WO2022172935A1 - ジナフチルエーテル化合物およびそれを含む潤滑油組成物 - Google Patents

ジナフチルエーテル化合物およびそれを含む潤滑油組成物 Download PDF

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WO2022172935A1
WO2022172935A1 PCT/JP2022/005004 JP2022005004W WO2022172935A1 WO 2022172935 A1 WO2022172935 A1 WO 2022172935A1 JP 2022005004 W JP2022005004 W JP 2022005004W WO 2022172935 A1 WO2022172935 A1 WO 2022172935A1
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compound
group
mol
dinaphthyl
dinaphthyl ether
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French (fr)
Japanese (ja)
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達也 前田
麻由美 林
孝平 山下
雅幸 畑
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Moresco Corp
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Moresco Corp
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Priority to CN202280014045.7A priority Critical patent/CN117015522B/zh
Priority to US18/276,162 priority patent/US12590048B2/en
Priority to EP22752758.7A priority patent/EP4273118A4/en
Priority to JP2022580643A priority patent/JP7603090B2/ja
Publication of WO2022172935A1 publication Critical patent/WO2022172935A1/ja
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    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/16—Ethers
    • 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
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—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
    • C10N2040/08—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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft 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 dinaphthyl ether compounds and lubricating oil compositions containing the same.
  • Lubricating oils and lubricating oil compositions are used to reduce friction and wear between moving parts and surfaces of various mechanical devices.
  • lubricating oils, lubricating greases, etc. are being used under more severe conditions such as high temperatures, high speeds, high loads, and under radiation, and there is a demand for lubricating oils with even better heat resistance.
  • Patent Document 1 a phenyl ether-based lubricating oil containing polyphenyl ether having 3 to 5 phenyl groups and at least one alkyl substituent having 10 to 20 carbon atoms as an active ingredient Synthetic lubricating oils (Patent Document 1) are known.
  • a lubricating oil having radiation resistance o-(m-phenoxyphenoxy)diphenyl 0 to 70% by weight, m-(m-phenoxyphenoxy)diphenyl 25 to 75%, and an alkyl carbon number of 10 to 20
  • o-(m-phenoxyphenoxy)diphenyl 0 to 70% by weight o-(m-phenoxyphenoxy)diphenyl 0 to 70% by weight, m-(m-phenoxyphenoxy)diphenyl 25 to 75%, and an alkyl carbon number of 10 to 20
  • Patent Document 2 A radiation-resistant lubricating oil containing 75 to 25% monoalkyldiphenyl ether or dialkyldiphenyl ether
  • the lubricating agents described in Patent Documents 1 and 2 have excellent heat resistance and radiation resistance. Therefore, there is a demand for a lubricating oil with even better heat resistance.
  • the object of the present invention is to solve the above problems. That is, it is an object of the present invention to provide a compound that has superior heat resistance and can be used as a lubricating oil under severer conditions.
  • the dinaphthyl ether compound according to one aspect of the present invention is a compound represented by the following formula (1).
  • R 1 and R 2 are the same or different and are straight or branched hydrocarbon groups having 6 to 32 carbon atoms; m and n are each a real number of 0 or more; and , satisfies 1.0 ⁇ m + n ⁇ 3.0)
  • FIG. 1 shows a gas chromatography (GC) chart of the dinaphthyl ether synthesized in Example 1.
  • FIG. 2 shows the 1 H-NMR spectrum of a model compound for determining the number of hydrocarbon group substitutions.
  • the dinaphthyl ether compound of the present invention is, as described above, a compound represented by the following formula (1).
  • R 1 and R 2 are the same or different and are straight or branched hydrocarbon groups having 6 to 32 carbon atoms. Moreover, m and n are each a real number equal to or greater than 0 and satisfy 1.0 ⁇ m+n ⁇ 3.0.
  • a dinaphthyl ether compound having such a structure is very useful as a lubricating oil because it has excellent heat resistance while maintaining lubricity equivalent to that of conventional compounds as described in the prior art. is. More specifically, the dinaphthyl ether compound has little evaporation loss at high temperatures and has a long life at high temperatures, so it can be suitably used as a base oil for high-temperature lubricating oils or heat-resistant greases that are used at higher temperatures. can be done.
  • a dinaphthyl ether compound that has superior heat resistance and can be used as a lubricating oil that can be used under more severe conditions.
  • the dinaphthyl ether compound of the present embodiment is a compound represented by the above formula (1).
  • R 1 and R 2 are the same or different and are a hydrocarbon group having 6 to 32 carbon atoms. In some cases, either one of R 1 and R 2 may be a hydrogen atom. That is, either one of R 1 and R 2 may be a hydrogen atom, but at least one of them is the aforementioned hydrocarbon group.
  • the number of carbon atoms in the hydrocarbon group is less than 6, the physical properties of the dinaphthyl ether that does not have a hydrocarbon group are considered to greatly affect the fluidity. Moreover, since the molecular weight is small, the amount of evaporation increases. On the other hand, if the number of carbon atoms exceeds 32, the interaction between molecules will increase and the viscosity will become too high, exceeding the viscosity range generally used. When the number of carbon atoms in the hydrocarbon group is 6 to 32, the balance between heat resistance and low temperature properties is well balanced, which is preferable. More preferably, the lower limit of the number of carbon atoms in the hydrocarbon group is 16 or more, and the upper limit is 28 or less.
  • linear hydrocarbon groups include, for example, hexyl group, octyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, icosyl group, docosyl group, tetracosyl group, hexacosyl group and octacosyl group.
  • alkyl groups such as groups; alkylene groups such as octene group, decene group, hexadecene group, dodecene group, octadecene group, icosene group, docosene group, tecoracosene group, hexacosene group and octacosene group; cyclohexyl group and the like.
  • Branched hydrocarbon groups include, for example, 1-methylundecyl group, 1-ethyldecyl group, 1-methyltridecyl group, 1-ethyldodecyl group, 1-methylpentadecyl group, 1-ethyltetradodecyl group, 1-methylheptadecyl group, 1-ethyloctadecyl group, 1-methylnonadecyl group, 1-ethyloctadecyl group, 2-ethylhexyl group, 2-octyldodecyl group, 2-decyltetradecyl group, 2-dodecylhexadecyl group, 1 -butyl-1-methylpentyl group, 1-butyl-1-methylheptyl group, 1-methyl-1-pentyloctyl group, 1-hexyl-1-methylnonyl group, 1-heptyl-1-methyldecyl group, 1 -methyl
  • hydrocarbon groups having 12 to 32 carbon atoms are preferred from the viewpoint of obtaining better heat resistance, and 1-methylundecyl and 1-methyltridecyl are preferred. group, 1-methylpentadecyl group, 1-methyl-1-octylundecyl group, 1-decyl-1-methyltridecyl group, 1-dodecyl-1-methylpentadecyl group, hexadecyl group, dodecyl group, tetradecyl group , 2-octyldodecyl group, 2-decyltetradecyl group, 2-dodecylhexadecyl group and the like.
  • the hydrocarbon group as described above may be bonded to any of the two naphthyl groups in the formula (1) as long as m and n satisfy 1.0 ⁇ m + n ⁇ 3.0, Moreover, it may be bonded to any position of the naphthyl group. Further, for example, when m+n is 1, either one of R 1 and R 2 may be a hydrogen atom.
  • each of m and n is a real number of 0 or more and satisfies 1.0 ⁇ m+n ⁇ 3.0.
  • m+n is less than 1.0, it is considered that the physical properties of dinaphthyl ether having no hydrocarbon group appear and the fluidity deteriorates. Moreover, since the molecular weight is small, the amount of evaporation cannot be sufficiently suppressed. On the other hand, when m+n exceeds 3.0, the interaction between molecules increases and the viscosity becomes too high.
  • m+n indicates the number of linear or branched hydrocarbon group substitutions (hereinafter simply referred to as the number of alkyl substitutions).
  • the compound of the present embodiment may be, for example, a mixture of a compound satisfying 0 ⁇ m+n ⁇ 2.0 and a compound satisfying 2.0 ⁇ m+n ⁇ 3.0.
  • the value of m+n means the average value of m+n in the dinaphthyl ether compounds contained in the compound of the present embodiment.
  • m+n is more preferably 1 or more and 2.5 or less.
  • the number of hydrocarbon group substitutions can be measured by the method shown in Examples below.
  • the weight average molecular weight of the dinaphthyl ether compound of the present embodiment is preferably about 450-800. If the weight average molecular weight of the dinaphthyl ether compound is large, there is an advantage that it is excellent in heat resistance. Therefore, if the mass average molecular weight is within the above range, the kinematic viscosity and the pour point are not too high, and the heat resistance is excellent. On the other hand, when the weight average molecular weight is smaller than the above range, the heat resistance tends to be poor.
  • the weight-average molecular weight of the dinaphthyl ether compound in the present embodiment is a value measured using 1 H-NMR as shown in Examples below.
  • a mass average molecular weight is also simply called "average molecular weight.”
  • the method for producing the dinaphthyl ether compound as described above is not particularly limited, it can be obtained, for example, by the following synthesis method.
  • NMP N-methyl-2-pyrrolidone
  • the dinaphthyl ether compound of the present embodiment can be obtained by reacting the naphthyl ether with a linear or branched olefin or the like using, for example, aluminum chloride or the like as a catalyst.
  • the present invention also includes a lubricating oil composition containing the dinaphthyl ether compound as described above.
  • lubricating oil composition of the present embodiment in addition to the dinaphthyl ether compound, for the purpose of further improving its performance, or for imparting further performance as necessary, within a range that does not impair the effects of the present invention
  • mineral oils synthetic oils such as ⁇ -olefin oligomers, polyol esters, diesters, polyalkylene glycols, silicone oils, modified silicone oils, alkyldiphenyl ether oils, multiple alkylate cyclopentane oils, and silahydrocarbon oils are mixed. be able to.
  • various additives such as antioxidants, extreme pressure agents, friction modifiers, metal deactivators, antifoaming agents, thickeners, and colorants may be blended alone or in combination as necessary. Also good.
  • antioxidants that are generally used in lubricating oils can be used without particular limitation. compounds and the like.
  • extreme pressure agents include phosphorus-based compounds and sulfur-based compounds.
  • friction modifiers examples include molybdenum compounds such as molybdenum dithiocarbamate and fatty acid derivatives such as glycerin monostearate.
  • metal deactivators examples include benzotriazole-based, tolyltriazole-based, thiadiazole-based, and imidazole-based compounds.
  • Antifoaming agents include, for example, polyacrylates and styrene ester polymers.
  • Thickeners include, for example, metal soap (eg lithium soap), silica, expanded graphite, polyurea, clay (eg hectorite or bentonite).
  • the content thereof is 50 to 100% by mass with respect to the entire lubricating oil composition (total mass) from the viewpoint of ensuring heat resistance. It is preferable that it is a degree. In that case, the content of additives and the like in the lubricating oil composition is preferably about 50 to 0% by mass.
  • the dinaphthyl ether compound can be used as an additive in a lubricating oil composition, in which case the content of the dinaphthyl ether compound is 1 to 1 with respect to the entire lubricating oil composition (total mass) It is preferably about 49% by mass.
  • the present invention also includes high-temperature lubricating oils and heat-resistant greases containing dinaphthyl ether compounds as described above.
  • the lubricating oil composition, high-temperature lubricating oil, and heat-resistant grease as described above are suitably used as bearing lubricants, impregnated bearing lubricants, grease base oils, refrigerator oils, plasticizers, and the like.
  • various lubricating oils used under high temperature conditions such as bearing oil, hydrodynamic bearing oil, oil-impregnated bearing oil, grease base oil, oil-impregnated plastics oil, gear oil, jet engine oil, heat insulating engine oil, gas turbine oil, It can be suitably used as automatic transmission oil, vacuum pump oil, hydraulic fluid, and the like.
  • the dinaphthyl ether compound as described above also has excellent radiation resistance, it is thought that it can be suitably used as a radiation-resistant lubricating oil and radiation-resistant grease.
  • a dinaphthyl ether compound according to one aspect of the present invention is a compound represented by the following formula (1).
  • R 1 and R 2 are the same or different and are straight or branched hydrocarbon groups having 6 to 32 carbon atoms; m and n are each a real number of 0 or more; and , satisfies 1.0 ⁇ m + n ⁇ 3.0)
  • a lubricating oil composition relating to another aspect of the present invention is characterized by containing the dinaphthyl ether compound described above.
  • a high-temperature lubricating oil and a radiation-resistant lubricating oil relating to still another aspect of the present invention are characterized by containing the dinaphthyl ether compound described above.
  • a heat-resistant grease and a radiation-resistant grease relating to still another aspect of the present invention are characterized by containing the dinaphthyl ether compound described above.
  • the lubricating oil composition, high-temperature lubricating oil, and heat-resistant grease according to the present invention have extremely excellent heat resistance, so they are suitable for use under severe conditions (especially at high temperatures).
  • Example 2 Compound 2
  • 120 g (0.44 mol) of the dinaphthyl ether obtained in Example 1 1.05 g (0.0078 mol) of anhydrous aluminum chloride, and 37 g (0.22 mol) of 1-dodecene were mixed. mol) and distilled under reduced pressure from 260°C to 300°C at 80 Pa to obtain a monoalkyl-substituted product as a distillate.
  • a dinaphthyl ether compound 2: alkyl (C12)-1-(2-naphthyloxy)naphthalene (C12-1,2-DNO) was obtained.
  • Example 3 Compound 3
  • a four-necked flask with a volume of 500 mL was used for the reaction, and 100 g (0.37 mol) of the dinaphthyl ether obtained in Example 1, 1.57 g (0.012 mol) of anhydrous aluminum chloride, and 56 g (0.33 mol) of 1-dodecene were mol) and distilled under reduced pressure at 80 Pa at 300° C. under the same conditions as in Example 1, except that unreacted raw materials, monoalkyl-substituted products, etc. were removed.
  • a dinaphthyl ether compound 3: dialkyl (C12)-1-(2-naphthyloxy)naphthalene (diC12-1,2-DNO) was obtained.
  • Example 4 Compound 4
  • a 500 mL four-necked flask for the reaction 135 g (0.50 mol) of the dinaphthyl ether obtained in Example 1, 2.46 g (0.019 mol) of anhydrous aluminum chloride, and 70 g of 2-octyl-1-dodecene were mixed. (0.25 mol), under the same conditions as in Example 1, an alkyl-substituted dinaphthyl ether (compound 4: branched alkyl (C20)-1-(2 -naphthyloxy)naphthalene (bC20-1,2-DNO)).
  • Example 5 Compound 5
  • 30 g (0.11 mol) of the dinaphthyl ether obtained in Example 1 0.53 g (0.0040 mol) of anhydrous aluminum chloride, and 19 g of 2-decyl-1-tetradecene were mixed. (0.060 mol), under the same conditions as in Example 1, an alkyl-substituted dinaphthyl ether (compound 5: branched alkyl (C24)-1-(2 -naphthyloxy)naphthalene (bC24-1,2-DNO)).
  • Example 6 Compound 6
  • 30 g (0.11 mol) of the dinaphthyl ether obtained in Example 1 0.61 g (0.0046 mol) of anhydrous aluminum chloride, and 22 g of 2-dodecyl-1-hexadecene were mixed. (0.060 mol), under the same conditions as in Example 1, alkyl-substituted dinaphthyl ether (compound 6: branched alkyl (C28)-1-(2 -naphthyloxy)naphthalene (bC28-1,2-DNO)).
  • Example 7 Compound 11
  • 120 g (0.83 mol) of 1-naphthol, 230 g (1.66 mol) of potassium carbonate, and 32 g (0.17 mol) of copper iodide were placed in a 2-liter four-necked flask equipped with a stirrer, thermometer, dropping funnel and condenser.
  • 300 g of NMP were added, and the temperature of the reaction system was heated to 175° C. after nitrogen substitution was performed.
  • dropwise addition of 345 g (1.66 mol) of 1-bromonaphthalene was started. After the dropwise addition was completed, the mixture was stirred at 175° C. for 6 hours.
  • Kyoward 1000s was added in an amount 5.5 times the amount of anhydrous aluminum chloride, followed by stirring for 30 minutes. Subsequently, 3.65 times as much activated clay as that of anhydrous aluminum chloride was added, and after stirring at 90°C for 30 minutes, anhydrous aluminum chloride and other by-produced acidic substances were removed by filtration under reduced pressure.
  • the filtrate obtained here (reaction filtrate A) was distilled under reduced pressure at 250° C. to 260° C. at 80 Pa to obtain a monoalkyl-substituted alkyl diphenyl ether (compound 7: alkyl (C16) diphenyl ether (C16-DPO)) as a fraction. Obtained. 5% by weight of activated clay was added to the compound obtained here, and the mixture was stirred at 90° C. for 30 minutes, and mixed grease and the like were removed by filtration under reduced pressure.
  • Comparative Example 2 Compound 8
  • the reaction filtrate A obtained in Comparative Example 1 was distilled under reduced pressure at 80 Pa and 290° C. to remove unreacted raw materials, monoalkyl-substituted products, etc., and alkyl-substituted diphenyl ether (compound 8 : Dialkyl (C16) diphenyl ether (diC16-DPO)) was obtained.
  • Kyoward 1000s was added in an amount 5.5 times the amount of anhydrous aluminum chloride, followed by stirring for 30 minutes. Subsequently, 3.65 times as much activated clay as that of anhydrous aluminum chloride was added, and after stirring at 90°C for 30 minutes, anhydrous aluminum chloride and other by-produced acidic substances were removed by filtration under reduced pressure.
  • the filtrate obtained here was distilled under reduced pressure at 80 Pa and 320° C. to remove the reaction raw materials, etc., and the compound 9 (alkyl (C16)-2- (3-Phenoxyphenoxy)diphenyl (C16-4P2E)) was obtained. 5% by weight of activated clay was added to the compound obtained here, and the mixture was stirred at 90° C. for 30 minutes, and mixed grease and the like were removed by filtration under reduced pressure.
  • 1 H-NMR measurement conditions and hydrocarbon group substitution number calculation conditions 1 H-NMR was measured using a nuclear magnetic resonance apparatus JNM-ECX400 manufactured by JEOL Ltd. The measurement conditions were a temperature of 80° C. and no solvent or standard substance.
  • the chemical shift was obtained by measuring the same compound using deuterated chloroform as the solvent and TMS as the standard substance and comparing them. This is because the peaks of deuterated chloroform and the benzene ring overlap and an accurate integrated value cannot be obtained.
  • the obtained compounds 1 to 11 were analyzed using 1 H-NMR under the above conditions to determine the mass average molecular weight of each compound.
  • the number of hydrocarbon group substitutions of compounds 1 to 11 was determined by analyzing the 1 H-NMR spectrum of each compound. Specifically, the calculation method will be described using the 1 H-NMR spectrum of the model compound shown in FIG.
  • a (chemical shift 6.5 to 7.3) indicates the peak of hydrogen on the aromatic ring.
  • b 1 (chemical shifts 2.8-3.3) and b 2 (chemical shifts 2.2-2.7) show peaks of hydrogen at the benzylic position.
  • c (chemical shift 0.5 to 1.9) indicates the hydrogen peak of the hydrocarbon group.
  • Hydrocarbon group substitution number (m+n) (number of hydrogen atoms in aromatic ring) ⁇ (b 1 +b 2 +c)/[(average number of hydrogen atoms in hydrocarbon group) ⁇ a+b 1 +b 2 +c]
  • ⁇ Purity measurement> [Gas chromatography (GC) measurement conditions] Gas chromatography was measured using Shimadzu GC-2010 Plus. Ultra ALLOY+-17 was used as the column, and nitrogen gas was used as the carrier gas. The measurement temperature was maintained at 50°C for 2 minutes, then increased by 25°C per minute to 100°C, increased from 100°C by 15°C per minute to 350°C, and was maintained at 350°C for 15 minutes.
  • evaporation amount by the TG method was measured using ST7200RV manufactured by Hitachi High-Technologies Corporation.
  • the carrier gas is air (200 ml/min)
  • the sample container is an aluminum deep dish pan
  • the sample amount is 5 mg
  • the temperature is 250 ° C.
  • Lubricity test Lubricity was measured using OPTIMOL SRV-5. A 1/2 inch SUJ2 ball was used for the upper specimen and an SK-5 plate was used for the lower specimen. After running-in for 50 seconds at a temperature of 40 ° C, a load of 50 N, and a speed of 40 mm / s, the main test is performed at a temperature of 40 ° C, a load of 100 N, and a speed of 40 mm / s for 600 seconds to measure the coefficient of friction (COF). and the average COF at 100N was obtained. In this test, an average COF of 0.150 or less is judged as pass.
  • COF coefficient of friction
  • the dinaphthyl ether compound of the present invention has extremely excellent heat resistance, it can be suitably used as a high-temperature lubricating oil, a heat-resistant grease, etc., and has wide industrial applicability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
PCT/JP2022/005004 2021-02-12 2022-02-09 ジナフチルエーテル化合物およびそれを含む潤滑油組成物 Ceased WO2022172935A1 (ja)

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CN202280014045.7A CN117015522B (zh) 2021-02-12 2022-02-09 二萘醚化合物以及含有该二萘醚化合物的润滑油组合物
US18/276,162 US12590048B2 (en) 2021-02-12 2022-02-09 Dinaphthyl ether compound and lubricant composition containing same
EP22752758.7A EP4273118A4 (en) 2021-02-12 2022-02-09 Dinaphthyl ether compound and lubricant composition containing same
JP2022580643A JP7603090B2 (ja) 2021-02-12 2022-02-09 ジナフチルエーテル化合物およびそれを含む潤滑油組成物

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61179296A (ja) * 1984-11-26 1986-08-11 ナショナル　スターチ　アンド　ケミカル　コーポレーション 合成ベ−スオイル
JPS6244797B2 (https=) 1982-06-29 1987-09-22 Matsumura Sekiyu Kenkyusho
JPS6259760B2 (https=) 1982-12-01 1987-12-12 Nippon Genshiryoku Kenkyusho
JPH01261487A (ja) * 1988-04-13 1989-10-18 Nippon Oil Co Ltd 熱媒体油
JPH01316340A (ja) * 1988-02-08 1989-12-21 Nippon Oil Co Ltd 合成潤滑油
JP2000044976A (ja) * 1998-07-29 2000-02-15 Nippon Steel Chem Co Ltd 潤滑油組成物
JP2013018861A (ja) * 2011-07-11 2013-01-31 Nsk Ltd グリース組成物及び工作機械用転がり軸受
JP2021020368A (ja) 2019-07-26 2021-02-18 理想科学工業株式会社 インクジェット印刷装置

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6244797A (ja) 1985-08-23 1987-02-26 株式会社東芝 ドツトマトリツクスｌｃｄドライバコントロ−ル方式
JPS6259760A (ja) 1985-09-06 1987-03-16 東海ゴム工業株式会社 タイル装飾面付コンクリ−ト体の製法
US4892680A (en) * 1988-01-11 1990-01-09 Nippon Oil Co., Ltd. Synthetic lubricating oils and specified naphthalene derivatives for use therein
JP5659422B2 (ja) 2010-11-10 2015-01-28 株式会社Moresco アルキル化ジフェニルエーテルおよび該化合物を含む潤滑油剤
JP5994082B2 (ja) * 2012-10-31 2016-09-21 株式会社Moresco アルキル化ジフェニルエーテル化合物および該化合物を含む潤滑油剤

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6244797B2 (https=) 1982-06-29 1987-09-22 Matsumura Sekiyu Kenkyusho
JPS6259760B2 (https=) 1982-12-01 1987-12-12 Nippon Genshiryoku Kenkyusho
JPS61179296A (ja) * 1984-11-26 1986-08-11 ナショナル　スターチ　アンド　ケミカル　コーポレーション 合成ベ−スオイル
JPH01316340A (ja) * 1988-02-08 1989-12-21 Nippon Oil Co Ltd 合成潤滑油
JPH01261487A (ja) * 1988-04-13 1989-10-18 Nippon Oil Co Ltd 熱媒体油
JP2000044976A (ja) * 1998-07-29 2000-02-15 Nippon Steel Chem Co Ltd 潤滑油組成物
JP2013018861A (ja) * 2011-07-11 2013-01-31 Nsk Ltd グリース組成物及び工作機械用転がり軸受
JP2021020368A (ja) 2019-07-26 2021-02-18 理想科学工業株式会社 インクジェット印刷装置

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP4273118A4

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JP7603090B2 (ja) 2024-12-19
CN117015522A (zh) 2023-11-07
EP4273118A1 (en) 2023-11-08
EP4273118A4 (en) 2024-07-17

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