JP7067918B2 - Method for producing a composition containing a poorly water-soluble aromatic compound - Google Patents

Description

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

Aromatic compounds are widely used in products such as cosmetics, pharmaceuticals, foods, and daily necessities. Many aromatic compounds are solid at room temperature and poorly soluble in water, and are generally used by dissolving them in alcohol or oil, but their solubility is not sufficient and they are irritating to the skin. There are problems such as. In addition, the applicable composition is limited.

Therefore, conventionally, in the presence of an aqueous medium, a poorly water-soluble aromatic compound and a polyol such as a dihydric alcohol are heat-treated at 110 to 180 ° C. to produce a composition having improved solubility of the poorly water-soluble aromatic compound. A method has been proposed (Patent Document 1).

Japanese Unexamined Patent Publication No. 2014-139164

However, the present inventors have found that in the technique of Patent Document 1, when the aqueous medium volatilizes, it may be difficult to maintain the solubility of the poorly water-soluble aromatic compound.
Therefore, the present invention produces a poorly water-soluble aromatic compound-containing composition which not only has excellent solubility of a poorly water-soluble aromatic compound but also realizes stable solubility even when an aqueous medium volatilizes. Regarding providing a method.

The present inventors conducted diligent studies in view of the above problems, and found that if a poorly water-soluble aromatic compound and polyvinylpyrrolidone were heat-treated at 100 to 180 ° C. in the presence of an aqueous medium, they were compared with the case where no heat treatment was performed. As a result, the dissolution concentration of the poorly water-soluble aromatic compound increases, and when the composition subjected to such treatment is applied, a coating film is formed even when the aqueous medium volatilizes, and the coating film is stable in the coating film. We have found that the solubility of sparingly water-soluble aromatic compounds is realized.

That is, the present invention comprises a step of heat-treating (A) a poorly water-soluble aromatic compound and (B) polyvinylpyrrolidone at 100 to 180 ° C. in the presence of an aqueous medium, and the present invention comprises a poorly water-soluble aromatic compound-containing composition. It provides a manufacturing method.

According to the present invention, the poorly water-soluble aromatic compound has excellent solubility, and when applied to the skin or hair, a coating film is formed even if the aqueous medium volatilizes after application, and the solubility in the coating film. It is possible to obtain a composition containing a poorly water-soluble aromatic compound in which the amount is stably maintained.

The method for producing a poorly water-soluble aromatic compound-containing composition of the present invention includes a step of heat-treating (A) the poorly water-soluble aromatic compound and (B) polyvinylpyrrolidone at 100 to 180 ° C. in the presence of an aqueous medium. , The manufacturing method.
As used herein, the (A) sparingly water-soluble aromatic compound means an aromatic compound having a solubility in water at 25 ° C. of 5.0 g / L or less. In the present invention, an aromatic compound having a solubility in water at 25 ° C. of 1.0 g / L or less is preferably applicable.
Here, the solubility represents the number of grams of the solute dissolved in 1 L of the solution, and the unit is [g / L].

Further, in the present invention, as the (A) sparingly water-soluble aromatic compound, a compound having one or more hydroxyl groups in the molecule can be preferably applied. For example, phenols and polyphenols can be mentioned. Phenols or polyphenols that can be preferably applied are those that are externally applied to the skin and body hair from the viewpoint of effectively exerting the effects of the present invention, and are, for example, plant-derived flavonoids, tannins, phenolic acids, alkylphenols, and chloro. Examples thereof include phenols and flavanonol derivatives.
Specifically, flavonols such as rutin, kercitrin, isokercitrin, kercetin, myricitrin, mylicetin, and kenferol; isoflavones such as daizein, daidin, glycitein, glycitin, genistine, and genistin; hesperidin, neohesperidin, hesperetin, Flabanones such as naringin; flavones such as lingenin, purnin, astragalin, apiin, apigenin; Anthocyanidins such as idein, mecosianin, pelargonidin, and calistefin; ellagic acid; hydroxysilicic acid derivatives such as resveratrol, caffeic acid, ferulic acid, p-kumalic acid; methyl paraoxybenzoate (methylparaben), ethyl paraoxybenzoate (methylparaben) Paraoxy such as ethyl paraben), propyl paraoxybenzoate (propylparaben), isopropyl paraoxybenzoate (isopropylparaben), butyl paraoxybenzoate (butylparaben), isobutyl paraoxybenzoate (isobutylparaben), benzyl paraoxybenzoate (benzylparaben), etc. Parabenic acid esters; Alkylphenols such as isopropylmethylphenol; Chlorophenols such as triclosan, chlortimol, carbachlor, chlorophen, dichlorophen, hexachlorophen, chloroxylenol, chlorocresol; trans-3,4'-dimethyl-3- Flabanonol derivatives such as hydroxyflabanone; curcumins such as curcumin and the like can be mentioned.
Of these, hydroxycinnamic acid derivatives and flavanonol derivatives are preferable, and ferulic acid and trans-3,4'-dimethyl-3-hydroxyflavanone are more preferable.
(A) The poorly water-soluble aromatic compound may be one kind or a mixture of two or more kinds.

In the present invention, a heat-treated raw material containing an aqueous medium, (A) a poorly water-soluble aromatic compound and (B) polyvinylpyrrolidone is prepared and heat-treated.
The content of the (A) sparingly water-soluble aromatic compound in the heat-treated raw material varies depending on the type thereof, but is preferably 0.2 mass because the amount of the (A) sparingly water-soluble aromatic compound solubilized can be increased. % Or more, preferably 0.5% by mass or more, more preferably 1.0% by mass or more, and (A) preferably 5.0% by mass from the viewpoint of dissolution stability of the poorly water-soluble aromatic compound. It is as follows.

The (B) polyvinylpyrrolidone used in the present invention is a linear polymer of N-vinyl-2-pyrrolidone.
(B) Polyvinylpyrrolidone has a K value of 10 or more in terms of (A) solubility of the poorly water-soluble aromatic compound and (A) dissolution stability of the (A) poorly water-soluble aromatic compound after formation of the coating film. Is preferable, and from the viewpoint of the thermal stability of polyvinylpyrrolidone itself, those of 60 or less are preferable, those of 40 or less are more preferable, and those of 30 or less are further preferable. The K value of polyvinylpyrrolidone can be determined by Fikentscher's formula using a capillary viscometer.
As the (B) polyvinylpyrrolidone, commercially available products such as PVPK-15 and PVPK-30 (Wako Pure Chemical Industries, Ltd.) can be used.

The content of (B) polyvinylpyrrolidone in the heat-treated raw material is preferably 0.1% by mass or more, more preferably 0.5, from the viewpoint of the solubility and dissolution stability of (A) the poorly water-soluble aromatic compound. It is preferably 40% by mass or less, and more preferably 20% by mass or less from the viewpoint of fluidity.

In the present invention, the mass ratio [(A) / (B)] of the (A) poorly water-soluble aromatic compound to (B) polyvinylpyrrolidone in the heat-treated raw material is the dissolution of (A) the poorly water-soluble aromatic compound. From the viewpoint of stability, it is preferably 0.5 or less, more preferably 0.3 or less, and (A) preferably 0.05 or more from the viewpoint that the solubilization amount of the poorly water-soluble aromatic compound can be increased. Is.

The aqueous medium used in the present invention refers to water and an aqueous solution of an organic solvent. Examples of water include tap water, distilled water, ion-exchanged water, and purified water. The organic solvent is not particularly limited as long as it is uniformly mixed with water, but monohydric alcohol and dihydric alcohol can be preferably used.
The monohydric alcohol is preferably a monohydric alcohol having 4 or less carbon atoms, more preferably ethanol and propanol, and even more preferably ethanol.
The dihydric alcohol is, for example, alkylene glycols such as ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol and 1,3-butanediol; diethylene glycol, dipropylene glycol and polyethylene. Examples thereof include polyalkylene glycols such as glycol and polypropylene glycol. The weight average molecular weight of polyethylene glycol is preferably 200 to 20,000. Of these, propylene glycol, 1,3-propanediol, and 1,3-butanediol are preferable.

When an organic solvent is used, the dissolution concentration of (A) the poorly water-soluble aromatic compound can be increased. Therefore, when the concentration of (A) the poorly water-soluble aromatic compound in the composition containing the poorly water-soluble aromatic compound is increased, heating is performed. The content of the organic solvent in the treatment raw material is preferably 3% by mass or more, more preferably 5% by mass or more, still more preferably 8% by mass or more, still more preferably 13% by mass or more, still more preferably 15% by mass or more. Also, from the viewpoint of economic efficiency, it is preferably 40% by mass or less, more preferably 30% by mass or less, still more preferably 25% by mass or less, still more preferably 22% by mass or less, still more preferably 20% by mass or less. ..
On the other hand, since organic solvents, especially ethanol, are irritating to the skin, the content of ethanol in the heat treatment raw material is preferably 0 to 60 when the amount of ethanol used is reduced from the viewpoint of reducing the irritation to the skin. It is preferably mass% or less, more preferably 0 to 10% by mass, still more preferably 0 to 1% by mass, and further preferably substantially 0% by mass, that is, it does not contain ethanol.

In addition to the above-mentioned components, the heat-treated raw material may appropriately contain other components, for example, a surfactant, as long as the effects of the present invention are not impaired. The content of the surfactant in the heat treatment raw material is preferably 0 to 0.1% by mass, more preferably 0 to 0.05% by mass, from the viewpoint of maintaining the function and reducing irritation to the skin. It is more preferably 0 to 0.01% by mass, and more preferably substantially 0% by mass, that is, it does not contain a surfactant.

The method for heat-treating the heat-treated raw material is not particularly limited, and a known method can be applied. The heat treatment is preferably performed in a closed system. The closed system is a closed system in which (A) a poorly water-soluble aromatic compound, (B) polyvinylpyrrolidone, or an aqueous medium is not added or removed during the heat treatment, but is in a completely closed state. It is not necessary, and the heat treatment of the heat treatment raw material may be performed. For example, an autoclave, a pressure-resistant heat-resistant container, or the like can be used.

The heating temperature is 100 ° C. to 180 ° C., but is preferably 101 ° C. or higher, more preferably 110 ° C. or higher, still more preferably 120 ° C. or higher from the viewpoint of (A) solubility of the poorly water-soluble aromatic compound. Further, from the viewpoint of thermal stability, it is preferably 175 ° C. or lower, more preferably 170 ° C. or lower, and further preferably 160 ° C. or lower.
In the present invention, the heating temperature means the temperature of the heat source for heating the heat-treated raw material.

The pressure during the heat treatment is preferably set to be equal to or higher than the saturated vapor pressure of water. When pressurizing with a back pressure valve, the gauge pressure is preferably 0 to 10 MPa. The gauge pressure is preferably 0.1 MPa or more, more preferably 0.2 MPa or more, still more preferably 0.25 MPa or more, still more preferably 0.3 MPa or more, and preferably 8 MPa or less, still more preferably 6 MPa. Below, it is more preferably 4 MPa or less, further preferably 2 MPa or less, still more preferably 1.5 MPa or less. The gauge pressure is a pressure with the atmospheric pressure as 0 MPa. A gas may be used for pressurization, and examples of the gas used include an inert gas, steam, nitrogen gas, helium gas and the like.

The heat treatment can be carried out by any method such as a batch method, a semi-batch method, or a distribution method. Above all, the distribution method is preferable in that the heat treatment time can be easily controlled. In the present invention, the heat treatment time starts from the time when the heat treatment raw material starts contacting with a heat source of 100 ° C. or higher, and the end point when the heat treatment liquid starts contact with a refrigerant of 90 ° C. or lower. The time to do.
The heat treatment time may be appropriately selected depending on the treatment method, and in the case of a batch type, 1.0 minute or more is preferable, 3.0 minutes or more is more preferable, and 4.0 minutes or more is further preferable from the viewpoint of improving solubility. It is more preferably 5.0 minutes or more, more preferably 30 minutes or less, still more preferably 15 minutes or less, still more preferably 10 minutes or less from the viewpoint of thermal stability.
When the heat treatment is performed by the distribution method, the average residence time calculated by dividing the volume of the high temperature and high pressure portion of the heating device by the supply rate of the heat treatment raw material is used as the heat treatment time. In the case of the distribution type, the heat treatment time is preferably 0.1 minutes or longer, more preferably 0.3 minutes or longer, further preferably 0.5 minutes or longer, and further preferably 1.0 minutes or longer from the viewpoint of improving solubility. preferable. From the viewpoint of thermal stability, 5 minutes or less is preferable, 3 minutes or less is more preferable, and 2 minutes or less is further preferable.

The flow velocity of water in the case of the distribution method varies depending on the volume of the heating device, but for example, when the volume of the heating portion is 500 L, it is preferably 15 to 5,000 L / min, and more preferably 30 to 2,500 L / min. Further, 60 L / min to 1,000 L / min is preferable.

After the heat treatment, it is preferable to include a step of cooling the heat treatment liquid to 90 ° C. or lower. The cooling temperature (refrigerant temperature) of the heat treatment liquid is preferably 50 ° C. or lower, more preferably 30 ° C. or lower, from the viewpoint of the cooling rate described later. Further, it is preferably 0 ° C. or higher, more preferably 10 ° C. or higher.
Cooling may be performed in multiple stages. For example, after cooling to 95 ° C., cooling may be interrupted once, and then further cooled to 90 ° C. or lower.

The cooling rate of the heat treatment liquid calculated from the time required for the temperature to drop from the heat treatment temperature to 90 ° C. is preferably 0.2 ° C./s or more, more preferably 0.4 ° C./s or more. The higher the cooling rate, the more preferable it is in terms of the thermal stability of (A) the poorly water-soluble aromatic compound. Therefore, the upper limit of the cooling rate is not particularly defined, but from the viewpoint of restrictions on the manufacturing equipment, for example, 100 ° C./s or less, further 50 ° C./s or less is preferable.

Further, it is preferable to include a step of removing the residual solid matter that does not dissolve from the heat treatment liquid. The method for removing the solid matter is not particularly limited, and examples thereof include centrifugation, decantation, and filtration.

Thus, a poorly water-soluble aromatic compound-containing composition is obtained. In the poorly water-soluble aromatic compound-containing composition, (A) the poorly water-soluble aromatic compound has high solubility, and (A) precipitation of the poorly water-soluble aromatic compound is suppressed at room temperature (25 ° C.). Further, when the poorly water-soluble aromatic compound-containing composition is applied, a coating film is formed even if the aqueous medium volatilizes, and the solubility of (A) the poorly water-soluble aromatic compound is stable in the coating film. Is maintained.
In the poorly water-soluble aromatic compound-containing composition of the present invention, (A) the solubility of the poorly water-soluble aromatic compound is improved, and (A) the poorly water-soluble aromatic is stable even if the aqueous medium volatilizes after application. The reason why the solubility of the group compound is obtained is not clear, but it is presumed as follows. Normally, even if a poorly water-soluble aromatic compound is heated under an aqueous solvent and is in a molecularly dispersed state, the aromatic rings of each other interact with each other by π-π during cooling to self-assemble and recrystallize. However, in the present invention, by coexisting polyvinylpyrrolidone, the cyclic portion of the five-membered ring lactam structure of polyvinylpyrrolidone acts on the aromatic ring of the poorly water-soluble aromatic compound by van der Waals force during cooling, and is also poorly water-soluble. When the aromatic compound has a hydroxyl group, the poorly water-soluble aromatic compound and polyvinylpyrrolidone form a stable structure by forming a hydrogen bond with the carbonyl group of the five-membered ring lactam structure, and the poorly water-soluble aromatic compound and polyvinylpyrrolidone form a stable structure. It is considered that the self-assembly of aromatic compounds can be prevented. Further, when the poorly water-soluble aromatic compound-containing composition of the present invention is applied to skin, hair, etc., polyvinylpyrrolidone forms a coating film, and even when the solvent is volatilized, the poorly water-soluble aromatic compound and polyvinylpyrrolidone are formed. It is considered that stable solubility of the poorly water-soluble aromatic compound is realized because the structure of the above is maintained in a dispersed state without being broken.

The content of the (A) poorly water-soluble aromatic compound in the poorly water-soluble aromatic compound-containing composition of the present invention varies depending on the type thereof, but is preferably 0.2% by mass or more, preferably 0.2% by mass or more, from the viewpoint of usability. Is 0.5% by mass or more, more preferably 1.0% by mass or more, and (A) preferably 5.0% by mass or less from the viewpoint of solubility and dissolution stability of the poorly water-soluble aromatic compound. Is.

The content of (B) polyvinylpyrrolidone in the poorly water-soluble aromatic compound-containing composition of the present invention is preferably 0.1% by mass from the viewpoint of the solubility and dissolution stability of (A) the poorly water-soluble aromatic compound. % Or more, more preferably 0.5% by mass or more, and from the viewpoint of economic efficiency, it is preferably 20% by mass or less.

The mass ratio [(A) / (B)] of the (A) poorly water-soluble aromatic compound to (B) polyvinylpyrrolidone in the poorly water-soluble aromatic compound-containing composition of the present invention is (A) poorly water-soluble. From the viewpoint of dissolution stability of the aromatic compound, it is preferably 0.5 or less, more preferably 0.3 or less, and (A) it is preferable from the viewpoint that the solubilization amount of the poorly water-soluble aromatic compound can be increased. Is 0.05 or more.

The content of the organic solvent in the poorly water-soluble aromatic compound-containing composition of the present invention is preferably 10% by mass or more, more preferably 20% by mass, from the viewpoint of (A) solubility of the poorly water-soluble aromatic compound. From the above, and from the viewpoint of reducing irritation to the skin, it is preferably 60% by mass or less.

Further, the content of the surfactant in the poorly water-soluble aromatic compound-containing composition of the present invention is preferably 0 to 0.1 from the viewpoint of advantageously exerting the effect of (A) the poorly water-soluble aromatic compound. It is preferably 0% to 0.05% by mass, more preferably 0 to 0.01% by mass, and substantially 0% by mass, that is, it does not contain a surfactant.

The composition containing a poorly water-soluble aromatic compound of the present invention can be used for products in various fields such as pharmaceuticals, quasi-drugs, cosmetics, foods and drinks, and is applied to skin and hair by application and spraying. It is useful to use it as an external preparation. The skin refers to the skin of the body, preferably the scalp and the skin of the face. Body hair is preferably hair.
Examples of the external preparation include make-up cosmetics, sunscreen cosmetics, acne cosmetics, deodorant cosmetics, whitening cosmetics, hair conditioning agents, hair growth agents and the like.

[raw materials]
Ferulic acid (FA, manufactured by Tsukino Food Industry Co., Ltd., purity 98% or more)
Trance-3,4'-dimethyl-3-hydroxyflavanone (t-flavanone, manufactured by Kao Corporation, purity 99% or higher)
Polyvinylpyrrolidone K-30 (PVP, manufactured by Wako Pure Chemical Industries, Ltd.)
99.5 degree ethanol (EtOH, manufactured by Wako Pure Chemical Industries, Ltd.)
1,3-Butanediol (1,3-BG, manufactured by KH Neochem Co., Ltd., 100% purity)

[Quantification of ferulic acid, trans-3,4'-dimethyl-3-hydroxyflavanone]
Using a high performance liquid chromatograph manufactured by Hitachi, Ltd., a column Cadenza CD-C18 (4.6 mmφ × 150 mm, 3 μm) manufactured by Intact Co., Ltd. was attached, and the procedure was performed by a gradient method at a column temperature of 40 ° C. The mobile phase A solution was a 0.05 mol / L acetic acid aqueous solution, and the B solution was acetonitrile, and the solution was sent at 1.0 mL / min. The gradient conditions are as follows.
Hours (minutes) Solution A (%) Solution B (%)
0 85 15
20 80 20
35 10 90
50 10 90
50.1 85 15
60 85 15
The sample injection volume was 10 μL, and the detection was quantified by the absorbance at a wavelength of 320 nm for ferulic acid and the absorbance at a wavelength of 254 nm for trans-3,4′-dimethyl-3-hydroxyflavanone.

[Evaluation of solubility]
The ferulic acid composition or trans-3,4'-dimethyl-3-hydroxyflavanone composition is stored at room temperature (25 ° C.) for 1 month, filtered through a PTFE filter having a pore size of 0.2 μm, and composed by the above-mentioned quantification method. The dissolved concentration of ferulic acid or trans-3,4'-dimethyl-3-hydroxyflavanone in the substance was measured.

[Application evaluation]
25 μL of the sample was uniformly applied to a PTFE uneven substrate (SPF MASTER-PA01: manufactured by Shiseido Medical Technology Co., Ltd.) and dried at room temperature for 30 minutes. Immediately after application and after drying for 30 minutes, the absorbance at the maximum absorption wavelength at a wavelength of 300-350 nm was measured using a spectrophotometer (manufactured by JASCO Corporation). The absorbance was taken as the average of the values measured at any three points on the substrate.

Hereinafter,% shall represent mass%.

Example 1
Purified water was added to make ferulic acid 0.5% and polyvinylpyrrolidone K-30 5%, and the obtained slurry was heated with a stainless steel batch reactor (manufactured by Nitto High Pressure Co., Ltd.) with an internal volume of 190 mL. Processing was performed. The heat treatment is carried out by raising the temperature to 120 ° C., holding it for 1 minute, quickly cooling it to room temperature (25 ° C.) (cooling rate 0.5 ° C./s), and extracting the heat treatment liquid to obtain a ferulic acid composition. rice field. Table 1 shows the results of evaluation of the heat treatment raw material composition, the heat treatment conditions, and the solubility of the ferulic acid composition.

Examples 2-5
Purified water was added to ferulic acid, polyvinylpyrrolidone K-30, 99.5 degree ethanol, and 1,3-butanediol in the amounts shown in Table 1, and heat treatment was performed in the same manner as in Example 1. An acid composition was obtained. Table 1 shows the results of evaluation of the heat treatment raw material composition, the heat treatment conditions, and the solubility of the ferulic acid composition.

Comparative Examples 1 to 5
Add purified water to each of ferulic acid, polyvinylpyrrolidone K-30, 99.5 degree ethanol, and 1,3-butanediol to the amounts shown in Table 1, and stir the slurry solution obtained at room temperature for 3 days (stirrer). , 500 r / min), and then filtered through a PTFE filter having a pore size of 0.2 μm, and the results of measuring the ferulic acid concentration in the solution are shown in Table 1.

Comparative Example 6
Purified water was added so that ferulic acid was 0.77% and 1,3-butanediol was 20%, and heat treatment was carried out in the same manner as in Example 1 to obtain a ferulic acid composition. Table 1 shows the results of evaluation of the heat treatment raw material composition, the heat treatment conditions, and the solubility of the ferulic acid composition.

Example 6
Purified water was added so that trans-3,4'-dimethyl-3-hydroxyflavanone was 0.5%, polyvinylpyrrolidone K-30 was 10%, and 99.5 degrees ethanol was 40%, and the same as in Example 1. Was heat-treated to obtain a trans-3,4'-dimethyl-3-hydroxyflavanone composition. Table 2 shows the results of evaluation of the composition of the heat-treated raw material, the heat-treated conditions, and the solubility of the trans-3,4'-dimethyl-3-hydroxyflavanone composition.

Comparative Example 7
A slurry solution obtained by adding purified water so that the amounts of trans-3,4'-dimethyl-3-hydroxyflabanone, polyvinylpyrrolidone K-30, and 99.5 degree ethanol are shown in Table 2 is 3 at room temperature. After stirring for a day (stirrer, 500 r / min), the mixture was filtered through a PTFE filter having a pore size of 0.2 μm, and the trans-3,4'-dimethyl-3-hydroxyflabanone concentration in the solution was measured. The results are shown in Table 2. ..

As is clear from Tables 1 and 2, the dissolution concentration of the poorly water-soluble aromatic compound was significantly increased by the method of the present invention. In addition, the composition containing the component (A) obtained in Examples 1 to 6 was kept clear at room temperature for 1 month or longer.

Example 7
A ferulic acid composition was obtained in the same manner as in Example 1. Table 3 shows the results of the heat treatment raw material composition, the heat treatment conditions, and the application evaluation of the ferulic acid composition.

Example 8
A ferulic acid composition was obtained in the same manner as in Example 4. Table 3 shows the results of the heat treatment raw material composition, the heat treatment conditions, and the application evaluation of the ferulic acid composition.

Comparative Example 8
A slurry solution was obtained in the same manner as in Comparative Example 1, stirred at room temperature for 3 days (stirrer, 500 r / min), and then filtered through a PTFE filter having a pore size of 0.2 μm. Table 3 shows the composition of the slurry solution and the results of application evaluation of the filtrate.

Comparative Example 9
A ferulic acid composition was obtained in the same manner as in Example 7 except that purified water was added so that the content of ferulic acid was 0.5% and the content of 1,3-butanediol was 5% to prepare a slurry. Table 3 shows the results of the heat treatment raw material composition, the heat treatment conditions, and the application evaluation of the ferulic acid composition.

Comparative Example 10
Ferulic acid was prepared in the same manner as in Example 8 except that purified water was added so that ferulic acid was 1.5%, 99.5 degrees ethanol was 20%, and 1,3-butanediol was 5%. The composition was obtained. Table 3 shows the results of the heat treatment raw material composition, the heat treatment conditions, and the application evaluation of the ferulic acid composition.

Example 9
Example 1 except that purified water was added so that trans-3,4'-dimethyl-3-hydroxyflavanone was 0.2%, 99.5 degree ethanol was 40%, and polyvinylpyrrolidone K-30 was 5%. The same heat treatment was carried out in the same manner as in the above to obtain a trans-3,4'-dimethyl-3-hydroxyflavanone composition. Table 4 shows the results of the heat treatment raw material composition, the heat treatment conditions, and the coating evaluation of the trans-3,4'-dimethyl-3-hydroxyflavanone composition.

Comparative Example 11
Purified water was added so that trans-3,4'-dimethyl-3-hydroxyflabanone was 0.2%, 99.5 degrees ethanol was 40%, and polyvinylpyrrolidone K-30 was 5% to obtain a slurry solution. After stirring at room temperature for 3 days (stirrer, 500 r / min), the mixture was filtered through a PTFE filter having a pore size of 0.2 μm. Table 4 shows the composition of the slurry solution and the results of application evaluation of the filtrate.

Comparative Example 12
Examples except that purified water was added so that trans-3,4'-dimethyl-3-hydroxyflavanone was 0.2%, 99.5 degree ethanol was 40%, and 1,3-butylene glycol was 5%. The same heat treatment as in No. 1 was carried out to obtain a trans-3,4'-dimethyl-3-hydroxyflavanone composition. Table 4 shows the results of the heat treatment raw material composition, the heat treatment conditions, and the coating evaluation of the trans-3,4'-dimethyl-3-hydroxyflavanone composition.

As is clear from Tables 3 and 4, the component (A) -containing compositions obtained in Examples 7 to 9 showed high absorbance immediately after application and after drying for 30 minutes. As a result, when the composition of the present invention is applied, a uniform coating film can be formed immediately after application as compared with the composition of the comparative example, and stable solubility of the poorly water-soluble aromatic compound can be realized even after drying. It shows that it can be done.

Claims (4)

The above-mentioned difficulty includes a step of heat-treating (A) a poorly water-soluble aromatic compound having a solubility in water at 25 ° C. of 5.0 g / L or less and (B) polyvinylpyrrolidone at 100 to 180 ° C. in the presence of an aqueous medium. A poorly water-soluble aromatic compound in which the water-soluble aromatic compound is one or more selected from resveratrol, caffeic acid, ferulic acid, p-coumaric acid and trans-3,4'-dimethyl-3-hydroxyflabanone . A method for producing a group-containing compound-containing composition. (B) The method for producing a poorly water-soluble aromatic compound-containing composition according to claim 1, wherein the K value of polyvinylpyrrolidone is 10 to 60. The poor water solubility according to claim 1 or 2, wherein in the step of heat treatment, the mass ratio [(A) / (B)] of the (A) poorly water-soluble aromatic compound to (B) polyvinylpyrrolidone is 0.5 or less. A method for producing an aromatic compound-containing composition. The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of claims 1 to 3, wherein the aqueous medium is an aqueous solution of water or an organic solvent.