JP2013136545A - Emulsified composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an emulsified composition, though being blended with a poorly water-soluble substance, which has quick skin fitness, has a feeling reduced in stickiness, and has stability, particularly, has excellent salt resistance.SOLUTION: The emulsified composition includes the following components (A) to (D), and in which the average emulsification particle diameter is ≤0.2 μm: (A) a poorly water-soluble substance; (B) N-acylamino acid ester; (C) N-acylamino acid and/or its salt; and (D) a nonionic surfactant having an HLB value of 1 to 6.

Description

  The present invention relates to an emulsified composition that stably blends a poorly water-soluble substance.

  Products in which various functional substances are blended in the emulsion composition are on the market. As a functional substance, for example, a biphenyl compound having a hydroxyl group is known to have excellent tyrosinase activity inhibitory effect and melanin production inhibitory effect and high safety, and is useful as a component for whitening cosmetics (patent) Reference 1). In addition, ultraviolet absorbers are used in many cosmetics in order to prevent damage to the skin and the composition from ultraviolet rays. Recently, 2- (4-diethylamino-2-hydroxybenzoyl) -hexyl ether such as 2- (4-diethylamino-2-hydroxybenzoyl) benzoate is used. The use of UVA ultraviolet absorbers is progressing. Furthermore, coenzyme Q10 is also called “ubiquinone” or “ubidecalenone”, and is expected to be effective for whitening, antioxidant, cell activation, and the like (see Patent Document 2). On the other hand, ceramide is generally known to be a constituent of keratin intercellular lipid, and attempts have been made to blend it stably in cosmetics and the like (see Patent Document 3).

  However, many of these functional substances are insoluble or poorly soluble in water, that is, have a problem of poor water solubility. Even if the functional substance itself is stable, crystals are precipitated during storage, and it has been difficult to mix stably in the composition. It was difficult to obtain an emulsified composition.

Therefore, in order to stably blend these poorly water-soluble substances into the emulsion composition, coenzyme Q10 is dissolved in N-lauroyl-L-glutamic acid diester, and an emulsion having an average emulsion particle size of 0.2 μm or less is obtained. An emulsified cosmetic is disclosed (see Patent Document 4).
Moreover, the aerosol cosmetics which emulsified the dimethyl ethyl methoxy benzoyl methane with stearoyl glutamate Na to about 100 nm are disclosed (refer patent document 5).
However, in the emulsion compositions described in Patent Documents 4 and 5, although attempts have been made to emulsify poorly water-soluble substances by a fine emulsification method, there is a problem that the salt tolerance of the preparation is low. In general, an emulsion composition product contains salts such as ascorbate, EDTA, sodium benzoate and the like in order to ensure functionality and quality assurance. If the salt resistance is low, the emulsified particles are likely to be agglomerated and separated.

  Then, the emulsion which combined N-acylamino-acid diester and the polysaccharide which has an aliphatic group in order to improve salt tolerance is disclosed (refer patent document 6).

JP-A-6-145040 JP 2004-107262 A JP 2001-199872 A JP 2007-153866 A JP 2004-224706 A JP 2011-184432 A

The emulsified composition described in Patent Document 6 has attempted to combine N-acylamino acid diesters and polysaccharides in order to overcome the problem relating to salt tolerance, but it can only emulsify a very small amount of oil phase, which is difficult. It has been difficult to add a water-soluble substance in an amount that has a sufficient effect.
Accordingly, an object of the present invention is to provide an emulsified composition having a feeling of being familiar with the skin, having less stickiness and having excellent stability, particularly salt resistance, while blending a poorly water-soluble substance.

  Accordingly, as a result of various studies, the present inventor has (C) N-acylamino acid and / or a salt thereof and (D) in addition to (A) a poorly water-soluble substance and (B) N-acylamino acid ester. ) Emulsion composition having a good feeling of skin, less stickiness, and excellent stability by using a nonionic surfactant having an HLB value of 1 to 6 and a specific average emulsion particle size. And the present invention was completed.

That is, the present invention provides an emulsion composition comprising the following components (A) to (D) and having an average emulsion particle size of 0.25 μm or less.
(A) Slightly water-soluble substance (B) N-acyl amino acid ester (C) N-acyl amino acid and / or salt thereof (D) Nonionic surfactant having an HLB value of 1 to 6

  The emulsified composition of the present invention blends a poorly water-soluble substance, has a quick skin familiarity, has a feeling of less stickiness, and is excellent in storage stability. Moreover, it is excellent in salt resistance.

  The emulsified composition of the present invention comprises (A) a poorly water-soluble substance, (B) an N-acyl amino acid ester, (C) an N-acyl amino acid and / or a salt thereof, and (D) a nonionic property having an HLB value of 1 to 6. A surfactant is contained as an essential component.

  The (A) poorly water-soluble substance in the present invention refers to a compound having a solubility in water at 25 ° C. of 10 mg / ml or less. Specific examples of the poorly water-soluble substance include a biphenyl compound represented by the general formula (1) or (2), a UV absorber solid at 25 ° C., a ceramide, a carotenoid or a derivative thereof, a tocopherol or a derivative thereof, Retinol or a derivative thereof, coenzyme Q10 and the like are exemplified, and the biphenyl compound represented by the general formula (1) or (2), an ultraviolet absorber solid at 25 ° C., ceramides, represented by the following general formula (3) Rubiquinone can be preferably used.

  The biphenyl compound represented by the following general formula (1) or (2) is a known substance that is a powdery substance at room temperature and is known to have an excellent tyrosinase activity inhibitory effect and melanin production inhibitory effect. . For example, dichloroeosol, tetrahydrodioigenol, tetrahydromagnolol and the like can be mentioned. These biphenyl compounds can be synthesized and used by a conventional method, or those obtained from plants and the like can be hydrogenated.

(Wherein R ¹ and R ² each represent a hydrogen atom or a linear or branched alkyl group or alkenyl group having 1 to 10 carbon atoms)

(Wherein R ³ and R ⁴ each represent a linear or branched alkyl group, alkenyl group, hydroxyalkyl group or hydroxyalkenyl group, aldehyde group or acetyl group having 1 to 5 carbon atoms)

Among these, from the viewpoint of its whitening effect and stability, as the R ¹ and R ² in the general formula (1), a hydrogen atom, or a straight-chain alkyl group having 1 to 10 carbon atoms preferably from 1 to carbon atoms Eight linear alkyl groups are more preferred. In the general formula (2), R ³ and R ⁴ are preferably a linear or branched alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group, an aldehyde group, or an acetyl group, and a linear chain having 1 to 3 carbon atoms. The alkyl group is more preferable.

In the general formula (1), specific examples of R ¹ and R ² are H, CH ₃ , C ₂ H ₅ , C ₃ H ₇ , C ₄ H ₉ , C ₅ H ₁₁ , C ₆ H ₁₃ , C, respectively. One type selected from ₇ H ₁₅ , C ₈ H _{17 and the} like can be mentioned. In the general formula (2), specific examples of R ³ and R ⁴ are CH ₃ , C ₂ H ₅ , C ₃ H ₇ , CH ₂ OH, C ₃ H ₆ OH, CHO, COCH ₃ , CH ₂ CH, respectively. = 1 type selected from CH _{2 and the} like. More preferably, it is preferably 2,2′-dihydroxy-5,5′-di-n-propylbiphenyl (general formula (1): R ¹ and R ² are C ₂ H ₅ ).

Examples of the UV absorber solid at 25 ° C. include 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester, 2,4,6-tris [4- (2-ethylhexyloxycarbonyl) anilino] -1 , 3,5-triazine, diethylhexylbutamide triazone, 4-tert-butyl-4′-methoxy-dibenzoylmethane and the like.
These are commercially available, UVINUL A PLUS (2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester; manufactured by BASF), UVINUL T-150 (2,4,6-Tris [4- ( 2-ethylhexyloxycarbonyl) anilino] -1,3,5-triazine (manufactured by BASF), diethylhexylbutamide triazone includes UVASORB HEB (manufactured by 3V GROUP) and the like.

Examples of ceramides include ceramides having various structures generally referred to as type 1 to type 6. Either sphingosine or phytosphingosine is used as a skeleton, and fatty acid, α-hydroxy acid or ω-hydroxy acid is bonded by an amide bond. There are several compounds with different fatty acid carbon numbers and unsaturation levels. All of them are high in crystallinity and have a high melting point, so that they are difficult to be stably mixed in a preparation. Of these, (2S, 3R) -2-octadecanoylaminooctadecane-1,3-diol (hereinafter referred to as ceramide 2), N-2-hydroxystearoyl phyto is preferable because of easy availability in the market. Sphingosine (hereinafter referred to as ceramide 6). These are obtained by extraction or synthesis from animals and plants, but are not limited thereto.
Specifically, N-stearoyl phytosphingosine (made by Nikko Chemicals), ceramide HO3 (made by Croda Japan), ceramide TIC-001 (made by Takasago International Corporation), etc. are mentioned.

  Ubiquinone represented by the following general formula (3) is present in the living body and is an essential substance as a coenzyme for energy production in intracellular mitochondria. However, since it is sparingly soluble in water and highly crystalline, it is a substance that is difficult to be stably blended in a preparation.

(However, n in the formula represents an integer of 7 to 10)

  In particular, in general formula (3), those with n = 10 are known as coenzyme Q10, ubidecalenone or coenzyme Q10, and are preferred in terms of availability in the market. Coenzyme Q10 is known as a vitamin-like substance having not only a biological activity as a coenzyme but also an effect of improving oxygen utilization efficiency, and has been widely used for quasi-drugs and cosmetics in recent years. As coenzyme Q10, reduced CoQ10 is more preferable because it has higher absorbability in the body than oxidized CoQ10.

  Among these components (A), the biphenyl compound represented by the general formula (1) or (2), 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester, 2,4,6-tris [4- (2-ethylhexyloxycarbonyl) anilino] -1,3,5-triazine, diethylhexylbutamide triazone, 4-tert-butyl-4′-methoxy-dibenzoylmethane, ceramide, coenzyme Q10 1 type or 2 types or more are preferable. In this invention, even if it is a case where 2 or more types of these components are contained, it can mix | blend stably and a favorable usability | use_condition is obtained.

  The content of the component (A) is desirably a blending amount that exhibits effectiveness, and the optimum amount varies depending on the substance, but from the viewpoint of emulsification stability, 0.01 to 10 mass% is preferable, More preferably, it is 0.05-5 mass%, More preferably, it is 0.1-5 mass%.

  The (B) N-acyl amino acid ester used in the present invention is an ester of an N-acyl amino acid and an alcohol. The N-acyl amino acid moiety is not particularly limited, but is preferably an N-acyl acidic amino acid such as N-acyl aspartic acid or N-acyl glutamic acid, and more preferably N-acyl glutamic acid is used. These amino acid structures may be either optically active or racemic. The acyl group is preferably an acyl group derived from a saturated or unsaturated fatty acid having 8 to 22 carbon atoms. For example, the acyl group of a fatty acid having a single composition such as lauric acid, palmitic acid, stearic acid, oleic acid, etc. In addition, it may be a mixed fatty acid obtained from nature such as coconut oil fatty acid, beef tallow fatty acid, hardened beef tallow fatty acid, or an acyl group of fatty acids (including branched fatty acids) obtained by synthesis.

  The ester-generating residue is not particularly limited, and sterols, alkyl or alkenyl alcohols having 8 to 38 carbon atoms are used, sterols, liquid higher alkyl or alkenyl alcohols having 8 to 30 carbon atoms, and solids having 12 to 38 carbon atoms. A higher alkyl alcohol having a shape is preferably used. In the case of an N-acyl acidic amino acid ester, it may be a monoester or a diester, but is particularly preferably a diester in which at least one of two ester-generating residues is a sterol residue. . The sterol may be animal-derived or plant-derived, and examples thereof include cholesterol, phytosterol, and hydrogenated products thereof. The liquid higher alkyl or alkenyl alcohol having 8 to 30 carbon atoms is a natural or synthetic aliphatic alcohol having 8 to 30 carbon atoms and exhibits a liquid state at room temperature, for example, a branched alcohol such as 2-octyldodecyl alcohol, Examples thereof include unsaturated alcohols such as oleyl alcohol. Solid higher alkyl alcohols having 12 to 38 carbon atoms are saturated monohydric alcohols having 12 to 38 carbon atoms and exhibit a solid form at room temperature, and examples thereof include cetyl alcohol and behenyl alcohol.

  Component (B) is used singly or in combination of two or more, and preferably contains a component having a sterol residue as at least one ester residue.

  Specifically, N-lauroyl-L-glutamate di (phytosteryl 2-octyldodecyl), N-lauroyl-L-glutamate di (cholesteryl behenyl octyldodecyl), N-lauroyl-L-glutamate di (cholesteryl. Octyldodecyl), N-lauroyl-L-glutamate di (phytosteryl, behenyl, 2-octyldodecyl), and the like. Of these, N-lauroyl-L-glutamate di (phytosteryl 2-octyldodecyl) is particularly preferable.

  Component (B) is generally commercially available and sold by Ajinomoto Co., Inc. “Elduu PS-203” (N-lauroyl-L-glutamate di (phytosteryl / octyldecyl)), “Elduu CL-301” ( N-lauroylglutamate di (cholesteryl / behenyl / octyldodecyl)), “Eldue Cl-202” (N-lauroylglutamate di (cholesteryl / octyldodecyl)), “Elduu PS-304” (N-lauroylglutamate di (phytosteryl / Behenyl / octyldodecyl)), “El Deu PS-306” (N-lauroyl glutamate di (octyldodecyl / phytosteryl / behenyl)) and the like.

  (B) A component may be used independently and may be used in mixture of 2 or more types. (B) The content of the N-acylamino acid ester in the total amount of the emulsified composition is preferably 0.01 to 10% by mass, more preferably 0, from the viewpoint of the solubility of the poorly water-soluble substance and the non-sticky feeling of use. 0.05 to 8 mass%, more preferably 0.1 to 5 mass%.

  As the amino acid constituting the (C) N-acylamino acid and / or salt thereof used in the present invention, glutamic acid, aspartic acid, glycine, alanine, threonine, methylalanine, sarcosine, lysine, arginine and the like can be used. These amino acids may be L-form, D-form or DL-form. One of these may be used, or two or more selected from the above group may be mixed and used. From the viewpoints of irritation, dispersion stability, and stickiness, acidic amino acids or neutral amino acids are more preferable. Specifically, glutamic acid, aspartic acid, glycine, and alanine are more preferable, and glutamic acid is particularly preferable.

  As the acyl group constituting the N-acylamino acid of component (C), an acyl group derived from a saturated or unsaturated linear or branched fatty acid having 8 to 22 carbon atoms can be used. For example, examples of fatty acids include caprylic acid, capric acid, lauric acid, myristic acid, stearic acid, isostearic acid, palmitic acid, oleic acid, linoleic acid, behenic acid, coconut oil fatty acid, palm oil fatty acid, and hardened beef tallow fatty acid. These may be used alone or in combination of two or more. In particular, lauric acid, myristic acid, stearic acid, coconut oil fatty acid, and palm oil fatty acid are preferable from the viewpoint of stability with time and lack of stickiness, and lauric acid, myristic acid, and stearic acid are particularly preferable.

  The salt of the component (C) is not particularly limited, and examples thereof include alkali metals such as sodium and potassium, inorganic salts such as calcium, magnesium, aluminum and zinc, or organic such as ammonia, monoethanolamine, diethanolamine and triethanolamine. Examples thereof include organic salts such as amines and basic amino acids such as arginine and lysine. Among these, one kind or a mixture of two or more kinds can be used. Sodium, potassium, triethanolamine, and arginine are preferable because they are easily available on the market.

  Specific examples of component (C) include coconut oil fatty acid-derived acylated glutamic acid, palm oil fatty acid-derived acylated glutamic acid, lauroyl aspartic acid, myristoyl glutamic acid, lauroyl glutamic acid, stearoyl glutamic acid, and alkali metal salts thereof. Preferred are sodium myristoyl glutamate, sodium lauroyl glutamate, and sodium stearoyl glutamate.

  The content of the component (C) with respect to the total amount of the emulsified composition is preferably 0.001 to 5% by mass, more preferably 0.01 to 2% by mass, from the viewpoint of irritation, dispersion stability, and no stickiness. %, More preferably 0.1 to 2% by mass.

  The (D) nonionic surfactant having an HLB value of 1 to 6 used in the present invention is preferably a nonionic surfactant having an HLB value of 1.5 to 5.5. Although it does not specifically limit as a nonionic surfactant, For example, propylene glycol fatty acid ester, glycerol fatty acid ester, sorbitan fatty acid ester, polyglycerol fatty acid ester, polyoxyethylene hydrogenated castor oil, etc. are mentioned.

  Examples of the fatty acid propylene glycol include propylene glycol stearate (HLB: 3.5), propylene glycol isostearate (HLB: 3.5), and propylene glycol oleate (HLB: 3.5). Examples of the glycerin fatty acid ester include glyceryl myristate (HLB: 3.5), glyceryl stearate (HLB: 1.5 to 4.0), glyceryl isostearate (HLB: 4.0), and glyceryl oleate (HLB: 2). .5), glyceryl distearate (HLB: 2). Examples of sorbitan fatty acid esters include sorbitan monostearate (HLB = 4.7), sorbitan monoisostearate (HLB = 5), sorbitan sesquiisostearate (HLB = 4.5), and sorbitan sesquioleate (HLB = 3.7). ), Sorbitan monooleate (HLB = 4.7), and sorbitan trioleate (HLB = 1.7). Polyglyceryl fatty acid esters include polyglyceryl-2 stearate (HLB: 5.0), polyglyceryl-2 oleate (HLB: 5.5), polyglyceryl-2 isostearate (HLB: 5.5), polyglyceryl triisostearate -2 (HLB: 3), polyglyceryl stearate-4 (HLB: 6), polyglyceryl oleate-4 (HLB: 6.0), polyglyceryl tristearate-6 (HLB: 2.5), polyglyceryl pentastearate -10 (HLB: 3.5), polyglyceryl pentahydroxystearate-10 (HLB: 3.5), polyglyceryl pentaisostearate-10 (HLB: 3.5), polyglyceryl pentaoleate-10 (HLB: 3. 5). Examples of the polyoxyethylene hydrogenated castor oil include PEG-5 hydrogenated castor oil (HLB: 6.0).

  Of these, propylene glycol fatty acid ester, glycerin fatty acid ester, and sorbitan fatty acid ester are preferable, and propylene glycol stearate, propylene glycol isostearate, propylene glycol oleate, glyceryl palmitate, glyceryl stearate, glyceryl isostearate are more preferable. Glyceryl oleate, sorbitan monostearate, sorbitan monoisostearate, sorbitan monooleate, more preferably propylene glycol isostearate, glyceryl stearate, and glyceryl isostearate.

  Here, the HLB (hydrophilic-lipophilic balance) value is generally a value indicating the affinity of a surfactant to water and oil, and can be easily determined by the Griffin method.

  (D) A component may be used independently and may mix and use 2 or more types. The content of the component (D) in the total amount of the emulsified composition is preferably 0.001 to 10% by mass, more preferably 0.01 to 8% by mass, from the viewpoint of emulsion stability and solubility of the hardly water-soluble substance. %, More preferably 0.1 to 6% by mass.

  In view of emulsification stability, irritation to the skin, and stickiness, the content mass ratio (B / C) of the component (C) to the component (B) is preferably 1 to 10, and more preferably 1 to 6. Moreover, 0.5-10 are preferable and, as for the content mass ratio (D / C) of (D) component and (C) component, 0.5-7 are more preferable from the point of emulsification stability and skin familiarity.

Since the emulsion composition of the present invention is excellent in salt resistance, an electrolyte that releases cations (for example, metal ions) when dissolved in an aqueous solution can be used. Specifically, potassium carbonate, potassium chloride, potassium sulfate, potassium sulfite, sodium carbonate, sodium chloride, sodium sulfate, sodium sulfite, sodium hydrogen sulfate, sodium hydrogen sulfite, calcium carbonate, calcium chloride, calcium sulfate, magnesium carbonate, chloride Inorganic salts such as magnesium, magnesium sulfate, zinc chloride, zinc sulfate, aluminum chloride, and aluminum sulfate; glycyrrhizinate such as dipotassium glycyrrhizinate; α-hydroxy such as aminocaproic acid, citric acid, salicylic acid, lactic acid, glycolic acid, and tartaric acid Acid salt; serine, glycine, asparagine, aspartic acid, tranexamic acid, lysine, threonine, alanine, tyrosine, valine, leucine, proline, arginine, threonine, cysteine, cysteine Amino acids such as methionine, tryptophan, glutamic acid, pyrrolidone carboxylic acid and derivatives thereof; ascorbic acid, sodium ascorbate, potassium ascorbate, magnesium ascorbate, sodium ascorbate ester, magnesium ascorbate phosphate, calcium ascorbate phosphate, Sodium ascorbate sulfate, magnesium ascorbate sulfate, calcium ascorbate sulfate, glucoside ascorbate (2-O-α-D-glucopyranosyl-L-ascorbic acid), glucosamine ascorbate, dehydroascorbic acid, vitamin B2, vitamin B6, vitamin B12, vitamin B13, biotin, pantothenic acid, niacin, folic acid, inositol, carnitine, thiamine, chi Vitamins such as mindisulfide, fursultiamine, dicetiamine, bisbuthiamine, bisbenchamine, benfotiamine, thiamine monophosphate disulfide, chicotiamine, octothiamine, prosultiamine; others, disodium ethylenediaminetetraacetate, ethylenediaminetetra Trisodium acetate, tetrasodium ethylenediaminetetraacetate, sodium benzoate, trisodium edetate, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, adenosine-3'-5'-cyclic monophosphate, adenosine monophosphate Examples thereof include acids, adenosine diphosphate, adenosine triphosphate, and salts thereof.

  Among these, even electrolytes that need to be incorporated in a considerable amount in order to exert physiological functions when applied to the skin can be suitably used. Inorganic salts, amino acids and derivatives thereof, vitamins, edetic acid Examples of suitable electrolytes include salts and benzoates.

  The salt of the electrolyte is not particularly limited, for example, alkali metals such as sodium and potassium, inorganic salts such as calcium, magnesium, aluminum and zinc, or organic amines such as ammonia, monoethanolamine, diethanolamine and triethanolamine, Organic salts such as basic amino acids such as arginine and lysine can be mentioned, and one or more of these can be used in combination. Sodium, potassium, triethanolamine, and arginine salts are preferred because they are readily available on the market.

  The content of the electrolyte in the emulsion composition is preferably from 0.1 to 8 mass, more preferably from 0.5 to 6 mass%, more preferably from 0.5 to 5.5, based on the total amount of the emulsion composition. % By mass. If it is in the said range, since the effect which electrolyte has is fully exhibited and it is excellent in storage stability, it is preferable.

  The average particle size (average emulsion particle size) of the emulsified particles at 25 ° C. in the emulsified composition of the present invention is 0.25 μm or less and 0.005 to 0.25 μm from the viewpoint of storage stability and lack of stickiness. Is preferable, and it is more preferable that it is 0.005-0.15 micrometer. The average emulsified particle size is measured by a dynamic light scattering method.

Such an emulsified composition is, for example, a high-pressure emulsification method, that is, an oily component together with a surfactant and water at a high shear force, for example, 10 ⁴ s ⁻¹ or more, preferably 10 ⁴ to 10 ⁸ s ⁻¹ , particularly Preferably, it can be produced by emulsifying with an emulsifier (high-pressure homogenizer or the like) capable of obtaining a shear rate of 10 ⁷ to 10 ⁸ s ^-1 or an emulsifier using ultrasonic waves. Further, it can also be produced by utilizing interfacial chemical characteristics which are adjusted by raising the temperature of the system once to a temperature above the solubilization limit temperature of the system and then cooling.

When emulsifying with a high-pressure homogenizer, it is preferable to carry out at 10 ⁵ s ^-1 or more, preferably 10 ⁷ to 10 ⁸ s ^-1 at 20 ° C. Such a high shearing force can be obtained by using a high-pressure emulsifier such as Philmix (made by Tokushu Kika Co., Ltd.), Claremix (made by Mtechnics), Microfluidizer (made by Microfluidics), DeBEE2000 (BEE). (Made by International Co., Ltd.) etc.

For example, a finely emulsified emulsion can be obtained by setting the injection pressure to a range of 300 to 3000 kg / cm ² and a temperature of 5 to 50 ° C. However, the above operating conditions such as pressure and temperature vary depending on the specifications of the apparatus and are not particularly limited. Moreover, the emulsion which has the fine emulsion particle | grains of a desired particle diameter can also be obtained by performing the same high shearing force process to the preliminary | backup emulsion obtained by the normal emulsification method. Moreover, you may perform this high shearing force process repeatedly as needed. Further, an emulsion having a high concentration of the oil component can be produced and then diluted with water or an aqueous medium to obtain an emulsion having a desired concentration.

  In the emulsion composition of the present invention, water, a surfactant other than the above components, an oily component, an ultraviolet absorber, a resin, a sticky agent, a fungicide and antiseptic, a fragrance, Components such as humectants, salts, solvents, antioxidants, chelating agents, neutralizing agents, pH adjusting agents, insect repellents, and physiologically active ingredients can be used.

  There is no restriction | limiting in particular as an application of the emulsion composition of this invention, It can use suitably for cosmetics, a pharmaceutical, a quasi-drug, etc. Specifically, hair cosmetics such as shampoos, rinses and conditioners, face wash, cleansing cosmetics, lotions, emulsions, beauty creams, base cosmetics, sunscreen cosmetics, packs, massage cosmetics and other skin cosmetics, It can be suitably used as an external medicine such as an ointment or cream containing various drugs. In particular, the external preparation for skin of the present invention is preferably used as a type of external preparation for skin that is not washed off and is retained on the skin.

  The dosage form of the emulsified composition of the present invention can be applied to a cream, a paste, a solid and the like in addition to a lotion and emulsion. Moreover, as an emulsion type of the emulsion composition of this invention, it is an oil-in-water type.

Embodiments of the present invention are shown below.
[1] An emulsified composition comprising the following components (A) to (D) and having an average emulsified particle size of 0.25 μm or less.
(A) Slightly water-soluble substance (B) N-acyl amino acid ester (C) N-acyl amino acid and / or salt thereof (D) Nonionic surfactant having an HLB value of 1 to 6 [2] Component (A) A biphenyl compound represented by the general formula (1) or (2), a UV absorber solid at 25 ° C., a ceramide, a carotenoid or a derivative thereof, a tocopherol or a derivative thereof, a retinol or a derivative thereof, and a general formula (3) The emulsified composition according to [1], which is one or more selected from ubiquinone represented.

(Wherein R ¹ and R ² are the same as above)

(Wherein R ³ and R ⁴ are the same as above)

(Where n is the same as above)

[3] The component (A) is a biphenyl compound represented by the general formula (1) or (2), a UV absorber solid at 25 ° C., a ceramide, and a ubiquinone represented by the general formula (3). The emulsified composition according to [1] or [2], which is one or more selected.
[4] The component (A) is a biphenyl compound represented by the general formula (1) or (2), 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester, 2,4,6-tris [4- (2-ethylhexyloxycarbonyl) anilino] -1,3,5-triazine, diethylhexylbutamide triazone, 4-tert-butyl-4′-methoxy-dibenzoylmethane, ceramide, coenzyme Q10 The emulsified composition according to any one of [1] to [3], which is one type or two or more types.
[5] Component (A) is 2,2′-dihydroxy-5,5′-di-n-propylbiphenyl, 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester, 2,4,6 From tris [4- (2-ethylhexyloxycarbonyl) anilino] -1,3,5-triazine, diethylhexylbutamide triazone, 4-tert-butyl-4′-methoxy-dibenzoylmethane, ceramide, coenzyme Q10 The emulsified composition according to any one of [1] to [4], which is one or more selected.
[6] The content of the component (A) is 0.01 to 10% by mass, preferably 0.05 to 5% by mass, more preferably 0.1 to 5% by mass with respect to the total amount of the emulsion composition. The emulsion composition according to any one of 1] to [5].
[7] Component (B) is a mono- or diester of an N-acylamino acid having an acyl group derived from a fatty acid having 8 to 22 carbon atoms and a sterol or an alkyl or alkenyl alcohol having 8 to 38 carbon atoms [1] -Emulsion composition in any one of [6].
[8] Component (B) is N-lauroyl-L-glutamate di (phytosteryl 2-octyldodecyl), N-lauroyl-L-glutamate di (cholesteryl behenyl octyldodecyl), N-lauroyl-L-glutamic acid [1] to [7], which is one or more selected from di (cholesteryl octyldodecyl) and N-lauroyl-L-glutamate di (phytosteryl behenyl 2-octyldodecyl). Emulsified composition.
[9] The content of the component (B) is 0.01 to 10% by mass, preferably 0.05 to 8% by mass, more preferably 0.1 to 5% by mass with respect to the total amount of the emulsion composition. 1]-[8] The emulsion composition in any one of.
[10] The emulsion composition according to any one of [1] to [9], wherein the component (C) is an N-acylated amino acid having an acyl group derived from a fatty acid having 8 to 22 carbon atoms and / or a salt thereof. .
[11] The content of the component (C) is 0.001 to 5 mass%, preferably 0.01 to 2 mass%, more preferably 0.1 to 2 mass%, based on the total amount of the emulsion composition. 1]-[10] The emulsion composition in any one of.
[12] The component (D) is one or more selected from propylene glycol fatty acid ester, glycerin fatty acid ester, sorbitan fatty acid ester, polyglycerin fatty acid ester and polyoxyethylene hydrogenated castor oil [1] to [11 ] The emulsion composition in any one of.
[13] The content of component (D) is 0.001 to 10 mass%, preferably 0.01 to 8 mass%, more preferably 0.1 to 6 mass%, based on the total amount of the emulsion composition. [1] The emulsion composition according to any one of [12].
[14] The emulsion composition according to any one of [1] to [13], wherein the content ratio (B / C) of the component (B) to the component (C) is 1 to 10, preferably 1 to 6.
[15] The content mass ratio (D / C) of the component (D) and the component (C) is 0.5 to 10, preferably 0.5 to 7, according to any one of [1] to [14] Emulsified composition.
[16] The emulsion composition according to any one of [1] to [15], further comprising (E) an electrolyte that releases cations when dissolved in water.
[17] The content of the component (B) is 0.1 to 8% by mass, preferably 0.5 to 6% by mass, more preferably 0.5 to 5.5% by mass based on the total amount of the emulsion composition. The emulsion composition according to [16].
[18] The emulsified composition according to any one of [1] to [17], wherein the average particle diameter of the emulsified particles is 0.005 to 0.25 μm, preferably 0.005 to 0.15 μm.

  EXAMPLES Hereinafter, although an Example demonstrates this invention in more detail, this invention is not limited by these.

Examples 1-22 and Comparative Examples 1-10
Emulsified compositions having the compositions described in Tables 1 and 2 below were prepared by the following production method. The obtained emulsion composition was subjected to the following sensory evaluation, dispersion stability evaluation, and temporal stability evaluation. These evaluation results are shown together in Tables 1 and 2.

(1) Average particle size For the obtained emulsion composition, the average particle size of oil droplets is prepared by a conventional method using a dynamic light scattering particle size distribution measuring device LB-550 (manufactured by Horiba Seisakusho). It was measured by. The average particle diameter refers to the arithmetic average diameter.

(2) Stability evaluation with time After each sample was stored in a thermostatic bath at 0 ° C. for 1 month, the sample was observed with a microscope to confirm the presence or absence of crystallization, and the stability was evaluated. Moreover, after preserve | saving for 1 month at 40 degreeC with a thermostat, the external appearance observation of the sample was performed and stability was evaluated.

[Stability test (0 ° C) evaluation criteria]
○: No crystals Δ: Slightly crystals ×: Crystals [Stability test (40 ° C) evaluation criteria]
○: No change in appearance △: Part of oil floating is observed ×: Completely separated

(3) Sensory evaluation Prepare five specialized panelists for each evaluation item (however, the panelists may overlap depending on the item), the panelists actually use the formulation, "good skin familiarity", "stickiness" “None” was evaluated in accordance with the following evaluation criteria, and the following criteria were shown based on the average score of all panelists.

[Paneler criteria]
Judgment criteria Score Feels highly effective 3
The effect is felt 2
The effect is not felt 1

〔Evaluation criteria〕
Evaluation criteria Evaluation The average score of panel evaluation is more than 2 points and 3 points or less.
The average panel evaluation score is more than 1 point and 2 points or less △
The average panel evaluation score is 1 point or less ×

(4) Skin flexibility evaluation Using 5 panelists, a site was provided on the inner side of the upper arm, and skin flexibility was measured using “Venustron” (manufactured by AXIOM) in an untreated state. . The Venustron emits a certain frequency (Hz) from the probe, and evaluates the softness by the frequency difference Δf when it comes into contact with the object. Specifically, when a soft object is touched, the frequency decreases, so Δf becomes negative, and when a hard object is touched, the frequency increases, so Δf becomes positive. Using this, Δf before the treatment was measured, and then 30 μL of the sample was applied to the site (3 cm × 3 cm) and left for 5 minutes, and then Δf after the treatment was measured. Using these values, a value obtained by subtracting the measured value before the treatment from the measured value after the treatment was calculated. As this value is a negative number and the absolute value is larger, it can be distinguished that the effect of imparting flexibility to the skin is greater. In the evaluation, the average value of the panel was shown.

〔Evaluation criteria〕
Evaluation criteria Evaluation Δf exceeds 5 points ○
Δf is more than 3 points and less than 5 points
Δf is 3 points or less ×

(Production method)
In Table 1, components 1 to 9 heated and dissolved at 80 ° C., and components 10 to 12 heated and dissolved at 80 ° C. were gradually added under propeller stirring (200 r / min) and pre-emulsified. Thereafter, using a high-pressure emulsifier Microfluidizer (manufactured by Microfluidics Co., Ltd.), the mixture was passed three times under an injection pressure of 2000 kgf / cm ² to prepare an emulsion composition. Moreover, about the comparative example 4, the thing which heat-dissolved the components 1-9 at 80 degreeC to the thing which heat-dissolved the components 10-12 at 80 degreeC performs a homomixer process (9000r / min), and is an emulsion composition A product was prepared. In addition, when the aqueous solution was dropped into the emulsion, the mixture was uniformly mixed, and water droplets of the aqueous solution were not formed. Therefore, it was confirmed that the emulsion was an oil-in-water emulsion composition.

  It was confirmed from Examples 1-11 that the emulsified composition of the present invention can stably contain various poorly water-soluble substances. On the other hand, Comparative Example 1 is the same as Example 1 except that component (B) is not blended, and it is understood that emulsification stability and skin flexibility are improved by blending component (B). . Comparative Example 2 is the same as Example 1 except that component (C) is not blended, and it is understood that emulsification stability is improved by blending component (C). Comparative Example 3 is the same as Example 1 except that component (D) is not blended, and it is understood that the blending of component (D) improves the emulsion stability and lack of stickiness. Comparative Example 4 is the same as Example 1 except that the average particle diameter of the emulsified particles is large, and it is understood that emulsification stability and sensory evaluation are improved by making the emulsion particles smaller (0.2 μm or less). The

  Next, in order to confirm the salt tolerance of the emulsified composition of the present invention, sodium chloride, ascorbic acid glucoside, and EDTA (ethylenediaminetetraacetic acid) were added as electrolytes to perform the above evaluation.

(Production method)
In Table 2, components 1 to 11 heated and dissolved at 80 ° C. and components 12 to 14 heated and dissolved at 80 ° C. were gradually added under propeller stirring (200 r / min) for preliminary emulsification. Then, using a high-pressure emulsifier Microfluidizer (manufactured by Microfluidics), the emulsion was passed 3 to 5 times under an injection pressure of 2000 kgf / cm ² to obtain an emulsion. An aqueous solution in which components 15 to 19 were mixed with this emulsion was added with stirring to prepare an emulsion composition.

  The emulsion composition of the present invention exhibits excellent salt resistance, and a stable emulsion can be obtained regardless of the amount and type of electrolyte. Moreover, a component (B) and a component (D) are not specifically limited, It is understood that it may select suitably from the components generally marketed and may be used, and may mix and use 2 or more types. On the other hand, Comparative Examples 5 to 7 are the same as Example 15 except that the essential components of the present application are not blended, and Comparative Example 8 is obtained by replacing component (D) with POE (60) hardened castor oil. In Comparative Example 9, the component (D) was further replaced with decaglyceryl laurate. In Comparative Example 9, the component (B), hydrogenated soybean lecithin, decaglyceryl laurate described in the prior art document 4 was used. When the component (A) and salt were blended, they were separated and could not be formulated. From the comparison of these examples and comparative examples, it is clear that the salt resistance of the examples of the present invention was remarkably improved.

Formulation Examples 1-7
Next, lotion and cream were prepared according to the following formulation.

(Production method)
In Table 3, components 1 to 17 heated and dissolved at 80 ° C. and components 18 to 24 heated and dissolved at 80 ° C. were gradually added under propeller stirring (200 r / min) for preliminary emulsification. Then, using a high-pressure emulsifier Microfluidizer (manufactured by Microfluidics), the emulsion was passed 3 to 5 times under an injection pressure of 2000 kgf / cm ² to obtain an emulsion. An aqueous solution in which components 25 to 35 were mixed with this emulsion was added with stirring to prepare an emulsion composition.

  The emulsified composition of the present invention is excellent in storage stability, has a good skin fit, has a less sticky feel, and is particularly excellent in salt resistance. For example, the oily and aqueous functional components are sufficiently effective. Can be blended in an amount of

Claims (3)

An emulsified composition comprising the following components (A) to (D) and having an average emulsified particle size of 0.25 μm or less.
(A) Slightly water-soluble substance (B) N-acyl amino acid ester (C) N-acyl amino acid and / or salt thereof (D) Nonionic surfactant having an HLB value of 1 to 6 The component (A) is selected from a biphenyl compound represented by the following general formula (1) or (2), a UV absorber solid at 25 ° C., ceramides, and a ubiquinone represented by the following general formula (3) The skin external preparation according to claim 1, which is a seed or two or more kinds.

(Wherein R ¹ and R ² each represent a hydrogen atom or a linear or branched alkyl group or alkenyl group having 1 to 10 carbon atoms)

(Wherein R ³ and R ⁴ each represent a linear or branched alkyl group, alkenyl group, hydroxyalkyl group or hydroxyalkenyl group, aldehyde group or acetyl group having 1 to 5 carbon atoms)

(However, n in the formula represents an integer of 7 to 10)   The emulsified composition according to claim 1 or 2, wherein a content mass ratio (D / C) of the component (C) and the component (D) is 0.5 to 10.