JP7738404B2 - Oil-in-water emulsion composition - Google Patents

Description

The present invention relates to an oil-in-water emulsion composition containing a novel compound that functions as an emulsifier, and a method for stabilizing the emulsion.

In oil-in-water emulsion compositions, particularly oil-in-water emulsion cosmetics, attempts are being made to incorporate various ingredients to improve emulsion stability and other properties, the feel upon application, and moisturizing effects, and new compounds that can be used in such compositions are being researched on a daily basis. For example, phospholipids are natural surface-active substances that have good affinity for the skin and a high moisturizing effect, and are functional substances that can also be used as emulsifiers (surfactants). Furthermore, research is also being conducted on a daily basis to develop compounds with phospholipid-like structures that further enhance the functionality of phospholipids.

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

The applicant therefore embarked on research and development of novel compounds with improved surfactant properties that have a structure similar to phospholipids.

Japanese Patent Application Laid-Open No. 2011-213602

Under the above circumstances, the present applicants developed novel compounds having a structure similar to phospholipids and improved surfactant properties, and further developed formulations of compositions (particularly oil-in-water emulsion compositions) using such novel compounds, resulting in the present invention.
An object of the present invention is to provide an oil-in-water emulsion composition containing a novel compound having a phospholipid-like structure that functions as an emulsifier. Another object of the present invention is to provide a method for emulsion stabilization of an oil-in-water emulsion composition containing the compound that functions as an emulsifier.

The present invention includes, but is not limited to, the following embodiments.
[1] The following components (A) to (C):
(A) Formula (1):
[In the formula, ^R1 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, ^R4 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, and at least one of R1 and ^R4 is an unsaturated hydrocarbon group having ¹² to 22 carbon atoms; and ^R2 and ^R3 may be the same or different and are each independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and a polyoxyalkylene group having 4 to 60 carbon atoms.]
A compound represented by
(B) one or more oils selected from the group consisting of oils having a viscosity of 1000 mPa s or more at 20°C and oils that are semi-solid at 20°C, and
(C) one or more polymers selected from the group consisting of acrylic acid polymers and methacrylic acid polymers;
An oil-in-water emulsion composition (hereinafter referred to as "the emulsion composition") comprising:
[2] The oil-in-water emulsion composition according to [1], wherein in formula (1), at least one of R ¹ and R ⁴ is an unsaturated hydrocarbon group having 18 carbon atoms.
[2-1]
The oil-in-water emulsion composition according to [1], wherein in formula (1), at least one of R ¹ and R ⁴ is an unsaturated hydrocarbon group having 18 carbon atoms and 1 to 3 carbon-carbon double bonds.
[3] The oil-in-water emulsion composition according to [1] or [2], wherein in formula (1), R ² and R ³ are each independently a methyl group or a hydroxyethyl group.
[4] The oil-in-water emulsion composition according to any one of [1] to [3], wherein component (C) is one or more polymers selected from the group consisting of carboxyvinyl polymers and alkyl-modified carboxyvinyl polymers.
[5] The oil-in-water emulsion composition according to any one of [1] to [4], wherein the ratio of component (A) to component (B) ((A)/(B)) is 0.1 or more in mass ratio.
[6] The oil-in-water emulsion composition according to any one of [1] to [5], wherein the ratio of component (C) to component (A) ((C)/(A)) is 0.04 or more in mass ratio.
[7] The oil-in-water emulsion composition according to any one of [1] to [6], wherein component (B) is an oily agent that is semi-solid at 20°C.
[8] The oil-in-water emulsion composition according to any one of [1] to [7], further comprising a component (D) a surfactant.
[9] The oil-in-water emulsion composition according to [8], wherein the ratio of component (D) to component (A) ((D)/(A)) is 0.01 or more in mass ratio.
[10] The oil-in-water emulsion composition according to [8] or [9], wherein component (D) is a nonionic surfactant.
[11] The oil-in-water emulsion composition according to [10], wherein the nonionic surfactant is a nonionic surfactant having a fatty acid residue having 12 to 22 carbon atoms and a polyoxyethylene group.
[12] The oil-in-water emulsion composition according to any one of [1] to [11], which is a cosmetic.
[13] A method for emulsifying and stabilizing an oil-in-water emulsion composition comprising the following components (A) and (B):
(A) Formula (1):
[In the formula, ^R1 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, ^R4 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, and at least one of R1 and ^R4 is an unsaturated hydrocarbon group having ¹² to 22 carbon atoms; and ^R2 and ^R3 may be the same or different and are each independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and a polyoxyalkylene group having 4 to 60 carbon atoms.]
and a compound represented by
(B) one or more oil agents selected from the group consisting of oil agents having a viscosity of 1000 mPa s or more at 20°C and oil agents that are semi-solid at 20°C;
A method (hereinafter referred to as "the present emulsion stabilization method") comprising blending component (C), one or more polymers selected from the group consisting of acrylic acid polymers and methacrylic acid polymers, together with components (A) and (B).

The present invention provides an oil-in-water emulsion composition containing a novel compound with a phospholipid-like structure that functions as an emulsifier. The present invention also provides a method for stabilizing emulsion of an oil-in-water emulsion composition containing the compound that functions as an emulsifier.

The oil-in-water emulsion composition of the present invention comprises the following components (A) to (C):
(A) Formula (1):
[In the formula, ^R1 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, ^R4 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, and at least one of R1 and ^R4 is an unsaturated hydrocarbon group having ¹² to 22 carbon atoms; and ^R2 and ^R3 may be the same or different and are each independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and a polyoxyalkylene group having 4 to 60 carbon atoms.]
(hereinafter referred to as "PC compound" in this specification),
(B) one or more oils selected from the group consisting of oils having a viscosity of 1000 mPa s or more at 20°C and oils that are semi-solid at 20°C; and
(C) one or more polymers selected from the group consisting of acrylic acid polymers and methacrylic acid polymers;
Contains:
In this specification, (A) to (C) and (D) are symbolic symbols of the components, and hereinafter may be referred to as component (A), etc.

Component (A)
As described above, component (A) is a compound containing a phosphorylcholine-like group (PC compound).
In formula (1), ^R1 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, i.e., ^R1 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms, or a saturated hydrocarbon group having 12 to 22 carbon atoms. Furthermore, ^R4 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, i.e., ^R4 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms, or a saturated hydrocarbon group having 12 to 22 carbon atoms. However, at least one of ^R1 and ^R4 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms. In other words, both ^R1 and ^R4 are unsaturated hydrocarbon groups having 12 to 22 carbon atoms, or ^R1 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms and ^R4 is a saturated hydrocarbon group having 12 to 22 carbon atoms, or ^R1 is a saturated hydrocarbon group having 12 to 22 carbon atoms and ^R4 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms. There is no case where both R ¹ and R ⁴ are saturated hydrocarbon groups having 12 to 22 carbon atoms.

In one preferred embodiment, one of ^R1 and ^R4 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, it is preferred that ^R1 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms and ^R4 is a saturated hydrocarbon group having 12 to 22 carbon atoms, or that ^R1 is a saturated hydrocarbon group having 12 to 22 carbon atoms and ^R4 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms. In this case, emulsion stability can be further improved. It is even more preferred that ^R1 is an unsaturated hydrocarbon group having 12 to 22 carbon atoms and ^R4 is a saturated hydrocarbon group having 12 to 22 carbon atoms. In this case, the uniformity of the oil phase is more likely to be improved. Of course, both ^R1 and ^R4 may be unsaturated hydrocarbon groups having 12 to 22 carbon atoms. Even in this case, the uniformity of the oil phase is more likely to be improved, especially when mixed with one or more highly viscous or semi-solid oil agents such as component (B). The compound of formula (1) has an unsaturated bond in its molecule, which increases its solubility, and it is presumed that this enhances the interaction between the oil agent (B) and the polymer (C) and the lipophilic chain of the compound of formula (1), thereby further improving the stability of the emulsion.The saturated hydrocarbon group may be, for example, what is called an alkyl group.The unsaturated hydrocarbon group may be, for example, what is called an alkenyl group or an alkynyl group.

In ^R1 and ^R4 (the following descriptions of ^R1 and ^R4 apply independently unless otherwise specified), the unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms may be linear, branched, or cyclic. The unsaturated or saturated hydrocarbon group of ^R1 and ^R4 is preferably a linear or branched hydrocarbon group, more preferably a linear hydrocarbon group. In particular, it is preferable that both ^R1 and ^R4 are linear or branched hydrocarbon groups, and it is even more preferable that both are linear hydrocarbon groups. The unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms may be a hydrocarbon group (e.g., an aliphatic alkyl group or alkenyl group) having a structure obtained by removing a hydroxy group (OH) from a monohydric aliphatic alcohol. The saturated hydrocarbon group of ^R1 and ^R4 preferably has 16 to 22 carbon atoms, and even more preferably has 18 to 22 carbon atoms.

The saturated hydrocarbon group having 12 to 22 carbon atoms for ^R1 and ^R4 is not limited thereto, but examples of linear groups include lauryl (12 carbon atoms; also called dodecyl group), myristyl (14 carbon atoms; also called tetradecyl group), cetyl (16 carbon atoms; also called hexadecyl group), stearyl (18 carbon atoms; also called octadecyl group), and behenyl (22 carbon atoms; also called docosyl group), and examples of branched groups include isostearyl (18 carbon atoms; also called 16-methylheptadecyl group). Of these, stearyl and behenyl groups are preferred, with behenyl being more preferred.

In the unsaturated hydrocarbon groups having 12 to 22 carbon atoms in ^R1 and ^R4 , the unsaturation may be either a carbon-carbon double bond unsaturation or a carbon-carbon triple bond unsaturation, but is preferably a carbon-carbon double bond unsaturation. Unsaturated hydrocarbon groups having a carbon-carbon double bond are also called alkenyl groups. The number of unsaturations is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. When the number of unsaturations is two or more, it is preferable that all of them are carbon-carbon double bond unsaturations. The number of carbon atoms in the unsaturated hydrocarbon groups in ^R1 and ^R4 is preferably 16 to 22.

In formula (1), it is more preferable that at least one of ^R1 and ^R4 is an unsaturated hydrocarbon group having 18 carbon atoms. In this case, the stability of the present emulsion composition can be further improved. Furthermore, it is even more preferable that at least one of ^R1 and ^R4 is an unsaturated hydrocarbon group having 18 carbon atoms and having 1 to 3 carbon-carbon double bonds. This can further improve emulsion stability. The number of carbon-carbon double bonds is more preferably 1 or 2, and even more preferably 1. Examples of unsaturated hydrocarbon groups having 18 carbon atoms include an oleyl group, an elaidyl group, a linoleyl group (multiple unsaturated), and a linoleyl group (multiple unsaturated), and of these, an oleyl group is more preferable. The oleyl group is also called a cis-9-octadecenyl group.

In one preferred embodiment, one of ^R1 and ^R4 is an oleyl group, and the other is a group selected from the group consisting of an oleyl group, a behenyl group, and a stearyl group.

Specific combinations of ^R1 and ^R4 , when expressed as ( ^R1 , ^R4 ), include, but are not limited to, combinations such as (oleyl group, oleyl group), (oleyl group, behenyl group), (behenyl group, oleyl group), (oleyl group, stearyl group), (stearyl group, oleyl group), etc. Among these, combinations such as (oleyl group, oleyl group), (oleyl group, behenyl group), and (behenyl group, oleyl group) are preferred, and combinations such as (oleyl group, behenyl group), and (behenyl group, oleyl group) are more preferred.

In formula (1), ^R2 and ^R3 (the following explanations of ^R2 and ^R3 apply independently unless otherwise specified) are each independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and a polyoxyalkylene group having 4 to 60 carbon atoms. Here, the alkyl or alkylene moiety in the alkyl, hydroxyalkyl, and polyoxyalkylene may be linear or branched. Preferably, the alkyl or alkylene moiety is linear. ^R2 and ^R3 may be the same or different, but from the viewpoint of production of the PC compound, it is more preferable that they are the same.

In ^R2 and ^R3 , examples of the alkyl group having 1 to 6 carbon atoms include, for example, linear methyl, ethyl, propyl, butyl, pentyl, and hexyl groups, and branched alkyl groups include _isopropyl and isobutyl groups. Preferred examples of the alkyl group having 1 to 6 carbon atoms include a methyl group ( _-CH3 ), an ethyl group ( _-CH2CH3 ), and a _propyl group ( _-CH2CH2CH3 ), with a _methyl group ( _-CH3 ) being more preferred.

In ^R2 and ^R3 , the hydroxyalkyl group having 1 to 6 carbon atoms is preferably a hydroxyalkyl group having a hydroxy group at its terminal. Examples of the hydroxyalkyl group having 1 to 6 carbon atoms include a hydroxymethyl group, a hydroxyethyl group, and a hydroxypropyl group. As the hydroxyalkyl group having 1 to 6 carbon atoms, a _hydroxyethyl group ( _-CH2CH2OH ) having a hydroxy group at its terminal is more preferred.

In ^R2 and ^R3 , the polyoxyalkylene group having 4 to 60 carbon atoms is a group having a repeating oxyalkylene structure, and can be expressed, for example, by the formula -(alkylene-O) _n -H) [wherein n is an integer of 2 or more]. This n is preferably 2 to 30, more preferably 2 to 10, and even more preferably 2 to 6. This alkylene may be linear or branched. Examples of polyoxyalkylene groups having 4 to 60 carbon atoms include polyoxyethylene groups and polyoxypropylene groups, and in particular, -( _CH2CH2O ) _nH , -( _CH2CH2CH2O ) _nH , -( _{CH2CH ( CH3 )} O) _nH , and the like (wherein _n is as defined above).

It is preferable that ^R2 and ^R3 are each independently a methyl group or a hydroxyethyl group. In this case, emulsion stability can be further improved. Furthermore, it is more preferable that both ^R2 and ^R3 are methyl groups or both are _hydroxyethyl groups (particularly _-CH2CH2OH ).

In a preferred embodiment of the compound of formula (1), at least one of ^R1 and ^R4 is an unsaturated hydrocarbon group having 18 carbon atoms, and ^R2 and ^R3 are each independently a methyl group or a _hydroxyethyl group (particularly _-CH2CH2OH ). In this case, emulsion stability can be further improved.

Specific combinations of R ¹ , R ² , R ³ and R ⁴ are not limited to these, but when expressed as (R ¹ , R ² , R ³ , R ⁴ ), examples of combinations include (oleyl group, methyl group, methyl group, oleyl group), (oleyl group, methyl group, methyl group, behenyl group), (behenyl group, methyl group, methyl group, oleyl group), (oleyl group, hydroxyethyl group, hydroxyethyl group, behenyl group), (behenyl group, hydroxyethyl group, hydroxyethyl group, oleyl group), and the like.

A method for producing a PC compound will now be described. The PC compound represented by formula (1) is obtained by reacting an alcohol represented by formula (2) with 2-chloro-2-oxo-1,3,2-dioxaphospholane (hereinafter abbreviated as COP) in the presence of an organic base to produce an intermediate, and then ring-opening the intermediate with a tertiary amine represented by formula (3). The resulting PC compound can be purified by common purification methods such as reprecipitation and recrystallization.
R ¹ , R ² , R ³ and R ⁴ in formula (2) and formula (3) have the same meanings as those in formula (1).

The PC compound represented by formula (1) is a compound that contains within its molecule a group (hereinafter referred to as a "phosphorylcholine-like group") with a structure similar to that of phosphorylcholine (-N ⁺ (CH ₃ ) ₂ (CH ₂ ) ₂ -O-PO ₃ ^- -). The phosphorylcholine-like group is a polar group that functions as a hydrophilic group. Furthermore, unsaturated or saturated hydrocarbon groups are bonded to both sides of the phosphorylcholine-like group, and these hydrocarbon groups function as hydrophobic groups. Therefore, PC compounds can function as surface-active components (surfactants, emulsifiers). More specifically, because PC compounds contain both cationic and anionic moieties, they can be classified as amphoteric surfactants (zwitterionic surfactants). Furthermore, PC compounds are gemini surfactants that have two hydrophobic groups and two hydrophilic groups. That is, PC compounds can be said to have a structure in which two molecules of a single-chain, single-hydrophilic group surfactant are covalently linked via a spacer. Furthermore, because PC compounds have a structure similar to that of phospholipids, they are thought to have a high affinity for the skin, and when the present emulsion composition (particularly a cosmetic) is applied to the skin, it can provide a good feeling of use, such as a fresh feeling of use, and moisturizing properties.

Here, in compounds of formula (1) in which both ^R1 and ^R4 are saturated hydrocarbon groups having 12 to 22 carbon atoms, it is difficult to achieve emulsion stability as high as that of component (A). An example of such a compound is behendimonium ethyl stearyl phosphate. Behendimonium ethyl stearyl phosphate is a compound of formula (1) in which ^R1 is a behenyl group, ^R2 and ^R3 are both methyl groups, and ^R4 is a stearyl group, and is not included in component (A). Compounds that do not have an unsaturated hydrocarbon group, such as behendimonium ethyl stearyl phosphate, have problems such as low solubility in oil phases, which limits formulation possibilities, and the tendency for the cosmetic to leave a thick film on the skin after application. However, it has been discovered that the compound of formula (1) above has improved solubility in oil phases compared to behendimonium ethyl stearyl phosphate and the like, and can improve the thick film on the skin after application. Furthermore, the compound of formula (1) has a gemini structure and may also have the advantages of behendimonium ethyl stearyl phosphate, such as a low CMC (critical micelle concentration) and a low Krafft point. It has been demonstrated that, in oil-in-water emulsion compositions, the PC compound of formula (1) provides superior emulsion stability when compared with compositions using compounds without unsaturated hydrocarbon groups, such as behendimonium ethyl stearyl phosphate (see Examples).

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).

The content of component (A) in the emulsion composition (the total amount if multiple components are present) is not limited to the above, but from the viewpoints of emulsion stability and achieving a good feel when used, it can be, for example, 0.01 to 10% by mass, and preferably 0.1 to 5% by mass, relative to the total amount of the emulsion composition (100% by mass). Furthermore, the content of component (A) is preferably 0.1 to 3% by mass, more preferably 0.5 to 3% by mass, and even more preferably 0.5 to 2% by mass, relative to the total amount of the emulsion composition. In this case, an emulsion composition with high emulsion stability can be obtained.

Ingredient (B)
Component (B) is one or more oils selected from the group consisting of oils having a viscosity of 1,000 mPa·s or more at 20° C. and oils that are semi-solid at 20° C. In the present invention, component (A) can be used to stably emulsify a composition that contains one or more highly viscous or semi-solid oils such as component (B), and even when a highly viscous or semi-solid oil is incorporated, it is possible to obtain an emulsion composition (particularly a cosmetic) that does not impair the fresh feeling of use and that excels in the sustained moisturizing feeling and appropriate film-like feel on the skin after application that are derived from the highly viscous or semi-solid oil.

The viscosity of an oil agent (hereinafter referred to as "oil agent (B1)") having a viscosity of 1,000 mPa·s or more at 20°C can be measured using a Brookfield viscometer. There is no particular upper limit to the viscosity of oil agent (B1), but it may be, for example, 500,000 mPa·s or less. A viscosity of 1,500 to 500,000 mPa·s is particularly preferred.

For an oil agent that is semi-solid at 20°C (hereinafter referred to as "oil agent (B2)"), the term "semi-solid" refers to a state that is different from a liquid but different from a solid, and has fluidity, i.e., a state between a solid and a liquid. For example, a semi-solid state may be a state in which the viscosity is higher than the upper limit of measurable viscosity by the viscosity measurement method described above and is therefore unmeasurable, but still has fluidity. Oil agent (B2) is preferably an oil agent with a melting point of 30°C or higher and lower than 61°C. One embodiment of the semi-solid state may be a paste state.

Examples of the oil agent for component (B) include natural or synthetic ester oils, hydrocarbon oils, higher alcohols, and fatty acids that have a viscosity of 1,000 mPa·s or more at 20°C or are semi-solid at 20°C.

Examples of oils (B1) with a viscosity of 1,000 mPa·s or more at 20°C include, but are not limited to, polyglyceryl-2 diisostearate (e.g., viscosity (20°C): 1,160 mPa·s), di(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), highly polymerized dimethylpolysiloxane (1 00,000 CS) (for example, viscosity (20°C): 1,412,000 mPa·s), polyglyceryl monoisostearate (for example, viscosity (20°C): 4,450 mPa·s), dipentaerythrityl tri-polyhydroxystearate (for example, viscosity (20°C): 10,300 mPa·s), hydrogenated polyisobutene (with a viscosity at 20°C of 1,000 mPa·s or more; for example, viscosity (20°C) of 26,200 mPa·s or 44,100 mPa·s). These may be used alone or in combination of two or more.

Examples of oils (B2) that are semi-solid at 20°C include, but are not limited to, di(octyldodecyl/phytosteryl/behenyl) lauroyl glutamate, di(cholesteryl/behenyl/octyldodecyl) lauroyl glutamate, phytosteryl/isostearyl/cetyl/stearyl/behenyl dimer dilinoleate, petrolatum, phytosteryl isostearate, dipentaerythrityl hexa(hydroxystearate/stearic acid/rosinate), hydrogenated palm oil, and cholesteryl hydroxystearate. These may be used alone or in combination of two or more.

The oil of component (B) may be either oil (B1) having a viscosity of 1,000 mPa·s or more at 20°C or oil (B2) that is semi-solid at 20°C, or both. Component (B) may be used alone or in combination of two or more of the above oils.

The content of component (B) (or the total amount if multiple components are present) is not limited to the above, but from the perspective of achieving excellent usability and emulsion stability, it can be 0.1 to 20% by mass, preferably 0.5 to 15% by mass, and more preferably 1 to 10% by mass, relative to the total amount of the emulsion composition (100% by mass).

Here, the ratio of component (A) to component (B) ((A)/(B)) is preferably 0.1 or greater by mass. By making the ratio of the content of component (A) to the content of component (B) 0.1 or greater, component (B) can be emulsified more effectively, further improving the emulsion stability of the emulsion composition. From the viewpoints of emulsion stability and a good usability, the ratio of component (A) to component (B) ((A)/(B)) is preferably 30 or less by mass. This ratio ((A)/(B)) is preferably 0.1 to 30, and more preferably 0.2 to 15.

Ingredient (C)
Component (C) is one or more polymers (macromolecules) selected from the group consisting of acrylic acid polymers and methacrylic acid polymers. In this emulsion composition, emulsion stability can be significantly improved by incorporating the polymer of component (C) when emulsifying the oil of component (B) with the surfactant of component (A). Specifically, when a composition containing one or more highly viscous or semi-solid oils such as component (B) is emulsified with a phospholipid analog, the resulting emulsion stability can be insufficient. However, it was discovered that the stability of the resulting emulsion composition can be significantly improved by using component (A) as a surfactant and combining it with a specific polymer of component (C), leading to the invention. Furthermore, when used as a cosmetic, an emulsion composition combining components (A) to (C) can impart a pleasant feel during use, such as a moisturizing feel and a moderate film-like texture to the skin after application. Thus, the present invention provides an oil-in-water emulsion composition containing components (A) to (C) that has high emulsion stability and an excellent feel during use.

The polymer of component (C) can typically be a water-soluble or hydrophilic polymer. Therefore, it is believed that this polymer is primarily dissolved or dispersed in the aqueous phase of the present emulsion composition. Furthermore, the polymer of component (C) can exhibit a thickening effect when dissolved or dispersed in water, for example. This thickening effect can further improve emulsion stability. Furthermore, the polymer of component (C) possesses ionicity derived from acrylic acid residues or methacrylic acid residues, and this ionicity enhances the thickening effect, further improving emulsion stability. Here, the lipophilic chain of the main chain of acrylic acid polymers and methacrylic acid polymers typically consists of a hydrocarbon chain, and it is believed that this lipophilic chain interacts with the lipophilic portion of component (A), thereby enhancing stability.

Examples of component (C) include, but are not limited to, polyacrylic acid and its salts, carboxyvinyl polymers, alkyl-modified carboxyvinyl polymers, methacrylic acid polymers, alkyl-modified methacrylic acid polymers, acrylate copolymers, copolymers of acrylic acid and acryloyldimethyltaurate (e.g., sodium acrylate-sodium acryloyldimethyltaurate copolymer), copolymers of hydroxyethyl acrylate and acryloyldimethyltaurate, and polymers containing acryloyldimethyltaurate monomer units, such as copolymers of acrylic acid, acrylate, acrylamide, and acryloyldimethyltaurate.

Component (C) is preferably one or more polymers selected from the group consisting of carboxyvinyl polymers and alkyl-modified carboxyvinyl polymers. In this case, emulsion stability can be significantly improved. Carboxyvinyl polymers are also known as carbomers. Examples of alkyl-modified carboxyvinyl polymers include (acrylates/C10-30 alkyl acrylate) crosspolymers. Component (C) may be one of the above polymers, or a combination of two or more of them.

The content of component (C) (or the total amount if multiple components are present) is not limited to the above, but from the perspective of achieving high emulsion stability and an excellent feel when used, it can be 0.01 to 1% by mass, preferably 0.03 to 0.5% by mass, and more preferably 0.04 to 0.4% by mass, relative to the total amount of the emulsion composition (100% by mass).

Here, the ratio of component (C) to component (A) ((C)/(A)) is preferably 0.04 or greater by mass. By making the ratio of the content of component (C) to the content of component (A) 0.04 or greater, the composition obtained by emulsifying component (B) with component (A) can be more stabilized, and the emulsion stability of the emulsion composition can be further improved. From the viewpoint of emulsion stability and a good usability, the ratio of component (C) to component (A) ((C)/(A)) is preferably 20 or less by mass. This ratio ((C)/(A)) is preferably 0.04 to 20, and more preferably 0.04 to 10.

Ingredient (D)
The present emulsion composition may further contain a surfactant as component (D). By incorporating a surfactant, the emulsion stability of the present emulsion composition can be further improved. Note that component (A) is not included in the surfactant as component (D). When component (A) is considered to be a surfactant, the surfactant as component (D) can be said to be a surfactant other than component (A).

Component (D) can be one or more surfactants selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants. Component (D) is preferably a nonionic surfactant (hereinafter referred to as "(D1)"). In this case, high emulsion stability and an excellent feel during use can be achieved. Furthermore, nonionic surfactant (D1) is preferably a nonionic surfactant having a fatty acid residue with 12 to 22 carbon atoms and a polyoxyethylene group (hereinafter referred to as "(D2)"). In this case, the interaction with components (A) to (C) is enhanced, making it possible to achieve even higher emulsion stability and an excellent feel during use. Examples of fatty acid residues with 12 to 22 carbon atoms include oleic acid, stearic acid, myristic acid, and lauric acid.

Nonionic surfactants include, but are not limited to, POE-sorbitan fatty acid esters such as polyoxyethylene sorbitan monooleate (20E.O.) and polyoxyethylene sorbitan monosterate (20E.O.), POE sorbitan fatty acid esters such as PEG-40 sorbit oleate, and POE-fatty acid esters such as PEG-150 stearate, PEG-55 stearate, PEG-40 stearate, and PEG-10 laurate. Furthermore, examples of nonionic surfactants other than (D2) that fall under (D1) include POE-hydrogenated castor oils such as PEG-80 hydrogenated castor oil, PEG-60 hydrogenated castor oil, and PEG-40 hydrogenated castor oil; sorbitan fatty acid esters such as sorbion sesquiisostearate and sorbion palmitate; glyceryl fatty acid esters such as polyglyceryl-10 laurate, polyglyceryl-10 oleate, and polyglyceryl-10 diisostearate; and sucrose fatty acid esters.

When surfactants other than the nonionic surfactant (D1) are used, examples of anionic surfactants include, but are not limited to, acyl methyl taurines of higher fatty acids such as sodium N-stearoyl-N-methyl taurate, acyl lactates such as sodium stearoyl lactylate, N-acyl glutamates such as sodium N-stearoyl-L-glutamate, fatty acid soaps such as sodium distearoyl glutamate lysine, sodium dilauryl glutamate lysine, and sodium laurate, higher alkyl sulfates such as sodium lauryl sulfate, alkyl ether sulfates such as POE-lauryl triethanolamine sulfate, and phosphates such as sodium POE-oleyl ether phosphate. Examples of cationic surfactants include, but are not limited to, quaternary ammonium salts such as behenyl PG trimonium chloride and lauryl trimethylammonium chloride, and amidoamine compounds such as behenic acid dimethylaminopropylamide. Examples of amphoteric surfactants include, but are not limited to, phospholipids, phospholipid analogues, alkyl betaine amphoteric surfactants such as lauryl dimethyl betaine, amidopropyl betaine amphoteric surfactants such as oleic acid amidopropyl betaine, and amino acid amphoteric surfactants such as sodium lauryl aminopropionate.

It is also preferable to incorporate a phospholipid or phospholipid analogue (particularly a compound containing a phosphorylcholine analogue group other than the above-mentioned PC compounds) as a surfactant as component (D). Phospholipids or phospholipid analogues have a high affinity with the above-mentioned PC compounds and can further improve emulsion stability. Examples of phospholipids include hydrogenated soybean phospholipids, lecithin, and hydrogenated lecithin. Examples of phospholipid analogues include behendimonium ethyl stearyl phosphate.
Component (D) may be one of the above surfactants or a combination of two or more of them.

When the emulsion composition contains component (D), the content of component (D) (or the total amount if multiple components are present) is not limited to this, but from the perspective of achieving high emulsion stability and an excellent feel when used, it can be 0.01 to 10% by mass, preferably 0.1 to 5% by mass, and more preferably 0.3 to 5% by mass, relative to the total amount of the emulsion composition (100% by mass).

When component (D) is contained, the ratio of component (D) to component (A) ((D)/(A)) is preferably 0.01 or greater by mass. When the ratio of the content of component (D) to the content of component (A) is 0.01 or greater, the emulsifying power of component (A) and the emulsifying power of component (D) are combined, making the emulsifying power more effective, and the emulsion stability of the emulsion composition can be further improved. From the perspective of a good usability, the ratio of component (D) to component (A) ((D)/(A)) is preferably 100 or less by mass. This ratio ((D)/(A)) is preferably 0.01 to 100, and more preferably 0.1 to 50.

In addition, component (D) is an optional component in the present emulsion composition, and the present emulsion composition does not necessarily contain component (D). In other words, the present emulsion composition does not necessarily contain any surface-active components (surfactants) other than component (A). In the present emulsion composition, the surface-active properties of component (A) make it possible to obtain an oil-in-water emulsion composition (particularly a cosmetic) that has good emulsion stability and a pleasant feel when used, even without the addition of other surfactants. However, as described above, the addition of component (D) not only improves emulsion stability and the feel when used, but also enables further variation in the formulation.

Other components: Water The present emulsion composition may contain water as another component other than those described above. In an oil-in-water emulsion composition, the emulsion is in the form of an oil-in-water (O/W) emulsion, with the aqueous phase being the external phase and the oil phase being the internal phase. The aqueous phase may contain water-soluble substances and hydrophilic substances. The water is not limited to these, but purified water is preferably used.

The water content in the present oil-in-water emulsion composition is not limited to, 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. Furthermore, depending on the formulation, the water content may be 50% by mass or more, or 60% by mass or more.

The present emulsion composition may contain various components that can be formulated as an oil-in-water emulsion composition (particularly a cosmetic preparation). Examples of such components include oils other than component (B), polymers (macromolecules) other than component (C), alcohols, moisturizers, thickeners, powders, pigments, film-forming agents, pH adjusters, anti-fading agents, antioxidants, antifoaming agents, cosmetic ingredients, plant extracts, preservatives, and fragrances.

Examples of oils other than component (B) include natural or synthetic ester oils, hydrocarbon oils, higher alcohols, and fatty acids. Specific examples of oils include, but are not limited to, liquid paraffin, PG dicaprate, cetyl 2-ethylhexanoate, glyceryl tri-2-ethylhexanoate, isotridecyl isononanoate, ethyl oleate, di-2-ethylhexyl succinate, ethylhexyl methoxycinnamate, polysilicone-15, squalane, octyldodecanol, caprylic/capric triglyceride, and trimethylolpropane triisostearate. Pan, pentaerythritol tetraisostearate, isohexadecane, isododecane, jojoba oil, macadamia nut oil, meadowfoam oil, hydrogenated coconut oil, olive oil, behenyl alcohol, cetostearyl alcohol, stearic acid, palmitic acid, isostearic acid, dimethicone, methylphenylpolysiloxane, diphenylsiloxyphenyl trimethicone, tritridecyl trimellitate, ascorbyl tetrahexyldecanoate, etc.

Polymers (macromolecules) other than component (C) include natural or synthetic polymers or macromolecules, such as gums and cellulose-based polymers. Specific examples of polymers include, but are not limited to, xanthan gum, gellan gum, carrageenan, gum arabic, karaya gum, tragacanth gum, carob gum, quince seed, casein, dextrin, gelatin, sodium pectinate, methylcellulose, ethylcellulose, carboxymethylcellulose (CMC), hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinyl alcohol (PVA), polyvinyl methyl ether (PVM), PVP (polyvinylpyrrolidone), locust bean gum, guar gum, tamarind gum, and dialkyldimethylammonium cellulose sulfate.

Alcohols include water-soluble monohydric alcohols and polyhydric alcohols. Examples of water-soluble monohydric alcohols include, but are not limited to, ethanol, methanol, propanol, and isopropanol. Examples of polyhydric alcohols include, but are not limited to, glycerin, diglycerin, ethylhexylglycerin, 1,3-butylene glycol, and dipropylene glycol.

The present emulsion composition may contain a pH adjuster. The pH adjuster can be used to adjust the pH range suitable for cosmetics. Furthermore, when a pH adjuster is added, the viscosity can also be adjusted by the acrylic acid polymer and methacrylic acid polymer of component (C) above. pH adjusters are not particularly limited, but examples include sodium hydroxide, potassium hydroxide, and triethanolamine.

The emulsion composition may contain a preservative. Examples of preservatives include, but are not limited to, phenoxyethanol and methyl parahydroxybenzoate (also known as methylparaben).

The present emulsion composition is preferably a cosmetic. The cosmetic may be a skin cosmetic or a hair cosmetic. The present emulsion composition is particularly preferably a skin cosmetic (oil-in-water emulsion cosmetic for skin). Furthermore, the present emulsion composition can be used in emulsion cosmetics for a variety of purposes, including skin care products and makeup products. The present emulsion composition can provide a fresh feel when used, a sustained moisturizing feeling after application, and an appropriate film-like feel on the skin after application, making it possible to obtain an emulsion cosmetic with a good feel when used.

Skin cosmetics are not particularly limited as long as they are in the form of an oil-in-water emulsion, and can be used as cosmetics for a variety of purposes. Examples include emulsions, creams, serums, hand creams, eye creams, body creams, makeup cosmetics, concealers, blushers, eye shadows (eye colors), makeup bases, foundations (e.g., liquid foundations, solid foundations), and sunscreens. Methods of using skin cosmetics include applying them to hands or fingers, using cotton, impregnating nonwoven fabric, and spraying or misting them.

Hair cosmetics are not particularly limited as long as they are in the form of an oil-in-water emulsion, and can be used as cosmetics for a variety of purposes. Examples include cosmetics such as hair cream, hair wax, hair rinse, hair mask, hair treatment, and sunscreen for hair. Methods of using hair cosmetics include applying them to the hands or fingers, or spraying them as a mist or spray.

The present emulsion composition (particularly the emulsion cosmetic) can be produced by mixing the above-mentioned components. For example, a method can be used in which a preheated and mixed aqueous component and a preheated and mixed oily component are mixed and emulsified, followed by cooling. In production, an appropriate emulsifier or kneader (e.g., a three-roller mixer, homomixer, etc.) can be used. Of course, the method for producing the present emulsion composition is not limited to this.

This specification discloses a method for stabilizing an emulsion of an oil-in-water emulsion composition containing components (A) and (B), the method comprising blending component (C) with components (A) and (B). As described above, emulsion can be stabilized by further blending component (C) in an oil-in-water emulsion composition containing components (A) and (B). Furthermore, emulsion can be further stabilized by further blending component (D). Thus, the combination of components (A) to (C) and the combination of components (A) to (D) improves emulsion stability.

The oil-in-water emulsion composition of the present invention will be described below using examples, but the present invention is not limited to these examples.

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

Synthesis of PC Compounds Synthesis Example 1 (Synthesis of PC Compound 1)
A combination of (R ¹ , R ² , R ³ , R ⁴ ) = (oleyl group, hydroxyethyl group, hydroxyethyl group, behenyl group) 65.3 g (0.2 mol) of behenyl alcohol as the raw material alcohol, 20.2 g (0.2 mol) of triethylamine, and 280 g of tetrahydrofuran were added to a 1 L round flask equipped with a thermometer, a dropping funnel, and a stirrer, and the mixture was cooled to 4°C and stirred and mixed. Next, a mixed solution of 28.5 g (0.2 mol) of 2-chloro-2-oxo-1,3,2-dioxaphosphorane and 60 g of tetrahydrofuran was added dropwise to the cooled mixed solution using the dropping funnel. The dropwise addition was carried out gradually over 2 hours while stirring the cooled mixed solution and ensuring that the reaction temperature did not exceed 10°C. After the dropwise addition was completed, stirring was continued for another 1 hour. Subsequently, triethylamine hydrochloride, which precipitated as a by-product, was filtered off. The entire amount 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 as a tertiary amine and 380 g of acetonitrile were added, followed by stirring at 70°C for 12 hours. The reaction solution was then cooled to obtain a precipitate, which was filtered off and dried under reduced pressure at 70°C to obtain crude crystals. The obtained crude crystals were recrystallized from a mixed solvent of tetrahydrofuran and acetonitrile to obtain 15.7 g of white crystals (yield 10%).
The results of ¹ H-NMR and ³¹ P-NMR analysis of the PC compound 1 obtained are shown below.
¹ H-NMR (δ (ppm)): 0.88 (t, J (HH) = 6.6 Hz, 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)

Synthesis Example 2 (Synthesis of PC Compound 2)
Combination of (R ¹ , R ² , R ³ , R ⁴ ) = (oleyl group, methyl group, methyl group, behenyl group) The same procedure as in Synthesis Example 1 was carried out except that 118.2 g (0.4 mol) of N,N-dimethyloleylamine was used instead of N,N-diethanololeylamine as the raw material amine, to obtain 72.8 g (yield 50%) of white crystals.
The results of ¹ H-NMR and ³¹ P-NMR analysis of the PC compound 2 obtained are shown below.
¹ H-NMR (δ (ppm)): 0.88 (t, J (HH) = 7.2 Hz, 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)

Synthesis Example 3 (Synthesis of PC Compound 3)
Combination of (R ¹ , R ² , R ³ , R ⁴ ) = (oleyl group, methyl group, methyl group, oleyl group) The same procedure as in Synthesis Example 1 was carried out except that 53.6 g (0.2 mol) of oleyl alcohol was used instead of behenyl alcohol as the raw material alcohol, and 118.2 g (0.4 mol) of N,N-dimethyloleylamine was used instead of N,N-diethanololeylamine as the raw material amine, to obtain 16.08 g (yield 12%) of white crystals.
The results of ¹ H-NMR and ³¹ P-NMR analysis of the PC compound 3 obtained are shown below.
¹ H-NMR (δ (ppm)): 0.88 (t, J (HH) = 7.2 Hz, 6H,), 1.2-1.4 (m, 48H), 1.56-1.62 (m, 2H), 1.65-1.7 (m, 2H), 1. 93-2.05 (m, 4H), 3.34 (s, 6H), 3.44-3.47 (m, 2H), 3.76-3.84 (m, 4H), 4.28-4.31 (m, 2H), 5.3-5.4 (m, 4H)
³¹ P-NMR (δ (ppm)): 0.56 (s)

Synthesis Example 4 (Synthesis of PC Compound 4)
Combination of (R ¹ , R ² , R ³ , R ⁴ ) = (behenyl group, hydroxyethyl group, hydroxyethyl group, oleyl group) The same procedure as in Synthesis Example 1 was carried out except that 53.6 g (0.2 mol) of oleyl alcohol was used instead of behenyl alcohol as the raw material alcohol, and 165.4 g (0.4 mol) of N,N-diethanolbehenylamine was used instead of N,N-diethanololeylamine as the raw material amine, to obtain 15.5 g of white crystals (yield 10%).
The results of ¹ H-NMR and ³¹ P-NMR analysis of the obtained PC compound 4 are shown below.
¹ H-NMR (δ (ppm)): 0.88 (t, J (HH) = 6.6 Hz, 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)

Synthesis Example 5 (Synthesis of PC Compound 5)
Combination of (R ¹ , R ² , R ³ , R ⁴ ) = (behenyl group, methyl group, methyl group, oleyl group) The same procedure as in Synthesis Example 1 was carried out except that 53.6 g (0.2 mol) of oleyl alcohol was used instead of behenyl alcohol as the raw material alcohol, and 141.4 g (0.4 mol) of N,N-dimethylbehenylamine was used instead of N,N-diethanololeylamine as the raw material amine, to obtain 43.6 g (yield 30%) of white crystals.
The results of ¹ H-NMR and ³¹ P-NMR analysis of the obtained PC compound 5 are shown below.
¹ H-NMR (δ (ppm)): 0.88 (t, J (HH) = 7.2 Hz, 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)

Examples 1 to 21, Comparative Examples 1 to 6
Oil-in-water emulsion composition (emulsion cosmetic)
The PC compounds 1 to 5 thus produced were used to produce the following emulsion compositions.

Tables 1 and 2 show the ingredients and their blend amounts (mass%) of the emulsion cosmetics (specifically, emulsions) of Examples 1 to 21 and Comparative Examples 1 to 6, as well as the results of evaluations of emulsion stability, usability, etc.

In the Examples and Comparative Examples in Tables 1 and 2, the names of raw materials and the like that should be particularly noted are shown below.
Dimer dilinoleic acid (phytosteryl/isostearyl/cetyl/stearyl/behenyl): PLANDOOL-S (Nippon Fine Chemicals Co., Ltd.), petrolatum: SNOW WHITE SPECIAL (SONNEBORN REFINED PRODUCTS B.V.), lauroyl glutamic acid di(phytosteryl/octyldodecyl): PLANDOOL-LG2 (Nippon Fine Chemicals Co., Ltd.).

The examples and comparative examples shown in Tables 1 and 2 were produced by the following methods.
Production Method of Examples 1 to 21 (1) Components (A), (B), (D) and liquid paraffin were mixed and heated to 75°C to dissolve, thereby obtaining a solution (oil phase).
(2) Component (C), purified water, and sodium hydroxide were mixed and heated to 75°C to dissolve, thereby obtaining a solution (aqueous phase).
(3) The solution (1) above was added to the solution (2) above and mixed to emulsify.
(4) The mixture of (3) above was cooled to obtain an emulsion composition.

Production Methods of Comparative Examples 1 to 6 Comparative Example 1 was produced in the same manner as Example 1, except that component (A) was not added (the same amount was replaced with purified water), to obtain an emulsion composition.
In Comparative Example 2, an emulsion composition was obtained in the same manner as in Example 1, except that component (A) was not blended and instead behendimonium ethyl stearyl phosphate was blended.
In Comparative Example 3, an emulsion composition was obtained in the same manner as in Example 1, except that component (B) was not added (the same amount was replaced with liquid paraffin).
In Comparative Example 4, an emulsion composition was obtained in the same manner as in Example 1, except that component (C) was not added (the same amount was replaced with purified water).
In Comparative Example 5, an emulsion composition was obtained in the same manner as in Example 1, except that component (C) was not blended and xanthan gum was blended instead.
In Comparative Example 6, an emulsion composition was obtained in the same manner as in Example 1, except that component (C) was not blended and carrageenan was blended instead.

Evaluation The cosmetics of the Examples and Comparative Examples shown in Tables 1 and 2 were evaluated by the following methods.
Uniformity of oil phase (70°C)
A mixture of component (A), component (B), and liquid paraffin was heated to 70°C to prepare an oil phase (A + B + liquid paraffin), and the appearance of this oil phase was evaluated according to the following criteria.
◎: No undissolved matter is visible and it is transparent. ○: No undissolved matter is visible but it is opaque. △: A very small amount of undissolved matter is visible. ×: Undissolved matter is visible.

Emulsion stability (50°C, 30 days)
The emulsion composition was left to stand in a thermostatic chamber at 50°C for one month (30 days), and the presence or absence of changes in appearance such as separation was visually observed. The number of days until a change in appearance (such as phase separation) was observed was counted.
◎: No change in appearance was observed up to 30 days. 〇: A change in appearance was observed between 14 and 29 days. △: A change in appearance was observed between 2 and 13 days. ×: A change in appearance was observed between 1 day and 1 day after being left in the thermostatic chamber.

Fresh feeling when used Twenty expert evaluation panel members evaluated the product on a four-point scale using the absolute standards (scores) below, and the average score was calculated from the total scores of all panel members, and judged according to the following criteria.
Specifically, each sample was placed on the skin and evaluated to see if it felt moisturizing when spread.
<Rating>
3: Sufficient freshness 2: Freshness can be felt, but it is slightly insufficient 1: Freshness is slightly insufficient 0: Freshness is insufficient <Evaluation criteria>
(Average score): (Judgment)
2.5 points or more: ◎
2 points or more but less than 2.5 points: 〇 1 point or more but less than 2 points: △
Less than 1 point: ×

Leaves skin with a moderate film-like firmness after application
A panel of 20 experts evaluated the product on a four-point scale using the absolute standards (scores) below, and the average score was calculated from the total scores of all the panelists, and judged according to the following criteria.
Specifically, each sample was placed on the skin, spread, and then evaluated to see if it gave a firm feeling.
A moderate film feeling on the skin after application means a comfortable firmness after application, and a stiff film feeling or a sticky film feeling was rated as poor (NG).
<Rating>
3: Sufficient firmness is felt. 2: Firmness is felt, but slightly insufficient. 1: Firmness is felt, but a stiff film or sticky feeling is also felt. 0: No firmness is felt, and a stiff film or sticky feeling is felt. <Evaluation criteria>
(Average score): (Judgment)
2.5 points or more: ◎
2 points or more but less than 2.5 points: 〇 1 point or more but less than 2 points: △
Less than 1 point: ×

Moisturizing feeling (moist feeling) 5 hours after application
A panel of 20 experts evaluated the product on a four-point scale using the absolute standards (scores) below, and the average score was calculated from the total scores of all the panelists, and judged according to the following criteria.
Specifically, each sample was placed on the skin, spread, and then after 5 hours, it was evaluated whether the skin felt moist (having a moisturizing feeling) (or whether the skin felt dry).
<Rating>
3: Feels moist and does not feel dry at all 2: Moisture is slightly insufficient, but does not feel dry 1: Moisture is insufficient, and there is a slight dry feeling 0: No moisturizing feeling, and there is a dry feeling <Evaluation criteria>
(Average score): (Judgment)
2.5 points or more: ◎
2 points or more but less than 2.5 points: 〇 1 point or more but less than 2 points: △
Less than 1 point: ×

Results Examples 1 to 21 containing components (A) to (C) were rated ◯ or ⊚ in all evaluation items (oil phase uniformity, emulsion stability, fresh feel in use, appropriate film-like feel on the skin after application, and moisturizing feel), indicating that both the stability and feel of the formulation were good. On the other hand, Comparative Example 1 exhibited unstable emulsion, and Comparative Example 2 exhibited poor oil phase uniformity and poor appropriate film-like feel on the skin after application. Furthermore, Comparative Example 3 exhibited poor appropriate film-like feel on the skin after application, and Comparative Examples 4 to 6 exhibited poor emulsion stability. Note that, as shown in Comparative Examples 5 and 6, it is presumed that highly hydrophilic polymers, such as those having a sugar skeleton, have low interaction with the lipophilic portion of component (A), making it difficult for the effect of stability to be achieved.

Example (prescription example)
The following examples were produced as oil-in-water emulsion compositions. In the following examples, the content refers to the blending ratio (% by mass), and the "remaining amount" refers to the amount that makes the total amount 100% by mass. All viscosities for component B1 are measured at 20°C. The viscosity was measured using a B-type viscometer (manufactured by Toki Sangyo Co., Ltd., TVB-10 model, measurement temperature: 20°C, measurement conditions: rotor number 2 to 4, rotation speed 0.3 to 6.0 rpm, measurement time 1 to 3 minutes).

Example 22: Emulsion (Components) (% by mass)
1. PC compound 1 (component A) 1.0%
2. Dimer dilinoleic acid (phytosteryl/isostearyl/cetyl/stearyl/behenyl) (ingredient B; B2) (*1) 0.2%
3. Phytosteryl isostearate (ingredient B; B2) (*2) 0.5%
4. Phytosteryl/octyldodecyl lauroyl glutamate (ingredient B: B1; viscosity 1,650 mPa·s) (*3) 0.3%
5. Vaseline (ingredient B; B2) (*4) 1.0%
6. Polyglyceryl-2 diisostearate (component B; B1; viscosity 1160 mPa·s)
1.0%
7. Di(octyldodecyl/phytosteryl/behenyl) lauroyl glutamate (ingredient B; B2) (*5) 0.4%
8. Di(cholesteryl/behenyl/octyldodecyl) lauroyl glutamate (ingredient B; B2) (*6) 0.1%
9. PG dicaprylate 1.0%
10. Glyceryl tri-2-ethylhexanoate 1.0%
11. Isotridecyl isononanoate 1.0%
12. Liquid paraffin 1.4%
13. Ethyl oleate 0.5%
14. Jojoba oil 0.5%
15. Glyceryl stearate (ingredient D; D1) 0.1%
16. Behenyl alcohol 0.5%
17. Cetostearyl alcohol 1.5%
18. Sorbion sesquistearate (ingredient D; D1) 0.1%
19. Polyglyceryl-10 monooleate (component D; D1) 0.1%
20. Polyoxyethylene sorbitan monooleate (20 E.O.) (component D; D2)
0.2%
21. Carbomer (component C) 0.05%
22. (Acrylates/C10-30 alkyl acrylate crosspolymer) (component C) 0.15%
23. Xanthan gum 0.03%
24. Hydroxypropyl methylcellulose (*7) 0.02%
25. Gellan gum (*8) 0.01%
26. 1,3-butylene glycol 8.0%
27. Dipropylene glycol 2.0%
28. Glycerin 0.5%
29. Sodium hydroxide 0.06%
30. Ethanol 3.0%
31. Phenoxyethanol 0.5%
32. Mixture of Jasminum Sambac Flower Extract, Grape Leaf Extract, Mentha Piperita Leaf Extract, Bifidobacterium Culture Lysate, Prunus Satsuma Flower Extract, Polyquaternium-51, Rosa Multiflora Fruit Extract, Rugosa Rose Flower Extract, Rosa Izayoi Extract, Water-Soluble Collagen, Royal Jelly Extract, Angelica Acetic Acid Root Extract, Rosa Centifolia Flower Extract, Rosa Damascena Flower Water, Rosemary Leaf Extract, Acerola Fruit Extract, Acetyl Glutamic Acid, Theanine, Glycine, Hydrolyzed Hyaluronic Acid, and Sodium Hyaluronate (Mixture of Cosmetic Ingredients)
1.0%
33. Remaining purified water (*1) PLANDOOL-S (Nippon Fine Chemical Co., Ltd.)
(*2) PLANDOOL-ISS (Nippon Fine Chemical Co., Ltd.)
(*3) PLANDOOL-LG2 (Nippon Fine Chemical Co., Ltd.)
(*4) SNOW WHITE SPECIAL (SONNEBORN REFINED PRODUCTS B.V.)
(*5) Eldew PS-304 (Ajinomoto Co., Inc.)
(*6) Eldew CL-301 (Ajinomoto Co., Inc.)
(*7) Metrolose 60SH-4000 (Shin-Etsu Chemical Co., Ltd.)
(*8) Kelcogel LT100 (Dainippon Pharmaceutical Co., Ltd.)

(Manufacturing method)
(1) Components 1 to 18 were mixed and dissolved by heating at 75°C to obtain a solution (oil phase).
(2) Components 19 to 28 were mixed, a portion of component 33 was added, and the mixture was heated to 75°C and mixed to obtain a solution.
(3) To the solution of (2) above, component 29 and the remainder of component 33 were added to obtain a solution (aqueous phase).
(4) The solution (1) above was added to the solution (3) above and emulsified to obtain an emulsion.
(5) After cooling the emulsion of (4) above, ingredients 30 and 31 were added, which had been uniformly mixed, and then ingredient 32 was added and mixed to obtain an emulsion composition.
(evaluation)
The emulsion of Example 22 was confirmed to have good oil phase uniformity, emulsion stability, a fresh feel when used, and a moderate film-like feel and moisturizing feel on the skin after use.
The mass ratios were as follows: the total amount of component (A) was 1.0%, the total amount of component (B) was 3.5%, the total amount of component (C) was 0.2%, and the total amount of component (D) was 0.5%. Therefore, (A)/(B) was 0.286, (C)/(A) was 0.2, and (D)/(A) was 0.5.

Example 23: Emulsion (Components) (% by mass)
1. PC compound 1 (component A) 0.5%
2. PC compound 2 (component A) 0.5%
3. PC compound 3 (component A) 0.2%
4. PC compound 4 (component A) 0.2%
5. Hydrogenated soybean phospholipid (hydrogenated soybean lecithin) (ingredient D) 0.1%
6. Dimer dilinoleic acid (phytosteryl/isostearyl/cetyl/stearyl/behenyl) (ingredient B; B2) (*1) 1.0%
7. Phytosteryl/octyldodecyl lauroyl glutamate (ingredient B; B1; 1,650 mPa·s) (*9) 0.3%
8. Phytosteryl isostearate (ingredient B; B2) (*2) 0.5%
9. Tridecyl trimellitate (*10) 0.2%
10. Hydrogenated polyisobutene (component B; B1; 26,200 mPa s) (*11)
0.5%
11. Vaseline (ingredient B; B2) (*4) 1.0%
12. Isotridecyl isononanoate 1.0%
13. Dipentaerythrityl hexa(hydroxystearate/stearic acid/rosinate) (ingredient B; B2) (*12) 0.5%
14. Liquid paraffin 3.5%
15. Dimethicone (6CS) 0.5%
16. Olive oil 0.5%
17. Jojoba oil 0.5%
18. Macadamia nut oil 0.2%
19. Meadowfoam oil 0.5%
20. Hydrogenated palm oil (component B; B2) 0.19%
21. Ceramide 2 0.01%
22. Ceramide 3 0.01%
23. Tocopherol acetate (component B; B1; 2,800 mPa·s) 0.01%
24. Glyceryl stearate (ingredient D; D1) 1.5%
25. Behenyl alcohol 0.5%
26. Cetostearyl alcohol 1.5%
27. Stearic acid 0.2%
28. Palmitic acid 0.1%
29. Isostearic acid 0.5%
30. Sucrose fatty acid ester (component D; D1) 0.1%
31. Polyoxyethylene sorbitan monooleate (20 E.O.) (component D; D2) 0.2%
32. PEG-80 hydrogenated castor oil (HLB: 15.0) (component D; D1) 0.2%
33. PEG-40 hydrogenated castor oil (HLB: 12.5) (component D; D1) 0.1%
34. Sodium N-stearoyl-N-methyl taurine (ingredient D) 0.05%
35. Carbomer (component C) 0.08%
36. (Acrylates/C10-30 alkyl acrylate crosspolymer) (component C) 0.12%
37. Xanthan gum 0.03%
38. Sodium acrylate/sodium acryloyldimethyltaurate copolymer (component C) 0.2%
39. Carrageenan 0.01%
40. Alcaligenes polysaccharides 0.01%
41. 1,3-butylene glycol 8.0%
42. Dipropylene glycol 2.0%
43. Glycerin 0.5%
44. Sodium hydroxide 0.06%
45. Ethanol 3.0%
46. Phenoxyethanol 0.5%
47. Ethylhexylglycerin 0.05%
48. Mixture of Elderflower Extract, Camellia Sinensis Leaf Extract, Angelica Root Extract, Jasminum Sambac Flower Extract, Polyquaternium-51, Rosa Multiflora Fruit Extract, Rugosa Rose Flower Extract, Rosa Izayoi Extract, Water-Soluble Collagen, Royal Jelly Extract, Angelica Root Extract, Rosa Centifolia Flower Extract, Rosa Damascena Flower Water, Rosemary Leaf Extract, Acerola Fruit Extract, Acetyl Glutamic Acid, Theanine, Glycine, Hydrolyzed Hyaluronic Acid, and Sodium Hyaluronate (Mixture of Cosmetic Ingredients)
2.0%
49. Remaining purified water (*9) Eldew PS-203 (Ajinomoto Co., Inc.)
(*10) LIPONATE TDTM (LIPO CHEMICALS INC.)
(*11) Pearleem 18 (NOF Corporation)
(*12) Cosmol 168ARNV (Nisshin Oillio Group Co., Ltd.)

(Manufacturing method)
(1) Components 1 to 30 were mixed and dissolved by heating at 75°C to obtain a solution (oil phase).
(2) Components 31 to 43 were mixed, a portion of component 49 was added, and the mixture was heated to 75°C and mixed to obtain a solution.
(3) To the solution of (2) above, component 44 and the remainder of component 49 were added to obtain a solution (aqueous phase).
(4) The above (1) was added to the solution of the above (3) and emulsified to obtain an emulsion.
(5) After cooling the emulsion of (4) above, ingredients 45, 46, and 47, which had been uniformly mixed, were added, and then ingredient 48 was added and mixed to obtain an emulsion composition.
(evaluation)
The emulsion of Example 23 was confirmed to have good oil phase uniformity, emulsion stability, fresh feel when used, and a moderate film-like feel and moisturizing feel on the skin after use.
The mass ratios were as follows: the total amount of component (A) was 1.4%, the total amount of component (B) was 4.0%, the total amount of component (C) was 0.4%, and the total amount of component (D) was 2.25%. Therefore, (A)/(B) was 0.35, (C)/(A) was 0.286, and (D)/(A) was 1.61.

Example 24: Cream (Components) (% by mass)
1. PC compound 1 (component A) 1.5%
2. PC compound 2 (component A) 0.5%
3. Behendimonium ethyl stearyl phosphate (ingredient D) 0.1%
4. Dimer dilinoleic acid (phytosteryl/isostearyl/cetyl/stearyl/behenyl) (ingredient B; B2) (*1) 1.5%
5. Phytosteryl/octyldodecyl lauroyl glutamate (ingredient B; B1; 1,650 mPa·s) (*3) 0.7%
6. Hydrogenated polyisobutene (component B; B1; 26,200 mPa s) (*11)
2.0%
7. Hydrogenated polyisobutene (component B; B1; 678,000 mPa s)) (*13)
0.5%
8. Diisostearyl malate (component B; B1; 2,520 mPa s) (*14)
1.0%
9. Tridecyl trimellitate (*10) 0.5%
10. PG dicaprylate 2.0%
11. Glyceryl tri-2-ethylhexanoate 2.0%
12. Liquid paraffin 3.5%
13. Ethyl oleate 0.5%
14. Methylphenylpolysiloxane 0.5%
15. Glyceryl stearate (ingredient D; D1) 0.9%
16. Behenyl alcohol 1.5%
17. Cetostearyl alcohol 2.5%
18. Ascorbyl tetrahexyldecanoate 0.2%
19. PEG-60 hydrogenated castor oil (HLB: 14.0) (component D; D1) 0.1%
20. Sodium N-stearoyl-N-methyl taurine (ingredient D) 0.05%
21. Carbomer (component C) 0.05%
22. (Acrylates/C10-30 alkyl acrylate crosspolymer) (component C) 0.20%
23. Xanthan gum 0.03%
24. Hydroxypropyl methylcellulose 0.02%
25. Gellan gum 0.01%
26. 1,3-butylene glycol 5.0%
27. Dipropylene glycol 2.0%
28. Diglycerin 1.5%
29. Sodium hydroxide 0.075%
30. Ethanol 3.0%
31. Phenoxyethanol 0.5%
32. Methylparaben 0.05%
33. A mixture of hydrolyzed conchiolin solution, gentian extract, hydrolyzed silk solution, hydrolyzed rice extract, seaweed extract, L-serine, Iwashobu leaf extract, Artemisia capillaris flower extract, Alpinia speciosa leaf extract, Saccharomyces cerevisiae extract, Pomegranate fruit extract, Pomegranate peel extract, Arisaema globulus fruit extract, Eggplant fruit extract, Harpagophytum root extract, Parsley extract, Royal jelly extract, Rosa alba flower extract, Avocado extract, Gynostemma pentaphyllum extract, Chamomilla recutita (matricaria) water, Barberry fruit extract, Apple extract, Lemongrass extract, Ichinoseki extract, Asparagus extract, Artemia extract, Guava extract, Coffee extract, Euonymus chinensis extract, Grape leaf extract, and Sanguisorba officinalis extract (a mixture of cosmetic ingredients)
2.0%
34. Purified water (ingredient F) Remaining amount (*13) Pearleem 46 (NOF Corporation)
(*14) Cosmol 222 (Nisshin Oillio Group Co., Ltd.)

(Manufacturing method)
(1) Components 1 to 18 were mixed and dissolved by heating at 75°C to obtain a solution (oil phase).
(2) Components 19 to 28 were mixed, a portion of component 34 was added, and the mixture was heated to 75°C and mixed to obtain a solution.
(3) To the solution of (2) above, component 29 and the remainder of component 34 were added to obtain a solution (aqueous phase).
(4) The above (1) was added to the solution of the above (3) and emulsified to obtain an emulsion.
(5) After cooling the emulsion of (4) above, ingredients 30, 31, and 32, which had been uniformly mixed, were added, and then ingredient 33 was added and mixed to obtain an emulsion composition.
(evaluation)
The cream of Example 24 was confirmed to have good oil phase uniformity, emulsion stability, fresh feel when used, and a moderate film-like feel and moisturizing feel on the skin after use.
The mass ratios were as follows: the total amount of component (A) was 2.0%, the total amount of component (B) was 5.7%, the total amount of component (C) was 0.25%, and the total amount of component (D) was 1.15%. Therefore, (A)/(B) was 0.351, (C)/(A) was 0.125, and (D)/(A) was 0.575.

Example 25: Cream (Components) (% by mass)
1. PC compound 1 (component A) 1.5%
2. PC compound 2 (component A) 0.5%
3. Behendimonium ethyl stearyl phosphate (ingredient D) 0.1%
4. Highly polymerized dimethylpolysiloxane (1 million CS) (component B; B1; 1,412,000 mPa·s) 2.0%
5. Rice bran oil fatty acid phytosteryl (ingredient B; B2) (*15) 2.0%
6. Di(phytosteryl/octyldodecyl) lauroyl glutamate (ingredient B: B1; viscosity 1,650 mPa·s) (*9) 3.5%
7. Di (2-ethylhexyl) succinate 1.5%
8. Liquid paraffin 3.5%
9. Methylphenylpolysiloxane 0.2%
10. Dimethicone (10CS) 0.2%
11. Behenyl alcohol 1.0%
12. Stearyl alcohol 2.5%
13. Behenyl PG trimonium chloride (ingredient D) 0.001%
14. Behenic acid dimethylaminopropylamide (ingredient D) 0.001%
15. (Acrylates/C10-30 alkyl acrylate crosspolymer) (component C) 0.3%
16. Hydroxypropyl methylcellulose 0.2%
17. Tremella fuciformis polysaccharide 0.05%
18. Propylene glycol 0.3%
19. Glycerin 1.0%
20. Glycosyltrehalose 1.0%
21. Sorbitol 1.0%
22. 1,3-butylene glycol 1.0%
23. Dipropylene glycol 1.0%
24. Diglycerin 0.5%
25. Sodium hydroxide 0.09%
26. Ethanol 3.0%
27. Phenoxyethanol 0.5%
28. Mixture of Sodium Hyaluronate, L-Proline, Sodium Hydrolyzed Conchiolin Solution, Gentian Extract, Hydrolyzed Silk Solution, Hydrolyzed Rice Extract, Seaweed Extract, L-Serine, Iwashobu Leaf Extract, Artemisia Capillaris Flower Extract, Alpinia Speciosa Leaf Extract, Saccharomyces Cerevisiae Extract, Pomegranate Fruit Extract, Pomegranate Peel Extract, Arisaema Fruit Extract, Eggplant Fruit Extract, Harpagophytum Root Extract, Parsley Extract, Royal Jelly Extract, Rosa Alba Flower Extract, Avocado Extract, Gynostemma Pentaphyllum Extract, Chamomilla Recutita (Matricaria) Water, Barberry Fruit Extract, Apple Extract, Lemongrass Extract, Ichinoseki Extract, Asparagus Extract, Artemia Extract, Guava Extract, Coffee Extract, Euonymus Root Extract, Grape Leaf Extract, and Sanguisorba Officinalis (Bull's Worm) Extract (Mixture of Cosmetic Ingredients)
2.0%
29. Purified water (ingredient F) Remaining amount (*15) Rice sterol ester (Tsukuno Rice Fine Chemicals Co., Ltd.)

(Manufacturing method)
(1) Components 1 to 14 were heated and dissolved at 75°C to obtain a solution (oil phase).
(2) Components 15 to 24 were mixed, a portion of component 29 was added, and the mixture was heated to 75°C and mixed to obtain a solution (aqueous phase).
(3) To the solution of (2) above, component 25 and the remainder of component 29 were added to obtain a solution (aqueous phase).
(4) The above (1) was added to the solution of the above (3) and emulsified to obtain an emulsion.
(5) After cooling the emulsion of (4) above, ingredients 26 and 27, which had been uniformly mixed, were added, and then ingredient 28 was added and mixed to obtain an emulsion composition.
(evaluation)
The cream of Example 25 was confirmed to have good oil phase uniformity, emulsion stability, fresh feel when used, and a moderate film-like feel and moisturizing feel on the skin after use.
The mass ratios were as follows: the total amount of component (A) was 2.0%, the total amount of component (B) was 7.5%, the total amount of component (C) was 0.3%, and the total amount of component (D) was 0.102%. Therefore, (A)/(B) was 0.267, (C)/(A) was 0.15, and (D)/(A) was 0.051.

Example 26: Sunscreen (Components) (% by mass)
1. PC compound 1 (component A) 0.4%
2. PC compound 2 (component A) 0.1%
3. Behendimonium ethyl stearyl phosphate (ingredient D) 0.1%
4. Hydrogenated soybean phospholipid (hydrogenated soybean lecithin) (ingredient D) 0.1%
5. Polyoxyethylene sorbitan monooleate (20 E.O.) (component D; D2)
0.5%
6. PEG-5 phytosterol (ingredient D; D1) 0.6%
7. PEG-30 Phytosterol (Component D; D1) 0.4%
8. Isostearic acid 1.0%
9. Ethylhexyl methoxycinnamate 7.0%
10. Diethylaminohydroxybenzoylhexyl benzoate 1.0%
11. Polysilicone-15 2.0%
12. Bis-ethylhexyloxyphenol methoxyphenyl triazine
1.5%
13. Glyceryl stearate (ingredient D; D1) 1.0%
14. Behenyl alcohol 1.5%
15. Cetostearyl alcohol 0.5%
16. Tocopherol acetate (component B; B1; 2,800 mPa·s) 0.2%
17. Ceramide 3 0.1%
18. Ascorbyl tetrahexyldecanoate 0.1%
19. Squalane 2.0%
20. Liquid paraffin 1.0%
21. Octyldodecanol 0.1%
22. Caprylic/capric triglyceride 0.5%
23. Polyglyceryl monoisostearate (component B; B1; 4,450 mPa·s)
0.5%
24. Dipentaerythrityl tripolyhydroxystearate (ingredient B; B1; 10,300 mPa·s) 0.5%
25. Trimethylolpropane triisostearate 0.1%
26. Pentaerythritol tetraisostearate 0.1%
27. Cholesteryl hydroxystearate (component B; B2) 1.2%
28. Isohexadecane 0.01%
29. Isododecane 0.01%
30. Diphenylsiloxyphenyl trimethicone 0.5%
31. Dimethicone (6CS) 0.5%
32. Stearic acid 1.0%
33. (Acrylates/C10-30 alkyl acrylate crosspolymer) (component C) 0.4%
34. Sodium acrylate/sodium acryloyldimethyltaurate copolymer (component C) 0.4%
35. 1,3-butylene glycol 6.0%
36. Glycerin 2.0%
37. Methylenebisbenzotriazolyltetramethylbutylphenol 1.0%
38. Sodium hydroxide 0.12%
39. Ethanol 5.0%
40. Phenoxyethanol 0.2%
41. Fragrance 0.1%
42. Isopropyl titanium triisostearate/hydrogen dimethicone-treated zinc oxide (average particle size 0.025 μm) 15.0%
43. (Vinyl dimethicone/methicone silsesquioxane) crosspolymer
0.5%
44. Polyhydroxystearic acid (component B; B1; 2,670 mPa·s)
2.5%
45. Sorbitan sesquioleate (component D; D1) 0.5%
46. Mixture of Elderflower Extract, Camellia Sinensis Leaf Extract, Tea Leaves Extract, Jasminum Sambac Flower Extract, Polyquaternium-51, Rosa Multiflora Fruit Extract, Rugosa Rose Flower Extract, Rosa Izayoi Extract, Water-Soluble Collagen, Royal Jelly Extract, Angelica Root Extract, Rosa Centifolia Flower Extract, Rosa Damascena Flower Water, Rosemary Leaf Extract, Acerola Fruit Extract, Acetyl Glutamic Acid, Theanine, Glycine, Hydrolyzed Hyaluronic Acid, and Sodium Hyaluronate (Mixture of Cosmetic Ingredients)
1.0%
47. Remaining purified water (ingredient F)

(Manufacturing method)
(1) Components 1 to 32 were heated and dissolved at 75°C to obtain a solution (oil phase).
(2) The uniformly dispersed components 42 to 45 were added to (1) above and mixed to obtain a solution (oil phase).
(3) Components 33 to 36 were mixed, and a portion of component 47 was added to obtain a solution (aqueous phase).
(4) Most of the components 37 and 47 were added to the solution of (3) above, and the mixture was heated to 75°C and mixed to obtain a solution (aqueous phase).
(5) The above (2) was added to the solution of the above (4) and emulsified to obtain an emulsion.
(6) After cooling the emulsion of (5) above, the remainder of component 38 and component 47 were added, and then components 39 to 41 and 46 were added and mixed to obtain an emulsion composition.
(evaluation)
The sunscreen of Example 26 was confirmed to have good oil phase uniformity, emulsion stability, a fresh feel when used, and a moderate film-like feel and moisturizing feel on the skin after application.
The mass ratios were as follows: the total amount of component (A) was 0.5%, the total amount of component (B) was 4.9%, the total amount of component (C) was 0.8%, and the total amount of component (D) was 3.2%. Therefore, (A)/(B) was 0.102, (C)/(A) was 1.6, and (D)/(A) was 6.4.

Example 27: Foundation (Components) (% by mass)
1. PC compound 1 (component A) 0.5%
2. PC compound 2 (component A) 0.5%
3. Behendimonium ethyl stearyl phosphate (ingredient D) 0.1%
4. Hydrogenated soybean phospholipid (hydrogenated soybean lecithin) (ingredient D) 0.1%
5. Dipentaerythrityl hexa(hydroxystearate/stearic acid/rosinate) (ingredient B) (ingredient B; B2) (*12) 0.5%
6. Hydrogenated polyisobutene (component B; B1; 44,100 mPa s) (*16)
0.5%
7. Dimer dilinoleic acid (phytosteryl/isostearyl/cetyl/stearyl/behenyl) (ingredient B; B2) (*1) 0.5%
8. Glyceryl tri-2-ethylhexanoate 1.0%
9. Cetyl 2-ethylhexanoate 1.0%
10. Stearic acid 1.5%
11. Isostearic acid 2.0%
12. Ethylhexyl methoxycinnamate 5.0%
13. Diethylaminohydroxybenzoylhexyl benzoate 1.0%
14. Glyceryl stearate (ingredient D; D1) 0.4%
15. Behenyl alcohol 0.2%
16. Cetostearyl alcohol 0.6%
17. Squalane 2.0%
18. Liquid paraffin 3.0%
19. Dimethicone 0.5%
20. Polyoxyethylene sorbitan monostearate (20 E.O.) (component D; D2) 0.3%
21. Carbomer (ingredient C) 0.1%
22. (Acrylates/C10-30 alkyl acrylate crosspolymer) (component C) 0.2%
23. Xanthan gum 0.1%
24. Alcaligenes polysaccharides 0.01%
25. Carrageenan 0.01%
26. Sodium acrylate/sodium acryloyldimethyltaurate copolymer (component C) 0.2%
27. 1,3-butylene glycol 7.0%
28. Triethanolamine 2.0%
29. Ethanol 3.0%
30. Phenoxyethanol 0.3%
31. Titanium oxide treated with 0.5% lecithin and 3% aluminum hydroxide (average particle size: 0.25 μm) 6.0%
32. Dimethicone, aluminum hydroxide, and hydrous silica-treated titanium dioxide (average particle size: 0.030 μm) 1.0%
33. Lecithin 0.5% treated red iron oxide 0.3%
34. Lecithin 0.5% treated yellow iron oxide 2.0%
35. Lecithin 0.5% treated black iron oxide 0.2%
36. Talc treated with 1% lecithin (average particle size: 10.5 μm) 3.0%
37. Zinc oxide (average particle size 0.3 μm) (*17) 1.5%
38. Silica (*18) 0.2%
39. Silica (*19) 0.3%
40. Sorbitan sesquioleate (ingredient D) 0.5%
41. Polyoxyethylene sorbitan monooleate (20 E.O.) (component D; D2)
0.8%
42. Mixture of Jasminum Sambac Flower Extract, Grape Leaf Extract, Mentha Piperita Leaf Extract, Bifidobacterium Culture Lysate, Prunus Satsuma Flower Extract, Polyquaternium-51, Rosa Multiflora Fruit Extract, Rugosa Rose Flower Extract, Rosa Izayoi Extract, Water-Soluble Collagen, Royal Jelly Extract, Angelica Acetic Acid Root Extract, Rosa Centifolia Flower Extract, Rosa Damascena Flower Water, Rosemary Leaf Extract, Acerola Fruit Extract, Acetyl Glutamic Acid, Theanine, Glycine, Hydrolyzed Hyaluronic Acid, and Sodium Hyaluronate (Mixture of Cosmetic Ingredients)
1.0%
43. Remaining purified water (*16) Pearleem 24 (NOF Corporation)
(*17) XZ-300F (Sakai Chemical Industry Co., Ltd.)
(*18) God Ball E-90C (Suzuki Oil & Fat Industries Co., Ltd.)
(*19) Sylosphere C-1504 (Fuji Silysia Chemical Ltd.)

(Manufacturing method)
(1) Components 1 to 19 were heated and dissolved at 75°C to obtain a solution (oil phase).
(2) Components 20 to 27 were mixed, a portion of component 43 was added, and the mixture was heated to 75°C and mixed to obtain a solution (aqueous phase).
(3) To the solution of (2) above, component 28 and the remainder of component 43 were added to obtain a solution (aqueous phase).
(4) The above (1) was added to the solution of the above (3) and emulsified to obtain an emulsion.
(5) After cooling the emulsion of (4) above, uniformly mixed components 29 and 30 were added, followed by component 42, and then uniformly dispersed components 31 to 41 were added and mixed to obtain an emulsion composition.
(evaluation)
The foundation of Example 27 was confirmed to have good oil phase uniformity, emulsion stability, fresh feel when used, and a moderate film-like feel and moisturizing feel on the skin after use.
The mass ratios were as follows: the total amount of component (A) was 1.0%, the total amount of component (B) was 1.5%, the total amount of component (C) was 0.5%, and the total amount of component (D) was 2.2%. Therefore, (A)/(B) was 0.667, (C)/(A) was 0.5, and (D)/(A) was 2.2.

Example 28: Eye shadow (eye color)
(Component) (mass%)
1. PC compound 1 (component A) 0.5%
2. PC compound 2 (component A) 0.5%
3. Hydrogenated soybean phospholipid (hydrogenated soybean lecithin) (ingredient D) 0.1%
4. Hydrogenated polyisobutene (component B; B1; 44,100 mPa s) (*16)
0.5%
5. Hydrogenated polyisobutene (component B; B1; 678,000 mPa s) (*13)
3.0%
6. Dimer dilinoleic acid (phytosteryl/isostearyl/cetyl/stearyl/behenyl) (ingredient B; B2) (*1) 1.0%
7. Dipentaerythrityl hexa(hydroxystearate/stearic acid/rosinate) (ingredient B; B2) (*12) 1.5%
8. Glyceryl tri-2-ethylhexanoate 1.0%
9. Stearic acid 1.0%
10. Glyceryl stearate (ingredient D; D1) 0.5%
11. Behenyl alcohol 0.4%
12. Cetostearyl alcohol 0.6%
13. Liquid paraffin 1.0%
14. Diphenylsiloxyphenyl trimethicone 0.5%
15. Carbomer (ingredient C) 0.1%
16. (Acrylates/C10-30 alkyl acrylate crosspolymer) (component C) 0.2%
17. Sodium acrylate/sodium acryloyldimethyltaurate copolymer (component C) 0.2%
18. 1,3-butylene glycol 7.0%
19. Triethanolamine 1.5%
20. Ethanol 5.0%
21. Phenoxyethanol 0.3%
22. Perfluorooctyltriethoxysilane 3% treated red iron oxide 0.2%
23. Perfluorooctyltriethoxysilane 3% treated yellow iron oxide 0.5%
24. Perfluorooctyltriethoxysilane 3% treated black iron oxide 0.05%
25. Perfluorooctyltriethoxysilane 3% treated sericite (average particle size 12.5 μm) 3.0%
26. Titanium oxide/tin oxide coated borosilicate (Ca/Al) (*20) 1.0%
27. Titanium oxide/silica coated mica (*21) 3.0%
28. Titanium oxide/iron oxide coated mica (*22) 1.0%
29. Sorbitan sesquioleate (ingredient D) 0.5%
30. Polyoxyethylene sorbitan monooleate (20 E.O.) (component D; D2)
0.8%
31. Mixture of Elderflower Extract, Camellia Sinensis Leaf Extract, Angelica Root Extract, Jasminum Sambac Flower Extract, Polyquaternium-51, Rosa Multiflora Fruit Extract, Rugosa Rose Flower Extract, Rosa Izayoi Extract, Water-Soluble Collagen, Royal Jelly Extract, Angelica Root Extract, Rosa Centifolia Flower Extract, Rosa Damascena Flower Water, Rosemary Leaf Extract, Acerola Fruit Extract, Acetyl Glutamic Acid, Theanine, Glycine, Hydrolyzed Hyaluronic Acid, and Sodium Hyaluronate (Mixture of Cosmetic Ingredients)
1.0%
32. Purified water remaining (*20) Microglass Metashine MT1080RS (Nippon Sheet Glass Co., Ltd.)
(*21) TIMIRON SPLEMDID RED (Merck Ltd.)
(*22) TIMICA RADIANT GOLD 222G (BASF Japan Ltd.)

(Manufacturing method)
(1) Components 1 to 14 were heated and dissolved at 75°C to obtain a solution (oil phase).
(2) Components 15 to 18 were mixed, a portion of component 32 was added, and the mixture was heated to 75°C and mixed to obtain a solution (aqueous phase).
(3) To the solution of (2) above, component 19 and the remainder of component 32 were added to obtain a solution (aqueous phase).
(4) The above (1) was added to the solution of the above (3) and emulsified to obtain an emulsion.
(5) After cooling the emulsion of (4) above, uniformly mixed components 20 and 21 were added, followed by component 31, and then uniformly dispersed components 22 to 30 were added and mixed to obtain an emulsion composition.
(evaluation)
The eye shadow (eye color) of Example 28 was confirmed to have good oil phase uniformity, emulsion stability, a fresh feel when used, and a moderate film-like feel and moisturizing feel on the skin after application.
The mass ratios were as follows: the total amount of component (A) was 1.0%, the total amount of component (B) was 6.0%, the total amount of component (C) was 0.5%, and the total amount of component (D) was 1.9%. Therefore, (A)/(B) was 0.167, (C)/(A) was 0.5, and (D)/(A) was 1.9.

Claims (13)

The following components (A) to (C):
0.01 to 3 mass% of (A) formula (1):
[In the formula, ^R1 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, ^R4 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, and at least one of R1 and ^R4 is an unsaturated hydrocarbon group having ¹² to 22 carbon atoms; and ^R2 and ^R3 may be the same or different and are each independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and a polyoxyalkylene group having 4 to 60 carbon atoms.]
A compound represented by
0.1 to 10 mass% of (B) one or more oil agents selected from the group consisting of oil agents having a viscosity of 1000 mPa s or more at 20°C and oil agents that are semi-solid at 20°C, and
0.01 to 0.4 mass% of (C) one or more polymers selected from the group consisting of acrylic acid polymers and methacrylic acid polymers;
An oil-in-water emulsion composition comprising: 2. The oil-in-water emulsion composition according to claim 1, wherein in formula (1), at least one of R ¹ and R ⁴ is an unsaturated hydrocarbon group having 18 carbon atoms. 3. The oil-in-water emulsion composition according to claim 1, wherein in formula (1), ^R2 and ^R3 each independently represent a methyl group or a hydroxyethyl group. The oil-in-water emulsion composition according to any one of claims 1 to 3, wherein component (C) is one or more polymers selected from the group consisting of carboxyvinyl polymers and alkyl-modified carboxyvinyl polymers. The oil-in-water emulsion composition according to any one of claims 1 to 4, wherein the ratio of component (A) to component (B) ((A)/(B)) is 0.1 or more by mass. The oil-in-water emulsion composition according to any one of claims 1 to 5, wherein the ratio of component (C) to component (A) ((C)/(A)) is 0.04 or more by mass. The oil-in-water emulsion composition according to any one of claims 1 to 6, wherein component (B) is an oil that is semi-solid at 20°C. The oil-in-water emulsion composition according to any one of claims 1 to 7, further comprising component (D) a surfactant. The oil-in-water emulsion composition according to claim 8, wherein the ratio of component (D) to component (A) ((D)/(A)) is 0.01 or more by mass. The oil-in-water emulsion composition according to claim 8 or 9, wherein component (D) is a nonionic surfactant. The oil-in-water emulsion composition according to claim 10, wherein the nonionic surfactant is a nonionic surfactant having a fatty acid residue having 12 to 22 carbon atoms and a polyoxyethylene group. The oil-in-water emulsion composition according to any one of claims 1 to 11, which is a cosmetic. A method for emulsifying and stabilizing an oil-in-water emulsion composition comprising the following components (A) and (B):
0.01 to 3 mass% of (A) formula (1):
[In the formula, ^R1 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, ^R4 is an unsaturated or saturated hydrocarbon group having 12 to 22 carbon atoms, and at least one of R1 and ^R4 is an unsaturated hydrocarbon group having ¹² to 22 carbon atoms; and ^R2 and ^R3 may be the same or different and are each independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and a polyoxyalkylene group having 4 to 60 carbon atoms.]
and a compound represented by
0.1 to 10 mass% of (B) one or more oil agents selected from the group consisting of oil agents having a viscosity of 1000 mPa s or more at 20°C and oil agents that are semi-solid at 20°C;
A method comprising blending, together with components (A) and (B), 0.01 to 0.4% by weight of component (C), one or more polymers selected from the group consisting of acrylic acid polymers and methacrylic acid polymers.