Water-soluble creatine agglomerate

Abstract

The present invention relates to a creatine agglomerate having improved solubility characteristics in aqueous systems and improved handling, thus simplifying the intake of creatine. The agglomerate is characterised in that it contains 30 to 99.9 wt.% of ground creatine and / or ground creatine derivatives and / or ground creatine salts and 0.1 to 30 wt.% of a binder containing at least one oligosaccharide, in particular maltodextrin, based on the total weight of the agglomerate.

Description

[0001] Water-soluble creatine agglomerate

[0002] Description

[0003] The present invention relates to a creatine agglomerate with improved solubility in aqueous systems and improved handling, which simplifies the intake of creatine.

[0004] Creatine is obtained through chemical synthesis. During synthesis, the product is a crystalline material that is easy to filter. The resulting creatine has relatively low water solubility. For example, the solubility of creatine monohydrate in water at 20°C is 13 g / L. Furthermore, due to its crystalline nature, complete dissolution of creatine is often delayed or not achieved at all in practical use. This is particularly disadvantageous when the crystalline creatine is dissolved in a liquid and taken. A residue often remains, making it unpleasant for the consumer.

[0005] A number of "micronized" creatine products are available on the market, with an average particle size (x50) typically ranging between 2 pm and 70 pm. For example, application WO 2007 / 095734 A1 discloses a method for improving the bioavailability of dietary supplements, including creatine. For this purpose, the use of micronized dietary supplements with reduced particle size is recommended, which, among other things, have improved solubility properties in water.

[0006] Although the dissolution properties of micronized creatine products are improved compared to coarsely crystalline products, they are still not optimal. Furthermore, the handling properties of micronized products typically correspond to those of finely ground products. These products generally have a low bulk density and poor flow and pouring properties, which are disadvantageous in practical use. If the powder is too fine, the wettability of the creatine with water suffers, making it difficult to stir the creatine powder and thus difficult to dissolve in water.

[0007] In order to further improve the solubility properties of creatine and thus the oral absorption of creatine using aqueous liquids, various proposals have already been made.

[0008] Patent application CN 104 432 095 A describes spray-dried creatine particles, which are spray-dried using a creatine suspension. Large quantities of spray-drying and instantizing additives are required to produce the suspension, resulting in a correspondingly low amount of creatine in the resulting granules.

[0009] US Patent No. 9,445,622 B2 describes a method for improving the solubility of nitrogen-containing organic acids, such as creatine. This involves adding certain proteins to ground creatine.

[0010] US 2002-0151593 A1 describes creatine monohydrate formulations with improved water solubility. For this purpose, creatine monohydrate with a mean particle diameter of 40 pm or less and an anti-agglomeration agent, such as dextrose, are mixed and ground.

[0011] WO 2017 / 106687 A1 discloses a method for increasing muscle protein synthesis in mammals by administering essential amino acids, amino acid derivatives, and nitrogen-containing organic acids. The administered compositions can contain, among other things, polysaccharides as binders. WO 94 / 17794 A1 describes pharmaceutical mixtures of glycine derivatives and sugars, including maltodextrin, which can be administered, among other things, in aqueous solution.

[0012] Despite the improvements achieved so far in the solubility of creatine products, there remains a high demand for products that can be easily incorporated into aqueous liquids, thus offering easy handling, and dissolving quickly and reliably. A further aim of the invention is to ensure the highest possible creatine content in the product without compromising the solubility or handling of the product.

[0013] Furthermore, the present invention is based on the object of finding a dosage form for creatine that requires as few additives as possible.

[0014] The task is solved with finely ground creatine, which is agglomerated after the addition of a binder containing at least one oligosaccharide.

[0015] Thus, an agglomerate containing a) 30 to 99.9 wt.% of ground creatine and / or ground creatine derivatives and / or ground creatine salts, based on the total weight of the agglomerate and b) 0.1 to 30 wt.% of a binder containing at least one oligosaccharide, based on the total weight of the agglomerate,

[0016] Subject of the present invention.

[0017] Binders are additives whose addition can be helpful for agglomeration by increasing the stability of the agglomerated particles. For the agglomerates described here, oligosaccharide-based binders have proven suitable for increasing the stability of the creatine particles and simultaneously improving their dissolution behavior in aqueous liquids. Furthermore, such binders also significantly improve the handling of the creatine agglomerates, which are intended to be dissolved as bulk materials in aqueous media.

[0018] In addition to oligosaccharides, the binder b) may also contain monosaccharides (simple sugars) and polysaccharides, particularly if it is produced by partial hydrolysis from naturally occurring polysaccharides, as is the case, for example, in the production of maltodextrin from starch.

[0019] The claimed agglomerate preferably comprises 1 to 20 wt.% binder b), particularly preferably 3 to 18 wt.%, in particular 5 to 15 wt.%.

[0020] The binders b) consist essentially of a carbohydrate selected from the group of oligosaccharides or a mixture of carbohydrates from monosaccharides, oligosaccharides and / or polysaccharides, wherein the carbohydrate(s) preferably constitute(s) at least 90% by weight, better at least 95% by weight and in particular at least 99% by weight based on the total weight of the binder b).

[0021] The average molecular weight M w (Weight average) of preferred carbohydrate mixtures that can be used as binder b) is in the range of 5,000 to 250,000 g / mol, in particular between 9,000 and 150,000 g / mol and particularly preferably between 12,000 and 100,000 g / mol, even better between 15,000 and 75,000 g / mol. The average molecular weight MnThe (number average) molecular weight of preferred carbohydrate mixtures is in the range from 500 to 10,000 g / mol, in particular between 1,250 and 7,500 g / mol, and particularly preferably between 1,500 and 6,000 g / mol, even better between 1,500 and 5,000 g / mol. The weight average or number average molecular weight can be determined by size exclusion chromatography as described in Avaltroni F. et al., Carbohydrate Polymers 58 (2004), 323-334 under section 2.4. Oligosaccharides within the meaning of the present invention are preferably polysaccharides with 2 to 15 sugar units, particularly preferably with 3 to 10 sugar units, in particular 3 to 6 sugar units, which are linked to one another via glycosidic bonds. The longer-chain polysaccharides are considered polysaccharides within the meaning of the present invention. Typically, polysaccharides, such as starch, can contain molecules with up to 20,000 sugar units or more.If the double sugars can no longer be classified as oligosaccharides according to the preferred oligosaccharide definition, they are referred to as disaccharides.

[0022] The proportion of simple sugars, such as glucose, should be below 25 mol%, particularly preferably between 0.1 and 15 mol%, in particular between 1 and 10 mol%, based on the total weight of the carbohydrate mixture of the binder b). The molar proportion of disaccharides, such as maltose, in the carbohydrate mixture should preferably be below 30 mol%, in particular between 1 mol% and 25 mol%, particularly preferably between 5 mol% and 20 mol%. The molar proportion of oligosaccharides with 3 to 6 sugar units in the carbohydrate mixture is preferably above 20 mol%, in particular in the range from 25 mol% to 80 mol%, particularly preferably in the range from 30 mol% to 70 mol%. The proportion of higher oligosaccharides and polysaccharides is preferably below 60 mol%, in particular between 10 mol% and 55 mol%, particularly preferably between 20 mol% and 50 mol%.

[0023] The sugars from which the oligosaccharides or polysaccharides are made up are preferably hexoses, such as aldohexoses, in particular glucose, mannose, and galactose, or ketohexoses, such as fructose, or pentoses, such as ribose or arabinose. The sugars can be present in their D- or L-configuration or as a mixture of both configurations. Particular preference is given to oligo- and polysaccharides which are made up of or consist of more than 90% by weight of hexoses. The sugar units of the oligo- and polysaccharides are preferably linked to one another via glycosidic bonds. Particular preference is given to oligo- and polysaccharides which contain 50% or more, or even better at least 80%, glucose units as building blocks. Gluco-oligosaccharides which are made up exclusively of glucose units, such as maltodextrin, are particularly suitable.

[0024] The use of maltodextrin as a binder for creatine agglomerates has proven particularly preferred. Maltodextrin is a water-soluble mixture of carbohydrates, usually produced by partial hydrolysis of starch (poly-α-glucose). The starch used for this can come from grains or vegetables, such as corn, potatoes, or tapioca. Hydrolysis can be carried out using methods such as acid or enzymatic methods, or a combination of both.

[0025] Maltodextrin is a mixture of glucose monomers, oligomers, and polymers. The composition of the mixture varies depending on the degree of hydrolysis. The mixture is usually described by the dextrose equivalent. According to the invention described here, products whose dextrose equivalent is between 3 and 20 are referred to as maltodextrin. The creatine agglomerates disclosed here preferably comprise maltodextrins with a dextrose equivalent of 3 to 15, particularly preferably in the range of 4 to 12, especially 4 to 10.

[0026] The dextrose equivalent of a polysaccharide mixture refers to the percentage by mass of reducing sugars (calculated as glucose) in the dry matter. It therefore corresponds to the mass of glucose (= dextrose) that would have the same reducing power per 100 g of dry matter. The DE value is a measure of the extent to which starch has been broken down; therefore, products with a low DE value contain a high proportion of polysaccharides and a low content of low-molecular-weight sugars, while products with a high DE value consist primarily of low-molecular-weight sugars. The dextrose equivalent (DE) is usually stated by maltodextrin manufacturers. However, the DE value can also be determined by Lane-Eynon titration (Lane, J.H. and Eynon, L., J. Soc. Chem. Ind. Trans. 42 (1923), 32-36) according to DIN EN ISO 5377-1994.

[0027] In a particularly preferred embodiment of the present invention, 0.5 to 20 wt.%, preferably 0.5 to 18 wt.%, in particular 1 to 15 wt.% or 5 to 12 wt.% of maltodextrin, based on the total weight of the agglomerate, are used as binder b).

[0028] Particularly preferred maltodextrins contain less than 5 wt.%, in particular 0.05 to 3 wt.% glucose as a simple sugar and less than a maximum of 20 wt.%, preferably between 0.1 and 15 wt.%, in particular between 0.5 and 10 wt.% maltose. The wt.% data refer to the total weight of the carbohydrate mixture of the binder b).

[0029] The agglomerate according to the invention contains 0.1 to 30 wt.% of a binder containing at least one oligosaccharide, based on the total weight of the agglomerate. According to the invention, all carbohydrates contained in the agglomerate, in particular all monosaccharides, oligosaccharides and polysaccharides, are preferably assigned to the binder b). Particularly preferably, the binder consists of at least 95 wt.%, more preferably at least 99 wt.% and even more preferably at least 99.9 wt.% and in particular exclusively (i.e., 100 wt.%) carbohydrates, i.e., mono-, oligo- and polysaccharides. In a particularly preferred embodiment, further additives, if present, are not assigned to the binder b), but to the further additives c).

[0030] The binder b) can consist entirely of oligosaccharides. In this case, the proportion of oligosaccharides in the binder b) is 100 wt.%. However, it is also possible for the binder b) to contain further carbohydrates, in particular monosaccharides or polysaccharides, in addition to the oligosaccharides. In a preferred embodiment, the proportion of oligosaccharide in the binder b) is preferably at least 0.1 wt.%, more preferably at least 0.5 wt.%, and even more preferably at least 1 wt.%, based on the total weight of the binder b). More preferably, the proportion of oligosaccharide in the binder b) is at least 10 wt.%, even more preferably at least 20 wt.%, and most preferably at least 30 wt.%, based on the total weight of the binder b). The proportion of oligosaccharide in the binder b) can be up to 100 wt.%, preferably up to 99 wt.%, more preferably up to 90 wt.%, even more preferably up to 80 wt.-% and most preferably up to 70 wt.% and especially up to 50 wt.%.

[0031] Particularly preferably, the binder b) consists of > 90 wt.% carbohydrates, of which 10 to 90 wt.%, preferably 20 to 80 wt.% and even more preferably 30 to 70 wt.% are oligosaccharides.

[0032] In a further preferred embodiment, the proportion of oligosaccharide in the binder b) is preferably at least 0.1 mol%, more preferably at least 0.5 mol%, and even more preferably at least 1 mol%, based on the total binder b). More preferably, the proportion of oligosaccharide in the binder b) is at least 10 mol%, even more preferably at least 20 mol%, and most preferably at least 30 mol%, based on the total binder b). The proportion of oligosaccharide in the binder b) can be up to 100 mol%, preferably up to 99 mol%, more preferably up to 90 mol%, even more preferably up to 80 mol%, and most preferably up to 70 mol%, based on the total binder b).

[0033] Particularly preferably, the binder b) consists of > 90 wt.%, in particular at least 99 wt.% carbohydrates, of which 10 to 90 mol.%, preferably 20 to 80 mol.%, and even more preferably 30 to 70 mol.% are oligosaccharides. Creatine is a substance naturally present in the body that plays a central role in cellular energy metabolism. Creatine can be produced in the body through biosynthesis or obtained through food. The common form in which creatine is administered as a dietary supplement includes, in addition to pure creatine, creatine derivatives, such as creatine hydrates, especially creatine monohydrate. But creatine salts such as creatine citrate, pyruvate, hydrochloride, hydrobromide, hydrogen citrate, maleate, malate, nitrate, mesylate, dihydrogen phosphate, hydrogen oxalate, fumarate, tartrate, lipoate, bicarbonate and ascorbate are also used in dietary supplements.

[0034] For the purposes of this description, the term creatine refers not only to pure creatine but also to creatine derivatives and salts, unless explicitly stated otherwise. Thus, the term creatine agglomerate also includes agglomerates of creatine derivatives and creatine salts. Since pure creatine is hygroscopic, creatine is preferably used as a hydrate, with creatine monohydrate usually present in equilibrium with the air humidity.

[0035] Creatine monohydrate is typically produced by chemical synthesis and is obtained during production as a colorless, crystalline solid (Figure 1a). The solubility of creatine monohydrate in water is 13 g / L at 20 °C. As a dietary supplement, creatine monohydrate is often offered as a powder, which is taken by dissolving it in an aqueous liquid, e.g., mineral water or juice. A disadvantage has proven to be that conventional creatine monohydrate powders dissolve only slowly due to the relatively low solubility of the crystalline creatine monohydrate, often leaving a residue behind. Although creatine monohydrate dissolves relatively well when ground, the ground powders have poor wetting properties and require improvement in handling.Poor wetting is evident from the fact that the creatine powder sinks into the liquid only slowly upon contact with the surface and / or forms aggregates. It is often observed that the aggregates formed in this way dissolve only extremely slowly. In addition, handling fine powders poses further difficulties, as they often do not flow freely and are difficult to fill or transfer. The high dustiness of the powder also makes it difficult to pour the entire powder into a glass, for example, without the suspended solids drifting away. The pouring properties of the creatine powder are also not optimal; parts of the powder easily clump and stick to the packaging material, the angle of repose is high, and the flow and pourability are poor.

[0036] Other creatine salts, creatine derivatives and pure creatine show similar behavior.

[0037] The described disadvantages can be overcome by agglomerating ground creatine in the presence of an oligosaccharide-containing binder, such as maltodextrin. In this process, the ground creatine particles form agglomerates whose structure differs significantly from the crystalline particles of unground creatine (Figure 1b and c).

[0038] With the described binders, a high content of ground creatine can be ensured in the agglomerates without any significant impairment of dissolution behavior compared to the direct use of ground creatine powder. This was not to be expected, as the binders exhibit very good adhesive properties during agglomeration, which should counteract dissolution in aqueous liquids. Furthermore, the described handling parameters are significantly improved compared to simply ground creatine.

[0039] When starch is used as a binder, very stable creatine agglomerates are obtained, but the dissolution behavior deteriorates significantly. When dextrose is used as a binder, moist agglomerated creatine can be produced, which, however, disintegrates again upon drying. The binding properties of dextrose are insufficient for the production of creatine agglomerates. These disadvantages were eliminated according to the invention by using a binder containing at least one oligosaccharide. Milled creatine is used to produce the creatine agglomerates according to the invention. Milled creatine is preferably characterized by a particle size distribution with a x50 value in the range from 2 pm to 150 pm, a x10 value in the range from 0.01 pm to 20 pm, and a x90 value in the range from 15 pm to 250 pm.The x50 value of the ground creatine is preferably in the range from 3 pm to 80 pm, particularly preferably between 5 pm and 50 pm, and even more preferably between 5 pm and 30 pm. Preferred x10 values ​​are in the range from 0.1 pm to 10 pm, in particular between 0.5 pm and 5 pm. The x90 value is preferably in the range from 20 pm to 100 pm, particularly preferably from 30 pm to 70 pm. The values ​​x10, x50, and x90 are each based on the mass fraction of the respective particle group in the ground creatine. This means that the particles with a particle size above the x50 value make up 50 wt.% of the agglomerate, while the remaining 50 wt.% of the agglomerate comprises particles with a particle size smaller than x50. Accordingly, the agglomerate contains 10 wt.% of particles with a particle size below the x10 value and 10 wt.% above the x90 value.

[0040] Particularly preferred ground creatine powders have a x98 value in the range of 50 pm to 300 pm, especially between 60 and 120 pm. The x98 value is also based on the mass fraction in the ground creatine powder.

[0041] The amount of ground creatine in the agglomerate is preferably over 45 wt.%, particularly preferably at least 60 wt.%, more preferably over 60 wt.%, even more preferably at least 75 wt.%, in particular over 80 wt.%, based on the total weight of the agglomerates. The upper limit is 99.9 wt.%, preferably 99 wt.%, in particular 95 wt.%.

[0042] In a preferred embodiment, the invention relates to an agglomerate comprising a) 30 to 99.9 wt.%, preferably at least 45 wt.%, more preferably at least 60 wt.% and even more preferably at least 75 wt.% of ground creatine and / or ground creatine derivatives and / or ground creatine salts, in particular creatine monohydrate, based on the total weight of the agglomerate; and b) 0.1 to 30 wt.%, preferably 1 to 18 wt.% and more preferably 5 to 15 wt.% of a binder comprising at least one oligosaccharide, in particular maltodextrin, based on the total weight of the agglomerate; and c) 0 to 20 wt.%, preferably at most 10 wt.%, more preferably at most 5 wt.% of further additives; and d) 0 to less than 5 wt.%, preferably to less than 2 wt.% of free water.

[0043] Components a), b), c) and d) preferably make up 100% of the agglomerate, i.e. no other substances are contained in the agglomerate.

[0044] In a preferred embodiment, the invention relates to an agglomerate comprising a) 30 to 99.9 wt.%, preferably at least 45 wt.%, more preferably at least 60 wt.% and even more preferably at least 75 wt.% of ground creatine and / or ground creatine derivatives and / or ground creatine salts, in particular creatine monohydrate, based on the total weight of the agglomerate; and b) 0.1 to 30 wt.%, preferably 1 to 18 wt.% and more preferably at most 5 to 15 wt.% of a binder comprising at least one oligosaccharide, in particular maltodextrin, based on the total weight of the agglomerate; and d) 0 to less than 5 wt.%, preferably to less than 2 wt.% of free water.

[0045] Components a), b) and d) preferably make up 100% of the agglomerate, i.e. no other substances are contained in the agglomerate. In a particularly preferred embodiment, the agglomerate according to the invention consists of a) 30 to 99.9% by weight, in particular 90 to 99.9% by weight and particularly preferably 95 to 99.9% by weight of ground creatine and / or ground creatine derivatives and / or ground creatine salts, in particular creatine monohydrate, based on the total weight of the agglomerate and b) 0.1 to 30% by weight, preferably 1 to 18% by weight and particularly preferably 5 to 15% by weight of a binder containing at least one oligosaccharide, based on the total weight of the agglomerate, wherein the binder is particularly preferably maltodextrin; and d) up to a maximum of 1% by weight of free water.

[0046] In particular, the agglomerate which is particularly preferred according to the invention does not contain any further substances or additives.

[0047] The agglomerates according to the invention preferably have the following composition: a) 60 wt.% to 99.9 wt.%, preferably 75 wt.% to 99 wt.%, based on the total weight of the agglomerate, of ground creatine, in particular creatine monohydrate; b) 0.1 wt.% to 30 wt.%, preferably 1 wt.% to 25 wt.%, even more preferably 5 to 15 wt.%, based on the total weight of the agglomerate, of a binder containing at least one oligosaccharide; and c) 0 wt.% to 10 wt.%, in particular up to 5 wt.%, of further additives. Apart from the water bound to creatine as a hydrate, as little free water as possible should be present in the agglomerate, since excessive moisture tends to cause the agglomerate to clump. Preferably, the proportion of free water in the agglomerate should be less than 5 wt.%, particularly preferably between 0.01 and 2 wt.%, in particular between 0.05 and 1 wt.%.

[0048] In principle, agglomeration also allows the addition of further additives. Additional additives c) include, for example, additional binding agents that do not fall under binding agents b); solubility enhancers; antioxidants, buffers, sweeteners, colorings and flavorings, proteins, amino acids, vitamins, minerals, trace elements, etc.

[0049] Other binders and solubility improvers included under additives c) include, in particular, water-soluble substances approved as food additives or pharmaceutical additives, such as polyvinylpyrrolidone (PVP); propylvinyl alcohol; sugar alcohols, including sorbitol, xylitol; amino acids and glycerol; or mixtures of these substances.

[0050] The minerals include, in particular, inorganic salts such as sulfates, chlorides, carbonates, bicarbonates, acetates, citrates, gluconates, ascorbates, pantothenates, lactates, particularly their sodium, potassium, calcium, and magnesium salts, as well as mixtures thereof. Trimagnesium dicitrate, magnesium hydrogen citrate, sodium chloride (table salt), sodium sulfate, sodium acetate, sodium citrate, sodium gluconate, sodium ascorbate, sodium pantothenate, and sodium lactate, or mixtures of these salts, are particularly preferred.

[0051] The agglomerates can contain a buffer if required. Buffer systems are preferably selected that, when dissolved in an aqueous liquid, adjust the pH of the liquid to between 7 and 12, preferably between 9 and 11. Buffer systems consisting of a combination of a weak acid and a corresponding base are suitable for this purpose. Suitable buffer systems include mixtures of sodium hydrogen phosphate and sodium phosphate, L-lysine and L-lysine sodium salt, or L-arginine and L-arginine sodium salt. A mixture of sodium carbonate and sodium hydrogen carbonate is particularly preferred as the buffer system.

[0052] The use of buffer systems that create an alkaline environment is preferred because, on the one hand, they increase the stability of creatine against acids and thus prevent its degradation in the stomach. Furthermore, sodium ions, in particular, improve the absorption of creatine into the cells, although this effect can be further enhanced by the addition of additional sodium salts.

[0053] Sweeteners that fall under additives c) are sweeteners that do not contain carbohydrates. Common carbohydrate-based sweeteners, in particular natural sweeteners such as glucose and fructose, can be contained in the binder b), so that the agglomerates described can already be sufficiently sweet. If required, however, other, preferably water-soluble sweeteners such as cyclamate, aspartame, acesulfame, sucralose, stevia or sugar alcohols such as sorbitol, xylitol, mannitol, erythritol or lactitol can be added to the agglomerates. This can be particularly advantageous if the content of simple sugars in the binder is low. However, simple sugars such as glucose and fructose can be mixed with the finished agglomerate to achieve sufficient sweetness of the mixture.The latter can be advantageous since the content of simple sugars in the binder b) cannot be increased arbitrarily without impairing the handleability of the agglomerate.

[0054] Compounds with sufficient water solubility are particularly used as coloring and flavoring agents. Natural, nature-identical, and artificial flavorings can be used, preferably those approved for food or pharmaceutical use. Examples of flavoring agents that can be used include lemon or orange flavoring, as well as citric acid or tartaric acid or their salts. Bitter substances such as quinine or ginger extracts are also considered flavoring agents.

[0055] Vitamins and trace elements can also be added to the agglomerates, particularly those that are highly soluble in water. Preferably, vitamins from the group consisting of vitamin B1 (thiamine), vitamin B2 (riboflavin), vitamin B3 (niacin), vitamin B5 (pantothenic acid), vitamin B6 (pyridoxine), vitamin B7 (biotin), vitamin B9 (folic acid), vitamin B12 (cobalamin), vitamin C, and vitamin D3 (cholecalciferol), or mixtures thereof, can be added to the agglomerates. Trace elements are preferably used in the form of their water-soluble salts and are preferably selected from the group consisting of zinc, selenium, molybdenum, manganese, copper, iodine, fluorine, iron, and chromium, or mixtures thereof.

[0056] The additives c) are preferably added during the agglomeration process so that the additives are part of the agglomerates.

[0057] In a particular embodiment, the creatine agglomerates described contain no further additives c), in particular no suspension stabilizers from the group of celluloses, gelatins and gum resins, such as microcrystalline celluloses, carboxymethylcelluloses and xanthan gum, gellan gum and gum arabic.

[0058] Overall, the amount of additives c) in the agglomerate is preferably less than 20% by weight, in particular less than 10% by weight, based on the total weight of the agglomerate.

[0059] The compounds described as additives c) can also be easily mixed into the creatine agglomerate if necessary, provided they do not adversely affect the product's handling and water solubility. When mixed, higher proportions of these substances can also be administered together with the creatine agglomerate. In addition to additives c), non-agglomerable compounds can also be easily mixed in. As already mentioned, mono- and disaccharides can also be mixed with the agglomerate to adjust the sweetness of the mixture. Another important group of additives that can be easily mixed in are flow aids, such as SiO2.

[0060] The proportion of admixed substances should preferably be below 80% by weight. The mixtures typically contain between 10 and 70% by weight, particularly preferably between 20 and 60% by weight of such additives, based on the total weight of the mixture, especially when used as beverage powder. Accordingly, such mixtures comprise at least 20% by weight or more of the creatine agglomerate, particularly between 30 and 90% by weight, and very particularly preferably between 40 and 80% by weight, based on the total weight of the mixture.

[0061] Agglomeration is understood here as the process of grain enlargement of particulate creatine, whereby small creatine particles in the presence of the binding agent form larger, permanently aggregated creatine-containing agglomerates in which the original particles can usually still be identified.

[0062] Various methods can be used to agglomerate the ground creatine powder. Agglomeration in a fluidized bed, agglomeration by granulation in a mixer, e.g., an intensive mixer, and agglomeration by extrusion, especially wet extrusion, have proven advantageous.

[0063] Consequently, for the purposes of the present invention, the term "agglomeration" also includes the production of agglomerated particles by granulation and extrusion. Furthermore, other common agglomeration processes are also encompassed, such as agglomeration in a fluidized bed. Accordingly, the term "agglomerate" also includes, in particular, granules, fluidized bed agglomerates, and extrudates. Irregularly shaped, porous agglomerates are produced by spray agglomeration of creatine in the presence of a binder based on oligosaccharides in a fluidized bed. They have good flowability, are sufficiently abrasion-resistant, and have a medium bulk density. In water, they display very uniform wetting behavior, which causes the agglomerates to disintegrate immediately and the primary particles to dissolve within a very short time.

[0064] Stable agglomerated extrudates can also be produced by extrusion with the addition of the oligosaccharide-containing binder. If an appropriate amount of the binder is used, compact, highly abrasion-resistant, and uniform extrudates are obtained.

[0065] It has been shown that the granules and extrudates, despite their high stability and their partially compact nature, dissolve very quickly in liquids, e.g., water.

[0066] The amount of binder required to produce the agglomerates is relatively small. For example, between 0.5% and 15% by weight of maltodextrin in an agglomerate consisting essentially, i.e., 90% or more, of binder b) and creatine, e.g., in the form of creatine monohydrate, is often sufficient to agglomerate the creatine.

[0067] Suitable methods for producing the agglomerates described include dry and wet agglomeration. In dry agglomeration, the particles are compressed into compacted shapes under pressure in the presence of a binder without the addition of liquid. These compacted particles are then often reduced to a defined grain size. In wet agglomeration, liquid, usually water or a binder dissolved in water, is added during the agglomeration process. This increases the interfacial forces between the particles in the dried agglomerate and thus stabilizes the structure. In all of these processes, it has proven particularly advantageous to use the gentlest possible process to ensure that the chemical purity of the creatine is maintained and that no undesirable foreign substances are introduced.It has also been shown that the agglomerates are already sufficiently stable if only a binder consisting essentially of carbohydrates is added and no or only a small amount of water of less than 5 wt.%, based on the total weight of the agglomerate, is contained in the product.

[0068] The grain size distribution, also known as the particle size distribution, indicates the frequency distribution of the particle diameters. Various parameters can be read from the distribution function. For example, the x10 value indicates the particle diameter below which 10% of the particles fall. The x50 value is the indication of the average grain size or the particle diameter below which 50% of the particles fall. Analogously, 90% of the particles are smaller than the x90 value. A creatine agglomerate according to the invention with good properties preferably has a low fines fraction, represented by the x10 value, which should be at least 1 pm or more, in particular in the range between 5 pm and 800 pm, preferably between 10 pm and 600 pm. Furthermore, the average grain size, represented by the x50 value, should be at least 30 pm, and the upper grain size, represented by the x90 value, should not exceed 1800 pm. The average grain sizes x50 are from 50 pm to 1200 pm respectively.from 70 pm to 1000 pm is preferred. The x90 value is preferably between 100 pm and 1500 pm, especially above 200 pm. Typically, the difference between the x90 and x10 values ​​is between 100 pm and 1500 pm, preferably between 200 pm and 1000 pm.

[0069] The values ​​x10, x50 and x90 are based on the mass of the particles, which means that the particles with a particle size above the x50 value make up 50 wt.% of the agglomerate, while the remaining 50 wt.% of the agglomerate comprises particles with a particle size less than x50. Accordingly, the agglomerate contains 10 wt.% of particles with a particle size below the x10 value and 10 wt.% above the x90 value. Preferred agglomerates have a flowability [ffc] of greater than 4, preferably greater than 8 and in particular greater than 10 (free-flowing). Typically, the [ffc] value is less than 30, but higher values ​​are not harmful. The bulk density of preferred agglomerates is greater than 200 g / L. In particular, the bulk density should be at least in the range of pure ground creatine. Therefore, agglomerates with a bulk density between 250 g / L and 1,000 g / L are particularly preferred. However, higher bulk densities are not harmful.To facilitate pouring the agglomerates into a beverage, a low angle of repose is advantageous. Preferred agglomerates have an angle of repose of less than 50°, in particular less than 45°. The angle of repose is usually above 25°, but smaller angles of repose are not harmful. The flowability of preferred agglomerates is at least satisfactory (i.e. the agglomerate trickles through a vessel outlet with a diameter of 8 mm). Furthermore, preferred agglomerates are less dusty than ground creatine. The dust number is preferably less than 25, in particular between 2 and 20 or between 3 and 15. From these parameters, it can be seen that the agglomerates described here have excellent handling properties. They can be easily poured into beverages and have good wettability in water.

[0070] In addition, the agglomerates described here dissolve quickly and with minimal residue in aqueous media, such as beverages. The dissolution rate is comparable to or even faster than that of ground creatine.

[0071] The agglomerates according to the invention can be produced, for example, by granulation in high-shear mixers, by agglomeration in a fluidized bed, or by extrusion. The properties of the resulting agglomerates vary slightly depending on the production process.

[0072] Thus, granulation in the mixer produces a free-flowing agglomerate ([ffc] > 10) with acceptable dissolution behavior but with good flowability and good pouring properties (very good bulk density > 400 g / L and good angle of repose < 40°). Furthermore, the granules exhibit very low dustiness (dust number < 12, usually even < 10).

[0073] Fluidized bed agglomeration produces easily flowing ([ffc] > 4), usually even free-flowing ([ffc] > 10) agglomerates with satisfactory flowability. However, fluidized bed agglomerates generally exhibit very good dissolution behavior, even better than that of ground creatine. Furthermore, the fluidized bed agglomerates have good bulk properties (bulk density > 200 g / L, especially between 250 g / L and 600 g / L, good angle of repose < 45°, especially < 40°). The fluidized bed agglomerates are also characterized by low dustiness (dust number < 20, especially < 15).

[0074] The extrudates are also free-flowing ([ffc] > 10) and have good flow properties. The pouring properties are very good (bulk density > 400 g / L, angle of repose < 40°). Furthermore, the extrudates have low dustiness (dust number < 15). The extrudates exhibit very good dissolution behavior, significantly better than that of ground creatine.

[0075] The granules have a preferred particle size distribution which is characterized by a x10 value in the range from 10 pm to 800 pm, in particular between 100 pm and 600 pm, a x50 value in the range from 80 pm to 1,200 pm, in particular from 550 pm to 1,000 pm and a x90 value in the range from 200 pm to 1,800 pm, in particular from 800 pm to 1,500 pm.

[0076] The fluidized bed agglomerates have a preferred particle size distribution which is characterized by a x10 value in the range from 1 pm to 300 pm, in particular between 5 pm and 100 pm or even between 5 pm and 50 pm, a x50 value in the range from 30 pm to 500 pm, in particular from 50 pm to 300 pm and a x90 value in the range from 100 pm to 1,500 pm, in particular from 200 pm to 800 pm. The extrudates have a preferred grain size distribution which is characterized by a x10 value in the range from 100 pm to 800 pm, in particular between 300 pm, better 400 pm and 750 pm, a x50 value in the range from 200 pm to 1,200 pm, in particular from 500 pm to 1,000 pm and a x90 value in the range from 300 pm to 1,800 pm, in particular from 800 pm to 1,500 pm.

[0077] The agglomerates described here are particularly suitable as bulk powders for stirring the creatine they contain into beverages such as mineral water, fruit juices, or sweet drinks. However, the agglomerates can also be used as direct agglomerates. In this case, the agglomerate is poured directly onto the tongue and, if desired, washed down with a drink.

[0078] Examples of implementation:

[0079] I) Test methods and properties:

[0080] 1 . Method for determining the dissolution rate:

[0081] Place 175 mL of water at 23 °C into a 250 mL beaker with a 5.5 cm inner diameter and stir with a glass stirrer at 60 revolutions per minute. Then, add 1.75 g of creatine or creatine agglomerate and stir for 10 seconds. The stirrer is then turned off and the suspension is immediately filtered through a ceramic suction filter fitted with a blue band filter and a suction flask. The moist filter residue is dried. The mass of the filter residue serves as a measure of the dissolution rate; the lower the mass, the better the dissolution rate.

[0082] 2. Determination of flowability (outlet funnel):

[0083] The test equipment consists of five test funnels with the same diameter (36 mm inner diameter) and a 28-degree inclination angle, but with different outlet diameters (2.5 mm; 5 mm; 8 mm; 12 mm; and 18 mm). A 50 mL sample of creatine or the creatine formulation is poured into the test funnels, with the outlet sealed from below to prevent any spillage during filling. In the next step, the outlet is fully opened—without shaking the test funnel—so that the entire outlet cross-section is exposed. The evaluation criterion is the diameter at which the solid trickles through independently and without external influence. The following applies:

[0084] - Solids trickle through the 2.5 mm outlet: Grade 1

[0085] - Solids trickle through the 5 mm outlet: Grade 2

[0086] - Solids trickle through the 8 mm outlet: Grade 3

[0087] - Solids trickle through the 12 mm outlet: Grade 4

[0088] - Solids trickle through the 18 mm outlet: Grade 5

[0089] - Solids do not trickle through the 18 mm outlet: Grade 6

[0090] The lower the rating, the better the flowability.

[0091] 3. Determination of the angle of repose

[0092] The angle of repose was determined according to the method DIN ISO 4324 (1983-12) Surfactants; Powders and Granules; Determination of the Angle of Repose. The smaller the angle of repose, the better the flow properties.

[0093] 4. Determination of flowability

[0094] The flowability of solids (powders and agglomerates) is determined using the "Evolution Powder Tester" measuring device from PS Prozesstechnik GmbH, Basel, Switzerland. Flowability is expressed as a dimensionless number [ff c]. The method used is compression determination on the Evolution Powder Tester; time consolidation is not performed. For this purpose, 25 mL of the solid is weighed into the measuring cell and placed in the measuring device. After the measurement has started, the solid is compressed in the measuring cell with a punch speed of 15 mm per minute and a force (Fi) of 10,000 kPa for 30 seconds. The resulting solid compact in the measuring cell is then subjected to a further punch speed of 10 mm per minute and a slowly increasing force (F2) until the solid compact breaks. The ratio of the force (Fi) for compression and the force (F2) for breaking the compact corresponds to the flowability [ff c ] and is calculated using the formula:

[0095] Fi

[0096] Flowability [ff c ] = —

[0097] F2

[0098] For the classification of flowability [ff c] the following rating applies:

[0099] 5. Determination of dustiness

[0100] The dustiness of solids (powders and agglomerates) is expressed as a dimensionless dust number. The dust number is determined using the DustView II dust measuring device from Palas GmbH, Karlsruhe.

[0101] For this purpose, 30.0 g of a sample is weighed and placed in the filling funnel on the flap. The measurement is then started by pressing the control panel. The flap opens and the solid falls freely into the dust box. The impact of the solid stirs up the dusty portion. As a result, the light beam emitted by the laser is attenuated by the stirring up dust, and the attenuated light beam is detected at the receiver. The degree of attenuation (transmission signal) in comparison to the light beam emitted by the light source is a measure of the dustiness of the solid. A value of 100 means the maximum possible attenuation of the light beam, and a value of 0 means no attenuation of the light beam. To determine the dust count, the value of the maximum attenuation of the light beam is added to the value 30 seconds after the start of the measurement and output as the dust count.

[0102] The lower the dust number, the less dusty the solid is.

[0103] 6. Determination of bulk density

[0104] The determination of bulk density was carried out according to the method DIN ISO 697 (1984-01) Surfactants; Detergents; Determination of bulk density; Method by measuring the mass of a given volume.

[0105] The higher the bulk density, the more advantageous it is to handle.

[0106] 7. Determination of the grain size distribution

[0107] The particle size distribution was determined using a laser diffraction method on a "HELOS / KR" particle size measuring device from Sympatec GmbH. The R6 orifice plate was used, which covers a measuring range from 0.5 to 1750 pm. The sample was introduced via a vibrating chute at 60% power and a dispersion pressure of 2.5 bar. The software version "WINDOX 5.1.2.0, LD" was used for the evaluation.

[0108] Trigger condition settings: Time base 100.00 ms, start at c.opt >= 1.0%, c.opt validity from 1.0% to 14.0%, stop at 5.000s c.opt <= 0.9% or 10.000s real time. The x10, x50, and x90 values ​​were used to assess agglomerate quality, represented as the distribution sum Q3 in a histogram of the grain size distribution. II) Examples

[0109] Where percentages are given in the examples, these are percentages by weight unless explicitly stated otherwise.

[0110] Example 1 (comparison): Agglomeration in the Eirich mixer - use of modified starch as binder.

[0111] 1500 g of fine creatine monohydrate and 45 g of modified starch (product name: Spezialstärke 6023 FF from Südstärke GmbH) were placed in a 10-liter intensive mixer (Eirich). The mixer contents were then stirred countercurrently at 1500 rpm, and 335 g of water were continuously added to the mixer contents over a period of 3 minutes. After the water addition, the mixer contents were further stirred countercurrently at 1500 rpm, and granulation began. After a granulation time of 9 minutes, granules in the desired particle size range were obtained. The resulting moist creatine monohydrate granules were dried in a fluidized bed dryer.

[0112] Example 2: Agglomeration in the Eirich mixer - use of maltodextrin 6 as a binder.

[0113] 1500 g of fine creatine monohydrate were placed in a 10-liter intensive mixer (Eirich). 42 g of maltodextrin (Glucidex IT 6 from Roquette) dissolved in 450 g of water were then added to the creatine monohydrate in the mixer while stirring slowly. The mixer contents were then stirred countercurrently at 1500 rpm, and granulation began. After a granulation time of 7 minutes, granules in the desired particle size range were obtained. The resulting moist creatine monohydrate granules were dried in a fluidized bed dryer.

[0114] Example 3: Agglomeration in the Eirich mixer - Use of maltodextrin 6 as a binder. TI

[0115] 1500 g of fine creatine monohydrate were placed in a 10-liter intensive mixer (Eirich). Then, while stirring slowly, 75 g of maltodextrin (Glucidex IT 6 from Roquette) dissolved in 400 g of water was added to the creatine monohydrate in the mixer. The mixer contents were then stirred countercurrently at 1500 rpm, and granulation began. After a granulation time of 15 minutes, granules in the desired particle size range were obtained. The resulting moist creatine monohydrate granules were dried in a fluidized bed dryer.

[0116] Example 4 (comparison): Agglomeration in the Eirich mixer - use of dextrose as a binding agent.

[0117] 1500 g of fine creatine monohydrate were placed in a 10-liter intensive mixer (Eirich). Then, while stirring slowly, 135 g of dextrose (product name: "Zec+ Dextrose" from Zec+ Nutrition) dissolved in 350 g of water were added to the creatine monohydrate in the mixer. The mixer contents were then stirred countercurrently at 1500 rpm, and granulation began. After a granulation time of 7 minutes, granules in the desired particle size range were obtained. The resulting moist creatine monohydrate granules were placed in a fluidized bed dryer and dried as described in Examples 1 to 3. During this process, the granules disintegrated into fine particles; the binding effect of dextrose was insufficient to produce stable granules.

[0118] Example 5 (comparison): Agglomeration in the Eirich mixer - granulation of the composition according to an example from US 2002 / 0151593 A1.

[0119] In a 10-liter intensive mixer (Eirich), 3000 g of finely ground dextrose (product name: "Zec+ Dextrose" from Zec+ Nutrition) and 750 g of fine creatine monohydrate were placed. 375 g of water were then added to the solid mixture in the mixer while stirring slowly. The mixer contents were then stirred countercurrently at 1500 rpm, and granulation began. After a granulation time of 5 minutes, granules in the desired particle size range were obtained. The resulting moist creatine monohydrate granules were placed in a fluidized bed dryer and dried analogously to Examples 1 to 3.

[0120] The granules disintegrated into fine particles; the binding effect of dextrose was insufficient to produce stable granules. Example 6 (Comparison): For further comparison, ground, pure creatine monohydrate was used.

[0121] The resulting products are then characterized, where possible, using the methods described under I). The results are summarized in Table 1.

[0122] Table 1 : Results of agglomeration by granulation Example 7: Agglomeration in the fluidized bed - use of maltodextrin 6 (Glucidex IT 6 from Roquette) as a binder.

[0123] In a fluidized bed agglomeration apparatus, 12.0 kg of fine creatine monohydrate were placed in the process chamber, and the apparatus was then tightly sealed for the agglomeration process. A suitable and preheated air flow rate was then set, which enabled the creatine monohydrate particles to fluidize in the fluidized bed. This warmed the internal temperature of the apparatus. Once the appropriate flow rate was set, 9.2 kg of a 20% aqueous maltodextrin 6 solution was sprayed countercurrently into the fluidized bed using a two-fluid nozzle over a period of 25 minutes, with an agglomerate forming as the spraying time increased. After the spraying was complete, the resulting agglomerate was further dried in the fluidized bed until the water not bound to the creatine monohydrate was removed.

[0124] Example 8: Agglomeration in the fluidized bed - use of maltodextrin 6 (Glucidex IT 6 from Roquette) as a binder.

[0125] In a fluidized bed agglomeration apparatus, 12.0 kg of fine creatine monohydrate were placed in the process chamber, and the apparatus was then tightly sealed for the agglomeration process. A suitable and preheated air flow rate was then set, which enabled the creatine monohydrate particles to fluidize in the fluidized bed. This warmed the internal temperature of the apparatus. Once the appropriate flow rate was set, 5.6 kg of a 20% aqueous maltodextrin 6 solution was sprayed countercurrently into the fluidized bed using a two-fluid nozzle over a period of 16 minutes, with an agglomerate forming with increasing spraying time. After spraying, the resulting agglomerate was further dried in the fluidized bed until the water not bound to the creatine monohydrate was removed.Example 9: Agglomeration in the fluidized bed - use of maltodextrin 6 (Glucidex IT 6 from Roquette) as a binder.

[0126] In a fluidized bed agglomeration apparatus, 12.0 kg of fine creatine monohydrate were placed in the process chamber, and the apparatus was then tightly closed for the agglomeration process. A suitable and preheated air flow rate was then set, which enabled the creatine monohydrate particles to fluidize in the fluidized bed. This warmed the internal temperature of the apparatus. Once the appropriate flow rate was set, 4.8 kg of a 20% aqueous maltodextrin 6 solution was sprayed countercurrently into the fluidized bed using a two-fluid nozzle over a period of 24 minutes, with an agglomerate forming with increasing spraying time. After spraying, the resulting agglomerate was further dried in the fluidized bed until the water not bound to the creatine monohydrate was removed.

[0127] The resulting products are then characterized, where possible, using the methods described under I). The results are summarized in Table 2.

[0128] Table 2: Results of agglomeration in the fluidized bed: Example 10: Agglomeration by wet extrusion - use of maltodextrin 6 (Glucidex IT 6 from Roquette) as binder.

[0129] In an intensive mixer, 16.0 kg of fine creatine monohydrate and 4.7 kg of a 20% maltodextrin 6 solution were homogeneously mixed. The moist powder was then fed into a low-pressure extruder and extruded through a 0.7 mm die, initially producing rod-shaped extrudates. The rods were rounded into pellets in a spheronizer and subsequently dried in a fluidized bed.

[0130] Example 11 : Agglomeration by wet extrusion - Use of maltodextrin

[0131] 6 (Glucidex IT 6 from Roquette) as a binding agent.

[0132] In an intensive mixer, 16.0 kg of fine creatine monohydrate and 4.0 kg of a

[0133] The mixture was homogeneously mixed with a 7% maltodextrin 6 solution. The moist powder was then fed into a low-pressure extruder and extruded through a 0.7 mm die, initially producing rod-shaped extrudates. The rods were rounded into pellets in a spheronizer and subsequently dried in a fluidized bed.

[0134] The resulting products are then characterized, where possible, using the methods described under I). The results are summarized in Table 3.

[0135] Table 3: Results of agglomeration by moisture extrusion: Example 12: Comparison of the dissolution rate and dissolution behavior of different products containing creatine monohydrate.

[0136] The dissolution behavior of 1.75 g of creatine or 1.75 g of creatine agglomerate is determined according to the test method described in section I) 1. The results are shown in Table 4.

[0137] Table 4

[0138] The finely ground creatine monohydrate has a high dissolution rate, whereas coarsely crystalline creatine monohydrate has a slow dissolution rate. Although the creatine monohydrates according to the invention (Examples 2, 8, and 10) are large particles, they exhibit a high dissolution rate while simultaneously being low in dustiness and exhibiting good pouring properties. Example 13: Microscopic examinations

[0139] The microscopic images shown as examples in Figure 1 show that the shape of the creatine particles according to the invention differs significantly from the crystalline form of pure, unmilled creatine monohydrate.

[0140] Figure 1 shows micrographs of the unmilled creatine monohydrate with a x50 value of 171 pm (Fig. 1a), which is present in large, symmetrical, angular, elongated, almost colorless crystals; of the creatine monohydrate agglomerated according to Example 8, which is present in large, loose, irregular, irregularly arranged, angular, almost colorless particles (Fig. 1b); and of the creatine monohydrate agglomerated according to Example 10 (Fig. 1c), which is present in large, compact, rounded, white, shiny particles.

[0141] In summary, the examples show that ground creatine monohydrate dissolves faster in water than coarsely crystalline creatine monohydrate. The finer the grind, the better the dissolution rate. At the same time, however, the wetting properties of ground creatine powder deteriorate due to water and handling (dustiness).

[0142] By agglomerating the ground creatine in the presence of a suitable binder, such as maltodextrin, the adverse handling properties (e.g., bulk properties, dustiness) can be significantly improved. As the examples further demonstrate, the presence of maltodextrin during agglomeration also significantly improves the mechanical stability of the agglomerates (reduced dustiness). The addition of maltodextrin, in particular, significantly improves the dissolution behavior compared to unground, crystalline creatine. The addition of maltodextrin as a binder therefore improves the granule quality and simultaneously ensures a high dissolution rate of the creatine monohydrate, which was unexpected.

Claims

Patent claims 1. Agglomerate comprising a) 30 to 99.9 wt.% ground creatine and / or ground creatine derivatives and / or ground creatine salts, based on the total weight of the agglomerate and b) 0.1 to 30 wt.% of a binder containing at least one oligosaccharide, based on the total weight of the agglomerate.

2. Agglomerate according to claim 1, characterized in that the milled creatine derivative is a creatine hydrate, in particular creatine monohydrate.

3. Agglomerate according to claim 1 or 2, characterized in that the ground creatine, creatine derivative or creatine salt has a particle size distribution with an x50 value in the range of 2 pm to 150 pm, an x10 value in the range of 0.01 pm to 20 pm and an x90 value in the range of 15 pm to 250 pm, each based on the mass fraction.

4. Agglomerate according to any one of claims 1 to 3, characterized in that the binder b) comprises at least 90 wt.% of a carbohydrate mixture, based on the binder b), wherein the carbohydrate mixture consists of carbohydrates of the group consisting of monosaccharides, oligosaccharides and polysaccharides and the carbohydrate mixture has an average molecular weight M n in the range of 500 to 10,000 g / mol.

5. Agglomerate according to one of claims 1 to 4, characterized in that the agglomerate comprises a binder b) containing 0.5 wt.% to 20 wt.% maltodextrin, based on the total weight of the agglomerate.

6. Agglomerate according to claim 5, characterized in that the maltodextrin has a dextrose equivalent of 3 to 15.

7. Agglomerate according to any one of claims 1 to 6, characterized in that the agglomerate comprises no or less than 5 wt.%, in particular less than 2 wt.%, free water.

8. Agglomerate according to any one of claims 1 to 7, characterized in that the agglomerate contains 80 wt.% to 99.5 wt.% creatine, creatine derivatives and / or creatine salts, in particular creatine monohydrate, based on the total weight of the agglomerate.

9. Agglomerate according to any one of claims 1 to 8, characterized in that the angle of repose is less than 45° and / or the bulk density is greater than 200 g / L and / or the flowability [ffc] is greater than 4, and / or the dust number is less than 25.

10. Agglomerate according to any one of claims 1 to 9, characterized in that the agglomerate is a fluidized bed agglomerate, a granulate or an extrudate.

11. Agglomerate according to any one of claims 1 to 10 comprising: a) 30 to 99.9 wt.%, preferably at least 45 wt.%, more preferably at least 60 wt.% and even more preferably at least 75 wt.% milled creatine and / or milled creatine derivatives and / or milled creatine salts, in particular creatine monohydrate, based on the total weight of the agglomerate; and b) 0.1 to 30 wt.%, preferably 1 to 18 wt.% and more preferably 5 to 15 wt.% of a binder comprising at least one oligosaccharide, in particular maltodextrin, based on the total weight of the agglomerate; and c) 0 to 20 wt.%, preferably not more than 10 wt.%, more preferably not more than 5 wt.% further additives; and d) 0 to less than 5 wt.%, preferably less than 2 wt.% free water.

12. Use of an agglomerate according to any one of the preceding claims as a bulk material for dissolution in beverages or as a direct agglomerate.

13. Process for producing an agglomerate according to any one of claims 1 to 10, characterized in that milled creatine is agglomerated in the presence of 0.1 wt.% to 30 wt.%, based on the total weight of the agglomerate, of a binder containing at least one oligosaccharide in a mixer, in a fluidized bed, or by extrusion.

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