JP7777396B2 - Glycerin fatty acid ester composition and lubricating oil composition or fuel oil composition containing the glycerin fatty acid ester composition - Google Patents

Description

The present invention relates to a glycerin fatty acid ester composition with excellent friction-reducing properties.

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 demands for more fuel-efficient automobiles. Reducing friction in engine lubricants has therefore become a major challenge, and various friction reducers have been developed and added to engine lubricants. Among existing friction modifiers, organic molybdenum compounds are generally well known for their high friction-reducing effects (Patent Documents 1 and 2). Organic molybdenum compounds are said to exert their friction-reducing effects by forming a molybdenum disulfide film, and this effect has been recognized in all lubricants, including engine oils. However, organic molybdenum compounds do not exert their friction-reducing effects under all conditions, and depending on the application and purpose, organic molybdenum compounds alone may not be able to exert sufficient friction-reducing effects.

To address these issues, Patent Document 3 describes a lubricating oil composition for internal combustion engines containing a glycerin partial fatty acid ester with 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 a hydroxyl value of 150 to 300 mgKOH/g. However, even when such glycerin-based compounds are added to lubricating oils or fuel oils, sufficient friction-reducing effects cannot be achieved, and there is still a demand in the market for compounds with excellent friction-reducing properties.

Japanese Patent Application Publication No. 7-053983 Japanese Patent Application Publication No. 10-017586 Japanese Patent Application Laid-Open No. 2005-082709 JP 2014-025040 A

Therefore, an object of the present invention is to provide a glycerin fatty acid ester composition with excellent friction-reducing properties.

As a result of extensive research aimed at solving the above-mentioned problems, the inventors discovered that a specific glycerin fatty acid ester composition has excellent friction-reducing properties, leading to the completion of the present invention. Specifically, 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.

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.

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. For example, it may contain 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; or 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 also 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.

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.

Examples of monoesters of glycerin with 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.

Examples of the 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 linear saturated fatty acids having 12 to 24 carbon atoms and glycerin, diesters of branched saturated fatty acids having 12 to 24 carbon atoms and glycerin, diesters of linear unsaturated fatty acids having 12 to 24 carbon atoms and glycerin, diesters of branched unsaturated 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 even more preferable that the diester contain at least one diester of a fatty acid having 16 to 20 carbon atoms and glycerin.

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, etc. 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 even more preferable that the triester contain at least one triester of a fatty acid having 16 to 20 carbon atoms and glycerin.

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 exhibits excellent friction-reducing properties due to the specific ratio of the monoester content. From the perspective of achieving 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 monoesters of fatty acids 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. Furthermore, in the present invention, the content of monoesters of fatty acids 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.

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%, relative to 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 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.

In addition, 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 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 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 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.

In addition, 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 with glycerin and the triester of a fatty acid having 12 to 24 carbon atoms with 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.

The glycerin fatty acid ester composition of the present invention may contain unavoidable impurities. 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.

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 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.

From the viewpoint of the friction-reducing properties of the glycerin fatty acid ester composition, the glycerin fatty acid ester composition of the present invention preferably contains glyceryl monolinoleate. In this case, 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. In this case, 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.

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).

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

The use of the glycerin fatty acid ester composition of the present invention is not particularly limited as long as it uses glycerin fatty acid esters, and it can be used by blending it with, for example, lubricating oils, greases, hydraulic oils, fuel oils, surface treatment agents, etc. Among these, from the standpoint of the effects of the present invention, use in lubricating oils or fuel oils is preferred, and use as a friction modifier for lubricating oils or fuel oils is particularly preferred.

The lubricating oil composition of the present invention is a lubricating oil composition containing the above-described 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 application and properties. However, from the perspective 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, relative to the total amount of the lubricating oil composition. By configuring the lubricating oil composition as described above, the present invention can be a lubricating oil composition with excellent friction-reducing properties.

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 commonly used in lubricating oils. It can be selected from mineral base oils, chemically synthesized base oils, animal and vegetable base oils, and mixed base oils thereof, as appropriate depending on the intended use and conditions. Examples of mineral base oils include paraffinic crude oil, naphthenic crude oil, intermediate crude oil, and aromatic crude oil. These include distillate oils obtained by atmospheric distillation of these, and distillate oils obtained by vacuum distillation of the residual oil from atmospheric distillation. These also include refined oils obtained by refining these oils using conventional methods, such as solvent refined oil, hydrogenated refined oil, dewaxed oil, and clay-treated oil.

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.

Examples of animal and vegetable base oils include vegetable oils such as castor oil, olive oil, cocoa 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 combinations of two or more.

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 paraffinic 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 paraffinic highly refined mineral oil, the poly-α-olefin-based, or the GTL-based chemically synthetic base oil preferably accounts for a total amount of 50 mass% or more of the total amount of base oil, and even 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. However, from the viewpoint of the friction-reducing properties of the lubricating oil composition, it is preferable that the content be, for example, 20 to 98 mass% of the total amount of the lubricating oil composition.

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, more preferably 1.0 to 8.0 mm ² /s, and even more preferably 1.2 to 6.0 mm ² /s. 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.

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

Examples of metallic detergents include alkaline earth metal sulfonates, alkaline earth metal phenates, alkaline earth metal salicylates, and alkaline earth metal phosphonates. Examples of alkaline earth metals include magnesium, calcium, and barium. Among these, in order to further enhance 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. However, for example, the total content of calcium atoms and magnesium atoms is preferably 0.05 to 0.50 mass%, and more preferably 0.10 to 0.40 mass%, based on the total amount of the lubricating oil composition.

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 from the group consisting of phenol-based antioxidants and amine-based antioxidants. The content of antioxidant 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 10 mass% based on the total amount of the lubricating oil composition.

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, as well as phosphorus-based compounds such as organic phosphines, organic phosphine oxides, organic phosphinites, organic phosphonites, organic phosphinates, organic phosphites, organic phosphonates, organic phosphates, and organic phosphoramidates. The amount of anti-friction and wear agent contained 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.

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, for example, 0.01 to 10 mass% based on the total amount of the lubricating oil composition.

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 versions of these with boric acid or the like. The amount of ashless dispersant in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, but can be, for example, 0.01 to 10 mass% of the total amount of the lubricating oil composition.

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 as appropriate depending on the intended use, but can be, for example, 0.01 to 30 mass% of the total amount of the lubricating oil composition.

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 approximately 100 to 300), sorbitan monoester, pentaerythritol monoester, glycerin monoester, nonylphenol ethoxylate, lanolin fatty acid ester, and lanolin fatty acid calcium salt. 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, for example, 0.01 to 20 mass% based on the total amount of the lubricating oil composition.

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. These may have an average molecular weight of approximately 10,000 to 1,500,000. The content of viscosity index improver in the lubricating oil composition is not particularly limited and can be adjusted appropriately depending on the intended use, but can be, for example, 0.01 to 20 mass% based on the total amount of the lubricating oil composition.

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, and 2,5-bis(N,N-dialkylthiocarbamoyl)-1,3,4-thiadiazole. 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, for example, 0.1 to 10 mass% based on the total amount of the lubricating oil composition.

Examples of antifoaming agents include polydimethyl silicone, trifluoropropylmethyl silicone, colloidal silica, polyalkyl acrylate, polyalkyl methacrylate, alcohol ethoxy/propoxylate, fatty acid ethoxy/propoxylate, and sorbitan partial fatty acid ester. The content of 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, for example, 0.01 to 10 mass% of the total amount of the lubricating oil composition.

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, and melamine isocyanurate. 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, but can be, for example, 0.01 to 5 mass% of the total amount of the lubricating oil composition.

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, but from the viewpoint of the effects of the present invention, the kinematic viscosity at 100°C is preferably 0.8 to 8.0 mm ² /s, more preferably 1.0 to 8.0 mm ² /s, and even more preferably 1.2 to 6.0 mm ² /s. In the present invention, the 100°C kinematic viscosity is a value obtained by measurement according to the method described in JIS K 2283.

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

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

The fuel oil composition of the present invention is a fuel oil composition containing the above-described 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 perspective 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.

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 commonly used in fuel oils, and examples thereof include Special No. 1 Diesel Oil, No. 1 Diesel Oil, No. 2 Diesel Oil, No. 3 Diesel Oil, Special No. 3 Diesel Oil, Heavy Oil A, Heavy Oil B, Heavy Oil C, No. 1 Kerosene, No. 2 Kerosene, Marine Gas Oil (MGO), Marine Fuel Oil (MFO), Marine Diesel Oil (MDO), Marine Diesel Fuel (MDF), Heavy Fuel Oil (HFO), Residual Fuel Oil (RFO), Low Sulfur Marine Gas Oil (LSMGO), and Low Sulfur Marine Diesel Oil (LSMDO). Examples of suitable fuel oils include very low sulfur fuel oil (VLSFO), very low sulfur fuel oil (ULSFO), palm oil, coconut oil, rapeseed oil, soybean oil, sunflower oil, corn oil, sesame oil, tall oil, bone oil, and whale oil. One or more of these can be used. Among these, the diesel or heavy oil may be a straight-run diesel fraction, a vacuum diesel fraction, a desulfurized diesel fraction, a cracked base oil fraction, a straight-depleted diesel fraction, an atmospheric distillation residue, a vacuum distillation residue, a straight-depleted heavy oil, or a cracked heavy oil. In the present invention, the aforementioned fuel oils may also be hydrotreated before use.

The sulfur content of the base oil used in the fuel oil composition of the present invention is not particularly limited. However, from the perspective of the effects of the present invention, the sulfur content is preferably 0.01 to 0.50 mass%, more preferably 0.03 to 0.48 mass%, and even more preferably 0.10 to 0.45 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 mass% sulfur and a base oil containing less than 0.50 mass% sulfur may be mixed to obtain a base oil with a sulfur content of 0.01 to 0.50 mass%.

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

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 oils A, B, C, MDO, VLSFO, and ULSFO) as the base oil for 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 by mass. 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. In this case, 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 perspective 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, relative to the total amount of base oil, is preferably 10 to 100 mass%, more preferably 40 to 100 mass%, even more preferably 80 to 100 mass%, and particularly preferably 100 mass%. Furthermore, when the total amount of MGO and heavy oil in the base oil is 100 mass%, the content ratio of MGO to heavy oil is not particularly limited; for example, the content ratio of MGO to heavy oil can be 0:100 to 100:0 by mass, and preferably 0:100 to 90:10.

The fuel oil composition of the present invention may contain known fuel oil additives to improve combustibility, storage stability, oxidation stability, anti-wear, uniformity, safety, environmental compatibility, startability, low-temperature fluidity, and handleability. Examples of fuel oil additives that may be included include 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, and dyes. One or more types of each fuel oil additive may be included.

Examples of surface ignition inhibitors include organophosphorus compounds such as tributyl phosphite, trimethyl phosphite, tricresyl phosphate, tricyclohexyl phosphate, cresyl diphenyl phosphate, trimethyl phosphate, and methyl phenyl phosphate; and organoboron compounds such as 2-ethylhexyl boronate and butyl diisobutyl boronate. 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% of the total amount of the fuel oil composition.

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, and tetraethyl lead, and one or more of these can be used. The content of the octane improver is not particularly limited, but can be, for example, 0.001 to 10 mass% of the total amount of the fuel oil composition.

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. 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% of the total amount of the fuel oil composition.

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 Examples of isothiazoline antibacterial agents include 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 N-n-butyl-1,2-benzisothiazolin-3-one, and these may be used alone or in combination. The content of the antibacterial/bactericide is not particularly limited, but can be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

Examples of rust inhibitors include aliphatic amines and their salts, organic phosphate esters, and organic sulfonates, 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% of the total amount of the fuel oil composition.

Examples of deposit improvers include tricresyl phosphate, trimethyl phosphate, tris(chloroethyl)phosphate, polypropylene, polybutene, polyisobutyleneamine, polyetheramine, polyalkylamine, polyoxyalkyleneamine, polyalkylphenoxyaminoalkane, and polyalkylene succinimide, 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% of the total amount of the fuel oil composition.

Examples of antioxidants 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; Examples of antioxidants include phenol-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 sulfur-based antioxidants such as dilauryl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate, distearyl β,β'-thiodibutyrate, and dilauryl sulfide. One or more of these antioxidants can be used. The content of the antioxidant is not particularly limited, but can be, for example, 0.001 to 10 mass% based on the total amount of the fuel oil composition.

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-1,2,4-triazole, ...1-[bis(2-ethylhexyl)aminomethyl-1,2,4-triazole, Examples of suitable metal deactivators include 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. 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.

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, triphenyl phosphorothioate, β-dithiophosphorylated propionic acid, methylene bis(dibutyldithiocarbamate), O,O-diisopropyl-dithiophosphorylethylpropionate, 2,5-bis(n-nonyldithio)-1,3,4-thiazol-1-one, sulfur-based antiwear agents such as azole, 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, tricresyl phosphate, monoisopropyl phenyl phosphate, diisopropyl phenyl phosphate, triisopropyl phenyl phosphate phosphate, mono-tert-butylphenyl phosphate, di-tert-butylphenyl phosphate, tri-tert-butylphenyl phosphate, triphenylthiophosphate, monooctyl phosphite, dioctyl phosphite, trioctyl phosphite, monobutyl phosphite, dibutyl phosphite, tributyl phosphite, monophenyl phosphite, diphenyl phosphite, triphenyl phosphite, monoisopropylphenyl phosphite, diisopropylphenyl phosphite, triisopropylphenyl phosphite, mono-tert-butylphenyl phosphite Examples of suitable anti-wear agents include phosphorus compounds such as hexyl phosphate, 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, arachidin, and behenic acid; organometallic compounds such as metal naphthenates, metal fatty acid salts, metal phosphates, metal phosphate esters, and metal phosphites; and boron compounds, alkylamine salts of mono- and dihexyl phosphates, amine salts of phosphate esters, and mixtures of triphenyl thiophosphate and tert-butylphenyl derivatives. The amount of anti-wear agent is not particularly limited, but can be, for example, 0.01 to 10 mass% of the total amount of the fuel oil composition.

Examples of detergents and dispersants include phosphoric acid amides, aminoalkanes, alkylamine phosphate esters, polyetheramines, polybutenylamines, alkenyl succinimides, alkenyl succinate 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% of the total amount of the fuel oil composition.

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 monofatty acid esters, sorbitan difatty acid esters, sorbitan trifatty acid esters, sorbitan sesquifatty acid esters, and polyoxyalkylene-condensed sorbitan fatty acid esters. One or more of these may 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.

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

The flash point of the fuel oil composition of the present invention is not particularly limited, but from the viewpoint of the 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).

The pour point of the fuel oil composition of the present invention is not particularly limited, but from the viewpoint of the 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).

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, more preferably 2 to 200 mm ² /s, and most preferably 2 to 100 mm ² /s. 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).

The density 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 density at 15°C is preferably 0.70 g/ ^cm3 or more and 1.00 g/ ^cm3 or less, and more preferably 0.80 g/ ^cm3 or more and 0.98 g/ ^cm3 or less. In the present invention, the density of the fuel oil composition is measured by the method described in JIS K 2249 (2011).

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 liquid fuel oil. For example, it can be used as automotive fuel oil for passenger cars, trucks, etc., marine fuel oil for passenger ships, cargo ships, etc., aviation fuel oil for airplanes, helicopters, etc., railroad vehicle fuel oil for diesel locomotives, agricultural machinery fuel oil, construction machinery fuel oil, etc., and among these, it is preferably used as marine fuel oil.

The present invention will be explained in more detail below using examples. In the following examples, "%" is by weight unless otherwise specified.

<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 ester 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 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. 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."

<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 the 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.

<Friction reduction property evaluation>
The friction coefficients of the prepared glycerin fatty acid ester compositions 1 to 5 were measured under the following test conditions to evaluate their friction-reducing properties. 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% by mass. The friction coefficients were measured using an MTM tester (manufactured by PCS Instruments) by a ball-on-plate test under the following test conditions. Furthermore, as 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. The smaller the friction coefficient, the better the friction-reducing properties.

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

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 with excellent friction-reducing properties.

Claims (4)

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;
A friction modifier, wherein the ratio of glyceryl monooleate to glyceryl monolinoleate contained in a glycerin fatty acid ester composition is 95:5 to 85:15 by mass, and the total content of a diester of a fatty acid having 12 to 24 carbon atoms with glycerin and a triester of a fatty acid having 12 to 24 carbon atoms with glycerin is 0.2 to 5.0% by mass, based on the total amount of the glycerin fatty acid ester composition. 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. 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;
A lubricating oil composition or a fuel oil composition, wherein 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 the total content of a diester of a fatty acid having 12 to 24 carbon atoms with glycerin and a triester of a fatty acid having 12 to 24 carbon atoms with glycerin is 0.2 to 5.0 mass%. 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.