Granular products and their production process

Abstract

The present invention relates to a process for producing an agglomerated granular product containing one or more flavoring agents and / or flavor enhancers. By spraying certain binders, the storage stability of the granular product is significantly improved and, in particular, the flavoring agents and / or flavor enhancers are protected from oxidation. The present invention also relates to a granular product containing one or more flavoring agents and / or flavor enhancers, preferably produced by the process according to the present invention, and the use of certain substances for improving the storage stability of granular products containing one or more flavoring agents and / or flavor enhancers.

Description

Technical Field

[0001] The present invention relates to a process for producing an agglomerated granular product containing one or more flavoring agents and / or flavor enhancers. By spraying certain binders, the storage stability of the granular product is significantly improved and, in particular, the flavoring agents and / or flavor enhancers are protected from oxidation. The present invention also relates to a granular product containing one or more flavoring agents and / or flavor enhancers. Preferably, the product is prepared by a process according to the present invention. The present invention also relates to the use of certain substances for improving the storage stability of granular products containing one or more flavoring agents and / or flavor enhancers. Background Art

[0002] The production of granules with active ingredients is important for applications in the food and beverage industry as well as in the pharmaceutical industry. For example, instant products are often in dry powder form and spice granules are used in tea bags or seasoning mixes. But the granular form can also facilitate the processing of active ingredients in pharmaceuticals. Often, depending on the application, it is necessary to provide granules of a certain size that form a powder with flowability and that do not agglomerate, abrade or form dust even during long-term storage. In addition, the active ingredient incorporated into the granules should not decompose and be released before the final application.

[0003] EP0705062B1 relates to a process for producing agglomerated powders of dairy products such as baby food, in which a concentrated liquid is first atomized and agglomerated in a drying chamber. The agglomerated particles are then placed in an internal fluidized bed and finally transferred to an external fluidized bed. The powder is divided by returning a portion of the powder thus obtained to the drying chamber, while water is atomized on another portion of the powder to further agglomerate the product.

[0004] GB 1167692A describes a process in which an agglomerating agent is sprayed onto particles in a fluidized bed, thereby wetting the particles and causing them to adhere to each other. The process is particularly applicable to foods such as sugar, flour, milk powder or starch, and for example water, sugar solution or condensed milk are used as agglomerating agent.

[0005] AU2007336516B2 discloses a process for producing agglomerates by fluidized spray drying, wherein larger particles are separated and dust that has not yet agglomerated is returned to a drying chamber by an air stream for further agglomeration. According to AU2007336516B2, the process is advantageously used for the preparation of medicaments containing low-solubility active ingredients. For example, the active ingredient is spray dried together with a polymer as a carrier.

[0006] Flavor substances in granular form are used in a wide variety of foods and luxury foods. In the production of such flavor granules, certain requirements must generally be met with regard to particle size distribution, mechanical stability of the granules and storage stability. In particular, it is ideal to achieve the maximum possible flavor loading of the granules while ensuring that the flavor is incorporated into the granules in such a way that it is not released prematurely or decomposed or volatilized before the final application. Flavoring agents and flavor enhancers are also often particularly sensitive to oxidation by atmospheric oxygen, which greatly limits storage stability. Therefore, there is a need to improve the known manufacturing processes and the choice of materials used.

[0007] EP1064856B1 describes a process for producing microcapsules containing active ingredients such as flavorants in a matrix. The process comprises a number of steps in which the active ingredient is first spray-dried together with at least one low molecular weight carbohydrate or polyol and a film-forming component in an emulsion or suspension and then transferred to a fluidized bed for further drying.

[0008] In a known process from EP 3 117 720 A1, powder particles having a certain minimum size are produced. The apparatus used in the process according to EP 3 117 720 A1 is Figure 1 The method comprises the following steps:

[0009] (i) producing powdery particles by spray drying in a spray drying agglomeration apparatus having a spray drying section (A) at the upper part of a chamber for drying the feed liquid sprayed from a feed liquid sprayer (Z1),

[0010] (ii) spraying the powdered particles with a binder liquid in an integrated fluidized bed (B) in a spray drying agglomeration apparatus, wherein the integrated fluidized bed is located in the lower part of a chamber, in which the powder in the spray drying section of step (i) is sprayed with a binder liquid through a nozzle or sprayer structure (Z2) attached to the bottom of the fluidized bed (B),

[0011] As a result, the particles are kept in motion and swirled upwards during the production process.

[0012] The process described in EP3117720A1 can be used to produce fragrance particles. In the example of EP3117720A1, the particles produced by this method were stored in an artificial climate chamber for 144 hours, and it was determined that the weight of the particles increased due to hygroscopicity. However, EP3117720A1 does not involve the storage stability of fragrance particles, especially the stability of fragrance over several months. Summary of the invention

[0013] One object of the present invention is to provide a spice particle and a production process thereof, so that the spice particle should be suitable for food and light luxury food. In particular, the particle should have a suitable size, wear resistance, low dust value and good fluidity, that is, not easy to agglomerate.

[0014] Furthermore, it is an object of the present invention to ensure that the fragrance particles can be produced by an efficient process and have good storage stability, preferably storage stability over several months to several years. In particular, the fragrance substances should not be released too early and should be protected from oxidation.

[0015] The above object is achieved by a process for producing a granular product containing one or more flavoring agents and / or flavor enhancers, the process comprising:

[0016] (i) producing particles comprising or consisting of one or more flavorants and / or flavor enhancers and one or more carriers by spray drying in a drying chamber of a spray drying apparatus,

[0017] (ii) spraying one or more binders selected from the group consisting of monosaccharides or polysaccharides having reducing groups and sugar alcohols or mixtures thereof on the particles in a fluidized bed integrated into the drying chamber, wherein the binders are used in a total amount of 10 vol% to 30 vol%, preferably 10 vol% to 20 vol%, in aqueous solution.

[0018] wherein steps (i) and (ii) are performed simultaneously, and the particles are kept moving and agglomerated in the drying chamber, and

[0019] The aqueous solution of the binder does not contain any flavoring agents and / or flavor enhancers.

[0020] Preferably, the process as described above is a continuous process, wherein agglomerates which have reached a certain size are continuously removed from the drying chamber without interrupting the process.

[0021] The particles are kept moving, stirred and / or circulated in the drying chamber. This ensures that smaller particles and dust are constantly wetted by the adhesive, and then the two are likely to collide with other particles and further agglomerate. Due to the frequent collisions of the particles wetted by the adhesive, what is formed in this process is a loose agglomerate of porous structure, rather than a single particle coated with an adhesive. Advantageously, the process according to the present invention can be carried out in a spray drying chamber with an integrated fluidized bed, without the need to transfer to another device. The method for separating such particles agglomerated to a desired size, as well as the effective wetting and circulation of particles with an adhesive are described in EP3117720A1. Preferably, the process according to the present invention is carried out in a spray drying agglomeration device as disclosed in EP3117720A1.

[0022] In the context of the present invention, a granular product refers to any product consisting of particles. In particular, a granular product is a granule or a powder. A granular product may also include or consist of agglomerated particles.

[0023] In the context of the present invention, it has been found that the choice and composition of the binder play a decisive role in stabilizing the flavoring agents and / or odorants in the agglomerated particles. Particularly good results are obtained when the binder is used in a concentration of 10% to 30%, preferably 10% to 20%. In this context, the concentration of the binder determines the drying rate of the binder on the surface of the particles to be agglomerated. The choice of the binder can also control the strength with which the particles "stick together" in the process. The higher the molecular weight of the binder, the slower the drying; if it is then still used in too high a concentration, the fluidized bed will collapse because the particles stick together too quickly or stick too tightly so that the existing airflow can no longer fluidize and dry the particles. In addition, it has been shown that the choice of the binder has a significant impact on the stability and storage stability of the flavoring particles. By using the binder of the present invention, large bulk density, low dust value, flowable, non-bonded, agglomerated particles can be produced. Monosaccharides or polysaccharides and sugar alcohols are particularly suitable, and the use of substances or mixtures containing reducing groups is particularly advantageous in that the flavoring agents and / or odorants are effectively protected from oxidation. This can significantly improve the storage stability of the flavoring particles.

[0024] The binder liquid used in step (ii) is prepared at a concentration of about 10% to 30%, and the feed amount is calculated according to the feed amount of the spray emulsion used in step (i). For example, about 10 liters of binder liquid are added for every 100 liters of spray emulsion, or if it is solid, about 1 kg of dry weight of binder is sprayed for every 50 kg of solid in the spray emulsion.

[0025] Monosaccharides or polysaccharides include monosaccharides, disaccharides, oligosaccharides and polysaccharides. The monosaccharides and polysaccharides to be used according to the present invention contain reducing groups, i.e. free aldehyde groups with reducing properties. In particular, the monosaccharides or polysaccharides or mixtures thereof with reducing groups have at least 8, preferably at least 12, particularly preferably at least 18 dextrose equivalents.

[0026] The process as described above is preferred, wherein the binder is selected from the group consisting of sugar alcohols, in particular mannitol; monosaccharides, disaccharides and oligosaccharides with reducing groups or mixtures containing or consisting of monosaccharides, disaccharides and / or oligosaccharides with reducing groups, in particular glucose, mannose, galactose, maltose, lactose, cellobiose and maltodextrin; and polysaccharides with reducing groups, preferably plant gums, in particular gum arabic, tragacanth, ghatti gum, agar, carrageenan, guar flour and carob gum (carubin).

[0027] The monosaccharides, disaccharides and oligosaccharides having reducing groups or a mixture containing or consisting of monosaccharides, disaccharides and / or oligosaccharides having reducing groups preferably have at least 8, preferably at least 12, particularly preferably at least 18 dextrose equivalents.

[0028] In particular, also according to the invention, a combination of vegetable gum and modified starch is used as binder.

[0029] Using the preferred binders mentioned, particularly stable granules can be obtained in which the flavoring agents and / or flavorants are not released prematurely or decomposed even after a relatively long storage period. Surprisingly, it has been found that the reducing groups in the binder are particularly effective in protecting the flavoring agents or flavorants from oxidation, even if the binder is initially used only for agglomeration and does not completely cover or seal the granules.

[0030] Further preferred is a process as described above, wherein the flavoring agent and / or flavor enhancer is selected from the group consisting of: fruit flavors, especially citrus flavors; meat, vegetable and condiment flavors; and meat, vegetable and condiment extracts. Specific flavoring agents and / or flavor enhancers are described below.

[0031] Citrus flavors are particularly sensitive to oxidation and the above-mentioned adhesives will effectively protect the citrus flavors from oxidation.

[0032] Also preferred is a process as described above, wherein said carrier is selected from the group consisting of maltodextrin, dextrin, starch, flour and fibrous material.

[0033] The fibrous material is insoluble dietary fiber from cellulose, modified cellulose, cereal fiber (e.g. wheat or oat), fruit and vegetable fiber (e.g. apple, carrot, potato, pea or bamboo).Preferably, the fibrous material has a typical particle size of 10 μm to 500 μm.

[0034] Preferred according to the invention is a process as described above, wherein in step i), an emulsion comprising one or more flavoring agents and / or flavor enhancers, one or more carriers and at least one emulsifier is sprayed, preferably wherein the flavoring agents and / or flavor enhancers are used in a ratio of 2:1 to 1:2, preferably 1.5:1 to 1:1.5, to the at least one emulsifier, and / or wherein the flavoring agents and / or flavor enhancers are used in a ratio of 1:2 to 1:4, preferably 1:2.5 to 1:3.5, to the carrier.

[0035] Further preferred is a process as described above, wherein the at least one emulsifier is selected from the group consisting of gum arabic, modified starches, proteins, in particular vegetable proteins, natural or modified pectins and soluble fractions of soy polysaccharides.

[0036] Preferably, the (spray) emulsion used in step (i) comprises 10 wt% to 30 wt%, preferably 15 wt% to 25 wt% of flavoring and / or flavor enhancer, 10 wt% to 30 wt%, preferably 15 wt% to 25 wt% of emulsifier and 40 wt% to 80 wt%, preferably 50 wt% to 70 wt% of carrier, which are adjusted to have sufficient viscosity with water, the amount of water used being approximately equal to or slightly less than the weight of the aforementioned components.

[0037] Also preferred according to the invention is a process wherein the emulsion of step (i) is used in a volume ratio of 5:1 to 15:1, preferably 8:1 to 12:1 to the binder solution of step (ii), and / or the solids in the emulsion of step (i) are used in a weight ratio of 30:1 to 70:1, preferably 40:1 to 60:1 to the solids in the binder solution of step (ii).

[0038] The present invention also relates to a granular product, preferably produced or producible by a process as described above, wherein the product consists of particles comprising or consisting of flavorants and / or flavor enhancers and one or more carriers agglomerated with a binder, wherein the agglomerated particles have a porous structure, and wherein the binder is selected from the group consisting of: monosaccharides or polysaccharides having reducing groups and sugar alcohols or mixtures thereof, and wherein the binder does not contain flavorants and / or flavor enhancers.

[0039] In particular, the monosaccharide or polysaccharide or mixture thereof having a reducing group has at least 8, preferably at least 12, more preferably at least 18 dextrose equivalents.

[0040] The product according to the invention is a loose agglomeration of flavoring and / or flavor enhancer particles. Therefore, the binder only incompletely covers the surface of the particles. In particular, the product according to the invention differs from individual coated particles having an "onion structure" in which there is a core that is completely and uniformly covered by one of several layers of binder. In contrast, the product according to the invention has a "grape structure" in which the individual particles are bound together by the binder. The product has a porous structure and is therefore easy to disperse or dissolve quickly in water, which is particularly advantageous for use in instant products.

[0041] Since the binder itself does not contain any flavorants and / or flavor enhancers, the flavorants and / or flavor enhancers cannot be evenly distributed on the agglomerates and are hardly attached to the surface, so the binder effectively protects the flavorants and / or flavor enhancers from oxidation. It is worth noting that the binder merely sticks the particles together and does not form a sealing layer on their surface. However, surprisingly, the reducing groups present on the surface seem to be sufficient to protect the flavorants and / or flavor enhancers from oxidation.

[0042] Figure 2 Unagglomerated spray-dried particles with lemon flavour are shown. Figure 3 The same spray-dried particles agglomerated with water are shown. Although the same spray-dried particles as the products according to the invention ( Figure 4 , agglomerated with gum arabic, Figure 5 , agglomerated with maltodextrin) but water cannot protect the particles from oxidation.

[0043] Preferred is a granular product as described above, wherein the binder is selected from the group consisting of sugar alcohols, in particular mannitol; monosaccharides, disaccharides and oligosaccharides with reducing groups or mixtures containing or consisting of monosaccharides, disaccharides and / or oligosaccharides with reducing groups, in particular glucose, mannose, galactose, maltose, lactose, cellobiose and maltodextrin; and polysaccharides with reducing groups, preferably vegetable gums, in particular gum arabic, tragacanth, gum ghatti, agar, carrageenan, guar flour and carob gum.

[0044] The monosaccharides, disaccharides and oligosaccharides having reducing groups or a mixture containing or consisting of monosaccharides, disaccharides and / or oligosaccharides having reducing groups preferably have at least 8, preferably at least 12, particularly preferably at least 18 dextrose equivalents.

[0045] Further preferred is the granular preparation as described above, comprising or consisting of the following substances:

[0046] - 2 to 35 wt%, preferably 15 to 25 wt%, of flavorants and / or taste enhancers, and

[0047] - 65 wt% to 98 wt% of carriers, binders and emulsifiers,

[0048] Where the binder or one, more or all binders are different from the carrier and / or emulsifier, the granular product comprises 1 wt% to 10 wt%, preferably 5 wt% to 8 wt% of binder, in each case based on the total weight of the product.

[0049] Preferably, the product according to the invention is produced by a process as described above. In this process, the carrier and / or emulsifier used in step (i) may be or include the same substance as the binder used in step (ii). The particles produced thus correspond to the sum of the carrier, emulsifier and binder in a weight percentage of 65% to 89%. If the carrier and emulsifier used in step (i) are different from the binder used in step (ii), the weight percentage of the binder is 1% to 10% of the particles.

[0050] Particularly preferred is a granular product as described above, wherein the carrier is selected from the group consisting of maltodextrin, dextrin, starch, flour and fibrous material, and / or wherein the emulsifier is selected from the group consisting of gum arabic, modified starch, proteins, in particular vegetable proteins, natural or modified pectin and soluble components of soy polysaccharides.

[0051] Particularly preferred is a granular product as described above which is produced or producible by a process as described above.

[0052] In a preferred embodiment, the D50 value of the agglomerated particles of the article is from 100 μm to 600 μm, preferably from 200 μm to 500 μm, more preferably from 300 μm to 400 μm.

[0053] The particle size and particle size distribution of the product play a role in many applications. For example, the size of the particles should be as uniform as possible and no larger agglomerates should stand out.

[0054] In another preferred embodiment, the granular product has a flowability having an FFC value of 14 or less, preferably 12 or less.

[0055] Granular products according to the invention having a flow value of 14 or less or 12 or less are non-sticky and preferably have good solubility. This property has a significant impact on the end use and range of applications and is therefore particularly important for powders and granules for the food industry. The granules thus obtained therefore have improved product quality. Preferably, the granules are free-flowing and dust-free. Such granules are easy to dose, easier to process, and can be used in a wide range of applications.

[0056] In another preferred embodiment, the bulk density of the granular product is at least 300 g / L, preferably at least 400 g / L.

[0057] Further preferably, the bulk density of the granular product is in the range of 200 g / L to 600 g / L, preferably, in the range of 300 g / L to 500 g / L.

[0058] A larger density volume means that the particles have a stable core and therefore have a higher stability, especially abrasion resistance. A good binder improves the cohesion of the agglomerated particles and thus improves their stability, so the choice of binder directly affects the bulk density. Advantageously, the binder used according to the invention can also achieve the bulk density as described above.

[0059] Further preferred is a granular product as described above, wherein the dust value is 13 or less, preferably 12 or less, more preferably 10 or less.

[0060] The dust value of the granular product according to the invention is 13 or less, preferably 12 or less, which means that the agglomerates are particularly stable and can be advantageously filled, stored and transported without causing abrasion or dust formation. In this context, the correct choice of binder is also crucial, and it has been shown that the binders used according to the invention meet the necessary requirements for maintaining the above-mentioned dust values.

[0061] In another preferred embodiment of the granular product according to the invention, the taste enhancer and / or flavoring is selected from the group consisting of: fruit flavors, in particular citrus flavors; meat, vegetable and condiment flavors; and meat, vegetable and condiment extracts.

[0062] In the granular product according to the invention, the contained flavor enhancers and / or flavorings are stably incorporated and, in particular, protected from oxidation. This significantly improves the storage stability and stabilizes oxidation-sensitive flavors, such as citrus flavors, for several months.

[0063] The flavor enhancers and / or flavoring agents used according to the invention are selected in particular from the group consisting of acetophenone, allyl hexanoate, α-ionone, β-ionone, anisaldehyde, anisyl acetate, anisyl formate, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, butyl butyrate, butyl hexanoate, butenylphthalide, carvone, camphene, caryophyllene, eucalyptol, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascenone, decalactone , dihydrocoumarin, methyl dimethyl anthranilate, lauryl lactone, ethoxyethyl acetate, ethyl butyrate, ethyl butyrate, ethyl decanoate, ethyl caproate, ethyl butenoate, ethyl furanone, ethyl guaiacol, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, methyl ethyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptanoate, 4-(p-hydroxyphenyl)-2-butanone, γ-decanoyl lactone, geraniol, geranyl acetate, geranyl acetate, grapefruit aldehyde, methyl dihydrojasmonate (e.g. B. ), jasminaldehyde, 2-heptanone, 3-heptanone, 4-heptanone, trans-2-heptenal, cis-4-heptenal, trans-2-hexenal, cis-3-hexenol, trans-2-hexenoic acid, trans-3-hexenoic acid, cis-2-hexenyl acetate, cis-3-hexenyl acetate, cis-3-hexenyl hexanoate, trans-2-hexenyl hexanoate, cis-3-hexenyl formate, cis-2-hexyl acetate, cis-3-hexyl acetate, trans-2-hexyl acetate, cis-3-hexyl formate, parahydroxybenzyl acetone, isopentanol, isopentanyl isovalerate, isobutyl butyrate, isobutylaldehyde, isoeugenol methyl ether, isopropyl methylthiazole, lauric acid, levulinic acid, linalool, linalool Oxide, linalyl acetate, menthol, menthofuran, methyl anthranilate, methyl butanol, methyl butyric acid, 2-methyl butyl acetate, methyl caproate, methyl cinnamate, 5-methyl furfural, 3,2,2-methylcyclopentenolone, 6,5,2-methylheptenone, methyl dihydrojasmonate, methyl jasmonate, methyl 2-methylbutyrate, 2-methyl-2-pentenoic acid, methyl thiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexyl acetate, nerol, nerol acetate, trans, trans-2,4-nonadienal, 2,4-nonadienol, 2,6-nonadienol, 2,4-nonadienol, naringenone, delta-octalactone, gamma-octalactone, 2-octanol, 3-octanol, 1, 3-octenol, 1-octyl acetate, 3-octyl acetate, palmitic acid, paraldehyde, phellandrene, pentanedione, phenylethyl acetate, phenylethyl alcohol, phenylethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, pulegone, menthol, sweet orange aldehyde, thiothiazole, terpinene, terpineol, terpinolene, 8,3-thiomenthone, 4,4,2-thiomethylpentanone, thymol, δ-undecanolactone, γ-undecanolactone, valencene, valeric acid, vanillin, acetoin, ethyl vanillin, ethyl vanillin isobutyrate (= 3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone and its derivatives (preferably homofuranol (= 2-ethyl -4-hydroxy-5-methyl-3(2H)-furanone), homofuranol (=2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and its derivatives (preferably ethyl maltol), coumarin and its derivatives, γ-lactones (preferably γ-undecalactone, γ-nonalactone, γ-decanolactone), δ-lactones (preferably 4-methyl δ-decanolactone, dihydropentylpyrone, δ-decanolactone, tuber lactone), methyl sorbate, divanillin, 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone, 2-hydroxy-3-methyl-2-cyclopentenone, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, isopentyl acetate, ethyl butyrate, n-butyl butyrate, isopentyl butyrate, ethyl 3-methyl butyrate, ethyl hexanoate, allyl hexanoate, n-butyl hexanoate, ethyl octanoate, ethyl 3-methyl-3-phenylglycidate, ethyl 2-trans-4-cis-decadienoate, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5 -heptene-1-aldehyde and phenylacetaldehyde, 2-methyl-3-(methylthio)furan, 2-methyl-3-furanthiol, bis(2-methyl-3-furanyl) disulfide, furfurylthiol, methylthiopropionaldehyde, 2-acetyl-2-thiazoline, 3-mercapto-2-pentanone, 2,5-dimethyl-3-furanthiol, 2,4,5-trimethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-ethylthiazole, 2-acetyl-1-pyrroline, 2-methyl-3-ethyl 2-Ethyl-3,5-dimethylpyrazine, 2-Ethyl-3,6-dimethylpyrazine, 2,3-Diethyl-5-methylpyrazine, 3-Isopropyl-2-methoxypyrazine, 3-Isobutyl-2-methoxypyrazine, 2-Acetylpyrazine, 2-Amylpyridine, (E,E)-2,4-Decadienal, (E,E)-2,4-Nonadienal, (E)-2-Octenal, (E)-2-Nonenal, 2-Undecenal, 12-Methyltridecal, 1 -penten-3-one, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, guaiacol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 3-hydroxy-4-methyl-5-ethyl-2(5H)-furanone, cinnamaldehyde, cinnamyl alcohol, methyl salicylate, isopulegol, and stereoisomers, enantiomers, positional isomers, diastereomers, cis / trans isomers and epimers of these substances (not explicitly mentioned in this article).

[0064] The invention also relates to a product containing the granular product as described above, which product is selected from the group consisting of food and beverage products, in particular hot and cold, alcoholic and non-alcoholic beverages, fruit and vegetable juice products, instant beverages, meat products, egg products, dairy products, products made from soya protein and other vegetable protein sources, fatty and oily products or emulsions thereof, fruit and vegetable products, snacks, baked goods, confectionery, soups, sauces, spice and seasoning mixes, instant products, ready-to-eat products, semi-finished products, oral care products, pet food and food supplements.

[0065] The granular product according to the present invention can be applied to a variety of different products. The products according to the present invention particularly include: baked products, such as bread, biscuits, cakes, other pastries; confectionery products, such as chocolate, chocolate bar products, other bar products, fruit gelatin, soft and hard caramels, chewing gum; alcoholic or non-alcoholic beverages, such as coffee, tea, ice tea, wine, wine beverages, beer, beer beverages, liqueurs, spirits, wine spirits, (carbonated) fruit sodas, (carbonated) isotonic beverages, (carbonated) soft drinks, nectar, soda, fruit and vegetable juices, fruit or vegetable juice products; instant beverages, such as instant cocoa drinks, instant tea, instant coffee, instant fruit drinks; meat products, such as ham, fresh sausage or raw sausage products, seasoned or pickled fresh or air-dried meat products; eggs or egg products (egg powder, egg whites, egg yolks); cereal products, such as breakfast cereals, granola bars, pre-cooked instant rice products; dairy products, such as milk drinks, buttermilk drinks, milk ice cream, yogurt, kefir, Cream cheese, soft cheese, hard cheese, dry milk powder, whey, whey beverages, butter, buttermilk, partially or completely hydrolyzed milk protein-containing products; products made from soy protein or other soy components, such as soy milk and products made therefrom, fruit beverages containing soy protein, products containing soy lecithin; fermented products, such as tofu or tempeh or products made therefrom; products made from other plant protein sources, such as oat protein beverages; fruit products, such as jam, fruit ice cream, fruit sauce, fruit fillings; vegetable products (such as ketchup, sauce, dried vegetables, frozen vegetables, precooked vegetables, canned vegetables; snacks, such as baked or fried potato chips or potato dough products, corn or peanut presses; fatty and oily products or their emulsions, such as mayonnaise, tartar sauce, spices; and other convenience foods and soups used in the snack industry (such as dry soups, instant soups, precooked soups, spices, seasoning mixtures, especially seasonings).

[0066] The present invention also relates to the use of one or more substances as binders for improving the storage stability of a granular product containing one or more flavorants and / or odorants, in particular for improving the oxidative stability of one or more flavorants and / or odorants in a granular product as described above, wherein the one or more substances are selected from monosaccharides or polysaccharides having reducing groups and sugar alcohols, and the granular product is preferably produced or producible by a process as described above.

[0067] In particular, the monosaccharide or polysaccharide or mixture thereof having a reducing group has at least 8, preferably at least 12, more preferably at least 18 dextrose equivalents.

[0068] Preferred is the use as described above, wherein the substance is selected from the group consisting of sugar alcohols, in particular mannitol; monosaccharides, disaccharides and oligosaccharides with reducing groups or mixtures containing or consisting of monosaccharides, disaccharides and / or oligosaccharides with reducing groups, in particular glucose, mannose, galactose, maltose, lactose, cellobiose and maltodextrin; and polysaccharides with reducing groups, preferably plant gums, in particular gum arabic, tragacanth, ghatti gum, agar, carrageenan, guar flour and carob gum.

[0069] The monosaccharides, disaccharides and oligosaccharides having reducing groups or a mixture containing or consisting of monosaccharides, disaccharides and / or oligosaccharides having reducing groups preferably has at least 8, preferably at least 12, particularly preferably at least 18 dextrose equivalents.

[0070] Preferably, in the use according to the invention, the taste enhancer and / or flavoring is selected from the group consisting of: fruit flavors, in particular citrus flavors; meat, vegetable and condiment flavors; and meat, vegetable and condiment extracts.

[0071] By using the selected binder according to the invention in the production of a granular product containing one or more flavorants and / or odorants, the storage stability of the granular product is significantly improved. In particular, a plurality of flavorants and / or odorants are protected from oxidation by atmospheric oxygen and thus remain stable even when stored for several months until final use. BRIEF DESCRIPTION OF THE DRAWINGS

[0072] Figure 1 A spray drying agglomeration apparatus as described in EP3117720 is shown, wherein (Z2) is a nozzle or atomizer structure, (H) is a weir (with cover G) and (B) is a fluidized bed.

[0073] Figure 2 Unagglomerated spray-dried particles with lemon flavor are shown.

[0074] Figure 3 Shown are spray dried particles with lemon flavour agglomerated with water.

[0075] Figure 4 Shown are spray dried granules with lemon flavour agglomerated with 10% gum arabic.

[0076] Figure 5 Shown are spray dried granules with lemon flavour agglomerated with 30% maltodextrin DE8.

[0077] Figure 6Cuvettes are shown in which the reducing properties of gum arabic and modified starch from various sources were tested using the Folin-Ciocart reagent (see Example 3). Cuvettes 1 and 2 contain gum arabic (Seyal batch 32), cuvettes 3 and 4 contain gum arabic (Seyal batch 59), cuvettes 5 and 6 contain gum arabic (Senegal batch 55), and cuvettes 7 and 8 contain modified starch (batch 70). DETAILED DESCRIPTION

[0078] Example 1: Shelf life of spray products using different adhesives

[0079] A standard preparation is selected which has a relatively short shelf life due to sensitivity to the flavor or which may have a new application by extending the shelf life. Citrus flavors are used herein because their oxidation sensitivity is very high. The preparation comprises about 20% flavors, 20% emulsifiers and 60% carriers as solids. Modified starch or gum arabic is used as an emulsifier and maltodextrin is used as a carrier.

[0080] The spray products were agglomerated using different binder liquids at different concentrations. The binder liquids are as follows:

[0081]

[0082] DE 17-20 and DE 8-10 are the dextrose equivalents of the maltodextrins used.

[0083] The product was physically characterized and stored for accelerated storage testing by increasing the temperature and oxygen partial pressure to simulate a one-year storage period over 12 to 24 hours. Depending on the shelf life of the liquid seasoning, stability was tested after 6 or 12 months of accelerated storage. The results are shown in Table 1, where Oxipress 12 months and Oxipress 6 months represent accelerated storage under conditions simulating 12 months and 6 months, respectively.

[0084] As can be seen from the results, both the material itself and the spray concentration affect the storage stability. The conclusions can be drawn from the different spraying methods and drying properties of the adhesive liquid. However, surprisingly, the substance used only to bond the particles can actually improve the storage stability more than pure surface reduction (simulated by bonding with water or steam). This is because the substance does not cover the entire surface of the particles and therefore cannot seal the particles. Physical parameters also support the results of the stability test.

[0085] Table 1: Physical properties and storage test results

[0086]

[0087]

[0088]

[0089] Example 2: Sample Difference Test

[0090] Because the panelists' descriptions in Example 1 showed substantial differences that were not reflected in the "pass, fail" classification, another experimental approach was used to further tease out such differences.

[0091] According to the DoD (degree of difference) test procedure, the stored samples that passed the test in Example 1 were tasted against each other. No more than 5 samples should be compared at the same time, otherwise there is an increased risk of panelist fatigue, so the tests must be separated to avoid overloading the panelists.

[0092] The task of the panelists was to describe the differences of the samples from the standard (STD) using the given terms. To verify the results, the standard was also tasted as a sample. Fresh samples without agglomeration produced by spray drying were used as standards. The slight differences therefore mean that the stored samples are very close to the fresh product, which indicates that agglomeration by means of adhesive substances has a good protective effect. The % values ​​given refer to the proportion of panelists who completed the respective evaluation.

[0093] Tastings were performed with 0.2% of the samples in a test solution containing sugar and citric acid.

[0094] The results show that the stored samples

[0095] Lemon with glucose as a binder

[0096] Lemon with binder maltodextrin EN 17-20

[0097] Lemon with adhesive gum / modified starch

[0098] Shows better protection effect than other adhesives used for agglomeration.

[0099] The protective effect of glucose and maltodextrin may be due to the reducing action of sugar. However, surprisingly, the reducing sugar applied to the outside of the particle has such an effect. For agglomerates, a mixture of gum arabic and modified starch is used as a binder, and it can be inferred that due to the high interfacial activity of these materials, the spreadability of the binder liquid is very good, and therefore evenly coated on the particles, it is sealed. In addition, as shown in Example 3, gum arabic has reducing groups, so it is of benefit to oxidation stability.

[0100] Table 2: Tasting without binder and with mannitol and glucose as binders

[0101]

[0102]

[0103] STD lemon SD fresh

[0104] 237 Lemon Mannitol

[0105] 134 Lemon Glucose

[0106] 456 Lemon SD

[0107] 890 Lemon SD Fresh

[0108] SD = spray drying (spray drying)

[0109] Table 3: Tasting without binder and with maltodextrin, dextrose and gum / modified starch as binder

[0110]

[0111]

[0112] STD lemon SD fresh

[0113] 569 Lemon Maltodextrin De 17-20

[0114] 134 Lemon Glucose

[0115] 862 Lemon SD

[0116] 709 Lemon SD Fresh

[0117] 302 lemon gum / modified starch

[0118] Table 4: Tasting without binder and with maltodextrin, whey and gum / modified starch as binder

[0119]

[0120]

[0121] STD lemon SD fresh

[0122] 234 Lemon Maltodextrin De 17-20

[0123] 890 Lemon SD Fresh

[0124] 410 Lemon Whey

[0125] 622 Lemon SD

[0126] 398 Lemon Gum / Modified Starch

[0127] Example 3: Reduction performance test of gum arabic and modified starch

[0128] In the presence of reducing groups, the Folin-Ciocart reagent reacts, showing a color change from yellow to blue: Mo(VI)+e-->Mo(V).

[0129] For each determination, 500 μl of 10% gum arabic solution was shaken with +750 μl Folin-Ciocart reagent, then 750 μM 8% Na2CO3 solution was added, shaken again, and then stored in a cuvette for 2 h.

[0130] After 2 hours, the absorbance was measured at 765 nm.

[0131]

[0132] Figure 6 The cuvettes are shown. The darker the solution color, the stronger the reducing properties of the substance tested. Cuvettes 1 and 2 contain gum arabic (Seyal batch 32), cuvettes 3 and 4 contain gum arabic (Seyal batch 59), cuvettes 5 and 6 contain gum arabic (Senegal batch 55), and cuvettes 7 and 8 contain modified starch (batch 70). Modified starch is almost colorless and therefore contains very few reducing groups.

Claims

1. A process for producing a granular product containing one or more flavorants and / or flavor enhancers, comprising: (i) producing particles comprising or consisting of one or more flavorants and / or flavor enhancers and one or more carriers by spray drying in a drying chamber of a spray drying apparatus, (ii) spraying one or more binders selected from the group consisting of monosaccharides or polysaccharides having reducing groups and sugar alcohols or mixtures thereof onto the particles in a fluidized bed integrated into the drying chamber, wherein the binders are used in a total amount of 10 vol% to 30 vol% in aqueous solution. wherein steps (i) and (ii) are performed simultaneously, and the particles are kept moving and agglomerated in the drying chamber, and wherein the aqueous solution of the adhesive does not contain any flavoring agents and / or flavor enhancers, wherein in step (i), an emulsion comprising one or more flavoring agents and / or flavor enhancers, one or more carriers and at least one emulsifier is sprayed, and The solids in the emulsion in step (i) are used in a weight ratio of 30:1 to 70:1 to the solids in the binder solution in step (ii).

2. The process according to claim 1, wherein the binder is used in a total amount of 10 vol% to 20 vol% in aqueous solution.

3. The process according to claim 1, wherein the binder is selected from the group consisting of: sugar alcohols; monosaccharides, disaccharides and oligosaccharides having reducing groups or mixtures containing or consisting of monosaccharides, disaccharides and / or oligosaccharides having reducing groups; and polysaccharides having reducing groups.

4. The process according to claim 3, wherein the binder is selected from the group consisting of: mannitol; glucose, mannose, galactose, maltose, lactose, cellobiose and maltodextrin; and vegetable gums.

5. A process as claimed in claim 4, wherein the vegetable gums are gum arabic, gum tragacanth, gum ghatti, agar, carrageenan, guar flour and carob bean gum.

6. The process of claim 1 or 3, wherein the flavorants and / or taste enhancers are selected from the group consisting of: fruit flavors; meat, vegetable and condiment flavors; and meat, vegetable and condiment extracts.

7. The process of claim 6, wherein the fruit flavor is citrus flavor.

8. The process according to any one of claims 1 to 5, wherein the carrier is selected from the group consisting of maltodextrin, dextrin, starch, flour and fibrous material.

9. The process according to claim 1, wherein the flavorant and / or flavor enhancer is used in a ratio of 2:1 to 1:2 with the at least one emulsifier, and / or wherein the flavorant and / or flavor enhancer is used in a ratio of 1:2 to 1:4 with the carrier.

10. The process according to claim 9, wherein the flavorant and / or flavor enhancer is used in a ratio of 1.5:1 to 1:1.5 with the at least one emulsifier and / or wherein the flavorant and / or flavor enhancer is used in a ratio of 1:2.5 to 1:3.5 with the carrier.

11. The process of claim 1, wherein the at least one emulsifier is selected from the group consisting of gum arabic, modified starch, protein, natural or modified pectin, and soluble fractions of soy polysaccharides.

12. The process of claim 11, wherein the protein is a plant protein.

13. The process according to claim 1 or 11, wherein the emulsion in step (i) is used in a volume ratio of 5:1 to 15:1 to the binder solution in step (ii).

14. The process according to claim 13, wherein the emulsion in step (i) is used in a volume ratio of 8:1 to 12:1 to the binder solution in step (ii), and / or wherein the solids in the emulsion in step (i) are used in a weight ratio of 40:1 to 60:1 to the solids in the binder solution in step (ii).

15. A granular product produced by a process according to any one of claims 1 to 14, wherein the product consists of granules comprising or consisting of a flavorant and / or flavor enhancer and one or more carriers agglomerated with a binder, wherein the agglomerated granules have a porous structure, and wherein the binder is selected from the group consisting of: monosaccharides or polysaccharides having reducing groups and sugar alcohols or mixtures thereof, and The adhesive does not contain any edible flavoring and / or flavor enhancer.

16. The granular product according to claim 15, wherein the binder is selected from the group consisting of: sugar alcohols; monosaccharides, disaccharides and oligosaccharides having reducing groups or mixtures containing or consisting of monosaccharides, disaccharides and / or oligosaccharides having reducing groups; and polysaccharides having reducing groups.

17. The granular product according to claim 16, wherein the binder is selected from the group consisting of: mannitol; glucose, mannose, galactose, maltose, lactose, cellobiose and maltodextrin; and vegetable gums.

18. The granular product according to claim 17, wherein the vegetable gum is gum arabic, gum tragacanth, gum ghatti, agar, carrageenan, guar flour and carob bean gum.

19. The granular product according to claim 15 or 16, consisting of the following substances: - 2 to 35 wt% of flavorants and / or flavor enhancers, and - 65 wt% to 98 wt% of carriers, binders and emulsifiers, Where the binder or one, more or all of the binders are different from the carrier and / or the emulsifier, the granular product comprises 1 wt % to 10 wt % of binder, in each case based on the total weight of the product.

20. The granular product according to claim 19, consisting of: - 15 to 25 wt% of flavorants and / or flavor enhancers, and - 65 wt% to 98 wt% of carriers, binders and emulsifiers, Wherein, in the case where the binder or one, more or all of the binders are different from the carrier and / or the emulsifier, the granular product comprises 5 wt % to 8 wt % of binder, in each case based on the total weight of the product.

21. A granular product according to any one of claims 15 to 18, wherein the carrier is selected from the group consisting of maltodextrin, dextrin, starch, flour and fibrous material, and / or wherein the emulsifier is selected from the group consisting of gum arabic, modified starch, protein, natural or modified pectin and soluble components of soy polysaccharides.

22. A granular product according to claim 21, wherein the protein is a vegetable protein.

23. A granular product according to any one of claims 15 to 18, wherein the flavour enhancer and / or flavouring agent is selected from the group consisting of: fruit flavours; meat, vegetable and condiment flavours; and meat, vegetable and condiment extracts.

24. A granular product according to claim 23, wherein the fruit flavour is citrus flavour.

25. A product comprising the particulate product according to any one of claims 15 to 24, the product being selected from food and beverage products.

26. The product according to claim 25, wherein the product is hot and cold, alcoholic and non-alcoholic beverages, fruit and vegetable juice products, instant beverages, meat products, egg products, dairy products, products made from soy protein and other vegetable protein sources, fatty and oily products or emulsions thereof, fruit and vegetable products, snacks, soups, spice and seasoning mixes, instant products, ready-to-eat products, semi-finished products and food supplements.

27. The product according to claim 26, wherein the product is a baked good, a confectionery, a sauce.

28. Use of one or more substances selected from monosaccharides or polysaccharides having reducing groups and sugar alcohols as a binder for improving the oxidative stability of one or more flavorants and / or taste enhancers in a granular product according to any one of claims 15 to 24, the granular product being produced or producible by a process according to any one of claims 1 to 14.

29. The use according to claim 28, wherein the substance is selected from the following substances: sugar alcohols; monosaccharides, disaccharides and oligosaccharides having reducing groups or mixtures containing or consisting of monosaccharides, disaccharides and / or oligosaccharides having reducing groups; and polysaccharides having reducing groups.

30. The use according to claim 29, wherein the substance is selected from the group consisting of: mannitol; glucose, mannose, galactose, maltose, lactose, cellobiose and maltodextrin; and vegetable gums.

31. Use according to claim 30, wherein the vegetable gum is gum arabic, gum tragacanth, gum ghatti, agar, carrageenan, guar flour and carob bean gum.

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