TW201620489A - Manufacturing method for composition containing poorly water-soluble aromatic compound - Google Patents

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 DEG 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 composition containing poorly water-soluble aromatic compound

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

Aromatic compounds are widely used in cosmetics, pharmaceuticals, foods, daily necessities and other products. Many of the aromatic compounds are solid at room temperature, and those which are poorly soluble in water are usually dissolved in an alcohol and used (for example, Patent Documents 1 and 2).

However, the feeling of use is easily impaired by the stimulation of the skin by the alcohol. Also, the compositions that can be applied are limited.

Therefore, studies have been conducted on a technique in which a water-insoluble aromatic compound is soluble in water, and for example, an isopropylmethylphenol glucoside in which a sugar such as glucose is bonded to isopropylmethylphenol is reported (Patent Document 3) Or a method in which a surfactant and a humectant are used together to dissolve isopropylmethylphenol (Patent Document 4).

In addition, it is reported that a water-insoluble component such as a poorly water-soluble hair-generating component and a water-soluble aromatic compound such as polyphenol glycoside are heat-treated at 100 to 180 ° C in the presence of an aqueous medium to dissolve a water-insoluble hair growth component (Patent Document) 5).

[Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2009-96777

[Patent Document 2] Japanese Patent Laid-Open Publication No. 2011-153122

[Patent Document 3] Japanese Patent Laid-Open Publication No. 2005-82506

[Patent Document 4] Japanese Patent Laid-Open Publication No. 2011-98919

[Patent Document 5] Japanese Patent Laid-Open Publication No. 2013-124225

The present invention provides a step of heat-treating (A) a poorly water-soluble aromatic compound, (B) a glycol, and (C) a trivalent or higher alcohol in a presence of an aqueous medium at 100 to 180 ° C. A method for producing a composition of a poorly water-soluble aromatic compound, a composition containing a poorly water-soluble aromatic compound obtained by the production method, and a cosmetic containing the composition containing the poorly water-soluble aromatic compound.

However, the so-called glycoside obtained by adding sugar to the poorly water-soluble aromatic compound itself, such as isopropylmethylphenol glucoside, has high solubility in water, but the manufacturing steps are complicated, so the cost is high. Therefore, it is economically disadvantageous to use isopropylmethylphenol glycoside instead of isopropylmethylphenol or to use polyphenol glycoside as a solubilizing agent.

On the other hand, in the method of dissolving a water-insoluble aromatic compound by using a surfactant, there is a case where a physiological effect of an aromatic compound such as a sufficient solubility and an antibacterial effect cannot be obtained.

Therefore, the present invention is to provide a composition containing a poorly water-soluble aromatic compound (the component (A) of the present invention) which is excellent in water solubility (hereinafter referred to as "containing component (A)). A novel method of composition").

Further, the present invention is intended to provide a cosmetic which stably contains a water-insoluble aromatic compound and which exerts its effects sufficiently.

The inventors of the present invention conducted various studies on the solubilization technique of a poorly water-soluble aromatic compound, and found that the water-insoluble aromatic compound, the diol, and the trihydric or higher alcohol are present at 100 ° C in the presence of an aqueous medium. The heat treatment is carried out at the above temperature, so that the water is insoluble in water compared with the solubility of water in a water-insoluble aromatic compound. The dissolution concentration of the fragrance compound is drastically increased, and it has been found that the composition treated as described above can suppress the precipitation of the aromatic compound even at room temperature, and stably maintain the high solubility of the component (A) with respect to water.

In addition, it has been found that by combining the composition containing the component (A) treated as described above with one or more selected from the group consisting of a deodorizing component, a sterilizing component, and a tactile sensation component, it is possible to obtain a water-insoluble aromatic A cosmetic which has an effect of a compound and which sufficiently exhibits the effects of the components to be combined.

According to the present invention, the composition containing the component (A) which is excellent in solubility in water of the component (A) can be produced at low cost. By using the composition containing the component (A), the use of ethanol can be reduced or avoided, and thus an aqueous product having less skin irritation can be provided.

Moreover, the cosmetic of the present invention can sufficiently exhibit the effect of the poorly water-soluble aromatic compound by using the composition containing the component (A) which is excellent in water solubility of the component (A). When an aromatic antibacterial component is used as the water-insoluble aromatic compound, an excellent deodorizing effect and a sterilizing effect can be obtained, and a smooth feeling can be obtained without a sticky feeling.

In the method for producing a composition containing the component (A) of the present invention, the (A) poorly water-soluble aromatic compound, (B) glycol, and (C) trihydric or higher alcohol are contained in the presence of an aqueous medium. The step of heat treatment is carried out at 100 to 180 °C.

As the (A) water-insoluble aromatic compound used in the present invention, those having poor water solubility can be preferably used. For example, the solubility in water at 25 ° C is 0.5 g / L or less, further 0.3 g / L or less, and further 0.2 g. An aromatic compound below /L.

Further, an aromatic compound having a solubility of (B) diol at 25 ° C of 5 g/L or more, further 10 g/L or more, and further 20 g/L or more can be preferably used. Here, the solubility indicates the number of grams of the solute dissolved in 1 L of the solution, and the unit is [g/L].

The aromatic compound is not particularly limited, and examples thereof include an aromatic compound which can be used as an antibacterial component, a whitening component, and a hair growth component. (A) The water-insoluble aromatic compound may be one type or a mixture of two or more types.

Examples of the aromatic antibacterial component include a phenolic antibacterial agent and a preservative.

The phenolic antibacterial agent is preferably a chlorophenol antibacterial agent such as triclosan, clariparin, cyancholine, chlorophenol, dichlorophenol, hexachlorophenol, xylenol or chlorocresol; o-phenylphenol Further, isopropylmethylphenol is further preferably triclosan or isopropylmethylphenol, and further preferably isopropylmethylphenol.

The preservative is preferably methyl p-hydroxybenzoate, ethyl p-hydroxybenzoate, propyl p-hydroxybenzoate, isopropyl p-hydroxybenzoate, butyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate, Parabens such as benzyl hydroxybenzoate.

Examples of the aromatic whitening component include a chromone derivative and the like.

The chromone derivative preferably has a linear or branched alkyl group having 1 to 15 carbon atoms at the 2-position of the chromone, 4H-1-benzopyran-4-one, and has 7 positions. A compound of a hydrogen atom, a hydroxyl group or an alkoxy group.

As an example of such a chromone derivative, 2-butyl chromone, 2-pentyl chromone, 2-heptyl chromone, 2-mercapto chromone, 2-hexadecyl chromone, 2-(1- Ethylpentyl chromone, 2-butyl-7-methoxy chromone, 2-pentyl-7-methoxy chromone, 2-heptyl-7-methoxy chromone, 2-mercapto-7 -methoxy chromone, 2-pentadecyl-7-methoxy chromone, 2-(1-ethylpentyl)-7-methoxy chromone, 7-hydroxy-2-methyl chromone, 7 -hydroxy-2-butyl chromone, 7-hydroxy-2-pentyl chromone, 7-hydroxy-2-heptyl chromone, 7-hydroxy-2-indolyl ketone, 7-hydroxy-2-pentadecyl chromone , 7-hydroxy-2-(1-ethylpentyl) chromone, and the like. Among them, 2-(1-ethylpentyl)-7-methoxychromone is preferred.

The chromone derivative can be produced by a known method, for example, the method described in JP-A-7-108208.

Examples of the aromatic hair growth component include a flavanol derivative such as trans-3,4'-dimethyl-3-hydroxyflavanone; benzyl nicotinic acid, niacin acid vitamin E, and nicotine. Nicotinic acid such as β-butoxyethyl acid; α-vitamin E, dl-α-vitamin E, niacin vitamin E, natural vitamin E and other vitamin E; Mineledine, bimatoprost, tafluprost, vanillyl citrate, digestive extract, capsicum and so on.

Among them, trans-3,4'-dimethyl-3-hydroxyflavanone, benzyl nicotinic acid, niacin acid vitamin E, nicotinic acid β-butoxyethyl ester, and α-vitamin are preferred. E, citric acid dl-α-vitamin E, niacin acid vitamin E, natural vitamin E, minulidine, bimatoprost, tafluprost, vanillyl citrate, digestive extract and capsicum, preferably It is trans-3,4'-dimethyl-3-hydroxyflavanone. The flavanol derivative can be produced by a known method, for example, the method described in JP-A-2000-198779.

The general name of the alcohol in which two hydrogens of the (B) diol-based hydrocarbon used in the present invention are substituted with a hydroxy group, for example, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl Alkyl glycols such as 1,3-propanediol and 1,3-butanediol; and polyalkylene glycols such as diethylene glycol, dipropylene glycol, polyethylene glycol, and polypropylene glycol. Among them, in terms of solubilization of the water-insoluble aromatic compound, ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, 1,3-butylene glycol, dipropylene glycol, and more preferably 1,2-propanediol, 1,3-propanediol, and 1,3-butanediol. The weight average molecular weight of the polyethylene glycol is preferably from 200 to 20,000.

(B) The diol may be used singly or in combination of two or more.

The general name of the alcohol in which three or more hydrogens of the trivalent or higher alcohol-based hydrocarbons used in the present invention are substituted with a hydroxyl group, for example, glycerol such as glycerin, diglycerin or triglycerin; 1, 2, 4-butanetriol, 1,2,5-pentanetriol, 2-methylpropanetriol, 2-methyl-1,2,4-butanetriol, trimethylolethane, trimethylol The triol such as propane is preferably a three- to five-membered alcohol, more preferably a three-valent alcohol. In particular, in view of the solubility of the water-insoluble aromatic compound, glycerin is preferred, and glycerin or diglycerin is preferred from the viewpoint of application to a cosmetic.

(C) The trihydric or higher alcohol may be used singly or in combination of two or more.

The aqueous medium used in the present invention means an aqueous solution of water and an organic solvent. Examples of the water include tap water, distilled water, ion-exchanged water, and purified water. As having The organic solvent is not particularly limited as long as it can be uniformly mixed with water. The organic solvent is preferably one of a carbon number of 4 or less, more preferably propanol or ethanol, and is preferably ethanol from the viewpoint of application to a cosmetic. Further, in the present invention, the organic solvent is a compound of (B) diol and (C) ternary or higher alcohol.

When an organic solvent is used, the solubility of the (A) poorly water-soluble aromatic compound in water is high, but from the viewpoint of irritation to the skin, it is preferred to reduce the amount of the organic solvent used. The concentration of the organic solvent in the aqueous solution is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, still more preferably 0 to 10% by mass, still more preferably 0 to 1% by mass, and further preferably substantially Above 0% by mass, ie no organic solvent is included.

(A) The poorly water-soluble aromatic compound may be dispersed in a solution obtained by dissolving (B) a diol and (C) a trihydric or higher alcohol in an aqueous medium, and supplying it in a state of a slurry. Further, the (A) poorly water-soluble aromatic compound may be temporarily dissolved or dispersed in the (B) diol and the (C) ternary or higher alcohol, and the mixture may be mixed with an aqueous medium and then subjected to heat treatment.

In the case of heat treatment, a heat-treated raw material containing an aqueous medium, (A) a poorly water-soluble aromatic compound, (B) a glycol, and (C) a trihydric or higher alcohol is prepared and heat-treated.

The content of the (A) poorly water-soluble aromatic compound in the heat-treated raw material varies depending on the type thereof, and is usually preferably 0.1 g/L or more, further 0.5 g/L or more, and further 0.7 g in terms of productivity. /L or more, further 0.9 g/L or more, further 1 g/L or more, further 2 g/L or more, further 7.5 g/L or more, and further 30 g/L, and further preferably 150 g/ in terms of fluidity. L is not more than 100 g/L, 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, it is preferably 0.1 to 150 g/L, more preferably 0.1 to 100 g/L, still more preferably 0.5 to 75 g/L, still more preferably 0.7 to 60 g/L, still more preferably 0.9 to 55 g/L, and further It is preferably 1 to 55 g/L, more preferably 1 to 50 g/L, still more preferably 2 to 50 g/L, still more preferably 7.5 to 50 g/L, still more preferably 30 to 50 g/L.

The content of the (B) diol in the heat-treated raw material varies depending on the type thereof, and is usually preferably 1 g/L or more, further 10 g/L or more, and further 20 g in terms of solubility of the component (A). It is more preferably 100 g/L or more, further preferably 300 g/L or more, and more preferably 700 g/L or less, further 600 g/L or less, and further 500 g/L in terms of fluidity. the following. Further, it is preferably from 1 to 700 g/L, more preferably from 10 to 600 g/L, still more preferably from 20 to 500 g/L, still more preferably from 100 to 500 g/L, still more preferably from 300 to 500 g/L.

The content of the (C) trihydric or higher alcohol in the heat-treated raw material varies depending on the type thereof, and in terms of the solubility of the component (A), it is preferably 1 g/L or more and further 10 g/L or more. 50 g/L or more and further 100 g/L or more, in terms of storage stability and fluidity, it is preferably 500 g/L or less, further 300 g/L or less, further 250 g/L or less, and further 200 g/ L or less. Further, it is 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.

Regarding the mass ratio [(A)/(B)] of the component (A) to the component (B) in the heat-treated raw material, the dissolution of the component (A) in the composition containing the component (A) obtained after cooling In terms of properties, it is preferably 0.001 or more, further 0.002 or more, further 0.02 or more, further 0.025 or more, and further preferably 0.06 or more, and further preferably 1 or less, further 0.5 or less, further 0.2 or less, further 0.15 or less, and further 0.13. Hereinafter, it is further 0.12 or less, and further 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, still more preferably 0.002 to 0.13, still more preferably 0.002 to 0.12, and further It is preferably from 0.002 to 0.11, further preferably from 0.02 to 0.11, still more preferably from 0.025 to 0.11, still more preferably from 0.06 to 0.11.

When the composition containing the component (A) obtained by the production method of the present invention is used in the case of the following cosmetic, the mass ratio of the component (A) to the component (B) in the heat-treated raw material is [ (A)/(B)], in the composition containing the component (A) obtained after cooling The solubility of the component (A) is preferably 0.02 or more, further preferably 0.025 or more, further preferably 0.06 or more, and further preferably 1 or less, further 0.5 or less, and further 0.15 or less. Further, it is preferably 0.02 to 1, more preferably 0.025 to 0.5, still more preferably 0.06 to 0.15.

Regarding the mass ratio [(A)/(C)] of the component (A) to the component (C) in the heat-treated raw material, the dissolution of the component (A) in the composition containing the component (A) obtained after cooling In terms of properties, it is preferably 0.001 or more, further 0.005 or more, further 0.01 or more, further 0.12 or more, further 0.15 or more, and further 0.17 or more, and further preferably 1.5 or less, further 1 or less, further 0.7 or less, and further 0.55. the following. Further, it is preferably 0.001 to 1.5, further preferably 0.001 to 1, further preferably 0.005 to 0.7, further preferably 0.01 to 0.55, still more preferably 0.12 to 0.55, still more preferably 0.15 to 0.55, and further It is preferably 0.17 to 0.55.

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

Regarding the mass ratio [(B)/(C)] of the component (B) to the component (C) in the heat-treated raw material, the dissolution of the component (A) in the composition containing the component (A) obtained after cooling In terms of properties, it is preferably 1.5 or more, further 2 or more, and further 2.5 or more, and more preferably 10 or less, further preferably 8 or less, and further preferably 6 or less. Further, it is preferably 1.5 to 10, more preferably 2 to 8, and still more preferably 2.5 to 6.

Further, 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-treated raw material is obtained after cooling. The solubility of the component (A) in the composition containing the component (A) and the storage stability of the composition containing the component (A) are preferably 0.001 or more, further 0.002 or more, and further preferably 0.015 or more. , Further, it is preferably 0.015 or more, further 0.05 or more, and further 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, it is preferably 0.001 to 0.5, more preferably 0.001 to 0.2, still more preferably 0.002 to 0.15, still more preferably 0.002 to 0.12, still more preferably 0.002 to 0.10, still more preferably 0.015 to 0.10, and further Preferably, it is from 0.019 to 0.10, and more preferably from 0.05 to 0.10.

When the composition containing the component (A) obtained by the production method of the present invention is blended in the case of the following cosmetic, the component (A) relative to the component (B) and the component (C) in the heat-treated raw material is used. The mass ratio of the total amount of [(A)/{(B)+(C)}]), the solubility of the component (A) in the composition containing the component (A) obtained after cooling, and the content The storage stability of the composition of the component (A) is preferably 0.015 or more, further preferably 0.019 or more, further preferably 0.05 or more, and further preferably 0.5 or less, further 0.2 or less, and further 0.1 or less. Further, it is preferably from 0.015 to 0.5, more preferably from 0.019 to 0.5, still more preferably from 0.05 to 0.2, still more preferably from 0.05 to 0.1.

In the production method of the present invention, a surfactant may be used, and from the viewpoint of maintaining the physiological activity of the (A) poorly water-soluble aromatic compound or reducing the irritation to the skin, it is preferred to use the surfactant. cut back. The content of the surfactant in the heat-treated 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, and further preferably substantially 0 g/L. That is, no surfactant is included.

The method of heat-treating (A) the poorly water-soluble aromatic compound, (B) glycol, and (C) trivalent or more alcohol in the presence of an aqueous medium is not specifically limited, and a well-known method can apply.

The heat treatment temperature is 100 to 180 ° C, and in terms of improving the solubility of the (A) poorly water-soluble aromatic compound, it is preferably 110 ° C or higher, more preferably 120 ° C or higher, and further, in terms of thermal stability. More preferably, it is 170 ° C or less, more preferably 160 ° C or less. Further, the temperature of the heat treatment is preferably from 110 to 170 ° C, more preferably from 120 to 160 ° C, still more preferably from 120 to 150 ° C. Examples of the mechanism for heating include water vapor and electricity.

The pressure at the time of 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, still more preferably 0.2 to 4 MPa, more preferably 0.2 to 4 MPa. 0.25 to 2 MPa, further preferably 0.3 to 1.5 MPa, further preferably 0.3 to 0.6 MPa. In addition, the gauge pressure is a pressure at which the atmospheric pressure is set to 0 MPa. Further, it is preferably set to be equal to or higher than the saturated vapor pressure of water. A gas may be used for pressurization, and examples of the usable gas include an inert gas, steam, nitrogen, helium, and the like. For pressurization, it is also possible to adjust by means of a back pressure valve without using a gas.

The heat treatment can also be carried out by any one of a batch method, a half batch method, a circulation method, and the like. Among them, the circulation method is preferable in terms of easy control of the heat treatment time.

With respect to the time of the heat treatment, in view of improving the solubility of the (A) poorly water-soluble aromatic compound, it is preferred that the aqueous medium is at least 0.1 minutes after the temperature of the heat treatment, more preferably 0.2 minutes or more, and further preferably. In the case of 0.5 minutes or more, in terms of thermal stability, it is preferably 30 minutes or shorter, more preferably 15 minutes or shorter, and still more preferably 8 minutes or shorter. Further, the heat treatment time is preferably from 0.1 to 30 minutes, more preferably from 0.2 to 15 minutes, even more preferably from 0.5 to 8 minutes, after the aqueous medium reaches the temperature of the heat treatment.

In the case of the flow-through method, the heat treatment time is an average residence time calculated by dividing the volume of the high-temperature high-pressure portion of the reactor by the supply rate of the aqueous medium.

The heat treatment can also be carried out by any one of a batch method, a half batch method, a circulation method, and the like. Among them, the circulation method is preferable in terms of easy control of the heat treatment time.

With respect to the time of the heat treatment, in view of improving the solubility of the (A) poorly water-soluble aromatic compound, it is preferred that the heat-treated raw material is at least 0.1 minutes after the temperature of the heat treatment, more preferably 0.2 minutes or more, and further Good for more than 0.5 minutes, it is stable In terms of properties, it is preferably 30 minutes or shorter, more preferably 15 minutes or shorter, and still more preferably 8 minutes or shorter. Further, the heat treatment time is preferably 0.1 to 30 minutes, more preferably 0.2 to 15 minutes, still more preferably 0.5 to 8 minutes, after the heat treatment raw material reaches the temperature of the heat treatment.

In the case of the flow-through method, the heat treatment time is an average residence time calculated by dividing the volume of the high-temperature high-pressure portion of the reactor by the supply rate of the heat-treated raw material.

The flow rate of the aqueous medium in the case of the flow-through 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 preferably from 60 L/min to 1,000 L/min.

In the production method of the present invention, it is preferred to include a step of cooling the heat treatment liquid obtained by the heat treatment to 90 ° C or lower, preferably 50 ° C or lower, more preferably 30 ° C or lower. In the case of obtaining a composition containing the component (A) in a liquid form, it is preferably cooled to 0 ° C or higher, more preferably to 10 ° C or higher.

The cooling rate of the heat treatment liquid calculated based on the time required for the temperature of the heat treatment to be lowered to 90 ° C is preferably 0.2 ° C / s or more, more preferably 0.5 ° C / s or more, and still more preferably 1 ° C / s or more. Further, it is preferably 3 ° C / s or more, and more preferably 5 ° C / s or more. The greater the cooling rate, the more the solubility of the poorly water-soluble aromatic compound can be improved. Therefore, the upper limit of the cooling rate is not particularly limited, and is preferably, for example, 100 ° C / s or less, and more preferably 50 ° C / s or less from the viewpoint of restrictions on the production equipment.

In terms of the solubility stability of the component (A) in the composition containing the component (A) obtained, it is preferred to further carry out the step of removing the solid matter remaining undissolved from the heat treatment liquid. The method for removing the solid matter is not particularly limited, and can be carried out, for example, by centrifugation or decantation or filtration.

The composition containing the component (A) thus obtained contains (A) poorly water-soluble in an aqueous medium. An aromatic compound, (B) diol, or (C) ternary or higher alcohol, although (A) the content of the poorly water-soluble aromatic compound is high, even at room temperature, it is difficult to store at room temperature. The precipitation of the soluble aromatic compound is also suppressed. Moreover, it is excellent in solubility in water.

The content of the component (A) in the composition containing the component (A) of the present invention is preferably 0.5 g/L or more, further 1 g/L or more, and further 1.5 g/% in terms of logistics or usability. L or more, further 2 g/L or more, further 7.5 g/L or more, and further 30 g/L, more preferably 150 g/L or less, further 100 g/L or less, further 75 g/L or less, and further 60 g/L or less, and further 55 g / L or less, and further 50 g / L or less.

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

In the composition containing the component (A) of the present invention, the content of the (C) trihydric or higher alcohol is in terms of the solubility and stability of the component (A) in the composition of the component (A). In the total composition, it is preferably 1 g/L or more, more preferably 10 g/L or more, further preferably 50 g/L or more, further preferably 100 g/L or more, and more preferably 500 g/L or less. Further, it is preferably 300 g/L or less, more preferably 250 g/L or less, still more preferably 200 g/L or less. Further, it is 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.

Regarding the mass ratio [(A)/(B)] of the component (A) to the component (B) in the composition containing the component (A) of the present invention, the stability of the composition containing the component (A) is contained. In particular, it is preferably 0.001 or more, further 0.002 or more, further 0.02 or more, and further preferably 0.025 or more. Further, it is preferably 0.0 or more, further preferably 1 or less, further 0.5 or less, further 0.2 or less, further 0.15 or less, further 0.13 or less, further 0.12 or less, and further 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, still more preferably 0.002 to 0.13, still more preferably 0.002 to 0.12, and further It is preferably from 0.002 to 0.11, further preferably from 0.02 to 0.11, still more preferably from 0.025 to 0.11, still more preferably from 0.06 to 0.11.

The mass ratio [(A)/(C)] of the component (A) to the component (C) in the composition containing the component (A) of the present invention contains the component in the composition of the component (A) ( The solubility of A) is preferably 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, and further preferably 1.5 or less, further 1 or less, and further 0.7. Hereinafter, it is further 0.55 or less. Further, it is preferably 0.001 to 1.5, further preferably 0.001 to 1, further preferably 0.005 to 0.7, further preferably 0.01 to 0.55, still more preferably 0.12 to 0.55, still more preferably 0.15 to 0.55, and further It is preferably 0.17 to 0.55.

The mass ratio [(B)/(C)] of the component (B) to the component (C) in the composition containing the component (A) of the present invention contains the component in the composition of the component (A) ( The solubility of A) is preferably 1.5 or more, further 2 or more, and further 2.5 or more, and more preferably 10 or less, further 8 or less, or further 6 or less. Further, it is preferably 1.5 to 10, more preferably 2 to 8, and still more preferably 2.5 to 6.

Further, the mass ratio of the component (A) to the total amount of the component (B) and the component (C) in the composition containing the component (A) of the present invention [(A)/{(B)+(C) }], in terms of the stability of the composition containing the component (A), it is preferably 0.001 or more, further 0.002 or more, further 0.015 or more, further 0.019 or more, further 0.05 or more, and further preferably 0.5 or less. Further, it is 0.2 or less, further 0.15 or less, further 0.12 or less, and further 0.1 or less. Further, it is preferably 0.001 to 0.5, preferably 0.001 to 0.2, more preferably 0.002 to 0.15, still more preferably 0.002 to 0.12, still more preferably 0.002 to 0.1, still more preferably 0.015 to 0.1. It is preferably from 0.019 to 0.1, more preferably from 0.05 to 0.1.

The content of the organic solvent, particularly the one-carbon alcohol having a carbon number of 4 or less, in the composition containing the component (A) of the present invention is preferably a reduction in the amount of the organic solvent used from the viewpoint of irritation to the skin. The content of the organic solvent in the composition containing the component (A) is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, still more preferably 0 to 10% by mass, still more preferably 0 to 1% by mass. %, further preferably substantially 0% by mass, that is, does not contain an organic solvent.

The content of the surfactant in the composition containing the component (A) of the present invention desirably exhibits the effect of the (A) poorly water-soluble aromatic compound, and it is preferable to reduce the content of the surfactant. The content of the surfactant in the composition containing the component (A) is preferably 0 to 1 g/L, more preferably 0 to 0.5 g/L, still more preferably 0 to 0.1 g/L, and further preferably Essentially 0 g/L, ie no surfactant is included.

The composition containing the component (A) of the present invention can be used for various products such as cosmetics, pharmaceuticals, foods, and daily necessities. In particular, it is useful for a product used in a water system and further applied to a cosmetic. Examples of the cosmetic or pharmaceutical products include skin care materials such as washing materials, lotions, cosmetics for makeup, cosmetics for sunscreen, cosmetics for acne, cosmetics for deodorization, cosmetics for whitening, and shampoos. , hair restorer, toothpaste, mouthwash, mouthwash and so on.

The composition containing the component (A) of the present invention may also 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 preferably 0.1 to 50 g/L, further 0.2 to 30 g/L, further 0.5 to 10 g/L, and further 0.5 to 5 g/L. And further 0.5~2g/L. In the composition containing the component (A) of the present invention, the solubility of the poorly water-soluble aromatic compound is drastically increased as compared with the solubility of the usual poorly water-soluble aromatic compound in water, but it can be diluted to a desired level. Even in this case, the concentration of the poorly water-soluble aromatic compound is suppressed and the stability is high. Further, it is expected that the physiological activity of the poorly water-soluble aromatic compound is high.

The cosmetic of the present invention contains the composition containing the component (A) obtained as described above, and preferably contains the mass ratio of the (B) diol to the (C) ternary or higher alcohol [(B)/ (C)] The composition containing the component (A) of 1.5 to 10 is further preferably further contained (D) one or more selected from the group consisting of a deodorizing component, a sterilizing component, and a tactile sensation improving component. Thereby, the effect of the poorly water-soluble aromatic compound can be fully exhibited, and the effect of the component to be combined can be fully exhibited.

In the case where the composition containing the component (A) of the present invention is used for a cosmetic, the mass ratio of the component (B) to the component (C) in the composition containing the component (A) [(B)/ (C)], in terms of solubility of the component (A) in the composition containing the component (A), it is preferably 1.5 or more, further 2 or more, further 2.5 or more, and more preferably 10 or less. Further, it is 8 or less and further 6 or less. Further, it is preferably 1.5 to 10, more preferably 2 to 8, and still more preferably 2.5 to 6.

Further, in the case where the composition containing the component (A) of the present invention is used for a cosmetic, the content of the component (A) in the composition containing the component (A) is in terms of logistics or usability. It is preferably 1 g/L or more, further 2 g/L or more, further 7.5 g/L or more, and further 30 g/L or more.

In the case where the composition containing the component (A) of the present invention is used for a cosmetic, the mass ratio of the component (A) to the component (B) in the composition containing the component (A) [(A)/ (B)] From the viewpoint of improving the stability of the poorly water-soluble aromatic compound, it is preferably 0.02 or more, further preferably 0.025 or more, further preferably 0.06 or more, and further preferably 1 or less, further 0.5 or less, and further 0.15 or less. Further, it is preferably 0.02 to 1, more preferably 0.025 to 0.5, still more preferably 0.06 to 0.15.

In the case where the composition containing the component (A) of the present invention is used for a cosmetic, the mass ratio of the component (A) to the component (C) in the composition containing the component (A) [(A)/ (C)], from the viewpoint of improving the stability of the composition containing the component (A), it is preferably 0.12 or more, further 0.15 or more, further 0.17 or more, more preferably 1.5 or less, further 1 or less, and further 0.6 or less. Further, it is preferably 0.12 to 1.5, further preferably 0.15 to 1, and further preferably 0.17 to 0.6.

In the case where the composition containing the component (A) of the present invention is used for a cosmetic, the total amount of the component (A) in the composition containing the component (A) relative to the component (B) and the component (C) The mass ratio [(A)/{(B)+(C)}]] is preferably 0.015 or more, further preferably 0.019 or more, further preferably 0.05 or more, and further preferably 0.5 in terms of stability. Hereinafter, it is further 0.2 or less, and further 0.1 or less. Further, it is preferably from 0.015 to 0.5, more preferably from 0.019 to 0.5, still more preferably from 0.05 to 0.2, still more preferably from 0.05 to 0.1.

In the cosmetic of the present invention, the content of the poorly water-soluble aromatic compound of the component (A) is such that the effect of the poorly water-soluble aromatic compound is sufficiently exhibited, and the aromatic antimicrobial component is used as the poorly water-soluble aromatic compound. In the case of a compound, an excellent deodorizing effect and a bactericidal effect are obtained, and from the viewpoint of obtaining a smooth feeling without a sticky feeling, the total composition is preferably 0.01% by mass or more, more preferably 0.02% by mass or more, and further It is preferably 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. Further, the content of the component (A) is preferably from 0.01 to 1% by mass, more preferably from 0.02 to 0.5% by mass, even more preferably from 0.05 to 0.3% by mass, based on the total composition.

In the cosmetic of the present invention, the content of the glycol of the component (B) is such that the effect of the poorly water-soluble aromatic compound is sufficiently exhibited, and the aromatic antimicrobial component is used as the poorly water-soluble aromatic compound. In the case of obtaining a superior deodorizing effect and a bactericidal effect, and having a feeling of smoothness without a sticky feeling, the total composition is preferably 0.09% by mass or more, more preferably 0.18% by mass or more, and further preferably. It is 0.3% by mass or more, more preferably 0.45% by mass or more, and is preferably 8.4% by mass or less, more preferably 7% by mass or less, further preferably 5.5% by mass or less, and still more preferably 5% by mass or less. Further, the content of the component (B) is preferably from 0.09 to 8.4% by mass, more preferably from 0.18 to 7% by mass, still more preferably from 0.3 to 5.5% by mass, even more preferably from 0.45 to 5% by mass. .

In the cosmetic of the present invention, the content of the trihydric or higher alcohol of the component (C) is sufficient to exert the effect of the poorly water-soluble aromatic compound and to use aromatic When the antibacterial component is used as a water-insoluble aromatic compound, an excellent deodorizing effect and a bactericidal effect can be obtained, and from the viewpoint of obtaining a smooth feeling without a sticky feeling, the total composition is preferably 0.01% by mass or more. It is preferably 0.03 mass% or more, more preferably 0.06 mass% or more, further preferably 0.09% by mass or more, and more preferably 2.86 mass% or less, more preferably 2.5% by mass or less, still more preferably 2 mass% or less. More preferably, it is 1.72 mass% or less. Further, the content of the component (C) is preferably from 0.01 to 2.86 mass%, more preferably from 0.03 to 2.5 mass%, still more preferably from 0.06 to 2 mass%, still more preferably from 0.09 to 1.72 mass%, based on the total composition. .

The component (D) used in the present invention is one or more selected from the group consisting of the deodorizing component, the sterilizing component, and the tactile sensation improving component.

In the component (D), the deodorizing component may be any one of a chemical deodorizing method; a physical deodorizing method; a biological deodorizing method; and a sensory deodorizing method.

Examples of the chemical deodorization method include a metal oxide such as zinc oxide or titanium oxide which chemically adsorbs a relatively odorous substance, and a tris(hydroxymethyl)aminomethane (2-amino-2-) which neutralizes a relatively odorous substance. An amine such as hydroxymethyl-1,3-propanediol or an antioxidant such as dibutylhydroxytoluene which inhibits decomposition to a relatively odorous substance.

Examples of the physical deodorizing method include a porous substance such as cyclodextrin, hydroxyapatite, chitosan fine particles, and activated carbon which physically adsorb a relatively odorous substance.

As a biological deodorization method, a yellow eucalyptus extract, oleic acid, etc. are mentioned.

As the person who feels the deodorant, a fragrance such as L-menthol can be mentioned.

Among these, from the viewpoint of the quick-acting effect of the deodorizing effect, it is preferably a deodorizing component selected from the group consisting of amines, and more preferably tris(hydroxymethyl)aminomethane (2) from the viewpoint of usability. -Amino-2-hydroxymethyl-1,3-propanediol).

When the deodorizing component is used as the component (D), the total composition is preferably 0.01% by mass or more, and more preferably 0.05% by mass or more, from the viewpoint of reducing the slipping feeling at the time of coating. Further, it is preferably 0.07% by mass or more, and more preferably 0.09% by mass. From the viewpoint of reducing the stickiness at the time of coating, it is preferably 2% by mass or less, more preferably 1.5% by mass or less, further preferably 1% by mass or less, and still more preferably 0.9% by mass or less. In the case where the deodorizing component is used as the component (D), the total content thereof is 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. More preferably, it is 0.09 to 0.9% by mass.

In the component (D), examples of the bactericidal component include alkyltrimethylammonium bromide, cetylpyridinium chloride, silver-supported inorganic particles, hydrochloric acid lysozyme, benzalkonium chloride, and cetyl chloride. Ammonium (CPC), hydrazine, and the like. Examples of the silver-supporting inorganic particles include silver-supported zeolite and silver-supported calcium nepheline.

Among these, from the viewpoint of the persistence of the dry feeling and the feeling of slipping, it is preferably benzalkonium chloride.

When the sterilizing component is used as the component (D), the content of the sterilizing component is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, and more preferably from the viewpoint of obtaining a high bactericidal effect. It is preferably 0.02% by mass or more, more preferably 0.03% by mass or more, and is preferably 4% by mass or less, more preferably 3% by mass or less, further preferably 1% by mass or less, and still more preferably 0.5% by mass or less. . In the case where the sterilizing component is used as the component (D), the content thereof is preferably 0.005 to 4% by mass, more preferably 0.01 to 3% by mass, still more preferably 0.02 to 1% by mass, based on the total composition. More preferably, it is 0.03 to 0.5% by mass.

In the component (D), the touch-sensing component may be a powder, or may be any of an inorganic powder, an organic powder, and a composite powder.

Examples of the organic powder include a nylon resin (a commercially available product, manufactured by Elf Atochem Co., Ltd., ORGASOL 2002 EXD NAT COS TypeS, ORGASOL 4000 EXD NAT COS; manufactured by Toray Industries, SP-500, etc.), and a polystyrene resin (as a resin). Commercial product, manufactured by Sumitomo Chemical Industries Co., Ltd., Fine Pearl; manufactured by Sekisui Chemicals Co., Ltd., TECHPOLYMER SB; manufactured by Research Chemical Co., Ltd., Fine Powder SGP Etc.), polyethylene resin (sold as a commercial product, manufactured by Asahi Kasei Co., Ltd., Suntec PAK0025; manufactured by Sumitomo Seika Co., Ltd., flowable particles, etc.), polymethyl methacrylate resin (available as a commercial product, manufactured by Matsumoto Oil & Fats Pharmaceutical Co., Ltd.) Matsumoto Microsphere M; manufactured by Sekisui Chemicals Co., Ltd., TECHPOLYMER MB; manufactured by Synthetic Chemical Co., Ltd., Fine Powder MP, etc., (meth)acrylate resin, polyoxynoxy resin (as a commercial product, manufactured by Shin-Etsu Chemical Co., Ltd.) KMP-590; manufactured by Toshiba Silicone, Tospearl 145, Tospearl 2000B, etc., polyoxyxene rubber powder (sold as a commercial product, manufactured by Shin-Etsu Chemical Co., Ltd., KMP-597, KMP-598; manufactured by Toray Industries, TORAYFIL 501 TORAYFIL 505, TORAYFIL 506, TORAYFIL 601, etc.), cellulose granules (commercially available, manufactured by Asahi Kasei Corporation, Avicel RC-A591NF, etc.). Further, a crosslinked (meth) acrylate resin powder such as lauryl methacrylate, dimethyl methacrylate or sodium methacrylate (Japanese Patent Laid-Open Publication No. 2006-8659) may be used. .

Examples of the inorganic powder include talc, sericite, mica, kaolin, clay, bentonite, citric acid, phthalic anhydride, magnesium citrate, mica, magnesium oxide, zinc oxide, titanium oxide, aluminum oxide, aluminum sulfate, and sulfuric acid. Calcium, barium sulfate, magnesium sulfate, and the like.

Further, as a powder having an intermediate structure in which an inorganic powder and an organic powder are combined, a network structure in which a siloxane chain is three-dimensionally extended and a ruthenium atom is bonded to a methyl group is exemplified. Methyl sesquioxane powder and the like.

In the case where the powder is used as the tactile sensation improving component, it is also included as a deodorizing component in the deodorizing component.

The average particle diameter is preferably 0.01 μm or more, more preferably 0.05 μm or more, and further preferably 0.2 μm or more, from the viewpoint of reducing the dry feel, and the roughness is suppressed and the smoothness is further improved. The average particle diameter is preferably 50 μm or less, more preferably 20 μm or less, and still more preferably 8 μm or less from the viewpoint of improvement.

When the tactile sensation component is used as the component (D), the content is reduced. From the viewpoint of less dryness, suppression of roughness, and improvement of smoothness, it is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, still more preferably 1% by mass or more, and further preferably from the viewpoint of the total composition. It is 1.5% by mass or more, and preferably 20% by mass or less, more preferably 10% by mass or less, and still more preferably 5% by mass or less. Further, when the touch-sensing component is used as the component (D), the content thereof is preferably from 0.01 to 20% by mass, more preferably from 0.1 to 20% by mass, even more preferably from 1 to 10% by mass, based on the total composition. More preferably, it is 1.5 to 5% by mass.

In addition, the component (D) is selected from one or more of a deodorizing component, a sterilizing component, and a tactile sensation improving component, and may be used, for example, in combination with a sterilizing component and/or a tactile sensation component.

The total content of the component (D) cannot be determined depending on the type of the component to be used, and for example, in terms of the function of each component, that is, the function of deodorizing, sterilizing, and tactile sensation, It is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, further preferably 0.02% by mass or more, and more preferably 20% by mass or less, more preferably 15% by mass or less, still more preferably 10% by mass or less. Further, it is more preferably 5% by mass or less. Further, the total content of the 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, still more preferably 0.02 to 5% by mass, based on the total composition. .

The cosmetic of the present invention preferably further contains an aqueous medium such as water. The composition containing the component (A) may be added to an aqueous medium, and then the component (D) may be added to the other component to be mixed, or the composition (D) containing the component (A) or the component (D) may be added. The other components are added independently or simultaneously.

The concentration of the poorly water-soluble aromatic compound relative to the aqueous medium is preferably 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 0.5 to 2 g/L.

The cosmetic of the present invention may contain, in addition to the above components, components used in usual cosmetics, such as oily components, surfactants, water-soluble polymers, and extracts. Classes, antioxidants, pigments, pH adjusters, UV absorbers, blood flow promoters, fragrances, etc.

The aspects and preferred embodiments of the present invention are shown below.

<1> A method for producing a composition containing a poorly water-soluble aromatic compound, which comprises (A) a poorly water-soluble aromatic compound, (B) a glycol, and (C) a trivalent or higher amount in the presence of an aqueous medium. The step of heating the alcohol at 100 to 180 ° C.

<2> The method for producing a composition containing a poorly water-soluble aromatic compound according to <1>, wherein (A) the poorly water-soluble aromatic compound has a solubility in water of preferably 0.5 g/L or less at 25 ° C, more preferably It is an aromatic compound of 0.3 g/L or less, more preferably 0.2 g/L or less.

<3> A method for producing a composition containing a poorly water-soluble aromatic compound according to <1> or <2>, wherein (A) the poorly water-soluble aromatic compound has a solubility in (B) diol at 25 ° C. It is an aromatic compound of 5 g/L or more, more preferably 10 g/L or more, further preferably 20 g/L or more.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of the above aspects, wherein the (A) poorly water-soluble aromatic compound is preferably selected from the group consisting of an antibacterial component and a whitening component. One or two or more kinds of the hair growth component are more preferably one or more selected from the group consisting of a phenolic antibacterial agent, a preservative, a chromone derivative, and a flavanol derivative.

<5> The method for producing a composition containing a poorly water-soluble aromatic compound according to <4>, wherein the phenol-based antibacterial agent is preferably selected from the group consisting of triclosan, clariparin, carbachol, chlorophenol, and One or more selected from the group consisting of chlorophenol, hexachlorophenol, chloroxylenol, chlorocresol, o-phenylphenol and isopropylmethylphenol, more preferably selected from the group consisting of triclosan and isopropylmethyl One or two kinds of phenols are further preferably isopropylmethylphenol.

<6> The method for producing a composition containing a poorly water-soluble aromatic compound according to <4>, wherein the preservative is preferably one or two selected from the group consisting of p-hydroxybenzoic acid esters, more preferably selected from the group consisting of p-hydroxyl groups. Methyl benzoate, ethyl p-hydroxybenzoate, propyl p-hydroxybenzoate, pair One or two kinds of isopropyl hydroxybenzoate, butyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate and benzyl p-hydroxybenzoate.

<7> The method for producing a composition containing a poorly water-soluble aromatic compound according to <4>, wherein the chromone derivative is preferably selected from the group consisting of 2-butyl chromone, 2-pentyl chromone, and 2-heptyl chromone. 2-nonyl chromone, 2-hexadecyl chromone, 2-(1-ethylpentyl) chromone, 2-butyl-7-methoxy chromone, 2-pentyl-7-methoxy chromone , 2-heptyl-7-methoxy chromone, 2-mercapto-7-methoxy chromone, 2-pentadecyl-7-methoxy chromone, 2-(1-ethylpentyl)- 7-methoxychromone, 7-hydroxy-2-methyl chromone, 7-hydroxy-2-butyl chromone, 7-hydroxy-2-pentyl chromone, 7-hydroxy-2-heptyl chromone, 7- One or more of hydroxy-2-indolyl ketone, 7-hydroxy-2-pentadecyl chromone, and 7-hydroxy-2-(1-ethylpentyl) chromone, more preferably 2- (1-Ethylpentyl)-7-methoxychromone.

<8> The method for producing a composition containing a poorly water-soluble aromatic compound according to <4>, wherein the hair growth component is preferably selected from the group consisting of a flavanol derivative, a nicotinic acid, a vitamin E, a leuprolide, and a horse. One or more of prostaglandin, tafluprost, vanillyl citrate, distillate extract and capsicum, more preferably selected from trans-3,4'-dimethyl-3-hydroxyl Flavanone, benzyl nicotinic acid, niacin acid vitamin E, nicotinic acid β-butoxyethyl ester, α-vitamin E, acetic acid dl-α-vitamin E, niacin acid vitamin E, natural vitamin E, One or more of minoxidin, bimatoprost, tafluprost, vanillyl citrate, distillate extract and capsicum, and more preferably trans-3,4'-dimethyl Base-3-hydroxyflavanone.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <8> wherein the (B) glycol is preferably selected from the group consisting of ethylene glycol and 1,2- One or more of propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, diethylene glycol, dipropylene glycol, polyethylene glycol, and polypropylene glycol More preferably, it is one or more selected from the group consisting of ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, and dipropylene glycol, and more preferably selected from 1,2. - one or two of propylene glycol, 1,3-propanediol and 1,3-butylene glycol on.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <9> wherein (C) the trivalent or higher alcohol is preferably selected from the group consisting of glycerin, diglycerin, and trisole. Glycerin, 1,2,4-butanetriol, 1,2,5-pentanetriol, 2-methylpropanetriol, 2-methyl-1,2,4-butanetriol, Trimethylol B One or two or more kinds of the alkane and the trimethylolpropane are more preferably one or more selected from the group consisting of glycerin, diglycerin and triglycerin, and more preferably glycerin and/or diglycerin.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <10> wherein the aqueous medium is preferably an aqueous solution of water or an organic solvent, more preferably water or carbon number. An aqueous solution of one of the following lower alcohols is more preferably an aqueous solution of water or ethanol, and further preferably water.

<12> The method for producing a composition containing a poorly water-soluble aromatic compound according to <11>, wherein 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. Further, it is preferably 0 to 10% by mass, more preferably 0 to 1% by mass, and further preferably contains no organic solvent.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <12> wherein, in the step of performing heat treatment, an aqueous medium is contained, and (A) a poorly water-soluble aroma is contained. In the heat-treated raw material of the group compound, (B) diol, and (C) trihydric or higher alcohol, the content of the (A) poorly water-soluble aromatic compound is preferably 0.1 g/L or more, more preferably 0.5 g/L. The above is more preferably 0.7 g/L or more, further preferably 0.9 g/L or more, further preferably 1 g/L or more, further preferably 2 g/L or more, and further preferably 7.5 g/L or more. Further, it is preferably 30 g/L or more, more preferably 150 g/L or less, still more preferably 100 g/L or less, further preferably 75 g/L or less, further preferably 60 g/L or less, and further preferably 55 g. It is preferably 50 g/L or less, more preferably 0.1 to 150 g/L, still more preferably 0.1 to 100 g/L, still more preferably 0.5 to 75 g/L, still more preferably 0.7 to 60 g. /L, further preferably 0.9 to 55 g / L, further preferably 1 to 55 g / L, and further preferably 1 to 50 g/L, more preferably 2 to 50 g/L, still more preferably 7.5 to 50 g/L, still more preferably 30 to 50 g/L.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <13> wherein, in the step of performing heat treatment, the aqueous medium is contained, and (A) the water-insoluble aromatic In the heat-treated raw material of the group compound, (B) diol, and (C) trihydric or higher alcohol, the content of the (B) diol is preferably 1 g/L or more, more preferably 10 g/L or more, and further It is preferably 20 g/L or more, more preferably 100 g/L or more, further preferably 300 g/L or more, further preferably 700 g/L or less, more preferably 600 g/L or less, and further preferably 500 g/L. Hereinafter, it is preferably 1 to 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, and still more preferably 300 to 500 g/ L.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <14> wherein, in the step of performing heat treatment, the aqueous medium is contained, and (A) the water-insoluble aromatic In the heat-treated raw material of the group compound, (B) diol, and (C) trihydric or higher alcohol, the content of the (C) trihydric or higher alcohol is preferably 1 g/L or more, more preferably 10 g/L or more. Further, it is preferably 50 g/L or more, more preferably 100 g/L or more, further preferably 500 g/L or less, more preferably 300 g/L or less, further preferably 250 g/L or less, and further preferably 200 g. /L or less, further 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 200g/L.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <15> wherein, in the step of performing heat treatment, the aqueous medium is contained, and (A) the water is insoluble aromatic In the heat-treated raw material of the group compound, (B) diol, and (C) trihydric or higher alcohol, the mass ratio [(A)/(B)] of the component (A) to the component (B) is preferably 0.001. The above is more preferably 0.002 or more, further preferably 0.02 or more, further preferably 0.025 or more, further preferably 0.06 or more, further preferably 1 or less, more preferably 0.5 or more. Further, it is preferably 0.2 or less, more preferably 0.15 or less, further preferably 0.13 or less, further preferably 0.12 or less, further preferably 0.11 or less, further preferably 0.001 to 1, more preferably 0.001. ~0.5, further preferably 0.001 to 0.2, more preferably 0.002 to 0.15, still more preferably 0.002 to 0.13, still more preferably 0.002 to 0.12, still more preferably 0.002 to 0.11, still more preferably 0.02 to 0.11. Further, it is preferably from 0.025 to 0.11, more preferably from 0.06 to 0.11.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <16> wherein, in the step of performing heat treatment, an aqueous medium is contained, and (A) a poorly water-soluble aroma is contained. In the heat-treated raw material of the group compound, (B) diol, and (C) trihydric or higher alcohol, the mass ratio [(A)/(C)] of the component (A) to the component (C) is preferably 0.001. The above is more preferably 0.005 or more, further preferably 0.01 or more, further preferably 0.12 or more, further preferably 0.15 or more, further preferably 0.17 or more, further preferably 1.5 or less, and more preferably 1 or less. Further, it is preferably 0.7 or less, further preferably 0.55 or less, further 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, still more preferably 0.12 to 0.55, further preferably 0.15 to 0.55, further preferably 0.17 to 0.55.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <17> wherein, in the step of performing heat treatment, an aqueous medium is contained, and (A) a poorly water-soluble aroma is contained. In the heat-treated raw material of the group compound, (B) diol, and (C) trihydric or higher alcohol, the mass ratio [(B)/(C)] of the component (B) to the component (C) is preferably 1.5. The above is more preferably 2 or more, further preferably 2.5 or more, further preferably 10 or less, more preferably 8 or less, still more preferably 6 or less, further preferably 1.5 to 10, more preferably 2 to 2 8, further preferably 2.5 to 6.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <18> wherein, in the step of performing heat treatment, an aqueous medium is contained, and (A) a poorly water-soluble aroma is contained. Group compound, (B) diol and (C) ternary or higher alcohol In the heat-treated raw material, the mass ratio [(A)/{(B)+(C)}]] of the component (A) to the total amount of the component (B) and the component (C) is preferably 0.001 or more, more preferably 0.002 or more, further preferably 0.015 or more, further preferably 0.019 or more, further preferably 0.05 or more, further preferably 0.5 or less, more preferably 0.2 or less, further preferably 0.15 or less, further preferably 0.12 Hereinafter, it is preferably 0.10 or less, more preferably 0.001 to 0.5, still more preferably 0.001 to 0.2, still more preferably 0.002 to 0.15, still more preferably 0.002 to 0.12, still more preferably 0.002 to 0.10. It is preferably from 0.015 to 0.10, more preferably from 0.019 to 0.10, still more preferably from 0.05 to 0.10.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <19> wherein, in the step of performing heat treatment, the aqueous medium is contained, and (A) the water is insoluble aromatic The content of the surfactant in the heat-treated raw material of the group compound, (B) diol, and (C) ternary or higher alcohol is preferably 0 to 1 g/L, more preferably 0 to 0.5 g/L, and further Preferably, it is 0 to 0.1 g/L, or further preferably does not contain a surfactant.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <20> wherein the temperature of the heat treatment is preferably 110 ° C or higher, more preferably 120 ° C or higher. Preferably, it is 170 ° C or less, more preferably 160 ° C or less, further preferably 120 to 160 ° C, more preferably 120 to 150 ° C.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <21>, wherein the pressure during the heat treatment is preferably 0 to 10 MPa, more preferably 0.1, in terms of gauge pressure. ~8 MPa, further preferably 0.1 to 6 MPa, further preferably 0.2 to 6 MPa, further preferably 0.2 to 4 MPa, further preferably 0.25 to 2 MPa, further preferably 0.3 to 1.5 MPa, and further preferably 0.3 to 0.6 MPa.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <22> wherein the heat treatment time is from the temperature of the heat treatment as described in <20> Preferably, it is 0.1 minute or more, more preferably 0.2 minute or more, further preferably 0.5 minute or more, and further preferably 30 minutes or less, more preferably 15 minutes or less, further preferably 8 minutes or less, further preferably 0.1 to 30 minutes, more preferably 0.2 to 15 minutes, still more preferably 0.5 to 8 minutes.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <22> wherein the heat treatment time reaches the temperature of the heat treatment as described in <20>. After that, it is preferably 0.1 minute or longer, more preferably 0.2 minute or longer, further preferably 0.5 minute or longer, further preferably 30 minutes or shorter, more preferably 15 minutes or shorter, further preferably 8 minutes or shorter, and further, It is preferably 0.1 to 30 minutes, more preferably 0.2 to 15 minutes, and still more preferably 0.5 to 8 minutes.

The method for producing a composition containing a poorly water-soluble aromatic compound according to any one of <1> to <24>, further comprising the step of heating the liquid to be obtained by heat treatment, preferably Cooling is performed at a cooling rate of 0.2 ° C/s or more.

<26> The method for producing a composition containing a poorly water-soluble aromatic compound according to <25>, wherein 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 / More preferably, it is 0.5 ° C / s or more, more preferably 1 ° C / s or more, further preferably 3 ° C / s or more, further preferably 5 ° C / s or more, and more preferably 100 ° C / Below s, more preferably 50 ° C / s or less.

<27> A composition containing a poorly water-soluble aromatic compound, which is obtained by the production method according to any one of <1> to <26>.

<28> The composition containing a poorly water-soluble aromatic compound according to <27>, wherein the content of the (A) poorly water-soluble aromatic compound in the composition containing a poorly water-soluble aromatic compound is preferably 0.5 g/L or more. It is more preferably 1 g/L or more, further preferably 1.5 g/L or more, and further preferably 2 g/L or more.

<29> The composition containing a poorly water-soluble aromatic compound according to <27> or <28>, wherein the content of the (B) diol in the composition containing the poorly water-soluble aromatic compound is preferably 1 g/L or more. More preferably, it is 10 g/L or more, further preferably 20 g/L or more, further preferably 100 g/L or more, further preferably 300 g/L or more, and further preferably 700. It is preferably g/L or less, more preferably 600 g/L or less, further preferably 500 g/L or less, further preferably 1 to 700 g/L, more preferably 10 to 600 g/L, and still more preferably 20 to 500 g/ L is further preferably 100 to 500 g/L, and further preferably 300 to 500 g/L.

The composition containing a poorly water-soluble aromatic compound according to any one of <27> to <29>, wherein the content of the (C) trivalent or higher alcohol in the composition containing the poorly water-soluble aromatic compound is higher. It is preferably 1 g/L or more, more preferably 10 g/L or more, further preferably 50 g/L or more, further preferably 100 g/L or more, further preferably 500 g/L or less, more preferably 300 g/L or less. Further, it is preferably 250 g/L or less, more preferably 200 g/L or less, further preferably 1 to 500 g/L, more preferably 1 to 300 g/L, still more preferably 10 to 250 g/L, and further It is preferably 50 to 250 g/L, and more preferably 100 to 200 g/L.

<31> The composition containing a poorly water-soluble aromatic compound according to any one of <27> to <30>, wherein the mass ratio of the component (A) to the component (B) [(A)/(B)] It is preferably 0.001 or more, more preferably 0.002 or more, further preferably 0.02 or more, further preferably 0.025 or more, further preferably 0.06 or more, further preferably 1 or less, more preferably 0.5 or less, and further preferably It is 0.2 or less, more preferably 0.15 or less, further preferably 0.13 or less, further preferably 0.12 or less, further preferably 0.11 or less, further preferably 0.001 to 1, more preferably 0.001 to 0.5, and further Preferably, it is 0.001 to 0.2, more preferably 0.002 to 0.15, still more preferably 0.002 to 0.13, still more preferably 0.002 to 0.12, still more preferably 0.002 to 0.11, still more preferably 0.02 to 0.11, still more preferably 0.025 to 0.11, and more preferably 0.06 to 0.11.

<32> The composition containing a poorly water-soluble aromatic compound according to any one of <27> to <31>, wherein a mass ratio of the component (A) to the component (C) [(A)/(C)] It is preferably 0.001 or more, more preferably 0.005 or more, further preferably 0.01 or more, further preferably 0.12 or more, further preferably 0.15 or more, further preferably 0.17 or more, further preferably 1.5 or less, more preferably It is 1 or less, more preferably 0.7 or less, further preferably 0.55 or less, further preferably 0.001 to 1.5, more preferably 0.001 to 1, and still more preferably 0.005 to 0.7. It is preferably from 0.01 to 0.55, more preferably from 0.12 to 0.55, still more preferably from 0.15 to 0.55, still more preferably from 0.17 to 0.55.

<33> The composition containing a poorly water-soluble aromatic compound according to any one of <27> to <32>, wherein the mass ratio of the component (B) to the component (C) is [(B)/(C)] It is preferably 1.5 or more, more preferably 2 or more, still more preferably 2.5 or more, further preferably 10 or less, more preferably 8 or less, further preferably 6 or less, and further preferably 1.5 to 10, more preferably Preferably, it is 2 to 8, and more preferably 2.5 to 6.

<34> The composition containing a poorly water-soluble aromatic compound according to any one of <27> to <31>, wherein the mass ratio of the component (A) to the total amount of the component (B) and the component (C) is [ (A)/{(B)+(C)}] is preferably 0.001 or more, more preferably 0.002 or more, still more preferably 0.015 or more, still more preferably 0.019 or more, still more preferably 0.05 or more, and more preferably It is preferably 0.5 or less, more preferably 0.2 or less, further preferably 0.15 or less, further preferably 0.12 or less, further preferably 0.10 or less, further preferably 0.001 to 0.5, more preferably 0.001 to 0.2, more preferably It is 0.002 to 0.15, more preferably 0.002 to 0.12, still more preferably 0.002 to 0.10, still more preferably 0.015 to 0.1, still more preferably 0.019 to 0.1, still more preferably 0.05 to 0.1.

The composition containing a poorly water-soluble aromatic compound according to any one of <27> to <34>, wherein the content of the organic solvent is preferably 0 to 60 by mass in the composition containing the poorly water-soluble aromatic compound. More preferably, it is 0 to 30% by mass, further preferably 0 to 10% by mass, further preferably 0 to 1% by mass, and further preferably contains no organic solvent.

The composition containing a poorly water-soluble aromatic compound according to any one of <27> to <35>, wherein the composition containing a water-insoluble aromatic compound preferably has a carbon number of 4 or less. It is 0 to 60% by mass, more preferably 0 to 30% by mass, still more preferably 0 to 10% by mass, still more preferably 0 to 1% by mass, still more preferably a non-carbon number of 4 or less.

<37> A water-insoluble aromatic salt as described in any one of <27> to <36> In the composition of the compound, the content of the surfactant in the composition containing the poorly water-soluble aromatic compound is preferably from 0 to 1% by mass, more preferably from 0 to 0.5% by mass, still more preferably from 0 to 0.1% by mass, Further preferably, no surfactant is included.

<38> A cosmetic containing a composition containing a poorly water-soluble aromatic compound according to any one of <27> to <37>.

<39> The cosmetic according to <38>, further comprising (D) one or more selected from the group consisting of a deodorizing component, a sterilizing component, and a tactile sensation improving component.

<40> A cosmetic comprising: a composition containing a poorly water-soluble aromatic compound, wherein (A) a poorly water-soluble aromatic compound, (B) a glycol, and (in the presence of an aqueous medium) C) A method in which a trihydric or higher alcohol is subjected to a heat treatment step at 100 to 180 ° C, and (B) a mass ratio of the diol to (C) a trivalent or higher alcohol [(B)/(C) ) is 1.5 to 10; and (D) is at least one selected from the group consisting of a deodorizing component, a bactericidal component, and a tactile sensation component.

<41> The cosmetic according to any one of <38> to <40>, wherein the mass ratio of the component (B) to the component (C) in the composition containing the poorly water-soluble aromatic compound [(B)/ (C)] is preferably 1.5 or more, more preferably 2 or more, still more preferably 2.5 or more, further preferably 10 or less, more preferably 8 or less, further preferably 6 or less, and further preferably 1.5. ~10, more preferably 2~8, and even more preferably 2.5~6.

<42> The cosmetic according to any one of <38> to <41> wherein the content of the component (A) in the composition containing the poorly water-soluble aromatic compound is preferably 1 g/L or more, more preferably 2 g. More preferably, it is 7.5 g/L or more, and further preferably 30 g/L or more.

<43> The cosmetic according to any one of <38> to <42> wherein the mass ratio of the component (A) to the component (B) in the composition containing the poorly water-soluble aromatic compound [(A)/ (B)] is preferably 0.02 or more, more preferably 0.025 or more, further preferably 0.06 or more, further preferably 1 or less, more preferably 0.5 or less, still more preferably 0.15 or less, and further preferably It is 0.02 to 1, more preferably 0.025 to 0.5, and further preferably 0.06 to 0.15.

<44> The cosmetic according to any one of <38> to <43> wherein the mass ratio of the component (A) to the component (C) in the composition containing the poorly water-soluble aromatic compound [(A)/ (C)] is preferably 0.12 or more, more preferably 0.15 or more, further preferably 0.17 or more, further preferably 1.5 or less, more preferably 1 or less, further preferably 0.6 or less, and further preferably 0.12. ~1.5, more preferably 0.15 to 1, and further preferably 0.17 to 0.6.

<45> The cosmetic according to any one of <38> to <44> wherein the component (A) in the composition containing the poorly water-soluble aromatic compound is based on the total amount of the component (B) and the component (C). The mass ratio [(A) / {(B) + (C)}] is preferably 0.015 or more, more preferably 0.019 or more, still more preferably 0.05 or more, further preferably 0.5 or less, more preferably 0.2 or less. Further, it is preferably 0.1 or less, more preferably 0.015 to 0.5, still more preferably 0.019 to 0.5, still more preferably 0.05 to 0.2, still more preferably 0.05 to 0.1.

The content of the water-insoluble aromatic compound of the component (A) in the cosmetic is preferably 0.01% by mass or more, and more preferably 0.01% by mass or more, based on the total composition of the cosmetic composition. It is preferably 0.02% by mass or more, more preferably 0.05% by mass or more, further preferably 1% by mass or less, more preferably 0.5% by mass or less, still more preferably 0.3% by mass or less, and further preferably 0.01% by mass. 1% by mass, more preferably 0.02 to 0.5% by mass, still more preferably 0.05 to 0.3% by mass.

<47> The cosmetic according to any one of <38> to <46> wherein the content of the (B) diol in the cosmetic is preferably 0.09% by mass or more, more preferably 0.18 by mass in the total composition. % or more, more preferably 0.3% by mass or more, further preferably 0.45 mass% or more, further preferably 8.4 mass% or less, more preferably 7% by mass or less, still more preferably 5.5% by mass or less, and further more preferably It is preferably 5% by mass or less, more preferably 0.09 to 8.4% by mass, still more preferably 0.18 to 7% by mass, still more preferably 0.3 to 5.5% by mass, still more preferably 0.45 to 5% by mass.

<48> A cosmetic according to any one of <38> to <47>, wherein the cosmetic is a cosmetic The content of the above-mentioned (C) trivalent or higher alcohol is preferably 0.01% by mass or more, more preferably 0.03% by mass or more, further preferably 0.06% by mass or more, and further preferably 0.09% by mass or more, based on the total composition. Further, it is preferably 2.86 mass% or less, more preferably 2.5% by mass or less, further preferably 2 mass% or less, further preferably 1.72 mass% or less, further preferably 0.01 to 2.86 mass%, more preferably 0.03 to 2.5% by mass, more preferably 0.06 to 2% by mass, still more preferably 0.09 to 1.72% by mass.

<49> The cosmetic according to any one of <38> to <48> wherein the mass ratio of the component (A) to the component (B) in the step of performing the heat treatment [(A)/(B) It is preferably 0.02 or more, more preferably 0.025 or more, further preferably 0.06 or more, further preferably 1 or less, more preferably 0.5 or less, further preferably 0.15 or less, and further preferably 0.02 to 1. More preferably, it is 0.025 to 0.5, and further preferably 0.06 to 0.15.

<50> The cosmetic according to any one of <38> to <49> wherein the mass ratio of the component (A) to the component (C) in the step of performing the heat treatment [(A)/(C) It is preferably 0.12 or more, more preferably 0.15 or more, further preferably 0.17 or more, further preferably 1.5 or less, more preferably 1 or less, further preferably 0.6 or less, and further preferably 0.12 to 1.5. More preferably, it is 0.15 to 1, and further preferably 0.17 to 0.6.

<51> The cosmetic according to any one of <38> to <50> wherein, in the step of performing heat treatment, (A) a poorly water-soluble aromatic compound relative to (B) a glycol and (C) three The mass ratio [(A) / {(B) + (C))] of the total amount of the alcohols of the above or more is preferably 0.015 or more, more preferably 0.019, still more preferably 0.05 or more, further preferably 0.5 or less. More preferably, it is 0.2 or less, further preferably 0.1 or less, further 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 <39> to <50> wherein the deodorizing component in the component (D) is preferably selected from those related to chemical deodorization, physical deodorization, and biological One or more of the deodorant and the deodorant method are more preferably selected from the group consisting of zinc oxide, titanium oxide, and tris(hydroxymethyl)aminomethane (2-amino-2-hydroxymethyl-1). , 3-propanediol), two One or more kinds of porous substances such as butylhydroxytoluene, cyclodextrin, hydroxyapatite, chitosan fine particles, and activated carbon, and extracts of sassafras, oleic acid, and L-menthol, and more preferably three ( Hydroxymethyl)aminomethane (2-amino-2-hydroxymethyl-1,3-propanediol).

In the case of using the deodorizing component as the component (D), the content of the cosmetic composition is preferably 0.01% by mass or more, and more preferably 0.01% by mass or more of the total composition. The content is preferably 0.05% by mass or more, more preferably 0.07% by mass or more, further preferably 0.09% by mass or more, more preferably 2% by mass or less, still more preferably 1.5% by mass or less, still more preferably 1% by mass. In the following, it is preferably 0.9% by mass or less, more preferably 0.01% to 2% by mass, still more preferably 0.05% to 1.5% by mass, still more preferably 0.07% to 1% by mass, still more preferably 0.09% to 0.9% by mass. .

<54> The cosmetic according to any one of <39> to <53> wherein the bactericidal component in the component (D) is preferably selected from the group consisting of alkyltrimethylammonium bromide and cetylpyridinium chloride. And silver-supporting one or more of inorganic particles, hydrochloric acid lysozyme, benzalkonium chloride, cetylpyridinium chloride (CPC), ruthenium, silver-supported zeolite, and silver-supported calcite, more preferably benzyl chloride Alkyl ammonium.

In the case of using the sterilizing component as the component (D), the content of the cosmetic according to any one of the above-mentioned items is preferably 0.005% by mass or more, more preferably It is 0.01% by mass or more, more preferably 0.02% by mass or more, further preferably 0.03% by mass or more, more preferably 4% by mass or less, still more preferably 3% by mass or less, still more preferably 1% by mass or less. Further, it is preferably 0.5% by mass or less, more preferably 0.005 to 4% by mass, still more preferably 0.01 to 3% by mass, still more preferably 0.02 to 1% by mass, still more preferably 0.03 to 0.5% by mass.

The cosmetic according to any one of <39> to <55>, wherein the touch-sensing component in the component (D) is preferably an inorganic powder, an organic powder or a composite powder thereof. More preferably, it is selected from the group consisting of nylon resin, polystyrene resin, polyethylene resin, polymethyl methacrylate resin, (meth) acrylate resin, polyoxyn oxy resin, polyoxyethylene rubber powder, and cellulose granules. , lauryl methacrylate ‧ dimethacrylate ‧ methyl propyl Sodium silicate copolymer, talc, sericite, mica, kaolin, clay, bentonite, tannic acid, phthalic anhydride, magnesium citrate, mica, magnesium oxide, zinc oxide, titanium oxide, aluminum oxide, aluminum sulfate, calcium sulfate, sulfuric acid钡, magnesium sulfate, and a network structure in which a siloxane chain is three-dimensionally extended, and one or more kinds of polymethylsilsesquioxane powder in which a ruthenium atom is bonded with a methyl group.

<57> The cosmetic material according to <56>, wherein the average particle diameter of the tactile sensation improving component is preferably 0.01 μm or more, more preferably 0.05 μm or more, further preferably 0.2 μm or more, and further preferably 50 μm or less. More preferably, it is 20 μm or less, and further preferably 8 μm or less.

In the case of using the touch-sensing component as the component (D), the content of the cosmetic composition according to any one of the above-mentioned items is preferably 0.01% by mass or more based on the total composition. It is more preferably 0.1% by mass or more, further preferably 1% by mass or more, further preferably 1.5% by mass or more, more preferably 20% by mass or less, still more preferably 10% by mass or less, and still more preferably 5% by mass. % or less, more preferably 0.01 to 20% by mass, still more preferably 0.1 to 20% by mass, still more preferably 1 to 10% by mass, still more preferably 1.5 to 5% by mass.

<59> The cosmetic according to any one of the items <39> to <58>, wherein the total content of the component (D) is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, based on the total composition. It is preferably 0.02% by mass or more, more preferably 20% by mass or less, still more preferably 15% by mass or less, further preferably 10% by mass or less, further preferably 5% by mass or less, and further preferably 0.005%. 20% by mass, more preferably 0.01 to 15% by mass, still more preferably 0.02 to 10% by mass, still more preferably 0.02 to 5% by mass.

<60> The cosmetic according to any one of <38> to <59> which further preferably contains an aqueous medium, more preferably water.

<61> The cosmetic according to <60>, wherein the concentration of the poorly water-soluble aromatic compound relative to 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 is further preferably 0.5 to 5 g/L, and further preferably 0.5 to 2 g/L.

[Examples] [Quantification of isopropylmethylphenol and trans-3,4'-dimethyl-3-hydroxyflavanone and 2-(1-ethylpentyl)-7-methoxyxanthone]

High-performance liquid chromatograph manufactured by Hitachi, Ltd., and installed Cadenza CD-C18 (4.6mm) manufactured by Imtakt ×150 mm, 3 μm), quantified by a gradient method at a column temperature of 40 °C. The mobile phase A liquid system was set to 0.05 mol/L acetic acid aqueous solution, the B liquid system was set to acetonitrile, and the liquid was supplied at 1.0 mL/min. The gradient conditions are as follows.

The sample injection amount was 10 μL. For the detection, isopropylmethylphenol was quantified based on the absorbance at a wavelength of 283 nm, and trans-3,4'-dimethyl-3-hydroxyflavanone was based on the absorbance at a wavelength of 254 nm. Quantitative, 2-(1-ethylpentyl)-7-methoxychromone was quantified based on the absorbance at a wavelength of 300 nm.

[raw materials]

Isopropyl methylphenol (IPMP, manufactured by Osaka Chemical Industry Co., Ltd., purity 100%)

2-(1-ethylpentyl)-7-methoxy chromone (methoxy ketone, manufactured by Kao Co., Ltd., purity 99% or more)

Trans-3,4'-dimethyl-3-hydroxyflavanone (third flavanone, manufactured by Kao Co., Ltd., purity 99% or more)

1,3-butanediol (1,3-BG, manufactured by KH Neochem Co., Ltd., purity 100%)

1,3-propanediol (1,3-PG, manufactured by DuPont Co., Ltd., purity 100%)

Glycerin (Gly, manufactured by Kao Co., Ltd., purity 100%)

Diglycerin (DG, manufactured by Sakamoto Pharmaceutical Co., Ltd., purity 100%)

Example 1

1,3-butanediol was added to distilled water so that 1,3-butanediol was 300 g/L so that 1,3-butanediol was 7.5 g/L, and the obtained glycerol was added to distilled water so as to be 100 g/L. The slurry was heat-treated in a 190 mL stainless steel batch reactor (manufactured by Nitto High Pressure Co., Ltd.). The temperature was maintained at 150 ° C for 1 minute and rapidly cooled to room temperature (25 ° C) (cooling rate 0.5 ° C / s). The pressure in the heat treatment was 0.4 MPa. After cooling, the heat treatment liquid was quickly taken out, and filtered using a PTFE (Polytetrafluoroethylene) filter having a pore size of 0.2 μm to obtain an isopropylmethylphenol composition.

The results of the treatment conditions and the measurement of the isopropylmethylphenol concentration, the 1,3-butanediol concentration and the glycerin concentration in the composition at 25 ° C are shown in Table 1.

Example 2~11

Isopropylmethylphenol, 1,3-butanediol or 1,3-propanediol, glycerin or diglycerin was added to distilled water in the amounts shown in Table 1, and heated in the same manner as in Example 1. The treatment was carried out to obtain an isopropylmethylphenol composition.

The treatment conditions and the results of measuring the concentration of isopropylmethylphenol, 1,3-butanediol, 1,3-propanediol, glycerol and diglycerol in the composition at 25 ° C are shown in Table 1. .

Comparative example 1

The isopropylmethylphenol composition was obtained in the same manner as in Example 1 except that 1,3-butanediol and glycerin were not added, and 1.5 g/L of isopropylmethylphenol was dispersed in distilled water. The results obtained by treating the conditions and the concentration of isopropylmethylphenol in the composition are shown in Table 2.

Comparative example 2~7

Isopropylmethylphenol, 1,3-butanediol, and glycerin were added to distilled water in the amounts shown in Table 2, and the slurry was stirred at room temperature for 3 days (agitator, 500 rpm). Thereafter, the solid matter was separated by filtration. The results of the treatment conditions and the isopropylmethylphenol concentration, the 1,3-butanediol concentration, and the glycerin concentration in the measurement liquid portion are shown in Table 2.

Comparative Example 8~10

The isopropylmethylphenol combination was obtained in the same manner as in Example 1 except that glycerol was not added, and isopropyl methylphenol and 1,3-butanediol were added to distilled water in the amounts shown in Table 2, respectively. Things. The results of the treatment conditions and the concentration of isopropylmethylphenol and the concentration of 1,3-butanediol in the measurement composition are shown in Table 2.

Comparative Example 11~12

Isopropylmethylphenol was obtained in the same manner as in Example 1 except that 1,3-butanediol was not added, and isopropylmethylphenol and glycerin were added to distilled water in the amounts shown in Table 2, respectively. Things. The results of the treatment conditions and the concentration of isopropylmethylphenol and the concentration of glycerol in the measurement composition are shown in Table 2.

Example 12-15

2-(1-ethylpentyl)-7-methoxyxanone, 1,3-butanediol, and glycerin were added to distilled water in the amounts shown in Table 3, respectively, in the same manner as in Example 1. The heat treatment was carried out to obtain a 2-(1-ethylpentyl)-7-methoxyxanone composition. The results of the treatment conditions and the concentration of 2-(1-ethylpentyl)-7-methoxychromone in the measurement composition, the concentration of 1,3-butanediol, and the concentration of glycerol are shown in Table 3.

Comparative Example 13

2-(1-ethylpentyl)-7-methoxychromone 1.0 g/L was dispersed in distilled water without adding 1,3-butanediol and glycerin, and 2-(2-) was obtained in the same manner as in Example 10. 1-Ethylpentyl)-7-methoxychromone composition. The results of the treatment conditions and the concentration of 2-(1-ethylpentyl)-7-methoxychromone in the measurement composition are shown in Table 3.

Comparative Example 14~16

2-(1-ethylpentyl)-7-methoxyxanone, 1,3-butanediol, and glycerin were added to distilled water in the amounts shown in Table 3, and the slurry was placed in a room. After stirring for 3 days under temperature (agitator, 500 rpm), the solid matter was separated by filtration. Table 3 shows the results of the concentration of 2-(1-ethylpentyl)-7-methoxychromone in the measurement liquid portion, the concentration of 1,3-butanediol, and the glycerin concentration.

Comparative Example 17~18

2-(1-ethylpentyl)-7-methoxyxanone and 1,3-butanediol were added to distilled water in an amount shown in Table 3, respectively, without adding glycerin, and Example 10 The 2-(1-ethylpentyl)-7-methoxychromone composition was obtained in the same manner. The results of the treatment conditions and the concentration of 2-(1-ethylpentyl)-7-methoxychromone in the measurement composition and the concentration of 1,3-butanediol are shown in Table 3.

Examples 16~17

Trans-3,4'-dimethyl-3-hydroxyflavanone, 1,3-butanediol, and glycerin were added to distilled water in the amounts shown in Table 4, respectively, in the same manner as in Example 1. The heat treatment was carried out in the same manner to obtain a trans-3,4'-dimethyl-3-hydroxyflavanone composition. The results of the treatment conditions and the trans-3,4'-dimethyl-3-hydroxyflavanone concentration, the 1,3-butanediol concentration, and the glycerin concentration in the measurement composition are shown in Table 4.

Comparative Example 19

The trans-3,4'-dimethyl-3-hydroxyflavanone 1.0 g/L was dispersed in distilled water without adding 1,3-butanediol and glycerin, and trans was obtained in the same manner as in Example 14. a -3,4'-dimethyl-3-hydroxyflavanone composition. The results of the treatment conditions and the concentration of trans-3,4'-dimethyl-3-hydroxyflavanone in the measurement composition are shown in Table 4.

Comparative Example 20

The trans-3,4'-dimethyl-3-hydroxyflavanone was adjusted to 1.0 g/L, and the 1,3-butanediol was 500 g/L, and the glycerin was made into 100 g/ The form of L was added to distilled water, and the slurry was stirred at room temperature for 3 days (agitator, 500 rpm), and then the solid matter was separated by filtration. The results obtained by measuring the trans-3,4'-dimethyl-3-hydroxyflavanone concentration, the 1,3-butanediol concentration, and the glycerin concentration in the measurement liquid portion are shown in Table 4.

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 was obtained in the same manner as in Example 14. '-Dimethyl-3-hydroxyflavanone composition. The results of the treatment conditions and the trans-3,4'-dimethyl-3-hydroxyflavanone concentration and the 1,3-butanediol concentration in the measurement composition are shown in Table 4.

As is clear from Tables 1 to 4, a composition containing the component (A) having a large content of a poorly water-soluble aromatic compound can be obtained, and the solubility of the poorly water-soluble aromatic compound can be remarkably increased.

Further, even when the composition containing the component (A) obtained in Examples 1 to 17 was cooled to room temperature, precipitation did not occur, and a stable dissolved state was maintained.

Examples 18 to 24 and Comparative Examples 22 to 26

Using the isopropylmethylphenol (IPMP) compositions obtained in Examples 5 to 11, Comparative Examples 1, 6, 8, 10 and 12, the deodorant cosmetics shown in Tables 5 and 6 were produced, and the adhesive was applied. The greasy, deodorizing effect, bactericidal effect, smoothness and deodorizing effect were evaluated.

The concentration of water in the IPMP composition (25 ° C) was 370.0 g / L (Example 18), 360.0 g / L (Example 19), 350.1 g / L (Example 20), 345.0 g / L (Examples 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), and 389.6 g/L (Comparative Example) 23), 698.7g/L (Comparative Example 24), 492.9 g/L (Comparative Example 25) and 599.64 g/L (Comparative Example 26).

The results are shown together in Tables 5 and 6.

(Production method)

Based on the IPMP concentration analysis values of the IPMP compositions obtained in Examples 5 to 11, Comparative Examples 1, 6, 8, 10, and 12, the IPMP composition was added dropwise to room temperature so that the IPMP concentration became 0.1% by mass. Dilute in water at 25 ° C under stirring. At this time, the component (D) is preliminarily mixed in water so as to be a specific concentration before the dropwise addition of the IPMP composition.

(evaluation method)

Five men who left the room after entering the environmental adjustment room (38 ° C, relative humidity 40%) for 30 minutes and sweating all over the body, used each deodorant cosmetic for the whole body, and evaluated the deodorizing effect.

(1) Sticky feeling:

The user himself scored the sticky feeling of the chest to which the deodorant cosmetic was applied on the basis of the following criteria, and calculated the average value of the five persons.

0: not sticky

1: Slightly sticky.

2: Sticky.

3; very sticky.

(2) Deodorization effect:

The user himself/herself judges the sweat odor intensity of the whole body immediately after applying the deodorant cosmetic on the basis of the following criteria. In other words, the standard was divided into five grades, the case where the total smell was not evaluated was evaluated as 4, and the case where there was no change before the coating was evaluated as 0, and the average value of the five persons was calculated.

(3) Sterilization effect:

The labeling medium (Nissui "SCDLP Cold Space Medium, Nishui Pharmaceutical Co., Ltd." was pressed against the crotch portion coated with the deodorant cosmetic, and the number of the culture medium after 24 hours at 35 ° C was measured, and the following The benchmark was scored and the average of 5 was calculated.

0: The number of communities is 0/cm ² .

1: The number of colonies is 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) Smoothness:

The user himself/herself determined the smoothness of the chest after 6 hours of daily life after applying the deodorant cosmetic on the basis of the following criteria. That is, the reference was divided into five levels, the case of being very smooth was evaluated as 4, the case of being completely unsmooth was evaluated as 0, and the average of 5 persons was calculated.

(5) Sustainability of deodorizing effect:

The user himself/herself determined the sweat odor intensity of the whole body after 6 hours of daily application after applying the deodorant cosmetic on the basis of the following criteria, and calculated the average value of the five persons.

0: Stronger than before coating.

1: No change before coating.

2: weaker than before coating.

3; completely not stinky.

When the IPMP is combined with the deodorizing component, in addition to the effect of suppressing the sweat odor caused by the bactericidal effect of IPMP, the effect of deodorizing the already existing sweat odor can be obtained.

When the IPMP is combined with the sterilizing component, the bactericidal performance of the skin-inherent bacteria which is insufficient in the bactericidal effect in IPMP is improved by using other sterilizing components in combination, and the sweat odor suppressing effect is improved.

When IPMP is combined with a powder which is a tactile sensation improving component, the effect of evapotranspiration of the sweat of the powder becomes an environment in which the bacteria are hard to proliferate, and the bactericidal effect of IPMP is improved. Also, a smooth feeling can be obtained.

Example 25

10 g of aluminum hydroxychloride, 0.2 g of polyoxyethylene hydrogenated castor oil, and 0.05 g of a 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 deodorant. . The composition is as follows.

Example 26

To 3.33 g of the isopropylmethylphenol composition produced in Example 5, 6 g of 1,3 butanediol, 0.1 g of oleyl alcohol, 0.4 g of POE (20) oleyl ether, and 0.2 g of methyl p-hydroxybenzoate were added. 0.2 g of dipotassium glycyrrhizinate and 0.04 g of perfume, and 100 g of acne lotion was prepared by adding purified water. The composition is as follows.

Example 27

12 g of stearic acid, 14 g of myristic acid, 5 g of lauric acid, 3 g of jojoba oil, 14.047 g of sorbitol, 10 g of glycerin, and 10 g of 1,3-butanediol were dissolved and dissolved as an oil phase. At 70 ° C. 20 g of purified water was added to 2.0 g of the isopropylmethylphenol composition produced in Example 7, and 5 g of potassium hydroxide was dissolved, and the oil phase was gradually added while stirring. Further, 4 g of N-methyltaurine was added, and the mixture was stirred for 10 minutes to sufficiently carry out the neutralization reaction, and then 1.9 g of POE (20) glyceryl monostearate was added. The hand sanitizer was prepared by slowly cooling (cooling) to 25 °C. The composition is as follows.

Claims (15)

A method for producing a composition containing a poorly water-soluble aromatic compound, comprising (A) a poorly water-soluble aromatic compound, (B) a glycol, and (C) a trihydric or higher alcohol in the presence of an aqueous medium; The step of heat treatment at ~180 °C. The method for producing a composition containing a poorly water-soluble aromatic compound according to claim 1, wherein the (A) poorly water-soluble aromatic compound is an aromatic compound having a solubility in water of 0.5 g/L or less at 25 °C. The method for producing a composition containing a poorly water-soluble aromatic compound according to claim 1 or 2, wherein (A) the poorly water-soluble aromatic compound is one selected from the group consisting of a phenolic antibacterial agent, a chromone derivative, and a flavanol derivative. Kind or more than two. A process for producing a composition containing a poorly water-soluble aromatic compound according to claim 1 or 2, wherein (A) the poorly water-soluble aromatic compound is selected from the group consisting of isopropylmethylphenol, triclosan, and 2-(1-ethyl) One or two or more kinds of pentyl)-7-methoxy chromone and trans-3,4'-dimethyl-3-hydroxyflavanone. A process for producing a composition containing a poorly water-soluble aromatic compound according to claim 1 or 2, wherein (B) the diol is selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, and 1,3- One or more of butylene glycol, dipropylene glycol, and polyethylene glycol. A method for producing a composition containing a poorly water-soluble aromatic compound according to claim 1 or 2, wherein the (C) trivalent or higher alcohol is glycerin or diglycerin. A method for producing a composition containing a poorly water-soluble aromatic compound according to claim 1 or 2, wherein (A) a mass ratio of the poorly water-soluble aromatic compound to the (B) diol in the step of performing heat treatment [( A)/(B)] is 0.001 to 1. A method for producing a composition containing a poorly water-soluble aromatic compound according to claim 1 or 2, wherein in the step of performing heat treatment, (B) a mass ratio of the diol to (C) a trihydric or higher alcohol [( B) / (C)] is 1.5 to 10. A method for producing a composition containing a poorly water-soluble aromatic compound according to claim 1 or 2, wherein in the step of performing heat treatment, (A) a poorly water-soluble aromatic compound relative to (B) a glycol and (C) three The mass ratio of the total amount of alcohols above the element [[A)/{(B)+(C)}] is 0.001 to 0.5. The method for producing a composition containing a poorly water-soluble aromatic compound according to claim 1 or 2, further comprising the step of cooling the heat treatment liquid obtained by the heat treatment at a cooling rate of 0.2 ° C/s or more. A composition containing a poorly water-soluble aromatic compound obtained by the production method according to any one of claims 1 to 10. The composition containing the poorly water-soluble aromatic compound according to claim 11, wherein (A) the mass ratio of the poorly water-soluble aromatic compound to the total amount of the (B) diol and the (C) ternary or higher alcohol [(A) ) /{(B)+(C)}] is 0.001~0.5. A cosmetic comprising a composition comprising the poorly water-soluble aromatic compound of claim 11 or 12. The cosmetic of claim 13 further contains (D) at least one selected from the group consisting of a deodorizing component, a sterilizing component, and a tactile sensation improving component. The cosmetic of claim 14, wherein the mass ratio of the (B) diol to the (C) trihydric or higher alcohol in the composition containing the poorly water-soluble aromatic compound is 1.5 (B)/(C)] ~10.