Polyglycerol fatty acid ester, and cosmetic and external preparation comprising the same

Abstract

To provide a polyglycerol fatty acid ester which enables preparation of a cosmetic and an external preparation which can give transparency while having excellent use feeling.SOLUTION: To provide a polyglycerol fatty acid ester which, in its 10-90 wt.% aqueous solution and in a graph of a logarithmic scale with concentration as the X axis and viscosity at a shear of 0.1 s-1 as the Y axis, has no maximum point in the range of 30-70 wt.%.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to a polyglycerol fatty acid ester, and a cosmetic composition and an external preparation containing the same. [Background technology]

[0002] Solubilizers are used to blend oily ingredients such as fragrances, hydrocarbon oils, ester oils, and fat-soluble vitamins, as well as active ingredients that are poorly soluble in water, in cosmetics, quasi-drugs, and topical skin preparations, etc. The most commonly used solubilizers have a structure with a PEG chain as the main backbone and hydrogenated castor oil as the side chain, but they have a problem with the feel when touching the skin after spreading it out.

[0003] In recent years, the use of polyglycerol fatty acid esters has been proposed from the standpoints of reducing the environmental load, high safety, and low irritation to the skin, etc. (Patent Documents 1 and 2). However, the polyglycerol fatty acid esters reported thus far have a weak solubilizing power, and in order to prepare a solubilized cosmetic preparation with a transparent appearance, it is necessary to incorporate a large amount of them, and the obtained cosmetic preparation has a heavy feel when used and is sticky after application, which are problems with the feel when used. Therefore, there has been a demand for the development of polyglycerol fatty acid esters that can provide solubilized cosmetic preparations with an excellent feel when used and a translucent or transparent appearance. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 06-219923 [Patent Document 2] Japanese Patent Application Publication No. 11-071256 Summary of the Invention [Problem to be solved by the invention]

[0005] The problem to be solved by the present invention is to provide a polyglycerol fatty acid ester which can be used to prepare cosmetic compositions and topical preparations which have excellent usability and transparency. [Means for solving the problem]

[0006] As a result of intensive research to solve the above problems, the inventors of the present invention have found that, in a 10 to 90 wt % aqueous solution, the concentration is plotted on the X-axis, and the shear rate is 0.1 s -1 The inventors have found that a polyglycerol fatty acid ester that does not have a maximum point in the range of 30 to 70% by weight in a graph with a logarithmic scale where the Y axis represents the viscosity at 200° C. can solve the above problems, and have thus completed the present invention. Effect of the Invention

[0007] By using a specific polyglycerol fatty acid ester, the present invention can provide cosmetics and topical preparations that have a good feel when used and also have transparency, which cannot be achieved with hydrogenated castor oil having a PEG chain. [Brief description of the drawings]

[0008] [Figure 1] Viscosity behavior graphs of 10-90% by weight aqueous solutions of each polyglycerol fatty acid ester or hydrogenated castor oil containing PEG chains DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] The present invention will be described in detail below. The scope of the present invention is not limited to this embodiment, and the present invention also includes modifications and the like within the scope of the present invention. Note that the range "~" includes the upper and lower limits.

[0010] The polyglycerol fatty acid ester according to the present invention is, in a 10 to 90% by weight aqueous solution, the concentration is plotted on the X-axis, and the shear rate is 0.1 s -1The graph is a logarithmic scale graph with the viscosity at 0.1 s on the Y axis and has no maximum point in the range of 30 to 70% by weight. -1 In a graph with a logarithmic scale where the viscosity at 100°C is plotted on the Y-axis, cosmetics and topical preparations containing a polyglycerol fatty acid ester that does not have a maximum point in the range of 30 to 70% by weight do not feel sticky (squeaky) on the skin even after a while after spreading, and are excellent in feel when used. The detailed mechanism by which the cosmetics and topical preparations of the present invention achieve the above-mentioned effects is unknown, but is thought to be as follows. Note that the following mechanism does not limit the scope of the present invention in any way.

[0011] Many of the highly hydrophilic surfactants that are usually used as solubilizers form high-viscosity structures such as cubic liquid crystals, lamellar liquid crystals, and hexagonal liquid crystals when mixed with water. It is known that many liquid crystal structures are highly viscous, and it was hypothesized that highly viscous liquid crystal structures cause stickiness and snagging when skin is rubbed against another skin. Therefore, the inventors focused on the shear viscosity of high-concentration aqueous solutions, and found that for aqueous solutions of 10 to 90% by weight, the concentration is plotted on the X-axis, and the shear rate is 0.1 s -1 It was found that polyglycerol fatty acid esters, which are characterized by not having a maximum point in the range of 30 to 70% by weight in a graph with a logarithmic scale of viscosity at 1000 g / m2 on the Y-axis, provide an extremely excellent feel when applied and spread without any stickiness or tackiness.

[0012] The shear viscosity measurements were performed using the following equipment and according to the following procedure. Sample to be measured: Aqueous solution with a weight ratio of polyglycerol fatty acid ester to water of 10 / 90 to 90 / 10 Equipment used: Dynamic viscoelasticity measuring device (TA instruments, Discovery Hybrid Rheometer-2) Measurement jig: 40mm diameter parallel plate Aqueous solutions with a weight ratio of polyglycerol fatty acid ester to water of 10 / 90 to 90 / 10 were measured at a temperature of 25°C, a gap width of 500 μm, and a shear rate of 0.1 s -1 The change in viscosity was measured.

[0013] The polyglycerol fatty acid ester according to the present invention is -1 It is preferable that the viscosity of a 50% by weight aqueous solution in the above-mentioned composition is 100 Pa s or less. Cosmetics and topical preparations containing a polyglycerol fatty acid ester having a viscosity of 100 Pa s or less in a 50% by weight aqueous solution are preferable because they do not cause a sticky or squeaky feeling after being spread with fingers or hands.

[0014] The polyglycerol fatty acid ester according to the present invention preferably does not form an anisotropic structure in a 50% by weight aqueous solution. When a polyglycerol fatty acid ester that does not form an anisotropic structure is used, it is preferable in that it does not form a highly viscous hydrate on the skin after being spread on the skin, the moisture evaporates, and the skin is penetrated, and therefore no squeaky feeling occurs.

[0015] The method for producing polyglycerol, which is the raw material of the polyglycerol fatty acid ester according to the present invention, is not particularly limited, and includes a conventional method for producing polyglycerol, in which glycerol is heated in the presence of an alkali catalyst under normal or reduced pressure.

[0016] The polyglycerol fatty acid ester according to the present invention can be produced by a conventionally known esterification reaction, for example, a method of producing the polyglycerol fatty acid ester by esterification reaction of a fatty acid and a polyglycerol in the presence of an alkali catalyst such as sodium hydroxide.

[0017] The fatty acid constituting the polyglycerol fatty acid ester of the present invention is not particularly limited and can be appropriately selected from fatty acids constituting ordinary polyglycerol fatty acid esters. For example, caprylic acid, 2-ethylhexanoic acid, isononanoic acid, capric acid, lauric acid, myristic acid, isomyristic acid, palmitic acid, isopalmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, 12-hydroxystearic acid, ricinoleic acid, arachidic acid, behenic acid, erucic acid, etc. Among them, from the viewpoint of transparency of cosmetics and external preparations containing polyglycerol fatty acid ester, saturated fatty acids are preferred, and caprylic acid, capric acid, lauric acid, and myristic acid are more preferred.

[0018] The polyglycerol fatty acid ester according to the present invention is suitable for use as a solubilizing agent. The oily components to be solubilized are not particularly limited as long as they are used as oily components for cosmetics, and examples thereof include plant-based fragrances such as rose oil, jasmine oil, peppermint oil, anise oil, lavender oil, and bergamot oil, animal-based fragrances such as musk, leopard tree, sea urchin, and limonene, and synthetic fragrances such as hydrocarbon-based fragrances such as limonene, alcohol-based fragrances such as linalool, geraniol, and menthol, aldehyde-based fragrances such as citral, ketone-based fragrances such as β-ionone, and phenol-based fragrances such as eugenol. Other examples include compound fragrances prepared by mixing plant-based fragrances, animal-based fragrances, and synthetic fragrances according to purpose, fat-soluble vitamins such as tocopherol acetate, α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, α-tricoenol, β-tricoenol, γ-tricoenol, and δ-tricoenol as vitamin E, and retinol and β-carotene as vitamin A. In addition to these, fragrances and fat-soluble vitamins used in cosmetics can also be used.

[0019] Further oily ingredients include ethyl oleate, ethyl linoleate, isopropyl myristate, isopropyl palmitate, isopropyl isostearate, isopropyl lanolate, hexyl laurate, myristyl myristate, cetyl myristate, octyldodecyl myristate, decyl oleate, octyldodecyl oleate, hexyldecyl dimethyloctanoate, cetyl octanoate, isocetyl octanoate, cetostearyl octanoate, and ethylhexyl octanoate. Allyl, stearyl octanoate, isostearyl octanoate, acetylated lanolin alcohol, cetyl lactate, diisostearyl malate, dioctyl succinate, isononyl isononanoate, glyceryl tricaprylate, trioctanoin, glyceryl trilaurate, glyceryl tripalmitate, glyceryl tristearate, glyceryl triisostearate, glyceryl trioleate, glyceryl triundecylate, glyceryl tribehenate, glyceryl trilanolinate, glyceryl trimyristate, glyceryl tri(caprylic / capric acid), propylene glycol dicaprylate, propylene glycol dicaprate, propylene glycol dinonanoate, propylene glycol di(caprylic / capric acid), propylene glycol distearate, propylene glycol diisostearate, propylene glycol dioleate, liquid paraffin, liquid isopaniline Examples of oils that can be used include roughine, squalane, orange roughy oil, jojoba oil, liquid lanolin, safflower oil, soybean oil, evening primrose oil, grape seed oil, rosehip oil, kukui nut oil, almond oil, sesame oil, wheat germ oil, corn oil, cottonseed oil, avocado oil, olive oil, camellia oil, persic oil, castor oil, peanut oil, hazelnut oil, macadamia nut oil, and meadowfoam oil. In addition to these, oils used in cosmetics can also be used.

[0020] Active ingredients in quasi-drugs include allantoin, isopropylmethylphenol, estradiol, photosensitizer No. 201, d-camphor, dl-camphor, glycyrrhizinic acid, β-glycyrrhetinic acid, stearyl glycyrrhetinate, salicylic acid, tocopherol acetate, tocopherol nicotinate, peppermint oil, hinokitiol, l-menthol, dl-menthol, eucalyptus oil, pyridoxine dicaprylate, ascorbyl dipalmitate, vitamin A oil, and retinol palmitate.

[0021] The method for solubilization is not particularly limited, and the solubilization can be carried out by a conventional method. For example, the polyglycerol fatty acid ester of the present invention and the substance to be solubilized, such as a flavoring or a fat-soluble vitamin, are dissolved in ethanol or the like, and then the solution is diluted with purified water to easily prepare a solubilized aqueous solution.

[0022] The amount of the polyglycerol fatty acid ester of the present invention relative to the fragrance, fat-soluble vitamin, or oil is not particularly limited, but from an economical standpoint, it is preferable to use a polyglycerol fatty acid ester in an amount of 10 times or less, by weight, the amount of the substance to be solubilized, and more preferably 5 times or less.

[0023] The applications of the present invention are not particularly limited, but in cosmetics, water-based cosmetic preparations such as skin lotions, lotions, milky lotions, and creams are preferred, and in external preparations for the skin, lotion-based external preparations are preferred.

[0024] In addition, within the scope that does not impair the effect of the present invention, it can be appropriately blended with ingredients that are usually blended in skin external preparations, cosmetics, and medicines.For example, it can be blended with polyhydric alcohols such as glycerin, propylene glycol, dipropylene glycol, 1,3-butylene glycol, polyethylene glycol, etc., sugars such as hyaluronic acid, maltitol, etc., thickeners such as alginates, cellulose derivatives, quince seed gum, carboxyvinyl polymers, acrylic acid polymers, etc., preservatives such as parabens, phenoxyethanol, salicylic acid, sorbic acid, isopropylmethylphenol, etc., whitening agents such as arbutin, ellagic acid, kojic acid, ascorbate derivatives, astringents, ultraviolet absorbers, amino acids, glycyrrhizic acid derivatives, plant extracts, pH adjusters, etc. EXAMPLES

[0025] The present invention will be described in more detail below with reference to examples and comparative examples, but the scope of the present invention is not limited to these examples.

[0026] The polyglycerol fatty acid ester and hydrogenated castor oil having a PEG chain used in the examples were dissolved in water at a shear rate of 0.1 s -1 Table 1 shows the shear viscosity and the presence or absence of anisotropic structures.

[0027] [Viscosity behavior with concentration change] For each polyglycerol fatty acid ester or hydrogenated castor oil with PEG chain, the shear rate of 0.1 s for 10-90 wt% aqueous solution was -1 The shear viscosity was measured and the viscosity behavior is shown in Figure 1.

[0028] [Anisotropic structure] Hydrates containing 50% by weight of each polyglycerol fatty acid ester or hydrogenated castor oil having a PEG chain and 50% by weight of water were observed under crossed Nicols with a polarizing microscope to determine the presence or absence of anisotropic structures.

[0029] [Table 1]

[0030] The solubilized solutions of Examples 1 to 6 and Comparative Examples 1 to 3 containing 3% by weight of polyglycerol fatty acid ester or hydrogenated castor oil having a PEG chain, 5% by weight of ethanol, 0.5% by weight of fragrance, and 91.5% by weight of water shown in Table 1 were prepared, and the spreadability, squeaky feeling, and transparency were evaluated based on the following indices. The results are shown in Table 2.

[0031] [Good stretchability] A sensory evaluation was carried out by six panelists. 1 g of each of the solubilized solutions of Examples 1 to 8 and Comparative Examples 1 to 3 was applied to the forearm, and the solution was spread with the index finger. The spreadability was evaluated on a scale of 1 to 10, and the average score was calculated. The evaluation was based on the following criteria. (standard) ◎: 8.0 points or more ○: 6.0 points or more, less than 8.0 points △: 4.0 points or more, less than 6.0 points ×: Less than 4.0 points

[0032] [Creasing sensation] A sensory evaluation was carried out by six panelists. 1 g of the solubilized solution of Examples 1 to 8 and Comparative Examples 1 to 3 was applied to the forearm and spread with the index finger. If the solubilized solution did not feel sticky when touched with the finger after a few minutes, the maximum score was 10 points, and the average score was calculated and evaluated according to the following criteria. (standard) ◎: 8.0 points or more ○: 6.0 points or more, less than 8.0 points △: 4.0 points or more, less than 6.0 points ×: Less than 4.0 points

[0033] [Transparency] The transmittance of the solubilized solutions obtained in the Examples and Comparative Examples was measured at a wavelength of 660 nm using a spectrophotometer and evaluated according to the following criteria. (standard) ◎: 98.0% or more ○: 90.0% or more but less than 98.0% △: 80.0% or more but less than 90.0% ×: Less than 80.0%

[0034] [Table 2]

[0035] In a 10-90% by weight aqueous solution, the concentration is on the x-axis and the shear rate is 0.1 s -1 In a graph with a logarithmic scale of viscosity at 100°C on the Y-axis, the solubilized solutions of Examples 1 to 6 using polyglycerol fatty acid esters that do not have a maximum point in the range of 30 to 70% by weight spread well when spread, and did not feel squeaky even after time had passed after spreading. The solubilized solutions of Examples 1 to 5 also had excellent transparency. On the other hand, the solubilized solution of Comparative Example 1 using polyglycerol fatty acid ester having a maximum point in the range of 30 to 70% by weight had good spreadability, but after a period of time, it felt squeaky and was inferior in feel to the ones in the Examples. Also, the transparency was low. Furthermore, the solubilized solutions of Comparative Examples 2 and 3, which used hydrogenated castor oil having a PEG chain, had good transparency, but gave a squeaky feeling after spreading, and were poor in feel when used.

[0036] (Formulation example 1: Lotion) A phase (wt%) Polyglycerol fatty acid ester 2 0.5 Ethanol 5.0 Lavender oil 0.1 B phase Wednesday 94.4 ------------------------------------------------------------------ Total 100.0

[0037] Phase A was heated to 70°C and homogenized. Phase A was added to Phase B and stirred until transparent. The lotion of Formulation Example 1 was highly transparent, spread well when applied, and had an excellent feel when used without any squeaky feeling after time had passed.

[0038] (Formulation Example 2: Emulsion) (% by weight) Phase A Macadamia nut oil polyglyceryl-6 esters behenate *1 1.5 Squalane 9.0 Meadowfoam Oil 3.0 Behenyl Alcohol 1.0 Glyceryl stearate 1.0 B phase Glycerin 6.0 Diglycerin 4.0 Polyglycerol fatty acid ester 2 1.0 Butylene Glycol 6.0 Agar xanthan gum 0.3 Xanthan gum 0.1 Lavender oil 0.2 Water 66.9 Preservatives qs ---------------------------------------------------------------------------------- Total 100.0 *1: S-Face VL-211 (manufactured by Sakamoto Pharmaceutical Co., Ltd.)

[0039] Phase A and Phase B were heated to 80°C and homogenized. Phase A was gradually added to Phase B at 80°C to emulsify. The emulsion of Formulation Example 2 spread well when applied and had no squeaky feeling after time had passed, making it an emulsion with excellent usability.

[0040] (Formulation Example 3: Cleansing Lotion) (% by weight) Polyglycerol fatty acid ester 2 5.0 Polyglyceryl-6 isostearate *2 2.0 Pentylene glycol 10.0 Butylene glycol 10.0 Water 73.0 Preservatives qs ---------------------------------------------------------------------------------- Total 100.0 *2: S-Face IS-601P

[0041] All the raw materials were heated to 60°C, then stirred to homogenize, to prepare a cleansing lotion. The cleansing lotion of Formulation Example 3 had excellent cleansing properties and was excellent in feel when used without any squeaking sensation when blended with makeup.

Claims

1. In 10 to 90% by weight aqueous solutions, the concentration is on the X-axis and the shear rate is 0.1 s －１ 4. A polyglycerol fatty acid ester according to claim 1, wherein the polyglycerol fatty acid ester has no maximum point in the aqueous solution concentration range of 30 to 70% by weight in a logarithmic graph with the viscosity at 200° C. as the Y-axis.

2. Shear rate 0.1 s －１ 2. The polyglycerol fatty acid ester according to claim 1, characterized in that the viscosity of a 50% by weight aqueous solution thereof is 100 Pa·s or less.

3. 3. The polyglycerol fatty acid ester according to claim 2, which does not form an anisotropic structure in a 50% by weight aqueous solution.

4. A cosmetic or external preparation comprising the polyglycerol fatty acid ester according to claim 1.

5. The cosmetic or topical preparation according to claim 4, which is in the form of a skin lotion, a lotion, a cream, or a milky lotion.

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