JP6061594B2 - Oil-in-water emulsion composition - Google Patents

Description

  The present invention relates to an oil-in-water emulsion composition. More specifically, the present invention relates to an oil-in-water emulsion composition prepared by using polymersomes formed from alkylene oxide derivatives as an emulsifier.

Usually, in an oil-in-water emulsion composition used for cosmetics, a surfactant is frequently used because an emulsified state can be easily formed. However, when the surfactant is added in a large amount, the composition has a sticky feeling and there is a problem that the freshness expected of an oil-in-water emulsion composition is impaired. In addition, some low molecular weight synthetic surfactants are known to exhibit skin irritation, and from consumers who place importance on safety, the amount of surfactant is very small or not contained at all. A voice for cosmetics was heard.
Under such circumstances, various attempts have been made to produce an oil-in-water emulsion composition without using a surfactant.

In the early 1900s, it was reported that when powder particles or colloidal particles were mixed in two incompatible liquids, the particles were adsorbed on the interface and the emulsification system was stabilized. Emulsions prepared by this method are called Pickering emulsions and are widely used in various natural and industrial processes (Non-patent Document 1). The use of pickering emulsions has also been proposed in the field of cosmetics, but the powders and colloidal particles that can be used have various restrictions (size, non-aggregation, wettability, etc.) and can be applied to cosmetics. The thing was limited (refer patent documents 1-3).
Furthermore, the pickering emulsion emulsion has a problem of low stability against stirring and shaking. For example, in an oil-in-water pickering emulsion, the powder is adsorbed at the interface between the emulsified particles of the inner oil phase and the outer aqueous phase when left standing, so that the emulsified particles can be stably dispersed in the aqueous phase. However, if the emulsified particles collide with each other by stirring and shaking during product transportation, the concentration of the powder decreases on the colliding surface, which causes coalescence of the emulsified particles and emulsion breakage.

Therefore, by combining the amphipathic substance (Non-patent Document 2) or the specific amphiphilic lipid (ceramide), the cationic surfactant, and the polyhydric alcohol (Patent Document 4), Picker Attempts have been made to stabilize ring emulsions. In particular, Patent Document 4 uses the property that a cationic surfactant and an amphiphilic lipid form a liquid crystal (α-gel) structure in the presence of a polyhydric alcohol and thicken the oil-in-water emulsion. It is stabilized.
However, these emulsions are not sufficiently stable against stirring and shaking, and there are cases where stickiness is caused due to the high concentration of amphiphilic substances.
In addition, an oil-in-water pickering emulsion with improved stability and stickiness was prepared by adding a cationic surfactant having two alkyl chains. Particles (hydrophobized fine particle titanium dioxide, red iron oxide, yellow iron oxide, black iron oxide, and aluminum oxide) need to be blended at a high concentration, resulting in a squeaky feeling and a powdery appearance (patent Reference 5).

  In general, inorganic powder particles used in pickering emulsions (for example, Patent Document 1: Polyalkylsilsesquioxane particles, Patent Document 2: Metal oxide, Patent Document 3: Silica / Titanium dioxide / Zinc oxide, Patent Document) 4: The emulsifying ability of the inorganic powder) is inferior to the emulsifying ability of surfactants commonly used in cosmetics, so that it is necessary to add a large amount of the powder to improve the emulsion stability. As a result, a squeaky feeling and a powdery feeling are generated due to the high-concentration powder particles, and there is a tendency that the freshness is impaired. In order to solve such problems, pickering emulsions in which spherical organic particles are used as emulsifiers instead of inorganic powder particles have also been prepared. However, it is necessary to add 10% or more in combination with elastomeric organopolysiloxane. For this reason, the problem of the squeakiness and powderiness has not been solved so far (Patent Document 6).

  Thus, the emulsification stability of the pickering emulsion prepared without using a surfactant is low, and when the powder is increased or an amphiphile is co-blended to improve the stability, a squeaky or sticky feeling There was a problem that the freshness that is an excellent characteristic of the oil-in-water emulsion composition was impaired. In addition, even if an oil-soluble fragrance component is blended, it is difficult to stably maintain the inner phase, and thus it has been difficult to obtain an oil-in-water composition having a sufficient scent sustaining effect.

Japanese Patent No. 2656226 JP-T-2001-518111 JP 2007-332037 A JP 2006-36763 A JP 2008-291026 A Japanese Patent Laid-Open No. 11-158030 JP 2011-184367 A Japanese Patent No. 3855203 Japanese Patent No. 4825931

B. Binks et. al, Advances in Colloid and Interface Science, 100-102 (2003). Mukul M, Sharma et. al, Journal of Colloid and Interface Science, 157, 244-253 (1993). Science, 297, 967-973 (2002). Proceedings of the National Academy of Sciences of the United States of America (PNAS), 102, 2922-2927 (2005).

  The present invention has been made in view of the above circumstances, and provides an oil-in-water emulsion composition having high emulsification stability, no squeaky or sticky feeling, excellent freshness, and no worry of skin irritation. The purpose is to do.

As a result of intensive studies by the present inventors in order to achieve the above object, it has been found that polymersomes formed from specific alkylene oxide derivatives have excellent emulsifying ability.
Here, the polymersome means a closed endoplasmic reticulum having a bilayer structure formed from an amphiphilic block copolymer (diblock or multiblock copolymer each having one or more hydrophobic and hydrophilic blocks), that is, a vesicle. That is. Since the polymersome can hold a substance inside the vesicle like the liposome, it has recently attracted attention as a carrier in a drug delivery system (Non-patent Documents 3 and 4).

  So far, polymersomes have been produced from (polyethylene oxide-polyethylethylene) diblock copolymer, (polyethylene oxide-polybutadiene) block copolymer, block type alkylene oxide derivatives, etc., and the polymersome has high mechanical stability. It has been reported that a specific chemical substance can be stably held in the inside (Non-patent Documents 3 and 4, Patent Document 7). However, there has been no example of using these polymersomes as an emulsifier, and there has been no suggestion that the polymersomes have sufficient emulsifying ability to produce a stable emulsion composition.

  In addition, although a three-phase emulsification method using a closed vesicle formed spontaneously from an amphiphilic substance typified by a polyoxyethylene hydrogenated castor oil derivative or a quaternary ammonium compound as an emulsifier (Patent Document 8) is also known, There was a problem in terms of stability. Therefore, in Patent Document 9, a three-phase emulsified oil-in-water composition with improved stability is prepared by adjusting closed vesicles in the presence of a lower alcohol.

  By using polymersomes formed from a specific alkylene oxide derivative as an emulsifier, the present inventor has high emulsification stability, no squeaky or sticky feeling, excellent freshness, and low skin irritation. The present inventors have found that a mold emulsion composition can be obtained, and have completed the present invention.

That is, according to the present invention,
(A) polymersome particles having an alkylene oxide derivative represented by the following general formula (1) or (2) as a membrane component,
(B) an oil component as an internal phase,
(C) an aqueous component as the outer phase,
An oil-in-water emulsion composition comprising:
The polymersome particles of (a) are present at the interface between the inner phase formed from the component (b) and the outer phase formed from the component (c).
An oil-in-water emulsion composition is provided.
(In the formula, AO is an oxyalkylene group having 3 to 4 carbon atoms, EO is an oxyethylene group, and these addition forms are block-like. M is an average addition mole number of the oxyalkylene group, and l and n are The average added mole number of the oxyethylene group is 1 ≦ m ≦ 70, 1 ≦ l + n ≦ 70, and the ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 carbon atoms and the oxyethylene group is 20 to 80. (R ¹ and R ² are the same or different hydrocarbon groups having 1 to 4 carbon atoms.)
(In the formula, AO is an oxyalkylene group having 3 to 4 carbon atoms, EO is an oxyethylene group, Z is a residue obtained by removing a hydroxyl group from dimer diol, and these addition forms are block-like. A ¹ and a ² the average addition mole number of the oxyalkylene group, ^{b 1} and ^{b 2} are the average addition mole number of the oxyethylene group, a ^{1 ≦ a 1 + a 2 ≦} 150,1 ≦ b 1 + b 2 ≦ 150. carbon The ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 and the oxyethylene group is 10 to 99% by mass, and R ¹ and R ² may be the same or different and may be the same or different. It is a hydrogen group.)

In the membrane of the polymersome of (a), (d) the oily component retained in the polymersome membrane may contain the same and / or different type of oily component as the oily component as the internal phase (b). Is possible.
Further, in the inner pore surrounded by the polymersome membrane of (a), (e) as an aqueous component retained in the polymersome, (c) the same type and / or different type as the aqueous phase component constituting the outer phase It is also possible to include an aqueous component.

  Furthermore, a fragrance | flavor component can be mix | blended as said (b) oil-based component as an internal phase and / or (d) oil-based component hold | maintained in the polymersome membrane.

  The AO group of the alkylene oxide derivative represented by the above formulas (1) and (2) is preferably an oxybutylene group.

In addition, the present invention provides a method for producing an oil-in-water emulsion composition comprising the following steps (i) to (iii).
(I) a step of mixing an alkylene oxide derivative represented by the following general formula (1) or (2) and a water-soluble alcohol;
(Ii) dropping the mixed liquid into an aqueous solvent composed of an aqueous component while stirring to obtain an aqueous dispersion of polymersomes using the (a) alkylene oxide derivative as a membrane component;
(Iii) (a) The polymersome aqueous dispersion is mixed and dispersed in (c) an aqueous component as an outer phase, and (b) an oily component as an inner phase is added, followed by stirring and applying a shearing force. A step of obtaining an oil-in-water emulsion composition by emulsification.
(In the formula, AO is an oxyalkylene group having 3 to 4 carbon atoms, EO is an oxyethylene group, and these addition forms are block-like. M is an average addition mole number of the oxyalkylene group, and l and n are The average added mole number of the oxyethylene group is 1 ≦ m ≦ 70, 1 ≦ l + n ≦ 70, and the ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 carbon atoms and the oxyethylene group is 20 to 80. (R ¹ and R ² are the same or different hydrocarbon groups having 1 to 4 carbon atoms.)
(In the formula, AO is an oxyalkylene group having 3 to 4 carbon atoms, EO is an oxyethylene group, Z is a residue obtained by removing a hydroxyl group from dimer diol, and these addition forms are block-like. A ¹ and a ² the average addition mole number of the oxyalkylene group, ^{b 1} and ^{b 2} are the average addition mole number of the oxyethylene group, a ^{1 ≦ a 1 + a 2 ≦} 150,1 ≦ b 1 + b 2 ≦ 150. carbon The ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 and the oxyethylene group is 10 to 99% by mass, and R ¹ and R ² may be the same or different and may be the same or different. It is a hydrogen group.)

In the method for producing an oil-in-water emulsified composition, (d) an oil component that is the same and / or different from the oil component as the internal phase (b) is added as the oil component retained in the polymersome membrane. Then, the step (i) may be performed.
And a fragrance | flavor component can be mix | blended as said (b) oil-based component as an internal phase and / or (d) oil-based component hold | maintained in the polymersome membrane.
In the method for producing the oil-in-water emulsion composition, the amount of the alkylene oxide derivative in the step (i) is 0.1 to 20% by mass, and the amount of the water-soluble alcohol is 0.1 to 50% by mass. Is preferred.

  In the oil-in-water emulsion composition according to the present invention, the polymersome preferably has a particle size of 50 to 300 nm.

According to the present invention, an oil-in-water emulsified composition having high emulsification stability, no squeakiness or stickiness, excellent freshness, and low skin irritation can be easily obtained.
Furthermore, an oil-in-water emulsified composition having an excellent fragrance sustaining effect can be obtained by blending an oil-soluble fragrance component.

In the oil-in-water emulsion composition according to the present invention, (a) polymersome, (b) oily component as inner phase, (c) aqueous component as outer phase, (d) oily component retained in polymersome membrane (E) It is a schematic diagram which shows the presence state of the aqueous component hold | maintained inside the polymersome. The optical micrograph of the oil-in-water emulsion composition (Test Example 10-1) concerning this invention which mix | blended the fragrance | flavor component is shown. The time-dependent change of the fragrance intensity | strength of the oil-in-water emulsion composition (Test Example 10-1) concerning this invention which mix | blended the fragrance | flavor component is shown.

According to the present invention, using the excellent emulsifying ability of the polymersome, which is a vesicle formed from a specific alkylene oxide derivative, the emulsified particles are uniform and stable over time, and there is no squeaky or sticky feeling. Thus, an oil-in-water emulsified composition having excellent usability and low skin irritation can be easily prepared. In the present invention, the alkylene oxide derivative used for polymersome formation does not show skin irritation and has high safety but low emulsifying ability, and it is difficult to produce a stable emulsion. However, by adopting a structure called polymersome, it becomes possible to exist stably at the interface between the oil phase and the water phase, and the coalescence of the oil phase can be effectively suppressed even when stirring or shaking. It becomes like this. For this reason, oil-soluble perfume ingredients that have been difficult to maintain stably with conventional pickering emulsions can be blended stably and in large quantities, and an oil-in-water emulsion composition having an excellent scent sustaining effect can be produced.
The emulsifying ability of the polymersome according to the present invention is high, and a very stable oil-in-water emulsion composition can be produced when the internal oil phase ratio is in the range of 10 to 85% by mass.
Further, since the polymersome according to the present invention can exhibit an excellent emulsifying ability with a relatively small amount (0.125-2.25% by mass), the squeaky feeling and the powder which have been problematic in the conventional pickering emulsion It does not cause a feeling of stickiness and does not cause an unpleasant feeling of use such as a sticky feeling due to the high blending of the surfactant.

  Hereinafter, preferred embodiments of the present invention will be described.

[(A) Polymersome]
The polymersome according to the present invention is formed of a block-type alkylene oxide derivative having a specific structure and uses this as a membrane component. The block-type alkylene oxide derivative constituting the polymersome of the present invention is represented by the following formula (1) or (2).
In the formula (1), AO is an oxyalkylene group having 3 to 4 carbon atoms, and specific examples include an oxypropylene group, an oxybutylene group, an oxyisobutylene group, an oxytrimethylene group, and an oxytetramethylene group. It is done. An oxypropylene group and an oxybutylene group are preferable, and an oxybutylene group is particularly preferable. EO represents an oxyethylene group.
In the formula (1), m represents an average addition mole number of the oxyalkylene group, and 1 ≦ m ≦ 70, preferably 5 ≦ m ≦ 55. l and n represent the average number of added moles of an oxyethylene group having 3 to 4 carbon atoms, and 1 ≦ l + n ≦ 70, preferably 5 ≦ l + n ≦ 60. When the oxyalkylene group or oxyethylene group having 3 to 4 carbon atoms is 0, that is, when m or l + n is 0, a stable polymersome structure cannot be formed. There is a tendency for a sticky feeling to occur in a composition prepared using the polymersomes formed.

  In the said Formula (1), it is preferable that the ratio of the oxyethylene group with respect to the sum total of a C3-C4 oxyalkylene group and an oxyethylene group is 20-80 mass%, More preferably, it is 30-70 mass%. It is. If the oxyethylene group is less than 20% by mass, the block type alkylene oxide derivative represented by the formula (1) has low hydrophilicity, and if it exceeds 80% by mass, the block type alkylene oxide derivative has low lipophilicity. In some cases, the target polymersome structure may not be formed. Moreover, it is preferable that the molecular weight of the alkylene oxide derivative represented by Formula (1) is 1000-5000. If the molecular weight is less than 1000, a sufficient amount of polymersomes may not be obtained.

  In the formula (1), the oxyalkylene group having 3 to 4 carbon atoms and the oxyethylene group are added in a block form.

In the formula (1), R ¹ and R ² are hydrocarbon groups having 1 to 4 carbon atoms, which may be the same or different. Examples of the hydrocarbon group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an N-propyl group, an isopropyl group, an N-butyl group, a sec-butyl group, and a tert-butyl group, preferably a methyl group, An ethyl group. When R ¹ or R ² has 5 or more carbon atoms, freshness tends to be reduced only in the composition prepared using the polymersome formed from the alkylene oxide derivative.
Further, in the oil-in-water emulsion composition of the present invention, in the alkylene oxide derivative represented by the formula (1), either or both of R ¹ and R ² are within the range that does not impair the effects of the present invention. Derivatives of hydrogen atoms may be present. When the ratio of the derivative in which either one or both of R ¹ and R ² are hydrogen atoms is too large, the oil-in-water emulsion composition using the polymersome composed of the alkylene oxide derivative may be sticky. .

  The block-type alkylene oxide derivative according to the present invention can be produced by a known method. For example, it can be obtained by subjecting a compound having a hydroxyl group to addition polymerization of ethylene oxide and an alkylene oxide having 3 to 4 carbon atoms, and then subjecting an alkyl halide to an ether reaction in the presence of an alkali catalyst.

Examples of the block-type alkylene oxide derivative represented by the formula (1) that can be used in the present invention include POE (9) POP (2) dimethyl ether, POE (14) POP (7) dimethyl ether, and POE (10) POP. (10) dimethyl ether, POE (6) POP (14) dimethyl ether, POE (15) POP (5) dimethyl ether, POE (25) POP (25) dimethyl ether, POE (7) POP (12) dimethyl ether, POE (22) POP (40) Dimethyl ether, POE (35) POP (40) Dimethyl ether, POE (50) POP (40) Dimethyl ether, POE (55) POP (30) Dimethyl ether, POE (30) POP (34) Dimethyl ether, POE (25) POP (30) Jime Luether, POE (27) POP (14) dimethyl ether, POE (55) POP (28) dimethyl ether, POE (36) POP (41) dimethyl ether, POE (7) POP (12) dimethyl ether, POE (17) POP (4) Dimethyl ether, POE (9) POB (2) Dimethyl ether, POE (14) POB (7) Dimethyl ether, POE (15) POB (14) Dimethyl ether, POE (18) POB (17) Dimethyl ether, POE (23) POB (21) Dimethyl ether, POE (27) POB (25) dimethyl ether, POE (32) POB (29) dimethyl ether, POE (35) POB (32) dimethyl ether, POE (10) POB (15) dimethyl ether, POE (20) PO (28) Dimethyl ether, POE (17) POB (10) Dimethyl ether, POE (28) POB (17) Dimethyl ether, POE (45) POB (27) Dimethyl ether, POE (34) POB (14) Dimethyl ether, POE (55) POB (22) Dimethyl ether, POE (44) POB (12) Dimethyl ether, POE (10) POP (10) Diethyl ether, POE (10) POP (10) Dipropyl ether, POE (10) POP (10) Dibutyl ether, POE (35) POP (30) glycol, POE (35) POB (32) glycol and the like.
The POE, POP, and POB are abbreviations for polyoxyethylene, polyoxypropylene, and polyoxybutylene, respectively, and the numbers in parentheses after the POE, POP, and POB represent the number of added moles. Hereinafter, this may be abbreviated.

In the alkylene oxide derivative represented by the formula (2), Z is a residue obtained by removing a hydroxyl group from dimer diol, and EO is an oxyethylene group. AO is an oxyalkylene group having 3 to 4 carbon atoms, and examples thereof include an oxypropylene group, an oxybutylene group, an oxyisobutylene group, and an oxy t-butylene group. Preferably, it is an oxypropylene group, an oxybutylene group, and more preferably an oxybutylene group. These additional forms are block-shaped.

a ¹ and ^{a 2} are the average addition mole number of the oxyalkylene group, ^{b 1} and ^{b 2} represents the average molar number of addition of oxyethylene group, with ^{1 ≦ a 1 + a 2 ≦} 150,1 ≦ b 1 + b 2 ≦ 150 is there. Preferably, 2 ≦ a ¹ + a ² ≦ 70, 5 ≦ b ¹ + b ² ≦ 120, and more preferably 2 ≦ a ¹ + a ² ≦ 50, 10 ≦ b ¹ + b ² ≦ 100. When a ¹ + a ² is 0, a stable polymersome structure is not formed, and when a ¹ + a ² exceeds 150, an oil-in-water emulsion composition prepared using a polymersome formed from the alkylene oxide derivative Things tend to be inferior in moisturizing effect. If b ¹ + b ² is 0, polymersomes cannot be formed, and if it exceeds 150, the oil-in-water emulsion composition prepared using the polymersomes formed from the alkylene oxide derivative gives a sticky feeling. Tend.

  The ratio of EO to the total of AO and EO in the formula (2) is 10 to 99% by mass, preferably 20 to 70% by mass. If it is less than 10% by mass, the block-type alkylene oxide derivative has insufficient hydrophilicity, and if it exceeds 99% by mass, the block-type alkylene oxide derivative has insufficient lipophilicity, and the target polymersome is not formed or formed. However, the stability may be insufficient.

In the formula (2), the addition form of the oxyethylene group and the oxyalkylene group having 3 to 4 carbon atoms is a block shape from the viewpoint of polymersome formation. The addition order is preferably such that the dimer diol is bonded in the order of AO and EO.
Moreover, it is preferable that the molecular weight of the alkylene oxide derivative represented by Formula (2) is 1000-6000. If the molecular weight is too small, the formation rate of polymersomes may be reduced, so a sufficient amount of polymersomes may not be obtained. The usability of the emulsion composition may be reduced.

R ¹ and R ² are hydrocarbon groups having 1 to 4 carbon atoms. By etherifying the terminal hydroxyl group that causes stickiness, familiarity with the skin is improved and a good feeling of use is brought about. Examples of the hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, and a mixed group thereof. In the present invention, a methyl group and an ethyl group are preferable. When the number of carbon atoms is larger than 5, there is a tendency that the moisturizing effect and the rough skin improving effect of the oil-in-water emulsion composition prepared using the polymersome formed from the alkylene oxide derivative are inferior.
In addition, R ¹ and R ² may be the same or different, and R ¹ and R ² may form the polymersome by combining one or more block type alkylene oxide derivatives that are the same or different. .

In the alkylene oxide derivative represented by the formula (2), Z is a residue obtained by removing a hydroxyl group from dimer diol. Here, the dimer diol is a diol obtained by reducing dimer acid. When Z is another diol that is not a dimer diol, polymersomes may not be formed, or even if it can, stability may be insufficient.
The dimer acid used as a raw material of the dimer diol used in the present invention is a dimer obtained by polymerizing an unsaturated fatty acid or a lower alcohol ester thereof, for example. Specifically, it can be synthesized by a method of reacting an unsaturated fatty acid such as oleic acid, linoleic acid or linolenic acid or an ester of these lower alcohols by thermal polymerization such as Diels-Alder reaction, or other reaction methods. Any unreacted fatty acid may remain in the generated dimer acid as long as the effects of the present invention are not impaired.

The dimer acid is preferably a dimerized unsaturated fatty acid having 12 to 24 carbon atoms or a lower alcohol ester thereof. In this case, Z is a dimer diol residue having 24 to 48 carbon atoms. Such unsaturated fatty acids include myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, erucic acid, nervonic acid, linoleic acid, linolenic acid and their lower alcohols having 1 to 3 carbon atoms. Examples thereof include unsaturated fatty acids having 18 carbon atoms, and oleic acid, linoleic acid or lower alcohol esters thereof are particularly preferable. Alternatively, dimer acid obtained by hydrogenating the remaining unsaturated double bond after dimerization may be used.
As dimer diol, those derived from animal fats and oils and vegetable fats and oils are distributed, and both can be used in the present invention, but those derived from vegetable fats and oils are more preferable. Examples of such dimer diols include Sovermol 908 (manufactured by Cognis Japan), PRIPOL 2033 (manufactured by Unikema), PESPOL HP-1000 (manufactured by Toagosei Co., Ltd.), and the like.

Specific examples of the block-type alkylene oxide derivative represented by the formula (2) that can be used in the present invention include POB (25) POE (34) dimethyl dimer diol ether, POB (25) POE (35) dimethyl. Dimer diol ether, POB (4) POE (13) dimethyl dimer diol ether, POB (5) POE (15) dimethyl dimer diol ether, POB (6) POE (18) dimethyl dimer diol ether, POB (7) POE (20 ) Dimethyl dimer diol ether, POB (10) POE (24) dimethyl dimer diol ether, POB (10) POE (30) dimethyl dimer diol ether, POB (25) POE (52) dimethyl dimer diol ether, POB (18) OE (41) dimethyl dimer diol ether, POB (18) POE (41) diethyl dimer diol ether, POB (18) POE (41) dipropyl dimer diol ether, POB (18) POE (41) dibutyl dimer diol ether, POB (11) POE (30) dimethyl dimer diol ether, POB (15) POE (45) dimethyl dimer diol ether, POB (18) POE (50) dimethyl dimer diol ether, POB (21) POE (56) dimethyl dimer diol ether , POB (12) POE (50) dimethyl dimer diol ether, POB (18) POE (61) dimethyl dimer diol ether, POB (3) POE (40) dimethyl dimer diol ether POB (6) POE (82) dimethyl dimer diol ether, POB (40) POE (120) dimethyl dimer diol ether, POB (100) POE (40) dimethyl dimer diol ether, POE (35) POP (30) dimethyl dimer diol And ether, POE (52) POP (30) dimethyl dimer diol ether, and the like.
The added moles of POE, POP, and POB are expressed as total added moles in the molecule, that is, values of a ¹ + a ² and b ¹ + b ² .

  Such a block-type alkylene oxide derivative can be produced by a known method. For example, it can be obtained by subjecting a compound having a hydroxyl group to addition polymerization of ethylene oxide and an alkylene oxide having 3 to 4 carbon atoms, and then subjecting an alkyl halide to an ether reaction in the presence of an alkali catalyst.

  In the oil-in-water emulsion composition according to the present invention, the blending amount of the block-type alkylene oxide derivative is 0.1 to 20% by mass, more preferably 0. 0% by mass with respect to the finally produced oil-in-water emulsion composition. 1 to 10% by mass. When the blending amount of the block-type alkylene oxide derivative is less than 0.1% by mass, the effect of the blending may not be sufficiently exhibited, and when it exceeds 20% by mass, a sticky feeling may occur.

[(B) Oil component as internal phase]
In a conventional emulsion composition using a surfactant as an emulsifier, it is necessary to select a surfactant having physical properties suitable for the oil to be blended, and therefore, the types of surfactant and oil that can be blended are limited. Moreover, when changing an oil phase component, it was necessary to consider change of the kind of surfactant. On the other hand, the polymersome (a) used as an emulsifier in the present invention can be stably present at the interface between the oil phase and the water phase almost independently of the physical properties of the oil. Therefore, in this invention, it is possible to mix | blend a wider kind of oil component than before as (b) oily component as an internal phase, and it is also possible to change this oil phase component flexibly.

  In the oil-in-water emulsion composition according to the present invention, (b) the oily component as the internal phase includes hydrocarbon oils, higher fatty acids, higher alcohols, synthetic ester oils, silicone oils commonly used in cosmetics, quasi drugs, etc. In addition to liquid oils and fats, solid oils and fats, waxes, etc., it is also possible to mix a large amount and a stable amount of low molecular weight oils and high polarity oils that were difficult to mix with conventional oil-in-water emulsion compositions. . Here, the low molecular oil component is an oil component having a molecular weight of 500 or less, and the high polar oil component is an oil component having an IOB value of 0.15 or more. The IOB value refers to the ratio of the inorganic value (IV) to the organic value (OV) in the organic conceptual diagram, that is, “inorganic value (IV) / organic value (OV)”. An organic conceptual diagram is based on the assumption that all organic compounds are derived from methane (CH4) and all other compounds are all derived from methane, and the number of carbon atoms, substituents, transformations, rings, etc. are set to certain values. Then, the score is added to obtain the organic value and the inorganic value, and the organic value is plotted on the X-axis and the inorganic value is plotted on the Y-axis (“Organic Conceptual Diagram— Fundamentals and Applications ”(Yoshio Koda, Sankyo Publishing, 1984), etc.).

  Examples of the hydrocarbon oil include isododecane, isohexadecane, isoparaffin, liquid paraffin, ozokerite, squalane, pristane, paraffin, ceresin, squalene, petrolatum, microcrystalline wax, and the like.

  Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, toluic acid, isostearic acid, linoleic acid, linolenic acid, eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA) ) And the like.

  Examples of higher alcohols include linear alcohols (eg, lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol), branched chain alcohols (eg, monostearyl glycerin ether (batyl alcohol)) -2-decyltetradecinol, lanolin alcohol, cholesterol, phytosterol, hexyl decanol, isostearyl alcohol, octyldodecanol, etc.).

  Synthetic ester oils include, for example, octyl octoate, nonyl nonanoate, cetyl octanoate, isopropyl myristate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, dimethyloctane Hexyldecyl acid, cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearate, ethylene glycol di-2-ethylhexanoate, dipentaerythritol fatty acid ester, N-alkyl monoisostearate Glycol, neopentyl glycol dicaprate, tripropylene glycol pivalate, diisostearyl malate, di-2-heptyl undeca Glyceryl acid, glyceryl diisostearate, trimethylolpropane tri-2-ethylhexanoate, trimethylolpropane triisostearate, pentaerythritol tetra-2-ethylhexanoate, glycerin tri-2-ethylhexanoate, glyceryl trioctanoate, tri Glyceryl isopalmitate, trimethylolpropane triisostearate, cetyl 2-ethylhexanoate-2-ethylhexyl palmitate, glyceryl trimyristate, glyceride tri-2-heptylundecanoate, castor oil fatty acid methyl ester, oleyl oleate, Acetoglyceride, 2-heptylundecyl palmitate, diisobutyl adipate, N-lauroyl-L-glutamic acid-2-octyldodecyl ester, adip Di-2-heptylundecyl acid, ethyl laurate, di-2-ethylhexyl sebacate, 2-hexyldecyl myristate, 2-hexyldecyl palmitate, 2-hexyldecyl adipate, diisopropyl sebacate, 2-succinic acid 2- Examples include ethylhexyl and triethyl citrate.

  Examples of the silicone oil include linear polysiloxanes (for example, dimethylpolysiloxane, methylphenylpolysiloxane, diphenylpolysiloxane, etc.), cyclic polysiloxanes (for example, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexa Siloxane etc.) Silicone resin, silicone rubber, various modified polysiloxanes (amino-modified polysiloxane, polyether-modified polysiloxane, alkyl-modified polysiloxane, fluorine-modified polysiloxane, etc.), acrylic silicones forming a three-dimensional network structure Etc.

  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, sasanca oil, castor oil, linseed oil , Safflower oil, cottonseed oil, eno oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, cinnagiri oil, Japanese kiri oil, jojoba oil, germ oil-triglycerin and the like.

  Examples of the solid fat include cacao butter, palm oil, horse fat, hydrogenated palm oil, palm oil, beef tallow, sheep fat, hydrogenated beef tallow, palm kernel oil, pork fat, beef bone fat, owl kernel oil, hydrogenated oil, cattle Leg fats, moles, hydrogenated castor oil and the like.

  Examples of 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, hexyl laurate, and reduced lanolin. Jojoba 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.

In the oil-in-water emulsified composition according to the present invention, one or more of these oily components can be blended as the oily component of the internal phase (b). Moreover, you may mix | blend the fragrance | flavor component mentioned later as an oil-based component of (b) internal phase.
Moreover, in the oil-in-water emulsion composition of this invention, the oil-based component of (b) internal phase can be mix | blended in 10-85 mass%. Therefore, according to the present invention, an oil-in-water emulsion composition (cleansing cream, sunscreen, hair cream, etc.) having a high internal oil phase ratio from an oil-in-water emulsion composition (beauty liquid, emulsion, etc.) having a low internal oil phase ratio, etc. ) Products with a wide internal oil phase ratio.

[(C) Aqueous component as outer phase]
(C) As an aqueous component as an external phase, water (purified water, ion-exchanged water, tap water, etc.), water-soluble alcohols, thickeners, etc. that are usually used for cosmetics, quasi drugs, etc. Furthermore, a moisturizer, a chelating agent, a preservative, a pigment, and the like can be appropriately blended as desired.

Water-soluble alcohols include lower alcohols, polyhydric alcohols, polyhydric alcohol polymers, dihydric alcohol alkyl ethers, dihydric alcohol ether esters, glycerin monoalkyl ethers, sugar alcohols, monosaccharides, oligosaccharides, polysaccharides and their One or more selected from derivatives.

  Examples of the lower alcohol include ethanol, propanol, isopropanol, isobutyl alcohol, t-butyl alcohol and the like.

  Examples of the polyhydric alcohol include dihydric alcohols (for example, dipropylene glycol, 1,3-butylene glycol, ethylene glycol, trimethylene glycol, 1,2-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, Pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol, octylene glycol, etc.), trihydric alcohol (eg, glycerin, trimethylolpropane, etc.), tetrahydric alcohol (eg, diglycerin, 1,2, , 6-hexanetriol, etc.), pentahydric alcohol (eg, xylitol, triglycerin, etc.), hexavalent alcohol (eg, sorbitol, mannitol, etc.), polyhydric alcohol polymer (eg, diethylene glycol, Propylene glycol-triethylene glycol, polypropylene glycol, tetraethylene glycol, diglycerin-triglycerin, tetraglycerin, polyglycerin, etc.), dihydric alcohol alkyl ethers (eg, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono) Butyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono 2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl Ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether triethylene glycol monomethyl ether triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl Ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol butyl ether, etc.), dihydric alcohol ether ether Steal (eg, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, ethylene glycol diazinate, ethylene glycol disuccinate, diethylene glycol monoethyl ether acetate, diethylene glycol monoacetate Butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monophenyl ether acetate, etc., glycerin monoalkyl ether (eg, xyl alcohol, ceralkyl alcohol, bee Alcohol, etc.), sugar alcohols (eg, maltotriose, mannitol, sucrose, erythritol, glucose, fructose, amylolytic sugar, maltose, amylolytic sugar reducing alcohol, etc.), glycolide, tetrahydrofluol Furyl alcohol, POE-tetrahydrofurfuryl alcohol, POP-butyl ether, POP / POE-butyl ether tripolyoxypropylene glycerin ether, POP-glycerin ether, POP-glycerin ether phosphate, POP / POE-pentaneerythritol ether, polyglycerin, etc. Can be mentioned.

  Examples of monosaccharides include tricarbon sugars (for example, D-glyceryl aldehyde, dihydroxyacetone, etc.), tetracarbon sugars (for example, D-erythrose, D-erythrose, D-toreose, erythritol, etc.), Pentose sugars (for example, L-arabinose, D-xylosose, L-lyxose, D-arabinose, D-ribose, D-ribose, D-xylulose, L- Xylose, etc.), hexose (e.g., D-glucose, D-talose, D-busicoose, D-galactose, D-fructose, L-galactose, L- Mannose, D-tagatose, etc.), heptosaccharide (eg, aldoheptose, heproose, etc.), octose sugar (eg, octulose, etc.), deoxy sugar (eg, 2-deoxy-D Ribose, 6-deoxy-L-galactose, 6-deoxy-L Mannose, etc.), amino sugars (eg, D-glucosamine, D-galactosamine, sialic acid, aminouronic acid, muramic acid, etc.), uronic acids (eg, D-glucuronic acid, D-mannuronic acid, L-guluronic acid, D-galacturonic acid, L-iduronic acid and the like).

  Examples of the oligosaccharide include sucrose, gnocyanose, umbelliferose, lactose, planteose, isolicnose, α, α-trehalose, raffinose, lycnose, umbilicin, stachyose verbus course and the like.

  Examples of the polysaccharide include cellulose, quince seed, starch, galactan, dermatan sulfate, glycogen, gum arabic, heparan sulfate-tragacanth gum, keratan sulfate, chondroitin, xanthan gum, guar gum, dextran, kerato sulfate, locust bean gum, succinoglucan, etc. Is mentioned.

  Other polyols include polyoxyethylene methyl glucoside (Glucam E-10), polyoxypropylene methyl glucoside (Glucam P-10) and the like.

  Examples of thickeners include gum arabic, carrageenan, colored gum, tragacanth gum, carob gum, quince seed (malmello), casein, dextrin, gelatin, sodium pectate, sodium alginate, methylcellulose, ethylcellulose, CMC, hydroxyethylcellulose, hydroxypropyl Cellulose, PVA, PVM, PVP, sodium polyacrylate, carboxyvinyl polymer, locust bean gum, guar gum, tamarind gum, cellulose dialkyldimethylammonium sulfate, xanthan gum, magnesium aluminum silicate, bentonite, hectorite, silicate A1Mg (bee gum), Examples thereof include laponite and silicic anhydride.

  Examples of natural water-soluble polymers include plant-based polymers (for example, gum arabic, gum tragacanth, galactan, guar gum, carob gum, colored yam, carrageenan, pectin, agar, quince seed (malmello), alge colloid (guckweed extract), starch (Rice, corn, potato, wheat), glycyrrhizic acid), microbial polymers (eg, xanthan gum, dextran, succinoglucan, pullulan, etc.), animal polymers (eg, collagen, casein, albumin, gelatin, etc.), etc. Is mentioned.

  Examples of semi-synthetic water-soluble polymers include starch polymers (eg, carboxymethyl starch, methylhydroxypropyl starch, etc.), cellulose polymers (methylcellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate). Hydroxypropylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, crystalline cellulose, cellulose powder, etc.), alginic acid polymers (for example, sodium alginate, propylene glycol alginate, etc.) and the like.

  Examples of the synthetic water-soluble polymer include vinyl polymers (for example, polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer, etc.) and polyoxyethylene polymers (for example, polyethylene glycol 20,000, 40). , 000, 60,000, etc.), acrylic polymers (for example, sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.), polyethyleneimine, cationic polymers and the like.

  Examples of the humectant include chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, bile salt, DL-pyrrolidone carboxylate, short chain soluble collagen, Diglycerin (EO) PO adduct, Izayoi rose extract, Achillea millefolium extract, Merirot extract and the like can be mentioned.

  Examples of the sequestering agent include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, and tetrasodium edetate. Sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid, trisodium ethylenediaminehydroxyethyl triacetate and the like.

  Examples of amino acids include neutral amino acids (eg, threonine, cysteine, etc.), basic amino acids (eg, hydroxylysine, etc.), and the like. Examples of amino acid derivatives include acyl sarcosine sodium (lauroyl sarcosine sodium), acyl glutamate, acyl β-alanine sodium, glutathione and the like.

  Examples of the pH adjuster include buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate.

  In the oil-in-water emulsion composition of the present invention, (c) an aqueous component as an outer phase can be blended in the range of 15 to 90% by mass.

[(D) Oily component retained in the membrane of polymersome]
The polymersome according to the present invention is a vesicle formed from a film in which the alkylene oxide derivative has a lamellar structure (see FIG. 1). Therefore, in the step of forming the polymersome from the alkylene oxide derivative, it is possible to stably hold the oily component in the membrane of the polymersome by adding a specific oily component. As such (d) oily component retained in the polymersome membrane, one or more of the oily components listed as the oil phase component as (b) internal phase can be selected. Moreover, you may mix | blend the fragrance | flavor component mentioned later.
Moreover, it is not necessary to match (b) the oily component as the inner phase and (d) the oily component retained in the membrane of the polymersome. By selecting different oily components, they are derived from the different oily components. An oil-in-water emulsion composition having various effects and feelings of use can be produced.

[(E) Aqueous component retained inside polymersome]
In the polymersome according to the present invention, the aqueous component used as a solvent in the polymersome formation step is held in the inner pore surrounded by the film formed from the alkylene oxide derivative (see FIG. 1). Therefore, in the formation step, it is possible to stably hold the aqueous component inside the polymersome by adding a specific aqueous component to the solvent. As such (e) aqueous component retained inside the polymersome, one or more types can be selected from the aqueous components listed as (c) the aqueous phase component as the outer phase.
In addition, it is not necessary to match (c) the aqueous phase component as the outer phase and (e) the aqueous component retained inside the polymersome, and various types derived from the different aqueous components by selecting different aqueous components. An oil-in-water emulsion composition having a good effect and a feeling of use can be produced.

[Perfume ingredients]
Examples of the fragrance component used in the present invention include natural fragrances obtained from animals or plants, synthetic fragrances produced by chemical synthesis means, and blended fragrances that are mixtures thereof, and are not particularly limited. For example, acetylenol, anisaldehyde, anethole, amyl acetate, amyl salicylate, allyl amyl glycolate, allyl caproate, aldehyde C6-20, amblet ride, amblet lid, ambroxan, ionone, iso-Esuper, eugenol, uranium Thiol, galaxolide, carone, coumarin, geraniol, geranyl acetate, sandaroa, santalol, sandera, cyclamenaldehyde, cis-3-hexenyl acetate, cis-3-hexenol, citral, citronellyl acetate, citronellol, cineol, dihydromilse Nord, Jasmolactone, Cynamic alcohol, Cynamic aldehyde, Styraryl acetate, Cedryl acetate, Cedrol, Damascon, Damacenone, decalactone, terpinyl acetate, terpineol, tonalid, tonalide, tripral, nerol, bacdanol, vanillin, hydroxycitronellal, phenylethyl acetate, phenylethyl alcohol, hexyl salicylate, vetiberyl acetate, hedion, heliotropin, helional, Belt fix, benzyl acetate, benzyl salicylate, benzyl benzoate, pentalid, pentalide, bornyl acetate, myol, musk ketone, methyl anthranilate, methyl dihydrojasmonate, yarayara, lime oxide, linalyl acetate, linalool, limonene, laral, Lilyal, Rose oxide, Rosinol, Angelica oil, Anise oil, Al Aze oil, basil oil, bay oil, bergamot oil, columnus oil, camphor oil, cananga oil, cardamom oil, cassia oil, cedarwood oil, celery oil, chamomile oil, cinnamon oil, clove oil, coriander oil, cumin oil, dill oil, Elemi oil, estragon oil, eucalyptus oil, fennel oil, fenugreek oil, galvanum oil, geranium oil, ginger oil, grapefruit oil, gayakwood oil, hiba oil, hinoki oil, juniper berry oil, lavandin oil, lavender oil, lemon oil, lime Oil, mandarin oil, marjoram oil, mimosa oil, peppermint oil, spearmint oil , Mill oil, myrtle oil, nutmeg oil, oak moss oil, olive nam oil, opoponax oil, orange oil, parsley oil, patchouli oil, pepper oil, perilla oil, petit glen oil, neroli oil, orange flower oil, pimento oil, allspice oil, Pine oil, rose oil, rosemary oil, clari sage oil, sage oil, sandalwood oil, stylax oil, tage oil, thyme oil, tuberose oil, valerian oil, vetiver oil, violet leaf oil, winter green oil, wormwood oil, Ylang Ylang Oil, Yuzu Oil, Cassie Absolute, Genet Absolute, Hyacinth Absolute, Inmorte Examples include, but are not limited to, Ruabsolute, Jasmine Absolute, Jonquil Absolute, Narcis Absolute, Rose Absolute, Violet Leaf Absolute, Benzoin and the like.
In the present invention, any one or two or more of these fragrances may be selected from (b) an oily component as an internal phase and / or (d) a polymersome membrane. It can mix | blend as an oil-based component hold | maintained.
In general, the polarity of fragrances commonly used in cosmetics varies greatly depending on the compound, and it is necessary to select oils and emulsifiers according to the polarity. Therefore, oil-in-water emulsification containing multiple types of fragrances with different polarities. It is difficult to make a composition. However, since the oil-in-water emulsion composition according to the present invention has very high emulsification stability, even a mixture of perfume ingredients having different polarities can be stably and retained in a large amount. In addition, a highly volatile fragrance component (for example, a fragrance component having a vapor pressure of 0.01 mmHg or higher at 20 ° C.) is known to have a low scent sustaining effect, but the oil-in-water emulsion composition according to the present invention In a thing, even if it is such a highly volatile fragrance | flavor component, the sustained effect of a high fragrance can be acquired.
The compounding quantity of a fragrance | flavor component is 0.5-40 mass% with respect to the composition whole quantity, More preferably, it is 1-30 mass%, More preferably, it is 2-20 mass%. If it is less than 0.5% by mass, a sufficiently strong scent and sustainability cannot be obtained, and it is preferably 1% by mass or more in order to produce a sufficient scent as a fragrance composition. Moreover, the compounding quantity exceeding 40 mass% is not necessary practically and is not preferable because it is uneconomical.
In addition, although the fragrance | flavor component used by this invention is not limited, since the fragrance | flavor component whose vapor pressure in 20 degreeC is 0.01 mmHg or more cannot obtain the sustainability of a fragrance | flavor by a normal method, this invention It is advantageous to utilize

  The oil-in-water emulsified composition according to the present invention is not limited to the effects of the present invention, and other components usually used for external preparations for skin such as cosmetics and quasi-drugs, such as ultraviolet absorbers, powders, etc. Organic amines, polymer emulsions, vitamins, antioxidants and the like can be appropriately blended.

Examples of the water-soluble ultraviolet absorber include 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′-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, Benzophenone ultraviolet absorbers such as 2-ethylhexyl-4′-phenyl-benzophenone-2-carboxylate, 2-hydroxy-4-n-octoxybenzophenone, 4-hydroxy-3-carboxybenzophenone, phenylbenzimidazole-5 Sulfonic acid and Benzimidazole ultraviolet absorbers such as salts thereof, phenylene-bis-benzimidazole-tetrasulfonic acid and salts thereof, 3- (4′-methylbenzylidene) -d, l-camphor, 3-benzylidene-d, l-camphor , Urocanic acid, urocanic acid ethyl ester and the like.
Examples of the oil-soluble ultraviolet absorber include paraaminobenzoic acid (PABA), PABA monoglycerin ester, N, N-dipropoxy PABA ethyl ester, N, N-diethoxy PABA ethyl ester, N, N-dimethyl PABA ethyl ester, N Benzoic acid ultraviolet absorbers such as N-dimethyl PABA butyl ester; Anthranilic acid ultraviolet absorbers such as homomenthyl-N-acetylanthranilate; Amyl salicylate, menthyl salicylate, homomentyl salicylate, octyl salicylate, phenyl salicylate, benzyl Salicylic acid-based UV absorbers such as salicylate and p-isopropanolphenyl salicylate; octylcinnamate, ethyl-4-isopropylcinnamate, methyl-2,5-diisopropylcin Mate, ethyl-2,4-diisopropylcinnamate, methyl-2,5-diisopropylcinnamate, propyl-p-methoxycinnamate, isopropyl-p-methoxycinnamate, isoamyl-p-methoxycinnamate, octyl-p- Methoxycinnamate, 2-ethylhexyl-p-methoxycinnamate, 2-ethoxyethyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β-phenylcinnamate, 2-ethylhexyl-α -Cyano-β-phenylcinnamate, glyceryl mono-2-ethylhexanoyl-diparamethoxycinnamate, 3,4-, 5-trimethoxycinnamate 3-methyl-4- [methylbis (trimethylsiloxy) silyl] Cinnamic acid ultraviolet rays such as butyl Absorbent; 2-phenyl-5-methylbenzoxazole, 2,2′-hydroxy-5-methylphenylbenzotriazole, 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole, 2- ( 2'-hydroxy-5'-methylphenylbenzotriazole, dibenzalazine, dianisoylmethane, 4-methoxy-4'-tert-butyldibenzoylmethane, 5- (3,3-dimethyl-2-norbornylidene) -3-pentane -2-one, octocrylene and the like.

  Examples of the powder component include inorganic powders (for example, talc, kaolin, mica, sericite (sericite), muscovite, phlogopite, synthetic mica, saucite, biotite, permiculite, magnesium carbonate, calcium carbonate, silicic acid. Aluminum, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate (baked gypsum), calcium phosphate, fluorine apatite, hydroxyapatite, ceramic powder , Metal soap (eg, zinc myristate, calcium palmitate, aluminum stearate), boron nitride, etc.), organic powder (eg, polyamide resin powder (nylon powder), polyethylene powder, polymethyl methacrylate powder, Styrene powder, copolymer resin powder of styrene and acrylic acid, benzoguanamine resin powder, polytetrafluoroethylene powder, cellulose powder, etc.), inorganic white pigment (eg, titanium dioxide, zinc oxide, etc.), inorganic red pigment (eg, , Iron oxide (Bengara), iron titanate, etc.), inorganic brown pigments (eg, γ-iron oxide, etc.), inorganic yellow pigments (eg, yellow iron oxide, loess, etc.), inorganic black pigments (eg, black) Iron oxide, low-order titanium oxide, etc.), inorganic purple pigments (eg, mango violet, cobalt violet, etc.), inorganic green pigments (eg, chromium oxide, chromium hydroxide, cobalt titanate, etc.), inorganic blue pigments (eg, For example, ultramarine blue, bitumen, etc.), pearl pigments (eg titanium oxide coated mica, titanium oxide coated bismuth oxychloride, titanium oxide coated tar) , Colored titanium oxide coated mica, bismuth oxychloride, fish scale foil, etc.), metal powder pigments (eg, aluminum powder, copper powder, etc.), organic pigments such as zirconium, barium or aluminum lake (eg, red 201, Red 202, Red 204, Red 205, Red 220, Red 226, Red 228, Red 405, Orange 203, Orange 204, Yellow 205, Yellow 401, Blue 404, etc. Organic pigment, Red No. 3, Red No. 104, Red No. 106, Red No. 227, Red No. 230, Red No. 401, Red No. 505, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203 , Green No. 3 and Blue No. 1 etc.), natural pigments (eg chlorophyll, β-carotene etc.) and the like.

  Examples of the organic amine include monoethanolamine, diethanolamine, triethanolamine, morpholine, tetrakis (2-hydroxypropyl) ethylenediamine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, and 2-amino. -2-methyl-1-propanol and the like.

  Examples of the polymer emulsion include an acrylic resin emulsion, a polyethyl acrylate emulsion, an acrylic resin liquid, a polyacryl alkyl ester emulsion, a polyvinyl acetate resin emulsion, and a natural rubber latex.

  Examples of vitamins include vitamins A, B1, B2, B6, C, E and derivatives thereof, pantothenic acid and derivatives thereof, biotin and the like.

Examples of the antioxidant include tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid esters and the like.
Examples of the antioxidant assistant include phosphoric acid, citric acid, ascorbic acid, maleic acid, malonic acid, succinic acid, fumaric acid, kephalin, hexametaphosphate, phytic acid, and ethylenediaminetetraacetic acid.

  Other ingredients that can be blended include, for example, preservatives (methylparaben, ethylparaben, butylparaben, phenoxyethanol, etc.), anti-inflammatory agents (eg, glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.) Whitening agents (eg, placenta extract, yukinoshita extract, arbutin, etc.), various extracts (eg, buckwheat, auren, shikon, peonies, assembly, birch, sage, loquat, carrot, aloe, mallow, iris, grape, yokoinin , Loofah, lily, saffron, senkyu, ginger, hypericum, onionis, garlic, pepper, chimpi, toki, seaweed, etc.), activator (for example, royal jelly, photosensitizer, cholesterol derivative, etc.), blood circulation promoter (for example, Nonyl acid valenylamide, nicotinic acid benzyl ester, nicotinic acid β-butoxyethyl ester, capsaicin, gingerone, cantalis tincture, ictamol, tannic acid, α-borneol, nicotinic acid tocopherol, inositol hexanicotinate, cyclandrate, cinnarizine, trazoline Acetylcholine, verapamil, cephalanthin, γ-oryzanol, etc.), antiseborrheic agents (eg, sulfur, thianthol, etc.), anti-inflammatory agents (eg, tranexamic acid, thiotaurine, hypotaurine, etc.).

  In the present invention, by using only the polymersome according to the present invention as an emulsifier, an oil-in-water emulsion composition having uniform emulsified particles and high stability over time can be produced. However, as long as the effect of the present invention is not impaired, an emulsifier other than the polymersome of the present invention may be blended. Specifically, surfactants commonly used in cosmetics and the like are used at a concentration that does not impair the effects of the present invention, for the purpose of controlling the wash-out after use as a cleaning agent, the control of the feeling of use, the drug permeability, and the like. Can be blended.

The amphoteric surfactant has at least one cationic functional group and one anionic functional group, becomes cationic when the solution is acidic, and anionic when the solution is alkaline, and is close to a nonionic surfactant near the isoelectric point. It has properties.
Amphoteric surfactants are classified into carboxylic acid type, sulfuric acid ester type, sulfonic acid type and phosphoric acid ester type depending on the type of anionic group. The carboxylic acid type, sulfate type and sulfonic acid type are preferred in the present invention. Carboxylic acid types are further classified into amino acid types and betaine types. Particularly preferred is a betaine type.
Specifically, for example, an imidazoline-based amphoteric surfactant (for example, 2-undecyl-N, N, N- (hydroxyethylcarboxymethyl) -2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide) 1-carboxyethyloxy disodium salt, etc.); betaine surfactants (for example, 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryldimethylaminoacetic acid betaine, alkylbetaine, amide betaine, sulfone) Betaine) and the like.

  Examples of the cationic surfactant include quaternary ammonium salts such as cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, behenyldimethylhydroxyethylammonium chloride, stearyldimethylbenzylammonium chloride, and cetyltriethylammonium methylsulfate. Can be mentioned. Also, stearic acid diethylaminoethylamide, stearic acid dimethylaminoethylamide, palmitic acid diethylaminoethylamide, palmitic acid dimethylaminoethylamide, myristic acid diethylaminoethylamide, myristic acid dimethylaminoethylamide, behenic acid diethylaminoethylamide, behenic acid dimethyl Aminoethylamide, stearic acid diethylaminopropylamide, stearic acid dimethylaminopropylamide, palmitic acid diethylaminopropylamide, palmitic acid dimethylaminopropylamide, myristic acid diethylaminopropylamide, myristic acid dimethylaminopropylamide, behenic acid diethylaminopropylamide, behenine Amidoamino such as dimethylaminopropylamide Compounds.

Anionic surfactants include fatty acid soap, N-acyl glutamate, carboxylate type such as alkyl ether acetic acid, sulfonic acid type such as α-olefin sulfonate, alkane sulfonate, alkylbenzene sulfonic acid, higher alcohol sulfate It is classified into a sulfate ester salt type such as a salt and a phosphate ester salt type. Carboxylate type, sulfonic acid type and sulfate ester type are preferred, and sulfate ester type is particularly preferred.
Specifically, for example, fatty acid soap (for example, sodium laurate, sodium palmitate, etc.), higher alkyl sulfate ester salt (for example, sodium lauryl sulfate, potassium lauryl sulfate, etc.), alkyl ether sulfate ester salt (for example, POE- Lauryl sulfate triethanolamine, POE-sodium lauryl sulfate, etc.), N-acyl sarcosine acid (eg, sodium lauroyl sarcosine, etc.), higher fatty acid amide sulfonate (eg, sodium N-myristoyl-N-methyl taurate, coconut oil fatty acid) Methyl tauride sodium, lauryl methyl tauride sodium, etc.), phosphate ester salts (POE-oleyl ether sodium phosphate, POE-stearyl ether phosphate, etc.), sulfosuccinate (eg, di-2-ethyl Sodium xylsulfosuccinate, monolauroyl monoethanolamide polyoxyethylene sodium sulfosuccinate, sodium lauryl polypropylene glycol sulfosuccinate, etc.), alkylbenzene sulfonates (eg, linear dodecyl benzene sulfonate sodium, linear dodecyl benzene sulfonate triethanolamine, linear Dodecylbenzene sulfonic acid, etc.), higher fatty acid ester sulfate ester salts (for example, hydrogenated coconut oil fatty acid sodium glycerol sulfate, etc.), N-acyl glutamate (for example, monosodium N-lauroyl glutamate, disodium N-stearoyl glutamate, N- Myristoyl-L-monoglutamate monosodium, etc.), sulfated oil (eg funnel oil etc.), POE-alkyl ether cal Acid, POE-alkyl allyl ether carboxylate, α-olefin sulfonate, higher fatty acid ester sulfonate, secondary alcohol sulfate, higher fatty acid alkylolamide sulfate, lauroyl monoethanolamide sodium succinate, N-palmitoyl aspartate ditriethanolamine, sodium caseinate and the like.

  A nonionic surfactant is a surfactant that is not ionized in an aqueous solution and has no charge. As the hydrophobic group, a type using alkyl and a type using dimethyl silicone are known. Specifically, as the former, for example, glycerin fatty acid ester, ethylene oxide derivative of glycerin fatty acid ester, polyglycerin fatty acid ester, propylene glycol fatty acid ester, ethylene oxide derivative of propylene glycol fatty acid ester, polyethylene glycol fatty acid ester, polyethylene glycol alkyl ether, Examples include polyethylene glycol alkylphenyl ether, polyethylene glycol castor oil derivatives, polyethylene glycol hydrogenated castor oil derivatives, and the like. Examples of the latter include polyether-modified silicone and polyglycerin-modified silicone. A type using alkyl as a hydrophobic group is preferred.

  Specifically, as the lipophilic nonionic surfactant, for example, sorbitan fatty acid esters (for example, sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, Sorbitan sesquioleate, sorbitan trioleate, diglycerol sorbitan penta-2-ethylhexylate, diglycerol sorbitan tetra-2-ethylhexylate), glycerin polyglycerin fatty acids (eg mono cottonseed oil fatty acid glycerin, glyceryl monoerucate, sesquiolein) Acid glycerin, glyceryl monostearate, α, α'-oleic acid pyroglutamate glycerin, monostearate glycerin malate, etc.), propylene glycol fatty acid ester (For example, propylene glycol monostearate), hydrogenated castor oil derivative, glycerin alkyl ether and the like.

  Examples of the hydrophilic nonionic surfactant include POE-sorbitan fatty acid esters (for example, POE-sorbitan monooleate, POE-sorbitan monostearate, POE-sorbitan monooleate, POE-sorbitan tetraoleate). POE sorbite fatty acid esters (for example, POE-sorbite monolaurate, POE-sorbite monooleate, POE-sorbite pentaoleate, POE-sorbite monostearate, etc.), POE-glycerin fatty acid esters (for example, POE- Glycerol monostearate, POE-glycerol monoisostearate, POE-monooleate such as POE-glycerol triisostearate, etc.), POE-fatty acid esters (for example, POE-distearate, P E-monodiolate, ethylene glycol distearate, etc.), POE-alkyl ethers (for example, POE-lauryl ether, POE-oleyl ether, POE-stearyl ether, POE-behenyl ether, POE-2-octyldodecyl ether, POE-core) Stanol ether, etc.), pluronic types (for example, pluronic, etc.), POE • POP-alkyl ethers (for example, POE • POP-cetyl ether, POE • POP-2-decyltetradecyl ether, POE • POP-monobutyl ether, POE / POP-hydrogenated lanolin, POE / POP-glycerin ether, etc.), tetra-POE / tetra-POP-ethylenediamine condensates (eg, Tetronic, etc.), POE-castor oil hardened castor oil derivatives For example, POE-castor oil, POE-hardened castor oil, POE-hardened castor oil monoisostearate, POE-hardened castor oil triisostearate, POE-hardened castor oil monopyroglutamic acid monoisostearic acid diester, POE-hardened castor Oil maleic acid etc.), POE-beeswax lanolin derivatives (eg POE-sorbite beeswax etc.), alkanolamides (eg coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, fatty acid isopropanolamide etc.), POE-propylene glycol fatty acid Examples include esters, POE-alkylamines, POE-fatty acid amides, sucrose fatty acid esters, alkylethoxydimethylamine oxide-trioleyl phosphoric acid, and the like.

The oil-in-water emulsion composition according to the present invention can be applied to makeup cosmetics, skin care cosmetics, hair cosmetics, and the like, and can take various dosage forms and product forms according to the purpose. Examples of dosage forms include liquids, emulsions, creams, etc. Examples of product forms include lotions, cleansing lotions, emulsions, sunscreen emulsions, foundations, creams, sunscreen creams, cleansing creams, hair creams, etc. It is done.
These products can be manufactured according to conventional methods, but the present invention is not limited to these products.

[Method for producing polymersome]
In the polymersome according to the present invention, the alkylene oxide derivative represented by the above formulas (1) and (2) is sufficiently mixed with a water-soluble alcohol, and then the mixed solution is dropped into an aqueous solvent while stirring, It can be produced as a polymersome aqueous dispersion. The mixed state of the alkylene oxide derivative and the water-soluble alcohol only needs to be confirmed that the mixed solution is transparent and in a one-phase state, and can be achieved, for example, by mixing at room temperature to 90 ° C. for 1 to 30 minutes. it can. By this method, polymersome particles having an average particle diameter measured by a dynamic light scattering method of 50 to 300 nm are obtained.

  Examples of the water-soluble alcohol include the water-soluble alcohols exemplified as the components (c) and (e), that is, lower alcohol, polyhydric alcohol, polyhydric alcohol polymer, divalent alcohol alkyl ethers, dihydric alcohol alkyl. One kind or two or more kinds selected from ethers, dihydric alcohol ether esters, glycerin monoalkyl ethers, sugar alcohols, monosaccharides, oligosaccharides, polysaccharides and derivatives thereof can be used.

The aqueous solvent corresponds to (e) an aqueous component retained inside the polymersome. Therefore, as the aqueous solvent, components exemplified as (c) the aqueous component as the outer phase can be used. Further, as the aqueous solvent, (c) a part or all of the aqueous component as the outer phase can be used. In addition, when blending a water-soluble component having a high melting point among the components, it is desirable that the aqueous solution be preliminarily heated and uniformly dissolved in water, and then the aqueous solution is returned to about room temperature before being used for production of polymersomes.
Further, by dissolving or dispersing a water-soluble drug or the like in the aqueous solvent, it is possible to produce a polymersome encapsulating the drug or the like.

  Further, in the step of mixing the alkylene oxide derivative and the water-soluble alcohol, (d) an oily component retained in the polymersome membrane is added and mixed to retain the oily component in the polymersome membrane. be able to. And (d) The fragrance | flavor component widely used for cosmetics can be suitably mix | blended as an oil-based component hold | maintained in the film | membrane of a polymersome.

  In the step of mixing the alkylene oxide derivative and the water-soluble alcohol, it is preferable that the amount of the alkylene oxide derivative is 0.1 to 20% by mass and the amount of the water-soluble alcohol is 0.1 to 50% by mass. It is. When the amount of the water-soluble alcohol is less than 0.1% by mass or more than 50% by mass, polymersomes may not be formed.

[Polymersome evaluation method]
The polymersome aqueous dispersion obtained by the above-described method can be used to form polymersomes by measuring the polymersome particle size by the dynamic light scattering method described below and / or by conducting an encapsulation experiment with a water-soluble dye. Can be confirmed.
The dynamic light scattering measurement and the inclusion experiment are simple evaluation methods. In addition, polymersomes and vesicles can be formed by confirming the presence or absence of a Maltese cross image by observation with a polarizing microscope or by observation with a transmission electron microscope. It is also possible to confirm.

-Dynamic light scattering method Generally, the particle diameter of so-called colloidal particles such as emulsified particles or polymer emulsions can be measured by a method called dynamic light scattering method or photon correlation method. This measurement method measures the translational diffusion coefficient (average value) of sample particles by irradiating a sample dispersion prepared to a sufficiently dilute concentration with laser light and measuring the intensity of scattered light scattered from the sample particles. It is a method to do. The sample particles are always moving in Brownian motion in the dispersion. The moving speed of the particles by the Brownian motion, that is, the translational diffusion coefficient (average value) can be analyzed from the result of the temporal change in the scattered light intensity. The hydrodynamic size of the sample particles can be calculated from the translation diffusion coefficient (average value) thus obtained according to the Stokes-Einstein equation (Equation 1).
Where D is the diffusion coefficient, k is the Boltzmann constant, T is the absolute temperature (K), η is the viscosity of the solvent, and r is the radius of the particles. This measurement can be easily performed with a commercially available measuring apparatus. For example, measurement is possible with DLS7000 (manufactured by Otsuka Electronics Co., Ltd.), Zetasizer 4700 (manufactured by Malvern), Zeta Plus (manufactured by Brookhaven), and the like.
The above-mentioned commercially available measuring apparatus is equipped with data analysis software, and can automatically analyze measurement data. By using this analysis software, values of average particle diameter and degree of dispersion can be obtained. Here, the degree of dispersion is a value indicating a variation from the average value of the particle diameter, and is a value of the secondary cumulant in the cumulant analysis, that is, a value obtained by normalizing the dispersion value. In general, if the degree of dispersion is 0.01 or less, the particle size distribution of the sample can be regarded as almost monodisperse.

[Method for producing oil-in-water emulsion composition using polymersome as emulsifier]
(A) The aqueous dispersion of polymersomes obtained by the above production method was mixed and dispersed in (c) the aqueous component as the outer phase, and (b) the oily component and other components as the inner phase were added. An oil-in-water emulsion composition can be produced by emulsification by applying stirring and shearing force by the method. That is, the oil-in-water emulsion composition of the present invention has high commercial value because it can be produced by a very simple method using a general-purpose stirrer.

  EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. A compounding quantity is shown by the mass% unless there is particular notice.

[Production Example: Production of polymersome from alkylene oxide derivative]
A polymersome aqueous dispersion was prepared from the alkylene oxide derivatives described in Table 1 or Table 2 using the following production method. The presence or absence of polymersomes in the aqueous dispersion and the particle size of the polymersomes were analyzed according to the following method, and the ability of the alkylene oxide derivatives to form polymersomes was evaluated.

<Method for producing polymersome aqueous dispersion>
5 g of an alkylene oxide derivative, 30 g of ethanol, and 2 g of glycerin tri-2-ethylhexanoate were mixed thoroughly, and then the mixed solution was added dropwise to 63 g of purified water with stirring to obtain a polymersome aqueous dispersion. Therefore, the content of the polymersome contained in the polymersome aqueous dispersion is substantially 5% by mass.

<Method for evaluating polymersome-forming ability>
When all of the following three criteria were satisfied for the polymersome aqueous dispersion, it was determined that “Polymersome-forming ability: ◯”, and even if one criterion was not satisfied, “Polymersome-forming ability: ×”.
Criteria 1: Confirmation of particles having a particle diameter of 50 to 500 nm in dynamic light scattering measurement 2: Confirmation criteria of inclusion of the dye in bromophenol blue inclusion experiment 3: Turbidity and precipitation are observed visually In addition, the measurement / experiment technique used in the reference 1 and the reference 2 is as follows.

・ Measurement method of polymersome particle size by dynamic light scattering measurement The polymersome aqueous dispersion prepared by the above method is diluted so that the polymersome concentration is about 0.1%, and is filtered with a filter having a pore size of 0.45 μm. After filtration (removal of impurities), the scattering intensity at 25 ° C. and a scattering angle of 90 ° was measured using a dynamic light scattering measuring device (Zetasizer, Malvern). The average particle diameter (analyzed by the cumulant analysis method) and the degree of dispersion (a numerical value obtained by standardizing the value of the secondary cumulant obtained by the cumulant analysis) were calculated using analysis software installed in the measuring apparatus. The degree of dispersion is a commonly used parameter, and can be automatically analyzed by using a commercially available dynamic light scattering measurement device. The viscosity of the solvent required for particle size analysis was 25 ° C. pure water, that is, 0.89 mPas.
-Bromophenol blue inclusion experiment In the method for producing the polymersome aqueous dispersion, the pH of the purified water is adjusted to 6.0 or more, and the polymersome is dispersed using purified water in which bromophenol blue, which is a water-soluble dye, is dissolved. A liquid was prepared. When the polymersome is formed, bromophenol blue having absorption around 600 nm is included in the polymersome. Therefore, the obtained polymersome aqueous dispersion is dialyzed to remove the external solution, and the absorbance is measured. When significant absorption is confirmed at around 600 nm, polymersome is contained (the alkylene oxide derivative contains a polymer). It was judged that there was a capability of forming a liposome.

Table 1 shows the polymersome-forming ability of the alkylene oxide derivative represented by the following formula (1) and the analysis results of the polymersome particle size.
(In the formula, AO represents an oxyalkylene group having 3 to 4 carbon atoms, EO represents an oxyethylene group, m represents the oxyalkylene group, and l and n represent the average number of moles added of the oxyethylene group.)
Thus, for example, in the formula (1), when AO is an oxybutylene group, l + n = 15, m = 14, and R ¹ and R ² are methyl groups, (BO) ₁₄ (EO) ₁₅ , R ^1, expressed as ² = CH _3.

From Table 1, it was confirmed that polymersomes were formed from the block type alkylene oxide derivatives of Production Examples 1-7, 10 and 11 having an oxybutylene group and an oxyethylene group in the molecule. However, formation of polymersomes was not confirmed from the block type alkylene oxide derivative of Production Example 9 containing no oxyethylene group or Production Example 10 containing no oxybutylene group. Therefore, in order to form a polymersome, it is necessary to have both an oxyalkylene group having 3 to 4 carbon atoms (AO) and an oxyethylene group (EO) in the formula (1), and 1 ≦ m, 1 ≦ It can be seen that it must be l + n.
Further, Production Example 3 and Production Example 12 are alkylene oxide derivatives that differ only in the addition form of the oxybutylene group and the oxyethylene group. In Production Example 3 (block type), polymersomes were formed, whereas Production Example 12 ( In the random type, no polymersome was formed. Therefore, in order to form a polymersome, in the formula (1), the oxyalkylene group (AO) having 3 to 4 carbon atoms and the oxyethylene group (EO) need to be added in a block form.
Furthermore, a polymersome is formed from an alkylene oxide derivative in which R ¹ and R ² are a hydrocarbon group having 1 carbon atom (Production Example 1-7), 6 carbon atoms (Production Example 11), or hydrogen (Production Example 10). Rukoto has been shown.

Next, Table 2 shows the analysis results of the polymersome-forming ability and the polymersome particle size of the alkylene oxide derivative represented by the following formula (2).
(In the formula, AO represents an oxyalkylene group having 3 to 4 carbon atoms, EO represents an oxyethylene group, Z represents a residue obtained by removing a hydroxyl group from dimer diol, and a ¹ and a ² are average addition moles of the oxyalkylene group. The numbers b ¹ and b ² are the average number of moles added of the oxyethylene group.)

From Table 2, it was confirmed that polymersomes were formed from the block type alkylene oxide derivatives of Production Examples 13-16, 19 and 20 having an oxybutylene group and an oxyethylene group in the molecule. However, no polymersome was formed from the block-type alkylene oxide derivative of Production Example 17 containing no oxyethylene group or Production Example 18 containing no oxybutylene group. Therefore, in order to form a polymersome, it is necessary to have both an oxyalkylene group having 3 to 4 carbon atoms (AO) and an oxyethylene group (EO) in the formula (2), and 1 ≦ a ¹ + a ² It can be seen that 1 ≦ b ¹ + b ² must be satisfied.
Further, Production Example 13 and Production Example 21 are alkylene oxide derivatives that differ only in the addition form of the oxybutylene group and the oxyethylene group. In Production Example 13 (block type), polymersomes were formed, whereas Production Example 21 ( In the random type, no polymersome was formed. Therefore, in order to form a polymersome, in the formula (2), the oxyalkylene group (AO) having 3 to 4 carbon atoms and the oxyethylene group (EO) need to be added in a block form.
Furthermore, a polymersome is formed from an alkylene oxide derivative in which R ¹ and R ² are each a hydrocarbon group having 1 carbon atom (Production Example 13-16), 6 carbon atoms (Production Example 20), or hydrogen (Production Example 19). Rukoto has been shown.

  Next, an oil-in-water emulsion composition is prepared using these polymersomes as an emulsifier, and the emulsion stability (evaluation 1-3), feeling of use (evaluation 4-6), and skin irritation (evaluation 7) of the composition are prepared. ) Was evaluated. Furthermore, about the composition which mix | blended the fragrance | flavor component, the continuous effect (evaluation 8) of the fragrance originating in the said fragrance | flavor and / or the time-dependent change (evaluation 9) of the said fragrance intensity | strength were also evaluated. Below, the manufacturing method and evaluation method which were used by this-application test example are demonstrated.

<Method for producing oil-in-water emulsion composition>
(A) The polymersome aqueous dispersion prepared in the above production example was added to (c) the aqueous component as the outer phase and stirred and mixed, and then (b) the oil phase component as the inner phase was added and the homomixer was used. Shear mixing was performed until uniform, to obtain an oil-in-water emulsion composition.

<Evaluation method of oil-in-water emulsion composition>
Evaluation (1): State of emulsified particles The composition immediately after production was observed with an optical microscope, and the state of the emulsified particles was evaluated.
○: The emulsified particles were uniform, and coalescence and aggregation were not observed.
Δ: The emulsified particles were almost uniform, but slight coalescence or aggregation was observed.
X: The emulsified particles were not uniform, and significant coalescence or aggregation was observed.

Evaluation (2): Emulsification stability 1 (within 24 hours)
The emulsified state of the composition within 24 hours from the production was visually evaluated.
○: The sample was uniform, and no oil floating or aggregation of emulsified particles was observed.
Δ: The sample was almost uniform, but slight oil floating or aggregation of emulsified particles was observed.
X: The sample was not uniform, or significant oil phase separation or aggregation of emulsified particles was observed.

Evaluation (3): Emulsification stability 2 (after one month)
The emulsified state of the composition one month after production was visually evaluated.
(Double-circle): The emulsified state immediately after manufacture was maintained.
○: Some precipitation was observed, but the emulsified state immediately after the production was generally kept.
Δ: Precipitation and coalescence of emulsified particles were observed.
X: Phase separation was observed.

Evaluation (4): Freshness The actual use test of the composition was conducted using 10 professional panels, and the freshness was evaluated only during application.
A: More than 8 panelists felt freshness during application.
○: 6 or more panelists and less than 8 panelists felt freshness during application.
(Triangle | delta): The panel 3 to 6 persons felt freshness at the time of application | coating.
X: Less than 3 panelists felt freshness at the time of application.

Evaluation (5): Sensation of sensation An actual use test of the composition was conducted using 10 professional panels, and the squeaking sensation during application was evaluated.
A: Eight or more panel members recognized that they were not damaged during application.
○: 6 or more panelists and less than 8 panelists recognized that they were not damaged during coating.
(Triangle | delta): The panel 3 or more and less than 6 persons recognized that it did not come off during application | coating.
X: Less than 3 panelists recognized that it was not damaged during application.

Evaluation (6): Stickiness The actual use test of the composition was conducted using 10 professional panels, and the stickiness after application was evaluated.
A: More than 8 panelists recognized that there was no stickiness after application.
○: 6 or more and less than 8 panelists recognized that there was no stickiness after application.
Δ: 3 or more and less than 6 panelists recognized that there was no stickiness after application.
X: Less than 3 panelists recognized that there was no stickiness after application.

Evaluation (7): Skin irritation An occlusion patch test (24 hours) was performed by applying the composition to the inner side of the upper arm of 10 specialist panels, and the test results were digitized according to the following criteria. The average value of 10 persons was calculated and the skin irritation of the composition was evaluated.
-Numerical value of the occlusion patch test result 0 point: No abnormality is recognized.
1 point: Slight redness is observed.
2 points: Redness is observed.
3 points: Redness and papules are observed.
-Evaluation of skin irritation of composition A: The average value of 10 panelists is 0 or more and less than 0.15.
A: The average value of 10 panelists is 0.15 or more and less than 0.2.
Δ: The average value of 10 panelists is 0.2 or more and less than 0.3.
X: The average value of 10 panelists is 0.3 points or more.

Evaluation (8): Sustained effect of fragrance A fixed amount (10 μl) of the composition was applied to the inner side of the upper arm of one specialist panel, and the intensity of the fragrance after 1 hour was evaluated.
A: I felt that the fragrance was strong.
○: I felt that the scent was slightly strong.
(Triangle | delta): The fragrance felt that it was a normal level (it is neither strong nor weak).
X: I felt that the fragrance was weak.

Evaluation (9): Change in scent intensity over time A certain amount of the composition (10 μl) was applied to a filter paper spot or on the inner side of the upper arm of a special panel, and the change over time in the intensity of each scent Two people evaluated it. The intensity of the scent was evaluated in the following seven stages, and the average values of the two were graphed. For the control, a solution in which the same kind and amount of the fragrance component as the fragrance component contained in the predetermined amount of the composition was dissolved in ethanol was used.
Level 6: I felt the scent was very strong.
Level 5: I felt that the fragrance was strong.
Level 4: I felt that the scent was slightly strong.
Level 3: I felt the scent was normal (not strong or weak).
Level 2: I felt that the scent was slightly weak.
Level 1: I felt the fragrance was weak.
Level 0: The scent was hardly felt.

In addition, the following compounds were used for this-application test example.
* 1: KF-96A-6cs (manufactured by Shin-Etsu Chemical Co., Ltd.)
* 2: Adecanol GT-700 (manufactured by ADEKA)

[Test Example 1: Emulsified composition with polymersomes]
The oil-in-water emulsion compositions having the formulations described in Table 3 below were prepared and evaluated for the items in the table.

In the emulsified composition prepared by blending the polymersome of Production Example 1 or Production Example 15, the emulsified particles were uniform, no coalescence or aggregation was observed, no slight oil floating was observed, and even after one month. It was shown that the emulsified state was maintained and the emulsion stability was extremely excellent (Test Examples 1-1 and 1-2). Further, in microscopic observation (Evaluation 1), oil droplets having almost the same particle diameter were dispersed in the water phase, and it was confirmed that the composition was an oil-in-water emulsion composition. Furthermore, in the actual use test of the composition, it was excellent in use feeling such as freshness, squeaky feeling and no stickiness, and almost no skin irritation by the occlusion patch test was observed (Test Examples 1-1 and 1-2). .
On the other hand, in the composition of Test Example 1-3 prepared without blending polymersomes or other emulsifiers, the water phase and the oil phase were separated without becoming an emulsifying system, so the freshness was greatly impaired. It was.
Therefore, it has been shown that the polymersome according to the present invention can produce an oil-in-water emulsion composition by emulsifying (b) an oily component and (c) an aqueous component, that is, can function as an emulsifier. Furthermore, the oil-in-water emulsion composition produced using the polymersome according to the present invention has very high emulsification stability, no squeaky feeling or stickiness, and freshness, and further low skin irritation. It became clear.

[Test Example 2: Comparison with emulsion composition using surfactant]
Next, the emulsifying ability of the polymersome according to the present invention was compared with the emulsifying ability of conventional low molecular surfactants. An oil-in-water emulsion composition having the formulation described in Table 4 was prepared, and the items in the table were evaluated.

The oil-in-water emulsion composition (Test Examples 2-2 and 2-3) prepared using a surfactant widely used in cosmetics as an emulsifier had high stability of emulsion particles and excellent stability over time. However, it was inferior to freshness, and squeaky and sticky. On the other hand, in the oil-in-water emulsion composition prepared by using the polymersome of Production Example 2 as an emulsifier (Test Example 2-1), the composition prepared using the low molecular surfactant (Test Example 2- It was shown that the emulsion stability as excellent as 2, 2-3) was obtained, and that the feeling in use was also excellent.
Therefore, when the polymersome according to the present invention is used as an emulsifier, the oil-in-water type has less squeakiness and stickiness and is superior to freshness compared to the case where a low molecular surfactant generally used in cosmetics is used as an emulsifier. It became clear that an emulsified composition could be prepared.

[Test Example 3: Comparison with emulsion composition using powder particles]
Subsequently, the emulsifying ability of the polymersome according to the present invention was compared with the emulsifying ability of the powder particles in the pickering emulsion. An oil-in-water emulsion composition having the formulation described in Table 5 was prepared, and the items in the table were evaluated. The composition of Test Example 3-2 was produced according to the following method.
-Production method of Test Example 3-3 Silica-coated zinc oxide powder particles were added to (c) an aqueous component as an outer phase and mixed. To this, dimethyl distearyl ammonium chloride separately dispersed in ion-exchanged water was added and subjected to heating ultrasonic treatment. After uniformly dispersing the powder component, (b) an oil component as an internal phase was added and mixed with a mixer until uniform, to obtain an oil-in-water emulsion composition.

The oil-in-water emulsion composition (Test Example 3-1) produced using the polymersome of Production Example 5 as an emulsifier was excellent in emulsion stability, free of squeakiness and stickiness, and excellent in freshness. On the other hand, in the composition (Pickering emulsion) of Test Example 3-2 using high-concentration hydrophobized silica powder as an emulsifier, a squeaky feeling and a sticky feeling were felt. In addition, in the composition of Test Example 3-3 (Pickering emulsion of Patent Document 5) containing a high-concentration silica-coated zinc oxide powder and a cationic surfactant having two alkyl chains as an emulsifier, the stickiness is improved. However, this resulted in a strong squeaky feeling due to the high concentration of powder particles.
Therefore, when the polymersome according to the present invention is used as an emulsifier, an oil-in-water emulsified composition with less squeakiness and stickiness and more excellent freshness than that when powder particles are used as an emulsifier is produced. It became clear that we could do it.

[Test Example 4: Comparison with emulsion composition by three-phase emulsification method]
Next, a comparison was made with an oil-in-water emulsion composition prepared by a three-phase emulsification method. An oil-in-water emulsion composition having the formulation described in Table 6 was prepared, and the items in the table were evaluated. The closed endoplasmic reticulum used in Test Example 4-2 was prepared according to the following procedure according to the method described in Patent Document 9.
-Production method of closed endoplasmic reticulum of Test Example 4-2 After thoroughly mixing 5 g of polyoxyethylene (10) hydrogenated castor oil and 30 g of ethanol and stirring the mixture into 65 g of water, using a homomixer Then, shear mixing was performed for 1 minute to obtain an aqueous dispersion of closed vesicles made of polyoxyethylene (10) hydrogenated castor oil.

The composition emulsified using the polymersome of Production Example 13 (Test Example 4-1) had high emulsification stability and was excellent in use feeling such as freshness, squeaky feeling and no stickiness. On the other hand, the composition (Test Example 4-2) emulsified using closed vesicles made of polyoxyethylene (10 mol) hydrogenated castor oil has high emulsification stability, and a fresh feeling of use was obtained. A sticky feeling was recognized.
Therefore, it is clear that when the polymersome according to the present invention is used as an emulsifier, an oil-in-water emulsion composition with less stickiness can be obtained compared to the case where closed vesicles used in the three-phase emulsification method are used as an emulsifier. It became.

[Test Example 5: Emulsifying ability of non-polymersome-forming alkylene oxide derivative]
The polyoxyethylene (10 mol) hydrogenated castor oil used in Test Example 4-2 is a low molecular surfactant having a strong emulsifying ability without forming closed vesicles. Therefore, the emulsifying ability of the polymersome according to the present invention in a state where the polymersome was not formed was evaluated. The composition of Test Example 5-2 was produced according to the following method.
Production method of Test Example 5-2 Block type alkylene oxide derivative used in Production Example 4 (in the above formula (1), l + n = 27, m = 25, R ^1,2 = CH ₃ ), tri-2- An oil-in-water emulsion composition was prepared by mixing glycerin ethylhexanoate and ethanol with (b) the oil phase component, and gradually adding the mixture to the aqueous phase component (c), which was previously mixed uniformly, using a homomixer. .

Test Examples 5-1 and 5-2 are compositions prepared using the same alkylene oxide derivative as an emulsifier. However, in Test Example 5-1, in which the derivative was used after forming polymersomes, an oil-in-water emulsion composition excellent in emulsion stability and usability was obtained, but without forming polymersomes. In Test Example 5-2 used, the emulsified state was maintained within 24 hours after production, but the coalescence of the emulsified particles proceeded thereafter, and phase separation occurred after one month. Moreover, the freshness was also impaired in the composition of Test Example 5-2.
Therefore, it was shown that the alkylene oxide derivative according to the present invention can obtain a sufficient emulsifying ability by taking a polymersome form, and can produce an oil-in-water emulsion composition having high stability with time.

[Test Example 6: Examination of types of block-type alkylene oxide derivatives of formula (1)]
Next, the types of alkylene oxide derivatives represented by the formula (1) and the emulsifying ability of polymersomes formed from the derivatives were examined. An oil-in-water emulsion composition having the formulation described in Table 8 was prepared, and the items in the table were evaluated.

In the composition (Test Example 6-1) using the polymersome of Production Example 3 having both an oxybutylene group and an oxyethylene group and formed from a block-type alkylene oxide derivative in which R ¹ and R ² are methyl groups, The emulsification stability was high, and the feeling of use such as freshness, squeakiness and no stickiness was also excellent. On the other hand, only an oxyethylene group (Production Example 8), only an oxybutylene group (Production Example 9), or an alkylene oxide derivative (Production Example 12) that is randomly added even if it has an oxybutylene group and an oxyethylene group. In the aqueous dispersion prepared from (1), a polymersome structure was not formed, and thus a stable emulsion could not be prepared (Test Examples 6-2, 6-3, and 6-6). In addition, in the block-type alkylene oxide derivative (Production Example 10) in which R ¹ and R ² are hydrogen, a polymer oil is formed to produce a stable oil-in-water emulsion composition, but it is clear that a sticky feeling occurs. (Test Example 6-4). In Test Example 6-5 using a polymersome formed from a block-type alkylene oxide derivative (Production Example 11) in which R ¹ and R ² are hydrocarbon groups having 6 carbon atoms, an oil-in-water emulsion composition is obtained. Although produced, the stability over time was low, and a squeaky feeling was also felt, so that the feeling of use was inferior.

Therefore, in order to obtain an oil-in-water emulsion composition having high emulsification stability, excellent freshness, and no squeakiness or stickiness, in the formula (1), an oxyalkylene group having 3 to 4 carbon atoms and oxyethylene It is considered that a polymersome formed from an alkylene oxide derivative having both groups, the addition form of the group being a block, and R ¹ and R ² being a hydrocarbon group having 1 to 5 carbon atoms may be used. . As a result of further studies, in the formula (1), 1 ≦ m ≦ 70, 1 ≦ l + n ≦ 70, and the number of oxyethylene groups relative to the total of oxyalkylene groups having 3 to 4 carbon atoms and oxyethylene groups is The ratio was 20 to 80% by mass, and R ¹ and R ² were found to be suitably block-type alkylene oxide derivatives having 1 to 4 carbon atoms which may be the same or different.

[Test Example 7: Examination of types of block-type alkylene oxide derivatives of formula (2)]
Subsequently, the types of alkylene oxide derivatives represented by the formula (2) and the emulsifying ability of polymersomes formed from the derivatives were examined. An oil-in-water emulsion composition having the formulation described in Table 9 was prepared, and the items in the table were evaluated.

In the composition (Test Example 7-1) using the polymersome of Production Example 13 having both an oxybutylene group and an oxyethylene group and formed from a block-type alkylene oxide derivative in which R ¹ and R ² are methyl groups, The emulsification stability was high, and the feeling of use such as freshness, squeakiness and no stickiness was also excellent. On the other hand, only an oxybutylene group (Production Example 17), only an oxyethylene group (Production Example 18), or an alkylene oxide derivative (Production Example 21) which is randomly added even if it has an oxybutylene group and an oxyethylene group. In the aqueous dispersion prepared from (1), a polymersome structure was not formed, and thus a stable emulsion could not be prepared (Test Examples 7-2, 7-3, and 7-6). In addition, in the block-type alkylene oxide derivative (Production Example 19) in which R ¹ and R ² are hydrogen, polymersomes were formed to produce a stable oil-in-water emulsion composition, but a sticky feeling was felt ( Test Example 7-4). In Test Example 7-5 using polymersomes formed from a block-type alkylene oxide derivative (Production Example 20) in which R ¹ and R ² are hydrocarbon groups having 6 carbon atoms, the oil-in-water emulsion composition is Although it was produced, the stability over time was low, and a feeling of squeakiness and stickiness was felt, and the feeling of use was inferior.
Therefore, in order to obtain an oil-in-water emulsion composition having high emulsification stability, excellent freshness, and no squeakiness or stickiness, in the formula (2), an oxyalkylene group having 3 to 4 carbon atoms and oxyethylene It is considered that a polymersome formed from an alkylene oxide derivative having both groups, the addition form of the group being a block, and R ¹ and R ² being a hydrocarbon group having 1 to 5 carbon atoms may be used. . Then, was carried out further investigation results, in the formula (2), in ^{1 ≦ a 1 + a 2 ≦} 150,1 ≦ b 1 + b 2 ≦ 150, the oxyalkylene groups and oxyethylene groups having 3 to 4 carbon atoms The ratio of the oxyethylene group to the total is 10 to 99% by mass, and R ¹ and R ² may be the same or different, and it is clear that a block type alkylene oxide derivative of a hydrocarbon group having 1 to 4 carbon atoms is preferable. It became.

[Test Example 8: Investigation of oil phase component / water phase component ratio]
In the oil-in-water emulsion composition, (c) the ratio of the oil phase component as the inner phase to the water phase component as the outer phase, that is, the ratio of the inner oil phase (= (b) the oil phase component as the inner phase When (/ c) the mass ratio of the water phase component as the outer phase) is increased, the emulsion stability is decreased, and the coalescence and phase separation of the emulsified particles are likely to occur. Therefore, the oil-in-water emulsion composition using the polymersome of the present invention as an emulsifier was examined for the internal oil phase ratio and the emulsion stability. In addition, the 2 times concentrated liquid of polymersome aqueous dispersion used in Test Example 8-6 was prepared by the following method.
-Preparation method of the polymersome double concentrate of Test Example 8-6 The polymersome aqueous dispersion of Production Example 6 (= polymersome content is 5% by mass) is allowed to stand in a constant temperature bath at 37 ° C. for 2 days, and the solvent It was concentrated by volatilizing (ethanol and purified water). Usually, this operation reduces the mass of the polymersome aqueous dispersion to less than half. After returning the aqueous dispersion to room temperature, the concentration rate is calculated from the mass of the aqueous dispersion before and after standing, and the concentration rate is doubled (= polymersome content is 10% by mass). As described above, purified water was added to prepare a 2-fold concentrated solution.

As is apparent from Table 8, by using the polymersome of Production Example 6 as an emulsifier, an oil-in-water emulsion composition having a very high emulsification stability in a wide range of an internal oil phase ratio of 20 to 80% by mass is obtained. It was shown that it can be produced (Test Examples 8-1 to 8-5). However, when the internal oil phase ratio was 90% by mass, an oil-in-water emulsion composition with a uniform emulsion particle diameter could be produced, but the emulsion system could not be maintained (Test Example 8-6).
Therefore, it was clarified that by using the polymersome according to the present invention as an emulsifier, a very stable oil-in-water emulsion composition can be prepared in the range of the internal oil phase ratio of 10 to 85% by mass.

[Test Example 9: Polymersome blending amount]
Then, the compounding quantity of the polymersome in the oil-in-water type emulsion composition of this invention was examined.

In the composition containing 5-40% by mass of the polymersome aqueous dispersion of Production Example 7 (= 0.25-2% by mass in terms of the actual polymersome content), the emulsion stability is high, freshness, squeakiness, It was excellent in use feeling such as no stickiness, and no skin irritation was observed (Test Examples 9-2 to 9-5). On the other hand, a composition having a blending amount of the polymersome aqueous dispersion of 2% by mass (= 0.1% by mass in terms of the actual polymersome content) has no skin irritation and excellent usability. However, the emulsion stability was decreased (Test Example 9-6). In addition, a composition containing 67.5% by mass of the polymersome aqueous dispersion (= 3.375% by mass in terms of polymersome) has excellent emulsification stability, no skin irritation, and a feeling of use. Although it was generally good (fresh and not squeaky), a sticky sensation was caused due to the high concentration of the alkylene oxide derivative (Test Example 9-1).
Therefore, the polymersome aqueous dispersion according to the present invention is 2.5 to 65% by mass, more preferably 3 to 50% by mass, that is, 0.125 to 3.25% by mass in terms of the actual polymersome, and more preferably 0.15 to 2.5% by mass blended with an oil-in-water emulsion composition with high emulsification stability, excellent use feeling such as freshness, squeakiness and no stickiness, and low skin irritation. It became clear that we could do it.

[Test Example 10: Blending of perfume ingredients]
Next, (b) as the oily component as the internal phase, the perfume component, limonene ((R) -1-methyl-4- (1-methylethenyl) cyclohexene) and citral (3,7-dimethyl-2,6- The composition which mix | blended (octadienal) was produced, and the said item (1)-(8) was evaluated.

From the results of Table 12, (b) the oil-in-water emulsion composition prepared by blending limonene and citral as the oil component as the internal phase and using the polymersome of Production Example 3 as an emulsifier has high emulsion stability. There was no squeaky feeling, stickiness, skin irritation, excellent freshness, and excellent fragrance sustainability (Test Examples 10-1 to 10-4). In contrast, an oil-in-water emulsion composition using polyoxyethylene (10) hydrogenated castor oil, an emulsifier widely used in cosmetics, as an emulsifier has low emulsification stability, does not feel freshness, and maintains fragrance. The effect was also inferior (Test Example 10-5). Therefore, by using the polymersome according to the present invention as an emulsifier, the perfume component is stably retained, the fragrance sustaining effect is high, and there is no squeaky feeling, stickiness, skin irritation, and it is excellent in freshness. It became clear that an emulsified composition could be prepared.
FIG. 2 is an optical micrograph of the oil-in-water emulsion composition obtained in Test Example 10-1. In the oil-in-water emulsified composition according to the present invention, it can be seen that fine emulsified particles containing a perfume component are stably held without being united.

  About the compounding quantity of a fragrance | flavor component, it is 10 mass% (Test Example 10-1), 20 mass% (Test Example 10-2), 30 mass% (Test Example 10-) combining limonene and citral with respect to the whole composition. 3) In the oil-in-water emulsion composition containing 40% by mass (Test Example 10-4), it was confirmed that the emulsion stability and the feeling of use were excellent, and the fragrance sustaining effect was also excellent (Table 12). Therefore, in the oil-in-water emulsion composition according to the present invention, the fragrance component can be blended in an amount of 0.5 to 40% by mass, more preferably 1 to 30% by mass, and further preferably 2 to 20% by mass with respect to the entire composition. I understood. In addition, in a composition containing 20% by mass of limonene and citral using polyoxyethylene (10) hydrogenated castor oil as an emulsifier, remarkable coalescence and aggregation of the emulsified particles occur, and a stable emulsified base material can be obtained. (Test Example 10-6).

Furthermore, about the oil-in-water type emulsion composition obtained by Test Example 10-1, (9) The time-dependent change of fragrance intensity was evaluated (FIG. 3). First, when spotted on the filter paper (FIG. 3, left figure), the fragrance was significantly weakened within 1 hour in the ethanol solution of the fragrance component (control), whereas the composition of Test Example 10-1 Then, even after 2 hours, the scent was almost as strong as that immediately after the spot.
When applied to the arm (FIG. 3, right figure), the ethanol solution rapidly lost scent, and the scent was completely lost after 2 hours from application. Even in the composition of Test Example 10-1, the scent strength decreased greatly immediately after application, but this caused the emulsion particles to be destroyed by friction during application, and the fragrance component retained in the inner oil phase was released onto the skin. This is probably because However, the decrease in scent intensity was very gradual compared to the control, and a scent was felt even 3 hours after application.
Although omitted in the present application, the present inventor obtained (b) a result suggesting that a part of the fragrance component blended as the oily component as the inner phase is retained in the (d) polymersome membrane. Yes. Since the fragrance component retained in the polymersome membrane remains in the film even after the emulsified particles are broken and is considered to exert a fragrance sustaining effect over a long period of time, a part of the fragrance is also present in Test Example 10-1. May have been retained in the membrane of the polymersome.
From the above results, it was shown that the oil-in-water emulsion composition according to the present invention is excellent in the intensity and duration of the scent when a fragrance is blended.

Examples of various cosmetics formulated with the oil-in-water emulsion composition of the present invention will be given below, but the present invention is not limited thereto. The cosmetics obtained in the following examples all had high emulsification stability, were not squeaky or sticky, were excellent in freshness, and almost no skin irritation was observed. Furthermore, in the cosmetics (Examples 3, 4, 7, 10, and 12) in which the fragrance component was blended, a sustained effect with a high fragrance was recognized.
In addition, the composition of the mixing | blending fragrance | flavor mix | blended with the Example is as follows. These blended fragrances contain components with greatly different polarities, such as low-polar orange oil and high-polar rose base, and in conventional methods, they can be blended stably and in large quantities into oil-in-water emulsion compositions. It was difficult.

<Floral blended fragrance A>
(1) Orange oil 5
(2) Dihydromyrcenol 5
(3) Linalool 7
(4) Linalyl acetate 3
(5) Benzyl acetate 5
(6) Rose base 15
(7) Hexylcinnamaldehyde 5
(8) Methyl Yonon Gamma 5
(9) Garaxoride 10
(10) Edion 20
(11) Lilianal 10
(12) Other perfume 10
<Floral compound fragrance B>
(1) Orange oil 4
(2) Lemon oil 3
(3) Dihydromyrcenol 3
(4) Linalool 15
(5) Rose base 10
(6) Turpineol 5
(7) Methyl Yonon Gamma 5
(8) Beta Yonon 5
(9) Weltfix 10
(10) Edion 15
(11) Florosa (FLOROSA, QUEST) 20
(12) Other fragrances 5

[Example 1: Emulsion]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (21) POE (23) Dimethyl ether 0.95
Trimyristic acid glycerin 0.2
Ethanol 5.0
(Oil component)
Dimethylpolysiloxane ^{* 1} 3.0
Decamethylcyclopentasiloxane 4.0
Squalane 2.0
Sunflower oil 1.0
(Aqueous component)
Glycerin 6.0
1,3-butylene glycol 5.0
Polyoxyethylene (10) methyl glucoside 3.0
Potassium hydroxide 0.1
Sodium hexametaphosphate 0.05
Hydroxypropyl-β-cyclodextrin 0.1
Dipotassium glycyrrhizinate 0.05
Loquat leaf extract 0.1
Sodium L-glutamate 0.05
Fennel extract 0.1
Yeast extract 0.1
Lavender oil 0.1
Giant extract 0.1
Dimorpholinopyridazinone 0.1
Xanthan gum 0.1
Carboxyvinyl polymer 0.1
Bengala appropriate amount Yellow iron oxide appropriate amount Paraben appropriate amount Purified water Residue <Production method>
Polymersome components (POB (21) POE (23) dimethyl ether, ethanol, glyceryl trimyristate) were weighed and stirred to prepare a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was dropped to obtain a polymersome aqueous dispersion. An oil phase component separately mixed and dissolved was gradually added to the aqueous dispersion and shear mixed with a homomixer until uniform, to obtain an oil-in-water emulsion.

[Example 2: Moisturizing cream]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (18) POE (41) dimethyl dimer diol ether 1
Tri-2-ethylhexanoic acid glycerin 0.4
1,3-butylene glycol 5
(Oil component)
Liquid paraffin 10
Dimethylpolysiloxane ^{* 1} 5
Squalane 15
Tetra 2-ethylhexanoic acid pentaerythlit 10
(Aqueous component)
Glycerin 10
Erythritol 1
Polyethylene glycol (molecular weight 1500) 5
Potassium hydroxide 0.1
Sodium hexametaphosphate 0.05
Tocopherol acetate 0.05
P-Hydroxybenzoic acid ester hydroxypropyl methylcellulose 0.3
Polyvinyl alcohol 0.1
Carboxyvinyl polymer 0.2
Purified water residue <Production method>
Polymersome components (POB (18) POE (41) dimethyl dimer diol ether, 1,3-butylene glycol, glycerin tri-2-ethylhexanoate) were weighed and stirred to prepare a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was dropped to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and dissolved in the aqueous dispersion was gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water moisturizing cream.

[Example 3: Cleansing cream]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (20) POE (20) dimethyl ether 3
Tripropylene glycol pivalate 0.2
Dipropylene glycol 15
(Oil component)
α-olefin oligomer 20
Tripropylene glycol pivalate 0.8
Vaseline 5
Glyceryl tri-2-ethylhexanoate 20
Dimethylpolysiloxane ^{* 1} 2
Methylphenylpolysiloxane 15
Batyl alcohol 0.5
Polyoxyethylene (60) hydrogenated castor oil 1
Floral-type compounding fragrance A 5.0
(Aqueous component)
Polyoxyethylene (60) hydrogenated castor oil 1
Palm oil fatty acid sodium methyl taurine 1
L-serine 0.1
Oat extract 0.1
Sodium alginate 0.1
Purified water residue <Production method>
Polymersome components (POB (20) POE (20) dimethyl ether, dipropylene glycol, tripropylene glycol pivalate) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was added dropwise to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and dissolved in the aqueous dispersion was gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water cleansing cream.

[Example 4: Sunscreen emulsion]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (15) POE (44) dimethyl dimer diol ether 0.95
Octyl octoate 0.3
Ethanol 5
(Oil component)
Isododecane 8
Dimethylpolysiloxane ^{* 1} 5
Octyl methoxycinnamate 5
Octocrylene 2
Bisethylhexyloxyphenol methoxyphenyl triazine 3
Oxybenzone 1
Floral-type blended fragrance A 2
(Aqueous component)
1,3-butylene glycol 5
Triethanolamine 0.1
Xanthan gum 0.1
(Acrylic acid / alkyl acrylate (C10-30)) copolymer 0.1
Carboxyvinyl polymer 0.1
Tranexamic acid 2
Talc 3
Phenoxyethanol Appropriate amount Disodium edetate Appropriate amount Purified water Residue <Production method>
Polymersome components (POB (15) POE (44) dimethyl dimer diol ether, ethanol, octyl octoate) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was added dropwise to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and dissolved in the aqueous dispersion was gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water sunscreen emulsion.

[Example 5: Sunscreen emulsion]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (21) POE (23) Dimethyl ether 1
Tri-2-ethylhexanoic acid glycerin 0.2
Ethanol 5
(Oil component)
Decamethylcyclopentasiloxane 22
Isododecane 12.5
Tetra-2-ethylhexanoic acid pentaerythlit 8
Dimethylpolysiloxane ^{* 1} 1
Caprylyl Methicone 5
Isostearic acid 0.2
Octyl methoxycinnamate 7.5
Diethylaminohydroxybenzoyl hexyl benzoate 2
Octocrylene 3
Dimethicodiethylbenzalmalonate 3
2,4-bis-[{4- (2-ethylhexyloxy) -2-hydroxy} -phenyl] -6- (4-methoxyphenyl) -1,3,5-triazine 0.5
(Aqueous component)
Glycerin 3.5
Succinoglycan 0.15
Ethanol 5
Phenylbenzimidazolesulfonic acid 0.5
2-Amino-2-methyl-1,3-propanediol 0.2
Salt 0.3
Phenoxyethanol Appropriate amount Disodium edetate Appropriate amount Purified water Residue <Production method>
Polymersome components (POB (21) POE (23) dimethyl ether, ethanol, glycerin tri-2-ethylhexanoate) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was added dropwise to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and heated and dissolved in the aqueous dispersion was gradually added and shear mixed with a homomixer until uniform to obtain an oil-in-water sunscreen emulsion.

[Example 6: Cleansing lotion]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (21) POE (23) Dimethyl ether 1
Glyceryl tri-2-ethylhexanoate 0.4
1,3-butylene glycol 5
(Oil component)
Liquid paraffin 10
Vaseline 5
Cetanol 1
Stearic acid 2
Monolauric acid polyoxyethylene sorbitan (20E.O.) 0.2
(Aqueous component)
Diglycerin 0.5
Polyethylene glycol (molecular weight 1500) 3
Triethanolamine 1
Tocopherol acetate 0.1
Carboxyvinyl polymer 0.03
Paraben Appropriate amount Purified water Residue <Production method>
Polymersome components (POB (21) POE (23) dimethyl ether, 1,3-butylene glycol, glyceryl tri-2-ethylhexanoate) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was added dropwise to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and dissolved in the aqueous dispersion was gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water cleansing lotion.

[Example 7: Hair cream]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (15) POE (15) dimethyl ether 2
Tetra-2-ethylhexanoic acid pentaerythritol 0.5
1,3-butylene glycol 10
(Oil component)
Liquid paraffin 5
Vaseline 2
Dimethylpolysiloxane ^{* 1} 5
Cetanol 2
Stearyl alcohol 1
Polyoxypropylene (7) glyceryl ether 2
Lipophilic glyceryl monostearate 2
Floral-type compounding fragrance B 2
(Aqueous component)
Paraoxybenzoic acid ester Appropriate amount Perfume Appropriate amount Purified water Residue <Production method>
Polymersome components (POB (15) POE (15) dimethyl ether, 1,3-butylene glycol, tetra-2-ethylhexanoic acid pentaerythritol) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was added dropwise to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and dissolved in the aqueous dispersion was gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water hair cream.

[Example 8: Hair styling cream]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (20) POE (25) dimethyl ether 2
Octyl methoxycinnamate 0.4
Ethanol 10
(Oil component)
Volatile isoparaffin 5
Dimethylpolysiloxane ^{* 1} 2
Isobutene-terminated polyoxyethylene / dimethylpolysiloxane block copolymer (FZ-2250, manufactured by Toray Dow Corning Co., Ltd.) 2
Isostearic acid 1
(Aqueous component)
Glycerin 5
Sodium hydroxide 0.15
P-Hydroxybenzoate appropriate amount phenoxyethanol appropriate amount edetate trisodium appropriate amount xanthan gum 0.5
Carrageenan 0.3
Vinyl acetate / vinyl pyrrolidone copolymer 2
(PVA-6450, manufactured by Osaka Organic Chemical Industry Co., Ltd.)
Carboxyvinyl polymer 0.5
Purified water residue <Production method>
Polymersome components (POB (20) POE (25) dimethyl ether, ethanol, octyl methoxycinnamate) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was dropped to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and dissolved in the aqueous dispersion was gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water hair styling cream.

[Example 9: Hair oil cream]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (21) POE (23) Dimethyl ether 1
Camellia oil 0.3
Ethanol 10
(Oil component)
Hydrogenated polyisobutene 50
Camellia oil 9.7
Oxybenzone Appropriate amount Highly polymerized methylpolysiloxane 10
(BY25-320, Toray Dow Corning Co., Ltd.)
(Aqueous component)
Purified water residue <Production method>
Polymersome components (POB (21) POE (23) dimethyl ether, ethanol, camellia oil) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was dropped to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and dissolved in the aqueous dispersion was gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water hair oil cream.

[Example 10: Hair treatment]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (6) POE (18) dimethyl dimer diol ether 0.95
Cetyl 2-ethylhexanoate 0.4
Propylene glycol 6
(Oil component)
Dimethylpolysiloxane ^{* 1} 2.6
Cetanol 0.5
Behenyl alcohol 3
Floral perfume B 3
(Aqueous component)
Stearyltrimethylammonium chloride 0.7
Citric acid 0.05
Sodium lactate solution 0.01
Dipotassium glycyrrhizinate 0.1
Lily extract 0.1
Hydroxyethyl cellulose 0.1
Paraoxybenzoate appropriate amount Purified water Residue <Production method>
Polymersome components (POB (6) POE (18) dimethyl dimer diol ether, propylene glycol, cetyl 2-ethylhexanoate) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was dropped to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and dissolved in the aqueous dispersion was gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water hair treatment.

[Example 11: Emulsification foundation]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (29) POE (32) dimethyl ether 2
Octyl methoxycinnamate 0.5
Ethanol 5.0
(Oil component)
Alkyl-modified silicone resin-coated titanium oxide 9.0
Alkyl-modified silicone resin-coated ultrafine titanium oxide (particle size 40 nm) 5.0
Alkyl-modified silicone resin coated iron oxide (red) 0.5
Alkyl-modified silicone resin-coated iron oxide (yellow) 1.5
Alkyl-modified silicone resin coated iron oxide (black) 0.2
Polyoxyalkylene-modified organopolysiloxane 0.5
Decamethylpentacyclosiloxane 5.0
Octyl paramethoxycinnamate 5.0
Acrylic silicone 4.0
(Aqueous component)
Glycerin 6.0
Xanthan gum 0.1
Carboxymethylcellulose 0.3
Acryloyldimethyltaurine sodium / hydroxyethyl acrylate copolymer (content: 35-40 mass%) 1.5
Ion-exchanged water residue <Production method>
Polymersome components (POB (29) POE (32) dimethyl ether, ethanol, octyl methoxycinnamate) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was dropped to obtain a polymersome aqueous dispersion. An oil phase component and a powder component separately mixed, dissolved, and dispersed in the aqueous dispersion were gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water emulsion foundation.

[Example 12: Water-based fragrance]
<Prescription>
Ingredient Amount (% by mass)
(Polymersome component)
POB (21) POE (23) Dimethyl ether 0.95
Cetyl 2-ethylhexanoate 0.4
Ethanol 10
(Oil component)
Dimethylpolysiloxane ^{* 1} 10
Methylphenyl polysiloxane 1
Floral perfume B 20
(Aqueous component)
Glycerin 4
Paraoxybenzoate appropriate amount Purified water Residue <Production method>
Polymersome components (POB (21) POE (23) dimethyl ether, cetyl 2-ethylhexanoate, ethanol) were weighed and stirred to obtain a uniform transparent mixed solution. While stirring the aqueous phase in which the aqueous component was sufficiently dissolved, the mixed solution was dropped to obtain a polymersome aqueous dispersion. The oil phase component separately mixed and dissolved in the aqueous dispersion was gradually added, and shear mixed with a homomixer until uniform to obtain an oil-in-water fragrance.

Claims (10)

(A) polymersome particles having an alkylene oxide derivative represented by the following general formula (1) or (2) as a membrane component,
(B) an oil component as an internal phase,
(C) an aqueous component as the outer phase,
An oil-in-water emulsion composition comprising:
The polymersome particles of (a) are present at the interface between the inner phase formed from the component (b) and the outer phase formed from the component (c).
An oil-in-water emulsion composition characterized by that.
(In the formula, AO is an oxyalkylene group having 3 to 4 carbon atoms, EO is an oxyethylene group, and these addition forms are block-like. M is an average addition mole number of the oxyalkylene group, and l and n are The average added mole number of the oxyethylene group is 1 ≦ m ≦ 70, 1 ≦ l + n ≦ 70, and the ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 carbon atoms and the oxyethylene group is 20 to 80. (R ¹ and R ² are the same or different hydrocarbon groups having 1 to 4 carbon atoms.)
(In the formula, AO is an oxyalkylene group having 3 to 4 carbon atoms, EO is an oxyethylene group, Z is a residue obtained by removing a hydroxyl group from dimer diol, and these addition forms are block-like. A ¹ and a ² the average addition mole number of the oxyalkylene group, ^{b 1} and ^{b 2} are the average addition mole number of the oxyethylene group, a ^{1 ≦ a 1 + a 2 ≦} 150,1 ≦ b 1 + b 2 ≦ 150. carbon The ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 and the oxyethylene group is 10 to 99% by mass, and R ¹ and R ² may be the same or different and may be the same or different. It is a hydrogen group.) In the oil-in-water emulsion composition according to claim 1, in the polymersome membrane of (a),
(D) an oily component retained in the polymersome membrane;
And (b) an oil-in-water emulsified composition comprising the same and / or different oily component as the oily component as the internal phase. In the oil-in-water emulsion composition according to claim 1 or 2, the inner pore surrounded by the polymersome membrane of (a),
(E) an aqueous component retained within the polymersome,
And (c) an oil-in-water emulsion composition comprising an aqueous component that is the same and / or different from the aqueous phase component constituting the outer phase.   The oil-in-water emulsion composition according to claim 1, wherein (b) an oily component as an inner phase and / or (d) an oily component retained in a polymersome membrane includes a fragrance component. A featured oil-in-water emulsion composition.   The oil-in-water emulsion composition according to claim 1, wherein the AO group of the alkylene oxide derivative represented by the formulas (1) and (2) is an oxybutylene group. Composition. The manufacturing method of the oil-in-water type emulsion composition characterized by including the following process (i)-(iii).
(I) a step of mixing an alkylene oxide derivative represented by the following general formula (1) or (2) and a water-soluble alcohol to obtain a mixed solution;
(Ii) dropping the mixed liquid into an aqueous solvent composed of an aqueous component while stirring to obtain an aqueous dispersion of polymersomes using the (a) alkylene oxide derivative as a membrane component;
(Iii) (a) The polymersome aqueous dispersion is mixed and dispersed in (c) an aqueous component as an outer phase, and (b) an oily component as an inner phase is added, followed by stirring and applying a shearing force. A step of obtaining an oil-in-water emulsion composition by emulsification.
(In the formula, AO is an oxyalkylene group having 3 to 4 carbon atoms, EO is an oxyethylene group, and these addition forms are block-like. M is an average addition mole number of the oxyalkylene group, and l and n are The average added mole number of the oxyethylene group is 1 ≦ m ≦ 70, 1 ≦ l + n ≦ 70, and the ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 carbon atoms and the oxyethylene group is 20 to 80. (R ¹ and R ² are the same or different hydrocarbon groups having 1 to 4 carbon atoms.)
(In the formula, AO is an oxyalkylene group having 3 to 4 carbon atoms, EO is an oxyethylene group, Z is a residue obtained by removing a hydroxyl group from dimer diol, and these addition forms are block-like. A ¹ and a ² the average addition mole number of the oxyalkylene group, ^{b 1} and ^{b 2} are the average addition mole number of the oxyethylene group, a ^{1 ≦ a 1 + a 2 ≦} 150,1 ≦ b 1 + b 2 ≦ 150. carbon The ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 and the oxyethylene group is 10 to 99% by mass, and R ¹ and R ² may be the same or different and may be the same or different. It is a hydrogen group.)   7. The method for producing an oil-in-water emulsion composition according to claim 6, further comprising: (d) an oily component retained in the polymersome membrane, and (b) the same type and / or different type as the oily component as the internal phase. A process for producing an oil-in-water emulsion composition, wherein the step (i) is carried out by adding the oily component.   The method for producing an oil-in-water emulsion composition according to claim 6 or 7, wherein a fragrance component is used as the oil component (b) and / or (d) the oil component retained in the polymersome membrane. An oil-in-water emulsified composition comprising:   In the manufacturing method of the oil-in-water type emulsion composition of Claims 6-8, the compounding quantity of the said alkylene oxide derivative in the said process (i) is 0.1-20 mass%, and the compounding quantity of water-soluble alcohol is 0.00. The manufacturing method of the oil-in-water type emulsion composition which is 1-50 mass%.   6. The oil-in-water emulsion composition according to claim 1, wherein the polymersome has a particle size of 50 to 300 nm.