WO2005080305A1 - アルキルアセタール化合物とその製造方法及び潤滑油組成物 - Google Patents
アルキルアセタール化合物とその製造方法及び潤滑油組成物 Download PDFInfo
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- 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
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
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- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- 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
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M141/00—Lubricating 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
- C10M141/02—Lubricating 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 oxygen-containing compound
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- C10M141/00—Lubricating 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
- C10M141/06—Lubricating 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 nitrogen-containing compound
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
- C10M2205/0265—Butene used as base material
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- 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
- C10M2207/042—Epoxides
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- 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
- C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
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- 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
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
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- 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
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- 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
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- 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
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/243—Cold working
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/245—Soft metals, e.g. aluminum
Definitions
- Alkyl acetal compound method for producing the same, and lubricating oil composition
- the present invention relates to an alkylacetal mixture suitable as a compounding component of a lubricating oil composition, particularly a copper pipe drawing oil composition, and a method for producing the same.
- the present invention has excellent lubricating properties even in a high temperature region using such a compound, and can be used for metal working (cold rolling, drawing, punching, forging, coining, bending, stretch forming, drawing, etc.).
- the present invention relates to a lubricating oil composition for metal working suitable for (1), and particularly to a lubricating oil composition for metal working suitable for processing of a copper-based metal (copper or copper-containing metal).
- Cutting oil, grinding oil, polishing oil, rolling oil, drawing oil, press oil, forging oil, and metal working oil used for processing such as polishing and cutting of silicon wafers are required to have lubricity.
- water-insoluble oils obtained by adding various additives to mineral oil or water-soluble oils obtained by adding various additives to mineral oil or synthetic oil diluted with water are used as metalworking oils.
- metal processing oils such as emulsion-based cutting oils based on mineral oil and non-aqueous cutting oils have been used as oiliness improvers such as fatty acid esters and fatty acids, and extreme pressure agents containing elements such as sulfur, chlorine and phosphorus. Is added to improve lubricity.
- alkylene oxide adducts of polyhydric alcohols having 3 to 6 hydroxyl groups and alkylene oxides of polyhydric alcohols having 3 to 6 hydroxyl groups have been used. It contains an oxygen-containing compound selected from hydrated carbyl ethers of a sulfide adduct, a specific polyalkylene glycol, a hydrated carbyl ether of a specific polyalkylene glycol, and an oxygenated compound selected from dihydric alcohols having 2 to 8 carbon atoms.
- Metal working oil composition (for example, see Patent Document 1), a fatty acid having 12 to 22 carbon atoms was reacted with a 3- to 6-valent polyol so that the remaining hydroxyl group of the polyol became 2.0 to 2.5.
- Lubricating oil composition including polyester composition for lubricating oil containing polyester of $ 3000-1250 cps obtained by reacting 0.7-1.10 monobasic dibasic acid against partial monoester (See, for example, Patent Document 2), a metal working oil composition containing a metal working oil additive containing a reaction product of an epoxidized fatty acid alkyl ester and an amine compound (for example, Patent Document 3), metal working oils composed of a specific polyether having an HLB of 6.0 or less and a weight average molecular weight of 500,30,000 (for example, see Patent Document 4) are disclosed.
- these metalworking oil compositions or lubricating oil composition compositions did not simultaneously satisfy annealing properties and lubrication properties.
- copper-based metals are characterized by excellent thermal conductivity and workability.
- copper pipes used for heat exchangers for air conditioners are among the most strict standards.
- copper tubes are manufactured by drawing, washed, dried, and then shipped through an annealing operation.
- a lubricating oil oil agent
- it is usually necessary to use a lubricating oil (oil agent) having high viscosity and good processability under severe processing conditions for example, see Patent Document 5.
- lubricating oil oil agent
- polymers such as easily decomposable polybutene are Copper pipe drawing oils based on oil have been developed (for example, see Patent Documents 6-10).
- Patent Document 1 Japanese Patent Application Laid-Open No. 10-8080
- Patent Document 2 JP-A-8-208814
- Patent Document 3 Japanese Patent Application Laid-Open No. 2000-186292
- Patent Document 4 JP 2003-238978 A
- Patent Document 5 JP-A-2000-263125
- Patent Document 6 JP-A-11-193390
- Patent Document 7 JP-A-11-209781
- Patent Document 8 JP-A-11-349975
- Patent Document 9 JP-A-2000-96073
- Patent Document 10 JP-A-2000-186291
- the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a compound that satisfies annealing characteristics and lubrication characteristics simultaneously, and a method for producing the same.
- the present invention has excellent lubricating properties (low friction) even in a high temperature range, and has a metal working (cold rolling, drawing, punching, forging, coining, bending, stretch forming, drawing, etc.).
- the inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that the alkylacetal compound having a straight-chain alkyl group branched at the 2-position of the alkyl group S, annealing properties and lubrication properties. At the same time, and found to have higher performance than, for example, benzotriazole derivatives.
- a lubricating oil composition in which a specific compound is blended in a base oil has a lubricating oil composition equivalent to or higher than a conventionally used fatty acid ester. It has properties and processability, and has been found not to remain after annealing, which has a wider use temperature range than fatty acid esters and alcohols conventionally used.
- the present invention has been completed based on strong knowledge. That is, the present invention provides the following alkyl acetal compound and a method for producing the same. Further, the present invention provides the following lubricating oil composition for metal working.
- R 1 and R 2 each independently represent a hydrocarbon group.
- I and j are each an integer that satisfies 8-98.
- R 3 —R 8 each independently represent a hydrogen atom or a hydrocarbon group.
- K is 0 or 1
- i And j are integers each of which satisfies 8-98.
- i and j are integers each of which satisfies 8-98.
- the epoxide has the following general formula (5) [0015] [Formula 5]
- n is an integer of 3 to 48.
- i and j are integers each of which satisfies 8-98.
- the aldehyde is represented by the following general formula (7)
- n is an integer of 3 to 48.
- R 3 to R 8 each independently represent a hydrogen atom or a hydrocarbon group.
- K is 0 or 1.
- glycol is a compound selected from ethylene glycol, propylene glycol, 1,3-trimethylene glycolone, 1,3-trimethylene glycol derivative, and 1,2-butanediol.
- a lubricating oil composition for metalworking comprising one or more compounds selected from the dioxane compounds represented by 14) in an amount of 1% by mass or more based on the composition.
- R u independently includes a hydrogen atom, a saturated hydrocarbon group having 130 to 130 carbon atoms, an unsaturated hydrocarbon group having 130 to 130 carbon atoms, and an ether bond, an ester bond or a hydroxyl group. Represents a group selected from hydrocarbon groups having 1 to 30 carbon atoms.
- the base oil is one or more selected from polybutene, polyisobutylene, and water-insoluble polyalkylene glycol having a kinematic viscosity at 40 ° C in the range of 5 to 3,000 mm 2 / s.
- R 39 and R 4 ° each independently include a saturated hydrocarbon group having 130 to 130 carbon atoms, an unsaturated hydrocarbon group having 130 to 130 carbon atoms, and an ether bond, an ester bond or a hydroxy group. Represents a group selected from hydrocarbon groups having 1 to 30 carbon atoms.
- a lubricating oil composition that satisfies annealing characteristics and lubricating characteristics simultaneously and is suitable as a copper pipe drawing oil or the like can be obtained.
- the present invention has excellent lubricating properties (low friction) even in a high temperature region, and has metal working (cold rolling, drawing, punching, forging, coining, bending, stretch forming, drawing, etc. ),
- metal working cold rolling, drawing, punching, forging, coining, bending, stretch forming, drawing, etc.
- a lubricating oil composition for metal working suitable for working of copper-based metal (copper or copper-containing metal).
- FIG. 1 is a diagram showing the sign of the hydrogen atom of a 1,3-dioxolane compound by NMR analysis.
- FIG. 2 is a diagram showing signs of carbon atoms of 1,3-dioxolane compounds by 13 C-NMR analysis.
- FIG. 3 is a graph showing a 1 H-NMR data profile in a detailed analysis of a 1,3-dioxolane compound.
- FIG. 4 is a graph showing a 13 C-NMR data profile in a detailed analysis of a 1,3-dioxolane compound.
- FIG. 5 is a graph showing a data profile of 13 C-NMR in a detailed analysis of a 1,3-dioxolane compound.
- FIG. 6 is a diagram showing the results of analysis of 1,3-dioxolane compounds by the 2D-COSY method.
- FIG. 7 is a view showing an analysis result of a 1,3-dioxolane compound by a 2D-HMQC method.
- FIG. 8 is a diagram showing the results of analysis of 1,3-dioxolane compounds by the 2D-HMBC method.
- FIG. 9 is a diagram showing the results of 2D-HMBC analysis of 1,3-dioxolane compounds.
- FIG. 10 is a graph showing the results of analysis of 1,3-dioxolane compounds by 2D-INADEQUATE.
- FIG. 11 is a view showing the results of analysis of 1,3-dioxolane compounds by the 2D-INADEQUATE method.
- FIG. 12 is a partially enlarged view of FIG. 11.
- FIG. 13 is a graph showing the results of a reciprocating friction test in Examples and Comparative Examples.
- FIG. 14 is a graph showing the results of a reciprocating friction test in Examples and Comparative Examples.
- FIG. 15 is a graph showing the results of a reciprocating friction test in Examples and Comparative Examples.
- FIG. 16 is a graph showing the results of a reciprocating friction test in Examples and Comparative Examples.
- the alkyl acetal compound of the present invention is a novel compound not described in any literature and has a structure represented by the following general formulas (1) and (2).
- R 1 and R 2 each independently represent a hydrocarbon group, and i and j are integers each of which satisfies 898.
- R 3 R 8 each independently represents a hydrogen atom or a hydrocarbon group, and k is 0 or 1. i and j are the same as above.
- hydrocarbon group examples include a hydrocarbon group having an appropriate substituent or a heteroatom and having a total carbon number of 120. Further, as the sum of i and j, an integer of 16 to 32 is particularly preferable, and an integer of 16 to 32 is particularly preferable.
- the alkyl acetal compound of the present invention has a structure in which a straight-chain alkyl group is branched at the 2-position of a straight-chain alkyl group.
- i is n
- j is n + 2
- n is more preferably an integer of 3-33, particularly preferably an integer of 7-15.
- k is 0, i is n and +2, and the following general formula (3)
- the alkyl cyclic acetal conjugate represented by the formula (1) is preferably exemplified.
- R 3 R 8 in the above general formula (2) and R 3 R 6 in the above general formula (3) are determined by the kind of glycol used for producing the alkyl cyclic acetal compound. Further, n is preferably an integer of 3-33.
- the method for producing the alkyl acetal compound represented by the general formulas (1) and (2) is not particularly limited, but according to the production method of the present invention shown below, the alkyl acetal aldehyde compound can be used. It can be manufactured efficiently.
- Epoxides represented by the above general formula (4) include the following general formula (5)
- the compound represented by is preferable.
- aldehydes represented by the general formula (1) or (2) By reacting an aldehyde represented by the formula with an alcohol, the alkyl acetal compound represented by the general formula (1) or (2) is produced.
- the aldehydes represented by the general formula (6) include the following general formula (7)
- the alkyl acetal compound represented by the general formula (1) can be obtained. Further, as alcohols, the following general formula (8)
- the alkyl cyclic acetal compound represented by the general formula (2) can be obtained.
- glycols for example, ethylene glycol, propylene glycol, 1,3-trimethylene glycol, 1,3-trimethylene glycol derivatives, and 1,2-butanediol are preferably used, and ⁇ , -alkanediol is particularly preferable.
- the ⁇ , ⁇ _alkanediol is represented by the following general formula (9) [0044]
- ⁇ ⁇ -alkanediol represented by the general formula (9)
- ethylene glycol, propylene glycol, 1,2-butanediol and the like are preferably used.
- the reaction temperature is usually about 0 to 200 ° C, preferably 20 to 140 ° C. is there.
- the reaction time is generally about 114 hours, preferably 415 hours.
- the aldehyde represented by the general formula (6) includes A garbet aldehyde obtained by oxidizing monobet alcohol with an oxidizing agent such as chromium oxide, and an aldehyde synthesized from the above epoxides are preferred.
- garbet aldehyde when garbet aldehyde is used as the aldehyde and ethylene glycol is used as the alcohol, ethylene glycol containing a small amount of sulfuric acid is heated to about 50 to 200 ° C, preferably 50 to 140 ° C. With stirring, garbetaldehyde is slowly added dropwise, and after the addition, the mixture is stirred for about 1 to 48 hours, preferably for 4 to 15 hours. The reaction is stopped, and the reactants are separated. An alkyl cyclic acetal compound can be removed.
- the alkyl acetal oil conjugate of the present invention when blended with a base oil, can provide a composition that satisfies annealing properties and lubrication properties at the same time and is suitable as a metalworking oil such as a copper pipe drawing oil. it can.
- a metalworking oil such as a copper pipe drawing oil.
- 2-long chain branched alkyl-1,3-dioxolane is preferred.
- Mineral oil and / or synthetic oil can be used as the base oil. This mineral oil or synthetic oil is not particularly limited as long as it is generally used as a base oil for lubricating oils.However, from the viewpoint of performance as a metalworking oil, the kinematic viscosity at 40 ° C is low.
- the pour point which is an indicator of the low-temperature fluidity of the base oil, is not particularly limited, but is preferably 110 ° C or lower.
- mineral oils and synthetic oils there are various types of such mineral oils and synthetic oils, and they may be appropriately selected according to the application.
- examples of the mineral oil include paraffinic mineral oil, naphthenic mineral oil, intermediate mineral oil, and the like. Specific examples include light neutral oil, medium neutral oil, heavy neutral oil, and bright neutral oil obtained by solvent refining or hydrogenation. Stocks can be mentioned.
- synthetic oils for example, polyolefin, polyolefin copolymer, polybutene, polyisobutylene, water-insoluble polyalkylene glycol, alkylbenzene, polyol ester, dibasic acid ester, polyoxyalkylene glycol, polyoxyalkylene Examples include norecylene glycolone ester, polyoxyanolequinylene glycolone ether, hinderester, silicone oil, and the like. Each of these base oils can be used alone or in combination of two or more, and mineral oil and synthetic oil may be used in combination.
- a thermally decomposable polymer such as polybutene, polyisobutylene and water-insoluble polyalkylene glycol having a kinematic viscosity at 40 ° C. in the range of 10 to 3,000 mm 2 / s is preferred.
- the lubricating oil composition comprising the easily heat-decomposable polymer and the alkyl acetal compound of the present invention has an annealing property (easily heat-decomposable, low residual oil, no discoloration) and a lubricating property (low friction) in metal processing. ) Are more satisfied.
- the copper-based metal acts specifically on the copper-based metal, forms an adsorption film equal to or more than that of the case where the fatty acid ester-based additive is blended, and can maintain a low friction coefficient even in a high temperature range.
- the above mineral oil or the like may be used.
- the compounding amount of the alkyl acetal compound of the present invention is usually 1% by mass or more based on the composition, and can be appropriately adjusted according to the processing method and processing conditions. .
- the processing method and processing conditions for example, in the case of cold rolling of pure copper, etc., about 115% by mass is appropriate, and in the case of drawing copper pipe, about 5 to 30% by mass is preferable.
- the lubricating oil composition usually contains a stabilizer, an oil agent, an extreme pressure agent, a dispersant, and a corrosion inhibitor within a range that does not impair the effects of the present invention in order to maintain basic performance as a lubricating oil agent.
- Known additives such as a stopping agent, an antioxidant, and an antifoaming agent can be appropriately added.
- the total amount of these additives is usually in the range of 0.01 to 20% by mass, based on the composition. The same applies to these additives in the lubricating oil composition for metal working described below.
- the lubricating oil composition for metalworking of the present invention comprises a dioxolan compound represented by the following general formula (11), a dioxolan compound represented by the following general formula (12), and a dioxolan compound represented by the following general formula:
- a dioxolan compound represented by the following general formula One or more compounds selected from dioxane conjugates represented by (13) and dioxane compounds represented by the following general formula (14) in an amount of 1% by mass or more based on the composition. It is.
- R u —R 38 are each independently a hydrogen atom, a saturated hydrocarbon group having 113 to 30 carbon atoms, preferably 428 to 28 carbon atoms, and a carbon atom having 110 to 30, preferably 41 to carbon atoms. It represents a group selected from among 28 unsaturated hydrocarbon groups and hydrocarbon groups having an ether bond, an ester bond or a hydroxyl group and having 1 to 30 carbon atoms, preferably 428 carbon atoms. At least one of R 11 to R 38 may be a hydrocarbon group having a hydrocarbon chain containing a nitrogen atom. Examples of saturated hydrocarbon groups having 1 to 30 carbon atoms include methyl group, ethyl group, n-propyl group and isopropanol.
- Examples of the unsaturated hydrocarbon group having 130 to 130 carbon atoms include alkenyl groups such as a butyl group, a propenyl group, an aryl group, a cyclohexenyl group and an oleyl group.
- Examples of the dioxolane compound represented by the general formula (11) include 2_alkyl-1,3-dioxolane having an alkyl group having 1 to 30 carbon atoms (for example, 2_hexyl-1,3-dioxolan, 2_heptinole).
- It also has an ether bond, an ester bond or a hydrocarbon group having 130 carbon atoms including a hydroxyl group.
- Examples of the two compounds include 2-alkyl-14-alkanol-1,3-dioxolane [for example, 2_ (2-otatyldodecyl) -a, i3_glycerin formal and the like].
- Dioxolani conjugates having a group in the side chain are preferred.
- dioxolane compound represented by the above general formula (12) there are 2_hexylol 2′-methyl-1,3-dioxolane, 2_heptinole-1, 2′-methinole-1,3-dioxolane, and 2-octinole-1 ′.
- the dioxane conjugate represented by the above general formula (13) includes 2_alkyl-11,3_dioxane having a straight-chain hydrocarbon group having 1 to 30 carbon atoms, and 2-alkene-2-1, 3-dioxane, 2_alkyl-1,3-dioxane and 2_alkenyl-1,3-dioxane having a branched hydrocarbon group having 1 to 30 carbon atoms, an alkyl group is bonded to the 2-position, and 4- or Z- and 6- Examples include 1,3-dioxane compounds in which a hydrocarbon group having a carbon number of 110 to 130, such as an ether bond, an ester bond, or a hydroxyl group is bonded.
- Examples of the dioxane conjugate represented by the above general formula (14) include 2-alkyl-11,4-dioxane having a straight-chain hydrocarbon group having 130 carbon atoms and 2-alkane-1,4-dioxane.
- Examples include 1,4-dioxane compounds having a hydrocarbon group having a prime number of 130, such as an ether bond, an ester bond, or a hydroxy group.
- the compounding amount of these compounds in the lubricating oil composition is 1% by mass or more based on the composition, and can be appropriately adjusted according to the processing method and processing conditions. For example, in the case of cold rolling of pure copper, etc., about 115% by mass is appropriate, and in the case of drawing a copper tube, about 5-30% by mass is preferable.
- the lubricating oil composition of the present invention has the following general formula (I) in order to prevent the acetal bond from being hydrolyzed by a trace amount of chloride ions present in the base oil or a trace amount of water mixed during processing. It is preferable to contain one or more of the 2,2-dialkylepoxide compounds represented by 15) in an amount of 0.01% by mass or more based on the composition. The upper limit of the addition amount is usually about 5% by mass. [0056]
- R 39 and R 4 ° each independently include a saturated hydrocarbon group having 130 to 130 carbon atoms, an unsaturated hydrocarbon group having 130 to 130 carbon atoms, and an ether bond, an ester bond or a hydroxy group. Represents a group selected from hydrocarbon groups having 1 to 30 carbon atoms.
- Examples of the compound represented by the general formula (15) include 2-octyl-1,2-epoxide dodecane.
- the lubricating oil composition of the present invention may contain benzotriazole and / or a derivative thereof, which is known as a copper-based metal stabilizer, in an amount of 0.01 to 10% by mass based on the composition. This content is preferably 0.055% by mass. When the content is 0.01% by mass or more, the effect of addition is obtained, and when the content is 10% by mass or less, the composition is easily dissolved.
- Benzotriazonole is a compound represented by the following formula (16).
- R represents an alkyl group having 1 to 4 carbon atoms.
- A is a number of 1 to 3.
- R 42 and R 43 each independently represent an alkyl group having 14 to 14 carbon atoms.
- B is a number from 0 to 3.
- R represents an alkyl group having 114 carbon atoms
- R 45 represents a methylene group or an ethylene group
- R 46 and R 47 each independently represent a hydrogen atom or an alkyl group having 11 to 12 carbon atoms.
- the organic layer was subjected to vacuum distillation to obtain 2.5 kg of a fraction (decene dimer) having a boiling point of 120 125 ° C, Z26.7 Pa (0.2 Torr).
- this fraction was analyzed by gas chromatography, the dimer concentration was 99% by mass, and the vinylidene olefin ratio in the dimer was 97% by mass.
- the purity of the 2-long-chain branched alkyl 1,3, -dioxolane compound thus improved can be reduced to 1 H_NMR, 13 C—NMR, two-dimensional NMR (2D—COSY: Correlation Spectroscopy / 2D-HMQC: Hetero Nuclear). Analysis was performed using Multi Quantum Coherence / 2D—INA DEQUATE: Incredible Natural Abundance Double Quantum Transfer Experiment, and the structure of 1,3_dioxolane compounds was ascertained.
- FIG. 1 shows the sign of the hydrogen atom of the 1,3-dioxolane compound by NMR analysis
- FIG. 2 shows the sign of the carbon atom of the 1,3-dioxolane compound by 13 C-NMR analysis.
- FIG. 3 is a data profile of ifi-NMR and shows a chemical shift of a hydrogen atom.
- FIGS. 4 and 5 are 13 C-NMR data profiles showing the chemical shifts of carbon atoms.
- ' ⁇ - ⁇ MR (Fig. 3) also shows the coupling value of each proton (hydrogen atom).
- FIG. 7 is a diagram showing an analysis result by the 2D-HMQC method. From Fig. 7, it can be seen that the CH carbon in (1) is spin-coupled to a (lH). Also, the CH carbon in (2) is b (2H) and c (2H)
- FIG. 8 is a diagram showing an analysis result by the 2D-HMBC method. From Fig. 8, the (1) CH carbon has remote spin coupling with b and c protons (), and the (2) CH carbon has remote spin coupling with a proton and ( 3 J)
- FIG. 9 is a diagram showing an analysis result by 2D-HMBC.
- Figure 9 shows that the CH carbon in (11)
- FIG. 10 is a diagram showing an analysis result by 2D-INADEQUATE. From Fig. 10, the (1) CH carbon is bonded to the (3) CH carbon, and the (14) CH carbon is bonded to the (13) CH carbon.
- FIG. 11 is a diagram showing an analysis result by the 2D-INADEQUATE method. From Fig. 11, the CH carbon in (3) is bonded to the CH carbon in (11). The (11) CH carbon is linked to the (12) CH carbon.
- FIG. 12 is a partially enlarged view of FIG.
- reaction product was distilled under reduced pressure, and 112 g of a fraction at 125 135 ° C. [degree of reduced pressure of 13.3 Pa (0.1 Torr)] (crude yield: 56%) was collected.
- this fraction was analyzed by gas chromatography,
- a lubricating oil composition for metal working was prepared by blending 15 parts by mass of butyl stearate with 85 parts by mass of polyisobutylene as described above.
- the lubricating oil properties of these lubricating oil compositions were evaluated in the following manner.
- the coefficient of friction was 0.10 for the lubricating oil composition containing the 2-long chain branched alkyl-1,3-dioxolane compound.
- a lubricating oil composition containing butyl stearate was 0.28. From this result, it can be seen that 2_ long-chain branched alkyl-1,3-dioxo It can be seen that the lubricating oil composition containing the orchid compound has a remarkably improved coefficient of friction and is suitable as a lubricating oil composition for metal working.
- Example 1 (1) 1-hexene was used in place of 1-decene, and a hexene dimer was synthesized in the same manner as in Example (1), and this hexene dimer was used.
- 2-butyl-1,2-epoxyoctane was synthesized.
- Example 1 (3) 2-butyl-1,2-epoxy octane was used in place of 2-otachinolate 1,2-epoxidedodecane, and the method was repeated in the same manner as in Example 1 (3).
- (2-Butylheptyl) 1-1,3-dioxolan was obtained.
- Example 1 In Example (1), 1-otaten was used in place of 1-decene, and an otaten dimer was synthesized in the same manner as in Example (1). 1 2-Hexyl-1,2-epoxydecane was synthesized in a similar manner to (2). Then, in Example 1 (3), 2_hexyl-1,2-epoxyside decane was used in place of 2-otatinole 1,2_epoxide decane. —Hexylnonyl-1,3-dioxolane was obtained.
- Example 1 (3) instead of ethylene glycol, glycerin was used. ) was obtained in a similar manner as described in (2) (2-Octylpandecyl) -a, i3-glycerol formal.
- Example 1 (3) 2-octylone-1,2-epochidodecane was used instead of 2-octyl-1,2-epoxidedodecane.
- 2_ 2-Otaturdindecyl-1,3-Dioxolan was obtained.
- a lubricating oil composition The types and amounts of the components shown in Table 1 were mixed to prepare a lubricating oil composition.
- the resulting lubricating oil composition was subjected to a reciprocating friction test and a flat plate pull-out test under the following conditions, and the lubricating properties were evaluated.
- the results of the reciprocating friction test are shown in Figure 13-16, and the results of the flat plate pull-out test are shown in Table 1.
- Fig. 13 and Fig. 14 show the variation of the average friction coefficient with temperature up to the 1st to 5th sliding
- Figs. 15 and 16 show the variation of the average friction coefficient with the temperature up to the 45th sliding. Show.
- Evaluation items Number of sliding times 11 Average friction coefficient up to 5 times and number of sliding times 45 Average friction coefficient up to 50 times
- Press machine 150 ton press machine (Burrak)
- Stroke speed 0.5m / sec.
- Forming hole shape 6.35 / 20.32mm (2.5 8 inches) (circular)
- Rolling mill 4-high rolling mill
- a lubricating oil thread composition particularly suitable as a copper pipe drawing oil can be provided.
- the lubricating oil composition for metal working of the present invention has excellent lubricating properties (low friction) even in a high-temperature region, and is particularly suitable for processing copper-based metals (copper or copper-containing metals). .
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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US10/590,603 US7838692B2 (en) | 2004-02-25 | 2005-02-22 | Alkyl acetal compound, process for producing the same, and lubricating oil composition |
JP2006510281A JP4926698B2 (ja) | 2004-02-25 | 2005-02-22 | アルキルアセタール化合物とその製造方法及び潤滑油組成物 |
KR1020067017081A KR101173707B1 (ko) | 2004-02-25 | 2005-02-22 | 알킬 아세탈 화합물과 그의 제조방법 및 윤활유 조성물 |
CN2005800056133A CN1922125B (zh) | 2004-02-25 | 2005-02-22 | 烷基缩醛化合物、制备该化合物的方法以及润滑油组合物 |
US12/421,428 US8158564B2 (en) | 2004-02-25 | 2009-04-09 | Alkyl acetal compound, process for producing the same, and lubricating oil composition |
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JP2004049093 | 2004-02-25 | ||
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JP2004049180 | 2004-02-25 |
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US10/590,603 A-371-Of-International US7838692B2 (en) | 2004-02-25 | 2005-02-22 | Alkyl acetal compound, process for producing the same, and lubricating oil composition |
US12/421,428 Division US8158564B2 (en) | 2004-02-25 | 2009-04-09 | Alkyl acetal compound, process for producing the same, and lubricating oil composition |
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JP (1) | JP4926698B2 (ja) |
KR (2) | KR101173707B1 (ja) |
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WO2007119400A1 (ja) * | 2006-03-31 | 2007-10-25 | Idemitsu Kosan Co., Ltd. | 潤滑油添加剤、それを含有する潤滑油組成物、各種低摩擦摺動部材、転がり軸受およびすべり軸受 |
WO2008153015A1 (ja) * | 2007-06-11 | 2008-12-18 | Idemitsu Kosan Co., Ltd. | 清浄分散剤、潤滑剤用添加剤組成物及び潤滑油組成物 |
WO2009019941A1 (ja) * | 2007-08-08 | 2009-02-12 | Idemitsu Kosan Co., Ltd. | 耐摩耗剤、潤滑剤用添加剤組成物及び潤滑油組成物 |
JP2013543047A (ja) * | 2010-11-22 | 2013-11-28 | シェブロン・オロナイト・カンパニー・エルエルシー | 摩耗防止添加剤として1,3−ジオキソラン−4−メタノール化合物を含有する潤滑組成物 |
WO2017164124A1 (ja) * | 2016-03-24 | 2017-09-28 | 出光興産株式会社 | 2位に分岐構造を有するエーテル系基油の製造方法、冷凍機油組成物の製造方法及び潤滑油組成物の製造方法 |
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RU2015122800A (ru) | 2012-11-16 | 2017-01-10 | Басф Се | Смазывающие композиции, содержащие эпоксиды для улучшения совместимости с фторполимерным уплотнением |
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CN115161100A (zh) * | 2022-07-29 | 2022-10-11 | 宁波金田铜管有限公司 | 一种用于铜管成型的润滑油及铜管 |
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WO2009019941A1 (ja) * | 2007-08-08 | 2009-02-12 | Idemitsu Kosan Co., Ltd. | 耐摩耗剤、潤滑剤用添加剤組成物及び潤滑油組成物 |
JP2009040869A (ja) * | 2007-08-08 | 2009-02-26 | Idemitsu Kosan Co Ltd | 耐摩耗剤、潤滑剤用添加剤組成物及び潤滑油組成物 |
US8841242B2 (en) | 2007-08-08 | 2014-09-23 | Idemitsu Kosan Co., Ltd. | Anti-wear agent, additive composition for lubricant, and lubricant composition |
JP2013543047A (ja) * | 2010-11-22 | 2013-11-28 | シェブロン・オロナイト・カンパニー・エルエルシー | 摩耗防止添加剤として1,3−ジオキソラン−4−メタノール化合物を含有する潤滑組成物 |
WO2017164124A1 (ja) * | 2016-03-24 | 2017-09-28 | 出光興産株式会社 | 2位に分岐構造を有するエーテル系基油の製造方法、冷凍機油組成物の製造方法及び潤滑油組成物の製造方法 |
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JPWO2005080305A1 (ja) | 2007-10-25 |
JP4926698B2 (ja) | 2012-05-09 |
KR101173707B1 (ko) | 2012-08-13 |
US20090270288A1 (en) | 2009-10-29 |
CN101955837B (zh) | 2012-10-10 |
KR20120034744A (ko) | 2012-04-12 |
KR20060132915A (ko) | 2006-12-22 |
TW200540143A (en) | 2005-12-16 |
CN101955837A (zh) | 2011-01-26 |
US20080234152A1 (en) | 2008-09-25 |
US7838692B2 (en) | 2010-11-23 |
CN1922125A (zh) | 2007-02-28 |
US8158564B2 (en) | 2012-04-17 |
CN1922125B (zh) | 2010-12-01 |
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