WO2013172428A1 - Composé de type imide-amide et son procédé de production, épaississant pour graisse et composition de graisse - Google Patents

Composé de type imide-amide et son procédé de production, épaississant pour graisse et composition de graisse Download PDF

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WO2013172428A1
WO2013172428A1 PCT/JP2013/063713 JP2013063713W WO2013172428A1 WO 2013172428 A1 WO2013172428 A1 WO 2013172428A1 JP 2013063713 W JP2013063713 W JP 2013063713W WO 2013172428 A1 WO2013172428 A1 WO 2013172428A1
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imide
general formula
represented
monoisocyanate
amide compound
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PCT/JP2013/063713
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English (en)
Japanese (ja)
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健太郎 山口
実希 藤原
龍一 上野
設楽　裕治
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Ｊｘ日鉱日石エネルギー株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • 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
    • C10M115/00—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof
    • C10M115/08—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof containing nitrogen
    • 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C10M2215/0813—Amides used as thickening agents
    • 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
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
    • C10M2215/1026—Ureas; Semicarbazides; Allophanates used as thickening 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
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2040/02—Bearings
    • 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
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • the present invention relates to an imide-amide compound, a production method thereof, a thickener for grease, and a grease composition.
  • double-row angular contact ball bearings were mainly used for compressor pulleys and car air conditioner electromagnetic clutch bearings.
  • single-row bearings have been used to reduce the weight and cost of pulleys and electromagnetic clutches. Tend to use.
  • the PV value the product of the bearing surface pressure P and the sliding speed V representing the limit of the load capacity of the bearing is increased. Due to its small space volume, it tends to be used under conditions where the amount of grease filled is small and the amount of heat generated by the grease is large.
  • Patent Documents 1 to 5 disclose grease compositions using urea-based thickeners.
  • the heat resistant temperature of these urea greases is about 180 ° C.
  • fluorine greases are known as greases that can withstand higher temperatures.
  • Fluorine grease is a grease composition containing perfluoropolyether as a base oil and ethylene tetrafluoride as a thickener, but it is very expensive because it uses a special chemically synthesized base oil. A cheaper heat resistant grease is required.
  • Patent Documents 6 to 7 disclose a grease composition using an imide thickener as an example of a grease having high heat resistance.
  • JP 2004-359809 A JP 2003-342593 A JP 2010-073320 A JP 2009-197162 A JP 2008-231310 A JP 54-113605 A Japanese Unexamined Patent Publication No. 57-109896
  • the present invention provides an imide-amide compound represented by the following general formula (1). [Wherein, R and X each represent a monovalent organic group. ]
  • the imide-amide compound of the present invention preferably has a structure represented by the following general formula (2) or (3). [Wherein R 1 and R 2 represent a monovalent organic group, X 1 represents a divalent organic group, X 2 represents a monovalent organic group, and R 1 and R in formula (2) 2 may be the same or different. ]
  • the present invention provides an imidocarboxylic acid represented by the following general formula (6) by reacting a trimellitic anhydride represented by the following formula (4) with a monoamine represented by the following general formula (5).
  • the present invention also provides a thickener for grease containing the imide-amide compound of the present invention.
  • the present invention also provides a grease composition containing a lubricating base oil and the imide-amide compound of the present invention.
  • FIG. 2 is a graph showing an infrared absorption spectrum of an imide-amide compound obtained in Example 1.
  • FIG. 2 is a diagram showing an FD-MS spectrum of an imide-amide compound obtained in Example 1.
  • the imide-amide compound according to the first embodiment of the present invention has a structure represented by the following general formula (1). [Wherein, R and X each represent a monovalent organic group. ]
  • the imide-amide compound according to this embodiment include imide-amide compounds represented by the following general formula (2) or general formula (3).
  • the imide-amide compound represented by the general formula (1) has two imide groups and two amide groups.
  • the imide-amide compound represented by the general formula (2) has one imide group and one amide group. [Wherein R 1 and R 2 represent a monovalent organic group, X 1 represents a divalent organic group, X 2 represents a monovalent organic group, and R 1 and R in formula (2) 2 may be the same or different. ]
  • X 1 represents a divalent organic group, preferably a divalent residue obtained by removing two isocyanate groups from diisocyanate.
  • Diisocyanate is defined as a compound in which two isocyanate groups are added to an aliphatic, aromatic hydrocarbon or heterocyclic compound, or a derivative thereof.
  • diisocyanate monomers from which X 1 is derived there are the following or a mixture thereof, but the present invention is not limited to these.
  • aliphatic diisocyanate examples include diisocyanates having a saturated and / or unsaturated linear, branched, or alicyclic hydrocarbon group. Specifically, methylene diisocyanate, ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 2,5-dimethylhexamethylene diisocyanate, 3-methoxyhexamethylene diisocyanate, heptamethylene diisocyanate, 2,5- Dimethylheptamethylene diisocyanate, 3-methylheptamethylene diisocyanate, 4,4-dimethylheptamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, 5-methylnonamethylene diisocyanate, decamethylene diisocyanate, 1,4-diisocyanatocyclohexane, 1 , 3-Bis (
  • Aromatic diisocyanates include o-phenylene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, o-xylylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, 1,4-diisocyanatonaphthalene, 1, 5-diisocyanatonaphthalene, 1,8-diisocyanatonaphthalene, 2,6-diisocyanatonaphthalene, 2,7-diisocyanatonaphthalene, 1,8-diisocyanatoanthracene, 2,6-diisocyanato Anthracene, 2,7-diisocyanatoanthracene, 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, 2,4-diisocyanato (m-xylene),
  • X 2 represents a monovalent organic group, preferably a monovalent residue obtained by removing one isocyanate group from monoisocyanate.
  • Monoisocyanates are defined as compounds in which one isocyanate group is added to an aliphatic, aromatic hydrocarbon or heterocyclic compound, or derivatives thereof.
  • monoisocyanate monomers that form the structure of X 2 there are the following or a mixture thereof, but the invention is not limited to these.
  • aliphatic monoisocyanate examples include linear or branched aliphatic monoisocyanates, alicyclic monoisocyanates, and aromatic monoisocyanates, and hydrocarbon residues having 6 to 20 carbon atoms, preferably 8 to 18 carbon atoms.
  • Linear or branched alkyl monoisocyanate, linear or branched alkenyl monoisocyanate, cycloalkyl monoisocyanate, alkylcycloalkyl monoisocyanate, aryl monoisocyanate, alkylaryl monoisocyanate, arylalkyl A monoisocyanate etc. are mentioned.
  • Specific examples include hexyl monoisocyanate, heptyl monoisocyanate, octyl monoisocyanate, nonyl monoisocyanate, decyl monoisocyanate, undecyl monoisocyanate, dodecyl monoisocyanate, tridecyl monoisocyanate, tetradecyl monoisocyanate, pentadecyl monoisocyanate, hexadecyl.
  • Linear or branched alkyl monoisocyanates such as monoisocyanate, heptadecyl monoisocyanate, octadecyl monoisocyanate, nonadecyl monoisocyanate, eicosyl monoisocyanate; cyclohexyl monoisocyanate; methylcyclohexyl monoisocyanate, dimethylcyclohexyl monoisocyanate, ethyl Cyclohexyl monoisocyanate, die L-cyclohexyl monoisocyanate, propylcyclohexyl monoisocyanate, isopropylcyclohexyl monoisocyanate, 1-methyl-3-propylcyclohexyl monoisocyanate, butylcyclohexyl monoisocyanate, amylcyclohexyl monoisocyanate, amylmethylcyclohexyl monoisocyanate, hexylcyclohexy
  • the former become monoisocyanate monomer X 2 made structure, in terms of lubricity and grease performance, straight-chain or branched aliphatic monoisocyanates are preferred.
  • the carbon number of the linear or branched aliphatic monoisocyanate is preferably 4 to 20, more preferably 8 to 20.
  • the aliphatic monoisocyanate may be either a linear or branched saturated aliphatic monoisocyanate or an unsaturated aliphatic monoisocyanate. However, since the aliphatic monoisocyanate is excellent in oxidative stability, the linear or branched saturated aliphatic monoisocyanate. Isocyanates are preferred.
  • alicyclic monoisocyanate is preferable from the viewpoint of heat resistance.
  • the carbon number of the alicyclic monoisocyanate is preferably 4 to 20, more preferably 4 to 10.
  • the alicyclic monoisocyanate may be either a saturated alicyclic monoisocyanate or an unsaturated alicyclic isocyanate, but a saturated alicyclic isocyanate is preferred because of excellent oxidation stability.
  • aromatic monoisocyanate is preferable from the viewpoint of lubricity and heat resistance.
  • the carbon number of the aromatic monoisocyanate is preferably 6 to 20, more preferably 8 to 20.
  • R 1 and R 2 each represent a monovalent organic group, preferably a monovalent residue obtained by removing one amino group from an aliphatic monoamine, alicyclic monoamine or aromatic monoamine.
  • Examples of the monoamine that is the base of the structure of R 1 and R 2 include, but are not limited to, the following monoamines or mixtures thereof.
  • Examples of monoamines include aliphatic amines, alicyclic amines, and aromatic amines, which have a hydrocarbon residue having 6 to 20 carbon atoms, preferably 8 to 18 carbon atoms, and are linear or branched alkyls. Examples include amines, linear or branched alkenylamines, cycloalkylamines, alkylcycloalkylamines, arylamines, alkylarylamines, arylalkylamines, and the like.
  • linear or branched aliphatic monoamines are preferable from the viewpoint of lubricity and grease performance.
  • the carbon number of the linear or branched aliphatic monoamine is preferably 4 to 20, more preferably 8 to 20.
  • the aliphatic monoamine may be either a saturated aliphatic monoamine or an unsaturated aliphatic monoamine, but is preferably a saturated aliphatic amine because of excellent oxidation stability.
  • alicyclic monoamines are preferable.
  • the carbon number of the alicyclic monoamine is preferably 4 to 20, more preferably 4 to 10.
  • the alicyclic monoamine may be either a saturated alicyclic monoamine or an unsaturated alicyclic monoamine, but is preferably a saturated alicyclic monoamine because of excellent oxidation stability.
  • a mixture of an aliphatic chain monoamine, an alicyclic monoamine, and an aromatic monoamine is preferable.
  • the method for producing an imide-amide compound according to the second embodiment of the present invention comprises the steps of reacting trimellitic anhydride represented by the following formula (4) with a monoamine represented by the following general formula (5).
  • the first step of obtaining an imide carboxylic acid represented by the general formula (6) and the imide carboxylic acid reacted with an isocyanate represented by the following general formula (7) are represented by the following general formula (1).
  • a second step of obtaining an imide-amide compound [Wherein, R and X each represent a monovalent organic group. ]
  • the second step in the present embodiment is preferably performed by reacting the imide carboxylic acid with a diisocyanate represented by the following general formula (8) or a monoisocyanate represented by the following general formula (9).
  • an imide-amide compound represented by the general formula (2) or (3) is obtained.
  • R 1 and R 2 represent a monovalent organic group
  • X 1 represents a divalent organic group
  • X 2 represents a monovalent organic group
  • R 1 and R in formula (2) 2 may be the same or different.
  • an imide-amide compound represented mainly by the general formula (2) is formed.
  • an imide carboxylic acid represented by the general formula (6) and a compound obtained by reacting only one of the two isocyanate groups of the diisocyanate (that is, an imide represented by the general formula (3)) -Amide compounds) can be formed.
  • a mixture of the imide-amide compound represented by the general formula (2) and the imide-amide compound represented by the general formula (3) may be used as it is.
  • an imide-amide compound represented by the general formula (2) obtained by isolating a by-product from the mixture may be used.
  • Specific examples and preferred examples of the diisocyanate represented by the general formula (8) are the same as the specific examples and preferred examples of the diisocyanate which is the base of the structure of X 1 in the first embodiment. Further, specific examples and preferred examples of monoisocyanates of the general formula (9) are the same as the specific examples and preferred examples of the underlying monoisocyanate X 2 becomes the structure of the first embodiment. Specific examples and preferred examples of monoamines represented by the general formula (5) (including R 1 and R 2 in the general formula (2) and a monoamine that is the basis of the structure R 1 in the general formula (2)) are also included. Examples are the same as the specific examples and preferred examples of the diisocyanate that is the base of the structure X 1 in the first embodiment.
  • the charging ratio of trimellitic anhydride represented by formula (4) and monoamine represented by general formula (5) is trimellitic anhydride represented by general formula (4).
  • the monoamine represented by the general formula (5) is preferably 0.8 to 1.2 mol, particularly 0.9 to 1.1 mol, per 1 mol.
  • the reaction temperature is preferably 100 to 350 ° C., particularly 130 to 260 ° C. By reacting at such a temperature, the reaction intermediate represented by the general formula (6) can be obtained in high yield by dehydration cyclization.
  • the reaction is preferably carried out at 0 ° C. to 100 ° C. initially, and then 100 to 350 ° C., particularly 130 to 260 ° C.
  • the reaction time is preferably 1 to 24 hours, particularly 4 to 12 hours.
  • the reaction of the trimellitic anhydride represented by the general formula (4) and the monoamine represented by the general formula (5) in the first step is performed without solvent, in a solvent, or in a lubricating base oil described later.
  • the solvent organic solvents such as N-methyl-2-pyrrolidone, dimethylformamide, dimethyl sulfoxide, acetone, tetrahydrofuran, toluene, or a mixed solvent of two or more of these can be used.
  • the reaction between the imide carboxylic acid represented by the general formula (6) and the diisocyanate represented by the general formula (8) or the monoasocyanate represented by the general formula (9) is carried out in a solvent.
  • a solvent organic solvents such as N-methyl-2-pyrrolidone, dimethylformamide, dimethyl sulfoxide, acetone, tetrahydrofuran, toluene, or a mixed solvent of two or more of these can be used.
  • organic solvents such as N-methyl-2-pyrrolidone, dimethylformamide, dimethyl sulfoxide, acetone, tetrahydrofuran, toluene, or a mixed solvent of two or more of these can be used.
  • a lubricating base oil it can be used as it is as a grease composition.
  • the usage-amount of the diisocyanate represented by General formula (8) in a 2nd process in particular is not restrict
  • the reaction temperature is preferably 80 to 200 ° C, particularly 130 to 180 ° C.
  • the reaction time is preferably 0.5 to 10 hours, particularly 1 to 4 hours.
  • the usage-amount of the monoisocyanate represented by General formula (9) in a 2nd process in particular is not restrict
  • the reaction temperature is preferably 80 to 200 ° C, particularly 130 to 180 ° C.
  • the reaction time is preferably 0.5 to 10 hours, particularly 1 to 4 hours.
  • the thickener for grease according to the third embodiment of the present invention contains an imide-amide compound represented by the general formula (1).
  • Specific examples and preferred examples of the imide-amide compound represented by the general formula (1) are the same as the specific examples and preferred examples of the imide-amide compound according to the first embodiment.
  • the grease thickener according to the present embodiment may contain a thickener component other than the imide-amide compound.
  • thickener components include soap-type thickener components such as metal soaps and composite metal soaps; non-soap-type thickener components such as benton, silica gel, urea compounds, urea / urethane compounds, urethane compounds, imide compounds, etc. Any thickener component can be used.
  • the soap-based thickener component include sodium soap, calcium soap, aluminum soap, lithium soap and the like.
  • urea compound, urea / urethane compound, and urethane compound examples include diurea compounds, triurea compounds, tetraurea compounds, other polyurea compounds, urea / urethane compounds, diurethane compounds, and mixtures thereof.
  • the imide-amide compound according to the first embodiment and the thickener for grease according to the third embodiment are excellent in heat resistance, so that they are used for constant speed gears, transmission gears, steel making equipment, It is particularly preferably used as a grease thickener for ball bearings and roller bearings.
  • the use temperature in these applications is preferably ⁇ 40 ° C. to 300 ° C., more preferably ⁇ 40 ° C. to 250 ° C.
  • the grease composition according to the fourth embodiment of the present invention contains a lubricating base oil and an imide-amide compound represented by the above general formula (1), and the content of the imide-amide compound is the grease composition. 2 to 50% by mass based on the total amount of the product.
  • the content of the imide-amide compound represented by the general formula (1) is 2% by mass or more, preferably 5% by mass or more based on the total amount of the grease composition. , 50% by mass or less, preferably 40% by mass or less. If the content of the imide-amide compound is less than 2% by mass, the effect as a thickener is small, so that it does not become a sufficient grease, and if it exceeds 50% by mass, it becomes too hard as a grease and sufficient lubrication Since performance cannot be demonstrated, it is not preferable respectively.
  • the lubricating base oil of the grease composition according to this embodiment includes mineral oil and / or synthetic oil.
  • Mineral oil can be obtained by a method commonly used in the oil refining industry's lubricating oil production process.
  • a lubricating oil fraction obtained by subjecting crude oil to atmospheric distillation and vacuum distillation can be desolvated, solvent extracted, Examples include those purified by one or more treatments such as hydrocracking, solvent dewaxing, catalytic dewaxing, hydrorefining, sulfuric acid washing, and clay treatment.
  • synthetic oils include poly- ⁇ -olefins such as polybutene, 1-octene oligomer, 1-decene oligomer or hydrides thereof; ditridecyl glutarate, di-2-ethylhexyl adipate, diisodecyl adipate, ditridecyl adipate, Diesters such as di3-ethylhexyl sebacate; polyol esters such as trimethylolpropane caprylate, trimethylolpropane pelargonate, pentaerythritol 2-ethylhexanoate, pentaerythritol pelargonate; alkyl naphthalenes; alkylbenzenes, polyoxyalkylene glycols; Polyphenyl ethers; dialkyl diphenyl ethers; silicone oils; or mixtures thereof.
  • poly- ⁇ -olefins such as polybutene, 1-o
  • synthetic oils are preferable, and polyol esters, polyphenyl ethers, alkyl diphenyl ethers, and alkyl naphthalenes are more preferable.
  • the kinematic viscosity at 100 ° C. of the lubricating base oil is preferably 2 to 40 mm 2 / s, more preferably 3 to 20 mm 2 / s.
  • the viscosity index of the lubricating base oil is preferably 90 or higher, more preferably 100 or higher.
  • the grease composition according to the present embodiment other than the imide-amide compound represented by the above general formula (1), as necessary, in order to further improve the performance, as long as the properties are not impaired.
  • Thickeners other than the imide-amide compound represented by the general formula (1) include soap-type thickeners such as metal soaps and composite metal soaps; Benton, silica gel, urea compounds, urea / urethane compounds, urethanes Any thickeners such as non-soap thickeners such as compounds and imide compounds can be used.
  • the soap-based thickener include sodium soap, calcium soap, aluminum soap, lithium soap and the like.
  • Examples of the urea compound, urea / urethane compound, and urethane compound include diurea compounds, triurea compounds, tetraurea compounds, other polyurea compounds, urea / urethane compounds, diurethane compounds, and mixtures thereof.
  • an imide-amide compound other than the imide-amide compound represented by the general formula (1) may be contained.
  • solid lubricants include graphite, carbon black, fluorinated graphite, polytetrafluoroethylene, molybdenum disulfide, antimony sulfide, and alkali (earth) metal borates.
  • extreme pressure agent examples include organic zinc compounds such as zinc dialkyldithiophosphate and zinc diaryldithiophosphate; sulfur-containing compounds such as dihydrocarbyl polysulfide, sulfide ester, thiazole compound and thiadiazole compound; phosphates and phosphites Etc.
  • antioxidants include phenol compounds such as 2,6-di-t-butylphenol and 2,6-di-t-butyl-p-cresol; dialkyldiphenylamine, phenyl- ⁇ -naphthylamine, p- Examples thereof include amine compounds such as alkylphenyl- ⁇ -naphthylamine; sulfur compounds; phenothiazine compounds.
  • oily agents include amines such as laurylamine, myristylamine, palmitylamine, stearylamine, oleylamine; higher alcohols such as lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol; laurin Higher fatty acids such as acid, myristic acid, palmitic acid, stearic acid, oleic acid; fatty acid esters such as methyl laurate, methyl myristate, methyl palmitate, methyl stearate, methyl oleate; laurylamide, myristylamide, Amides such as palmitylamide, stearylamide, oleylamide; oils and fats.
  • amines such as laurylamine, myristylamine, palmitylamine, stearylamine, oleylamine
  • higher alcohols such as lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol
  • rust inhibitor examples include metal soaps; partial alcohol esters such as sorbitan fatty acid esters; amines; phosphoric acid;
  • viscosity index improver examples include polymethacrylate, polyisobutylene, and polystyrene.
  • cleaning dispersant examples include sulfonate, salicylate, phenate, and the like.
  • the lubricant base oil contains the imide-amide compound represented by the general formula (1) or a thickener containing the imide-amide compound, and further necessary.
  • other additives may be mixed and the mixture stirred and then passed through a roll mill or the like.
  • the grease composition according to the fourth embodiment is excellent in heat resistance, it is used for constant speed gears, transmission gears, automobiles, steelmaking equipment, industrial machinery, precision machinery, ball bearings used at high temperatures. It is particularly preferably used as grease for roller bearings and the like.
  • the use temperature in these applications is preferably ⁇ 40 ° C. to 300 ° C., more preferably ⁇ 40 ° C. to 250 ° C.
  • Example 1 In 250 mL of NMP (N-methyl-2-pyrrolidone) solvent, 43.8 g of trimellitic anhydride represented by the following formula (4) and 42.3 g of dodecylamine represented by the following formula (10) The reaction was carried out at 25 ° C. for 4 hours while cooling. Subsequently, 250 mL of toluene was added, and the mixture was heated for 4 hours while being azeotropically dehydrated using a Dean-Stark apparatus at reflux temperature.
  • NMP N-methyl-2-pyrrolidone
  • the infrared absorption spectrum of imide-amide compound-1 (manufactured by JASCO Corporation, FT / IR-410) was measured by the KBr method. The result is shown in FIG. As shown in FIG. 1, about 1720 cm -1 and derived from cyclic imido group, absorption of about 1660 cm -1 derived from about 1780 cm -1, and an amide group is confirmed, about attributed to isocyanide groups of the reaction raw material Absorption at 2270 cm ⁇ 1 was not confirmed. From this result, it was confirmed that the obtained solid was an imide-amide compound.
  • imide-amide compound-1 was subjected to FD-MS measurement (JEOL Ltd. JMS-T100GC, ionization method: FD +, solvent: on-propylphenol). The result is shown in FIG. The peak attributed to the imide-amide compound represented by the general formula (14) was 97% with respect to the total ionic strength.
  • Examples 2 to 18 monoamines represented by the above formulas (10) to (12) or the following formulas (15) to (18) as monoamines represented by the general formula (4) are represented by the general formula (8).
  • imide compounds -2 to 18 were obtained as solids.
  • Examples 5 to 7, 14 and 16 use two types of monoamines, and after synthesizing each of the intermediates in the same manner as in Example 1, the molar ratio was 1: 1 and the two types of intermediates were combined.
  • the infrared absorption spectra were measured in the same manner as in Example 1.
  • imide-amide compounds-2 to 18 obtained in Examples 2 to 18 were subjected to FD-MS measurement in the same manner as in Example 1.
  • the imide-amide compounds contained are shown in Tables 1 to 6, respectively. Peaks attributed to imide-amide compounds (compounds represented by the following formulas (23) to (39)) were observed.
  • the intensity ratios of the contained imide-amide compounds to the total ion intensity observed in each example are shown in Tables 1 to 6.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Rolling Contact Bearings (AREA)
  • Indole Compounds (AREA)

Abstract

La présente invention concerne un composé de type imide-amide représenté par la formule générale (1). Ledit composé imide-amide présente une remarquable longévité à haute température, notamment lorsqu'il est utilisé en tant qu'épaississant pour graisse (Dans la formule, R et X représentent chacun un groupe organique monovalent).
PCT/JP2013/063713 2012-05-17 2013-05-16 Composé de type imide-amide et son procédé de production, épaississant pour graisse et composition de graisse WO2013172428A1 (fr)

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US3483217A (en) * 1966-12-02 1969-12-09 Allied Chem 9,10-dihydro-9,10-dioxoanthracenediyl- bis-(4'-carbamoylphthalimides
JPS4837422A (fr) * 1971-09-16 1973-06-02
JPS4989795A (fr) * 1972-12-28 1974-08-27
JPS5477661A (en) * 1977-12-02 1979-06-21 Teijin Ltd Crosslinked or uncrosslinked linear aromatic polyester composition and its production
JPS54113605A (en) * 1978-02-27 1979-09-05 Nippon Koyu Kk Lubricating grease composition intensified with imide base compound
JPS56139592A (en) * 1981-03-18 1981-10-31 Nippon Kouyu:Kk Lubricating grease composition
JPS57109896A (en) * 1980-12-26 1982-07-08 Toshiba Chem Corp Heat-resistant grease
JPH06501048A (ja) * 1991-04-25 1994-01-27 コンゾルテイウム　フユール　エレクトロケミツシエインヅストリー　ゲゼルシヤフト　ミツト　ベシユレンクテル　ハフツング 付加的にエステル基および／またはアミド基を有するポリシロキサン
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* Cited by examiner, † Cited by third party
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US3483217A (en) * 1966-12-02 1969-12-09 Allied Chem 9,10-dihydro-9,10-dioxoanthracenediyl- bis-(4'-carbamoylphthalimides
JPS4837422A (fr) * 1971-09-16 1973-06-02
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JPS57109896A (en) * 1980-12-26 1982-07-08 Toshiba Chem Corp Heat-resistant grease
JPS56139592A (en) * 1981-03-18 1981-10-31 Nippon Kouyu:Kk Lubricating grease composition
JPH06501048A (ja) * 1991-04-25 1994-01-27 コンゾルテイウム　フユール　エレクトロケミツシエインヅストリー　ゲゼルシヤフト　ミツト　ベシユレンクテル　ハフツング 付加的にエステル基および／またはアミド基を有するポリシロキサン
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