WO2015156317A1

WO2015156317A1 - Manufacturing method for composition containing poorly water-soluble aromatic compound

Info

Publication number: WO2015156317A1
Application number: PCT/JP2015/060976
Authority: WO
Inventors: 阿部　哲也; 晶宏宇田; 秀隆岩井; 小松　利照
Original assignee: 花王株式会社
Priority date: 2014-04-09
Filing date: 2015-04-08
Publication date: 2015-10-15
Also published as: CN106132389B; JP5901818B2; TW201620489A; CN106132389A; JP2015205873A; TWI668011B

Abstract

　Provided is a new method for manufacturing a composition containing a poorly water-soluble aromatic compound, wherein the dissolution of the poorly water-soluble aromatic compound (component (A) of the present invention) in water is excellent.　The method for manufacturing a composition containing a poorly water-soluble aromatic compound includes a step in which the following are heat-treated at a temperature of 100-180°C in the presence of an aqueous medium: (A) a poorly water-soluble aromatic compound; (B) a divalent alcohol; and (C) an alcohol that is at least trivalent.

Description

Method for producing hardly water-soluble aromatic compound-containing composition

The present invention relates to a method for producing a slightly water-soluble aromatic compound-containing composition and a cosmetic.

Aromatic compounds are widely used in products such as cosmetics, pharmaceuticals, foods and daily necessities. Aromatic compounds are solid at room temperature and are often insoluble in water, and their usage is generally dissolved in alcohol and used (for example, Patent Documents 1 and 2).
However, the feeling of use is liable to be impaired by the stimulation of alcohol to the skin. Moreover, the composition which can be applied will be restrict | limited.

Therefore, a technique for solubilizing a poorly water-soluble aromatic compound in water has been studied. For example, an isopropylmethylphenol glycoside in which a sugar such as glucose is bound to isopropylmethylphenol (Patent Document 3), or a surfactant. And a method of solubilizing isopropylmethylphenol using a wetting agent in combination (Patent Document 4) has been reported.
Also reported is a method for solubilizing sparingly water-soluble hair-grown ingredients by heat-treating sparingly water-soluble hair-grown ingredients and water-soluble aromatic compounds such as polyphenol glycosides at 100 to 180 ° C. in the presence of an aqueous medium. (Patent Document 5).
(Patent Literature)

(Patent Document 1) JP 2009-96777 (Patent Document 2) JP 2011-153122 (Patent Document 3) JP 2005-82506 (Patent Document 4) JP 2011-98919 (Patent Document 3) Reference 5) Japanese Unexamined Patent Publication No. 2013-124225

The present invention includes a step of heat-treating (A) a poorly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol at 100 to 180 ° C. in the presence of an aqueous medium. The manufacturing method of a water-soluble aromatic compound containing composition, the sparingly water-soluble aromatic compound containing composition obtained by this manufacturing method, and the cosmetics containing this sparingly water-soluble aromatic compound containing composition are provided.

Detailed Description of the Invention

However, a so-called glycoside obtained by adding a sugar to a poorly water-soluble aromatic compound itself such as isopropylmethylphenol glycoside has high solubility in water, but its production process is complicated, so that the cost is high. Therefore, it is economically disadvantageous to use isopropylmethylphenol glycoside instead of isopropylmethylphenol or to use polyphenol glycoside as a solubilizer.
On the other hand, in the method of solubilizing a poorly water-soluble aromatic compound using a surfactant, the physiological effect of the aromatic compound such as sufficient solubility and antibacterial effect may not be obtained.
Therefore, the present invention provides a hardly water-soluble aromatic compound-containing composition (hereinafter referred to as “component (A) -containing composition”) having excellent solubility in water of the hardly water-soluble aromatic compound (component (A) of the present invention). To provide a new method of manufacturing.
In addition, the present invention is intended to provide a cosmetic that stably contains a poorly water-soluble aromatic compound and sufficiently exhibits its effect.

The inventors of the present invention have made various studies on the solubilization technique of a poorly water-soluble aromatic compound. By performing the heat treatment as described above, the dissolution concentration of the hardly water-soluble aromatic compound is drastically increased as compared with the solubility in water of a normal poorly water-soluble aromatic compound, and the composition subjected to such treatment In the product, precipitation of the aromatic compound was suppressed even at room temperature, and it was found that the solubility of the component (A) in water was stably maintained.
Moreover, the effect of a poorly water-soluble aromatic compound is sufficiently exhibited by combining the component (A) -containing composition that has undergone such treatment with at least one selected from a deodorant component, a bactericidal component, and a touch-improving component. In addition, the present inventors have found that a cosmetic capable of sufficiently expressing the effects of the combined ingredients can be obtained.

According to this invention, the component (A) containing composition excellent in the solubility to the water of a component (A) can be manufactured cheaply. By using this component (A) -containing composition, the use of ethanol can be reduced or avoided, so that it is possible to provide an aqueous product with less skin irritation.
Moreover, the cosmetics of this invention can fully exhibit the effect of a slightly water-soluble aromatic compound by using the component (A) containing composition which is excellent in the solubility of the component (A) in water. When an aromatic antibacterial component is used as the hardly water-soluble aromatic compound, an excellent deodorizing effect and bactericidal effect are obtained, and there is no stickiness and a smooth feeling can be obtained.

In the method for producing the component (A) -containing composition of the present invention, 100 to 100 of (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol in the presence of an aqueous medium. Including a step of heat treatment at 180 ° C.
As the (A) poorly water-soluble aromatic compound used in the present invention, a poorly water-soluble one, for example, solubility in water at 25 ° C. is 0.5 g / L or less, further 0.3 g / L or less, and further 0 An aromatic compound having a molecular weight of 2 g / L or less is preferably applicable.
Further, (B) an aromatic compound having a solubility in dihydric alcohol at 25 ° C. of 5 g / L or more, more preferably 10 g / L or more, and further 20 g / L or more can be preferably applied. Here, the solubility represents the number of grams of solute dissolved in 1 L of the solution, and the unit is [g / L].
It does not specifically limit as an aromatic compound, The aromatic compound used as an antibacterial component, a whitening component, and a hair growth component is mentioned as an example. (A) The poorly water-soluble aromatic compound may be one type or a mixture of two or more types.

Examples of aromatic antibacterial components include phenolic antibacterial agents and preservatives.
Phenol antibacterial agents are chlorophenol antibacterial agents such as triclosan, chlorthymol, carbachlor, chlorophene, dichlorophen, hexachlorophene, chloroxylenol, chlorocresol; O-phenylphenol and isopropylmethylphenol are preferred, and triclosan and isopropyl are further preferred. Methylphenol is preferred, and isopropylmethylphenol is more preferred.
The preservative is preferably a paraoxybenzoic acid ester such as methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, benzylparaben.

Examples of the aromatic whitening component include chromone derivatives.
The chromone derivative has a chromone, ie, a linear or branched alkyl group having 1 to 15 carbon atoms at the 2-position of 4H-1-benzopyran-4-one, and a hydrogen atom, a hydroxy group or an alkoxy group at the 7-position. Compounds having a group are preferred.
Examples of such chromone derivatives include 2-butylchromone, 2-pentylchromone, 2-heptylchromone, 2-nonylchromone, 2-hexadecylchromone, 2- (1-ethylpentyl) chromone, 2-butyl-7 -Methoxychromone, 2-pentyl-7-methoxychromone, 2-heptyl-7-methoxychromone, 2-nonyl-7-methoxychromone, 2-pentadecyl-7-methoxychromone, 2- (1-ethylpentyl) -7 -Methoxychromone, 7-hydroxy-2-methylchromone, 7-hydroxy-2-butylchromone, 7-hydroxy-2-pentylchromone, 7-hydroxy-2-heptylchromone, 7-hydroxy-2-nonylchromone, 7- Hydroxy-2-pentadesilchromone, 7-hydroxy-2- (1- Chirupenchiru) chromone, and the like. Of these, 2- (1-ethylpentyl) -7-methoxychromone is preferable.
The chromone derivative can be produced by a known method, for example, the method described in JP-A-7-188208.

Examples of the aromatic hair-growth component include flavanol derivatives such as trans-3,4′-dimethyl-3-hydroxyflavanone; nicotinic acids such as benzyl nicotinate, tocopherol nicotinate and β-butoxyethyl nicotinate; α-tocopherol And vitamin E such as dl-α-tocopherol acetate, tocopherol nicotinate and natural vitamin E; minoxidil, bimatoprost, tafluprost, nonyl acid vanillamide, hypericum extract, capsicum tincture and the like.
Among them, trans-3,4'-dimethyl-3-hydroxyflavanone, benzyl nicotinate, tocopherol nicotinate, β-butoxyethyl nicotinate, α-tocopherol, dl-α-tocopherol acetate, tocopherol nicotinate, natural vitamin E Minoxidil, bimatoprost, tafluprost, nonylic acid vanillyl amide, hypericum herb extract and capsicum tincture are preferred, and trans-3,4′-dimethyl-3-hydroxyflavanone is more preferred. The flavanol derivative can be produced by a known method, for example, a method described in JP-A-2000-198779.

The (B) dihydric alcohol used in the present invention is a general term for alcohols in which two hydrogen atoms of a hydrocarbon are substituted with a hydroxyl group. For example, ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl Alkylene glycols such as 1,3-propanediol and 1,3-butanediol; and polyalkylene glycols such as diethylene glycol, dipropylene glycol, polyethylene glycol, and polypropylene glycol. Of these, ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, and dipropylene glycol are preferred from the viewpoint of solubilization of poorly water-soluble aromatic compounds, and propylene glycol, 1,3- Propanediol and 1,3-butanediol are preferred. The weight average molecular weight of polyethylene glycol is preferably 200 to 20,000.
(B) Dihydric alcohol can be used individually or in combination of 2 or more types.

The (C) trivalent or higher alcohol used in the present invention is a generic name for alcohols in which 3 or more hydrogen atoms of a hydrocarbon are substituted with a hydroxyl group. For example, glycerins such as glycerin, diglycerin and triglycerin; , 2,4-butanetriol, 1,2,5-pentanetriol, 2-methylpropanetriol, 2-methyl-1,2,4-butanetriol, trimethylolethane, trimethylolpropane and the like. Trivalent to pentavalent alcohols are preferred, and trivalent alcohols are more preferred. Among these, glycerins are preferable from the viewpoint of solubilization of the poorly water-soluble aromatic compound, and glycerin and diglycerin are more preferable from the viewpoint of being applicable to cosmetics.
(C) Trivalent or higher alcohols may be used alone or in combination of two or more.

The aqueous medium used in the present invention refers to water and an aqueous solution of an organic solvent. Examples of water include tap water, distilled water, ion exchange water, and purified water. The organic solvent is not particularly limited as long as it is uniformly mixed with water. As the organic solvent, monohydric alcohols having 4 or less carbon atoms are preferable, propanol and ethanol are more preferable, and ethanol is more preferable from the viewpoint of being applicable to cosmetics. In addition, the organic solvent as used in the field of this invention excludes (B) dihydric alcohol and (C) trihydric or more alcohol.
When an organic solvent is used, the solubility of the (A) poorly water-soluble aromatic compound in water increases, but it is desirable to reduce the amount used from the viewpoint of irritation to the skin. The concentration of the organic solvent in the aqueous solution is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, further preferably 0 to 10% by mass, further preferably 0 to 1% by mass, and substantially 0% by mass. That is, it is more preferable not to contain an organic solvent.

(A) The slightly water-soluble aromatic compound may be dispersed in a solution in which (B) dihydric alcohol and (C) trihydric or higher alcohol are dissolved in an aqueous medium, and may be subjected to heat treatment in a slurry state. (A) A slightly water-soluble aromatic compound once dissolved or dispersed in (B) a dihydric alcohol and (C) a trihydric or higher alcohol may be mixed with an aqueous medium and then subjected to a heat treatment.

When the heat treatment is performed, a heat treatment raw material containing an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol is prepared, and the heat treatment is performed.
The content of the (A) poorly water-soluble aromatic compound in the heat-treated raw material varies depending on the type, but is usually 0.1 g / L or more, more preferably 0.5 g / L or more, and further 0 from the viewpoint of productivity. 0.7 g / L or more, further 0.9 g / L or more, further 1 g / L or more, further 2 g / L or more, more preferably 7.5 g / L or more, and further preferably 30 g / L, and 150 g from the viewpoint of fluidity. / L or less, more preferably 100 g / L or less, further 75 g / L or less, further 60 g / L or less, further 55 g / L or less, and further 50 g / L or less. Further, 0.1 to 150 g / L is preferable, 0.1 to 100 g / L is more preferable, 0.5 to 75 g / L is more preferable, 0.7 to 60 g / L is still more preferable, and 0.9 to 55 g. / L is more preferred, 1 to 55 g / L is more preferred, 1 to 50 g / L is more preferred, 2 to 50 g / L is more preferred, 7.5 to 50 g / L is still more preferred, and 30 to 50 g / L is more preferred. Further preferred.

The content of the (B) dihydric alcohol in the heat treatment raw material varies depending on the type, but is usually 1 g / L or more, further 10 g / L or more, and further 20 g / L from the solubility point of the component (A). The above is preferable, more preferably 100 g / L or more, further preferably 300 g / L or more, and from the viewpoint of fluidity, 700 g / L or less, further 600 g / L or less, and further 500 g / L or less is preferable. Further, it is preferably 1 to 700 g / L, more preferably 10 to 600 g / L, further preferably 20 to 500 g / L, further preferably 100 to 500 g / L, and further preferably 300 to 500 g / L.

The content of the (C) trivalent or higher alcohol in the heat treatment raw material varies depending on the type, but from the viewpoint of the solubility of the component (A), it is 1 g / L or more, further 10 g / L or more, and further 50 g / L. More preferably, it is 100 g / L or more, and from the viewpoint of storage stability and fluidity, it is preferably 500 g / L or less, more preferably 300 g / L or less, further 250 g / L or less, and even more preferably 200 g / L or less. Further, it is preferably 1 to 500 g / L, more preferably 1 to 300 g / L, further preferably 10 to 250 g / L, further preferably 50 to 250 g / L, and further preferably 100 to 200 g / L.

The mass ratio [(A) / (B)] of the component (A) to the component (B) in the heat-treated raw material is the solubility point of the component (A) in the component (A) -containing composition obtained after cooling. 0.001 or more, further 0.002 or more, further 0.02 or more, further 0.025 or more, and further 0.06 or more, preferably 1 or less, further 0.5 or less, further 0.2 or less, Further, it is preferably 0.15 or less, more preferably 0.13 or less, further 0.12 or less, and further preferably 0.11 or less. Further, it is preferably 0.001 to 1, more preferably 0.001 to 0.5, still more preferably 0.001 to 0.2, still more preferably 0.002 to 0.15, and 0.002 to 0.13. Is more preferable, 0.002 to 0.12 is more preferable, 0.002 to 0.11 is further preferable, 0.02 to 0.11 is further preferable, 0.025 to 0.11 is further preferable, and 0.02. More preferably, it is from 06 to 0.11.

When the component (A) -containing composition obtained by the production method of the present invention is used in a cosmetic described later, the mass ratio of the component (A) to the component (B) in the heat-treated raw material [(A) / (B) ] Is 0.02 or more, more preferably 0.025 or more, and further preferably 0.06 or more, from the viewpoint of the solubility of the component (A) in the component (A) -containing composition obtained after cooling. It is preferably 1 or less, more preferably 0.5 or less, and further preferably 0.15 or less. Moreover, 0.02 to 1 is preferable, 0.025 to 0.5 is more preferable, and 0.06 to 0.15 is still more preferable.

The mass ratio [(A) / (C)] of the component (A) to the component (C) in the heat-treated raw material is the solubility point of the component (A) in the component (A) -containing composition obtained after cooling. 0.001 or more, further 0.005 or more, further 0.01 or more, further 0.12 or more, further 0.15 or more, further 0.17 or more, preferably 1.5 or less, further 1 or less, Further, it is preferably 0.7 or less, more preferably 0.55 or less. Further, it is preferably 0.001 to 1.5, more preferably 0.001 to 1, further preferably 0.005 to 0.7, still more preferably 0.01 to 0.55, and 0.12 to 0.55. Is more preferred, 0.15 to 0.55 is more preferred, and 0.17 to 0.55 is even more preferred.

When the component (A) -containing composition obtained by the production method of the present invention is used in a cosmetic described later, the mass ratio of the component (A) to the component (C) in the heat-treated raw material [(A) / (C) ] Is preferably 0.12 or more, more preferably 0.15 or more, and further preferably 0.17 or more from the viewpoint of the solubility of the component (A) in the component (A) -containing composition obtained after cooling. It is preferably 5 or less, more preferably 1 or less, and further preferably 0.6 or less. Further, it is preferably 0.12 to 1.5, more preferably 0.15 to 1, and further preferably 0.17 to 0.6.

In the heat treatment raw material, the mass ratio [(B) / (C)] of the component (B) to the component (C) is the solubility point of the component (A) in the component (A) -containing composition obtained after cooling. Therefore, 1.5 or more, further 2 or more, further 2.5 or more is preferable, 10 or less, further 8 or less is preferable, and 6 or less is more preferable. Further, it is preferably 1.5 to 10, more preferably 2 to 8, and further preferably 2.5 to 6. *

In addition, the mass ratio [(A) / {(B) + (C)}] of the component (A) to the total amount of the component (B) and the component (C) in the heat treatment raw material is the component ( A) From the point of solubility of the component (A) in the containing composition and from the point of storage stability of the component (A) -containing composition, 0.001 or more, further 0.002 or more, further 0.015 or more, further It is preferably 0.019 or more, more preferably 0.05 or more, and is preferably 0.5 or less, further 0.2 or less, further 0.15 or less, further 0.12 or less, and further 0.10 or less. Further, 0.001 to 0.5 is preferable, 0.001 to 0.2 is more preferable, 0.002 to 0.15 is more preferable, 0.002 to 0.12 is still more preferable, and 0.002 to 0 is preferable. .10 is more preferable, 0.015 to 0.10 is more preferable, 0.019 to 0.10 is further preferable, and 0.05 to 0.10 is still more preferable.

When mix | blending the component (A) containing composition obtained by the manufacturing method of this invention with the cosmetics mentioned later, the mass of the component (A) with respect to the total amount of the component (B) and component (C) in a heat processing raw material. The ratio [(A) / {(B) + (C)}] is the solubility point of the component (A) in the component (A) -containing composition obtained after cooling, and the preservation of the component (A) -containing composition. From the viewpoint of stability, it is preferably 0.015 or more, more preferably 0.019 or more, further preferably 0.05 or more, and is preferably 0.5 or less, more preferably 0.2 or less, and further preferably 0.1 or less. Moreover, 0.015 to 0.5 is preferable, 0.019 to 0.5 is more preferable, 0.05 to 0.2 is still more preferable, and 0.05 to 0.1 is still more preferable.

In the production method of the present invention, a surfactant may be used. From the viewpoint of maintaining the physiological activity of the (A) poorly water-soluble aromatic compound and reducing the irritation to the skin, It is desirable to reduce the amount used. The content of the surfactant in the heat treatment raw material is preferably 0 to 1 g / L, more preferably 0 to 0.5 g / L, further preferably 0 to 0.1 g / L, substantially 0 g / L, That is, it is more preferable not to contain a surfactant.

The method of heat-treating (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol in the presence of an aqueous medium is not particularly limited, and a known method can be applied.
The temperature of the heat treatment is 100 to 180 ° C., but (A) from the viewpoint of improving the solubility of the poorly water-soluble aromatic compound, it is preferably 110 ° C. or higher, more preferably 120 ° C. or higher, and heat stability. From the point, 170 ° C. or lower is more preferable, and 160 ° C. or lower is more preferable. The temperature for the heat treatment is preferably 110 to 170 ° C, more preferably 120 to 160 ° C, and further preferably 120 to 150 ° C. Examples of the heating means include water vapor and electricity.

The pressure during the heat treatment is preferably 0 to 10 MPa, more preferably 0.1 to 8 MPa, further preferably 0.1 to 6 MPa, further preferably 0.2 to 6 MPa, and further preferably 0.2 to 4 MPa in terms of gauge pressure. Preferably, 0.25 to 2 MPa is more preferable, 0.3 to 1.5 MPa is more preferable, and 0.3 to 0.6 MPa is further preferable. The gauge pressure is a pressure at atmospheric pressure of 0 MPa. Moreover, it is preferable to set it more than the saturated vapor pressure of water. Gas may be used for pressurization, and examples of the gas used include inert gas, water vapor, nitrogen gas, helium gas, and the like. The pressurization may be adjusted by a back pressure valve without using gas.

The heat treatment can be performed by any method such as a batch method, a semi-batch method, and a distribution method. Among these, the flow method is preferable in terms of easy control of the heat treatment time.
The heat treatment time is preferably 0.1 minutes or more, more preferably 0.2 minutes or more after the aqueous medium reaches the temperature of the heat treatment, from the viewpoint of improving the solubility of the (A) poorly water-soluble aromatic compound. Preferably, 0.5 minutes or more is more preferable, and from the viewpoint of thermal stability, 30 minutes or less is preferable, 15 minutes or less is more preferable, and 8 minutes or less is still more preferable. The heat treatment time is preferably 0.1 to 30 minutes, more preferably 0.2 to 15 minutes, and further preferably 0.5 to 8 minutes after the aqueous medium reaches the temperature of the heat treatment.
When the flow method is used, the heat treatment time is an average residence time calculated by dividing the volume of the high-temperature and high-pressure part of the reactor by the supply rate of the aqueous medium.

The heat treatment can be performed by any method such as a batch method, a semi-batch method, and a distribution method. Among these, the flow method is preferable in terms of easy control of the heat treatment time.
The heat treatment time is preferably 0.1 minutes or more after the heat treatment raw material reaches the temperature of the heat treatment, and 0.2 minutes or more from the viewpoint of improving the solubility of the (A) poorly water-soluble aromatic compound. More preferably, 0.5 minutes or more is further preferable, and from the viewpoint of thermal stability, 30 minutes or less is preferable, 15 minutes or less is more preferable, and 8 minutes or less is still more preferable. The heat treatment time is preferably 0.1 to 30 minutes, more preferably 0.2 to 15 minutes, and further preferably 0.5 to 8 minutes after the heat treatment raw material reaches the temperature of the heat treatment.
When the flow method is used, the heat treatment time is an average residence time calculated by dividing the volume of the high-temperature and high-pressure part of the reactor by the supply rate of the heat treatment raw material.

The flow rate of the aqueous medium in the flow method varies depending on the volume of the reactor. For example, when the reactor volume is 500 L, it is preferably 15 to 5,000 L / min, and more preferably 30 to 2,500 L / min. Further, 60 L / min to 1,000 L / min is preferable.

In the production method of the present invention, it is preferable to include a step of cooling the heat treatment liquid obtained by heat treatment to 90 ° C. or less, preferably 50 ° C. or less, more preferably 30 ° C. or less. When obtaining a liquid component (A) containing composition, 0 degreeC or more is preferable and 10 degreeC or more is preferable.

The cooling rate of the heat treatment liquid calculated from the time required to decrease from the heat treatment temperature to 90 ° C. is 0.2 ° C./s or more, further 0.5 ° C./s or more, 1 ° C./s or more, and further 3 It is preferably at least 5 ° C / s, more preferably at least 5 ° C / s. As the cooling rate increases, the solubility of the poorly water-soluble aromatic compound can be improved. For this reason, although the upper limit of a cooling rate is not specifically defined, 100 degree C / s or less, for example, 50 degrees C / s or less are preferable from viewpoints, such as restrictions of manufacturing equipment.

Furthermore, it is preferable from the viewpoint of dissolution stability of the component (A) in the obtained component (A) -containing composition, to perform a step of removing the solid matter remaining without being dissolved from the heat treatment liquid. The method for removing the solid matter is not particularly limited, and can be performed by, for example, centrifugation, decantation, or filtration.

The component (A) -containing composition thus obtained contains (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol in an aqueous medium. ) Although the content of the hardly water-soluble aromatic compound is high, precipitation of the hardly water-soluble aromatic compound can be suppressed even at room temperature and during storage at room temperature. Moreover, it is excellent in solubility in water.
The content of the component (A) in the component (A) -containing composition of the present invention is preferably 0.5 g / L or more, more preferably 1 g / L or more, and further 1.5 g / L from the viewpoint of physical distribution and usability. L or more, further 2 g / L or more, more preferably 7.5 g / L or more, and further preferably 30 g / L, and 150 g / L or less, further 100 g / L or less, further 75 g / L or less, further 60 g / L or less, It is preferably 55 g / L or less, more preferably 50 g / L or less.

In the component (A) -containing composition of the present invention, the content of the (B) dihydric alcohol is in the total composition from the viewpoint of the solubility and stability of the component (A) in the component (A) -containing composition. 1 g / L or more, further 10 g / L or more, more preferably 20 g / L or more, more preferably 100 g / L or more, further preferably 300 g / L or more, and from the viewpoint of fluidity, 700 g / L or less, and further 600 g / L or less, more preferably 500 g / L or less. Further, it is preferably 1 to 700 g / L, more preferably 10 to 600 g / L, further preferably 20 to 500 g / L, further preferably 100 to 500 g / L, and further preferably 300 to 500 g / L.

In the component (A) -containing composition of the present invention, the content of the (C) trivalent or higher alcohol is the total composition from the viewpoint of the solubility and stability of the component (A) in the component (A) -containing composition. 1 g / L or more, further 10 g / L or more, further 50 g / L or more, more preferably 100 g / L or more, more preferably 500 g / L or less, further 300 g / L or less, further 250 g / L or less, and further 200 g / L. The following is preferred. Further, it is preferably 1 to 500 g / L, more preferably 1 to 300 g / L, further preferably 10 to 250 g / L, further preferably 50 to 250 g / L, and further preferably 100 to 200 g / L.

In the component (A) -containing composition of the present invention, the mass ratio [(A) / (B)] of the component (A) to the component (B) is 0 from the viewpoint of the stability of the component (A) -containing composition. 0.001 or more, further 0.002 or more, further 0.02 or more, further 0.025 or more, and further 0.06 or more, preferably 1 or less, further 0.5 or less, further 0.2 or less, and further preferably 0.00. It is preferably 15 or less, more preferably 0.13 or less, further 0.12 or less, and further preferably 0.11 or less. Further, it is preferably 0.001 to 1, more preferably 0.001 to 0.5, still more preferably 0.001 to 0.2, still more preferably 0.002 to 0.15, and 0.002 to 0.13. Is more preferable, 0.002 to 0.12 is more preferable, 0.002 to 0.11 is further preferable, 0.02 to 0.11 is further preferable, 0.025 to 0.11 is further preferable, and 0.02. More preferably, it is from 06 to 0.11.

In the component (A) -containing composition of the present invention, the mass ratio [(A) / (C)] of the component (A) to the component (C) is the dissolution of the component (A) in the component (A) -containing composition. From the viewpoint of properties, 0.001 or more, further 0.005 or more, further 0.01 or more, further 0.12 or more, further 0.15 or more, further 0.17 or more are preferable, and 1.5 or less, It is preferably 1 or less, more preferably 0.7 or less, and further preferably 0.55 or less. Further, it is preferably 0.001 to 1.5, more preferably 0.001 to 1, further preferably 0.005 to 0.7, still more preferably 0.01 to 0.55, and 0.12 to 0.55. Is more preferred, 0.15 to 0.55 is more preferred, and 0.17 to 0.55 is even more preferred.

In the component (A) -containing composition of the present invention, the mass ratio [(B) / (C)] of the component (B) to the component (C) is the dissolution of the component (A) in the component (A) -containing composition. From the viewpoint of property, 1.5 or more, further 2 or more, and further 2.5 or more are preferable, and 10 or less, further 8 or less, and further 6 or less are preferable. Further, it is preferably 1.5 to 10, more preferably 2 to 8, and further preferably 2.5 to 6.

In the component (A) -containing composition of the present invention, the mass ratio [(A) / {(B) + (C)}] of the component (A) to the total amount of the component (B) and the component (C) is From the viewpoint of the stability of the component (A) -containing composition, 0.001 or more, further 0.002 or more, further 0.015 or more, further 0.019 or more, more preferably 0.05 or more is preferable. 5 or less, further 0.2 or less, further 0.15 or less, further 0.12 or less, and further preferably 0.1 or less. Further, 0.001 to 0.5 is preferable, 0.001 to 0.2 is preferable, 0.002 to 0.15 is more preferable, 0.002 to 0.12 is still more preferable, and 0.002 to 0.00. 1 is more preferred, 0.015 to 0.1 is more preferred, 0.019 to 0.1 is still more preferred, and 0.05 to 0.1 is still more preferred.

In the component (A) -containing composition of the present invention, it is desirable to reduce the amount of organic solvent, particularly monohydric alcohol having 4 or less carbon atoms, from the viewpoint of irritation to the skin. The content of the organic solvent in the component (A) -containing composition is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, further preferably 0 to 10% by mass, and further preferably 0 to 1% by mass. More preferably, it is substantially 0% by mass, that is, it does not contain an organic solvent.

In the component (A) -containing composition of the present invention, the content of the surfactant is desirably reduced from the viewpoint of advantageously exhibiting the effect of the (A) poorly water-soluble aromatic compound. The content of the surfactant in the component (A) -containing composition is preferably 0 to 1 g / L, more preferably 0 to 0.5 g / L, still more preferably 0 to 0.1 g / L, substantially More preferably, 0 g / L, that is, no surfactant is contained.

The component (A) -containing composition of the present invention can be used for various products such as cosmetics, pharmaceuticals, foods and daily necessities. In particular, it is useful to use in water-based products and cosmetics. As cosmetics or pharmaceuticals, skin cosmetics such as cleaning products, skin lotions, cosmetics for makeup, cosmetics for sunscreen, cosmetics for acne, cosmetics for deodorants, whitening cosmetics, hair washing agents, hair restorers Toothpaste, mouthwash, mouthwash, etc.

The component (A) -containing composition of the present invention may be diluted with water or the like depending on the use of the product. The concentration of the component (A) in the composition containing the component (A) after dilution is 0.1 to 50 g / L, further 0.2 to 30 g / L, further 0.5 to 10 g / L, and further 0.5. ~ 5 g / L, more preferably 0.5 to 2 g / L. Although the component (A) -containing composition of the present invention has a drastically increased dissolution concentration of the hardly water-soluble aromatic compound as compared with the solubility of the usual poorly water-soluble aromatic compound in water, In this case, the precipitation of the hardly water-soluble aromatic compound is suppressed and the stability is high. Moreover, high physiological activity expression of a poorly water-soluble aromatic compound can be expected.

The cosmetic of the present invention contains the component (A) -containing composition obtained as described above, and preferably (C) a mass ratio of (B) dihydric alcohol to trihydric or higher alcohol [ (B) / (C)] contains a component (A) -containing composition of 1.5 to 10, more preferably (D) selected from a deodorant component, a bactericidal component, and a feel improving component. It further contains more than seeds. As a result, the effects of the poorly water-soluble aromatic compound are fully exhibited, and the effects of the combined components can be fully expressed.
When the component (A) -containing composition of the present invention is used in a cosmetic, the mass ratio [(B) / (C)] of the component (B) to the component (C) in the component (A) -containing composition is: (A) From the solubility point of the component (A) in the containing composition, it is preferably 1.5 or more, more preferably 2 or more, and further preferably 2.5 or more, and is preferably 10 or less, more preferably 8 or less, and further preferably 6 or less. . Further, it is preferably 1.5 to 10, more preferably 2 to 8, and further preferably 2.5 to 6.

In addition, when the component (A) -containing composition of the present invention is used in cosmetics, the content of the component (A) in the component (A) -containing composition is preferably 1 g / L from the viewpoint of physical distribution and usability. More preferably, it is 2 g / L or more, more preferably 7.5 g / L or more, and further preferably 30 g / L or more.

When the component (A) -containing composition of the present invention is used in cosmetics, the mass ratio [(A) / (B)] of the component (A) to the component (B) in the component (A) -containing composition is difficult. From the viewpoint of improving the stability of the water-soluble aromatic compound, it is preferably 0.02 or more, more preferably 0.025 or more, and further preferably 0.06 or more, and 1 or less, further 0.5 or less, and further 0.15 or less. preferable. Further, it is preferably from 0.02 to 1, more preferably from 0.025 to 0.5, and still more preferably from 0.06 to 0.15.

When the component (A) -containing composition of the present invention is used in cosmetics, the mass ratio [(A) / (C)] of the component (A) to the component (C) in the component (A) -containing composition is: (A) From the viewpoint of improving the stability of the containing composition, it is preferably 0.12 or more, more preferably 0.15 or more, and further preferably 0.17 or more, and is 1.5 or less, further 1 or less, and further 0.6 or less. Is preferred. Further, it is preferably 0.12 to 1.5, more preferably 0.15 to 1, and further preferably 0.17 to 0.6.

When the component (A) -containing composition of the present invention is used in a cosmetic, the mass ratio of the component (A) to the total amount of the component (B) and the component (C) in the component (A) -containing composition [(A) / {(B) + (C)}] is preferably 0.015 or more, more preferably 0.019 or more, still more preferably 0.05 or more, more preferably 0.5 or less, and further preferably 0.00 from the viewpoint of stability. 2 or less, more preferably 0.1 or less. Moreover, 0.015 to 0.5 is preferable, 0.019 to 0.5 is more preferable, 0.05 to 0.2 is still more preferable, and 0.05 to 0.1 is still more preferable.

In the cosmetics of the present invention, the content of the poorly water-soluble aromatic compound of the component (A) is sufficient from the viewpoint of sufficiently exhibiting the effect of the poorly water-soluble aromatic compound. In the case of using the components, excellent deodorizing effect and bactericidal effect are obtained, there is no stickiness, and from the viewpoint of obtaining a smooth feeling, 0.01% by mass or more is preferable in the total composition, and 0.02% by mass The above is more preferable, 0.05 mass% or more is further preferable, 1 mass% or less is preferable, 0.5 mass% or less is more preferable, and 0.3 mass% or less is still more preferable. The content of component (A) is preferably 0.01 to 1% by mass, more preferably 0.02 to 0.5% by mass, and still more preferably 0.05 to 0.3% by mass in the total composition. .

In the cosmetic of the present invention, the content of the dihydric alcohol of the component (B) is such that an aromatic antibacterial component is used as the poorly water-soluble aromatic compound from the viewpoint of sufficiently exerting the effect of the poorly water-soluble aromatic compound. In that case, 0.09% by mass or more is preferable in the total composition, and 0.18% by mass or more is more preferable from the viewpoint of obtaining an excellent deodorizing effect and bactericidal effect, no stickiness, and a smooth feeling. Preferably, 0.3% by mass or more is more preferable, 0.45% by mass or more is further more preferable, 8.4% by mass or less is preferable, 7% by mass or less is more preferable, and 5.5% by mass or less is further preferable. 5 mass% or less is still more preferable. The content of component (B) is preferably 0.09 to 8.4% by mass, more preferably 0.18 to 7% by mass, and still more preferably 0.3 to 5.5% by mass in the total composition. 0.45 to 5% by mass is even more preferable.

In the cosmetic of the present invention, the content of the trivalent or higher alcohol of the component (C) is a viewpoint of sufficiently exerting the effect of the poorly water-soluble aromatic compound. From the viewpoint of obtaining an excellent deodorizing effect and bactericidal effect, no stickiness, and a smooth feeling, 0.01% by mass or more is preferable in the total composition, and 0.03% by mass or more. Is more preferably 0.06% by mass or more, still more preferably 0.09% by mass or more, more preferably 2.86% by mass or less, more preferably 2.5% by mass or less, and further more preferably 2% by mass or less. Preferably, 1.72% by mass or less is even more preferable. The content of component (C) is preferably 0.01 to 2.86% by mass, more preferably 0.03 to 2.5% by mass, and still more preferably 0.06 to 2% by mass in the total composition. 0.09 to 1.72% by mass is even more preferable.

The component (D) used in the present invention is one other than the component (A), and is one or more selected from a deodorizing component, a bactericidal component and a touch improving component.
Among the components (D), the deodorant component may be any of chemical deodorization methods; physical deodorization methods; biological deodorization methods; sensory deodorization methods.
Regarding chemical deodorization methods, metal oxides such as zinc oxide and titanium oxide that chemically adsorb odorous substances; tris (hydroxymethyl) aminomethane (2-amino-2-hydroxymethyl) that neutralizes odorous substances 1,3-propanediol) and the like, and antioxidants such as dibutylhydroxytoluene that suppress decomposition to odorous substances.
Examples of physical deodorization methods include cyclodextrins that physically adsorb odorous substances, hydroxyapatite, chitosan fine particles, and porous substances such as activated carbon.
Examples of biological deodorization methods include yellowfin extract and oleic acid.
Examples of sensory deodorization methods include fragrances such as L-menthol.
Of these, a deodorizing component selected from amines is preferable from the viewpoint of immediate effect of the deodorizing effect. From the viewpoint of usability, tris (hydroxymethyl) aminomethane (2-amino-2-hydroxymethyl-1, 3-propanediol) is more preferred.

When a deodorant component is used as the component (D), the content is preferably 0.01% by mass or more, and 0.05% by mass or more in the total composition from the viewpoint of reducing the feeling of slimness during application. More preferably, 0.07% by mass or more is further preferable, 0.09% by mass or more is further more preferable, and from the viewpoint of reducing stickiness during coating, 2% by mass or less is preferable, and 1.5% by mass or less is more preferable. Preferably, 1% by mass or less is more preferable, and 0.9% by mass or less is even more preferable. Further, when a deodorant component is used as component (D), the content thereof is preferably 0.01 to 2% by mass, more preferably 0.05 to 1.5% by mass in the total composition, and 0.07 To 1% by mass is more preferable, and 0.09 to 0.9% by mass is even more preferable.

Among the components (D), examples of the bactericidal component include alkyltrimethylammonium bromide, cetylpyridinium chloride, silver-supporting inorganic particles, lysozyme chloride, benzalkonium chloride, cetylpyridinium chloride (CPC), alum and the like. Examples of the silver-supported inorganic particles include silver-supported zeolite and silver-supported cancrinite.
Of these, benzalkonium chloride is preferred from the standpoint of the durability of the smooth feeling and the low sliminess.

When a sterilizing component is used as the component (D), the content is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, in the total composition, from the viewpoint of obtaining a high sterilizing effect. 0.02% by mass or more is more preferable, 0.03% by mass or more is further more preferable, 4% by mass or less is preferable, 3% by mass or less is more preferable, 1% by mass or less is further preferable, and 0.5% by mass or less is preferable. Even more preferred. When a sterilizing component is used as component (D), the content thereof is preferably 0.005 to 4% by mass, more preferably 0.01 to 3% by mass, and 0.02 to 1% by mass in the total composition. % Is more preferable, and 0.03 to 0.5% by mass is even more preferable.

After the component (D), examples of the touch improving component include powders, and any of inorganic powders, organic powders, and composite powders thereof may be used.
Examples of the organic powder include nylon resin (commercially available, Elf Atchem, ORGASOL 2002EXD NAT COS TypeS, ORGASOL 4000EXD NAT COS; Toray, SP-500, etc.), polystyrene resin (commercially available, Sumitomo Chemical) Manufactured by Kogyo Co., Ltd., Fine Pearl; manufactured by Sekisui Plastics Kogyo Co., Ltd., Techpolymer SB; Beads), polymethyl methacrylate resin (commercially available from Matsumoto Yushi Seiyaku, Matsumoto Microsphere M; Sekisui Plastics, Techpolymer MB; Soken Chemicals, Fine Powder MP, etc.), (Meth) acrylic ester resin, silicone resin (Commercially available products, Shin-Etsu Chemical Co., Ltd., KMP-590; Toshiba Silicone Corp., Tospearl 145, Tospearl 2000B, etc.), silicone rubber powder (commercially available products, Shin-Etsu Chemical Co., Ltd., KMP-597, KMP-598; Toray Industries, Inc., Trefil 501, Trefil 505, Trefil 506, Trefil 601 and the like), cellulose beads (commercially available, Asahi Kasei Co., Ltd., Apicel RC-A591NF, etc.) and the like. Further, a crosslinked (meth) acrylic acid ester resin powder such as lauryl methacrylate / ethylene glycol / methacrylic acid / sodium methacrylate copolymer (Japanese Patent Laid-Open No. 2006-8659) can also be used.
Examples of inorganic powders include talc, sericite, mica, kaolin, clay, bentonite, silicic acid, anhydrous silicic acid, magnesium silicate, mica, magnesium oxide, zinc oxide, titanium oxide, aluminum oxide, aluminum sulfate, and calcium sulfate. , Barium sulfate, magnesium sulfate and the like.
In addition, as a powder having an intermediate structure in which an inorganic powder and an organic powder are compounded, polymethyl having a network structure in which a siloxane bond extends three-dimensionally and a methyl group bonded to one silicon atom. Examples thereof include silsesquioxane powder.
In addition, when using powder as a touch improvement component, what is also contained in a deodorant component shall be handled as a deodorant component.

From the viewpoint of reducing the feeling of squeak, these feel improving components preferably have an average particle size of 0.01 μm or more, more preferably 0.05 μm or more, further preferably 0.2 μm or more, and suppress roughness. From the viewpoint of further improving the smooth feeling, it is preferably 50 μm or less, more preferably 20 μm or less, and even more preferably 8 μm or less.

When a feel improving component is used as the component (D), the content is preferably 0.01% by mass or more in the total composition from the viewpoint of reducing squeakiness, suppressing roughness, and further improving smoothness. More preferably 1% by weight or more, still more preferably 1% by weight or more, still more preferably 1.5% by weight or more, more preferably 20% by weight or less, more preferably 10% by weight or less, and even more preferably 5% by weight or less. preferable. Further, when a feel improving component is used as the component (D), the content thereof is preferably 0.01 to 20% by mass, more preferably 0.1 to 20% by mass in the total composition, and 1 to 10% by mass. Is more preferable, and 1.5 to 5% by mass is even more preferable.

In addition, the component (D) is one or more selected from a deodorant component, a bactericidal component, and a feel improving component. For example, the deodorizing component may be used in combination with a bactericidal component and / or a touch improving component. it can.
The total content of component (D) is not generally determined depending on the type of component used. For example, from the viewpoint of expressing the function of each component, that is, the deodorizing function, the bactericidal function, and the touch improving function, the total composition 0.005% by mass or more is preferable, 0.01% by mass or more is more preferable, 0.02% by mass or more is more preferable, 20% by mass or less is preferable, 15% by mass or less is more preferable, and 10% by mass or less. Is more preferable, and 5 mass% or less is still more preferable. In addition, the total content of component (D) is preferably 0.005 to 20% by mass, more preferably 0.01 to 15% by mass, still more preferably 0.02 to 10% by mass, based on the total composition. Even more preferred is 02-5% by weight.

The cosmetic of the present invention preferably further contains an aqueous medium such as water. The blending method may be performed by adding the component (A) -containing composition to the aqueous medium and then adding and mixing the component (D) and other components, or mixing the component (A) -containing composition and component (D ), And other components may be added separately and mixed together.
The concentration of the hardly water-soluble aromatic compound in the aqueous medium is 0.1 to 50 g / L, further 0.2 to 30 g / L, further 0.5 to 10 g / L, further 0.5 to 5 g / L, and further 0. 0.5 to 2 g / L is preferable.

In addition to the above-mentioned components, the cosmetics of the present invention are components used in ordinary cosmetics, such as oily components, surfactants, water-soluble polymers, extracts, antioxidants, pigments, pH adjusters, ultraviolet absorption. An agent, a blood circulation promoter, a fragrance | flavor, etc. can be contained.

Embodiments and preferred embodiments of the present invention are shown below.

<1> comprising a step of heat-treating (A) a poorly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol at 100 to 180 ° C. in the presence of an aqueous medium. A method for producing an aromatic compound-containing composition.

<2> (A) The poorly water-soluble aromatic compound has a solubility in water at 25 ° C. of preferably 0.5 g / L or less, more preferably 0.3 g / L or less, and still more preferably 0.2 g / L or less. The manufacturing method of the hardly water-soluble aromatic compound containing composition as described in <1> which is an aromatic compound of this.
<3> (A) The poorly water-soluble aromatic compound has a solubility in (B) dihydric alcohol at 25 ° C. of preferably 5 g / L or more, more preferably 10 g / L or more, and still more preferably 20 g / L or more. The method for producing a poorly water-soluble aromatic compound-containing composition according to <1> or <2>, which is an aromatic compound.
<4> (A) The poorly water-soluble aromatic compound is preferably one or more selected from an antibacterial component, a whitening component, and a hair growth component, and more preferably a phenolic antibacterial agent, an antiseptic, and a chromone derivative. And a method for producing a poorly water-soluble aromatic compound-containing composition according to any one of <1> to <3>, wherein the composition is one or more selected from flavanol derivatives.
<5> The phenolic antibacterial agent is preferably one or two selected from triclosan, chlorthymol, carbachlor, chlorophene, dichlorophen, hexachlorophene, chloroxylenol, chlorocresol, O-phenylphenol and isopropylmethylphenol The method for producing a poorly water-soluble aromatic compound-containing composition according to <4>, which is one or more selected from triclosan and isopropylmethylphenol, more preferably isopropylmethylphenol. .
<6> The preservative is preferably one or two selected from paraoxybenzoates, and more preferably selected from methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben and benzylparaben. The manufacturing method of the slightly water-soluble aromatic compound containing composition as described in <4> which is 1 type or 2 types.
<7> The chromone derivative is preferably 2-butylchromone, 2-pentylchromone, 2-heptylchromone, 2-nonylchromone, 2-hexadecylchromone, 2- (1-ethylpentyl) chromone, 2-butyl-7- Methoxychromone, 2-pentyl-7-methoxychromone, 2-heptyl-7-methoxychromone, 2-nonyl-7-methoxychromone, 2-pentadecyl-7-methoxychromone, 2- (1-ethylpentyl) -7- Methoxychromone, 7-hydroxy-2-methylchromone, 7-hydroxy-2-butylchromone, 7-hydroxy-2-pentylchromone, 7-hydroxy-2-heptylchromone, 7-hydroxy-2-nonylchromone, 7-hydroxy -2-pentadecylchromone and 7-hydroxy-2- (1-d 1 or 2 or more types selected from rupentyl) chromone, more preferably 2- (1-ethylpentyl) -7-methoxychromone. Production method.
<8> The hair-growth component is preferably one or more selected from flavanol derivatives, nicotinic acids, vitamin Es, minoxidil, bimatoprost, tafluprost, nonyl acid vanillylamide, hypericum herb extract and chili pepper tincture, and more Preferably, trans-3,4'-dimethyl-3-hydroxyflavanone, benzyl nicotinate, tocopherol nicotinate, β-butoxyethyl nicotinate, α-tocopherol, dl-α-tocopherol acetate, tocopherol nicotinate, natural vitamin E, One or more selected from minoxidil, bimatoprost, tafluprost, nonylic acid vanillylamide, hypericum herb extract and capsicum tincture, more preferably trans-3,4'-dimethyl-3-hydroxyflavanone Method for producing sparingly water-soluble aromatic compound-containing composition according to one <4>.
<9> (B) The dihydric alcohol is preferably ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, diethylene glycol, dipropylene glycol, One or more selected from polyethylene glycol and polypropylene glycol, more preferably one selected from ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol and dipropylene glycol Or two or more, more preferably one or more selected from propylene glycol, 1,3-propanediol and 1,3-butanediol, and any one of <1> to <8> Method for producing a composition containing a hardly water-soluble aromatic compound as described .
<10> (C) Trivalent or higher alcohol is preferably glycerin, diglycerin, triglycerin, 1,2,4-butanetriol, 1,2,5-pentanetriol, 2-methylpropanetriol, 2-methyl -One or more selected from 1,2,4-butanetriol, trimethylolethane and trimethylolpropane, more preferably one or more selected from glycerin, diglycerin and triglycerin More preferably, the method for producing a poorly water-soluble aromatic compound-containing composition according to any one of <1> to <9>, which is glycerin and / or diglycerin.
<11> The aqueous medium is preferably an aqueous solution of water or an organic solvent, more preferably an aqueous solution of water or a monohydric alcohol having 4 or less carbon atoms, more preferably an aqueous solution of water or ethanol, and still more preferably. The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of <1> to <10>, which is water.
<12> The concentration of the organic solvent in the aqueous solution of the organic solvent is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, still more preferably 0 to 10% by mass, and still more preferably 0 to 1% by mass. The manufacturing method of the slightly water-soluble aromatic compound containing composition as described in <11> which exists and is more preferably not included.
<13> In the heat treatment step, (A) a hardly water-soluble aromatic compound contains an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol. In the heat treatment raw material, preferably 0.1 g / L or more, more preferably 0.5 g / L or more, still more preferably 0.7 g / L or more, still more preferably 0.9 g / L or more, still more preferably 1 g. / L or more, further 2 g / L or more, further 7.5 g / L or more, further 30 g / L or more, preferably 150 g / L or less, more preferably 100 g / L or less, still more preferably 75 g / L or less. More preferably 60 g / L or less, still more preferably 55 g / L or less, still more preferably 50 g / L or less, preferably 0.1 to 150 g / L, more preferably 0.1 to 100 g / L, Further Preferably 0.5 to 75 g / L, more preferably 0.7 to 60 g / L, more preferably 0.9 to 55 g / L, still more preferably 1 to 55 g / L, still more preferably 1 to 50 g / L, More preferably 2 to 50 g / L, more preferably 7.5 to 50 g / L, still more preferably 30 to 50 g / L, The poorly water-soluble aromatic compound according to any one of <1> to <12> The manufacturing method of a containing composition.
<14> In the heat treatment step, (B) the dihydric alcohol is treated with an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol. The raw material preferably contains 1 g / L or more, more preferably 10 g / L or more, still more preferably 20 g / L or more, still more preferably 100 g / L or more, still more preferably 300 g / L or more, and preferably 700 g. / L or less, more preferably 600 g / L or less, still more preferably 500 g / L or less, preferably 1 to 700 g / L, more preferably 10 to 600 g / L, still more preferably 20 to 500 g / L, More preferably, the water-insoluble aromatic compound according to any one of <1> to <13>, containing 100 to 500 g / L, more preferably 300 to 500 g / L. Method for producing a composition containing.
<15> In the heat treatment step, (C) a trivalent or higher alcohol contains an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trivalent or higher alcohol. The heat treatment raw material preferably contains 1 g / L or more, more preferably 10 g / L or more, further preferably 50 g / L or more, more preferably 100 g / L or more, and preferably 500 g / L or less, more preferably Is 300 g / L or less, more preferably 250 g / L or less, further preferably 200 g / L or less, preferably 1 to 500 g / L, more preferably 1 to 300 g / L, still more preferably 10 to 250 g / L. L, more preferably 50 to 250 g / L, and still more preferably 100 to 200 g / L, The poorly water-soluble aromatization according to any one of <1> to <14> Method for producing a goods-containing composition.
<16> In the heat treatment step, in the heat treatment raw material containing an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol, with respect to the component (B) The mass ratio [(A) / (B)] of component (A) is preferably 0.001 or more, more preferably 0.002 or more, still more preferably 0.02 or more, still more preferably 0.025 or more, and further Preferably it is 0.06 or more, preferably 1 or less, more preferably 0.5 or less, still more preferably 0.2 or less, still more preferably 0.15 or less, still more preferably 0.13 or less, still more preferably. Is 0.12 or less, more preferably 0.11 or less, preferably 0.001 to 1, more preferably 0.001 to 0.5, still more preferably 0.001 to 0.2, and still more preferably. 0.0 2 to 0.15, more preferably 0.002 to 0.13, more preferably 0.002 to 0.12, more preferably 0.002 to 0.11, and still more preferably 0.02 to 0.11. The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of <1> to <15>, more preferably 0.025 to 0.11, and further preferably 0.06 to 0.11.
<17> In the heat treatment step, in the heat treatment raw material containing an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol, the component (C) The mass ratio [(A) / (C)] of component (A) is preferably 0.001 or more, more preferably 0.005 or more, still more preferably 0.01 or more, still more preferably 0.12 or more, and further Preferably it is 0.15 or more, more preferably 0.17 or more, preferably 1.5 or less, more preferably 1 or less, still more preferably 0.7 or less, still more preferably 0.55 or less, Further, it is preferably 0.001 to 1.5, more preferably 0.001 to 1, still more preferably 0.005 to 0.7, still more preferably 0.01 to 0.55, still more preferably 0.12 to 0.55, even better Ku 0.15 to 0.55, more preferably the production method of 0.17 to 0.55 <1> to poorly water-soluble aromatic compound-containing composition according to any one of <16>.
<18> In the heat treatment step, in the heat treatment raw material containing an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol, the component (C) The mass ratio [(B) / (C)] of component (B) is preferably 1.5 or more, more preferably 2 or more, still more preferably 2.5 or more, and preferably 10 or less, more preferably Is any one of <1> to <17>, which is 8 or less, more preferably 6 or less, preferably 1.5 to 10, more preferably 2 to 8, and still more preferably 2.5 to 6. The manufacturing method of the hardly water-soluble aromatic compound containing composition as described in any one of.
<19> In the heat treatment step, in the heat treatment raw material containing an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol, component (B) and The mass ratio [(A) / {(B) + (C)}] of the component (A) to the total amount of the component (C) is preferably 0.001 or more, more preferably 0.002 or more, and still more preferably. 0.015 or more, more preferably 0.019 or more, still more preferably 0.05 or more, preferably 0.5 or less, more preferably 0.2 or less, still more preferably 0.15 or less, still more preferably Is 0.12 or less, more preferably 0.10 or less, preferably 0.001 to 0.5, more preferably 0.001 to 0.2, still more preferably 0.002 to 0.15, More preferably 0.002-0 12, more preferably 0.002 to 0.10, more preferably 0.015 to 0.10, still more preferably 0.019 to 0.10, still more preferably 0.05 to 0.10 <1> The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of to <18>.
<20> In the heat treatment step, the surfactant is an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trivalent or higher alcohol heat treatment raw material. Preferably 0 to 1 g / L, more preferably 0 to 0.5 g / L, still more preferably 0 to 0.1 g / L, or even more preferably <1> to <19> Of producing a slightly water-soluble aromatic compound-containing composition.
<21> The temperature of the heat treatment is preferably 110 ° C. or higher, more preferably 120 ° C. or higher, preferably 170 ° C. or lower, more preferably 160 ° C. or lower, and preferably 120 to 160 ° C., The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of <1> to <20>, more preferably 120 to 150 ° C.
<22> The pressure during the heat treatment is preferably 0 to 10 MPa, more preferably 0.1 to 8 MPa, still more preferably 0.1 to 6 MPa, still more preferably 0.2 to 6 MPa, and still more preferably 0 in terms of gauge pressure. Any one of <1> to <21>, which is 2 to 4 MPa, more preferably 0.25 to 2 MPa, more preferably 0.3 to 1.5 MPa, and still more preferably 0.3 to 0.6 MPa. Of producing a slightly water-soluble aromatic compound-containing composition.
<23> The heat treatment time is preferably 0.1 minutes or more, more preferably 0.2 minutes or more, and even more preferably 0.5 minutes after the aqueous medium reaches the temperature of the heat treatment described in <20>. Or more, preferably 30 minutes or less, more preferably 15 minutes or less, still more preferably 8 minutes or less, preferably 0.1 to 30 minutes, more preferably 0.2 to 15 minutes, The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of <1> to <22>, more preferably 0.5 to 8 minutes.
<24> The heat treatment time is preferably 0.1 minutes or more, more preferably 0.2 minutes or more, and still more preferably 0.8 minutes after the heat treatment raw material reaches the heat treatment temperature described in <20>. 5 minutes or more, preferably 30 minutes or less, more preferably 15 minutes or less, still more preferably 8 minutes or less, and preferably 0.1 to 30 minutes, more preferably 0.2 to 15 minutes. More preferably, the method for producing a poorly water-soluble aromatic compound-containing composition according to any one of <1> to <22>, which is 0.5 to 8 minutes.
<25> Further, the slightly water-soluble solution according to any one of <1> to <24>, further including a step of cooling the heat treatment liquid obtained by the heat treatment, preferably at a cooling rate of 0.2 ° C./s or more. For producing a composition containing a functional aromatic compound.
<26> In the step of cooling the heat treatment liquid, the cooling rate from the heat treatment temperature to 90 ° C. is preferably 0.2 ° C./s or more, more preferably 0.5 ° C./s or more, and further preferably 1 ° C. Or more, more preferably 3 ° C./s or more, further preferably 5 ° C./s or more, preferably 100 ° C./s or less, more preferably 50 ° C./s or less. A method for producing a composition containing a hardly water-soluble aromatic compound.

<27> A slightly water-soluble aromatic compound-containing composition obtained by the production method according to any one of <1> to <26>.
<28> The content of the (A) sparingly water-soluble aromatic compound in the sparingly water-soluble aromatic compound-containing composition is preferably 0.5 g / L or more, more preferably 1 g / L or more, still more preferably 1. The poorly water-soluble aromatic compound-containing composition according to <27>, which is 5 g / L or more, more preferably 2 g / L or more.
<29> The content of the dihydric alcohol (B) in the hardly water-soluble aromatic compound-containing composition is preferably 1 g / L or more, more preferably 10 g / L or more, still more preferably 20 g / L or more, and further Preferably it is 100 g / L or more, more preferably 300 g / L or more, preferably 700 g / L or less, more preferably 600 g / L or less, still more preferably 500 g / L or less, and preferably 1 to <27> or <28>, which is 700 g / L, more preferably 10 to 600 g / L, still more preferably 20 to 500 g / L, still more preferably 100 to 500 g / L, still more preferably 300 to 500 g / L. A slightly water-soluble aromatic compound-containing composition.
The content of the (C) trivalent or higher alcohol in the <30> hardly water-soluble aromatic compound-containing composition is preferably 1 g / L or more, more preferably 10 g / L or more, and even more preferably 50 g / L or more. More preferably, it is 100 g / L or more, preferably 500 g / L or less, more preferably 300 g / L or less, still more preferably 250 g / L or less, still more preferably 200 g / L or less, and preferably 1 to 500 g / L, more preferably 1 to 300 g / L, still more preferably 10 to 250 g / L, still more preferably 50 to 250 g / L, still more preferably 100 to 200 g / L <27> to <29> The water-insoluble aromatic compound containing composition of any one of these.
<31> The mass ratio [(A) / (B)] of the component (A) to the component (B) is preferably 0.001 or more, more preferably 0.002 or more, still more preferably 0.02 or more, and further Preferably it is 0.025 or more, More preferably, it is 0.06 or more, Preferably it is 1 or less, More preferably, it is 0.5 or less, Furthermore, 0.2 or less, More preferably, it is 0.15 or less, More preferably, it is 0 .13 or less, more preferably 0.12 or less, further preferably 0.11 or less, preferably 0.001 to 1, more preferably 0.001 to 0.5, and still more preferably 0.001 to 0.2, more preferably 0.002 to 0.15, more preferably 0.002 to 0.13, more preferably 0.002 to 0.12, more preferably 0.002 to 0.11, and even more preferably. Is 0.02 ~ .11, more preferably 0.025 ~ 0.11 and more preferably is from 0.06 to 0.11 <27> - a poorly water-soluble aromatic compound-containing composition according to any one of <30>.
<32> The mass ratio [(A) / (C)] of the component (A) to the component (C) is preferably 0.001 or more, more preferably 0.005 or more, still more preferably 0.01 or more, and further 0.12 or more, further 0.15 or more, further 0.17 or more, preferably 1.5 or less, more preferably 1 or less, still more preferably 0.7 or less, still more preferably 0.55 or less. And preferably 0.001 to 1.5, more preferably 0.001 to 1, still more preferably 0.005 to 0.7, still more preferably 0.01 to 0.55, still more preferably 0.00. 12 to 0.55, more preferably 0.15 to 0.55, more preferably 0.17 to 0.55, containing the poorly water-soluble aromatic compound according to any one of <27> to <31> Composition.
<33> The mass ratio [(B) / (C)] of the component (B) to the component (C) is preferably 1.5 or more, more preferably 2 or more, still more preferably 2.5 or more. It is preferably 10 or less, more preferably 8 or less, even more preferably 6 or less, and preferably 1.5 to 10, more preferably 2 to 8, and further preferably 2.5 to 6 <27> The sparingly water-soluble aromatic compound-containing composition according to any one of to <32>.
<34> Mass ratio [(A) / {(B) + (C)}] of component (A) to the total amount of component (B) and component (C) is preferably 0.001 or more, more preferably 0.002 or more, more preferably 0.015 or more, more preferably 0.019 or more, still more preferably 0.05 or more, preferably 0.5 or less, more preferably 0.2 or less, still more preferably Is 0.15 or less, more preferably 0.12 or less, further preferably 0.10 or less, preferably 0.001 to 0.5, more preferably 0.001 to 0.2, more preferably 0.002 to 0.15, more preferably 0.002 to 0.12, more preferably 0.002 to 0.10, still more preferably 0.015 to 0.1, still more preferably 0.019 to 0. 1, more preferably 0.05-0. In a <27> - a poorly water-soluble aromatic compound-containing composition according to any one of <31>.
In the <35> hardly water-soluble aromatic compound-containing composition, the content of the organic solvent is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, still more preferably 0 to 10% by mass, and still more preferably. The hardly water-soluble aromatic compound-containing composition according to any one of <27> to <34>, which is 0 to 1% by mass, and more preferably not contained.
In the <36> hardly water-soluble aromatic compound-containing composition, the content of monohydric alcohol having 4 or less carbon atoms is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, and still more preferably 0 to 10%. The poorly water-soluble aromatic compound-containing composition according to any one of <27> to <35>, which is contained by mass%, more preferably 0 to 1% by mass, and still more preferably not contained.
<37> In the composition containing a hardly water-soluble aromatic compound, the content of the surfactant is preferably 0 to 1% by mass, more preferably 0 to 0.5% by mass, and still more preferably 0 to 0.1% by mass. %, And more preferably, the hardly water-soluble aromatic compound-containing composition according to any one of <27> to <36>.

<38> A cosmetic comprising the sparingly water-soluble aromatic compound-containing composition according to any one of <27> to <37>.
<39> The cosmetic according to <38>, further comprising (D) one or more selected from a deodorizing component, a bactericidal component, and a feel improving component.
<40> Obtained by a method comprising a step of heat-treating (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol and (C) a trihydric or higher alcohol at 100 to 180 ° C. in the presence of an aqueous medium. ,
(C) a hardly water-soluble aromatic compound-containing composition having a mass ratio [(B) / (C)] of (B) dihydric alcohol to trihydric or higher alcohol of 1.5 to 10,
(D) Cosmetics containing 1 or more types chosen from a deodorant component, a bactericidal component, and a touch improvement component.
<41> The mass ratio [(B) / (C)] of the component (B) to the component (C) in the hardly water-soluble aromatic compound-containing composition is preferably 1.5 or more, more preferably 2 or more. More preferably, it is 2.5 or more, preferably 10 or less, more preferably 8 or less, still more preferably 6 or less, and preferably 1.5 to 10, more preferably 2 to 8, still more preferably. The cosmetic according to any one of <38> to <40>, in which is 2.5 to 6.
<42> The content of the component (A) in the hardly water-soluble aromatic compound-containing composition is preferably 1 g / L or more, more preferably 2 g / L or more, still more preferably 7.5 g / L or more, still more preferably. Is a cosmetic according to any one of <38> to <41>, which is 30 g / L or more.
<43> The mass ratio [(A) / (B)] of component (A) to component (B) in the hardly water-soluble aromatic compound-containing composition is preferably 0.02 or more, more preferably 0.025. Or more, more preferably 0.06 or more, preferably 1 or less, more preferably 0.5 or less, still more preferably 0.15 or less, and preferably 0.02 to 1, more preferably The cosmetic according to any one of <38> to <42>, which is 0.025 to 0.5, more preferably 0.06 to 0.15.
In the <44> hardly water-soluble aromatic compound-containing composition, the mass ratio [(A) / (C)] of the component (A) to the component (C) is preferably 0.12 or more, more preferably 0.15. Or more, more preferably 0.17 or more, preferably 1.5 or less, more preferably 1 or less, still more preferably 0.6 or less, and preferably 0.12 to 1.5, more The cosmetic according to any one of <38> to <43>, preferably 0.15 to 1, more preferably 0.17 to 0.6.
<45> The mass ratio [(A) / {(B) + (C)}] of the component (A) to the total amount of the component (B) and the component (C) in the hardly water-soluble aromatic compound-containing composition is , Preferably 0.015 or more, more preferably 0.019 or more, still more preferably 0.05 or more, and preferably 0.5 or less, more preferably 0.2 or less, still more preferably 0.1 or less. And preferably 0.015 to 0.5, more preferably 0.019 to 0.5, still more preferably 0.05 to 0.2, and still more preferably 0.05 to 0.1. Cosmetics according to any one of 38> to <44>.
<46> The content of the poorly water-soluble aromatic compound of the component (A) in the cosmetic is preferably 0.01% by mass or more, more preferably 0.02% by mass or more, and still more preferably in the total composition. 0.05% by mass or more, preferably 1% by mass or less, more preferably 0.5% by mass or less, still more preferably 0.3% by mass or less, and preferably 0.01 to 1% by mass. %, More preferably 0.02 to 0.5% by mass, and still more preferably 0.05 to 0.3% by mass, according to any one of <38> to <45>.
<47> The content of (B) dihydric alcohol in the cosmetic is preferably 0.09% by mass or more, more preferably 0.18% by mass or more, and still more preferably 0.3% by mass in the total composition. More preferably, it is 0.45% by mass or more, preferably 8.4% by mass or less, more preferably 7% by mass or less, still more preferably 5.5% by mass or less, and further preferably 5% by mass or less. Moreover, it is preferably 0.09 to 8.4% by mass, more preferably 0.18 to 7% by mass, still more preferably 0.3 to 5.5% by mass, and still more preferably 0.45 to 5% by mass. % Of cosmetics according to any one of <38> to <46>.
<48> The content of the (C) trivalent or higher alcohol in the cosmetic is preferably 0.01% by mass or more, more preferably 0.03% by mass or more, and still more preferably 0.06% in the total composition. % By mass or more, more preferably 0.09% by mass or more, preferably 2.86% by mass or less, more preferably 2.5% by mass or less, still more preferably 2% by mass or less, still more preferably 1.% by mass. 72 mass% or less, preferably 0.01 to 2.86 mass%, more preferably 0.03 to 2.5 mass%, still more preferably 0.06 to 2 mass%, still more preferably 0.8. The cosmetic according to any one of <38> to <47>, which is 09 to 1.72% by mass.
<49> In the heat treatment step, the mass ratio [(A) / (B)] of the component (A) to the component (B) is preferably 0.02 or more, more preferably 0.025 or more, and still more preferably. 0.06 or more, preferably 1 or less, more preferably 0.5 or less, still more preferably 0.15 or less, and preferably 0.02 to 1, more preferably 0.025 to 0. 5. More preferably, the cosmetic according to any one of <38> to <48>, which is 0.06 to 0.15.
<50> In the heat treatment step, the mass ratio [(A) / (C)] of the component (A) to the component (C) is preferably 0.12 or more, more preferably 0.15 or more, and still more preferably. 0.17 or more, preferably 1.5 or less, more preferably 1 or less, still more preferably 0.6 or less, and preferably 0.12 to 1.5, more preferably 0.15. The cosmetic according to any one of <38> to <49>, which is from 1 to 1, more preferably from 0.17 to 0.6.
<51> In the heat treatment step, the mass ratio of (A) poorly water-soluble aromatic compound to the total amount of (B) dihydric alcohol and (C) trihydric or higher alcohol [(A) / {(B) + (C)}] is preferably 0.015 or more, more preferably 0.019, still more preferably 0.05 or more, and preferably 0.5 or less, more preferably 0.2 or less, still more preferably. Is 0.1 or less, preferably 0.015 to 0.5, more preferably 0.019 to 0.5, still more preferably 0.05 to 0.2, still more preferably 0.05 to 0. 1. The cosmetic according to any one of <38> to <50>, which is 1.
Of the <52> component (D), the deodorant component is preferably selected from those related to chemical deodorization methods, physical deodorization methods, biological deodorization methods and sensory deodorization methods. One or more, more preferably zinc oxide, titanium oxide, tris (hydroxymethyl) aminomethane (2-amino-2-hydroxymethyl-1,3-propanediol), dibutylhydroxytoluene, cyclodextrin, hydroxyapatite, One or more selected from porous materials such as chitosan fine particles, activated carbon, yellowfin extract, oleic acid and L-menthol, more preferably tris (hydroxymethyl) aminomethane (2-amino-2-hydroxymethyl-1,3 -The cosmetic according to any one of <39> to <50>, which is propanediol).
When a deodorant component is used as the <53> component (D), the content thereof is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and still more preferably 0.07 in the total composition. % By mass or more, more preferably 0.09% by mass or more, preferably 2% by mass or less, more preferably 1.5% by mass or less, still more preferably 1% by mass or less, still more preferably 0.9% by mass. % Or less, preferably 0.01 to 2% by mass, more preferably 0.05 to 1.5% by mass, still more preferably 0.07 to 1% by mass, and still more preferably 0.09 to 0. The cosmetic according to any one of <39> to <52>, which is 9% by mass.
Among the <54> component (D), the sterilizing component is preferably alkyltrimethylammonium bromide, cetylpyridinium chloride, silver-supported inorganic particles, lysozyme chloride, benzalkonium chloride, cetylpyridinium chloride (CPC), alum, silver-supported zeolite and The cosmetic according to any one of <39> to <53>, which is at least one selected from silver-carrying cancrinite, more preferably benzalkonium chloride.
When a sterilizing component is used as the <55> component (D), the content thereof is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, and still more preferably 0.02% by mass in the entire composition. % Or more, more preferably 0.03% by mass or more, preferably 4% by mass or less, more preferably 3% by mass or less, still more preferably 1% by mass or less, and further preferably 0.5% by mass or less. And preferably 0.005 to 4% by mass, more preferably 0.01 to 3% by mass, still more preferably 0.02 to 1% by mass, and still more preferably 0.03 to 0.5% by mass. The cosmetic according to any one of <39> to <54>.
<56> The component (D) and the touch improving component is preferably an inorganic powder, an organic powder or a composite powder thereof, more preferably a nylon resin, a polystyrene resin, a polyethylene resin, or a polymethyl methacrylate resin. , (Meth) acrylic ester resin, silicone resin, silicone rubber powder, cellulose beads, lauryl methacrylate / ethylene glycol / sodium methacrylate copolymer, talc, sericite, mica, kaolin, clay, bentonite, Silicic acid, anhydrous silicic acid, magnesium silicate, mica, magnesium oxide, zinc oxide, titanium oxide, aluminum oxide, aluminum sulfate, calcium sulfate, barium sulfate, magnesium sulfate, and siloxane bonds have a three-dimensional network structure , 1 silicon atom Is one or more methyl groups are selected from the polymethylsilsesquioxane powder bound <39> - cosmetic according to any one of <55>.
<57> The average particle diameter of the feel improving component is preferably 0.01 μm or more, more preferably 0.05 μm or more, still more preferably 0.2 μm or more, and preferably 50 μm or less, more preferably 20 μm or less, The cosmetic according to <56>, more preferably 8 μm or less.
<58> When a feel improving component is used as the component (D), the content thereof is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and still more preferably 1% by mass in the total composition. More preferably, it is 1.5% by mass or more, preferably 20% by mass or less, more preferably 10% by mass or less, still more preferably 5% by mass or less, and preferably 0.01 to 20%. The makeup according to any one of <39> to <57>, wherein the makeup is 0.1% by mass, more preferably 0.1 to 20% by mass, still more preferably 1 to 10% by mass, and still more preferably 1.5 to 5% by mass. Fee.
The total content of <59> component (D) is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, still more preferably 0.02% by mass or more, in the total composition. , Preferably 20% by mass or less, more preferably 15% by mass or less, further preferably 10% by mass or less, further preferably 5% by mass or less, and preferably 0.005 to 20% by mass, more preferably 0%. The cosmetic according to any one of <39> to <58>, which is 0.01 to 15% by mass, more preferably 0.02 to 10% by mass, and further preferably 0.02 to 5% by mass.
<60> The cosmetic according to any one of <38> to <59>, further comprising an aqueous medium, more preferably water.
<61> The concentration of the hardly water-soluble aromatic compound in the aqueous medium is preferably 0.1 to 50 g / L, more preferably 0.2 to 30 g / L, still more preferably 0.5 to 10 g / L, still more preferably. The cosmetic according to <60>, in which is 0.5 to 5 g / L, more preferably 0.5 to 2 g / L.

[Quantification of isopropylmethylphenol and trans-3,4'-dimethyl-3-hydroxyflavanone and 2- (1-ethylpentyl) -7-methoxychromone]
Using a high-performance liquid chromatograph manufactured by Hitachi, Inc., a column Cadenza CD-C18 (4.6 mmφ × 150 mm, 3 μm) manufactured by Intact Inc. was mounted, and a gradient method was performed at a column temperature of 40 ° C. The mobile phase A solution was 0.05 mol / L acetic acid aqueous solution, the B solution was acetonitrile, and the solution was fed at 1.0 mL / min. The gradient conditions are as follows.
Time (min) A liquid (%) B liquid (%)
0 85 15
20 80 20
35 10 90
50 10 90
50.1 85 15
60 85 15
Sample injection volume is 10 μL, detection is absorbance at 283 nm for isopropylmethylphenol, wavelength is 254 nm for trans-3,4′-dimethyl-3-hydroxyflavanone, and absorbance is 300 nm for 2- (1-ethylpentyl) -7-methoxychromone Was quantified.

[raw materials]
Isopropylmethylphenol (IPMP, Osaka Kasei Co., Ltd., purity 100%)
2- (1-Ethylpentyl) -7-methoxychromone (methoxychromone, manufactured by Kao Corporation, purity 99% or more)
Trans-3,4′-dimethyl-3-hydroxyflavanone (t-flavanone, manufactured by Kao Corporation, purity 99% or more)
1,3-butanediol (1,3-BG, manufactured by KH Neochem, purity 100%)
1,3-propanediol (1,3-PG, manufactured by DuPont, purity 100%)
Glycerin (Gly, Kao Corporation, purity 100%)
Diglycerin (DG, Sakamoto Pharmaceutical Co., Ltd., purity 100%)

Example 1
A stainless batch reactor with an internal volume of 190 mL was added to distilled water so that isopropylmethylphenol was 7.5 g / L, 1,3-butanediol was 300 g / L, and glycerin was 100 g / L. The heat treatment was performed with Nitto Koatsu Co., Ltd. After reaching 150 ° C., the temperature was maintained for 1 minute and quickly cooled to room temperature (25 ° C.) (cooling rate 0.5 ° C./s). The pressure during the heat treatment was 0.4 MPa. After cooling, the heat treatment solution was immediately extracted and filtered through a PTFE filter having a pore size of 0.2 μm to obtain an isopropylmethylphenol composition.
Table 1 shows the results of measurement of the treatment conditions and the isopropylmethylphenol concentration, 1,3-butanediol concentration, and glycerin concentration in the composition at 25 ° C.

Examples 2 to 11
Isopropylmethylphenol, 1,3-butanediol or 1,3-propanediol, glycerin or diglycerin was added to distilled water to the amounts shown in Table 1, respectively, and heat-treated in the same manner as in Example 1 to obtain isopropyl. A methylphenol composition was obtained.
Table 1 shows the treatment conditions and the results of measurement of the isopropylmethylphenol concentration, 1,3-butanediol concentration, 1,3-propanediol concentration, glycerin concentration and diglycerin concentration in the composition at 25 ° C.

Comparative Example 1
Without adding 1,3-butanediol and glycerin, isopropylmethylphenol 1.5 g / L was dispersed in distilled water, and an isopropylmethylphenol composition was obtained in the same manner as in Example 1. Table 2 shows the treatment conditions and the results of measuring the isopropylmethylphenol concentration in the composition.

Comparative Examples 2-7
Isopropylmethylphenol, 1,3-butanediol, and glycerin were added to distilled water to the amounts shown in Table 2, and the slurry was stirred at room temperature for 3 days (stirrer, 500 rpm). did. Table 2 shows the treatment conditions and the results of measurement of the isopropylmethylphenol concentration, 1,3-butanediol concentration, and glycerin concentration in the liquid part.

Comparative Examples 8-10
Without adding glycerin, isopropylmethylphenol and 1,3-butanediol were added to distilled water to the amounts shown in Table 2, respectively, and an isopropylmethylphenol composition was obtained in the same manner as in Example 1. Table 2 shows the treatment conditions and the measurement results of the isopropylmethylphenol concentration and the 1,3-butanediol concentration in the composition.

Comparative Examples 11-12
Without adding 1,3-butanediol, isopropylmethylphenol and glycerin were added to distilled water to the amounts shown in Table 2, respectively, and an isopropylmethylphenol composition was obtained in the same manner as in Example 1. Table 2 shows the treatment conditions and the results of measuring the isopropylmethylphenol concentration and the glycerin concentration in the composition.

Examples 12-15
2- (1-Ethylpentyl) -7-methoxychromone, 1,3-butanediol, and glycerin were added to distilled water to the amounts shown in Table 3, respectively, and heat-treated in the same manner as in Example 1. A 2- (1-ethylpentyl) -7-methoxychromone composition was obtained. Table 3 shows the treatment conditions and the results of measurement of 2- (1-ethylpentyl) -7-methoxychromone concentration, 1,3-butanediol concentration and glycerin concentration in the composition.

Comparative Example 13
Without adding 1,3-butanediol and glycerin, 1.0 g / L of 2- (1-ethylpentyl) -7-methoxychromone was dispersed in distilled water, and 2- (1- Ethylpentyl) -7-methoxychromone composition was obtained. Table 3 shows the treatment conditions and the measurement results of 2- (1-ethylpentyl) -7-methoxychromone concentration in the composition.

Comparative Examples 14-16
2- (1-Ethylpentyl) -7-methoxychromone, 1,3-butanediol, and glycerin were added to distilled water to the amounts shown in Table 3, respectively, and the slurry was stirred at room temperature for 3 days (stirrer). , 500 rpm), the solid was filtered off. Table 3 shows the results of measurement of 2- (1-ethylpentyl) -7-methoxychromone concentration, 1,3-butanediol concentration and glycerin concentration in the liquid part.

Comparative Examples 17-18
Without adding glycerin, 2- (1-ethylpentyl) -7-methoxychromone and 1,3-butanediol were added to distilled water so as to have the amounts shown in Table 3, respectively. A-(1-ethylpentyl) -7-methoxychromone composition was obtained. Table 3 shows the treatment conditions and the results of measurement of 2- (1-ethylpentyl) -7-methoxychromone concentration and 1,3-butanediol concentration in the composition.

Examples 16-17
Trans-3,4′-dimethyl-3-hydroxyflavanone, 1,3-butanediol, and glycerin were added to distilled water to the amounts shown in Table 4, respectively, and heat-treated in the same manner as in Example 1. A trans-3,4′-dimethyl-3-hydroxyflavanone composition was obtained. Table 4 shows the treatment conditions and the results of measurement of the trans-3,4′-dimethyl-3-hydroxyflavanone concentration, 1,3-butanediol concentration, and glycerin concentration in the composition.

Comparative Example 19
Without adding 1,3-butanediol and glycerin, 1.0 g / L of trans-3,4′-dimethyl-3-hydroxyflavanone was dispersed in distilled water, and in the same manner as in Example 14, trans-3,4 A '-dimethyl-3-hydroxyflavanone composition was obtained. Table 4 shows the treatment conditions and the measurement results of the trans-3,4′-dimethyl-3-hydroxyflavanone concentration in the composition.

Comparative Example 20
Trans-3,4′-dimethyl-3-hydroxyflavanone was added to distilled water so as to be 1.0 g / L, 1,3-butanediol was 500 g / L, and glycerin was 100 g / L. After stirring for 3 days (stirrer, 500 rpm), the solid was filtered off. Table 4 shows the results of measurement of the trans-3,4′-dimethyl-3-hydroxyflavanone concentration, 1,3-butanediol concentration, and glycerin concentration in the liquid part.

Comparative Example 21
Trans-3,4′-dimethyl-3-hydroxyflavanone and 1,3-butanediol were added to distilled water without adding glycerin, and trans-3,4′-dimethyl-3- A hydroxyflavanone composition was obtained. Table 4 shows the treatment conditions and the results of measurement of the trans-3,4′-dimethyl-3-hydroxyflavanone concentration and the 1,3-butanediol concentration in the composition.

As is apparent from Tables 1 to 4, a component (A) -containing composition having a high content of a hardly water-soluble aromatic compound can be obtained, and the solubility of the hardly water-soluble aromatic compound can be remarkably increased. It was.
Further, the component (A) -containing compositions obtained in Examples 1 to 17 did not precipitate even when cooled to room temperature, and maintained a stable dissolved state.

Examples 18 to 24, Comparative Examples 22 to 26
Using the isopropylmethylphenol (IPMP) compositions obtained in Examples 5 to 11 and Comparative Examples 1, 6, 8, 10 and 12, the deodorant cosmetics shown in Tables 5 and 6 were produced, and the stickiness, The sustainability of odor effect, bactericidal effect, smooth feeling and deodorizing effect was evaluated.
The concentration (25 ° C.) of water in the IPMP composition was 370.0 g / L (Example 18), 360.0 g / L (Example 19), 350.1 g / L (Example 20), 345.0 g. / L (Example 21), 265.0 g / L (Example 22), 360.1 g / L (Example 23), 361.6 g / L (Example 24), 999.8 g / L (Comparative Example 22) ), 389.6 g / L (Comparative Example 23), 698.7 g / L (Comparative Example 24), 492.9 g / L (Comparative Example 25), and 599.64 g / L (Comparative Example 26).
The results are shown in Tables 5 and 6.

(Production method)
Based on the IPMP concentration analysis values of the IPMP compositions obtained in Examples 5 to 11 and Comparative Examples 1, 6, 8, 10, and 12, the mixture was stirred at room temperature (25 ° C.) so that the IPMP concentration was 0.1% by mass. Dilute to lower water and dilute. In that case, the component (D) was previously mixed with water so that it might become a predetermined density | concentration before dripping of an IPMP composition.

(Evaluation methods)
The deodorant effect was evaluated by using each deodorant cosmetic for the whole body for five men who entered the environmental conditioning room (38 ° C., relative humidity 40%) for 30 minutes and left after sweating the whole body.

(1) Stickiness:
The user himself / herself scored the stickiness of the chest to which the deodorant cosmetic was applied, based on the following criteria, and the average value of five people was calculated.
0: Not sticky.
1: Slightly sticky.
2: Sticky.
3; very sticky.

(2) Deodorizing effect:
The user himself / herself scored the strength of the sweat odor of the whole body immediately after applying the deodorant cosmetic according to the following criteria. That is, the standard was divided into five stages, and the case where no odor was observed was evaluated as 4, and the case where it was not changed from before application was evaluated as 0, and the average value of 5 persons was calculated.

(3) Bactericidal effect:
Stamp medium (clean stamp "Nissui" SCDLP agar medium, Nissui Pharmaceutical Co., Ltd.) was pressed against the buttock where deodorant cosmetic was applied, and the number of colonies after 24 hours at 35 ° C was measured. The average value of 5 persons was calculated.
0: Number of colonies 0 / cm ² .
1: Number of colonies 1 to 10 / cm ² or less.
2: The number of colonies is 11 to 100 / cm ² or less.
3: The number of colonies is 101 / cm ² or more.

(4) Smooth feeling:
After applying the deodorant cosmetic, the user himself / herself scored the smooth feeling of the chest when 6 hours of daily life passed based on the following criteria. That is, the standard was divided into five stages, and the case of very slipping was evaluated as 4 and the case of not sliding at all was evaluated as 0, and the average value of 5 people was calculated.

(5) Persistence of deodorizing effect:
After applying the deodorant cosmetic, the user himself / herself scored the intensity of sweat odor of the whole body when daily life passed for 6 hours, and calculated the average value of 5 persons.
0: Stronger than before application.
1: Same as before application.
2: It became weaker than before application.
3; no smell at all.

When IPMP and the deodorizing component were combined, the effect of immediately deodorizing sweat odor that had already been expressed was obtained in addition to the effect of suppressing sweat odor expression due to the bactericidal effect of IPMP.
When IPMP and a bactericidal component were combined, the bactericidal performance was enhanced by using other bactericidal components in combination with the resident bacteria having insufficient bactericidal effect in IPMP, and the sweat odor suppressing effect was improved.
Combining IPMP and the powder that is a feel-enhancing component combined with the effect of promoting the transpiration of sweat by the powder resulted in an environment in which bacteria did not easily grow, and the sterilizing effect of IPMP was improved. Moreover, a smooth feeling was obtained.

Example 25
10 g of aluminum hydroxychloride, 0.2 g of polyoxyethylene hydrogenated castor oil and 0.05 g of fragrance were added to 2.5 g of the isopropylmethylphenol composition produced in Example 6, and purified water was added to prepare 100 g of a deodorant lotion. The composition is as follows.
IPMP 0.1 (mass%)
1,3-BG 1.25
Glycerin 0.25
Aluminum hydroxychloride 10.0
Polyoxyethylene (40) hydrogenated castor oil 0.2
Fragrance 0.05
Purified water balance
Total 100.0

Example 26
3.33 g of the isopropylmethylphenol composition produced in Example 5 was 6 g of 1,3 butylene glycol, 0.1 g of oleyl alcohol, 0.4 g of POE (20) oleyl alcohol ether, 0.2 g of methyl paraben, and 0.2 g of dipotassium glycyrrhizinate. 0.04 g of fragrance was added, and purified water was added to prepare 100 g of acne lotion. The composition is as follows.
IPMP 0.1 (mass%)
1,3-BG 7.67
Glycerin 0.33
Oleyl alcohol 0.1
POE (20) oleyl alcohol ether 0.4
Methylparaben 0.2
Dipotassium glycyrrhizinate 0.2
Perfume 0.04
Purified water balance
Total 100.0

Example 27
As the oil phase, 12 g of stearic acid, 14 g of myristic acid, 5 g of lauric acid, 3 g of jojoba oil, 14.047 g of sorbit, 10 g of glycerin, and 10 g of 1,3-butylene glycol were heated and dissolved and kept at 70 ° C. 20 g of purified water was added to 2.0 g of the isopropylmethylphenol composition produced in Example 7 to dissolve 5 g of potassium hydroxide, and the oil phase was slowly added while stirring. After further adding 4 g of N-methyltaurine and stirring for 10 minutes to sufficiently carry out a neutralization reaction, 1.9 g of POE (20) glycerol monostearate was added. A hand wash was prepared by slowly cooling to 25 ° C (cooling). The composition is as follows.
Stearic acid 12.0 (mass%)
Myristic acid 14.0
Lauric acid 5.0
Jojoba oil 3.0
Sorbit (70% aqueous solution of sorbitol)
Glycerin 10.2
1,3-BG 11.0
Potassium hydroxide 5.0
N-methyl taurine 4.0
POE (20) glycerol monostearate 1.9
IPMP 0.1
PG 8.421
Purified water balance
Total 100.0

Claims

A hardly water-soluble aromatic compound comprising a step of heat-treating (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol at 100 to 180 ° C. in the presence of an aqueous medium. The manufacturing method of a containing composition.
The method for producing a poorly water-soluble aromatic compound-containing composition according to claim 1, wherein the (A) poorly water-soluble aromatic compound is an aromatic compound having a solubility in water at 25 ° C of 0.5 g / L or less.
(A) The poorly water-soluble aromatic compound-containing composition according to claim 1 or 2, wherein the poorly water-soluble aromatic compound is one or more selected from phenolic antibacterial agents, chromone derivatives and flavanol derivatives. Production method.
(A) The poorly water-soluble aromatic compound is selected from isopropylmethylphenol, triclosan, 2- (1-ethylpentyl) -7-methoxychromone and trans-3,4′-dimethyl-3-hydroxyflavanone The method for producing a poorly water-soluble aromatic compound-containing composition according to claim 1 or 2, wherein the composition is a seed or two or more.
(B) The dihydric alcohol is one or more selected from ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, dipropylene glycol and polyethylene glycol. 5. The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of 4 above.
(C) The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of claims 1 to 5, wherein the trihydric or higher alcohol is glycerin or diglycerin.
The mass ratio [(A) / (B)] of (A) poorly water-soluble aromatic compound to (B) dihydric alcohol in the heat treatment step is 0.001-1. A process for producing the poorly water-soluble aromatic compound-containing composition according to claim 1.
The mass ratio [(B) / (C)] of (B) dihydric alcohol to (C) trihydric or higher alcohol is 1.5 to 10 in the heat treatment step. The manufacturing method of the hardly water-soluble aromatic compound containing composition of 1 item | term.
In the heat treatment step, the mass ratio of (A) poorly water-soluble aromatic compound to the total amount of (B) dihydric alcohol and (C) trihydric or higher alcohol [(A) / {(B) + (C) The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of claims 1 to 8, wherein 0.00] is 0.001 to 0.5.
The water-insoluble aromatic compound-containing composition according to any one of claims 1 to 9, further comprising a step of cooling the heat treatment liquid obtained by heat treatment at a cooling rate of 0.2 ° C / s or more. Manufacturing method.
A poorly water-soluble aromatic compound-containing composition obtained by the production method according to any one of claims 1 to 10.
The mass ratio [(A) / {(B) + (C)}] of (A) poorly water-soluble aromatic compound to the total amount of (B) dihydric alcohol and (C) trihydric or higher alcohol is 0.001. The hardly water-soluble aromatic compound-containing composition according to claim 11, wherein the composition is ˜0.5.
Cosmetics containing the poorly water-soluble aromatic compound-containing composition according to claim 11 or 12.
Furthermore, (D) Cosmetics of Claim 13 containing 1 or more types chosen from a deodorizing component, a bactericidal component, and a touch improvement component.
15. The mass ratio [(B) / (C)] of (B) dihydric alcohol to (C) trihydric or higher alcohol in the hardly water-soluble aromatic compound-containing composition is 1.5-10. Cosmetics.