JP2014073971A - Emulsion, composition, cosmetic composition, and pharmaceutical composition - Google Patents

Abstract

The present invention provides an emulsion that has good stability and does not impair the properties of an oil component, and a composition containing the emulsion stably.
An emulsion comprising at least one silicone derivative having a side chain represented by the following formula, an oily component, and water.

(In the formula, A is an m + 1 valent hydrocarbon group having a nitrogen atom, R ³ is each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, and R ⁴ is each independently , A hydrocarbon group having 1 to 23 carbon atoms, and each Y is independently a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group or a salt thereof, and m is an integer of 1 to 10. And j and k are each independently an integer of 0, 1 or 2, and j and k are not 0 at the same time.)
[Selection figure] None

Description

  The present invention relates to emulsions, compositions, cosmetic compositions and pharmaceutical compositions containing them.

  In general, oily ingredients are used in hair cosmetics for the purpose of imparting gloss and smoothness to hair. As such an oil component, silicone is preferably used because of its excellent performance. As means for blending silicone into cosmetics, many methods are employed in which silicone and a large amount of emulsifier are added to a cosmetic composition and mixed and stirred to dissolve (see, for example, Patent Document 1).

JP 7-173294 A

  However, oily components, particularly silicone, are difficult to stably emulsify. Therefore, the conventional method as shown in Patent Document 1 has a problem that separation occurs even when emulsified with a very large shearing force during blending. Moreover, since it is necessary to add a large amount of an emulsifier, there is also a problem that the inherent characteristics of silicone cannot be obtained.

  The present invention has been made in view of the above problems, and has an emulsion that has good stability and does not impair the characteristics of the oil component, and a composition and a cosmetic composition that stably contain the emulsion. And to provide a pharmaceutical composition.

  As a result of intensive studies to solve the above problems, the present inventors have paid attention to a specific compound, that is, a compound of formulas (1), (2), and (3) having silicone in the structure, It has been found that by making this an emulsion mixed with an oily component, an emulsion can be obtained that does not impair the properties of the oily component, has good stability, and can be easily blended into cosmetic compositions and pharmaceutical compositions. The present invention has been completed.

That is, the present invention is as follows.
[1]
Component (A): one or more silicone derivatives selected from the group consisting of silicone derivatives represented by formulas (1), (2) and (3);
Component (B): an oily component,
water and,
An emulsion containing
(1)
(In formula (1), each R is independently an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, It is a polyether group having a molecular weight of 10,000,000 or less, an alkyl ester group having 1 to 24 carbon atoms, or a hydroxyl group, and may have a nitrogen atom,
X ¹ , X ² , and X ³ are each independently a group similar to R or a group represented by formula (4), and at least one of X ¹ , X ² , and X ³ is A group represented by formula (4),
n is an integer of 0 to 300,000. )
(2)
(In the formula (2), R is the same group as described above,
Each R ¹ is independently a divalent hydrocarbon group having 1 to 22 carbon atoms;
R ² each independently represents an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, or a molecular weight of 10,000,000. The following polyether groups, alkyl ester groups having 1 to 24 carbon atoms, hydroxyl groups, or hydrogen atoms,
X ⁴ is each independently a group similar to R or a group represented by formula (4), and at least one of X ⁴ is a group represented by formula (4);
Each Z is independently a polyalkylene oxide group;
h is each independently an integer of 0 to 300,000, i is each independently an integer of 1 to 300,000, and l is an integer of 1 to 300,000. )
(3)
(In formula (3), each R is independently the same group as described above,
X ⁵ is a group represented by the following formula (4),
p is each independently an integer of 1 to 300,000. )
(4)
(In Formula (4), A is a m + 1 valent hydrocarbon group having a nitrogen atom,
R ³ is each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms,
Each R ⁴ is independently a hydrocarbon group having 1 to 23 carbon atoms;
Y is each independently a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group or a salt thereof;
m is an integer of 1 to 10, j and k are each independently an integer of 0, 1 or 2, and j and k are not 0 at the same time. )
[2]
In the above formula (4), the emulsion according to [1], wherein m is 1 and A is a group represented by the formula (5).
(5)
(In formula (5), R ⁵ is a hydrocarbon group having 1 to 22 carbon atoms, and R ⁸ is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.)
[3]
In the above formula (4), the emulsion according to the above item [1], wherein m is 2, and A is a group represented by the formula (6).
(6)
(In formula (6), R ⁶ and R ⁷ are each independently a hydrocarbon group having 1 to 22 carbon atoms.)
[4]
In the formula (1), R is a methyl group, and X ¹ , X ² , and X ³ satisfy any one of the following (a) to (d): The emulsion according to item.
(A) One of X ¹ and X ³ is a group represented by Formula (4), and the other is a group represented by Formula (4) or a hydrocarbon group having a nitrogen atom, and X ² Is a methyl group.
(B) X ¹ is the same as R defined in formula (1), X ³ is a group represented by formula (4), and X ² is a methyl group.
(C) X ¹ and X ³ are the same as R defined in the formula (1), and at least one of X ² is a group represented by the formula (4).
(D) One of X ¹ and X ³ is a group represented by Formula (4), and the other is a group represented by Formula (4) or a hydrocarbon group having a nitrogen atom, and X ² Is at least one group represented by formula (4).
[5]
The emulsion according to any one of [1] to [4], wherein R ^{3 in the} formula (4) is a hydrogen atom, and Y is a carboxyl group or a salt thereof.
[6]
The emulsion according to any one of [1] to [5], wherein the component (B) contains silicone.
[7]
Component (C): The emulsion according to any one of [1] to [6], further comprising an N-acylamino acid type surfactant.
[8]
The emulsion according to any one of [1] to [7], wherein an average particle diameter of the emulsion particles is 0.01 to 100 μm.
[9]
A composition comprising the emulsion according to any one of [1] to [8] above.
[10]
A cosmetic composition comprising the emulsion according to any one of [1] to [8] above.
[11]
A pharmaceutical composition comprising the emulsion according to any one of [1] to [8] above.

  ADVANTAGE OF THE INVENTION According to this invention, the stability which has favorable stability and does not impair the characteristic of an oil-based component, and the composition, cosmetic composition, and pharmaceutical composition which contain it stably can be provided. .

  Hereinafter, although the form for implementing this invention (henceforth "this embodiment") is demonstrated concretely, this invention is not limited to this, Various in the range which does not deviate from the summary. Deformation is possible.

[Emulsion]
The emulsion of this embodiment is
Component (A): one or more silicone derivatives selected from the group consisting of silicone derivatives represented by formulas (1), (2), and (3);
Component (B): an oily component,
Contains water.

[Component (A): Silicone derivative]
Hereinafter, the silicone derivative will be described.
The silicone derivative used in this embodiment is represented by the formula (1), (2), or (3).
(1)
(In formula (1), each R is independently an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, It is a polyether group having a molecular weight of 10,000,000 or less, an alkyl ester group having 1 to 24 carbon atoms, or a hydroxyl group, and may have a nitrogen atom,
X ¹ , X ² , and X ³ are each independently a group similar to R or a group represented by formula (4), and at least one of X ¹ , X ² , and X ³ is A group represented by formula (4),
n is an integer of 0 to 300,000. )
(2)
(In the formula (2), R is the same group as described above,
Each R ¹ is independently a divalent hydrocarbon group having 1 to 22 carbon atoms;
R ² each independently represents an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, or a molecular weight of 10,000,000. The following polyether groups, alkyl ester groups having 1 to 24 carbon atoms, hydroxyl groups, or hydrogen atoms,
X ⁴ is each independently the same group as R or a group represented by the formula (4), and at least one of X ⁴ is a group represented by the following formula (4);
Each Z is independently a polyalkylene oxide group;
h is each independently an integer of 0 to 300,000, i is each independently an integer of 1 to 300,000, and l is an integer of 1 to 300,000. )
(3)
(In the formula (3), R is the same group as described above,
X ⁵ is a group represented by the following formula (4),
p is each independently an integer of 1 to 300,000. )
(4)
(In Formula (4), A is a m + 1 valent hydrocarbon group having a nitrogen atom,
R ³ is each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms,
Each R ⁴ is independently a hydrocarbon group having 1 to 23 carbon atoms;
Y is each independently a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group or a salt thereof;
m is an integer of 1 to 10, j and k are each independently an integer of 0, 1 or 2, and j and k are not 0 at the same time. )

<Silicone derivative represented by the formula (1)>
The silicone derivative represented by the formula (1) will be described. In formula (1), R is an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, and a molecular weight of 10,000,000. The following polyether groups, alkyl ester groups having 1 to 24 carbon atoms, or hydroxyl groups may have a nitrogen atom, and a plurality of R may be the same or different.

  The alkyl group having 1 to 22 carbon atoms is not particularly limited, and specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, Octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, heicosyl, docosyl, trifluoropropyl, etc. Is mentioned.

  Although it does not specifically limit as a C1-C22 alkoxy group, Specifically, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a phenoxy Groups and the like.

  Although it does not specifically limit as a C2-C22 alkenyl group, Specifically, a vinyl group and an allyl group are mentioned.

  Although it does not specifically limit as a C6-C22 aryl group, Specifically, a phenyl group, a benzyl group, a tolyl group, a xylyl group etc. are mentioned.

  The polyether group having a molecular weight of 10,000,000 or less is not particularly limited. Specifically, it is a linear polymer chain having an ether bond in the main chain, and is a polyalkylene such as polyethylene glycol or polypropylene glycol. Examples thereof include oxide and polyphenylene oxide.

  Although it does not specifically limit as a C1-C24 alkylester group, Specifically, methyl ester, ethyl ester, propyl ester, butyl ester, etc. are mentioned.

  R may be a group in which hydrogen is fluorine-substituted. R may be a group having a substituent such as a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group, or a salt thereof, and the solubility in weak acidity is improved by having these substituents. To do.

  Further, R represents a phenyl group, a phenol group, a hydroxy group, a carboxy group, an amino group (0 to 14 carbon atoms), an imino group, an (aminoethyl) amino group, a (dimethylaminoethyl) amino group, a polyoxyalkylene group, a mercapto group. You may have substituents, such as a group and an epoxy group.

  R is preferably an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a polyalkylene oxide, and more preferably. Is a C 1-3 alkyl group or a phenyl group, more preferably a methyl group, a propyl group or a phenyl group. Among these, a methyl group is particularly preferable from the viewpoint of versatility and price, and a phenyl group is particularly preferable from the viewpoint of heat resistance of the emulsion.

In the formula (1), at least one of X ¹ , X ² and X ³ is a group represented by the formula (4), and other than that is the same as the above R, and the same is preferably used. It is done. A plurality of X ² may be the same or different.

  In formula (1), n is an integer of 0 to 300,000. Preferably n is from 0 to 100,000. More preferably, n is 0 to 20,000.

  The molecular weight of the silicone derivative represented by the formula (1) is not particularly limited, but is preferably 50 to 10,000,000, more preferably 100 to 100,000, and more preferably 500 to 10 More preferably, it is 1,000.

<Silicone derivative represented by formula (2)>
The silicone derivative represented by the formula (2) will be described. In Formula (2), R is defined similarly to Formula (1), and the same is preferably used.

In formula (2), R ¹ is a divalent hydrocarbon group having 1 to 22 carbon atoms and is not particularly limited, and specific examples include an alkyl group, an aryl group, and an alkenyl group. Although it does not specifically limit as an alkyl group, Specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, etc. Is mentioned. Although it does not specifically limit as an alkenyl group, Specifically, a vinyl group and an allyl group are mentioned. The aryl group is not particularly limited, and specific examples include a phenyl group, a benzyl group, a tolyl group, and a xylyl group.

R ² is an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, a polyether group having a molecular weight of 10,000,000 or less. , An alkyl ester group having 1 to 24 carbon atoms, a hydroxyl group, or a hydrogen atom, and a plurality of R ^{2 s} may be the same or different.

An alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, a polyether group having a molecular weight of 10,000,000 or less, and the number of carbon atoms Examples of the alkyl ester group of 1 to 24 include the same groups as R in formula (1). R ² is preferably the same as R in formula (1) and hydrogen.
Z is a polyalkylene oxide, and examples thereof include polyethylene glycol and polypropylene glycol, and the preferred molecular weight is 10,000,000 or less. When there are a plurality of R ¹ , R ² and Z, they may be the same or different.

In the formula (2), at least one X ⁴ among the plurality of X ⁴ is a group represented by the following formula (4), and the other X ⁴ is the same as the above R, and the same is preferable. Used. The X ⁴ when there are a plurality may be the same or different.

  In Formula (2), h is an integer of 0 to 300,000, preferably 0 to 100,000, and more preferably 0 to 20,000. i is an integer of 1 to 300,000, preferably 1 to 100,000, and more preferably 1 to 20,000. l is an integer of 1 to 300,000, preferably 1 to 100,000, and more preferably 1 to 20,000.

  The molecular weight of the silicone derivative represented by the formula (2) is not particularly limited, but is preferably 50 to 10,000,000, more preferably 100 to 100,000, and 500 to 10 More preferably, it is 1,000.

<Silicone derivative represented by formula (3)>
The silicone derivative represented by the formula (3) will be described. In formula (3), R is defined similarly to formula (1), and the same is preferably used. When there are a plurality of R, they may be the same or different. In formula (3), X ⁵ is a group represented by formula (4).

  In Formula (3), p is an integer of 1 to 300,000, preferably 1 to 100,000, more preferably 1 to 20,000, and a plurality of p may be the same or different.

  The molecular weight of the silicone derivative represented by the formula (3) is not particularly limited, but is preferably 50 to 10,000,000, more preferably 100 to 100,000, and more preferably 500 to 10 More preferably, it is 1,000.

<Group represented by Formula (4)>
Next, the group represented by formula (4) will be described. First, in order to explain A in Expression (4), the following Expression (4) is set as the following Expression (7).
(4)
(7)

  In the formula (4), A is an m + 1 valent hydrocarbon group having a nitrogen atom. A in Formula (4) is equivalent to Q represented by Formula (7) and the joint part of the silicone part. The nitrogen atom of A is preferably directly bonded to Q. Since the nitrogen atom of A and Q are bonded to each other, the stability as a silicone derivative is high, and it can be used without problems even in high temperature, acid or alkali environments.

  In addition, since the silicone derivative has a group represented by the formula (4), the emulsion of the present embodiment has an effect of having high affinity for skin and hair.

  In Formula (4), m is an integer of 1 to 10, and m Qs are bonded to A. m is preferably 1 to 3. More preferably, m is 1 or 2. When a plurality of nitrogen atoms are present in A, m is greater than 3.

As a specific example, the case where m is 1 (formula (7-1)) and the case where m is 2 (formula (7-2)) are shown below.

In Formula (4), R ³ is a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms. When R ³ is a hydrocarbon group having 1 to ³ carbon atoms, it may have a hydroxyl group, a carboxyl group or a sulfonic acid group as a substituent. Specific examples of the hydrocarbon group having 1 to 3 carbon atoms are not particularly limited, and specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a hydroxymethyl group, a hydroxyethyl group, and a hydroxy (iso) propyl group. Group, dihydroxy (iso) propyl group, carboxymethyl group, carboxyethyl group, carboxypropyl group, sulfoethyl group and the like. Preferably, it is a hydrogen atom.

In formula (4), R ⁴ is a hydrocarbon group having 1 to 23 carbon atoms. Preferred is a hydrocarbon group having 7 to 17 carbon atoms, and more preferred is a hydrocarbon group having 11 to 17 carbon atoms. R ⁴ may be any of a straight chain, a branched chain, or a cyclic chain (aromatic hydrocarbon chain), and may have a substituent. Preferably, it is a straight chain. The hydrocarbon group can be used either saturated or unsaturated, but is preferably saturated. When there are a plurality of R ³ and R ⁴ , they may be the same or different.

  In formula (4), Y represents a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group or a salt thereof. Preferably, it is a carboxyl group or a salt thereof.

  When Y is a salt, examples of the basic substance that forms the salt include alkyl metals, alkaline earth metals, and the like. Alkali metals are not particularly limited, and specific examples include sodium, potassium, and lithium. Although a metal is mentioned and it is not specifically limited as an alkaline-earth metal, Specifically, metals, such as calcium and magnesium, are mentioned. Other metals include aluminum, zinc, iron, cobalt, titanium, zirconium, and silver. In addition, polyvalent metals other than those described above can be used.

  In addition, the basic substance capable of forming a salt other than a metal is not particularly limited, and specific examples include organic amines and basic amino acids. The organic amine is not particularly limited, and specific examples include ammonia, monoethanolamine, diethanolamine, triethanolamine and triisopropanolamine, and the basic amino acid is not particularly limited, but specifically Arginine and lysine. Y can include two or more salts arbitrarily selected from the above-mentioned salts.

  In formula (4), j and k each independently represent 0, 1, or 2, but j and k are not 0 at the same time. When there are a plurality of Y, j, and k, they may be the same or different.

Among these, R ³ in formula (4) is a hydrogen atom, and Y is preferably a combination of a carboxyl group or a salt thereof. If Formula (4) is such a group, it exists in the tendency for biodegradability to become favorable.

As one aspect | mode of the silicone derivative used by this embodiment, it is preferable in formula (4) that A is group represented by following formula (5), and m is 1. Having such a group represented by the formula (8) is preferable from the viewpoint of the feeling of use of the emulsion.
(5)
(In formula (5), R ⁵ is a hydrocarbon group having 1 to 22 carbon atoms, and R ⁸ is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.)
(8)
(In Formula (8), R ³ , R ⁴ , Y, j, and k are the same as those defined in Formula (4), and R ⁵ and R ⁸ are the same as those defined in Formula (5). .)

In formulas (5) and (8), R ⁵ is a hydrocarbon group having 1 to 22 carbon atoms, preferably a hydrocarbon group having 1 to 18 carbon atoms. R ⁵ may be a straight chain, a branched chain, or a cyclic chain, and may have a substituent. R ⁵ may be substituted with fluorine.

In formulas (5) and (8), R ⁸ is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms. In particular, R ⁸ is preferably a hydrogen atom from the viewpoint of the stability of the silicone derivative.

Since —NR ⁸ — in formulas (5) and (8) strengthens the bond between the silicone moiety and Q shown in formula (7), the stability as a silicone derivative increases. Therefore, the silicone derivative used in the present embodiment does not break the bond even under high temperature, acid or alkali environment. Moreover, the silicone compound used for this embodiment becomes high in emulsion stability by the strong coupling | bonding of the silicone compound and Q shown in Formula (7). Furthermore, since the odor of the silicone derivative can be suppressed, the odor of the emulsion can also be reduced.

As one aspect | mode of the silicone derivative used by this embodiment, it is preferable in formula (4) that A is group represented by following formula (6), and m is 2. By having such a group represented by the formula (9), it is preferable from the viewpoint of emulsion stability.
(6)
(In formula (6), R ⁶ and R ⁷ are each independently a hydrocarbon group having 1 to 22 carbon atoms.)
(9)
(In Formula (9), R ³ , R ⁴ , Y, j, and k are the same as those defined in Formula (4), and R ⁶ and R ⁷ are the same as those defined in Formula (6). .)

In formulas (6) and (9), R ⁶ and R ⁷ are each independently a hydrocarbon group having 1 to 22 carbon atoms, and those similar to R ⁵ in formula (5) are preferably used.

The emulsion of the present embodiment uses a silicone derivative in which all Rs are methyl groups in formula (1) and X ¹ , X ² , and X ³ satisfy any of the following (a) to (d): Is preferred.
(A) One of X ¹ and X ³ is a group represented by Formula (4), and the other is a group represented by Formula (4) or a hydrocarbon group having a nitrogen atom, and X ² Is a methyl group.
(B) X ¹ is the same as R defined in formula (1), X ³ is a group represented by formula (4), and X ² is a methyl group.
(C) X ¹ and X ³ are the same as R defined in the formula (1), and at least one of X ² is a group represented by the formula (4).
(D) One of X ¹ and X ³ is a group represented by Formula (4), and the other is a group represented by Formula (4) or a hydrocarbon group having a nitrogen atom, and X ² Is at least one group represented by formula (4).

In formula (1), R is a methyl group, and a silicone derivative in which X ¹ , X ² , and X ³ satisfy the above (a) is represented by formula (10). The silicone derivative represented by the formula (10) is a silicone derivative having the formula (4) at both ends of the silicone part, or having a hydrocarbon having a nitrogen atom with the formula (4).
(10)
(In Formula (10), ^one of X ¹ or X ³ is a group represented by Formula (4), and the other is a group represented by Formula (4) or a hydrocarbon group having a nitrogen atom. , N is the same as defined in formula (1).)

In formula (1), R is a methyl group, and a silicone derivative in which X ¹ , X ² , and X ³ satisfy the above (b) is represented by formula (11). The silicone derivative represented by the formula (11) is a silicone derivative having the formula (4) at one end of the silicone part.
(11)
(In Formula (11), X ³ is a group represented by Formula (4), and R and n are the same as those defined in Formula (1).)

In formula (1), R is a methyl group, and a silicone derivative in which X ¹ , X ² , and X ³ satisfy the above (c) is represented by formula (12). The silicone derivative represented by the formula (12) is a silicone derivative having the formula (4) in the side chain of the silicone part.
(12)
(In the formula (12), at least one of the plurality of X ² is a group represented by the formula (4), and other X ² is the same as R defined in the formula (1). n is the same as that defined in Formula (1).)

In formula (1), R is a methyl group, and a silicone derivative in which X ¹ , X ² , and X ³ satisfy the above (d) is represented by formula (13). The silicone derivative represented by the formula (13) is a silicone having the formula (4) or the formula (4) and a hydrocarbon having a nitrogen atom at both ends of the silicone part, and the side chain having the formula (4). Is a derivative.
(13)
(In Formula (13), ^one of X ¹ and X ³ is a group represented by Formula (4), and the other is a group represented by Formula (4) or a hydrocarbon group having a nitrogen atom. And at least one of the plurality of X ² is a group represented by the formula (4), the other X ² is the same as R defined in the formula (1), and n is defined in the formula (1). The same as

Of the silicone derivatives represented by the formulas (10) to (13), the silicone derivative represented by the formula (10) is preferable from the viewpoint of stability.
In addition, as for the group represented by Formula (4) in Formula (10)-(13), the case where A is group represented by Formula (5) or Formula (6) is preferable.

[Method for producing silicone derivative]
Below, the specific example of the manufacturing method of the silicone derivative used for this embodiment is given and demonstrated.

<Production method 1 N-acyl acidic amino acid anhydride and modified organopolysiloxane compound>
Although it does not specifically limit as a manufacturing method of the silicone derivative represented by said Formula (1), (2), or (3), Specifically, N-acyl acidic amino acid anhydride shown by following formula (14) And a modified organopolysiloxane compound having one or more amino groups can be obtained by reacting them at −5 ° C. to 250 ° C. without solvent or in the presence of a solvent.
(14)
(In formula (14), R ³ , R ⁴ , j, and k are the same as in formula (4).)

  The N-acyl acidic amino acid anhydride represented by the formula (14) used as a raw material is an anhydride of an N-acylated acidic amino acid. An N-acyl acidic amino acid anhydride can be obtained by reacting an N-acyl acidic amino acid with a dehydrating agent such as carboxylic anhydride such as acetic anhydride.

  The N-acyl acidic amino acid anhydride may be any of D-form, L-form, and racemate which are optical isomers. The L-form is preferable because it is excellent in biodegradability.

  Acidic amino acids are those having more carboxyl groups than amino groups in the molecule. Examples thereof include monoaminodicarboxylic acid having 2 and 1 carboxyl groups and amino groups, respectively. The hydrogen of the amino group may be substituted with a hydrocarbon group having 1 to 3 carbon atoms.

  Although it does not specifically limit as an acidic amino acid, Specifically, glutamic acid, aspartic acid, lanthionine, (beta) -methyllanthionine, cystathionine, diencholic acid, ferrinin, aminomalonic acid, (beta) -oxyaspartic acid, (alpha) -amino- α-methylsuccinic acid, β-oxyglutamic acid, γ-oxyglutamic acid, γ-methylglutamic acid, γ-methyleneglutamic acid, γ-methyl-γ-oxyglutamic acid, α-aminoadipic acid, α-amino-γ-oxyadipic acid, Examples include α-aminopimelic acid, α-amino-γ-oxypimelic acid, β-aminopimelic acid, α-aminosuberic acid, α-aminosebacic acid, pantothenic acid, and the like. Among these, L-acidic amino acid is preferable because biodegradability is particularly excellent. More preferred is L-glutamic acid or L-aspartic acid, and even more preferred is L-glutamic acid.

  The modified organopolysiloxane compound having one or more amino groups used as the other raw material is not particularly limited, and specific examples include amino-modified organopolysiloxane. Use of an amino-modified organopolysiloxane is preferable because the production purity and stability of the silicone derivative used in this embodiment are improved. The modified site of the modified organopolysiloxane compound may be any of both ends, one end, side chain type, and both side chain end types.

  The modified organopolysiloxane compound and the N-acyl acidic amino acid anhydride form an acid amide bond. This bond corresponds to -A- in the formula (4).

  Further, the modified organopolysiloxane compound may be an optical isomer of D-form, L-form, and racemate, or may be each isomer.

  Although it does not specifically limit as a modified organopolysiloxane compound which has an amino group, The following are mentioned.

  For example, as modified organopolysiloxane compounds made by Shin-Etsu Silicone, specifically, KF-868, KF-865, KF-864, KF-859, KF-393, KF-860, KF-877, KF-880 , KF-8004, KF-8002, KF-8005, KF-867, X-22-3820W, KF-869, KF-861, X-22-3939A, PAM-E, KF-8010, X-22-161A X-22-161B, KF-8012, KF-8008, X-22-1660B-3, KF-857, KF-8001, KF-862, X-22-9192, and KF-858.

  Specific examples of modified organopolysiloxane compounds manufactured by Toray Dow Coding include BY16-205, FZ-3760, SF8417, BY16-849, BY16-892, FZ-3785, BY16-872, BY16-213, BY16. -203, BY16-898, BY16-890, BY16-891, BY16-889, BY16-871, BY16-853U, and FZ-3789.

  Specific examples of the modified organopolysiloxane compound manufactured by Chisso include FM-3311, FM-3321, and FM-3325.

  Specific examples of modified organopolysiloxane compounds manufactured by Momentive Performance Materials include TSF4702, TSF4703, TSF4704, TSF4705, TSF4706, TSF4707, TSF4708, TSF4709, XF42-B1989, XF42-B8922, XF42-C0330, and XF49. -C1109, SILSOFT A-553, SILSOFT A-843, SILSOFT A-858, XF42-A3335, TSF4702, TSF4703.

  Specific examples of modified organopolysiloxane compounds manufactured by Asahi Kasei Wacker Silicone include: WACKER L652, WACKER L653, WACKER L655, WACKER L656, WACKER FINISH WR1100, WACKER FINISH WR1200, WACKER FINISH WR1IS, WACKER WR1IS WACKER FINISH WT1650.

  When reacting the N-acyl acidic amino acid anhydride and the modified organopolysiloxane compound, a solvent may be used. The solvent used in the reaction is not particularly limited. Specifically, water, a mixed solvent of water and an organic solvent, or a non-solvent such as tetrahydrofuran, benzene, toluene, xylene, carbon tetrachloride, chloroform and acetone. An active solvent is mentioned. The reaction temperature is preferably −5 ° C. to 250 ° C. and mixed and reacted at a temperature equal to or higher than the melting point of the above compound.

<Production Method 2 N-Acyl Acidic Amino Acid Mono-Lower Ester and Modified Organopolysiloxane Compound>
As another method for producing the silicone derivative represented by the formula (1), (2), or (3), an N-acyl acidic amino acid mono-lower ester (for example, methyl ester, There is a method obtained by reacting an ethyl ester) with the modified organopolysiloxane compound.

An N-acyl acidic amino acid mono-lower ester and a modified organopolysiloxane compound are dissolved in a suitable solvent such as dimethylformamide, a catalyst such as potassium carbonate is added, and the mixture is heated at -5 ° C to 250 ° C under reduced pressure. Then, the silicone solvent is obtained by removing the reaction solvent. Or it can also obtain by carrying out heat-melting without a solvent without using a solvent, adding a catalyst, such as sodium hydroxide, and carrying out transesterification at room temperature-250 degreeC. The N-acyl acidic amino acid mono-lower ester used in this case is preferably L-form.
As the modified organopolysiloxane, the same ones as described above can be used.

<Production Method 3 N-Acyl Acidic Amino Acid and Modified Organopolysiloxane Compound>
Furthermore, as another method for producing the silicone derivative represented by the formula (1), (2), or (3), an N-acyl acidic amino acid, not an N-acyl acidic amino acid anhydride, and the modified organopolysiloxane There is a method obtained by reacting with a compound.

  The N-acyl acidic amino acid and the modified organopolysiloxane compound are dissolved in an appropriate solvent such as toluene, a catalyst is added if necessary, and the mixture is heated at -5 ° C to 250 ° C, and then the reaction solvent is removed. Can be obtained. Alternatively, it can also be obtained by heating and melting without solvent without using a solvent, adding a catalyst as necessary, and reacting at room temperature to 250 ° C. The N-acyl acidic amino acid used in this case is preferably an N-acyl-L-acidic amino acid. As the modified organopolysiloxane, the same ones as described above can be used.

  Furthermore, the alkali salt can be obtained by neutralizing the silicone derivative obtained by the above-described production methods 1 to 3 with an alkali. From the silicone derivatives obtained by these methods, the silicone derivatives represented by the formula (1), (2), or (3) can be isolated by appropriate purification means.

Hereinafter, the reaction in the production of the silicone derivative used in this embodiment will be described with specific examples. For example, the following reaction formula (15) is an example of a reaction for producing a silicone derivative by reacting the N-acyl acidic amino acid anhydride of the formula (14) with a one-terminal amino-modified organopolysiloxane.
(15)
(In the reaction formula (15), R and n are the same as in the formula (1), and R ³ , R ⁴ , j and k are the same as in the formula (4). R ⁹ is a carbon atom having 1 to 22 carbon atoms. It is a hydrogen group.)

  In the emulsion, the content of the component (A) is preferably 0.001 to 40% by mass, more preferably 0.005 to 10% by mass, and still more preferably 0.01 to 5% by mass. By setting it as the above range, the emulsion feel tends to be good.

[Component (B): Oily component]
As the component (B) contained in the emulsion of the present embodiment, either liquid or solid can be used, and an oily component commonly used as a component of cosmetics, external medicines and the like may be used. Hereinafter, it illustrates about a component (B). The component (B) does not include those corresponding to the component (A).

  Fats and oils are not particularly limited, and specifically, avocado oil, turtle oil, corn oil, almond oil, olive oil, cacao oil, sesame oil, safflower oil, soybean oil, camellia oil, persic oil, castor oil, grape seed Oil, macadamia nut oil, mink oil, cottonseed oil, owl, palm oil, egg yolk oil, palm oil, palm kernel oil, glyceryl triisooctanoate, glyceryl triisoethylhexanoate, wheat germ oil, southern oil, flaxseed oil , Evening primrose oil, eno oil, peanut oil, tea seed oil, kaya oil, rice bran oil, cinnagyl oil, Japanese kiri oil, jojoba oil, germ oil, trioctanoic acid glycerin, triisopalmitic acid glycerin, horse oil, hydrogenated palm oil , Beef tallow, beef tallow, sheep fat, hardened beef tallow, pork tallow, beef bone fat, owl kernel oil, hardened oil, owl, hard Castor oil and the like.

  The hydrocarbon is not particularly limited, and specific examples include liquid paraffin, petrolatum, ceresin, microcrystalline wax, isoparaffin, ozokerite, squalene, pristane, squalane and the like.

  The wax is not particularly limited, and specifically, beeswax, whale wax, lanolin, carnauba wax, candelilla wax, cotton wax, bayberry wax, ibota wax, montan wax, nuka wax, lanolin, cabbage wax, lanolin acetate, liquid lanolin, sugar cane wax Lanolin fatty acid isopropyl, hexyl laurate, reduced lanolin, jojoba wax, hard lanolin, shellac wax, polyoxyethylene lanolin alcohol ether, polyoxyethylene lanolin alcohol acetate, lanolin fatty acid polyethylene glycol, polyoxyethylene hydrogenated lanolin alcohol ether and its Derivatives and the like.

  The higher fatty acid is not particularly limited, and specifically, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, behenic acid, undecylenic acid, lanolin fatty acid, hard lanolin fatty acid, soft lanolin fatty acid, Linoleic acid, linolenic acid, eicosapentaenoic acid, 12-hydroxystearic acid and the like can be mentioned.

  Specific examples of the higher alcohol include, but are not limited to, lauryl alcohol, cetanol, cetostearyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, lanolin alcohol, hydrogenated lanolin alcohol, hexyldecanol, octyldodecanol, and the like. Can be mentioned.

  Although it does not specifically limit as sterols, Specifically, cholesterol, phytosterol, etc. are mentioned.

  The ester oil is not particularly limited, and specifically, isopropyl myristate, butyl stearate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate, hexyl laurate, myristyl myristate, decyl oleate, dimethyloctane Hexyldecyl acid, cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearylate, ethylene glycol di-2-ethylhexylate, dipentaerythritol fatty acid ester, N-alkyl glycol monoisostearate , Neopentyl glycol dicaprate, diisostearyl malate, glycerin di-2-heptylundecanoate, trimethyl tri-2-ethylhexylate Propane, trimethylolpropane triisostearate, pentaerythritol tetra-2-ethylhexylate, glycerin tri-2-ethylhexylate, trimethylolpropane triisostearate, cetyl-2-ethylhexanoate, 2-ethylhexyl palmitate, trimyristin Acid glycerin, tri-2-heptylundecanoic acid glyceride, castor oil fatty acid methyl ester, oleic acid oil, cetostearyl alcohol, acetoglyceride, palmitate-2-heptylundecyl, diisopropyl adipate, N-lauroyl-L-glutamic acid 2-octyldodecyl ester, di-2-heptylundecyl adipate, ethyl laurate, di-2-ethylhexyl sepatate, 2-hexyl myristate Decyl, palmitic acid-2-hexyl decyl adipate 2-hexyl decyl, Sebachiru acid diisopropyl succinate 2-ethylhexyl, ethyl acetate, butyl acetate, amyl acetate, and triethyl citrate.

  The metal soap is not particularly limited, and specifically, zinc stearate, aluminum stearate, calcium stearate, magnesium stearate, zinc myristate, magnesium myristate, zinc cetyl phosphate, calcium cetyl phosphate, sodium cetyl phosphate, etc. Is mentioned.

  Although it does not specifically limit as volatile and a non-volatile oil component, Specifically, Chain polysiloxanes, such as dimethyl polysiloxane, methylphenyl polysiloxane, diphenyl polysiloxane; Octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane , Cyclic polysiloxanes such as dodecamethylcyclohexasiloxane; silicone resin forming a three-dimensional network structure; silicone rubber; alcohol-modified silicone, epoxy-modified silicone, amino-modified polysiloxane, polyether-modified polysiloxane, alkyl-modified polysiloxane And various modified polysiloxanes such as alkoxy-modified silicone and fluorine-modified polysiloxane; silicones such as volatile silicone.

  These oil components may be used alone or in combination of two or more. Among these oil components, it is preferable to contain silicone, particularly from the viewpoint of slipperiness. Among silicones, it is more preferable to use one or more volatile cyclic silicones from the viewpoint of usability. More preferably, a volatile cyclic silicone and a non-volatile silicone are combined.

  It is preferable that content of a component (B) is 0.001-95 mass%, More preferably, it is 1-60 mass%, More preferably, it is 10-50 mass%. By setting it as the above range, the touch of the emulsion tends to be better.

[water]
The emulsion of this embodiment contains water. The water content in the emulsion of this embodiment is preferably 1% by mass to 99% by mass, more preferably 20% by mass to 90% by mass, and even more preferably 40% by mass to 80% by mass. By setting it as the said range, it exists in the tendency which is more excellent in stability.

[Component (C): N-acylamino acid type surfactant]
The emulsion of this embodiment preferably further contains a component (C) N-acylamino acid type surfactant. By containing the component (C), the irritation tends to be further reduced.

  In the present embodiment, the N-acylamino acid of (C) N-acylamino acid type surfactant is an acyl group derived from a saturated or unsaturated fatty acid having 2 to 24 carbon atoms into the amino group of the amino acid. It is a thing. The amino acid residue in the N-acyl amino acid is not particularly limited, and specific examples include various amino acids such as α-amino acid, β-amino acid, γ-amino acid and ω-amino acid, and the amino group includes Specific examples include, but are not limited to, an N-methyl form and an N-ethyl form. The N-acylamino acid may be an optical isomer, that is, any of D-form, L-form, and racemate. Further, the N-acylamino acid may form a salt.

  Specific examples of the amino acid are not particularly limited, and specific examples include glutamic acid, aspartic acid, glycine, alanine, lanthionine, β-methyllanthionine, cystathionine, diencholic acid, ferrinin, aminomalonic acid, β-oxyasparagine. Acid, α-amino-α-methylsuccinic acid, β-oxyglutamic acid, γ-oxyglutamic acid, γ-methylglutamic acid, γ-methyleneglutamic acid, γ-methyl-γ-oxyglutamic acid, α-aminoadipic acid, α, α ' -Diaminoadipic acid, β, β'-diaminoadipic acid, α-amino-γ-oxyadipic acid, α-aminopimelic acid, α-amino-γ-oxypimelic acid, β-aminopimelic acid, α-aminosuberic acid, α -Amino sebacic acid, pantothenic acid, etc. are mentioned.

  Although it does not specifically limit as a specific example of an acyl group, Specifically, what is necessary is just to be derived from a C2-C24 saturated or unsaturated fatty acid, and any of linear, branched, and cyclic Good. It is preferably derived from a saturated or unsaturated fatty acid having 7 to 24 carbon atoms, more preferably derived from a saturated or unsaturated fatty acid having 12 to 24 carbon atoms.

  The N-acylamino acid is preferably L-form. By being L-form, biodegradability tends to be better. (C) As a component, More preferably, N-acyl-L-acidic amino acid is mentioned, More preferably, N-acyl-L-glutamic acid is mentioned.

  In the emulsion of this embodiment, the content of the (C) N-acylamino acid type surfactant is preferably 0.1 to 30% by mass, more preferably 1 to 10% by mass, and 2 to 5%. More preferably, it is mass%. By being in the above range, the feeling of use tends to be further improved. (C) N-acylamino acid type surfactants may be used alone or in combination of two or more.

[Component (D): Polyhydroxyl compound]
Moreover, it is preferable that the emulsion of this embodiment further contains a component (D) polyhydroxyl compound. By containing a component (D), it exists in the tendency for moisture retention to improve more.

  Content of a component (D) becomes like this. Preferably it is 0.1-30 mass%, More preferably, it is 1-10 mass%, More preferably, it is 2-5 mass%. By being the said range, it exists in the tendency which is excellent by stability and a usability | use_condition.

  Furthermore, when the mass ratio of component (A) / component (D) is 10/1 to 1/100, the touch tends to be further improved. The mass ratio of component (A) / component (D) is more preferably 5/1 to 1/50, still more preferably 5/1 to 1/20.

  Examples of the polyhydroxyl compound of component (D) contained in a preferred aspect of the emulsion of the present embodiment include polyhydric compounds having a valence of 2 or more.

  Although it does not specifically limit as a bivalent polyhydroxyl compound, Specifically, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1 , 4-butanediol, pentanediol, 1,6-hexanediol, cyclohexanediol, dimethylolcyclohexane, neopentyl glycol, 1,8-octanediol, 2,2,4-trimethyl-1,3-pentanediol, isoprene Glycol, 3-methyl-1,5-pentanediol, sorbite, catechol, resorcin, hydroquinone, bisphenol A, bisphenol F, hydrogenated bisphenol A, hydrogenated bisphenol F, dimer diol, dimethylolpropionic acid, dimethylolbutanoic acid, Liquor Acid, dihydroxytartaric acid, mevalonic acid, 3,4-dihydroxycinnamic acid, 3,4-dihydroxyhydrocinnamic acid, dihydroxybenzoic acid, dihydroxystearic acid, dihydroxyphenylalanine, diethanolamine and the isomers thereof. .

  Although it does not specifically limit as a trivalent polyhydroxyl compound, Specifically, glycerol, trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol, 2-methyl-1,2, 3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol, 2,3,4-hexanetriol, 4 -Propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-pentanetriol, 1,2,4-butanetriol, 1,2,4-pentanetriol, trimethylolethane, tri Examples include methylolpropane, triethanolamine, and trihydroxystearic acid.

  Although it does not specifically limit as tetravalent polyhydroxyl compound, Specifically, pentaerythritol, erythritol, 1,2,3,4-pentanetetrol, 2,3,4,5-hexanetetrol, 1,2 , 4,5-pentanetetrol, 1,3,4,5-hexanetetrol, diglycerin, sorbitan and the like.

  The pentavalent polyhydroxyl compound is not particularly limited, and specific examples include adonitol, arabitol, xylitol, triglycerin, talose, allose and the like.

  Although it does not specifically limit as a hexavalent polyhydroxyl compound, Specifically, a dipentaerythritol, sorbitol, a mannitol, an idiitol, an inositol, a dulcitol, etc. are mentioned, These dehydration condensates, polyglycerol, etc. are also mentioned.

  Moreover, saccharides are also mentioned as a polyhydroxyl compound. Specific examples of the saccharide include, but are not limited to, tetroses such as erythrose, throse, and erythrulose; pentoses such as ribose, arabinose, xylose, lyxose, xylulose, and ribulose; allose, altrose, glucose, mannose, and guylose. Monosaccharides such as hexose such as idose, galactose, talose, fructose, sorbose, psicose, tagatose; maltose, isomaltose, cellobiose, gentiobiose, melibiose, lactose, turanose, trehalose, saccharose, mannitolose, cellotriose, gentianose , Oligosaccharides such as meretitol, serotose, stachyose and the like.

  In addition, other saccharides such as heptose, deoxy sugar, amino sugar, thio sugar, seleno sugar, aldone sugar, uronic acid, sugar acid, ketoaldonic acid, anhydro sugar, unsaturated sugar, sugar ester, sugar ether, glycoside, etc. And polysaccharides such as starch, glycogen, cellulose, chitin and chitosan, or hydrolyzed polysaccharides thereof.

  These (D) polyhydroxyl compounds may be used alone or in combination of two or more. The polyhydroxyl compound is preferably a trihydroxy or higher polyhydroxyl compound. By being trivalent or higher, the emulsion tends to become more stable.

[Average particle diameter of emulsion particles]
The average particle size of the emulsion particles in the emulsion of this embodiment is preferably 0.01 to 100 μm, more preferably 0.01 to 10 μm, and still more preferably 0.01 to 5 μm. When the average particle size is 100 μm or less, the stability of the emulsion tends to be more excellent, and when the average particle size is 0.01 μm or more, the emulsion tends to be more easily adjusted. The “emulsion particle” refers to a dispersoid in an emulsion composed of a dispersoid and a dispersion medium. The average particle size of the emulsion particles can be controlled by controlling the content of each component, the mixing method, and other conditions.

  The average particle size of the emulsion according to the present embodiment is obtained by directly measuring the diameters of 20 emulsified particles in the same field of view with respect to a digital image taken with a digital microscope (manufactured by KEYENCE: product name VHX-900). The average was taken as the emulsified particle size.

  The emulsion of this embodiment is an emulsion containing component (A), component (B) and water, and the mass ratio of component (A) / component (B) is 50/1 to 1 / 100,000. It is preferable. If the mass ratio is 50/1 or less, the characteristics of the component (B) such as moisture retention and protection by film formation tend to be improved, while if the mass ratio is 1 / 100,000 or more, emulsion stability is obtained. Tend to be improved. The mass ratio of component (A) / component (B) is more preferably 30/1 to 1/100, and further preferably 20/1 to 1/50.

[Method for producing emulsion]
The emulsion of this embodiment can be produced by a method using an apparatus equipped with a normal stirrer, mixer, disperser and the like. The emulsion of the present embodiment can be produced, for example, by emulsifying component (A), component (B), and water in an aqueous phase or an oil phase. Moreover, it can manufacture by adding and mixing a component (C) N-acyl amino acid type surfactant, a component (D) polyhydroxyl compound, etc. as needed.

  When component (C) is added and mixed, for example, when component (A), component (B), and water are emulsified in an aqueous phase or an oil phase, they can be mixed and emulsified in an aqueous phase or an oil phase. .

  In the case of adding and mixing the component (D), after adding the component (B) while stirring the mixed solution containing the component (A), the component (D), and water to form an oily gel-like composition, A method of emulsifying the gel composition by adding water or the like is preferred. Here, the oily gel-like composition has a property that it becomes a stable emulsion-dispersed state of several μm to sub-μm order very easily when water is added and stirred. In addition, an emulsion having a very fine average particle size can be produced simply by adding necessary components.

  Here, the oily gel composition can be produced by stirring and mixing the component (A), the component (D), the component (B), and optionally water under a high shearing force. As a preferred production method of the oily gel composition, a production method in which components other than the oily component are first sufficiently stirred and mixed, and the oily component is added thereto is preferable.

  Moreover, when manufacturing said oil-based gel-like composition, there exists the method of making it gelatinous by adding a gelatinizer etc. Here, as the gelling agent, a known gelling agent capable of gelling the oil component can be used. For example, as such a gelling agent, dextrin fatty acid ester, glycerin fatty acid ester, hydroxystearic acid, long-chain acylglutamic acid dibutylamide and the like can be mentioned.

  Examples of the dextrin fatty acid ester include Leopard TT [(palmitic acid / octanoic acid) dextrin], Leopard MKL [dextrin myristic acid], Leopard KL [dextrin palmitate] (all trade names: manufactured by Chiba Flour Milling Co., Ltd.). It is done.

  Examples of the glycerin fatty acid ester include NOMCOAT HK-G (trade name: manufactured by Nisshin Oil Co., Ltd.), which is an oligomer ester composed of behenic acid, eicosanedioic acid and glycerin.

[Composition]
The emulsion of this embodiment obtained in this way becomes a stable emulsion even if the amount of component (A) used is small, and does not impair the original characteristics of (B) oily component. Moreover, this emulsion can be blended into various compositions including cosmetic compositions and pharmaceutical compositions stably and easily.

  The emulsion of the present embodiment is widely applied to, for example, household cleaners (clothing, kitchens, houses, tableware, contact lenses, etc.), cleaning compositions for cosmetics, foods, pharmaceuticals, etc., and industrial cleaners. be able to. In particular, it is useful as a cosmetic composition and a pharmaceutical composition.

[Other additives]
Moreover, in the emulsion of this embodiment, various additives can be added according to a use and the objective.

  Although it does not specifically limit as a dispersing agent, Specifically, Natural rubbers, such as gum arabic and tragacanth rubber; Glucosides, such as saponin; Cellulose derivatives, such as methylcellulose, carboxycellulose, and hydroxymethylcellulose; Lignin sulfonate, shellac, etc. Natural polymers of polyacrylic acid salt, styrene-acrylic acid copolymer salt, vinyl naphthalene-maleic acid copolymer salt, β-naphthalenesulfonic acid formalin condensate sodium salt, anion such as phosphate Nonionic polymers such as polyvinyl alcohol, polyvinyl pyrrolidone, and polyethylene glycol.

  Although it does not specifically limit as a higher fatty acid salt (soap), Specifically, the salt of a C2-C20 higher fatty acid of a hydrophobic group part etc. are mentioned.

  Although it does not specifically limit as an anionic surfactant, Specifically, alkyl ether carboxylate, amide ether carboxylate, etc., alkyl sulfate ester salt (AS), polyoxyethylene alkyl ether sulfate ester salt (AES) , Alkyl ether sulfates, sulfates of higher fatty acid esters, sulfates of higher fatty acid alkylolamides, sulfated oils and fats, polyoxyethylene styrenated phenyl ether sulfates, alpha-olefin sulfonates (AOS), alkylbenzene sulfonates , Alkylnaphthalene sulfonate, alkyl sulfonate (SAS), dialkyl sulfosuccinate, alpha-sulfonated fatty acid salt, alkane sulfonate, sulfonate of higher fatty acid ester, alpha-sulfonated fatty acid salt, higher fatty acid amide Sulfonate, N-acyl-N-alkyl taurate, N-acyl-N-methyl taurate, alkyl phosphate, alkyl ether phosphate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether Examples thereof include phosphate, naphthalene sulfonate, formalin condensate, tetradecene sulfonate, and myristate.

  The amphoteric surfactant is not particularly limited, and specific examples thereof include alkylbetaines, alkylamidobetaines, alkylsulfobetaines, imidazolinium betaines, and lecithins.

  Although it does not specifically limit as a nonionic surfactant, Specifically, polyoxyethylene alkyl ether (AE), polyoxyethylene alkyl phenyl ether, polyoxyethylene polystyryl phenyl ether, polyoxyethylene polyoxypropylene glycol, Polyoxyethylene polyoxypropylene alkyl ether, polyoxyalkylene fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, polyoxyalkylene fatty acid alkanolamide, polyoxyalkylene alkyl glucoside, polyoxyalkylene hydrogenated castor oil, polyoxyalkylene alkylamine, polyoxyalkylene Ethylene oxide condensation type such as alkyl phenyl ether, polyhydric alcohol fatty acid partial ester, polyoxyethylene poly Alcohol fatty acid partial ester, polyoxyethylene fatty acid ester, (poly) glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkylamine, triethanolamine fatty acid partial ester, alkyl polyglucoside, propylene glycol fatty acid ester, sorbitan fatty acid ester, Polyhydric alcohol esters such as fatty acid esters, fatty acid alkanolamides, sugar amine acylates, triethanolamine fatty acid partial esters, fatty acid alkylolamides, alkylamine oxides, fatty acid diethanolamides, polyoxyethylene dioleic acid methyl glucoside, distearic acid Examples include polyethylene glycol.

  The cationic surfactant is not particularly limited, and specific examples include primary to tertiary fatty amine salts, alkylammonium chlorides, tetraalkylammonium salts, trialkylbenzylammonium salts, alkylpyridinium salts, alkylhydroxys. Examples include ethyl imidazolinium salt, dialkylmorpholinium salt, alkylisoquinolium salt, benzethonium salt, benzalkonium salt, myristyldimethylamine and the like.

  Although it does not specifically limit as a polymeric surfactant, Specifically, sodium alginate, a starch derivative, tragacanth gum, etc. are mentioned.

  Although it does not specifically limit as a natural surfactant, Specifically, a phospholipid, a lecithin, lanolin, cholesterol, saponin etc. are mentioned.

  Although it does not specifically limit as a moisturizer, Specifically, alkyl glycines, such as N-methylglycine, N, N-dimethylglycine, N, N, N-trimethylglycine, N-ethylglycine, glycylbetaine; (Poly) saccharides and derivatives thereof such as sorbitol, raffinose, pyrrolidonecarboxylates lactates, hyaluronates, ceramides, trehalose, xylobiose, maltose, sucrose, glucose, vegetable viscous polysaccharides; water-soluble chitin, chitosan, Glycosaminoglycans and salts thereof such as pectin, chondroitin sulfate and salts thereof; amino acids and salts thereof such as glycine, serine, threonine, alanine, aspartic acid, tyrosine, valine, leucine, arginine, glutamine and prophosphoric acid; aminocarbonyl Sugar amino acid compounds such as reactants Aloe, plant extracts, such as horse chestnut, urea, uric acid, ammonia, glucosamine, creatinine, DNA, include nucleic acid-related substances such as RNA and the like.

  The water-soluble and oil-soluble polymer is not particularly limited, and specifically, hydroxyethyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose hydroxypropyltrimethylammonium chloride ether, methylcellulose, ethylcellulose, hydroxypropylcellulose, methylhydroxypropylcellulose, soluble starch , Carboxymethyl starch, methyl starch, propylene glycol alginate, polyvinyl alcohol, polyvinyl pyrrolidone, polyvinyl methyl ether, carboxyvinyl polymer, polyacrylate, guar gum, locust bin gum, quince seed, carrageenan, galactan, gum arabic, pectin, mannan Starch, xanthan gum, dextran, Xinoglucan, curdlan, hyaluronic acid, gelatin, casein, albumin, collagen, methoxyethylene maleic anhydride copolymer, amphoteric methacrylate copolymer, polydimethylmethylenepiperidinium chloride, polyacrylate copolymer, poly Examples include vinyl acetate, nitrocellulose, and silicone resin.

  Although it does not specifically limit as a cationic polymer, Specifically, a cationized cellulose derivative, a cationic starch, a cationized guar gum derivative, a diallyl quaternary ammonium salt / acrylamide copolymer, a quaternized polyvinylpyrrolidone derivative, Quaternized vinylpyrrolidone / vinylimidazole polymer, polyglycol / amine condensate, quaternized collagen polypeptide, polyethyleneimine, cationic silicone polymer, adipic acid / dimethylaminohydroxypropyldiethylenetriamine copolymer, polyaminopolyamide, cationic chitin derivative, A quaternized polymer etc. are mentioned.

  The thickening and foam increasing components are not particularly limited, and specific examples include polyethylene glycol fatty acid ester, polyoxyethylene fatty acid ester methyl glycoside, tetradecene sulfonate, and the like.

  The oil gelling agent is not particularly limited. Specifically, dextrin fatty acid esters such as (palmitic acid / octanoic acid) dextrin, dextrin myristic acid, dextrin palmitate, inulin stearate; glycerin fatty acid ester, hydroxystearic acid Amide or ester derivatives of long-chain acylamino acids such as lauroylglutamic acid dibutylamide, glycerin fatty acid esters such as (behenic acid eicosanedioic acid) glyceryl, and the like.

  The sequestering agent is not particularly limited. Specifically, ethylenediaminetetraacetic acid and its salts, hydroxyethylenediaminetriacetic acid and its salts, phosphoric acid, ascorbic acid, succinic acid, gluconic acid, polyphosphates, metaphosphoric acid Examples include salts and hinokitiles.

  Antiseptic and antibacterial agents are not particularly limited, and specifically, paraoxybenzoic acid esters, benzoic acid and its salts, phenoxyethanol, hinokitile, salicylic acid and its salts, sorbic acid and its salts, dehydroacetic acid and its salts, Parachlorometacresol, hexachlorophene, boric acid, resorcin, tribromosaran, orthophenylphenol, thiram, photosensitizer 201, halocarban, trichlorocarbanide, tocopherol acetate, zinc pyrithione, phenol, isopropylmethylphenol, 2, 4, 4-trichloro-2-hydroxyphenol, hexachlorophene, chlorhexidine, benzethonium chloride, benzalkonium chloride, cetylpyridinium chloride, decalinium chloride, stearyldimethylammonium chloride , Stearyl trimethyl ammonium chloride, cetyl trimethyl ammonium chloride, methyl benzethonium, lauryl trimethyl ammonium chloride, lauroyl Kola amino formyl methyl pyridinium chloride, triclosan, Biozoru and the like.

  Although it does not specifically limit as a pH adjuster, Specifically, a citric acid, malic acid, adipic acid, glutamic acid, aspartic acid etc. are mentioned.

  Although it does not specifically limit as a dandruff or an itching prevention agent, Specifically, a trichloro carbanilide, a salicylic acid, a zinc pyrithione, isopropyl methyl phenol, etc. are mentioned.

  Although it does not specifically limit as a ultraviolet absorber, Specifically, a benzophenone derivative, a paraamino benzoic acid derivative, a paramethoxycinnamic acid derivative, a salicylic acid derivative, etc. are mentioned.

  Although it does not specifically limit as a whitening agent, Specifically, ascorbic acid and its salt (In addition to alkali metal salt or alkaline-earth metal salt like sodium salt, potassium salt, magnesium salt, calcium salt, ammonium salt, Amino acid salts, etc.), ascorbic acid derivatives (L-ascorbic acid alkyl esters, L-ascorbic acid phosphates and salts thereof, L-ascorbic acid-2-sulfates and salts thereof, L-ascorbic acid glucosides, etc.), alkoxysalicylic acid And salts thereof (alkoxy groups include, for example, methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, etc.), hydroquinone glycosides and derivatives thereof (arbutin, etc.), kojic acid and derivatives thereof, ellag Acid, chamomile extract, altea extract, licorice Extract, Sakuhakuhi extract, raspberry extract, apple flavonoid, bran extract, vitamin E and its derivatives, hinokitiol, placenta extract, lucinol, chamomile ET, glutathione, clove extract, tea extract, astaxanthin, cow placenta extract, tranexamic acid and its derivatives, Examples include resorcin derivatives, azulene, and γ-hydroxybutyric acid.

  The blood circulation promoter is not particularly limited, and specific examples include assembly extract, cephalanthin, vitamin E and its derivatives, gamma oryzanol and the like.

  Specific examples of the local stimulant include, but are not limited to, pepper tincture, ginger tincture, cantalis tincture, and nicotinic acid benzyl ester.

  Although it does not specifically limit as a nutrient, Specifically, various vitamins, an amino acid, etc. are mentioned.

  Although it does not specifically limit as a female hormone agent, Specifically, an estradiol, ethinyl estradiol, etc. are mentioned.

  The hair root activator is not particularly limited, and specific examples thereof include pantothenic acid and derivatives, laurel extract components, placenta extract, allantoin, and photosensitive element 301.

  The anti-inflammatory agent is not particularly limited, and specific examples include glycyrrhetinic acid, glycyrrhizic acid derivatives, allantoin, azulene, aminocaproic acid, hydrocortisone and the like.

  The astringent is not particularly limited, and specific examples include zinc oxide, zinc sulfate, allantoin hydroxyaluminum, aluminum chloride, aluminum sulfate, zinc sulfocolate, tannic acid, citric acid, and lactic acid.

  Although it does not specifically limit as a refreshing agent, Specifically, a menthol, camphor, etc. are mentioned.

  Although it does not specifically limit as an antihistamine, Specifically, diphenhydramine hydrochloride, chlorpheniramine maleate, a glycyrrhizic acid derivative, etc. are mentioned.

  The antioxidant is not particularly limited, and specific examples include tocopherols, butylhydroxyanisole (BHA), dibutylhydroxytoluene (BHT), gallic acid, nordihydroguaiaretic acid (NDGA), and the like.

  The sebum inhibitor is not particularly limited, and specific examples include estradiol, estrone, ethinyl estradiol, and the like.

  The exfoliating and solubilizing agent is not particularly limited, and specific examples include sulfur, salicylic acid, resorcin and the like.

  The α-hydroxy acid is not particularly limited, and specific examples include glycolic acid, lactic acid, malic acid, tartaric acid, and citric acid.

  Although it does not specifically limit as (beta) -hydroxylic acid, Specifically, salicylic acid etc. are mentioned.

  Organic synthetic dyes (dyes, lakes, organic pigments), natural dyes, inorganic pigments (external pigments, colored pigments, white pigments), pearlescent pigments, polymer powders, functional pigments are spherical, plate-like, and needle-like Etc .; particle size such as fumes, fine particles, pigment grade; and particle structure such as porous and nonporous, etc.

  For example, talc, kaolin, sericite, calcium carbonate, zinc oxide, aluminum oxide, magnesium oxide, zirconium oxide, magnesium carbonate, calcium carbonate, barium sulfate, chromium oxide, chromium hydroxide, tar dyes, mica, (synthesis) Sericite, silicon carbide, boron nitride, titanium dioxide, black titanium oxide, conger, red iron oxide, black iron oxide, yellow iron oxide, ultramarine, titanium coated mica, bismuth oxychloride, bengara, caking pigment, gunjo pink, Gunjo violet, chromium hydroxide, mica titanium, chromium oxide, aluminum cobalt oxide, carbon black, anhydrous silicic acid, magnesium silicate, bentonite, (synthetic) mica, zirconium oxide, magnesium (meth) silicate aluminate, silicic acid Calcium aluminate Polyethylene powder, nylon powder, polymethyl methacrylate, polyethylene terephthalate-polymethyl methacrylate laminated powder, acrylonitrile-methacrylic acid copolymer powder, vinylidene chloride-methacrylic acid copolymer powder, wool powder, silk powder, crystalline cellulose, N-acyl lysine, poly Methyl silsesquioxane powder, plant fruit or skin powder, bismuth oxychloride, mica titanium, iron oxide coated mica, iron oxide mica titanium, organic pigment treated mica titanium, aluminum powder, fine titanium oxide, fine particles Zinc oxide, fine titanium oxide coated mica titanium, fine zinc oxide coated mica titanium, barium sulfate coated mica titanium, carmine, β-carotene, chlorophyll, sunset yellow FCF, Ponceau SX, eosin YS , Tetrabromofluorescein, rhodamine B, quinoline yellow SS, quinoline yellow WS, alizanin cyanine green, quinizarin green, resolbin BCA, resolbin BCA, permaton red, herringdon pink CN, phthalocyanine blue, β-apo-8- Carotenal, capsanthin, lilopine, bixin, crocin, canthaxanthin, shisonin, raphanin, ninocyanin, calsamine, safrole yellow, rutin, quercetin, cacao pigment, lipoflavin, lacaic acid, carminic acid, kermesic acid, alizanin, shikonin, alkanine, niquinochrome, Examples include colorants for cosmetics such as hemoglobin, curcumin, and betanin.

  In addition, purified water, others, oyster extract, N-methyl-L-serine, whey, nicotinamide, diisopropylamine dichloroacetic acid, mevalonic acid, γ-aminobutyric acid (including γ-amino-β-hydroxybutyric acid) , Altea extract, Aloe extract, Apricot kernel extract, Turmeric extract, Oolong tea extract, Seawater dried product, Hydrolyzed wheat powder, Hydrolyzed silk, Carrot extract, Cucumber extract, Gentian extract, Yeast extract, Rice germ oil, Comfrey extract, Soap extract, Giant extract, Shikon extract, Birch extract, Atlantic mint extract, Assembly extract, Bisabolol, Propolis, Loofah extract, Bodaige extract, Hop extract, Marronnier extract, Mucloj extract, Melissa extract, Eucalyptus extract, Yukinoshita extract Rosemary extract, Roman chamomile extract, royal jelly extract, seaweed, rice bran, licorice, chimpi, touki, sweet potato pulverized product, sphingolipid, guaiazulene, vitamin C, ethanol, isopropanol, butyl alcohol, benzyl alcohol and other lower alcohols, cholesterol And sterols such as phytosterol.

  In particular, combined use with fatty acid diethanolamide, polyoxyethylene dioleic acid methyl glucoside, polyethylene glycol distearate, tetradecene sulfonate, myristic acid salts, myristyl dimethylamine is useful in terms of increasing viscosity and foaming power. . Further, the combined use with each zwitterionic surfactant is extremely useful in terms of reducing irritation.

[Cosmetic composition]
The cosmetic composition containing the emulsion of this embodiment is in the form of liquid, solid, gel, paste, cream, slurry, emulsion, suspension, mist, liquid crystal, powder, aerosol, etc. It can be used in various forms accordingly. However, it is not limited to this form.

  In the present embodiment, the “cosmetic composition” is a general term for quasi-drugs and cosmetics referred to in the Pharmaceutical Affairs Law. Specifically, quasi-drugs include mouth refreshing agents, anti-smell agents, fry powder, hair nourishing agents, hair removal agents, hair dyes, permanent wave agents, bath preparations, medicated cosmetics, medicated toothpastes, etc. Can be enumerated.

  Cosmetics include cosmetic soaps, facial cleansers (creams or pastes, liquids or gels, granules or powders, use of aerosols, etc.), shampoos, rinses, etc .; hair dyes, hair treatments (creams) , Mist, oil, gel and other forms and split coats, hair set (hair oil, set lotion, curler lotion, pomade, tics, bottled oil, hair spray, hair mist, hair Cosmetics for hair such as liquid, hair foam, hair gel, water grease); general cream, milky lotion (cleansing cream, cold cream, burnishing cream, hand cream, etc.), shaving cream (after shaving cream, shaving cream, etc.), makeup Water (hand lotion, general makeup) Etc.), cologne, shaving lotion (after shaving lotion, shaving lotion, etc.), cosmetic oil, basic cosmetics such as packs; white (cream white, solid white, powder white, talcum powder, kneading white, baby powder, body powder ), Powder, foundation (cream, liquid, solid, etc.), make-up cosmetics such as blusher, eyebrows, eye cream, eye shadow mascara, etc .; perfumes such as general perfume, paste perfume, powder perfume; gel Fragrances, deodorants, deodorizers of types, liquid types, ceramic types, etc .; suntan / sunscreen lotions, suntan / sunscreen lotions, suntan / sunscreen cosmetics such as sunscreen oils; nail cream, enamel, enamel Nail cosmetics such as remover; Liner cosmetics; lipstick, lip cosmetics lip balm and the like; toothpaste, etc. of oral cosmetics; bath salts, bath oils, you are possible to enumerate the bath cosmetics such as bubble bath.

  Preferable representative examples of the use of the emulsion of the present embodiment include hair cosmetics such as hair styling agents, hair treatments, and conditioning agents, among cosmetic compositions. As a method of use as a cosmetic for hair, it can be applied to dry hair or hair that has been applied and towel-dried to give a moist feeling and a smooth finish. Further, the emulsion of the present embodiment can be applied to, for example, emulsions, creams, lotions, skin lotions, and the like, as well as cleansing lotions, facial cleansers, body shampoos, and the like for skin cleaning purposes.

  Moreover, the emulsion of this embodiment can also be used suitably for various external preparation uses, cleaner uses, and the like. As external preparations, various cosmetics such as creams for cleansing or cleansing, cold creams, burnishing creams and moisturizing creams; skin or hair cosmetics such as massage creams and hair styling agents; anti-inflammatory agents and creamy pharmaceuticals; or Examples include drugs such as pest repellents.

  In addition, as a cleaner, using the properties that are well-suited with oil-based components, for example, oil stain cleaners around kitchens, ranges, etc., as well as cleaners such as machine oil stain cleaners and hand cleaners; or metal coatings such as automobiles Examples include film surfaces, wooden painted surfaces such as Buddhist altars, Buddhist utensils, baskets, desks, etc., plastic surfaces of household appliances such as TVs and PCs, and cleaner applications such as glass surfaces.

[Pharmaceutical composition]
In the present embodiment, the “pharmaceutical composition” is a generic term for pharmaceuticals referred to in the Pharmaceutical Affairs Law, and includes pharmaceutical preparations for external use, and can be used for the purpose of treatment, prevention, and improvement of specific skin diseases and symptoms. . Examples of the external medicine containing the emulsion of the present embodiment include, for example, for hemostasis, bactericidal disinfection, antipruritic, hair restoration, hair growth, melanin production suppression, anti-inflammatory, antibacterial, acne care, antioxidant , Whitening, pigmentation prevention or improvement, wrinkle improvement, sagging improvement, hand roughening treatment, insect bite treatment, myalgia treatment, cold sickness improvement, athlete's foot treatment, acne treatment, dry skin improvement And external preparations such as acupuncture, acupuncture, sunburn prevention, abrasion treatment, burn treatment, and bruise treatment.

  Hereinafter, the present invention will be described more specifically with reference to examples and the like. However, the present invention is not limited to the examples and the like. In addition, the unit in a table | surface is the mass%.

The evaluation means used in the examples of the present invention are as follows.
(Emulsion stability test)
The emulsion was placed in a glass tube and sealed, and allowed to stand at 50 ° C. for 1 week. After standing, the amount of oil separated from the emulsion layer was measured. The stability of the emulsion was evaluated by the amount of oil that maintained the emulsion state according to the following formula.
Emulsion stability (%) = 100 {1- (height of separated oil) / (height of total amount)}
○: Emulsion stability is 85% or more Δ: Emulsion stability is 70% or more and less than 85% ×: Emulsion stability is less than 70%

(Measurement of average particle size)
The diameter of 20 emulsified particles in the same field of view was directly measured on a digital image taken with a digital microscope (manufactured by Keyence Corporation: product name VHX-900), and the average was taken as the emulsified particle size.
○: Average particle size is 100 μm or less ×: Average particle size is more than 100 μm

(Stability test of cosmetic composition)
The cosmetic composition containing the emulsion was stored at 50 ° C., the state after 2 weeks was observed, and the stability was evaluated according to the following criteria.
○: Good with no change in state △: Slight separation is observed ×: Clear separation is observed

(sensory evaluation)
The evaluation was performed by five panelists on the moist feeling and smoothness of the cosmetic composition according to the following criteria, and the average score was calculated.
◎: Average score is 1.8 or more ○: Average score is 1.5 or more and less than 1.8 △: Average score is 1.0 or more and less than 1.5 ×: Average score is 0 or more and less than 1.0 (standard)
"Moist feeling" 2 points that are very moist
One point that doesn't feel moist
No moist feeling 0 point “smoothness” Very smooth 2 points
Slightly lacking 1 point
No smoothness 0 points

[Production example of silicone derivative]
(Production Example 1)
Hereinafter, in formula (1), R and X ² are methyl groups, one of X ¹ and X ³ is a group represented by formula (4), and the other is represented by formula (4). The production example of the silicone derivative which is a group represented by a hydrocarbon group having a nitrogen atom or a nitrogen atom is shown.

  65.0 g of both terminal amino-modified silicone (Shin-Etsu Silicone; KF-8010) was mixed in 293.4 g of acetone. While stirring at room temperature, 60.7 g of N-palmitoyl-L-glutamic anhydride was added to this mixed solution over 30 minutes, and the reaction was carried out at 50 ° C. for 3 hours. Further, stirring was continued at room temperature for 24 hours, and then the solvent was removed from the resulting reaction solution to obtain 124.0 g of a silicone derivative. Progression of the reaction was observed by GPC (column (Tosoh; G1000HHR + G2000HXL, solvent: THF), differential refractive index detector (Shimadzu Corporation; RID-10A)), peak of reaction product and increase in relative area ratio, N-palmitoyl-L -Decrease in relative area ratio of glutamic anhydride peak and NMR (AVANCE 600 MHz (BRUKER BIOSPIN)). The obtained silicone derivative was completely neutralized with sodium hydroxide and dried to obtain a sodium salt of the silicone derivative (silicone derivative (I)).

(Production Example 2)
Hereinafter, production examples of silicone derivatives in which R, X ¹ , and X ³ in the formula (1) are methyl groups and at least one of a plurality of X ² is a group represented by the formula (4) will be shown.

  Side-chain amino-modified silicone (Shin-Etsu Silicone; KF-868) 88.0 g was mixed in acetone 213.3 g. To this mixed solution, 3.4 g of N-myristoyl-L-glutamic anhydride was added over 30 minutes while stirring at room temperature, and the reaction was carried out at 50 ° C. for 5 hours. Furthermore, after continuing stirring at normal temperature for 24 hours, the solvent was removed from the resulting reaction solution to obtain 90.5 g of a silicone derivative. The reaction product was confirmed by NMR. The obtained silicone derivative was completely neutralized with sodium hydroxide and dried to obtain a sodium salt of the silicone derivative (silicone derivative (II)).

(Production Example 3)
Hereinafter, in formula (1), R is a methyl group, one of X ¹ and X ³ is a group represented by formula (4), and the other is a group represented by formula (4) or A production example of a silicone derivative, which is a group represented by a hydrocarbon group having a nitrogen atom and at least one of a plurality of X ² is a group represented by the formula (4), is shown.

  65.0 g of both side chain terminal amino-modified silicone (Shin-Etsu Silicone; KF-862) was mixed in 237.4 g of acetone. To this mixed solution, 36.7 g of N-palmitoyl-L-glutamic anhydride was added over 45 minutes while stirring at room temperature, and the reaction was carried out at 50 ° C. for 5 hours. Further, stirring was continued at room temperature for 24 hours, and then the solvent was removed from the resulting reaction solution to obtain 99.7 g of a silicone derivative. The reaction product was confirmed by NMR. The obtained silicone derivative was completely neutralized with sodium hydroxide and dried to obtain a sodium salt of the silicone derivative (silicone derivative (III)).

(Production Example 4)
Below, the manufacture example of the silicone derivative represented by Formula (3) is shown.
50.0 g of single-ended amino-modified silicone (Momentive Performance Materials; TSF4701) was mixed in 135.1 g of acetone. To this mixed solution, 7.9 g of N-stearoyl-L-glutamic anhydride was added over 45 minutes while stirring at room temperature, and the reaction was carried out at 50 ° C. for 5 hours. Further, stirring was continued at room temperature for 24 hours, and then the solvent was removed from the resulting reaction solution to obtain 57.3 g of a silicone derivative. The reaction product was confirmed by NMR. The obtained silicone derivative was completely neutralized with sodium hydroxide and dried to obtain a sodium salt of the silicone derivative (silicone derivative (IV)).

(Production Example 5)
Hereinafter, in formula (1), R, X ¹ , and X ³ are methyl groups, and at least one of the plurality of X ² is represented by formula (4) including a group represented by formula (6) The production example of the silicone derivative which is group is shown.

  Side chain amino-modified silicone (Shin-Etsu Silicone; KF-393) 50.0 g was mixed in acetone 220.5 g. To this mixed solution, 44.5 g of N-lauroyl-L-glutamic anhydride was added over 30 minutes while stirring at room temperature, and the reaction was carried out for 5 hours. Further, stirring was continued at room temperature for 24 hours, and then the solvent was removed from the obtained reaction solution to obtain 93.5 g of a silicone derivative. The reaction product was confirmed by NMR. The obtained silicone derivative was completely neutralized with sodium hydroxide and dried to obtain a sodium salt of the silicone derivative (silicone derivative (V)).

(Production Example 6)
Hereinafter, a production example of a silicone derivative in which at least one of a plurality of X ² in formula (2) is represented by formula (6) is shown.

Side chain type amino-modified silicone (Toray Dow silicone; FZ-3789) 120.0 g
Were mixed in 365.7 g of acetone. While stirring this mixed solution, 36.7 g of N-palmitoyl-L-glutamic anhydride was added over 30 minutes at room temperature, and the reaction was carried out at 50 ° C. for 3 hours. Furthermore, after stirring for 24 hours at room temperature, the solvent was removed from the reaction solvent,
155.2 g of silicone derivative was obtained. The reaction product was confirmed by NMR. The obtained silicone derivative was completely neutralized with potassium hydroxide and dried to obtain a potassium salt of the silicone derivative (silicone derivative (VI)).

[Examples 1 to 9, Comparative Examples 1 and 2: Preparation of emulsion]
The water phase and the oil phase containing each component shown in Table 1 were mixed in the same volume, and the emulsions of Examples 1 to 9 and Comparative Examples 1 and 2 were formed using a homogenizer (10000 rpm × 5 minutes). A stability test and an average particle size were measured. From Table 1, it can be seen that the emulsion containing the silicone derivative of the present invention and the oil component has high stability.

[Example 10, Comparative Example 3: Preparation of cosmetic composition]
The component (A) and glycerin shown in Table 2 were heated to 80 ° C. and stirred at 1000 rpm for 2 minutes. The component (B) heated at 80 degreeC was gradually added there, and it stirred at 1000 rpm for 2 minutes. Purified water heated to 80 ° C. was gradually added to the gel composition thus obtained and stirred at 2000 rpm for 3 minutes to obtain the cosmetic compositions of Example 10 and Comparative Example 3. The obtained cosmetic composition was subjected to a stability test, measurement of particle diameter, and sensory evaluation of “moist feeling” and “smoothness”. The results are shown in Table 2.

[Example 11: Production of whitening milk]
100 g of whitening milk having the composition shown in Table 3 was prepared by the following method.
The component group (1) and the component group (2) were dissolved by heating at 80 ° C., and the component group (3) and the component group (4) were dissolved at room temperature. After adding the component group (2) to the component group (1), the mixture was stirred and emulsified at 5000 rpm for 10 minutes and then stirred and cooled at 2000 rpm. On the other hand, it added in order of the component group (3) and the component group (4) at 50 degrees C or less, it cooled to room temperature, and whitening milk of Example 11 was obtained. The obtained whitening milk was subjected to a stability test and a sensory evaluation of “moist feeling” and “smoothness”. The results are shown in Table 3.

[Example 12: Preparation of sunscreen cream]
100 g of an on-screen cream having the composition shown in Table 4 was prepared by the following method.
Ingredient group (1) and ingredient group (2) were each heated to 80 ° C. and dissolved. The component group (2) was added while stirring the component group (1), and the mixture was stirred for 10 minutes at 500 rpm with a homomixer to emulsify. Then, it cooled to room temperature, stirring with a paddle mixer, and obtained the sunscreen cream of Example 12. The obtained sunscreen cream was subjected to a stability test and a sensory evaluation of “moist feeling” and “smoothness”. The results are shown in Table 4.

[Example 13: Production of highly moisturized emulsion]
100 g of a highly moisturizing emulsion having the composition shown in Table 5 was prepared by the following method.
Ingredient group (1) and ingredient group (2) were each heated to 80 ° C. and uniformly dissolved. Ingredient group (2) was stirred at a homomixer of 5000 rpm at 80 ° C. and ingredient group (1) was added and stirred for 10 minutes to emulsify. Thereafter, the mixture was cooled with paddle stirring, the component group (3) and the component group (4) were added at 50 ° C. or less, and the adjustment was terminated at 35 ° C., whereby a highly moisturizing emulsion of Example 13 was obtained. The obtained highly moisturized emulsion was subjected to a stability test and a sensory evaluation of “moist feeling” and “smoothness”. The results are shown in Table 5.

[Example 14: Preparation of hair treatment]
100 g of a hair treatment having the composition shown in Table 6 was prepared by the following method.
After heating and dissolving component group (1) and component group (2), component group (1) was added to the component group (2) little by little while maintaining about 80 ° C., and emulsification was carried out at homomixer 5000 rpm for 10 minutes after completion of the addition. Thereafter, the mixture was cooled with stirring, and the component group (3) was added at about 50 ° C. The mixture was cooled to 30 ° C. with stirring to obtain the hair treatment of Example 14. The obtained hair treatment was subjected to a stability test and a sensory evaluation of “moist feeling” and “smoothness”. The results are shown in Table 6.

  INDUSTRIAL APPLICABILITY The present invention can provide an emulsion composition that has good stability and does not impair the original characteristics of oily components, particularly silicone, and the composition containing the emulsion has excellent moist and smooth sensory characteristics. In particular, it can be suitably used as a cosmetic composition.

Claims (11)

Component (A): one or more silicone derivatives selected from the group consisting of silicone derivatives represented by formulas (1), (2) and (3);
Component (B): an oily component,
water and,
An emulsion containing
(1)
(In formula (1), each R is independently an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, It is a polyether group having a molecular weight of 10,000,000 or less, an alkyl ester group having 1 to 24 carbon atoms, or a hydroxyl group, and may have a nitrogen atom,
X ¹ , X ² , and X ³ are each independently a group similar to R or a group represented by formula (4), and at least one of X ¹ , X ² , and X ³ is A group represented by formula (4),
n is an integer of 0 to 300,000. )
(2)
(In the formula (2), R is the same group as described above,
Each R ¹ is independently a divalent hydrocarbon group having 1 to 22 carbon atoms;
R ² each independently represents an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an aryl group having 6 to 22 carbon atoms, or a molecular weight of 10,000,000. The following polyether groups, alkyl ester groups having 1 to 24 carbon atoms, hydroxyl groups, or hydrogen atoms,
X ⁴ is each independently a group similar to R or a group represented by formula (4), and at least one of X ⁴ is a group represented by formula (4);
Each Z is independently a polyalkylene oxide group;
h is each independently an integer of 0 to 300,000, i is each independently an integer of 1 to 300,000, and l is an integer of 1 to 300,000. )
(3)
(In formula (3), each R is independently the same group as described above,
X ⁵ is a group represented by the following formula (4),
p is each independently an integer of 1 to 300,000. )
(4)
(In Formula (4), A is a m + 1 valent hydrocarbon group having a nitrogen atom,
R ³ is each independently a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms,
Each R ⁴ is independently a hydrocarbon group having 1 to 23 carbon atoms;
Y is each independently a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group or a salt thereof;
m is an integer of 1 to 10, j and k are each independently an integer of 0, 1 or 2, and j and k are not 0 at the same time. ) The emulsion of Claim 1 whose m is 1 in said Formula (4), and A is group represented by Formula (5).
(5)
(In formula (5), R ⁵ is a hydrocarbon group having 1 to 22 carbon atoms, and R ⁸ is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.) The emulsion of Claim 1 whose m is 2 in said Formula (4), and A is group represented by Formula (6).
(6)
(In formula (6), R ⁶ and R ⁷ are each independently a hydrocarbon group having 1 to 22 carbon atoms.) Formula (1), R is a methyl ^group, X 1, ^{X 2,} and ^{X 3} satisfy one of the following (a) ~ (d), according to any one of claims 1 to 3 Emulsion.
(A) One of X ¹ and X ³ is a group represented by Formula (4), and the other is a group represented by Formula (4) or a hydrocarbon group having a nitrogen atom, and X ² Is a methyl group.
(B) X ¹ is the same as R defined in formula (1), X ³ is a group represented by formula (4), and X ² is a methyl group.
(C) X ¹ and X ³ are the same as R defined in the formula (1), and at least one of X ² is a group represented by the formula (4).
(D) One of X ¹ and X ³ is a group represented by Formula (4), and the other is a group represented by Formula (4) or a hydrocarbon group having a nitrogen atom, and X ² Is at least one group represented by formula (4). The emulsion according to any one of claims 1 to 4, wherein R ^{3 in the} formula (4) is a hydrogen atom, and Y is a carboxyl group or a salt thereof.   The emulsion according to any one of claims 1 to 5, wherein the component (B) comprises silicone.   The emulsion according to any one of claims 1 to 6, further comprising a component (C): an N-acylamino acid type surfactant.   The emulsion according to any one of claims 1 to 7, wherein an average particle diameter of the emulsion particles is 0.01 to 100 µm.   The composition containing the emulsion of any one of Claims 1-8.   A cosmetic composition comprising the emulsion according to any one of claims 1 to 8.   The pharmaceutical composition containing the emulsion of any one of Claims 1-8.