Glycerin fatty acid ester composition and lubricating oil composition or fuel oil composition containing the glycerin fatty acid ester composition

Abstract

To provide a glycerin fatty acid ester composition having an excellent friction reducing property.SOLUTION: A glycerin fatty acid ester composition of the present invention comprises an ester of a fatty acid having 12 to 24 carbon atoms and glycerin. A content of monoester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition is 90.0 to 99.8 mass% with respect to a total amount of the glycerin fatty acid ester composition, a content of glyceryl monooleate in the glycerin fatty acid ester composition is 60.0 to 90.0 mass% with respect to the total amount of the glycerin fatty acid ester composition, and an iodine value is 65.0 to 70.0. A provided friction modifier and a provided lubricant or fuel oil composition containing the friction modifier comprise the glycerin fatty acid ester composition.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a glycerin fatty acid ester composition having excellent friction-reducing properties. [Background technology]

[0002] In recent years, concerns about environmental issues such as global warming and air pollution, as well as the depletion of petroleum resources, have led to a demand for improved fuel economy in automobiles. Therefore, reducing friction in engine lubricating oils has become a major challenge, and various friction reducers have been developed and added to engine lubricating oils. Among existing friction modifiers, organomolybdenum compounds are generally well known for their high friction-reducing effect (Patent Documents 1 and 2). It is said that organomolybdenum compounds exert their friction-reducing effect by forming a molybdenum disulfide film, and this effect has been recognized in various lubricating oils, including engine oils. However, organomolybdenum compounds do not exert their friction-reducing effect under all conditions, and depending on the application and purpose, organomolybdenum compounds alone may not exert a sufficient friction-reducing effect.

[0003] To solve these problems, Patent Document 3 describes a lubricating oil composition for internal combustion engines containing a glycerin partial fatty acid ester having a monoester content of at least 90% by mass, and Patent Document 4 describes a lubricating oil composition for internal combustion engines containing a monoglyceride having a hydrocarbon group with 8 to 22 carbon atoms and characterized by a hydroxyl value of 150 to 300 mgKOH / g. However, even when such glycerin-based compounds are added to lubricating oils or fuel oils, a sufficient friction-reducing effect cannot be obtained, and there is still a demand on the market for compounds with excellent friction-reducing properties. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 7-053983 [Patent Document 2] Japanese Patent Application Publication No. 10-017586 [Patent Document 3] Japanese Patent Application Laid-Open No. 2005-082709 [Patent Document 4] Japanese Patent Application Laid-Open No. 2014-025040 Summary of the Invention [Problem to be solved by the invention]

[0005] Therefore, an object of the present invention is to provide a glycerin fatty acid ester composition having excellent friction-reducing properties. [Means for solving the problem]

[0006] As a result of intensive research aimed at solving the above problems, the present inventors discovered that a specific glycerin fatty acid ester composition has excellent friction-reducing properties, leading to the completion of the present invention. That is, the present invention is a glycerin fatty acid ester composition comprising an ester of a fatty acid having 12 to 24 carbon atoms and glycerin, wherein the content of a monoester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition is 90.0 to 99.8 mass% based on the total amount of the glycerin fatty acid ester composition, the content of glyceryl monooleate in the glycerin fatty acid ester composition is 60.0 to 90.0 mass% based on the total amount of the glycerin fatty acid ester composition, and the iodine value is 65.0 to 70.0. [Effects of the Invention]

[0007] The glycerin fatty acid ester composition of the present invention has excellent friction-reducing properties and can provide a useful lubricating oil composition or fuel oil composition. DETAILED DESCRIPTION OF THE INVENTION

[0008] The glycerin fatty acid ester composition of the present invention is a glycerin fatty acid ester composition consisting of an ester of a fatty acid having 12 to 24 carbon atoms and glycerin, and can include, for example, a monoglycerin fatty acid ester, which is a monoester of a fatty acid having 12 to 24 carbon atoms and glycerin; a diglycerin fatty acid ester, which is a diester of a fatty acid having 12 to 24 carbon atoms and glycerin; and a triglycerin fatty acid ester, which is a triester of a fatty acid having 12 to 24 carbon atoms and glycerin. Because glycerin has three hydroxyl groups, glycerin fatty acid monoesters exist in two isomers: one in which the hydroxyl group at the α-position is esterified, and one in which the hydroxyl group at the β-position is esterified. In the present invention, either isomer may be used, or a mixture of these isomers may be used. Furthermore, the fatty acids constituting the diglycerin fatty acid ester and the triglycerin fatty acid ester may be the same or different fatty acids.

[0009] The glycerin fatty acid ester composition of the present invention is a glycerin fatty acid ester composition in which the content of glyceryl monooleate in the glycerin fatty acid ester composition is 60.0 to 90.0 mass% relative to the total amount of the glycerin fatty acid ester composition. From the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, the content of glyceryl monooleate in the glycerin fatty acid ester composition is preferably 65.0 to 88.0 mass%, more preferably 70.0 to 85.0 mass%, and even more preferably 75.0 to 84.0 mass% relative to the total amount of the glycerin fatty acid ester composition. In the present invention, the content of monooleate in the glycerin fatty acid ester composition is calculated from the fatty acid composition ratio of the glycerin fatty acid ester composition determined by the method described in "Standard Test Methods for the Analysis of Fats, Oils, and Related Materials, 2.4.2.3 Fatty Acid Composition (Capillary Gas Chromatography)" of the Japan Oil Chemists' Society.

[0010] Examples of monoesters of glycerin and fatty acids having 12 to 24 carbon atoms other than glyceryl monooleate that can be contained in the glycerin fatty acid ester composition of the present invention include monoesters of linear saturated fatty acids having 12 to 24 carbon atoms and glycerin, monoesters of branched saturated fatty acids having 12 to 24 carbon atoms and glycerin, monoesters of linear unsaturated fatty acids having 12 to 24 carbon atoms and glycerin (excluding glyceryl monooleate), and monoesters of branched unsaturated fatty acids having 12 to 24 carbon atoms and glycerin. Among these, from the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, it is preferable to contain at least one monoester selected from the group consisting of glyceryl monolaurate, glyceryl monomyristate, glyceryl monopalmitate, glyceryl monostearate, glyceryl monoarachidate, glyceryl monobehenate, and glyceryl monolignocerate, it is more preferable to contain at least one monoester selected from the group consisting of glyceryl monomyristate, glyceryl monopalmitate, glyceryl monostearate, and glyceryl monoarachidate, it is even more preferable to contain at least one monoester selected from the group consisting of glyceryl monopalmitate and glyceryl monostearate, and it is particularly preferable to contain glyceryl monopalmitate and glyceryl monostearate.

[0011] Examples of diesters of glycerin and fatty acids having 12 to 24 carbon atoms that can be contained in the glycerin fatty acid ester composition of the present invention include diesters of saturated linear fatty acids having 12 to 24 carbon atoms and glycerin, diesters of saturated branched fatty acids having 12 to 24 carbon atoms and glycerin, diesters of unsaturated linear fatty acids having 12 to 24 carbon atoms and glycerin, diesters of unsaturated branched fatty acids having 12 to 24 carbon atoms and glycerin, and diesters of two types of fatty acids having 12 to 24 carbon atoms and glycerin. When the glycerin fatty acid ester composition of the present invention contains a diester of a fatty acid having 12 to 24 carbon atoms and glycerin, from the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, it is preferable that the diester of a fatty acid having 12 to 24 carbon atoms and glycerin contains at least one diester of a fatty acid having 14 to 22 carbon atoms and glycerin, and it is more preferable that the diester contain at least one diester of a fatty acid having 16 to 20 carbon atoms and glycerin.

[0012] Examples of triesters of glycerin and fatty acids having 12 to 24 carbon atoms that can be contained in the glycerin fatty acid ester composition of the present invention include triesters of linear saturated fatty acids having 12 to 24 carbon atoms and glycerin, triesters of branched saturated fatty acids having 12 to 24 carbon atoms and glycerin, triesters of linear unsaturated fatty acids having 12 to 24 carbon atoms and glycerin, triesters of branched unsaturated fatty acids having 12 to 24 carbon atoms and glycerin, triesters of two or three fatty acids having 12 to 24 carbon atoms and glycerin, and the like. When the glycerin fatty acid ester composition of the present invention contains a triester of a fatty acid having 12 to 24 carbon atoms and glycerin, from the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, it is preferable that the triester of a fatty acid having 12 to 24 carbon atoms and glycerin contains at least one triester of a fatty acid having 14 to 22 carbon atoms and glycerin, and it is more preferable that the glycerin fatty acid ester composition contains at least one triester of a fatty acid having 16 to 20 carbon atoms and glycerin.

[0013] The glycerin fatty acid ester composition of the present invention is a glycerin fatty acid ester composition in which the content of a monoester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition is 90.0 to 99.8 mass% relative to the total amount of the glycerin fatty acid ester composition. The glycerin fatty acid ester composition of the present invention has excellent friction-reducing properties due to the specific ratio of the monoester content. From the viewpoint of obtaining a glycerin fatty acid ester composition with even more excellent friction-reducing properties, the content of the monoester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition is preferably 95.0 to 99.8 mass%, more preferably 97.0 to 99.6 mass%, even more preferably 97.8 to 99.4 mass%, and particularly preferably 97.8 to 99.2 mass%, relative to the total amount of the glycerin fatty acid ester composition. In the present invention, the content of the monoester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition can be adjusted by selecting the raw materials when producing the glycerin fatty acid ester composition, adjusting the raw material ratio, distilling and extracting the product after the reaction, etc. In addition, in the present invention, the content of the monoester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition is calculated from the fatty acid composition ratio of the glycerin fatty acid ester composition specified by the method described in "Standard Test Methods for the Analysis of Fats, Oils and Related Materials, 2.4.2.3 Fatty Acid Composition (Capillary Gas Chromatography)" of the Japan Oil Chemists' Society.

[0014] From the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, the content of the diester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition of the present invention is, for example, preferably 0.0 to 5.0 mass%, more preferably 0.0 to 3.0 mass%, and even more preferably 0.0 to 1.0 mass%, based on the total amount of the glycerin fatty acid ester composition. In the present invention, the content of the diester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition can be adjusted by selecting the raw materials used in producing the glycerin fatty acid ester composition, adjusting the raw material ratio, distilling and extracting the reaction product, etc. In addition, in the present invention, the content of the diester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition is calculated from the fatty acid composition ratio of the glycerin fatty acid ester composition determined by the method described in "Standard Methods for the Analysis of Fats, Oils, and Related Materials, 2.4.2.3 Fatty Acid Composition (Capillary Gas Chromatography)" of the Japan Oil Chemists' Society.

[0015] From the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, the content of the triester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition of the present invention is, for example, preferably 0.0 to 5.0 mass%, more preferably 0.0 to 3.0 mass%, and even more preferably 0.0 to 1.0 mass%, relative to the total amount of the glycerin fatty acid ester composition. In the present invention, the content of the triester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition can be adjusted by selecting raw materials when producing the glycerin fatty acid ester composition, adjusting the raw material ratio, distilling and extracting the reaction product, etc. In the present invention, the content of the triester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition is calculated from the fatty acid composition ratio of the glycerin fatty acid ester composition determined by the method described in "Standard Methods for the Analysis of Fats, Oils, and Related Materials, 2.4.2.3 Fatty Acid Composition (Capillary Gas Chromatography)" of the Japan Oil Chemists' Society.

[0016] Furthermore, from the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, the total content of the diester of a fatty acid having 12 to 24 carbon atoms and glycerin and the triester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition of the present invention is, for example, preferably 0.1 to 10.0 mass%, more preferably 0.2 to 10.0 mass%, even more preferably 0.5 to 5.0 mass%, even more preferably 0.6 to 3.0 mass%, and particularly preferably 0.8 to 2.2 mass%, relative to the total amount of the glycerin fatty acid ester composition.

[0017] The glycerin fatty acid ester composition of the present invention may contain unavoidable impurities, and the amount of such impurities is preferably less than 0.1% by mass, more preferably 0.05% by mass or less, and even more preferably 0.01% by mass or less, based on the total amount of the glycerin fatty acid ester composition.

[0018] From the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition of the present invention, the total content of glyceryl monolaurate, glyceryl monomyristate, glyceryl monopalmitate, glyceryl monostearate, glyceryl monoarachidate, glyceryl monobehenate, and glyceryl monolignocerate in the glycerin fatty acid ester composition is preferably 3.0 to 20.0 mass%, more preferably 5.0 to 16.0 mass%, even more preferably 7.0 to 12.0 mass%, and particularly preferably 8.0 to 10.0 mass%, relative to the total amount of the glycerin fatty acid ester composition. In the present invention, the total content of glyceryl monolaurate, glyceryl monomyristate, glyceryl monopalmitate, glyceryl monostearate, glyceryl monoarachidate, glyceryl monobehenate, and glyceryl monolignocerate in the glycerin fatty acid ester composition is calculated from the fatty acid composition ratio of the glycerin fatty acid ester composition specified by the method described in "Standard Test Methods for the Analysis of Fats, Oils and Related Materials, 2.4.2.3 Fatty Acid Composition (Capillary Gas Chromatography)" by the Japan Oil Chemists' Society.

[0019] The glycerin fatty acid ester composition of the present invention preferably contains glyceryl monolinoleate from the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition. Here, from the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, the glyceryl monolinoleate content is more preferably 0.1 to 15.0 mass%, even more preferably 2.0 to 12.0 mass%, and particularly preferably 3.0 to 10.0 mass%, based on the total amount of the glycerin fatty acid ester composition. Here, from the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, the ratio of glyceryl monooleate to glyceryl monolinoleate in the glycerin fatty acid ester composition is preferably 95:5 to 85:15 by mass, more preferably 94.5:5.5 to 88:12, even more preferably 94:6 to 90:10, and particularly preferably 93.5:6.5 to 91:9.

[0020] From the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition of the present invention, the iodine value of the glycerin fatty acid ester composition is preferably 65.0 to 70.0, more preferably 66.0 to 69.6, and even more preferably 66.5 to 69.2. In the present invention, the iodine value of the glycerin fatty acid ester composition is measured by the method described in JIS K 0070 (1992).

[0021] The glycerin fatty acid ester composition of the present invention can be produced by adjusting production conditions in a known method for producing a glycerin fatty acid ester, such as a method for producing a glycerin fatty acid ester by a direct esterification reaction between glycerin and fatty acids obtained by synthesis from petroleum feedstocks or fatty acids produced from animal and vegetable oils and fats, a method for producing a glycerin fatty acid ester by purifying and / or separating from oils and fats such as vegetable oils and animal oils, or a method for producing a glycerin fatty acid ester by mixing two or more glycerin fatty acid esters, so that the monoester ratio, monooleic acid content ratio, and iodine value in the glycerin fatty acid ester composition are specific values.

[0022] The use of the glycerin fatty acid ester composition of the present invention is not particularly limited as long as the glycerin fatty acid ester is used, and can be used by blending it with, for example, lubricating oil, grease, hydraulic oil, fuel oil, surface treatment agent, etc. Among these, from the viewpoint of the effects of the present invention, use in lubricating oil or fuel oil is preferred, and use as a friction modifier for lubricating oil or fuel oil is particularly preferred.

[0023] The lubricating oil composition of the present invention is a lubricating oil composition containing the above-mentioned glycerin fatty acid ester composition and a base oil. The content of the glycerin fatty acid ester composition in the lubricating oil composition of the present invention is not particularly limited and can be adjusted appropriately depending on the intended use and properties. From the viewpoint of the friction-reducing properties of the lubricating oil composition, the content of the glycerin fatty acid ester composition is preferably 0.01 to 10.0 parts by mass, more preferably 0.1 to 5.0 parts by mass, and most preferably 0.2 to 3.0 parts by mass, based on the total amount of the lubricating oil composition. By configuring the lubricating oil composition as described above, it is possible to obtain a lubricating oil composition with excellent friction-reducing properties.

[0024] The base oil that can be used in the lubricating oil composition of the present invention is not particularly limited as long as it is a base oil that is commonly used in lubricating oils, and can be appropriately selected from mineral base oils, chemically synthesized base oils, animal and vegetable base oils, and mixed base oils thereof, etc., depending on the purpose and conditions of use. Examples of mineral base oils include paraffinic crude oils, naphthenic crude oils, intermediate crude oils, and aromatic crude oils, as well as distillate oils obtained by atmospheric distillation of these or distillate oils obtained by vacuum distillation of residual oils from atmospheric distillation, and refined oils obtained by refining these according to conventional methods, specifically solvent refined oils, hydrogenated refined oils, dewaxed oils, and clay-treated oils.

[0025] Examples of chemically synthesized base oils include poly-α-olefins, polyisobutylene (polybutene), monoesters, diesters, polyol esters, silicate esters, polyalkylene glycols, polyphenyl ethers, silicones, fluorinated compounds, alkylbenzenes, and GTL base oils. Among these, poly-α-olefins, polyisobutylene (polybutene), diesters, and polyol esters are widely used. Examples of poly-α-olefins include polymers or oligomers of 1-hexene, 1-octene, 1-nonene, 1-decene, 1-dodecene, and 1-tetradecene, as well as hydrogenated versions of these. Examples of diesters include diesters of dibasic acids such as glutaric acid, adipic acid, azelaic acid, sebacic acid, and dodecanedioic acid with alcohols such as 2-ethylhexanol, octanol, decanol, dodecanol, and tridecanol. Examples of polyol esters include esters of polyols such as neopentyl glycol, trimethylolethane, trimethylolpropane, pentaerythritol, dipentaerythritol, and tripentaerythritol with fatty acids such as caproic acid, caprylic acid, lauric acid, capric acid, myristic acid, palmitic acid, stearic acid, and oleic acid.

[0026] Examples of the animal and vegetable base oils include vegetable oils such as castor oil, olive oil, cacao butter, sesame oil, rice bran oil, safflower oil, soybean oil, camellia oil, corn oil, rapeseed oil, palm oil, palm kernel oil, sunflower oil, cottonseed oil, and coconut oil, and animal oils such as beef tallow, lard, milk fat, fish oil, and whale oil. These various base oils listed above may be used alone or in appropriate combination of two or more.

[0027] From the viewpoint of friction-reducing properties, the lubricating oil composition of the present invention preferably contains at least one mineral base oil or chemically synthetic base oil as the base oil, and more preferably contains a paraffin-based highly refined mineral oil, a poly-α-olefin-based, or a GTL-based chemically synthetic base oil. In this case, from the viewpoint of friction-reducing properties, the paraffin-based highly refined mineral oil, the poly-α-olefin-based, or the GTL-based chemically synthetic base oil preferably accounts for 50 mass% or more of the total amount of base oil, and more preferably 90 mass% or more. Furthermore, the content of the base oil in the lubricating oil composition of the present invention is not particularly limited and can be adjusted depending on the intended use, but from the viewpoint of the friction-reducing properties of the lubricating oil composition, it is preferably 20 to 98 mass% of the total amount of the lubricating oil composition.

[0028] The viscosity of the base oil used in the present invention is not particularly limited, but from the viewpoint of the friction reducing properties of the lubricating oil composition, the kinematic viscosity at 100°C is preferably 0.8 to 8.0 mm 2 / s, and 1.0 to 8.0 mm 2 / s is more preferable, and 1.2 to 6.0 mm 2 In the present invention, the kinematic viscosity at 100°C is a value obtained by measurement according to the method described in JIS K 2283.

[0029] The lubricating oil composition of the present invention may be blended with known lubricating oil additives as appropriate depending on the intended use, provided that the effects of the present invention are not impaired, such as metal detergents, antioxidants, antifriction and wear agents, extreme pressure agents, ashless dispersants, oiliness improvers, rust inhibitors, viscosity index improvers, metal deactivators, antifoaming agents, solid lubricants, etc. One or more types of each lubricating oil additive may be blended.

[0030] Examples of metallic detergents include alkaline earth metal sulfonates, alkaline earth metal phenates, alkaline earth metal salicylates, and alkaline earth metal phosphonates, and examples of alkaline earth metals include magnesium, calcium, and barium. Among these, from the viewpoint of further enhancing the effects of the present invention, it is preferable to use at least one metallic detergent selected from the group consisting of calcium-based detergents and magnesium-based detergents, and it is more preferable to use one or more calcium-based detergents and one or more magnesium-based detergents. The content of the metallic detergent in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, etc., but for example, the total content of calcium atoms and magnesium atoms is preferably 0.05 to 0.50 mass%, more preferably 0.10 to 0.40 mass%, based on the total amount of the lubricating oil composition.

[0031] Examples of antioxidants include amine-based antioxidants, phenol-based antioxidants, phenothiazine-based antioxidants, thioether-based antioxidants, and phosphite-based antioxidants. Among these, it is preferable to use at least one antioxidant selected from the group consisting of phenol-based antioxidants and amine-based antioxidants. The content of the antioxidant in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, but it can be contained in an amount of, for example, 0.01 to 10 mass% based on the total amount of the lubricating oil composition.

[0032] Examples of anti-friction and wear agents include organic molybdenum compounds such as molybdenum dithiocarbamate, molybdenum dithiophosphate, molybdenum long-chain amine salts, and molybdenum alkenyl succinimide complexes, and phosphorus compounds such as organic phosphines, organic phosphine oxides, organic phosphinites, organic phosphonites, organic phosphinates, organic phosphites, organic phosphonates, organic phosphates, and organic phosphoramidates. The content of the anti-friction and wear agent in the lubricating oil composition is not particularly limited, but can be, for example, 0.01 to 10 mass% based on the total amount of the lubricating oil composition.

[0033] Examples of extreme pressure agents include sulfur-based extreme pressure agents such as sulfurized oils and fats, sulfurized mineral oils, organic mono- or polysulfides, polyolefin sulfides, 1,3,4-thiadiazole derivatives, thiuram disulfides, and dithiocarbamic acid esters, and thiophosphate-based extreme pressure agents such as organic trithiophosphites and organic thiophosphates. The content of the extreme pressure agent in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, etc., but can be contained in an amount of, for example, 0.01 to 10 mass% based on the total amount of the lubricating oil composition.

[0034] Examples of ashless dispersants include alkenyl succinimides, alkenyl succinic anhydrides, alkenyl succinic acid esters, alkyl methacrylate polymers, high molecular weight amides and polyamides, polyesters, polyvinyl polystearates, Mannich base dispersants, polystearamides, and modified products thereof modified with boric acid, etc. The content of the ashless dispersant in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, etc., but can be contained in an amount of, for example, 0.01 to 10 mass% based on the total amount of the lubricating oil composition.

[0035] Examples of oiliness improvers include fatty acids, fats and oils, or hydrogenated or partially saponified products thereof, epoxidized esters, polycondensates of hydroxystearic acid or esters of such polycondensates with fatty acids, higher alcohols, higher amides, glycerides, polyglycerol esters, polyglycerol ethers, and adducts of the above compounds with α-olefin oxides. The content of the oiliness improver in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, etc., but can be contained in an amount of, for example, 0.01 to 30 mass% based on the total amount of the lubricating oil composition.

[0036] Examples of rust inhibitors include oxidized paraffin wax calcium salt, oxidized paraffin wax magnesium salt, tallow fatty acid alkali metal salt, alkaline earth metal salt or amine salt, alkenylsuccinic acid or alkenylsuccinic acid half ester (the molecular weight of the alkenyl group is about 100 to 300), sorbitan monoester, pentaerythritol monoester, glycerin monoester, nonylphenol ethoxylate, lanolin fatty acid ester, lanolin fatty acid calcium salt, etc. The content of the rust inhibitor in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, etc., but can be contained in an amount of, for example, 0.01 to 20 mass% based on the total amount of the lubricating oil composition.

[0037] Examples of viscosity index improvers include poly(C1-18) alkyl methacrylate, (C1-18) alkyl acrylate / (C1-18) alkyl methacrylate copolymer, diethylaminoethyl methacrylate / (C1-18) alkyl methacrylate copolymer, ethylene / (C1-18) alkyl methacrylate copolymer, polyisobutylene, polyalkylstyrene, ethylene / propylene copolymer, styrene / maleic acid ester copolymer, styrene / maleic acid amide copolymer, styrene / hydrogenated butadiene copolymer, and styrene / hydrogenated isoprene copolymer, and the average molecular weight may be about 10,000 to 1,500,000. The content of the viscosity index improver in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, etc., but can be, for example, 0.01 to 20 mass% based on the total amount of the lubricating oil composition.

[0038] Examples of metal deactivators include N,N'-salicylidene-1,2-propanediamine, alizarin, tetraalkylthiuram disulfide, benzotriazole, benzimidazole, 2-alkyldithiobenzimidazole, 2-alkyldithiobenzothiazole, 2-(N,N-dialkylthiocarbamoyl)benzothiazole, 2,5-bis(alkyldithio)-1,3,4-thiadiazole, 2,5-bis(N,N-dialkylthiocarbamoyl)-1,3,4-thiadiazole, etc. The content of the metal deactivator in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, etc., but can be contained in an amount of, for example, 0.1 to 10 mass% based on the total amount of the lubricating oil composition.

[0039] Examples of antifoaming agents include polydimethyl silicone, trifluoropropylmethyl silicone, colloidal silica, polyalkyl acrylate, polyalkyl methacrylate, alcohol ethoxy / propoxylate, fatty acid ethoxy / propoxylate, sorbitan partial fatty acid ester, etc. The content of the antifoaming agent in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, etc., but can be contained in an amount of, for example, 0.01 to 10 mass % relative to the total amount of the lubricating oil composition.

[0040] Examples of solid lubricants include graphite, molybdenum disulfide, polytetrafluoroethylene, alkaline earth metal salts of fatty acids, mica, cadmium dichloride, cadmium diiodide, calcium fluoride, lead iodide, lead oxide, titanium carbide, titanium nitride, aluminum silicate, antimony oxide, cerium fluoride, polyethylene, diamond powder, silicon nitride, boron nitride fluorocarbon, melamine isocyanurate, etc. The content of the solid lubricant in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, etc., but can be contained in an amount of, for example, 0.01 to 5 mass% based on the total amount of the lubricating oil composition.

[0041] The viscosity of the lubricating oil composition of the present invention is not particularly limited and can be adjusted appropriately depending on the intended use and properties. From the viewpoint of the effects of the present invention, however, it is preferable that the kinematic viscosity at 100°C is 0.8 to 8.0 mm 2 / s, and 1.0 to 8.0 mm 2 / s is more preferable, and 1.2 to 6.0 mm 2 In the present invention, the kinematic viscosity at 100°C is a value obtained by measurement according to the method described in JIS K 2283.

[0042] The low-temperature viscosity grade of the lubricating oil composition of the present invention is not particularly limited, but from the viewpoint of the effects of the present invention, the low-temperature viscosity grade is preferably a grade of 0 to 25, more preferably a grade of 0 to 15, even more preferably a grade of 0 to 10, and particularly preferably a grade of 0 to 5. Furthermore, the high-temperature viscosity grade of the lubricating oil composition of the present invention is not particularly limited, but from the viewpoint of the effects of the present invention, the high-temperature viscosity grade is preferably a grade of 8 to 30, more preferably a grade of 8 to 20, and even more preferably a grade of 8 to 16. In the present invention, the low-temperature viscosity grade and high-temperature viscosity grade are defined in accordance with the engine oil viscosity standard SAE J300 established by SAE International.

[0043] The lubricating oil composition of the present invention can be used in any manner generally used for lubricating oils, without any particular limitation, and can be used, for example, as a lubricating oil for internal combustion engines (for example, gasoline engine oils and diesel engine oils for automobiles, motorcycles, etc.), industrial lubricating oils (for example, gear oils, turbine oils, compressor oils, oil film bearing oils, insulating oils, refrigeration oils, hydraulic oils, vacuum pump oils, rock drill oils, compression lubricating oils, metal working oils, plastic working oils, heat treatment oils, multi-purpose lubricating oils, etc.) Among these, it is preferred to use it as a lubricating oil for internal combustion engines such as gasoline engines and diesel engines, as the effects of the present invention can be easily obtained.

[0044] The fuel oil composition of the present invention is a fuel oil composition containing the above-mentioned glycerin fatty acid ester composition and a base oil. The content of the glycerin fatty acid ester composition in the fuel oil composition of the present invention is not particularly limited and can be adjusted appropriately depending on the intended use and properties. However, from the viewpoint of the friction-reducing properties of the fuel oil composition, the content of the glycerin fatty acid ester composition is preferably 0.001 to 10.0 parts by mass, more preferably 0.01 to 5.0 parts by mass, and most preferably 0.1 to 3.0 parts by mass, relative to the total amount of the fuel oil composition. By configuring the fuel oil composition as described above, the present invention can be a fuel oil composition with excellent friction-reducing properties.

[0045] The base oil that can be used in the fuel oil composition of the present invention is not particularly limited as long as it is a base oil that is commonly used in fuel oils, and examples thereof include Special No. 1 light oil, No. 1 light oil, No. 2 light oil, No. 3 light oil, Special No. 3 light oil, A heavy oil, B heavy oil, C heavy oil, No. 1 kerosene, No. 2 kerosene, MGO (Marine Gas Oil), MFO (Marine Fuel Oil), MDO (Marine Diesel Oil), MDF (Marine Diesel Fuel), HFO (Heavy Fuel Oil), RFO (Residual Fuel Oil), LSMGO (Low Sulfur Marine Gas Oil), LSMDO (Low Sulfur Marine Diesel Oil), VLSFO (Very Low Sulfur Fuel Oil), ULSFO (Ultra Low Sulfur Fuel Oil), and the like. Oil, palm oil, coconut oil, rapeseed oil, soybean oil, sunflower oil, corn oil, sesame oil, tall oil, bone oil, whale oil, etc., and one or more of these can be used. Among these, the light oil or heavy oil may be a straight-run light oil fraction, a vacuum light oil fraction, a desulfurized light oil fraction, a cracked base oil fraction, a straight-run light oil fraction, an atmospheric distillation residue, a vacuum distillation residue, a straight-run heavy oil, a cracked heavy oil, etc. Furthermore, in the present invention, the above-mentioned fuel oil may be hydrotreated before use.

[0046] The sulfur content of the base oil used in the fuel oil composition of the present invention is not particularly limited. However, from the viewpoint of the effects of the present invention, the sulfur content is preferably 0.01 to 0.50% by mass, more preferably 0.03 to 0.48% by mass, and even more preferably 0.10 to 0.45% by mass. In the present invention, the sulfur content is measured by the ultraviolet fluorescence method described in JIS K 2541-6 (2003). The method for adjusting the sulfur content of the base oil is not particularly limited. For example, the sulfur content may be adjusted by subjecting a base oil containing a high amount of sulfur to direct or indirect desulfurization treatment. Alternatively, for example, a base oil containing more than 0.50% by mass of sulfur and a base oil containing less than 0.50% by mass of sulfur may be mixed to adjust the sulfur content to 0.01 to 0.50% by mass.

[0047] From the viewpoint of the effects of the present invention, the viscosity of the base oil used in the fuel oil composition of the present invention is, in particular, a kinematic viscosity at 40°C of 1 to 600 mm 2 / s is preferably 2 to 500 mm 2 / s is more preferable, and 2 to 400 mm 2 / s is even more preferable, and 2 to 250 mm 2 In the present invention, the kinematic viscosity is measured by the method described in JIS K 2283 (2000).

[0048] In the present invention, from the viewpoint of the effects of the present invention, it is preferable to use at least one selected from light oils (including Special No. 1 light oil, No. 1 light oil, No. 2 light oil, No. 3 light oil, Special No. 3 light oil, and MGO) or heavy oils (including heavy oil A, heavy oil B, heavy oil C, MDO, VLSFO, and ULSFO) as the base oil used in the fuel oil composition. In this case, the total content of light oil and heavy oil in the base oil is not particularly limited, but from the viewpoint of the effects of the present invention, the total amount of light oil and heavy oil relative to the total amount of base oil is preferably 10 to 100 mass%, more preferably 40 to 100 mass%, and even more preferably 80 to 100 mass%. Among such base oils, it is preferable that the content ratio of light oil to heavy oil is 0:100 to 90:10 in mass ratio. Furthermore, from the viewpoint of the effects of the present invention, it is particularly preferable to use a base oil containing at least one selected from MGO or heavy oil as the base oil. At this time, the content of MGO or heavy oil in the base oil or the total content of MGO and base oil is not particularly limited, but from the viewpoint of the effects of the present invention, the content of MGO or heavy oil in the base oil or the total amount of MGO and base oil is preferably 10 to 100% by mass, more preferably 40 to 100% by mass, even more preferably 80 to 100% by mass, and particularly preferably 100% by mass. In addition, when the total amount of MGO and heavy oil in the base oil is 100% by mass, the content ratio of MGO and heavy oil is not particularly limited, for example, the content ratio of MGO and heavy oil can be 0:100 to 100:0 in mass ratio, and preferably 0:100 to 90:10.

[0049] The fuel oil composition of the present invention may contain known fuel oil additives for improving combustibility, storage stability, oxidation stability, anti-wear, uniformity, safety, environmental compatibility, startability, low-temperature fluidity, handleability, etc. For example, fuel oil additives such as surface ignition agents, octane improvers, cetane improvers, antibacterial / fungicides, rust inhibitors, deposit improvers, antioxidants, metal deactivators, anti-wear agents, detergents / dispersants, flow improvers, anti-icing agents, anti-knock agents, corrosion inhibitors, antistatic agents, combustion improvers, dyes, etc. One or more types of each fuel oil additive may be blended.

[0050] Examples of the surface ignition inhibitor include organic phosphorus compounds such as tributyl phosphite, trimethyl phosphite, tricresyl phosphate, tricyclohexyl phosphate, cresyl diphenyl phosphate, trimethyl phosphate, and methyl phenyl phosphate; and organic boron compounds such as 2-ethylhexyl boronate and butyl diisobutyl boronate, and one or more of these can be used. The content of the surface ignition inhibitor is not particularly limited, but can be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

[0051] Examples of octane improvers include methanol, ethanol, butanol, butyl acetate, methyl tert-butyl ether, ethyl tert-butyl ether, methyl tert-amyl ether, N-methylaniline, methylcyclopentadienyl manganese tricarbonyl, tetraethyl lead, etc., and one or more of these may be used. The content of the octane improver is not particularly limited, but may be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

[0052] Examples of cetane number improvers include aliphatic nitrates such as ethyl nitrate, methoxyethyl nitrate, isopropyl nitrate, amyl nitrate, hexyl nitrate, heptyl nitrate, octyl nitrate, 2-ethylhexyl nitrate, and cyclohexyl nitrate; and peroxides such as di-tert-butyl peroxide, and one or more of these may be used. The content of the cetane number improver is not particularly limited, but can be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

[0053] Examples of antibacterial and disinfectant agents include inorganic disinfectants such as silver sulfate, silver nitrate, zinc sulfate, zinc nitrate, copper sulfate, and ethylenediaminetetracopper acetate; organic nitrogen-based antibacterial agents such as hexahydro-1,3,5-tris(2-hydroxyethyl)-triazine; organic bromine-based antibacterial agents such as 2,2-dibromo-3-nitrilopropionamide, 1,4-bis(bromoacetoxy)-2-ethane, and bistribromomethylsulfone; 2-methyl-4-isothiazolin-3-one, 2 and isothiazoline antibacterial agents such as 2-n-methyl-4,5-trimethylene-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-n-octylisothiazolin-3-one, 4,5-dichloro-2-n-octylisothiazolin-3-one, 1,2-benzisothiazolin-3-one, and Nn-butyl-1,2-benzisothiazolin-3-one, and one or more of these may be used. The content of the antibacterial / bactericide is not particularly limited, and may be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

[0054] Examples of the rust inhibitor include aliphatic amines and their salts, organic phosphates, organic sulfonates, etc., and one or more of these can be used. The content of the rust inhibitor is not particularly limited, but can be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

[0055] Examples of the deposit improver include tricresyl phosphate, trimethyl phosphate, tris(chloroethyl)phosphate, polypropylene, polybutene, polyisobutyleneamine, polyetheramine, polyalkylamine, polyoxyalkyleneamine, polyalkylphenoxyaminoalkane, polyalkylene succinimide, etc., and one or more of these can be used. The content of the deposit improver is not particularly limited, but can be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

[0056] Examples of the antioxidant include amine-based antioxidants such as N,N'-diisopropyl-p-phenylenediamine, N,N'-dibutyl-p-phenylenediamine, N,N'-dioctyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-ditolyl-p-phenylenediamine, and N-tolyl-N'-xylenyl-p-phenylenediamine; 2-t-butylphenol, 2,6-ditertiarybutylphenol, and 2,6-ditertiarybutyl-4-methylphenol; and sulfur-based antioxidants such as dilauryl 3,3'-thiodipropionate, distearyl 3,3'-thiodipropionate, laurylstearyl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate, distearyl β,β'-thiodibutyrate, and dilauryl sulfide, and one or more of these can be used. The content of the antioxidant is not particularly limited, but can be, for example, 0.001 to 10% by mass based on the total amount of the fuel oil composition.

[0057] Examples of metal deactivators include amino compounds such as ethylenediamine; salicylidene compounds such as N,N'-disalicylidene-1,2-diaminopropane, N,N'-disalicylidene-2-cyclohexanediamine, N,N'-disalicylideneethylenediamine, N,N'-bis(dimethylsalicylidene)ethylenediamine, N,N'-bis(dimethylsalicylidene)ethylenetetramine, and salicylaldoxime; 1-[bis(2-ethylhexyl)aminomethyl-1,2,4-triazole, 1-(1-butoxyethyl)-1,2,4-triazole, 4,4'-methylenebis(2-undecyl-5-methyl)-2,3-dimethyl-2,4-dimethyl ... triazole compounds such as bis[(N-methyl)imidazol-2-yl]carbinol octyl ether; and benzotriazole compounds such as 4-alkylbenzotriazole, 4,5,6,7-tetrahydrobenzotriazole, 5,5'-methylenebisbenzotriazole, 1-[bis(2-ethylhexyl)aminomethyl)triazole, 1-[bis(2-ethylhexyl)aminomethyl)benzotriazole, 1-(nonyloxymethyl)benzotriazole, and 1-(1-butoxyethyl)benzotriazole, and one or more of these may be used. The content of the metal deactivator is not particularly limited, but can be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

[0058] Examples of anti-wear agents include sulfurized oils and fats, olefin polysulfides, sulfurized olefins, dibenzyl sulfide, ethyl-3-[[bis(1-methylethoxy)phosphinothioyl]thio]propionate, tris-[(2, or 4)-isoalkylphenol]thiophosphate, 3-(di-isobutoxy-thiophosphorylsulfanyl)-2-methyl-propionic acid, triphenylphosphorothionate, β-dithiophosphorylated propionic acid, methylenebis(dibutyldithiocarbamate), O,O-diisopropyl-dithiophosphoryl sulfur-based antiwear agents such as ethyl ethyl propionate, 2,5-bis(n-nonyldithio)-1,3,4-thiadiazole, 2,5-bis(1,1,3,3-tetramethylbutanethio)-1,3,4-thiadiazole, and 2,5-bis(1,1,3,3-tetramethyldithio)-1,3,4-thiadiazole; monooctyl phosphate, dioctyl phosphate, trioctyl phosphate, monobutyl phosphate, dibutyl phosphate, tributyl phosphate, monophenyl phosphate, diphenyl phosphate, triphenyl phosphate; phosphate, tricresyl phosphate, monoisopropyl phenyl phosphate, diisopropyl phenyl phosphate, triisopropyl phenyl phosphate, monotert-butyl phenyl phosphate, di-tert-butyl phenyl phosphate, tri-tert-butyl phenyl phosphate, triphenyl thiophosphate, monooctyl phosphite, dioctyl phosphite, trioctyl phosphite, monobutyl phosphite, dibutyl phosphite, tributyl phosphite, monophenyl phosphate Phosphorus compounds such as phenyl phosphite, diphenyl phosphite, triphenyl phosphite, monoisopropyl phenyl phosphite, diisopropyl phenyl phosphite, triisopropyl phenyl phosphite, mono-tert-butylphenyl phosphite, di-tert-butylphenyl phosphite, and tri-tert-butylphenyl phosphite; fatty acids such as caprylic acid, 2-ethylhexanoic acid, nonanoic acid, isononanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidonic acid, and behenic acid;Examples of suitable antiwear agents include organometallic compounds such as metal naphthenates, metal fatty acid salts, metal phosphates, metal phosphate ester salts, and metal phosphites; boron compounds, alkylamine salts of mono- and dihexyl phosphates, amine salts of phosphate esters, and mixtures of triphenyl thiophosphate esters and tert-butylphenyl derivatives. The content of the antiwear agent is not particularly limited, but can be, for example, 0.01 to 10 mass% of the total amount of the fuel oil composition.

[0059] Examples of detergents and dispersants include phosphoric acid amides, aminoalkanes, alkylamine phosphate esters, polyetheramines, polybutenylamines, alkenyl succinimides, alkenyl succinic acid esters, metal salicylates, metal sulfonates, metal carboxylates, and metal phosphonates, and one or more of these can be used. The content of the detergents and dispersants is not particularly limited, but can be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

[0060] Examples of flow improvers include polymethacrylate polymers, polyacrylate polymers, olefinically unsaturated polymers, ethylene-vinyl acetate copolymers, polyolefin-substituted phenol polymers, alkenyl succinamides, fatty acid esters of alkylene oxide adducts of alkane polyols, fatty acid esters of alkylene oxide adducts of alkanolamines, sorbitan fatty acid esters such as sorbitan mono-fatty acid esters, sorbitan di-fatty acid esters, sorbitan tri-fatty acid esters, sorbitan sesqui-fatty acid esters, and polyoxyalkylene-condensed sorbitan fatty acid esters. One or more of these can be used. The content of the flow improver is not particularly limited, but can be, for example, 0.001 to 10% by mass based on the total amount of the fuel oil composition.

[0061] The CCAI (Calculated Carbon Aromatic Index) of the fuel oil composition of the present invention is not particularly limited, but from the viewpoint of various properties of the fuel oil composition, it is preferably from 780 to 900, and more preferably from 800 to 860. In the present invention, the CCAI of the fuel oil composition is calculated in accordance with ISO 8217.

[0062] The flash point of the fuel oil composition of the present invention is not particularly limited, but from the viewpoint of various properties of the fuel oil composition, it is preferably 40° C. or higher and 120° C. or lower. In the present invention, the flash point of the fuel oil composition is measured by the Pensky-Martens closed-cell method described in JIS K 2265-3 (2007).

[0063] The pour point of the fuel oil composition of the present invention is not particularly limited, but from the viewpoint of various properties of the fuel oil composition, it is preferably −40° C. or higher and 30° C. or lower. In the present invention, the pour point of the fuel oil composition is measured by the method described in JIS K 2269 (1987).

[0064] The kinematic viscosity of the fuel oil composition of the present invention is not particularly limited, but from the viewpoint of various properties of the fuel oil composition, the kinematic viscosity at 40°C is preferably 1 to 400 mm 2 / s is preferably 2 to 200 mm 2 / s is more preferable, and 2 to 100 mm 2 In the present invention, the kinematic viscosity at 40°C of the fuel oil composition is measured by the method described in JIS K 2283 (2000).

[0065] The density of the fuel oil composition of the present invention is not particularly limited. However, from the viewpoint of various properties of the fuel oil composition, it is preferable that the density at 15°C is 0.70 g / cm. 3 More than 1.00g / cm 3 Preferably, it is 0.80 g / cm or less. 3 More than 0.98g / cm 3 It is more preferable that the density of the fuel oil composition is not more than 100%. In the present invention, the density of the fuel oil composition is measured by the method described in JIS K 2249 (2011).

[0066] The fuel oil composition of the present invention can be used without particular limitation as long as it is used in an embodiment that uses a liquid fuel oil, and can be used, for example, as automotive fuel oil for passenger cars, trucks, etc., marine fuel oil for passenger ships, cargo ships, etc., aircraft fuel oil for airplanes, helicopters, etc., railroad vehicle fuel oil for diesel locomotives, etc., agricultural machinery fuel oil, construction machinery fuel oil, etc., and among these, it is preferably used as marine fuel oil. [Example]

[0067] The present invention will be described in more detail below with reference to examples. In the following examples, "%" is by weight unless otherwise specified.

[0068] <Preparation of Glycerin Fatty Acid Ester Composition 1> A glycerin fatty acid ester composition 1 consisting of a mixture of esters of fatty acids having 12 to 24 carbon atoms and glycerin was prepared by reacting fatty acids with glycerin using a known method and then distilling the mixture. The types and contents of fatty acids constituting the glycerin fatty acid esters in the resulting glycerin fatty acid ester composition 1 were determined using a gas chromatograph (GC-2014, manufactured by Shimadzu Corporation) according to the method specified in "Standard Methods for the Analysis of Fats, Oils, and Related Materials, 2.4.2.3 Fatty Acid Composition (Capillary Gas Chromatography)" of the Japan Oil Chemists' Society. Table 1 also shows the iodine value of glycerin fatty acid ester composition 1, measured according to the method specified in JIS K 0070 (1992). In Table 1, "%" indicates "% by mass."

[0069] <Preparation of Glycerin Fatty Acid Ester Compositions 2 to 5> Glycerin fatty acid ester compositions 2 to 5 were each prepared in the same manner as in the preparation of glycerin fatty acid ester composition 1, except that the type of fat or oil used, the raw material ratio, and the distillation conditions were changed. The type and content of fatty acids constituting the glycerin fatty acid ester in each of the obtained glycerin fatty acid ester compositions, as well as the iodine value of each glycerin fatty acid ester composition measured according to the method specified in JIS K 0070 (1992), are shown in Table 1. In Table 1, % represents % by mass.

[0070] <Friction reduction characteristics evaluation> The friction-reducing properties of the prepared glycerin fatty acid ester compositions 1 to 5 were evaluated by measuring the friction coefficient under the following test conditions. Specifically, test oils 1 to 5 were prepared by blending glycerin fatty acid ester compositions 1 to 5 with a lubricating base oil (mineral base oil, 0W-8 grade) so that the content of the glycerin fatty acid ester composition relative to the total amount of the lubricating base oil and the glycerin fatty acid ester composition was 0.50 mass%. The friction coefficients of the test oils 1 to 5 were measured using an MTM tester (manufactured by PCS Instruments) by a ball-on-plate test under the following test conditions. In Comparative Example 3, the friction coefficient was measured using only the lubricating base oil in the same manner. The measurement results are shown in Table 1. A smaller friction coefficient indicates better friction-reducing properties.

[0071] [Friction coefficient measurement conditions] Temperature: 80℃ Load: 10N Rolling speed: 10mm / sec, 31mm / sec, 55mm / sec Slip rate: 50%

[0072] [Table 1]

[0073] As described above, the glycerin fatty acid ester composition of the present invention exhibited excellent friction-reducing properties. Therefore, it can be seen that the glycerin fatty acid ester composition of the present invention can be suitably used as a friction modifier, and that lubricating oil compositions and fuel oil compositions containing the glycerin fatty acid ester composition of the present invention can be used as lubricating oil compositions and fuel oil compositions having excellent friction-reducing properties.

Claims

1. A friction modifier comprising a glycerin fatty acid ester composition comprising an ester of a fatty acid having 12 to 24 carbon atoms and glycerin, wherein the content of the monoester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition is 95.0 to 99.8 mass% based on the total amount of the glycerin fatty acid ester composition, the content of glyceryl monooleate in the glycerin fatty acid ester composition is 65.0 to 90.0 mass% based on the total amount of the glycerin fatty acid ester composition, and the iodine value is 65.0 to 70.0, the total content of glyceryl monolaurate, glyceryl monomyristate, glyceryl monopalmitate, glyceryl monostearate, glyceryl monoarachidate, glyceryl monobehenate, and glyceryl monolignocerate in the glycerin fatty acid ester composition is 3.0 to 16.0% by mass, based on the total amount of the glycerin fatty acid ester composition; The ratio of the contents of glyceryl monooleate and glyceryl monolinoleate in the glycerin fatty acid ester composition is 95:5 to 85:15 by mass, and A friction modifier in which the total content of a diester of a fatty acid having 12 to 24 carbon atoms and glycerin and a triester of a fatty acid having 12 to 24 carbon atoms and glycerin is 0.2 to 5.0 mass% based on the total amount of the glycerin fatty acid ester composition.

2. 2. The friction modifier according to claim 1, wherein the content of glyceryl monooleate in the glycerin fatty acid ester composition is 75.0 to 90.0 mass% based on the total amount of the glycerin fatty acid ester composition.

3. A lubricating oil composition or a fuel oil composition comprising a glycerin fatty acid ester composition comprising an ester of a fatty acid having 12 to 24 carbon atoms and glycerin, and a base oil, the content of a monoester of a fatty acid having 12 to 24 carbon atoms and glycerin in the glycerin fatty acid ester composition is 95.0 to 99.8% by mass, based on the total amount of the glycerin fatty acid ester composition, the content of glyceryl monooleate in the glycerin fatty acid ester composition is 65.0 to 90.0% by mass, based on the total amount of the glycerin fatty acid ester composition, and the iodine value is 65.0 to 70.0; the total content of glyceryl monolaurate, glyceryl monomyristate, glyceryl monopalmitate, glyceryl monostearate, glyceryl monoarachidate, glyceryl monobehenate, and glyceryl monolignocerate in the glycerin fatty acid ester composition is 3.0 to 16.0% by mass, based on the total amount of the glycerin fatty acid ester composition; The ratio of the contents of glyceryl monooleate and glyceryl monolinoleate in the glycerin fatty acid ester composition is 95:5 to 85:15 by mass, and A lubricating oil composition or a fuel oil composition, in which the total content of a diester of a fatty acid having 12 to 24 carbon atoms and glycerin and a triester of a fatty acid having 12 to 24 carbon atoms and glycerin is 0.2 to 5.0 mass%.

4. 4. The lubricating oil composition or fuel oil composition according to claim 3, wherein the content of glyceryl monooleate in the glycerin fatty acid ester composition is 75.0 to 90.0 mass% based on the total amount of the glycerin fatty acid ester composition.

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