Polyglycerol fatty acid ester

Abstract

Disclosed is a polyglycerol fatty acid ester which is an ester of a fatty acid that has 6 to 22 carbon atoms and a polyglycerol that has an average polymerization degree of 5 to 25 and a ratio of a branched glycerol group represented by formula (1) of 14% to 60%, and which has an HLB of 13 or more. The present invention is capable of providing a polyglycerol fatty acid ester which has excellent ability of solubilizing a poorly water-soluble substance; and this polyglycerol fatty acid ester is suitable for use in cosmetic preparations, food, drink and the like.

Description

[Technical field]

[0001] The present invention relates to a polyglycerol fatty acid ester, a solubilizer containing said compound, a composition containing said compound, and cosmetics, foods and beverages containing these. [Background technology]

[0002] Poorly water-soluble substances such as fragrances, essential oils, vegetable oils, hydrocarbon oils, ester oils, and fat-soluble vitamins that are blended into transparent cosmetics such as lotions and beauty serums are solubilized by surfactants. However, since fragrances, essential oils, and vegetable oils are highly polar, it is necessary to blend a large amount of surfactants to solubilize them. As a result, there is a problem that the usability of the cosmetics when applied to the skin is poor.

[0003] As a technique for solving such problems, for example, Patent Document 1 proposes a polyglycerol fatty acid ester in which a polyglycerol containing less than 10% of glycerol polymers having a degree of polymerization of 3 or less is esterified with a fatty acid.

[0004] The same is true for food and beverages, where transparency of the appearance is required when solubilizing poorly water-soluble substances in beverages. In addition, since the addition of a large amount of surfactants affects the flavor, there is a demand to reduce the amount of surfactants. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2018-70529 A Summary of the Invention [Problem to be solved by the invention]

[0006] However, the solubilizing power of Patent Document 1 is not satisfactory, and further improvement is required.

[0007] An object of the present invention is to provide a polyglycerol fatty acid ester which is excellent in solubilizing ability for poorly water-soluble substances. [Means for solving the problem]

[0008] The present invention relates to the following [1] to [6]. [1] A polyglycerol fatty acid ester, which is an ester of a polyglycerol having a branched glycerol group ratio of 14 to 60% and an average degree of polymerization of 5 to 25, represented by the following formula (1), and a fatty acid having 6 to 22 carbon atoms, and has an HLB of 13 or more. [ka] [2] A solubilizer comprising the polyglycerol fatty acid ester according to [1]. [3] A cosmetic composition comprising the polyglycerol fatty acid ester according to [1] and a poorly water-soluble substance. [4] A cosmetic comprising the polyglycerol fatty acid ester according to [1] or the cosmetic composition according to [3]. [5] A composition for food or beverage use, comprising the polyglycerol fatty acid ester described in [1] and a poorly water-soluble substance. [6] A food or beverage comprising the polyglycerol fatty acid ester described in [1] or the food or beverage composition described in [5]. Effect of the Invention

[0009] According to the present invention, a polyglycerol fatty acid ester having excellent solubilizing power for poorly water-soluble substances can be provided. Since the amount of solubilization varies depending on the type of poorly water-soluble substance, etc., in the present invention, a polyglycerol fatty acid ester having improved solubilizing power compared to a polyglycerol fatty acid ester prepared using a commercially available polyglycerol product (Polyglycerol 7) described in the Examples below was determined to have "excellent solubilizing power." [Brief description of the drawings]

[0010] [Figure 1] 13C-NMR spectrum of Production Example 1 DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] As a result of intensive research into the above-mentioned problems, the inventors have found that by providing an appropriate branched structure to the hydrophilic group of polyglycerin in polyglycerol fatty acid ester, the ability to solubilize poorly water-soluble substances is excellent, and have completed the present invention. As for the mechanism, it is presumed that the hydrophilic group of polyglycerin has an appropriate branched structure, which makes it easier to form micelles.

[0012] The polyglycerol fatty acid ester of the present invention is an ester of polyglycerol having a ratio of branched glycerol groups represented by the above formula (1) of 14 to 60% and an average degree of polymerization of 5 to 25, and a fatty acid having 6 to 22 carbon atoms. The HLB of the polyglycerol fatty acid ester of the present invention is 13 or more, preferably 13 to 19.5, more preferably 13.5 to 19, even more preferably 14 to 18.5, and even more preferably 14.5 to 18, from the viewpoint of solubilizing power of poorly water-soluble substances.

[0013] In this specification, HLB refers to a value measured by the following Griffin calculation method. The saponification value and neutralization value are measured by known methods. HLB=20(1-S / A) S: Saponification value of polyglycerol fatty acid ester A: Neutralization value of raw fatty acid

[0014] In the polyglycerol related to the polyglycerol fatty acid ester of the present invention, the ratio of the branched glycerol group represented by the above formula (1) is 14 to 60%, preferably 14 to 36%, from the viewpoint of the solubilizing power of poorly water-soluble substances, and the average degree of polymerization is 5 to 25, preferably 7 to 22. In addition, the number of the branched glycerol groups represented by the above formula (1) per one molecule of polyglycerol is preferably 1 to 15 on average, more preferably 1 to 8 on average, from the viewpoint of solubility in oils. Here, the ratio and number of the branched glycerol groups can be adjusted by the ratio of raw materials during the production of polyglycerol. For example, in the examples described later, the ratio and number of the branched glycerol groups are increased by increasing the amount of glycerol triglycidyl ether used, and the ratio and number of the branched glycerol groups are decreased by decreasing the amount of glycerol triglycidyl ether used. The ratio and number of the branched glycerol groups are measured by the method described in the examples described later.

[0015] The average degree of polymerization of polyglycerol in this specification means the average degree of polymerization of polyglycerol calculated from the hydroxyl value by terminal group analysis, and is the average degree of polymerization calculated from (Equation 1) and (Equation 2). (Equation 1) Average degree of polymerization = (112.2 × 103 - 18 × hydroxyl value) / (74 × hydroxyl value - 56.1 × 103) (Equation 2) Hydroxyl value = (ab) x 28.05 / sample amount (g) a: Amount of 0.5N potassium hydroxide solution consumed in the blank test (ml) b: Amount of 0.5N potassium hydroxide solution consumed in this test (ml) The hydroxyl value in the above formula (1) is calculated using formula (2) in accordance with the "Standard Methods for Analysis of Fats, Oils and Related Materials (I) 1996 Edition" compiled by the Japan Oil Chemists' Society.

[0016] In addition, the polyglycerin related to the polyglycerin fatty acid ester of the present invention has a total content of glycerin and diglycerin of preferably 0.01 to 30% by mass, more preferably 0.01 to 15% by mass, from the viewpoint of the solubilizing power of poorly water-soluble substances. The total content of glycerin and diglycerin in the polyglycerin can be adjusted by adjusting the degree of purification using a column or by adding them separately after purification. The total content of glycerin and diglycerin in the polyglycerin is measured by the method described in the Examples below.

[0017] From the viewpoint of solubilizing power of poorly water-soluble substances, the fatty acid in the polyglycerol fatty acid ester of the present invention has a carbon number of 6 to 22, preferably 8 to 20, and more preferably 8 to 18. The carbon number may also be 6 to 12, 8 to 12, 14 to 22, 14 to 20, or 14 to 18. Specific examples of the fatty acid include, but are not limited to, lauric acid, myristic acid, oleic acid, stearic acid, and isostearic acid.

[0018] The polyglycerol fatty acid ester of the present invention can be prepared by esterification reaction of polyglycerol and fatty acid by a general synthesis method. Since the polyglycerol fatty acid ester of the present invention has excellent solubilizing power of poorly water-soluble substances, it can be suitably used as a solubilizer containing polyglycerol fatty acid ester, a cosmetic composition containing polyglycerol fatty acid ester and a poorly water-soluble substance, a food and beverage composition, etc. In addition, it can be used for known applications of polyglycerol fatty acid ester. Hereinafter, preferred embodiments of the solubilizer, cosmetic composition, and food and beverage composition using the polyglycerol fatty acid ester of the present invention will be described.

[0019] (Solubilizer) The solubilizer of this embodiment contains the polyglycerol fatty acid ester of the present invention, and may optionally contain known components used in solubilizers, such as glycerin, 1,3-butylene glycol (BG), dipropylene glycol (DPG), sugar alcohols, etc.

[0020] The content of the polyglycerol fatty acid ester in the solubilizer of this embodiment is preferably 20 to 80% by mass, more preferably 20 to 50% by mass.

[0021] (Cosmetic composition) The cosmetic composition of this embodiment contains the polyglycerol fatty acid ester of the present invention and a poorly water-soluble substance.

[0022] The content of the polyglycerol fatty acid ester of the present invention in the cosmetic composition of this embodiment is preferably 0.1 to 10 mass %, more preferably 0.1 to 5 mass %.

[0023] In this specification, the poorly water-soluble substance means a substance that is hardly soluble in water or that dissolves only in a small amount, and has a solubility in water of preferably 0.1% or less, more preferably 0.01% or less. Examples of poorly water-soluble substances include fragrances, essential oils, ester oils, hydrocarbon oils, animal and vegetable oils, fat-soluble vitamins, ceramides, preservatives, antibacterial agents, and compositions containing these components.

[0024] Examples of fragrances include hydrocarbon-based fragrances such as limonene, alcohol-based fragrances such as linalool, geraniol, and menthol (L-menthol), aldehyde-based fragrances such as citral, ketone-based fragrances such as β-ionone, and phenol-based fragrances such as eugenol.

[0025] Examples of essential oils include plant-based essential oils such as lavender oil, eucalyptus oil, rose oil, jasmine oil, peppermint oil, anise oil, rosemary oil, and bergamot oil, as well as musk, leopard oil, sea cucumber, and amaranth.

[0026] Ester oils include isononyl isononanoate, isostearyl isostearate, cetyl 2-ethylhexanoate, 2-ethylhexyl palmitate, triethylhexanoin, and tri(caprylic / capric acid)glyceryl.

[0027] Examples of the hydrocarbon oil include hydrogenated polyisobutene, liquid paraffin, light liquid isoparaffin, squalane, phytosqualane, isododecane, and alkanes.

[0028] Examples of vegetable oils include avocado oil, almond oil, olive oil, wheat germ oil, rice germ oil, rice bran oil, safflower oil, soybean oil, corn oil, rapeseed oil, palm oil, palm kernel oil, castor oil, sunflower oil, jojoba oil, macadamia nut oil, and coconut oil; examples of animal oils include EPA oil, DHA oil, beef tallow, chicken fat, lard, and lanolin.

[0029] Examples of fat-soluble vitamins include vitamin E such as tocopherol (tocopherol acetate), α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, α-tricoenol, β-tricoenol, γ-tricoenol, and δ-tricoenol, and fat-soluble vitamins such as vitamin A such as retinol and β-carotene.

[0030] Examples of ceramides include ceramide NP, ceramide NG, ceramide AP, ceramide 2, and ceramide 3.

[0031] Preservatives and antibacterial agents include glyceryl monocaprylate, glyceryl monocaprate, glyceryl monolaurate, methylparaben, propylparaben, ethylhexylglycerin, and caprylyl glycol.

[0032] The content of the poorly water-soluble substance in the cosmetic composition of this embodiment is preferably 0.01 to 3 mass%, more preferably 0.1 to 2 mass%. When two or more poorly water-soluble substances are used, the content of the poorly water-soluble substances refers to the total amount of the poorly water-soluble substances.

[0033] In addition to the above-mentioned components, the cosmetic composition of this embodiment can contain other components that are normally used in cosmetics, as appropriate, depending on the application and purpose. Examples of such optional components include water, surfactants, polyhydric alcohols, aqueous gelling agents, oily gelling agents, UV absorbers, powders, antioxidants, preservatives, fragrances, colorants, chelating agents, cooling agents, thickeners, plant extracts, vitamins, neutralizing agents, moisturizing agents, anti-inflammatory agents, pH adjusters, amino acids, etc.

[0034] The surfactant is not particularly limited, but examples thereof include polyoxyethylene fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene (hydrogenated) castor oil, sodium cocoyl glutamate, TEA-cocoyl glutamate, sodium lauroyl glutamate, potassium cocoyl glycine, sodium lauroyl methylalanine, sodium cocoyl methyl taurine, and sodium lauroyl aspartate.

[0035] Examples of polyhydric alcohols include, but are not limited to, glycerin, diglycerin, ethylhexylglycerin, 1,3-butylene glycol (BG), propylene glycol (PG), propanediol, dipropylene glycol (DPG), pentylene glycol, 1,2-hexanediol, caprylyl glycol, 1,10-decanediol, isopentyldiol, sorbitol, mannitol, maltitol, and xylitol.

[0036] The cosmetic composition of this embodiment can be prepared by mixing the above-mentioned components in a conventional manner.

[0037] The cosmetic composition of this embodiment can be suitably used in various cosmetic preparations. That is, the present invention also provides a cosmetic preparation containing the cosmetic composition of this embodiment. Here, the cosmetic composition of this embodiment may be used as a cosmetic preparation as it is, or may further contain the above-mentioned optional components to form a cosmetic preparation.

[0038] Examples of cosmetics include lotions, beauty essences, perfumes, mouthwashes, hair mists, cleansing lotions, cleansing sheets, and deodorant sheets.

[0039] Examples of the method for producing a cosmetic preparation include a production method that includes a step of incorporating each of the above-mentioned components. Here, the "step of incorporating each of the above-mentioned components" includes a mode in which a cosmetic composition prepared in advance is added, as well as a mode in which each of the above-mentioned components is individually blended to prepare the cosmetic preparation.

[0040] (Composition for food and drink) The food and beverage composition of this embodiment contains the polyglycerol fatty acid ester of the present invention and a poorly water-soluble substance.

[0041] The content of the polyglycerol fatty acid ester of the present invention in the food and beverage composition of this embodiment is preferably 0.5 to 40 mass %, more preferably 1 to 20 mass %, and even more preferably 1 to 10 mass %.

[0042] The content of the poorly water-soluble substance in the food and beverage composition of this embodiment is preferably 1 to 20 mass %, more preferably 1 to 10 mass %. When two or more poorly water-soluble substances are used, the content of the poorly water-soluble substances refers to the total amount of the poorly water-soluble substances.

[0043] In the food and beverage composition of this embodiment, other than the above-mentioned components, components usually used in food and beverages can be appropriately blended according to the application and purpose. Examples of such optional components include water, surfactants, polyhydric alcohols, powders, antioxidants, preservatives, flavorings, colorants, chelating agents, cooling agents, thickeners, plant extracts, vitamins, neutralizing agents, pH adjusters, amino acids, etc.

[0044] The food and beverage composition of this embodiment can be prepared by mixing the above-mentioned components in a conventional manner.

[0045] The food and beverage composition of this embodiment can be suitably used in various foods and beverages. By solubilizing poorly water-soluble substances transparently with a small amount of surfactant, the flavor peculiar to the surfactant can be reduced. That is, the present invention provides a food and beverage with good flavor that contains the food and beverage composition of this embodiment.

[0046] The food and drink products are not particularly limited, and examples thereof include beverages such as non-fruit juice beverages, beverages containing fruit juice, vegetable beverages, carbonated beverages, coffee, alcoholic beverages, beverages containing minerals, beverages containing vitamins, beverages containing functional food materials, milk beverages, lactic acid bacteria beverages, fermented milk, yogurt, ice cream, and other milk-based products, dessert foods such as jelly, bavarois, and pudding, processed foods and retort-processed foods that have been heat-treated, such as beef bowls, pork bowls, oyakodon, Chinese rice bowls, soups, pasta sauces, curries, stews, porridge, canned beverages, canned foods, bottled beverages, and bottled foods, and confectioneries such as candies and snack foods. In particular, the present invention is suitable for beverages that require transparency, such as non-fruit juice beverages, beverages containing fruit juice, vegetable beverages, carbonated beverages, coffee, alcoholic beverages, beverages containing minerals, beverages containing vitamins, and beverages containing functional food materials.

[0047] Examples of the method for producing a food or beverage include a production method including a step of incorporating each of the above-mentioned components. Here, the "step of incorporating each of the above-mentioned components" includes a mode in which a previously prepared composition for food or beverage is added, as well as a mode in which each of the above-mentioned components is individually mixed and prepared. EXAMPLES

[0048] EXAMPLES The present invention will be specifically described below with reference to examples and comparative examples, but the present invention is not limited to these.

[0049] Polyglycerol Production Example 1 100g of glycerin and an alkali catalyst were added to a three-neck flask equipped with a Dimroth and a stirrer, and the temperature was raised to 120°C. 28.26g of glycerin triglycidyl ether was added dropwise at a rate of 10g / hr, and the reaction was continued for another hour after the completion of the addition. The mixture was then passed through an ion exchange resin column to remove unreacted glycerin. The obtained fraction was concentrated to obtain polyglycerin 1.

[0050] Polyglycerol Production Example 2 100g of glycerin and an alkali catalyst were added to a three-neck flask equipped with a Dimroth and a stirrer, and the temperature was raised to 120°C. 47.1g of glycerin triglycidyl ether was added dropwise at a rate of 10g / hr, and the reaction was continued for another hour after the completion of the addition. The mixture was then passed through an ion exchange resin column to remove unreacted glycerin. The obtained fraction was concentrated to obtain polyglycerin 2.

[0051] Polyglycerol Production Example 3 100g of diglycerin and an alkali catalyst were added to a three-neck flask equipped with a Dimroth and a stirrer, and the temperature was raised to 140°C. 19.56g of glycerin triglycidyl ether was added dropwise at a rate of 10g / hr, and the reaction was continued for another hour after completion of the addition. The mixture was then passed through an ion exchange resin column to remove unreacted diglycerin. The obtained fraction was concentrated to obtain polyglycerin 3.

[0052] Polyglycerol Production Example 4 100g of diglycerin and an alkali catalyst were added to a three-neck flask equipped with a Dimroth and a stirrer, and the temperature was raised to 140°C. 39.13g of glycerin triglycidyl ether was added dropwise at a rate of 10g / hr, and the reaction was continued for another hour after completion of the addition. The mixture was then passed through an ion exchange resin column to remove unreacted diglycerin. The obtained fraction was concentrated to obtain polyglycerin 4.

[0053] Polyglycerol Production Example 5 100g of diglycerin and an alkali catalyst were added to a three-neck flask equipped with a Dimroth and a stirrer, and the temperature was raised to 140°C. 78.26g of glycerin triglycidyl ether was added dropwise at a rate of 10g / hr, and the reaction was continued for another hour after completion of the addition. The mixture was then passed through an ion exchange resin column to remove unreacted diglycerin. The obtained fraction was concentrated to obtain polyglycerin 5.

[0054] Polyglycerol Production Example 6 100g of glycerin and an alkali catalyst were added to a three-neck flask equipped with a Dimroth and a stirrer, and the temperature was raised to 140°C. 141.3g of glycerin triglycidyl ether was added dropwise at a rate of 10g / hr, and the reaction was continued for another hour after completion of the addition. The mixture was then passed through an ion exchange resin column to remove unreacted glycerin. The obtained fraction was concentrated to obtain polyglycerin 6.

[0055] Polyglycerin 7, 8 In addition, "Polyglycerin #750" manufactured by Sakamoto Pharmaceutical Industry Co., Ltd. was used as polyglycerin 7, and "Polyglycerin #500" manufactured by Sakamoto Pharmaceutical Industry Co., Ltd. was used as polyglycerin 8.

[0056] Polyglycerol Production Example 9 100g of glycerin and an alkali catalyst were added to a three-neck flask equipped with a Dimroth and a stirrer, and the temperature was raised to 120°C. 28.26g of glycerin triglycidyl ether was added dropwise at a rate of 10g / hr, and the reaction was continued for another hour after the completion of the addition. The mixture was then passed through an ion exchange resin column twice to remove as much unreacted glycerin as possible. The obtained fraction was concentrated to obtain polyglycerin 9.

[0057] Polyglycerol Production Examples 10-13 Polyglycerins 10 to 13 were prepared by adding glycerin or diglycerin to polyglycerin 9. The contents of glycerin or diglycerin are shown in Table 1.

[0058] <Measurement of branched glycerol ratio and number of branched glycerols per molecule> The ratio of branched glycerol and the number of branched glycerols per molecule were calculated by 13C-NMR as follows. The results are shown in Table 1. As a representative example of 13C-NMR spectra, the 13C-NMR spectrum of polyglycerol 1 is shown in Figure 1. Pretreatment: Dissolve 200 mg of polyglycerin in 0.6 mL of heavy water. Equipment used: 800MHz 13C-NMR, JEOL Ltd., "JNM-ECZ800R" Number of times accumulated: 256 Measurement conditions: Temperature 30°C, measurement sequence single pulse 1H decoupling, pulse repetition time 7 seconds, acetone measured as standard peak (δ: 30.89 ppm) Peak ranges used for integration: Total Integrals(TI):60.0-83.0ppm Dendritic (D): 76.5-80.0 ppm

[0059] How to calculate the branched glycerol ratio TI is the integral value of all carbon atoms involved in polyglycerol, and D is the integral value of secondary carbon atoms involved in branched glycerol. The proportion (%) of branched glycerol is calculated from the integral values ​​of each peak above using the following formula: Ratio of branched glycerol (%) = (D × 3 / TI) × 100

[0060] How to calculate the number of branched glycerol units per molecule The number of branched glycerols per polyglycerol molecule is calculated by the following formula: Number of branched glycerols per molecule = (D × 3 / TI) × average degree of polymerization

[0061] <Measurement of glycerin and diglycerin content> The content of glycerin and diglycerin in polyglycerin was measured by converting polyglycerin into a derivative by trimethylsilylation, and then isolating and quantifying the polyglycerin derivative by GC (gas chromatography). The results are shown in Table 1. Equipment used: GC-14B (Shimadzu Corporation) Column: OL-17 (50% phenylmethyl silicone, GL Sciences Inc.) Column size: 0.5m x 3mm Measurement temperature: 100→300℃ Heating rate: 10℃ / min

[0062] [Table 1]

[0063] Preparation of polyglycerol fatty acid esters Examples 1 to 18, Comparative Examples 1 to 10 As shown in Tables 2 to 4, polyglycerol fatty acid esters were prepared in each of the Examples and Comparative Examples. The preparation method of Example 1 will be described in more detail as a representative example. 32.4 g of polyglycerol 1 obtained in Polyglycerol Production Example 1, 7.6 g of lauric acid, and an alkali catalyst were added to a four-neck flask equipped with a stirrer, and an esterification reaction was carried out at 250°C. The reaction was continued until the acid value of the reaction product became 0.5 or less, and the polyglycerol fatty acid ester of Example 1 was obtained. Other Examples and Comparative Examples were also prepared in the same manner. In Examples 16 to 18 and Comparative Examples 5, 7, and 8, the esterification reaction was carried out at 260°C. The HLB of the polyglycerol fatty acid ester can be adjusted by changing the ratio of polyglycerol to fatty acid. For example, in the case of Example 12 (HLB 13.8), 70 g of polyglycerin and 30 g of lauric acid were reacted, in the case of Example 13 (HLB 17.6), 88.1 g of polyglycerin and 11.9 g of lauric acid, and in the case of Example 14 (HLB 18.6), 93 g of polyglycerin and 7 g of lauric acid were reacted to prepare the copolymer.

[0064] <Test Example 1: Solubilization Test 1> 0.5 g of the polyglycerol fatty acid ester of Examples 1 to 16 and Comparative Examples 1 to 8 was mixed with an appropriate amount of lavender oil at 50°C, and the mixture was poured into 100 g of water at 70°C while stirring. After stirring for 5 minutes and cooling to 25°C, the transmittance was measured at a wavelength of 650 nm using a spectrophotometer (Shimadzu Corporation: UV-260). The amount of lavender oil at which the transmittance was 98% or more was defined as the solubilized amount. The results are shown in Tables 2 and 3.

[0065] [Table 2]

[0066] [Table 3]

[0067] <Test Example 2: Solubilization Test 2> 0.5 g of the polyglycerol fatty acid esters of Examples 16 to 18 and Comparative Examples 8 to 10 and an appropriate amount of cetyl ethylhexanoate were mixed at 50°C and poured into 100 g of water at 70°C while stirring. After stirring for 5 minutes and cooling to 25°C, the transmittance was measured at a wavelength of 650 nm using a spectrophotometer (Shimadzu Corporation: UV-260). The amount of cetyl ethylhexanoate when the transmittance was 98% or more was taken as the solubilized amount. The results are shown in Table 4.

[0068] <Test Example 3: Solubilization Test 3> 0.5 g of the polyglycerol fatty acid ester of Examples 16 to 18 and Comparative Examples 8 to 10 and an appropriate amount of phytosqualane were mixed at 50°C and added to 100 g of water at 70°C while stirring. After stirring for 5 minutes and cooling to 25°C, the transmittance was measured at a wavelength of 650 nm using a spectrophotometer (Shimadzu Corporation: UV-260). The amount of phytosqualane at which the transmittance was 98% or more was taken as the solubilized amount. The results are shown in Table 4.

[0069] [Table 4]

[0070] Details of the components listed in Tables 2 to 4 are shown below. Lavender oil: Ogawa Fragrance Co., Ltd. Cetyl ethylhexanoate: Kao Corporation Phytosqualane: manufactured by SOPHIM

[0071] As shown in Tables 2 to 4, all of Examples 1 to 18, which used the polyglycerol fatty acid esters of the present invention, had excellent solubilizing power for poorly water-soluble substances compared to Comparative Examples 1, 2, 4 to 10, which were prepared using commercially available polyglycerols 7 and 8, and Comparative Example 3, which had a low HLB.

[0072] Preparation of lotion A lotion was prepared by a conventional method using the polyglycerol fatty acid ester of the present invention and the composition shown in Table 5. The transmittance of the obtained lotion was measured in the same manner as in Test Examples 1 to 3. The results are shown in Table 5. When the lotion was applied to the skin, it had a suitable feel with little stickiness when it dried.

[0073] [Table 5]

[0074] Preparation of Food and Beverage Composition 1 7.8 g of glycerin as a polyhydric alcohol was added with 1 g of ion-exchanged water and 0.4 g of the polyglycerol fatty acid ester of Example 14, and dissolved by heating at 65° C. 0.8 g of extracted tocopherol was added as a poorly water-soluble substance (antioxidant), and finely emulsified at a pressure of 150 MPa in a homomixer to obtain composition 1 for food and beverage.

[0075] Preparation of Food and Beverage Composition 2 A food and beverage composition 2 was obtained in the same manner as above, except that 0.4 g of the polyglycerol fatty acid ester of Comparative Example 7 was added instead of the polyglycerol fatty acid ester of Example 14.

[0076] <Test Example 4: Solubilization Test 4> The transmittance of 0.1 g of the composition for food or beverage solubilized in 100 g of water was measured at a wavelength of 650 nm using a spectrophotometer (Shimadzu Corporation: UV-260). The results are shown in Table 6.

[0077] <Test Example 5: Particle size measurement> The average particle size of 0.1 g of the composition for food or beverage was solubilized in 100 g of water and measured using a particle size distribution analyzer (L-230, manufactured by Beckman Coulter, Inc.). The results are shown in Table 6.

[0078] [Table 6]

[0079] As shown in Table 6, the composition for food and beverage using the polyglycerol fatty acid ester of Example 14 has high transmittance when solubilized in water, and is clearly excellent in appearance transparency. In addition, since the average particle size of the poorly water-soluble substance is small, it can be said that the composition is also excellent in long-term stability. [Industrial Applicability]

[0080] INDUSTRIAL APPLICABILITY According to the present invention, a polyglycerol fatty acid ester having excellent solubilizing power for poorly water-soluble substances can be provided, and can be suitably used in applications such as cosmetics, food and beverages.

Claims

1. A polyglycerol fatty acid ester, which is an ester of a polyglycerol having a ratio of branched glycerol groups represented by the following formula (1) of 14 to 60% and an average degree of polymerization of 5 to 25 and a fatty acid having 6 to 22 carbon atoms, wherein the fatty acid is lauric acid, myristic acid, oleic acid, stearic acid, or isostearic acid, and has an HLB of 13 or more and 19 or less. 【Chemistry 1】

2. 2. The polyglycerol fatty acid ester according to claim 1, wherein the total content of glycerol and diglycerol in the polyglycerol is 0.01 to 30% by mass.

3. 2. The polyglycerol fatty acid ester according to claim 1, wherein the number of the branched glycerol groups per one polyglycerol molecule is 1 to 15 on average.

4. 2. The polyglycerol fatty acid ester of claim 1, wherein the fatty acid is lauric acid, myristic acid, or oleic acid.

5. A solubilizer comprising an ester of a polyglycerol having a ratio of branched glycerol groups represented by the following formula (1) of 14 to 60% and an average degree of polymerization of 5 to 25 and a fatty acid having 6 to 22 carbon atoms, the fatty acid being lauric acid, myristic acid, oleic acid, stearic acid, or isostearic acid, and having an HLB of 13 or more and 19 or less. 【Chemistry 2】

6. A cosmetic composition comprising: an ester of polyglycerol having a ratio of branched glycerol groups represented by the following formula (1) of 14 to 60% and an average degree of polymerization of 5 to 25 and a fatty acid having 6 to 22 carbon atoms, the fatty acid being lauric acid, myristic acid, oleic acid, stearic acid, or isostearic acid and having an HLB of 13 or more and 19 or less; and a poorly water-soluble substance having a solubility in water of 0.1% or less. 【Chemistry 3】

7. A cosmetic comprising the polyglycerol fatty acid ester according to any one of claims 1 to 4 or the cosmetic composition according to claim 6.

8. A composition for food and beverage, comprising: an ester of polyglycerol having a ratio of branched glycerol groups represented by the following formula (1) of 14 to 60% and an average degree of polymerization of 5 to 25, and a fatty acid having 6 to 22 carbon atoms, the fatty acid being lauric acid, myristic acid, oleic acid, stearic acid, or isostearic acid, and having an HLB of 13 or more and 19 or less; and a poorly water-soluble substance having a solubility in water of 0.1% or less. 【Chemistry 4】

9. A food or drink comprising the polyglycerol fatty acid ester according to any one of claims 1 to 4 or the composition for food or drink according to claim 8.

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