Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
  • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
  • C10L1/2418—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides containing a carboxylic substituted; derivatives thereof, e.g. esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
• • 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
  • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
  • C10M135/20—Thiols; Sulfides; Polysulfides
  • C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M135/26—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
• • 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
  • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
• • 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
  • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Definitions

• Lubricating oil and fuel oil additives lubricating oil compositions and fuel oil compositions
• the present invention relates to a lubricating oil and fuel oil additive, and a lubricating oil composition and a fuel oil composition. More specifically, the present invention relates to a friction modifier, particularly an extreme pressure additive, which is used for lubricating oils and fuel oils containing as a main component a disulfide compound having a specific structure having an excellent function as an antiwear agent. The present invention also relates to a lubricating oil composition and a fuel oil composition each containing the above-mentioned additives. Background art
• lubricating oil has been used in internal combustion engines, drive systems such as automatic transmissions, shock absorbers, and power steering to facilitate their operation. It is well known that lubricating performance is initially insufficient, and the lubricated surface friction and wear occurs, eventually causing seizure. Therefore, lubricating oils containing extreme pressure additives and antiwear agents are used. However, conventional extreme pressure additives are not always satisfactory because they do not exhibit sufficient anti-seizure effects due to interaction with other additives, corrode metals, or have poor abrasion resistance. It was not.
• Metal working oils used for metal working such as cutting, grinding or plastic working include mineral oils and synthetic hydrocarbon oils, and alcohols. It is prepared by blending oily agents such as oils, fatty acid esters, and fatty acids and extreme pressure additives, and attempts have been made to improve processability.
• an oil agent obtained by adding an active-containing olefin sulfide and an overbased sulfonate to a base oil is commercially available.
• metalworking oils have good resistance to welding and have the ability to prevent abnormal wear (for example, chipping) of tools and peeling of machined surfaces.
• abnormal wear for example, chipping
• machining with relatively low load friction corrosion and wear of the tool due to active erosion progress, shortening the time until tool replacement or re-polishing, often hindering production efficiency.
• metal processing in which abnormal wear is not a problem from the beginning, often led to a reduction in production efficiency.
• hydraulic oil is a power transmission fluid used for operations such as power transmission, force control, and shock absorption in hydraulic systems such as hydraulic equipment and devices, and also functions to lubricate sliding parts. .
• gear oils especially gear oils for automobiles
• extreme pressure additives or anti-wear additives such as sulfurized oils and fats, sulfided olefins, phosphoric acid dithiophosphoric acid compounds, and zinc dithiophosphate have been mainly blended with lubricating base oils.
• further reduction in wear resistance, oxidation stability, and wear coefficient ratio (low speed Z high speed) are required.
• sulfur-based extreme pressure additives have been frequently used as extreme pressure additives for lubricating oils.
• This sulfur-based extreme pressure additive has a sulfur atom in the molecule and is dissolved or uniformly dispersed in the base oil to exert an extreme pressure effect.
• sulfurized fats and oils, sulfurized fatty acids, sulfurized esters, polysulfides, sulfided olefins, thiocarbamates, thioterpenes, and dialkylthiodipropionates are known.
• these sulfur-based extreme pressure additives corrode metals, do not exhibit sufficient seizure prevention effects due to interaction with other additives, or have insufficient abrasion resistance However, it was not always satisfactory.
• 19 and 1 ° are each a hydrocarbon group having 1 to 20 carbon atoms
• a 5 and A 6 are each a hydrocarbon group having 0 to 20 carbon atoms
• X is an integer of 1 to 6.
• the compound of the general formula (VII) is composed of a chlorinated ester such as a monomethyl acetate and a polysulfide. Since it is produced by reacting with tritium, it is inevitable that the mixture will be a mixture of monosulfide, disulfide, and trisulfide or higher polysulfide.
• a chlorinated ester such as a monomethyl acetate and a polysulfide. Since it is produced by reacting with tritium, it is inevitable that the mixture will be a mixture of monosulfide, disulfide, and trisulfide or higher polysulfide.
• the divalent hydrocarbon groups tables in A 5 ⁇ Pi A 6, Les describes the number of carbon atoms, in Runomi, any description is not made for that structure, any good Una structure It is not entirely clear if one is preferred. Disclosure of the invention
• the present invention provides a Sulfur-based extreme pressure additives used for lubricating oils and fuel oils, which have excellent load-bearing capacity and wear resistance and low corrosiveness to non-ferrous metals, and lubricating oil compositions containing the additives And a fuel oil composition.
• the present inventors have conducted intensive studies to achieve the above object, and as a result, the object can be achieved by a lubricant and fuel oil additive containing a disulfide compound having a specific structure as a main component. I found that.
• the present invention has been completed based on such findings.
• R 1 ⁇ Pi R 2 each independently represent an oxygen atom, a sulfur atom, or human Dorokarubiru group for the nitrogen atom optionally containing an carbons 1 be ⁇ 3 0.
• a 1 and A 2 Each is independently a group represented by CR 3 R 4 , wherein R 3 and R 4 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms, and X represents 2.
• An additive for lubricating oil comprising a disulfide compound represented by the following formula: 2.
• R 1 is a hydrocarbyl group having 1 to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom
• a 1 is a group represented by CR 3 R 4 , R 3 and R 4 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms.
• R 2 OOC -A 2 -SH (III) (Wherein, R 2 is a hydrocarbyl group having 1 to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom, A 2 is a group represented by CR 3 R 4 , 3 and R 4 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms.)
• a lubricating oil additive comprising a disulfide compound as a main component obtained by oxidatively coupling the mercaptoalkanecarboxylic acid ester represented by
• R 1 and R 2 are each independently a hydrocarbyl group having 1 to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom.
• a 3 and A 4 are each And each independently represents a group represented by CR 5 R 6 —CR 7 R 8 , wherein R 5 to R 8 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms, and X represents 2.
• R 1 is a hydrocarbyl group having ⁇ to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom
• a 3 is represented by CR 5 R 6 — CR 7 R 8
• R 5 to R s are each independently hydrogen or a hydrocanoleville group having 1 to 20 carbon atoms.
• R 2 is a hydrocarbyl group having 1 to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom
• a 4 is CR 5 R 6 — CR 7 A group represented by R 8 , wherein R 5 to R 8 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms.
• a lubricating oil additive mainly comprising a disulfide compound obtained by oxidizing the mercaptoalcarboxylic acid ester represented by
• R 1 and R 2 are each independently a hydrocarbyl group having 1 to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom.
• R 1 and 2 are each independently a group represented by CR 3 R 4 , R 3 and R 4 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms, and X is 2 Is shown.
• R 1 is a hydrocarbyl group having 1 to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom, and A ! Is a group represented by CR 3 R 4 , R 3 and R 4 are each independently hydrogen or carbon number 1 to 20 Is a hydrocarbyl group.
• R 2 is a hydrocarbyl group having 1 to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom
• a 2 is a group represented by CR 3 R 4 , 3 and R 4 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms.
• a fuel oil additive mainly comprising a disulfide compound obtained by oxidative coupling of a mercaptoalkanecarboxylic acid ester represented by the formula:
• R 1 and R 2 are each independently a hydrocarbyl group having 1 to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom.
• a 3 and A 4 are each And each independently represents CR 5 R 6 —CR 7 R 8 , wherein R 5 to R 8 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms, and X represents 2.
• a fuel oil additive comprising a disulfide compound represented by the following formula: 10.
• R 1 is a hydrocarbyl group having 1 to 30 carbon atoms which may contain an oxygen atom, a sulfur atom, or a nitrogen atom
• a 3 is represented by CR 5 R 6 — CR 7 R 8
• R 5 to R 8 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms.
• R 2 OOC -A 4 -SH (VI)
• R 2 is a carbon number which may contain an oxygen atom, a sulfur atom, or a nitrogen atom: a hydrocarbyl group of from 30 to 30, and A 4 is represented by CR 5 R 6 — CR 7 R 8 R 5 to R 8 are each independently hydrogen or a hydrocarbyl group having 1 to 20 carbon atoms.
• a lubricating oil composition comprising: (A) a lubricating base oil; and (B) the lubricating oil additive according to any one of 1 to 6 above.
• a fuel oil composition comprising: (X) a fuel oil; and (Y) the fuel oil additive according to any one of the above items 7 to 12.
• the compound represented by the general formula (I) used in the lubricating oil and fuel oil additives of the present invention has the following structure
• R 1 and R 2 are each independently a hydrocarbyl group having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 2 to 18 carbon atoms, particularly Hydrocarbyl groups having 3 to 18 carbon atoms are preferred.
• the hydrocarbyl group may be linear, branched, or cyclic, and may contain an oxygen atom, a sulfur atom, or a nitrogen atom.
• the R 1 and R 2 may be mutually identical, but may be different, for manufacturing reasons, arbitrary preferable to be identical.
• a 1 and A 2 are each independently a group represented by CR 3 R 4
• R 3 and R 4 are each independently hydrogen represented by a monovalent hydrocarbyl group having 1 to 20 carbon atoms. It is.
• the hydrocarbyl group preferably has 1 to 12 carbon atoms, and more preferably has 1 to 8 carbon atoms.
• a 1 and A 2 specifically a methylene group, Echiriden group, propylidene group, and the levator Gerare, among them a methylene group is particularly preferred.
• X is 2.
• the content of the polysulfide in which X in the general formula (I) is 3 or more is a compound represented by the general formula (I) (X is 2) 30% by mass based on the total amount of The following is preferred.
• the content of the polysulfide compound having X of 3 or more is more preferably 10% by mass or less, and particularly preferably 5% by mass or less.
• the disulfide compound represented by the general formula (I) it is important to adopt a method in which the by-product amount of the polysulfide compound having X of 3 or more is in the above range. It is.
• Oxidative coupling is carried out using the carboxylic acid ester represented by the following formula. According to such a production method, by-products of polysulfide compounds higher than trisulfide are substantially not generated.
• oxidizing agent examples include oxygen, hydrogen peroxide, halogen (iodine, bromine), hypohalous acid (salt), sulfoxide (dimethylsulfoxide, diisopropylpropylsulfoxide), and manganese oxide (IV).
• oxygen, hydrogen peroxide, and dimethyl sulfoxide are preferable because they are inexpensive and easy to produce disulfide.
• the compound represented by the general formula (IV) used for the lubricating oil and fuel oil additives of the present invention has the following structure:
• R 1 ⁇ Pi R 2 are the same as your Keru R 1 and R 2 in the general formula (I).
• R 1 and R 2 may be the same or different, but are preferably the same for manufacturing reasons.
• a 3 and A 4 are each independently a group represented by CR 5 R 6 —CR 7 R 8 , wherein R 5 to R 8 are each independently hydrogen or a group having 1 to 20 carbon atoms.
• a hydrocarbyl group Those having carbon numbers of ⁇ to ⁇ 2, and more preferably those having 1 to 8 carbon atoms are preferred.
• a 3 and A 4 may be mutually identical or may be different, for manufacturing reasons, and this is preferably the same.
• X is 2.
• the content of the polysulfide in which X is 3 or more in the general formula (IV) is a compound represented by the general formula (IV) (where X is 2). ) Is preferably 30% by mass or less based on the total amount. When the content is 30% by mass or less, corrosiveness to nonferrous metals can be sufficiently suppressed.
• the content of the polysulfide compound in which X is 3 or more is more preferably 10% by mass or less, and particularly preferably 5% by mass or less.
• Oxidative coupling is performed using a mercaptan carboxylic acid ester represented by the following formula. According to such a production method, by-products of a polysulfide compound higher than trisulfide are substantially not generated.
• R 2 OOC ⁇ A 4 - S 2 -A 4 - C ⁇ R 2 is manufactured ⁇
• the oxidizing agent used to produce the corresponding disulfide by oxidizing the mercaptocarboxylic acid ester can be used.
• Oxidizing agents include oxygen, hydrogen peroxide, halogens (iodine and bromine), hypohalous acid (salt), sulfoxide (dimethyl sulfoxide, diisopropyl sulfoxide), and manganese oxide (IV). And the like.
• oxygen, hydrogen peroxide, and dimethyl sulfoxide are preferred because of their low cost and easy production of disulfide.
• disulfide compound represented by the above general formula (IV) examples include 1,1—bis (2-methoxycanoleponinoleethyl) disulfide and 1,1bis (2—ethoxycanolepo- Nolechinole) disulfide, 1,1bis (2_ ⁇ -propoxycanolepo-noletinole) disulfide, 1,1bis (2—isopropoxycarboninoleetinole) disnosulfide, 1,1bis (2 —Cyclopropoxycanoleboenolechinole) disulfide, 1,1bis (2—methoxycarburyl ⁇ —propyl) disnorefide, 1,1—bis (2—methoxycarboninole ⁇ —Petinole) Disulphide, 1,1-bis (2-methoxycanoleponinole ⁇ -hexyl) Disulphide, 1,1bis (2—Methoxycarbinole- ⁇ —P Pill) disulfide,
• These disulfide compounds are load-bearing as sulfur-based extreme pressure additives. It has excellent versatility and abrasion resistance, and is used as an additive for lubricating oil and fuel oil.
• the disulfide compound represented by (I) and / or the disulfide compound represented by the general formula (IV) may contain one kind or two or more kinds.
• the lubricating oil composition of the present invention, and (A) a lubricating base oil is one that contains a lubricant additive comprising (B) the aforementioned disulfide compounds
• Oil compositions include internal combustion engines, drive systems such as automatic transmissions, shock absorbers, and power steering; automotive lubricating oils used for gears; metal processing such as cutting, grinding, and plastic working. Includes metal working oils used for metalworking, hydraulic fluids used in hydraulic systems such as hydraulic equipment and devices, power control, and hydraulic fluids that are also used as power transmission fluids for damping and other operations.
• the lubricating oil base oil used as the component (A) is not particularly limited, and may be selected from mineral oils and synthetic oils according to the purpose and conditions of use of the composition. Appropriately selected from among them.
• the mineral oil for example, a distillate obtained by distilling a paraffin-based crude oil, an intermediate-base crude oil or a naphthenic-based crude oil under normal pressure, or a residual oil obtained by distillation under normal pressure under reduced pressure, Or, refined oils obtained by refining them according to a conventional method, specifically, refined oils of solvent, refined hydrogenated oils, dewaxed oils, and clay treated oils may be mentioned.
• Examples of synthetic oils include low-molecular-weight polybutene, low-molecular-weight polypropylene, ⁇ -olefin oligomers having 8 to 14 carbon atoms, and Esters such as polyol hydrides (such as fatty acid esters of trimethylol pulp and fatty acid esters of pentaerythritol), dibasic acid esters, aromatic polycarboxylic acid esters, and esterol phosphates Examples thereof include alkyl aromatic compounds such as danield products, anolequinolebenzene, and anolequinolenaphthalene, polyglycol oils such as polyalkylene glycol, and silicone oil.
• Esters such as polyol hydrides (such as fatty acid esters of trimethylol pulp and fatty acid esters of pentaerythritol), dibasic acid esters, aromatic polycarboxylic acid esters, and esterol phosphates
• alkyl aromatic compounds such as danield products, anole
• One of these base oils may be used, or two or more of them may be used in an appropriate combination.
• the content of the lubricating oil additive of the component (B) in the lubricating oil composition of the present invention is appropriately selected according to the purpose and conditions of use of the composition.
• the range is 0% by mass.
• the additive alone may be used.
• it is usually selected in the range of 0.1 to 60% by mass, preferably 0.1 to 50% by mass.
• various additives for example, other friction modifiers (oiliness agents, other extreme pressure additives) ⁇ ⁇ antiwear agents, ashless dispersants, metal cleaning agents , A viscosity index improver, a pour point depressant, an antioxidant, a metal corrosion inhibitor, an antifoaming agent, a surfactant, an antioxidant, and the like.
• friction modifiers and antiwear agents include, for example, sulfur-based compounds such as olefin sulfide, dialkyl alkyl polysulfide, dialkyl alkyl polyphenol, and diaryl polysulfide, phosphoric acid esters, and sulfide.
• sulfur-based compounds such as olefin sulfide, dialkyl alkyl polysulfide, dialkyl alkyl polyphenol, and diaryl polysulfide, phosphoric acid esters, and sulfide.
• Acid ester, estenol phosphite, alkylhydrogenphos Phosphorus compounds such as phyto, phosphoric acid ester amine salts, phosphorous acid ester amine salts, chlorinated fats and oils, chlorinated paraffins, chlorinated fatty acid esters, chlorinated fatty acid esters and other alkyl compounds
• ester compounds such as alkyl or alkenyl succinic acid ester, or organic compounds such as alkyl or alkenyl succinic acid, alkyl or alkenyl succinic acid, naphthenate, Organic compounds such as zinc dithiophosphate (Zn DTP), zinc dithiophosphate zinc zinc (Zn DTC), oxymolybdenum sulphide, organodiphospho-dithioate (Mo DTP), oxymolybdenum pudendithiocarbamate (Mo DTC) Metallic compounds and the like can be mentioned.
• Typical examples of ashless dispersants include succinic imids, boron-containing succinic imids, benzylamines, boron-containing benzylamines, succinic esters, fatty acids and succinic acid.
• the metal-based detergent include neutral metal sulfonates, neutral metal phosphates, neutral metal salicylates, and the like. Neutral metal phosphonates, basic sulfonates, basic phenates, basic salicylates, basic phosphonates, overbased sulfonates, overbased phenates, overbased salicylates, overbased phosphonates And the like.
• viscosity index improver examples include polymethacrylate, dispersed polymethacrylate, an olefin copolymer (for example, an ethylene-propylene copolymer, etc.), and a dispersed olefin copolymer.
• polymers, styrene-based copolymers (eg, styrene-gen hydrogenated copolymers), etc., and pour point depressants include, for example, polymethacrylate. I can do it.
• alkenyl succinic acid or its partial ester may be used as an antioxidant
• benzotriazole, benzimidazonole, benzothiazonole, thiadiazole, etc. may be used as metal corrosion inhibitor, for example.
• the defoaming agent for example, dimethylpolysiloxane, polyacrylate and the like are used
• surfactant for example, polyoxyethylene alkylphenyl ether and the like are used.
• antioxidants examples include an amine antioxidant such as alkylated diphenylamine, phenyl-1-a-naphthylamine, and alkylated naphthinoreamin; 2,6-di-tert-butylcresol; Examples include phenolic antioxidants such as 4, -methylenebis (2,6-di-t-butylphenol).
• the lubricating oil composition of the present invention can be used for, for example, automotive lubricating oils used in internal combustion engines, drive systems such as automatic transmissions, shock absorbers, power steering, gears, etc., such as cutting, grinding, and plastic working.
• Metalworking oil used for metalworking, power transmission in hydraulic systems such as hydraulic equipment and devices, power control used for actuation of damping, etc. Used as hydraulic fluid.
• the fuel oil composition of the present invention contains (X) a fuel oil and (Y) a fuel oil additive containing the above-mentioned disulfide compound.
• a highly hydrorefined fuel oil for example, a high-performance turbine fuel oil, is preferably used as the component (X).
• the fuel oil composition of the present invention contains the fuel oil additive (Y).
• the weight is usually in the range from 0.01 to 100 mass 111, preferably from 0.01 to 100 mass ppm.
• additives can be appropriately compounded as necessary.
• additives include antioxidants such as phenylenediamine, diphenylamine, alkylphenol, and amidephenol, and detergents such as polyetheramine and polyalkylamine.
• Metal deactivators such as Schiff-type compounds and thioamide-type compounds; surface ignition inhibitors such as organic phosphorus compounds; anti-freezing agents such as polyhydric alcohols and ethers; Antioxidants such as earth metal salts, sulfuric acid esters of higher alcohols, such as sulfuric acid esters of higher alcohols, aionic surfactants, cationic surfactants, amphoteric surfactants, etc .; Known fuel oil additives such as discriminants such as quinizarin and coumarin, odorants such as natural essential oils and synthetic flavors, and coloring agents such as azo dyes. . . Example
• the coefficient of friction, wear scar diameter, and corrosiveness of the lubricating oil composition were determined according to the methods described below.
• the Soda four-ball test was performed under the following conditions.
• each hydraulic load [0.5, 0. 7, 0. 9, 1. 1 , 1. 3, 1. 5 kgf / cm 2 (XO. 0 9 8 0 7 MP a) while holding] 1 8 0 seconds, will stepwise raised load
• the test was performed for 180 seconds, the friction coefficient under each load was determined, and the diameter of the friction scar was measured according to the test termination law.
• Production Example 2 Bis (n-butoxycarbonylmethyl) disulfide was oxidized in the same manner as in Production Example 1 except that n-butyl mercaptoacetate of bis (1-butoxycarbolmethyl) disulfide was used to produce bis (n-butoxycarbonylmethyl) disulfide. did. No trisulfide or higher polysulfide was found in this compound.
• Production Example 3 Production of bis (n-octoxycarbonylmethyl) disulfide
• Oxidation was carried out in the same manner as in Production Example 1 except that ethyl ⁇ -mercaptopropionate was used to produce 1,1-bis (1-ethoxycarbonylethyl) disulphide. In this compound, no polysulfide higher than trisulfide was found. Comparative Production Example 1 Production of bis ( ⁇ -butoxycarbonylmethyl) polysulfide
• Bis ( ⁇ -butoxycarbonylmethyl) polysulfide was produced by producing sodium and sodium polysulfides from sodium sulfide and sulfur, and then reacting with sodium ⁇ -butyl acetate.
• the sulfur flatness of sodium polysulfide Na 2 S x
• the molar ratio between sodium sulfide and sulfur was adjusted so that the average number (x) was 2.
• sodium polysulfide was used in an excess of 5% so that n-butyl acetate was not remained.
• the reaction was carried out according to the following method to produce bis (n-butoxycarboermethyl) polysulfide.
• O g of sulfonic acid monohydrate was added, and the mixture was heated and refluxed for 5 hours. After cooling, separate the reaction mixture onto a separatory funnel. And washed twice with an aqueous solution of sodium hydrogencarbonate and then five times with water. Toluene was distilled off under reduced pressure to obtain 12.0 g of bis (2-ethylhexyloxyboninolemethynole) snoresulfide.
• Example 1 was carried out in the same manner as in Example 1 except that the bis (2-ethylhexyloxycarbonylmethyl) sulfide obtained in Comparative Production Example 1 was used. The results are shown in Table 1. Comparative Example 2
• Example 1 the bis (n-ptoxica) obtained in Comparative Production Example 2 was used. (Rubonylmethylene) The procedure was the same as in Example 1, except that polysulfide was used. The results are shown in Table 1. Comparative Example 3
• a-Ethyl mercaptopropionate was oxidized with dimethyl sulfoxide according to the method shown below to produce 1,1-bis (2-ethoxycarbonylylethyl) disulfide. No polysulfide higher than trisulfide was found in this compound.
• the 1,1-bis (2-ethoxycarbonyldiethyl) disulfide obtained in Production Example 8 was combined with a mineral oil P 500 ON of a 500 neutral fraction (100 ° C. kinematic viscosity of 10.9 ° C.). mm 2 / s,% CA 0.1 or less) to prepare a lubricating oil composition by adding 1% by mass based on the total amount of the composition, and evaluated the performance. The results are shown in Table 1.
• Example 8 was carried out in the same manner as in Example 8, except that 1,1-bis (2-2-ethylhexoxycarbonylethyl) disulfide obtained in Production Example 9 was used. The results are shown in Table 2.
• the lubricating oil composition using the additive of the present invention has a small wear scar diameter and extremely high load resistance and wear resistance.
• a non-ferrous metal is used in comparison with Comparative Example 1, when a lubricant additive having a high content of a polysulfide compound in which X in the general formula (I) and the general formula (IV) is 3 or more is used. It shows that the lubricating oil composition of the present invention has a low corrosiveness to non-ferrous metals, and is very good, whereas the lubricating oil composition of the present invention has a low corrosiveness.
• ADVANTAGE OF THE INVENTION compared with the conventional sulfur type extreme pressure additive, it has excellent load-bearing performance and abrasion resistance, and has a low corrosiveness to non-ferrous metals. It is possible to provide a sulfur-based extreme pressure additive to be used, and a lubricating oil composition and a fuel oil composition containing the additive.

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• 2004
  • 2004-02-04 WO PCT/JP2004/001093 patent/WO2004069966A1/ja active Application Filing
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