JP2008143841A - Composition containing highly crystalline substance - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a composition containing a highly crystalline substance, enabling easy and homogeneous dispersion of the highly crystalline substance in water, having high stability not to form crystals and precipitates even by storing for a long period under a severe condition at high or low temperature and having excellent acid resistance, salt resistance, heat resistance and alcohol resistance and to provide foods, drinks and cosmetics containing the composition. <P>SOLUTION: The problem can be solved by using a composition containing (A) a highly crystalline substance, (B) a polyglycerol fatty acid ester produced by the esterification of a polyglycerol having a hydroxyl value of ≤1,200, a primary hydroxyl group content of ≥50 wt.% based on total hydroxyl groups and a cyclic group content of ≤25 wt.% with a fatty acid, and (C) a liquid oil having an IOB (inorganic/organic balance) value of 0.20-0.60. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention comprises a highly crystalline material-containing composition that is easily dispersed uniformly in water and has high stability that does not produce crystals or precipitates even when stored under severe conditions of low and high temperatures, and The present invention relates to a food or drink containing a highly crystalline substance-containing composition, or a cosmetic.

There are many highly crystalline substances that have important functions for living organisms. There are many things such as poorly water-soluble amino acids, γ-oryzanol, folic acid, and vitamin B ₁ that are desirable for constant consumption, and there is a great demand for applying them to foods. However, it is impeded that the crystallinity of highly crystalline substances and the dispersibility in aqueous and oily media are poor. Therefore, as a method for solving these problems, a method of making a soybean oil unsaponifiable product into an oil-in-water emulsion using an emulsifier and oil (for example, see Patent Document 1), or an emulsifier such as polyglycerin fatty acid ester is used. In addition, a water-soluble composition of plant sterols that maintains a homogeneous emulsified, dispersed or solubilized state even after long-term storage (see, for example, Patent Document 2) is disclosed.

  On the other hand, as crystallization of highly crystalline substances progresses in the product, the content becomes uneven due to emulsion breakage, the dispersibility in foods decreases, the absorption to the living body is inhibited, and the appearance deteriorates, greatly reducing the product value. Therefore, a technique using a strongly dispersible emulsifying device is desired to uniformly disperse a fat-soluble highly crystalline substance in water uniformly over time. Accordingly, there is a technique (for example, see Patent Document 3) in which a carotenoid pigment is uniformly dispersed in water stably over time by performing emulsification using a highly dispersible emulsifier such as a high-pressure emulsifier. It is disclosed.

JP-A-11-152229 JP 2002-291442 A JP-A-10-120933

  However, general polyglycerin fatty acid esters currently on the market have a primary hydroxyl group content of less than 50% by weight and contain a large amount of cyclic products. The ester of polyglycerin and fatty acid cannot exhibit high emulsification and solubilizing power, and further has a problem of preventing the high crystalline substance from being stably dispersed in water due to the presence of the cyclic product. Moreover, it is not designed considering the structure of the hydrophilic group of polyglycerin according to the purpose of use, and there is no technique that focuses on the cyclic body in polyglycerin.

  On the other hand, the technique using a high-dispersion high-pressure emulsifier is not necessarily equipped with a high-pressure emulsifier in any production line, and is less versatile. It is necessary to transfer the mixed raw material to the emulsifier, and during that time, there is a high risk of quality deterioration due to an increase in the possibility of line contamination and the associated complaints. In addition, since it is emulsified at a high pressure, energy consumption is high and it is difficult to say that the method is necessarily highly productive.

  In addition, a highly crystalline substance is generally dissolved in a liquid oil such as vegetable oil by heating and then emulsified, but it is difficult to emulsify while maintaining a dissolved state because of its crystallinity. In addition, even if temporarily emulsified and solubilized and dispersed, problems such as turbidity and crystals occur due to repeated low-temperature and high-temperature storage in an acidic solution or alcohol solution as expected in beverages and the like, causing emulsion breakage. There is. Such a highly crystalline substance is extremely difficult to stably disperse and has extremely low versatility in food and cosmetic applications.

  Therefore, in these methods, it is possible to maintain a stable emulsification and solubilization state of a highly crystalline substance for a long period of time, and it is possible to prepare a composition that can be satisfactorily satisfied as a composition that can be blended in foods and beverages and cosmetics with confidence. difficult.

  Accordingly, the present invention has been made in view of the above-described prior art, and an object of the present invention is to easily and uniformly disperse a highly crystalline substance in water, and to store it for a long time under severe conditions of low and high temperatures. A highly crystalline substance-containing composition having high stability that does not cause crystal or precipitation, and excellent in acid resistance, salt resistance, heat resistance, and alcohol resistance, and a food or drink containing the composition, or To provide cosmetics.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have identified a special polyglycerin fatty acid ester having an excellent crystallization inhibiting effect, emulsification and solubilizing effect, and for dissolving and stabilizing crystals. By using the liquid oil, a highly crystalline substance-containing composition can be obtained without using a special emulsifier, and crystal precipitation does not occur after emulsification. It has been found that a highly crystalline substance-containing composition that maintains excellent acid resistance, salt resistance, heat resistance, and alcohol resistance, and maintains stable emulsification or solubilization even in long-term storage, particularly low-temperature storage. The present invention has been completed.

That is, the present invention
[1] A highly crystalline substance-containing composition containing the following (A) to (C).
(A) Highly crystalline substance (B) Polyglycerin and fatty acid having a hydroxyl value of 1200 or less and a primary hydroxyl group of 50% by weight or more of all the hydroxyl groups and a cyclic content of 25% by weight or less Esterified polyglycerin fatty acid ester (C) Liquid oil with IOB (inorganic / organic balance) value of 0.20 to 0.60 [2] The composition is an oil-in-polyhydric alcohol type (O / D type) The highly crystalline substance-containing composition according to [1], which is an emulsion.
[3] The highly crystalline substance-containing composition according to [1] or [2], wherein the polyglycerol fatty acid ester has an HLB value of 10 to 18.
[4] A food or drink comprising the highly crystalline substance-containing composition according to any one of [1] to [3].
[5] A cosmetic comprising the highly crystalline substance-containing composition according to any one of [1] to [3].
About.

  The highly crystalline material-containing composition of the present invention can easily and uniformly disperse the highly crystalline material in water, and is highly stable without crystallizing or precipitating even when stored under severe conditions at low and high temperatures. And has an effect of being excellent in acid resistance, salt resistance, heat resistance, and alcohol resistance.

  The highly crystalline substance-containing composition of the present invention comprises (A) a highly crystalline substance, (B) a hydroxyl value of 1200 or less, and among all the hydroxyl groups, the primary hydroxyl group is 50% by weight or more, and further contains a ring. Polyglycerin fatty acid ester in which polyglycerin and fatty acid whose amount is 25% by weight or less is esterified, and (C) liquid oil having an IOB (inorganic / organic balance) value of 0.20 to 0.60. Has one feature. When the above (A) to (C) are satisfied, the highly crystalline substance is dissolved in the specific liquid oil, and the crystallization is suppressed by the special polyglycerin ester. It is presumed that it is stably dispersed and crystallization is suppressed.

  In the present specification, a highly crystalline substance is a crystalline organic compound that is solid at room temperature, and 0.1 g is added to 100 ml of water at 20 ° C., including immediately after addition, every 5 minutes until 30 minutes immediately after addition. Substances that, when vigorously shaken for 30 seconds, do not completely dissolve by visual observation within 30 minutes, and substances that form crystals or precipitates when the dissolved one is cooled at 3 ° C. for 24 hours. This is not the case, and various organic substances are targeted. In addition, normal temperature as used in this specification means 15-25 degreeC. A crystal refers to a substance whose atomic arrangement has a spatially repeated pattern. Generally, a covalent bond crystal, an ionic crystal, a molecular crystal, a metal crystal, a hydrogen bond crystal, and the like are known as the type of crystal, but the type is not limited as long as it is a crystal taken by an organic compound. Confirmation that the target substance of the present invention is in a crystalline state can be achieved by various methods, for example, by using an X-ray diffractometer, or simply by observing the presence or absence of polarized light using a polarizing microscope. it can.

  Examples of highly crystalline substances include poorly water-soluble amino acids such as leucine and tyrosine; peptides; poorly water-soluble vitamins such as folic acid and vitamin K; polysaccharides; pigments such as β-carotene, astaxanthin and lutein; waxes Oils and fats such as milk fat, palm kernel oil, and cacao butter; physiologically active ingredients and useful ingredients such as unsaponifiable matter such as soybean, rice, rapeseed, and sesame can be exemplified. Further, if the compound is exemplified by focusing on the chemical structure from another point of view, fatty acids; sphingophospholipids such as ceramide; flavonoids such as flavones, flavonols, flavanones, flavonols, isoflavones, anthocyanes, flavanols, chalcones, aurones, etc. Phenylpropanoids such as ferulic acid, γ-oryzanol, lignin and lignan; benzoic acid derivatives; coumarin derivatives; stilbene derivatives; oxyanthraquinone derivatives; phenol derivatives such as phloroglucinol and orcinol; xanthone derivatives; Phthalide derivatives; acetylene derivatives; isoprenoids such as terpenoids, carotenoids and polyterpenoids; steroids; alkaloids; acid amide compounds such as sanshool and capsaicin; Le, pyrrole derivatives heme like; allantoin, imidazole derivatives such as biotin; indole derivatives; pyridine derivatives; pyrimidine derivatives; purine derivatives; pteridine derivatives; guanidine derivatives; sulfur-containing compounds such as α- lipoic acid. Furthermore, when classified from another viewpoint, aglycones from which the sugar is removed from the glycoside are also included in the category, and examples thereof include naringenin, quercetin, daidzein and the like. These may be used alone or in combination of two or more, and a composite effect or an additive synergistic effect can be expected. Among them, steroids, phenylpropanoids, sparingly water-soluble vitamins, flavonoids, sparingly water-soluble amino acids are more recommended as objects of the present invention from the viewpoint of usefulness when added to food and consumer demand. .

  The polyglycerin used in the polyglycerin fatty acid ester used in the highly crystalline substance-containing composition of the present invention has a hydroxyl value of 1200 or less, a primary hydroxyl group of 50% by weight or more of all the hydroxyl groups, and a cyclic product. One major characteristic is that polyglycerin having a content of 25% by weight or less and a fatty acid are esterified.

  By having the characteristics as described above, the polyglycerin fatty acid ester used in the highly crystalline substance-containing composition of the present invention is excellent in imparting water dispersibility of the highly crystalline substance and as a surfactant that suppresses crystallization. It can be used. That is, conventional polyglycerin fatty acid esters and food surfactants have insufficient performance and cannot be replaced.

  The polyglycerol in the polyglycerol fatty acid ester refers to a substance having a hydroxyl group and an ether bond in the molecule with a glycerol skeleton obtained by dehydration condensation of glycerol as a basic unit.

  The polyglycerol in the polyglycerol fatty acid ester used in the present invention is a polyglycerol having a primary hydroxyl group of 50% by weight or more among all the hydroxyl groups in the molecule. Solubilization performance and emulsion stability of the resulting polyglycerol fatty acid ester From the viewpoint of further improving the above, the primary hydroxyl group is preferably 55% by weight or more of polyglycerol, more preferably 60% by weight or more of polyglycerol. Further, the upper limit value is not particularly specified, but is desirably 90% by weight or less in order to maximize the effect. The proportion of primary hydroxyl groups in the total hydroxyl groups in the polyglycerol of the present application changes depending on the degree of condensation of the polyglycerols, and the types of polyglycerols that are generally distributed are tetra, penta, hexa, and deca. In consideration of this, the upper limit value is exemplified by tetraglycerin 70 wt% or less, preferably 65 wt% or less, pentaglycerin 75 wt% or less, preferably 70 wt% or less, and hexaglycerin 80 wt%. In the following, numerical values such as preferably 75% by weight or less, decaglycerin 85% by weight or less, preferably 80% by weight or less can be shown.

  Moreover, the hydroxyl value of polyglycerol is 1200 or less, 1100 or less are more preferable from a viewpoint which can adjust the hydrophilicity (HLB) of polyglycerol fatty acid ester according to a use, and 1000 or less are further more preferable. Further, from the viewpoint of workability and ease of esterification with a fatty acid, the hydroxyl value is preferably 770 or more.

  The proportion of primary hydroxyl groups among all hydroxyl groups is measured using a method of measuring a nuclear magnetic resonance spectrum (NMR) for carbon atoms. The hydroxyl value can be measured by a method known in the art.

In addition, the nuclear magnetic resonance spectrum (NMR) with respect to a carbon atom can be measured as follows. Polyglycerin 500 mg is dissolved in 2.8 ml of heavy water, and after filtration, ¹³ C-NMR (125 MHz) spectrum is obtained by gated decoupling. The peak intensity is proportional to the carbon number by the gate decoupled measurement method. The ¹³ C chemical shifts indicating the presence of primary hydroxyl groups and secondary hydroxyl groups are about 63 ppm for methylene carbon (CH ₂ OH) and about 71 ppm for methine carbon (CHOH), respectively. The abundance ratio of the primary hydroxyl group and the secondary hydroxyl group is calculated. However, the methine carbon (CHOH) indicating the secondary hydroxyl group overlaps with the methylene carbon peak further adjacent to the methine carbon bonded to the methylene carbon indicating the primary hydroxyl group, and the integral value of itself cannot be obtained. The integrated value is calculated from the signal intensity around 74 ppm of methylene carbon (CH ₂ ) adjacent to (CHOH).

  Furthermore, from the viewpoint of the stable water dispersibility of the highly crystalline substance, the polyglycerin cyclic body content is 25% by weight or less, preferably 5 to 20% by weight, more preferably 5 to 10% by weight. It is. In the present specification, the cyclic content refers to the content measured using a liquid chromatograph-mass spectrometer (LC / MS) method, and is calculated by the method described in the examples below.

  The method for preparing polyglycerol is not limited. For example, it can be obtained from dehydration condensation, commercially available polyglycerol by fractional purification or synthesis method, etc., but it is easy to keep the cyclic content low. The glycidol ring-opening polymerization method is preferable in that it can be produced.

  Fatty acid, which is another component of polyglycerin fatty acid ester, is a substance containing a carboxylic acid as a functional group obtained by hydrolyzing and extracting oils and fats extracted from natural animals and plants. There is no particular limitation. Alternatively, it may be a fatty acid obtained by chemically synthesizing petroleum or the like as a raw material. Alternatively, these fatty acids may be reduced by hydrogenation or the like, condensed fatty acids obtained by condensation polymerization of fatty acids containing hydroxyl groups, or polymerized fatty acids obtained by heat polymerization of fatty acids having unsaturated bonds. Good. The selection of these fatty acids may be appropriately determined in consideration of the desired effect. Specific examples of fatty acids used in the present invention include saturated or unsaturated fatty acids having 6 to 22 carbon atoms, that is, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitooleic acid, stearin. In addition to acids, isostearic acid, oleic acid, linoleic acid, linolenic acid, behenic acid, erucic acid, ricinoleic acid having a hydroxyl group in the molecule, 12-hydroxystearic acid, and their condensates are mentioned, among others, emulsification From the viewpoint of stability, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, and condensed ricinoleic acid are preferable, and myristic acid, palmitic acid, stearic acid, and oleic acid are more preferable. The degree of esterification is not particularly limited, but those having a high monoester content and a low esterification degree are preferred.

  Esterification of polyglycerol and fatty acid is performed according to a method known in the art. For example, the esterification can be performed under normal pressure or reduced pressure in the presence of an alkali catalyst, an acid catalyst, or no catalyst. Moreover, the polyglycerol fatty acid ester which has various properties can be prepared by changing the mixing amount of polyglycerol and a fatty acid. For example, when obtaining a polyglycerin fatty acid ester for use in a hydrophilic surfactant, the polyglycerin and the fatty acid are charged by calculating the weight so as to be equimolar by calculation from the hydroxyl value of the polyglycerin and the molecular weight of the fatty acid. What is necessary is just to increase the number-of-moles of a fatty acid, when obtaining the polyglyceryl fatty acid ester for using for lipophilic surfactant. The resulting polyglycerol fatty acid ester may be further purified according to the usage requirements of the product used. The purification method may be any known method and is not particularly limited. For example, adsorption treatment with activated carbon or activated clay, deodorization treatment under reduced pressure using water vapor or nitrogen as a carrier gas, washing with acid or alkali, or molecular distillation. And may be purified.

The HLB value of the polyglycerol fatty acid ester used in the present invention is 10 to 18, preferably 12 to 16, and more preferably 13 to 16, from the viewpoint of dispersibility of the highly crystalline substance in the aqueous phase. In addition, the HLB value here is the following formula:
HLB = 20 × (1-S / A)
(Wherein S: saponification value of ester, A: acid value of constituent fatty acid)
Means the value calculated by.

  The polyglycerin fatty acid ester used in the highly crystalline substance-containing composition of the present invention may be used alone or in combination with other surfactants from the viewpoint of improving the emulsion stability. For example, as the surfactant to be mixed, glycerin fatty acid ester, organic acid monoglyceride, monoglyceride derivative, propylene glycol fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene derivative, polyglycerin fatty acid ester (however, in the present invention) Nonionic surfactants (excluding polyglycerin fatty acid esters), amphoteric surfactants, anionic surfactants, cationic surfactants, lecithins, enzymatically decomposed lecithins, surfactants derived from natural products such as saponin, quilla extract, etc. Is mentioned. These may be used alone or in combination of two or more. Among them, it is preferable to use one or more of glycerin fatty acid ester, sucrose fatty acid ester and organic acid monoglyceride in combination. Furthermore, in consideration of stabilization and crystallization suppression when using highly crystalline substances in beverages, the constituent fatty acids of glycerin fatty acid esters are preferably stearic acid, isostearic acid, palmitic acid, oleic acid, myristic acid, and organic acid monoglycerides. Desirably, the organic acid moiety is citric acid, succinic acid, diacetyltartaric acid.

The liquid oil used in the present invention has an IOB value of 0.20 to 0.60, preferably 0.20 to 0.50, more preferably 0.20, from the viewpoint of the solubility of the highly crystalline substance and the low temperature stability. ~ 0.40. When the IOB value is outside this range, it is not preferable because sufficient dissolution and crystallization inhibition of the highly crystalline oil and fat cannot be obtained. In addition, the IOB value here is a numerical value obtained from the inorganic value and the organic value of the functional group of the compound in the organic conceptual diagram, and the following formula:
IOB = A value calculated by inorganic value / organic value, meaning that the larger the value, the higher the polarity. (Yoshio Koda "Organic Conceptual Diagram-Fundamentals and Applications-" (Sankyo Publishing, 1984) Issue).

  Specific examples of liquid oils having an IOB of 0.20 to 0.60 include neopentyl glycol dicaprylate (0.29), neopentyl glycol dicaprate (0.25), di (capryl / capric acid) propylene glycol ( 0.29), propylene glycol dicaprate (0.27), diglycene triisostearate (0.26), octyldodecyl lactate (0.36), glycerin diisostearate (0.29), pentaerythritol tetraoctanoate ( 0.35), dodeca (capryl / capric acid) decaglycerin (0.34), glycerin tricaprylate (0.35), tri (capryl / capric acid) glycerin (0.30), castor oil (0.40) 2-ethyl propanediol 2-ethylpropanediol (0.48), linalool (0. 8), polypropylene glycol (0.58), rosin (0.55), triglycerin diisostearate (0.59), and the like, and are not limited to these examples. The above can be used. The numbers in parentheses indicate IOB values.

  In the highly crystalline substance-containing composition of the present invention, it is of course possible that the composition is uniformly and stably dispersed in food and drink for a long period of time. , Stability during water dispersion is improved. Although it does not specifically limit as a polyhydric alcohol in this case, it is a general term for the compound which has two or more hydroxyl groups in 1 molecule, Propylene glycol, Dipropylene glycol, Glycerin, Diglycerin, Triglycerin, Polyglycerin, Ethylene glycol, diethylene glycol, polyethylene glycol, 3-methyl-1,3-butanediol, 1,3-butylene glycol, sorbitol, xylitol, 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, fructose, glucose liquid sugar, and solutions thereof. More than seeds It may be used in conjunction look. Among these, propylene glycol, glycerin, diglycerin, triglycerin, and polyglycerin can be preferably used from the viewpoint of ease of preparation and stability, and further, from the viewpoint that propylene glycol and glycerin can be used in foods.

  Furthermore, by making the highly crystalline substance-containing composition of the present invention into an oil-in-polyhydric alcohol (O / D type) emulsion, it can be easily dispersed in water, and crystals and precipitates are produced over time. No composition.

  The oil-in-polyol (O / D-type) emulsification in the present invention is obtained by dispersing an oil component in a polyhydric alcohol solution of a surfactant, and the oil and the polyhydric alcohol are passed through the surfactant. It is thought that it has a bicontinuous structure (bicontinuous structure). When a composition containing a highly crystalline substance has a bicontinuous structure, it becomes possible not only to form nano micelles easily without a strong stirring force, but also to a highly crystalline substance simultaneously in the nano micelles. It is presumed that it becomes possible to encapsulate. Conventionally, when a highly crystalline substance is blended as it is into a food or drink product or cosmetic, it can be blended only to such an extent that the highly crystalline substance does not precipitate. However, since this composition has a bicontinuous structure, it is possible to add a high crystalline substance in a stable and transparent state to foods and beverages or cosmetics. It has been found that it is possible to prepare water-based foods such as high-value beverages or cosmetics such as lotions and emulsions. Whether or not the composition has a bicontinuous structure can be easily identified by creating a three-component phase diagram with a surfactant, a polyhydric alcohol, and oil.

  The order of mixing the highly crystalline substance-containing composition of the present invention is not particularly limited. For example, a solution obtained by dissolving the polyglycerin fatty acid ester of the present invention in a polyhydric alcohol is an aqueous phase, separately from the highly crystalline substance and a liquid. It is obtained by a method of emulsifying an oil phase in which oil is dissolved and mixed, or a method of dissolving and mixing the polyglycerin fatty acid ester of the present invention, a liquid oil, and a highly crystalline substance, and then adding a polyhydric alcohol and further mixing. Can be done.

  The mixing ratio of the highly crystalline substance and the liquid oil is not particularly limited, but is preferably in the range of 99: 1 to 1:99, more preferably 90:10 to 2:98, and even more preferably 50: The range of 50-5: 95 is desirable.

  Further, the mixing temperature of the highly crystalline substance, liquid oil and polyglycerin fatty acid ester is not particularly limited, but from the viewpoint of uniformly mixing both substances, a state in which transparent dissolution can be confirmed visually is preferable. It is preferable to dissolve at the melting point of the highly crystalline substance.

  The mixing method with a highly crystalline substance is not particularly limited, and it can be obtained by emulsification using a stirring and emulsifying apparatus. For example, propeller type, anchor type, paddle type agitator, rotor / stator type emulsifier that can give stronger shearing force, mill type emulsifier with grinding function, high pressure nozzle type emulsifier that generates cavitation at high pressure , High-pressure collision emulsifiers that collide liquids under high pressure, and emulsify by impact force, shear force due to turbulent flow and cavitation, ultrasonic emulsifiers that generate cavitation with ultrasonic waves, membrane emulsification that uniformly emulsifies through pores Examples thereof include a static mixer that repeats a dispersed assembly of liquids in a machine and an element and uniformly mixes them. These can be used alone or in combination of two or more. From the viewpoint of high versatility, a rotor / stator type emulsifier and a paddle type stirrer are preferable.

  The composition of the highly crystalline substance-containing composition of the present invention is not particularly limited, and may be arbitrarily prepared according to the degree of purification of the highly crystalline substance to be used, the food or drink to be added, or the design of the cosmetic. The lower limit of the highly crystalline substance is preferably 0.1% by weight or more, more preferably 1% by weight or more from the viewpoint of physiological effects and influence on the flavor when applied to foods and drinks. And most preferably 15% by weight or more. The upper limit is preferably 80% by weight or less, more preferably 60% by weight or less, from the viewpoint of stability of emulsification. The polyglycerol fatty acid ester is preferably 0.01 to 80% by weight, more preferably 1 to 40% by weight. The liquid oil is preferably 0.1 to 30% by weight, more preferably 10 to 25% by weight. The polyhydric alcohol is preferably 1 to 99% by weight, more preferably 10 to 80% by weight.

  Other additive materials may be added in order to improve the product value of the highly crystalline substance-containing composition of the present invention or to adjust the fluidity to facilitate handling. Illustrative examples of such ingredients are sweeteners such as licorice extract, sodium saccharin, aspartame, gum arabic, pectin, carrageenan, farseleran, guar gum, locust bean gum, xanthan gum, alginic acid, methylcellulose, etc., gardenia Pigments, coloring agents such as yellow No. 4, preservatives such as sorbic acid and hinokitiol, antioxidants such as erythorbic acid, ascorbic acid, tocopherol, ferulic acid, rice bran oil extract, and acidulants such as citric acid and phytic acid Seasonings such as sodium inosinate and sodium glutamate, fragrances such as citrus flavors, milk flavors, yogurt flavors, vitamins such as vitamin A, vitamin D, vitamin E, vitamin C, vitamin B group, pantothenic acid, L- Lysine salt, L Threonine, amino acids such as L- tryptophan, calcium, iron, zinc, copper, minerals such as magnesium, fats, proteins, dextrin, ethanol, and a food material such as water.

  The highly crystalline substance-containing composition of the present invention can be used as a supplement to a living body of a highly crystalline substance by ingesting it as it is. For example, there are liquids, tablets, powder formulations, capsules and the like for the purpose of high crystallinity. Therefore, the food / beverage products which comprise the composition of this invention are provided as 1 aspect of this invention.

  As another aspect of the present invention, the present invention provides a food or drink comprising the high crystalline substance-containing progeny. The food / beverage products containing the highly crystalline substance-containing progeny of the present invention are particularly intended for humans, but do not exclude feed such as livestock and domestic pets. Below, although the food / beverage products for humans are demonstrated, the said feed is also included in the food / beverage products of this invention.

  It does not specifically limit as food / beverage products, What is necessary is just food / beverage products containing the highly crystalline substance containing composition of this invention. Examples of such foods and drinks include instant noodles, cup noodles, retort / cooked food, cooked canned food, microwave food, instant soup / stew, instant miso soup / soup, canned soup, freeze-dried food, carbonated drinks, Natural fruit juice, juice drink, soft drink with fruit juice, fruit drink, fruit food with fruit granules, vegetable drink, soy milk / soy milk drink, coffee drink, tea drink, powdered drink, concentrated drink, sports drink, nutrition drink, alcoholic drink Beverages such as bread, macaroni / spaghetti, noodles, cake mix, fried flour / bread crumbs, gyoza / spring rolls and other flour foods, caramel candy, chewing gum, chocolate, cookies / biscuits, cakes / pies, Snack crackers, Japanese confectionery, rice confectionery, bean confectionery, dessert confectionery, soy sauce, mi , Sauces, processed tomato seasonings, mirins, vinegars, sweeteners, fish sauce, nyocumam and other basic seasonings, flavor seasonings, cooking mix, curry base, sauces, dressing, noodle soup, spices, etc. Complex seasonings, fat and fat foods such as butter, margarine, mayonnaise, milk and processed milk, milk drinks, yogurts, lactic acid bacteria drinks, cheese, ice cream, prepared milk powder, dairy products such as cream, semi-cooked frozen food, cooking Frozen foods such as finished frozen foods, canned fish and paste, fish ham and sausages, fish paste products, marine products, marine products such as dried fish, boiled fish, canned and pasted livestock products, meat ham and sausages, and livestock products Processed livestock products such as vegetables, canned agricultural products, canned fruits, jams and marmalades, pickles, boiled beans, dried agricultural products, cereals and other processed agricultural products, baby food, baby food, pretend Only, it can be exemplified Ochazuke glue, supplements and the like.

  As one embodiment of the present invention, there is provided a cosmetic comprising the highly crystalline substance-containing composition of the present invention. The cosmetic is not particularly limited, and examples thereof include lotion, emulsion, shampoo, rinse, hair cosmetic, foundation, lipstick, and moisturizing cream.

  The food / beverage products or cosmetics of the present invention can be obtained, for example, by adding the highly crystalline substance-containing composition of the present invention to an existing food / beverage product. It can be prepared by adding the composition of the present invention to the raw materials used in advance or by blending it together during the preparation process. If the food / beverage products or cosmetics which can express the desired effect of this invention are obtained, it will not specifically limit about the addition time and addition method of the composition of this invention to this product.

  Since the food / beverage product containing the highly crystalline substance-containing composition of the present invention has a high crystalline substance dispersed stably, the food / beverage product or cosmetic of the present invention is a crystal formed by precipitation of the highly crystalline substance. No cloudiness or precipitation is observed, and there is no roughness or oiliness. In particular, it is excellent in stability in salt, acid, and alcohol solutions assumed in food and drink, poor circulation such as repeated high and low temperatures, and no generation of crystals even under storage conditions. A highly crystalline substance can be imparted to a food or drink or a cosmetic without deteriorating the feeling of use. Among these, beverages such as sports drinks, functional beverages, and tea beverages are regarded as transparent, but the composition of the present invention has a highly crystalline substance stably emulsified or solubilized, so that beverages and the like are transparent. A highly crystalline substance can be highly blended in a beverage without impairing the feeling.

  The content of the highly crystalline substance-containing composition of the present invention in the food / beverage product or cosmetic of the present invention is not particularly limited as long as the content of the present invention is not impaired. From the viewpoint that the emulsifying agent does not affect the flavor of the food and drink and the feeling of use of cosmetics, it is preferably 0.005 to 50% by weight, more preferably 0.01 to 20% by weight, and still more preferably 0.1 to 10%. It is desirable to be weight percent.

  EXAMPLES Hereinafter, although an Example is shown and this invention is demonstrated concretely, this invention is not restrict | limited to the following Example.

Examples 1-24 and Comparative Examples 1-12
The surfactant and liquid oil shown in Tables 2 to 4 were put into a beaker, heated to 80 ° C., and then stirred and mixed at 6000 r / min using a homomixer. Highly crystalline substances shown in Tables 2 to 4 were added to the resulting mixture, and the mixture was further heated and stirred to mix. After visually confirming that the highly crystalline substance is completely dissolved and the solution is transparent, polyhydric alcohol previously heated to 80 ° C. in another beaker was added, and Table 2 Water or alcohol was added according to the formulation of ˜4, and the mixture was stirred and mixed at 6000 rpm to obtain compositions of Examples 1 to 24 and Comparative Examples 1 to 12. The HLB of the polyglycerin fatty acid ester used, the hydroxyl value of the polyglycerin, the primary hydroxyl group content and the cyclic body content are as shown in Table 1.

  In addition, the cyclic body content of the used polyglycerol was analyzed using the liquid chromatograph-mass spectrometer (LC / MS) on the conditions shown below.

<LC / MS conditions>
Ionization mode; APCI, negative
Measurement range: 90-2000 m / z
Column; TSKgel α-2500 (7.8 × 300 mm)
Temperature: 40 ° C
Eluent: H ₂ O / acetonitrile 7/3
Flow rate: 0.8ml / min
Injection volume: 10 μl, 100 ppm
Analysis time: 20 minutes

  Moreover, the hydroxyl value of the used polyglycerol was computed according to the 7th edition food additive process manual "Oil and fats test method".

The proportion of primary hydroxyl groups was determined by spectral analysis using a nuclear magnetic resonance apparatus. That is, using a nuclear magnetic resonance apparatus ( ¹³ C-NMR: JNM-A500, manufactured by JEOL Ltd.), the ratio of primary hydroxyl groups and secondary hydroxyl groups of polyglycerol was analyzed. Polyglycerin 500 mg is dissolved in 2.8 ml of heavy water, and after filtration, ¹³ C-NMR (125 MHz) spectrum is obtained by gated decoupling. The peak intensity is proportional to the carbon number by the gate decoupled measurement method. The ¹³ C chemical shifts indicating the presence of primary hydroxyl groups and secondary hydroxyl groups are about 63 ppm for methylene carbon (CH ₂ OH) and about 71 ppm for methine carbon (CHOH), respectively. The abundance ratio of the primary hydroxyl group and the secondary hydroxyl group is calculated. However, the methine carbon (CHOH) indicating the secondary hydroxyl group overlaps with the methylene carbon peak further adjacent to the methine carbon bonded to the methylene carbon indicating the primary hydroxyl group, and the integral value of itself cannot be obtained. The integrated value was calculated from the signal intensity around 74 ppm of methylene carbon (CH ₂ ) adjacent to (CHOH).

  In addition, it was confirmed by observing under a polarizing microscope that the substance to be formulated used in this example was in a crystalline state at room temperature by showing polarized light.

Test Example 1 [Emulsification stability]
The obtained compositions of Examples 1 to 24 and Comparative Examples 1 to 12 were filled into a 100 ml transparent bottle and then sealed. About each composition, the state after storage for 4 weeks in the dark place of 5 degreeC, 25 degreeC, and 50 degreeC was confirmed visually, and the emulsion stability was evaluated from the following evaluation criteria. The results are shown in Tables 2-4.

<Evaluation criteria for emulsion stability>
◎: Crystal precipitation and turbidity are not observed and transparent ○: Turbidity is observed △: Turbidity is observed and crystals are slightly deposited (about several to a dozen or so)
X: Turbidity is observed, and many crystals are deposited (several tens or more)
XX: A lot of crystals are precipitated and the phases are completely separated. In all temperature ranges, ◎ and ○ are acceptable products.

Test Example 2 [Stability in aqueous solution]
The compositions of Examples 1 to 24 and Comparative Examples 1 to 12 were mixed with 0.24% by weight of citric acid, 0.04% by weight of sodium citrate and 1% by weight of sodium chloride so that the concentration of the highly crystalline substance was 0.05% by weight. % And diluted with an aqueous solution of pH 2.8 to prepare a diluted solution containing a highly crystalline substance. The obtained diluted solution was filled into a 100 ml transparent glass bottle, stored at 55 ° C. for 72 hours, and then stored at 3 ° C. for 72 hours as one cycle, and this cycle was repeated 5 cycles and stored in the dark. About the sample after a preservation | save, a state was confirmed visually and the external appearance was evaluated from the following evaluation criteria. The results are shown in Tables 2-4.

<Stability evaluation criteria>
A: Transparent with no crystal precipitation or turbidity (characters can be confirmed through the container bottle)
○: Turbidity is observed △: Crystals are slightly precipitated (about several to a dozen)
×: Many crystals are deposited (several tens or more)
◎ and ○ are acceptable products.

Examples 25-39 and Comparative Examples 13-19
The sports drink ingredients in Table 5 were mixed to obtain a beverage base having a pH of 3.4. The compositions of Examples 1, 5, 6, 12 to 24 and Comparative Examples 1 to 7 were diluted with a beverage base so that the concentration of the highly crystalline substance was 0.01% by weight, and sterilized by heating at a temperature of 93 ° C. Thereafter, a colorless and transparent 500 ml PET bottle was hot-packed and cooled to obtain a transparent to milky white sports drink containing a highly crystalline substance.

Test Example 3 [Stability in Beverages]
The sports drinks of Examples 25 to 39 and Comparative Examples 13 to 19 were stored at 37 ° C. for 24 hours, −10 ° C. for 24 hours, and then stored at 5 ° C. for 24 hours as one cycle. Was repeated in the dark for 10 cycles. About the drink after a preservation | save, a state was confirmed visually and the external appearance was evaluated from the following evaluation criteria. In addition, the crystal generation | occurrence | production date was shown about the sample in which the crystal | crystallization generate | occur | produced before completion | finish of evaluation. The results are shown in Table 6.

<Evaluation criteria for dispersion stability>
A: Translucent solution, no crystals or precipitates observed (ability to recognize characters through the container)
○: White turbid solution with no crystals or precipitates △: White turbid solution with fine crystals ×: Many crystals and precipitates recognized
◎ and ○ are acceptable products.

Test Example 4 [Change in Turbidity]
Moreover, the turbidity of the sports drinks of Examples 25 to 39 and Comparative Examples 13 to 19 stored under the same conditions as in Test Example 3 was measured as absorption light intensity at a wavelength of 650 nm using a spectrophotometer. Based on the turbidity of the sample before storage, the change rate after storage was calculated by the following formula. In addition, the thing which the crystal | crystallization generate | occur | produced was made impossible to measure. The results are shown in Table 6.

<Calculation formula>
Rate of change (%) = (turbidity after storage / turbidity before storage) × 100

Examples 40-42 and Comparative Examples 20-22
The alcoholic beverage ingredients in Table 7 were mixed to make a beverage base. The compositions of Examples 1, 4, 10 and Comparative Examples 8, 11, 12 were diluted with a beverage base so that the concentration of the highly crystalline substance was 0.05% by weight, filled into a 180 ml can, It was sterilized and cooled in minutes to obtain a transparent to milky white alcoholic beverage containing a highly crystalline substance.

Test Example 5 [Stability in Beverages]
For the alcoholic beverages of Examples 40 to 42 and Comparative Examples 20 to 22, after storage at 37 ° C. for 24 hours, storage at −10 ° C. for 24 hours, and then storage at 5 ° C. for 24 hours as one cycle, this cycle Was repeated in the dark for 10 cycles. The sample after storage was transferred to a 100 ml beaker, the state was visually confirmed, and the appearance was evaluated according to the same evaluation criteria as in Test Example 3. In addition, the crystal generation | occurrence | production date was shown about the sample in which the crystal | crystallization generate | occur | produced before completion | finish of evaluation. The results are shown in Table 8.

Test Example 6 [Change in particle diameter]
Moreover, the average particle diameter of the alcoholic beverage of Examples 40-42 and Comparative Examples 20-22 preserve | saved on the same conditions as Test Example 5 was measured with the particle size distribution measuring device (Beckman Coulter company make: LS-230). The change rate of turbidity after storage was calculated using the following equation based on the particle size of the sample before storage. The results are shown in Table 8.

<Calculation formula>
Rate of change (%) = (average particle diameter after storage (μm) / average particle diameter before storage (μm)) × 100

Example 43 and Comparative Example 23
The cosmetic ingredients shown in Table 9 were stirred and mixed to obtain the lotions of Example 43 and Comparative Example 23. The ferulic acid used in Comparative Example 23 is the same as that in Example 23.

Test Example 7 [Stability of aqueous solution]
The lotion of Example 43 and Comparative Example 23 was stored at 55 ° C. for 1 week, then stored at 3 ° C. for 1 week as one cycle, and this cycle was repeated 12 cycles and stored in the dark. About the sample after a preservation | save, a state was confirmed visually and the external appearance was evaluated by the evaluation criteria similar to Test Example 3. In addition, the crystal generation | occurrence | production date was shown about the sample in which the crystal | crystallization generate | occur | produced before completion | finish of evaluation. The results are shown in Table 10.

Example 44 and Comparative Example 24
Emulsions were prepared according to the proportions shown in Table 11. Propylene glycol, glycerin and triethanolamine were added to purified water and mixed by heating to obtain an aqueous phase. Further, other components were mixed at 70 ° C., and this oil phase part was added to the aqueous phase part for preliminary emulsification. The compositions of Example 2 and Comparative Example 1 were mixed so that the concentration of the highly crystalline substance was 0.5% by weight, uniformly emulsified with a homomixer, and cooled to 30 ° C. after emulsification to obtain an emulsion. It was.

Test Example 8 [Confirmation of Usability]
The emulsions of Example 44 and Comparative Example 24 were stored at 55 ° C. for 1 week and then stored at 3 ° C. for 1 week as one cycle, and this cycle was repeated 12 cycles and stored in the dark. About the sample after a preservation | save, the usability | use_condition was apply | coated and confirmed and it evaluated from the following evaluation criteria. The results are shown in Table 12. In addition, the score of evaluation in Table 12 is the average score of each panel scored on the following reference | standard.

<Evaluation criteria>
Smooth and good elongation: 4 points Smooth but poor elongation: 3 points Slightly rough feel: 2 points Very rough feel: 1 point

  From the above results, the highly crystalline substance-containing composition prepared with a specific polyglycerin fatty acid ester is a good emulsified state even in the presence of factors that adversely affect the emulsification of salts, acids, alcohols, etc. It was found to maintain. This is considered to be because the highly crystalline substance is stably emulsified or solubilized by containing a specific polyglycerin fatty acid ester and liquid oil. Thereby, in preparing food and drink and cosmetics containing highly crystalline substances, it was confirmed that they were widely used for cosmetics without any difficulty.

  As shown in the above test examples, the highly crystalline substance-containing composition of the present invention prepared with a specific polyglycerin fatty acid ester is a highly crystalline substance that could not be stably dispersed in the past. It is apparent that crystallization, separation, etc. can be suppressed and added to foods and drinks or cosmetics.

Claims (5)

A highly crystalline substance-containing composition containing the following (A) to (C).
(A) Highly crystalline substance (B) Polyglycerin and fatty acid having a hydroxyl value of 1200 or less and a primary hydroxyl group of 50% by weight or more of all the hydroxyl groups and a cyclic content of 25% by weight or less Esterified polyglycerin fatty acid ester (C) Liquid oil having an IOB (inorganic / organic balance) value of 0.20 to 0.60 2. The highly crystalline substance-containing composition according to claim 1, wherein the composition is an oil-in-polyol (O / D) emulsion. The highly crystalline substance-containing composition according to claim 1 or 2, wherein the polyglycerol fatty acid ester has an HLB value of 10 to 18. Food-drinks containing the highly crystalline substance containing composition in any one of Claims 1-3. Cosmetics containing the highly crystalline substance containing composition in any one of Claims 1-3.