JP2011046701A - Emulsifier, dispersion stabilizer, and skin care preparation containing them - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an emulsifier which uses a naturally occurring polymer emulsifier with both safety of the polymer emulsifier and multiple usage of a low-molecular emulsifier so that skin irritation is reduced and defect on feel peculiar in utilizing a common polymer emulsifier and restriction on dosage form are canceled; a dispersion stabilizer which stably disperses a nano emulsifying particle into an aqueous phase; and a skin care preparation using them. <P>SOLUTION: Glycidyl ether having a 4-30C alkyl group is reacted with inulin having an average molecular weight of 500-10,000, to form alkyl glyceryl etherized inulin in which a hydroxy group in inulin is substituted with the degree of substitution (DS) in range of 0.001-1 per 1 residue of constituent fructose. The emulsifier containing alkyl glyceryl etherized inulin as an effective component, the dispersion stabilizer and the skin care preparation containing them, are provided. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to an emulsifier and a dispersion stabilizer containing alkyl glyceryl etherified inulin as an active ingredient, and a skin external preparation containing the same.

  Conventionally, naturally-occurring polymers such as alkylated cellulose and synthetic polymers such as acrylic acid copolymers have been used as polymer emulsifiers. Since these polymer emulsifiers are polymers, they are difficult to absorb percutaneously, and can therefore reduce irritation to the skin. Further, since the solubilization of the preservative which is a concern in the low molecular emulsifier hardly occurs, the preservative can be reduced, so that it is very superior to the conventional low molecular emulsifier in terms of safety.

  For these polymer emulsifiers, those using natural ingredients as raw materials reflecting the natural orientation and plant orientation of consumers are desired. For example, modified cellulose ethers (Patent Document 1) and fructooligosaccharide fatty acids. Esters (Patent Document 2) are used. However, although these naturally-derived polymer emulsifiers are said to have emulsifying ability, their functions are not sufficiently exhibited as emulsifiers, and they are used substantially as thickening gelling agents. Most (Patent Document 3). Therefore, in order to produce an external preparation for skin including cosmetics, other surfactants must be used in combination, and it has been difficult to produce a surfactant-free product. In the case of lotion and low-viscosity emulsions, there is also a drawback that a sticky feeling derived from the water-soluble surfactant used in combination occurs.

  Many polymer emulsifiers, including synthetic polymer emulsifiers, have viscoelasticity derived from polymers, so cosmetics prepared using polymer emulsifiers are poorly handled and are familiar to the skin. In addition, there was a problem in terms of feel such as stickiness.

  In addition, nano-emulsions or microemulsions with a transparent to translucent appearance in which nano-emulsified particles having an average particle size of 1 to 500 nm are dispersed in an aqueous phase are generally solubilized by solubilizing oil with a large amount of a surfactant. Compared to liquids, a large amount of oil phase can be emulsified and dispersed transparently and translucently with a small amount of surfactant, so in skin external preparations, oil is applied to lotions and cosmetic liquids that have a transparent to translucent appearance. It is suitable when blending. On the other hand, when these nanoemulsions or microemulsions are blended into lotions or the like, the stability is significantly reduced due to the addition of surfactants, dipotassium glycyrrhizinate, amino acids or sodium citrate in the formulation, and the system There was a problem that the quality of the product greatly deteriorated due to white turbidity and precipitation.

  Inulin, an alkyl carbamate in which molecular weight of several thousand inulin is oleophilic is a polymer emulsifier that solves these problems (Patent Document 4), but the raw material alkyl carbamate is substantially only inulin lauryl carbamate. There are few raw material variations, and there are problems in product development. Moreover, it is difficult to sufficiently emulsify a high concentration silicone oil.

  By the way, although an inulin derivative using an epoxidized alkane is known (Patent Document 5), the introduced alkyl group is short, so that the expected emulsification performance is not obtained. In addition, a surfactant (Patent Document 6) in which one hydroxyl group of a sugar molecule is substituted with a (poly) glycerin derivative is known, but the introduction rate of alkyl groups is high, and sufficient emulsifying ability and surfactant ability are exhibited. could not.

Japanese Patent Laid-Open No. 03-012401 Japanese Patent Laid-Open No. 03-197409 JP 2004-352689 A JP-A-2005-504630 JP 07-149802 A Japanese Patent Application Laid-Open No. 08-188588

  The present invention reduces skin irritation and uses general polymer emulsifiers by using a naturally occurring polymer emulsifier that combines the safety of polymer emulsifiers with the versatility of low molecular emulsifiers. When applied to the skin, there is no specific stickiness, poor handling, and poor skin fit, and a skin external preparation that feels good when emulsified with a low molecular emulsifier, more preferably a polyoxyethylene-based surfactant. An object of the present invention is to provide the above-mentioned external preparation for skin which does not use an agent.

  Also provided are low-viscosity skin external preparations that have been difficult to prepare using conventional polymer emulsifiers, and skin external preparations that contain high concentrations of silicone oils that were difficult to emulsify with existing inulin emulsifiers. That is.

  Furthermore, the present invention provides a skin external preparation by using a specific dispersion stabilizer in a skin external preparation having a transparent or translucent appearance in which nano-emulsified particles having an average particle diameter of 1 to 500 nm are dispersed in an aqueous phase. It is an object to provide a skin external preparation having a transparent or translucent appearance including the nano-emulsified particles which are not easily affected by the contained surfactant or electrolyte and have excellent stability.

  As a result of intensive studies in view of the above-mentioned circumstances, the present inventors have surprisingly made inulin having an average molecular weight of 500 to 10,000 react with glycidyl ether having an alkyl group having 4 to 30 carbon atoms, thereby producing the inulin. A compound in which the hydroxyl group is substituted with a substitution degree (DS) in the range of 0.001 to 1 per constituent fructose residue is a polymer emulsifier, but it has a thickening action peculiar to polymers. It was found that the touch defects can be eliminated. Moreover, it discovered that a high concentration silicone oil could be emulsified.

  Further, the alkyl glyceryl etherified inulin (component (A)) is one or more selected from the group consisting of (B) a lipophilic surfactant of HLB 9 or less, a higher alcohol, a higher fatty acid, and an alkyl glyceryl ether. , (C) polyhydric alcohol, (D) a liquid oil at 25 ° C. and combined with other than component (B), resulting in a dosage form with better emulsion stability, moisture retention, and feel and a rich variety It has been found that an external preparation for skin can be provided.

  Furthermore, the alkyl glyceryl etherified inulin (component (A)) is a dispersion stabilizer in a skin external preparation having a transparent or translucent appearance in which nano-emulsified particles having an average particle diameter of 1 to 500 nm are dispersed in an aqueous phase. As found useful.

  And, by using the alkylglyceryl etherified inulin (component (A)) as a dispersion stabilizer, it was found that an external preparation for skin in which nano-emulsified particles having an average particle size of 1 to 500 nm were stably dispersed could be provided. The invention has been completed.

  By using the alkyl glyceryl etherified inulin of the present invention, the skin irritation is reduced and the drawbacks of general polymer emulsifiers are eliminated. Skin external preparations and low-viscosity skin external preparations can be provided. Moreover, the external preparation for skin containing the silicone oil which was difficult to emulsify with the existing inulin emulsifier can be provided.

  In addition, combining the alkyl glyceryl etherified inulin of the present invention with the component (B), component (C), and component (D) results in low skin irritation, higher emulsification stability and moisture retention, and better feel. A variety of skin preparations can be provided.

  Furthermore, in a skin external preparation having a transparent or translucent appearance in which nano-emulsified particles having an average particle diameter of 1 to 500 nm are dispersed in an aqueous phase, by using the alkylglyceryl etherified inulin of the present invention as a dispersion stabilizer, It is possible to provide a skin external preparation having a transparent or translucent appearance including the nano-emulsified particles which are not easily affected by the surfactant or electrolyte contained in the external preparation for skin and are excellent in stability.

  The alkyl glyceryl etherified inulin of the present invention which is the component (A) of the present invention is synthesized, for example, by the following method. It can be obtained by reacting inulin and alkyl glycidyl ether in an aprotic polar solvent at a temperature of 80 ° C. to 150 ° C. for 1 to 5 hours in the presence of a basic catalyst. For example, after the reaction, the solvent can be distilled off under reduced pressure, and a low-boiling solvent can be added to the residue and washed. It is sufficient to change the stoichiometric proportion of the reactants to produce a derivative with the desired degree of substitution.

  The alkyl glyceryl etherified inulin of the present invention is obtained by reacting an inulin having an average molecular weight of 500 to 10,000 with a glycidyl ether having an alkyl group having 4 to 30 carbon atoms to convert the hydroxyl group in the inulin to a constituent fructose residue. The degree of substitution (DS) is in the range of 0.001-1.

  Preferably, it is desirable to react an alkyl glycidyl ether having an average molecular weight of inulin of 1,000 to 5,000 and having 8 to 22 carbon atoms.

  As for the substitution degree (DS) for inulin, the substitution degree of the alkyl glyceryl ether group is preferably 0.002 to 0.8, more preferably 0.01 to 0.5, for each fructose unit.

The degree of substitution (DS) for inulin is given as an equivalent number of alkyl glyceryl ether groups relative to a monosaccharide. In general, the greater the amount of alkyl glycidyl ether charged to the reaction, the more hydroxyl groups of the inulin molecule are substituted. The For example, a substitution degree of 1 indicates a case where 1 equivalent number of glyceryl ether groups are introduced with respect to a monosaccharide. The degree of substitution can be determined from the ratio of the integral area value of monosaccharide protons to the integral area value of protons of alkyl glyceryl ether groups by a known ¹ H-NMR method.

  The alkyl glyceryl etherified inulin of the present invention can achieve the effects of the present invention only with this component, and can also achieve the effects of the present invention using two or more different alkyl groups and / or alkyl substitution degrees of this component. .

  Although details of the emulsification mechanism by the alkyl glyceryl etherified inulin of the present invention are not clear, in the water-in-oil emulsion composition, an alkyl group is coordinated at the oil interface, and the inulin as the hydrophilic group is outside the oil phase. By forming a hydrophilic layer film appropriately, it is considered that stable emulsification can be achieved without causing a thickening action as found in existing polymer emulsifiers.

  The compounding amount of the alkyl glyceryl etherified inulin of the present invention in the external preparation for skin varies depending on the use and form of the external preparation for skin, but is usually 0.1 to 40% by mass, preferably 0.2 to 30% by mass. More preferably, it is 0.5 to 10% by mass. If it is this range, the effect of this invention can be exhibited more.

  By combining the components (B), (C), and (D) described below together with the above component (A), the skin of the dosage form with higher emulsion stability and moisture retention, good touch and rich variety An external preparation can be prepared.

  The lipophilic surfactant of HLB 9 or less as the component (B) used in the present invention is usually HLB 1 to 9, preferably HLB 3 to 9. As the lipophilic surfactant having an HLB of 9 or less, phospholipid, polyglycerin fatty acid ester, glycerin fatty acid ester, propylene glycol fatty acid ester, sorbitan fatty acid ester and the like are preferable, and these can be used alone or in combination of two or more. .

  Specifically, phospholipids include lecithins such as soybean lecithin, egg yolk lecithin, hydrogenated soybean lecithin, hydrogenated egg yolk lecithin, lysolecithin and / or hydrogenated lysolecithin obtained by converting these lecithins into a monoacyl form by enzymatic treatment. Hydroxylecithin that has been converted into a non-crystalline form. In addition, phospholipid fractions in lecithin such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidic acid, and phosphatidylserine can be used individually or in combination. Of these, soybean lecithin and hydrogenated soybean lecithin are particularly preferable.

  Polyglyceryl fatty acid esters include diglyceryl monostearate, diglyceryl monooleate, diglyceryl monoisostearate, diglyceryl triisostearate, tetraglyceryl monostearate, tetraglyceryl monooleate, and tetraglyceryl pentastearate. , Hexaglyceryl monostearate, Hexaglyceryl monooleate, Hexaglyceryl tristearate, Hexaglyceryl pentastearate, Hexaglyceryl polyricinoleate, Decaglyceryl tristearate, Decaglyceryl trioleate, Decaglyceryl pentastearate, Pentas Decaglyceryl hydroxystearate, decaglyceryl pentaisostearate, decaglyceryl pentaoleate, heptaster Examples include decaglyceryl phosphate, decaglyceryl heptaoleate, decaglyceryl decastearate, decaglyceryl decaisostearate, decaglyceryl dekaoleate, decaglyceryl polyricinoleate, and one or a combination of two or more of these can do. Particularly preferred among these are diglyceryl monostearate, tetraglyceryl monostearate, tetraglyceryl monooleate, hexaglyceryl monostearate, hexaglyceryl monooleate, hexaglyceryl tristearate, decaglyceryl pentastearate Decaglyceryl pentaisostearate.

  Examples of glycerin fatty acid esters include glyceryl undecylate, glyceryl monomyristate, glyceryl monostearate, glyceryl monoisostearate, glyceryl distearate, glyceryl monooleate, and the like, or a combination of one or more of these. can do. Of these, glyceryl monostearate, glyceryl monoisostearate, and glyceryl distearate are particularly preferred.

  Examples of the propylene glycol fatty acid ester include propylene glycol monolaurate, propylene glycol monopalmitate, propylene glycol monostearate, propylene glycol monooleate, propylene glycol monobehenate, and the like. Can be used. Of these, propylene glycol monostearate, propylene glycol monopalmitate, and propylene glycol monooleate are particularly preferred.

  Examples of sorbitan fatty acid esters include sorbitan laurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquistearate, sorbitan tristearate, sorbitan monoisostearate, sorbitan sesquiisostearate, sorbitan monooleate, sorbitan sesquioleate, Examples include sorbitan trioleate and the like, and one or more of these can be used in combination. Particularly preferred are sorbitan monostearate, sorbitan trioleate, and sorbitan monooleate.

  Examples of higher alcohols include lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol, and the like. These may be used alone or in combination of two or more. it can. Particularly preferred are cetyl alcohol, stearyl alcohol, and behenyl alcohol.

  Examples of the higher fatty acid include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, 12-hydroxystearic acid, and isostearic acid. These can be used alone or in combination of two or more. Particularly preferred are palmitic acid, stearic acid, behenic acid and isostearic acid.

  Examples of the alkyl glyceryl ether include batyl alcohol, chimyl alcohol, cerachiral coal and fatty acid esters thereof, and these can be used alone or in combination of two or more. Particularly preferred are batyl alcohol and chimyl alcohol.

  Examples of the polyhydric alcohol (C) used in the present invention include polyethylene glycol, propylene glycol, 1,3-butylene glycol, dipropylene glycol, glycerin, sorbitol, xylitol, maltitol and the like. Particularly preferred are 1,3-butylene glycol and glycerin.

  As the component (D) used in the present invention which is a liquid oil at 25 ° C. and other than the component (B), any oily raw material generally used in cosmetics can be suitably used. Specifically, squalane, liquid paraffin, α-olefin oligomer, hydrocarbons such as polyethylene, fluorinated oils, vegetable oils such as olive oil, macadamia nut oil, jojoba oil, animal oils such as beef tallow, glyceryl triisooctanoate, tri (Caprylic acid / capric acid) glyceryl, glyceryl tri-2-ethylhexanoate, trimethylolpropane triethylhexanoate, cetyl 2-ethylhexanoate, 2-ethylhexyl myristate, isopropyl myristate, cetyl isooctanoate, isooctyl palmitate, capryl And esters such as propylene glycol acid. In addition, according to this invention, the silicone oil which was conventionally difficult to emulsify with the existing inulin emulsifier can be mix | blended in high concentration.

  Examples of the silicone oil include dimethyl silicone, phenylmethyl silicone, and cyclomethicone. Particularly preferred are dimethyl silicone and cyclomethicone. It is preferable that a silicone oil contains 10-100 mass% in the said whole oil agent. More preferably, it is 20-50 mass%. Within this range, the skin external preparation of the present invention has a better feel.

In the present invention, the ratio (mass ratio) of the components (A) to (D) is:
(A) / (B) = 10/90 to 95/5 is preferable, more preferably (A) / (B) = 20/80 to 80/20, and still more preferably (A) / (B) = 25/75 to 50/50.
(A) / (C) = 1/99 to 75/25 is preferable, (A) / (C) = 5/95 to 50/50, more preferably (A) / (C) = 10/90 to 20/80.
(A) / (D) = 5/95 to 95/5 is preferable, more preferably (A) / (D) = 15/85 to 80/20, and still more preferably (A) / (D) = 20/80 to 75/25.
(A) + (B) / (C) = 20/80 to 95/5 is preferable, (A) + (B) / (C) = 25/75 to 80/20, more preferably (A) + (B) / (C) = 30/70 to 75/25.
(A) + (B) / (D) = 10/90 to 95/5 is preferable, more preferably (A) + (B) / (D) = 20/80 to 85/15, still more preferably, (A) + (B) / (D) = 30/70 to 70/30.
In this range, the external preparation for skin can be prepared more stably.

  When preparing a skin external preparation containing the alkyl glyceryl etherified inulin of the present invention, a normal emulsification apparatus such as a paddle mixer, a homomixer, a high-pressure homomixer or the like can be used. The preparation method is a method in which an alkyl glyceryl etherified inulin, a water-soluble raw material and water are previously melt-mixed at 50 to 80 ° C., and an oily raw material at 50 to 80 ° C. is added under stirring with a homomixer or the like, or In addition, an alkyl glyceryl etherified inulin, a water-soluble raw material, and water previously melted and mixed at 50 to 80 ° C. are put into an oily raw material heated to 50 to 80 ° C. while stirring with a homomixer or the like. The method etc. are mentioned.

  Furthermore, the alkyl glyceryl etherified inulin which is the component (A) of the present invention can be used as a dispersion stabilizer. The dispersion stabilizer in the present invention is for stably dispersing nanoemulsified particles in an aqueous phase.

  In the external preparation for skin using the alkyl glyceryl etherified inulin which is the component (A) of the present invention as a dispersion stabilizer, nano-emulsified particles having an average particle size of 1 to 500 nm, preferably 5 to 200 nm, more preferably 10 to 10 nm. 100 nm nanoemulsified particles can be included. Nano-emulsified particles are obtained by dispersing an oil phase containing liquid and / or solid oil at room temperature as emulsified particles having an average particle diameter of 1 to 500 nm using a surfactant. Such nano-emulsified particles dispersed in an aqueous phase are called nanoemulsions or microemulsions.

  This nanoemulsion or microemulsion has a transparent or translucent appearance, and generally a large amount of oil phase is transparent with a small amount of surfactant compared to a solubilized liquid in which oil is solubilized with a large amount of surfactant. Alternatively, it can be emulsified and dispersed translucently. Therefore, the external preparation for skin is suitable for blending oil into a lotion or cosmetic liquid having a transparent or translucent appearance.

  In addition, an active ingredient can be blended in the oil phase of such nanoemulsion or microemulsion, but such nanoemulsion or microemulsion can improve their stability and transdermal absorbability. Are known.

  The skin external preparation of the present invention having a transparent or translucent appearance is obtained by placing a certain amount thereof in a quartz cell as a measurement sample, and measuring the transmittance at a wavelength of 680 nm with a spectrophotometer using purified water as a control solution. When the transmittance is less than 60%, white turbidity, from 60 to 85% is translucent, and the state exceeding 85% is transparent.

  Active ingredients that can be incorporated into the oil phase of these nanoemulsions or microemulsions include vitamin A and its derivatives (derivatives such as retinol, retinol palmitate, retinol linoleate, retinol acetate, hydrogenated retinol, etc.), carotenoids (carotene, lycopene) , Astaxanthin, lutein, etc.), vitamin B and derivatives thereof (pyridoxine dioctanoate, pyridoxine dipalmitate, pyridoxine trihexyldecanoate, etc.), vitamin C and derivatives thereof (ascorbic acid alkyl esters such as ascorbyl dipalmitate and ascorbyl tetrahexyldecanoate) Ascorbic acid alkyl ethers such as 3-O-cetylascorbic acid), vitamin D and its derivatives (ergocalciferol, cholecalcifero Such as vitamin E and its derivatives (natural vitamin E, tocopherols such as dl-α (β, γ) -tocopherol, dl-α-tocopheryl acetate, tocopheryl retinoic acid, derivatives thereof, tocotrienol, etc.) In addition to fat-soluble vitamins, examples include oil-soluble drugs such as stearyl glycyrrhetinate, glycyrrhetinic acid, and coenzyme Q10.

  The stability and dispersibility of nanoemulsions or microemulsions can be improved in products such as lotions and serums using the alkyl glyceryl etherified inulin of the present invention as a dispersion stabilizer. That is, by using the alkylglyceryl etherified inulin of the present invention, the nano-emulsified particles can be stably blended into a skin external preparation having a transparent or translucent appearance without causing cloudiness or precipitation.

  The method of blending the nanoemulsified particles using the alkyl glyceryl etherified inulin which is the component (A) of the present invention as a dispersion stabilizer is not particularly limited, but a predetermined amount of the alkyl glyceryl ether of the present invention in advance. A lotion containing fluorinated inulin may be prepared, and a desired amount of nanoemulsion or microemulsion may be added thereto. In addition, it is also preferable to previously add a mixture of the alkyl glyceryl etherified inulin of the present invention and a nanoemulsion or microemulsion to a product such as lotion.

  The amount of the alkyl glyceryl etherified inulin of the present invention in a topical skin preparation containing nano-emulsified particles having an average particle size of 1 to 500 nm using the alkyl glyceryl etherified inulin which is the component (A) of the present invention as a dispersion stabilizer Is preferably 0.05 to 10.0% by mass, more preferably 0.1 to 2.0% by mass, and still more preferably 0.5 to 2.0% by mass in the final composition of the external preparation for skin. is there.

  In the external preparation for skin of the present invention, various components usually used in cosmetics, for example, UV absorbers, inorganic powders, humectants, pH adjusters, neutralizers, antioxidants, antiseptics, antibacterial agents, Active ingredients, drugs, extracts, fragrances, pigments, etc. can be blended. Examples of the ultraviolet absorber include dibenzoylmethane compounds, benzophenone compounds, benzoic acid compounds, salicylic acid compounds, and methoxycinnamic acid compounds. Examples of the inorganic powder include titanium oxide, zinc oxide, talc, and mica. Examples of the humectant include NMF components such as amino acids, water-soluble collagen, elastin, chondroitin sulfate, hyaluronic acid, sodium pyrrolidone carboxylate and the like. Examples of the pH adjuster and neutralizer include lactic acid, citric acid, and sodium edetate. Examples of the antioxidant include α-tocopherol and gallic acid. Examples of antiseptics and antibacterial agents include paraoxybenzoic acid esters, phenoxyethanol, and sorbic acid. As an active ingredient, ascorbic acid, ascorbic acid magnesium phosphate ester, ascorbyl palmitate, ascorbyl stearate, ascorbyl tetraisopalmitate, ascorbyl glucoside, arbutin, ellagic acid, resinol and other whitening agents, glycyrrhizic acid, glycyrrhetic acid, Examples thereof include a rough skin preventive agent such as ceramide, retinol and derivatives thereof, anti-aging agents such as vitamin A acid and derivatives thereof, various vitamins and derivatives thereof, and the like.

  Surfactants that can be used in the present invention include POE sorbitan fatty acid esters such as POE sorbitan monooleate and POE sorbitan monostearate, POE sorbite fatty acid esters such as POE sorbite monolaurate and POE sorbite monooleate, and POE glycerin monoester. POE glycerin fatty acid esters such as stearate, POE glycerin monoisostearate, POE glycerin triisostearate, POE fatty acid esters such as POE monooleate and POE monoisostearate, POE lauryl ether, POE oleyl ether, POE isostearyl POE alkyl ethers such as ether and POE stearyl ether, POE / POP cetyl ether, POE / POP decyl tetradecyl ether Nonionic surfactants such as POE / POP alkyl ethers such as sucrose fatty acid esters and glycerin fatty acid esters, fatty acid soaps such as sodium laurate and sodium palmitate, sulfate esters such as sodium lauryl sulfate and sodium lauryl sulfate , Acylated amino acid salts such as sodium lauroyl sarcosine, sodium cocoyl-N-methyltaurate, sodium lauryl glutamate, anionic surfactants such as phosphate ester salts such as sodium monolauryl phosphate, cations such as quaternary ammonium salts These are surfactants, etc., but these can be used alone or in combination of two or more. However, since the product of the present invention is a naturally derived emulsifier, it is more desirable not to add a polyoxyethylene surfactant when preparing a cosmetic comprising only naturally derived components.

  The use application of the external preparation for skin according to the present invention is not particularly limited, for example, lotion, milky lotion, cream, foundation, lipstick, cleansing foam, cleansing cream, shampoo, hair rinse, lip balm, hair spray, mousse, It can be applied to various products such as sunscreen or tanning cream, eyeliner, mascara, hair or nail care, massage cream, body make-up preparation, or skin treatment such as ointment.

  In addition, the alkylglyceryl etherified inulin, which is also the component (A) of the present invention, can be used as an emulsifier and as a dispersion stabilizer for nanoemulsified particles, as a solubilizer, a powder dispersant, and a gelling agent. Available

  Further, since the alkyl glyceryl etherified inulin (A) has little interaction with other surfactants, oil can be added to the formulation without causing emulsion breakage. For example, in general, when blended with oil in shampoo, a method of emulsifying and adding oil in advance for the purpose of suppressing a reduction in foaming power is known, but even in such a case, the interface in the shampoo Foaming often decreases due to demulsification by the active agent. By using the emulsion obtained by using the alkyl glyceryl etherified inulin of the component (A) of the present invention, a shampoo that does not affect foaming can be prepared even if oil is blended. Specifically, using the alkyl glyceryl etherified inulin of component (A) of the present invention as an emulsion in advance, it is blended into a shampoo or prepared by blending oil into a shampoo containing this product. can do.

  The present invention will be described more specifically with reference to the following examples, but the present invention is not limited thereto.

  Example 1

  As shown in Table 1, various alkyl glyceryl etherified inulins were synthesized, and the emulsion compositions shown in Table 2 were prepared to evaluate the emulsification performance. In the determination of the emulsifying performance, a good emulsified state in which the emulsion particle size is small and no oil floating occurs is ◎, a good emulsified state in which no oil floating occurs is ○, and an oil phase separated is ×.

（調製方法）
Ａ、Ｂを８０℃に加温した。ＡにＢを添加し、ホモミキサーにて乳化し（５，０００ｒｐｍ、２分間）、２４時間後の乳化状態を観察した。
As a result, as shown in Table 1, it was confirmed that the alkyl glyceryl etherified inulin of the present invention has excellent emulsifying performance.

(Preparation method)
A and B were heated to 80 ° C. B was added to A and emulsified with a homomixer (5,000 rpm, 2 minutes), and the emulsified state after 24 hours was observed.

  (Example 2)

Table 3 shows external preparations for skin using alkyl glyceryl etherified inulin as an emulsifier. Evaluation of the emulsified state of the external preparation for skin immediately after emulsification was evaluated based on the same criteria as in Example 1. The stability was evaluated according to the following criteria.
◎: No change in emulsified particle size, no separation ○: Some change in the emulsified particle size is not observed, but not separated Δ: Emulsified particle size is changed slightly separated ×: Separated

（調製方法）
Ａ、Ｂをそれぞれ８０℃に加温溶解する。ＢにＡを添加し、ホモミキサーを用いて乳化した後、Ｃを添加する。
As a result, it was confirmed that the external preparation for skin of the present invention has a good feel, has a low viscosity, and can stably emulsify silicone oil.

(Preparation method)
A and B are each dissolved by heating to 80 ° C. A is added to B and emulsified using a homomixer, and then C is added.

  Example 3

Derivative No. 1 of Example 1 shown in Table 4. 4 or No. Eight blends of the external preparation for skin of the present invention were prepared and subjected to a moisturizing test. The measurement method is as follows: the present invention product and the comparative product are each 3 mg / inside the forearm of 12 volunteer men and women (25 to 38 years old) who have been waiting for 15 minutes in a constant temperature and humidity room adjusted to 22 ° C. and 45% relative humidity. After applying cm ^2, the skin conductance of the application site over time was evaluated by SKICON 200 for the moisturizing effect. The stability was evaluated based on the same criteria as in Example 2.

（調製方法）
Ａ、Ｂをそれぞれ７0℃に加温溶解する。ＢにＡを徐々に添加し、ホモミキサーを用いて５，０００ｒｐｍで５分間攪拌３０℃まで冷却した。

As a result, as shown in Table 5, it was shown that the skin conductance (average value) by application of the product of the present invention was significantly increased compared to the comparative product. That is, the moisturizing effect of the product of the present invention was confirmed.

(Preparation method)
A and B are each dissolved by heating to 70 ° C. A was gradually added to B, and the mixture was stirred at 5,000 rpm for 5 minutes and cooled to 30 ° C. using a homomixer.

  (Example 4)

About the emulsion composition containing the alkyl glyceryl etherified inulin of Table 4 prepared in Example 3, sensory evaluation was performed using 12 volunteer men and women.
The evaluation method took an appropriate amount of the product of the present invention or a comparative product, and evaluated the feel when applied in five stages. (Evaluation of feel)
5: very favorable 4: favorable 3: unfriendly 2: unfavorable 1: very unfavorable

As a result, the product of the present invention was not sticky as compared with the comparative product, and the hand riding and skin familiarity were good, giving a moist feeling. Therefore, it was shown that the product of the present invention can provide a cosmetic with a good feel.

  (Example 5)

  Table 7 shows a transparent or translucent lotion or serum. In the evaluation of the state of the preparation immediately after the APV treatment, the product in a uniform state without separation was regarded as “good”, and the product in a uniform state after separation was regarded as “separation”. About transparency, the cosmetic liquid was evaluated by the transmittance | permeability in 680 nm with a spectrophotometer. The stability was evaluated based on the same criteria as in Example 2.

（調製方法）
Ａ、Ｂをそれぞれ７０℃に加温溶解する。ＢにＡを添加し、ホモミキサーを用いて乳化する。続いて、これをＡＰＶ用いて、７００ｂａｒ、７０℃で３回パースする。
As a result, it was confirmed that the external preparation for skin of the present invention was transparent or translucent and stable and had a good feel. In addition, 10 panelists with sensitive skin were used twice a day to report the presence or absence of skin irritation, but no one complained of skin irritation.

(Preparation method)
A and B are each dissolved by heating to 70 ° C. A is added to B and emulsified using a homomixer. Subsequently, this is parsed three times at 700 bar and 70 ° C. using APV.

  (Example 6)

（調製方法）
常法に従い、調製した。
Table 8 shows preparations (beauty serum) in which the derivative of Example 1 and phospholipid were used in combination. The stability was evaluated based on the same criteria as in Example 2.

(Preparation method)
Prepared according to a conventional method.

  (Example 7)

  An external preparation for skin containing nano-emulsified particles was prepared by adding a nano-emulsion or micro-emulsion in advance, and blended with a lotion containing the alkylglyceryl etherified inulin of the present invention.

<Preparation of nanoemulsion>
Weigh 8 parts by weight of macadamian nut oil, 1.5 parts by weight of δ-tocopherol and 0.5 parts by weight of β-carotene, melt and mix at 70 ° C using a paddle mixer, and release to 30 ° C with stirring. A uniform oil phase was prepared by cooling. Thereafter, 20 parts by weight of the oil phase and 5 parts by weight of hydrogenated soybean lecithin were weighed and melted and mixed at 70 ° C. using a paddle mixer to obtain nano-emulsified particles. While maintaining the prepared nano-emulsified particles at 70 ° C., using a homomixer, add the mixture to 75 parts by mass of water phase (a mixture of 20 parts by mass of purified water and 80 parts by mass of glycerin) with stirring at 5000 rpm, and then A pre-emulsion was obtained by stirring for 10 minutes under the same conditions. The pre-emulsified product was subjected to a 3-pass treatment at 700 bar and 70 ° C. using a high-pressure homogenizer (APV), and then allowed to cool to 30 ° C. with stirring by a paddle mixer, so that the average emulsion particle size was 59.degree. A nanoemulsion of 0 nm was obtained.

<Preparation of lotion with nanoemulsion>
The lotion stability shown in Table 9 was confirmed based on the same criteria as in Example 2 using the lotion containing the nanoemulsion. For the transparency, the lotion was evaluated by a transmittance at 680 nm with a spectrophotometer, and the stability was evaluated by the same standard as in Example 2. The lotion state (room temperature) immediately after preparation was evaluated according to the following criteria.
Good: Uniform without separation Separation: Non-uniform by separation

（調製方法） As a result, it was confirmed that the external preparation for skin containing nano-emulsified particles using alkylglyceryl etherified inulin is transparent or translucent and stable and has a good touch. This indicates that the alkyl glyceryl etherified inulin of the present invention improves the stability and dispersibility of the nanoemulsion or microemulsion.

(Preparation method)

Using a paddle mixer, all components other than the nanoemulsion were mixed at room temperature to obtain a uniform transparent liquid. The nanoemulsion was added there, and the lotion was obtained by mixing for 10 minutes at room temperature.

(Example 8)
Latex liquid paraffin 1.0% by mass
Triethylhexanoic acid trimethylolpropane 0.5
Ethylhexyl palmitate 2.0
Dimethicone 3.0
Glyceryl monostearate 0.2
Glyceryl monoisostearate 0.2
Glyceryl distearate 0.1
Polyglyceryl monostearate-2 0.2
Polyglyceryl monostearate-4 0.2
Polyglyceryl monooleate-6 0.1
Stearyl alcohol 0.5
Behenyl alcohol 0.5
Derivative No. 1 of Example 1 4 1.0
1,3-butylene glycol 2.0
Glycerin 5.0
Biosaccharide gum-1 0.3
Xanthan gum 0.1
Preservative Appropriate amount of purified water Residue (Preparation method)
Prepared according to a conventional method.

Example 9
Moisturizing cream 1
Squalane 3.0% by mass
Glyceryl tri-2-ethylhexanoate 2.0
Cetyl isooctanoate 5.0
Dimethicone 6mm ² / s 6.0
Glyceryl stearate 0.5
Polyglyceryl tristearate-6 1.0
Cetyl alcohol 0.8
Stearyl alcohol 0.5
Behenyl alcohol 1.0
Derivative No. 1 of Example 1 8 3.0
1,3-butylene glycol 5.0
Glycerin 5.0
Hydroxyethyl cellulose 0.3
Xanthan gum 0.1
Carbomer 0.1
Sodium hydroxide Appropriate amount Preservative Appropriate amount of purified water Residue (Preparation method)
Prepared according to a conventional method.

(Example 10)
Moisturizing cream 2
Glyceryl tri-2-ethylhexanoate 6.0% by mass
Cetyl 2-ethylhexanoate 4.0
Squalane 3.0
Jojoba oil 2.0
Cyclopentasiloxane 3.0
Tri (caprylic / capric) glyceryl 1.0
Dimethicone 6mm ² / s 1.0
Tri-2-ethylhexanoic acid pyridoxine 0.3
Hydrogenated retinol 0.1
Glyceryl monostearate 0.5
Sorbitan monostearate 0.2
Sorbitan trioleate 0.2
Sorbitan monooleate 0.1
Palmitic acid 0.5
Stearic acid 2.8
Isostearic acid 0.5
Batyl alcohol 0.3
Kimyl alcohol 0.2
Derivative No. 1 of Example 1 8 1.5
Derivative No. 1 of Example 1 9 1.5
1,3-butylene glycol 7.0
Dipropylene glycol 3.0
Carbomer 0.2
Arginine Suitable amount Preservative Suitable amount Purified water Residue (Preparation method)
Prepared according to a conventional method.

(Example 11)
Whitening cream 1
α-olefin oligomer 10.0% by mass
Glyceryl triisooctanoate 8.0
Cyclopentasiloxane 5.0
Ascorbyl tetrahexyldecanoate 1.0
Soy lecithin 0.2
Hydrogenated soybean lecithin 0.3
Sorbitan monostearate 1.0
Propylene glycol monostearate 0.5
Cetyl alcohol 1.2
Stearyl alcohol 2.5
Batyl alcohol 0.8
Derivative No. 1 of Example 1 4 3.0
1,3-butylene glycol 5.0
Glycerin 3.0
Carbomer 0.1
Xanthan gum 0.1
Citric acid Appropriate amount Na citrate Appropriate amount Potassium hydroxide Appropriate amount Preservative Appropriate amount Purified water Residue (Preparation method)
Prepared according to a conventional method.

(Example 12)
Whitening cream 2
Ethylhexyl palmitate 5.0% by mass
Tri (caprylic / capric) glyceryl 8.5
Macadamia nut oil 3.0
Dimethicone 350mm ² / s 0.3
Tocopheryl retinoic acid 0.05
Glyceryl monostearate 0.5
Propylene glycol monostearate 0.5
Stearyl alcohol 1.8
Palmitic acid 0.3
Batyl alcohol 0.3
Derivative No. 1 of Example 1 5 2.5
Xanthan gum 0.1
Carbomer 0.2
Hydroxyethyl cellulose 0.1
1,3-butylene glycol 5.0
Glycerin 5.0
Alcorbyl phosphate Mg 2.0
Citric acid Appropriate amount Na citrate Appropriate amount Arginine Appropriate amount Preservative Appropriate amount Purified water Residue (Preparation method)
Prepared according to a conventional method.

(Example 13)
Cream cyclopentasiloxane with high silicone content 8.0% by mass
Dimethicone 350mm ² / s 7.0
Polyglyceryl monostearate-4 0.5
Polyglyceryl monooleate-6 0.3
Polyglyceryl pentaisostearate-10 0.2
Stearyl alcohol 2.0
Behenyl alcohol 1.5
Derivative No. 1 of Example 1 5 2.0
1,3-butylene glycol 7.0
Glycerin 5.0
Hydroxyethyl cellulose 0.2
Xanthan gum 0.3
Carbomer 0.1
EDTA-2Na Appropriate amount Sodium hydroxide Appropriate amount Preservative Appropriate amount of purified water Residue (Preparation method)
Prepared according to a conventional method.

(Example 14)
Sunscreen cream (SPF40 / UVA ++)
Liquid paraffin 3.0% by mass
Trimethylolpropane triethylhexanoate 2.0
Titanium oxide (silicone-treated product) 5.0
Zinc oxide (silicone-treated product) 5.0
Dimethicone 6mm ² / s 3.0
Ethylhexyl palmitate 2.0
Polyglyceryl monostearate-4 1.0
Stearyl alcohol 1.6
Behenyl alcohol 1.8
Ferric oxide young iron (red) Appropriate amount Ferric oxide ferric oxide (yellow) Appropriate amount 6 2.0
1,3-butylene glycol 7.0
Glycerin 5.0
Hydroxyethyl cellulose 0.2
Xanthan gum 0.3
EDTA-2Na Appropriate amount Arginine Appropriate amount Preservative Appropriate amount Purified water Residue (Preparation method)
Prepared according to a conventional method.

(Example 15)
Foundation cream Ethylhexyl methoxycinnamate 7.5% by mass
Ethylhexyl salicylate 5.0
Titanium oxide 8.0
Zinc oxide 5.0
Dimethicone 6mm ² / s 4.0
Phenylmethyl silicone 3.0
Trimethylolpropane triethylhexanoate 2.0
Ethylhexyl palmitate 5.0
Polyglyceryl monostearate-2 0.8
Stearyl alcohol 1.4
Behenyl alcohol 1.6
Derivative No. 1 of Example 1 7 2.0
1,3-butylene glycol 7.0
Glycerin 5.0
Hydroxyethyl cellulose 0.2
Xanthan gum 0.3
EDTA-2Na Appropriate amount Arginine Appropriate amount Preservative Appropriate amount Purified water Residue (Preparation method)
Prepared according to a conventional method.

(Example 16)
Massage cream mineral oil 20.0% by mass
Squalane 20.0
Macadamia nut oil 5.0
Jojoba oil 5.0
Tocopherol acetate 0.1
Glyceryl monostearate 0.5
Propylene glycol monostearate 0.2
Propylene glycol monopalmitate 0.2
Propylene glycol monooleate 0.1
Stearyl alcohol 1.2
Behenyl alcohol 0.8
Batyl alcohol 0.3
Derivative No. 1 of Example 1 5 3.5
Xanthan gum 0.1
Carbomer 0.2
1,3-butylene glycol 5.0
Glycerin 5.0
Citric acid Appropriate amount Na citrate Appropriate amount Arginine Appropriate amount Preservative Appropriate amount Purified water Residue (Preparation method)
Prepared according to a conventional method.

(Example 17)
Cleansing cream mineral oil 20.0% by mass
Squalane 10.0
Isononyl isononanoate 10.0
Isopropyl myristate 5.0
Ethylhexyl palmitate 5.0
Tocopherol acetate 0.1
Glyceryl monostearate 0.5
Propylene glycol monostearate 0.2
Stearyl alcohol 2.4
Palmitic acid 0.3
Batyl alcohol 0.5
Derivative No. 1 of Example 1 8 3.0
Xanthan gum 0.1
Carbomer 0.1
1,3-butylene glycol 3.0
Glycerin 3.0
Citric acid Appropriate amount Na citrate Appropriate amount Arginine Appropriate amount Preservative Appropriate amount Purified water Residue (Preparation method)
Prepared according to a conventional method.

  The skin external preparations of Examples 6 to 17 were each confirmed to have a moisturizing effect and a very good feel by performing a moisturizing test of Example 3 and a sensory evaluation of Example 4.

Claims (10)

Substitution of the hydroxyl group in the inulin in the range of 0.001 to 1 per constituent fructose by reacting inulin having an average molecular weight of 500 to 10,000 with glycidyl ether having an alkyl group having 4 to 30 carbon atoms An emulsifier containing an alkyl glyceryl etherified inulin as an active ingredient, which is substituted with a degree (DS). Substitution of the hydroxyl group in the inulin in the range of 0.001 to 1 per constituent fructose by reacting inulin having an average molecular weight of 500 to 10,000 with glycidyl ether having an alkyl group having 4 to 30 carbon atoms Dispersion stabilizer containing alkyl glyceryl etherified inulin as an active ingredient, characterized by being substituted with a degree (DS). A skin external preparation containing the alkyl glyceryl etherified inulin. A skin external preparation containing the following components (A) to (D).
(A) One or more selected from the group consisting of the above-mentioned alkyl glyceryl etherified inulin (B) lipophilic surfactant of HLB 9 or less, higher alcohol, higher fatty acid, alkyl glyceryl ether (C) polyhydric alcohol ( D) Oil that is liquid at 25 ° C. and other than component (B) The lipophilic surfactant of the component (B) contains one or more selected from the group consisting of phospholipid, polyglycerol fatty acid ester, glycerol fatty acid ester, propylene glycol fatty acid ester, sorbitan fatty acid ester. The external preparation for skin according to claim 4, wherein the preparation is external. The said external component (D) contains the 1 type (s) or 2 or more types of silicone oil, The skin external preparation of Claim 4 or 5 characterized by the above-mentioned. The skin external preparation according to any one of claims 4 to 6, wherein the silicone oil of the component (D) is 10 to 100% by mass in the total oil. The skin external preparation according to any one of claims 3 to 7, which does not contain a polyoxyethylene-type surfactant. The skin external preparation according to any one of claims 3 to 8, comprising nano-emulsified particles having an average particle diameter of 1 to 500 nm. The external preparation for skin according to claim 9, wherein the appearance is transparent or translucent.