), overhead stirrer with centrifugal stirrer bar ( ⁇ 400rpm), temperature feedback loop, condenser set for distillation removal and collection flask. The collection flask was fitted with both a dreschel bottle, to ensure a nitrogen atmosphere, and vacuum capabilities. The reaction was heated to 110°C and then vacuum was applied ( ⁇ 5 mbar). Reaction conditions were maintained for 3 hours before the reaction was re-pressurized and the product discharged and filtered, using Celite® 512 as a filter aid. The product was a clear, amber, viscous liquid.
  • Example 8 Example 8
  • the reaction was heated to and maintained at 100°C for approximately 5 hours before the reaction was reconfigured for steam stripping: a subsurface nitrogen sparge was connected to a 1 liter, 3 necked round bottomed flask filled with water, ⁇ 500g, and anti-bumping granules. The nitrogen / steam exhaust tube from the 3 necked flask was connected to a sub-surface sparge in the reactor vessel. The reaction was heated to 110°C and vacuum applied ( ⁇ 20 mbar), the nitrogen flow to the vessel was reduced to a minimal amount.
  • the water in the flask was heated gently with a heat gun to allow the water to remain at room temperature and a vigorous bubbling of gas (nitrogen + steam) in the reaction vessel observed: for a constant vacuum, the temperature of the water will dictate the vigor of the steam strip process. These conditions were maintained for 3 hours before repressurizing and replacing the steam sparge with the nitrogen purge. Activated carbon ( ⁇ 1 wt%) was added to the vessel and vacuum was applied ( ⁇ 5 mbar). Reaction conditions were maintained for 3 hours before the reaction was repressurized and the product discharged and filtered, using Celite® 512 as a filter aid. The product, 2-ethylhexyl poly-12-hydroxystearyl acetylate, a clear, pale yellow, viscous liquid.
  • gas nitrogen + steam
  • the Dean and Stark trap initially filled with 2-EH but once this was displaced by the water of reaction the level of water in the trap was held at greater than ca. 80% maintained the excess of alcohol in the reaction vessel. After 3 h the temperature of the reaction had reached 200°C and the set point was increased to 220°C. After a further 1.5 h a total of 54 ml water had been removed from the reaction vessel. Catalyst (TNBT, 0.2 ml) was added and the reaction allowed to progress for a further 16 h after which the AV of the reaction had reached ⁇ 0.2mg KOH/g. An additional 0.2 ml TNBT was added and the reaction continued for a further 3 h.
  • the mixture was cooled to 110°C, de-colorizing charcoal (5g) added and vacuum applied cautiously to prevent foaming to remove excess 2-EH for 2h.
  • the charcoal was removed by filtration and full vacuum applied at 125°C with a nitrogen sparge until no free 2-EH was detected in the product by GC or odor.
  • Table 5 shows the oxidative stability (induction time) of the Examples described above.
  • Benchmark 1 is a commercially available endcapped estolide sold by Biosynthetics under the product code BT22.
  • Benchmark 2 is a commercially available high performing pentaerythritol tetraisostearate esters sold by Cargill Incorporated under the brand name Priolube 3987.
  • Tables 5, 6, and 7 show the comparison of the stability of a compounds of Formula 1 with an endcapped acylated version as well with two commercial benchmarks. It is very surprising that the Examples of formula 1 containing free hydroxyl groups (as demonstrated by the hydroxyl value) are approximately 7 times more stable than the corresponding acylated version. This is a dramatic and unexpected increase in oxidative stability that would be highly advantageous to an end user.
  • the vessel was inspected to ensure it was clean and in working order before the oil jacket was set to 90°C constant oil temperature.
  • the vessel was sealed, ensuring the main drain valves were shut before a full vacuum was applied to assess if the vessel was vacuum tight.
  • the vacuum was released with nitrogen before the 12-hydroxy stearic acid was charged via the sight glass port.
  • Table 8 Table 8 below. Once charged the sight glass port was closed and the constant oil temperature was increased to 160°C with 100 ml/min nitrogen headspace.
  • the vessel was cooled to ⁇ 140°C constant reactor temperature before a small access port on the lid of the vessel was unscrewed.
  • the required 2-ethyl hexanol was charged to the vessel before the port was reclosed.
  • the binary separator was filled with l/3 rd water and 2/3 rd 2-ethyl hexanol.
  • the vessel was then set to 190°C constant reactor temperature and once reached the pressure was reduced to 800 mbar. The pressure was then reduced periodically to maintain a suitable level of reflux.
  • the vessel was set to 125°C constant reactor temperature and the stirrer speed was increased to 200 rpm.
  • the binary separator was drained; with any water being discarded and any 2-ethyl hexanol kept for further batches.
  • the pressure in the vessel was reduced to ⁇ 50 mbar and free 2-ethyl hexanol distilled out of the vessel into the binary separator.
  • the vessel was set to 110°C and the vacuum was broken with nitrogen.
  • a vacuum rated nylon tube was attached to the reactor and the other end was attached to a valve fitted to a 500 ml three-neck flask.
  • a thermometer and a second valve were fitted to the other necks of the flask.
  • the three-neck flask was then placed into a DrySyn block on a hotplate with a feedback probe in the block. Water and anti-bumping granules were placed into the flask and the block was heated to 110°C.
  • the vessel was pressurized to 1100 mbar before the contents were sampled via the sparge valves and an acid value was measured. After sampling, nitrogen was blown down the sparge for 10 minutes. A 2-ethyl hexanol content was determine and if >100 ppm the steam stripping was continued. If the 2-ethyl content was ⁇ 100 ppm the stripping was deemed complete.
  • the vessel was set to a constant reactor temperature of 90°C and the pressure was reduced to ⁇ 50 mbar to dry. These conditions were maintained for 1 - 2 hours. The vacuum was broken with nitrogen and the vessel was pressurized to 1100 mbar. The bottom valves were opened and the material was discharged into pre-weighed containers.
  • the vessel was set to a constant reactor temperature of 90°C and pressurized to 1100 mbar. The bottom valves were opened and the material was discharged into preweighed containers. The material was then charged to the 30 L glass vessel with Norit SA. The oil jacket was set to 90°C and a vacuum of ⁇ 50 mbar was applied. These conditions were maintained for 1-2 hours before the vacuum was broken with nitrogen. The material was then discharged into preweighed containers.
  • Example 1 IB The material from Example 1 IB was sent through a 4” Pope wiped film evaporator (WFE) under vacuum at various condition to separate out the lower molecular weight components.
  • WFE Pope wiped film evaporator
  • TablelO shows that polymer content and properties may be modified by separation of components via treatment with a WFE. Materials with higher polymer content may be produced. Depending on desired characteristics, separation of components may be desirable in some applications.
  • Example 13 A 2-Ethylhexyl poly- 10-hydroxy stearic acid
  • the final product was bleached (10g Norit SA4) and steam stripped at 110°C for 4 hours.
  • the product was dried and 4g Supercel filter aid was added. After a time consuming filtration (24 h) the product 13A was isolated and analyzed (see below).
  • Example 13B Ethylhexyl poly 10-hydroxy stearate/stearate (86/14)
  • Example 14 Effects of unsaturation in backbone.
  • Example 14A 2-Ethylhexyl poly 12-hvdroxystearate/ricinoleate (O? 1 / ⁇ 1 /?)
  • Example 14B 2-Ethylhexyl polv-12-hvdroxystearate/ricinoleate (95/5)
  • the final product was bleached (11g Norit SA4) and steam stripped at 110°C for 4 hours.
  • the product was dried and 4.8g Supercel filter aid was added.
  • the acid value was higher than expected (0.86mg KOH/g). Therefore 975 g product was mixed with 50g 2-ethylhexanol and esterified at 190°C and 150 mbar until the AV was 0.12mg KOH/g. The excess 2-ethylhexanol was distilled off.
  • the final product was bleached (11g Norit SA4) and steam stripped at 110°C for 4 hours.
  • the product was dried and 4.8g Supercel filter aid was added. After filtration the final product 14B was isolated and analyzed (see Table 11).
  • Example 14C Ethylhexyl Dolv-12-hydroxystearate/ricinoleate (92 1 /2/7 1 /2)
  • 12-Hydroxy stearic acid (865g) and 65 g ricinoleic acid were heated in a 2 liter round bottom flask equipped with nitrogen inlet and a take-off adaptor connected to a horizonal water condenser to 190°C in approx. 1 h. Once at temperature the pressure was gradually decreased to 200 mbar in 2 hrs and then further reduced to ⁇ 50 mbar. After reaching the acid value (73mg KOH/g) the reaction was stopped and cooled.
  • Example 15 A Acetylation to Hydroxyl Value of 29 mg KOH g -1
  • Poly-12-HSA from Example 11B (1264.2g, 1.01 mol) was placed into a round bottom 5-neck flask.
  • the flask was fitted with a stirrer, temperature probe, pressure equalizing dropping funnel, nitrogen headspace (30ml min -1 ) and a takeoff arm leading to a horizontal condenser.
  • the condenser was attached to a collection flask that was fitted with a nitrogen outlet leading to a Dreschel bottle filled with weak potassium hydroxide solution in water and phenolphthalein indicator.
  • the temperature of the vessel was increased to 130°C and acetic anhydride (48.8g, 0.48 mol) was placed into the dropping funnel. Once at temperature, acetic anhydride was slowly added to the vessel over 2 hours. The nitrogen flow was increased to 50ml min -1 and held for 1.75 hours before the material was steam stripped.
  • Example 15B Acetylation to Hydroxyl Value of 1 Img KOH g' 1
  • the Dreschel bottle was replaced with a vacuum pump and the pressure in the main vessel was reduced to ⁇ 30 mbar, thus reducing the pressure of the auxiliary vessel and causing steam to be generated.
  • the generated steam was carried into the main vessel through the sparge by the nitrogen.
  • Example 15C Acetylation to Hydroxyl Value of 3 mg KOH g' 1
  • the remaining material was acetylated further by placing acetic anhydride (20.0g, 0.20 mol) into the dropping funnel and heating the vessel to 130°C. Once at temperature, acetic anhydride over 1 hour and then allowed to react for a further 4 hours before the vessel was cooled to 110°C and steam stripped. Steam stripping was carried out by changing the nitrogen headspace to a nitrogen sparge (50ml min’ 1 ). The sparge was connected to an auxiliary vessel filled with reverse osmosis water and with a nitrogen inlet. The auxiliary vessel was placed in a water bath held at 60°C.
  • the Dreschel bottle was replaced with a vacuum pump and the pressure in the main vessel was reduced to ⁇ 20 mbar, thus reducing the pressure of the auxiliary vessel and causing steam to be generated.
  • the generated steam was carried into the main vessel through the sparge by the nitrogen.
  • Table 12 clearly demonstrates the dramatically surprising effect that increasing the proportion of free hydroxyl groups (as measured by hydroxyl value) has on oxidative stability. A modest increase in hydroxyl value from 3 to 11 over triples the oxidative stability. There is greater than a 10 fold difference between the starting material of Example 11 and the most acylated Example of 15C.
  • Example 16A Hexyl poly 12-hydroxy stearate
  • Example 16B 2-Octyl decyl polv-12-hydroxystearate
  • the product was distilled using a 2-stage molecular distillation set-up. The excess of Isofol 18 was distilled off (1 st stage 155-160°C/10’ 3 mbar ; 2 nd stage 185°C/10' 3 mbar). 1064g final product was bleached (10g Norit SA4) and steam stripped at 110°C for 4 hours. The product was dried and 5 g Supercel filter aid was added. After filtration the product was analyzed (see below).
  • Example 16C Isostearyl poly 12-hydroxy stearate
  • the product was distilled using a 2-stage molecular distillation set-up. The excess of isostearyl alcohol was distilled off (1 st stage 150-160°C/10' 3 mbar ; 2 nd stage 185°C/10’ 3 mbar). 935 g final product was bleached (10g Norit SA4) and steam stripped at 110°C for 4 hours. The product was dried and 5 g Supercel filter aid was added. After filtration the product was analyzed (see below).
  • Example 16D Stearyl poly- 12-hydroxy stearate
  • the product was distilled using a 2-stage molecular distillation set-up. The excess of isostearyl alcohol was distilled off (1 st stage 150-160°C/10' 3 mbar ; 2 nd stage 185°C/10‘ 3 mbar). 935g final product was bleached (10g Norit SA4) and steam stripped at 110°C during 4 hours. The product was dried and 5g Supercel filter aid was added. After filtration the product was analyzed (see below).
  • Example 16E Methyl poly 12-hydroxy stearate
  • the final product (methyl poly- 12-hydroxy stearate) was a mixture of 837g of the preliminary product and 148g of the top fraction of the molecular distilled repeat.
  • Example 16F Isopropyl poly 12-hydroxy stearate
  • the first batch was prepared by esterifying poly 12HSA with isopropanol.
  • the isopropyl ester was prepared by esterifying 12HSA with isopropanol to a low acid value. Both batches were molecular distilled to separate the low molecular components from the mix.
  • the isopropyl ester was prepared by mixing molecular distilled top and bottom fractions in the ratio described below.
  • the final product was a mixture of 360g top fraction of molecular distilled 16F1, 120g top fraction of molecular distilled 16F2 and 700g bottom fraction of molecular distilled 16F3. [0123] The combined fractions were bleached (12g Norit SA4) and steam stripped at 110°C during 3 hours. The product was dried and 5g Supercel filter aid was added. After filtration the product (16F) was analyzed (see below).
  • a tank was filled with 280 liters of demineralized water. Citric acid (473 g) and Na2HPO4 (1.65 kg) were added to the tank. The pH of the entire mixture was 7.0 ⁇ 0.5. MgSO4.7H2O (689 g) was added to the tank and the mixture was stirred for 15 minutes. The temperature of the resulting mixture was adjusted to 20-25 °C. Oleic acid (7 kg) was added to the solution, followed by the addition the of the hydratase enzyme PDN Cl 00 V2 from Biocatalysts Ltd (140 g) and the resulting mixture was stirred for 24 hours 20-25 °C. The mixture was then heated to 50°C and kept at this temperature for 1 hour. The mixture was then cooled to 30°C and filtered over a 1pm nylon filter. The solid precipitate was dried and taken from the filter affording 10-hydroxy stearic acid.
  • esters were prepared by standard esterification techniques through the dehydration of an acid and an alcohol or were acquired commercially from Cargill, Incorporated.
  • the lubricant blends in Table 16 below were prepared as follows.
  • the lubricant blends in Table 16 below were prepared by measuring each component into a suitable 250 ml glass beaker using a Mettler Toledo G2002-S balance. Where used, Example 3 and Example 1 IB were measured into the beaker first. Once all the required components were measured into the beaker, the beaker was placed on an IKA C-MAG HS7 hotplate and was stirred using an appropriate stirrer placed in an IKA OS20-S overhead stirrer. The material was blended at 300 rpm with the temperature set at 60°C for 1 hour.
  • Figures 2 and 3 are a comparison of Examples 19A (control) with Examples 19D and 19G at 40°C and 100°C.
  • Figures 4 and 6 are a comparison of Examples 19B (control) with Examples 19E and 19H at 40°C and 100°C.
  • Figures 6 and 7 are a comparison of Examples 19C (control) with Examples 19F and 19I at 40°C and 100°C.
  • Example 20 Inclusion rate traction study
  • the lubricant blends in Table 17 below were prepared as follows.
  • the lubricant blends in Table 17 below were prepared by measuring each component into a suitable 250 ml glass beaker using a Mettler Toledo G2002-S balance. Where used, Example 3 and Example 1 IB were measured into the beaker first. Once all the required components were measured into the beaker, the beaker was placed on an IKA C-MAG HS7 hotplate and was stirred using an appropriate stirrer placed in an IKA OS20-S overhead stirrer. The material was blended at 300 rpm with the temperature set at 60°C for 1 hour.
  • the MTM for Example 20 was run according to the following method. Stribeck and traction curves were measured at two different temperatures specifically 60°C and finally 80°C.
  • the idle speed when the temperature in the pot is being established is set to 1,000 mms-1 with a slide roll ratio of 0% and a load of 5N.
  • the test is performed at 60°C with a rolling speed of 50 mms-1 with a slide roll ratio of 50% and a load of 30N for 30 minutes.
  • the Stribeck and traction curves are measured at 60°C before the temperature is increased to 80°C and the Stribeck and traction curves measured again.
  • Stribeck curve the test was performed at 60°C or 80°C using a mean slide roll ratio of 50% and a load of 36N.
  • the Stribeck curve was run from 3200 mms-1 to 10 mms-1 in 50 steps evenly distributed in a logarithmic manner.
  • Viscosity of the samples was measured on an Anton Parr Stabinger Viscometer SVM3001 Viscometer in accordance with method ASTM D445. Material was added to the viscometer and the kinematic viscosity measured at 40°C (KV40) and at 100°C (KV100); with the machine also measuring the viscosity index (VI) and density.
  • OIT should be determined on compounds of Formulas 1 and 3, and on base oils, and lubricant formulations, without addition of any additives or antioxidants.
  • the OIT of the lubricating compositions, base oils, compounds of Formula 1, and Compounds of Formula 3 is greater than 500hr as determined according to ASTM D8206 at 160°C.
  • the OIT of the lubricating compositions, base oils, compounds of Formula, 1 and Compounds of Formula 3 is greater than 750hr as determined according to ASTM D8206 at 160°C.
  • the OIT of the lubricating compositions, base oils, compounds of Formula, 1 and Compounds of Formula 3 is greater than lOOOhr as determined according to ASTM D8206 at 160°C.
  • Samples from Example 11B we also evaluated for thermal degradation via Thermogravimetric analysis (TGA) under a nitrogen atmosphere to ensure the oxidative stability data was not skewed at a higher temperature do to degradation. Samples were evaluated from 90°C to 900°C under nitrogen on standard equipment. No significant degradation was seen to occur at temperatures under 240°C.
  • TGA Thermogravimetric analysis
  • Acid Value as used herein is defined as the weight of KOH in mg needed to neutralize the organic acids present in 1g of test sample and it is a measure of the free fatty acids present in the composition. AV can be determined by the AOCS Official Method Cd 3d-63.
  • Hydroxyl Value is defined as the hydroxyl value, expressed in milligrams of potassium hydroxide and corresponds to the number of hydroxyl groups present in 1g of a sample, is one of the traditional characteristics of oils and fats. Hydroxyl Value may be determined by AOCS Standard Method Cd 13-60.
  • Example 18 all testing was completed using a standard MTM-2 from PCS Instruments. During the test, standard MTM test specimens specifically a %” diameter steel ball and a 46mm diameter steel disc. Both the ball and disc were produced by PCS using AISI 5200 bearing grade steel and polished to a surface finish of respectively Ra ⁇ 0.01 and ⁇ 0.02.
  • test chamber in the MTM was cleaned with N- heptane and then dried and followed by laboratory grade nitrogen.
  • the ball and disc along with the test pieces required by the MTM were sonicated in N-heptane in separate pots for 15 minutes.
  • the test pieces include: a ball retaining screw, a splash guard, a disc holder, a disc securing nut, pot lid, tweezers and a hex torque drive supplied by PCS.
  • the N-heptane is drained and more N-heptane is poured into the pots and sonicated again for a further 15 minutes for a total cleaning time of 30 minutes.
  • the heptane is drained from the containers and then all test components were dried using nitrogen.
  • the ball is installed by placing the disc into the MTM chamber such that is aligns with the pins at the bottom of the chamber.
  • the disc holder is then placed on top of the disc and the disc securing nut is placed onto the screw in the bottom of the chamber and tightened.
  • the securing nut is tightened until the torque drive supplied by PCS clicks three times.
  • the ball retaining screw is then placed inside the ball and this is placed into the ball adaptor on the MTM using the tweezers.
  • the securing nut is tightened until the torque drive supplied by PCS clicks three times.
  • the splash guard is then installed on top of the disc and the appropriate lubricant is added until the oil covers the top of the splash guard.
  • the ball is then lowered using the PCS software and the pot lid and plastic lid placed on top of the pot.
  • the securing handle is then moved such that it rests in the divot in the top of the plastic lid and the PCS software displays the ‘locked’ sign.
  • the MTM is run using a 6 temperature traction profile. All traction tests are performed using a mean speed of 2,000 mm-1 with a ball load of 16N. The idle speed when the temperature in the pot is being established is set to 1,000 mm-1 with a slide roll ratio of 0% and a load of 5N. During the test, 6 different traction curves are recorded at different temperatures specifically 40°C, 60°C, 75°C, 100°C, 120°C and finally 150°C.
  • the traction curves themselves are run according to the following slide roll ratio parameters: a) Starting at 0.00% increasing in steps of 0.1% to 2.00% b) Then increasing in steps c) Then increasing in steps of 1.00% to 10.00% d) Then increasing in steps of 10.00% to 100.00%
  • the data is saved and used to prepare the appropriate slide roll curves.
  • the compounds of Formula 1 may have an acid value (AV) of less than 0.25, or less than 0.2, or between 0.05 and 0.2.
  • the compounds of Formula 3 may an acid value (AV) of less than 0.25, or less than 0.2, or between 0.05 and 0.2.
  • the compounds of Formula 1 may have a hydroxyl value of more than 10, or more than 20 or more than 35. In some aspects, the compounds of Formula 1 may have a hydroxyl value of between 10 and 70 or between 35 and 70. In some aspects, the compounds of Formula 1 may have a hydroxyl value of between 35 and 60.
  • the compounds of Formula 3 may have a hydroxyl value of more than 10, or more than 20 or more than 35. In some aspects, the compounds of Formula 3 may have a hydroxyl value of between 10 and 70 or between 35 and 70. In some aspects, the compounds of Formula 3 may have a hydroxyl value of between 35 and 60.
  • the compounds of Formula 1 and compounds of Formula 4 may have a hydroxyl value of more than 10, or more than 20 or more than 35. In some aspects, the compounds of Formula 1 and compounds of Formula 4 may have a hydroxyl value of between 10 and 70 or between 35 and 70. In some aspects, the compounds of Formula 1 and compounds of Formula 4 may have a hydroxyl value of between 35 and 60.
  • the compounds of Formula 3 and compounds of Formula 4 may have a hydroxyl value of more than 10, or more than 20 or more than 35. In some aspects, the compounds of Formula 3 and compounds of Formula 4 may have a hydroxyl value of between 10 and 70 or between 35 and 70. In some aspects, the compounds of Formula 3 and compounds of Formula 4 may have a hydroxyl value of between 35 and 60. [0158] Another aspect of the present disclosure is a method of lubricating two surfaces comprising contacting the interface of the surfaces with a lubricating composition of any of the compositions described herein.
  • the surfaces are part of hydraulic system.
  • the surfaces are gears.
  • the gears are in an industrial gear box, marine gear box, vehicle gear box, or vehicle transmission.
  • the lubricating composition comprises 0.5 - 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl.
  • the lubricating composition comprises 0.5 - 9.9% of one or more compounds of the Formula 1 wherein R is C1-C22 alkyl, R2 is a saturated or unsaturated C7 or C9 alkyl; and R3 is a C6 or C8 alkyl.
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl.
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil is selected from the group consisting of polyalphaolefins (PAOs), synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof.
  • PAOs polyalphaolefins
  • PAGs polyalkylene glycols
  • OSPs oil soluble polyalkylene glycols
  • mineral oils Groups I, II, and III
  • fatty acid esters and mixtures thereof.
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil comprises a polyalphaolefin (PAO).
  • PAO polyalphaolefin
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil selected from the group consisting of polyalphaolefins (PAOs), synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof, and has a hydroxyl value greater than 10.
  • PAOs polyalphaolefins
  • PAGs polyalkylene glycols
  • OSPs oil soluble polyalkylene glycols
  • mineral oils Groups I, II, and III
  • fatty acid esters and mixtures thereof, and has a hydroxyl value greater than 10.
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and further comprises a polyalphaolefin (PAO) and the base oil has a hydroxyl value greater than 35.
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil comprises a polyalphaolefin (PAO) and the compounds of Formula 3 have a hydroxyl value greater than 35.
  • the lubricating composition comprises comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil is selected from the group consisting of polyalphaolefins (PAOs), synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof, and the compounds of Formula 3 have a hydroxyl value greater than 35.
  • PAOs polyalphaolefins
  • synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof
  • PEOs polyalphaolefins
  • PAGs polyalkylene glycols
  • OSPs oil soluble polyalkylene glycols
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil comprises a polyalphaolefin (PAO) and the compounds of Formula 3 have a hydroxyl value greater than 35 and an acid value of less than 0.2 or less than 0.15.
  • PAO polyalphaolefin
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil is selected from the group consisting of polyalphaolefins (PAOs), synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof, and the compounds of Formula 3 have a hydroxyl value greater than 35 and an acid value of less than 0.2 or less than 0.15.
  • PAOs polyalphaolefins
  • synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof
  • the compounds of Formula 3 have a hydroxyl value greater than 35 and an acid value of less than 0.2 or less
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil comprises a polyalphaolefin (PAO), and the Compounds of Formula 3 have a hydroxyl value greater than 35.
  • R is 2-ethylhexyl
  • PAO polyalphaolefin
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, the base oil comprises a polyalphaolefin (PAO) and has a hydroxyl value between 35 and 70.
  • PAO polyalphaolefin
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, and wherein the base oil has an oxidation induction time (OIT) is improved by 25% as determined according to ASTM D8206 at 160°C and wherein the base oil does not contain any additional additives or antioxidants.
  • OIT oxidation induction time
  • the lubricating composition comprises 2% to 8% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, and wherein the base oil has an oxidation induction time (OIT) is improved by 25% as determined according to ASTM D8206 at 160°C and wherein the base oil does not contain any additional additives or antioxidants.
  • OIT oxidation induction time
  • the lubricating composition comprises 2% to 8% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, and wherein the base oil has an oxidation induction time (OIT) is improved by 25% as determined according to ASTM D8206 at 160°C and wherein the base oil does not contain any additional additives or antioxidants.
  • OIT oxidation induction time
  • the lubricating composition 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, and wherein the base oil has an oxidation induction time (OIT) is improved by 25% as determined according to ASTM D8206 at 160°C and wherein the base oil does not contain any additional additives or antioxidants.
  • the lubricating composition comprises 2% to 9.9% of one or more compounds of the Formula 1 and the base oil is improved by 25% as determined according to ASTM D8206 at 160°C.
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil has an OIT is improved by 25% as determined according to ASTM D8206 at 160°C.
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises a PAO and 2% 9.9% to of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil has an OIT is improved by 25% as determined according to ASTM D8206 at 160°C.
  • the lubricating composition comprises a base oil wherein the base oil comprises 0.5 - 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl.
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl.
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil is selected from the group consisting of polyalphaolefins (PAOs), synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof.
  • PAOs polyalphaolefins
  • synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof.
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil comprises a polyalphaolefin (PAO).
  • PAO polyalphaolefin
  • the lubricating composition comprises a base oil wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil selected from the group consisting of polyalphaolefins (PAOs), synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof, and has a hydroxyl value greater than 10.
  • PAOs polyalphaolefins
  • synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof, and has a hydroxyl value greater than 10.
  • the lubricating composition comprises a base oil wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and further comprises a polyalphaolefin (PAO) and the base oil has a hydroxyl value greater than 35.
  • PAO polyalphaolefin
  • the lubricating composition comprises a base oil wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil comprises a polyalphaolefin (PAO) and the compounds of Formula 3 have a hydroxyl value greater than 35.
  • PAO polyalphaolefin
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil is selected from the group consisting of polyalphaolefins (PAOs), synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof, and the compounds of Formula 3 have a hydroxyl value greater than 35.
  • PAOs polyalphaolefins
  • synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof
  • mineral oils Groups I, II, and III
  • the lubricating composition comprises a base oil wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil comprises a polyalphaolefin (PAO) and the compounds of Formula 3 have a hydroxyl value greater than 35 and an acid value of less than 0.2 or less than 0.15.
  • PAO polyalphaolefin
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil is selected from the group consisting of polyalphaolefins (PAOs), synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof, and the compounds of Formula 3 have a hydroxyl value greater than 35 and an acid value of less than 0.2 or less than 0.15.
  • PAOs polyalphaolefins
  • synthetic esters such as polyol esters, polyalkylene glycols (PAGs), oil soluble polyalkylene glycols (OSPs), mineral oils (Groups I, II, and III), fatty acid esters, and mixtures thereof
  • the compounds of Formula 3 have a hydroxyl value greater
  • the lubricating composition comprises a base oil wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil comprises a polyalphaolefin (PAO), and the Compounds of Formula 3 have a hydroxyl value greater than 35.
  • the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil comprises a polyalphaolefin (PAO), and the Compounds of Formula 3 have a hydroxyl value greater than 35.
  • PAO polyalphaolefin
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, the base oil comprises a polyalphaolefin (PAO) and has a hydroxyl value between 35 and 70.
  • the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl
  • the base oil comprises a polyalphaolefin (PAO) and has a hydroxyl value between 35 and 70.
  • PAO polyalphaolefin
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, and wherein the base oil has an oxidation induction time (OIT) is improved by 25% as determined according to ASTM D8206 at 160°C and wherein the base oil does not contain any additional additives or antioxidants.
  • OIT oxidation induction time
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 8% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, and wherein the base oil has an oxidation induction time (OIT) is improved by 25% as determined according to ASTM D8206 at 160°C and wherein the base oil does not contain any additional additives or antioxidants.
  • OIT oxidation induction time
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 8% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, and wherein the base oil has an oxidation induction time (OIT) is improved by 25% as determined according to ASTM D8206 at 160°C and wherein the base oil does not contain any additional additives or antioxidants.
  • OIT oxidation induction time
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl, and wherein the base oil has an oxidation induction time (OIT) is improved by 25% as determined according to ASTM D8206 at 160°C and wherein the base oil does not contain any additional additives or antioxidants.
  • OIT oxidation induction time
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 1 and the base oil is improved by 25% as determined according to ASTM D8206 at 160°C.
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises 2% to 9.9% of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil has an OIT is improved by 25% as determined according to ASTM D8206 at 160°C.
  • the lubricating composition comprises a base oil and additives wherein the base oil comprises a PAO and 2% 9.9% to of one or more compounds of the Formula 3 wherein R is 2-ethylhexyl and the base oil has an OIT is improved by 25% as determined according to ASTM D8206 at 160°C.
  • the compounds of Formula 1 or the compounds of Formula 3 can be present as a mixture of oligomers wherein with the majority of the oligomers contain between 2 and 6 units and greater than 50% of the oligomers contain 3 or more units.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente divulgation concerne de nouvelles compositions lubrifiantes d'origine biologique présentant une stabilité oxydative élevée et destinées à être utilisées dans toutes les applications de lubrification, telles que des engrenages, des moteurs et des dispositifs hydrauliques. Plus particulièrement, des compositions lubrifiantes comprennent une huile de base et un ou plusieurs additifs, et comprennent moins de 9,9 % en poids d'un ou de plusieurs des composés de formule 1 : dans laquelle n est un nombre entier compris entre 2 et 6 ; R est un alkyle en C1-C22 ; R2 est un alkyle en C3-C12 ; R3 est un hydrogène ou un alkyle en C1-C10.
PCT/US2025/024968 2024-04-16 2025-04-16 Nouveaux modificateurs de frottement Pending WO2025221891A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140100150A1 (en) * 2011-06-28 2014-04-10 Dow Global Technologies Llc Estolide derivatives useful as biolubricants
US20160264907A1 (en) * 2013-10-29 2016-09-15 Croda, Inc. Lubricant composition comprising hydroxycarboxylic acid derived friction modifier
WO2022258664A1 (fr) 2021-06-09 2022-12-15 Equus Uk Topco Ltd Composition lubrifiante comprenant un additif de coefficient de traction
WO2024206034A1 (fr) * 2023-03-28 2024-10-03 Cargill, Incorporated Lubrifiants d'origine biologique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140100150A1 (en) * 2011-06-28 2014-04-10 Dow Global Technologies Llc Estolide derivatives useful as biolubricants
US20160264907A1 (en) * 2013-10-29 2016-09-15 Croda, Inc. Lubricant composition comprising hydroxycarboxylic acid derived friction modifier
WO2022258664A1 (fr) 2021-06-09 2022-12-15 Equus Uk Topco Ltd Composition lubrifiante comprenant un additif de coefficient de traction
WO2024206034A1 (fr) * 2023-03-28 2024-10-03 Cargill, Incorporated Lubrifiants d'origine biologique

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
no. 106-14-9
THAKUR ROHAN ET AL: "Synthesis of 12-hydroxystearic estolide and its esters to study the effect of molecular structure on physicochemical properties", INDUSTRIAL CROPS AND PRODUCTS, ELSEVIER, NL, vol. 205, 15 September 2023 (2023-09-15), XP087427862, ISSN: 0926-6690, [retrieved on 20230915], DOI: 10.1016/J.INDCROP.2023.117435 *

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