WO2018003965A1 - Procédé de production d'une formulation en poudre d'acide fumarique - Google Patents

Procédé de production d'une formulation en poudre d'acide fumarique Download PDF

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Publication number
WO2018003965A1
WO2018003965A1 PCT/JP2017/024108 JP2017024108W WO2018003965A1 WO 2018003965 A1 WO2018003965 A1 WO 2018003965A1 JP 2017024108 W JP2017024108 W JP 2017024108W WO 2018003965 A1 WO2018003965 A1 WO 2018003965A1
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Prior art keywords
fumaric acid
powdered
mass
disaccharide
acid
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PCT/JP2017/024108
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English (en)
Japanese (ja)
Inventor
段王　保文
克彦 日野
西本　友之
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株式会社林原
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Priority to JP2018525288A priority Critical patent/JPWO2018003965A1/ja
Publication of WO2018003965A1 publication Critical patent/WO2018003965A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B7/00—Preservation or chemical ripening of fruit or vegetables
    • A23B7/10—Preserving with acids; Acid fermentation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen

Definitions

  • the present invention relates to a method for producing a powdered fumaric acid formulation containing fumaric acid as an active ingredient, and a powdered fumaric acid formulation obtained by the production method.
  • Fumaric acid is an organic acid that has the strongest acidity next to acetic acid and succinic acid, and its acidity is said to be about 1.5 times that of citric acid and malic acid widely used in fruit juice beverages. ing.
  • acetic acid and succinic acid are volatile, while fumaric acid is non-volatile, and succinic acid is physiologically harmful, whereas fumaric acid is harmless.
  • fumaric acid is relatively inexpensive and has a strong sterilizing power, it has been widely used as a food additive such as a sour agent and a food preservative.
  • fumaric acid has a very low solubility in water (the solubility in water at 25 ° C.
  • solution-form fumaric acid preparations such as acidulants, preservatives, and disinfectants containing fumaric acid as an active ingredient is usually inefficient and requires a lot of labor.
  • Patent Document 1 proposes that a polyglycerin fatty acid ester is mixed and supported in a hydrophobic powder containing fumaric acid. ing.
  • Patent Document 2 discloses a disinfecting detergent that improves the dissolution rate by coating fumaric acid particles with a hydrophilic nonionic surfactant.
  • Patent Document 3 discloses a fumaric acid preparation containing 2.5 to 10% by weight of a dextrose equivalent maltextrin wetting agent containing 75% by weight of a polysaccharide of trisaccharides or more based on fumaric acid.
  • Patent Document 4 is characterized in that glucose or sucrose is blended as an auxiliary agent in an intimate mixture of finely powdered fumaric acid and a surfactant. Methods for producing fumaric acid-containing compositions with improved dissolution rates are disclosed respectively.
  • the methods described in Patent Documents 1 to 4 are used to treat the surface of the fumaric acid particles with polyglycerol fatty acid ester or Since it coats with sucrose fatty acid ester etc., there exists a problem that the obtained fumaric acid formulation is easy to aggregate and solidify under the influence of these surfactant.
  • the present invention has been made to solve the above-mentioned drawbacks of the prior art, exhibits excellent solubility in solvents such as water, is difficult to agglomerate and solidify in the manufacturing process, and is easy to prepare. It is another object of the present invention to provide a method for producing a powdered fumaric acid preparation that maintains the original effects of fumaric acid such as a sterilizing effect at a satisfactory level, and a powdered fumaric acid preparation obtained by the production method. To do.
  • Patent Document 1 or 2 In the process of examining the solution of the above problems, the present inventors have disclosed a method disclosed in Patent Document 1 or 2 in which the surface of fumaric acid particles is coated with a hydrophilic nonionic surfactant such as glycerin fatty acid ester.
  • a powdered fumarate formulation When a powdered fumarate formulation is prepared, the dissolution rate of the fumaric acid powder is improved, but the powdered fumaric acid formulation is agglomerated in the production process and the passage of the sieve is reduced, so that the workability in the production of the powdered formulation is reduced and the final product As a result, it was found that the yield of the powdered fumaric acid preparation was significantly reduced.
  • the present invention is a method for producing a powdered fumaric acid preparation containing fumaric acid as an active ingredient, (1) 0.5% by mass or more and less than 10.0% by mass of non-reducing disaccharide or disaccharide in terms of anhydride with respect to fumaric acid powder, hydrophilic nonionic surfactant and fumaric acid powder A sugar alcohol in the presence of a solvent to obtain a fumaric acid-containing wet mixture; (2) The obtained fumaric acid-containing wet mixture is dried, and the fumaric acid-containing granular composition in which the fumaric acid particles are coated with a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol less than a disaccharide.
  • this invention solves said subject by providing the powder fumaric acid formulation manufactured by said manufacturing method,
  • the powder fumaric acid formulation manufactured by the said manufacturing method is solvent, such as water.
  • the fumaric acid, which is an active ingredient, is contained at a concentration that provides a satisfactory level of the original action and effect of fumaric acid. Since it is hard to tie, it has the characteristic of stably maintaining fluidity as a powder even during storage and distribution.
  • a powdered fumaric acid preparation having stable powder fluidity and an excellent dissolution rate is industrially produced while maintaining the original sterilizing effect of fumaric acid, which is an active ingredient, at a satisfactory level. Can be provided easily, in large quantities, and stably at low cost.
  • the powdered fumaric acid preparation obtained by the production method of the present invention is a high-quality powdered fumaric acid preparation excellent in powder flowability and dissolution rate.
  • the present invention relates to a method for producing a powdered fumaric acid preparation containing fumaric acid as an active ingredient, which comprises the following steps (1) to (3): (1) 0.5% by mass or more and less than 10.0% by mass of non-reducing disaccharide or disaccharide in terms of anhydride with respect to fumaric acid powder, hydrophilic nonionic surfactant and fumaric acid powder A sugar alcohol in the presence of a solvent to obtain a fumaric acid-containing wet mixture; (2) The obtained fumaric acid-containing wet mixture is dried, and the fumaric acid-containing granular composition in which the fumaric acid particles are coated with a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol less than a disaccharide. And (3) a step of pulverizing and classifying the obtained fumaric acid-containing granular composition as necessary to obtain a powdered fumaric acid preparation.
  • the manufacturing method of the powder fumaric acid formulation of this invention The outline of the method for producing the powdered fumaric acid preparation of the present invention will be described below.
  • a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol less than a disaccharide are added in the presence of a solvent.
  • the fumaric acid particles are coated with a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol less than a disaccharide, and then dried to remove the solvent, and the resulting granules
  • commercially available fumaric acid powder can be used as the raw material.
  • Commercially available fumaric acid powder is usually a white crystalline powder, has no odor, and has a strong acidity.
  • trade name “Fumaric acid” sold by Nippon Shokubai Co., Ltd. trade name “Fumaric acid” sold by Fuso Kogyo Co., Ltd. can be used.
  • the particle size of fumaric acid used as the active ingredient of the preparation is not particularly limited, but the smaller the particle size, the better the water dispersibility and dissolution rate.
  • the particle size of commercially available fumaric acid as a raw material is relatively large, it is preferable to pulverize in advance and adjust the particle size of fumaric acid to usually 150 ⁇ m or less, desirably 75 ⁇ m or less.
  • the particle size of fumaric acid exceeds 150 ⁇ m, the dissolution rate in water tends to decrease.
  • a nonionic surfactant is preferable, and the surface of the fumaric acid particles is coated to improve the dispersibility and dissolution rate of fumaric acid in water. Therefore, a hydrophilic nonionic surfactant is more preferable than a lipophilic nonionic surfactant.
  • hydrophilic nonionic surfactants include sucrose fatty acid esters, sorbitan fatty acid esters, glycerin fatty acid esters, and polyglycerin fatty acid esters. Especially, polyglycerin fatty acid esters are highly effective in improving the fumaric acid dissolution rate. Is preferred.
  • hydrophilic nonionic surfactant a hydrophilic / lipophilic balance (hereinafter abbreviated as “HLB”).
  • HLB takes a value from 0 to 20, and the closer to 0, the more lipophilic.
  • HLB hydrophilic nonionic surfactant having an HLB in the range of 14 to 18, preferably using a hydrophilic nonionic surfactant having a range of 14 to 18.
  • the advantage that the effect of improving the dissolution rate of fumaric acid in water is the highest is obtained.
  • the powder fumaric acid preparation of the present invention obtained, for example, for foods can be obtained even if it is added. It also has the advantage of not hindering its use as a disinfectant cleaning agent.
  • the amount of the hydrophilic nonionic surfactant used for coating the fumaric acid particles is not particularly limited as long as the dispersibility and dissolution rate of fumaric acid in water are improved.
  • anhydride it is usually 0.1 to 3.0% by mass, preferably 0.3 to 1.0% by mass, more preferably about 0.5% by mass.
  • the greater the amount of hydrophilic nonionic surfactant added the better the effect of improving the dissolution rate of the powdered fumaric acid preparation, and a sufficient effect is usually obtained at 0.1% by mass or more.
  • the addition amount is too large, the fumaric acid particles are liable to aggregate, so the addition amount of the hydrophilic nonionic surfactant is preferably 3.0% by mass or less.
  • examples of the saccharide used for coating the fumaric acid particles include a non-reducing disaccharide or a sugar alcohol having a disaccharide or less.
  • the non-reducing disaccharides or the sugar alcohols below the disaccharide trehalose, sorbitol, and maltitol are preferable from the viewpoint of improving the cohesiveness and sieving ability of the powdered fumaric acid preparation.
  • trehalose, sorbitol or maltitol By using trehalose, sorbitol or maltitol, the dissolution rate of fumaric acid in the powdered fumaric acid preparation in water can be improved, and the cohesiveness and sieving ability of the powdered fumaric acid preparation can be improved.
  • trehalose, sorbitol and maltitol all have no reducing aldehyde group and have low reactivity, there is also an advantage that the obtained powdered fumaric acid preparation is difficult to be colored.
  • the addition amount of the non-reducing disaccharide or the disaccharide or less sugar alcohol used for coating the fumaric acid particles is usually 0.5% by mass or more in terms of anhydride with respect to fumaric acid.
  • the content is preferably less than 10.0% by mass, and more preferably 1.0 to 5.0% by mass.
  • the addition amount of non-reducing disaccharide or sugar alcohol less than disaccharide is 10.0% by mass or more, the fumaric acid particles coated with the hydrophilic nonionic surfactant and the saccharide in the production process are blocked. It is easy to solidify and solidify, making it difficult to pulverize, and there is a disadvantage that the work efficiency in production is reduced.
  • the addition amount of non-reducing disaccharide or sugar alcohol less than disaccharide is less than 0.5% by mass, it is difficult to obtain the effect of improving the cohesiveness and sieving ability of the powdered fumaric acid preparation.
  • the solvent used to obtain the fumaric acid-containing wet mixture is particularly limited as long as it dissolves a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol having a disaccharide or less.
  • a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol having a disaccharide or less.
  • water or ethyl alcohol and more preferably water.
  • the amount of the solvent to be used is not particularly limited as long as it is an amount capable of dissolving the added hydrophilic nonionic surfactant and the non-reducing disaccharide or the sugar alcohol less than the disaccharide. Usually, it is preferably 50% by mass or more and more preferably 80% by mass or more with respect to the acid. When the amount of the solvent used is less than 50% by mass, the fluidity of the fumaric acid-containing wet mixture during mixing is significantly reduced, and a large load is imposed on the mixing operation, so that uniform mixing becomes difficult and workability is poor. This is not desirable.
  • the amount of solvent used is too large, it takes a lot of time and energy in the process of drying the fumaric acid-containing wet mixture and removing the solvent. 300 mass% or less is preferable, and 200 mass% or less is more preferable.
  • a fumaric acid powder is mixed with a hydrophilic nonionic surfactant solution and a non-reducing disaccharide or a sugar alcohol solution of a disaccharide or less, and then the solvent is removed to obtain fumaric acid powder particles. It is coated with a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol less than the disaccharide.
  • a mixer or the like it is preferable to grind to about 150 ⁇ m or less, more preferably about 75 ⁇ m or less.
  • the step of mixing a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol of a disaccharide or less with fumaric acid powder in the presence of a solvent is performed by simultaneously mixing these three in the presence of a solvent.
  • the fumaric acid powder may be mixed with a nonionic disaccharide or a sugar alcohol having a disaccharide or less in the presence of an appropriate amount of solvent, and then further mixed with a hydrophilic nonionic surfactant. Is more preferable.
  • the surface of the fumaric acid particles is first coated with a non-reducing disaccharide or a sugar alcohol less than the disaccharide, and further coated with a hydrophilic nonionic surfactant. The effect of improving the dissolution rate is improved.
  • the step of mixing the fumaric acid powder, the hydrophilic nonionic surfactant and the non-reducing disaccharide or the sugar alcohol of the disaccharide or less in the presence of a solvent is performed by any means. Although it may be sufficient and it does not restrict
  • the conditions at the time of mixing are not particularly limited as long as the fumaric acid powder particles are coated with a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol of a disaccharide or less, and heating conditions as necessary It can also be mixed below.
  • fumaric acid powder, a hydrophilic nonionic surfactant, and a non-reducing disaccharide or a sugar alcohol less than a disaccharide are mixed, and then the solvent is dried and removed from the wet mixture.
  • the step of making the acid-containing granular composition may be carried out by any means and is not particularly limited, but examples thereof include spray drying, drum drying, reduced pressure drying, heat drying, freeze drying and the like. Can be carried out using any appropriate means widely used. Although the drying conditions vary depending on the type of solvent, etc., when the solvent is, for example, water, it is desirable to remove it by drying under reduced pressure by heating to about 70 to 100 ° C. in order to reduce cost and increase efficiency.
  • the production method of the present invention includes a step of pulverizing the fumaric acid-containing granular composition obtained by drying, if necessary. That is, if the particle size of the obtained fumaric acid-containing granular composition satisfies the particle size conditions required for a powdered fumaric acid formulation, the fumaric acid-containing granular composition obtained by drying is directly used as a powdered fumaric acid formulation. However, when the particle size of the obtained fumaric acid-containing granular composition is larger than the particle size required for the powdered fumaric acid preparation, it may be appropriately pulverized.
  • the pulverizing means is not particularly limited, and can be performed using appropriate pulverizing means widely used in the field such as a mortar, a mill, a fine pulverizer, and an atomizer.
  • appropriate pulverizing means widely used in the field such as a mortar, a mill, a fine pulverizer, and an atomizer.
  • the addition amount of the non-reducing disaccharide or the sugar alcohol below the disaccharide to the fumaric acid powder is 10% by mass or more in terms of anhydride
  • the entire fumaric acid-containing granular composition is solidified (blocked).
  • the amount of the saccharide added is small, such a problem relating to pulverization does not occur.
  • the production method of the present invention includes a step of classifying the fumaric acid-containing granular composition obtained by drying or a pulverized product thereof as necessary, and adjusting the particle size distribution required for the powdered fumaric acid preparation.
  • the classifying means is not particularly limited, and can be performed using appropriate classifying means widely used in the field such as a wire mesh, a test sieve, a vibration sieve, and an ultrasonic vibration sieve. Since the dispersibility and dissolution rate of fumaric acid in water are also related to the particle size of the preparation, the particle size is usually adjusted to 500 ⁇ m or less, preferably 300 ⁇ m or less by classification.
  • the present invention is a powdered fumaric acid preparation produced by the production method of the present invention described above, that is, fumaric acid particles are coated with a hydrophilic nonionic surfactant and a non-reducing disaccharide or a sugar alcohol less than a disaccharide. It is also related to powdered fumaric acid preparation, and the powdered fumaric acid preparation corresponds to the addition ratio of various compounds in the production method, and is 0.5% by mass or more and less than 10.0% in terms of anhydride with respect to fumaric acid. % Non-reducing disaccharides or sugar sugars less than or equal to disaccharides.
  • the powdered fumaric acid preparation of the present invention is in a form in which a crystalline powder of fumaric acid is coated with a hydrophilic nonionic surfactant and a specific amount of a non-reducing disaccharide or a sugar alcohol less than a disaccharide. It is the formulation characterized by this.
  • powdered fumaric acid preparation of the present invention other components such as a chelating agent, a thickening agent, an emulsifying agent, a fragrance, a coloring agent, and the like can be appropriately blended as necessary.
  • other edible disinfectants can be added to the powdered fumaric acid preparation of the present invention.
  • examples of other edible sterilizing agents include sodium hypochlorite, sodium chlorite, high-grade salty powder, and hydrogen peroxide.
  • an organic acid other than fumaric acid, a derivative thereof, or a salt thereof can be used in appropriate combination.
  • organic acids other than fumaric acid include citric acid, malic acid, tartaric acid, succinic acid, lactic acid, acetic acid, propionic acid, sorbic acid, benzoic acid, ascorbic acid, and the like.
  • glycosyl derivatives, acylated derivatives, phosphorylated derivatives and the like can be mentioned, and examples of salts thereof include sodium salts, potassium salts, magnesium salts, calcium salts, ammonium salts and the like.
  • a combination of fumaric acid and citric acid, malic acid, tartaric acid and ascorbic acid is preferable, and a combination of ascorbic acid or a derivative thereof or a salt thereof is particularly preferable.
  • the amount of an organic acid other than fumaric acid, a derivative thereof, or a salt thereof is preferably more than an equivalent amount, and more preferably twice or more the amount of fumaric acid. If the amount of the organic acid other than fumaric acid, its derivative or their salt is equal to or less than that, it is not desirable because the effect of improving the antibacterial activity and / or expanding the antibacterial target is reduced.
  • the amount of the organic acid other than fumaric acid to be combined, the derivative thereof or the salt thereof is too large, the effect of improving the cohesiveness and sieving property of the powdered fumaric acid preparation is difficult to be obtained. 20 times or less is preferable and 12 times or less is more preferable.
  • step (1) it may be added and mixed with other components, and in the step (2), a wet mixture before or during drying, Or it can mix with the granular composition after drying, and, in the process of (3), it can be mixed before, during or after pulverization or classification.
  • step (2) it may be added and mixed with other components
  • step (3) it can mix with the granular composition after drying
  • step (3) it can be mixed before, during or after pulverization or classification.
  • the organic acid other than fumaric acid, its derivative, or salt thereof may be mixed at the same time at any one of the timings described above, or may be mixed at two or more timings divided into two or more. .
  • the intended use of the powdered fumaric acid preparation of the present invention is not particularly limited, but as it is or after being dispersed, dissolved and diluted, and further containing an alcohol such as ethanol, an antibacterial agent, etc. It can be used as a sour agent, a preservative, a sterilizing detergent, or as a detergent for tanks and lines in foods and food factories, and can also be used as a general sterilizing detergent. . *
  • the powdered fumaric acid preparation of the present invention is used as a sterilizing detergent for foods, it is usually dispersed and dissolved uniformly in water or warm water, and the concentration of fumaric acid is preferably 0.05 to 1% by mass, More preferably, it is used as a treatment liquid of about 0.1 to 0.5% by mass.
  • concentration of the treatment liquid is less than 0.05% by mass, it is difficult to obtain the intended sterilizing effect.
  • concentration of the treatment liquid is too high, the food has a strong acidity and may deteriorate the flavor.
  • the treatment liquid for the sterilization detergent for food can be used as a treatment liquid for sterilization of food materials such as vegetables, fruits, seafood, and meat. *
  • the powdered fumaric acid preparation of the present invention when used for processing foodstuffs of vegetables, fruits, seafood, meat, etc., the powdered fumaric acid preparation of the present invention has a concentration of 0.05-1 mass as the fumaric acid concentration.
  • Bacteria are sterilized by immersing the ingredients in a treatment solution that is dispersed and dissolved to about%. Immersion time is appropriately set according to the purpose. For example, in the case of vegetables such as cabbage, about 30 seconds to 10 minutes, in the case of seafood such as squid, octopus and shrimp, about 10 seconds to 10 minutes, in the case of meat such as chicken, pork, and beef Soak and disinfect for about 60 minutes.
  • the washed and cut vegetables are immersed in the treatment solution for a short time, and then rinsed with water for cooking.
  • the sanitary detergent for food obtained by dissolving the powdered fumaric acid preparation of the present invention is fumaric acid which is recognized as a food additive.
  • the main component it is extremely safe and at the same time exerts extremely strong sterilizing power against food poisoning bacteria such as Escherichia coli, Pseudomonas aeruginosa, Salmonella, etc., vegetables, fruits, seafood, meat, etc. It can be used effectively for the purpose of preventing the occurrence of food poisoning caused by food.
  • Patent Documents 1 and 2 The present inventors have disclosed in Patent Documents 1 and 2 that the solubility is improved by coating the surface of fumaric acid particles with a nonionic surfactant (hydrophilic nonionic surfactant) exhibiting hydrophilicity.
  • a nonionic surfactant hydrophilic nonionic surfactant
  • each fumaric acid-containing granular composition obtained was pulverized in a mortar, and then a sieve having an opening of 500 ⁇ m (trade name “THE IIDA TESTING SIEVE” manufactured by Iida Manufacturing Co., Ltd.
  • the test samples 2 to 6 of powdered fumaric acid preparations coated with various hydrophilic nonionic surfactants having different HLB values were obtained.
  • a test sample 1 was prepared by only adding a hydrophilic nonionic surfactant to the fumaric acid powder used as a raw material and passing through a sieve having an opening of 500 ⁇ m.
  • the obtained test samples 2 to 6 each contain 0.5% by mass of various hydrophilic nonionic surfactants with respect to fumaric acid.
  • the absorbance at a wavelength of 280 nm was taken as 100%, and the relative fumaric acid dissolution rate (%) of each test sample was relatively evaluated. That is, the percentage of the value (Y) at the wavelength 280 nm of the 10-fold diluted solution of each test sample with respect to the absorbance value (X) at the wavelength 280 nm of the standard fumaric acid aqueous solution of 0.15 mg / mL ⁇ (Y / X) ⁇ 100 ⁇ was determined and taken as the relative fumaric acid dissolution rate.
  • Table 1 It has been confirmed that under the conditions tested, the influence of the addition of various hydrophilic nonionic surfactants on the absorbance at a wavelength of 280 nm is negligible.
  • the relative fumaric acid dissolution rate with respect to the control in which the fumaric acid powder was completely dissolved was as low as 82.0%. It was confirmed that stirring for 2 minutes did not sufficiently dissolve (dissolution rate was slow).
  • the powdered fumaric acid preparations (test samples 2 to 6) to which various hydrophilic nonionic surfactants were added and coated were shown to have a relative fumaric acid solubility of 97.0% or more. It was confirmed that the addition of the nonionic surfactant has the effect of improving the dissolution rate of fumaric acid.
  • the HLB value of the hydrophilic nonionic surfactant did not significantly affect the dissolution rate within the tested range, but among the hydrophilic nonionic surfactant, HBL was 15.5 and Since the test samples 2 and 4 to which the polyglycerin fatty acid ester of 17.0 was added showed a relative fumaric acid dissolution rate of 100%, the HBL is preferably in the range of about 14.0 to 18.0, In addition, among the same hydrophilic nonionic surfactants, it was considered that polyglycerol fatty acid ester is more effective in improving dissolution rate than sucrose fatty acid ester and polyoxyalkyl branched decyl ester.
  • test samples 2 to 6 Although it was confirmed that the dissolution rate of the powdered fumaric acid preparation (test samples 2 to 6) in water was improved by adding a hydrophilic nonionic surfactant, these preparations (test samples 2 to 6) Were easily aggregated, and it was difficult to obtain a sufficient amount of test sample that passed through a sieve having an opening of 500 ⁇ m in the test sample preparation step (a). Therefore, the following sieve passability test was performed in order to objectively evaluate the sieve passability of the test samples 2 to 6.
  • Table 2 shows the evaluation of the calculated passage rate of each test sample in the following three stages: +++: sieve passing rate after shaking for 30 seconds 50% or more; ++: sieve passage rate after shaking for 30 seconds 25 to less than 50%; +: Sieve passing rate after shaking for 30 seconds is less than 25%.
  • test sample 1 in which only fumaric acid powder is passed through a 500 ⁇ m sieve and test samples 2 to 6 which are powdered fumaric acid preparations to which various hydrophilic nonionic surfactants are added.
  • the sieve passing rate after shaking for 30 seconds was less than 25% (+), and the sieve passing ability was extremely low.
  • ⁇ Preliminary experiment 2 Effect of addition amount of polyglycerol fatty acid ester on dissolution rate improvement of powdered fumaric acid preparation> Subsequently, using polyglycerin fatty acid ester (HLB17), which was confirmed in the preliminary experiment 1 to be excellent in the dissolution rate improvement effect, the effect of the addition amount of the hydrophilic nonionic surfactant on the dissolution rate improvement of fumaric acid Further, the following preliminary experiment was conducted.
  • test samples 7 to 14 various powdered fumaric acid preparations coated with polyglycerin fatty acid ester were obtained.
  • or 14 are polyglycerol fatty acid ester 0.001, 0.05, 0.1, 0.5, 1.0, 3.0, 5 with respect to fumaric acid, respectively. 0.0 and 7.0% by mass.
  • the relative fumaric acid dissolution rate is improved as the amount of the polyglycerin fatty acid ester to be mixed increases, and the amount becomes 1.0% by mass or more (test samples 11 to 14) with respect to fumaric acid. It was confirmed that the dissolution rate was improved to the extent of complete dissolution in water by stirring for 2 minutes.
  • test samples 15 to 22 coated with various sugars together with a polyglycerin fatty acid ester.
  • the various powdered fumaric acid preparations (test samples 15 to 22) obtained contain 0.5% by mass of various carbohydrates in terms of anhydride with respect to fumaric acid.
  • the fumaric acid powder is obtained by adding and mixing a certain amount of polyglycerin fatty acid ester and various sugars, and coating the fumaric acid particles with polyglycerin fatty acid ester and various sugars.
  • the powdered fumaric acid preparations (test samples 15 to 22) are improved in passing through the sieve. It was confirmed that Regarding the sieving ability, there is a difference between sugars, and non-reducing disaccharide trehalose (test sample 17), sugar alcohol sorbitol (test sample 18) below disaccharide, and maltitol (test sample 19). ) was evaluated as “++++: sieve passing rate after shaking for 30 seconds, 50% or more”, and particularly excellent sieve passing ability was exhibited.
  • test samples 23 to 32 were obtained by adding trehalose to fumaric acid in terms of anhydrides of 0.05, 0.1, 0.2, 0.3, 0, respectively. .4, 0.5, 1.0, 2.0, 5.0, 10.0, 20.0, and 30.0 mass%.
  • fumaric acid powder and polyglycerin fatty acid ester are mixed in the above quantity ratio in the presence of water, and fumaric acid particles are coated only with polyglycerin fatty acid ester.
  • a mixture powder (comparative sample) of powdered fumaric acid and trehalose powder coated with fumaric acid only with a polyglycerin fatty acid ester was prepared by first preparing the mixed powder and mixing it as a powder.
  • the amount of trehalose added to the fumaric acid was 0. 0 compared to the control fumaric acid powder (control 1) and the coating with only the surfactant (polyglycerin fatty acid ester) (control 2).
  • control 1 the control fumaric acid powder
  • control 2 the coating with only the surfactant
  • the sieve passability of a powder fumaric acid formulation improves.
  • the effect increased as the amount of trehalose added increased.
  • the comparative sample obtained by coating the fumaric acid particles only with the polyglycerin fatty acid ester and then simply mixing the trehalose powder the effect of improving the sieve passing amount was not confirmed.
  • test sample 30 indicated by “*” in Table 5
  • the sieve passing property was improved and the coagulation improvement effect was observed
  • the test The degree of solidification of the dried product obtained in the sample preparation process became stronger, and powdering by pulverization became partly difficult.
  • the amount of trehalose added is 20% by mass or 30% by mass (test samples 31 and 32: indicated by “**” in Table 5)
  • the dry matter obtained in the test sample preparation step is The block-shaped lump solidified and became extremely difficult to grind.
  • the agent prepared by adding 10% by mass or more of trehalose in terms of anhydride to fumaric acid becomes difficult to grind, and the workability in the manufacturing process of the powdered fumaric acid preparation is significantly reduced. It became clear to do.
  • Patent Document 4 in order to improve the dissolution rate and stability of a powdered fumaric acid preparation, it has been essential to add a large amount of carbohydrate of 10% by mass or more.
  • the present inventors have confirmed through experiments that in order to achieve both improvement in dissolution rate and improvement in cohesion, the amount of sugar alcohol less than the non-reducing disaccharide or disaccharide is as follows: Rather, the result was that a smaller amount of less than 10% by weight with respect to fumaric acid was better. This is a new finding that overturns conventional technical common sense.
  • Acetic acid is known as an organic acid generally used as a sterilizing detergent for foods, and acetic acid is generally known to act more effectively against gram-negative bacteria than gram-positive bacteria. (Japan Food Industry Association, Vol. 41, No. 10, pp. 687-701, 1994). Although the difference in the antibacterial activity is not clarified, it is due to the structural difference between the Gram-negative bacterium having two lipid membranes, the cell membrane and the outer membrane, and the Gram-positive bacterium having no outer membrane and a thick peptidoglycan layer. It is considered a thing. Therefore, the present inventors intended to improve antibacterial activity and / or expand antibacterial targets, and as a model experiment, conducted experiments combining fumaric acid and ascorbic acid. It was confirmed that there was a fungus effect. Therefore, the present inventors conducted the following experiment to confirm the influence of the difference in the concentration of ascorbic acid when fumaric acid and ascorbic acid were combined on the sterilizing action against Gram-positive bacteria.
  • test sample Fumaric acid powder (trade name “Fumaric acid (fine powder)”, sold by Fuso Chemical Industry Co., Ltd.) dissolved in pure water to a concentration of 0.3% by mass 1.5 mL of a separately prepared ascorbic acid aqueous solution having an ascorbic acid concentration of 0.6% by mass was mixed with 1.5 mL of the acid-containing aqueous solution to obtain a total of 3 mL of a mixed solution of fumaric acid and ascorbic acid (test sample 33). .
  • the obtained mixed solution (test sample 33) contains fumaric acid at a concentration of 0.15% by mass and ascorbic acid at a concentration of 0.3% by mass.
  • test samples 34 and 35 a mixed solution of two types of fumaric acid and ascorbic acid (test samples 34 and 35) (each 3 mL) in the same manner except that the concentration of the ascorbic acid aqueous solution to be mixed was changed to 1.8 or 3.6% by mass. )
  • the obtained mixed solution (test samples 34 and 35) contains fumaric acid at a concentration of 0.15% by mass and ascorbic acid at concentrations of 0.9 and 1.8% by mass, respectively. .
  • the obtained seed culture solution was inoculated to 1.0% in an Erlenmeyer flask containing 100 mL of a new nutrient broth liquid medium, and cultured with shaking at 37 ° C. for 4 hours. After completion of the culture, 50 mL of the bacterial solution was centrifuged at 5,000 rpm for 5 minutes, the supernatant was removed, and after washing three times with phosphate buffered saline (PBS), Absorbance at a wavelength of 660 nm was measured, and PBS was added so that the number of bacteria was 5 ⁇ 10 6 CFU / mL to prepare a bacterial solution.
  • PBS phosphate buffered saline
  • the inventor conducted the following experiment in order to confirm the sterilization effect of the combination of fumaric acid and alcorbic acid against Gram-negative bacteria.
  • Ascorbic acid mixed solution (test samples 33 to 35) was used, and as gram-negative bacteria, Escherichia coli NBRC3301 strain was used as a gram-negative bacterium, and cultured under the same conditions as in Experiment 3. Centrifugation of 50 mL of the bacterial solution at a rotation speed of 5,000 rpm for 5 minutes, removing the supernatant, washing three times with phosphate buffered saline (PBS), and then absorbance at a wavelength of 660 nm Was measured, and PBS was added so that the number of bacteria was 5 ⁇ 10 6 CFU / mL to prepare a bacterial solution.
  • PBS phosphate buffered saline
  • the numbers of bacteria after the treatment time of 80 seconds are 9.3 ⁇ 10 3 CFU / mL and 6.2 ⁇ 10 3 CFU / mL, respectively. It was 4.4 ⁇ 10 3 CFU / mL and a further decrease in the number of bacteria was confirmed.
  • a powdered fumaric acid preparation containing ascorbic acid was prepared by the method described in Example 5 described later, and a powdered fumaric acid preparation was separately prepared by the method described in Example 1, 4 was subjected to the same bactericidal effect comparison test.
  • the powdered fumaric acid preparations prepared by the methods of Examples 1 and 5 were both confirmed as sterilization effects and effective as a sterilization detergent for foods. It was confirmed that.
  • the powdered fumaric acid preparation prepared by the method of Example 1 did not show the sterilization effect, but was prepared by the method of Example 5 containing ascorbic acid. It was found that the powdered fumaric acid preparation showed an excellent sterilizing effect and a wide antibacterial effect.
  • ⁇ Powdered fumaric acid preparation 200 parts by mass of commercially available fumaric acid powder (trade name “fumaric acid (fine powder)”, sold by Fuso Chemical Industry Co., Ltd.) was pulverized in a mortar, passed through a sieve having an opening of 500 ⁇ m, and adjusted to a particle size of 500 ⁇ m or less.
  • polyglycerin fatty acid ester (trade name “Ryoto Polyglycerin L-7D”, HLB17, manufactured by Mitsubishi Chemical Foods Co., Ltd.) was added and dissolved in water to prepare 10 parts by mass of a 10% by mass aqueous solution.
  • trehalose (trade name “Treha”, sold by Hayashibara Co., Ltd.) was dissolved in water to prepare 20 parts by mass of a 50% by mass aqueous solution of trehalose. Put 199 parts by mass of the pulverized fumaric acid powder in a plastic container, add the polyglycerin fatty acid ester aqueous solution and the trehalose aqueous solution at the same time, add 331 parts by mass of pure water, and mix using a blender. A mixture was obtained. Next, the obtained wet mixture was spread on a tray, preliminarily dried by heating at 70 ° C.
  • the amount of sugar relative to fumaric acid is reduced to less than 10% by weight in terms of anhydride, and the agent does not harden into blocks during the manufacturing process (after drying), which hinders crushing It was a powder having the advantage of not being.
  • this product is coated with fumaric acid using trehalose together with polyglycerin fatty acid ester, the phenomenon that hinders the aggregation of the resulting powdered fumaric acid preparation and classification with a sieve has been reduced. .
  • this product has improved the dissolution rate in water, it has an excellent property of easily preparing a sterilizing solution for foods.
  • ⁇ Powdered fumaric acid preparation> First, an aqueous trehalose solution was mixed with a commercially available fumaric acid powder, then a polyglycerol fatty acid ester aqueous solution was mixed with the resulting mixture, and the same procedure as in Example 1 was performed except that the pure water added was changed to 181 parts by mass. A powdered fumaric acid preparation containing 94.8% by mass of fumaric acid, 0.48% by mass of polyglycerol fatty acid ester, and 4.8% by mass of trehalose was obtained.
  • the amount of sugar relative to fumaric acid is reduced to less than 10% by weight in terms of anhydride, and the agent does not harden into blocks during the manufacturing process (after drying), which hinders crushing It was a powder having the advantage of not being.
  • this product coat covers the fumaric acid using trehalose with polyglyceryl fatty acid ester, the phenomenon which becomes obstructive when the obtained powder aggregates and classifies with a sieve was also reduced. Furthermore, since this product has improved the dissolution rate in water, it has an excellent property of easily preparing a sterilizing solution for foods.
  • sorbitol (“reagent”, sold by Wako Pure Chemical Industries, Ltd.) is used instead of trehalose, the amount of a 50 mass% aqueous solution of sorbitol is 15 parts by mass, and pure water to be added is 142.
  • the amount of sugar relative to fumaric acid is reduced to less than 10% by weight in terms of anhydride, and the agent does not harden into blocks during the manufacturing process (after drying), which hinders crushing It was a powder having the advantage of not being.
  • this product coat covers the fumaric acid using sorbitol with polyglyceryl fatty acid ester, the phenomenon which becomes obstructive when the obtained powder aggregates and classifies with a sieve was also reduced. Furthermore, since this product has improved the dissolution rate in water, it has an excellent property of easily preparing a sterilizing solution for foods.
  • Maltitol (trade name “Crystalline Maltitol”, sold by Mitsubishi Corporation Foodtech Co., Ltd.) is used as a carbohydrate covering the fumaric acid particles instead of trehalose, and the amount of 50% by weight aqueous solution of maltitol is 25 parts by mass.
  • sucrose fatty acid ester (trade name “Ryoto Sugar Ester S-1670”, HLB16, manufactured by Mitsubishi Chemical Foods Co., Ltd.) is used as a hydrophilic nonionic surfactant, and the amount of 10% by mass aqueous solution of sucrose fatty acid ester A powdered fumaric acid preparation containing the same treatment as in Example 1 except that the amount of the fumaric acid was changed to 20 parts by mass and containing 93.2% by mass of fumaric acid, 0.94% by mass of sucrose fatty acid ester and 5.85% by mass of maltitol Got.
  • the amount of sugar relative to fumaric acid is reduced to less than 10% by weight in terms of anhydride, and the agent does not harden into blocks during the manufacturing process (after drying), which hinders crushing. It was a powder having the advantage of not being.
  • this product coat covers fumaric acid using maltitol with sucrose fatty acid ester, the phenomenon which becomes obstructive when the obtained powder aggregates and classifies with a sieve was also reduced. Furthermore, since this product has improved the dissolution rate in water, it has an excellent property of easily preparing a sterilizing solution for foods.
  • ⁇ Powdered fumaric acid preparation 6 parts by weight of ascorbic acid (reagent grade, sold by Wako Pure Chemical Industries, Ltd.) is added to 1 part by weight of fumaric acid in the powdered fumaric acid preparation obtained in Example 1, and pulverized and mixed in a mortar. An open 500 ⁇ m sieve was passed through to obtain a powdered fumaric acid preparation containing an organic acid other than fumaric acid (ascorbic acid).
  • ascorbic acid ascorbic acid
  • this product contains a relatively large amount of ascorbic acid, it covers the fumaric acid particles using trehalose together with the polyglycerin fatty acid ester. The phenomenon was reduced. Furthermore, since this product has improved the dissolution rate in water, it has an excellent property of easily preparing a sterilizing solution for foods.
  • ⁇ Powdered fumaric acid preparation 3 parts by mass of ascorbic acid 2-glucoside (reagent grade, sold by Wako Pure Chemical Industries, Ltd.) is added to 1 part by mass of fumaric acid in the powdered fumaric acid preparation obtained in Example 1, and pulverized and mixed in a mortar. Then, it was passed through a sieve having an opening of 500 ⁇ m to obtain a powdered fumaric acid preparation containing an organic acid derivative (ascorbic acid 2-glucoside) other than fumaric acid.
  • ascorbic acid 2-glucoside additive grade, sold by Wako Pure Chemical Industries, Ltd.
  • This product contains a relatively large amount of ascorbic acid 2-glucoside, which is a derivative of ascorbic acid, but because the fumaric acid particles are coated with trehalose together with polyglycerin fatty acid ester, the resulting powder aggregates. The phenomenon that hinders classification with a sieve was reduced. Furthermore, since this product has improved the dissolution rate in water, it has an excellent property of easily preparing a sterilizing solution for foods.
  • ⁇ Vegetable sanitizer for vegetables> The powdered fumaric acid preparation obtained in Example 2 was dissolved in pure water so as to have a fumaric acid concentration of 0.3% by mass to obtain a sterilizing detergent for vegetables. By immersing the cut vegetables in this sanitizing detergent for 30 seconds or more, the number of viable bacteria in the cut vegetables can be significantly reduced.
  • ⁇ Decontamination detergent for meat> The powdered fumaric acid preparation obtained in Example 3 was dissolved in pure water so as to have a fumaric acid concentration of 0.5% by mass to obtain a sanitizing detergent for meat. By immersing the chicken cut into this sterilizing detergent at 25 ° C. for 60 minutes, the number of viable bacteria in chicken can be significantly reduced.
  • ⁇ Powdered fumaric acid preparation> The same treatment as in Example 1 was performed except that the addition amount of 50% by mass aqueous solution of trehalose was 50 parts by mass, 88.4% by mass of fumaric acid, 0.44% by mass of polyglycerol fatty acid ester, 11.1% by mass of trehalose. % Powdered fumaric acid formulation was obtained.
  • This product contains more than 10% by mass of saccharides relative to fumaric acid in terms of anhydride, and because the agent solidified into blocks during the manufacturing process (after drying), it became difficult to grind and work The property decreased significantly.
  • ⁇ Powdered fumaric acid preparation> A powder fumaric acid preparation containing 99.5% by weight of fumaric acid and 0.5% by weight of polyglycerol fatty acid ester was obtained except that a 50% by weight aqueous solution of trehalose was not added. .
  • the surface of the fumaric acid particles is only coated with polyglycerin fatty acid ester, which is a surfactant, and the fumaric acid dissolution rate itself is improved, but the powdered fumaric acid preparation is agglomerated in the manufacturing process.
  • the passability of the sieve was lowered, and the workability in the production of the powdered fumaric acid preparation and the recovery rate of the preparation were significantly reduced.
  • a powdered fumaric acid preparation excellent in powder flowability and dissolution rate can be easily produced.
  • the powdered fumaric acid preparation obtained by the production method of the present invention is superior in powder fluidity, hard to solidify, easy to handle as a powdered preparation, and soluble in water, compared to conventional powdered fumaric acid preparations. Since (dissolution rate) is also good, it can be advantageously used in the food field as a sour agent, preservative, disinfectant and the like. The influence of the present invention on the world is so great that the industrial applicability of the present invention is extremely large.

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Abstract

La présente invention aborde le problème consistant à fournir une formulation de poudre d'acide fumarique présentant d'excellentes propriétés d'écoulement de poudre et une excellente vitesse de dissolution. En vue de résoudre ce problème, la présente invention porte sur une formulation en poudre d'acide fumarique et un procédé de production de ladite formulation en poudre d'acide fumarique, la formulation en poudre d'acide fumarique étant caractérisée comme suit : elle comprend un acide fumarique, un tensioactif non ionique hydrophile, et un disaccharide non réducteur ou un alcool de sucre comprenant deux sucres ou moins, le pourcentage en masse de ce dernier par rapport à l'acide fumarique étant supérieur ou égal à 0,5 mais inférieur à 10 en termes de contenu anhydre ; et l'acide fumarique est recouvert du tensioactif non ionique hydrophile et du disaccharide non réducteur ou de l'alcool de sucre comprenant deux sucres ou moins.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53146978A (en) * 1977-05-28 1978-12-21 Ueno Seiyaku Oyo Kenkyujo Kk Improved powder or glanule containing sorbic acid
JPS60133863A (ja) * 1983-12-23 1985-07-17 Nippon Shokubai Kagaku Kogyo Co Ltd 速溶性食品製剤の製法
WO2001052820A1 (fr) * 2000-01-17 2001-07-26 Kyowa Hakko Kogyo Co., Ltd. Pastille a effet moussant, pastille d'addition pour le bain a effet moussant, pastille detergente de lavage a effet moussant, pastille a effet moussant pour administration orale et procedes de production de ces pastilles
JP2003147392A (ja) * 2001-11-14 2003-05-21 Fuso Chemical Co Ltd 食品用除菌洗浄剤および食品の除菌方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53146978A (en) * 1977-05-28 1978-12-21 Ueno Seiyaku Oyo Kenkyujo Kk Improved powder or glanule containing sorbic acid
JPS60133863A (ja) * 1983-12-23 1985-07-17 Nippon Shokubai Kagaku Kogyo Co Ltd 速溶性食品製剤の製法
WO2001052820A1 (fr) * 2000-01-17 2001-07-26 Kyowa Hakko Kogyo Co., Ltd. Pastille a effet moussant, pastille d'addition pour le bain a effet moussant, pastille detergente de lavage a effet moussant, pastille a effet moussant pour administration orale et procedes de production de ces pastilles
JP2003147392A (ja) * 2001-11-14 2003-05-21 Fuso Chemical Co Ltd 食品用除菌洗浄剤および食品の除菌方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SHIMIZU, TAKAMASA ET AL.: "Antibacterial Activity of Several Organic Acids commonly used as Food Additives", FOOD HYGIENE AND SAFETY SCIENCE, vol. 36, no. 1, 1995, pages 50 - 54, XP009105079 *

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