JP2017002099A - Emulsion composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an emulsion composition having excellent emulsion stability while reducing skin irritation and stickiness.SOLUTION: An emulsion composition comprises a water-soluble copolymer having one or more constitutional unit induced from a specific hydrophobic monomer (a), and one or more constitutional unit induced from a hydrophilic monomer (b) as essential constitutional units, and comprises no emulsifier except the water-soluble copolymer.SELECTED DRAWING: None

Description

  The present invention relates to an emulsified composition emulsified with a water-soluble copolymer.

An emulsified composition in which an oil phase component and an aqueous phase component are mixed with an emulsifier is widely used as a cosmetic dosage form. However, general low molecular weight emulsifiers may cause problems such as irritation to the skin and stickiness.
In order to solve such problems, various emulsification techniques using a polymer emulsifier have been recently proposed.

Patent Document 1 discloses an emulsified composition using hydroxyethyl cellulose as an emulsifier.
Patent Document 2 discloses an emulsified composition using an alkyl-modified carboxyvinyl polymer as an emulsifier.

JP 2011-231049 A JP 09-019631 A

  The above-mentioned polymer emulsifier has less irritation to the skin and, when contained at a low concentration, has advantages such as less stickiness, but is inferior in emulsifying power compared to conventional low-molecular emulsifiers. . Therefore, in order to ensure the stability of the emulsified state, it is necessary to highly blend the polymer emulsifier in the emulsified composition so as to have a high viscosity.

  In view of such a situation, an object of the present invention is to provide an emulsified composition having excellent emulsification stability while having little irritation to the skin and less stickiness.

  The present invention for solving the above-mentioned problems is characterized in that one or more structural units (a) derived from a hydrophobic monomer represented by the following general formula (I), (II) or (III) are hydrophilic and An emulsification comprising a water-soluble copolymer having one or more structural units (b) derived from monomers as essential structural units, and substantially free of an emulsifier other than the water-soluble copolymer. It is a composition.

Formula (I)
(I)
(In the general formula (I), R1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R2 does not include a branched hydrocarbon group having no ring structure having 13 to 30 carbon atoms or a ring structure. (A hydrocarbon group having 6 to 12 carbon atoms having two or more branches is represented.)

Formula (II)
(II)
(In the general formula (II), R3 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R4 and R5 may be the same or different, have no ring structure, and have a branched structure having 6 to 22 carbon atoms. X represents a group in which an OH group is eliminated from a trivalent alcohol.)

Formula (III)
(III)
(In the general formula (III), R6 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R7, R8, and R9 may be the same or different, have no ring structure, have a branch, and have 6 carbon atoms. Represents an acyl group of ˜22, and Y represents a group in which an OH group is eliminated from a tetravalent alcohol.

  The emulsified composition of the present invention has less stickiness during use by including the water-soluble copolymer.

  In a preferred embodiment of the present invention, the hydrophilic monomer is a polymerizable carboxylic acid, a hydrophilic monomer represented by the following general formula (IV), a hydrophilic monomer represented by the following general formula (VI), or the following general formula ( VII) and one or more hydrophilic monomers selected from the group consisting of a hydrophilic monomer represented by the following general formula (VIII).

Formula (IV)
(IV)
(In general formula (IV), R10 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R11 represents an alkylene group having 2 to 4 carbon atoms which may have a hydroxyl group, and R12 represents a hydrogen atom or carbon. An aromatic hydrocarbon group having 6 to 10 carbon atoms, an aliphatic hydrocarbon group having 1 to 14 carbon atoms, or an acyl group having 1 to 12 carbon atoms, and n represents an integer of 6 to 40.)

Formula (VI)
(VI)
(In the general formula (VI), R15 represents a hydrogen atom or a methyl group.)

Formula (VII)
(VII)
(In the general formula (VII), R16 represents a hydrogen atom or a methyl group, G-O- represents a group obtained by removing hydrogen from the hydroxyl group at the 1-position of the reducing sugar, m is 2 or 3, and l is 1-5. Represents an integer.)

Formula (VIII)
(VIII)
(In the general formula (VIII), R17 represents a hydrogen atom or a methyl group, R18 represents an amino acid residue, a polyamine residue or an amino alcohol residue. Q represents an oxygen atom or a group represented by NH.)

  By including the water-soluble copolymer containing the structural unit (b) derived from such a hydrophilic monomer, stickiness during use of the emulsion composition of the present invention can be further reduced.

In a preferred embodiment of the present invention, the hydrophobic monomer is a hydrophobic monomer represented by the general formula (II), and the water-soluble monomer is a hydrophilic monomer represented by the general formula (IV).
Such a water-soluble copolymer having a structural unit derived from a hydrophobic monomer and a hydrophilic monomer is excellent in emulsifying power and excellent in the effect of reducing stickiness during use of the emulsified composition of the present invention.

In a preferred embodiment of the present invention, the content of the water-soluble copolymer is 0.5 to 30% by mass.
By setting the content of the water-soluble copolymer in the above range, the stability of the emulsion composition can be improved.

In the preferable form of this invention, content of an oil phase component is 0.1-70 mass%.
The emulsion composition of the present invention in which the content of the oil phase component is in the above range is excellent in stability.

  Since the emulsified composition of the present invention has less stickiness, it is preferably a cosmetic.

Further, the present invention is derived from one or more structural units (a) derived from the hydrophobic monomer represented by the general formula (I), (II) or (III) and a hydrophilic monomer. The present invention also relates to an emulsifier composed of a water-soluble copolymer having one or more structural units (b) as essential structural units.
Such an emulsifier has excellent emulsifying power while being mild.

The present invention also relates to a method for producing an emulsified composition comprising a step of emulsifying using the emulsifier, wherein the emulsifier other than the emulsifier is substantially not used. .
According to such a method, it is possible to easily produce an emulsified composition without using a conventional emulsifier that can cause stickiness and without adding a high amount of emulsifier.

  ADVANTAGE OF THE INVENTION According to this invention, although there is little irritation | stimulation to skin and there is little stickiness, the emulsion composition excellent in emulsion stability can be provided.

The three component phase diagram which plotted the compounding ratio of the (glyceryl diisostearate methacrylate / methacrylic acid methoxy PEG-23) copolymer, squalane, and water in Examples 1-23 is represented. The three-component phase diagram which plotted the compounding ratio of the (glyceryl diisostearate methacrylate / methacrylic acid methoxy PEG-23) copolymer, tri (caprylic acid / capric acid) glyceryl, and water in Examples 24-54 is represented. The three-component phase diagram which plotted the compounding ratio of the (glyceryl diisostearate methacrylate / methacrylic acid methoxy PEG-23) copolymer, dimethicone, and water in Examples 55-81 is represented.

  A feature of the emulsion composition of the present invention is that it contains a water-soluble copolymer having a structural unit (a) derived from a hydrophobic monomer and a structural unit (b) derived from a hydrophilic monomer. Hereinafter, in the item <1>, a hydrophobic monomer, a hydrophilic monomer, and a water-soluble copolymer that is a copolymer thereof will be described.

<1> Water-soluble copolymer (1) Hydrophobic monomer In the present invention, a structural unit derived from a hydrophobic monomer represented by the general formula (I), (II) or (III) (hereinafter simply referred to as “ A water-soluble copolymer containing one or more of the structural units (sometimes referred to as “structural unit I”) as an essential structural unit is used.
In the present invention, the “structural unit derived from a monomer” refers to a structural unit formed by cleavage of a carbon-carbon unsaturated bond of a corresponding monomer by a polymerization reaction.
Hereinafter, the hydrophobic monomer represented by the general formula (I), (II) or (III) will be described.

(1-1) Hydrophobic monomer represented by general formula (I) In the general formula (I), R1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R2 represents a ring having 13 to 30 carbon atoms. A branched hydrocarbon group that does not include a structure or a hydrocarbon group having 6 to 12 carbon atoms that includes two or more branches that does not include a ring structure.
Here, examples of the alkyl group represented by R1 include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a cyclopropyl group. In the present invention, R1 is preferably a hydrogen atom or a methyl group.

  Examples of the branched hydrocarbon group not containing a ring structure having 13 to 30 carbon atoms represented by R2 include 1-methyldodecanyl group, 11-methyldodecanyl group, 3-ethylundecanyl group, 3- Ethyl-4,5,6-trimethyloctyl group, 1-methyltridecanyl group, 1-hexyloctyl group, 2-butyldecanyl group, 2-hexyloctyl group, 4-ethyl-1-isobutyloctyl group, 1-methyl Pentadecanyl group, 2-hexyldecanyl group, 2-octyldecanyl group, 2-hexyldecanyl group, 16-methylheptadecanyl group, 9-methylheptadecanyl group, 7-methyl-2- (3 -Methylhexyl) decanyl group, 3,7,11,15-tetra-methylhexadecanyl group, 2-octyldodecanyl group, 2-decyltetradecanyl group, 2-dodecylhexade It may be exemplified sulfonyl groups and the like.

  Moreover, as a C6-C12 hydrocarbon group which does not contain the ring structure represented by R2 and has two or more branches, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, 3, 3-dimethylbutyl group, 1,3-dimethylbutyl group, 1,2,2-trimethylpropyl group, 1,1-dimethylpentanyl group, 1-isopropylbutyl group, 1-isopropyl-2-methylpropyl group, 1 , 1-diethylpropyl group, 1-ethyl-1-isopropylpropyl group, 2-ethyl-4-methylpentyl group, 1-propyl-2,2-dimethylpropyl group, 1,1,2-trimethyl-pentyl group, 1-isopropyl-3-methylbutyl group, 1,2-dimethyl-1-ethylbutyl group, 1,3-dimethyl-1-ethylbutyl group, 1-ethyl-1-isopropyl-propyl group, , 1-dimethylhexyl group, 1-methyl-1-ethylpentyl group, 1-methyl-1-propylbutyl group, 1,4-dimethylhexyl group, 1-ethyl-3-methylpentyl group, 1,5-dimethyl Hexyl group, 1-ethyl-6-methylheptyl group, 1,1,3,3-tetramethylbutyl group, 1,2-dimethyl-1-isopropylpropyl group, 3-methyl-1- (2,2-dimethyl) Ethyl) butyl group, 1-isopropylhexyl group, 3.5.5-trimethylhexyl group, 2-isopropyl-5-methylhexyl group, 1,5-dimethyl-1-ethylhexyl group, 3,7-dimethyloctyl group, Examples include 2,4,5-trimethylheptyl group, 2,4,6-trimethylheptyl group, 3,5-dimethyl-1- (2,2-dimethylethyl) hexyl group and the like. Can.

(1-2) Hydrophobic monomer represented by general formula (II) or (III) In the general formulas (II) and (III), R3 and R6 represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. , R4, R5, R7, R8 and R9 may be the same or different and each represents a branched acyl group having 6 to 22 carbon atoms which does not contain a ring structure. X represents a group in which an OH group is eliminated from a trivalent alcohol.

  Here, examples of the alkyl group represented by R3 and R6 include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a cyclopropyl group. In the present invention, R3 is preferably a hydrogen atom or a methyl group.

  Moreover, as a branched C6-C22 acyl group which does not contain the ring structure represented by R4, R5, R7, R8, R9, 2-methylpentanoyl group, 3-methylpentanoyl group, 4 -Methylpentanoyl group, 2-ethylbutanoyl group, 2-ethylbutanoyl group, 2,2-dimethylbutanoyl group, 3,3-dimethylbutanoyl group, 2-methylhexanoyl group, 4-methylhexanoyl group Group, 5-methylhexanoyl group, 2,2-dimethylpentanoyl group, 4,4-dimethylpentanoyl group, 2-methylheptanoyl group, 2-ethylhexyl group, 2-propylpentanoyl group, 2,2- Dimethylhexanoyl group, 2,2,3-trimethylpentanoyl group, 2-methyloctanoyl group, 3,3,5-trimethylhexanoyl group, 2-methylnonanoyl 4-methylnonanoyl group, 8-methylnonanoyl group, 4-ethyloctanoyl group, 2-ethyloctanoyl group, 2-butylhexanoyl group, 2-tert-butylhexanoyl group, 2,2-diethylhexanoyl group, 2,2-dimethyloctanoyl group, 3,7-dimethyloctanoyl group, neodecanoyl group, 7-methyldecanoyl group, 2-methyl-2-ethyloctanoyl group, 2-methylundecanoyl group, 10-methyl Undecanoyl group, 2,2 dimethyldecanoyl group, 2-ethyldecanoyl group, 2-butyloctanoyl group, diethyloctanoyl group, 2-tert-butyl-2,2,4-trimethylpentanoyl group, 10 -Methyldodecanoyl group, 3-methyldodecanoyl group, 4-methyldodecanoyl group, 11-methyldodecanoyl group, 10- Tilundecanoyl group, 12-methyltridecanoyl group, 2-butyldecanoyl group, 2-hexyloctanoyl group, 2-butyl-2-ethyloctanoyl group, 12-methyltetradecanoyl group, 14-methyl Pentadecanoyl group, 2-butyldodecanoyl group, 2-hexyldecanoyl group, 16-methylheptadecanoyl group, 2,2-dimethylhexanoyl group, 2-butylhexadecanoyl group, 2-hexyldodecanoyl group 2,4,10,14-tetramethylpentanoyl group, 18-methylnonadecanoyl group, 3,7,11,15-tetra-methylhexadecanoyl group, 19-methyleicosanoyl group, etc. be able to.

  In a preferred embodiment of the present invention, in the general formulas (II) and (III), R4, R5, R7, R8, and R9 may be the same or different and do not include a ring structure and have a branch. An acyl group having 10 to 22 carbon atoms, or an acyl group having 6 to 9 carbon atoms having two or more branches that does not include a ring structure.

  Such a branched acyl group having 10 to 22 carbon atoms which does not contain a ring structure and is represented by R4, R5, R7, R8 and R9 in a preferred embodiment includes a 2-methylnonanoyl group, 4- Methylnonanoyl group, 8-methylnonanoyl group, 4-ethyloctanoyl group, 2-ethyloctanoyl group, 2-butylhexanoyl group, 2-tert-butylhexanoyl group, 2,2-diethylhexanoyl group), 2, 2-dimethyloctanoyl group, 3,7-dimethyloctanoyl group, neodecanoyl group), 7-methyldecanoyl group, 2-methyl-2-ethyloctanoyl group, 2-methylundecanoyl group, 10-methylun Decanoyl group, 2,2 dimethyldecanoyl group, 2-ethyldecanoyl group, 2-butyloctanoyl group, diethyloctanoyl group, 2 -Tert-butyl-2,2,4-trimethylpentanoyl group, 10-methyldodecanoyl group, 3-methyldodecanoyl group, 4-methyldodecanoyl group, 11-methyldodecanoyl group, 10-ethylundecanoyl group Group, 12-methyltridecanoyl group, 2-butyldecanoyl group, 2-hexyloctanoyl group, 2-butyl-2-ethyloctanoyl group, 12-methyltetradecanoyl group, 14-methylpentadecanoyl group 2-butyldodecanoyl group, 2-hexyldecanoyl group, 16-methylheptadecanoyl group, 2,2-dimethylhexanoyl group, 2-butylhexadecanoyl group, 2-hexyldecanoyl group, 2,4 , 10,14-tetramethylpentanoyl group, 18-methylnonadecanoyl group, 3,7,11,15-tetra-methylhexa A decanoyl group, a 19-methyl eicosanoyl group, etc. can be illustrated.

  Moreover, as a C6-C9 acyl group which does not contain a ring structure and has 2 or more branches, represented by R4, R5, R7, R8, R9 in a preferred embodiment, 2,2-dimethyl Butanoyl group, 3,3-dimethylbutanoyl group, 2,2-dimethylpentanoyl group, 4,4-dimethylpentanoyl group, 2,2-dimethylhexanoyl group, 2,2,3-trimethylpentanoyl group 3,5,5-trimethylhexanoyl group and the like.

  The group derived from the trihydric alcohol represented by X in the general formula (II) is not particularly limited as long as the OH group is released from the trihydric alcohol, but glycerin, trimethylolpropane, trimethylolethane. A group in which an OH group is eliminated from a trihydric alcohol selected from the group consisting of

  Further, the group derived from the tetrahydric alcohol represented by Y in the general formula (III) is not particularly limited as long as the OH group is removed from the tetrahydric alcohol, but diglycerin, pentaerythritol, erythritol. A group in which an OH group is eliminated from a tetrahydric alcohol selected from the group consisting of D-threitol and L-threitol can be preferably exemplified.

In the present invention, it is particularly preferable to use a water-soluble copolymer containing the structural unit II.
In a more preferred embodiment of the present invention, the hydrophobic monomer represented by the general formula (II) is a hydrophobic monomer represented by the following general formula (V).

General formula (V)
(V)
(In the general formula (V), R13 and R14 may be the same or different and each represents a branched acyl group having 16 to 22 carbon atoms that does not contain a ring structure. Z represents an OH group from a trivalent alcohol. Represents a leaving group.)

The carbon number of the acyl group of R13 and R14 in the general formula (V) is 12 to 22, more preferably 14 to 20, and still more preferably 16 to 20.
Moreover, the carbon number of the main chain of the acyl group of R13 and R14 in the general formula (V) is preferably 9 to 21, more preferably 12 to 20, and still more preferably 16 to 18.
Moreover, the number of branches in the acyl group of R13 and R14 in the general formula (V) is preferably 1 to 3, more preferably 1 or 2, and still more preferably 1.
Furthermore, in the acyl groups of R13 and R14 in the general formula (V), the position number of the main chain carbon to which the branched chain is bonded is preferably as large as possible. Specifically, the branched chain is bonded to carbon at the end of the main chain, preferably from the first to the third carbon, more preferably the first or second carbon, and even more preferably the first carbon. It is preferable.

  Specific examples of R13 and R14 include 10-methylundecanoyl group, 10-methyldodecanoyl group, 11-methyldodecanoyl group, 10-ethylundecanoyl group, 12-methyltridecanoyl group, and 12-methyl. Tetradecanoyl group, 14-methylpentadecanoyl group, 16-methylheptadecanoyl group, 2,4,10,14-tetramethylpentanoyl group, 18-methylnonadecanoyl group, 3,7,11,15 -A tetra-methylhexadecanoyl group, a 19-methyleicosanoyl group, etc. can be illustrated suitably.

  The group derived from the trihydric alcohol represented by Z in the general formula (V) is not particularly limited as long as the OH group is released from the trihydric alcohol, but glycerin, trimethylolpropane, trimethylolethane. A group in which an OH group is eliminated from a trihydric alcohol selected from the group consisting of

(2) Hydrophilic monomer The hydrophilic monomer in the present invention is represented by a polymerizable carboxylic acid, the general formula (IV), the following general formula (VI), the following general formula (VII), and the following general formula (VIII). Can be used.

(2-1) Polymerizable carboxylic acid In the present invention, as the polymerizable carboxylic acid or a salt thereof, specifically, acrylic acid, methacrylic acid, crotonic acid, itaconic acid, fumaric acid and its sodium salt, potassium salt, Examples thereof include ammonium salts and amine salts. Among these, acrylic acid, methacrylic acid and salts thereof are particularly preferable because of high polymerizability. When a structural unit derived from a polymerizable carboxylic acid salt is introduced into the water-soluble copolymer of the present invention, the polymerizable carboxylic acid may be converted into a salt in advance, and a polymerization reaction may be performed. A structural unit derived from a carboxylic acid may be derived into a water-soluble copolymer and then neutralized with a base to form a salt.

(2-2) Hydrophilic monomer represented by general formula (IV) In the general formula (IV), R10 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R11 may have a hydroxyl group. Represents a good alkylene group having 2 to 4 carbon atoms, and R12 represents a hydrogen atom, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aliphatic hydrocarbon group having 1 to 14 carbon atoms, or an acyl group having 1 to 12 carbon atoms. Represent. n represents an integer of 6 to 40.

  Examples of the alkyl group represented by R10 in the general formula (IV) include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a cyclopropyl group. In the present invention, R10 is preferably a hydrogen atom or a methyl group.

  Examples of the alkylene group represented by R11 include an ethylene group, a propylene group, an isopropylene group, a 2-hydroxypropylene group, a 1-hydroxy-2-methylethylene group, and a 2-hydroxy-1-methylethylene group. Of these, ethylene group or propylene group is preferable, and ethylene group is more preferable.

  Further, among the groups represented by R12, examples of the aromatic group having 6 to 10 carbon atoms include a phenyl group, a benzyl group, a methylphenyl group, and an ethylphenyl group; Preferred examples of the hydrogen group include a methyl group, an ethyl group, a butyl group, a tertiary butyl group, a hexyl group, a cyclohexyl group, an octyl group, a 2-ethylhexyl group, and a lauryl group; Preferred examples of the 12 acyl group include a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, and a lauroyl group. Of these, the group represented by R5 is preferably an aliphatic hydrocarbon group having 1 to 14 carbon atoms, and more preferably an alkyl group having 1 to 12 carbon atoms.

  Furthermore, n in general formula (IV) is a numerical range of 6-40.

  Specific examples of the monomer represented by the general formula (IV) in which R11 is a propylene group include polypropylene glycol (9) monoacrylate, polypropylene glycol (13) monoacrylate, and polypropylene glycol (9) monomethacrylate. And polypropylene glycol (13) monomethacrylate. The number in parentheses represents N. Many of these polymers are commercially available. Specific examples of these commercially available products include “Blemmer” AP-400, AP-550, AP-800, PP-500, PP-800 (all manufactured by NOF Corporation) and the like.

  Specific examples of the monomer represented by the general formula (IV) in which R11 is an ethylene group include polyethylene glycol (10) monoacrylate, polyethylene glycol (8) monomethacrylate, and polyethylene glycol (23) monoacrylate. , Polyethylene glycol (23) monomethacrylate, methoxypolyethylene glycol (9) acrylate, methoxypolyethylene glycol (9) methacrylate, methoxypolyethylene glycol (23) methacrylate, oleyloxypolyethylene glycol (18) methacrylate, lauroxypolyethylene glycol (18) acrylate , Lauroyloxy polyethylene glycol (10) methacrylate, stearoxy polyethylene glycol (30) monometa Relate and the like.

  The above-mentioned hydrophilic monomer can be obtained in high yield by esterification reaction of the corresponding polyethylene glycol, polyethylene glycol monoether, polyethylene glycol monoester and acrylic acid or methacrylic acid chloride or anhydride. Moreover, since there are already many commercial products, it is also possible to use such commercial products. Specific examples of such commercially available products include the trade names Blemmer, AE-400, PE-350, AME-400, PME-400, PME-1000, ALE-800, PSE-1300, etc. Etc.).

(2-3) Hydrophilic monomer represented by general formula (VI) As the hydrophilic monomer in the present invention, a hydrophilic monomer represented by the following general formula (VI) may be used.

(General Formula VI)
(VI)
(In the general formula (VI), R15 represents a hydrogen atom or a methyl group.)

Specific examples of the hydrophilic monomer represented by the general formula (VI) include 2-acryloyloxyethyl phosphorylcholine (APC) and 2-methacryloyloxyethyl phosphorylcholine (MPC). These monomers can be synthesized by the following method described in Polymer Journal, Vol 22, No. 5, for example.
<Synthesis method>
2-bromoethyl phosphoryl dichloride is reacted with 2-hydroxyethyl methacrylate or 2-hydroxyethyl acrylate, and 2-methacryloyloxyethyl-2′-bromoethyl phosphate or 2-acryloyloxyethyl-2′-bromoethyl phosphate Are obtained, and these compounds are reacted with triethylamine in methanol.

(2-4) Hydrophilic monomer represented by general formula (VII) As the hydrophilic monomer in the present invention, a hydrophilic monomer represented by the following general formula (VII) may be used.

Formula (VII)
(VII)
(In the general formula (VII), R16 represents a hydrogen atom or a methyl group, G-O- represents a group obtained by removing hydrogen from the hydroxyl group at the 1-position of the reducing sugar, m is 2 or 3, and l is 1-5. Represents an integer.)

  In the hydrophilic monomer represented by the general formula (VII), as the reducing sugar of the group obtained by removing hydrogen from the hydroxyl group at the 1-position of the reducing sugar represented by G-O-, specifically, glucose, mannose, Examples include one or more selected from the group consisting of monosaccharides such as galactose, arabinose, xylose and ribose, disaccharides such as maltose, lactose and cellobiose, trisaccharides such as maltotriose, and oligosaccharides such as malto-oligosaccharide However, among these, one or more selected from the group consisting of glucose, galactose, arabinose, xylose, ribose, maltose, and lactose cellobiose is preferable, and glucose is particularly preferable. The monomer represented by the general formula (VII) is preferably glucosyloxyethyl methacrylate (hereinafter abbreviated as GEMA) or glucosyloxyethyl acrylate (hereinafter abbreviated as GEA).

(2-5) Hydrophilic monomer represented by general formula (VIII) As the hydrophilic monomer in the present invention, a hydrophilic monomer represented by the following general formula (VIII) may be used.

Formula (VIII)
(VIII)
(In the general formula (VIII), R17 represents a hydrogen atom or a methyl group, R18 represents an amino acid residue, a polyamine residue or an amino alcohol residue. Q represents an oxygen atom or a group represented by NH.)

In the monomer of the general formula (VIII), the amino acid of the amino acid residue represented by R18 is not particularly limited as long as it is a commonly known amino acid. Specifically, glycine, alanine, glutamine, lysine, Arginine etc. are illustrated. Among these, the lysine residue is particularly preferable because the obtained water-soluble copolymer is excellent in the effect of restoring the skin barrier.

  Further, the polyamine in the polyamine residue represented by R18 means an amine having two or more amino groups which may be substituted with an alkyl group in the same molecule, specifically, diamine, triamine, tetraamine. Or the amine by which the hydrogen atom of these amino groups is substituted by the alkyl group is illustrated. Of these, diamines are preferred because the feeling of use of the resulting external preparation for skin containing the water-soluble copolymer is particularly excellent. Particularly preferred examples include ethylenediamine, 1 from the availability of raw materials for synthesis. , 4-diamino-n-butane, 1,6-diamino-n-hexane and the like.

  Furthermore, the amino alcohol in the amino alcohol residue represented by R18 means a compound having an amino group and an alcoholic hydroxyl group which may be substituted with an alkyl group in the same molecule. The amino alcohol is not particularly limited as long as it is generally known, but specific examples include ethanolamine and triethylaminoethanol.

  Although it does not specifically limit as a salt of the monomer represented by general formula (VIII), Specifically, the sodium salt, potassium salt, ammonium salt, amine salt, etc. which neutralized the acid part with the base, Examples thereof include hydrochlorides, sulfates, nitrates, phosphates, citrates, oxalates, carbonates, etc., in which the amino group is neutralized with an acid. When the structural unit derived from the salt of the monomer represented by the general formula (VIII) is introduced into the water-soluble copolymer of the present invention, the monomer represented by the general formula (VIII) is converted into a salt in advance to carry out the polymerization reaction. Alternatively, the structural unit derived from the monomer represented by formula (VIII) may be derived into a water-soluble copolymer by a polymerization reaction, and then neutralized to form a salt.

  Specific examples of the monomer represented by the general formula (VIII) and salts thereof include compounds having the following structures and salts thereof.

The hydrophilic monomer represented by the general formula (VIII) can be synthesized, for example, by an esterification reaction or amidation reaction using (meth) acrylic acid or (meth) acrylic acid chloride as shown below.
(In the reaction formula, R17 represents a hydrogen atom or a methyl group, R18 represents an amino acid residue, a polyamine residue or an aminoalcohol residue. Q represents an oxygen atom or a group represented by NH.)

As described above, as the hydrophilic polymer in the present invention, the general formula (IV), the general formula (VI), the general formula (VII), and the general formula (VIII) can be used.
In a preferred embodiment of the present invention, the water-soluble copolymer comprises a structural unit IV derived from the general formula (IV).

(3) Water-soluble copolymer In this invention, the water-soluble copolymer which has the structural unit II and the structural unit IV can be used preferably. More preferably, a water-soluble copolymer having the structural unit V and the structural unit IV is used.
Among such water-soluble copolymers, a (methacrylic acid methoxy PEG-23 / diisostearic acid glyceryl methacrylate) copolymer is particularly preferably used.
By containing such a water-soluble copolymer, the emulsion composition is low in irritation, less sticky, and excellent in emulsion stability.

(Methoxymethacrylic acid PEG-23 / glyceryl methacrylate) is a structural unit (a) in which, among the hydrophobic monomers represented by the general formula (V), R13 and R14 are 16-methylheptadecanoyl. It mainly contains a structural unit (a) derived from a hydrophobic monomer as a group.
Further, as the structural unit (b), among the hydrophilic monomers represented by the general formula (IV), R10 is derived from a hydrophilic monomer having a methyl group, R11 is an ethylene group, R12 is a methyl group, and n is 23. The structural unit (b) is mainly included.

Generally, a highly hydrophobic surfactant is suitable for forming a water-in-oil emulsion composition, and on the contrary, a highly hydrophilic surfactant is suitable for forming an oil-in-water emulsion composition. Similarly, the water-soluble copolymer in the present invention is suitable for forming a water-in-oil emulsion composition when the proportion of the structural unit (a) that is hydrophobic is high, When the proportion of a certain structural unit (b) is high, it is suitable for forming an oil-in-water emulsion composition.
Thus, the emulsification form of the emulsion composition to be formed can be adjusted by appropriately adjusting the proportion and ratio of the structural unit (a) and the structural unit (b).

In the present invention, the proportion of the structural unit (a) in all the structural units in the water-soluble copolymer is preferably 1 to 50% by mass, more preferably 20 to 50% by mass, and 30 to 40% by mass.
By setting the proportion of the structural unit (a) in the water-soluble copolymer within the above range, it is possible to provide an oil-in-water emulsion composition in which the sticky feeling is further reduced.

In the present invention, the proportion of the structural unit (b) in all the structural units in the water-soluble copolymer is preferably 50 to 99% by mass, more preferably 50 to 80% by mass, and 60 to 70% by mass.
By setting the proportion of the structural unit (b) in the water-soluble copolymer within the above range, it is possible to provide an oil-in-water emulsion composition with a reduced stickiness.

  In the present invention, the mass ratio of the structural unit (a) to the structural unit (b) constituting the water-soluble copolymer is preferably 10:90 to 50:50, more preferably 20:80 to 50:50, Preferably it is 30: 70-40: 60.

The molar ratio of the structural unit (a) to the structural unit (b) constituting the water-soluble copolymer is preferably 15:85 to 62:38, more preferably 29:71 to 62:38, and still more preferably 41. : 59-52: 48.
By making the mass ratio and the molar ratio of the structural unit (a) and the structural unit (b) in the water-soluble copolymer within the above ranges, the water-soluble water solution is excellent in emulsifying power and suitable for forming an oil-in-water emulsion composition. Copolymer.

In the present invention, the average molecular weight of the water-soluble copolymer is preferably 20000 to 110000, more preferably 20000 to 80000, more preferably 30000 to 80000, more preferably 40000 to 70000, still more preferably 50000 to 70000, still more preferably. 57000-66000.
In addition, an average molecular weight means here the weight average molecular weight of polystyrene conversion measured by GPC.

<2> Emulsified Composition The emulsified composition of the present invention is characterized by substantially not containing an emulsifier other than the above-mentioned water-soluble copolymer.
Here, “substantially free of an emulsifier other than the above-mentioned water-soluble copolymer” means that the content of the emulsifier other than the above-mentioned water-soluble copolymer is 0.3% by mass or less, preferably 0.1% by mass or less. More preferably, it means 0.01% by mass or less, more preferably 0.001% by mass or less. Moreover, it is especially preferable not to contain emulsifiers other than the above-mentioned water-soluble copolymer.

The content of the above water-soluble copolymer in the emulsion composition is preferably 0.1 to 50% by mass, more preferably 0.5 to 30% by mass.
By making content of the above-mentioned water-soluble copolymer into the said range, the emulsion stability of an emulsion composition can be improved more.

The contents of the aqueous phase and the oil phase in the emulsion composition of the present invention can be appropriately adjusted by changing the ratio of the structural unit (a) and the structural unit (b) in the water-soluble copolymer.
Hereinafter, the content of the oil phase and the water phase when a water-soluble copolymer containing the structural unit (a) and the structural unit (b) is used at a ratio suitable for forming the above-described oil-in-water emulsion composition, etc. Will be described.
In the present specification, the oil phase and the oil phase component, and the water phase and the water phase component are described as not including the water-soluble copolymer in the present invention.

The content of the oil phase component in the emulsion composition of the present invention is preferably 0.01 to 80% by mass, more preferably 0.1 to 70% by mass.
By making content of an oil phase component into the said range, the emulsification stability of an emulsion composition can be improved.
In addition, an oil phase component is an oil agent and a lipophilic component, and means the component contained in an oil phase in an emulsion composition.

In the emulsified composition of the present invention, the mass ratio of the water-soluble copolymer to the oil phase component is preferably 1: 100 to 1: 0.2, more preferably 1:70 to 1: 0.3.
By setting the mass ratio of the water-soluble copolymer and the oil phase component in the above range, the emulsion stability of the emulsion composition can be improved.

In the emulsion composition of the present invention, the mass ratio of the oil phase to the water phase is preferably 0.1: 99.9 to 80:20, more preferably 1:99 to 65:35.
By setting the mass ratio of the oil phase to the water phase in the above range, a stable oil-in-water emulsion composition can be formed.

The components contained in the oil phase and the aqueous phase are not particularly limited.
Examples of the oil agent constituting the oil phase include liquid oils and fats, solid oils and fats, waxes, hydrocarbon oils, higher fatty acids, higher alcohols, synthetic ester oils, silicone oils, and the like.

  Examples of liquid oils include avocado oil, camellia oil, turtle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, southern castor oil, castor oil, linseed oil , Safflower oil, cottonseed oil, eno oil, meadow foam oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, cinnagari oil, Japanese kiri oil, jojoba oil, germ oil, triglycerin, glycerin trioctanoate, Examples include glycerin triisopalmitate.

  Solid fats and oils include cocoa butter, coconut oil, horse fat, hydrogenated coconut oil, palm oil, beef tallow, sheep fat, hardened beef tallow, palm kernel oil, pork fat, beef bone fat, owl kernel oil, hydrogenated oil, and cow leg fat. , Mole, hardened castor oil, and the like.

  The waxes include beeswax, candelilla wax, cotton wax, carnauba wax, bayberry wax, ibota wax, whale wax, montan wax, nuka wax, lanolin, kapok wax, lanolin acetate, liquid lanolin, sugar cane wax, lanolin fatty acid isopropyl, lauryl hexyl, reduced lanolin, jojojo Examples thereof include a wax, hard lanolin, shellac wax, POE lanolin alcohol ether, POE lanolin alcohol acetate, POE cholesterol ether, lanolin fatty acid polyethylene glycol, POE hydrogenated lanolin alcohol ether, and the like.

  Examples of the hydrocarbon oil include liquid paraffin, ozokerite, pristane, paraffin, ceresin, squalene, petrolatum, and microcrystalline wax.

  Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behen (behenine) acid, 12-hydroxystearic acid, undecylenic acid, and toric acid.

  Examples of the higher alcohol include cetyl alcohol, stearyl alcohol, behenyl alcohol, batyl alcohol, myristyl alcohol, cetostearyl alcohol, and the like.

  Synthetic ester oils include isopropyl myristate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyl decyl dimethyloctanoate, cetyl lactate, myristyl lactate Lanolin acetate, isocetyl stearate, isocetyl isostearate, sucrose stearate, sucrose oleate, 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, tri-2-ethyl Trimethylolpropane xylate, trimethylolpropane triisostearate, pentane erythritol tetra-2-ethylhexylate, glycerin tri-2-ethylhexylate, trimethylolpropane triisostearate, cetyl 2-ethylhexanoate, 2-ethylhexyl palmitate Glyceryl trimyristate, glyceride tri-2-heptylundecanoate, castor oil fatty acid methyl ester, oleic acid oil, cetostearyl alcohol, acetoglyceride, 2-heptylundecyl palmitate, cetyl palmitate, diisobutyl adipate, N- Lauroyl-L-glutamic acid-2-octyldodecyl ester, di-2-heptylundecyl adipate, ethyl laurate, di-2-ethyl sebacate Hexyl myristate 2-hexyl decyl palmitate, 2-hexyldecyl, 2-hexyldecyl adipate, sebacic acid diisopropyl, 2-ethylhexyl succinate, ethyl acetate, butyl acetate, amyl acetate, and triethyl citrate.

  Examples of silicone oils include chain polysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, and methylhydrogenpolysiloxane, and cyclic polysiloxanes such as decamethylpolysiloxane, dodecamethylpolysiloxane, and tetramethyltetrahydrogenpolysiloxane. Is mentioned.

  1 type (s) or 2 or more types can be used for an oil agent.

  In the emulsified composition of the present invention, optional additive components that are usually blended in cosmetics may be blended within a range that does not impair the effects of the present invention. Examples of such additive components include humectants such as polyethylene glycol, glycerin, 1,3-butylene glycol, erythritol, sorbitol, xylitol, and maltitol; lower alcohols such as ethanol; butylhydroxytoluene, tocopherol, and phytin. Antioxidants; antibacterial agents such as benzoic acid, salicylic acid, sorbic acid, paraoxybenzoic acid alkyl ester, hexachlorophene; paraaminobenzoic acid (hereinafter abbreviated as “PABA”), PABA monoglycerin ester, N, N-dipropoxy PABA ethyl ester N, N-diethoxy PABA ethyl ester, N, N-dimethyl PABA methyl ester, N, N-dimethyl PABA ethyl ester, N, N-dimethyl PABA butyl ester, N, N-dimethyl P Benzoic acid UV absorbers such as BA2-ethylhexyl ester; Anthranilic acid UV absorbers such as homomenthyl-N-acetylanthranilate; Amyl salicylate, menthyl salicylate, homomenthyl salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate, p -Salicylic acid ultraviolet absorbers such as isopropanol phenyl salicylate; octylcinnamate, ethyl-4-isopropylcinnamate, methyl-2,5-diisopropylcinnamate, ethyl-2,4-diisopropylcinnamate, methyl-2,4- Diisopropyl cinnamate, propyl-p-methoxycinnamate, isopropyl-p-methoxycinnamate, isoamyl-p-methoxycinnamate, octyl-p-methoxy Cinnamate (2-ethylhexyl-p-methoxycinnamate), 2-ethoxyethyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β-phenylcinnamate, 2-ethylhexyl-α- Cinnamic acid-based UV absorbers such as cyano-β-phenylcinnamate and glyceryl mono-2-ethylhexanoyl-diparamethoxycinnamate; [3-bis (trimethylsiloxy) methylsilyl-1-methylpropyl] -3, 4,5-trimethoxycinnamate, [3-bis (trimethylsiloxy) methylsilyl-3-methylpropyl] -3,4,5-trimethoxycinnamate, [3-bis (trimethylsiloxy) methylsilylpropyl] -3 , 4,5-trimethoxycinnamate, [3-bis (to Methylsiloxy) methylsilylbutyl] -3,4,5-trimethoxycinnamate, [3-tris (trimethylsiloxy) silylbutyl] -3,4,5-trimethoxycinnamate, [3-tris (trimethylsiloxy) silylbutyl ] 3,4,5-trimethoxycinnamate, [3-tris (trimethylsiloxy) silyl-1-methylpropyl] -3,4-dimethoxycinnamate and other silicone-based cinnamic acid UV absorbers; 2,4 -Dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2'4,4'-tetrahydroxybenzophenone, 2-hydroxy-4- Methoxybenzophenone, 2-hydroxy-4-methoxy-4′-me Rubenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4′-phenyl-benzophenone-2-carboxylate, 2-hydroxy-4-n-octoxybenzophenone Benzophenone ultraviolet absorbers such as 4-hydroxy-3-carboxybenzophenone; 3- (4′-methylbenzylidene) -d, l-camphor, 3-benzylidene-d, l-camphor, urocanic acid ethyl ester, 2- Phenyl-5-methylbenzoxazole, 2,2′-hydroxy-5-methylphenylbenzotriazole, 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole, 2- (2′-hydroxy-) 5'-methylphenyl) benzotriazol , Dibenzalazine, dianisoylmethane, 4-methoxy-4′-t-butyldibenzoylmethane, 5- (3,3′dimethyl-2-norbornylidene) -3-pentan-2-one, etc .; Organic acids such as sarcosine acid (eg, lauroyl sarcosine sodium), glutathione, citric acid, malic acid, tartaric acid, lactic acid; vitamin A and its derivatives, vitamin B6 hydrochloride, vitamin B6 tripalmitate, vitamin B6 dioctanoate, vitamin B2 and its Derivatives, vitamin B such as vitamin B12, vitamin B15 and derivatives thereof, α-tocopherol, β-tocopherol, γ-tocopherol, vitamin E such as vitamin E acetate, vitamin D, vitamin H, pantothenic acid, panthetin, nicotine Acid amide, di Vitamins such as benzyltinate; γ-oryzanol, allantoin, glycyrrhizic acid (salt), glycyrrhetinic acid and derivatives thereof, tranexamic acid and derivatives thereof [tranexamic acid derivatives include tranexamic acid dimers (eg, trans- 4- (trans-aminomethylcyclohexanecarbonyl) aminomethylcyclohexanecarboxylic acid, etc.), esters of tranexamic acid and hydroquinone (for example, trans-4-aminomethylcyclohexanecarboxylic acid 4′-hydroxyphenyl ester, etc.), tranexamic acid And esters of gentisic acid (for example, 2- (trans-4-aminomethylcyclohexylcarbonyloxy) -5-hydroxybenzoic acid and its salts), amides of tranexamic acid (for example, (S-4-aminomethylcyclohexanecarboxylic acid methylamide and its salt, trans-4- (P-methoxyvinzoyl) aminomethylcyclohexanecarboxylic acid and its salt, trans-4-guanidinomethylcyclohexanecarboxylic acid and its salt, etc.) ), Saponins such as hinokitiol, bisabolol, eucalptone, thymol, inositol, psychosaponin, carrot saponin, hechimasaponin, muclodisaponin, pantothenyl ethyl ether, ethinyl estradiol, tranexamic acid, arbutin, cephalanthin, placenta extract, etc. Drugs: Barefoot, Clara, corn, orange, sage, yarrow, mallow, thyme, thyme, spruce, spruce, birch, horsetail, loofah, maronier, saxifrage Extracts of plants such as arnica, lily, mugwort, peonies, aloe, gardenia, sawara; pigments; porous and / or water-absorbing powders (eg starches derived from corn, potatoes, silicic acid, talc) , Powders of kaolin, aluminum magnesium silicate, calcium alginate, etc.); neutralizers; preservatives; fragrances; pigments and the like.

  The emulsified composition of the present invention can be produced by preparing an aqueous phase component and an oil phase component each containing the above-mentioned water-soluble copolymer, and stirring and mixing them in a conventional manner.

  The emulsified composition of the present invention has low irritation and less stickiness, so it can be used as cosmetics such as emulsions, creams, serums, sunscreens, liquid foundations, skin external preparations, quasi drugs and pharmaceuticals. Is preferred.

<3> Emulsifier The present invention also relates to an emulsifier comprising the above-mentioned water-soluble copolymer. The description regarding the water-soluble copolymer and the emulsion composition described above can be applied to the emulsifier of the present invention.

<4> Manufacturing method of emulsion composition This invention relates also to the method of manufacturing an emulsion composition using the emulsifier of this invention mentioned above. The method of the present invention is characterized in that no emulsifier other than the emulsifier of the present invention is used. The description regarding the water-soluble copolymer and the emulsion composition described above can be applied to the production method of the present invention.

The emulsified composition was manufactured by stirring and mixing the components shown in Tables 1 to 3 below.
In this example, as the water-soluble copolymer that is the emulsifier of the present invention, glyceryl diisostearate methacrylate, which is a hydrophobic monomer, and methoxy methacrylate PEG-23, which is a hydrophilic monomer, are approximately 3: 7. A (glyceryl diisostearate methacrylate / methoxymethacrylic acid methoxy PEG-23) copolymer having an average molecular weight of 61,000 copolymerized at a mass ratio was used.
Further, polyoxypropylene (polymerization degree 60) and polyoxyethylene (average polymerization degree 11) and PEG / PPG-60 / 11 glycerin (Adecanol M-3228) which is an ether of glycerin are used as the water-soluble copolymer. A product was produced (Comparative Examples 1, 3, 5).
Furthermore, an emulsion composition was produced using polyoxyethylene hydrogenated castor oil as a surfactant (Comparative Examples 2, 4, and 6).

FIG. 1 shows a three-component phase diagram in which the blending ratio of (glyceryl diisostearate methacrylate / methoxy methacrylate PEG-23) copolymer, squalane and water in Examples 1 to 23 is plotted.

FIG. 2 shows a three-component phase diagram in which the blending ratios of (glyceryl diisostearate methacrylate / methoxy methacrylic acid methoxy PEG-23) copolymer, tri (caprylic acid / capric acid) glyceryl and water in Examples 24-54 are plotted. .

FIG. 3 shows a three-component phase diagram in which the blending ratio of (glyceryl diisostearate methacrylate / methoxy methacrylic acid methoxy PEG-23) copolymer, dimethicone and water in Examples 55 to 81 is plotted.

The emulsified compositions of Examples 1 to 81 showed a stable emulsified form even after being stored at room temperature for 3 months. That is, (glyceryl diisostearate methacrylate / methoxymethoxy PEG-23 methacrylate) copolymer allows the nonpolar hydrocarbon oil squalane, the polar hydrocarbon oil tri (caprylic / capric) glyceryl, and silicone Even when any oil agent was used, a stable emulsion composition could be produced.
On the other hand, the compositions of Comparative Examples 1, 3, and 5 containing PEG / PPG-60 / 11 glycerin, which is a water-soluble copolymer, cannot be emulsified even if they are stirred and mixed. Completely separated.
This result shows that according to the water-soluble copolymer which is the emulsifier of the present invention, a stable emulsion composition can be produced using various oil agents.

In addition, as shown in Tables 1 to 3, the emulsified composition was prepared regardless of the content of the (glyceryl diisostearate methacrylate / methoxymethacrylic acid methoxy PEG-23) copolymer in the range of 1 to 30% by mass. Could be manufactured.
Moreover, as shown to Tables 1-3, even if it was any case whose content of an oil phase is 10-70 mass%, the emulsion composition was able to be manufactured.

Appropriate amounts of Examples 1 to 81 and Comparative Examples 2, 4, and 6 were applied to the skin. As a result, the emulsified compositions of Examples 1 to 81 had no irritation and less stickiness compared to the emulsified compositions of Comparative Examples 2, 4, and 6.
This result shows that the emulsified composition emulsified with the water-soluble copolymer which is the emulsifier of the present invention is superior in usability compared with a general emulsified composition emulsified with a surfactant.

  In particular, the emulsified composition of the example in which the content of the (glyceryl diisostearate methacrylate / methoxymethoxy methacrylate-23) copolymer is 15% by mass, more preferably 1% by mass, has a better feeling of use. It was.

The present invention can be applied to emulsified cosmetics.

Claims (8)

One or more structural units (a) derived from a hydrophobic monomer represented by the following general formula (I), (II) or (III), and one or two derived from a hydrophilic monomer An emulsified composition comprising a water-soluble copolymer having at least one kind of structural unit (b) as an essential structural unit, and substantially free of an emulsifier other than the water-soluble copolymer.
Formula (I)
(I)
(In the general formula (I), R1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R2 does not include a branched hydrocarbon group having no ring structure having 13 to 30 carbon atoms or a ring structure. (A hydrocarbon group having 6 to 12 carbon atoms having two or more branches is represented.)
Formula (II)
(II)
(In the general formula (II), R3 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R4 and R5 may be the same or different, have no ring structure, and have a branched structure having 6 to 22 carbon atoms. X represents a group in which an OH group is eliminated from a trivalent alcohol.)
Formula (III)
(III)
(In the general formula (III), R6 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R7, R8, and R9 may be the same or different, have no ring structure, have a branch, and have 6 carbon atoms. Represents an acyl group of ˜22, and Y represents a group in which an OH group is eliminated from a tetravalent alcohol. The hydrophilic monomer is a polymerizable carboxylic acid, a hydrophilic monomer represented by the following general formula (IV), a hydrophilic monomer represented by the following general formula (VI), and a hydrophilic monomer represented by the following general formula (VII) The emulsion composition according to claim 1, wherein the emulsion composition is one or more hydrophilic monomers selected from the group consisting of a hydrophilic monomer and a hydrophilic monomer represented by the following general formula (VIII).
Formula (IV)
(IV)
(In general formula (IV), R10 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R11 represents an alkylene group having 2 to 4 carbon atoms which may have a hydroxyl group, and R12 represents a hydrogen atom or carbon. An aromatic hydrocarbon group having 6 to 10 carbon atoms, an aliphatic hydrocarbon group having 1 to 14 carbon atoms, or an acyl group having 1 to 12 carbon atoms, and n represents an integer of 6 to 40.)
Formula (VI)
(VI)
(In the general formula (VI), R15 represents a hydrogen atom or a methyl group.)
Formula (VII)
(VII)
(In the general formula (VII), R16 represents a hydrogen atom or a methyl group, G-O- represents a group obtained by removing hydrogen from the hydroxyl group at the 1-position of the reducing sugar, m is 2 or 3, and l is 1-5. Represents an integer.)
Formula (VIII)
(VIII)
(In the general formula (VIII), R17 represents a hydrogen atom or a methyl group, R18 represents an amino acid residue, a polyamine residue or an amino alcohol residue. Q represents an oxygen atom or a group represented by NH.) The hydrophobic monomer is a hydrophobic monomer represented by the general formula (II), and the water-soluble monomer is a hydrophilic monomer represented by the general formula (IV). The emulsion composition described in 1. The emulsified composition according to any one of claims 1 to 3, wherein the content of the water-soluble copolymer is 0.5 to 30% by mass. The emulsified composition according to any one of claims 1 to 4, wherein the content of the oil phase component is 0.1 to 70% by mass. It is cosmetics, The emulsion composition as described in any one of Claims 1-5 characterized by the above-mentioned. One or more structural units (a) derived from a hydrophobic monomer represented by the following general formula (I), (II) or (III), and one or two derived from a hydrophilic monomer The emulsifier which consists of a water-soluble copolymer which has a structural unit (b) more than a seed | species as an essential structural unit.
Formula (I)
(I)
(In the general formula (I), R1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R2 does not include a branched hydrocarbon group having no ring structure having 13 to 30 carbon atoms or a ring structure. (A hydrocarbon group having 6 to 12 carbon atoms having two or more branches is represented.)
Formula (II)
(II)
(In the general formula (II), R3 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R4 and R5 may be the same or different, have no ring structure, and have a branched structure having 6 to 22 carbon atoms. X represents a group in which an OH group is eliminated from a trivalent alcohol.)
Formula (III)
(III)
(In the general formula (III), R6 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R7, R8, and R9 may be the same or different, have no ring structure, have a branch, and have 6 carbon atoms. Represents an acyl group of ˜22, and Y represents a group in which an OH group is eliminated from a tetravalent alcohol. One or more structural units (a) derived from a hydrophobic monomer represented by the following general formula (I), (II) or (III), and one or two derived from a hydrophilic monomer A method for producing an emulsified composition comprising a step of emulsifying using an emulsifier comprising a water-soluble copolymer having at least one type of structural unit (b) as an essential structural unit, wherein an emulsifier other than the emulsifier is substantially used. The manufacturing method characterized by not performing.

Formula (I)
(I)
(In the general formula (I), R1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R2 does not include a branched hydrocarbon group having no ring structure having 13 to 30 carbon atoms or a ring structure. (A hydrocarbon group having 6 to 12 carbon atoms having two or more branches is represented.)
Formula (II)
(II)
(In the general formula (II), R3 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R4 and R5 may be the same or different, have no ring structure, and have a branched structure having 6 to 22 carbon atoms. X represents a group in which an OH group is eliminated from a trivalent alcohol.)
Formula (III)
(III)
(In the general formula (III), R6 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R7, R8, and R9 may be the same or different, have no ring structure, have a branch, and have 6 carbon atoms. Represents an acyl group of ˜22, and Y represents a group in which an OH group is eliminated from a tetravalent alcohol.