Composite and method for producing the composite

Abstract

The present invention addresses the problem of providing a complex which contains a low oil-soluble substance having a function as an additive for lubricating oil. The problem is solved by a solid-in-oil-type complex containing an active ingredient and a surfactant, wherein the active ingredient is at least one low oil-soluble substance selected from the group consisting of an oil-sparingly soluble substance and an oil-insoluble substance, and the low oil-soluble substance has a function as an additive for lubricating oil.

Description

[Technical Field]

[0001] The present invention relates to a composite and a method for producing the composite. More specifically, the present invention relates to a composite and a method for producing the composite, a lubricating oil additive composition containing the composite, and a lubricating oil composition containing the composite or the lubricating oil additive composition. [Background technology]

[0002] Lubricating oil additives are added to lubricating base oils to impart or supplement desired properties and performance to the lubricating oil composition. For example, phosphate esters represented by the following general formula are known as lubricating oil additives (see, for example, Patent Document 1). The polar group portion (phosphate group) of phosphate esters binds to the metal surface to form an adsorption film, thereby functioning as an extreme pressure agent. Thus, lubricating oil additives often have a polar group portion in order to function as such.

[0003] [ka] [In the above general formula, m represents an integer of 1 or 2, and R represents a linear or branched hydrocarbon group having 6 to 22 carbon atoms.] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2017-88651 Summary of the Invention [Problem to be solved by the invention]

[0005] The polar group portion of a molecule generally has hydrophilic properties. Therefore, in order to use a substance with a polar group portion as a lubricating oil additive, it is necessary to introduce an appropriate lipophilic group into the substance to make it oil-soluble. The phosphate ester represented by the above general formula ensures oil solubility by making R a hydrocarbon group with 6 to 22 carbon atoms.

[0006] However, this limits the substances that can be used as lubricating oil additives. It is expected that, with further technological advances in the fields of automobiles, industrial machinery, and the like, the performance requirements for lubricating oil compositions will become even more stringent in the future. Therefore, from the perspective of expanding the substances that can be used as lubricating oil additives and achieving a dramatic advance in the technology related to lubricating oil additives, it is desirable to create lubricating oil additives that utilize poorly oil-soluble substances and oil-insoluble substances (hereinafter, these are also collectively referred to as "low oil-soluble substances").

[0007] The present inventors have conducted extensive research in light of the above-mentioned demands and have found that a specific complex containing a poorly oil-soluble substance that functions as an additive for lubricating oil is effective in meeting the above-mentioned demands.

[0008] Therefore, an object of the present invention is to provide a composite containing a poorly oil-soluble substance that functions as a lubricating oil additive, a lubricating oil additive composition containing the composite, a lubricating oil composition containing the composite or the lubricating oil additive composition, and a method for producing the composite. [Means for solving the problem]

[0009] As a result of extensive research, the present inventors have found that a solid-in-oil type composite containing a poorly oil-soluble substance that functions as a lubricating oil additive can solve the above-mentioned problems, and after further extensive research, have completed the present invention.

[0010] That is, the present invention relates to the following [1] to [6]. [1] A solid-in-oil type complex containing an active ingredient and a surfactant, the active ingredient is one or more low-oil-soluble substances selected from the group consisting of poorly oil-soluble substances and oil-insoluble substances, The complex, wherein the poorly oil-soluble substance is a substance that functions as an additive for lubricating oil. [2] A lubricating oil additive composition containing the complex described in [1] above. [3] A lubricating oil composition comprising a lubricating base oil and the composite according to [1] above or the lubricating oil additive composition according to [2] above. [4] A method for producing a solid-in-oil type complex containing an active ingredient and a surfactant, comprising: The method includes the following steps (S1) to (S4): Step (S1): A step of preparing an aqueous liquid (W) by dissolving and / or dispersing the active ingredient in water. Step (S2): A step of dissolving the surfactant in an organic solvent to prepare an oily liquid (O). Step (S3): A step of mixing the aqueous liquid (W) and the oily liquid (O) to prepare a water-in-oil emulsion. Step (S4): A step of removing the organic solvent from the water-in-oil emulsion and then drying the emulsion. the active ingredient is one or more low-oil-soluble substances selected from the group consisting of poorly oil-soluble substances and oil-insoluble substances, The method for producing a composite, wherein the poorly oil-soluble substance is a substance that functions as an additive for lubricating oil. [5] A method of using the complex according to [1] above as an additive for lubricating oil. [6] A method of using the complex according to [1] above in a lubricating oil composition. [Effects of the Invention]

[0011] According to the present invention, it is possible to provide a composite containing a poorly oil-soluble substance that functions as a lubricating oil additive, a lubricating oil additive composition containing the composite, a lubricating oil composition containing the composite or the lubricating oil additive composition, and a method for producing the composite. [Brief explanation of the drawings]

[0012] [Figure 1] FIG. 1 is a schematic cross-sectional view showing one embodiment of a solid-in-oil type composite of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0013] In this specification, for preferred numerical ranges (e.g., ranges of content, etc.), the lower limit and upper limit values ​​described in stages can be independently combined. For example, if the description is "preferably A to B, more preferably C to D," the "preferable lower limit (A)" and the "more preferable upper limit (D)" can be combined to form "A to D." Furthermore, unless otherwise specified, the numerical range "lower limit value to upper limit value" described in this specification means that the range is equal to or greater than the lower limit value and equal to or less than the upper limit value. In this specification, the numerical values ​​in the examples are numerical values ​​that can be used as upper or lower limit values.

[0014] In this specification, "Solid-in-Oil type" may be abbreviated as "S / O type," and "Water-in-Oil type" may be abbreviated as "W / O type."

[0015] In this specification, the term "poorly oil-soluble substance" is a concept that encompasses "poorly oil-soluble substance" and "oil-insoluble substance", as described above. Note that the term "poorly oil-soluble substance" also encompasses "extremely poorly oil-soluble substance". Specifically, when the poorly oil-soluble substance is a solid at room temperature (25°C), the term "poorly oil-soluble substance" refers to a substance whose solubility in hexane at room temperature (25°C) is, for example, 1 g / 100 mL or less, and the solubility may be 0.1 g / 100 mL or less or 0.01 g / 100 mL or less. When the poorly oil-soluble substance is a liquid at room temperature (25°C), the term "poorly oil-soluble substance" refers to a substance whose solubility in hexane at room temperature (25°C) is, for example, 1 mL / 100 mL or less, and the solubility may be 0.1 mL / 100 mL or less or 0.01 mL / 100 mL or less. In this specification, the term "oil-soluble substance" is a concept that also includes "slightly oil-soluble substance." When the poorly oil-soluble substance is a solid at room temperature (25°C), it means a substance whose solubility in hexane (n-hexane) at room temperature (25°C) is greater than 1 g / 100 mL (preferably 5 g / 100 mL, more preferably 10 g / 100 mL). When the poorly oil-soluble substance is a liquid at room temperature (25°C), it means a substance whose solubility in hexane (n-hexane) at room temperature (25°C) is greater than 1 mL / 100 mL (preferably 5 mL / 100 mL, more preferably 10 mL / 100 mL).

[0016] In this specification, the term "poorly water-soluble substance" is a general term that encompasses "poorly water-soluble substance" and "water-insoluble substance." Note that "poorly water-soluble substance" is a general term that also encompasses "extremely poorly water-soluble substance." Specifically, the term "poorly water-soluble substance" refers to a substance that, when it is solid at room temperature (25°C), has a solubility in water at room temperature (25°C) of, for example, 1 g / 100 mL or less, and may be 0.1 g / 100 mL or less or 0.01 g / 100 mL or less. Also, when it is liquid at room temperature (25°C), it refers to a substance that, when it is liquid at room temperature (25°C), has a solubility in water at room temperature (25°C) of, for example, 1 mL / 100 mL or less, and may be 0.1 mL / 100 mL or less or 0.01 mL / 100 mL or less. In this specification, the term "water-soluble substance" is a concept that also includes slightly water-soluble substances. When the water-soluble substance is solid at room temperature (25°C), it means a substance whose solubility in water at room temperature (25°C) is greater than 1 g / 100 mL (preferably 5 g / 100 mL, more preferably 10 g / 100 mL). When the low-water-soluble substance is liquid at room temperature (25°C), it means a substance whose solubility in water at room temperature (25°C) is greater than 1 mL / 100 mL (preferably 5 mL / 100 mL, more preferably 10 mL / 100 mL).

[0017] [Embodiments of the composite of the present invention] The complex of the present invention is an S / O type complex containing an active ingredient and a surfactant, wherein the active ingredient is one or more low oil-soluble substances selected from the group consisting of poorly oil-soluble substances and oil-insoluble substances, and the low oil-soluble substance is a substance that functions as an additive for lubricating oil.

[0018] FIG. 1 shows one embodiment of the S / O type complex of the present invention. The S / O type complex 1 has a structure in which the active ingredient (X) is coated with the surfactant (Y). The S / O complex 1 can be obtained by removing the internal aqueous phase from a W / O emulsion. The orientation of the surfactant (Y) in the S / O complex 1 is maintained as in the W / O emulsion. Therefore, in the S / O complex 1, the surfactant (Y) is oriented, as in the W / O emulsion, with the hydrophilic group (Ya) facing the encapsulated substance (i.e., the active ingredient (X) side) and the lipophilic group (Yb) facing outward. The size of the S / O complex 1 is reduced by the amount of the internal aqueous phase removed from the W / O emulsion. Specifically, the particle size (hydrodynamic diameter) of the S / O complex 1 according to one embodiment of the present invention, as measured by dynamic light scattering, is preferably 50 nm or more, more preferably 40 nm or more, and even more preferably 30 nm or more. The particle size is also preferably 600 nm or less, more preferably 500 nm or less, and even more preferably 400 nm or less. The upper and lower limits of these numerical ranges can be combined in any desired manner. Specifically, the first range is preferably 50 nm to 600 nm, more preferably 40 nm to 600 nm, and even more preferably 30 nm to 600 nm. The second range is preferably 50 nm to 500 nm, more preferably 40 nm to 500 nm, and even more preferably 30 nm to 500 nm. The third range is preferably 50 nm to 400 nm, more preferably 40 nm to 400 nm, and even more preferably 30 nm to 400 nm.

[0019] When the S / O type complex 1 of the present invention is added to a lubricating base oil, the active ingredient (X) is covered with surfactant (Y) with the lipophilic group (Yb) facing outward, and the particle size is nano-sized, so that the active ingredient (X) is uniformly dispersed in the lubricating base oil while maintaining a state in which it is encapsulated in the S / O type complex 1. Therefore, the active ingredient (X) in the S / O type complex 1 is in a state as if it were dissolved in the lubricating base oil. The S / O complex 1 then disintegrates in response to a trigger, which will be described later, releasing the encapsulated active ingredient (X), allowing the active ingredient (X) to function as a lubricating oil additive.

[0020] The active ingredients and surfactants constituting the complex of the present invention will be described in detail below.

[0021] <Active ingredient> The active ingredient is one or more poorly oil-soluble substances selected from the group consisting of poorly oil-soluble substances and oil-insoluble substances, and the poorly oil-soluble substances are substances that function as additives for lubricating oils. According to the present invention, it is now possible to use, as lubricating oil additives, poorly oil-soluble substances that could not previously be used as lubricating oil additives, thereby expanding the range of substances that can be used as lubricating oil additives. The poorly oil-soluble substances may be used alone or in combination of two or more.

[0022] Here, the poorly oil-soluble substance is preferably water-soluble from the viewpoint of facilitating the production of the complex by dissolving the poorly oil-soluble substance in water during the production process of the complex. From the same viewpoint, the octanol / water partition coefficient (logP оw The octanol / water partition coefficient can be measured, for example, by OECD Test Guideline (OECD Council Decision "C(81)30 Final Annex 1") 107 or Japanese Industrial Standard Z7260-107 (2000) "Measurement of partition coefficient (1-octanol / water) - Shake flask method." However, the poorly oil-soluble substance is not limited to being water-soluble, and may be poorly water-soluble. Even if the poorly oil-soluble substance is poorly water-soluble, the poorly oil-soluble substance can be dispersed in water during the production process of the complex to produce the complex.

[0023] The function of the poorly oil-soluble substance used in the composite of the present invention as an additive for lubricating oil is not particularly limited, and examples thereof include one or more functions selected from the group consisting of a load-bearing additive, a base number enhancer, an antioxidant, a passivating agent, a rust inhibitor, an anti-corrosion agent, a self-repairing agent, a coating agent, and an anti-foaming agent.

[0024] Hereinafter, poorly oil-soluble substances having functions as load-bearing additives, base number enhancers, antioxidants, passivating agents, rust inhibitors, anti-corrosion agents, self-repairing agents, coating agents, or anti-foaming agents will be described in detail, giving specific examples.

[0025] (load-bearing additive) The load-bearing additive can be any low-oil-soluble substance that functions as an oiliness improver, anti-wear agent, or extreme pressure agent, without any particular limitation. Specific examples of poorly oil-soluble substances that can be used as load-bearing additives include water-soluble compounds containing a P=O structure, such as phosphoric acids selected from phosphoric acid (phosphate), phosphorous acid (phosphite), phosphonate, and phosphinate, water-soluble esters of the phosphoric acids, water-soluble condensates of the phosphoric acids, water-soluble amine salts of the phosphoric acids, and water-soluble metal salts of the phosphoric acids; sulfonic acids selected from sulfonic acid, sulfide, sulfoxide, and sulfone, water-soluble esters of the sulfonic acids, water-soluble condensates of the sulfonic acids, water-soluble amine salts of the sulfonic acids, and water-soluble compounds containing an S=O structure, such as water-soluble metal salts of the sulfonic acids; water-soluble compounds containing a C=O structure, such as carboxylic acids selected from carboxylic acids, benzoic acid, and nitrobenzoic acid, water-soluble esters of the carboxylic acids, water-soluble condensates of the carboxylic acids, water-soluble amine salts of the carboxylic acids, and water-soluble metal salts of the carboxylic acids; phosphomolybdic acids such as 12-molybdo(VI)phosphate n-hydrate and water-soluble derivatives or water-soluble salts thereof; thiophosphates and thiocarbamates, and water-soluble derivatives or water-soluble salts thereof; ionic liquids, etc. Although all of the above substances are water-soluble, substances that can be used as load-bearing additives may be poorly water-soluble or water-insoluble. Specific examples of such substances include water-insoluble substances such as molybdenum disulfide, molybdenum oxide, and tungsten disulfide, as well as derivatives or salts thereof; carbon-based compounds such as carbon black, carbon graphite, graphene, carbon nanotubes, and fullerenes; and polymer compounds such as polytetrafluoroethylene and cellulose nanofibers. Carbon-based compounds and polymer compounds exert a friction-reducing effect by acting like a roller. Among these, molybdenum disulfide, molybdenum oxide, and tungsten disulfide, as well as carbon black, carbon graphite, graphene, carbon nanotubes, and fullerenes, are substances classified as "insoluble substances" that are insoluble in oil and water, and in the present invention, such substances can also be encapsulated in the complex as active ingredients. These may be used alone or in combination of two or more.

[0026] (Base number enhancer) The base number enhancer may be any low-oil-soluble substance capable of neutralizing the acidic substances that cause increased acidity in the lubricating oil composition, without particular limitation. The use of a base number enhancer contributes to improving the long drain of engine oils, for example. Specific examples of poorly oil-soluble substances that can be used as base number enhancers include polyalkylene polyamines, guanidines such as guanidine carbonate, aminoguanidines such as aminoguanidine bicarbonate, arginine, phenylamine, naphthylamine, phenylenediamine, methylaniline, imine, and water-soluble derivatives thereof; cyclic amines such as pyridine, piperazine, piperidine, morpholine, indole, imidazole, indazole, and triazole, and water-soluble derivatives thereof; and water-soluble inorganic metal compounds such as potassium carbonate. Although all of the above substances are water-soluble, substances that can be used as base number enhancers may be poorly water-soluble or water-insoluble. Specific examples of such substances include inorganic metal compounds such as barium carbonate, calcium carbonate, and magnesium carbonate. These inorganic metal compounds are classified as "insoluble substances" that are both oil-insoluble and water-insoluble. However, in the present invention, such substances can also be encapsulated in the complex as active ingredients. These may be used alone or in combination of two or more.

[0027] (antioxidant) The antioxidant can be any low-oil-soluble substance that has the function of suppressing oxidative degradation of the lubricating oil composition by absorbing ultraviolet light, stopping chain reactions, decomposing peroxides, and inactivating metals, without any particular limitation. Specific examples of poorly oil-soluble substances that can be used as antioxidants include catecholamines, acetylcholine, serotonin, histamine, and melatonin, as well as their water-soluble derivatives; ascorbic acid, phenol, hydroxyanisole, and catechin, as well as their water-soluble derivatives; poorly oil-soluble phenolic antioxidants such as di-tert-butylcresol; and poorly oil-soluble phenolic antioxidants such as naphthylamine. These may be used alone or in combination of two or more.

[0028] (passivating agent) There are no particular limitations on the passivating agent, so long as it is a low oil-soluble substance that has the function of forming an oxide film that has corrosion resistance on the metal surface. Specific examples of poorly oil-soluble substances that can be used as passivating agents include sodium nitrite, potassium sulfite, and sulfur dioxide, as well as water-soluble derivatives thereof.

[0029] (rust inhibitor, anti-corrosion agent) There are no particular limitations on the rust inhibitors and anti-corrosion agents that can be used, as long as they are low-oil-soluble substances that have the function of insulating metal surfaces from water and oxygen. Specific examples of substances that can be used as rust inhibitors and anti-corrosion agents include, for iron, dicyclohexylammonium nitrite, diisopropylammonium nitrite, caprate, laurate, and carbonate. For copper, benzotriazole is used. Other examples include water-soluble rust inhibitors such as amine salts, lower fatty acids, and their salts. These may be used alone or in combination of two or more.

[0030] (self-repairing agents, coating agents) The self-repairing agent or coating agent can be any low oil-soluble substance that has the function of repairing minute scratches or cracks that occur on metal or resin surfaces, without any particular limitations. Specific examples of low oil-solubility substances that can be used as self-repairing agents and coating agents include epoxy resin materials; thermosetting polyketones; self-repairing agents such as epoxy resins; crosslinking agents such as ethylene-methacrylic acid copolymers; and coating agents such as polyurethanes.

[0031] (Antifoaming agent) The antifoaming agent can be any low oil-soluble substance that has the function of suppressing or eliminating foaming that occurs in the lubricating oil composition, without any particular limitations. Specific examples of poorly oil-soluble substances that can be used as antifoaming agents include silicon-based compounds such as silicone, fluorine-based compounds, and derivatives thereof.

[0032] (Other ingredients) Other ingredients include colorants and marker substances such as fluorescent substances that are poorly oil-soluble. For example, in the case where degradation of the lubricating oil composition is a trigger for the collapse of the complex, by incorporating a marker substance such as a colorant into the complex, the marker substance is released when the complex collapses, making it possible to visually confirm the deterioration of the lubricating oil composition. As a specific example, by incorporating a marker substance into a complex together with the base number enhancer, the complex can be disintegrated by deterioration due to the accumulation of acidic substances in the lubricating oil composition, and upon disintegration, the marker substance can be released from inside the complex, allowing the deterioration to be visually confirmed.

[0033] <Surfactant> There are no particular restrictions on the surfactant that can be used, as long as it can coat the poorly oil-soluble substance to form an S / O type complex and is acceptable as an additive for lubricating oils. For example, nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, and the like can be mentioned. These may be used alone or in combination of two or more. By combining two or more surfactants, the coating formed by the surfactants and surrounding the poorly oil-soluble substance can be made strong and stable.

[0034] (nonionic surfactants) The nonionic surfactant may be one or more selected from ester-type, ether-type, ester ether-type, and alkanolamide-type surfactants. Specific examples of nonionic surfactants include alkyl fatty acid esters, glycerin fatty acid esters, polyglycerin fatty acid esters, polyoxyethylene glycerin fatty acid esters, sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene sorbit fatty acid esters, aliphatic polyalkylene polyamines, fatty acid amides, polyalkylene polyamine fatty acid amides, aminoimidazole fatty acid amides, and aminotriazole fatty acid amides. These may be used alone or in combination of two or more.

[0035] (anionic surfactants) The anionic surfactant may be one or more selected from carboxylic acid type, sulfonic acid type, sulfate type, and phosphate type surfactants. Specific examples of anionic surfactants include aliphatic carboxylates, polyoxyethylene ether carboxylates, N-acylsarcosinates, N-acylglutamates, dialkyl sulfosuccinates, alkanesulfonates, α-olefinsulfonates, alkylbenzenesulfonates, naphthalenesulfonate-formaldehyde condensates, alkylnaphthalenesulfonates, N-methyl-N-acyltaurates, alkyl sulfates, polyoxyethylene alkyl ether sulfates, fat and oil sulfate esters, alkyl phosphates, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkylphenyl ether phosphates. These may be used alone or in combination of two or more.

[0036] (cationic surfactant) The cationic surfactant may be one or more selected from alkylamine salt type and quaternary ammonium salt type surfactants. Specific examples of cationic surfactants include monoalkylamine salts, dialkylamine salts, trialkylamine salts, alkyltrimethylammonium halides, dialkyldimethylammonium halides, and alkylbenzalkonium chlorides. These may be used alone or in combination of two or more.

[0037] (Amphoteric surfactant) The amphoteric surfactant may be one or more selected from carboxybetaine type, 2-alkylimidazoline derivative type, glycine type, and amine oxide type surfactants. Specific examples of amphoteric surfactants include alkyl betaines, fatty acid amidopropyl betaines, 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaines, alkyl diethylene triamino acetic acids, dialkyl diethylene triamino acetic acids, and alkyl amine oxides. These may be used alone or in combination of two or more.

[0038] (Suitable surfactants) In one aspect of the present invention, from the viewpoint of facilitating improvement in the stability of the S / O type complex, it is preferable to use one or more surfactants selected from the group consisting of nonionic surfactants and anionic surfactants, and it is more preferable to use a nonionic surfactant.

[0039] When a nonionic surfactant is used as the surfactant, it is preferable to use an ester surfactant made from a fatty acid having 8 to 24 carbon atoms, in order to more easily improve the stability of the S / O type complex. From the viewpoint of further improving the stability of the S / O type complex, the number of carbon atoms in the fatty acid is more preferably 10 to 24, even more preferably 12 to 24, still more preferably 14 to 24, and even more preferably 16 to 24. The aliphatic group constituting the fatty acid may be saturated or unsaturated, and may be linear or branched, but is preferably linear. Furthermore, from the viewpoint of further improving the stability of the S / O type complex, the ester type surfactant is preferably one or more selected from the group consisting of glycerin fatty acid esters, sorbitan fatty acid esters, and sucrose fatty acid esters.

[0040] Specific examples of preferred compounds as glycerin fatty acid esters include glycerin octanoate (number of carbon atoms in constituent fatty acid: 8), glycerin nonanoate (number of carbon atoms in constituent fatty acid: 9), glycerin decanoate (number of carbon atoms in constituent fatty acid: 10), glycerin undecanoate (number of carbon atoms in constituent fatty acid: 11), glycerin laurate (number of carbon atoms in constituent fatty acid: 12), glycerin tridecanoate (number of carbon atoms in constituent fatty acid: 13), glycerin myristate (number of carbon atoms in constituent fatty acid: 14), glycerin pentadecanoate (number of carbon atoms in constituent fatty acid: 15), glycerin palmitate (number of carbon atoms in constituent fatty acid: 16), glycerin margarate (number of carbon atoms in constituent fatty acid: 17), glycerin sucrose (number of carbon atoms in constituent fatty acid: 18), glycerin sucrose (number of carbon atoms in constituent fatty acid: 19), glycerin sucrose (number of carbon atoms in constituent fatty acid: 20), glycerin sucrose (number of carbon atoms in constituent fatty acid: 21), glycerin sucrose (number of carbon atoms in constituent fatty acid: 22), glycerin sucrose (number of carbon atoms in constituent fatty acid: 23), glycerin sucrose (number of carbon atoms in constituent fatty acid: 24), glycerin sucrose (number of carbon atoms in constituent fatty acid: 25), glycerin sucrose (number of carbon atoms in constituent fatty acid: 26), glycerin sucrose (number of carbon atoms in constituent fatty acid: 27), glycerin sucrose (number of carbon atoms in constituent fatty acid: 28), glycerin sucrose (number of carbon atoms in constituent fatty acid: 29), glycerin sucrose (number of carbon atoms in constituent Examples include glyceryl thearate (18 carbon atoms in fatty acid), glyceryl oleate (18 carbon atoms in fatty acid, 1 double bond), glyceryl nonadecanoate (19 carbon atoms in fatty acid), glyceryl arachidate (20 carbon atoms in fatty acid), glyceryl eicosenoate (20 carbon atoms in fatty acid, 1 double bond), glyceryl heneicosylate (21 carbon atoms in fatty acid), glyceryl behenate (22 carbon atoms in fatty acid), glyceryl erucate (22 carbon atoms in fatty acid, 1 double bond), glyceryl tricosylate (23 carbon atoms in fatty acid), and glyceryl lignocerate (24 carbon atoms in fatty acid). These may be used alone or in combination of two or more. The ester valence of the glycerin fatty acid ester is preferably 1 or 2. That is, the glycerin fatty acid ester is preferably one or more selected from the group consisting of glycerin fatty acid monoesters and glycerin fatty acid diesters.

[0041] Specific examples of preferred compounds as sorbitan fatty acid esters include sorbitan octanoate (number of carbon atoms in constituent fatty acid: 8), sorbitan nonanoate (number of carbon atoms in constituent fatty acid: 9), sorbitan decanoate (number of carbon atoms in constituent fatty acid: 10), sorbitan undecanoate (number of carbon atoms in constituent fatty acid: 11), sorbitan laurate (number of carbon atoms in constituent fatty acid: 12), sorbitan tridecanoate (number of carbon atoms in constituent fatty acid: 13), sorbitan myristate (number of carbon atoms in constituent fatty acid: 14), sorbitan pentadecanoate (number of carbon atoms in constituent fatty acid: 15), sorbitan palmitate (number of carbon atoms in constituent fatty acid: 16), sorbitan margarate (number of carbon atoms in constituent fatty acid: 17), and sorbitan laurate. Examples include sorbitan thearate (18 carbon atoms in fatty acid), sorbitan oleate (18 carbon atoms in fatty acid, 1 double bond), sorbitan nonadecanoate (19 carbon atoms in fatty acid), sorbitan arachidate (20 carbon atoms in fatty acid), sorbitan eicosenoate (20 carbon atoms in fatty acid, 1 double bond), sorbitan heneicosylate (21 carbon atoms in fatty acid), sorbitan behenate (22 carbon atoms in fatty acid), sorbitan erucate (22 carbon atoms in fatty acid, 1 double bond), sorbitan tricosylate (23 carbon atoms in fatty acid), and sorbitan lignocerate (24 carbon atoms in fatty acid). These may be used alone or in combination of two or more. The ester valence of the sorbitan fatty acid ester is preferably 1, 2, or 3. That is, the sorbitan fatty acid ester is preferably one or more selected from the group consisting of sorbitan fatty acid monoesters, sorbitan fatty acid diesters, and sorbitan fatty acid triesters.

[0042] Specific examples of preferred compounds as sucrose fatty acid esters include sucrose octanoate (number of carbon atoms in constituent fatty acid: 8), sucrose nonanoate (number of carbon atoms in constituent fatty acid: 9), sucrose decanoate (number of carbon atoms in constituent fatty acid: 10), sucrose undecanoate (number of carbon atoms in constituent fatty acid: 11), sucrose laurate (number of carbon atoms in constituent fatty acid: 12), sucrose tridecanoate (number of carbon atoms in constituent fatty acid: 13), sucrose myristate (number of carbon atoms in constituent fatty acid: 14), sucrose pentadecanoate (number of carbon atoms in constituent fatty acid: 15), sucrose palmitate (number of carbon atoms in constituent fatty acid: 16), sucrose margarate (number of carbon atoms in constituent fatty acid: 17 ... Examples include sugar stearic acid ester (18 carbon atoms in fatty acid), sucrose oleic acid ester (18 carbon atoms in fatty acid, 1 double bond), sucrose nonadecanoic acid ester (19 carbon atoms in fatty acid), sucrose arachidic acid ester (20 carbon atoms in fatty acid), sucrose eicosenoic acid ester (20 carbon atoms in fatty acid, 1 double bond), sucrose heneicosyl acid ester (21 carbon atoms in fatty acid), sucrose behenic acid ester (22 carbon atoms in fatty acid), sucrose erucic acid ester (22 carbon atoms in fatty acid, 1 double bond), sucrose tricosyl acid ester (23 carbon atoms in fatty acid), and sucrose lignoceric acid ester (24 carbon atoms in fatty acid). These may be used alone or in combination of two or more. The ester valence of the sucrose fatty acid ester is preferably 1, 2, or 3. That is, the sucrose fatty acid ester is preferably one or more selected from the group consisting of sucrose fatty acid monoesters, sucrose fatty acid diesters, and sucrose fatty acid triesters.

[0043] Furthermore, by using a nonionic surfactant as the surfactant, when the complex disintegrates, the nonionic surfactant functions as a load-bearing additive, and also exerts the secondary effect of imparting wear resistance to the lubricating oil composition.

[0044] Furthermore, when an anionic surfactant is used as the surfactant, it is preferable to use a carboxylic acid surfactant made from a fatty acid having 8 to 24 carbon atoms, in order to more easily improve the stability of the S / O type complex. From the same viewpoint, the number of carbon atoms in the fatty acid is more preferably 10 to 24. The aliphatic group constituting the fatty acid may be saturated or unsaturated, and may be linear or branched, but is preferably linear. Specific examples of preferred compounds as carboxylic acid surfactants include octanoic acid (number of carbon atoms: 8), nonanoic acid (number of carbon atoms: 9), decanoic acid (number of carbon atoms: 10), undecanoic acid (number of carbon atoms: 11), lauric acid (number of carbon atoms: 12), tridecanoic acid (number of carbon atoms: 13), myristic acid (number of carbon atoms: 14), pentadecanoic acid (number of carbon atoms: 15), palmitic acid (number of carbon atoms: 16), margaric acid (number of carbon atoms: 17), stearyl alcohol (number of carbon atoms: 18), stearyl alcohol (number of carbon atoms: 19), stearyl alcohol (number of carbon atoms: 20), stearyl alcohol (number of carbon atoms: 21), stearyl alcohol (number of carbon atoms: 22), stearyl alcohol (number of carbon atoms: 23), stearyl alcohol (number of carbon atoms: 24), stearyl alcohol (number of carbon atoms: 25), stearyl alcohol (number of carbon atoms: 26), stearyl alcohol (number of carbon atoms: 27), stearyl alcohol (number of carbon atoms: 28), stearyl alcohol (number of carbon atoms: 29), stearyl alcohol (number of carbon atoms: 30), stearyl alcohol (number of carbon atoms: 31), stearyl alcohol (number of carbon atoms: 32), stearyl alcohol (number of carbon atoms: 33), stearyl alcohol (number of carbon atoms: 34), stearyl alcohol (number of carbon atoms: 35), stearyl alcohol (number of carbon atoms: 36), stearyl alcohol (number of carbon atoms: 37), stearyl alcohol (number of carbon atoms: 38), stearyl alcohol (number of carbon atoms: 39), stearyl alcohol (number of carbon atoms: 40), stearyl alcohol (number of carbon atoms: 41), stearyl alcohol (number of carbon atoms: 42), stearyl Examples include arachidic acid (carbon number: 18), oleic acid (carbon number: 18, double bond: 1), nonadecanoic acid (carbon number: 19), arachidic acid (carbon number: 20), eicosenoic acid (carbon number: 20, double bond: 1), heneicosylic acid (carbon number: 21), behenic acid (carbon number: 22), erucic acid (carbon number: 22, double bond: 1), tricosylic acid (carbon number: 23), and lignoceric acid (carbon number: 24). Furthermore, by using a carboxylic acid surfactant as the surfactant, when the complex disintegrates, the nonionic surfactant functions as a load-bearing additive, and also has the secondary effect of imparting wear resistance to the lubricating oil composition.

[0045] In one embodiment of the present invention, the surfactant is preferably a hydrophobic surfactant, from the viewpoint of facilitating the preparation of a W / O type emulsion, which is a precursor of an S / O type complex. Specifically, the HLB value is preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less. It is also preferably greater than 0, more preferably 1.0 or greater, and even more preferably 1.5 or greater. The upper and lower limits of these numerical ranges can be arbitrarily combined. Specifically, it is preferably greater than 0 to 10, more preferably 1.0 to 8.0, and even more preferably 1.5 to 6.0. The HLB value means the HLB (Hydrophilic-Lipophilic Balance) value calculated by the Griffin method. However, the surfactant is not limited to those having an HLB value of 10 or less, and a surfactant having an HLB value of 10 or less may be used in combination with a surfactant having an HLB value of more than 10, within the range in which an S / O type complex can be prepared.

[0046] <Additives for complex formation> The S / O type complex of one embodiment of the present invention may contain a complex-forming additive other than the active ingredient and surfactant, as long as the additive does not impair the effects of the present invention. Examples of additives for forming a complex include stabilizers such as polyvinyl alcohol and higher alcohols having 10 to 30 carbon atoms (for example, hexadecanol). Furthermore, the S / O type complex of one embodiment of the present invention may contain additives (for example, pH adjusters, buffers, etc.) that can be used in the process of producing the complex.

[0047] [Method of manufacturing the composite] The method for producing the composite of the present invention is a method for producing a solid-in-oil type composite containing an active ingredient and a surfactant, and includes the following steps (S1) to (S4). Step (S1): A step of preparing an aqueous liquid (W) by dissolving and / or dispersing the active ingredient in water. Step (S2): A step of dissolving the surfactant in an organic solvent to prepare an oily liquid (O). Step (S3): A step of mixing the aqueous liquid (W) and the oily liquid (O) to prepare a water-in-oil emulsion. Step (S4): A step of removing the organic solvent from the water-in-oil emulsion and then drying the emulsion. the active ingredient is one or more low-oil-soluble substances selected from the group consisting of poorly oil-soluble substances and oil-insoluble substances, The poorly oil-soluble substance is a substance that functions as an additive for lubricating oil.

[0048] <Process (S1)> In step (S1), an aqueous liquid (W) is prepared by at least either dissolving or dispersing a poorly oil-soluble substance, which is an active ingredient, in water. When the poorly oil-soluble substance is a water-soluble poorly oil-soluble substance, the water-soluble poorly oil-soluble substance is dissolved in water to prepare the aqueous liquid (W). The water solvent may be at room temperature (25°C), or may be warm water above 25°C and below 100°C (preferably 30°C to 90°C, more preferably 40°C to 80°C) from the viewpoint of improving the solubility of the water-soluble poorly oil-soluble substance in water. When the poorly oil-soluble substance is one or more poorly water-soluble substances (particularly insoluble substances) selected from the group consisting of poorly water-soluble substances and water-insoluble substances, a step (S0) is carried out in which the poorly water-soluble, poorly oil-soluble substance is pulverized in a bead mill to produce nano-powder, which is then dispersed in water to prepare an aqueous liquid (W). The concentration of the poorly oil-soluble substance in the aqueous liquid (W) is not particularly limited as long as it is a concentration that can substantially dissolve or disperse the poorly oil-soluble substance, but is preferably 0.1 g / 100 mL to 5.0 g / 100 mL.

[0049] (Bead mill grinding process (S0)) In the bead mill pulverization step (S0), the poorly water-soluble and poorly oil-soluble substance is wet-pulverized in water, which is a liquid solvent, to uniformly disperse nanopowder of the poorly water-soluble and poorly oil-soluble substance in water. The material of the beads used in the bead mill pulverization treatment may be titania, alumina, zirconia, etc., and is preferably zirconia. The material of the vessel used in the bead mill pulverization treatment is preferably the same as that of the beads. The diameter of the beads used is preferably 0.05 mm to 0.5 mm, more preferably 0.05 mm to 0.3 mm, and even more preferably 0.05 mm to 0.2 mm. In the bead mill pulverization treatment, the filling rate of the beads in the vessel is preferably 20% to 70% by volume, more preferably 25% to 60% by volume, and even more preferably 30% to 50% by volume. In the bead mill pulverization treatment, the rotation speed in the vessel of the bead mill is preferably 1,000 rpm to 5,000 rpm, more preferably 1,000 rpm to 4,000 rpm, and even more preferably 1,500 rpm to 3,000 rpm. The time for the pulverization treatment using a bead mill is usually 30 minutes to 12 hours, preferably 1 hour to 5 hours, and more preferably 1 hour to 4 hours. After the bead mill pulverization treatment, it is preferable to use filter paper (for example, No. 2 filter paper) to remove coarse particles from the poorly water-soluble and poorly oil-soluble substances. By carrying out the bead mill pulverization treatment, it is possible to encapsulate not only poorly water-soluble and poorly oil-soluble substances but also insoluble substances in the complex. In addition, if the poorly water-soluble, poorly oil-soluble substance is not an insoluble substance, the dissolution of the poorly water-soluble, poorly oil-soluble substance in water may be slightly promoted during the process of pulverizing the poorly water-soluble, poorly oil-soluble substance by ball milling. However, even in such cases, the poorly water-soluble, poorly oil-soluble substance, including both the soluble and dispersible portions in water, can be encapsulated in the complex.

[0050] <Process (S2)> In step (S2), a surfactant is dissolved in an organic solvent to prepare an oily liquid (O). The organic solvent is not particularly limited as long as it can dissolve the surfactant and can be distilled off in the next step (S3). Examples of the organic solvent include alcohols, aliphatic hydrocarbons, aromatic hydrocarbons, ester-based solvents, and halogenated aliphatic hydrocarbons. The alcohol is preferably one that separates into layers from water at room temperature, and for example, a C4 to C10 aliphatic alcohol is preferred. An example of the aliphatic hydrocarbon is hexane. An example of the aromatic hydrocarbon is toluene. Examples of ester solvents include ethyl acetate. Examples of halogenated aliphatic hydrocarbons include methylene chloride. The organic solvent may be used alone or in combination of two or more kinds. The concentration of the surfactant in the oily liquid (O) is not particularly limited, but from the viewpoint of facilitating the preparation of a W / O type emulsion, it is preferably at least twice the critical micelle concentration, specifically, 5 g / 100 mL to 25 g / 100 mL.

[0051] <Process (S3)> In step (S3), the aqueous liquid (W) and the oily liquid (O) are mixed to prepare a water-in-oil emulsion. Methods for preparing W / O type emulsions include, for example, high-speed stirring with a homogenizer, stirring with a stirrer such as a propeller mixer or disper, and membrane emulsification using a porous membrane.

[0052] From the viewpoint of reducing the amount of active ingredient remaining without being encapsulated in the complex, the mixing ratio of the amount of surfactant in the oily liquid (O) to the amount of active ingredient in the aqueous liquid (W) [(surfactant) / (active ingredient)] is preferably 2 / 1 or more by mass, more preferably 5 / 1 or more, even more preferably 10 / 1 or more, still more preferably 15 / 1 or more, and even more preferably 20 / 1 or more. Here, since surfactants are oil-soluble substances, excess surfactant not used in complex formation may occur as long as it does not adversely affect the lubricating oil composition. However, from the viewpoint of suppressing the excess surfactant not used in complex formation, it is preferable to reduce the amount of surfactant to the extent that the amount of active ingredient remaining without being encapsulated in the complex can be reduced. From this viewpoint, the mixing ratio of the amount of surfactant in the oily liquid (O) to the amount of active ingredient in the aqueous liquid (W) [(surfactant) / (active ingredient)] is preferably 100 / 1 or less. The upper and lower limits of these numerical ranges can be combined arbitrarily, and specifically, the ratio is preferably 2 / 1 to 100 / 1, more preferably 5 / 1 to 100 / 1, even more preferably 10 / 1 to 100 / 1, still more preferably 15 / 1 to 100 / 1, and even more preferably 20 / 1 to 100 / 1.

[0053] <Process (S4)> In step (S4), the organic solvent is distilled off from the water-in-oil emulsion, followed by drying. The drying method is not particularly limited, and examples thereof include freeze-drying and drying under reduced pressure, with freeze-drying being preferred. In this step, it is preferable to substantially completely remove water and the organic solvent. Specifically, it is preferable to dry the emulsion to such an extent that the water content is 1% or less, as measured by the Karl Fischer method.

[0054] [Lubricant additive composition] The lubricating oil additive composition of the present invention contains the S / O complex of the present invention. The lubricating oil additive composition of the present invention may consist solely of the S / O type complex of the present invention, but may also contain raw materials (specifically, excess surfactants used as raw materials) that remain unused in the W / O type emulsification process during the preparation of the S / O type complex, and the S / O type complex may also be diluted with diluent oil. The lubricating oil additive composition of one embodiment of the present invention may also contain other lubricating oil additives in addition to the S / O type complex of the present invention. For example, the lubricating oil additive composition of one embodiment of the present invention may be in the form of an additive package containing the S / O type complex of the present invention and other lubricating oil additives in addition to the complex, and diluted with diluent oil as necessary.

[0055] Other lubricating oil additives include oil-soluble lubricating oil additives that have been commonly used in lubricating oil compositions, such as at least one selected from the group consisting of metal detergents, antiwear agents, ashless dispersants, extreme pressure agents, pour point depressants, antioxidants, antifoaming agents, surfactants, demulsifiers, friction modifiers, oiliness improvers, rust inhibitors, and metal deactivators. These lubricating oil additives may be used singly or in combination of two or more.

[0056] [Lubricating oil composition] A lubricating oil composition according to one embodiment of the present invention contains a lubricating base oil and the S / O complex, and may further contain other lubricating oil additives as described above. Furthermore, the lubricating oil composition according to another embodiment of the present invention may contain a lubricating base oil and the lubricating oil additive composition.

[0057] <Lubricant base oil> The base oil used in the lubricating oil composition is not particularly limited, and any oil may be appropriately selected from mineral oils and synthetic oils that have conventionally been used as base oils for lubricating oils. Examples of mineral oils include oils refined by subjecting lubricating oil fractions obtained by vacuum distillation of atmospheric residue obtained by atmospheric distillation of crude oil to one or more, preferably all, of the following treatments: solvent deasphalting; at least one of solvent extraction or hydrocracking; at least one of solvent dewaxing or catalytic dewaxing; hydrorefining; or oils produced by isomerizing mineral oil wax; and GTL base oils produced by hydroisomerization dewaxing of residual wax (gas-to-liquid wax) in the GTL process. Of these, oils treated by hydrorefining are preferred. Examples of synthetic oils include poly-α-olefins such as polybutene, α-olefin homopolymers, and copolymers such as ethylene-α-olefin copolymers; various ethers such as polyphenyl ether; alkylbenzenes; and alkylnaphthalenes. These base oils may be used alone or in combination of two or more.

[0058] There is no particular limitation on the viscosity of the base oil, but the kinematic viscosity at 40°C is preferably 2 mm 2 / s or more, preferably 2 mm 2 / s~300mm 2 / s, more preferably 2 mm 2 / s~100mm 2 / s. The viscosity index of the base oil is preferably at least 50, more preferably at least 80, even more preferably at least 100, and even more preferably at least 105. When the viscosity index of the base oil is within this range, the viscosity characteristics of the lubricating oil composition can be easily improved. The 40°C kinematic viscosity and viscosity index of the base oil are measured and calculated by the methods described in the examples below.

[0059] In the lubricating oil composition of one embodiment of the present invention, the content of the S / O type complex is preferably 0.01 to 10 mass%, more preferably 0.1 to 5.0 mass%, and even more preferably 0.5 to 3.0 mass%, based on the total amount of the lubricating oil composition.

[0060] [Functions and uses of the complex] The composite of the present invention can uniformly disperse a poorly oil-soluble substance as an active ingredient in a lubricating base oil. Therefore, it becomes possible to use poorly oil-soluble substances that could not be used before as lubricating oil additives. Therefore, there is no need to perform structural transformation to impart oil solubility, and the range of substances that can be used as lubricating oil additives can be expanded.

[0061] Furthermore, the complex of the present invention can be disintegrated by being triggered by specific conditions (e.g., heat, ultraviolet light, radical generation, pH, load, stirring force, etc.), thereby releasing the encapsulated poorly oil-soluble substance. Therefore, in the absence of a trigger, the low-oil-soluble substance can remain encapsulated in the complex, preventing the cancellation of functions due to interactions with other lubricating oil additives contained in the lubricating oil composition, and the low-oil-soluble substance continues to be protected until the desired timing at which the trigger is applied. When the trigger is applied, the low-oil-soluble substance is released from within the complex, thereby exerting the required function. The necessary function referred to here is, as described above, one or more functions selected from the group consisting of load-bearing additives, base number enhancers, antioxidants, passivating agents, rust inhibitors, anti-corrosion agents, self-repairing agents, coating agents, and anti-foaming agents.

[0062] If the active ingredient contained in the complex is a low oil-soluble substance that functions as a load-bearing additive, when a high load is applied to the contact surface between two components, the complex that has penetrated into the contact surface will collapse, releasing the encapsulated material, thereby exerting its function as a load-bearing additive and suppressing seizure and other problems at the contact surface.

[0063] When the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a base number enhancer, when the acidity of the lubricating oil composition increases, the complex disintegrates, the encapsulated substance is released, and the function as a base number enhancer is exerted, thereby reducing the acidity of the lubricating oil composition.

[0064] When the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as an antioxidant, the complex gradually becomes unstable due to heat, pH fluctuations, radical generation, ultraviolet irradiation, etc., and after a predetermined time has passed, the encapsulated substance is released and its function as an antioxidant is exerted.

[0065] When the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a passivator, rust inhibitor, anti-corrosion agent, self-repairing agent, or coating agent, the complex gradually becomes unstable when exposed to high temperatures, and after a predetermined time, the encapsulated substance is released and its function is exerted. When the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a passivator, rust inhibitor, anti-corrosion agent, self-repairing agent, or coating agent, for example, when the lubricating oil composition is used as a heat-treated oil, the complex is likely to collapse when exposed to high temperatures. Therefore, it is preferable that the lubricating oil composition into which the complex is blended is a heat-treated oil. In addition, in the case of a rust inhibitor, anti-corrosion agent, self-repairing agent, or coating agent, the encapsulated substance may be released due to high load or pH fluctuation, thereby exerting its respective function.

[0066] When the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as an antifoaming agent, a stirring force that causes foaming is applied, and when the stirring force reaches a predetermined value or greater, the complex collapses, releasing the encapsulated substance, thereby exerting its function as an antifoaming agent and preventing foaming of the lubricating oil composition.

[0067] Therefore, the conjugate of the present invention also provides the following method. (1) A method of using the complex of the present invention as an additive for lubricating oil. (2) A method of using the complex of the present invention by blending it with a lubricating oil composition. In the above (1), examples of lubricating oil additives include load-bearing additives, base number enhancers, antioxidants, passivating agents, rust inhibitors, corrosion inhibitors, self-repairing agents, coating agents, and antifoaming agents. In addition, in the above (2), examples of the lubricating oil composition include gasoline engine oil, diesel engine oil, automatic transmission oil, automotive gear oil, lubricating oil for gas engine heat pumps and gas engine cogeneration systems, marine engine oil, hydraulic oil, lubricating oil for machine tools, compressor oil, turbine oil, gear oil, cutting oil, grinding oil, heat treatment oil, rolling oil, drawing oil, rust preventative oil, electrical insulating oil, rubber process oil, office automation equipment bearing oil, cleaning oil, and grease.

[0068] [One aspect of the present invention provided] According to one aspect of the present invention, the following [1] to

[13] are provided. [1] A solid-in-oil type complex containing an active ingredient and a surfactant, A complex wherein the active ingredient is one or more poorly oil-soluble substances selected from the group consisting of poorly oil-soluble substances and oil-insoluble substances, and the poorly oil-soluble substance is a substance that functions as an additive for lubricating oil. [2] The composite according to [1] above, wherein the function as a lubricating oil additive is one or more functions selected from the group consisting of a load-bearing additive, a base number enhancer, an antioxidant, a passivating agent, a rust inhibitor, a corrosion inhibitor, a self-repairing agent, a coating agent, and an anti-foaming agent. [3] The complex according to [1] or [2] above, which has a hydrodynamic diameter of 30 nm to 600 nm as measured by dynamic light scattering. [4] The complex according to any one of [1] to [3] above, wherein the surfactant is at least one selected from the group consisting of nonionic surfactants and anionic surfactants. [5] A lubricating oil additive composition containing the complex according to any one of [1] to [4] above. [6] A lubricating oil composition comprising a lubricating base oil and the composite according to any one of [1] to [4] above or the lubricating oil additive composition according to [5] above. [7] A method for producing a solid-in-oil type complex containing an active ingredient and a surfactant, comprising: The method includes the following steps (S1) to (S4): Step (S1): A step of preparing an aqueous liquid (W) by dissolving and / or dispersing the active ingredient in water. Step (S2): A step of dissolving the surfactant in an organic solvent to prepare an oily liquid (O). Step (S3): A step of mixing the aqueous liquid (W) and the oily liquid (O) to prepare a water-in-oil emulsion. Step (S4): A step of removing the organic solvent from the water-in-oil emulsion and then drying the emulsion. The active ingredient is one or more selected from the group consisting of poorly oil-soluble substances and oil-insoluble substances, The method for producing a composite, wherein the poorly oil-soluble substance is a substance that functions as an additive for lubricating oil. [8] The poorly oil-soluble substance is one or more poorly water-soluble substances selected from the group consisting of poorly water-soluble substances and water-insoluble substances, The method for producing the complex according to [7] above, further comprising a step (S0) of pulverizing the poorly oil-soluble substance with a bead mill. [9] A method of using the complex according to any one of the above [1] to [4] as an additive for lubricating oil.

[10] A method of using the complex according to any one of the above [1] to [4] in a lubricating oil composition.

[11] A method for using the complex according to any one of the above [1] to [4], wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a load-bearing additive, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient in the complex and allow it to function as a load-bearing additive.

[12] A method for using the complex according to any one of the above [1] to [4], wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a base value enhancer, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient and allow it to function as a base number enhancer.

[13] A method for using the complex according to any one of the above [1] to [4], comprising using one or more surfactants selected from a nonionic surfactant and a carboxylic acid surfactant, The method of use includes disintegrating the complex in a lubricating oil composition, and allowing one or more surfactants selected from the nonionic surfactant and the carboxylic acid surfactant to function as a load-bearing additive.

[0069] [One embodiment of the method of use of the present invention provided] According to one aspect of the present invention, there are provided the following uses [U1] to [U11] and [U1a] to [U10a]. [U1] A method for using the complex of the present invention, comprising: The method of use comprises disintegrating the complex in a lubricating oil composition to release the poorly oil-soluble substance in the complex. [U2] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a load-bearing additive, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient in the complex and allow it to function as a load-bearing additive. [U3] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a base value enhancer, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient and allow it to function as a base number enhancer. [U4] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as an antioxidant, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient and allow it to function as an antioxidant. [U5] A method for using the composite of the present invention, wherein the active ingredient encapsulated in the composite is a poorly oil-soluble substance that functions as one or more selected from the group consisting of a passivating agent, a rust inhibitor, a corrosion-resistant agent, a self-repairing agent, and a coating agent; The method of use includes disintegrating the complex in a lubricating oil composition to release the active ingredient, thereby allowing the complex to exhibit a function as one or more selected from the group consisting of a passivating agent, a rust inhibitor, a corrosion-resistant agent, a self-repairing agent, and a coating agent. [U6] The method for use according to the above [U5], wherein the lubricating oil composition is a heat-treated oil. [U7] A method for using the composite of the present invention, wherein the active ingredient encapsulated in the composite is a poorly oil-soluble substance that functions as one or more selected from the group consisting of a rust inhibitor, an anti-corrosion agent, a self-repairing agent, and a coating agent; The method of use includes disintegrating the complex in a lubricating oil composition to release the active ingredient, thereby allowing the complex to exhibit a function as one or more selected from the group consisting of a rust inhibitor, an anti-corrosion agent, a self-repairing agent, and a coating agent. [U8] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as an antifoaming agent, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient and allow it to function as an antifoaming agent. [U9] A method for using the complex of the present invention, comprising encapsulating a low-oil-soluble marker substance together with an active ingredient in the complex, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient and the marker substance from inside the complex, and visually confirming the release of the active ingredient by means of the marker substance. [U10] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a low oil-soluble substance that functions as a base value enhancer, and the complex encapsulates a low oil-soluble marker substance together with the active ingredient, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient and the marker substance from inside the complex, and visually confirming the release of the active ingredient by means of the marker substance. [U11] A method for using the complex of the present invention, comprising using one or more surfactants selected from a nonionic surfactant and a carboxylic acid surfactant, The method of use includes disintegrating the complex in a lubricating oil composition, and allowing one or more surfactants selected from the nonionic surfactant and the carboxylic acid surfactant to function as a load-bearing additive. [U1a] A method for using the conjugate of the present invention, comprising: The method of use comprises blending the complex into a lubricating oil composition, and disintegrating the complex with one or more triggers selected from the group consisting of heat, ultraviolet light, radical generation, pH, load, and stirring force, thereby releasing the poorly oil-soluble substance in the complex. [U2a] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a load-bearing additive, The method of use comprises blending the complex into a lubricating oil composition, and applying a load to the contact surface between two components filled with the lubricating oil composition, causing the complex that has penetrated into the contact surface to break down, releasing the active ingredient and suppressing seizure at the contact surface. [U3a] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a base value enhancer, The method of use comprises blending the complex in a lubricating oil composition, and disintegrating the complex to release the active ingredient by increasing the acidity of the lubricating oil composition, thereby reducing the acidity of the lubricating oil composition. [U4a] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as an antioxidant, The method for use comprises blending the complex into a lubricating oil composition, and disintegrating the complex with one or more triggers selected from the group consisting of heat, pH change, radical generation, and ultraviolet irradiation, thereby releasing the active ingredient and inhibiting oxidation of the lubricating oil composition. [U5a] A method for using the composite of the present invention, wherein the active ingredient encapsulated in the composite is a poorly oil-soluble substance that functions as one or more selected from the group consisting of a passivating agent, a rust inhibitor, a corrosion-resistant agent, a self-repairing agent, and a coating agent; A method of use in which the complex is blended into a lubricating oil composition, and the complex is decomposed by heat to release the active ingredient, thereby allowing the complex to exhibit the function of one or more selected from the group consisting of a passivating agent, a rust inhibitor, a corrosion-resistant agent, a self-repairing agent, and a coating agent. [U6a] The method of use according to [U5a] above, wherein the lubricating oil composition is a heat-treated oil. [U7a] A method for using the composite of the present invention, wherein the active ingredient encapsulated in the composite is a poorly oil-soluble substance that functions as one or more selected from the group consisting of a rust inhibitor, an anti-corrosion agent, a self-repairing agent, and a coating agent; The method of use includes blending the complex into a lubricating oil composition, and disintegrating the complex by one or more triggers selected from the group consisting of a high load and a pH change, thereby releasing the active ingredient and allowing the complex to exhibit one or more functions selected from the group consisting of a rust inhibitor, an anti-corrosion agent, a self-repairing agent, and a coating agent. [U8a] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as an antifoaming agent, The method of use comprises blending the complex into a lubricating oil composition, and disintegrating the complex by the stirring force when the lubricating oil composition is stirred, thereby releasing the active ingredient and suppressing foaming of the lubricating oil composition. [U9a] A method for using the complex of the present invention, comprising encapsulating a low-oil-soluble marker substance together with an active ingredient in the complex, The method of use comprises blending the complex into a lubricating oil composition, and causing the complex to collapse when the lubricating oil composition deteriorates, thereby releasing the marker substance from inside the complex, thereby visually confirming the deterioration of the lubricating oil composition. [U10a] A method for using the complex of the present invention, wherein the active ingredient encapsulated in the complex is a low oil-soluble substance that functions as a base value enhancer, and the complex encapsulates a low oil-soluble marker substance together with the active ingredient, The method of use comprises blending the complex into a lubricating oil composition, and triggering degradation of the lubricating oil composition due to accumulation of acidic substances to cause the complex to collapse and release the marker substance from inside the complex, thereby visually confirming the degradation of the lubricating oil composition. [Example]

[0070] The present invention will be specifically described with reference to the following examples, but the present invention is not limited to these examples.

[0071] [Production Examples 1 to 19: Preparation of Complexes] According to Production Examples 1 to 19 described below, conjugates A1 to A13, conjugates B1 to B4, and conjugates C1 and C2 were prepared. Details of the active ingredients and surfactants used in Production Examples 1 to 19 are shown below.

[0072] (active ingredient) Phosphoric acid: Fujifilm Wako Pure Chemical Industries, Ltd., water-soluble, poorly oil-soluble substance (solubility in n-hexane (25°C): less than 0.01 g / 100 mL) Phosphorous acid: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.; water-soluble, poorly oil-soluble substance (solubility in n-hexane (25°C): less than 0.01 g / 100 mL) "Molybdenum disulfide": Fujifilm Wako Pure Chemical Industries, Ltd., insoluble substance Carbon black: Mitsubishi Chemical Corporation, product name MA100, insoluble material "Giant fullerene (hereinafter referred to as fullerene)": NC Ecom, product name "G-MAX", insoluble substance "12-Molybdo(VI) phosphate n-hydrate (hereinafter referred to as phosphomolybdic acid)": A water-soluble, oil-soluble substance manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Guanidine carbonate: Water-soluble, poorly oil-soluble substance manufactured by Tokyo Chemical Industry Co., Ltd. (solubility in n-hexane (25°C): less than 0.01 g / 100 mL) "Aminoguanidine bicarbonate": manufactured by Tokyo Chemical Industry Co., Ltd., a water-soluble, poorly oil-soluble substance (solubility in n-hexane (25°C): less than 0.01 g / 100 mL) "Sodium nitrite": A water-soluble, oil-soluble substance manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. "Zinc phosphate": A water-soluble, oil-soluble substance manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.

[0073] (surfactant) "Sucrose erucate (SE)": Manufactured by Mitsubishi Chemical Foods Corporation, HLB value 2.0, a mixture of sucrose erucate monoester, sucrose erucate diester, and sucrose erucate triester "Glycerin Monooleate (GMO)": Manufactured by Tokyo Chemical Industry Co., Ltd., HLB value 4.3 Sorbitan monooleate (SMO): Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., HLB value 4.9 "Sorbitan trioleate (STO)": Manufactured by Tokyo Chemical Industry Co., Ltd., product name "Span85", HLB value 3.0 Lauric acid (LA): manufactured by Tokyo Chemical Industry Co., Ltd., HLB value 3.8

[0074] <Production Example 1: Preparation of Complex A1> Active ingredient: Phosphorous acid Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) 30 g of SE was dissolved in 200 mL of hexane (room temperature: 25°C) to prepare a SE hexane solution. Also, 1 g of phosphorous acid was dissolved in 100 mL of water (room temperature: 25° C.) to prepare an aqueous solution of phosphorous acid. The SE hexane solution and the aqueous phosphorous acid solution were mixed and stirred for 1 minute at 20,000 rpm using a homogenizer to obtain a W / O type emulsion. Next, the hexane was evaporated from the W / O emulsion, and the emulsion was then freeze-dried to prepare Complex A1.

[0075] <Production Example 2: Preparation of Complex A2> Active ingredient: Phosphorous acid Surfactant: Sucrose erucate (SE) + Glyceryl monooleate (GMO) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) Complex A2 was prepared in the same manner as in Production Example 1, except that 20 g of SE and 10 g of GMO were used instead of 30 g of SE.

[0076] <Production Example 3: Preparation of Complex A3> Active ingredient: Phosphoric acid Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) Complex A3 was prepared in the same manner as in Production Example 1, except that 1 g of phosphoric acid was used instead of 1 g of phosphorous acid.

[0077] <Production Example 4: Preparation of Complex A4> Active ingredient: Phosphoric acid Surfactant: Sucrose erucate (SE) + Glyceryl monooleate (GMO) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) Complex A6 was prepared in the same manner as in Production Example 2, except that 1 g of phosphoric acid was used instead of 1 g of phosphorous acid.

[0078] <Production Example 5: Preparation of Complex A5> Active ingredient: Phosphorous acid Surfactants: Sorbitan monooleate (SMO) + Sorbitan trioleate (STO) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) Complex A5 was prepared in the same manner as in Production Example 1, except that 15 g of SMO and 15 g of STO were used instead of 30 g of SE.

[0079] <Production Example 6: Preparation of Complex A6> Active ingredient: Phosphoric acid Surfactants: Sorbitan monooleate (SMO) + Sorbitan trioleate (STO) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) Complex A6 was prepared in the same manner as in Production Example 3, except that 15 g of SMO and 15 g of STO were used instead of 30 g of SE.

[0080] <Production Example 7: Preparation of Complex A7> Active ingredient: Molybdenum disulfide Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = approximately 90 / 1 (mass ratio) 30 g of SE was dissolved in 200 mL of hexane to prepare a SE hexane solution. Additionally, an aqueous dispersion of molybdenum disulfide powder was prepared using an RMB-08 bead mill manufactured by Imex Co., Ltd. Specifically, 1 g of molybdenum disulfide and 30 mL of water were placed in a 100 mL zirconia vessel, along with 40 mL of zirconia beads with a particle size of 0.1 mm. The vessel was then subjected to ball milling at room temperature (25°C) and a rotation speed of 2,000 rpm for 2 hours to obtain a mixture of zirconia beads and molybdenum disulfide powder. Next, the mixture was quickly filtered under reduced pressure using No. 2 filter paper while washing with 70 mL of water to remove the zirconia beads and coarse molybdenum disulfide powder, thereby preparing an aqueous dispersion of molybdenum disulfide powder. Considering the mass of molybdenum disulfide removed by the filter paper, it was estimated that approximately 0.3 g of molybdenum disulfide was dispersed in the water containing the molybdenum disulfide powder. The SE hexane solution and the water dispersion of molybdenum disulfide powder were mixed and stirred for 1 minute at 20,000 rpm using a homogenizer to obtain a W / O type emulsion. Next, the hexane was distilled off from the W / O emulsion, and the emulsion was freeze-dried to prepare Complex A7.

[0081] <Production Example 8: Preparation of Complex A8> Active ingredient: Carbon black Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = approximately 90 / 1 (mass ratio) Composite A8 was prepared in the same manner as in Production Example 7, except that 1 g of carbon black was used instead of 1 g of molybdenum disulfide. Considering the mass of carbon black removed by the filter paper, it was estimated that approximately 0.3 g of carbon black was dispersed in the carbon black dispersion water.

[0082] <Production Example 9: Preparation of Complex A9> Active ingredient: Fullerene Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = approximately 90 / 1 (mass ratio) Composite A9 was prepared in the same manner as in Production Example 7, except that 1 g of fullerene was used instead of 1 g of molybdenum disulfide. Considering the mass of fullerenes removed by the filter paper, it was estimated that about 0.3 g of fullerenes was dispersed in the water dispersion of fullerenes.

[0083] <Production Example 10: Preparation of Complex A10> Active ingredient: Phosphomolybdic acid Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) A composite A10 was prepared in the same manner as in Production Example 1, except that 1 g of phosphomolybdic acid was used instead of 1 g of phosphorous acid.

[0084] <Production Example 11: Preparation of Complex A11> Active ingredient: Phosphomolybdic acid Surfactant: Sucrose erucate (SE) + Glyceryl monooleate (GMO) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) A composite A11 was prepared in the same manner as in Production Example 2, except that 1 g of phosphomolybdic acid was used instead of 1 g of phosphorous acid.

[0085] <Production Example 12: Preparation of Complex A12> Active ingredient: Phosphorous acid Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = 20 / 1 (mass ratio) A composite A12 was prepared in the same manner as in Production Example 1, except that the amount of SE added was changed to 20 g.

[0086] <Production Example 13: Preparation of Conjugate A13> Active ingredient: Phosphorous acid Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = 10 / 1 (mass ratio) Complex A13 was prepared in the same manner as in Production Example 1, except that the amount of SE added was changed to 10 g.

[0087] <Production Example 14: Preparation of Complex B1> Active ingredient: Guanidine carbonate Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) 30 g of SE was dissolved in 200 mL of hexane (room temperature: 25°C) to prepare a SE hexane solution. Furthermore, 1 g of guanidine carbonate was dissolved in 100 mL of water (room temperature: 25° C.) to prepare an aqueous guanidine carbonate solution. The SE hexane solution and the guanidine carbonate aqueous solution were mixed and stirred for 1 minute at 20,000 rpm using a homogenizer to obtain a W / O type emulsion. Next, the hexane was distilled off from the W / O emulsion, and the emulsion was then freeze-dried to prepare Complex B1.

[0088] <Production Example 15: Preparation of Complex B2> Active ingredient: Guanidine carbonate Surfactant: Sucrose erucate (SE) + lauric acid (LA) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) Complex B2 was prepared in the same manner as in Production Example 14, except that 20 g of SE and 10 g of LA were used instead of 30 g of SE.

[0089] <Production Example 16: Preparation of Complex B3> Active ingredient: Aminoguanidine bicarbonate Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) Complex B3 was prepared in the same manner as in Production Example 14, except that 1 g of aminoguanidine bicarbonate was used instead of 1 g of guanidine carbonate and dissolved in 100 mL of warm water at 60°C.

[0090] <Production Example 17: Preparation of Complex B4> Active ingredient: Aminoguanidine bicarbonate Surfactant: Sucrose erucate (SE) + lauric acid (LA) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) Complex B4 was prepared in the same manner as in Production Example 15, except that 1 g of aminoguanidine bicarbonate was used instead of 1 g of guanidine carbonate and dissolved in 100 mL of warm water at 60°C.

[0091] <Production Example 18: Preparation of Complex C1> Active ingredient: sodium nitrite Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) 30 g of SE was dissolved in 200 mL of hexane (room temperature: 25°C) to prepare a SE hexane solution. In addition, 1 g of sodium nitrite was dissolved in 100 mL of water (room temperature: 25° C.) to prepare an aqueous sodium nitrite solution. The SE hexane solution and the aqueous sodium nitrite solution were then mixed and stirred for 1 minute at 20,000 rpm using a homogenizer to obtain a W / O type emulsion. Next, the hexane was evaporated from the W / O emulsion, and the emulsion was then freeze-dried to prepare complex C1.

[0092] <Production Example 19: Preparation of Conjugate C2> Active ingredient: Zinc phosphate Surfactant: Sucrose erucate (SE) [(surfactant) / (active ingredient)] = 30 / 1 (mass ratio) Complex C2 was prepared in the same manner as in Production Example 17, except that 1 g of zinc phosphate was used instead of 1 g of sodium nitrite.

[0093] [Study 1: Study of particle size (hydrodynamic diameter) of the complex] The particle size of the composites A1 to A9 and the composites B1 to B4 was measured.

[0094] (Method for measuring particle size) The particle size (hydrodynamic diameter) was measured using a Malvern Zetasizer Nano device by dynamic light scattering (DLS) at a wavelength of 633 nm at room temperature (25°C).

[0095] <Examples 1-1 to 1-13> The particle size (hydrodynamic diameter) of complexes A1 to A9 and complexes B1 to B4 was measured. Specifically, a sample prepared by adding 0.1 mass % of the complex to squalane (2,6,10,15,19,23-hexamethyltetracosane, manufactured by Junsei Chemical Co., Ltd., purity 98% or higher) was subjected to measurement of particle size (hydrodynamic diameter).

[0096] <Comparative Examples 1-1 to 1-4> As a reference, the particle size (hydrodynamic diameter) of squalane alone was measured (Comparative Example 1-1). In addition, samples prepared by adding 0.1% by mass of various surfactants to squalane were used to measure particle size (hydrodynamic diameter).

[0097] The results are shown in Tables 1-1 and 1-2.

[0098] [Table 1-1]

[0099] [Table 1-2]

[0100] The results shown in Tables 1-1 and 1-2 reveal that all of the complexes A1 to A9 and complexes B1 to B4 are nanoparticles of 400 nm or less.

[0101] [Study 2: Study on uniform dispersion of the complex in oil] The composites A1 to A11, composites B1 to B4, and composites C1 and C2 were examined for uniform dispersibility in oil.

[0102] <Examples 2-1 to 2-17> The composites A1 to A11, composites B1 to B4, and composites C1 and C2 were evaluated for uniform dispersibility in oil. Specifically, 1.0 mass% of the complex was added to a 500 neutral fraction mineral oil (hereinafter also referred to as "500N mineral oil") to prepare a sample for evaluating uniform dispersibility in oil, and the uniform dispersibility in oil was evaluated by the method described below.

[0103] <Examples 2-18 to 2-20> The composites A1, A12, and A13 were evaluated for uniform dispersibility in oil. Specifically, 1.0 mass % of the complex was added to hexane to prepare a sample for evaluating uniform dispersibility in oil, and the uniform dispersibility in oil was evaluated by the method described below.

[0104] <Comparative Examples 2-1 to 2-10> The active ingredients used in the preparation of Complexes A1 to A11, Complexes B1 to B4, and Complexes C1 and C2 were evaluated for uniform dispersibility in oil. Specifically, the active ingredients were added to 500N mineral oil in the amounts shown in Table 2-2 to prepare samples for evaluating uniform dispersibility in oil, and the uniform dispersibility in oil was evaluated by the method described below.

[0105] (Evaluation of uniform dispersion in oil) The prepared sample was left to stand at room temperature (25°C) for 24 hours, and the uniform dispersibility in oil was evaluated visually. The evaluation criteria were as follows: Rating A: No turbidity at all, transparent. · Rating B: Slight turbidity is observed, but transparency is sufficiently ensured. C: Turbidity is observed and transparency is insufficient, or sediment is observed. The results are shown in Tables 2-1 and 2-2.

[0106] [Table 2-1]

[0107] [Table 2-2]

[0108] The results shown in Table 2-1 indicate that all of the composites A1 to A13, composites B1 to B4, and composites C1 and C2 have good uniform dispersibility in oil. In particular, all of the composites with a mass ratio of [(surfactant) / (active ingredient)] of 20 / 1 or more have extremely good uniform dispersibility in oil. On the other hand, the results shown in Table 2-2 indicate that neither the poorly oil-soluble nor the insoluble substance, which are the active ingredients of the complex, are uniformly dispersed in oil, and therefore, the poorly oil-soluble and insoluble substances, which are the active ingredients of the complex, cannot be used as lubricating oil additives as they are.

[0109] [Study 3: Study on the effect of improving wear resistance] The lubricating oil compositions containing the complexes A1 to A10, A12, and A13 were examined for their effect in improving wear resistance. In Study 3, PAO (poly-α-olefin, kinematic viscosity at 40°C: 17 mm) was used as the base oil. 2 / s) was used.

[0110] <Examples 3-1 to 3-12> Lubricating oil compositions were prepared by adding 1.0 mass % each of the complexes A1 to A10, A12, and A13 to a base oil, and the wear resistance was evaluated by the method described below.

[0111] <Comparative Example 3-1> The base oil was used alone and the wear resistance was evaluated by the method described below.

[0112] <Comparative Examples 3-2 to 3-6> Lubricating oil compositions were prepared by adding 1.0 mass % of each surfactant to the base oil, and the wear resistance was evaluated by the method described below.

[0113] (Evaluation of abrasion resistance) The lubricating oil compositions of Examples 3-1 to 3-12 and Comparative Examples 3-1 to 3-6 were tested using a ball-on-disk reciprocating friction tester (Bauden-Leben type) under the conditions of a load of 80 N, a temperature of 100°C, a sliding speed of 15 mm / s, and a stroke of 15 mm, and the wear width of the disc after the test was measured. z ≦1.0 μm) was used. The smaller the wear width, the better the wear resistance. The results are shown in Tables 3-1 and 3-2.

[0114] [Table 3-1]

[0115] [Table 3-2]

[0116] The results shown in Tables 3-1 and 3-2 reveal the following: A comparison of Comparative Example 3-1 with Comparative Examples 3-2 to 3-6 reveals that the surfactants used, sucrose erucate (SE), glycerin monooleate (GMO), sorbitan monooleate (SMO), sorbitan trioleate (STO), and lauric acid (LA), have the function of improving abrasion resistance. Furthermore, since the wear width in Examples 3-1 to 3-12 is smaller than that in Comparative Examples 3-2 to 3-6, it is clear that the high load applied during the test triggers the collapse of the complex, and that in addition to the various components used as surfactants, the active ingredients in the complex contribute to improving the wear resistance. Furthermore, in Examples 3-7 to 3-9, which used insoluble substances such as molybdenum disulfide, carbon black, and fullerene, almost no wear was observed, demonstrating an extremely excellent effect in improving wear resistance.

[0117] [Study 4: Study on base number enhancers] The lubricating oil compositions containing Complexes B1 to B4 were examined for their base number enhancers.

[0118] <Examples 4-1 to 4-4> Composites B1 to B4 were each added in an amount of 1.0 mass % to a mixture of toluene, isopropyl alcohol (IPA), and water to prepare model oils. The mixing ratio of toluene, isopropyl alcohol (IPA), and water was toluene / IPA / water=50 / 45 / 5 (volume ratio).

[0119] <Comparative Example 4-1> The mixed liquids used in Examples 4-1 to 4-4 were used alone as model oils.

[0120] <Comparative Example 4-2> A model oil was prepared by adding 1.0 mass % of sucrose erucate (SE) to the mixed liquid used in Examples 4-1 to 4-4.

[0121] (Evaluation method) First, the pH of the prepared model oil was measured (initial pH). Next, in accordance with Clause 5 of JIS K2501:2003 "Petroleum products and lubricants - Test method for neutralization number," the model oil was gradually shifted toward the acidic region, and if the model oil shifted to the alkaline region due to the outflow of active ingredients caused by the breakdown of the complex, the pH just before the inflection point from the alkaline region to the acidic region was taken as the post-titration pH.If the model oil did not shift to the alkaline region, the pH when it reached a constant value was taken as the post-titration pH. The results are shown in Table 4.

[0122] [Table 4]

[0123] The results shown in Table 4 reveal that initially, the active ingredients of complexes B1 to B4 in the model oil are encapsulated within the complexes, but when the model oil shifts toward the acidic region, the complexes collapse, the active ingredients leak out, and the pH rises. [Explanation of symbols]

[0124] 1. Complex (X) Active ingredient (Y) Surfactant Ya hydrophilic group Yb lipophilic group

Claims

1. A solid-in-oil type complex containing an active ingredient and a surfactant, the surfactant is at least one selected from sucrose erucate, glycerin monooleate, sorbitan monooleate, sorbitan trioleate, and lauric acid; the active ingredient is one or more low-oil-soluble substances selected from the group consisting of poorly oil-soluble substances and oil-insoluble substances, The poorly oil-soluble substance is a substance that functions as an additive for lubricating oil, The complex, wherein the active ingredient is one or more selected from the group consisting of phosphorous acid, phosphoric acid, molybdenum disulfide, carbon black, fullerene, phosphomolybdic acid, guanidine carbonate, aminoguanidine bicarbonate, sodium nitrite, and zinc phosphate.

2. 2. The composite according to claim 1, wherein the function as an additive for a lubricating oil is one or more functions selected from the group consisting of a load-bearing additive, a base number enhancer, and a passivating agent.

3. 3. The complex according to claim 1, wherein the complex has a hydrodynamic diameter of 30 nm to 600 nm as measured by dynamic light scattering.

4. A lubricating oil additive composition comprising the complex according to any one of claims 1 to 3.

5. A lubricating oil composition comprising a lubricating base oil and the composite according to any one of claims 1 to 3 or the lubricating oil additive composition according to claim 4.

6. A method for producing a solid-in-oil type composite containing an active ingredient and a surfactant, comprising: The method includes the following steps (S1) to (S4): Step (S1): A step of preparing an aqueous liquid (W) by at least one of dissolving and dispersing the active ingredient in water. Step (S2): A step of dissolving the surfactant in an organic solvent to prepare an oily liquid (O). Step (S3): A step of mixing the aqueous liquid (W) and the oily liquid (O) to prepare a water-in-oil emulsion. Step (S4): A step of removing the organic solvent from the water-in-oil emulsion and then drying the emulsion. in the step (S3), a mixing ratio [(surfactant) / (active ingredient)] of the amount of the surfactant in the oily liquid (O) to the amount of the active ingredient in the aqueous liquid (W) is 2 / 1 to 100 / 1 in mass ratio, the active ingredient is one or more low-oil-soluble substances selected from the group consisting of poorly oil-soluble substances and oil-insoluble substances, The method for producing a composite, wherein the poorly oil-soluble substance is a substance that functions as an additive for lubricating oil.

7. the poorly oil-soluble substance is one or more poorly water-soluble substances selected from the group consisting of poorly water-soluble substances and water-insoluble substances, The method for producing a composite according to claim 6, further comprising a step (S0) of pulverizing the poorly oil-soluble substance with a bead mill.

8. A method of using the complex according to any one of claims 1 to 3 as an additive for lubricating oil.

9. A method of using the complex according to any one of claims 1 to 3 in a lubricating oil composition.

10. A method for using the complex according to any one of claims 1 to 3, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a load-bearing additive, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient in the complex and allow it to function as a load-bearing additive.

11. A method for using the complex according to any one of claims 1 to 3, wherein the active ingredient encapsulated in the complex is a poorly oil-soluble substance that functions as a base value enhancer, The method of use comprises disintegrating the complex in a lubricating oil composition to release the active ingredient and allow it to function as a base number enhancer.

12. A method for using the complex according to any one of claims 1 to 3, comprising using, as a surfactant, one or more surfactants selected from nonionic surfactants and carboxylic acid surfactants, and one or more surfactants selected from sucrose erucate, glycerin monooleate, sorbitan monooleate, sorbitan trioleate, and lauric acid; The complex is disintegrated in a lubricating oil composition, and one or more surfactants selected from the nonionic surfactant and the carboxylic acid surfactant, wherein the one or more surfactants selected from sucrose erucate, glycerin monooleate, sorbitan monooleate, sorbitan trioleate, and lauric acid function as a load-bearing additive.

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