US20040242440A1 - Metal working fluid composition for use as spray in mist form - Google Patents

Metal working fluid composition for use as spray in mist form Download PDF

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Publication number
US20040242440A1
US20040242440A1 US10/485,268 US48526804A US2004242440A1 US 20040242440 A1 US20040242440 A1 US 20040242440A1 US 48526804 A US48526804 A US 48526804A US 2004242440 A1 US2004242440 A1 US 2004242440A1
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Prior art keywords
group
metal working
oils
working fluid
mist form
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Abandoned
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US10/485,268
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English (en)
Inventor
Ryoichi Okuda
Toshio Saito
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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Assigned to IDEMITSU KOSAN CO., LTD. reassignment IDEMITSU KOSAN CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: OKUDA, RYOICHI, SAITO, TOSHIO
Publication of US20040242440A1 publication Critical patent/US20040242440A1/en
Abandoned legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/005Volatile oil compositions; Vaporous lubricants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C10M2207/126Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066Thiocarbamic type compounds
    • C10M2219/068Thiocarbamate metal salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/04Aerosols

Definitions

  • the present invention relates to a metal working fluid composition for use as a spray in the mist form and a process for metal working. More particularly, the present invention relates to a metal working fluid composition for use as a spray in the mist form in metal working such as cutting, grinding, rolling, drawing and forging and a process for metal working using the composition.
  • the metal working fluid in general, a fluid not soluble in water which is obtained by adding various additives to mineral oils or a fluid soluble in water which is obtained by adding various additives to mineral oils and synthetic oils and used after being diluted with water, is used. In recent years, it is required that the amount of waste fluids be decreased due to the environmental problems and the consumption of electric power be decreased. Therefore, processes for metal working using fluids in the mist form are studied. Since the mist is discharged into the atmosphere when the metal working fluid is used in the mist form, various biodegradable fluids are proposed. For example, processes using biodegradable plant oils as the metal working fluid are disclosed in Japanese Patent Application Laid-Open Nos.
  • the present invention is made to overcome the above drawbacks and has an object of providing a metal working fluid composition for use as a spray in the mist form which is inexpensive and exhibits excellent workability and a process for metal working using the composition.
  • a metal working fluid composition for use as a spray in a mist form which comprises (a) a base oil comprising at least one of mineral oils and synthetic oils and, based on an amount of an entire composition, (b) 1 to 50% by mass of a sulfur-based extreme pressure agent and (c) 0 to 30% by mass of an ester of a carboxylic acid;
  • a metal working fluid composition for use as a spray in a mist form described in (1) which comprises 50 to 90% by mass of component (a) based on the amount of an entire composition;
  • component (b) comprises at least one of dihydrocarbyl polysulfides and sulfurized oils and fats;
  • component (c) is at least one of oils, fats and triglycerides which are not oils or fats;
  • a process for metal working which comprises supplying a metal working fluid composition for use as a spray in a mist form described in any one of (1) to (4) in a mist form.
  • the base oil of component (a) constituting the metal working fluid composition for use as a spray in the mist form of the present invention a mineral oil, a synthetic oil or a mixture of these oils can be used.
  • the mineral oil and the synthetic oil are not particularly limited as long as these oils are used as the base oil for metal working fluids. It is preferable that the mineral oil and the synthetic oil have a kinematic viscosity at 40° C. in the range of 1 to 100 mm 2 /s and more preferably in the range of 3 to 50 mm 2 /s. When the kinematic viscosity exceeds the above range, there is the possibility that the mist is not formed.
  • the pour point which is the index of the fluidity of the base oil at low temperatures is not particularly limited. It is preferable that the pour point is ⁇ 10° C. or lower.
  • the base oil can be suitably selected from these oils in accordance with the application.
  • the mineral oil include distilled oils obtained by atmospheric distillation of paraffinic crude oils, intermediate crude oils and naphthenic crude oils, distilled oils obtained by vacuum distillation of residual oils of the atmospheric distillation and purified oils obtained by purifying the above oils in accordance with a conventional process such as oils purified with solvents, oils purified by hydrogenation, oils treated by dewaxing and oils treated with clay.
  • Examples of the synthetic oil include poly- ⁇ -olefins, ⁇ -olefin copolymers, polybutene, alkylbenzenes, esters of polyols, esters of dibasic acids, polyoxyalkylene glycols, esters of polyoxyalkylene glycols, ethers of polyoxyalkylene glycols and silicone oils.
  • base oil may be used singly, in combination of two or more or in combination of mineral oils and synthetic oils.
  • the amount of component (a) in the metal working fluid composition is in the range of 50 to 98% by mass based on the amount of the entire metal working fluid composition.
  • the amount of the base oil is less than the above range, there is the possibility that the mist is not formed.
  • the amount exceeds the above range there is the possibility that the workability such as the property for cutting cannot be maintained.
  • the sulfur-based extreme pressure agent of component (b) constituting the metal working fluid composition for use as a spray in the mist form of the present invention is not particularly limited as long as the agent has a sulfur atom in the molecule and can be dissolved or uniformly dispersed in the base oil of the lubricating oil so that the effect of the extreme pressure agent can be exhibited.
  • the sulfur-based extreme pressure agent include sulfurized oils and fats, sulfurized fatty acids, sulfurized esters, sulfurized olefins, dihydrocarbyl polysulfides, thiocarbamates, thioterpenes and dialkyl thiodipropionates.
  • the sulfurized oils and fats are obtained by the reaction of sulfur or compounds having sulfur with oils and fats such as lard, whale oil, plant oils and fish oils.
  • the content of sulfur is not particularly limited. In general, it is preferable that the content of sulfur is in the range of 5 to 30% by mass.
  • Examples of the sulfurized oil and fat include sulfurized lard, sulfurized rapeseed oil, sulfurized castor oil, sulfurized soy bean oil and sulfurized rice bran oil.
  • the sulfurized fatty acid include sulfurized oleic acid.
  • Examples of the sulfurized ester of a fatty acid include sulfurized methyl oleate and sulfurized octyl ester of rice bran fatty acid.
  • sulfurized olefin examples include compounds represented by the following general formula (1):
  • R 1 represents an alkenyl group having 2 to 15 carbon atoms
  • R 2 represents an alkyl group or alkenyl group having 2 to 15 carbon atoms
  • x represents an integer of 1 to 8.
  • This compound can be obtained by the reaction of an olefin having 2 to 15 carbon atoms, or a dimer, a trimer or a tetramer thereof with a sulfurizing agent such as sulfur and sulfur chloride.
  • a sulfurizing agent such as sulfur and sulfur chloride.
  • the olefin propylene, isobutene and diisobutene are preferable.
  • the dihydrocarbyl polysulfide is a compound represented by the following general formula (2):
  • R 3 and R 4 each represent an alkyl group or cyclic alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms and may represent the same group or different groups, and y represents an integer of 2 to 8.
  • R 3 and R 4 represent alkyl groups, the above compound is called a sulfurized alkyl.
  • Examples of the group represented by R 3 and R 4 in the above general formula (2) include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, various types of pentyl group, various types of hexyl group, various types of heptyl group, various types of octyl group, various types of nonyl group, various types of decyl group, various types of dodecyl group, cyclohexyl group, cyclooctyl group, phenyl group, naphthyl group, tolyl group, xylyl group, benzyl group and phenetyl group.
  • dihydrocarbyl polysulfide examples include dibenzyl polysulfide, di-tert-nonyl polysulfide, didodecyl polysulfide, di-tert-butyl polysulfide, dioctyl polysulfide, diphenyl polysulfide and dicyclohexyl polysulfide.
  • Examples of the thiocarbamate include zinc dithiocarbamate.
  • Examples of the thioterpene include reaction products of phosphorus pentasulfide and pinene.
  • Examples of the dialkyl thiodipropionate include dilauryl thiodipropionate and distearyl thiodipropionate.
  • dihydrocarbyl polysulfides, sulfurized fats and oils and mixtures of these substances are preferable from the standpoint of the properties as the extreme pressure agent.
  • component (b) described above may be used singly or in combination of two or more.
  • the amount of component (b) is in the range of 1 to 50% by mass and preferably in the range of 3 to 30% by mass based on the mass of the entire composition.
  • the amount is less than 1% by mass, the workability such as the property for cutting cannot be maintained.
  • the amount exceeds 50% by mass, viscosity of the composition increases and the effect of the present invention cannot be obtained.
  • the metal working fluid composition for use as a spray in the mist form of the present invention may further comprise an ester of a carboxylic acid as component (c) so that the workability is improved.
  • the ester of a carboxylic acid has at least one ester linkage (—CO 2 —) in the molecule and includes monoesters of carboxylic acids having one ester linkage and esters of carboxylic acids having two or more ester linkages.
  • the monoester having one ester linkage is a compound represented by R 5 —CO 2 —R 6 , wherein R 5 and R 6 each represent an alkyl group or an alkenyl group.
  • R 5 examples include n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, 2-methyldecyl group, 3-methyldecyl group, 4-methyldecyl group, 5-methyldecyl group, 6-methyldecyl group, 7-methyldecyl group, 9-methyldecyl group, 6-ethylnonyl group, 5-propyloctyl group, 3-methylundecyl group, 6-prop
  • Examples of the group represented by R 6 include the groups described above as the examples of the group represented by R 5 , methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-eicosyl group, 2-methylpentyl group, 3-methylpentyl group, 4-propylpentyl group, 4-ethylpentyl group, 3-methylnonadecyl group and 2-ethyloctadecyl group.
  • ester having two or more ester linkages examples include esters of oxalic acid, esters of malonic acid, esters of succinic acid, esters of maleic acid, esters of fumaric acid, esters of glutaric acid, esters of adipic acid, esters of pimellic acid, esters of suberic acid, esters of azelaic acid, esters of sebacic acid, esters of phthalic acid, esters of trimellitic acid, esters of pyromellitic acid, oils and fats (soy bean oil, rapeseed oil, lard and the like), triglycerides which are not oils or fats, esters of neopentyl glycol, esters of trimethylolpropane and esters of pentaerythritol.
  • the alcohol for the above esters of acids include alcohols having groups represented by R 6 described above.
  • examples of the acid for the above ester of alcohols include acids having groups represented by R 5
  • oils and fats, triglycerides which are not oils or fats and mixtures of these substances are preferable since the workability is improved.
  • component (c) described above may be used singly or in combination of two or more.
  • the amount of component (c) is in the range of 0 to 30% by mass and preferably in the range of 5 to 20% by mass based on the amount of the entire composition. When the amount exceeds 30% by mass, the effect of the extreme pressure agent is adversely affected and the workability becomes poor.
  • the metal working fluid composition for use as a spray in the mist form of the present invention can be obtained by mixing the base oil with component (b) described above and, where necessary, component (c) described above.
  • various conventional additives may be suitably added in the range such that the object of the present invention is not adversely affected so that the basic properties of the composition as the metal working oil are maintained.
  • the additive include extreme pressure agents other than the sulfur-based extreme pressure agents, oiliness agents, defoaming agents and antioxidants.
  • Mist preventives which adversely affect the formation of the mist additives containing metals which are hardly formed into the mist and additives having a great molecular weight cannot be used as the additives since there is the possibility that the formation of the mist becomes difficult or the effective component cannot be formed into the mist.
  • the present invention provides the process for metal working which comprises supplying the metal working fluid composition for use as a spray in the mist form described above in the mist form. This process provides excellent workability.
  • Tool for cutting a tool in accordance with the Japanese Industrial Standard SKH51 (the rake angle in the transverse direction: 15°; the clearance angle in the transverse direction: 1°)
  • the metal working fluid composition for use as a spray in the mist form which is inexpensive and exhibits excellent workability and the process for metal working using the composition can be provided.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US10/485,268 2001-08-17 2002-08-02 Metal working fluid composition for use as spray in mist form Abandoned US20040242440A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2001247867A JP2003055679A (ja) 2001-08-17 2001-08-17 ミスト状噴霧用金属加工油組成物及び金属加工方法
JP2001-247867 2001-08-17
PCT/JP2002/007926 WO2003016440A1 (fr) 2001-08-17 2002-08-02 Composition fluide pour usinage d'un metal utilisable en tant qu'aerosol sous forme de brouillard

Publications (1)

Publication Number Publication Date
US20040242440A1 true US20040242440A1 (en) 2004-12-02

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US10/485,268 Abandoned US20040242440A1 (en) 2001-08-17 2002-08-02 Metal working fluid composition for use as spray in mist form

Country Status (5)

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US (1) US20040242440A1 (ja)
JP (1) JP2003055679A (ja)
CN (1) CN100368513C (ja)
TW (1) TWI269807B (ja)
WO (1) WO2003016440A1 (ja)

Cited By (5)

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US20140162913A1 (en) * 2011-07-25 2014-06-12 David McCreery Corrosion-inhibiting lubricant and methods therefor
US20160251594A1 (en) * 2015-02-28 2016-09-01 Indian Oil Corporation Limited Hot rolling oil for steel
WO2016158534A1 (ja) * 2015-03-30 2016-10-06 出光興産株式会社 切削・研削加工油組成物
US11186800B2 (en) 2015-12-21 2021-11-30 Henkel Ag & Co. Kgaa Metalworking fluid
US11767486B2 (en) * 2019-01-29 2023-09-26 Dic Corporation Sulfur-based extreme-pressure agent and metalworking fluid

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JP2006249370A (ja) * 2005-03-14 2006-09-21 Nippon Oil Corp 金属加工油組成物
EP2132251B1 (en) * 2006-12-21 2016-10-12 Croda Americas LLC Composition and method
DE102007001190A1 (de) * 2007-01-05 2008-07-10 Wet-Protect-Gmbh Zusammensetzung zum Schutz vor Feuchtigkeit, insbesondere Korrosionsschutz
DE102007001189A1 (de) * 2007-01-05 2008-07-10 Wet-Protect-Gmbh Zusammensetzung zum Schutz vor Feuchtigkeit, insbesondere Korrosionsschutz
CN101717684B (zh) * 2009-11-20 2013-01-16 东莞市安默琳节能环保技术有限公司 用于金属材料切削加工的喷雾供给方式切削油

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US20140162913A1 (en) * 2011-07-25 2014-06-12 David McCreery Corrosion-inhibiting lubricant and methods therefor
US9453178B2 (en) * 2011-07-25 2016-09-27 David McCreery Corrosion-inhibiting lubricant and methods therefor
US20160251594A1 (en) * 2015-02-28 2016-09-01 Indian Oil Corporation Limited Hot rolling oil for steel
WO2016158534A1 (ja) * 2015-03-30 2016-10-06 出光興産株式会社 切削・研削加工油組成物
JPWO2016158534A1 (ja) * 2015-03-30 2018-01-25 出光興産株式会社 切削・研削加工油組成物
US11186800B2 (en) 2015-12-21 2021-11-30 Henkel Ag & Co. Kgaa Metalworking fluid
US11767486B2 (en) * 2019-01-29 2023-09-26 Dic Corporation Sulfur-based extreme-pressure agent and metalworking fluid

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CN100368513C (zh) 2008-02-13
TWI269807B (en) 2007-01-01
JP2003055679A (ja) 2003-02-26
CN1802426A (zh) 2006-07-12

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