EP4502125A1 - Lubrifiant - Google Patents

Lubrifiant Download PDF

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Publication number
EP4502125A1
EP4502125A1 EP23780248.3A EP23780248A EP4502125A1 EP 4502125 A1 EP4502125 A1 EP 4502125A1 EP 23780248 A EP23780248 A EP 23780248A EP 4502125 A1 EP4502125 A1 EP 4502125A1
Authority
EP
European Patent Office
Prior art keywords
lubricant
hydrogen bond
acid
mass
lubricant according
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
EP23780248.3A
Other languages
German (de)
English (en)
Other versions
EP4502125A4 (fr
Inventor
Tomoaki Okano
Kohei Yoshida
So Nakajima
Shunsuke KOYA
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.)
Idemitsu Kosan Co Ltd
Original Assignee
Idemitsu Kosan Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd
Publication of EP4502125A1 publication Critical patent/EP4502125A1/fr
Publication of EP4502125A4 publication Critical patent/EP4502125A4/fr
Pending legal-status Critical Current

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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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
    • C10M105/58—Amines, e.g. polyalkylene polyamines, quaternary amines
    • C10M105/60—Amines, e.g. polyalkylene polyamines, quaternary amines having amino groups bound to an acyclic or cycloaliphatic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/041—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms 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
    • 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

Definitions

  • the present invention relates to a lubricant.
  • PTL 1 discloses a lubricating oil composition containing an ionic liquid blended as a component.
  • the present invention was made in view of the above problems, and an object of the present invention is to provide a lubricant containing a carbon-neutral component, and showing a favorable lubricating property and low corrosiveness to metals.
  • a lubricant including a deep eutectic solvent consisting of a hydrogen bond acceptor and a hydrogen bond donor, the lubricant having a halogen atom content of 0.1% by mass or less, thereby completing the present invention.
  • the present invention provides the following [1] to [3].
  • the present invention can provide a lubricant containing a carbon-neutral component, and showing a favorable lubricating property and low corrosiveness to metals.
  • lower limit values and upper limit values described in a stepwise manner may be independently combined with each other.
  • the description "preferably 10 to 90, more preferably 30 to 60” may be meant to be “10 to 60" by the combination of a “preferred lower limit value (10)” and a “more preferred upper limit value (60)”.
  • numeral values accompanied by the terms “or more”, “or less”, “less than”, or “more than” may be arbitrarily combined.
  • a lubricant of the present embodiment includes a deep eutectic solvent consisting of a hydrogen bond acceptor and a hydrogen bond donor, and has a halogen atom content of 0.1% by mass or less.
  • the lubricant In cases where the halogen atom content in the lubricant is more than 0.1% by mass, the lubricant is highly corrosive to metals.
  • the deep eutectic solvent contained in the lubricant of the present embodiment consists of a hydrogen bond acceptor and a hydrogen bond donor, and mixing of these two components results in a decrease in the eutectic melting point.
  • the deep eutectic solvent may be either a liquid or solid at normal temperature (25°C)
  • the deep eutectic solvent is preferably a liquid at normal temperature (25°C) from the viewpoint of ease of handling as a lubricant.
  • the lubricant of the present embodiment contains the deep eutectic solvent at preferably 50% by mass or more, more preferably 70% by mass or more, still more preferably 90% by mass or more with respect to the total amount of the lubricant.
  • the lubricant may contain the deep eutectic solvent at about 0.1 to 10% by mass with respect to the total amount of the lubricant.
  • the hydrogen bond acceptor contained in the lubricant of the present embodiment is not limited as long as the hydrogen bond acceptor forms a eutectic with a hydrogen bond donor.
  • the hydrogen bond acceptor preferably does not contain a halogen atom, and specific examples of the hydrogen bond acceptor include betaine.
  • the betaine is preferably represented by the following General Formula (1).
  • R 1 to R 3 each independently represent a hydrocarbon group having 1 to 5 carbon atoms, and n represents an integer of 1 to 3.
  • R 1 to R 3 are preferably independently an alkyl group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 or 2 carbon atoms.
  • the n is preferably 1 or 2.
  • betaine represented by the General Formula (1) include N,N,N-trimethylglycine.
  • One of the hydrogen bond acceptors described above may be used individually, or two or more of the hydrogen bond acceptors may be used in combination.
  • the hydrogen bond donor contained in the lubricant of the present embodiment is not limited as long as the hydrogen bond donor forms a eutectic with a hydrogen bond acceptor.
  • the hydrogen bond donor preferably does not contain a halogen atom. More specifically, the hydrogen bond donor is more preferably one or more selected from an alcohol, a carboxylic acid, and a nitrogen-containing compound.
  • the alcohol is preferably an alcohol having 1 to 20 carbon atoms, more preferably 2 to 6 carbon atoms.
  • the alcohol include polyols such as ethylene glycol, triethylene glycol, glycerin, pentaerythritol, dipentaerythritol, hexanediol, 1,4-butanediol, glucose, sucrose, xylose, mannitol, sorbitol, xylitol, D-sorbitol, and fructose; and aromatic alcohols such as phenol, cresol, resorcinol, hydroquinone, and phloroglucinol.
  • polyols such as ethylene glycol, triethylene glycol, glycerin, pentaerythritol, dipentaerythritol, hexanediol, 1,4-butanediol, glucose, sucrose, xylose, mannitol, sorbitol, xylitol, D-sorbitol, and fructose
  • aromatic alcohols such
  • the carboxylic acid is preferably a carboxylic acid having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, still more preferably 2 to 6 carbon atoms.
  • carboxylic acid examples include fatty acids such as formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, eicosanoic acid, docosanoic acid, tetracosanoic acid, hexacosanoic acid, octacosanoic acid, and triacontanoic acid; hydroxy acids such as lactic acid, tartaric acid, malic acid, ascorbic acid, and citric acid; dicarboxylic acids such as adipic acid, malonic acid, oxalic acid, succinic acid, sube
  • the nitrogen-containing compound is preferably a nitrogen-containing compound having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, still more preferably 1 to 6 carbon atoms.
  • nitrogen-containing compound examples include urea, thiourea, 1-methylurea, 1,3-dimethylurea, 1,1-dimethylurea, acetamide, benzamide, imidazole, and benzimidazole.
  • One of the hydrogen bond donors described above may be used individually, or two or more of the hydrogen bond donors may be used in combination.
  • the content of the hydrogen bond acceptor with respect to the total amount of the lubricant is 25 to 75% by mass, and the content of the hydrogen bond donor with respect to the total amount of the lubricant is 25 to 75% by mass. More preferably, the content of the hydrogen bond acceptor with respect to the total amount of the lubricant is 35 to 65% by mass, and the content of the hydrogen bond donor with respect to the total amount of the lubricant is 35 to 65% by mass. Still more preferably, the content of the hydrogen bond acceptor with respect to the total amount of the lubricant is 40 to 60% by mass, and the content of the hydrogen bond donor with respect to the total amount of the lubricant is 40 to 60% by mass.
  • the hydrogen bond donor is preferably at 0.1 to 20 moles, more preferably at 0.2 to 5.0 moles, still more preferably at 0.5 to 4.0 moles, especially preferably at 0.8 to 3.0 moles with respect to 1 mole of the hydrogen bond acceptor.
  • the lubricant of the present embodiment preferably contains only the deep eutectic solvent from the viewpoint of carbon neutrality, but may contain one or more selected from a mineral oil and a synthetic oil, or may contain a mineral oil and a synthetic oil. Even in cases where the lubricant of the present embodiment contains one or more selected from a mineral oil and a synthetic oil, the amount of the mineral oil and the synthetic oil used can be reduced compared to conventional lubricating oils depending on the amount of the deep eutectic solvent blended. Therefore, the lubricant can contribute to the achievement of carbon neutrality.
  • the total content of the mineral oil and/or the synthetic oil in the lubricant of the present embodiment is preferably 0 to 50% by mass, more preferably 0 to 30% by mass, still more preferably 0 to 10% by mass with respect to the total amount of the lubricant.
  • mineral oil examples include atmospheric residues obtained by atmospheric distillation of a crude oil, such as paraffinic crude oil, intermediate base crude oil, and naphthenic crude oil; distillates obtained by distillation of these atmospheric residues under reduced pressure; and mineral oils obtained by subjecting the distillates to one or more of refining treatments such as solvent deasphalting, solvent extraction, hydrogenolysis, solvent dewaxing, catalytic dewaxing, and hydrorefining.
  • refining treatments such as solvent deasphalting, solvent extraction, hydrogenolysis, solvent dewaxing, catalytic dewaxing, and hydrorefining.
  • Examples of the synthetic oil include poly- ⁇ -olefins such as ⁇ -olefin homopolymers and ⁇ -olefin copolymers (for example, ⁇ -olefin copolymers having 8 to 14 carbon atoms, such as ethylene- ⁇ -olefin copolymers); isoparaffin; esters such as polyol esters and dibasic acid esters; ethers such as polyphenyl ethers; polyalkylene glycol; alkyl benzene; alkyl naphthalene; and GTL base oils obtained by isomerization of waxes (GTL waxes (Gas To Liquids WAX)) produced from natural gas by the Fischer-Tropsch process or the like.
  • poly- ⁇ -olefins such as ⁇ -olefin homopolymers and ⁇ -olefin copolymers (for example, ⁇ -olefin copolymers having 8 to 14 carbon atoms, such as ethylene
  • the kinematic viscosity and the viscosity index of the lubricant of the present embodiment are not limited.
  • the kinematic viscosity at 100°C is preferably 1.0 mm 2 /s or more, more preferably 2.0 mm 2 /s or more, still more preferably 2.5 mm 2 /s or more, and is preferably 50.0 mm 2 /s or less, more preferably 30.0 mm 2 /s or less, still more preferably 20.0 mm 2 /s or less.
  • These upper limit values and lower limit values may be arbitrarily combined.
  • the kinematic viscosity is preferably 1.0 to 50.0 mm 2 /s, more preferably 2.0 to 30.0 mm 2 /s, still more preferably 2.5 to 20.0 mm 2 /s.
  • the viscosity index of the lubricant is preferably 80 or more, more preferably 90 or more, still more preferably 100 or more.
  • kinematic viscosity and the viscosity index mean those values measured or calculated according to JIS K 2283:2000.
  • the lubricant of the present embodiment may contain a lubricant additive in addition to the deep eutectic solvent.
  • lubricant additive examples include those conventionally used as lubricating oil additives, such as one or more selected from the group consisting of an antioxidant, a detergent dispersant, an extreme pressure agent, an oiliness agent, a pour point depressant, a viscosity index improver, a rust inhibitor, a copper deactivator, and an anti-foaming agent.
  • the additives such as a pour point depressant, a viscosity index improver, and an anti-foaming agent may be in the forms of solutions in which the additives are diluted and dissolved in part of the lubricant, another base oil, or the like from the viewpoint of ease of handling and solubility in the lubricant.
  • the content of the deep eutectic solvent is not limited, and is, for example, preferably 60 to 99% by mass, more preferably 70 to 98% by mass, still more preferably 80 to 97% by mass, especially preferably 85 to 95% by mass with respect to the total amount (100% by mass) of the lubricant.
  • the lubricant of the present embodiment may be in the form of a grease composition containing a thickener as well as the lubricant additive.
  • a method for lubrication of the present embodiment uses the lubricant, and is, more specifically, a method in which lubrication between metal components is achieved by the presence of the lubricant.
  • a method for producing the lubricant of the present embodiment includes a step of obtaining a deep eutectic solvent by mixing a hydrogen bond acceptor with a hydrogen bond donor.
  • a method for producing the lubricant of the present embodiment includes: a step of mixing a lubricant additive at least one of a time during the step of obtaining the deep eutectic solvent in the method for producing the lubricant and a time after the step.
  • Examples of uses of the lubricant of the present embodiment include application for internal combustion engines, application for driving systems, hydraulic oils, automatic transmission oils, manual transmission oils, shock absorber oils, gear oils, fluid bearing oils, rolling bearing oils, oil retaining bearing oils, slideway oils, refrigerator oils, cutting oils, plastic working oils and other metal processing oils, heat treatment oils, and heating medium oils.
  • the present invention is described below in more detail by way of Examples. However, the present invention is not limited by these examples.
  • the components used in the Examples and Comparative Examples, and the properties of the lubricants obtained were measured by the following methods.
  • the lubricant obtained was subjected to measurement of the kinematic viscosity at 40°C and the viscosity index, and a reciprocating dynamic friction test was carried out under the following conditions to measure the coefficient of dynamic friction at the 30th reciprocating sliding movement.
  • the lubricant obtained was subjected to measurement of the kinematic viscosity at 40°C and the viscosity index, and a reciprocating dynamic friction test was carried out to measure the coefficient of dynamic friction at the 30th reciprocating sliding movement.
  • a mineral oil of 500 neutral fraction was subjected to measurement of the kinematic viscosity at 40°C and the viscosity index, and a reciprocating dynamic friction test was carried out to measure the coefficient of dynamic friction at the 30th reciprocating sliding movement.
  • a lubricant was prepared in the same manner as in Example 1 except that 27.8 g of tetrabutylammonium chloride (TBAC) was used as a hydrogen bond acceptor, and that 20.0 g of dodecanoic acid was used as a hydrogen bond donor.
  • TBAC tetrabutylammonium chloride
  • the lubricant obtained was subjected to measurement of the kinematic viscosity at 40°C and the viscosity index, and a reciprocating dynamic friction test was carried out to measure the coefficient of dynamic friction at the 30th reciprocating sliding movement.
  • a lubricant was prepared in the same manner as in Example 1 except that 13.9 g of choline chloride was used as a hydrogen bond acceptor, and that 13.4 g of glycerin was used as a hydrogen bond donor.
  • the lubricants prepared in Examples 1 and 2 had low coefficients of friction in the reciprocating dynamic friction test, and hence were found to have excellent lubricating properties.

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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)
EP23780248.3A 2022-03-31 2023-03-24 Lubrifiant Pending EP4502125A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022061404A JP2023151663A (ja) 2022-03-31 2022-03-31 潤滑剤
PCT/JP2023/011986 WO2023190238A1 (fr) 2022-03-31 2023-03-24 Lubrifiant

Publications (2)

Publication Number Publication Date
EP4502125A1 true EP4502125A1 (fr) 2025-02-05
EP4502125A4 EP4502125A4 (fr) 2026-03-25

Family

ID=88201684

Family Applications (1)

Application Number Title Priority Date Filing Date
EP23780248.3A Pending EP4502125A4 (fr) 2022-03-31 2023-03-24 Lubrifiant

Country Status (6)

Country Link
US (1) US20250215344A1 (fr)
EP (1) EP4502125A4 (fr)
JP (1) JP2023151663A (fr)
CN (1) CN118974218A (fr)
TW (1) TW202344674A (fr)
WO (1) WO2023190238A1 (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9957459B2 (en) * 2014-11-03 2018-05-01 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
WO2018144301A1 (fr) * 2017-02-06 2018-08-09 Exxonmobil Chemical Patents Inc. Mélanges à température de transition basse et huiles lubrifiantes contenant ceux-ci
US10793801B2 (en) * 2017-02-06 2020-10-06 Exxonmobil Chemical Patents Inc. Low transition temperature mixtures and lubricating oils containing the same
EP4011354A1 (fr) * 2020-12-09 2022-06-15 Beiersdorf AG Nouveaux solvants cosmétiques basés sur deux composants différents

Also Published As

Publication number Publication date
US20250215344A1 (en) 2025-07-03
TW202344674A (zh) 2023-11-16
CN118974218A (zh) 2024-11-15
EP4502125A4 (fr) 2026-03-25
WO2023190238A1 (fr) 2023-10-05
JP2023151663A (ja) 2023-10-16

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