Oil-based emulsions in water

Abstract

To provide an oil-in-water emulsion composition which comprises a novel compound having a phospholipid-like structure which functions as an emulsifier and has excellent emulsion stability.SOLUTION: There is provided an oil-in-water emulsion composition which comprises (A) a compound represented by the formula (1) [wherein, R1 and R4 are an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, here, at least one of R1 and R4 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms and R2 and R3 are an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms]; (B) a monovalent or divalent alcohol which is liquid at 20°C; (C) an oil solution such as an oil solution having a viscosity at 20°C of 1000 mPa s or more; (D) a surfactant such as a nonionic surfactant having a polyoxyethylene group and / or a polyglyceryl group in the hydrophilic group, (E) a water-soluble polymer and (F) water.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an oil-in-water emulsion composition comprising a novel compound that functions as an emulsifier. [Background technology]

[0002] In oil-in-water emulsion compositions, particularly oil-in-water emulsion cosmetics, various components are being incorporated to improve stability such as emulsion stability, feel upon application, and moisturizing effects. Novel compounds usable in such compositions are being researched daily. For example, phospholipids are natural surfactants with good affinity to the skin and high moisturizing effects, and they are also functional substances that can be used as emulsifiers (surfactants). Furthermore, the development of compounds with phospholipid-like structures that further enhance the functionality of phospholipids is also being researched daily.

[0003] As such a compound, Patent Document 1 discloses a compound containing a phosphorylcholine-like group, similar to that of a phospholipid. Furthermore, behendimonium ethyl phosphate stearyl is cited as one specific example of this compound as a cosmetic ingredient and is currently in commercial use. However, although the compound in Patent Document 1 has both hydrophilic and hydrophobic groups, its purpose is to promote transdermal absorption and improve moisturizing properties, and its function as an emulsifier is not very high. Phospholipids are generally known to have weak emulsifying power, and the compound in Patent Document 1 also has weak emulsifying power (surface activity) due to its low solubility.

[0004] Therefore, the applicant has commenced research and development of novel compounds with improved surfactant properties that have a structure similar to phospholipids.

[0005] On the other hand, in emulsified compositions, when high-viscosity, semi-solid, or solid oils are incorporated, problems such as decreased emulsification stability and crystal precipitation may occur. As a solution to these problems, Patent Document 2 proposes an oil-in-water cosmetic composition in which a specific 2-ethylhexanoic acid ester and a specific water-soluble polymer are incorporated to suppress the precipitation and separation of solid oils, resulting in a cosmetic composition with excellent skin compatibility. [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] Japanese Patent Publication No. 2011-213602 [Patent Document 2] Patent No. 4679350 [Overview of the project] [Problems that the invention aims to solve]

[0007] Under the circumstances described above, the applicants developed novel compounds with improved surfactant properties and a structure similar to phospholipids. Furthermore, the applicants developed formulations of compositions (particularly oil-in-water emulsion compositions) using such novel compounds, and discovered an emulsion composition that can stably incorporate high-viscosity, semi-solid, or solid oils, leading to the present invention. The present invention aims to provide an oil-in-water emulsion composition with excellent emulsification stability, comprising a novel compound having a phospholipid-like structure that functions as an emulsifier. [Means for solving the problem]

[0008] The present invention includes, but is not limited to, the embodiments listed below. [1] The following components (A) to (F): (A) Formula (1): [ka] [In the formula, R 1is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, and R 4 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, where R 1 and R 4 at least one of which is an unsaturated hydrocarbon group having 12 to 22 carbon atoms; and, R 2 and R 3 may be the same or different, and each independently is an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms.] a compound represented by (B) a monohydric or dihydric alcohol that is liquid at 20 °C, (C) one or more oil agents selected from the group consisting of an oil agent having a viscosity of 1000 mPa·s or more at 20 °C and an oil agent that is semi-solid or solid at 20 °C, (D) one or more surfactants selected from the group consisting of a nonionic surfactant having a polyoxyethylene group and / or a polyglyceryl group in the hydrophilic group and an anionic surfactant, (E) a water-soluble polymer, and (F) water, containing an oil-in-water type emulsion composition (hereinafter referred to as "this emulsion composition"). [2] In formula (1), one of R 1 and R 4 is an unsaturated hydrocarbon group having 18 carbon atoms, and one of R 1 and R 4 is a saturated hydrocarbon group having 22 carbon atoms, and, R 2 and R 3 are both hydroxyethyl groups, the oil-in-water type emulsion composition according to [1]. [3] The oil-in-water type emulsion composition according to [1] or [2], wherein component (B) is one or more selected from the group consisting of 1,3-butylene glycol, dipropylene glycol, and ethanol. [4] The oil-in-water type emulsion composition according to any one of [1] to [3], wherein the ratio of component (A) to component (D) ((A) / (D)) is 0.01 to 200 by mass ratio. [5] The oil-in-water emulsion composition according to any one of [1] to [4], wherein the ratio of component (A) to component (C) ((A) / (C)) is 0.1 to 100 by mass. [6] The oil-in-water emulsion composition according to any one of [1] to [5], wherein at least one of component (C) is an oil that is semi-solid or solid at 20°C. [7] The oil-in-water emulsion composition according to any one of [1] to [6], wherein at least one of component (C) is a solid oil at 20°C. [8] The oil-in-water emulsion composition according to any one of [1] to [7], wherein at least one of component (D) is a nonionic surfactant having a polyoxyethylene group in its hydrophilic group. [9] The oil-in-water emulsion composition according to any one of [1] to [8], wherein at least one of component (D) is a nonionic surfactant having a lipophilic group selected from the group consisting of phytosterol residues, cholesterol residues, saturated fatty acid residues, and unsaturated fatty acid residues.

[10] The oil-in-water emulsion composition according to any one of [1] to [9], wherein the oil-in-water emulsion composition has emulsion particles that can be identified as a Maltese cross when observed under a polarizing microscope.

[11] An oil-in-water emulsion composition according to any one of [1] to

[10] , which is an emulsified cosmetic. A method for producing an oil-in-water emulsion composition according to any one of [1] to

[10] , A step of preparing a first mixed solution by mixing components (A), (B), and (D); A step of mixing component (E) and component (F) to prepare a second mixed solution; A step of mixing the first mixed solution and the second mixed solution to prepare a mixed solution that forms the aqueous phase; and, A step to obtain an emulsion composition by adding component (C), which will be the oil phase, to a mixed solution that will be the aqueous phase and mixing it. Methods that include...

[13] A method for producing an oil-in-water emulsion composition according to

[12] , further comprising the step of heating and pressurizing the obtained emulsion composition. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide an oil-in-water emulsion composition that contains a novel compound having a phospholipid-like structure that functions as an emulsifier and exhibits excellent emulsification stability. [Modes for carrying out the invention]

[0010] The oil-in-water emulsion composition of the present invention comprises the following components (A) to (F): (A) Formula (1): [ka] [In the formula, R 1 R is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms. 4 R is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, where R 1 and R 4 At least one of them is an unsaturated hydrocarbon group having 12 to 22 carbon atoms; and, R 2 and R 3 These may be the same or different, and each is independently an alkyl group having 1 to 6 carbon atoms, or a hydroxyalkyl group having 1 to 6 carbon atoms. Compounds represented by (hereinafter referred to as "PC compounds" in this specification), (B) Monovalent or divalent alcohols that are liquid at 20°C, (C) One or more oils selected from the group consisting of oils with a viscosity of 1000 mPa·s or more at 20°C, and oils that are semi-solid or solid at 20°C. (D) One or more surfactants selected from the group consisting of nonionic surfactants having a polyoxyethylene group and / or a polyglyceryl group in the hydrophilic group, and anionic surfactants. (E) Water-soluble polymers, and (F) Water; It contains. In this specification, (A) to (F) are label symbols for the components, and are hereinafter also referred to as component (A), etc.

[0011] Ingredient (A) Component (A) is a compound containing a phosphorylcholine analog (PC compound), as described above. In equation (1), R 1 R is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, i.e., R 1 R is an unsaturated hydrocarbon group having 12 to 22 carbon atoms, or a saturated hydrocarbon group having 12 to 22 carbon atoms. 4 R is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, i.e., R 4 R is an unsaturated hydrocarbon group having 12 to 22 carbon atoms, or a saturated hydrocarbon group having 12 to 22 carbon atoms. However, R 1 and R 4 At least one of them is an unsaturated hydrocarbon group having 12 to 22 carbon atoms. That is, R 1 and R 4 Both are unsaturated hydrocarbon groups with 12 to 22 carbon atoms, or R 1 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms, and R 4 is a saturated hydrocarbon group with 12 to 22 carbon atoms, or R 1 is a saturated hydrocarbon group having 12 to 22 carbon atoms, and R 4 This is an unsaturated hydrocarbon group with 12 to 22 carbon atoms. 1 and R 4 There are no cases where both are saturated hydrocarbon groups with 12 to 22 carbon atoms.

[0012] R 1 and R 4 In one preferred embodiment, one of the groups is an unsaturated hydrocarbon group having 12 to 22 carbon atoms, and the other is a saturated hydrocarbon group having 12 to 22 carbon atoms. That is, R 1 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms, and R 4 is a saturated hydrocarbon group with 12 to 22 carbon atoms, or R 1 is a saturated hydrocarbon group having 12 to 22 carbon atoms, and R 4 It is preferable that is an unsaturated hydrocarbon group having 12 to 22 carbon atoms. In that case, emulsification stability may be further improved. Furthermore, R 1 and R 4 One of them is an unsaturated hydrocarbon group with 18 carbon atoms, R1 and R 4 Preferably, the other of the two groups is a saturated hydrocarbon group having 22 carbon atoms. In that case, the uniformity of the oil phase tends to be higher, especially when mixed with one or more oils, such as component (C), which are high viscosity or semi-solid or solid. The compound of formula (1) has increased solubility due to the presence of an unsaturated bond in its molecule, and it is presumed that the interaction between the oil of component (C) and the lipophilic chain of the compound of formula (1) is enhanced, thereby further improving the stability of this emulsion. The saturated hydrocarbon group may be, for example, an alkyl group. The unsaturated hydrocarbon group may be, for example, an alkenyl group or an alkynyl group.

[0013] R 1 and R 4 In (the following R 1 and R 4 The following explanations apply independently unless otherwise specified: the unsaturated or saturated hydrocarbon groups having 12 to 22 carbon atoms may be linear, branched, or cyclic. 1 and R 4 The unsaturated or saturated hydrocarbon group is preferably a linear or branched hydrocarbon group, and more preferably a linear hydrocarbon group. In particular, R 1 and R 4 It is preferable that both are linear or branched hydrocarbon groups, and more preferably that both are linear hydrocarbon groups. The unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms may be a hydrocarbon group having a structure obtained by removing the hydroxyl group (OH) from a monohydric aliphatic alcohol (e.g., an aliphatic alkyl group or alkenyl group). 1 and R 4 The number of carbon atoms in the saturated hydrocarbon group is more preferably 16 to 22, and even more preferably 18 to 22.

[0014] R 1 and R 4The saturated hydrocarbon groups having 12 to 22 carbon atoms in this compound are not limited to these, but examples of linear groups include the lauryl group (12 carbon atoms; also called the dodecyl group), myristyl group (14 carbon atoms; also called the tetradecyl group), cetyl group (16 carbon atoms; also called the hexadecyl group), stearyl group (18 carbon atoms; also called the octadecyl group), and behenyl group (22 carbon atoms; also called the docosyl group), while examples of branched groups include the isostearyl group (18 carbon atoms; also called the 16-methylheptadecyl group). Of these, the stearyl group and the behenyl group are preferred, and the behenyl group is more preferred.

[0015] R 1 and R 4 In the unsaturated hydrocarbon group having 12 to 22 carbon atoms, the unsaturation may be either carbon-carbon double bond unsaturation or carbon-carbon triple bond unsaturation, but preferably carbon-carbon double bond unsaturation. An unsaturated hydrocarbon group having a carbon-carbon double bond is also called an alkenyl group. The number of unsaturated atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. If there are two or more unsaturated atoms, it is preferable that all of them are carbon-carbon double bond unsaturation. 1 and R 4 The number of carbon atoms in the unsaturated hydrocarbon group is preferably 16 to 22.

[0016] In equation (1), R 1 and R 4 It is more preferable that at least one of them is an unsaturated hydrocarbon group having 18 carbon atoms. In that case, the stability of the emulsified composition can be further improved. Furthermore, R 1 and R 4It is even more preferable that at least one of the groups is an 18-carbon unsaturated hydrocarbon group having 1 to 3 carbon-carbon double bonds. This further improves emulsification stability. The number of carbon-carbon double bonds is more preferably 1 or 2, and more preferably 1. Examples of 18-carbon unsaturated hydrocarbon groups include the oleyl group, elaidyl group, linoleyl group (hepiunsaturated), and linoleyl group (hepiunsaturated), of which the oleyl group is more preferred. The oleyl group is also called the cis-9-octadecenyl group.

[0017] R 1 and R 4 In one preferred embodiment, for example, one of the groups is an oleyl group and the other is a group selected from the group consisting of a behenyl group and a stearyl group.

[0018] R 1 and R 4 The specific combinations are not limited to these, but (R 1 , R 4 When written as ), examples of possible combinations include (oleyl group, behenyl group), (behenyl group, oleyl group), (oleyl group, stearyl group), (stearyl group, oleyl group), etc.

[0019] In equation (1), R 2 and R 3 (R below) 2 and R 3 The explanations regarding (which apply independently unless otherwise specified) are independently selected from the group consisting of C1-C6 alkyl groups and C1-C6 hydroxyalkyl groups. Here, the alkyl portion in the alkyl and hydroxyalkyl groups may be linear or branched. Preferably, the alkyl portion is linear. 2 and R 3 These may be the same or different, but from the viewpoint of producing the PC compound, it is more preferable that they be the same.

[0020] R2 and R 3 Examples of C1-C6 alkyl groups include, in linear chains, methyl, ethyl, propyl, butyl, pentyl, and hexyl groups, and in branched chains, isopropyl and isobutyl groups. C1-C6 alkyl groups are preferably methyl (-CH3), ethyl (-CH2CH3), and propyl (-CH2CH2CH3), with methyl (-CH3) being more preferred.

[0021] R 2 and R 3 In this context, a C1-C6 hydroxyalkyl group is an alkyl group substituted with one or more hydroxyl groups, and a hydroxyalkyl group having hydroxyl groups (1-3, preferably 1-2, more preferably 1) at its terminus is preferred. Examples of C1-C6 hydroxyalkyl groups include hydroxymethyl, hydroxyethyl, and hydroxypropyl groups. A hydroxyethyl group (-CH2CH2OH) having one hydroxyl group at its terminus is more preferred as a C1-C6 hydroxyalkyl group.

[0022] R 2 and R 3 Preferably, each of these is independently a methyl group or a hydroxyethyl group. In that case, emulsion stability can be further improved. Furthermore, R 2 and R 3 It is more preferable that both of them are methyl groups, or that both are hydroxyethyl groups (especially -CH2CH2OH). Of these, R 2 and R 3 It is even more preferable that both are hydroxyethyl groups. 2 and R 3 If both are hydroxyalkyl groups (especially hydroxyethyl groups), then R 2 and R 3 Compared to cases where the alkyl group is an alkyl group (e.g., a methyl group), crystal precipitation may be suppressed and stability may be improved.

[0023] In the compound of formula (1), R 1 and R 4 One of them is an unsaturated hydrocarbon group having 18 carbon atoms, and R 1 and R 4 The other one of them is a saturated hydrocarbon group having 22 carbon atoms, and R 2 and R 3 Are both preferably a hydroxyethyl group (especially -CH2CH2OH). In that case, the emulsion stability can be further improved.

[0024] R 1 、R 2 、R[[ID=​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​

[0026] The PC compound represented by formula (1) has a structure similar to phosphorylcholine (-N) within its molecule. + (CH3)2(CH2)2-O-PO3 - PC compounds are compounds having a - group (hereinafter referred to as the "phosphorylcholine analog"). The phosphorylcholine analog is a polar group and functions as a hydrophilic group. In addition, unsaturated or saturated hydrocarbon groups are bonded to both sides of the phosphorylcholine analog, and these hydrocarbon groups function as hydrophobic groups. Therefore, PC compounds can function as surfactants and emulsifiers. More specifically, since PC compounds contain both a cationic and anionic part, they can be classified as amphoteric surfactants (amphoionic surfactants). Furthermore, PC compounds are gemini-type surfactants having two hydrophobic groups and two hydrophilic groups. In other words, PC compounds have a structure in which two molecules of a single-chain, single-hydrophilic surfactant are covalently linked via a spacer. And because PC compounds have a structure similar to phospholipids, they are thought to have high affinity for the skin, and when this emulsified composition (especially cosmetics) is applied to the skin, it is possible to obtain a good feel such as a non-sticky texture and moisturizing properties.

[0027] Here, in equation (1), R 1 and R 4 In the case of compounds where both are saturated hydrocarbon groups having 12 to 22 carbon atoms, it is difficult to obtain the same high emulsification stability as in the case of component (A). An example of such a compound is behendimonium ethyl phosphate stearyl. In the above formula (1), R 1 is a behenyl group, R 2 and R 3 Both are methyl groups, and R 4This compound is a stearyl group compound and is not included in component (A). Compounds without unsaturated hydrocarbon groups, such as behendimonium ethyl phosphate stearyl, have problems such as low solubility in the oil phase, which limits formulation, and a tendency to cause a hard film on the skin after application of cosmetics. However, it has been found that the compound of formula (1) above has improved solubility in the oil phase and improved emulsion stability compared to behendimonium ethyl phosphate stearyl and the like. Furthermore, the compound of formula (1) has a gemini-type structure and may also have advantages that behendimonium ethyl phosphate stearyl had, such as a low CMC (critical micelle concentration) and a low Krafft point.

[0028] Component (A) may consist of a single compound of formula (1), or it may contain multiple compounds of formula (1) with different structures (a mixture).

[0029] The content of component (A) in this emulsified composition (the total amount if there are multiple components) is not limited to this, but from the viewpoint of emulsification stability and obtaining a good feel, it can be, for example, 0.01 to 10% by mass, preferably 0.1 to 5% by mass, based on the total amount of this emulsified composition (100% by mass). Furthermore, the content of component (A) is preferably 0.1 to 5% by mass, more preferably 0.2 to 4% by mass, and even more preferably 0.3 to 3% by mass, based on the total amount of this emulsified composition. In this case, an emulsified composition with high emulsification stability can be obtained.

[0030] Ingredient (B) Component (B) is a monohydric or dihydric alcohol that is liquid at 20°C. By incorporating a monohydric or dihydric liquid alcohol, the PC compound can be stably incorporated, and the stability of the emulsion composition can be improved. Furthermore, incorporating a monohydric or dihydric liquid alcohol makes it easier to obtain emulsion particles in which the Maltese cross can be observed under polarized light microscopy. The monohydric or dihydric liquid alcohol is preferably water-soluble. In this specification, the water solubility of the alcohol may be, for example, soluble in water at a concentration of 1% by mass, more preferably soluble in water at 5%, 10%, 30%, or 50% (all by mass), and more preferably miscible with water in any ratio. The monohydric or dihydric liquid alcohol may be an alcohol having a carbon number preferably 1 to 12, more preferably 1 to 8, and even more preferably 2 to 6. Examples of liquid monohydric alcohols include, but are not limited to, ethanol, methanol, propanol, isopropanol, and phenoxyethanol. Ethanol is more preferred as the monohydric alcohol. Examples of liquid dihydric alcohols include, but are not limited to, 1,3-butylene glycol, dipropylene glycol, tripylene glycol, and ethylhexylglycerin. Component (B) is preferably one or more selected from the group consisting of 1,3-butylene glycol, dipropylene glycol, and ethanol. In this case, it becomes easier to obtain emulsion particles in which the Maltese cross can be observed under polarized light microscopy, and the emulsification stability can be further improved.

[0031] The content of component (B) (or the total amount if there are multiple components) is not limited to this, but from the viewpoint of obtaining emulsification stability, it can be 1 to 40% by mass, preferably 2 to 35% by mass, and more preferably 5 to 30% by mass, based on the total amount of the emulsified composition (100% by mass).

[0032] Ingredients (C) Component (C) is one or more oils selected from the group consisting of oils with a viscosity of 1,000 mPa·s or more at 20°C, and oils that are semi-solid or solid at 20°C. In the present invention, component (A) can be used to stably emulsify a composition containing one or more oils such as component (C), which are high viscosity, semi-solid, or solid. Even when high viscosity, semi-solid, or solid oils are included, stickiness can be suppressed, and an emulsified composition (especially a cosmetic) can be obtained that has excellent sustained moisturizing effect and sustained firmness due to the oil content after application, derived from the high viscosity, semi-solid, or solid oils.

[0033] For oils with a viscosity of 1,000 mPa·s or higher at 20°C (hereinafter referred to as "oil (C1)"), the viscosity can be measured using a B-type viscometer. There is no particular upper limit to the viscosity of oil (C1), but it may be, for example, 1,500,000 mPa·s or less. The viscosity of oil (C1) is preferably 1,000 to 1,000,000 mPa·s, and more preferably 1,500 to 500,000 mPa·s.

[0034] Semi-solid or solid oils at 20°C include semi-solid oils at 20°C (hereinafter referred to as "oil (C2)") and solid oils at 20°C (hereinafter referred to as "oil (C3)"). In oil (C2), semi-solid means an amorphous state that is different from a liquid but also different from a solid, i.e., an intermediate state between a solid and a liquid (e.g., paste-like, waxy, semi-paste). For example, a semi-solid state may be an amorphous state in which the viscosity is too high to be measured by the viscosity measurement method described above, and may also be a fluid state. Semi-solid oils (C2) at 20°C can be distinguished from oils (C1) (i.e., oils with a viscosity of 1,000 mPa·s or more at 20°C) by whether or not the viscosity can be measured. As the viscosity of oil (C1) increases, it approaches a semi-solid state, but in this specification, if the viscosity can be measured, it is considered liquid, and if the viscosity exceeds the measurement limit, it is considered semi-solid. For example, the upper limit of viscosity measurement in a Type B viscometer varies depending on the measuring instrument and its manufacturer, but for example, it is 2,000,000 mPa·s. The oil (C2) is preferably an oil with a melting point of 30°C or higher and less than 61°C. One form of the semi-solid state may be a paste. The solid state means a solid state in which there is no fluidity and it can take a molded shape. In this emulsion composition, a semi-solid oil (C2) at 20°C may be blended, a solid oil (C3) at 20°C may be blended, or both may be blended.

[0035] Examples of the oily component (C) include natural or synthetic ester oils, hydrocarbon oils, silicone oils, higher alcohols, and fatty acids, which have a viscosity of 1,000 mPa·s or more at 20°C, or are semi-solid or solid at 20°C.

[0036] The oils (C1) with a viscosity of 1,000 mPa·s or more at 20°C are not limited to these, but include, for example, polyglyceryl-2 diisostearate (e.g., viscosity (20°C): 1,160 mPa·s), phytosteryl / octyldodecyl lauroyl glutamate (e.g., viscosity (20°C): 1,650 mPa·s), diisostearyl malate (e.g., viscosity (20°C): 2,520 mPa·s or 5,500 mPa·s), and highly polymerized dimethylpolysiloxane (1 million CS) (e.g., viscosity (20°C)). Examples include polyglyceryl monoisostearate (e.g., viscosity (20°C): 4,450 mPa·s), dipentaerythrityl tripolyhydroxystearate (e.g., viscosity (20°C): 10,300 mPa·s), hydrogenated polyisobutene (with a viscosity of 1,000 mPa·s or more at 20°C; for example, viscosity (20°C) of 26,200 mPa·s or 44,100 mPa·s), polysilicone-15 (e.g., viscosity (20°C): 1,019 mPa·s), etc. These may be used individually or in combination of two or more.

[0037] Examples of semi-solid oils (C2) at 20°C include, but are not limited to, di(octyldodecyl / phytosteryl / behenyl) lauroyl glutamate, di(cholesteryl / behenyl / octyldodecyl) lauroyl glutamate, dimer dilinoleyl (phytosteryl / isostearyl / cetyl / stearyl / behenyl) dimer dilinoleate, phytosteryl isostearate, phytosteryl oleate, hexa(hydroxystearate / stearate / rosinate)dipentaerythrityl, petrolatum, hydrogenated palm oil, hydrogenated castor oil stearate, cholesteryl hydroxystearate, polyhydroxystearic acid, and hydrogenated polyisobutene (paste-like at 20°C). These may be used individually or in combination of two or more.

[0038] Examples of solid oils (C3) at 20°C include, but are not limited to, glyceryl stearate, candelilla wax, beeswax, shea butter, behenyl alcohol, cetostearyl alcohol, batyl alcohol, stearic acid, palmitic acid, diethylamino hydroxybenzoyl hexyl benzoate, bis-ethylhexyloxyphenol methoxyphenyl triazine, methylene bis-benzotriazolyl tetramethylbutylphenol, and others. These may be used individually or in combination of two or more.

[0039] The oily component (C) may be one of the following: an oily component (C1) with a viscosity of 1,000 mPa·s or more at 20°C, an oily component (C2) that is semi-solid at 20°C, and an oily component (C3) that is solid at 20°C. It may also be two of these, or all of them. Component (C) may be one of the above oily components, or a combination of two or more. Among these, it is preferable that at least one of the components (C) is an oily component that is semi-solid or solid at 20°C, and more preferably a solid oily component at 20°C. The higher the viscosity of component (C) and the more solid it becomes, the less sticky the composition will be, and the longer the firmness due to the oil content will last.

[0040] The content of component (C) (or the total amount if there are multiple components) is not limited to this, but from the viewpoint of obtaining excellent usability and emulsification stability, it can be 0.0001 to 20% by mass, preferably 0.001 to 15% by mass, and more preferably 0.01 to 10% by mass, based on the total amount of the emulsified composition (100% by mass).

[0041] Here, the ratio of component (A) to component (C) ((A) / (C)) is preferably 0.1 to 100 by mass, more preferably 0.2 to 50 by mass, and even more preferably 0.3 to 50. By setting the ratio of component (A) to component (C) as described above, it is possible to emulsify component (C) more effectively while obtaining a good feel from component (C), and further improve the emulsification stability of this emulsified composition. In addition, this ratio can suppress crystal precipitation, reduce stickiness, and further improve the persistence of the firmness provided by the oil. This ratio ((A) / (C)) is preferably 0.3 to 40, and more preferably 0.3 to 30.

[0042] Ingredients (D) Component (D) is one or more surfactants selected from the group consisting of nonionic surfactants having a polyoxyethylene group and / or a polyglyceryl group in its hydrophilic group, and anionic surfactants. By incorporating such surfactants, crystal precipitation can be suppressed, and the emulsion stability of this emulsion composition can be further improved.

[0043] In one preferred embodiment, at least one of component (D) is a nonionic surfactant having a polyoxyethylene group and / or a polyglyceryl group in its hydrophilic group. In this case, higher emulsification stability and a better feel can be obtained. In this embodiment, a nonionic surfactant having a polyoxyethylene group in its hydrophilic group may be used, or a nonionic surfactant having a polyglyceryl group in its hydrophilic group may be used. Alternatively, a nonionic surfactant having both a polyoxyethylene group and a polyglyceryl group in its hydrophilic group may be used. Among these, a nonionic surfactant having a polyoxyethylene group in its hydrophilic group is more preferred.

[0044] Furthermore, it is preferable that at least one of component (D) is a nonionic surfactant having a lipophilic group selected from the group consisting of phytosterol residues, cholesterol residues, saturated fatty acid residues, and unsaturated fatty acid residues. The presence of these nonionic surfactants increases the affinity with component (A) and can improve emulsification stability. It is even more preferable that component (D) includes a nonionic surfactant having a polyoxyethylene group and / or a polyglyceryl group as its hydrophilic group, and having a lipophilic group selected from the group consisting of phytosterol residues, cholesterol residues, saturated fatty acid residues, and unsaturated fatty acid residues. This increases the affinity with component (A) and can further improve emulsification stability. Furthermore, it is preferable that component (D) contains a nonionic surfactant having a polyoxyethylene group as its hydrophilic group and a group selected from the group consisting of phytosterol residues, cholesterol residues, saturated fatty acid residues, and unsaturated fatty acid residues as its lipophilic group, and it is even more preferable that it contains a nonionic surfactant having a polyoxyethylene group as its hydrophilic group and a phytosterol residue or cholesterol residue as its lipophilic group. As saturated fatty acid residues, saturated fatty acid residues having 12 to 22 carbon atoms are preferred, such as stearic acid, myristic acid, and lauric acid. As unsaturated fatty acid residues, unsaturated fatty acid residues having 12 to 22 carbon atoms are preferred, such as oleic acid.

[0045] Specific examples of nonionic surfactants used as component (D) are not limited to those listed above, but include, for example, nonionic surfactants having a polyoxyethylene group in the hydrophilic group, such as POE-phytosterols like PEG-5 phytosterol and PEG-30 phytosterol, PEG-cholesterols like Choleth-10, POE-saturated fatty acid esters like PEG-150 stearate, PEG-55 stearate, PEG-40 stearate, and PEG-10 laurate, and oleate P Examples of POE-unsaturated fatty acid esters include EG-10, POE-sorbitan fatty acid esters such as polysorbate 80 (also known as polyoxyethylene sorbitan monooleate (20 E.O.)), polyoxyethylene sorbitan monostearate (20 E.O.), POE-sorbitan fatty acid esters such as PEG-40 sorbitan oleate, and POE-hydrogenated castor oils such as PEG-80 hydrogenated castor oil, PEG-60 hydrogenated castor oil, and PEG-40 hydrogenated castor oil. Nonionic surfactants having a polyglyceryl group in the hydrophilic group include, for example, glyceryl fatty acid esters such as polyglyceryl-10 stearate, polyglyceryl-10 laurate, polyglyceryl-10 oleate, and polyglyceryl-10 diisostearate.

[0046] Specific examples of anionic surfactants used as component (D) include, but are not limited to, acylmethyltaurate salts of higher fatty acids such as sodium stearoylmethyltaurate, acyl lactates such as sodium stearoyl lactate, N-acyl glutamates such as sodium N-stearoyl-L-glutamate, fatty acid soaps such as sodium distearoyl glutamate lysine, sodium dilauroyl glutamate lysine, sodium laurate, higher alkyl sulfate esters such as sodium lauryl sulfate, alkyl ether sulfate esters such as POE-lauryl sulfate triethanolamine, and phosphate esters such as POE-oleyl ether sodium phosphate.

[0047] Component (D) may be one of the above-mentioned surfactants or a combination of two or more.

[0048] The content of component (D) (or the total amount if there are multiple components) is not limited to this, but from the viewpoint of obtaining high emulsification stability and excellent usability, it can be 0.01 to 10% by mass, preferably 0.02 to 5% by mass, and more preferably 0.1 to 1% by mass, based on the total amount of the emulsified composition (100% by mass).

[0049] Here, the ratio of component (A) to component (D) ((A) / (D)) is preferably 0.01 to 200 by mass, and more preferably 0.1 to 100 by mass. By setting the ratio of component (A) to component (D) as described above, crystal precipitation is further suppressed, making it easier to obtain an emulsified composition that is not sticky and has excellent stability. This ratio ((A) / (D)) is preferably 0.2 to 100, and more preferably 0.5 to 50.

[0050] Ingredient (E) Component (E) is a water-soluble polymer. The inclusion of a water-soluble polymer can improve emulsion stability. Since a water-soluble polymer can improve the viscosity of the aqueous phase, it can suppress the separation of the aqueous and oil phases and the collapse of the emulsion in compositions containing high-viscosity, semi-solid, or solid oils such as component (C).

[0051] Component (E) can be a natural or synthetic polymer, and examples include, but are not limited to, polysaccharides, celluloses, acrylic or methacrylic acid polymers, vinyl polymers, etc., but specifically include carrageenan, xanthan gum, gellan gum, gum arabic, karaya gum, tragacanth gum, carob gum, guar gum, tamarind gum, locust bean gum, quince seed (marmelo), casein, dextrin, gelatin, sodium pectinate, hydroxypropyl methylcellulose, hydroxypropylcellulose, hydroxyethylcellulose, methylcellulose, ethylcellulose, carboxymethylcellulose (CMC), dialkyldimethylammonium sulfate cellulose, cellulose gum, (acrylates / alkyl acrylate (C10-30)) crosspolymer, (sodium acrylate / sodium acryloyldimethyl taurate) copolymer, carboxyvinyl polymer (also called carbomer), polyvinyl alcohol (PVA), polyvinyl methyl ether (PVM), and PVP (polyvinylpyrrolidone). 、 Examples include sodium alginate and Tremella fuciformis polysaccharide. When incorporating into the composition, a mixture of water-soluble polymers and sugars may be used, or a mixture of polysaccharides and sugars, specifically, a mixture of carrageenan and sucrose (commercially available as a carrageenan-sucrose mixture). Component (E) may be one of the above water-soluble polymers or a combination of two or more.

[0052] The content of component (E) (or the total amount if there are multiple components) is not limited to this, but from the viewpoint of obtaining high emulsification stability and excellent usability, it can be 0.01 to 5% by mass, preferably 0.03 to 1% by mass, and more preferably 0.04 to 0.5% by mass, based on the total amount of the emulsified composition (100% by mass).

[0053] Ingredients (F) This emulsified composition contains water as component (F). In an oil-in-water emulsion composition, the emulsion is in the form of oil-in-water (O / W), with the aqueous phase being the outer phase and the oil phase being the inner phase. The aqueous phase may contain water-soluble substances and hydrophilic substances. Water is not limited to this, but purified water is preferably used.

[0054] The water content in this oil-in-water emulsion composition is not limited to this, but can be 1 to 99% by mass, preferably 10 to 98% by mass, more preferably 20 to 95% by mass, and even more preferably 30 to 90% by mass. Depending on the form of the formulation, the water content may be 50% by mass or more, or 60% by mass or more.

[0055] This emulsified composition may further contain oils other than component (C). Specifically, the oils other than component (C) are liquid oils (low-viscosity oils) with a viscosity of less than 1,000 mPa·s at 20°C. The inclusion of low-viscosity oils can enhance functionality such as usability. It can also help to balance the overall composition of the oils.

[0056] Other oils (low viscosity oils) besides component (C) include, for example, natural or synthetic ester oils, hydrocarbon oils, higher alcohols, and fatty acids. Specifically, while not limited to these, examples of oils include liquid paraffin (also called mineral oil), PG dicaprate, cetyl 2-ethylhexanoate, glyceryl tri-2-ethylhexanoate, isotridecyl isononanoate, ethyl oleate, di-2-ethylhexyl succinate, ethylhexyl methoxycinnamate, squalane, octyldodecanol, caprylic / capric triglyceride, trimethylolpropane triisostearate, pentaerythritol tetraisostearate, isohexadecane, isododecane, jojoba oil, macadamia nut oil, meadowfoam oil, hydrogenated coconut oil, olive oil, isostearic acid, dimethicone, methylphenylpolysiloxane, diphenylsiloxyphenyl trimethicone, tridecyl trimellitate, ascorbyl tetrahexyldecanoate, pentaerythritol tetraethylhexanoate, and others.

[0057] Here, the total amount of the oil is the sum of the oil other than component (C) (liquid oil with a viscosity of less than 1,000 mPa·s at 20°C: low viscosity oil) and component (C) mentioned above. By controlling the ratio of this total amount of oil to component (A), it is possible to further form an emulsion in which the Maltese cross can be confirmed and to obtain an even more stable emulsion composition. From the viewpoint of obtaining a stable emulsion composition, the ratio of the total amount of oil to component (A) (total amount of oil / component (A)) is preferably 0.0001 to 20 by mass, more preferably 0.01 to 20, and even more preferably 0.05 to 10.

[0058] Other ingredients This emulsified composition may contain various components that can be incorporated as an oil-in-water emulsion composition (especially cosmetics). Examples of such components include surfactants other than component (D), polyhydric alcohols of trivalent or higher, humectants, thickeners, powders, pigments, film-forming agents, pH adjusters, anti-fading agents, antioxidants, defoaming agents, cosmetic ingredients, plant extracts, preservatives, and fragrances.

[0059] Other surfactants besides component (D) include one or more surfactants selected from the group consisting of nonionic surfactants other than those mentioned above, cationic surfactants, and amphoteric surfactants. Examples of nonionic surfactants include sorbion fatty acid esters such as sorbion sesquiisostearate, sorbion palmitate, and sorbitan oleate, and sucrose fatty acid esters. Examples of cationic surfactants include quaternary ammonium salts such as behenyl PG-trimonium chloride and lauryltrimethylammonium chloride, and amidoamine compounds such as beheninate dimethylaminopropylamide. Examples of amphoteric surfactants include phospholipids (e.g., hydrogenated soybean phospholipids, lecithin, hydrogenated lecithin, etc.), phospholipid analogs (e.g., behendimonium ethyl phosphate stearyl, etc.), alkyl betaine-type amphoteric surfactants such as lauryldimethylbetaine, amidopropyl betaine-type amphoteric surfactants such as oleamide propyl betaine, and amino acid-type amphoteric surfactants such as sodium laurylaminopropionate.

[0060] Examples of polyhydric alcohols with a valency of 3 or higher include, but are not limited to, glycerin and diglycerin.

[0061] This emulsified composition may contain a pH adjuster. The pH adjuster can be used to adjust the pH to a range suitable for cosmetics. Furthermore, if the water-soluble polymer is an ionic polymer, the viscosity can also be adjusted when a pH adjuster is added. The pH adjuster is not particularly limited, but examples include sodium hydroxide, potassium hydroxide, and triethanolamine.

[0062] This emulsified composition may contain a preservative. Examples of preservatives, though not limited to those listed, include methyl parahydroxybenzoate (also known as methylparaben). Furthermore, phenoxyethanol, a monohydric alcohol, can also function as a preservative.

[0063] The emulsified composition preferably contains emulsion particles in which a Maltese cross can be observed under polarized light microscopy. For example, when an appropriate amount of the emulsified composition is placed on a glass slide, covered with a coverslip, and observed with an optical microscope (Olympus) (magnification: 400x, observation method: observed through a polarizing lens), a Maltese cross pattern (also called a Maltese cross) can be observed in the emulsion particles. The Maltese cross may be observed when the emulsion particles have a lamellar structure and / or a lipid bilayer structure. Of course, the emulsion particles do not need to have a lamellar structure and / or a lipid bilayer structure if the Maltese cross can be observed. The Maltese cross is observed when a more stable membrane structure is formed. For example, a lipid bilayer or lamellar structure may be formed on the surface of the emulsion particles, i.e., at the interface between the oil phase and the aqueous phase. These structures form a stable interface (membrane) structure and are less prone to collapse. Therefore, when emulsion particles in which a Maltese cross can be observed are formed, an emulsified composition with superior emulsification stability can be obtained. This emulsified composition, containing a combination of the above components (A) to (F), makes it possible to form emulsion particles in which the Maltese cross can be identified. In particular, the inclusion of component (A) makes it easier to form emulsion particles in which the Maltese cross can be identified. The Maltese cross originally refers to a shape in which four V-shaped emblems are joined at the base, but in the emulsion of this emulsified composition, an image resembling the Maltese cross can be confirmed using a polarizing microscope. The Maltese cross in the emulsion and its image are described in papers such as BDPark et al.'s Journal of Investigative Dermatology, Volume 121, Issue 4, October 2003, Pages 794-801 (especially Figure 2, etc.) and Cristhianne Moraes et al.'s Asian Journal of Pharmaceutical Sciences, Volume 13, Issue 2, March 2018, Pages 183-190. In this emulsified composition, a Maltese cross similar to the image shown in these papers can be confirmed.

[0064] This emulsified composition is preferably an emulsified cosmetic. The cosmetic may be a skin cosmetic or a hair cosmetic. It is particularly preferable that this emulsified composition be a skin cosmetic (an oil-in-water emulsified cosmetic for skin use). Furthermore, this emulsified composition is applicable to emulsified cosmetics for all uses, including skincare products and makeup products. This emulsified composition can produce an emulsified cosmetic that is non-greasy, provides long-lasting firmness due to its oil content, and offers a pleasant feel.

[0065] As a skin cosmetic, it is not particularly limited as long as it takes the form of an oil-in-water emulsion, and can be used as a cosmetic for various purposes. Examples of cosmetics include lotions, creams, serums, toners, hand creams, eye creams, body creams, makeup cosmetics, concealers, blushes, eyeshadows (eye colors), makeup bases, foundations (e.g., liquid foundations, solid foundations), and sunscreens. Methods of using skin cosmetics include applying it by hand or finger, using cotton, impregnating nonwoven fabrics, and spraying or misting.

[0066] As long as it takes the form of an oil-in-water emulsion, the hair cosmetic is not particularly limited and can be used as a cosmetic for various purposes. Examples include hair creams, hair waxes, hair rinses, hair masks, hair treatments, and hair sunscreens. Methods of using hair cosmetics include applying it with the hands or fingers, or spraying it on with a spray or mist.

[0067] This emulsified composition (especially emulsified cosmetic) can be manufactured by mixing the above-mentioned components. For example, a method can be used in which a preheated and mixed aqueous component is mixed with a preheated and mixed oily component to emulsify, and then cooled. In manufacturing, an appropriate emulsifier or kneader (e.g., a three-roller mixer, homomixer, etc.) can be used. Of course, the method for manufacturing this emulsified composition is not limited to this.

[0068] This emulsified composition (especially emulsified cosmetic) is preferably prepared by the following method: A step of preparing a first mixed solution by mixing components (A), (B), and (D); A step of mixing component (E) and component (F) to prepare a second mixed solution; A step of mixing the first mixed solution and the second mixed solution to prepare a mixed solution that forms the aqueous phase; and, A step to obtain an emulsion composition by adding component (C), which will be the oil phase, to a mixed solution that will be the aqueous phase and mixing it. It can be manufactured by a method that includes

[0069] In the production of the emulsified composition, it is preferable to further heat and high-pressure treat the emulsified composition produced above. That is, by heating and high-pressure treating the above emulsified composition (primary emulsified composition), the final emulsified composition is formed. This makes it possible to obtain an even more stable emulsified composition.

[0070] The emulsified composition can be manufactured by, for example, preparing a solution by mixing and heating components (A), (B), and (D), then adding a solution containing components (E), (F), and other water-soluble components to this solution to prepare an aqueous phase, and then adding a solution (oil phase) obtained by mixing and heating an oily component containing component (C) to this aqueous phase and mixing (emulsifying). The heating temperature can be, for example, 70-90°C (specifically 80°C). In the above method, components (A), (B), and (D) are mixed in advance to prepare a solution containing component (A). This allows for more stable formulation of component (A), making it easier to obtain an emulsified composition with excellent stability that confirms the Maltese Cross.

[0071] Furthermore, when the above emulsified composition is subjected to heating and high-pressure treatment, for example, the treatment can be performed under conditions of temperature: 40-90°C and pressure: 50-250 MPa, or further, under conditions of temperature: 40-90°C and pressure: 50-150 MPa, temperature: 50-90°C and pressure: 50-250 MPa, or temperature: 50-90°C and pressure: 50-150 MPa. The pressure may also be 70-250 MPa, 75-250 MPa, or even 80-250 MPa if high pressure is preferred to obtain a stable emulsified composition. The pressure may also be 70-150 MPa, 75-150 MPa, or 80-150 MPa. On the other hand, the temperature may be 40-90°C, 50-90°C, 60-90°C, or 70-90°C, and may even be 40-85°C, 50-85°C, 60-85°C, or 70-85°C. As for the apparatus, for example, a high-pressure homogenizer can be used. A pressure-type homogenizer can be used, and although not limited to this mechanism, homogenization can be performed by pressurizing the fluid (composition) and passing it through a homovalve, through collisions between particles or impact rings due to ejection from fine gaps, and shear force due to the pressure difference. Processing with a high-pressure homogenizer can be performed continuously, not in a batch manner. By passing the composition through a high-pressure homogenizer, for example, the particle size of emulsion particles can be made smaller, or the components in the composition can be further dispersed or dissolved. Such heated and high-pressure processing makes it easier to obtain emulsified compositions with excellent stability that can be confirmed by the Maltese Cross. [Examples]

[0072] The oil-in-water emulsion composition according to the present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[0073] PC compound NMR measurement The PC compounds obtained according to the synthesis example were dissolved in deuterated chloroform containing tetramethylsilane (TMS) as an internal standard, and then the compounds were analyzed using JNM-AL600 (manufactured by JEOL Ltd.).

[0074] PC compound synthesis Synthesis Example 1 (Synthesis of PC Compound 1) (R 1 , R 2 , R 3 , R 4 ) = (combination of oleyl group, hydroxyethyl group, hydroxyethyl group, behenyl group) In a 1 L round-bottom flask equipped with a thermometer, dropping funnel, and stirrer, 65.3 g (0.2 mol) of behenyl alcohol, 20.2 g (0.2 mol) of triethylamine, and 280 g of tetrahydrafuran were added as the starting alcohols, and the mixture was stirred and mixed after cooling to 4°C. Next, a mixed solution of 28.5 g (0.2 mol) of 2-chloro-2-oxo-1,3,2-dioxaphosphorane and 60 g of tetrahydrafuran was added dropwise to the cooled mixed solution using a dropping funnel. The dropwise addition was carried out gradually over 2 hours while stirring the cooled mixed solution, ensuring that the reaction temperature did not exceed 10°C. After the dropwise addition was complete, stirring was continued for another hour. Subsequently, the by-product, triethylamine hydrochloride, was filtered off. The entire volume of the obtained filtrate was placed in a 2 L round-bottom flask equipped with a stirrer, and 142 g (0.4 mol) of N,N-diethanololeylamine and 380 g of acetonitrile were added as tertiary amines. The mixture was stirred at 70°C for 12 hours. After that, the precipitate obtained by cooling the reaction mixture was filtered off and crude crystals were obtained by drying under reduced pressure at 70°C. The obtained crude crystals were recrystallized in a mixed solvent of tetrahydrafuran and acetonitrile to obtain 15.7 g of white crystals (yield 10%). Below, the obtained PC compound 1 1 H-NMR, 31 The results of the P-NMR analysis are shown. 1H-NMR (δ(ppm)): 0.88(t, J(HH)=6.6Hz, 6H, ), 1.21-1.39(m, 60H), 1.58-1.63(m, 2H), 1.65-1.73(m, 2H), 1.93-2.1 (m, 4H), 3.6-3.65(m, 4H), 3.7-3.75(m, 2H), 3.8-3.85(m, 4H), 3.95-4,05(m, 4H)4.51-4.55(m, 2H), 5.3-5.4(m, 2H) 31 P-NMR (δ(ppm)): -2.1(s)

[0075] Synthesis Example 2 (Synthesis of PC Compound 2) (R 1 , R 2 , R 3 , R 4 ) = (combination of behenyl group, hydroxyethyl group, hydroxyethyl group, oleyl group) The procedure was the same as in Synthesis Example 1, except that 53.6 g (0.2 mol) of oleyl alcohol was used as the starting alcohol instead of behenyl alcohol, and 165.4 g (0.4 mol) of N,N-diethanolbehenylamine was used as the starting amine instead of N,N-diethanololeylamine. 15.5 g of white crystals (10% yield) were obtained. Below, the obtained PC compound 2 1 H-NMR, 31 The results of the P-NMR analysis are shown. 1 H-NMR(δ(ppm)): 0.88(t, J(HH)=6.6Hz, 6H, ), 1.2-1.38(m, 64H), 1.58-1.64(m, 2H), 1.67-1.72(m, 2H), 1.93-2.09( m, 4H), 3.7-3.76(m, 4H), 3.83-3.86(m, 2H), 3.92-3.96(m, 4H), 4.0-4,05(m, 2H)4.17-4.25(m, 4H), 5.3-5.4(m, 2H) 31 P-NMR (δ(ppm)): -1.1(s)

[0076] Synthesis Example 3 (Synthesis of PC Compound 3) (R 1 , R2 , R 3 , R 4 ) = (behenyl group, methyl group, methyl group, oleyl group) combination The procedure was the same as in Synthesis Example 1, except that 53.6 g (0.2 mol) of oleyl alcohol was used as the starting alcohol instead of behenyl alcohol, and 141.4 g (0.4 mol) of N,N-dimethylbehenylamine was used as the starting amine instead of N,N-diethanololeylamine. 43.6 g of white crystals (30% yield) were obtained. Below, the obtained PC compound 3 1 H-NMR, 31 The results of the P-NMR analysis are shown. 1 H-NMR (δ(ppm)): 0.88(t, J(HH)=7.2Hz, 6H, ), 1.3-1.5(m, 60H), 1.5-1.6(m, 2H), 1.65-1.7(m, 2H), 1.9 5-2.02(m, 4H), 3.3(s, 6H), 3.3-3.46(m, 2H), 3.78-3.84(m, 4H), 4.27-4.31(m, 2H), 5.31-5.38(m, 2H) 31 P-NMR (δ(ppm)): 0.56(s)

[0077] Synthesis Example 4 (Synthesis of PC Compound 4) (R 1 , R 2 , R 3 , R 4 ) = (combination of oleyl group, methyl group, methyl group, behenyl group) The procedure was the same as in Synthesis Example 1, except that 118.2 g (0.4 mol) of N,N-dimethyloleylamine was used instead of N,N-diethanololeylamine as the starting amine, and 72.8 g of white crystals (yield 50%) were obtained. The following describes the obtained PC compound 4. 1 H-NMR, 31 The results of the P-NMR analysis are shown. 1H-NMR(δ(ppm)): 0.88(t, J(HH)=7.2Hz, 6H, ), 1.2-1.34(m, 48H), 1.54-1.61(m, 2H), 1.63-1.7(m, 2H), 1 .93-2.09(m, 4H), 3.36(s, 6H), 3.43-3.47(m, 2H), 3.78-3.87(m, 4H), 4.29-4.32(m, 2H), 5.3-5.4(m, 2H) 31 P-NMR (δ(ppm)): 0.39(s)

[0078] Examples 1-35, Comparative Examples 1-5 Oil-in-water emulsion composition (emulsified cosmetic) The following emulsified compositions were prepared using PC compounds 1 to 4 produced as described above.

[0079] Tables 1-3 show the components and their amounts (mass%), emulsion stability, and evaluation results for the emulsified cosmetic compositions (specifically lotions) of Examples 1-35 and Comparative Examples 1-5.

[0080] [Table 1]

[0081] [Table 2]

[0082] [Table 3]

[0083] In the examples and comparative examples listed in Tables 1-3, the names of the raw materials that deserve special mention are shown below. PEG-5 phytosterol: NIKKOL BPS-30 (manufactured by Nippon Surfactant Industry Co., Ltd.). PEG-30 phytosterol: NIKKOL BPS-5 (manufactured by Nippon Surfactant Industry Co., Ltd.). Choleth-10: EMALEX CS-10 (manufactured by Nippon Emulsion Co., Ltd.). PEG-55 stearate: NIKKOL MYS-55V (manufactured by Nippon Surfactant Industry Co., Ltd.). PEG-40 stearate: NIKKOL MYS-40V (manufactured by Nippon Surfactant Industry Co., Ltd.). Polysorbate 80: Leodol TW-O120V (manufactured by Kao Corporation). Polyglyceryl-10 stearate: NIKKOL Decaglyn 1-SV (manufactured by Nippon Surfactant Industry Co., Ltd.). Sodium stearoyl methyl taurate: NIKKOL SMT (manufactured by Nippon Surfactant Industry Co., Ltd.). Carrageenan-sucrose mixture: GENU VISCO TYPE JJ (manufactured by CP Kelco Co., Ltd.) (carrageenan 60% by mass or more).

[0084] Tables 1-3 show the R values ​​in PC compounds. 1 , R 2 , R 3 and R 4 Each of the groups is represented as "C18H35 (unsaturated)" (meaning the oleyl group), "CH2CH2OH" (meaning the hydroxyethyl group), "CH3" (meaning the methyl group), and "C22H45" (meaning the behenyl group).

[0085] The examples and comparative examples shown in Tables 1-3 were manufactured by the following methods. Manufacturing methods for Examples 1-35 (1) Components (A), (B), and (D) were mixed and heated to 80°C to dissolve and obtain a solution. (2) Components (E), (F), and sodium hydroxide as needed were mixed to obtain a solution, which was added to the solution from (1) above to obtain a solution (aqueous phase). (3) Component (C) and mineral oil were mixed and heated to 80°C to dissolve and obtain a solution (oil phase). (4) The solution from (3) above was added to the solution from (2) above at 80°C and mixed to emulsify. (5) The mixture from (4) above was cooled to obtain an emulsified composition. (6) The emulsified compositions of each example were obtained by heating and applying high pressure (80°C, 75MPa) to the emulsified compositions of (5) above using a high-pressure homogenizer.

[0086] Manufacturing methods for Comparative Examples 1-5 Comparative Example 1 was prepared in the same manner as Example 1, except that component (A) was not included (the same amount was replaced with purified water), and an emulsified composition was obtained. Comparative Example 2 was prepared in the same manner as in Example 1, except that component (B) was not included (it was replaced with the same amount of purified water), and an emulsified composition was obtained. Comparative Example 3 was prepared in the same manner as in Example 1, except that component (C) was not included (it was replaced with the same amount of mineral oil), and an emulsified composition was obtained. Comparative Example 4 was prepared in the same manner as in Example 1, except that component (D) was not included (it was replaced with the same amount of purified water), and an emulsified composition was obtained. Comparative Example 5 was prepared in the same manner as in Example 1, except that component (E) was not included (it was replaced with the same amount of purified water), and an emulsified composition was obtained.

[0087] evaluation The cosmetic compositions of Examples 1-35 and Comparative Examples 1-5 shown in Tables 1-3 were evaluated by the following method.

[0088] Checking for the presence of a Maltese cross For each sample, an appropriate amount of sample was placed on a glass slide, a coverslip was placed over it, and it was observed using an optical microscope (Olympus) (magnification: 400x, observation method: observation through a polarizing lens). The emulsion particles were observed visually to confirm the presence or absence of the Maltese cross. ○: A large number of Maltese crosses were found. △: A Maltese cross was faintly visible. ×: The Maltese Cross was not identified.

[0089] Suppression of crystal precipitation Each sample was left to stand in a 40°C constant temperature bath for one week (7 days), and the presence or absence of crystal precipitation was observed visually. ◎: No crystal precipitation is observed at all. ○: Almost no crystal precipitation is observed (only crystals smaller than 1 mm are confirmed). △: Slight crystal precipitation is observed (crystals between 1 mm and 2 mm in size are confirmed). ×: Crystal precipitation is clearly observed (crystals larger than 2 mm are confirmed).

[0090] Stability (50°C, 1 month) Each sample was left to stand in a 50°C constant temperature bath for one month (30 days), and the presence or absence of changes in appearance such as separation was observed visually. The number of days until changes in appearance (such as phase separation) were observed was noted. ◎: No external changes were observed after 30 days (Excellent). ○: A change in appearance was observed between the 14th and 29th (good). △: A change in appearance was observed between day 2 and day 13 (acceptable). ×: A change in appearance was observed within 1 day after being left in a constant temperature bath (bad).

[0091] Non-sticky Each sample was tested by a panel of 10 experts, who evaluated it on a 4-point scale using the absolute criteria (scoring) described below. The average score was calculated from the sum of all panel members' scores, and the final judgment was made according to the following criteria. Specifically, each sample was placed on the skin and spread to evaluate whether it felt non-sticky. (Absolute standard) 3: I really notice that it's not sticky at all. 2: I feel it's not sticky. 1: I feel it's not very sticky. 0: Does not feel sticky. (Judgment criteria) ◎: 2.5 points or higher (Excellent). ○: 2 points or more, less than 2.5 points (good). △: 1 point or more, but less than 2 points (acceptable). ×: Less than 1 point (defective).

[0092] The long-lasting firmness provided by oil. Each sample was tested by a panel of 10 experts, who evaluated it on a 4-point scale using the absolute criteria (scoring) described below. The average score was calculated from the sum of all panel members' scores, and the final judgment was made according to the following criteria. Specifically, each sample was placed on the skin, and the duration of its firming effect was evaluated 8 hours after application. Here, "firming effect" refers to a pleasant feeling of firmness after application. (Absolute standard) 3: I feel a very firming sensation. 2: I feel a firming sensation. 1: I feel a slight firmness. 0: I don't feel any firmness. (Judgment criteria) ◎: 2.5 points or higher (Excellent). ○: 2 points or more, less than 2.5 points (good). △: 1 point or more, but less than 2 points (acceptable). ×: Less than 1 point (defective).

[0093] result Examples 1 to 35, which contained components (A) to (F), showed a Maltese cross pattern and received no "X" ratings in any of the evaluation items (suppression of crystal precipitation, stability, lack of stickiness, and persistence of firmness due to oil). On the other hand, Comparative Examples 1 and 2 showed unstable emulsification, Comparative Example 3 lacked persistence of firmness, and Comparative Examples 4 and 5 clearly showed crystal precipitation.

[0094] Examples (Formula examples) The following examples were prepared as oil-in-water emulsion compositions. In the following examples, the content refers to the blending ratio (mass%), and "residual amount" refers to the amount that makes the total amount 100% by mass. The viscosity of component C (liquid) is all measured at 20°C. Viscosity was measured using a B-type viscometer (Toki Sangyo Co., Ltd., TVB-10 model, measurement temperature: 20°C, measurement conditions: rotor number No. 2-4, rotation speed 0.3-6.0 rpm, measurement time 1-3 minutes). In the description of the blended components, "paste-like" means semi-solid. The heating and high-pressure treatment conditions were all 80°C and 75 MPa using a high-pressure homogenizer.

[0095] Example 36: Emulsion (Component) (mass%) 1.PC compound 1 (component A) 1.0% 2. Candelilla wax (component C: solid) (*1) 0.05% 3. Lauroyl glutamate di(octyldodecyl / phytosteryl / behenyl) (Component C: Paste) (*2) 0.02% 4. Vaseline (Component C: Paste) (*3) 0.01% 5. Lauroyl glutamate di(cholesteryl / behenyl / octyldodecyl) (Component C: Paste) (*4) 0.02% 6. PEG-30 Phytosterol (Component D) 0.5% 7. Polysorbate 80 (Component D) 0.4% 8. PEG-40 Stearate (Component D) 0.1% 9. PG Dicaprate 0.5% 10. Pentaerythrityl tetraethylhexanoate 0.2% 11. Cetyl ethylhexanoate 0.1% 12. Squalane 0.3% 13. Mineral oil 0.1% 14. Polyglyceryl-2 Diisostearate (Component C: Liquid, Viscosity 1,160 mPa·s) 0.1% 15. Behenyl alcohol (component C: solid) 0.6% 16. Cetostearyl alcohol (Component C: Solid) 1.0% 17. Xanthan gum (ingredient E) 0.1% 18. Carbomer (Component E) 0.1% 19. Carrageenan (Component E) 0.3% 20. Sucrose 0.05% 21. Glycerin 0.5% 22,1,3-Butylene glycol (component B) 10.0% 23. Sodium hydroxide 0.06% 24. Ethanol (Component B) 5.0% 25. Phenoxyethanol (Component B) 0.5% 26.Fragrance 0.2% 27. A mixture of beauty ingredients including: *Hitorina* extract, asparagus extract, artemia extract, guava extract, coffee extract, jujube extract, grape leaf extract, burnet extract, peppermint leaf extract, Bifidobacterium culture lysate, *Prunus serrulata* flower extract, *Sambucus nigra* flower extract, green tea leaf extract, *Tencha* extract, *Jasminum sambac* flower extract, polyquaternium-51, *Rosa multiflora* fruit extract, *Rosa rugosa* flower extract, *Rosa rugosa* flower extract, water-soluble collagen, royal jelly extract, *Angelica acutiloba* root extract, *Rosa centifolia* flower extract, *Rosa damask* flower water, *Rosemary* leaf extract, *Acerola* fruit extract, acetylglutamic acid, theanine, glycine, hydrolyzed hyaluronic acid, and sodium hyaluronate. 2.0% 28. Purified water (Component F) Remaining amount (*1) Refined Candelilla Wax SR-3 (Nippon Natural Products Co., Ltd.) (*2) Eldew PS-304 (Ajinomoto Co., Inc.) (*3)SNOW WHITE SPECIAL(SONNEBORN REFINED PRODUCTS BV) (*4) Eldew CL-301 (Ajinomoto Co., Inc.)

[0096] (Manufacturing method) (1) Component 1 and a portion of components 6 and 22 were heated and dissolved at 80°C to obtain a solution (aqueous phase). (2) Components 17-20 and the remaining component 22 were mixed, a portion of component 28 was added, and the mixture was heated to 80°C to obtain a solution (aqueous phase). (3) The remaining components 7, 8, 21, 23, and 28 were added to the composition of (2) above to obtain a solution (aqueous phase). (4) Add the solution from (3) to the solution from (1) and mix. Add the solution (oil phase) obtained by heating and dissolving components 2-5 and 9-16 at 80°C and mix to obtain an emulsion. (5) After cooling the above (4), the homogeneously mixed components 24 and 25 were added, then components 26 and 27 were added and mixed to obtain an emulsified composition. (6) An emulsified composition (Example 36) was obtained by subjecting the emulsified composition of (5) above to heating and high pressure treatment.

[0097] (evaluation) The emulsion of Example 36 showed a Maltese cross pattern, and it was confirmed that it had good suppression of crystal precipitation, good stability, no stickiness, and good retention of firmness. The total amount of component (A) was 1.0%, the total amount of component (B) was 15.5%, the total amount of component (C) was 1.8%, the total amount of component (D) was 1.0%, and the total amount of component (E) was 0.5%. Therefore, (A) / (D) was 1.000, and (A) / (C) was 0.556.

[0098] Example 37: Emulsion (Component) (mass%) 1.PC compound 1 (component A) 0.6% 2.PC compound 2 (component A) 0.6% 3. Shea butter (component C: solid) (*5) 0.02% 4. Cholesteryl hydroxystearate (Component C: Paste) (*6) 0.02% 5. Beeswax (Component C: Solid) (*7) 0.01% 6. PEG-5 Phytosterol (Component D) 1.0% 7. Choleth-10 (Component D) 0.5% 8. PEG-55 Stearate (Component D) 0.5% 9. Meadowfoam oil 0.2% 10. Diisostearyl malate (Component C: liquid, viscosity 2,520 mPa·s (*8)) 0.01% 11. Caprylic / Capric Triglyceride 1.5% 12. Cetyl ethylhexanoate 0.5% 13. Hydrogenated polyisobutene (Component C: liquid, viscosity 44,100 mPa·s) (*9) 0.01% 14. Behenyl alcohol (component C: solid) 0.3% 15. Cetostearyl alcohol (Component C: Solid) 1.0% 16. Stearic acid (component C: solid) 0.01% 17. Palmitic acid (component C: solid) 0.02% 18. Carbomer (Component E) 0.15% 19. (Acrylates / C10-30 Alkyl Acrylate) Crosspolymer (Component E) 0.15% 20. Water-soluble polymers (Component E) 0.03% 21. Sodium alginate (Component E) 0.01% 22. Gellan gum (ingredient E) (*11) 0.01% 23,1,3-Butylene glycol (component B) 9.0% 24. Dipropylene glycol (Component B) 7.0% 25. Sodium hydroxide 0.12% 26. Ethanol (Component B) 3.0% 27. Phenoxyethanol (Component B) 0.5% 28.Fragrance 0.2% 29. A mixture of Rosa alba flower extract, avocado extract, Gynostemma pentaphyllum extract, chamomile water, Callicarpa japonica fruit extract, apple extract, lemongrass extract, Heloniopsis orientalis extract, asparagus extract, Artemia extract, guava extract, coffee extract, jujube extract, grape leaf extract, Sanguisorba officinalis extract, peppermint leaf extract, Bifidobacterium culture lysate, Prunus serrulata flower extract, Sambucus nigra flower extract, Camellia sinensis leaf extract, Chaenomeles speciosa extract, Jasminum sambac flower extract, Polyquaternium-51, Rosa multiflora fruit extract, Rosa rugosa flower extract, Rosa rugosa extract, Soluble collagen, Royal jelly extract, Angelica acutiloba root extract, Rosa centifolia flower extract, Rosa damask flower water, Rosmarinus officinalis leaf extract, Acerola fruit extract, Acetyl glutamic acid, Theanine, Glycine, Hydrolyzed hyaluronic acid, and sodium hyaluronate (a mixture of beauty ingredients) 2.0% 30. Purified water (Component F) Remaining amount (*5) Bioderma SX-19 <e>(Ichimaru Falcos Co., Ltd.) (*6) Saracos HS (Nisshin Oillio Group Ltd.) (*7) WHITE BEES WAX (Miki Chemical Industry Co., Ltd.) (*8) Cosmoll 222 (Nisshin Oillio Group Ltd.) (*9) Pearlream 24 (Nippon Oil & Fats Co., Ltd.) ( *11) Kelcogel LT100 (Dainippon Pharmaceutical Co., Ltd.)

[0099] (Manufacturing method) (1) Components 1 and 2, and components 6, 7, a portion of 23, and 24 were heated and dissolved at 80°C to obtain a solution (aqueous phase). (2) Components 18-22 and the remaining component 23 were mixed, a portion of component 30 was added, and the mixture was heated to 80°C to obtain a solution (aqueous phase). (3) The remainder of components 8, 25, and 30 were added to the composition of (2) above to obtain a solution (aqueous phase). (4) Add the solution from (3) to the solution from (1) and mix. Add the solution (oil phase) obtained by heating and dissolving components 3-5 and 9-17 at 80°C and mix to obtain an emulsion. (5) After cooling the above (4), the homogeneously mixed components 26 and 27 were added, then components 28 and 29 were added and mixed to obtain an emulsified composition. (6) The emulsified composition of (5) above was subjected to heating and high-pressure treatment to obtain an emulsified composition (Example 37).

[0100] (evaluation) The emulsion of Example 37 showed a Maltese cross pattern, and it was confirmed that it had good suppression of crystal precipitation, good stability, no stickiness, and good retention of firmness. The mass ratios were as follows: The total amount of component (A) was 1.2%, the total amount of component (B) was 19.5%, the total amount of component (C) was 1.4%, the total amount of component (D) was 2.0%, and the total amount of component (E) was 0.35%. Therefore, (A) / (D) was 0.600, and (A) / (C) was 0.857.

[0101] Example 38: Cream (Component) (mass%) 1.PC compound 1 (component A) 2.5% 2.PC compound 2 (component A) 0.3% 3. Stearyl behendimonium ethyl phosphate 0.1% 4. Candelilla wax (Component C: Solid) (*1) 0.01% 5. Lauroyl glutamate di(octyldodecyl / phytosteryl / behenyl) (Ingredient C: Paste) (*2) 0.01% 6. Shea butter (component C: solid) (*5) 0.01% 7. Phytosteryl oleate (Component C: Paste) (*12) 0.01% 8. Hydrogenated polyisobutene (Component C: liquid, viscosity 26,200 mPa·s) (*13) 0.02% 9. Hydrogenated polyisobutene (Component C: liquid, viscosity 115,300 mPa·s) (*14) 0.01% 10. Diisostearyl malate (Component C: Liquid, viscosity 5,500 mPa·s) 0.01% 11. Cetyl ethylhexanoate 0.5% 12. Dicaprate PG 0.1% 13. Glyceryl tri-2-ethylhexanoate 0.3% 14. PEG-5 Phytosterol (Component D) 1.0% 15. Sodium Stearoyl Methyl Taurate (Component D) 0.1% 16. Polyglyceryl-10 stearate (Component D) 0.1% 17. Isotridecyl isononanoate 0.01% 18. Caprylic / Capric Triglyceride 0.01% 19. Ethyl oleate 0.01% 20. Glyceryl stearate (Component C: Solid) 0.8% 21. Behenyl alcohol (component C: solid) 0.7% 22. Cetostearyl alcohol (Component C: Solid) 1.5% 23. Batyl alcohol (component C: solid) 0.02% 24. Carbomer (Component E) 0.05% 25. (Acrylates / C10-30 Alkyl Acrylate) Crosspolymer (Component E) 0.2% 26. Water-soluble polymers (Component E) 0.03% 27. Hydroxypropyl methylcellulose (component E) 0.02% 28,1,3-Butylene glycol (component B) 10.0% 29. Dipropylene glycol (Component B) 2.0% 30. Diglycerin 1.5% 31. Sodium hydroxide 0.06% 32. Ethanol (Component B) 3.7% 33. Phenoxyethanol (Component B) 0.3% 34.Fragrance 0.2% 35. Hydrolyzed conchiolin liquid, gentian extract, hydrolyzed silk liquid, hydrolyzed rice extract, seaweed extract, L-serine, Iris gracilis leaf extract, Artemisia capillaris flower extract, Alpinia speciosa leaf extract, Saccharomyces cerevisiae extract, pomegranate fruit extract, pomegranate peel extract, Myrica rubra fruit extract, Eggplant fruit extract, Harpagophytum root extract, parsley extract, royal jelly extract, Rosa alba flower extract, avocado extract, Gynostemma pentaphyllum extract, chamomile water, Callicarpa japonica fruit extract, apple extract, lemongrass extract, Heloniopsis orientalis extract, asparagus extract, Artemia extract, guava extract, coffee extract A mixture of jujube extract, grape leaf extract, and burnet extract, Artemisia capillaris extract, grape seed oil, Rosa rugosa extract, Rosa multiflora extract, Rosa japonica extract, Sambucus nigra flower extract, Camellia sinensis leaf extract, Chaenomeles speciosa extract, Jasminum sambac flower extract, Polyquaternium-51, Rosa multiflora fruit extract, Rosa rugosa flower extract, Rosa rugosa extract, soluble collagen, Angelica acutiloba root extract, Rosa centifolia flower extract, Rosa damask rose flower water, Rosmarinus officinalis leaf extract, Acerola fruit extract, acetylglutamic acid, theanine, glycine, hydrolyzed hyaluronic acid, and sodium hyaluronate (a mixture of beauty ingredients) 2.0% 36. Purified water (Component F) Remaining amount (*12) Rysterol ester (Tsukuno Rice Fine Chemicals Co., Ltd.) (*13) Pearl Ream 18 (Nippon Oil & Fats Co., Ltd.) (*14) Pearlream 46 (Nippon Oil & Fats Co., Ltd.)

[0102] (Manufacturing method) (1) Components 1-3 and parts of components 14, 28, and 29 were heated and dissolved at 80°C to obtain a solution (aqueous phase). (2) Components 24-27 and the remaining component 28 were mixed, a portion of component 36 was added, and the mixture was heated to 80°C to obtain a solution (aqueous phase). (3) The remainder of components 15, 30, 31, and 36 were added to the composition of (2) above to obtain a solution (aqueous phase). (4) Add the solution from (3) to the solution from (1) and mix. Add the solution (oil phase) obtained by heating and dissolving components 4-13 and 16-23 at 80°C and mix to obtain an emulsion. (5) After cooling the above (4), the homogeneously mixed components 32 and 33 were added, then components 34 and 35 were added and mixed to obtain an emulsified composition. (6) The emulsified composition of (5) above was subjected to heating and high-pressure treatment to obtain an emulsified composition (Example 38).

[0103] (evaluation) The cream of Example 38 showed a Maltese cross pattern, and it was confirmed to have suppressed crystal precipitation, good stability, non-greasy texture, and good sustained firmness. The mass ratios were as follows: The total amount of component (A) was 2.8%, the total amount of component (B) was 16.0%, the total amount of component (C) was 3.1%, the total amount of component (D) was 1.2%, and the total amount of component (E) was 0.3%. Therefore, (A) / (D) was 2.333, and (A) / (C) was 0.903.

[0104] Example 39: Cream (Component) (mass%) 1.PC compound 1 (component A) 1.6% 2.PC compound 2 (component A) 0.3% 3.PC compound 3 (component A) 0.3% 4.PC compound 4 (component A) 0.3% 5. Hydrogenated lecithin 0.1% 6. Lauroyl glutamate di(cholesteryl / behenyl / octyldodecyl) (Component C: Paste) (*4) 0.02% 7. Lauroyl glutamate di(octyldodecyl / phytosteryl / behenyl) (Ingredient C: Paste) (*2) 0.02% 8. Tridecyl Trimellitate 0.01% 9. Hydrogenated castor oil stearate (Component C: Paste) 0.02% 10. Vaseline (Component C: Paste) (*3) 0.02% 11. Hydrogenated polyisobutene (Component C: liquid, viscosity 26,200 mPa·s) (*13) 0.02% 12. Diisostearyl malate (Component C: liquid, viscosity 2,520 mPa·s) (*8) 0.02% 13. Cetyl ethylhexanoate 0.3% 14. Pentaerythritol tetraethylhexanoate 0.02% 15. Trimethylolpropane triisostearate 0.02% 16. Glyceryl tri-2-ethylhexanoate 0.6% 17. Ethyl oleate 0.1% 18. Cetearyl alcohol (Component C: Solid) 1.1% 19. Behenyl alcohol (Component C: Solid) 1.1% 20. Hexa(hydroxystearic acid / stearic acid / rosinic acid)dipentaerythrityl (component C: paste) (*15) 0.02% 21. Sorbitan oleate 0.1% 22. Polysorbate 80 (Component D) 0.1% 23. PEG-30 Phytosterol (Component D) 1.0% 24. Mineral oil 0.1% 25. Dimethicone 0.1% 26. PG Dicaprate 0.1% 27. PEG-40 Stearate (Component D) 0.5% 28. Caprylic / Capric Triglyceride 0.1% 29. Octyldodecanol 0.1% 30. Squalane 0.3% 31. Isotridecyl isononanoate 0.3% 32. Isohexadecane 0.01% 33,1,3-Butylene glycol (component B) 10.0% 34. Dipropylene glycol (Component B) 10.0% 35. Glycerin 6.0% 36. Citric acid 0.1% 37. (Sodium Acrylate / Sodium Acryloyldimethyl Taurate) Copolymer (Component E) 0.01% 38. (Acrylates / C10-30 Alkyl Acrylate) Crosspolymer (Component E) 0.2% 39. Gellan Gum (Component E) 0.03% 40. Tremella fuciformis polysaccharide (component E) 0.03% 41. Carrageenan (Component E) 0.1% 42. Sucrose 0.03% 43. Sodium hydroxide 0.1% 44. Ethanol (Component B) 2.2% 45. Phenoxyethanol (Component B) 0.3% 46.Fragrance 0.2% 47. Hydrolyzed conchiolin liquid, gentian extract, hydrolyzed silk liquid, hydrolyzed rice extract, seaweed extract, L-serine, Iris gracilis leaf extract, Artemisia capillaris flower extract, Alpinia speciosa leaf extract, Saccharomyces cerevisiae extract, pomegranate fruit extract, pomegranate peel extract, Myrica rubra fruit extract, Eggplant fruit extract, Harpagophytum root extract, parsley extract, royal jelly extract, Rosa alba flower extract, avocado extract, Gynostemma pentaphyllum extract, chamomile water, Callicarpa japonica fruit extract, apple extract, lemongrass extract, Heloniopsis orientalis extract, asparagus extract, Artemia extract, guava extract, coffee extract A mixture of jujube extract, grape leaf extract, and burnet extract, Artemisia capillaris extract, grape seed oil, Rosa rugosa extract, Rosa multiflora extract, Rosa japonica extract, Sambucus nigra flower extract, Camellia sinensis leaf extract, Chaenomeles speciosa extract, Jasminum sambac flower extract, Polyquaternium-51, Rosa multiflora fruit extract, Rosa rugosa flower extract, Rosa rugosa extract, soluble collagen, Angelica acutiloba root extract, Rosa centifolia flower extract, Rosa damask rose flower water, Rosmarinus officinalis leaf extract, Acerola fruit extract, acetylglutamic acid, theanine, glycine, hydrolyzed hyaluronic acid, and sodium hyaluronate (a mixture of beauty ingredients) 2.0% 48. Purified water (Component F) Remaining amount (*15) Cosmoll 168ARNV (Nisshin Oillio Group Ltd.)

[0105] (Manufacturing method) (1) Components 1-5 and parts of components 23, 33, and 34 were heated and dissolved at 80°C to obtain a solution (aqueous phase). (2) Components 37-42 and the remaining component 33 were mixed, a portion of component 48 was added, and the mixture was heated to 80°C to obtain a solution (aqueous phase). (3) The remaining components 22, 27, 35, 36, 43, and 48 were added to the composition of (2) above to obtain a solution (aqueous phase). (4) Add the solution from (3) to the solution from (1) and mix. Add the solution (oil phase) obtained by heating and dissolving components 6-21, 24-26, and 28-32 at 80°C and mix to obtain an emulsion. (5) After cooling the above (4), the homogeneously mixed components 44 and 45 were added, then components 46 and 47 were added and mixed to obtain an emulsified composition. (6) The emulsified composition of (5) above was subjected to heating and high-pressure treatment to obtain an emulsified composition (Example 39).

[0106] (evaluation) The cream of Example 39 showed a Maltese cross pattern, and it was confirmed that it had good suppression of crystal precipitation, good stability, was non-greasy, and had good sustained firmness. The mass ratios were as follows: The total amount of component (A) was 2.5%, the total amount of component (B) was 22.5%, the total amount of component (C) was 2.34%, the total amount of component (D) was 1.6%, and the total amount of component (E) was 0.37%. Therefore, (A) / (D) was 1.563, and (A) / (C) was 1.068.

[0107] Example 40: Lotion (Component) (mass%) 1.PC compound 1 (component A) 0.2% 2. Hydrogenated lecithin 0.1% 3. Cholesterol (component C: solids) 0.1% 4. Lauroyl glutamate di(cholesteryl / behenyl / octyldodecyl) (Component C: Paste) (*4) 0.02% 5. Shea butter (component C: solid) (*5) 0.02% 6. Ethyl oleate 0.01% 7. Choleth-10 (Component D) 0.2% 8. PEG-55 Stearate (Component D) 0.1% 9. Locust bean gum (ingredient E) 0.01% 10. Xanthan gum (ingredient E) 0.03% 11. Cellulose gum (Component E) 0.03% 12,1,3-Butylene glycol (component B) 10.0% 13. Dipropylene glycol (Component B) 5.0% 14. Citric acid 0.01% 15. Sodium citrate 0.01% 16. Nicotinamide 10.0% 17. Cyclohexane-1,4-dicarboxylic acid bisethoxydiglycol 0.1% 18. PEG-8 0.1% 19. PEG-32 0.1% 20. Glycerin 5.0% 21. Ethanol (Component B) 3.7% 22. Phenoxyethanol (Component B) 0.3% 23.Fragrance 0.2% 24. Hydrolyzed conchiolin liquid, gentian extract, hydrolyzed silk liquid, hydrolyzed rice extract, seaweed extract, L-serine, Iris gracilis leaf extract, Artemisia capillaris flower extract, Alpinia speciosa leaf extract, Saccharomyces cerevisiae extract, pomegranate fruit extract, pomegranate peel extract, Myrica rubra fruit extract, Eggplant fruit extract, Harpagophytum root extract, parsley extract, royal jelly extract, Rosa alba flower extract, avocado extract, Gynostemma pentaphyllum extract, chamomile water, Callicarpa japonica fruit extract, apple extract, lemongrass extract, Heloniopsis orientalis extract, asparagus extract, Artemia extract, guava extract, coffee extract A mixture of jujube extract, grape leaf extract, and burnet extract, Artemisia capillaris extract, grape seed oil, Rosa rugosa extract, Rosa multiflora extract, Rosa japonica extract, Sambucus nigra flower extract, Camellia sinensis leaf extract, Chaenomeles speciosa extract, Jasminum sambac flower extract, Polyquaternium-51, Rosa multiflora fruit extract, Rosa rugosa flower extract, Rosa rugosa extract, soluble collagen, Angelica acutiloba root extract, Rosa centifolia flower extract, Rosa damask rose flower water, Rosmarinus officinalis leaf extract, Acerola fruit extract, acetylglutamic acid, theanine, glycine, hydrolyzed hyaluronic acid, and sodium hyaluronate (a mixture of beauty ingredients) 2.0% 25. Purified water (Component F) Remaining amount

[0108] (Manufacturing method) (1) Components 1-3 and parts of components 7, 12, and 13 were heated and dissolved at 80°C to obtain a solution (aqueous phase). (2) Components 9 to 11 and the remaining 12 were mixed, a part of component 25 was added, and they were heated and mixed at 80 °C to obtain a solution (aqueous phase). (3) Component 8, 14 to 20, and the remaining of component 25 were added to the composition of (2) above to obtain a solution (aqueous phase). (4) The solution of (3) was added to the solution of (1) above, mixed, and a solution (oil phase) in which components 4 to 6 were dissolved by heating at 80 °C was added and mixed to obtain an emulsion. (5) After cooling (4) above, uniformly mixed components 21 and 22 were added, then components 23 and 24 were added and mixed to obtain an emulsified composition. (6) By subjecting the emulsified composition of (5) above to a high-temperature and high-pressure treatment, an emulsified composition (Example 40) was obtained.

[0109] (Evaluation) For the lotion of Example 40, a Maltese cross was confirmed, and it was confirmed that the suppression of crystal precipitation, good stability, non-stickiness, and persistence of firmness were good. The mass ratio relationship was as follows. The total amount of component (A) was 0.2%; the total amount of component (B) was 19.0%; the total amount of component (C) was 0.14%; the total amount of component (D) was 0.3%; the total amount of component (E) was 0.07%. Therefore, (A) / (D) was 0.667; (A) / (C) was 1.429.

[0110] Example 41: Sunscreen (Components) (mass %) 1. PC Compound 1 (Component A) 1.5% 2. Hydrogenated lecithin 0.5% [[ID=​​​​​​​​​​​​​9. Polysilicone-15 (Component C: Liquid, Viscosity 1,019 mPa·s) 0.2% 10. Bis-ethylhexyloxyphenol methoxyphenyl triazine (Component C: Solid) 0.1% 11. Dimer dilinoleate (phytosteryl / isostearyl / cetyl / stearyl / behenyl) (Component C: Paste) (*16) 0.01% 12. Zinc oxide 0.01% 13. Behenyl alcohol (Component C: Solid) 0.9% 14. Cetostearyl alcohol (Component C: Solid) 0.4% 15. Shea butter (component C: solid) (*5) 0.01% 16. BHT 0.1% 17. PG Dicaprate 0.1% 18. Trimethylolpropane triisostearate 0.1% 19. Isotridecyl isononanoate 0.1% 20. Mineral oil 0.1% 21. Diphenylsiloxy Phenylen Trimethicone 0.1% 22. Dimethicone 0.1% 23. Isododecane 0.1% 24. (Acrylates / C10-30 Alkyl Acrylate) Crosspolymer (Component E) 0.3% 25. Sodium acrylate / sodium acryloyldimethyl taurate copolymer (component E) 0.2% 26. Hydroxypropyl methylcellulose (component E) (*17) 0.01% 27. Dipropylene glycol (Component B) 4.0% 28,1,3-Butylene glycol (component B) 7.0% 29. Glycerin 2.0% 30. EDTA-2Na 0.02% 31. Methylenebisbenzotriazolyltetramethylbutylphenol (Component C: Solid) 3.0% 32. Polyglyceryl-10 Laurate (Component D) 1.0% 33. Potassium hydroxide 0.15% 34. Ethanol (Component B) 2.8% 35. Phenoxyethanol (Component B) 0.2% 36.Fragrance 0.2% 37. A mixture of gentian extract, hydrolyzed conchiolin liquid, hydrolyzed silk liquid, hydrolyzed rice extract, seaweed extract, L-serine, Iris gracilis leaf extract, Artemisia capillaris flower extract, Alpinia speciosa leaf extract, guava extract, coffee extract, jujube extract, grape leaf extract, water-soluble collagen, royal jelly extract, Angelica acutiloba root extract, Rosa centifolia flower extract, Rosa damask flower water, Rosmarinus officinalis leaf extract, Acerola serrata fruit extract, acetylglutamic acid, theanine, glycine, hydrolyzed hyaluronic acid, and sodium hyaluronate (a mixture of beauty ingredients). 2.0% 38. Purified water (Component F) Remaining amount (*16) PLANDOOL-S (Nippon Seika Co., Ltd.) (*17) Metroze 60SH-4000 (Shin-Etsu Chemical Co., Ltd.)

[0111] (Manufacturing method) (1) Components 1-4 and a portion of components 27 and 28 were heated and dissolved at 80°C to obtain a solution (aqueous phase). (2) Components 24-26 and the remaining component 28 were mixed, a portion of component 38 was added, and the mixture was heated to 80°C to obtain a solution (aqueous phase). (3) Components 5, 12, 29-30, and a portion of 38 were added to the composition described in (2) above to obtain a solution (aqueous phase). (4) Add the solution from (3) to the solution from (1) and mix. Add the solution (oil phase) obtained by heating and dissolving components 6-11 and 13-23 at 80°C and mix to obtain an emulsion. (5) After cooling the above (4), the remaining homogeneous mixture of components 31 and 32 and component 38 was added, followed by the addition of homogeneous mixture of components 34 and 35, then components 36 and 37 were added and mixed to obtain an emulsified composition. (6) The emulsified composition of (5) above was subjected to heating and high-pressure treatment to obtain an emulsified composition (Example 41).

[0112] (evaluation) The sunscreen of Example 41 showed a Maltese cross pattern, and it was confirmed that it had good suppression of crystal precipitation, good stability, no stickiness, and good retention of firmness. The mass ratios were as follows: The total amount of component (A) was 1.5%, the total amount of component (B) was 14.0%, the total amount of component (C) was 4.94%, the total amount of component (D) was 2.0%, and the total amount of component (E) was 0.51%. Therefore, (A) / (D) was 0.750, and (A) / (C) was 0.304.< / e>

Claims

1. The following components (A) to (F): (A) Formula (1): 【Chemistry 1】 [In the formula, R １ R is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms. ４ R is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, where R １ and R ４ At least one of them is an unsaturated hydrocarbon group having 12 to 22 carbon atoms; and R ２ and R ３ These may be the same or different, and each is independently an alkyl group having 1 to 6 carbon atoms, or a hydroxyalkyl group having 1 to 6 carbon atoms. The compound represented by is present in an amount of 0.1 to 5% by mass relative to the total amount (100% by mass) of the oil-in-water emulsion composition. (B) Monovalent or divalent alcohols that are liquid at 20°C, (C) One or more oils selected from the group consisting of oils with a viscosity of 1000 mPa·s or more at 20°C, and oils that are semi-solid or solid at 20°C. (D) One or more surfactants selected from the group consisting of nonionic surfactants having a polyoxyethylene group and / or a polyglyceryl group in the hydrophilic group, and anionic surfactants. (E) Water-soluble polymers, and (F) Water; An oil-in-water emulsion composition containing the following:

2. In formula (1), R １ and R ４ One of them is an unsaturated hydrocarbon group having 18 carbon atoms, and R １ and R ４ The other one of them is a saturated hydrocarbon group having 22 carbon atoms, and R ２ and R ３ The oil-in-water type emulsion composition according to claim 1, wherein both are hydroxyethyl groups.

3. The oil-in-water emulsion composition according to claim 1, wherein component (B) is one or more selected from the group consisting of 1,3-butylene glycol, dipropylene glycol, and ethanol.

4. The oil-in-water emulsion composition according to claim 1, wherein the ratio of component (A) to component (D) ((A) / (D)) is 0.01 to 200 by mass.

5. The oil-in-water emulsion composition according to claim 1, wherein the ratio of component (A) to component (C) ((A) / (C)) is 0.1 to 100 by mass.

6. The oil-in-water emulsion composition according to claim 1, wherein at least one of component (C) is an oil that is semi-solid or solid at 20°C.

7. The oil-in-water emulsion composition according to claim 1, wherein at least one of component (C) is a solid oil at 20°C.

8. The oil-in-water emulsion composition according to claim 1, wherein at least one of component (D) is a nonionic surfactant having a polyoxyethylene group in its hydrophilic group.

9. The oil-in-water emulsion composition according to claim 1, wherein at least one of component (D) is a nonionic surfactant having a lipophilic group with a group selected from the group consisting of phytosterol residues, cholesterol residues, saturated fatty acid residues, and unsaturated fatty acid residues.

10. The oil-in-water emulsion composition according to claim 1, wherein the oil-in-water emulsion composition has emulsion particles that can be identified as a Maltese cross when observed under a polarizing microscope.

11. An oil-in-water emulsion composition according to any one of claims 1 to 10, which is an emulsified cosmetic.

12. A method for producing an oil-in-water emulsion composition according to any one of claims 1 to 10, A step of preparing a first mixed solution by mixing component (A), component (B), and component (D); A step of mixing component (E) and component (F) to prepare a second mixed solution; A step of mixing the first mixed solution and the second mixed solution to prepare a mixed solution that forms the aqueous phase; and, A step to obtain an emulsion composition by adding an oil-forming component (C) to a mixed solution that forms the aqueous phase and mixing it. Methods that include...

13. A method for producing an oil-in-water emulsion composition according to claim 12, further comprising the step of heating and applying high pressure to the obtained emulsion composition.

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