JP5288407B2 - O / W emulsified composition of oil-soluble substance - Google Patents

Description

  The present invention relates to an O / W emulsion composition of an oil-soluble substance. More specifically, the present invention relates to an emulsified composition of an oil-soluble substance that has good emulsion stability, is less likely to cause separation of the oil-soluble substance, and is easily dispersed uniformly in water.

  Oil-soluble substances include various useful ingredients such as fats and oils, pigments, vitamins, functional substances, and fragrances, and the range of use covers various fields such as foods, cosmetics, pharmaceuticals, and quasi drugs.

  However, the oil-soluble substance is inconvenient to handle as it is and has a problem of low absorbability to living bodies. Oil-soluble substances generally have very low solubility in water, and are difficult to use as a stable aqueous solution by being uniformly dispersed or solubilized in water. Therefore, when using an oil-soluble substance, a method of dissolving and diluting with oil or the like, or suspending and emulsifying is employed. Therefore, a method for stably solubilizing an oil-soluble substance in an aqueous solvent is required.

As a general method for solubilizing an oil-soluble substance in an aqueous solvent, the oil-soluble substance is dissolved in an oily solvent such as edible oil, and this is mixed with an aqueous solvent in which a surfactant is dissolved in advance to emulsify. A method can be mentioned. Various compounds have been conventionally used as emulsifiers or solubilizers. For example, lecithin, saponin, gum arabic, gelatin, modified starch, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester (polysorbate) ), Polyglycerin fatty acid ester, polyglycerin condensed ricinoleic acid ester and the like are known.

  Many oil-soluble substances are difficult to obtain a stable emulsion even when emulsifiers are used. In order to emulsify them, emulsification over time is possible even for substances that are relatively easy to emulsify. Various emulsifier combinations have been devised to improve stability. For example, an oily fragrance or a vegetable oil / fat is prepared by drinking Claudia saponin alone or in combination with Quillaja saponin and polyglycerin fatty acid ester (Patent Document 1). A method for producing a stable emulsified preparation after adding a beverage (Patent Document 2), using a hardly soluble ceramide in combination with a polyglycerol fatty acid ester having 8 to 10 carbon atoms and a polyglycerol fatty acid ester having 12 to 18 carbon atoms. Emulsified and emulsified (Patent Document 3), natural essential oil and vegetable oil combined with chicle gum and other emulsifiers (such as gum arabic and sucrose fatty acid ester) to form an emulsified preparation (Patent Document 4), citrus oils and essential oils Varada and other emulsifiers (glycerin fatty acid ester or sucrose ester) A method of emulsifying in combination (Patent Document 5), a method of converting a ceramide, which is a poorly soluble substance, into an oil-in-water emulsion using a phospholipid derivative, a fatty acid dextrin and a polyglycerin fatty acid ester (Patent Document 6), etc. It is done. In addition to the combination of emulsifiers, for example, a solubilized preparation in which vitamin A is emulsified with polysorbate 80 or polyoxyethylene hydrogenated castor oil 60 (Patent Document 7), and purified polyglycerin fatty acid ester as an emulsifier is used. Discloses a method for improving the stability of a beverage to which an emulsified composition or an emulsified preparation is added (Patent Document 8).

  As a diluent for an oil-soluble substance, medium chain fatty acid triglyceride (MCT) is often used. MCT is tasteless and odorless, has high oxidation stability, is highly soluble in various oil-soluble substances, and is easy to emulsify. On the other hand, ordinary vegetable oils such as rice salad oil are generally disclosed as general examples of diluents of oil-soluble substances, but are actually used because they are extremely difficult to emulsify. Is hardly found. In addition, it is generally difficult to obtain a stable emulsified preparation for fragrances with a high proportion of esters, and therefore it is often emulsified using a diluent such as MCT. there were.

JP-A-63-98369 JP-A-63-219357 JP 2003-113393 A JP-A 48-68756 Japanese Patent Laid-Open No. 51-130561 JP 2008-156342 A JP-A-11-236331 JP 2007-116930 A

  The problem to be solved by the present invention is that O / W type emulsification of vegetable oils such as rice salad oil and perfume compounds containing a large amount of esters, etc. An object of the present invention is to provide an emulsified composition having good emulsification stability, easily dispersible uniformly in water, and stable over time after being dispersed in water.

  There are various oil-soluble substances that are difficult to emulsify. In order to solve the above problems, the present inventors have established a stable emulsion formulation in rice salad oil, which is extremely common as an oil-soluble substance that is difficult to emulsify. If it was obtained, we thought that it could be applied to other poorly emulsifiable oil-soluble substances, and conducted diligent research on the selection and combination of emulsifiers. For example, polyglycerin fatty acid ester is generally used as an emulsifier for various oil-soluble substances because of its excellent emulsifying power, but when a rice salad oil was emulsified, a stable emulsion could not be obtained. In addition, it was confirmed that even when polyoxyethylene sorbitan fatty acid ester and kiraya saponin, which are considered to have strong emulsifying power, were used as individual emulsifiers, the emulsified particles became larger with time and separated. .

  However, surprisingly, when emulsifying rice salad oil using both polyoxyethylene sorbitan fatty acid ester and Kirayasaponin as emulsifiers as an emulsifier, the emulsification stability of the emulsion was good, and the emulsified particles gradually changed over time. In addition, it was possible to obtain an emulsified composition that was not greatly increased and that was very dispersible in water and that was stable over time after being dispersed in water.

  In addition, in the prior art, many emulsifiers are listed, and many of them include polyoxyethylene sorbitan fatty acid ester and kiraya saponin. I can't find the technology.

Thus, the present invention is a method for producing an O / W emulsion composition, comprising: (A) 0.5 to 50% by mass of an oil-soluble substance, (B) 0.05 to 5% by mass of Kirayasaponin, (C ) 0.01% by mass to 10% by mass of polyoxyethylene sorbitan fatty acid ester, and (D) 10% by mass to 90% by mass of one or more selected from water, monohydric alcohol and polyhydric alcohol , ) (B) Quillaja saponin is mixed and dissolved in an aqueous phase composed of one or more selected from water, monohydric alcohol and polyhydric alcohol, and separately from this, (A) oil-soluble substance, (C) poly The present invention provides a method for producing an O / W type emulsion composition, which comprises dissolving oxyethylene sorbitan fatty acid ester, mixing both, and emulsifying .

  The oil-soluble substance O / W emulsified composition of the present invention has good emulsion stability, and the emulsion particles do not increase over time or cause separation. Moreover, since it is easy to disperse | distribute uniformly to water and is stable over time after disperse | distributing to water, it has the outstanding effect that it is easy to use for a drink and a foodstuff.

  The oil-soluble substance used in the present invention is not particularly limited, and various oils and fats, oil-soluble pigments, vitamins, functional substances, fragrances and the like can also be used. Examples of oils and fats include vegetable oils such as soybean oil, rice oil, rice salad oil, sesame oil, peanut oil, corn oil, rapeseed oil, coconut oil, palm oil, and hardened oils thereof; beef fat, pork fat, chicken oil, etc. Animal fats and oils and their hardened oils; medium chain fatty acid triglycerides (MCT) and the like can be mentioned, and examples of oil-soluble pigments include oil-soluble natural pigments such as β-carotene, paprika pigment, anato pigment and chlorophyll Examples of oil-soluble vitamins include liver oil, vitamin A, vitamin A oil, vitamin D3, vitamin B2 butyrate ester, vitamin E, vitamin F, vitamin K, and the like. , Docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), DHA and / or EPA-containing fish oil, linoleic acid γ-linolenic acid, α-linolenic acid, evening primrose oil, borage oil, lecithin, octacosanol, rosemary extract, sage extract, γ-oryzanol, β-carotene, palm carotene, perilla oil, etc. Can be used, for example, any of natural extracts such as various natural essential oils, extracts, oleoresin, resinoids, synthetic fragrance compounds, or blended fragrances prepared from these. Examples of natural essential oils include citrus essential oils such as orange, lemon, lime, and grapefruit, plant essential oils such as flower essential oil, peppermint oil, spearmint oil, spice oil, and natural product extracts such as, for example, Examples include oily extracts such as cola nut extract, coffee extract, vanilla extract, cocoa extract, tea extract, spice extract, resinoids, and oleoresins of these, and synthetic fragrance compounds include For example, "Survey on the use of food fragrance compounds in Japan" (FY 2000 Health and Welfare Research Report; Japan Fragrance Industry Association published in March 2001), "Synthetic fragrance chemistry and product knowledge" (March 22, 2005) Amendment revised edition published by Motoichi Into, Chemical Industry Daily) Synthesis of at least one or more selected from the group of esters, alcohols, aldehydes, ketones, phenols, ethers, lactones, hydrocarbons, nitrogen-containing and / or sulfur-containing compounds and acids Examples include fragrances. Among these, examples of substances that are particularly difficult to emulsify include rice salad oil, rice oil, soybean oil, sesame oil, corn oil, vitamin A, vitamin K, octacosanol, ceramide, and esters (fragrance).

  The blending amount of the oil-soluble substance used in the present invention can be 0.5 to 50% by mass, preferably 5 to 35% by mass in the emulsion composition. The blending amount of the oil-soluble substance is preferably as much as possible in consideration of the cost of transporting the emulsified preparation and the storage location, but when the oil-soluble substance is more than 50% by mass, the uniformity of the emulsification mixing is insufficient. Since it is easy to become, it is not preferable. In addition, when the blending ratio of the oil-soluble substance in the emulsion composition is less than 0.5% by mass, the amount of the emulsion composition added for blending the amount of the oil-soluble component required for the final product increases. It is uneconomical.

  The emulsifier used in the present invention is characterized in that both quillaja saponin and polyoxyethylene sorbitan fatty acid ester are used. By using both of these in combination, the emulsion has good emulsification stability, the emulsified particles do not increase over time, do not cause separation, and are easily dispersed uniformly in water. Thus, an emulsion that is stable over time can be obtained even after dispersion.

  Kirayasaponin is also called Kiraya extract and Kirayanin, and is listed as "Kiraya extract" in the 7th edition Food Additives Official Document. Quillaja saponin is a glycoside component contained in the bark of the Rosaceae plant Quillaia saponaria Molina, and is a natural interface composed mainly of several saponins consisting of triterpene saponins whose main component is aglycone. It is an active substance. Kiraya grows naturally in South America such as Chile, Bolivia, and Peru. Kirayasaponin not only has emulsifying power but also strong foaming ability, and locally, Kiraya is also called a soap tree, and its sap is used as a shampoo. Quillaja saponin is highly hydrophilic, has a strong surface tension reducing ability, and easily dissolves in water transparently. Therefore, it can be said that it is a surfactant having a high HLB. Moreover, since the emulsifying power is strong, it can also be used for transparent emulsification of oil-soluble substances (which appears transparent to the naked eye when finely emulsified).

  Quillaja saponin can be extracted from quinaya bark using water, lower alcohol, or a mixture thereof, but commercially available quillaja saponins can also be used. Examples of commercially available Kirayasaponins include Kirayanin S-100, Kirayanin C-100, and Kirayanin P-20 (manufactured by Maruzen Pharmaceutical Co., Ltd.).

  The amount of Kirayasaponin used in the present invention is 0.05 mass% to 5 mass%, preferably 0.5 mass% to 3 mass%, more preferably 1 mass% to 2 mass% in the emulsion composition. It can be illustrated. If the amount of Quillaja saponin is less than 0.05% by mass, a good emulsion may not be obtained, and even if it is used in an amount of more than 5% by mass, the emulsification effect is not so high.

  As described above, Kirayasaponin has a strong emulsifying power and can be used for transparent emulsification of oil-soluble substances. However, as a single emulsifier, it is not sufficient to emulsify rice salad oil. When rice salad oil is emulsified using Quillaja saponin alone as an emulsifier, the particle size of the emulsion increases with time and tends to separate over time.

  Polyoxyethylene sorbitan fatty acid ester, also called polysorbate, is a product in which polyoxyethylene is added to sorbitan fatty acid ester, and it exists in various combinations depending on the number of moles of polyoxyethylene added, the constituent fatty acid species of sorbitan fatty acid ester, and the degree of esterification To do. It has been used for a long time as an emulsifier for cosmetics and detergents, and as an emulsifier for foods overseas. In Japan, some polysorbates were approved as food additives in April 2008 and can be used for food. became.

  The polyoxyethylene sorbitan fatty acid ester that can be used in the present invention is not limited to the number of added moles, the type of fatty acid, and the degree of esterification, but the number of added ethylene units (degree of polymerization) is sorbitan fatty acid. The total number of oxyethylene units added to a plurality of hydroxyl groups of the ester is 1 to 100, more preferably 5 to 30, and still more preferably 15 to 25. The fatty acid species constituting the ester is preferably a saturated or unsaturated fatty acid having 8 to 22, more preferably 12 to 18, more preferably stearic acid, oleic acid, palmitic acid or lauric acid. The degree of esterification is not particularly limited and may be any of various ester forms such as monoesters, diesters, triesters, etc., but from the viewpoint of emulsion stability, safety to the environment, etc. Is particularly preferred. As preferable specific examples, the monoester type includes polysorbate 80 (polyoxyethylene sorbitan monooleate, 20EO), polysorbate 60 (polyoxyethylene sorbitan monostearate, 20EO), polysorbate 40 (polyoxyethylene sorbitan monopalmitate, 20EO). ), Polysorbate 20 (polyoxyethylene sorbitan monolaurate, 20EO), and the triester type is polysorbate 65 (polyoxyethylene sorbitan tristearate, 20EO).

  The compounding amount of the polyoxyethylene sorbitan fatty acid ester used in the present invention is preferably 0.01% by mass to 10% by mass, preferably 0.1% by mass to 5% by mass, and more preferably 0% in the emulsion composition. And 5 mass% to 3 mass% can be exemplified. When the amount of the polyoxyethylene sorbitan fatty acid ester is less than 0.01% by mass, a good emulsion may not be obtained, and even if it is used in an amount of more than 10% by mass, the emulsifying effect is not so high.

  Polyoxyethylene sorbitan fatty acid ester has a strong emulsifying power, but as a single emulsifier, it is not sufficient for emulsifying rice salad oil. The emulsion obtained when emulsifying rice salad oil using polyoxyethylene sorbitan fatty acid ester alone as an emulsifier is relatively good in the emulsified state immediately after emulsification, but the particle size of the emulsion increases over time, and eventually There is a tendency to separate.

  The present invention is characterized in that both of these alone are used in combination with Kirayasaponin and polyoxyethylene sorbitan fatty acid ester, which are not necessarily suitable for emulsifying rice salad oil. In the present invention, only when both are used in combination, the emulsion has good emulsification stability, the emulsified particles do not increase over time, do not cause separation, and are uniformly dispersed in water. It was possible to obtain an emulsion of rice salad oil that was easy to do and stable over time after being dispersed in water. The ratio of Quillaja saponin and polyoxyethylene sorbitan fatty acid ester is, for example, in the range of 50: 1 to 1: 5, preferably 20: 1 to 1: 2, more preferably 5: 1 to 1: 1 in terms of mass. It can be illustrated.

  In this invention, 1 or more types chosen from water, a monohydric alcohol, and a polyhydric alcohol are used in an emulsion composition. Polyoxyethylene sorbitan fatty acid ester has a high HLB and is easily miscible with oil-soluble substances. However, as described above, Kirayasaponin is a surfactant with high hydrophilicity and high HLB, so it is miscible with oil-soluble substances. In order to dissolve, a water-soluble medium is required. Examples of the monohydric alcohol and polyhydric alcohol that can be used in the present invention include ethanol, propylene glycol, glycerin, sorbitol, maltitol, starch syrup, reduced starch syrup, glucose, fructose, sucrose, maltose, liquid sugar, and the like. Examples thereof include saccharides and a mixture of two or more thereof. The compounding quantity of 1 or more types chosen from the water and / or polyhydric alcohol used by this invention is 10 mass%-90 mass% in an emulsion composition, Preferably it is 20 mass%-80 mass%, More preferably, it is 30 mass. % -70 mass% can be illustrated.

  In the present invention, other water-soluble raw materials can be blended as long as emulsification is not hindered. Examples of other components include water-soluble dyes, water-soluble functional substances, water-soluble antioxidants, emulsifiers other than those described above, thickeners, and stabilizers.

If the preparation method of the O / W type emulsion composition of this invention is illustrated, for example, Kirayasaponin is mixed and dissolved in an aqueous phase such as liquid sugar, and separately from this, polyoxyethylene sorbitan fatty acid ester is added to rice salad oil. Is mixed, and both are mixed and emulsified using an emulsifier such as TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) at a rotational speed of about 5000 rpm to about 10,000 rpm for about 5 minutes to about 20 minutes. Further, in place of the TK-homomixer (made by Tokushu Kika Kogyo Co., Ltd.), any emulsifier such as a conventionally known high-pressure homogenizer or colloid mill can be used as long as it has an equal or higher emulsifying capacity. It may be processed .

  The O / W type emulsion composition of rice salad oil thus obtained has good emulsion stability, and the emulsion particles do not increase over time or cause separation. Moreover, since it is easy to disperse | distribute uniformly in water, it is easy to use for a drink and a foodstuff, and the temporal stability after addition is also favorable.

Examples of foods and drinks that can be blended with the O / W emulsion composition of the present invention include beverages, seasonings, dressings, frozen desserts, desserts, retort foods, processed meat foods, processed fishery foods, and the like. . Although the usage-amount of the emulsification fragrance | flavor mix | blended with these food / beverage products changes with kinds, forms, etc. of food / beverage products, generally it is about 0.001 mass part-about 0.05 mass part with respect to 1 mass part of food / beverage products. Can be used within the range.
The following examples further illustrate the present invention.

Example 1
50 g of Kirayanin C-100 (manufactured by Maruzen Pharmaceutical Co., Ltd .: containing 25% Kiraya extract) is mixed and dissolved in 845 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. Separately from this, 5 g of Emazole L-120V (polysorbate 20, manufactured by Kao Corporation) is mixed and dissolved in 100 g of rice salad oil to obtain an oil phase part. The water phase part and the oil phase part were mixed and stirred at 6000 rpm for 10 minutes using a TK-homomixer (made by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of rice salad oil (Invention product 1: Contains 10% rice salad oil).

Example 2
In Example 1, except that 5 g of Emazole S-120V (Polysorbate 60, manufactured by Kao Corporation) was used instead of 5 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation), the same operation as in Example 1 was performed. An emulsion composition of rice salad oil (1000 g) was obtained (invention product 2: containing 10% rice salad oil).

Example 3
In Example 1, except that 5 g of Emazole O-120V (Polysorbate 80, manufactured by Kao Corporation) was used instead of 5 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation), the same operation as in Example 1 was performed. 1000 g of an emulsified composition of rice salad oil was obtained (product of the present invention 3: containing 10% rice salad oil).

Comparative Example 1 (using Kirayasaponin as an emulsifier)
50 g of Kirayanin C-100 (manufactured by Maruzen Pharmaceutical Co., Ltd .: containing 25% Kiraya extract) is mixed and dissolved in 850 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. This was mixed with 100 g of rice salad oil and stirred at 6000 rpm for 10 minutes using a TK-homomixer (manufactured by Koki Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of rice salad oil (comparative product 1: rice salad oil 10). % Content).

Comparative Example 2 (using polysorbate as an emulsifier)
20 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation) is mixed and dissolved in 100 g of rice salad oil to obtain an oil phase part. This was mixed with 880 g of isomerized liquid sugar (Bx75 °) and stirred for 10 minutes at 6000 rpm using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of a rice salad oil emulsified composition (comparative product). 2: Contains 10% rice salad oil).

Comparative Example 3 (using polysorbate as an emulsifier and ethanol and glycerin in the aqueous phase)
100 g of ethanol, 400 g of glycerin and 100 g of water are mixed and dissolved in 300 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation), 100 g of rice salad oil is added thereto, and 6000 rpm using a TK-homomixer (manufactured by Koki Kogyo Co., Ltd.). Was stirred for 10 minutes to obtain 1000 g of an emulsified composition of rice salad oil (Comparative product 3: containing 10% of rice salad oil).

Comparative Example 4 (using polyglycerin fatty acid ester as an emulsifier)
50 g of decaglycerin monooleate (trade name: Decaglyn 1-OV, manufactured by Nikko Chemicals) is mixed and dissolved in 850 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. To this, 100 g of rice salad oil was mixed and stirred at 6000 rpm for 10 minutes using a TK-homomixer (made by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of rice salad oil (Comparative product 4: Rice salad oil 10). % Content).

Comparative Example 5 (using sucrose fatty acid ester as an emulsifier)
To 860 g of isomerized liquid sugar (Bx75 °) and 30 g of water, 10 g of sucrose stearate (trade name: Sugar Ester DK-SS, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) is added and dissolved to obtain an aqueous phase. This was mixed with 100 g of rice salad oil and stirred at 6000 rpm for 10 minutes using a TK-homomixer (made by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of rice salad oil (Comparative product 5: Rice salad oil 10 % Content).

Comparative Example 6 (using gum arabic as an emulsifier)
500 g of gum arabic aqueous solution (concentration 30%) is sterilized at 85 ° C. to 95 ° C. for 15 minutes, cooled to 40 ° C. or less, dissolved by adding 400 g of glycerin to obtain an aqueous phase part. To this, 100 g of rice salad oil was mixed and stirred at 6000 rpm for 10 minutes using a TK-homomixer (made by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of rice salad oil (Comparative product 6: Rice salad oil 10). % Content).

Comparative Example 7 (using polyglycerin fatty acid ester and polysorbate as an emulsifier)
50 g of decaglycerin monooleate (trade name: Decaglyn 1-OV, manufactured by Nikko Chemicals) is mixed and dissolved in 845 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. Separately from this, 5 g of Emazole O-120V (polysorbate 80, manufactured by Kao Corporation) is mixed and dissolved in 100 g of rice salad oil to obtain an oil phase part. The water phase part and the oil phase part were mixed and stirred at 6000 rpm for 10 minutes using a TK-homomixer (made by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of rice salad oil (Comparative product 7: Rice Contains 10% salad oil).

Comparative Example 8 (using gum arabic and polysorbate as emulsifier)
After sterilizing 500 g of gum arabic aqueous solution (concentration 30%) at 85 ° C. to 95 ° C. for 15 minutes, the solution is cooled to 40 ° C. or less and dissolved by adding 395 g of glycerin to obtain an aqueous phase part. Separately from this, 5 g of Emazole O-120V (polysorbate 80, manufactured by Kao Corporation) is mixed and dissolved in 100 g of rice salad oil to obtain an oil phase part. The water phase part and the oil phase part were mixed and stirred at 6000 rpm for 10 minutes using a TK-homomixer (made by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of rice salad oil (Comparative product 8: Rice Contains 10% salad oil).

Comparative Example 9 (using polyglycerin fatty acid ester and Quillaja saponin as an emulsifier)
800 g of isomerized liquid sugar (Bx75 °) mixed with 50 g of decaglycerin monooleate (trade name: Decaglyn1-OV, manufactured by Nikko Chemicals Co., Ltd.) and 50 g of kirayanin C-100 (manufactured by Maruzen Pharmaceutical Co., Ltd .: containing 25% kiraya extract) Dissolve to make the aqueous phase. This was mixed with 100 g of rice salad oil and stirred at 6000 rpm for 10 minutes using a TK-homomixer (made by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of rice salad oil (Comparative product 9: Rice salad oil 10 % Content).

Example 4
Inventive products 1 to 3 and comparative products 1 to 9 were subdivided into 30-ml sample bottles by 30 g and subjected to a storage test at 5 ° C., 20 ° C. and 50 ° C. for 1 week, and the state of emulsification was observed with the naked eye. Further, the emulsified state was further observed with an optical microscope, and the emulsified state was determined. The results are shown in Table 1.

  As shown in Table 1, the product 1 of the present invention in which Kirayasaponin and polysorbate were used in combination as an emulsifier gave a stable emulsion immediately after emulsification, and the emulsified state was stable even after storage at 50 ° C. for 1 week.

  On the other hand, Comparative Product 1 using Kirayasaponin alone, which is one of the two types of emulsifiers used in the present invention, appeared to be in a good emulsified state immediately after emulsification, but was observed with an optical microscope. However, the particle size was large. In addition, oil separation was observed at 5 ° C., 20 ° C. and 50 ° C. after storage for 1 week, and emulsion breakage was observed.

Further, Comparative Product 2 and Comparative Product 3 using polysorbate, which is the other emulsifier of the two types of emulsifiers used in the present invention, showed oil floating immediately after emulsification, and were in poor condition.
Comparative products 4 and 5 use polyglycerin fatty acid ester and sucrose fatty acid ester, which are widely used emulsifiers because of their excellent emulsifying power, but those using either emulsifier floated immediately after emulsification. Was seen and the condition was poor.

  Comparative product 6 was obtained by using gum arabic as an emulsifier, but oil floating was observed immediately after emulsification, and the condition was poor.

  Moreover, the comparison product 7 combining polysorbate and polyglycerin fatty acid ester which is another emulsifier, the comparison product 8 combining gum arabic, and the combination using the product of the present invention, which are related to the combination of the product of the present invention. On the other hand, Comparative product 9 combining Kirayasaponin and polyglycerin fatty acid ester, which was one of the above, seemed to be in a good emulsified state immediately after emulsification, but when observed with an optical microscope, the particle size was large. In addition, oil separation was observed at 5 ° C., 20 ° C. and 50 ° C. after storage for 1 week, and emulsion breakage was observed.

Example 5
Inventive products 1 to 3 having good emulsification state in Example 4 were diluted with water by 0.1%, and the diluted solution was stored at 5 ° C. for 1 month. As a result, the emulsified state of the diluted solution was good, and no aggregation or coalescence of particles was observed even when observed with an optical microscope, and an extremely stable emulsified state was maintained.

Reference example 1
As an apple-like blended fragrance composition, a blended fragrance composition comprising the components shown in Table 2 below was prepared. In addition, ester compound content rate in a prescription is 87%.

Example 6 (using Kirayasaponin and polysorbate as emulsifiers)
50 g of Kirayanin C-100 (manufactured by Maruzen Pharmaceutical Co., Ltd .: containing 25% Kiraya extract) is mixed and dissolved in 845 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. Separately from this, 5 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation) is mixed and dissolved in 100 g of Reference Product 1 (Apple Blended Fragrance) to obtain an oil phase part. The water phase part and the oil phase part were mixed and stirred at 6000 rpm for 10 minutes using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an apple blended fragrance emulsion composition (Product 4 of the present invention). : Apple blended fragrance containing 10%).

Example 7
In Example 6, except that 5 g of Emazole S-120V (Polysorbate 60, manufactured by Kao Corporation) was used instead of 5 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation), the same operation as in Example 6 was performed, 1000 g of an emulsified composition of apple blended fragrance was obtained (invention product 5: containing 10% of apple blended fragrance).

Example 8
In Example 6, except that 5 g of Emazole O-120V (Polysorbate 80, manufactured by Kao Corporation) was used instead of 5 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation), the same operation as in Example 6 was performed, 1000 g of an emulsified composition of apple blended fragrance was obtained (invention product 6: containing 10% of apple blended fragrance).

Comparative Example 10 (using Kirayasaponin as an emulsifier)
50 g of Kirayanin C-100 (manufactured by Maruzen Pharmaceutical Co., Ltd .: containing 25% Kiraya extract) is mixed and dissolved in 850 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. This was mixed with 100 g of Reference Product 1 (Apple Blended Fragrance) and stirred at 6000 rpm for 10 minutes using TK-Homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsified composition of apple blended flavor ( Comparative product 10: containing 10% of apple blended fragrance).

Comparative Example 11 (using polysorbate as an emulsifier)
100 g of ethanol, 400 g of glycerin and 100 g of water are mixed and dissolved in 300 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation), and 100 g of Reference Product 1 (Apple Blended Fragrance) is added thereto, and TK-Homomixer (Special Machine Industries Co., Ltd.) The resulting mixture was stirred at 6000 rpm for 10 minutes to obtain 1000 g of an emulsified composition of apple blended fragrance (Comparative product 11: containing 10% of apple blended fragrance).

Comparative Example 12 (using polyglycerol fatty acid ester as an emulsifier)
50 g of decaglycerin monooleate (trade name: Decaglyn 1-OLV, manufactured by Nikko Chemicals) is mixed and dissolved in 850 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. This was mixed with 100 g of Reference Product 1 (Apple Blended Fragrance) and stirred at 6000 rpm for 10 minutes using TK-Homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsified composition of apple blended flavor ( Comparative product 12: containing 10% of apple blended fragrance).

Comparative Example 13 (using sucrose fatty acid ester as an emulsifier)
To 880 g of isomerized liquid sugar (Bx75 °), 20 g of sucrose stearate (trade name: Sugar Ester DK-SS, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) is added and dissolved to obtain an aqueous phase part. This was mixed with 100 g of Reference Product 1 (Apple Blended Fragrance) and stirred at 6000 rpm for 10 minutes using TK-Homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsified composition of apple blended flavor ( Comparative product 13: containing 10% of apple blended fragrance).

Comparative Example 14 (using gum arabic as an emulsifier)
500 g of gum arabic aqueous solution (concentration 30%) is sterilized at 85 ° C. to 95 ° C. for 15 minutes, cooled to 40 ° C. or less, dissolved by adding 400 g of glycerin to obtain an aqueous phase part. This was mixed with 100 g of Reference Product 1 (Apple Blended Fragrance) and stirred at 6000 rpm for 10 minutes using TK-Homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsified composition of apple blended flavor ( Comparative product 14: containing 10% of apple blended fragrance).

Comparative Example 15 (using polyglycerin fatty acid ester and polysorbate as an emulsifier)
50 g of decaglycerin monooleate (trade name: Decaglyn 1-OLV, manufactured by Nikko Chemicals) is mixed and dissolved in 845 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. Separately from this, 5 g of Emazole O-120V (Polysorbate 80, manufactured by Kao Corporation) is mixed and dissolved in 100 g of Reference Product 1 (Apple Blended Fragrance) to obtain an oil phase part. The water phase part and the oil phase part were mixed and stirred at 6000 rpm for 10 minutes using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an apple blended fragrance emulsion composition (Comparative Product 15: Containing 10% apple blended fragrance).

Comparative Example 16 (using gum arabic and polysorbate as emulsifier)
After sterilizing 500 g of gum arabic aqueous solution (concentration 30%) at 85 ° C. to 95 ° C. for 15 minutes, the solution is cooled to 40 ° C. or less and dissolved by adding 395 g of glycerin to obtain an aqueous phase part. Separately from this, 5 g of Emazole O-120V (Polysorbate 80, manufactured by Kao Corporation) is mixed and dissolved in 100 g of Reference Product 1 (Apple Blended Fragrance) to obtain an oil phase part. The water phase part and the oil phase part were mixed and stirred for 10 minutes at 6000 rpm using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an apple blended fragrance emulsion composition (Comparative Product 16: Containing 10% apple blended fragrance).

Comparative Example 17 (using polyglycerin fatty acid ester and Quillaja saponin as an emulsifier)
800 g of isomerized liquid sugar (Bx75 °) mixed with 50 g of decaglycerin monooleate (trade name: Decaglyn 1-OLV, manufactured by Nikko Chemicals) and 50 g of kirayanin C-100 (manufactured by Maruzen Pharmaceutical Co., Ltd .: 25% kiraya extract) Dissolve to make the aqueous phase. This was mixed with 100 g of Reference Product 1 (Apple Blended Fragrance) and stirred at 6000 rpm for 10 minutes using TK-Homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1070 g of an emulsified composition of Apple formulated flavor ( Comparative product 17: containing 10% of apple blended fragrance).

Example 9
Invention products 4 to 6 and comparative products 10 to 17 were subdivided into 30 ml sample bottles by 30 g, and a storage test was conducted at 5 ° C., 20 ° C. and 50 ° C. for 1 week, and the state of emulsification was observed with the naked eye. Further, the emulsified state was further observed with an optical microscope, and the emulsified state was determined. The results are shown in Table 3.

  As shown in Table 3, the same results as those shown in Table 1 were obtained when using Apple blended fragrance instead of rice salad oil. That is, the products 4 to 6 of the present invention in which Kirayasaponin and polysorbate were used in combination obtained a stable emulsion immediately after emulsification, and the emulsion state was stable with little change even after storage at 50 ° C. for 1 week. On the other hand, in Comparative Examples 10-17 using other emulsifiers or a combination thereof, an emulsion having good stability could not be obtained.

  Emulsification of Apple's blended fragrance, such as Reference Product 1 only with a fragrance compound, without using any solvent such as ethanol, propylene glycol, or medium chain fatty acid triglyceride seems to have been rarely performed. According to the method of the present invention, it was possible to obtain an emulsion composition with extremely good stability.

Example 10
Inventive products 4 to 6 having good emulsification state in Example 9 were diluted with water by 0.1%, and the diluted solution was stored at 5 ° C. for 1 month. As a result, the emulsified state of the diluted solution was good, and no aggregation or coalescence of particles was observed even when observed with an optical microscope, and an extremely stable emulsified state was maintained.

Example 11
50 g of Kirayanin C-100 (manufactured by Maruzen Pharmaceutical Co., Ltd .: containing 25% Kiraya extract) is mixed and dissolved in 845 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. Separately, 100 g of K2 oil M-1500 (manufactured by J-Oil Mills Co., Ltd .: Vitamin K2 content 0.15%) is mixed and dissolved with 5 g of Emazole L-120V (polysorbate 20, Kao Co., Ltd.) To do. The water phase part and the oil phase part were mixed and stirred for 10 minutes at 6000 rpm using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of K2 oil (Invention product 7: Containing 10% K2 oil).

Example 12
In Example 11, the same operation as in Example 11 was performed except that 5 g of Emazole S-120V (Polysorbate 60, manufactured by Kao Corporation) was used instead of 5 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation). 1000 g of an emulsion composition of K2 oil was obtained (Product 8 of the present invention: containing 10% of K2 oil).

Example 13
In Example 11, except for using 5 g of Emazole O-120V (Polysorbate 80, manufactured by Kao Corporation) instead of 5 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation), the same operation as in Example 11 was performed, 1000 g of an emulsion composition of K2 oil was obtained (Product 9 of the present invention: containing 10% of K2 oil).

Comparative Example 18 (using Kirayasaponin as an emulsifier)
50 g of Kirayanin C-100 (manufactured by Maruzen Pharmaceutical Co., Ltd .: containing 25% Kiraya extract) is mixed and dissolved in 850 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. This was mixed with 100 g of K2 oil and stirred at 6000 rpm for 10 minutes using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of K2 oil (Comparative product 18: K2 oil 10). % Content).

Comparative Example 19 (using polysorbate as an emulsifier)
100 g of ethanol, 400 g of glycerin and 100 g of water were mixed and dissolved in 300 g of Emazole L-120V (Polysorbate 20, manufactured by Kao Corporation), 100 g of K2 oil was added thereto, and 6000 rpm using a TK-homomixer (manufactured by Koki Kogyo Co., Ltd.). For 10 minutes to obtain 1000 g of an emulsion composition of K2 oil (Comparative product 19: containing 10% of K2 oil).

Comparative Example 20 (using polyglycerin fatty acid ester as an emulsifier)
50 g of decaglycerin monooleate (trade name: Decaglyn 1-OV, manufactured by Nikko Chemicals) is mixed and dissolved in 850 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. This was mixed with 100 g of K2 oil and stirred at 6000 rpm for 10 minutes using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of K2 oil (Comparative product 20: K2 oil 10). % Content).

Comparative Example 21 (using sucrose fatty acid ester as an emulsifier)
To 880 g of isomerized liquid sugar (Bx75 °), 20 g of sucrose stearate (trade name: Sugar Ester DK-SS, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) is added and dissolved to obtain an aqueous phase part. This was mixed with 100 g of K2 oil and stirred for 10 minutes at 6000 rpm using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of K2 oil (Comparative product 21: K2 oil 10). % Content).

Comparative Example 22 (using gum arabic as an emulsifier)
500 g of gum arabic aqueous solution (concentration 30%) is sterilized at 85 ° C. to 95 ° C. for 15 minutes, cooled to 40 ° C. or less, dissolved by adding 400 g of glycerin to obtain an aqueous phase part. This was mixed with 100 g of K2 oil, and stirred at 6000 rpm for 10 minutes using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of K2 oil (Comparative product 22: K2 oil 10). % Content).

Comparative Example 23 (using polyglycerin fatty acid ester and polysorbate as an emulsifier)
50 g of decaglycerin monooleate (trade name: Decaglyn 1-OLV, manufactured by Nikko Chemicals) is mixed and dissolved in 845 g of isomerized liquid sugar (Bx75 °) to obtain an aqueous phase part. Separately, 5 g of Emazole O-120V (Polysorbate 80, manufactured by Kao Corporation) is mixed and dissolved in 100 g of K2 oil to obtain an oil phase part. The water phase part and the oil phase part were mixed and stirred at 6000 rpm for 10 minutes using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of K2 oil (Comparative product 23: K2 Containing 10% oil).

Comparative Example 24 (using gum arabic and polysorbate as emulsifier)
After sterilizing 500 g of gum arabic aqueous solution (concentration 30%) at 85 ° C. to 95 ° C. for 15 minutes, the solution is cooled to 40 ° C. or less and dissolved by adding 395 g of glycerin to obtain an aqueous phase part. Separately, 5 g of Emazole O-120V (Polysorbate 80, manufactured by Kao Corporation) is mixed and dissolved in 100 g of K2 oil to obtain an oil phase part. The water phase part and the oil phase part were mixed and stirred at 6000 rpm for 10 minutes using a TK-homomixer (made by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of K2 oil (Comparative product 24: K2 Containing 10% oil).

Comparative Example 25 (using polyglycerin fatty acid ester and Quillaja saponin as an emulsifier)
800 g of isomerized liquid sugar (Bx75 °) mixed with 50 g of decaglycerin monooleate (trade name: Decaglyn 1-OLV, manufactured by Nikko Chemicals) and 50 g of kirayanin C-100 (manufactured by Maruzen Pharmaceutical Co., Ltd .: 25% kiraya extract) Dissolve to make the aqueous phase. This was mixed with 100 g of K2 oil and stirred at 6000 rpm for 10 minutes using a TK-homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) to obtain 1000 g of an emulsion composition of K2 oil (Comparative product 25: K2 oil 10). % Content).

Example 14
Invention products 7 to 9 and comparative products 18 to 25 were divided into 30-ml sample bottles in 30 g portions, and a storage test was conducted at 5 ° C., 20 ° C. and 50 ° C. for 1 week, and the state of emulsification was observed with the naked eye. Further, the emulsified state was further observed with an optical microscope, and the emulsified state was determined. The results are shown in Table 4.

  As shown in Table 4, when K2 oil was used instead of rice salad oil, the results were almost the same as in Table 1. That is, the products 7 to 9 of the present invention using Kirayasaponin and polysorbate in combination obtained a stable emulsion immediately after emulsification, and the emulsion state was stable with little change even after storage at 50 ° C. for 1 week. On the other hand, in Comparative Examples 18 to 25 using other emulsifiers or combinations thereof, emulsions having good stability could not be obtained.

Example 15
Inventive products 7 to 9 having good emulsification state in Example 14 were diluted 0.1% in water, and the diluted solution was stored at 5 ° C. for 1 month. As a result, the emulsified state of the diluted solution was good, and no aggregation or coalescence of particles was observed even when observed with an optical microscope, and an extremely stable emulsified state was maintained.

Claims (1)

It is a manufacturing method of an O / W type emulsion composition , Comprising : (A) 0.5-50 mass% of oil-soluble substances, (B) 0.05-5 mass% of Kirayasaponin, (C) polyoxyethylene sorbitan the fatty acid ester 0.01 wt% to 10 wt% and (D) water, one or more selected from monohydric alcohols and polyhydric alcohols containing 10 wt% to 90 wt%, (D) water, monovalent (B) Quillaja saponin is mixed and dissolved in an aqueous phase composed of at least one selected from alcohol and polyhydric alcohol, and separately from this, (A) oil-soluble substance, (C) polyoxyethylene sorbitan fatty acid ester A method for producing an O / W type emulsified composition, wherein the two are mixed and emulsified.