WO2015156317A1 - Procédé de fabrication d'une composition contenant un composé aromatique faiblement hydrosoluble - Google Patents

Procédé de fabrication d'une composition contenant un composé aromatique faiblement hydrosoluble Download PDF

Info

Publication number
WO2015156317A1
WO2015156317A1 PCT/JP2015/060976 JP2015060976W WO2015156317A1 WO 2015156317 A1 WO2015156317 A1 WO 2015156317A1 JP 2015060976 W JP2015060976 W JP 2015060976W WO 2015156317 A1 WO2015156317 A1 WO 2015156317A1
Authority
WO
WIPO (PCT)
Prior art keywords
aromatic compound
less
component
soluble aromatic
mass
Prior art date
Application number
PCT/JP2015/060976
Other languages
English (en)
Japanese (ja)
Inventor
阿部　哲也
晶宏 宇田
秀隆 岩井
小松　利照
Original Assignee
花王株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 花王株式会社 filed Critical 花王株式会社
Priority to CN201580016689.XA priority Critical patent/CN106132389B/zh
Publication of WO2015156317A1 publication Critical patent/WO2015156317A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • the present invention relates to a method for producing a slightly water-soluble aromatic compound-containing composition and a cosmetic.
  • Aromatic compounds are widely used in products such as cosmetics, pharmaceuticals, foods and daily necessities. Aromatic compounds are solid at room temperature and are often insoluble in water, and their usage is generally dissolved in alcohol and used (for example, Patent Documents 1 and 2). However, the feeling of use is liable to be impaired by the stimulation of alcohol to the skin. Moreover, the composition which can be applied will be restrict
  • Patent Document 3 an isopropylmethylphenol glycoside in which a sugar such as glucose is bound to isopropylmethylphenol
  • Patent Document 4 a method of solubilizing isopropylmethylphenol using a wetting agent in combination
  • Patent Document 5 a method for solubilizing sparingly water-soluble hair-grown ingredients by heat-treating sparingly water-soluble hair-grown ingredients and water-soluble aromatic compounds such as polyphenol glycosides at 100 to 180 ° C. in the presence of an aqueous medium.
  • Patent Document 1 JP 2009-96777 (Patent Document 2) JP 2011-153122 (Patent Document 3) JP 2005-82506 (Patent Document 4) JP 2011-98919 (Patent Document 3) Reference 5) Japanese Unexamined Patent Publication No. 2013-124225
  • the present invention includes a step of heat-treating (A) a poorly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol at 100 to 180 ° C. in the presence of an aqueous medium.
  • the manufacturing method of a water-soluble aromatic compound containing composition, the sparingly water-soluble aromatic compound containing composition obtained by this manufacturing method, and the cosmetics containing this sparingly water-soluble aromatic compound containing composition are provided.
  • 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.
  • the physiological effect of the aromatic compound such as sufficient solubility and antibacterial effect may not be obtained.
  • the present invention provides a hardly water-soluble aromatic compound-containing composition (hereinafter referred to as “component (A) -containing composition”) having excellent solubility in water of the hardly water-soluble aromatic compound (component (A) of the present invention).
  • component (A) -containing composition a hardly water-soluble aromatic compound-containing composition having excellent solubility in water of the hardly water-soluble aromatic compound (component (A) of the present invention).
  • component (A) -containing composition a hardly water-soluble aromatic compound-containing composition having excellent solubility in water of the hardly water-soluble aromatic compound (component (A) of the present invention).
  • component (A) -containing composition a hardly water-soluble aromatic compound-containing composition having excellent solubility in water of the hardly water-soluble aromatic compound (component (A) of the present invention.
  • the inventors of the present invention have made various studies on the solubilization technique of a poorly water-soluble aromatic compound.
  • the dissolution concentration of the hardly water-soluble aromatic compound is drastically increased as compared with the solubility in water of a normal poorly water-soluble aromatic compound, and the composition subjected to such treatment
  • precipitation of the aromatic compound was suppressed even at room temperature, and it was found that the solubility of the component (A) in water was stably maintained.
  • the effect of a poorly water-soluble aromatic compound is sufficiently exhibited by combining the component (A) -containing composition that has undergone such treatment with at least one selected from a deodorant component, a bactericidal component, and a touch-improving component.
  • the present inventors have found that a cosmetic capable of sufficiently expressing the effects of the combined ingredients can be obtained.
  • the component (A) containing composition excellent in the solubility to the water of a component (A) can be manufactured cheaply.
  • this component (A) -containing composition By using this component (A) -containing composition, the use of ethanol can be reduced or avoided, so that it is possible to provide an aqueous product with less skin irritation.
  • the cosmetics of this invention can fully exhibit the effect of a slightly water-soluble aromatic compound by using the component (A) containing composition which is excellent in the solubility of the component (A) in water.
  • an aromatic antibacterial component is used as the hardly water-soluble aromatic compound, an excellent deodorizing effect and bactericidal effect are obtained, and there is no stickiness and a smooth feeling can be obtained.
  • the component (A) -containing composition of the present invention 100 to 100 of (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol in the presence of an aqueous medium. Including a step of heat treatment at 180 ° C.
  • 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.
  • 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.
  • 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.
  • the poorly water-soluble aromatic compound may be one type or a mixture of two or more types.
  • aromatic antibacterial components include phenolic antibacterial agents and preservatives.
  • Phenol antibacterial agents are chlorophenol antibacterial agents such as triclosan, chlorthymol, carbachlor, chlorophene, dichlorophen, hexachlorophene, chloroxylenol, chlorocresol; O-phenylphenol and isopropylmethylphenol are preferred, and triclosan and isopropyl are further preferred. Methylphenol is preferred, and isopropylmethylphenol is more preferred.
  • the preservative is preferably a paraoxybenzoic acid ester such as methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, benzylparaben.
  • a paraoxybenzoic acid ester such as methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, benzylparaben.
  • the aromatic whitening component examples include chromone derivatives.
  • the chromone derivative has a chromone, ie, a linear or branched alkyl group having 1 to 15 carbon atoms at the 2-position of 4H-1-benzopyran-4-one, and a hydrogen atom, a hydroxy group or an alkoxy group at the 7-position. Compounds having a group are preferred.
  • chromone derivatives examples include 2-butylchromone, 2-pentylchromone, 2-heptylchromone, 2-nonylchromone, 2-hexadecylchromone, 2- (1-ethylpentyl) chromone, 2-butyl-7 -Methoxychromone, 2-pentyl-7-methoxychromone, 2-heptyl-7-methoxychromone, 2-nonyl-7-methoxychromone, 2-pentadecyl-7-methoxychromone, 2- (1-ethylpentyl) -7 -Methoxychromone, 7-hydroxy-2-methylchromone, 7-hydroxy-2-butylchromone, 7-hydroxy-2-pentylchromone, 7-hydroxy-2-heptylchromone, 7-hydroxy-2-nonylchromone, 7- Hydroxy-2-pentadesilchromone, 7-hydroxy-2- (1- Chir
  • aromatic hair-growth component examples include flavanol derivatives such as trans-3,4′-dimethyl-3-hydroxyflavanone; nicotinic acids such as benzyl nicotinate, tocopherol nicotinate and ⁇ -butoxyethyl nicotinate; ⁇ -tocopherol And vitamin E such as dl- ⁇ -tocopherol acetate, tocopherol nicotinate and natural vitamin E; minoxidil, bimatoprost, tafluprost, nonyl acid vanillamide, hypericum extract, capsicum tincture and the like.
  • flavanol derivatives such as trans-3,4′-dimethyl-3-hydroxyflavanone
  • nicotinic acids such as benzyl nicotinate, tocopherol nicotinate and ⁇ -butoxyethyl nicotinate
  • ⁇ -tocopherol And vitamin E such as dl- ⁇ -tocopherol
  • trans-3,4'-dimethyl-3-hydroxyflavanone benzyl nicotinate, tocopherol nicotinate, ⁇ -butoxyethyl nicotinate, ⁇ -tocopherol, dl- ⁇ -tocopherol acetate, tocopherol nicotinate, natural vitamin E Minoxidil, bimatoprost, tafluprost, nonylic acid vanillyl amide, hypericum herb extract and capsicum tincture are preferred, and trans-3,4′-dimethyl-3-hydroxyflavanone is more preferred.
  • the flavanol derivative can be produced by a known method, for example, a method described in JP-A-2000-198779.
  • the (B) dihydric alcohol used in the present invention is a general term for alcohols in which two hydrogen atoms of a hydrocarbon are substituted with a hydroxyl group.
  • ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, and dipropylene glycol are preferred from the viewpoint of solubilization of poorly water-soluble aromatic compounds, and propylene glycol, 1,3- Propanediol and 1,3-butanediol are preferred.
  • the weight average molecular weight of polyethylene glycol is preferably 200 to 20,000.
  • 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.
  • glycerins such as glycerin, diglycerin and triglycerin; , 2,4-butanetriol, 1,2,5-pentanetriol, 2-methylpropanetriol, 2-methyl-1,2,4-butanetriol, trimethylolethane, trimethylolpropane and the like.
  • Trivalent to pentavalent alcohols are preferred, and trivalent alcohols are more preferred.
  • 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.
  • water examples 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.
  • 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.
  • the organic solvent as used in the field of this invention excludes (B) dihydric alcohol and (C) trihydric or more alcohol.
  • the concentration of the organic solvent in the aqueous solution is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, further preferably 0 to 10% by mass, further preferably 0 to 1% by mass, and substantially 0% by mass. That is, it is more preferable not to contain an organic solvent.
  • 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 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.
  • a heat treatment raw material containing an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol is prepared, and the heat treatment is performed.
  • the content of the (A) poorly water-soluble aromatic compound in the heat-treated raw material varies depending on the type, but is usually 0.1 g / L or more, more preferably 0.5 g / L or more, and further 0 from the viewpoint of productivity.
  • / L or less more preferably 100 g / L or less, further 75 g / L or less, further 60 g / L or less, further 55 g / L or less, and further 50 g / L or less.
  • 0.1 to 150 g / L is preferable, 0.1 to 100 g / L is more preferable, 0.5 to 75 g / L is more preferable, 0.7 to 60 g / L is still more preferable, and 0.9 to 55 g. / L is more preferred, 1 to 55 g / L is more preferred, 1 to 50 g / L is more preferred, 2 to 50 g / L is more preferred, 7.5 to 50 g / L is still more preferred, and 30 to 50 g / L is more preferred. Further preferred.
  • the content of the (B) dihydric alcohol in the heat treatment raw material varies depending on the type, but is usually 1 g / L or more, further 10 g / L or more, and further 20 g / L from the solubility point of the component (A).
  • the above is preferable, more preferably 100 g / L or more, further preferably 300 g / L or more, and from the viewpoint of fluidity, 700 g / L or less, further 600 g / L or less, and further 500 g / L or less is preferable.
  • it is preferably 1 to 700 g / L, more preferably 10 to 600 g / L, further preferably 20 to 500 g / L, further preferably 100 to 500 g / L, and further preferably 300 to 500 g / L.
  • the content of the (C) trivalent or higher alcohol in the heat treatment raw material varies depending on the type, but from the viewpoint of the solubility of the component (A), it is 1 g / L or more, further 10 g / L or more, and further 50 g / L. More preferably, it is 100 g / L or more, and from the viewpoint of storage stability and fluidity, it is preferably 500 g / L or less, more preferably 300 g / L or less, further 250 g / L or less, and even more preferably 200 g / L or less.
  • it is preferably 1 to 500 g / L, more preferably 1 to 300 g / L, further preferably 10 to 250 g / L, further preferably 50 to 250 g / L, and further preferably 100 to 200 g / L.
  • the mass ratio [(A) / (B)] of the component (A) to the component (B) in the heat-treated raw material is the solubility point of the component (A) in the component (A) -containing composition obtained after cooling.
  • 0.001 to 1 more preferably 0.001 to 0.5, still more preferably 0.001 to 0.2, still more preferably 0.002 to 0.15, and 0.002 to 0.13.
  • 0.002 to 0.12 is more preferable
  • 0.002 to 0.11 is further preferable
  • 0.02 to 0.11 is further preferable
  • 0.025 to 0.11 is further preferable
  • 0.02. More preferably, it is from 06 to 0.11.
  • the mass ratio of the component (A) to the component (B) in the heat-treated raw material [(A) / (B) ] Is 0.02 or more, more preferably 0.025 or more, and further preferably 0.06 or more, from the viewpoint of the solubility of the component (A) in the component (A) -containing composition obtained after cooling. It is preferably 1 or less, more preferably 0.5 or less, and further preferably 0.15 or less. Moreover, 0.02 to 1 is preferable, 0.025 to 0.5 is more preferable, and 0.06 to 0.15 is still more preferable.
  • the mass ratio [(A) / (C)] of the component (A) to the component (C) in the heat-treated raw material is the solubility point of the component (A) in the component (A) -containing composition obtained after cooling.
  • the mass ratio of the component (A) to the component (C) in the heat-treated raw material [(A) / (C) ] is preferably 0.12 or more, more preferably 0.15 or more, and further preferably 0.17 or more from the viewpoint of the solubility of the component (A) in the component (A) -containing composition obtained after cooling. It is preferably 5 or less, more preferably 1 or less, and further preferably 0.6 or less. Further, it is preferably 0.12 to 1.5, more preferably 0.15 to 1, and further preferably 0.17 to 0.6.
  • the mass ratio [(B) / (C)] of the component (B) to the component (C) is the solubility point of the component (A) in the component (A) -containing composition obtained after cooling. Therefore, 1.5 or more, further 2 or more, further 2.5 or more is preferable, 10 or less, further 8 or less is preferable, and 6 or less is more preferable. Further, it is preferably 1.5 to 10, more preferably 2 to 8, and further preferably 2.5 to 6. *
  • the mass ratio [(A) / ⁇ (B) + (C) ⁇ ] of the component (A) to the total amount of the component (B) and the component (C) in the heat treatment raw material is the component ( A) From the point of solubility of the component (A) in the containing composition and from the point of storage stability of the component (A) -containing composition, 0.001 or more, further 0.002 or more, further 0.015 or more, further It is preferably 0.019 or more, more preferably 0.05 or more, and is preferably 0.5 or less, further 0.2 or less, further 0.15 or less, further 0.12 or less, and further 0.10 or less.
  • 0.001 to 0.5 is preferable, 0.001 to 0.2 is more preferable, 0.002 to 0.15 is more preferable, 0.002 to 0.12 is still more preferable, and 0.002 to 0 is preferable. .10 is more preferable, 0.015 to 0.10 is more preferable, 0.019 to 0.10 is further preferable, and 0.05 to 0.10 is still more preferable.
  • the ratio [(A) / ⁇ (B) + (C) ⁇ ] is the solubility point of the component (A) in the component (A) -containing composition obtained after cooling, and the preservation of the component (A) -containing composition.
  • 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.
  • 0.015 to 0.5 is preferable, 0.019 to 0.5 is more preferable, 0.05 to 0.2 is still more preferable, and 0.05 to 0.1 is still more preferable.
  • a surfactant may be used. From the viewpoint of maintaining the physiological activity of the (A) poorly water-soluble aromatic compound and reducing the irritation to the skin, It is desirable to reduce the amount used.
  • the content of the surfactant in the heat treatment raw material is preferably 0 to 1 g / L, more preferably 0 to 0.5 g / L, further preferably 0 to 0.1 g / L, substantially 0 g / L, That is, it is more preferable not to contain a surfactant.
  • the method of heat-treating (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol in the presence of an aqueous medium is not particularly limited, and a known method can be applied.
  • the temperature of the heat treatment is 100 to 180 ° C., but (A) from the viewpoint of improving the solubility of the poorly water-soluble aromatic compound, it is preferably 110 ° C. or higher, more preferably 120 ° C. or higher, and heat stability. From the point, 170 ° C. or lower is more preferable, and 160 ° C. or lower is more preferable.
  • the temperature for the heat treatment is preferably 110 to 170 ° C, more preferably 120 to 160 ° C, and further preferably 120 to 150 ° C. Examples of the heating means include water vapor and electricity.
  • the pressure during the heat treatment is preferably 0 to 10 MPa, more preferably 0.1 to 8 MPa, further preferably 0.1 to 6 MPa, further preferably 0.2 to 6 MPa, and further preferably 0.2 to 4 MPa in terms of gauge pressure.
  • 0.25 to 2 MPa is more preferable, 0.3 to 1.5 MPa is more preferable, and 0.3 to 0.6 MPa is further preferable.
  • the gauge pressure is a pressure at atmospheric pressure of 0 MPa.
  • Gas may be used for pressurization, and examples of the gas used include inert gas, water vapor, nitrogen gas, helium gas, and the like.
  • the pressurization may be adjusted by a back pressure valve without using gas.
  • the heat treatment can be performed by any method such as a batch method, a semi-batch method, and a distribution method. Among these, the flow method is preferable in terms of easy control of the heat treatment time.
  • the heat treatment time is preferably 0.1 minutes or more, more preferably 0.2 minutes or more after the aqueous medium reaches the temperature of the heat treatment, from the viewpoint of improving the solubility of the (A) poorly water-soluble aromatic compound.
  • 0.5 minutes or more is more preferable, and from the viewpoint of thermal stability, 30 minutes or less is preferable, 15 minutes or less is more preferable, and 8 minutes or less is still more preferable.
  • the heat treatment time is preferably 0.1 to 30 minutes, more preferably 0.2 to 15 minutes, and further preferably 0.5 to 8 minutes after the aqueous medium reaches the temperature of the heat treatment.
  • the heat treatment time is an average residence time calculated by dividing the volume of the high-temperature and high-pressure part of the reactor by the supply rate of the aqueous medium.
  • the heat treatment can be performed by any method such as a batch method, a semi-batch method, and a distribution method.
  • 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.
  • 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.
  • 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.
  • the heat treatment liquid obtained by heat treatment it is preferable to include a step of cooling the heat treatment liquid obtained by heat treatment to 90 ° C. or less, preferably 50 ° C. or less, more preferably 30 ° C. or less.
  • a liquid component (A) containing composition 0 degreeC or more is preferable and 10 degreeC or more is preferable.
  • the cooling rate of the heat treatment liquid calculated from the time required to decrease from the heat treatment temperature to 90 ° C. is 0.2 ° C./s or more, further 0.5 ° C./s or more, 1 ° C./s or more, and further 3 It is preferably at least 5 ° C / s, more preferably at least 5 ° C / s.
  • the solubility of the poorly water-soluble aromatic compound can be improved.
  • 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.
  • the method for removing the solid matter is not particularly limited, and can be performed by, for example, centrifugation, decantation, or filtration.
  • the component (A) -containing composition thus obtained contains (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol in an aqueous medium. ) Although the content of the hardly water-soluble aromatic compound is high, precipitation of the hardly water-soluble aromatic compound can be suppressed even at room temperature and during storage at room temperature. Moreover, it is excellent in solubility in water.
  • the content of the component (A) in the component (A) -containing composition of the present invention is preferably 0.5 g / L or more, more preferably 1 g / L or more, and further 1.5 g / L from the viewpoint of physical distribution and usability.
  • L or more further 2 g / L or more, more preferably 7.5 g / L or more, and further preferably 30 g / L, and 150 g / L or less, further 100 g / L or less, further 75 g / L or less, further 60 g / L or less, It is preferably 55 g / L or less, more preferably 50 g / L or less.
  • the content of the (B) dihydric alcohol is in the total composition from the viewpoint of the solubility and stability of the component (A) in the component (A) -containing composition.
  • it is preferably 1 to 700 g / L, more preferably 10 to 600 g / L, further preferably 20 to 500 g / L, further preferably 100 to 500 g / L, and further preferably 300 to 500 g / L.
  • the content of the (C) trivalent or higher alcohol is the total composition from the viewpoint of the solubility and stability of the component (A) in the component (A) -containing composition.
  • the following is preferred.
  • it is preferably 1 to 500 g / L, more preferably 1 to 300 g / L, further preferably 10 to 250 g / L, further preferably 50 to 250 g / L, and further preferably 100 to 200 g / L.
  • the mass ratio [(A) / (B)] of the component (A) to the component (B) is 0 from the viewpoint of the stability of the component (A) -containing composition.
  • 0.001 to 1 more preferably 0.001 to 0.5, still more preferably 0.001 to 0.2, still more preferably 0.002 to 0.15, and 0.002 to 0.13.
  • 0.002 to 0.12 is more preferable
  • 0.002 to 0.11 is further preferable
  • 0.02 to 0.11 is further preferable
  • 0.025 to 0.11 is further preferable
  • 0.02. More preferably, it is from 06 to 0.11.
  • the mass ratio [(A) / (C)] of the component (A) to the component (C) is the dissolution of the component (A) in the component (A) -containing composition.
  • 0.001 or more, further 0.005 or more, further 0.01 or more, further 0.12 or more, further 0.15 or more, further 0.17 or more are preferable, and 1.5 or less, It is preferably 1 or less, more preferably 0.7 or less, and further preferably 0.55 or less. Further, it is preferably 0.001 to 1.5, more preferably 0.001 to 1, further preferably 0.005 to 0.7, still more preferably 0.01 to 0.55, and 0.12 to 0.55. Is more preferred, 0.15 to 0.55 is more preferred, and 0.17 to 0.55 is even more preferred.
  • the mass ratio [(B) / (C)] of the component (B) to the component (C) is the dissolution of the component (A) in the component (A) -containing composition.
  • 1.5 or more, further 2 or more, and further 2.5 or more are preferable, and 10 or less, further 8 or less, and further 6 or less are preferable. Further, it is preferably 1.5 to 10, more preferably 2 to 8, and further preferably 2.5 to 6.
  • the mass ratio [(A) / ⁇ (B) + (C) ⁇ ] of the component (A) to the total amount of the component (B) and the component (C) is From the viewpoint of the stability of the component (A) -containing composition, 0.001 or more, further 0.002 or more, further 0.015 or more, further 0.019 or more, more preferably 0.05 or more is preferable. 5 or less, further 0.2 or less, further 0.15 or less, further 0.12 or less, and further preferably 0.1 or less.
  • 0.001 to 0.5 is preferable, 0.001 to 0.2 is preferable, 0.002 to 0.15 is more preferable, 0.002 to 0.12 is still more preferable, and 0.002 to 0.00. 1 is more preferred, 0.015 to 0.1 is more preferred, 0.019 to 0.1 is still more preferred, and 0.05 to 0.1 is still more preferred.
  • the component (A) -containing composition of the present invention it is desirable to reduce the amount of organic solvent, particularly monohydric alcohol having 4 or less carbon atoms, from the viewpoint of irritation to the skin.
  • the content of the organic solvent in the component (A) -containing composition is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, further preferably 0 to 10% by mass, and further preferably 0 to 1% by mass. More preferably, it is substantially 0% by mass, that is, it does not contain an organic solvent.
  • the content of the surfactant is desirably reduced from the viewpoint of advantageously exhibiting the effect of the (A) poorly water-soluble aromatic compound.
  • the content of the surfactant in the component (A) -containing composition is preferably 0 to 1 g / L, more preferably 0 to 0.5 g / L, still more preferably 0 to 0.1 g / L, substantially More preferably, 0 g / L, that is, no surfactant is contained.
  • the component (A) -containing composition of the present invention can be used for various products such as cosmetics, pharmaceuticals, foods and daily necessities. In particular, it is useful to use in water-based products and cosmetics.
  • cosmetics or pharmaceuticals skin cosmetics such as cleaning products, skin lotions, cosmetics for makeup, cosmetics for sunscreen, cosmetics for acne, cosmetics for deodorants, whitening cosmetics, hair washing agents, hair restorers Toothpaste, mouthwash, mouthwash, etc.
  • the component (A) -containing composition of the present invention may be diluted with water or the like depending on the use of the product.
  • the concentration of the component (A) in the composition containing the component (A) after dilution is 0.1 to 50 g / L, further 0.2 to 30 g / L, further 0.5 to 10 g / L, and further 0.5. ⁇ 5 g / L, more preferably 0.5 to 2 g / L.
  • the component (A) -containing composition of the present invention has a drastically increased dissolution concentration of the hardly water-soluble aromatic compound as compared with the solubility of the usual poorly water-soluble aromatic compound in water, In this case, the precipitation of the hardly water-soluble aromatic compound is suppressed and the stability is high. Moreover, high physiological activity expression of a poorly water-soluble aromatic compound can be expected.
  • the cosmetic of the present invention contains the component (A) -containing composition obtained as described above, and preferably (C) a mass ratio of (B) dihydric alcohol to trihydric or higher alcohol [ (B) / (C)] contains a component (A) -containing composition of 1.5 to 10, more preferably (D) selected from a deodorant component, a bactericidal component, and a feel improving component. It further contains more than seeds. As a result, the effects of the poorly water-soluble aromatic compound are fully exhibited, and the effects of the combined components can be fully expressed.
  • the mass ratio [(B) / (C)] of the component (B) to the component (C) in the component (A) -containing composition is: (A) From the solubility point of the component (A) in the containing composition, it is preferably 1.5 or more, more preferably 2 or more, and further preferably 2.5 or more, and is preferably 10 or less, more preferably 8 or less, and further preferably 6 or less. . Further, it is preferably 1.5 to 10, more preferably 2 to 8, and further preferably 2.5 to 6.
  • the content of the component (A) in the component (A) -containing composition is preferably 1 g / L from the viewpoint of physical distribution and usability. More preferably, it is 2 g / L or more, more preferably 7.5 g / L or more, and further preferably 30 g / L or more.
  • the mass ratio [(A) / (B)] of the component (A) to the component (B) in the component (A) -containing composition is difficult.
  • it is preferably 0.02 or more, more preferably 0.025 or more, and further preferably 0.06 or more, and 1 or less, further 0.5 or less, and further 0.15 or less.
  • it is preferably from 0.02 to 1, more preferably from 0.025 to 0.5, and still more preferably from 0.06 to 0.15.
  • the mass ratio [(A) / (C)] of the component (A) to the component (C) in the component (A) -containing composition is: (A) From the viewpoint of improving the stability of the containing composition, it is preferably 0.12 or more, more preferably 0.15 or more, and further preferably 0.17 or more, and is 1.5 or less, further 1 or less, and further 0.6 or less. Is preferred. Further, it is preferably 0.12 to 1.5, more preferably 0.15 to 1, and further preferably 0.17 to 0.6.
  • the mass ratio of the component (A) to the total amount of the component (B) and the component (C) in the component (A) -containing composition [(A) / ⁇ (B) + (C) ⁇ ] is preferably 0.015 or more, more preferably 0.019 or more, still more preferably 0.05 or more, more preferably 0.5 or less, and further preferably 0.00 from the viewpoint of stability. 2 or less, more preferably 0.1 or less.
  • 0.015 to 0.5 is preferable, 0.019 to 0.5 is more preferable, 0.05 to 0.2 is still more preferable, and 0.05 to 0.1 is still more preferable.
  • 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.
  • 0.01% by mass or more is preferable in the total composition, and 0.02% by mass
  • the above is more preferable, 0.05 mass% or more is further preferable, 1 mass% or less is preferable, 0.5 mass% or less is more preferable, and 0.3 mass% or less is still more preferable.
  • the content of component (A) is preferably 0.01 to 1% by mass, more preferably 0.02 to 0.5% by mass, and still more preferably 0.05 to 0.3% by mass in the total composition. .
  • 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.
  • 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.
  • 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.
  • the content of the trivalent or higher alcohol of the component (C) is a viewpoint of sufficiently exerting the effect of the poorly water-soluble aromatic compound. From the viewpoint of obtaining an excellent deodorizing effect and bactericidal effect, no stickiness, and a smooth feeling, 0.01% by mass or more is preferable in the total composition, and 0.03% by mass or more. Is more preferably 0.06% by mass or more, still more preferably 0.09% by mass or more, more preferably 2.86% by mass or less, more preferably 2.5% by mass or less, and further more preferably 2% by mass or less. Preferably, 1.72% by mass or less is even more preferable.
  • the content of component (C) is preferably 0.01 to 2.86% by mass, more preferably 0.03 to 2.5% by mass, and still more preferably 0.06 to 2% by mass in the total composition. 0.09 to 1.72% by mass is even more preferable.
  • the component (D) used in the present invention is one other than the component (A), and is one or more selected from a deodorizing component, a bactericidal component and a touch improving component.
  • the deodorant component may be any of chemical deodorization methods; physical deodorization methods; biological deodorization methods; sensory deodorization methods.
  • chemical deodorization methods metal oxides such as zinc oxide and titanium oxide that chemically adsorb odorous substances; tris (hydroxymethyl) aminomethane (2-amino-2-hydroxymethyl) that neutralizes odorous substances 1,3-propanediol) and the like, and antioxidants such as dibutylhydroxytoluene that suppress decomposition to odorous substances.
  • Examples of physical deodorization methods include cyclodextrins that physically adsorb odorous substances, hydroxyapatite, chitosan fine particles, and porous substances such as activated carbon.
  • Examples of biological deodorization methods include yellowfin extract and oleic acid.
  • Examples of sensory deodorization methods include fragrances such as L-menthol.
  • 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.
  • 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.
  • component (D) when a deodorant component is used as component (D), the content thereof is preferably 0.01 to 2% by mass, more preferably 0.05 to 1.5% by mass in the total composition, and 0.07 To 1% by mass is more preferable, and 0.09 to 0.9% by mass is even more preferable.
  • 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.
  • 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.
  • the content thereof is preferably 0.005 to 4% by mass, more preferably 0.01 to 3% by mass, and 0.02 to 1% by mass in the total composition. % Is more preferable, and 0.03 to 0.5% by mass is even more preferable.
  • examples of the touch improving component include powders, and any of inorganic powders, organic powders, and composite powders thereof may be used.
  • examples of the organic powder include nylon resin (commercially available, Elf Atchem, ORGASOL 2002EXD NAT COS TypeS, ORGASOL 4000EXD NAT COS; Toray, SP-500, etc.), polystyrene resin (commercially available, Sumitomo Chemical) Manufactured by Kogyo Co., Ltd., Fine Pearl; manufactured by Sekisui Plastics Kogyo Co., Ltd., Techpolymer SB; Beads), polymethyl methacrylate resin (commercially available from Matsumoto Yushi Seiyaku, Matsumoto Microsphere M; Sekisui Plastics, Techpolymer MB; Soken Chemicals, Fine Powder MP, etc.), (Meth) acrylic ester resin, silicone resin (Commercially available products, Shin-Etsu Chemical Co., Ltd., KMP-590;
  • a crosslinked (meth) acrylic acid ester resin powder such as lauryl methacrylate / ethylene glycol / methacrylic acid / sodium methacrylate copolymer (Japanese Patent Laid-Open No. 2006-8659) can also be used.
  • 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.
  • 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.
  • a deodorant component when using powder as a touch improvement component, what is also contained in a deodorant component shall be handled as a deodorant component.
  • these feel improving components preferably have an average particle size of 0.01 ⁇ m or more, more preferably 0.05 ⁇ m or more, further preferably 0.2 ⁇ m or more, and suppress roughness. From the viewpoint of further improving the smooth feeling, it is preferably 50 ⁇ m or less, more preferably 20 ⁇ m or less, and even more preferably 8 ⁇ m or less.
  • the content is preferably 0.01% by mass or more in the total composition from the viewpoint of reducing squeakiness, suppressing roughness, and further improving smoothness. More preferably 1% by weight or more, still more preferably 1% by weight or more, still more preferably 1.5% by weight or more, more preferably 20% by weight or less, more preferably 10% by weight or less, and even more preferably 5% by weight or less. preferable. Further, when a feel improving component is used as the component (D), the content thereof is preferably 0.01 to 20% by mass, more preferably 0.1 to 20% by mass in the total composition, and 1 to 10% by mass. Is more preferable, and 1.5 to 5% by mass is even more preferable.
  • component (D) is one or more selected from a deodorant component, a bactericidal component, and a feel improving component.
  • 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.
  • 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.
  • the total content of component (D) is preferably 0.005 to 20% by mass, more preferably 0.01 to 15% by mass, still more preferably 0.02 to 10% by mass, based on the total composition. Even more preferred is 02-5% by weight.
  • the cosmetic of the present invention preferably further contains an aqueous medium such as water.
  • the blending method may be performed by adding the component (A) -containing composition to the aqueous medium and then adding and mixing the component (D) and other components, or mixing the component (A) -containing composition and component (D ), And other components may be added separately and mixed together.
  • the concentration of the hardly water-soluble aromatic compound in the aqueous medium is 0.1 to 50 g / L, further 0.2 to 30 g / L, further 0.5 to 10 g / L, further 0.5 to 5 g / L, and further 0. 0.5 to 2 g / L is preferable.
  • 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.
  • flavor, etc. can be contained.
  • ⁇ 1> comprising a step of heat-treating (A) a poorly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol at 100 to 180 ° C. in the presence of an aqueous medium.
  • a method for producing an aromatic compound-containing composition comprising a step of heat-treating (A) a poorly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol at 100 to 180 ° C. in the presence of an aqueous medium.
  • the poorly water-soluble aromatic compound has a solubility in water at 25 ° C. of preferably 0.5 g / L or less, more preferably 0.3 g / L or less, and still more preferably 0.2 g / L or less.
  • the poorly water-soluble aromatic compound has a solubility in (B) dihydric alcohol at 25 ° C. of preferably 5 g / L or more, more preferably 10 g / L or more, and still more preferably 20 g / L or more.
  • the poorly water-soluble aromatic compound is preferably one or more selected from an antibacterial component, a whitening component, and a hair growth component, and more preferably a phenolic antibacterial agent, an antiseptic, and a chromone derivative.
  • the phenolic antibacterial agent is preferably one or two selected from triclosan, chlorthymol, carbachlor, chlorophene, dichlorophen, hexachlorophene, chloroxylenol, chlorocresol, O-phenylphenol and isopropylmethylphenol
  • the method for producing a poorly water-soluble aromatic compound-containing composition according to ⁇ 4> which is one or more selected from triclosan and isopropylmethylphenol, more preferably isopropylmethylphenol. .
  • the preservative is preferably one or two selected from paraoxybenzoates, and more preferably selected from methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben and benzylparaben.
  • the manufacturing method of the slightly water-soluble aromatic compound containing composition as described in ⁇ 4> which is 1 type or 2 types.
  • the chromone derivative is preferably 2-butylchromone, 2-pentylchromone, 2-heptylchromone, 2-nonylchromone, 2-hexadecylchromone, 2- (1-ethylpentyl) chromone, 2-butyl-7- Methoxychromone, 2-pentyl-7-methoxychromone, 2-heptyl-7-methoxychromone, 2-nonyl-7-methoxychromone, 2-pentadecyl-7-methoxychromone, 2- (1-ethylpentyl) -7- Methoxychromone, 7-hydroxy-2-methylchromone, 7-hydroxy-2-butylchromone, 7-hydroxy-2-pentylchromone, 7-hydroxy-2-heptylchromone, 7-hydroxy-2-nonylchromone, 7-hydroxy -2-pentadecylchromone and 7-hydroxy-2- (1
  • the hair-growth component is preferably one or more selected from flavanol derivatives, nicotinic acids, vitamin Es, minoxidil, bimatoprost, tafluprost, nonyl acid vanillylamide, hypericum herb extract and chili pepper tincture, and more Preferably, trans-3,4'-dimethyl-3-hydroxyflavanone, benzyl nicotinate, tocopherol nicotinate, ⁇ -butoxyethyl nicotinate, ⁇ -tocopherol, dl- ⁇ -tocopherol acetate, tocopherol nicotinate, natural vitamin E, One or more selected from minoxidil, bimatoprost, tafluprost, nonylic acid vanillylamide, hypericum herb extract and capsicum tincture, more preferably trans-3,4'-dimethyl-3-hydroxyflavanone Method for producing sparingly water-soluble aromatic compound-containing composition according to
  • the dihydric alcohol is preferably ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, diethylene glycol, dipropylene glycol, One or more selected from polyethylene glycol and polypropylene glycol, more preferably one selected from ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol and dipropylene glycol Or two or more, more preferably one or more selected from propylene glycol, 1,3-propanediol and 1,3-butanediol, and any one of ⁇ 1> to ⁇ 8> Method for producing a composition containing a hardly water-soluble aromatic compound as described .
  • Trivalent or higher alcohol is preferably glycerin, diglycerin, triglycerin, 1,2,4-butanetriol, 1,2,5-pentanetriol, 2-methylpropanetriol, 2-methyl -One or more selected from 1,2,4-butanetriol, trimethylolethane and trimethylolpropane, more preferably one or more selected from glycerin, diglycerin and triglycerin More preferably, the method for producing a poorly water-soluble aromatic compound-containing composition according to any one of ⁇ 1> to ⁇ 9>, which is glycerin and / or diglycerin.
  • the aqueous medium is preferably an aqueous solution of water or an organic solvent, more preferably an aqueous solution of water or a monohydric alcohol having 4 or less carbon atoms, more preferably an aqueous solution of water or ethanol, and still more preferably.
  • the method for producing a poorly water-soluble aromatic compound-containing composition according to any one of ⁇ 1> to ⁇ 10>, which is water.
  • the concentration of the organic solvent in the aqueous solution of the organic solvent is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, still more preferably 0 to 10% by mass, and still more preferably 0 to 1% by mass.
  • a hardly water-soluble aromatic compound contains an aqueous medium
  • A a hardly water-soluble aromatic compound
  • B a dihydric alcohol
  • C a trihydric or higher alcohol.
  • the heat treatment raw material preferably 0.1 g / L or more, more preferably 0.5 g / L or more, still more preferably 0.7 g / L or more, still more preferably 0.9 g / L or more, still more preferably 1 g.
  • / L or more further 2 g / L or more, further 7.5 g / L or more, further 30 g / L or more, preferably 150 g / L or less, more preferably 100 g / L or less, still more preferably 75 g / L or less.
  • the dihydric alcohol is treated with an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol.
  • the raw material preferably contains 1 g / L or more, more preferably 10 g / L or more, still more preferably 20 g / L or more, still more preferably 100 g / L or more, still more preferably 300 g / L or more, and preferably 700 g.
  • a trivalent or higher alcohol contains an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trivalent or higher alcohol.
  • the heat treatment raw material preferably contains 1 g / L or more, more preferably 10 g / L or more, further preferably 50 g / L or more, more preferably 100 g / L or more, and preferably 500 g / L or less, more preferably Is 300 g / L or less, more preferably 250 g / L or less, further preferably 200 g / L or less, preferably 1 to 500 g / L, more preferably 1 to 300 g / L, still more preferably 10 to 250 g / L.
  • 0.0 2 to 0.15 more preferably 0.002 to 0.13, more preferably 0.002 to 0.12, more preferably 0.002 to 0.11, and still more preferably 0.02 to 0.11.
  • the method for producing a poorly water-soluble aromatic compound-containing composition according to any one of ⁇ 1> to ⁇ 15>, more preferably 0.025 to 0.11, and further preferably 0.06 to 0.11.
  • component (C) In the heat treatment step, in the heat treatment raw material containing an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol, the component (C)
  • the mass ratio [(A) / (C)] of component (A) is preferably 0.001 or more, more preferably 0.005 or more, still more preferably 0.01 or more, still more preferably 0.12 or more, and further Preferably it is 0.15 or more, more preferably 0.17 or more, preferably 1.5 or less, more preferably 1 or less, still more preferably 0.7 or less, still more preferably 0.55 or less, Further, it is preferably 0.001 to 1.5, more preferably 0.001 to 1, still more preferably 0.005 to 0.7, still more preferably 0.01 to 0.55, still more preferably 0.12 to 0.55, even better Ku 0.15 to 0.55, more preferably the production method of 0.17 to 0.55 ⁇ 1> to poorly water-soluble
  • the component (C) in the heat treatment raw material containing an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trihydric or higher alcohol, the component (C)
  • the mass ratio [(B) / (C)] of component (B) is preferably 1.5 or more, more preferably 2 or more, still more preferably 2.5 or more, and preferably 10 or less, more preferably Is any one of ⁇ 1> to ⁇ 17>, which is 8 or less, more preferably 6 or less, preferably 1.5 to 10, more preferably 2 to 8, and still more preferably 2.5 to 6.
  • the manufacturing method of the hardly water-soluble aromatic compound containing composition as described in any one of.
  • the surfactant is an aqueous medium, (A) a hardly water-soluble aromatic compound, (B) a dihydric alcohol, and (C) a trivalent or higher alcohol heat treatment raw material.
  • a hardly water-soluble aromatic compound Preferably 0 to 1 g / L, more preferably 0 to 0.5 g / L, still more preferably 0 to 0.1 g / L, or even more preferably ⁇ 1> to ⁇ 19> Of producing a slightly water-soluble aromatic compound-containing composition.
  • the temperature of the heat treatment is preferably 110 ° C. or higher, more preferably 120 ° C. or higher, preferably 170 ° C. or lower, more preferably 160 ° C.
  • the method for producing a poorly water-soluble aromatic compound-containing composition according to any one of ⁇ 1> to ⁇ 20>, more preferably 120 to 150 ° C. ⁇ 22>
  • the pressure during the heat treatment is preferably 0 to 10 MPa, more preferably 0.1 to 8 MPa, still more preferably 0.1 to 6 MPa, still more preferably 0.2 to 6 MPa, and still more preferably 0 in terms of gauge pressure.
  • the heat treatment time is preferably 0.1 minutes or more, more preferably 0.2 minutes or more, and even more preferably 0.5 minutes after the aqueous medium reaches the temperature of the heat treatment described in ⁇ 20>. Or more, preferably 30 minutes or less, more preferably 15 minutes or less, still more preferably 8 minutes or less, preferably 0.1 to 30 minutes, more preferably 0.2 to 15 minutes, The method for producing a poorly water-soluble aromatic compound-containing composition according to any one of ⁇ 1> to ⁇ 22>, more preferably 0.5 to 8 minutes.
  • the heat treatment time is preferably 0.1 minutes or more, more preferably 0.2 minutes or more, and still more preferably 0.8 minutes after the heat treatment raw material reaches the heat treatment temperature described in ⁇ 20>.
  • the method for producing a poorly water-soluble aromatic compound-containing composition according to any one of ⁇ 1> to ⁇ 22>, which is 0.5 to 8 minutes.
  • the slightly water-soluble solution according to any one of ⁇ 1> to ⁇ 24> further including a step of cooling the heat treatment liquid obtained by the heat treatment, preferably at a cooling rate of 0.2 ° C./s or more.
  • the cooling rate from the heat treatment temperature to 90 ° C. is preferably 0.2 ° C./s or more, more preferably 0.5 ° C./s or more, and further preferably 1 ° C. Or more, more preferably 3 ° C./s or more, further preferably 5 ° C./s or more, preferably 100 ° C./s or less, more preferably 50 ° C./s or less.
  • a method for producing a composition containing a hardly water-soluble aromatic compound is preferably 0.2 ° C./s or more, more preferably 0.5 ° C./s or more, and further preferably 1 ° C. Or more, more preferably 3 ° C./s or more, further preferably 5 ° C./s or more, preferably 100 ° C./s or less, more preferably 50 ° C./s or less.
  • the content of the (A) sparingly water-soluble aromatic compound in the sparingly water-soluble aromatic compound-containing composition is preferably 0.5 g / L or more, more preferably 1 g / L or more, still more preferably 1.
  • the poorly water-soluble aromatic compound-containing composition according to ⁇ 27> which is 5 g / L or more, more preferably 2 g / L or more.
  • the content of the dihydric alcohol (B) in the hardly water-soluble aromatic compound-containing composition is preferably 1 g / L or more, more preferably 10 g / L or more, still more preferably 20 g / L or more, and further Preferably it is 100 g / L or more, more preferably 300 g / L or more, preferably 700 g / L or less, more preferably 600 g / L or less, still more preferably 500 g / L or less, and preferably 1 to ⁇ 27> or ⁇ 28>, which is 700 g / L, more preferably 10 to 600 g / L, still more preferably 20 to 500 g / L, still more preferably 100 to 500 g / L, still more preferably 300 to 500 g / L.
  • a slightly water-soluble aromatic compound-containing composition The content of the (C) trivalent or higher alcohol in the ⁇ 30> hardly water-soluble aromatic compound-containing composition is preferably 1 g / L or more, more preferably 10 g / L or more, and even more preferably 50 g / L or more.
  • it is 100 g / L or more, preferably 500 g / L or less, more preferably 300 g / L or less, still more preferably 250 g / L or less, still more preferably 200 g / L or less, and preferably 1 to 500 g / L, more preferably 1 to 300 g / L, still more preferably 10 to 250 g / L, still more preferably 50 to 250 g / L, still more preferably 100 to 200 g / L ⁇ 27> to ⁇ 29>
  • the mass ratio [(A) / (B)] of the component (A) to the component (B) is preferably 0.001 or more, more preferably 0.002 or more, still more preferably 0.02 or more, and further Preferably it is 0.025 or more, More preferably, it is 0.06 or more, Preferably it is 1 or less, More preferably, it is 0.5 or less, Furthermore, 0.2 or less, More preferably, it is 0.15 or less, More preferably, it is 0 .13 or less, more preferably 0.12 or less, further preferably 0.11 or less, preferably 0.001 to 1, more preferably 0.001 to 0.5, and still more preferably 0.001 to 0.2, more preferably 0.002 to 0.15, more preferably 0.002 to 0.13, more preferably 0.002 to 0.12, more preferably 0.002 to 0.11, and even more preferably.
  • the mass ratio [(A) / (C)] of the component (A) to the component (C) is preferably 0.001 or more, more preferably 0.005 or more, still more preferably 0.01 or more, and further 0.12 or more, further 0.15 or more, further 0.17 or more, preferably 1.5 or less, more preferably 1 or less, still more preferably 0.7 or less, still more preferably 0.55 or less.
  • the mass ratio [(B) / (C)] of the component (B) to the component (C) is preferably 1.5 or more, more preferably 2 or more, still more preferably 2.5 or more.
  • Mass ratio [(A) / ⁇ (B) + (C) ⁇ ] of component (A) to the total amount of component (B) and component (C) is preferably 0.001 or more, more preferably 0.002 or more, more preferably 0.015 or more, more preferably 0.019 or more, still more preferably 0.05 or more, preferably 0.5 or less, more preferably 0.2 or less, still more preferably Is 0.15 or less, more preferably 0.12 or less, further preferably 0.10 or less, preferably 0.001 to 0.5, more preferably 0.001 to 0.2, more preferably 0.002 to 0.15, more preferably 0.002 to 0.12, more preferably 0.002 to 0.10, still more preferably 0.015 to 0.1, still more preferably 0.019 to 0.
  • a ⁇ 27> - a poorly water-soluble aromatic compound-containing composition according to any one of ⁇ 31>.
  • the content of the organic solvent is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, still more preferably 0 to 10% by mass, and still more preferably.
  • the content of monohydric alcohol having 4 or less carbon atoms is preferably 0 to 60% by mass, more preferably 0 to 30% by mass, and still more preferably 0 to 10%.
  • the content of the surfactant is preferably 0 to 1% by mass, more preferably 0 to 0.5% by mass, and still more preferably 0 to 0.1% by mass. %, And more preferably, the hardly water-soluble aromatic compound-containing composition according to any one of ⁇ 27> to ⁇ 36>.
  • a cosmetic comprising the sparingly water-soluble aromatic compound-containing composition according to any one of ⁇ 27> to ⁇ 37>.
  • (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,
  • the mass ratio [(B) / (C)] of the component (B) to the component (C) in the hardly water-soluble aromatic compound-containing composition is preferably 1.5 or more, more preferably 2 or more. More preferably, it is 2.5 or more, preferably 10 or less, more preferably 8 or less, still more preferably 6 or less, and preferably 1.5 to 10, more preferably 2 to 8, still more preferably.
  • the content of the component (A) in the hardly water-soluble aromatic compound-containing composition is preferably 1 g / L or more, more preferably 2 g / L or more, still more preferably 7.5 g / L or more, still more preferably.
  • the mass ratio [(A) / (B)] of component (A) to component (B) in the hardly water-soluble aromatic compound-containing composition is preferably 0.02 or more, more preferably 0.025.
  • the mass ratio [(A) / (C)] of the component (A) to the component (C) is preferably 0.12 or more, more preferably 0.15.
  • the mass ratio [(A) / ⁇ (B) + (C) ⁇ ] of the component (A) to the total amount of the component (B) and the component (C) in the hardly water-soluble aromatic compound-containing composition is , Preferably 0.015 or more, more preferably 0.019 or more, still more preferably 0.05 or more, and preferably 0.5 or less, more preferably 0.2 or less, still more preferably 0.1 or less.
  • the content of the poorly water-soluble aromatic compound of the component (A) in the cosmetic is preferably 0.01% by mass or more, more preferably 0.02% by mass or more, and still more preferably in the total composition. 0.05% by mass or more, preferably 1% by mass or less, more preferably 0.5% by mass or less, still more preferably 0.3% by mass or less, and preferably 0.01 to 1% by mass.
  • the content of (B) dihydric alcohol in the cosmetic is preferably 0.09% by mass or more, more preferably 0.18% by mass or more, and still more preferably 0.3% by mass in the total composition. More preferably, it is 0.45% by mass or more, preferably 8.4% by mass or less, more preferably 7% by mass or less, still more preferably 5.5% by mass or less, and further preferably 5% by mass or less.
  • % of cosmetics according to any one of ⁇ 38> to ⁇ 46>.
  • the content of the (C) trivalent or higher alcohol in the cosmetic is preferably 0.01% by mass or more, more preferably 0.03% by mass or more, and still more preferably 0.06% in the total composition.
  • % By mass or more more preferably 0.09% by mass or more, preferably 2.86% by mass or less, more preferably 2.5% by mass or less, still more preferably 2% by mass or less, still more preferably 1.% by mass.
  • the mass ratio [(A) / (B)] of the component (A) to the component (B) is preferably 0.02 or more, more preferably 0.025 or more, and still more preferably. 0.06 or more, preferably 1 or less, more preferably 0.5 or less, still more preferably 0.15 or less, and preferably 0.02 to 1, more preferably 0.025 to 0. 5.
  • the mass ratio [(A) / (C)] of the component (A) to the component (C) is preferably 0.12 or more, more preferably 0.15 or more, and still more preferably. 0.17 or more, preferably 1.5 or less, more preferably 1 or less, still more preferably 0.6 or less, and preferably 0.12 to 1.5, more preferably 0.15.
  • the mass ratio of (A) poorly water-soluble aromatic compound to the total amount of (B) dihydric alcohol and (C) trihydric or higher alcohol [(A) / ⁇ (B) + (C) ⁇ ] is preferably 0.015 or more, more preferably 0.019, still more preferably 0.05 or more, and preferably 0.5 or less, more preferably 0.2 or less, still more preferably. Is 0.1 or less, preferably 0.015 to 0.5, more preferably 0.019 to 0.5, still more preferably 0.05 to 0.2, still more preferably 0.05 to 0. 1.
  • the deodorant component is preferably selected from those related to chemical deodorization methods, physical deodorization methods, biological deodorization methods and sensory deodorization methods.
  • One or more selected from porous materials such as chitosan fine particles, activated carbon, yellowfin extract, oleic acid and L-menthol, more preferably tris (hydroxymethyl) aminomethane (2-amino-2-hydroxymethyl-1,3 -The cosmetic according to any one of ⁇ 39> to ⁇ 50>, which is propanediol).
  • the content thereof is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and still more preferably 0.07 in the total composition.
  • % By mass or more, more preferably 0.09% by mass or more, preferably 2% by mass or less, more preferably 1.5% by mass or less, still more preferably 1% by mass or less, still more preferably 0.9% by mass.
  • % Or less preferably 0.01 to 2% by mass, more preferably 0.05 to 1.5% by mass, still more preferably 0.07 to 1% by mass, and still more preferably 0.09 to 0.
  • the cosmetic according to any one of ⁇ 39> to ⁇ 52>, which is 9% by mass.
  • the sterilizing component is preferably alkyltrimethylammonium bromide, cetylpyridinium chloride, silver-supported inorganic particles, lysozyme chloride, benzalkonium chloride, cetylpyridinium chloride (CPC), alum, silver-supported zeolite and
  • the content thereof is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, and still more preferably 0.02% by mass in the entire composition.
  • the cosmetic according to any one of ⁇ 39> to ⁇ 54>.
  • the component (D) and the touch improving component is preferably an inorganic powder, an organic powder or a composite powder thereof, more preferably a nylon resin, a polystyrene resin, a polyethylene resin, or a polymethyl methacrylate resin.
  • the average particle diameter of the feel improving component is preferably 0.01 ⁇ m or more, more preferably 0.05 ⁇ m or more, still more preferably 0.2 ⁇ m or more, and preferably 50 ⁇ m or less, more preferably 20 ⁇ m or less, The cosmetic according to ⁇ 56>, more preferably 8 ⁇ m or less.
  • the content thereof is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and still more preferably 1% by mass in the total composition. More preferably, it is 1.5% by mass or more, preferably 20% by mass or less, more preferably 10% by mass or less, still more preferably 5% by mass or less, and preferably 0.01 to 20%.
  • the total content of ⁇ 59> component (D) is preferably 0.005% by mass or more, more preferably 0.01% by mass or more, still more preferably 0.02% by mass or more, in the total composition. , Preferably 20% by mass or less, more preferably 15% by mass or less, further preferably 10% by mass or less, further preferably 5% by mass or less, and preferably 0.005 to 20% by mass, more preferably 0%.
  • the cosmetic according to any one of ⁇ 39> to ⁇ 58> which is 0.01 to 15% by mass, more preferably 0.02 to 10% by mass, and further preferably 0.02 to 5% by mass.
  • the cosmetic according to any one of ⁇ 38> to ⁇ 59> further comprising an aqueous medium, more preferably water.
  • the concentration of the hardly water-soluble aromatic compound in the aqueous medium is preferably 0.1 to 50 g / L, more preferably 0.2 to 30 g / L, still more preferably 0.5 to 10 g / L, still more preferably.
  • the cosmetic according to ⁇ 60> in which is 0.5 to 5 g / L, more preferably 0.5 to 2 g / L.
  • Sample injection volume is 10 ⁇ L
  • detection is absorbance at 283 nm for isopropylmethylphenol
  • wavelength is 254 nm for trans-3,4′-dimethyl-3-hydroxyflavanone
  • absorbance is 300 nm for 2- (1-ethylpentyl) -7-methoxychromone was quantified.
  • Example 1 A stainless batch reactor with an internal volume of 190 mL was added to distilled water so that isopropylmethylphenol was 7.5 g / L, 1,3-butanediol was 300 g / L, and glycerin was 100 g / L.
  • the heat treatment was performed with Nitto Koatsu Co., Ltd. After reaching 150 ° C., the temperature was maintained for 1 minute and quickly cooled to room temperature (25 ° C.) (cooling rate 0.5 ° C./s). The pressure during the heat treatment was 0.4 MPa. After cooling, the heat treatment solution was immediately extracted and filtered through a PTFE filter having a pore size of 0.2 ⁇ m to obtain an isopropylmethylphenol composition.
  • Table 1 shows the results of measurement of the treatment conditions and the isopropylmethylphenol concentration, 1,3-butanediol concentration, and glycerin concentration in the composition at 25 ° C.
  • Examples 2 to 11 Isopropylmethylphenol, 1,3-butanediol or 1,3-propanediol, glycerin or diglycerin was added to distilled water to the amounts shown in Table 1, respectively, and heat-treated in the same manner as in Example 1 to obtain isopropyl. A methylphenol composition was obtained. Table 1 shows the treatment conditions and the results of measurement of the isopropylmethylphenol concentration, 1,3-butanediol concentration, 1,3-propanediol concentration, glycerin concentration and diglycerin concentration in the composition at 25 ° C.
  • Comparative Examples 2-7 Isopropylmethylphenol, 1,3-butanediol, and glycerin were added to distilled water to the amounts shown in Table 2, and the slurry was stirred at room temperature for 3 days (stirrer, 500 rpm). did.
  • Table 2 shows the treatment conditions and the results of measurement of the isopropylmethylphenol concentration, 1,3-butanediol concentration, and glycerin concentration in the liquid part.
  • Comparative Examples 8-10 Without adding glycerin, isopropylmethylphenol and 1,3-butanediol were added to distilled water to the amounts shown in Table 2, respectively, and an isopropylmethylphenol composition was obtained in the same manner as in Example 1.
  • Table 2 shows the treatment conditions and the measurement results of the isopropylmethylphenol concentration and the 1,3-butanediol concentration in the composition.
  • Comparative Examples 11-12 Without adding 1,3-butanediol, isopropylmethylphenol and glycerin were added to distilled water to the amounts shown in Table 2, respectively, and an isopropylmethylphenol composition was obtained in the same manner as in Example 1.
  • Table 2 shows the treatment conditions and the results of measuring the isopropylmethylphenol concentration and the glycerin concentration in the composition.
  • Examples 12-15 2- (1-Ethylpentyl) -7-methoxychromone, 1,3-butanediol, and glycerin were added to distilled water to the amounts shown in Table 3, respectively, and heat-treated in the same manner as in Example 1.
  • a 2- (1-ethylpentyl) -7-methoxychromone composition was obtained.
  • Table 3 shows the treatment conditions and the results of measurement of 2- (1-ethylpentyl) -7-methoxychromone concentration, 1,3-butanediol concentration and glycerin concentration in the composition.
  • Examples 16-17 Trans-3,4′-dimethyl-3-hydroxyflavanone, 1,3-butanediol, and glycerin were added to distilled water to the amounts shown in Table 4, respectively, and heat-treated in the same manner as in Example 1. A trans-3,4′-dimethyl-3-hydroxyflavanone composition was obtained. Table 4 shows the treatment conditions and the results of measurement of the trans-3,4′-dimethyl-3-hydroxyflavanone concentration, 1,3-butanediol concentration, and glycerin concentration in the composition.
  • IPMP isopropylmethylphenol
  • Example 21 265.0 g / L (Example 22), 360.1 g / L (Example 23), 361.6 g / L (Example 24), 999.8 g / L (Comparative Example 22) ), 389.6 g / L (Comparative Example 23), 698.7 g / L (Comparative Example 24), 492.9 g / L (Comparative Example 25), and 599.64 g / L (Comparative Example 26). The results are shown in Tables 5 and 6.
  • 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.
  • Stamp medium clean stamp "Nissui” SCDLP agar medium, Nissui Pharmaceutical Co., Ltd.
  • stamp medium cleaned stamp "Nissui” SCDLP agar medium, Nissui Pharmaceutical Co., Ltd.
  • 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.
  • 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.
  • IPMP and a bactericidal component were combined, the bactericidal performance was enhanced by using other bactericidal components in combination with the resident bacteria having insufficient bactericidal effect in IPMP, and the sweat odor suppressing effect was improved.
  • Combining IPMP and the powder that is a feel-enhancing component combined with the effect of promoting the transpiration of sweat by the powder resulted in an environment in which bacteria did not easily grow, and the sterilizing effect of IPMP was improved. Moreover, a smooth feeling was obtained.
  • Example 25 10 g of aluminum hydroxychloride, 0.2 g of polyoxyethylene hydrogenated castor oil and 0.05 g of fragrance were added to 2.5 g of the isopropylmethylphenol composition produced in Example 6, and purified water was added to prepare 100 g of a deodorant lotion.
  • the composition is as follows. IPMP 0.1 (mass%) 1,3-BG 1.25 Glycerin 0.25 Aluminum hydroxychloride 10.0 Polyoxyethylene (40) hydrogenated castor oil 0.2 Fragrance 0.05 Purified water balance Total 100.0
  • Example 26 3.33 g of the isopropylmethylphenol composition produced in Example 5 was 6 g of 1,3 butylene glycol, 0.1 g of oleyl alcohol, 0.4 g of POE (20) oleyl alcohol ether, 0.2 g of methyl paraben, and 0.2 g of dipotassium glycyrrhizinate. 0.04 g of fragrance was added, and purified water was added to prepare 100 g of acne lotion. The composition is as follows.
  • Example 27 As the oil phase, 12 g of stearic acid, 14 g of myristic acid, 5 g of lauric acid, 3 g of jojoba oil, 14.047 g of sorbit, 10 g of glycerin, and 10 g of 1,3-butylene glycol were heated and dissolved and kept at 70 ° C. 20 g of purified water was added to 2.0 g of the isopropylmethylphenol composition produced in Example 7 to dissolve 5 g of potassium hydroxide, and the oil phase was slowly added while stirring. After further adding 4 g of N-methyltaurine and stirring for 10 minutes to sufficiently carry out a neutralization reaction, 1.9 g of POE (20) glycerol monostearate was added.
  • a hand wash was prepared by slowly cooling to 25 ° C (cooling).
  • the composition is as follows. Stearic acid 12.0 (mass%) Myristic acid 14.0 Lauric acid 5.0 Jojoba oil 3.0 Sorbit (70% aqueous solution of sorbitol) Glycerin 10.2 1,3-BG 11.0 Potassium hydroxide 5.0 N-methyl taurine 4.0 POE (20) glycerol monostearate 1.9 IPMP 0.1 PG 8.421 Purified water balance Total 100.0

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Communicable Diseases (AREA)
  • Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Oncology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

　La présente invention se rapporte à un nouveau procédé de fabrication d'une composition contenant un composé aromatique faiblement hydrosoluble, la dissolution du composé aromatique faiblement hydrosoluble (constituant (A) de la présente invention) dans de l'eau étant excellente. Le procédé de fabrication d'une composition contenant un composé aromatique faiblement hydrosoluble comprend une étape dans laquelle les éléments suivants sont traités thermiquement à une température de 100 à 180 °C en présence d'un milieu aqueux : (A) un composé aromatique faiblement hydrosoluble ; (B) un alcool divalent ; et (C) un alcool qui est au moins trivalent.
PCT/JP2015/060976 2014-04-09 2015-04-08 Procédé de fabrication d'une composition contenant un composé aromatique faiblement hydrosoluble WO2015156317A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201580016689.XA CN106132389B (zh) 2014-04-09 2015-04-08 含有水难溶性芳香族化合物的组合物的制造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014-079850 2014-04-09
JP2014079850 2014-04-09

Publications (1)

Publication Number Publication Date
WO2015156317A1 true WO2015156317A1 (fr) 2015-10-15

Family

ID=54287891

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2015/060976 WO2015156317A1 (fr) 2014-04-09 2015-04-08 Procédé de fabrication d'une composition contenant un composé aromatique faiblement hydrosoluble

Country Status (4)

Country Link
JP (1) JP5901818B2 (fr)
CN (1) CN106132389B (fr)
TW (1) TWI668011B (fr)
WO (1) WO2015156317A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5908635B1 (ja) * 2015-04-08 2016-04-26 花王株式会社 化粧料
JP2016199535A (ja) * 2016-03-23 2016-12-01 花王株式会社 化粧料

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6725470B2 (ja) * 2016-10-18 2020-07-22 花王株式会社 化粧料
EP4032524A1 (fr) * 2017-12-27 2022-07-27 Kao Corporation Procédé de fabrication d'une composition contenant un composé aromatique difficilement soluble dans l'eau
WO2023199908A1 (fr) * 2022-04-11 2023-10-19 株式会社ダイセル Procédé de production d'une composition émulsifiée

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000325043A (ja) * 1999-05-17 2000-11-28 Matsutani Chem Ind Ltd 可溶性イソフラボン組成物及びその製造方法
JP2003284525A (ja) * 2001-12-19 2003-10-07 Hayashibara Biochem Lab Inc ポリフェノールの水に対する溶解性の改善方法ならびにポリフェノール高含有水溶液
CN101475448A (zh) * 2009-01-21 2009-07-08 淮安万邦香料工业有限公司 一种可替代天然牛至的高含量香芹酚的绿色合成方法
WO2010090236A1 (fr) * 2009-02-03 2010-08-12 サンスター株式会社 Composition contenant de l'hespéridine
JP2011231082A (ja) * 2010-04-30 2011-11-17 Lion Corp にきび用外用剤組成物
WO2011155505A1 (fr) * 2010-06-09 2011-12-15 花王株式会社 Procédé de fabrication d'une composition de polyphénol
JP2012214427A (ja) * 2011-03-31 2012-11-08 Sumitomo Seika Chem Co Ltd １，２−ベンズイソチアゾリン−３−オンを含有する水性組成物の製造方法
WO2013089140A1 (fr) * 2011-12-14 2013-06-20 花王株式会社 Procédé de production d'une composition antimicrobienne
WO2014098231A1 (fr) * 2012-12-21 2014-06-26 花王株式会社 Procédé de fabrication d'une composition antimicrobienne

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US599123A (en) * 1898-02-15 Glycerol ether of aromatic compounds
JP4826740B2 (ja) * 2003-07-02 2011-11-30 不二製油株式会社 フラボノイドの可溶化剤及び可溶化方法
JP5921868B2 (ja) * 2011-12-14 2016-05-24 花王株式会社 育毛料組成物の製造方法
JP6247525B2 (ja) * 2013-12-24 2017-12-13 花王株式会社 難水溶性芳香族化合物含有組成物の製造方法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000325043A (ja) * 1999-05-17 2000-11-28 Matsutani Chem Ind Ltd 可溶性イソフラボン組成物及びその製造方法
JP2003284525A (ja) * 2001-12-19 2003-10-07 Hayashibara Biochem Lab Inc ポリフェノールの水に対する溶解性の改善方法ならびにポリフェノール高含有水溶液
CN101475448A (zh) * 2009-01-21 2009-07-08 淮安万邦香料工业有限公司 一种可替代天然牛至的高含量香芹酚的绿色合成方法
WO2010090236A1 (fr) * 2009-02-03 2010-08-12 サンスター株式会社 Composition contenant de l'hespéridine
JP2011231082A (ja) * 2010-04-30 2011-11-17 Lion Corp にきび用外用剤組成物
WO2011155505A1 (fr) * 2010-06-09 2011-12-15 花王株式会社 Procédé de fabrication d'une composition de polyphénol
JP2012214427A (ja) * 2011-03-31 2012-11-08 Sumitomo Seika Chem Co Ltd １，２−ベンズイソチアゾリン−３−オンを含有する水性組成物の製造方法
WO2013089140A1 (fr) * 2011-12-14 2013-06-20 花王株式会社 Procédé de production d'une composition antimicrobienne
WO2014098231A1 (fr) * 2012-12-21 2014-06-26 花王株式会社 Procédé de fabrication d'une composition antimicrobienne

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5908635B1 (ja) * 2015-04-08 2016-04-26 花王株式会社 化粧料
JP2016199535A (ja) * 2016-03-23 2016-12-01 花王株式会社 化粧料

Also Published As

Publication number Publication date
CN106132389B (zh) 2020-07-14
CN106132389A (zh) 2016-11-16
JP5901818B2 (ja) 2016-04-13
TW201620489A (zh) 2016-06-16
JP2015205873A (ja) 2015-11-19
TWI668011B (zh) 2019-08-11

Similar Documents

Publication Publication Date Title
WO2015156317A1 (fr) Procédé de fabrication d'une composition contenant un composé aromatique faiblement hydrosoluble
CN102481463B (zh) 化妆品或皮肤病学制剂
WO2020052916A1 (fr) Composition topique comprenant un isomérat de saccharide pour un équilibrage du microbiome
JP6987862B2 (ja) 微量作用金属を含む抗菌組成物
WO2014098231A1 (fr) Procédé de fabrication d'une composition antimicrobienne
JP2011037786A (ja) 充分な抗菌性を有し、かつ保湿性に優れた化粧料
JPH04139125A (ja) 尋常性▲ざ▼瘡用皮膚外用剤
TW200528132A (en) High lipid content sprayable emulsions
US20200016062A1 (en) Terminalia ferdinandiana leaf extract and products containing extract of terminalia ferdinandiana leaf
JP5908635B1 (ja) 化粧料
JP5695678B2 (ja) 多価アルコールを含有する消臭剤
JP2019513708A (ja) チモール、テルピネオール、及びカチオン性リン脂質を含む抗菌組成物
JP6611646B2 (ja) 化粧料
KR101674512B1 (ko) 항균력과 유산균 증식력이 우수한 화장품 조성물 및 이를 적용한 화장품 제조방법
JP2011153128A (ja) デオドラント組成物
JP2005289912A (ja) 植物性抗菌組成物
KR20190130035A (ko) 유기 화합물에서의 또는 이와 관련된 개선
CN115701974A (zh) 用于处理恶臭气味的抗微生物组合物
JP2004331577A (ja) 抗菌剤
JP6530616B2 (ja) 化粧料及び加齢臭抑制剤
Mukherjee et al. Harmful effect of personal care products on ecosystem and the possible alternative approach
JP4660088B2 (ja) 防臭剤、および該防臭剤を含む防臭用組成物、化粧料組成物、洗浄用組成物
JP4284305B2 (ja) 防臭活性剤及び防臭用皮膚外用組成物
JP2007031316A (ja) 抗変異原性を利用した抗紫外線刺激剤
JP4950421B2 (ja) 化粧料

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15776822

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 15776822

Country of ref document: EP

Kind code of ref document: A1