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WO2014076747A1 - Huile lubrifiante - Google Patents

Huile lubrifiante Download PDF

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Publication number
WO2014076747A1
WO2014076747A1 PCT/JP2012/079335 JP2012079335W WO2014076747A1 WO 2014076747 A1 WO2014076747 A1 WO 2014076747A1 JP 2012079335 W JP2012079335 W JP 2012079335W WO 2014076747 A1 WO2014076747 A1 WO 2014076747A1
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WIPO (PCT)
Prior art keywords
acid
methyl
mol adduct
mol
adduct
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Ceased
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English (en)
Japanese (ja)
Inventor
真也 辻本
川原　康行
康人 五十嵐
石田　寛
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New Japan Chemical Co Ltd
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New Japan Chemical Co Ltd
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Priority to PCT/JP2012/079335 priority Critical patent/WO2014076747A1/fr
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Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • 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
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • 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
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl 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
    • C10M2207/28—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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • 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
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/74—Noack Volatility
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/045—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for continuous variable transmission [CVT]
    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/135—Steam engines or turbines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • the present invention relates to a lubricating oil.
  • the lubricating oil used in these devices in order to achieve high efficiency.
  • the lubricating oil is used to reduce energy loss due to viscous friction. Viscosity is being reduced.
  • Mineral oil that is inexpensive and easily available has been mainly used as a lubricating oil.
  • Mineral oil is a mixture of hydrocarbon oils having various chemical structures, and is roughly divided into paraffinic and naphthenic (cycloparaffinic) depending on the main component hydrocarbon.
  • Paraffinic mineral oil and naphthenic mineral oil differ in viscosity characteristics (for example, viscosity index), lubrication characteristics, low-temperature fluidity, heat resistance and compatibility with additives depending on the degree of purification.
  • viscosity characteristics for example, viscosity index
  • lubricating oil is used in various places such as engine lubricating oil, gear lubricating oil, automatic transmission lubricating oil, and shock absorber lubricating oil.
  • engine lubricating oil gear lubricating oil
  • automatic transmission lubricating oil automatic transmission lubricating oil
  • shock absorber lubricating oil for these lubricating oils, studies are underway on lubricating oils with low viscosity and high lubricating performance for the purpose of improving fuel efficiency. More recently, emphasis has been placed on reducing friction at start-up and at low temperatures, and there is a need for lubricating oils having low viscosity and low frictional resistance over a wide temperature range from room temperature to low temperature.
  • mineral oil has been mainly used in the past, but in order to satisfy the low viscosity over a wide temperature range, the use of lubricating oils with high viscosity index, that is, synthetic hydrocarbons and esters.
  • esters aliphatic dibasic acid diester obtained from the reaction of aliphatic dibasic acid and monohydric alcohol, or neopentyl polyol (polyhydric alcohol having neopentyl type structure) and aliphatic carboxylic acid The use of neopentyl polyol esters obtained by reaction is known.
  • esters having a lower molecular weight are used. However, it has become difficult to satisfy heat resistance, particularly volatility resistance.
  • the hydrodynamic bearing supports the rotating shaft by the oil film pressure of the lubricating oil interposed in the gap between the outer peripheral surface of the shaft and the inner peripheral surface of the sleeve, and has a dynamic pressure groove on at least one of the outer peripheral surface of the shaft or the inner peripheral surface of the sleeve.
  • the sliding surface of the rotating shaft is levitated and supported by a lubricating oil film formed by the dynamic pressure effect.
  • a porous body made of sintered metal or the like is impregnated with lubricating oil or lubricating grease to provide a self-lubricating function, and a sintered oil-impregnated bearing that supports the rotating shaft, and also a bearing surface of the sintered oil-impregnated bearing
  • a hydrodynamic sintered oil-impregnated bearing provided with a hydrodynamic groove is also used in the rotating device.
  • Lubricating oils used in such hydrodynamic bearings and sintered oil-impregnated bearings have low viscosity even at low temperatures, good low-temperature fluidity, and low viscosity reduction even at high temperatures. Viscosity characteristics and low evaporation are required.
  • lubricating oils for hydrodynamic bearings or sintered oil-impregnated bearings include synthetic hydrocarbon oils such as poly- ⁇ -olefins, ester oils such as aliphatic dibasic acid diesters, neopentyl polyol esters, and fatty acid monoesters.
  • synthetic hydrocarbon oils such as poly- ⁇ -olefins
  • ester oils such as aliphatic dibasic acid diesters, neopentyl polyol esters, and fatty acid monoesters.
  • the used lubricating oil is disclosed (Patent Documents 1 to 5).
  • Japanese Unexamined Patent Publication No. 7-53984 Japanese Patent Laid-Open No. 9-1225086 Japanese Patent Laid-Open No. 11-172267 JP 2001-316687 A JP 2002-146374 A
  • An object of the present invention is to provide a lubricating oil having a small change rate of viscosity in a wide temperature range (high viscosity index), low viscosity even at low temperature, good conductivity and good volatility resistance. .
  • aliphatic dihydric alcohol diesters having a specific structure have a high viscosity index, low viscosity even at low temperatures, good conductivity, and resistance to volatilization. As a result, the present invention has been completed.
  • the present invention provides the following lubricating oil.
  • R 1 and R 2 are the same or different and each represents a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated monocarboxylic acid having 3 to 17 carbon atoms.
  • A represents a residue obtained by removing a hydroxyl group from a linear or branched aliphatic diol having 4 to 10 carbon atoms.
  • B represents a group represented by the following general formula (a), (b) or (c). ]
  • a in the general formula (1) is a branched chain having 4 to 10 carbon atoms, which is composed of a linear alkylene group as a main chain and one or more alkyl groups bonded thereto.
  • Item 4 The lubricating oil according to Item 1, which is a residue obtained by removing a hydroxyl group from the aliphatic diol.
  • a in the general formula (1) is composed of a linear alkylene group as a main chain and one or two or more alkyl groups bonded thereto, and has two or more alkyl groups
  • these alkyl groups are not bonded simultaneously to the same carbon atom of a linear alkylene group as the main chain, but are residues obtained by removing a hydroxyl group from a branched aliphatic diol having 4 to 10 carbon atoms
  • a in the general formula (1) is 1,4-butanediol residue, 1,5-pentanediol residue, 1,6-hexanediol residue, 1,7-heptanediol residue, 1,8 -Octanediol residue, 1,9-nonanediol residue, 1,10-decanediol residue, 2-methyl-1,3-propanediol residue, 1,3-butanediol residue, 2-methyl- 1,4-butanediol residue, 1,4-pentanediol residue, 2-methyl-1,5-pentanediol residue, 3-methyl-1,5-pentanediol residue, 1,5-hexanediol Residue, 2-methyl-1,6-hexanediol residue, 3-methyl-1,6-hexanediol residue, 1,6-heptanediol residue, 2-methyl-1,7
  • a in the general formula (1) is a 2-methyl-1,4-butanediol residue, a 2-methyl-1,5-pentanediol residue, a 3-methyl-1,5-pentanediol residue, 2-methyl-1,6-hexanediol residue, 3-methyl-1,6-hexanediol residue, 2-methyl-1,7-heptanediol residue, 3-methyl-1,7-heptanediol residue 4-methyl-1,7-heptanediol residue, 2-methyl-1,8-octanediol residue, 3-methyl-1,8-octanediol residue, 4-methyl-1,8-octane Diol residue, 2-methyl-1,9-nonanediol residue, 3-methyl-1,9-nonanediol residue, 4-methyl-1,9-nonanediol residue, 5-methyl-1,9 -Nonaned
  • Item 2 The lubricating oil according to Item 1, wherein A in the general formula (1) is a 3-methyl-1,5-pentanediol residue or a 2,4-diethyl-1,5-pentanediol residue.
  • R 1 and R 2 described in the general formula (1) are the same or different and each is a residue obtained by removing a carboxyl group from a linear aliphatic saturated monocarboxylic acid having 6 to 9 carbon atoms.
  • the lubricating oil according to any one of 1 to 6.
  • the lubricating oil is a refrigeration lubricant, an engine lubricant, a gear lubricant, a bearing lubricant, an automatic transmission lubricant, a continuously variable transmission lubricant, a power steering lubricant, and an active suspension.
  • Item 8 The lubricant according to any one of Items 1 to 7, which is a lubricant, a shock absorber lubricant, a turbine lubricant, a compressor lubricant, a hydraulic fluid, or a grease base oil.
  • Item 8 A lubricating oil composition for a spindle motor, comprising the lubricating oil according to any one of Items 1 to 7 and an antioxidant.
  • a hydrodynamic bearing comprising a shaft and a sleeve, wherein the lubricating oil composition for a spindle motor according to item 11 or 12 is used.
  • R 1 and R 2 are the same or different and each represents a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated monocarboxylic acid having 6 to 9 carbon atoms.
  • A represents a residue obtained by removing a hydroxyl group from 3-methyl-1,5-pentanediol or 2,4-diethyl-1,5-pentanediol.
  • B represents a group represented by the following general formula (a), (b) or (c). ]
  • An aliphatic dihydric alcohol diester represented by:
  • R 1 and R 2 described in the general formula (1) are the same or different and each is a residue obtained by removing a carboxyl group from a linear aliphatic saturated monocarboxylic acid having 6 to 9 carbon atoms. 15. The aliphatic dihydric alcohol diester according to 15.
  • R 1 and R 2 are the same or different and each represents a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated monocarboxylic acid having 6 to 9 carbon atoms.
  • A represents a residue obtained by removing a hydroxyl group from 3-methyl-1,5-pentanediol or 2,4-diethyl-1,5-pentanediol.
  • B represents a group represented by the following general formula (a), (b) or (c). ]
  • a process for producing an aliphatic dihydric alcohol diester represented by: (1) Addition of an alkylene oxide having a group represented by the general formula (a), (b) or (c) to 3-methyl-1,5-pentanediol or 2,4-diethyl-1,5-pentanediol And then purifying, and (2) including a step of esterifying the alkylene oxide 1 mol adduct of the aliphatic diol obtained in the step (1) with a linear or branched aliphatic saturated monocarboxylic acid having 6 to 9 carbon atoms.
  • a process for producing an aliphatic dihydric alcohol diester characterized by
  • A represents a residue obtained by removing a hydroxyl group from a linear or branched aliphatic diol having 4 to 10 carbon atoms.
  • B represents a group represented by the following general formula (a), (b) or (c). ]
  • a lubricating oil having a small viscosity change rate (high viscosity index) over a wide temperature range, a low viscosity even at a low temperature, good conductivity and good volatilization resistance.
  • 1 is an example of a sectional view schematically showing a schematic configuration of a fluid dynamic bearing according to the present invention.
  • 1 is an example of a cross-sectional view schematically showing a schematic configuration of a spindle motor of the present invention.
  • 1 is 1 H-NMR of Example 1.
  • 2 is an IR spectrum of Example 1.
  • 1 is 1 H-NMR of Example 2.
  • 2 is an IR spectrum of Example 2.
  • 1 is 1 H-NMR of Example 3.
  • 4 is an IR spectrum of Example 3.
  • 1 is 1 H-NMR of Example 4.
  • 1 is 1 H-NMR of Example 5.
  • 6 is an IR spectrum of Example 5.
  • 1 is 1 H-NMR of Example 6.
  • 7 is an IR spectrum of Example 6.
  • 1 is 1 H-NMR of Example 7.
  • 7 is an IR spectrum of Example 7.
  • 1 is 1 H-NMR of Example 8.
  • 1 is 1 H-NMR of Example 9.
  • 2 is 1 H-NMR
  • the lubricating oil of the present invention is a lubricating oil characterized by containing one or more aliphatic dihydric alcohol diesters represented by the general formula (1).
  • the aliphatic dihydric alcohol according to the present invention is represented by the general formula (1 ′).
  • A is a residue obtained by removing a hydroxyl group from a linear or branched aliphatic diol having 4 to 10 carbon atoms.
  • a “residue obtained by removing a hydroxyl group from an aliphatic diol” may be simply referred to as an “aliphatic diol residue”, but both expressions are synonymous.
  • the “carbon number” refers to the total carbon number of “residue obtained by removing a hydroxyl group from an aliphatic diol”.
  • linear aliphatic diol residues examples include 1,4-butanediol residue, 1,5-pentanediol residue, 1,6-hexanediol residue, 1,7-heptanediol residue, 1, Examples include 8-octanediol residue, 1,9-nonanediol residue, and 1,10-decanediol residue.
  • Examples of the branched aliphatic diol residue include 2-methyl-1,3-propanediol residue, 1,3-butanediol residue, 2-methyl-1,4-butanediol residue, 1 , 4-pentanediol residue, 2-methyl-1,5-pentanediol residue, 3-methyl-1,5-pentanediol residue, 1,5-hexanediol residue, 2-methyl-1,6 -Hexanediol residue, 3-methyl-1,6-hexanediol residue, 1,6-heptanediol residue, 2-methyl-1,7-heptanediol residue, 3-methyl-1,7-heptane Diol residue, 4-methyl-1,7-heptanediol residue, 1,7-octanediol residue, 2-methyl-1,8-octanediol residue, 3-methyl-1,8-octanediol
  • a of the aliphatic dihydric alcohol represented by the general formula (1 ′) is a linear alkylene group as a main chain and one or two or more alkyl groups (branched) bonded thereto. And a residue obtained by removing a hydroxyl group from a branched aliphatic diol having 4 to 10 carbon atoms.
  • B is a group represented by the general formula (a), (b) or (c).
  • the aliphatic dihydric alcohol according to the present invention is composed of an alkylene oxide 1 mol adduct of an aliphatic diol as represented by the above general formula (1 '). Specifically, ethylene oxide 1 mol adduct of 1,4-butanediol, ethylene oxide 1 mol adduct of 1,5-pentanediol, ethylene oxide 1 mol adduct of 1,6-hexanediol, 1,7-heptanediol Ethylene oxide 1 mol adduct, 1,8-octanediol ethylene oxide 1 mol adduct, 1,9-nonanediol ethylene oxide 1 mol adduct, 1,10-decanediol ethylene oxide 1 mol adduct, 2-methyl- 1,3-propanediol ethylene oxide 1 mol adduct, 1,3-butanediol ethylene oxide 1 mol adduct,
  • an aliphatic dihydric alcohol for example, it is produced by adding ethylene oxide or propylene oxide to an aliphatic diol and then purifying it to obtain an alkylene oxide 1 mol adduct of an aliphatic diol.
  • a method for producing an aliphatic dihydric alcohol for example, it is produced by adding ethylene oxide or propylene oxide to an aliphatic diol and then purifying it to obtain an alkylene oxide 1 mol adduct of an aliphatic diol.
  • an aliphatic diol is subjected to an addition reaction with an aliphatic diol in the presence of a catalyst to obtain an alkylene oxide addition reaction mixture of the aliphatic diol.
  • the step of obtaining an oxide 1 mol adduct is exemplified.
  • ethylene oxide or propylene oxide is usually 0.5 to 1.5 mol, preferably 0.8 to 1.2 mol, relative to 1 mol of the aliphatic diol.
  • the catalyst examples include base catalysts such as alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal alkoxides, alkaline earth metal oxides, amines, and acid catalysts such as mineral acids, carboxylic acids, and Lewis acids. Is done. More specifically, the alkali metal hydroxide includes sodium hydroxide and potassium hydroxide, the alkaline earth metal hydroxide includes calcium hydroxide and barium hydroxide, and the alkali metal alkoxide includes sodium methoxy. And lithium isopropoxide. Further, examples of the mineral acid include sulfuric acid and phosphoric acid, examples of the carboxylic acid include acetic acid, and examples of the Lewis acid include boron trifluoride and aluminum chloride. The amount used is, for example, usually about 0.01 to 5.0% by weight with respect to the aliphatic diol.
  • the addition reaction is usually performed at a reaction temperature of 50 to 250 ° C., preferably 100 to 200 ° C.
  • the aliphatic dihydric alcohol of the present invention can be used as an intermediate for obtaining an aliphatic dihydric alcohol diester described later.
  • aliphatic dihydric alcohol diester The aliphatic dihydric alcohol diester according to the present invention is represented by the general formula (1).
  • R 1 and R 2 are the same or different and are each a residue obtained by removing a carboxyl group from a linear or branched aliphatic saturated monocarboxylic acid having 3 to 17 carbon atoms. It is a group.
  • a “residue obtained by removing a carboxyl group from an aliphatic saturated monocarboxylic acid” may be simply referred to as an “aliphatic saturated monocarboxylic acid residue”. Expression is also synonymous.
  • the “carbon number” refers to the total carbon number of “residue obtained by removing a carboxyl group from an aliphatic saturated monocarboxylic acid”.
  • Linear aliphatic saturated monocarboxylic acid residues include n-butanoic acid residues, n-pentanoic acid residues, n-hexanoic acid residues, n-heptanoic acid residues, n-octanoic acid residues, n-nonanoic acid residue, n-decanoic acid residue, n-undecanoic acid residue, n-dodecanoic acid residue, n-tridecanoic acid residue, n-tetradecanoic acid residue, n-pentadecanoic acid residue, n -Hexadecanoic acid residue, n-heptadecanoic acid residue and n-octadecanoic acid residue.
  • Examples of the branched aliphatic saturated monocarboxylic acid residue include isobutanoic acid residue, isopentanoic acid residue, isohexanoic acid residue, isoheptanoic acid residue, isooctanoic acid residue, 2-ethylhexanoic acid residue, Examples include isononanoic acid residue, 3,5,5-trimethylhexanoic acid residue, isodecanoic acid residue, isoundecanoic acid residue and the like. These can be used alone or in combination of two or more.
  • linear aliphatic saturated monocarboxylic acid residues are preferable, and linear aliphatic saturated monocarboxylic acid residues having 6 to 9 carbon atoms are particularly preferable.
  • A is a residue obtained by removing a hydroxyl group from a linear or branched aliphatic diol having 4 to 10 carbon atoms.
  • a “residue obtained by removing a hydroxyl group from an aliphatic diol” may be simply referred to as an “aliphatic diol residue”, but both expressions are synonymous.
  • the “carbon number” refers to the total carbon number of “residue obtained by removing a hydroxyl group from an aliphatic diol”.
  • linear aliphatic diol residues examples include 1,4-butanediol residue, 1,5-pentanediol residue, 1,6-hexanediol residue, 1,7-heptanediol residue, 1, Examples include 8-octanediol residue, 1,9-nonanediol residue, and 1,10-decanediol residue.
  • Examples of the branched aliphatic diol residue include 2-methyl-1,3-propanediol residue, 1,3-butanediol residue, 2-methyl-1,4-butanediol residue, 1 , 4-pentanediol residue, 2-methyl-1,5-pentanediol residue, 3-methyl-1,5-pentanediol residue, 1,5-hexanediol residue, 2-methyl-1,6 -Hexanediol residue, 3-methyl-1,6-hexanediol residue, 1,6-heptanediol residue, 2-methyl-1,7-heptanediol residue, 3-methyl-1,7-heptane Diol residue, 4-methyl-1,7-heptanediol residue, 1,7-octanediol residue, 2-methyl-1,8-octanediol residue, 3-methyl-1,8-octanediol
  • a of the aliphatic dihydric alcohol diester represented by the general formula (1) is a linear alkylene group as a main chain and one or two or more alkyl groups (branched) bonded thereto. And a residue obtained by removing a hydroxyl group from a branched aliphatic diol having 4 to 10 carbon atoms.
  • B is a group represented by the general formula (a), (b) or (c).
  • the aliphatic dihydric alcohol diester according to the present invention is composed of a diester of an aliphatic diol alkylene oxide 1 mol adduct and a saturated aliphatic monocarboxylic acid, as represented by the general formula (1). .
  • ethylene oxide 1 mol adduct of 1,4-butanediol ethylene oxide 1 mol adduct of 1,5-pentanediol, ethylene oxide 1 mol adduct of 1,6-hexanediol, 1,7-heptanediol Ethylene oxide 1 mol adduct, 1,8-octanediol ethylene oxide 1 mol adduct, 1,9-nonanediol ethylene oxide 1 mol adduct, 1,10-decanediol ethylene oxide 1 mol adduct, 2-methyl- 1,3-propanediol ethylene oxide 1 mol adduct, 1,3-butanediol ethylene oxide 1 mol adduct, 2-methyl-1,4-butanediol ethylene oxide 1 mol adduct, 1,4-pentanediol 1 mol of ethylene oxide adduct, 2-methyl-1
  • diester of 2-methyl-1,4-butanediol with 1 mol of ethylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms Diester of 2-methyl-1,4-butanediol with 1 mol of ethylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms, Diester of 2-methyl-1,5-pentanediol with 1 mol of ethylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms, A diester of ethylene oxide 1 mol adduct of 3-methyl-1,5-pentanediol with a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms, A diester of propylene oxide 1 mol
  • diesters of 2-methyl-1,4-butanediol with 1 mol of ethylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2-methyl 1,4-butanediol ethylene oxide 1 mol adduct di (n-heptanoate), 2-methyl-1,4-butanediol ethylene oxide 1 mol adduct di (n-octanoate), 2-methyl-1 , 4-Butanediol ethylene oxide 1 mol adduct di (n-nonanoate), 2-methyl-1,4-butanediol ethylene oxide 1 mol adduct di (n-decanoate), 2-methyl-1,4-butane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 2-methyl-1,4-butyl Diester obtained from 1 mol
  • diester of 2-methyl-1,5-pentanediol ethylene oxide 1 mol adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2-methyl 1,5-pentanediol ethylene oxide 1 mol adduct di (n-heptanoate), 2-methyl-1,5-pentanediol ethylene oxide 1 mol adduct di (n-octanoate), 2-methyl-1 1,5-pentanediol ethylene oxide 1 mol adduct di (n-nonanoate), 2-methyl-1,5-pentanediol ethylene oxide 1 mol adduct di (n-decanoate), 2-methyl-1,5-pentane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 2-methyl Diester obtained from ethylene oxide 1 mol
  • diester of 2-methyl-1,5-pentanediol with 1 mol of propylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2- Propylene oxide 1-mole adduct di (n-heptanoate) of methyl-1,5-pentanediol, 2-methyl-1,5-pentanediol propylene oxide 1-mole adduct di (n-octanoate), 2- Propylene oxide 1 mol adduct di (n-nonanoate) of methyl-1,5-pentanediol, 2-methyl-1,5-pentanediol propylene oxide 1 mol adduct di (n-decanoate), 2-methyl- Diester obtained from 1 mol of propylene oxide adduct of 1,5-pentanediol and n-heptanoic acid and n-oct
  • diesters of ethylene oxide 1 mol adduct of 3-methyl-1,5-pentanediol and linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 3-methyl 1,5-pentanediol ethylene oxide 1 mol adduct di (n-heptanoate), 3-methyl-1,5-pentanediol ethylene oxide 1 mol adduct di (n-octanoate), 3-methyl-1 1,5-pentanediol ethylene oxide 1 mol adduct di (n-nonanoate), 3-methyl-1,5-pentanediol ethylene oxide 1 mol adduct di (n-decanoate), 3-methyl-1,5-pentane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 3-methyl Diester obtained from ethylene oxide 1 mol mol
  • diesters of 1-mol adduct of 3-methyl-1,5-pentanediol with propylene oxide and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 3- Propylene oxide 1 mol adduct di (n-heptanoate) of methyl-1,5-pentanediol, propylene oxide 1 mol adduct di (n-octanoate) of 3-methyl-1,5-pentanediol, 3- Propylene oxide 1 mol adduct di (n-nonanoate) of methyl-1,5-pentanediol, propylene oxide 1 mol adduct di (n-decanoate) of 3-methyl-1,5-pentanediol, 3-methyl- Diester obtained from 1 mol of propylene oxide adduct of 1,5-pentanediol and n-heptanoic acid and n-
  • diester of 2-methyl-1,6-hexanediol with 1 mol of ethylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2-methyl 1,6-hexanediol ethylene oxide 1 mol adduct di (n-heptanoate), 2-methyl-1,6-hexanediol ethylene oxide 1 mol adduct di (n-octanoate), 2-methyl-1 , 6-Hexanediol ethylene oxide 1 mol adduct di (n-nonanoate), 2-methyl-1,6-hexanediol ethylene oxide 1 mol adduct di (n-decanoate), 2-methyl-1,6-hexane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 2-methyl Diester obtained from ethylene
  • diesters of 1-mol adduct of 2-methyl-1,6-hexanediol with propylene oxide and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2- Propylene oxide 1 mol adduct di (n-heptanoate) of methyl-1,6-hexanediol, 2-propylene oxide 1 mol adduct di (n-octanoate) of 2-methyl-1,6-hexanediol, 2- Propylene oxide 1 mol adduct di (n-nonanoate) of methyl-1,6-hexanediol, 2-methyl-1,6-hexanediol propylene oxide 1 mol adduct di (n-decanoate), 2-methyl- Diester obtained from 1-mol propylene oxide adduct of 1,6-hexanediol and n-heptanoic acid and n-oc
  • diester of 3-methyl-1,6-hexanediol ethylene oxide 1 mol adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 3-methyl 1,6-hexanediol ethylene oxide 1 mol adduct di (n-heptanoate), 3-methyl-1,6-hexanediol ethylene oxide 1 mol adduct di (n-octanoate), 3-methyl-1 , 6-Hexanediol ethylene oxide 1 mol adduct di (n-nonanoate), 3-methyl-1,6-hexanediol ethylene oxide 1 mol adduct di (n-decanoate), 3-methyl-1,6-hexane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 3-methyl Diester obtained from ethylene oxide 1
  • diester of 3-methyl-1,6-hexanediol propylene oxide 1 mol adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 3- Propylene oxide 1 mol adduct di (n-heptanoate) of methyl-1,6-hexanediol, propylene oxide 1 mol adduct di (n-octanoate) of 3-methyl-1,6-hexanediol, 3- Propylene oxide 1 mol adduct di (n-nonanoate) of methyl-1,6-hexanediol, propylene oxide 1 mol adduct di (n-decanoate) of 3-methyl-1,6-hexanediol, 3-methyl- Diester obtained from 1-mol propylene oxide adduct of 1,6-hexanediol and n-heptanoic acid and n-oc
  • diesters of 2-methyl-1,7-heptanediol with 1 mol of ethylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2-methyl 1,7-heptanediol ethylene oxide 1 mol adduct di (n-heptanoate), 2-methyl-1,7-heptanediol ethylene oxide 1 mol adduct di (n-octanoate), 2-methyl-1 , 7-Heptanediol ethylene oxide 1 mol adduct di (n-nonanoate), 2-methyl-1,7-heptanediol ethylene oxide 1 mol adduct di (n-decanoate), 2-methyl-1,7-heptane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 2-methyl Diester obtained from 1 mol
  • diesters of 1-mol adduct of 2-methyl-1,7-heptanediol with propylene oxide and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2- Propylene oxide 1 mol adduct di (n-heptanoate) of methyl-1,7-heptanediol, 2-propylene oxide 1 mol adduct di (n-octanoate) of 2-methyl-1,7-heptanediol, 2- Propylene oxide 1 mol adduct di (n-nonanoate) of methyl-1,7-heptanediol, 2-methyl-1,7-heptanediol propylene oxide 1 mol adduct di (n-decanoate), 2-methyl- 1,7-heptanediol 1 mol propylene oxide adduct and diester obtained from n-heptanoic acid and n-oc
  • diesters of ethylene oxide 1 mol adduct of 3-methyl-1,7-heptanediol and linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 3-methyl 1,7-heptanediol ethylene oxide 1 mol adduct di (n-heptanoate), 3-methyl-1,7-heptanediol ethylene oxide 1 mol adduct di (n-octanoate), 3-methyl-1 , 7-Heptanediol ethylene oxide 1 mol adduct di (n-nonanoate), 3-methyl-1,7-heptanediol ethylene oxide 1 mol adduct di (n-decanoate), 3-methyl-1,7-heptane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 3-methyl Diester obtained from ethylene oxide 1 mol
  • diesters of 1-mol propylene oxide adduct of 3-methyl-1,7-heptanediol and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 3- Propylene oxide 1 mol adduct di (n-heptanoate) of methyl-1,7-heptanediol, Propylene oxide 1 mol adduct di (n-octanoate) of 3-methyl-1,7-heptanediol, 3- Propylene oxide 1 mol adduct di (n-nonanoate) of methyl-1,7-heptanediol, propylene oxide 1 mol adduct di (n-decanoate) of 3-methyl-1,7-heptanediol, 3-methyl- 1,7-heptanediol 1 mol propylene oxide adduct and diester obtained from n-heptanoic acid and n-oc
  • diesters of 4-methyl-1,7-heptanediol with 1 mol of ethylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 4-methyl 1,7-heptanediol ethylene oxide 1 mol adduct di (n-heptanoate), 4-methyl-1,7-heptanediol ethylene oxide 1 mol adduct di (n-octanoate), 4-methyl-1 , 7-Heptanediol ethylene oxide 1 mol adduct di (n-nonanoate), 4-methyl-1,7-heptanediol ethylene oxide 1 mol adduct di (n-decanoate), 4-methyl-1,7-heptane 4-Methyl diester obtained from 1 mol of ethylene oxide adduct of diol and n-heptanoic acid and n-octanoic acid Diester obtained
  • 2-methyl-1,8-octanediol ethylene oxide 1 mol adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms specifically, 2-methyl 1,8-octanediol ethylene oxide 1 mol adduct di (n-heptanoate), 2-methyl-1,8-octanediol ethylene oxide 1 mol adduct di (n-octanoate), 2-methyl-1 , 8-Octanediol ethylene oxide 1 mol adduct di (n-nonanoate), 2-methyl-1,8-octanediol ethylene oxide 1 mol adduct di (n-decanoate), 2-methyl-1,8-octane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 2-methyl-1,8-oc
  • diesters of a 1-mol adduct of 2-methyl-1,8-octanediol with propylene oxide and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2- Propylene oxide 1 mol adduct di (n-heptanoate) of methyl-1,8-octanediol, 2-propylene oxide 1 mol adduct di (n-octanoate) of 2-methyl-1,8-octanediol, 2- Propylene oxide 1 mol adduct di (n-nonanoate) of methyl-1,8-octanediol, propylene oxide 1 mol adduct di (n-decanoate) of 2-methyl-1,8-octanediol, 2-methyl- 1,8-octanediol propylene oxide 1 mol adduct and diester obtained from n-heptan
  • diesters of ethylene oxide 1 mol adduct of 3-methyl-1,8-octanediol and linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 3-methyl 1,8-octanediol ethylene oxide 1 mol adduct di (n-heptanoate), 3-methyl-1,8-octanediol ethylene oxide 1 mol adduct di (n-octanoate), 3-methyl-1 , 8-Octanediol ethylene oxide 1 mol adduct di (n-nonanoate), 3-methyl-1,8-octanediol ethylene oxide 1 mol adduct di (n-decanoate), 3-methyl-1,8-octane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 3-methyl Diester
  • diesters of 1-mol adduct of 3-methyl-1,8-octanediol with propylene oxide and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 3- Propylene oxide 1 mol adduct di (n-heptanoate) of methyl-1,8-octanediol, propylene oxide 1 mol adduct di (n-octanoate) of 3-methyl-1,8-octanediol, 3- Propylene oxide 1 mol adduct di (n-nonanoate) of methyl-1,8-octanediol, propylene oxide 1 mol adduct di (n-decanoate) of 3-methyl-1,8-octanediol, 3-methyl- 1,8-octanediol propylene oxide 1 mol adduct and diester obtained from n-heptanoic
  • diesters of 4-methyl-1,8-octanediol ethylene oxide 1 mol adduct and linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 4-methyl 1,8-octanediol ethylene oxide 1 mol adduct di (n-heptanoate), 4-methyl-1,8-octanediol ethylene oxide 1 mol adduct di (n-octanoate), 4-methyl-1 , 8-octanediol ethylene oxide 1 mol adduct di (n-nonanoate), 4-methyl-1,8-octanediol ethylene oxide 1 mol adduct di (n-decanoate), 4-methyl-1,8-octane 4-Methyl diester obtained from 1 mol of ethylene oxide adduct of diol and n-heptanoic acid and n-octanoic acid Die
  • diesters of 2-methyl-1,9-nonanediol with 1 mol of ethylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2-methyl 1,9-nonanediol ethylene oxide 1 mol adduct di (n-heptanoate), 2-methyl-1,9-nonanediol ethylene oxide 1 mol adduct di (n-octanoate), 2-methyl-1 1,9-nonanediol ethylene oxide 1 mol adduct di (n-nonanoate), 2-methyl-1,9-nonanediol ethylene oxide 1 mol adduct di (n-decanoate), 2-methyl-1,9-nonane Diester obtained from 1 mol of ethylene oxide 1 mol adduct of diol and n-heptanoic acid and n-octanoic acid, 2-methyl-1,9-n
  • diesters of ethylene oxide 1 mol adduct of 3-methyl-1,9-nonanediol and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 3-methyl 1,9-nonanediol ethylene oxide 1 mol adduct di (n-heptanoate), 3-methyl-1,9-nonanediol ethylene oxide 1 mol adduct di (n-octanoate), 3-methyl-1 1,9-nonanediol ethylene oxide 1 mol adduct di (n-nonanoate), 3-methyl-1,9-nonanediol ethylene oxide 1 mol adduct di (n-decanoate), 3-methyl-1,9-nonane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 3-methyl-1,9-no Diester obtained
  • diesters of 4-methyl-1,9-nonanediol with 1 mol of ethylene oxide adduct and linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 4-methyl 1,9-nonanediol ethylene oxide 1 mol adduct di (n-heptanoate), 4-methyl-1,9-nonanediol ethylene oxide 1 mol adduct di (n-octanoate), 4-methyl-1 1,9-nonanediol ethylene oxide 1 mol adduct di (n-nonanoate), 4-methyl-1,9-nonanediol ethylene oxide 1 mol adduct di (n-decanoate), 4-methyl-1,9-nonane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 4-methyl-1,9-no Diester obtained from
  • diesters of 1-mol adduct of 5-methyl-1,9-nonanediol with ethylene oxide and linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 5-methyl 1,9-nonanediol ethylene oxide 1 mol adduct di (n-heptanoate), 5-methyl-1,9-nonanediol ethylene oxide 1 mol adduct di (n-octanoate), 5-methyl-1 1,9-nonanediol ethylene oxide 1 mol adduct di (n-nonanoate), 5-methyl-1,9-nonanediol ethylene oxide 1 mol adduct di (n-decanoate), 5-methyl-1,9-nonane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and n-octanoic acid, 5-methyl-1,9-no Diester obtained from 1
  • diester of 5-methyl-1,9-nonanediol propylene oxide 1 mol adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include: Propylene oxide 1 mol adduct di (n-heptanoate) of methyl-1,9-nonanediol, propylene oxide 1 mol adduct di (n-octanoate) of 5-methyl-1,9-nonanediol, 5- Propylene oxide 1 mol adduct di (n-nonanoate) of methyl-1,9-nonanediol, propylene oxide 1 mol adduct di (n-decanoate) of 5-methyl-1,9-nonanediol, 5-methyl- 1,9-nonanediol propylene oxide 1 mol adduct, diester obtained from n-heptanoic acid and n-oc
  • diester of 2-ethyl-1,3-hexanediol with 1 mol of ethylene oxide adduct and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2-ethyl 1,3-hexanediol ethylene oxide 1 mol adduct di (n-heptanoate), 2-ethyl-1,3-hexanediol ethylene oxide 1 mol adduct di (n-octanoate), 2-ethyl-1 1,3-hexanediol ethylene oxide 1 mol adduct di (n-nonanoate), 2-ethyl-1,3-hexanediol ethylene oxide 1 mol adduct di (n-decanoate), 2-ethyl-1,3-hexane Diester obtained from 1 mol adduct of diol with ethylene oxide and n-heptanoic acid and
  • diesters of 1 mol adduct of 2-ethyl-1,3-hexanediol with propylene oxide and a linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2- Propylene oxide 1 mol adduct di (n-heptanoate) of ethyl-1,3-hexanediol, propylene oxide 1 mol adduct di (n-octanoate) of 2-ethyl-1,3-hexanediol, 2- Propylene oxide 1 mol adduct di (n-nonanoate) of ethyl-1,3-hexanediol, propylene oxide 1 mol adduct di (n-decanoate) of 2-ethyl-1,3-hexanediol, 2-ethyl- Diester obtained from 1 mol of propylene oxide adduct of 1,3-hexane
  • diesters of ethylene oxide 1 mol adduct of 2,4-diethyl-1,5-pentanediol and linear or branched saturated aliphatic monocarboxylic acid having 7 to 10 carbon atoms include 2 1,4-diethyl-1,5-pentanediol ethylene oxide 1 mol adduct di (n-heptanoate), 2,4-diethyl-1,5-pentanediol ethylene oxide 1 mol adduct di (n-octanoate) 2,4-diethyl-1,5-pentanediol ethylene oxide 1 mol adduct di (n-nonanoate), 2,4-diethyl-1,5-pentanediol ethylene oxide 1 mol adduct di (n-decanoate) 1,4-diethyl-1,5-pentanediol ethylene oxide 1 mol adduct and n-heptan
  • an alkylene oxide 1 mol adduct of an aliphatic diol is obtained, It is produced by esterifying the 1 mol adduct and an aliphatic saturated monocarboxylic acid (second step).
  • first step after adding an alkylene oxide to an aliphatic diol and then purifying (first step), an alkylene oxide 1 mol adduct of an aliphatic diol is obtained, It is produced by esterifying the 1 mol adduct and an aliphatic saturated monocarboxylic acid (second step).
  • First step> an addition reaction of an ethylene oxide or propylene oxide to an aliphatic diol in the presence of a catalyst to obtain an alkylene oxide addition reaction mixture of the aliphatic diol, followed by distillation purification, The process of obtaining 1 mol of alkylene oxide adduct is illustrated.
  • ethylene oxide or propylene oxide is usually 0.5 to 1.5 mol, preferably 0.8 to 1.2 mol, relative to 1 mol of the aliphatic diol.
  • the catalyst examples include base catalysts such as alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal alkoxides, alkaline earth metal oxides, amines, and acid catalysts such as mineral acids, carboxylic acids, and Lewis acids. Is done. More specifically, the alkali metal hydroxide includes sodium hydroxide and potassium hydroxide, the alkaline earth metal hydroxide includes calcium hydroxide and barium hydroxide, and the alkali metal alkoxide includes sodium methoxy. And lithium isopropoxide. Further, examples of the mineral acid include sulfuric acid and phosphoric acid, examples of the carboxylic acid include acetic acid, and examples of the Lewis acid include boron trifluoride and aluminum chloride. The amount used is, for example, usually about 0.01 to 5.0% by weight with respect to the aliphatic diol.
  • the addition reaction is usually performed at a reaction temperature of 50 to 250 ° C., preferably 100 to 200 ° C.
  • ⁇ Second step> As an example of the second step, an esterification reaction between an aliphatic oxide diol alkylene oxide adduct and an aliphatic saturated monocarboxylic acid is carried out in the presence of an esterification catalyst, followed by post-treatment and purification treatment. The process of obtaining the aliphatic dihydric alcohol diester which concerns on invention is illustrated.
  • the aliphatic saturated monocarboxylic acid is usually 2.01 to 2.10 mol, preferably 2.01 to 2.05 mol, based on 1 mol of an alkylene oxide 1 mol adduct of an aliphatic diol. Used.
  • esterification catalysts include Lewis acids and sulfonic acid derivatives. More specifically, examples of the Lewis acid include aluminum derivatives, tin derivatives, and titanium derivatives. Examples of the sulfonic acid derivative include p-toluenesulfonic acid, methanesulfonic acid, sulfuric acid and the like. The amount used is usually about 0.01 to 5.0% by weight based on the total weight of the aliphatic diol alkylene oxide 1 mol adduct and the aliphatic saturated monocarboxylic acid, for example.
  • the esterification reaction is preferably carried out at a reaction temperature of usually 120 to 250 ° C., preferably 140 to 230 ° C. in the presence of an inert gas.
  • the reaction time is usually about 3 to 30 hours.
  • the produced water may be distilled off azeotropically outside the system using a water entraining agent such as benzene, toluene, xylene, cyclohexane and the like.
  • the aliphatic dihydric alcohol diester can be purified by a conventional purification method such as neutralization, washing with water, liquid-liquid extraction, vacuum distillation, and purification of an adsorbent such as activated carbon.
  • a lower alkyl ester having 1 to 4 carbon atoms of the corresponding aliphatic saturated monocarboxylic acid may be used instead of the aliphatic saturated monocarboxylic acid.
  • the esterification catalyst an alkali metal catalyst having a transesterification catalytic ability is usually used.
  • examples of the alkali metal catalyst include sodium alkoxide and potassium alkoxide.
  • the amount used is usually about 0.01 to 5.0% by weight with respect to the total weight of the aliphatic diol alkylene oxide 1 mol adduct and the aliphatic saturated monocarboxylic acid ester, for example.
  • the resulting aliphatic dihydric alcohol diester is An ester mixture.
  • the resulting aliphatic dihydric alcohol diester is (I) a mixed ester comprising n-heptanoic acid and 2-ethylhexanoic acid, It is usually composed of (ii) a diester composed of n-heptanoic acid, and (iii) a diester composed of 2-ethylhexanoic acid.
  • the use ratio of the linear aliphatic saturated monocarboxylic acid and the branched aliphatic saturated monocarboxylic acid is not particularly limited and can be used at any ratio.
  • the lubricating oil of the present invention is characterized by containing one or more aliphatic dihydric alcohol diesters.
  • the lubricating oil of the present invention is a lubricating oil for refrigerators, lubricating oil for engines, lubricating oil for gears, lubricating oil for bearings, lubricating oil for automatic transmissions, lubricating oil for continuously variable transmissions, lubricating oil for power steering, active Used as suspension lubricating oil, shock absorber lubricating oil, turbine lubricating oil, compressor lubricating oil, hydraulic working oil or grease base oil.
  • the lubricating oil of the present invention is suitably used as a lubricating oil for spindle motors, and particularly suitably used as a lubricating oil for hydrodynamic bearings or sintered oil-impregnated bearings.
  • the lubricating oil of the present invention can be used for bearings of various materials such as iron bearings, copper bearings, lead bearings and the like.
  • the kinematic viscosity at 40 ° C. when used as a spindle motor lubricating oil is usually recommended to be in the range of 1 to 20 mm 2 / s, more preferably in the range of 5 to 14 mm 2 / s. A range of 7 to 13.5 mm 2 / s is recommended.
  • the said kinematic viscosity is a value obtained by the method described in the postscript Example.
  • the viscosity index when used as a spindle motor lubricating oil is usually 120 or higher, more preferably 130 or higher, and particularly 150 or higher.
  • the said viscosity index is a value obtained by the method described in the postscript Example.
  • the fluidity at a low temperature when used as a spindle motor lubricating oil can be evaluated by, for example, a low temperature fluidity test.
  • a low temperature fluidity test In the low temperature fluidity test, 0 ° C. or less is usually recommended, more preferably ⁇ 15 ° C. or less, and particularly preferably ⁇ 25 ° C. or less.
  • liquidity test is a value obtained by the method described in the postscript Example.
  • the conductivity when used as a lubricating oil for a spindle motor can be evaluated by, for example, volume resistivity.
  • the volume resistivity is usually recommended to be 8.0E + 12 ⁇ ⁇ cm or less, more preferably 5.0E + 12 ⁇ ⁇ cm or less, particularly 1.0E + 12 ⁇ ⁇ cm or less.
  • the said volume resistivity is a value obtained by the method described in the postscript Example.
  • the heat resistance when used as a lubricating oil for a spindle motor can be evaluated by, for example, a heat resistance test.
  • a heat resistance test usually 6% by weight or less is recommended, more preferably 5% by weight or less, and particularly preferably 4% by weight or less.
  • the said heat resistance test is a value obtained by the method described in the postscript Example.
  • the lubricating oil of the present invention is a lubricating oil containing an aliphatic dihydric alcohol diester for use as a lubricating base oil, or an aliphatic dihydric alcohol diester and another base oil (hereinafter referred to as “combined base oil”). And a mixture of the aliphatic dihydric alcohol diester with respect to the lubricating base oil in an amount of 15 to 100% by weight, preferably 40 to 100%. % By weight, more preferably 60 to 100% by weight, particularly preferably 80 to 100% by weight.
  • lubricating base oil refers to an aliphatic dihydric alcohol diester when the lubricating oil of the present invention contains only an aliphatic dihydric alcohol diester as the base oil.
  • the lubricating oil of the present invention contains a mixture of an aliphatic dihydric alcohol diester and a combined base oil for the purpose of use as a base oil, it indicates a mixture of an aliphatic dihydric alcohol diester and a combined base oil.
  • the combined base oil examples include mineral oil (hydrocarbon oil obtained by refining petroleum), poly- ⁇ -olefin, polybutene, alkylbenzene, alkylnaphthalene, alicyclic hydrocarbon oil, and synthetic hydrocarbon obtained by the Fischer-Tropsch process.
  • Synthetic hydrocarbon oils such as isomerized oils, animal and vegetable oils, organic acid esters other than the present esters, polyalkylene glycols, polyvinyl ethers, polyphenyl ethers, alkylphenyl ethers, silicone oils, and at least one of such combined base oils Species can be used together as appropriate.
  • the mineral oil examples include solvent refined mineral oil, hydrorefined mineral oil, and wax isomerized oil.
  • the kinematic viscosity at 100 ° C. is 1.0 to 25 mm 2 / s, preferably 2.0 to 20.0 mm 2. Those in the range of / s are used.
  • poly- ⁇ -olefins examples include ⁇ -olefins having 2 to 16 carbon atoms (for example, ethylene, propylene, 1-butene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, etc. ) And a copolymer having a kinematic viscosity at 100 ° C. of 1.0 to 25 mm 2 / s and a viscosity index of 100 or more. Those having a viscosity index of 120 mm or more at 0.0 mm 2 / s are preferable.
  • polybutene examples include those obtained by polymerizing isobutylene and those obtained by copolymerizing isobutylene with normal butylene, and generally include a wide range of those having a kinematic viscosity at 100 ° C. of 2.0 to 40 mm 2 / s.
  • alkyl benzene examples include monoalkyl benzene, dialkyl benzene, trialkyl benzene, and tetraalkyl benzene having a molecular weight of 200 to 450, which are substituted with a linear or branched alkyl group having 1 to 40 carbon atoms.
  • alkylnaphthalene examples include monoalkylnaphthalene and dialkylnaphthalene substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
  • animal and vegetable oils examples include beef tallow, lard, palm oil, coconut oil, rapeseed oil, castor oil, sunflower oil and the like.
  • organic acid esters other than aliphatic dihydric alcohol diesters include fatty acid monoesters, aliphatic dibasic acid diesters, polyol esters, and other esters.
  • the fatty acid monoester is an ester of an aliphatic linear or branched monocarboxylic acid having 5 to 22 carbon atoms and a linear or branched saturated or unsaturated aliphatic alcohol having 3 to 22 carbon atoms. Is mentioned.
  • Aliphatic dibasic acid diesters include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 1,9-nonamethylenedicarboxylic acid, 1,10-deca And a full ester of an aliphatic dibasic acid such as methylenedicarboxylic acid or an anhydride thereof and a linear or branched saturated or unsaturated aliphatic alcohol having 3 to 22 carbon atoms.
  • polyol esters examples include neopentyl glycols such as neopentyl glycol, 2,2-diethylpropanediol, 2-butyl-2-ethylpropandiol, trimethylolethane, trimethylolpropane, pentaerythritol, ditrimethylolpropane, and dipentaerythritol.
  • neopentyl glycols such as neopentyl glycol, 2,2-diethylpropanediol, 2-butyl-2-ethylpropandiol, trimethylolethane, trimethylolpropane, pentaerythritol, ditrimethylolpropane, and dipentaerythritol.
  • esters examples include polymerized fatty acids such as dimer acid and hydrogenated dimer acid, or hydroxy fatty acids such as condensed castor oil fatty acid and hydrogenated condensed castor oil fatty acid, and linear or branched chains having 3 to 22 carbon atoms. And esters with saturated or unsaturated fatty alcohols.
  • the polyalkylene glycol is exemplified by a ring-opening polymer of alcohol and a linear or branched alkylene oxide having 2 to 4 carbon atoms.
  • alkylene oxide include ethylene oxide, propylene oxide, and butylene oxide.
  • a polymer using one of these or a copolymer using a mixture of two or more can be used.
  • a compound in which one or both hydroxyl groups are etherified can also be used.
  • the kinematic viscosity of the polymer is 5.0 to 1000 mm 2 / s (40 ° C.), preferably 5.0 to 500 mm 2 / s (40 ° C.).
  • Polyvinyl ether is a compound obtained by polymerization of a vinyl ether monomer, and monomers include methyl vinyl ether, ethyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, sec-butyl vinyl ether, tert-butyl vinyl ether, n-pentyl vinyl ether. N-hexyl vinyl ether, 2-methoxyethyl vinyl ether, 2-ethoxyethyl vinyl ether and the like.
  • the kinematic viscosity of the polymer is 5.0 to 1000 mm 2 / s (40 ° C.), preferably 5.0 to 500 mm 2 / s (40 ° C.).
  • polyphenyl ether examples include compounds having a structure in which meta positions of two or more aromatic rings are connected by an ether bond or a thioether bond. Specifically, bis (m-phenoxyphenyl) ether, m-bis ( m-phenoxyphenoxy) benzene, and thioethers (commonly referred to as C-ether) in which one or more of these oxygens are substituted with sulfur.
  • alkylphenyl ether examples include compounds in which polyphenyl ether is substituted with a linear or branched alkyl group having 6 to 18 carbon atoms, and alkyl diphenyl ether substituted with one or more alkyl groups is particularly preferable.
  • silicone oil examples include dimethyl silicone and methylphenyl silicone, as well as modified silicones such as long chain alkyl silicone and fluorosilicone.
  • the lubricating oil composition for a spindle motor of the present invention is a lubricating oil (that is, a lubricating oil consisting only of an aliphatic dihydric alcohol diester, or an aliphatic dihydric alcohol diester and a combination thereof.
  • a lubricating oil composition for spindle motors containing an antioxidant In addition to a base oil, it is a lubricating oil composition for spindle motors containing an antioxidant.
  • antioxidants examples include phenolic antioxidants, amine antioxidants, sulfur antioxidants, and the like. Of these, phenolic antioxidants and amine antioxidants are recommended.
  • Antioxidants may be used singly or in combination of two or more, and the amount added is usually 0.01 to 5% by weight, preferably 0. 1 to 2% by weight.
  • phenolic antioxidant known ones used in this field can be used without any particular limitation.
  • these phenolic antioxidants those having 6 to 100 carbon atoms, preferably 10 to 80 carbon atoms, which do not contain sulfur in the molecule are particularly preferable.
  • the phenolic antioxidants may be used singly or in combination of two or more, and the addition amount is usually 0.01 to 5% by weight with respect to the spindle motor lubricating oil, preferably 0.1 to 2% by weight.
  • amine-based antioxidant known ones used in this field can be used without any particular limitation.
  • these amine-based antioxidants those having 6 to 60 carbon atoms and preferably 10 to 40 carbon atoms that do not contain sulfur in the molecule are particularly preferable.
  • a monoalkyldiphenylamine such as diphenylamine, monooctyl (including straight chain and branched chain) diphenylamine, particularly mono (C 4 -C 9 alkyl) diphenylamine (ie, one of the two benzene rings of diphenylamine is an alkyl group)
  • p, p′-dioctyl including linear and branched diphenylamine
  • p, p′-dinonyl including linear and branched diphenylamine
  • N-phenyl-1-naphthylamine are particularly preferable.
  • “(including straight chain and branched chain)” includes one or both of straight chain alkyl and branched chain alkyl.
  • Amine antioxidants are used alone or in combination of two or more, and the amount added is usually 0.01 to 5% by weight, preferably 0.1 to 2%, based on the spindle motor lubricating oil. % By weight.
  • the phenolic antioxidant and the amine antioxidant can be used alone or in combination of two or more.
  • the ratio of the two is not particularly limited and can be appropriately selected from a wide range.
  • Preferred combinations include 2,6-di-t-butyl-p-cresol, 4,4′-methylenebis (2,6-di-t-butylphenol) and 2,6-di-t-butyl-4-ethyl
  • the amount of the phenolic antioxidant combined with the amine antioxidant is usually 0.01 to 5% by weight, preferably 0.1 to 2% by weight, based on the spindle motor lubricating oil. is there.
  • metal detergents In order to further improve the performance of the above lubricating oil composition for spindle motors, metal detergents, ashless dispersants, oiliness agents, antiwear agents, extreme pressure agents, metal deactivators, rust inhibitors, viscosity index improvers
  • at least one additive such as a pour point depressant, an antifoaming agent, and a hydrolysis inhibitor can be appropriately blended.
  • Metal detergents include Ca-petroleum sulfonate, overbased Ca-petroleum sulfonate, Ca-alkyl benzene sulfonate, overbased Ca-alkyl benzene sulfonate, Ba-alkyl benzene sulfonate, overbased Ba-alkyl benzene sulfonate Phonates, Mg-alkylbenzenesulfonates, overbased Mg-alkylbenzenesulfonates, Na-alkylbenzenesulfonates, overbased Na-alkylbenzenesulfonates, Ca-alkylnaphthalenesulfonates, overbased Ca- Metal sulfonates such as alkyl naphthalene sulfonates, Ca-phenates, overbased Ca-phenates, Ba-phenates, overbased Ba-phenates and other metal phenates, Ca-salicylate, overbased Ca Metal salicylate
  • ashless dispersant examples include polyalkenyl succinimide, polyalkenyl succinamide, polyalkenyl benzylamine, polyalkenyl succinate and the like. These ashless dispersants may be used alone or in combination. When used, they are usually added in an amount of 1 to 10% by weight, preferably 2 to 7% by weight, based on the lubricating oil for the spindle motor. It is desirable.
  • oily agents include aliphatic saturated and unsaturated monocarboxylic acids such as stearic acid and oleic acid, polymerized fatty acids such as dimer acid and hydrogenated dimer acid, hydroxy fatty acids such as ricinoleic acid and 12-hydroxystearic acid, lauryl alcohol, Aliphatic saturated and unsaturated monoalcohols such as oleyl alcohol, aliphatic saturated and unsaturated monoamines such as stearylamine and oleylamine, aliphatic saturated and unsaturated monocarboxylic amides such as lauric acid amide, oleic acid amide, batyl alcohol, Glycerin ethers such as chimyl alcohol and ceralkyl alcohol, alkyl or alkenyl polyglyceryl ethers such as lauryl polyglyceryl ether and oleyl polyglyceryl ether, di (2-ethylhexyl) monoethanol alcohol Emissions, poly (alkylene oxide) alky
  • oil-based agents may be used alone or in combination, and when used, they are usually 0.01% to 5% by weight, preferably 0.1% by weight based on the lubricating oil for the spindle motor. It is desirable to add from 3% to 3% by weight.
  • Antiwear / extreme pressure agents include tricresyl phosphate, cresyl diphenyl phosphate, alkylphenyl phosphates, phosphate esters such as tributyl phosphate, dibutyl phosphate, tributyl phosphate, dibutyl phosphate, triisopropyl phosphate, etc.
  • Phosphorous esters of these and their amine salts such as phosphorus, sulfurized fats and oils, sulfurized fatty acids such as sulfurized oleic acid, sulfur such as dibenzyl disulfide, sulfurized olefin, dialkyl disulfide, Zn-dialkyldithiophosphate, Zn- Examples thereof include organometallic compounds such as dialkyldithiophosphate, Mo-dialkyldithiophosphate, and Mo-dialkyldithiocarbamate. These antiwear agents may be used alone or in combination. When used, they are usually 0.01 to 10% by weight, preferably 0.1 to 5% by weight based on the lubricating oil for the spindle motor. % Addition is desirable.
  • metal deactivators examples include benzotriazole-based, thiadiazole-based, and gallic acid ester-based compounds. These metal deactivators may be used alone or in combination, and when used, they are usually 0.01 to 0.4% by weight, preferably 0.01% with respect to the spindle motor lubricating oil. It is desirable to add up to 0.2% by weight.
  • rust preventives include alkyl or alkenyl succinic acid derivatives such as dodecenyl succinic acid half ester, octadecenyl succinic anhydride, dodecenyl succinic acid amide, sorbitan monooleate, glycerin monooleate, pentaerythritol monooleate and many others.
  • Monohydric alcohol partial ester Ca-petroleum sulfonate, Ca-alkyl benzene sulfonate, Ba-alkyl benzene sulfonate, Mg-alkyl benzene sulfonate, Na-alkyl benzene sulfonate, Zn-alkyl benzene sulfonate, Ca-alkyl naphthalene sulfate
  • metal sulfonates such as phonates, amines such as rosinamine and N-oleylsarcosine, dialkyl phosphiteamine salts and the like.
  • These rust inhibitors may be used alone or in combination, and when used, they are usually 0.01 to 5% by weight, preferably 0.05 to 2% by weight based on the lubricating oil for the spindle motor. % Addition is desirable.
  • viscosity index improver examples include olefin copolymers such as polyalkyl methacrylate, polyalkyl styrene, polybutene, ethylene-propylene copolymer, styrene-diene copolymer, and styrene-maleic anhydride ester copolymer. .
  • These viscosity index improvers may be used alone or in combination, and when used, they are usually 0.1 to 15% by weight, preferably 0.5 to 7%, based on the lubricating oil for the spindle motor. It is desirable to add by weight%.
  • pour point depressant examples include a condensate of chlorinated paraffin and alkylnaphthalene, a condensate of chlorinated paraffin and phenol, polyalkyl methacrylate, polyalkylstyrene, polybutene and the like as the viscosity index improvers described above.
  • These pour point depressants may be used alone or in combination, and when used, they are usually 0.01 to 5% by weight, preferably 0.1 to 3%, based on the lubricating oil for the spindle motor. It is desirable to add by weight%.
  • liquid silicone is suitable, and when it is used, the amount added is usually 0.0005 to 0.01% by weight based on the lubricating oil for the spindle motor.
  • Hydrolysis inhibitors include alkyl glycidyl ethers, alkyl glycidyl esters, alkylene glycol glycidyl ethers, alicyclic epoxies, epoxy compounds such as phenyl glycidyl ether, di-tert-butylcarbodiimide, 1,3-di- A carbodiimide compound such as p-tolylcarbodiimide can be used, and it is usually desirable to add 0.05 to 2% by weight to the lubricating oil for the spindle motor.
  • FIG. 1 is an example of a cross-sectional view schematically showing a schematic configuration of a fluid dynamic bearing according to the present invention.
  • the hydrodynamic bearing of the present invention does not have a mechanism such as a ball bearing, and includes a shaft and a sleeve, and the interval is maintained so as not to be in direct contact with each other by the lubricating oil composition accommodated therebetween.
  • the fluid bearing is not particularly limited mechanically.
  • the hydrodynamic bearing of FIG. 1 is provided with thrust dynamic pressure generating grooves (5) and (6) on the shaft (1) above and below the radial dynamic pressure generating grooves (3) and (4) and the thrust plate (7). It is an example of a fluid bearing.
  • These dynamic pressure grooves (3), (4), (5) and (6) are formed in a herringbone shape in this example, but are not necessarily limited to this shape, and are spiral shape, arc shape, straight line It may be formed in a shape or the like.
  • the radial dynamic pressure generating grooves (3) and (4) may be formed on the inner peripheral surface of the sleeve (2) instead of the outer peripheral surface of the shaft (1). 6) may be formed on the upper and lower surfaces of the thrust plate (7) instead of the lower end surface of the sleeve (2) and the upper surface of the counter plate (8), respectively.
  • the lubricating oil composition (9) of the present invention is enclosed in the minute gaps between these dynamic pressure grooves (3), (4), (5) and (6) and the facing surfaces facing each other. ing.
  • the hydrodynamic bearing of the present invention uses as a lubricating oil (9) a lubricating oil composition for a spindle motor that uses a lubricating oil for a spindle motor that has excellent stability, viscosity characteristics, low temperature characteristics, and volatility resistance of the base oil itself. Therefore, a bearing life longer than that of the fluid bearing using the conventional lubricating oil composition can be obtained without increasing the holding amount of the lubricating oil composition. Therefore, it is suitable as a fluid bearing applied to a spindle motor or the like that is small and requires high precision and high speed rotation.
  • the spindle motor of the present invention is characterized by using the above-described fluid bearing, and a specific example of the spindle motor is shown in FIG.
  • FIG. 2 is an example of a sectional view schematically showing a schematic configuration of the spindle motor of the present invention.
  • the stator coil (12) is provided on the wall formed on the base (11), and the rotor magnet (13) is opposed to the stator coil (12) on the inner peripheral surface of the hub (10).
  • the motor drive unit is configured by being attached.
  • Volatilization amount (%) [(W 0 ⁇ W) / W 0 ] ⁇ 100 [Wherein W 0 represents the weight before the test, and W represents the weight after the test. ].
  • the IR spectrum was obtained by using an aliphatic dihydric alcohol diester by an ATR method (attenuated total reflection method) using an infrared spectroscopic analyzer (PERKIN ELMER 400).
  • nC 8 acids n-Nonanoic acid: Used by distillation purification of [n-Pelargonic Acid] manufactured by OXEA (nC 9 acid)
  • n-decanoic acid used by distillation purification of [Capric acid] manufactured by Shin Nippon Rika Co., Ltd.
  • nC 10 acid n-Undecanoic acid: Distilled and refined [Undecanoic Acid] manufactured by Tokyo Chemical Industry Co., Ltd. (nC 11 acid).
  • ethylene oxide addition reaction product having an average addition mole number of 1 mol.
  • the resulting ethylene oxide addition reaction mixture was purified by distillation to obtain an ethylene oxide 1 mol adduct of 3-methyl-1,5-pentanediol.
  • the resulting propylene oxide addition reaction mixture was purified by distillation to obtain a 1 mol propylene oxide adduct of 3-methyl-1,5-pentanediol.
  • ethylene oxide addition reaction product having an average addition mole number of 1 mol.
  • the resulting ethylene oxide addition reaction mixture was purified by distillation to obtain an ethylene oxide 1 mol adduct of 2,4-diethyl-1,5-pentanediol.
  • Example 1 In a 1 liter four-necked flask equipped with a stirrer, a thermometer and a water fraction receiver with a condenser tube, 397.8 g (3.06 mol) of n-heptanoic acid and 3-methyl-1,5-pentanediol were mixed. 243.0 g (1.5 mol) of ethylene oxide 1 mol adduct, 30 g of xylene and 0.6 g of tin oxide as a catalyst were charged, and the temperature was gradually raised to 220 ° C. in a nitrogen atmosphere.
  • the esterification reaction was carried out for about 6 hours under reduced pressure while removing the produced water distilled off with a moisture fraction receiver with the theoretically produced water amount (54 g) as a guide. After completion of the reaction, excess acid was removed by distillation. Next, after neutralization with an excess of an aqueous caustic soda solution with respect to the total acid value after completion of the reaction, the mixture was washed with water until neutrality to obtain a crude esterification reaction product. Further, the obtained esterification reaction crude product was treated with activated carbon and filtered to obtain 534.4 g of 3-methyl-1,5-pentanediol ethylene oxide 1 mol adduct-di (n-heptanoate) of the present invention. Obtained. The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 2 Except that 440.6 g (3.06 mol) of n-octanoic acid was used instead of n-heptanoic acid, ethylene oxide of 3-methyl-1,5-pentanediol of the present invention was prepared in the same manner as in Example 1. 546.0 g of 1 molar adduct-di (n-octanoate) was obtained. The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • n-octanoic acid was used instead of n-heptanoic acid
  • ethylene oxide of 3-methyl-1,5-pentanediol of the present invention was prepared in the same manner as in Example 1.
  • 546.0 g of 1 molar adduct-di (n-octanoate) was obtained.
  • the structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 3 Except that 483.5 g (3.06 mol) of n-nonanoic acid was used in place of n-heptanoic acid, ethylene oxide of 3-methyl-1,5-pentanediol of the present invention was prepared in the same manner as in Example 1. 557.6 g of 1 molar adduct-di (n-nonanoate) was obtained. The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 4 By the same method as in Example 1 except that 526.3 g (3.06 mol) of n-decanoic acid was used instead of n-heptanoic acid, ethylene oxide of 3-methyl-1,5-pentanediol of the present invention was used. 569.1 g of 1 molar adduct-di (n-decanoate) was obtained. The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 5 Using 264.0 g (1.5 mol) of propylene oxide 1 mol adduct of 3-methyl-1,5-pentanediol instead of ethylene oxide 1 mol adduct of 3-methyl-1,5-pentanediol, the reaction Except for the time of 8 hours, 524.4 g of 3-methyl-1,5-pentanediol propylene oxide 1-mol adduct-di (n-heptanoate) was obtained in the same manner as in Example 1. . The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 6 Instead of n-heptanoic acid, 440.6 g (3.06 mol) of n-octanoic acid was used, and 3-methyl-1,5-pentanediol was substituted with 1 mol of ethylene oxide and 3-methyl-1,5 -In the same manner as in Example 1 except that 264.0 g (1.5 mol) of propylene oxide 1 mol adduct of pentanediol was used and the reaction time was 8 hours, 3-methyl-1, 580.0 g of propylene oxide 1 mol adduct of 5-pentanediol-di (n-octanoate) was obtained. The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 7 Instead of n-heptanoic acid, 483.5 g (3.06 mol) of n-nonanoic acid was used, and 3-methyl-1,5-pentanediol was substituted with 1 mol of ethylene oxide and 3-methyl-1,5 -In the same manner as in Example 1 except that 264.0 g (1.5 mol) of propylene oxide 1 mol adduct of pentanediol was used and the reaction time was 8 hours, 3-methyl-1, Propylene oxide 1 mol adduct of 5-pentanediol-di (n-nonanoate) 605.8 g was obtained. The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 8 Instead of n-heptanoic acid, 526.3 g (3.06 mol) of n-decanoic acid was used, and instead of 3-methyl-1,5-pentanediol ethylene oxide 1 mol adduct, 3-methyl-1,5 -In the same manner as in Example 1 except that 264.0 g (1.5 mol) of propylene oxide 1 mol adduct of pentanediol was used and the reaction time was 8 hours, 3-methyl-1, 633.8 g of 5-pentanediol propylene oxide 1 mol adduct-di (n-decanoate) was obtained. The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 9 Instead of n-heptanoic acid, 440.6 g (3.06 mol) of n-octanoic acid was used, and 2,4-diethyl-1 was substituted for 1 mol of ethylene oxide adduct of 3-methyl-1,5-pentanediol. 2,4-diethyl-1,5-pentanediol of the present invention in the same manner as in Example 1 except that 306.0 g (1.5 mol) of an ethylene oxide 1-mol adduct of 1,5-pentanediol was used. Of ethylene oxide 1 mol adduct-di (n-octanoate) was obtained. The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 10 Instead of n-heptanoic acid, 483.5 g (3.06 mol) of n-nonanoic acid was used, and 2,4-diethyl-1 was substituted for 1 mol of ethylene oxide adduct of 3-methyl-1,5-pentanediol. 2,4-diethyl-1,5-pentanediol of the present invention in the same manner as in Example 1 except that 306.0 g (1.5 mol) of an ethylene oxide 1-mol adduct of 1,5-pentanediol was used. Of ethylene oxide 1 mol adduct-di (n-nonanoate) was obtained. The structure of this compound was confirmed by 1 H-NMR and IR spectrum. Further, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results are shown in Table 1.
  • Example 11 Ethylene oxide 1 mol adduct of 3-methyl-1,5-pentanediol of Example 3—420.0 g of di (n-nonanoate) and ethylene oxide 1 of 2,4-diethyl-1,5-pentanediol of Example 9 Mole adduct-di (n-octanoate) 180.0g (weight ratio: 70/30) was mixed, kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity and heat resistance test were conducted, and the test results Are shown in Table 1.
  • Example 12 Ethylene oxide 1 mol adduct of 3-methyl-1,5-pentanediol of Example 3—180.0 g of di (n-nonanoate) and ethylene oxide 1 of 2,4-diethyl-1,5-pentanediol of Example 9 Mole adduct-di (n-octanoate) 420.0 g (weight ratio: 30/70) was mixed, and kinematic viscosity, viscosity index, low temperature fluidity test, volume resistivity test and heat resistance test were conducted. Are shown in Table 1.
  • Table 1 shows the kinetic viscosity, viscosity index, low-temperature fluidity test, volume resistivity test and heat resistance test of Sunsizer DIDA (di-isodecyl adipate: hereinafter referred to as “DIDA”) manufactured by Shin Nippon Rika Co., Ltd. It was shown to.
  • DIDA di-isodecyl adipate
  • this lubricating oil has viscosity characteristics (kinematic viscosity, viscosity index), low temperature fluidity, electrical conductivity, and heat resistance. It turns out that it is a lubricating oil which does not have a fault in all.
  • the lubricating oil of the present invention has a small change rate in viscosity over a wide temperature range (high viscosity index), a low viscosity even at a low temperature, good conductivity, and excellent volatility resistance. Therefore, various lubricating oils, that is, lubricating oil for refrigerators, lubricating oil for engines, lubricating oil for gears, lubricating oil for bearings, lubricating oil for automatic transmission, lubricating oil for continuously variable transmission, lubricating oil for power steering It can be suitably used as active suspension lubricating oil, shock absorber lubricating oil, turbine lubricating oil, compressor lubricating oil, hydraulic working oil or grease base oil.

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Abstract

La présente invention concerne une huile lubrifiante présentant un faible taux de variation de sa viscosité (par exemple un indice de viscosité élevé), dans un large intervalle de températures, une faible viscosité aux températures les plus basses, une bonne conductivité électrique et une bonne résistance à la volatilisation. Ladite huile lubrifiante est constituée d'un diester d'alcool aliphatique bivalent de structure spécifique.
PCT/JP2012/079335 2012-11-13 2012-11-13 Huile lubrifiante Ceased WO2014076747A1 (fr)

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AT518447A1 (de) * 2016-03-30 2017-10-15 Minebea Co Ltd Verfahren zur synthese von esterölen
JP2018080246A (ja) * 2016-11-15 2018-05-24 コスモ石油ルブリカンツ株式会社 潤滑油用基油及び潤滑油
JP6800498B1 (ja) * 2019-11-21 2020-12-16 竹本油脂株式会社 新規な化合物及びそれを含む洗浄剤組成物

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JP2010180331A (ja) * 2009-02-06 2010-08-19 New Japan Chem Co Ltd 動圧流体軸受用又は焼結含油軸受用潤滑油組成物
WO2011161908A1 (fr) * 2010-06-21 2011-12-29 三洋化成工業株式会社 Composition d'huile de graissage pour paliers

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AT518447A1 (de) * 2016-03-30 2017-10-15 Minebea Co Ltd Verfahren zur synthese von esterölen
AT518447B1 (de) * 2016-03-30 2017-12-15 Minebea Co Ltd Verfahren zur synthese von esterölen
JP2018080246A (ja) * 2016-11-15 2018-05-24 コスモ石油ルブリカンツ株式会社 潤滑油用基油及び潤滑油
JP6800498B1 (ja) * 2019-11-21 2020-12-16 竹本油脂株式会社 新規な化合物及びそれを含む洗浄剤組成物
JP2021080222A (ja) * 2019-11-21 2021-05-27 竹本油脂株式会社 新規な化合物及びそれを含む洗浄剤組成物

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