Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
  • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
  • C10M137/04—Phosphate esters
  • C10M137/08—Ammonium or amine salts
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/223—Five-membered rings containing nitrogen and carbon 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/043—Ammonium or amine salts thereof
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
• • 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
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/02—Groups 1 or 11
• • 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
  • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Definitions

• the present invention relates to an anti-wear agent.
• An ionic liquid such as a pyrrolidinium-type ionic liquid has been known as the following base material: while the base material has a viscosity lower than that of a MAC oil (cyclopentane oil such as tris(2-octyldodecyl)cyclopentane) generally used as a base material for a space lubricant, the base material has both of excellent low volatility and excellent thermal stability.
• MAC oil cyclopentane oil such as tris(2-octyldodecyl)cyclopentane
• the ionic liquid be used as a base material for a long-life lubricant by exploiting its features, that is, the low volatility and the thermal stability.
• the liquid in order that the liquid may be used in a lubricant for a long time period, the liquid needs to be excellent in wear resistance and anti-rust property.
• an additive to be blended into a lubricant composition using the ionic liquid as a base material desirably has a plurality of characteristics.
• an imidazolium-type phosphate compound whose cation has an imidazolium structure has been known as an additive to be blended into the ionic liquid (see, for example, PTL 1 and PTL 2).
• the inventors of the present invention have made an investigation, and as a result, have found that the imidazolium-type phosphate compound has a problem in that the compound has high metal corrosiveness, and is hence remarkably poor in anti-rust property, though the compound is excellent in wear resistance.
• the present invention has been made in view of the problems, and an object of the present invention is to provide an anti-wear agent excellent in wear resistance and maintenance of its anti-rust property.
• the inventors of the present invention have made extensive investigations, and as a result, have found that a specific anti-wear agent can solve the problems. Thus, the inventors have completed the present invention.
• the present invention provides the following item [1].
• the anti-wear agent excellent in wear resistance and maintenance of its anti-rust property can be provided.
• An anti-wear agent according to an embodiment of the present invention is an anti-wear agent including one or more kinds selected from compounds each represented by the following general formula (B1): wherein in the general formula (B1), respective symbols represent the following:
• the inventors of the present invention have made extensive investigations with a view to solving the problems.
• the inventors have found that when a pyrrolidinium-type ionic liquid is used, the preparation of an anti-wear agent including a pyrrolidinium-type phosphate compound whose cation moiety has a structure similar to that of the ionic liquid can suppress a reduction in anti-rust property after the lapse of a long time period.
• the inventors have found that the optimization of the carbon chain length of an alkyl group of a phosphate serving as the anion moiety of the compound provides excellent wear resistance.
• the inventors have completed the present invention on the basis of those findings.
• R B1 in the general formula (B1) represents an alkyl group having 1 to 9 carbon atoms, and the group has preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms.
• the alkyl group may be linear or branched.
• R B1 represents an alkyl group having 1 to 9 carbon atoms
• the wear resistance, anti-rust property, and thermal stability of the anti-wear agent become satisfactory.
• R B2 in the general formula (B1) represents an alkyl group having 1 to 9 carbon atoms, and the group has preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms.
• the alkyl group may be linear or branched.
• R B2 represents an alkyl group having 1 to 9 carbon atoms, the anti-rust property and thermal stability of the anti-wear agent, and the solubility thereof in an ionic liquid become satisfactory.
• R B2 may represent the same alkyl group as that represented by R B1 .
• R B3 in the general formula (B1) represents an alkyl group having 1 to 9 carbon atoms, and the group has preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms.
• the alkyl group may be linear or branched.
• R B3 represents an alkyl group having 1 to 9 carbon atoms
• the anti-rust property, thermal stability, and wear resistance of the anti-wear agent, and the solubility thereof in an ionic liquid become satisfactory.
• R B4 in the general formula (B1) represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms.
• R B4 represents an alkyl group
• the group has preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms.
• R B4 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, the wear resistance and thermal stability of the anti-wear agent become satisfactory.
• the alkyl group may be linear or branched.
• R B2 , R B3 , and R B4 in the general formula (B1) may represent the same alkyl group or different alkyl groups, the symbols preferably represent the same alkyl group from the viewpoint of synthesis.
• R B1 , R B2 , R B3 , and R B4 in the general formula (B1) each have preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms.
• R in the general formula (B1) represents an alkyl group having 1 to 3 carbon atoms, and the number of its carbon atoms is preferably 1.
• the alkyl group may be linear or branched.
• Y in the general formula (B1) represents a methylene group or an oxygen atom, preferably a methylene group.
• n1 in the general formula (B1) represents 1 or 2, preferably 1.
• n1 in the general formula (B1) represents 1, "m” represents an integer of from 0 to 8, preferably 0.
• n1 represents 2
• m represents an integer of from 0 to 10, preferably 0.
• the total of the number of the carbon atoms of the alkyl group represented by R B1 and the number of the carbon atoms of the alkyl group represented by R B2 is not particularly limited. However, the total is preferably 6 or less.
• the anti-wear agent is easily improved in wear resistance, and is excellent in thermal stability.
• the compound represented by the general formula (B1) is a salt structure containing a cation and an anion.
• the foregoing shows that the compound is excellent in solubility in an ionic liquid and low volatility.
• the anti-wear agent of this embodiment is excellent not only in wear resistance but also in maintenance of its anti-rust property.
• rust means a "product produced as a result of the advance of a corrosion phenomenon in a metal brought into contact with an ionic liquid.”
• the inventors of the present invention have made investigations, and as a result, have found that the rust tends to occur in a portion brought into contact with the ionic liquid on the surface of the metal (boundary surface between the ionic liquid and the metal).
• the ionic liquid contains a cation and an anion, and hence the occurrence of the rust is accelerated by the ionic conductivity of the ionic liquid.
• an anti-wear agent including a pyrrolidinium-type phosphate compound whose cation moiety has a structure similar to that of the ionic liquid suppresses a reduction in anti-rust property after the lapse of a long time period.
• the anti-wear agent of this embodiment can maintain its anti-rust property, by which the occurrence of rust is suppressed, for a long time period.
• the compound represented by the general formula (B1) may be obtained by, for example, ionizing an alkyl pyrrolidine and a trialkyl phosphate to synthesize the compound represented by the general formula (B 1).
• the anti-wear agent of this embodiment may be formed only of the one or more kinds selected from the compounds each represented by the general formula (B1), the agent may include any other component except the compound, or may be free of the component.
• the content of the one or more kinds selected from the compounds each represented by the general formula (B 1) in the anti-wear agent of this embodiment is preferably from 50 mass% to 100 mass%, more preferably from 60 mass% to 100 mass%, still more preferably from 70 mass% to 100 mass%, still further more preferably from 80 mass% to 100 mass%, yet still further more preferably from 90 mass% to 100 mass%, even more preferably from 95 mass% to 100 mass%, still even more preferably from 98 mass% to 100 mass% with respect to the total amount of the anti-wear agent.
• the agent When the anti-wear agent is used together with the ionic liquid, the agent may be used in, for example, a lubricant composition using the ionic liquid as a base material.
• the ionic liquid is a liquid compound including a cation and an anion, and various compounds that are free of metal contents may each be adopted.
• the compound represented by the general formula (B1) is not included in the ionic liquid.
• the ionic liquid preferably contains, as its anion, bis(trifluoromethanesulfonyl)imide.
• the ionic liquid preferably contains, as its cation, a cation represented by the following general formula (A1): wherein in the general formula (A1), respective symbols represent the following:
• the number of the carbon atoms of the alkyl group represented by each of R A11 and R A12 in the general formula (A1) is preferably from 1 to 6, more preferably from 1 to 4.
• R A11 preferably represents a methyl group.
• R A12 preferably represents a n-butyl group or a methoxyethyl group.
• Examples of the cation represented by the general formula (A1) include 1-butyl-1-methylpyrrolidinium, 1-pentyl-1-methylpyrrolidinium, 1-hexyl-1-methylpyrrolidinium, 1-heptyl-1methylpyrrolidinium, 1-octyl-1-methylpyrrolidinium, 1-nonyl-1-methylpyrrolidinium, 1-decyl-1-methylpyrrolidinium, 1-undecyl-1-methylpyrrolidinium, 1-dodecyl-1-methylpyrrolidinium, 1-methoxymethyl-1-methylpyrrolidinium, 1-(2-methoxyethyl)-1-methylpyrrolidinium, 1-(2-methoxy-2-oxoethyl)-1-methylpyrrolidinium, 1-cyanomethyl-1-methylpyrrolidinium, 1-trimethylsilylmethyl-1-methylpyrrolidinium, 1-butyl-1-methylpiperidinium, 1-pentyl-1-methylpiperidin
• 1-butyl-1-methylpyrrolidinium, 1-pentyl-1-methylpyrrolidinium, 1-hexyl-1-methylpyrrolidinium, 1-(2-methoxyethyl)-1-methylpyrrolidinium, 1-butyl-1-methylpiperidinium, 1-(2-methoxyethyl)-1-methylpiperidinium, and 1-(2-methoxyethyl)-1-methylmorpholinium are preferred, 1-butyl-1-methylpyrrolidinium, 1-(2-methoxyethyl)-1-methylpyrrolidinium, and 1-(2-methoxyethyl)-1-methylpiperidinium are more preferred, and 1-butyl-1-methylpyrrolidinium and 1-(2-methoxyethyl)-1-methylpyrrolidinium are still more preferred from the viewpoints of reducing the viscosity of the ionic liquid and improving the thermal stability thereof.
• the ionic liquid preferably contains at least one kind selected from a compound represented by the following general formula (A2) and a compound represented by the following general formula (A3): wherein in the general formula (A2), respective symbols represent the following:
• the number of the carbon atoms of R A21 is preferably from 2 to 8, more preferably from 3 to 6.
• the number of the carbon atoms of R A21 is 2 or more, a side chain of the compound can freely move, and the symmetry thereof reduces. Accordingly, the crystallization thereof is suppressed, and hence the function thereof as an ionic liquid can be improved.
• the number of the carbon atoms of R A21 is 12 or less, the side chain does not become excessively large, and hence the ionicity of the entirety of the compound is high. Accordingly, the oxidative degradation thereof is easily suppressed.
• the number of the carbon atoms of R A31 is preferably from 1 to 3, more preferably 1 or 2.
• the number of the carbon atoms of R A32 is preferably 1 or 2.
• the number of the carbon atoms of R A31 is 1 or more, a side chain of the compound can freely move, and the symmetry thereof reduces. Accordingly, the crystallization thereof is suppressed, and hence the function thereof as an ionic liquid can be improved.
• the number of the carbon atoms of R A31 is 5 or less, or the number of the carbon atoms of R A32 is 3 or less, the side chain does not become excessively large, and hence the ionicity of the entirety of the compound is high. Accordingly, the oxidative degradation thereof is easily suppressed.
• the content of the compound represented by the general formula (A2) in the ionic liquid is preferably from 60 mass% to 100 mass%, more preferably from 70 mass% to 100 mass%, still more preferably from 80 mass% to 100 mass% with respect to the total amount of the ionic liquid.
• the content of the compound represented by the general formula (A3) in the ionic liquid is preferably from 60 mass% to 100 mass%, more preferably from 70 mass% to 100 mass%, still more preferably from 80 mass% to 100 mass% with respect to the total amount of the ionic liquid.
• One or more kinds selected from the compounds each represented by the general formula (A2) may be used as the ionic liquid, or one or more kinds selected from the compounds each represented by the general formula (A3) may be used.
• One or more kinds selected from the compounds each represented by the general formula (A2), and one or more kinds selected from the compounds each represented by the general formula (A3) may be used in combination.
• the content of the ionic liquid is not particularly limited. However, from, for example, the viewpoint of improving the effect of the present invention, the content is preferably 50 mass% or more, more preferably 60 mass% or more, still more preferably 70 mass% or more, still further more preferably 80 mass% or more, yet still further more preferably 85 mass% or more with respect to the total amount (100 mass%) of the lubricant composition.
• the upper limit value of the content of the ionic liquid is appropriately set in accordance with the addition amount of a component except the ionic liquid, and is preferably 99.8 mass% or less, more preferably 99.7 mass% or less, still more preferably 99.5 mass% or less, still further more preferably 99.0 mass% or less, yet still further more preferably 98.5 mass% or less.
• the content is preferably from 50 mass% to 100 mass%, more preferably from 60 mass% to 100 mass%, still more preferably from 70 mass% to 100 mass%, still further more preferably from 90 mass% to 100 mass%, yet still further more preferably from 95 mass% to 100 mass%.
• a base material component except the above-mentioned ionic liquid may be incorporated as a base material into the lubricant composition.
• the content of the above-mentioned ionic liquid is preferably 50 mass% or more, more preferably 70 mass% or more, still more preferably 90 mass% or more, still further more preferably 100 mass% with respect to the total amount of the base material.
• the ratio (B/A) of the content B of the compound represented by the general formula (B1) to the content A of the ionic liquid is preferably 0.0005 or more and 0.15 or less, more preferably 0.001 or more and 0.111 or less, still more preferably 0.003 or more and 0.08 or less in terms of mass ratio.
• the ratio (B/A) is 0.0005 or more, the anti-rust property of the composition is easily made sufficient.
• the ratio (B/A) is 0.15 or less, the solubility of the compound represented by the general formula (B1) in the ionic liquid is easily made sufficient.
• the lubricant composition may contain any other component except the anti-wear agent of this embodiment as required to the extent that the effect of the present invention is not impaired.
• Examples of the other component include: a by-product produced in a synthesis process for the compound represented by the general formula (B1); and an unreacted raw material and a diluent remaining in the synthesis process for the compound represented by the general formula (B1).
• the examples of the other component except the anti-wear agent of this embodiment include: an additive such as a viscosity index improver; and a thickener.
• the wear width thereof is preferably 250 ⁇ m or less, more preferably 230 ⁇ m or less, still more preferably 200 ⁇ m or less.
• the anti-wear agent of this embodiment is excellent not only in wear resistance but also in maintenance of its anti-rust property. Accordingly, the agent may be blended into a lubricant composition that is required to have a high anti-rust property.
• the anti-wear agent according to this embodiment provides the following (1) and (2):
• Compound 1 is such a compound that the respective symbols in the general formula (B1) represent the following:
• Compound 2 is such a compound that the respective symbols in the general formula (B1) represent the following:
• Compound 3 is such a compound that the respective symbols in the general formula (B1) represent the following:
• Compound 4 is such a compound that the respective symbols in the general formula (B1) represent the following:
• N -(2-Methoxyethyl)- N -methylpyrrolidinium-bis(trifluoromethanesulfonyl)imide was used as an ionic liquid.
• lubricant compositions were prepared by blending Compounds 1 to 4 serving as anti-wear agents in Examples 1 to 5, and blending Comparative Compounds 1 to 5 serving as anti-wear agents in Comparative Examples 1 to 6, followed by the following evaluations.
• Examples 1 to 5 containing Compounds 1 to 4 serving as anti-wear agents are each excellent in wear resistance because the wear widths are 250 ⁇ m or less.
• Examples 1 to 5 were each also excellent in maintenance of its anti-rust property.
• Comparative Examples 1 to 5 containing Comparative Compounds 1 to 4 serving as anti-wear agents were each poor in at least one of wear resistance or maintenance of its anti-rust property. Specifically, in Comparative Example 4, the wear width was much more than 250 ⁇ m, and hence the wear resistance was extremely insufficient. In addition, the following results were obtained: Comparative Examples 1 to 3 and Comparative Example 5 were each poor in maintenance of the anti-rust property. In addition, in Comparative Example 6, the wear resistance and the maintenance of the anti-rust property were not able to be evaluated because Comparative Compound 5 was not dissolved in the ionic liquid.

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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)

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• 2022
  • 2022-11-16 JP JP2022183350A patent/JP2024072503A/ja active Pending
• 2023
  • 2023-11-13 CN CN202380078445.9A patent/CN120112619A/zh active Pending
  • 2023-11-13 WO PCT/JP2023/040805 patent/WO2024106393A1/ja not_active Ceased
  • 2023-11-13 EP EP23891540.9A patent/EP4621033A1/en active Pending

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