WO2005040081A1 - Compose de diphenylether a substitutions alkyle et composition contenant celui-ci - Google Patents

Compose de diphenylether a substitutions alkyle et composition contenant celui-ci Download PDF

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Publication number
WO2005040081A1
WO2005040081A1 PCT/JP2004/015951 JP2004015951W WO2005040081A1 WO 2005040081 A1 WO2005040081 A1 WO 2005040081A1 JP 2004015951 W JP2004015951 W JP 2004015951W WO 2005040081 A1 WO2005040081 A1 WO 2005040081A1
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Prior art keywords
alkyl
diphenyl ether
compound
substituted diphenyl
oil
Prior art date
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PCT/JP2004/015951
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English (en)
Japanese (ja)
Inventor
Nagayoshi Kobayashi
Masatsugu Kohno
Akinobu Wakabayashi
Tamio Akada
Original Assignee
Matsumura Oil Research Corp.
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Application filed by Matsumura Oil Research Corp. filed Critical Matsumura Oil Research Corp.
Priority to JP2005515026A priority Critical patent/JP4698422B2/ja
Publication of WO2005040081A1 publication Critical patent/WO2005040081A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M105/18—Ethers, e.g. epoxides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/02—Mixtures of base-materials and thickeners
    • 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
    • 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
    • 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
    • C10N2040/32—Wires, ropes or cables 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
    • 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 alkyl-substituted diphenyl ether compound and a composition containing the same.
  • the present invention relates to a novel alkyl-substituted diphenyl ether compound and a lubricant composition containing the same. More specifically, base oils for industrial greases, vacuum pump oils, lubricating oils for chains, lubricating oils for compressors, and other products that have a long life at high temperatures
  • the present invention relates to a grease composition containing the alkyl-substituted diphenyl ether compound of the present invention, which is used in applications requiring excellent low-temperature properties.
  • synthetic lubricating oils have been used in place of the mineral oils conventionally used.
  • phenyl ether-based synthetic oils are used for applications that do not undergo thermal or oxidative degradation at high temperatures and require a long life.
  • poly- ⁇ -olefin oil and ester oil that maintain fluidity even at low temperatures are used in order to achieve low torque during operation.
  • phenyl ether synthetic oils base oils for industrial greases, vacuum pump oils, lubricating oils for chains, lubricating oils for compressors, lubricating oils for sintered oil-impregnated bearings, lubricating oils for radiation resistance, and other thermal stability Widely used in applications that require (See, for example, Patent Document 1 and Non-Patent Document 1).
  • alkyl-substituted diphenyl ethers have been known as phenyl ether-based synthetic oils (for example, see Patent Documents 1 and 2). These alkyl-substituted diphenyl ethers are synthesized by a Friedel-Crafts reaction between diphenyl ether and ⁇ -olefin using aluminum chloride as a catalyst (for example, see Patent Document 3).
  • the compound bonded to diphenyl ether at the 2nd or higher position of the alkyl group is, for example, a diphenyl ether substituted with an sec-alkyl group, and bonded to diphenyl ether at the 1st position of the alkyl group.
  • the compound means diphenyl ether substituted with an n-alkyl group.
  • Patent Document 1 Japanese Patent Publication No. 58-222-515
  • Patent Document 2 Patent No. 2 5 7 2 8 14
  • Patent Document 3 Japanese Patent Application Laid-Open No. 6-5044-289
  • Patent Document 4 Japanese Patent No. 2544450
  • Patent Document 1 Masaji Kono, "Practical Examples and Effects of Phenyl Ether Synthetic Lubricants", Lubrication Economy, February 1, 2000, Vol. 4 17 (Vol. 2000) Month issue), p. 1 8-2 3
  • An object of the present invention is to provide a compound having both excellent high-temperature properties and excellent low-temperature properties, and to provide a lubricant composition containing the compound, especially a grease composition.
  • the present inventors have synthesized various compounds and studied their properties in order to solve the above problems. As a result, they have found that an alkyl-substituted diphenyl ether bonded to diphenyl ether at the 1-position of the alkyl group at a certain ratio or more solves the above-mentioned problems, and completed the present invention. Disclosure of the invention
  • the present invention relates to an alkyl-substituted diphenyl ether having at least two or more alkyl groups having 10 to 20 carbon atoms as a substituent, and having a 1-position addition ratio of the alkyl substituent of 5% or more.
  • the 1-position addition rate refers to the position of the terminal carbon atom (position 1) in the alkyl-substituted diphenyl ether represented by the following formula (1).
  • R is an alkyl group having 10 to 20 carbon atoms
  • m and n represent real numbers of 0 to 5, and 2 ⁇ m + n ⁇ 10. In this case, each R is the same or different. May be.
  • the 1-position addition ratio is 5% or more, preferably 10% or more, and more preferably 20% or more. Especially at the upper limit of the first place addition rate There is no limitation, but 50% or less is preferable. Therefore, the preferred range of the 1-position addition ratio is 5 to 50%, more preferably 10 to 50%, and most preferably 20 to 50%.
  • the alkyl group having 10 to 20 carbon atoms include decyl, pentadecyl, dodecyl, tetradecyl, hexadecyl, heptadecyl, octadecyl, eicosyl and the like. The numbers 12 to 16 are particularly preferred.
  • the ratio of the addition at the 1-position to the addition at the 2- or higher position can be calculated from the following NMR formulas (2) and (3).
  • N represents the total number of carbon atoms in the alkyl group.
  • ⁇ 1 H 2 and H 3 represent integral values of hydrogen atoms assigned to the following. Although the value of H 3 is not necessary in equation (2), it is shown in the examples for reference.
  • Hj: ⁇ 5 0.74 to 1.58 ppm [All hydrogen atoms excluding the hydrogen atoms on the carbon atom adjacent to the diphenyl ether skeleton among the hydrogen atoms of the alkyl group]
  • the result may be obtained in which the first-order addition rate is 0 or less, and in the equation (3), the addition rate of the second- or higher-order is 100 or more.
  • the addition position force S of the alkyl group is 2 or higher and the carbon atom serving as the addition position is quaternary carbon. Therefore, when the first place addition was calculated to be 0 or less, the first place addition rate was set to 0%, and the addition rate for the second place or more was set to 100%.
  • the method for synthesizing the alkyl-substituted diphenyl ether of the present invention is as follows.
  • a mono-halogenated alkane (preferably 1-alkane chloride) or a primary alcohol is used as a starting material for adding an alkyl group instead of the conventional ⁇ -olefin, It can be synthesized by adding an alkyl group by a Friedel-Crafts reaction.
  • an alkyl-substituted diphenylene ether having an alkyl group at the 1-position can be contained in a certain amount or more.
  • the present invention also relates to a lubricant composition containing the above-mentioned alkyl-substituted diphenyl ether.
  • the lubricant composition of the present invention contains 100% of the above-mentioned alkyl-substituted diphenyl ether, mineral oil, or other synthetic oils such as polyolefin oil, ester oil, silicone oil, and polybutene. It may contain oil, polyether oil, or fluorinated polyester oil, or may contain various additives known per se. Examples of usable additives include various additives such as sulfonate-based, phenol-based, amine-based, io-based, phosphorus-based, molybdenum-based, fatty acid-based, and polymethacrylate-based additives.
  • the lubricant composition of the present invention is not particularly limited, but contains the base oil as a base oil and various additives, for example, a grease containing a thickening agent, an extreme pressure additive, etc., and an antioxidant.
  • a grease containing a thickening agent for example, a grease containing a thickening agent, an extreme pressure additive, etc., and an antioxidant.
  • an antioxidant included vacuum pump oil, chain lubricating oil, sintered oil-impregnated bearing lubricating oil, radiation-resistant lubricating oil, and compressor lubricating oil.
  • a grease composition containing the alkyl-substituted diphenyl ether of the present invention as a base oil or a part of the base oil is preferable.
  • the present invention When used for various types of bearings, the Dully's composition is effective in reducing abnormal noise during machine operation and prolonging the life of the bearing.
  • the grease composition of the present invention contains the above-mentioned alkyl-substituted diphenyl ether as a base oil or a part of the base oil, and contains various additives such as a thickener, an extreme pressure additive and the like.
  • non-metallic stones, non-metallic stones such as composite metal stones, benton, silica gel, rare compounds, non-reactive compounds such as rare urethane compounds, etc.
  • Stone-based thickeners can be used. Above all, it has a wide usable temperature range and can be used universally from general industrial use to automotive parts and home appliances.It is also necessary for bearings for automotive electrical parts, continuous manufacturing equipment for steel manufacturers, and rolling mills. From the viewpoints of excellent heat resistance and water resistance, thickeners such as lithium stone, composite lithium stone, and rare compounds are preferred. Specific examples of the stone-based thickener include sodium stone, calcium stone, aluminum stone, and lithium stone.
  • rare compounds, urethane compounds, and rare urethane compounds include, for example, a reaction product of p-toluidine and tolylene diisocyanate, and a mixture of cyclohexylamine and 4,4'-diphenyl methane triisocyanate. Reaction of the diurea compound, p-dodecylaniline with 4,4'-diphenylmethane triisocyanate, the reactant diurea compound, tetraurea compound, diurethane compound, diurea urethane compound or a mixture thereof No.
  • extreme pressure additives include sulfurized coconut oil, zeolites such as dialkyldithiolrubaminic acid, phosphorus types such as dialkyldithiophosphates and phosphates, molybdenum types such as organic molybdenum compounds, graphite, molybdenum disulfide, and the like.
  • Solid lubricants such as boron nitride, potassium borate, and PTFE can be used.
  • oils, antioxidants, rust inhibitors and the like can be used.
  • the grease composition of the present invention is suitably used as a grease composition for bearings under particularly severe conditions such as low temperature, high temperature, high speed, and high load.
  • the lubricant composition containing the alkyl-substituted diphenyl ether of the present invention showed the same or better characteristics than the conventional alkyl-substituted diphenyl ether, and showed lubrication for grease, vacuum pump oil, and chain lubrication. It can be used as oil, lubricating oil for compressors, lubricating oil for sintered oil-impregnated bearings, and anti-radiation oil.
  • a grease composition for bearings it is possible to provide a lubricant composition having characteristics excellent in reducing abnormal noise during operation of a machine in a wide temperature range and prolonging a bearing life.
  • Diphenyl ether (510.0 g) and aluminum chloride (8.2 g) as a catalyst were heated and stirred at 120 ° C.
  • dodecyl monochloride (1171.8 g) was slowly added, and heating and stirring were continued for 2 hours. Thereafter, the mixture was filtered to remove the catalyst, and then vacuum distillation was performed at 300 to 130 ° C. at 13.3 to 200 Pa to remove unreacted raw materials and monododecyl-substituted diphenyl ether. 698.9 g) were obtained.
  • Diphenyl ether (510.0 g) and aluminum chloride (8.7 g) as a catalyst are heated and stirred at 120 ° C.
  • mixed alkyl chloride (126.7 g) consisting of C12: 65%, C14: 22% and C16: 13% was added slowly, and heating and stirring were continued for 2 hours. . Thereafter, the mixture was filtered to remove the catalyst, and then vacuum distillation was performed at 300 ° C at 13.3 to 200 Pa to remove unreacted raw materials and the monoalkyl-substituted diphenyl ether. 91 1.0 g) was obtained.
  • Comparative Example 1 ⁇ «Synthesis of dodecyl-substituted diphenyl ether (compound 3) using diolefin as a main ingredient and di- or more-compound as main component>
  • Diphenyl ether (510.0 g) and aluminum chloride (6.6 g) as a catalyst are heated and stirred at 90 ° C.
  • 1-dodecane (947.1 g) was slowly added, and heating and stirring were continued for 30 minutes. Thereafter, the mixture was filtered to remove the catalyst, and then vacuum distillation was performed at 280 ° C at 13.3 to 200 Pa to remove unreacted raw materials and the monoalkyl-substituted diphenyl ether, to obtain the desired compound 3 ( 1 150.6 g) were obtained.
  • Comparative Example 2 ⁇ -olefin was used as a raw material for synthesis, and the alkyl substituent was a dodecyl group or
  • Diphenyl ether (510.0 g) and aluminum chloride (7.2 g) as a catalyst were heated and stirred at 90 ° C.
  • a mixed ⁇ -olefin (1026.0 g) consisting of C12: 56% and C14: 44% was slowly added, and the mixture was heated and stirred for 30 minutes. Thereafter, the mixture was filtered to remove the catalyst, and then vacuum distillation was performed at 280 ° C at 13.3 to 200 Pa to remove unreacted raw materials and the monoalkyl-substituted diphenyl ether. 1 195.0 g) was obtained.
  • H x : 6 0.73 to 1.58 ppm (30.19H, all hydrogen atoms of the hydrogen atom of the alkyl group, excluding the hydrogen atom on the carbon atom adjacent to the diphenyl ether skeleton) atom ⁇
  • Table 1 shows the general properties of the compounds (Compounds 1 to 4) synthesized in Examples 1 and 2 and Comparative Examples 1 and 2. Also, for polyaolefin which is generally used as a synthetic lubricating oil other than the alkyl-substituted diphenyl ether type, PAO-801 (Compound 5) manufactured by Nippon Steel Chemical Co., Ltd. And ⁇ table 1 ⁇
  • the compounds (compounds 1 to 4) synthesized in Examples 1 and 2 and Comparative Examples 1 and 2 were each weighed into a glass beaker of 1502 Om1. This was allowed to stand in a 200 ° C. high-temperature bath, and the weight, kinematic viscosity and total acid value were measured after 5 days and 10 days. Based on the measured values before the thermal stability test, changes in properties due to the thermal stability test were evaluated. For comparison, a thermal stability test was also performed on poly- ⁇ -olefin oil. In addition, Compound 5 was used as polyolefin oil. Table 2 shows the results.
  • Test method 1-1 Measurement of evaporation loss rate
  • Test method 1-2 Measurement of kinematic viscosity change rate
  • the kinematic viscosity of Compounds 1 to 5 was measured at 40 ° C after 5 days and 10 days, and the rate of change in kinematic viscosity was calculated based on the value before the test.
  • Test method 1-3 Measurement of total acid value change
  • compounds 1 and 2 which are alkyl-substituted diphenyl ethers having a 1-position adduct of the present invention are compounds 3 and 4 which are conventional alkyl-substituted diphenyl ethers, and polyolefins.
  • Compound 5 the evaporation loss rate and the kinematic viscosity change rate were low, and the increase in the total acid value was also small, confirming that the high temperature characteristics were extremely excellent.
  • Test example 2 Low temperature fluidity test
  • the pour points of the compounds synthesized in Examples 1 and 2 and Comparative Examples 1 and 2 were measured in accordance with JIS-K2269. For comparison, pour point was also evaluated for poly- ⁇ -refined oil. Compound 5 was used as the poly- ⁇ -olefin oil. Table 3 shows the results. From these results, the alkyl-substituted diphenyl ether having a 1-position adduct of the present invention, Compound 1 and Compound 2, have a lower pour point than the conventional alkyl-substituted diphenyl ethers, Compound 3 and Compound 4. Was confirmed. Compounds 1 and 2 are generally flowable at low temperature. It was confirmed that the composition exhibited low-temperature fluidity comparable to that of poly-o-olefin oil (compound 5), which was recognized as having excellent properties.
  • Test example 3 Lubricity test
  • Example 5 The same operation as in Example 3 was performed, except that Compound 2 of Example 2 was used instead of Compound 1, to obtain a lithium stone grease composition. This was designated as grease composition 2.
  • Example 5 The same operation as in Example 3 was performed, except that Compound 2 of Example 2 was used instead of Compound 1, to obtain a lithium stone grease composition. This was designated as grease composition 2.
  • Example 5 The procedure of Example 5 was repeated, except that compound 2 was used instead of compound 1, to obtain a rare earth lease composition. This was designated as Darryth Composition 4.
  • Comparative Example 4 Lithium having the same composition as in Example 3 except that the conventional alkyl-substituted diphenyl ether (compound 3 of Comparative Example 1) was used instead of the alkyl-substituted diphenyl ether (compound 1) of the present invention. A stone grease composition was obtained. This was designated as grease composition 5.
  • Comparative Example 5 In place of the alkyl-substituted diphenyl ether (compound 1) of the present invention, A urea grease composition was obtained in the same composition as in Example 5, except that the following alkyl-substituted diphenyl ether (compound 4 of Comparative Example 2) was used. This was designated as grease composition 6.
  • Comparative Example 6 A peroxidase composition was prepared in the same manner as in Example 5 except that Compound 5 of Comparative Example 3 shown in Table 1 was used instead of the alkyl-substituted diphenyl ether (Compound 1) of the present invention. Obtained. This was designated as grease composition 7.
  • Tables 5 and 6 show the results of measuring the degree of miscibility and oil separation of each grease prepared in Examples 3 to 6 and Comparative Examples 4 to 6. Further, a lubricity test was conducted by the following method, and these results are also shown in Tables 5 and 6.
  • each grease prepared in Examples 5 and 6 and Comparative Examples 5 and 6 was sealed in a small bearing, and a bearing characteristic test was performed under the following operating conditions. Rotational torque, acoustic characteristics (acoustic life), and volatilization amount was measured.
  • the rotation torque was measured at normal temperature by a torque tester.
  • the acoustic properties were measured by measuring the Anderon value with an Anderon meter at ⁇ 10 ° C. and 10 ° C.
  • the volatilization amount was determined by performing a bearing rotation test at an ambient temperature of 100 ° C. for 1,000 hours, measuring the weight of the bearing before and after the test, and determining the difference.
  • Table 7 shows the results of each evaluation according to the performance required for motor bearing grease. The lower the torque value, the smaller the anderon value, and the smaller the volatilization amount, the better. Evaluation Was evaluated on the following four levels. A is particularly good. B is excellent. C is normal. D is inferior.
  • the grease compositions 3 and 4 of the present invention maintain fluidity even in a conventional drease composition 6 using an alkyl-substituted diphenyl ether or in a low temperature state. It was confirmed that the grease composition 7 exhibited lower torque, lower noise, and lower volatility than grease composition 7 using polyolefin as a base oil (compound 5).
  • the grease composition of the present invention can extend the bearing life in a wider temperature range than the grease composition using the conventional alkyl-substituted diphenyl ether.
  • Industrial applicability The application of the alkyl-substituted diphenyl ether of the present invention requires base oil of industrial dalyce, vacuum pump oil, lubricating oil for chains, lubricating oil for compressors, lubricating oil for sintered oil-impregnated bearings, and other thermal stability. In addition, there are applications where excellent low-temperature properties are required.
  • the lubricating oil containing the alkyl-substituted diphenyl ether of the present invention has excellent high-temperature characteristics and excellent low-temperature characteristics
  • industrial equipment using the lubricating oil can be used in a wide temperature range.
  • a grease composition it can be used for automotive electric components, cooling fans and wheels of automobile engines, home appliances, motors of information equipment such as computers, and bearings for continuous manufacturing facilities and rolling mills of steel manufacturers.
  • it can be used for sliding parts such as constant velocity joints for automobiles, gear boxes for various gears, and wire ropes.
  • the grease composition can also be used for applications that do not particularly require lubricity, for example, for sealing vacuum pumps, preventing rust, and for electrical contacts of household electrical appliances and automotive electrical components.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un diphényléther à substitutions alkyle qui comporte au moins deux substituants alkyle C10-20, et dans lequel la proportion des substituants alkyle en position 1 est égale ou supérieure à 5 %. Cet éther présente d'excellentes propriétés à haute température combinées à d'excellentes propriétés à basse température. L'invention concerne aussi une composition contenant cet éther, qui possède d'excellentes propriétés lorsqu'elle est utilisée comme composition lubrifiante, composition de graisse, etc.
PCT/JP2004/015951 2003-10-23 2004-10-20 Compose de diphenylether a substitutions alkyle et composition contenant celui-ci WO2005040081A1 (fr)

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JP2005515026A JP4698422B2 (ja) 2003-10-23 2004-10-20 アルキル置換ジフェニルエーテル化合物およびそれを含有する組成物

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JP2008208174A (ja) * 2007-02-23 2008-09-11 Nsk Ltd グリース組成物及び転動装置
JP2008239818A (ja) * 2007-03-27 2008-10-09 Nippon Oil Corp 冷凍機油及び冷凍機用作動流体組成物
JP2010138224A (ja) * 2008-12-09 2010-06-24 Mitsubishi Engineering Plastics Corp ポリカーボネート樹脂組成物及びその成形体
WO2014196599A1 (fr) 2013-06-05 2014-12-11 協同油脂株式会社 Composition de graisse
US10947477B2 (en) 2016-03-08 2021-03-16 Kyodo Yushi Co., Ltd. Grease composition

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JP2008208174A (ja) * 2007-02-23 2008-09-11 Nsk Ltd グリース組成物及び転動装置
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