JP6611646B2 - Cosmetics - Google Patents

Description

  The present invention relates to a cosmetic.

Aromatic compounds are widely used in products such as cosmetics, pharmaceuticals, foods and daily necessities. Aromatic compounds are solid at room temperature and are hardly soluble in water, and when used in cosmetics and the like, blending is difficult, and the physiological activity effect cannot be sufficiently obtained.
The use form of the slightly water-soluble aromatic compound is generally dissolved in alcohol and used (for example, Patent Documents 1 and 2).
However, the feeling of use is liable to be impaired by the stimulation of alcohol to the skin. Moreover, the composition which can be applied will be restrict | limited.

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

JP 2009-96777 A JP 2011-153122 A JP 2005-82506 A JP2011-98919A JP 2013-124225 A

However, a so-called glycoside obtained by adding a sugar to a poorly water-soluble aromatic compound itself such as isopropylmethylphenol glycoside has high solubility in water, but its production process is complicated, so that the cost is high. Therefore, it is economically disadvantageous to use isopropylmethylphenol glycoside instead of isopropylmethylphenol or to use polyphenol glycoside as a solubilizer.
On the other hand, in the method of solubilizing a poorly water-soluble aromatic compound using a surfactant, the physiological effect of the aromatic compound such as sufficient solubility and antibacterial effect may not be obtained.
Therefore, the present invention intends to provide a cosmetic that stably contains a poorly water-soluble aromatic compound and sufficiently exhibits its effect.

  In the presence of an aqueous medium, the present inventors heat-treat a poorly water-soluble aromatic compound, a dihydric alcohol, and a trihydric or higher alcohol at 100 to 180 ° C. to obtain a normal water-insoluble aromatic compound. Compared with the solubility in water, the concentration of the slightly water-soluble aromatic compound is dramatically increased. In addition, the composition that has undergone such a treatment suppresses the precipitation of the aromatic compound even at room temperature, and is stable. It was found that high solubility in water was maintained. And the effect of a poorly water-soluble aromatic compound is sufficiently exhibited by combining such a poorly water-soluble aromatic compound-containing composition and one or more selected from a deodorant component, a bactericidal component, and a feel improving component. In addition, the present inventors have found that a cosmetic capable of sufficiently expressing the effects of the combined ingredients can be obtained.

The present invention is obtained by a method comprising a step of heat-treating (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol at 100 to 180 ° C. in the presence of an aqueous medium. And
(C) a hardly water-soluble aromatic compound-containing composition having a mass ratio [(B) / (C)] of (B) dihydric alcohol to trihydric or higher alcohol of 1.5 to 10;
(D) It is related with the cosmetics containing 1 or more types chosen from a deodorizing component, a bactericidal component, and a touch improvement component.

  The cosmetics of this invention can fully exhibit the effect of a poorly water-soluble aromatic compound by using the poorly water-soluble aromatic compound containing composition excellent in the solubility to water. When an aromatic antibacterial component is used as the poorly water-soluble aromatic compound, an excellent deodorizing effect and bactericidal effect are obtained, and there is no stickiness and a smooth feeling can be obtained.

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

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

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

Examples of aromatic hair-growth ingredients include flavanol derivatives such as trans-3,4′-dimethyl-3-hydroxyflavanone; nicotinic acids such as benzyl nicotinate, tocopherol nicotinate and β-butoxyethyl nicotinate; α-tocopherol And vitamin E such as dl-α-tocopherol acetate, tocopherol nicotinate and natural vitamin E; minoxidil, bimatoprost, tafluprost, nonyl acid vanillylamide, hypericum extract, capsicum tincture and the like.
Among them, trans-3,4'-dimethyl-3-hydroxyflavanone, benzyl nicotinate, tocopherol nicotinate, β-butoxyethyl nicotinate, α-tocopherol, dl-α-tocopherol acetate, tocopherol nicotinate, natural vitamin E , Minoxidil, bimatoprost, tafluprost, nonylic acid vanillylamide, hypericum herb extract and chili tincture are preferred, and trans-3,4'-dimethyl-3-hydroxyflavanone is more preferred. A flavanol derivative can be manufactured by a well-known method, for example, the method of Unexamined-Japanese-Patent No. 2000-198779.

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

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

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

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

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

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

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

  In the heat treatment raw material, the mass ratio [(A) / (B)] of the component (A) to the component (B) is 0.02 or more from the solubility point of the aromatic compound-containing composition obtained after cooling. Further, 0.025 or more is preferable, 0.06 or more is more preferable, 1 or less, further 0.5 or less, and further 0.15 or less is preferable. Moreover, 0.02-1 are preferable, 0.025-0.5 are more preferable, and 0.06-0.15 are still more preferable.

  In the heat treatment raw material, the mass ratio [(A) / (C)] of the component (A) to the component (C) is 0.12 or more in terms of the solubility of the aromatic compound-containing composition obtained after cooling. Further, it is preferably 0.15 or more, more preferably 0.17 or more, and 1.5 or less, further 1 or less, and further preferably 0.6 or less. Moreover, 0.12-1.5 are preferable, 0.15-1 are still more preferable, and 0.17-0.6 are still more preferable.

  In the heat treatment raw material, the mass ratio [(B) / (C)] of the component (B) to the component (C) is 1.5 or more in terms of the solubility of the aromatic compound-containing composition obtained after cooling. Further, 2 or more, further 2.5 or more are preferable, 10 or less, further 8 or less are preferable, and 6 or less is more preferable. Moreover, 1.5-10 are preferable, 2-8 are still more preferable, and 2.5-6 are still more preferable.

  In addition, the mass ratio [(A) / {(B) + (C)}] of the component (A) to the total amount of the component (B) and the component (C) in the heat treatment raw material is an aromatic obtained after cooling. From the viewpoint of solubility and storage stability of the compound-containing composition, 0.015 or more, more preferably 0.019 or more, further preferably 0.05 or more, and 0.5 or less, further 0.2 or less. Furthermore, 0.1 or less is preferable. Moreover, 0.015-0.5 are preferable, 0.019-0.5 are more preferable, 0.05-0.2 are still more preferable, 0.05-0.1 are still more preferable.

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

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

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

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

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

  In the present invention, when producing a hardly water-soluble aromatic compound-containing composition, the heat treatment liquid obtained by heat treatment is cooled to 90 ° C. or less, preferably 50 ° C. or less, more preferably 30 ° C. or less. It is preferable that the process to include is included. When obtaining a liquid poorly water-soluble aromatic compound containing composition, 0 degreeC or more is preferable and 10 degreeC or more is preferable.

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

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

The hardly water-soluble aromatic compound-containing composition thus obtained contains (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol in an aqueous medium. (A) Despite the high content of the hardly water-soluble aromatic compound, precipitation of the hardly water-soluble aromatic compound can be suppressed even at room temperature and during storage at room temperature. Moreover, it is excellent in solubility in water.
The content of the component (A) in the hardly water-soluble aromatic compound-containing composition is preferably 1 g / L or more, more preferably 2 g / L or more, further 7.5 g / L or more, from the viewpoint of physical distribution and usability. Furthermore, 30 g / L or more is preferable.
In the hardly water-soluble aromatic compound-containing composition, the content of the dihydric alcohol of component (B) is 0.1% by mass in the total composition from the viewpoint of the solubility of the aromatic compound-containing composition obtained after cooling. The above is preferable, 1% by mass or more is more preferable, 2% by mass or more is further preferable, 10% by mass or more is more preferable, 30% by mass or more is further preferable, 70% by mass or less is preferable, and 60% by mass or less is more preferable. 50 mass% or less is still more preferable. Moreover, 0.1-70 mass% is preferable in the whole composition, as for content of the component (B) in a hardly water-soluble aromatic compound containing composition, 1-60 mass% is more preferable, and 2-50 mass%. More preferably, 10-50 mass% is more preferable, and 30-50 mass% is further more preferable.
In the hardly water-soluble aromatic compound-containing composition, the content of the trivalent or higher alcohol of component (C) is 0.1% in the total composition from the viewpoint of the solubility of the aromatic compound-containing composition obtained after cooling. % By mass or more, preferably 1% by mass or more, more preferably 5% by mass or more, further preferably 10% by mass or more, more preferably 50% by mass or less, more preferably 30% by mass or less, and 25% by mass or less. More preferred is 20% by mass or less. Moreover, 0.1-50 mass% is preferable in the whole composition, and, as for content of the component (C) in a slightly water-soluble aromatic compound containing composition, 0.1-30 mass% is more preferable, and 1-25 mass. % Is more preferable, 5 to 25% by mass is more preferable, and 10 to 20% by mass is further preferable.

In the hardly water-soluble aromatic compound-containing composition, the mass ratio [(A) / (B)] of the component (A) to the component (B) is 0 from the viewpoint of improving the stability of the hardly water-soluble aromatic compound. 0.02 or more, more preferably 0.025 or more, further preferably 0.06 or more, and 1 or less, further 0.5 or less, and further preferably 0.15 or less. Moreover, 0.02-1 is preferable, 0.025-0.5 is still more preferable, 0.06-0.15 is still more preferable.
The mass ratio [(A) / (C)] of the component (A) to the component (C) in the hardly water-soluble aromatic compound-containing composition is 0 from the viewpoint of improving the stability of the aromatic compound-containing composition. .12 or more, further 0.15 or more, and further 0.17 or more are preferable, and 1.5 or less, further 1 or less, and further 0.6 or less are preferable. Moreover, 0.12-1.5 are preferable, 0.15-1 are still more preferable, and 0.17-0.6 are still more preferable.

  The mass ratio [(B) / (C)] of the component (B) to the component (C) in the hardly water-soluble aromatic compound-containing composition is from the solubility point of the aromatic compound-containing composition obtained after cooling. 1.5 or more, further 2 or more, further 2.5 or more are preferable, and 10 or less, further 8 or less, and further 6 or less are preferable. Moreover, 1.5-10 are preferable, 2-8 are still more preferable, and 2.5-6 are still more preferable.

  Moreover, the mass ratio [(A) / {(B) + (C)}] of the component (A) to the total amount of the component (B) and the component (C) in the hardly water-soluble aromatic compound-containing composition is: From the viewpoint of stability, it is preferably 0.015 or more, more preferably 0.019 or more, further preferably 0.05 or more, and is preferably 0.5 or less, more preferably 0.2 or less, and further preferably 0.1 or less. Moreover, 0.015-0.5 are preferable, 0.019-0.5 are more preferable, 0.05-0.2 are still more preferable, 0.05-0.1 are still more preferable.

  In the hardly water-soluble aromatic compound-containing composition, the content of the organic solvent, particularly a monohydric alcohol having 4 or less carbon atoms, is desirably reduced from the viewpoint of irritation to the skin. The content of the organic solvent in the hardly water-soluble aromatic compound-containing composition is preferably 0 to 60%, more preferably 0 to 30%, still more preferably 0 to 10%, still more preferably 0 to 1%, substantially In particular, it is more preferable that 0%, that is, no organic solvent is contained.

  In the hardly water-soluble aromatic compound-containing composition, the content of the surfactant is preferably reduced from the viewpoint of advantageously exerting the effect of the (A) hardly water-soluble aromatic compound. The content of the surfactant in the hardly water-soluble aromatic compound-containing composition is preferably 0 to 1 g / L, more preferably 0 to 0.5 g / L, still more preferably 0 to 0.1 g / L, and substantially More preferably, it is 0 g / L, that is, it does not contain a surfactant.

  The cosmetic of the present invention contains a sparingly water-soluble aromatic compound-containing composition and component (D), but preferably further contains an aqueous medium such as water. The blending method may be performed by adding a slightly water-soluble aromatic compound-containing composition to an aqueous medium, and then adding and mixing the component (D) and other components, or a slightly water-soluble aromatic compound-containing composition. Component (D) and other components may be added independently or together and mixed. The concentration of the hardly water-soluble aromatic compound in the aqueous medium is 0.1 to 50 g / L, further 0.2 to 30 g / L, further 0.5 to 10 g / L, further 0.5 to 5 g / L, and further 0. 0.5-2 g / L is preferred. Although the hardly water-soluble aromatic compound-containing composition has a drastic increase in the solubility of the hardly water-soluble aromatic compound in comparison with the solubility in water of a normal poorly water-soluble aromatic compound, It can be set to a desired concentration, and even in that case, precipitation of a poorly water-soluble aromatic compound is suppressed and stability is high. Moreover, high physiological activity expression of a poorly water-soluble aromatic compound can be expected.

The hardly water-soluble aromatic compound-containing composition contains (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol in an aqueous medium. The cosmetic contains the poorly water-soluble aromatic compound-containing composition obtained as described above.
In the cosmetics of the present invention, the content of the poorly water-soluble aromatic compound of the component (A) is sufficient from the viewpoint of sufficiently exhibiting the effect of the poorly water-soluble aromatic compound. In the case of using the components, excellent deodorizing effect and bactericidal effect are obtained, there is no stickiness, and from the viewpoint of obtaining a smooth feeling, 0.01% by mass or more is preferable in the total composition, and 0.02% by mass The above is more preferable, 0.05 mass% or more is further preferable, 1 mass% or less is preferable, 0.5 mass% or less is more preferable, and 0.3 mass% or less is still more preferable. Further, the content of the component (A) is preferably 0.01 to 1% by mass, more preferably 0.02 to 0.5% by mass, and further preferably 0.05 to 0.3% by mass in the total composition. .
In the cosmetic of the present invention, the content of the dihydric alcohol of the component (B) is such that an aromatic antibacterial component is used as the poorly water-soluble aromatic compound from the viewpoint of sufficiently exerting the effect of the poorly water-soluble aromatic compound. In that case, 0.09% by mass or more is preferable in the total composition, and 0.18% by mass or more is more preferable from the viewpoint of obtaining an excellent deodorizing effect and bactericidal effect, no stickiness, and a smooth feeling. Preferably, 0.3% by mass or more is more preferable, 0.45% by mass or more is further more preferable, 8.4% by mass or less is preferable, 7% by mass or less is more preferable, and 5.5% by mass or less is further preferable. 5 mass% or less is still more preferable. The content of component (B) is preferably 0.09 to 8.4% by mass, more preferably 0.18 to 7% by mass, and still more preferably 0.3 to 5.5% by mass in the total composition. 0.45 to 5% by mass is even more preferable.
In the cosmetic of the present invention, the content of the trivalent or higher alcohol of the component (C) is such that the effect of the cold water-insoluble aromatic compound is sufficiently exhibited, and the antibacterial aromatic as an insoluble water-soluble aromatic compound. In the case of using the components, excellent deodorizing effect and bactericidal effect are obtained, there is no stickiness, and from the viewpoint of obtaining a smooth feeling, 0.01% by mass or more is preferable in the total composition, and 0.03% by mass The above is more preferable, 0.06% by mass or more is further preferable, 0.09% by mass or more and further more than 2% by mass is more preferable, 2.86% by mass or less is preferable, 2.5% by mass or less is more preferable, and 2% by mass. % Or less is more preferable, and 1.72 mass% or less is still more preferable. Further, the content of the component (C) is preferably 0.01 to 2.86% by mass in the total composition, more preferably 0.03 to 2.5% by mass, and still more preferably 0.06 to 2% by mass. 0.09 to 1.72% by mass is even more preferable.

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

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

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

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

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

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

  When using a feel improving component as the component (D), the content is preferably 0.01% by mass or more in the total composition from the viewpoint of reducing the squeaky feeling, suppressing the roughness and further improving the smooth feeling, 0.1% by mass or more is more preferable, 1% by mass or more is further preferable, 1.5% by mass or more is further more preferable, 20% by mass or less is preferable, 10% by mass or less is more preferable, and 5% by mass or less is further more preferable. Is more preferable. Moreover, when using a feeling improvement component as a component (D), 0.01-20 mass% is preferable in the whole composition, 0.1-20 mass% is more preferable, 1-10 mass% is preferable. Is more preferable, and 1.5 to 5% by mass is even more preferable.

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

In addition to the above-mentioned components, the cosmetics of the present invention are components used in ordinary cosmetics, such as oily components, surfactants, water-soluble polymers, extracts, antioxidants, pigments, pH adjusters, ultraviolet absorption. An agent, a blood circulation promoter, a fragrance | flavor, etc. can be contained.
The cosmetics of the present invention are suitable for making water-based products, and skins such as skin lotions, makeup cosmetics, sunscreen cosmetics, acne cosmetics, deodorant cosmetics, and whitening cosmetics. It is suitable as a cosmetic.

[Quantification of isopropylmethylphenol]
Using a high-performance liquid chromatograph manufactured by Hitachi, Inc., a column Cadenza CD-C18 (4.6 mmφ × 150 mm, 3 μm) manufactured by Intact was installed, and the gradient method was performed at a column temperature of 40 ° C. The mobile phase A solution was 0.05 mol / L acetic acid aqueous solution, the B solution was acetonitrile, and the solution was fed at 1.0 mL / min. The gradient conditions are as follows.
Time (min) A liquid (%) B liquid (%)
0 85 15
20 80 20
35 10 90
50 10 90
50.1 85 15
60 85 15
The sample injection amount was 10 μL, and the detection was quantified by measuring the absorbance of isopropylmethylphenol at a wavelength of 283 nm.

[raw materials]
Isopropylmethylphenol (IPMP, Osaka Kasei Co., Ltd., purity 100%)
1,3-butanediol (1,3-BG, manufactured by KH Neochem, purity 100%)
1,3-propanediol (1,3-PG, manufactured by DuPont, purity 100%)
Glycerin (Gly, Kao Corporation, purity 100%)
Diglycerin (DG, Sakamoto Pharmaceutical Co., Ltd., purity 100%)

Production Example 1
Isopropylmethylphenol was added to distilled water at 30 g / L, 1,3-butanediol at 500 g / L, and glycerin at 100 g / L, and the resulting slurry was added to a 190 mL stainless batch reactor (Nitto). Heat treatment was performed at a high pressure company. After reaching the temperature of 150 ° C., the temperature was maintained for 1 minute and quickly cooled to room temperature (25 ° C.) (cooling rate 0.5 ° C./s). The pressure during the heat treatment was 0.4 MPa. After cooling, the heat treatment solution was immediately extracted and filtered through a PTFE filter having a pore size of 0.2 μm to obtain an isopropylmethylphenol composition.
Table 1 shows the results of measurement of the treatment conditions and the isopropylmethylphenol concentration, 1,3-butanediol concentration, and glycerin concentration in the composition at 25 ° C.

Production Examples 2-7
Add isopropylmethylphenol, 1,3-butanediol or 1,3-propanediol, glycerin or diglycerin to distilled water so as to have the amounts shown in Table 1, respectively, and heat-treat in the same manner as in Production Example 1. An isopropylmethylphenol composition was obtained.
Table 1 shows the treatment conditions and the results of measuring the isopropylmethylphenol concentration, 1,3-butanediol concentration, 1,3-propanediol concentration, glycerin concentration and diglycerin concentration in the composition at 25 ° C.

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

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

Comparative production examples 3-4
Without adding glycerin, isopropylmethylphenol and 1,3-butanediol were added to distilled water to the amounts shown in Table 2, respectively, and an isopropylmethylphenol composition was obtained in the same manner as in Production Example 1. Table 2 shows the treatment conditions and the results of measuring the isopropylmethylphenol concentration and the 1,3-butanediol concentration in the composition.

Comparative Production Example 5
Without adding 1,3-butanediol, isopropylmethylphenol and glycerin were added to distilled water to the amounts shown in Table 2, respectively, and an isopropylmethylphenol composition was obtained in the same manner as in Production Example 1. Table 2 shows the treatment conditions and the results of measuring the isopropylmethylphenol concentration and the glycerin concentration in the composition.

As is clear from Tables 1 and 2, in Production Examples 1 to 7, a water-insoluble aromatic compound-containing composition having a high content of isopropylmethylphenol, which is a water-insoluble aromatic compound, can be obtained. The solubility of the aromatic compound can be remarkably increased.
Moreover, even if the poorly water-soluble aromatic compound-containing composition obtained in Production Examples 1 to 7 was cooled to room temperature, no precipitate was deposited, and a stable dissolved state was maintained.

Examples 1-7, Comparative Examples 1-5
Using the isopropylmethylphenol (IPMPF) compositions obtained in Production Examples 1 to 7 and Comparative Production Examples 1 to 5, the deodorant cosmetics shown in Tables 3 and 4 were produced, and the stickiness, deodorant effect, bactericidal effect, The smoothness and the deodorizing effect were evaluated. The results are shown in Table 3 and Table 4 together.

(Production method)
Based on the IPMP concentration analysis values of the IPMP compositions obtained in Production Examples 1 to 7 and Comparative Production Examples 1 to 5, it was dropped into water under stirring at room temperature (25 ° C.) so that the IPMP concentration was 0.1% by mass. And diluted. In that case, the component (D) was previously mixed with water so that it might become a predetermined density | concentration before dripping of an IPMP composition.

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

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

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

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

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

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

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

Claims (5)

Cosmetics containing the following component (1) and component (D) (detergent composition containing 4% by mass or more of a surfactant and external preparation composition for acne containing a nonionic surfactant of HLB 15 or more Except for things).
(1) obtained by a method comprising a step of heat-treating (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol at 100 to 180 ° C. in the presence of an aqueous medium. ,
(A) The poorly water-soluble aromatic compound is at least one selected from triclosan and isopropylmethylphenol . (B) The dihydric alcohol is ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1, 3-propanediol, 1,3-butanediol, at least one selected from dipropylene glycol and polyethylene glycol, with (C) one or more trivalent or higher alcohol is glycerin, selected from diglycerol and triglycerol There, the weight ratio [(B) / (C) ] is poorly water-soluble aromatic compound-containing composition is 1.5 to 10 (D) deodorant of component (B) to component (C), bactericidal component and One or more ingredients selected from feel-enhancing ingredients   (B) The dihydric alcohol is at least one selected from ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol and 1,3-butanediol. Cosmetics.   (C) The cosmetic according to claim 1 or 2, wherein the trivalent or higher alcohol is glycerin or diglycerin.   Cosmetics given in any 1 paragraph of Claims 1-3 whose mass ratio [(A) / (B)] of ingredient (A) to ingredient (B) in ingredient (1) is 0.02-1.   The mass ratio [(A) / {(B) + (C)}] of component (A) to the total amount of component (B) and component (C) in component (1) is 0.015 to 0.5. The cosmetic according to any one of claims 1 to 4.