JP4403783B2 - Emulsifying or solubilizing agent for low alcohol beverage, emulsifying or solubilizing preparation containing the same, and low alcohol beverage - Google Patents

Description

  The present invention relates to an emulsifying or solubilizing agent for low alcohol beverages, an emulsifying or solubilizing preparation containing the same, and a lower alcohol beverage. The emulsification or solubilizing agent of the present invention contains a polyglycerin fatty acid ester and an ionic emulsifier, and does not gel when stored at a low temperature, and is excellent in O / W type fine emulsification even under acidic conditions in the presence of alcohol. And has a good flavor and high stability at low temperatures, and is suitable for forming a low alcoholic beverage.

  Polyglycerin fatty acid ester (hereinafter sometimes abbreviated as “PoGE”) is known as a surfactant approved as a food additive, and is mainly used as an emulsifier for food. Recently, Widely used in medicine, cosmetics, industrial applications, etc. PoGE has a wide range of properties from hydrophilic to lipophilic by controlling the average degree of polymerization of polyglycerin (hereinafter sometimes abbreviated as “PoG”), the chain length of constituent fatty acids, the degree of substitution, etc. Is obtained.

It has been shown that PoGE having a polyglycerin polymerization degree of 6 or more and a fatty acid having 12 to 22 carbon atoms as a constituent component is effective for solubilization of oil-soluble substances (see Patent Document 1). Among them, PoGE having a C12-22 unsaturated fatty acid as a constituent component has excellent acid resistance, salt resistance, heat resistance not found in other food emulsifiers, and is represented by sauce, dressing, mayonnaise and the like. It is effective for O / W type emulsification under acidic or high salt concentration (see Patent Document 2). Among them, the cloud point of a 1% by weight solution of 8 wt% _Na 2 SO ₄ aqueous solution is preferred PoGE composition 65 to 90 ° C. (refer to Patent Document 3).
Japanese Patent Laid-Open No. 62-250941 Japanese Patent Laid-Open No. 61-234920 JP 2000-287631 A

  However, in general, the emulsifying performance of polyglycerin unsaturated fatty acid ester is said to be higher than that of polyglycerin saturated fatty acid ester, and it has acid resistance, and O under acidic conditions such as sauce, dressing, mayonnaise and the like. It is effective for / W type emulsification, and it is said that the emulsification performance under acidic conditions is higher than that of polyglycerin saturated fatty acid ester. However, unsaturated fatty acids have a characteristic odor and taste and have a bad influence on flavor. give.

  On the other hand, in the case of a polyglycerin saturated fatty acid ester, if the chain length is too long, the water solubility is lowered, and there is a problem that the emulsion precipitates during storage, and if it is too short, there is a problem that sufficient emulsifying ability is not exhibited. . Furthermore, in the case of a polyglycerin saturated fatty acid ester, if the fatty acid acid chain is long, there is a problem that the solubilized or emulsified preparation prepared thereby gelates when stored at low temperature.

  As a result of various studies to solve the above problems, the present inventor has prepared a combination of PoGE containing a large amount of palmitic acid as a constituent fatty acid and having a cloud point of a specific temperature or more in combination with an ionic emulsifier. Has been found to be a good product with good flavor and good balance between emulsifying power and stability at low temperatures.

The present invention has been completed based on the above findings, and the first gist thereof is that 70% by weight or more of the constituent fatty acid is palmitic acid and 1% by weight in a 7% by weight Na ₂ SO ₄ aqueous solution. It exists in the emulsification thru | or solubilizer for low-alcohol drinks characterized by containing the polyglyceryl fatty acid ester (a) and ionic emulsifier (b) whose cloud point of a solution is 55 degreeC or more.

  And another gist of the present invention resides in an emulsification or solubilization preparation for a low alcohol beverage characterized by containing the above emulsification or solubilizer, water-insoluble substance, polyhydric alcohol and / or water. .

  Still another subject matter of the present invention resides in a low alcohol beverage characterized by containing the above emulsifying or solubilizing agent, a water-insoluble substance, a polyhydric alcohol and / or water.

  The emulsification or solubilizing agent of the present invention does not gel the preparation, and has an excellent effect on O / W type fine emulsification even under acidic conditions in the presence of alcohol, and also has good flavor emulsification or solubilization. The composition can be provided and does not precipitate even when stored at low temperatures.

  Hereinafter, the present invention will be described in detail.

[Emulsification or solubilizer]
The emulsifying or solubilizing agent of the present invention is a polyglycerin fatty acid in which 70% by weight or more of the constituent fatty acid is palmitic acid, and the cloud point of a 1% by weight solution in a 7% by weight Na ₂ SO ₄ aqueous solution is 55 ° C. or more. The ester (a) and the ionic emulsifier (b) are essential components.

(1) Polyglycerol fatty acid ester:
The average degree of polymerization of polyglycerol in the polyglycerol fatty acid ester is usually 4 to 20, preferably 4 to 12. The proportion of palmitic acid in the constituent fatty acid needs to be 70% by weight or more, preferably 80% by weight or more, more preferably 90% by weight or more, and particularly preferably 95% by weight or more. When the proportion of palmitic acid is less than 70% by weight,
The emulsified or solubilized composition becomes unstable or precipitates during storage at low temperatures. The constituent fatty acid that can be used in combination with palmitic acid is not particularly limited, but is usually a fatty acid having 10 to 18 carbon atoms. Moreover, the polyglycerin fatty acid ester has a cloud point of 55 ° C. or higher in a 1 wt% solution in a 7 wt% Na ₂ SO ₄ aqueous solution.

  A method of using the cloud point for product management of polyglycerin fatty acid ester has been proposed (Japanese Patent Laid-Open No. 9-157386), and the advantages thereof are described as follows.

  Various chemical analysis methods have been used for the analysis of PoGE. For example, the acid value, ester value, and hydroxyl value are often used to determine the degree of esterification and the amount of residual fatty acid, and evaluation methods such as analysis of ignition residue to determine the amount of soap or residual catalyst are also used. It has been.

  The PoG skeleton of the hydrophilic part in PoGE is a composition having a polymerization degree distribution because it is a polycondensate of glycerin, and includes not only a linear polymer but also a branched polymer and a cyclic polymer. Yes. Generally, PoG increases in viscosity as the degree of polymerization increases, and purification such as separation of a cyclic polymer from a polycondensate is very difficult. Therefore, a reaction obtained by esterifying the hydroxyl group of PoG with fatty acids. The product PoGE usually consists of a composition comprising PoGE of various esterification degrees with different PoG skeletons and unreacted PoG. Further, the esterification reaction product may contain by-product soaps produced by the reaction between the alkali catalyst used in the reaction and the starting fatty acids. In addition, the esterification reaction product may contain unreacted fatty acids when the esterification reaction is insufficient, or when fatty acids exceeding the stoichiometric amount are used excessively. As described above, PoGE is a complex composition. For example, even if the average degree of esterification of PoGE is similar or the same, physical properties such as emulsion stability may be significantly different. Only the conventional chemical analysis method for the reaction PoG or the like cannot sufficiently grasp the physical properties, resulting in inconvenience in the physical property evaluation method.

  As a method for evaluating the physical properties of a surfactant other than the above chemical analysis, for example, a method using a cloud point in a polyoxyethylene-based nonionic surfactant derived from ethylene oxide is known (oil and fat terminology dictionary: Japan Oil Chemistry Association (Shoshobo)). In general, the cloud point is defined as the temperature at which a nonionic surfactant aqueous solution derived from ethylene oxide separates into two phases due to an increase in temperature and becomes inhomogeneous, and the system becomes homogeneous again when the temperature decreases. (Dictionary of fats and oils) In polyoxyethylene-based surfactants, there is a correlation between the cloud point and the average degree of polymerization of the polyoxyethylene chain, which is a hydrophilic group, and the average degree of polymerization of polyoxyethylene ethylene oxide increases and hydrophilicity increases. It is known that the cloud point increases as it increases. And when manufacturing the target surfactant, the clouding point was measured and reaction conditions were selected so that the addition polymerization degree of ethylene oxide might be in an appropriate range. It has been explained that such a manufacturing operation is possible because the hydrophilicity of the ether groups present in the ethylene oxide polymer of this type of surfactant decreases with increasing temperature.

  On the other hand, in PoGE, since the hydrophilic portion is a polycondensate of glycerin, unlike a polyoxyethylene chain, not only a hydroxyl group and an ether group exist simultaneously, but also the presence of this hydroxyl group causes branch condensation and cyclic polycondensation. Since this occurs, the composition is extremely complicated, and it has been difficult to measure the cloud point of PoGE. However, it is possible to measure the cloud point of PoGE by preparing a homogeneous aqueous solution by adding salts and / or polyhydric alcohols to PoGE and raising the temperature of the aqueous solution to form a heterogeneous aqueous solution. became. Even with PoGE, in which the difference does not clearly appear in the chemical analysis methods such as the analysis of the acid value, ester value, hydroxyl value, and ignition residue, the difference can be clarified at the cloud point. In addition, since there is a strong correlation between functions such as emulsifying ability and solubilizing ability and cloud point, it is very useful to use cloud point for PoGE product management (NEWSLETTER, 1998, 23 (1), 10 -13).

  As a cloud point measuring method, it is usually necessary to measure after dissolving a polyglycerin fatty acid ester in a 1 to 30% by weight sodium chloride or sodium sulfate solution. Specific measurement conditions vary depending on the solubility of the target sample. In the case of the present invention, first, polyglycerin fatty acid ester is dispersed in a 7% by weight sodium sulfate aqueous solution so as to be 1% by weight and stirred while heating to obtain a uniform aqueous solution. Next, the obtained polyglycerol fatty acid ester aqueous solution is changed in increments of 2 to 5 ° C. at an arbitrary temperature of 0 to 100 ° C., and is left to stand after shaking and stirring at a constant temperature. It is separated like a gel and the temperature at which it becomes a heterogeneous aqueous solution is measured. This change from the uniform state to the non-uniform state is called “cloud point phenomenon”, and the temperature at which the change occurs is called “cloud point”. In the present invention, the cloud point is obtained. If the measurement temperature is less than 0 ° C., the melting point is below the melting point of ice, and if it exceeds 100 ° C., the boiling point of water is exceeded.

  The polyglycerin fatty acid ester used in the present invention has a cloud point of 55 ° C. or higher in a 1 wt% solution in a 7 wt% sodium sulfate aqueous solution. When the cloud point is less than 55 ° C., the hydrophobicity is increased, it becomes difficult to form a stable fine emulsion composition, the transmittance of the emulsion or solubilized composition is lowered, and the emulsion composition is being stored. PoGE itself precipitates. The cloud point of the polyglycerol fatty acid ester is preferably higher, preferably 70 ° C. or higher, more preferably 80 ° C. or higher, particularly preferably 90 ° C. or higher, more preferably 100 ° C. or higher.

  The amount of unreacted polyglycerol contained in the polyglycerol fatty acid ester is preferably small, and is usually 80% by weight or less, preferably 60% by weight or less. Moreover, the average esterification rate (ratio of the esterified hydroxyl group in the hydroxyl group of PoG) of polyglycerol fatty acid ester is 10-30 weight% normally, Preferably it is 10-20 weight%.

  Various methods are known for producing polyglycerol fatty acid esters. Broadly speaking, (1) direct esterification of polyglycerin with fatty acids (fatty acid, fatty acid chloride, etc.), (2) method by transesterification of polyglycerin with fatty acid methyl ester, fats and oils, (3) glycidol and fatty acid A method based on an addition polymerization reaction with a fatty acid (fatty acid, fatty acid monoglyceride, etc.) is common. Moreover, as an industrial method, the direct esterification method of the polyglycerol of the said (1) and a fatty acid is employ | adopted widely.

  On the other hand, as a method for producing a raw material polyglycerol, a method using a dehydration condensation reaction of glycerol is widely adopted industrially, but a method using a polycondensation reaction of epichlorohydrin or an addition reaction of glycidol is also known. In the present invention, a dehydration condensation reaction of glycerin and a method using glycidol as a raw material are preferable.

  In the dehydration condensation reaction of glycerin, polyglycerol is obtained by heating to a high temperature of 200 ° C. or higher while adding an alkali catalyst to glycerin and blowing an inert gas such as nitrogen gas. The reaction time is usually 3 to 10 hours.

  In the addition reaction of glycidol, for example, (1) a method in which a phosphoric acid catalyst is used in an amount of 0.01 to 10% by weight with respect to glycerin, and glycidol is added according to the target degree of polymerization; And a method of removing carboxylic acid by hydrolysis after reacting the carboxylic acid with glycidol corresponding to the desired degree of polymerization. The addition reaction is usually carried out by adding glycidol to the system little by little. The reaction temperature is usually 80 to 140 ° C., and the reaction is preferably carried out under an inert gas stream such as nitrogen gas. After completion of the reaction, the phosphoric acid catalyst and the residual carboxylic acid are neutralized with an alkali and dehydrated. The product can be purified by diatomaceous earth filtration or the like depending on the purpose. The resulting polyglycerin is a viscous liquid with little coloration.

  The polyglycerin fatty acid ester used in the present invention is usually 0.001 to 3% by weight, preferably 0.001 based on the raw material (total of polyglycerin and fatty acid) in the direct esterification reaction of polyglycerin and fatty acid. It can be produced by using an alkali catalyst of ˜0.05% by weight, more preferably 0.001 to 0.01% by weight, and usually reacting at 150 to 300 ° C., preferably 180 to 260 ° C. When the amount of the alkali catalyst used is less than the above range, the esterification reaction hardly proceeds and it takes a long time to complete the reaction. Moreover, when the usage-amount of an alkali catalyst exceeds the said range, inconveniences, such as coloring of a product and superposition | polymerization of raw material PoG, will arise. Examples of the alkali catalyst include potassium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide and the like. The reaction is usually performed while charging polyglycerol, a fatty acid, and a catalyst into a stirred tank type reactor, heating to a predetermined temperature while stirring, and distilling the produced water out of the reaction system. During a series of reactions, it is preferable to circulate an inert gas such as nitrogen in the gas phase part of the reactor. The molar ratio of fatty acid to polyglycerol is usually 0.4 to 1.5, preferably 0.6 to 1.2, and more preferably 0.8 to 1.0.

  The content of the polyglycerol fatty acid ester contained in the emulsifying or solubilizing agent of the present invention is usually 20 to 99.99% by weight, preferably 40 to 99.99% by weight, more preferably 60 to 99.99% by weight. %.

(2) Ionic emulsifier:
Examples of the ionic emulsifier used in the present invention include monoglyceride organic acid esters and alkali metal salts thereof, lactic acid fatty acid esters and alkali metal salts thereof.

  Examples of the constituent organic acid of the monoglyceride organic acid ester include lactic acid, citric acid, succinic acid, diacetyltartaric acid and the like. Examples of the constituent fatty acid include saturated or unsaturated fatty acids having 8 to 18 carbon atoms, and unsaturated fatty acids are preferred. In particular, oleic acid monoglyceride citrate is preferred. Examples of the alkali metal that forms the alkali metal salt include sodium and potassium, and sodium is preferable.

  Examples of the constituent fatty acid of the lactic acid fatty acid ester include saturated or unsaturated fatty acids having 8 to 18 carbon atoms. Lactic acid stearate sodium salt is particularly preferable. Examples of the alkali metal include sodium and potassium, and sodium is preferable.

  The content of the ionic emulsifier contained in the emulsification or solubilizing agent of the present invention is usually 0.01% by weight or more, preferably 0.05% by weight or more, more preferably 1% by weight or more, and usually 20%. % By weight or less, preferably 10% by weight or less, more preferably 5% by weight or less.

(3) Other ingredients:
In the emulsification or solubilizing agent of the present invention, in addition to the polyglycerin fatty acid ester and the ionic emulsifier, the glycerin fatty acid ester, sucrose fatty acid ester, propylene glycol fatty acid ester, You may mix | blend other components, such as a lecithin and sorbitan fatty acid ester.

(4) Preparation method of emulsification or solubilizer The total content of the polyglycerin fatty acid ester and the ionic emulsifier contained in the emulsification or solubilizer of the present invention is usually 20 to 100% by weight, preferably 40 to 40% by weight. 100% by weight, more preferably 60-100% by weight. The ionic emulsifier / (polyglycerin fatty acid ester + ionic emulsifier) (weight ratio) is usually 0.0002 to 0.3, preferably 0.001 to 0.15, more preferably 0.01 to 0.00. 1.

  The emulsifying or solubilizing agent of the present invention is usually obtained by directly mixing an ionic emulsifier and other components with polyglycerin fatty acid ester and heating to about 40 to 60 ° C. to improve fluidity, and uniformly with a stirrer. It can be prepared by mixing. Moreover, what melt | dissolved these components sequentially or simultaneously in appropriate quantity of water may be used as it is, and what distilled water from there and made only solid content may be used.

[Emulsified or solubilized preparation]
The emulsification or solubilization preparation of the present invention contains the above emulsification or solubilizer (polyglycerin fatty acid ester and ionic emulsifier), a water-insoluble substance, a polyhydric alcohol and / or water. In the present specification, the term “solubilized composition” means a solution having a transparent appearance, including a solution having a transparent appearance by fine emulsification, and usually a uniform solution having a transmittance of 50% or more at 650 nm. The solubilized preparation means a preparation used for preparing this solubilized composition. In the present specification, the “emulsified composition” means an emulsified solution having an opaque appearance, usually refers to a uniform solution having a transmittance of less than 50% at 650 nm, and an emulsified preparation is used to prepare this emulsified composition. Means a formulation used for

  Examples of the water-insoluble component used in the present invention include coloring agents, flavoring agents, essential oils, oleodins or resinoids, waxes, fatty acids and esters, vitamins, antioxidants, saturated or unsaturated higher alcohols, hydrocarbons. , Preservatives, bactericides, animal and vegetable oils and the like.

  Specific examples of the colorant include β-carotene, paprika dye, anato dye, safrole yellow, riboflavin, lac dye, curcumin, chlorophyll, turmeric dye, and the like.

  Specific examples of flavoring agents include orange oil, lemongrass oil, tarragon oil, avocado oil, laurel leaf oil, cassia oil, cinnamon oil, pepper oil, columnus oil, sage oil, peppermint oil, peppermint oil, spear mint oil, Patchouli oil, rosemary oil, lavandin oil, lavender oil, curcuma oil, cardamom oil, ginger oil, angelica oil, anise oil, fennel oil, parsley oil, celery oil, carbanum oil, cumin oil, coriander oil, jill oil, carrot Oil, Kilauea Oil, Winter Grin Oil, Nutmeg Oil, Rose Oil, Cypress Oil, Sandalwood Oil, Allspice, Grapefruit Oil, Neroli Oil, Lemon Oil, Lime Oil, Bergamot Oil, Mandarin Oil, Onion Oil, Garlic Oil, Bitter Almond Oil, geranium oil, mimosa oil, jasmine oil Osmanthus oil, star anise oil, cananga oil, ylang ylang oil, eugenol, ethyl caprylate, geraniol, menthol, citral, citronellal, borneol, and the like.

  Specific examples of essential oils include amblet seed oil, mustard oil, saffron oil, sitonela oil, vetiver oil, valerian oil, mugwort oil, chamomile oil, camphor oil, sassafras oil, pepper oil, rosewood oil, clary sage oil, Examples include thyme oil, basil oil, carnation oil, cedarwood oil, cypress oil, hiba oil, clove oil, turpentine oil, and pine oil.

  Specific examples of oleodine or resinoid include pepper, ginger, ginger, parsley, coriander, himeweed, pimenta, vanilla, celery, clove, nutmeg, publica, iris resinoid, fragrant tree, omonics and the like.

  Specific examples of the wax include jojoba oil, rice wax, propolis, beeswax, honey beeswax, candelilla wax, carnauba wax, wood wax, spermaceti, sesilene and the like.

  Specific examples of fatty acids and esters include hexadecatrienoic acid, octadecatrienoic acid, eicosatetraenoic acid, docosatetraenoic acid, eicosapentaenoic acid, docosapentaenoic acid, docosahexaenoic acid, tetrahexaenoic acid, and their geometries Isomers, esters of these with alcohols.

  Specific examples of vitamins include vitamin A, vitamin D, vitamin E, vitamin K and the like.

  Specific examples of the antioxidant include ascorbic acid ester, dl-α-tocopherol, dibutylhydroxytoluene, butylhydroxyanisole, Enju extract, γ-oryzanol, clove extract, catechins, gentidine oil, gosipetin, rice bran oil Examples include saponified products, sezamorin, sezamonol, sage extract, natural vitamin E, pimenta extract, pepper extract, gallic acid derivatives, eucalyptus leaf extract, rosemary extract and the like.

  Specific examples of saturated or unsaturated higher alcohols include alcohols having 8 to 44 carbon atoms such as lauryl alcohol, myristyl alcohol, cetanol, stearyl alcohol, oleyl alcohol, lauric alcohol, isostearyl alcohol, 2-octyldodecanol octacosanol and the like. Can be mentioned.

  Specific examples of the hydrocarbons include light liquid paraffin, heavy liquid paraffin, liquid isoparaffin, light liquid isoparaffin, ceresin, paraffin, macrocristan wax, petrolatum, squalane, squalene, and the like.

  Specific examples of preservatives and bactericides include dehydroacetic acid. Specific examples of animal and vegetable oils and fats include safflower oil, soybean oil, corn oil, cottonseed oil, rapeseed oil, sesame oil, rice oil, sunflower oil, peanut oil, olive oil, palm oil, palm kernel oil, camellia oil, palm oil, Castor oil, linseed oil, cacao oil, milk fat, medium chain fatty acid triglyceride, beef tallow, lard, fish oil and the like.

  Polyhydric alcohols are propylene glycol, glycerin, sorbitol, xylitol, arabitol, maltitol, lactitol, sorbitan, xylose, arabinose, mannose, lactose, sugar, coupling sugar, glucose, enzyme starch syrup, acidified starch syrup, maltose starch syrup, maltose Isomerized sugar, fructose, reduced maltose starch syrup, reduced starch sugar syrup, honey and the like.

  As the water, normal tap water is used in addition to desalted water, and food additives may be added thereto.

  The emulsified or solubilized preparation of the present invention may contain a food additive such as a surfactant, ethanol, a stabilizer, a seasoning, an acid, and a salt, if necessary.

  The emulsified or solubilized preparation of the present invention is a composition emulsified or solubilized by itself, and becomes a raw material of an emulsified or solubilized composition (low alcohol beverage) described later. The emulsified or solubilized preparation of the present invention has the following composition.

  The polyglycerol fatty acid ester is usually 0.1% by weight or more, usually less than 90% by weight, preferably less than 50% by weight, more preferably less than 20% by weight.

The content of the ionic emulsifier is usually 1 × 10 ⁻⁵ wt% or more, preferably 5 × 10 ⁻⁵ wt% or more, more preferably 0.001 wt% or more, usually less than 18 wt%, preferably 5 Less than wt%, more preferably less than 1 wt%.

  The water-insoluble substance is usually at least 0.1% by weight, usually less than 90% by weight, preferably less than 50% by weight, more preferably less than 20% by weight.

  The polyhydric alcohol is usually 0% by weight or more, preferably 50% by weight or more, more preferably 80% by weight or more, and usually less than 99.8% by weight.

  Water is usually 0% by weight or more, usually less than 99.8% by weight, preferably less than 50% by weight, and more preferably less than 20% by weight.

  The weight ratio of water-insoluble substance / (water-insoluble substance + PoGE) is usually 0.01 or more and less than 0.99, preferably 0.09 or more and less than 0.9, and more preferably 0.33 or more and 0. Less than .66.

  The weight ratio of water-insoluble substance / (water-insoluble substance + water and / or polyhydric alcohol) is usually 0.0001 or more and less than 0.3, preferably 0.001 or more and less than 0.2. Preferably, it is 0.01 or more and less than 0.1.

  The weight ratio of polyhydric alcohol / (water + polyhydric alcohol) is usually 0 or more and 1 or less, preferably 0.6 or more and 1 or less, and more preferably 0.8 or more and 1 or less.

  The weight ratio of ionic emulsifier / (PoGE + ionic emulsifier) is usually 0.0002 to 0.3, preferably 0.001 to 0.15, and more preferably 0.01 to 0.1.

  An emulsified or solubilized preparation can be prepared by mixing and stirring each component by a known ordinary method. For example, an emulsifier such as a homomixer may be used for the preparation, or a high-pressure homogenizer may be used. Moreover, after melt | dissolving polyglyceryl fatty acid ester and ionic emulsifier (or said emulsification or solubilizer), polyhydric alcohol, and / or water at 40-80 degreeC, this and a water-insoluble substance are mixed, and an emulsification process is carried out. It can also be prepared by the following method.

[Low alcohol drink]
An emulsified or solubilized composition (low alcohol beverage) prepared by diluting the above emulsified or solubilized preparation (that is, an emulsified or solubilizer, a water-insoluble substance, a polyhydric alcohol and / or water) in an aqueous medium, The fine emulsified composition maintains a high transmittance even under acidic conditions and has a good taste, and further, precipitation of the emulsifier itself does not occur during storage. Depending on the application, for example, sugars such as sucrose, fructose, glucose, maltose, lactose, sorbitol, mannitol, xylose, xylitol, erythritol, citric acid, succinic acid, acetic acid, tartaric acid, lactic acid, fumaric acid, malic acid, etc. Contains organic acids.

The content of each component in the emulsified or solubilized composition is as follows. That is, the polyglycerin fatty acid ester is usually 0.001 to 50% by weight, the ionic emulsifier is usually 1 × 10 ^{−7 to} 10% by weight, and the water-insoluble substance is usually It is 0.001% or more and less than 50% by weight, polyhydric alcohol is usually 0.001% or more and less than 50% by weight, and water is usually 50% or more and less than 99.9% by weight.

  The weight ratio of the water-insoluble substance / (water-insoluble substance + PoGE) is usually 0.001 or more and less than 1, and the weight of the water-insoluble substance / (water-insoluble substance + water and / or polyhydric alcohol). The ratio is usually 0.000001 or more and less than 0.15, and the weight ratio of polyhydric alcohol / (water + polyhydric alcohol) is usually 0 or more and less than 0.5.

  The content of alcohol such as ethanol is usually 0.01% by weight or more, preferably 0.1% by weight or more, more preferably 1% by weight or more, usually 20% by weight or less, preferably 10% by weight or less, Preferably it is 5 weight% or less.

  Examples of the low alcohol beverage of the present invention include sour, strawberry high, cocktail, and sweet fruit wine. The pH of the low alcohol beverage is usually 2 to 8, preferably 2 to 6, and more preferably 2 to 4.

  The transmittance of the solubilized composition of the present invention is preferably high. For example, the transmittance at 650 nm is usually 60% or more, preferably 80% or more, and more preferably 90% or more.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further, this invention is not limited to a following example, unless the summary is exceeded. The cloud point of the polyglycerol fatty acid ester used in this example was measured by the following method.

[Poge cloud point measurement]
PoGE was dissolved in a 7 wt% sodium sulfate aqueous solution prepared in advance so that the PoGE concentration would be 1 wt%, and this solution was sealed in a glass tube. This glass tube is heated and stirred to make the solution uniform, then immersed in a thermostat set to a predetermined temperature, and left for a few minutes to an hour, and then visually observed for separation of the solution in the glass tube. went. The temperature of the thermostatic bath was raised in steps of 5 ° C., and the above method was repeated. The cloud temperature was defined as an intermediate temperature between the temperature at which PoGE was separated and the solution became cloudy for the first time and the highest temperature at which the solution was uniform.

[Production Example 1: Production of PoGE-A]
A reaction vessel having a capacity of 2 L equipped with a stirrer, thermometer, heating jacket, gas charging port, and raw material charging port was used. First, 1200 g of PoG (average polymerization degree 10) was charged, and then palmitic acid (purity 99% by weight) and a 10% by weight aqueous sodium hydroxide solution were charged. The amount of palmitic acid charged was such that the palmitic acid / PoG molar ratio was 0.8 / 1. The amount of sodium hydroxide added was 0.0025% by weight based on the total amount of PoG and fatty acid. Under a nitrogen stream, the internal temperature was raised to 240 ° C. at normal pressure and reacted at this temperature for 3 hours, and then the internal temperature was further raised to 260 ° C. and reacted at this temperature for 4 hours. After completion of the reaction, the internal temperature was cooled to room temperature to obtain polyglycerin palmitate (PoGE-A). About the obtained reaction product, the cloud point was measured by the said method. The results are shown in Table 1.

[Production Example 2: Production of PoGE-B]
Polyglycerin palmitic acid ester (PoGE-B) was obtained in the same manner as in Production Example 1 except that in Production Example 1, the palmitic acid / PoG molar ratio was 1.5 / 1. About the obtained reaction product, the cloud point was measured by the said method. The results are shown in Table 1.

Examples 1 to 3 Comparative Examples 1 and 2
Solubilized preparations were obtained with the compositions shown in Table 1. This preparation was stored at 5 ° C. for 1 month, and the appearance and transmittance at 650 nm were observed. Further, 3 g of this solubilized preparation was mixed and stirred with 27 g of an aqueous solution containing 0.9% by weight of citric acid and 18% by weight of ethanol to obtain a uniform diluted solution (final solubilized composition). One day later, the transmittance of the diluted solution at 650 nm was measured at room temperature. Furthermore, the diluted solution was stored at 5 ° C. for 1 week, and the presence or absence of precipitation was confirmed. In addition, Shimadzu "UV-1200" was used for the measurement of the transmittance | permeability. The results are shown in Table 2.

  From the results shown in Table 1 and Table 2, it can be seen that the preparations of Examples 1 to 3 do not cause gelation during low-temperature storage, have high permeability of the preparation and diluent, and do not precipitate during low-temperature storage. . On the other hand, it can be seen that the preparation of the comparative example has problems in any of gelation of the preparation, decrease in the permeability of the preparation and the diluent, and precipitation under low temperature storage of the diluent.

Claims (7)

Polyglycerin fatty acid ester (a) and ionic emulsifier (b) in which 70% by weight or more of the constituent fatty acid is palmitic acid and the cloud point of 1% by weight solution in a 7% by weight aqueous solution of Na ₂ SO ₄ is 55 ° C. or more ), An emulsifying or solubilizing agent for low alcohol beverages.   The emulsifying or solubilizing agent according to claim 1, wherein the ionic emulsifier (b) is a monoglyceride organic acid ester or an alkali metal salt thereof.   The emulsifying or solubilizing agent according to claim 1, wherein the ionic emulsifier (b) is a lactic acid fatty acid ester or an alkali metal salt thereof.   An emulsification or solubilization preparation for a low-alcohol beverage comprising the emulsification or solubilization agent, water-insoluble substance, polyhydric alcohol and / or water according to any one of claims 1 to 3.   A low alcohol beverage comprising the emulsifying or solubilizing agent, water-insoluble substance, polyhydric alcohol and / or water according to any one of claims 1 to 3.   The low alcohol drink according to claim 5 containing 0.1 to 20% by weight of ethanol.   The low alcohol beverage according to claim 5 or 6, wherein the beverage is acidic.