SOLUBILIZATION OF SLIGHTLY SOLIDLESS REFRIGERATIVES

Description

[0001] The present invention relates to a cooling composition for producing cooling particles comprising a solvent component and (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide dissolved therein. The present invention also relates to cooling particles comprising a cooling composition according to the invention. Furthermore, the present invention relates to oral preparations comprising cooling particles and to a use of cooling particles. Finally, the present invention also provides a process for producing cooling particles and describes a use of a solvent component for dissolving cooling agents.

[0002] Processes for producing cooling particles are described in the prior art. In EP 2 801 263 A1, a cooling composition is encapsulated in a spray granulation process. The cooling composition used in the process comprises a cooling agent and at least one hydrophobic compound, and optionally an alcohol. Before the spray granulation process, the components of the cooling composition are dissolved at an elevated temperature of up to 100°C and kept at elevated temperatures of 35°C to 65°C until further processing in order to prevent recrystallization of the components, in particular the cooling agent.

[0003] The process described in the prior art has the disadvantage that the cooling composition used is not storage-stable and must be kept at an elevated temperature until use. Maintaining the composition at this elevated temperature requires a special system that allows the reactants used to be kept warm. Furthermore, heating and maintaining the composition warm consumes a great deal of energy, which leads to increased production costs.

[0004] Another disadvantage of the process described in the prior art is that, due to the necessary warming of the dissolved composition, transport of the produced composition is impossible or only possible with enormous effort, so that the dissolution process and subsequent use of the composition must take place at the same location. Filling the dissolved composition into barrels with subsequent transport or storage at normal outside temperatures, possibly even at low temperatures in winter, is not currently possible with the compositions described in the prior art.

[0005] Since storage or transport of the composition has not been possible without permanent heating and the dissolution or production of the composition therefore only had to take place at the place of further processing, it is necessary for the compositions described in the prior art to divide the individual components of the composition into different components which were only mixed in the heat before dissolution and thus production of the composition.

[0006] WO 2018 / 028770 A1 describes solvents for (E)-3-benzo[I,3]dioxol-5-yl-N,N-diphenyl-2-propenamide, including 2-hydroxypropyl (2-isopropyl-5-methylcyclohexyl) carbonate. However, no reference is made to possible further uses of 2-hydroxypropyl (2-isopropyl-5-methylcyclohexyl) carbonate.

[0007] EP 2 186 506 A1 describes a composition containing WS-12 dissolved in the composition and menthol.

[0008] WO 2017 / 165882 A1 describes water-insoluble cooling agents encapsulated in a water-soluble matrix.

[0009] CN 107890074 A describes a cooling agent composition containing N-ethyl-p-menthyl-3-carboxamide (WS-3) and its manufacturing process.

[0010] The object of the present invention was to provide cooling compositions that do not have the above-mentioned disadvantages of previously known cooling compositions. In particular, the object of the present invention was to provide cooling compositions that meet at least one of the following requirements, namely can be stored at normal temperatures in a production hall in the range of 15 to 30°C without additional heating of the composition and can be transported without special precautions and without individual components of the composition crystallizing out

[0011] The object is achieved according to the invention by a cooling composition for producing cooling particles consisting of or comprising (A) a solvent component consisting of or comprising i) 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate and / or ii) (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate and dissolved therein (B) 0.5 to 12 wt.% (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide (CAS number 68489-09-8; FEMA number 4681) as a cooling agent, based on the total weight of the composition.

[0012] Surprisingly, it has been shown that the cooling agent (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide can be dissolved in 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate, (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate, or a mixture of both compounds, and that the resulting solution is storage-stable for days and weeks, even at temperatures of 25°C and below. This is particularly surprising because (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate is a solid with a melting point of approximately 40°C. Amounts of up to 12% by weight of the cooling agent, based on the total weight of the composition, can be dissolved.

[0013] In one embodiment of the present invention, the composition additionally contains N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide. Our own investigations have shown that N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide, which is also a solid, is not capable of dissolving the cooling agent, and that the melts obtained by heating from N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide and the cooling agent crystallize upon cooling. However, the addition of N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide can stabilize the compositions according to the invention so that no crystallization occurs. This is particularly surprising in this respect, since the skilled person would expect that the addition of further solids would reduce the maximum solubility of other solids and thus promote the crystallization of already dissolved solids.This effect, which is known to those skilled in the art, is exploited, for example, in salting-out, in which water-soluble substances are displaced from the aqueous phase by adding salt.

[0014] In the present invention, N-ethyl-2-isopropyl-5-methylcyclohexanecarboxamide is assigned to group (A), i.e., the solvent component, even though this compound itself is not suitable for dissolving (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide over a long period of time without the addition of other compounds. In this case, it serves as a solution stabilizer and improves the solvency of all solvent components with respect to the solubility of (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide.

[0015] Particularly preferred according to the invention are cooling compositions for producing cooling particles which (A) a solvent component consisting of or comprising i) 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate and ii) (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate and iii) N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide and dissolved therein (B) 0.5 to 12 wt.% (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide (CAS number 68489-09-8; FEMA number 4681) as a cooling agent, based on the total weight of the composition.

[0016] Our own investigations have shown, quite surprisingly, that the combination of 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate, (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate and N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide is particularly well suited to (1R,2S,5R)- N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide and that the resulting solutions remain stable for a particularly long time at temperatures of 25°C and below without individual components crystallizing out.

[0017] Cooling compositions are preferred according to the invention, wherein N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide is (1R,2S,5R)-N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide (CAS number 68489-00-9).

[0018] Cooling compositions are preferred according to the invention, wherein 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate is 2-hydroxypropyl [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] carbonate (CAS number 260781-16-6).

[0019] Our own investigations have surprisingly shown that the diastereomer of the compound used according to the invention described here has good properties regarding the solubility of (1R,2S,5R)- N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide.

[0020] Cooling compositions are preferred according to the invention, wherein (2-isopropyl-5-methylcyclohexyl) 2-hydroxypropanoate is [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl] (2S)-2-hydroxypropanoate (CAS number 61597-98-6).

[0021] Our own investigations have surprisingly shown that the diastereomer of the compound used according to the invention described here has good properties regarding the solubility of (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide.

[0022] It is particularly preferred according to the invention if the N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide used is (1R,2S,5R)-N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide (CAS number 68489-00-9), the 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate used is 2-hydroxypropyl [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] carbonate (CAS number 260781-16-6) and the (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate used is [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] (2S)-2-hydroxypropanoate (CAS number 61597-98-6).

[0023] Our own investigations have surprisingly shown that the combination of the three described diastereomers of the compound used according to the invention leads to excellent properties regarding the solubility of (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide.

[0024] The diastereomers of the solvent components described above have proven to be particularly advantageous, as they not only lead to excellent solubilization of the (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide, but also have a cooling effect and thus further improve the cooling effect of the composition according to the invention.

[0025] Cooling compositions are preferred according to the invention, wherein the solvent component 2 to 20 wt.%, preferably 4 to 15 wt.%, particularly preferably 6.4 to 11.8 wt.% of 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate, and / or 55 to 75 wt.%, preferably 60 to 70 wt.%, particularly preferably 63 to 67 wt.% of (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate, and / or 15 to 35 wt.%, preferably 20 to 30 wt.%, particularly preferably 23 to 27 wt.% of N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide, in each case based on the total weight of the solvent component.

[0026] A cooling composition according to the invention is preferred, wherein the composition contains 88 to 99.5 wt.%, preferably 90 to 94 wt.% of the solvent component (A), based on the total weight of the composition.

[0027] A cooling composition according to the invention is preferred, wherein the composition additionally contains 0.5 to 8 wt.%, preferably 4 to 7.5, particularly preferably 5 to 7 wt.% of medium-chain triglycerides, based on the total weight of the composition.

[0028] Our own investigations have surprisingly shown that the addition of medium-chain triglycerides improves the stability of (1R,2S,5R)- N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide in solution can be further improved. This result is surprising, since medium-chain triglycerides are considered poor solvents for (1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide. Upon addition of a poor solvent, one skilled in the art would expect the solute to crystallize out of the solution. Surprisingly, however, this is not the case in the present case. Up to a concentration of 8 wt.%, the medium-chain triglyceride stabilizes the solution.

[0029] Medium-chain triglycerides (MCTs), also known as MCT fats, are triglycerides that contain medium-chain fatty acids. Medium-chain fatty acids include caproic (C 6:0), caprylic (C 8:0), capric (C 10:0), and lauric acid (C 12:0). These are saturated fatty acids found primarily in tropical vegetable fats such as coconut fat (approx. 60%) and palm kernel oil (approx. 55%), as well as in butter. They are also found in small amounts in milk fat (approx. 10%). Medium-chain triglycerides are obtained industrially by hydrolysis of coconut fat and palm kernel oil, fractionation of the medium-chain fatty acids, and subsequent esterification with glycerol. A pure medium-chain triglyceride is colorless to yellowish, neutral in odor and taste, and of very low viscosity.

[0030] According to the invention, a medium-chain triglyceride preferably contains 50-80% caprylic acid C8, 25-45% capric acid C10, lauric acid max. 3% and max. 2% caproic acid.

[0031] A cooling composition according to the invention is preferred, wherein the composition contains more than 50 wt.%, preferably more than 65 wt.%, particularly preferably more than 80 wt.% of the solvent component (A), based on the total weight of the composition.

[0032] A cooling composition according to the invention is particularly preferred, wherein the composition contains 80 to 99 wt.%, preferably 80.5 to 95.5 wt.%, particularly preferably 81 to 94.5 wt.% of the solvent component (A), based on the total weight of the composition.

[0033] A cooling composition according to the invention is particularly preferred, wherein the composition contains 0.5 to 6 wt.%, preferably 1 to 4 wt.%, particularly preferably 1.5 to 3 wt.% (1R,2S,5R)- N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide (FEMA 4681) as a cooling agent, each based on the total weight of the composition.

[0034] Cooling compositions according to the invention with a proportion of 0.5 to 6 wt.% cooling agent are particularly preferred if the cooling composition is to be used directly in liquid semi-finished products or finished products.

[0035] A cooling composition according to the invention is particularly preferred, wherein the composition contains 6 to 12 wt.%, preferably 6.5 to 10 wt.%, particularly preferably 7 to 9 wt.% (1R,2S,5R)- N -(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide (FEMA 4681) as a cooling agent, each based on the total weight of the composition.

[0036] Cooling compositions according to the invention with a proportion of 6 to 12 wt.% cooling agent are particularly preferred if the cooling composition is to be used for the production of cooling particles or in solid semi-finished products or finished products.

[0037] Particularly preferred according to the invention are cooling compositions for producing cooling particles which (A) a solvent component consisting of or comprising i) 2 to 20 wt.%, preferably 4 to 15 wt.%, particularly preferably 6.4 to 11.8 wt.% of 2-hydroxypropyl [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] carbonate (CAS number 260781-16-6) and ii) 55 to 75 wt.%, preferably 60 to 70 wt.%, particularly preferably 63 to 67 wt.% of [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] (2S)-2-hydroxypropanoate (CAS number 61597-98-6) and iii) 15 to 35 wt.%, preferably 20 to 30 wt.%, particularly preferably 23 to 27 wt.% of (1R,2S,5R)- N-Ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide (CAS number 68489-00-9) comprises, in each case based on the total weight of the solvent component and dissolved therein (B) 0.5 to 12 wt.% (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide (CAS number 68489-09-8; FEMA number 4681) as a cooling agent, based on the total weight of the composition, and wherein the composition contains more than 50 wt.%, preferably more than 65 wt.%, particularly preferably more than 80 wt.% of the solvent component (A), based on the total weight of the composition.

[0038] According to the invention, cooling compositions for producing cooling particles are also particularly preferred, which (A) a solvent component consisting of or comprising i) 2 to 20 wt.%, preferably 4 to 15 wt.%, particularly preferably 6.4 to 11.8 wt.% of 2-hydroxypropyl [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] carbonate (CAS number 260781-16-6) and ii) 55 to 75 wt.%, preferably 60 to 70 wt.%, particularly preferably 63 to 67 wt.% of [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] (2S)-2-hydroxypropanoate (CAS number 61597-98-6) and iii) 15 to 35 wt.%, preferably 20 to 30 wt.%, particularly preferably 23 to 27 wt.% of (1R,2S,5R)- N -Ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide (CAS number 68489-00-9) comprises, in each case based on the total weight of the solvent component and dissolved therein (B) 0.5 to 12 wt.% (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide (CAS number 68489-09-8; FEMA number 4681) as a cooling agent, based on the total weight of the composition, and wherein the composition additionally contains 0.5 to 8 wt.%, preferably 4 to 7.5, particularly preferably 5 to 7 wt.% of medium-chain triglycerides, based on the total weight of the composition, wherein the composition contains more than 50 wt.%, preferably more than 65 wt.%, particularly preferably more than 80 wt.% of the solvent component (A), based on the total weight of the composition.

[0039] Even if the addition of other solvents, such as alcohols, to the cooling compositions according to the invention is not excluded, this is necessary for the solubilization of the (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide is not necessary. According to the invention, it is preferred if the cooling compositions do not contain alcohols, such as methanol, ethanol, propanol, or 1,2-propanediol.

[0040] A further aspect of the present invention relates to cooling particles comprising a cooling composition according to the invention.

[0041] Our own studies have shown that cooling particles according to the invention convey a stronger feeling of freshness due to the physiologically cooling effect of the cooling agent, compared to cooling particles containing the same amount of cooling agent but with a different composition of the solvent component. Due to the very good solubility of the cooling agent in the solvent component used according to the invention, the cooling agent does not crystallize in the particle. When the cooling particles are ingested orally, the cooling agent is already dissolved and can therefore be distributed much better in the mouth than if it were present as a crystalline solid. This accordingly leads to a stronger feeling of freshness.

[0042] However, this effect is not only observed with cooling particles according to the invention, but also with the oral intake of compositions according to the invention in general.

[0043] The cooling particles according to the invention may preferably be matrix particles or granules obtained, for example, by spray drying or spray granulation, or core-shell particles.

[0044] According to the invention, cooling particles with an average particle diameter D50 in the range from 10 to 2000 µm are preferred.

[0045] If the particles according to the invention are matrix particles obtained by spray drying, the average particle diameter D50 is preferably in the range from 10 to 200 µm, particularly preferably in the range from 15 to 150 µm, very particularly preferably in the range from 50 to 100 µm.

[0046] If the particles according to the invention are granules obtained by spray granulation, the average particle diameter D50 is preferably in the range from 200 to 2000 µm, particularly preferably in the range from 250 to 1500 µm, very particularly preferably in the range from 300 to 900 µm.

[0047] The mean particle diameter D50 is determined using laser light diffraction according to ISO13320:2009-10.

[0048] Cooling particles according to the invention are preferred, wherein the particles contain or consist of compounds selected from the group consisting of starch, starch derivatives (e.g. modified starch), cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g. pectin, dextrin, alginate, curdlan, carageenan, chitin, chitosan, pullulan, gum arabic), natural fats, natural waxes (e.g. beeswax, carnauba wax), proteins, e.g. gelatin and other natural products (e.g. shellac) as matrix materials or shell materials.

[0049] Cooling particles according to the invention are preferred, wherein the cooling particles comprise 5 to 40 wt.%, preferably 10 to 30 wt.% of the cooling composition according to the invention, based on the total weight of the particles.

[0050] A further aspect of the present invention relates to an oral preparation comprising cooling particles according to the invention or a composition according to the invention.

[0051] An oral preparation according to the invention is preferred, wherein the oral preparation is a beverage, a chewing gum, a mouthwash, toothpaste, lip balm or a candy.

[0052] An oral preparation according to the invention is preferred, comprising a) 5 to 95 wt.% chewing gum base, b) 5 to 95 wt.% fillers and sweeteners, c) 0.1 to 15 wt.% flavorings, d) 0.2 to 4 wt.% cooling particles according to the invention.

[0053] A further aspect of the present invention relates to a use of cooling particles according to the invention or a cooling composition according to the invention to impart a feeling of freshness in oral preparations through a physiologically cooling effect.

[0054] A further aspect of the present invention relates to a use of a composition according to the invention in an encapsulation process, preferably spray drying or spray granulation.

[0055] A further aspect of the present invention relates to a process for producing cooling particles comprising the following steps: Producing or providing a composition according to the invention, storing the produced or provided composition, producing or providing matrix materials, optionally mixing the produced or provided composition with the produced or provided matrix materials, carrying out an encapsulation process so that cooling particles result in which the composition is enclosed by the matrix materials.

[0056] According to the invention, a method is preferred wherein the encapsulation method is spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion method, coating or other suitable encapsulation method, preferably spray drying or spray granulation.

[0057] A method according to the invention is preferred, wherein the matrix materials are starch, starch derivatives (e.g. modified starch), cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g. pectin, dextrin, alginate, curdlan, carageenan, chitin, chitosan, pullulan, gum arabic), natural fats, natural waxes (e.g. beeswax, carnauba wax), proteins, e.g. gelatin and / or other natural products (e.g. shellac).

[0058] A method according to the invention is preferred, wherein the storage of the prepared or provided composition takes place at a temperature below 40°C, preferably below 35°C, particularly preferably below 30°C, further preferably below 25°C. In some embodiments of the present invention, it is preferred if the storage of the prepared or provided composition takes place at a temperature in the range from 0°C to 25°C, preferably in the range from 5°C to 15°C.

[0059] A process according to the invention is preferred, wherein the storage of the prepared or provided composition takes place at a temperature between 5°C and 65°C, preferably between 18°C ​​and 35°C, particularly preferably between 20 and 25°C.

[0060] A process according to the invention is preferred, wherein the storage of the prepared or provided composition takes place without the addition of heat energy.

[0061] A process according to the invention is preferred, wherein the cooling particles obtained have an average particle diameter D50 in the range from 10 to 2000 µm.

[0062] A further aspect of the present invention relates to a use of a solvent component consisting of or comprising i) 2-Hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate and / or ii) (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate to dissolve one or more cooling agents.

[0063] Our own investigations have surprisingly shown that the solvent component used in the composition according to the invention is also suitable for dissolving other cooling agents.

[0064] A use according to the invention is preferred, wherein the cooling agent, at least one of the plurality of cooling agents or all of the plurality of cooling agents are cooling agents selected from the group comprising (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide (FEMA GRAS 4681), Menthol Methyl Ether (FEMA GRAS 4054), Menthoxyethanol (FEMA GRAS 4154), Menthone Glyceryl Acetal (FEMA GRAS 3807 and 3808), Menthol ethylene glycol carbonate (FEMA GRAS 3805), Menthyl N-ethyloxamate, Monomethyl succinate (FEMA GRAS 3810), Monomenthyl glutarate (FEMA GRAS 4006), Menthoxy-1,2-propanediol (FEMA GRAS 3784),-Menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849), Isopropyltrimethylbutyramide (WS-23, FEMA GRAS 3804), N-((Ethoxycarbonyl)methyl)-p-menthyl-3-carboxamide (WS-5, FEMA GRAS 4309), Diethylhydroxydimethylethylbutanamide (WS-116, FEMA GRAS 4603), ethyldiisopropylbutanamide (WS-27, FEMA GRAS 4557), cyclopropy-imenthylcarboxamide (FEMA GRAS 4693),Mentholethylenglycolcarbonat (FEMA GRAS 3805), Menthanediol (FEMA GRAS 4053), Menthylpyrrolidoncarboxylat (FEMA GRAS 4155), Dimethylmenthylsuccinamid (FEMA GRAS 4230), 3,9-Dimethyl-6-(1-methylethyl)-1,4-dioxaspiro[4.5]decan-2-on (FEMA GRAS 4285), Menthylhydroxybutyrat (FEMA GRAS 4308), Menthyl acetoacetate (FEMA GRAS 4327), N-(4-cyanomethylphenyl)-p-menthyl-carboxamid (FEMA GRAS 4496), N-(2-pyridin-2-ylethyl)menthylcarboxamid (FEMA GRAS 4549), N-Hydroxyethyldimethyl-isopropylbutanamid (FEMA GRAS 4602), Dimenthylglutarat (FEMA GRAS 4604), N-[4-(2-Amino-2-oxoethyl)phenyl]-p-menthylcarboxamid (FEMA GRAS 4684), Menthoxyethoxyethanol (FEMA GRAS 4718), Hydroxymethylcyclohexylethanon (FEMA GRAS 4742), 2-(4-Methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamid (FEMA GRAS 4809), 2-(4-Ethylphenoxy)-, N -(1H-pyrazol-3-yl)- N -(thiophen-2-ylmethyl)acetamid (FEMA GRAS 4880), N-(3-Hydroxy-4-methoxyphenyl)-2-isopropyl-5,5-dimethylcyclohexanecarboxamide (FEMA GRAS 4881), N-(4-(Cyanomethyl)phenyl)-2-isopropyl-5,5-dimethylcyclohexanecarboxamide (FEMA GRAS 4882) and N-(2-Hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide (FEMA GRAS 4896).

[0065] Within the scope of the present invention, several of the aspects identified above as preferred are preferably implemented simultaneously; particularly preferred are the combinations of such aspects and the corresponding features resulting from the appended claims. Examples: Example 1:

[0066] 96 g of 2-hydroxypropyl(2-isopropyl-5-methyl-cyclohexyl)carbonate were placed in a 250 mL beaker and 4 g of (1R,2S,5R)- N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide was added. The mixture was stirred and heated in 20°C increments until a clear solution was formed. After each heating by 20°C, the solution was stirred for at least 20 minutes. The mixture was then allowed to cool to room temperature of approximately 25°C. The prepared solution was stable for 8 hours even after cooling, and no crystals formed. Example 2:

[0067] Example 1 was repeated, but instead of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl)carbonate, (2-isopropyl-5-methylcyclohexyl)2-hydroxypropanoate was used as the solvent. The resulting solution was stable even after cooling, and no crystals formed. Example 3:

[0068] Example 1 was repeated, except that instead of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl) carbonate, a mixture of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl) carbonate and (2-isopropyl-5-methylcyclohexyl)2-hydroxypropanoate was used as the solvent. The resulting solution was stable even after cooling, and no crystals formed. Example 4:

[0069] Example 1 was repeated, but instead of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl)carbonate, a mixture of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl)carbonate, (2-isopropyl-5-methylcyclohexyl)2-hydroxypropanoate and N-ethyl-2-isopropyl-5-methylcyclohexanecarboxamide was used as solvent and 10 g of (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide. The prepared solution remained stable even after cooling, and crystals only formed after more than 24 hours. Example 5:

[0070] Example 4 was repeated, but 8 g of (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide. The prepared solution was stable for more than 24 hours even after cooling, and no crystals formed. Example 6:

[0071] Example 4 was repeated, but 6 g of (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide. The prepared solution was stable for more than 24 hours even after cooling, and no crystals formed. Example 7:

[0072] Example 4 was repeated, but 4 g of (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide. The prepared solution remained stable for more than two weeks, even after cooling, and no crystals formed. Example 8:

[0073] Example 1 was repeated, but instead of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl)carbonate, a mixture of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl)carbonate, (2-isopropyl-5-methylcyclohexyl)2-hydroxypropanoate, N-ethyl-2-isopropyl-5-methylcyclohexanecarboxamide and 6 wt% medium-chain triglycerides was used as solvent and 6 g of (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide. The prepared solution remained stable for more than two weeks, even after cooling, and no crystals formed. Example 9: Production of granulate particles with a cooling composition according to the invention by spray granulation:

[0074] A cooling composition according to the invention from Example 8 was prepared and stored at approximately 20°C. A mixture of 50 parts by weight of modified starch, 25 parts by weight of gum arabic (Senegal), and 10 parts by weight of mannitol was then prepared as a carrier component. The cooling composition and the carrier component were mixed in a weight ratio of 1 to 4 and spray-granulated.

[0075] Cooling particles are obtained with an average particle diameter D50 of 600 µm, determined by laser light diffraction according to ISO ISO13320:2009-10, which comprise approximately 20 wt.% of the cooling composition according to the invention.

[0076] By varying the process parameters of the spray granulation process, it is also possible to produce particles with a size of, for example, 200 µm, 300 µm, 400 µm, 800 µm, 1400 µm, 1800 µm or 2000 µm. Example 10: Production of particles with a cooling composition according to the invention by spray drying:

[0077] A cooling composition according to the invention from Example 8 was prepared and stored at approximately 20°C. A mixture of 60 parts by weight of modified starch, 25 parts by weight of gum arabic (Senegal), and 10 parts by weight of sugar alcohol was then prepared as a carrier component. The cooling composition and the carrier component were mixed in a weight ratio of 3 to 7 and spray-dried.

[0078] Cooling particles are obtained with an average particle diameter D50 of 80 µm, determined by laser light diffraction according to ISO ISO13320:2009-10, which comprise approximately 27 wt.% of the cooling composition according to the invention.

[0079] By varying the process parameters of the spray drying process, it is also possible to produce particles with a size of, for example, 10 µm, 20 µm, 75 µm, 125 µm, 150 µm, 175 µm or 200 µm. Example 11: Making a mouthwash:

[0080] Part Ingredient Use in wt.% A Ethanol 10,00 Cremophor ®< CO 40 (BASF, detergent) 1,00 Benzoic acid 0,12 Solution from Example 8 1,00 B demineralized water 82,71 Sorbitol, 70% 5,00 Sodium saccharin 450 0,07 L-Blue 5000 ec, 1% in water (dye) 0,10

[0081] The ingredients of parts A and B were mixed separately. Part B was slowly stirred into Part A until the mixture was homogeneous.

[0082] When using the mouthwash produced in this way, a very strong cooling effect was observed. Example 12: Production of sugar-free chewing gum:

[0083] Part Ingredient Use in wt.% A Chewing gum base, Company "Jagum T" 30,00 B Sorbitol, powdered 39,00 Isomalt ®< (Palatinit GmbH) 9,50 Xylitol 2,00 Mannitol 3,00 Aspartame ®< 0,10 Acesulfame ®< K 0,10 Emulgum®< (Colloides Naturels, Inc.) 0,30 C Sorbitol, 70% 14,00 Glycerin 1,00 D Granules from Example 9 1,00

[0084] Parts A to D were mixed and kneaded thoroughly. The raw mixture was processed into thin strips, for example, to make ready-to-eat chewing gum.

[0085] When using the chewing gum produced in this way, a significant cooling effect was observed. Comparison example 1:

[0086] Example 1 was repeated, but ethanol was used as the solvent instead of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl) carbonate. The resulting solution crystallized upon cooling to room temperature. Comparison example 2:

[0087] Example 1 was repeated, but instead of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl) carbonate, medium-chain triglycerides were used as solvent and 1 g of (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide dissolved. No solution could be prepared. (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide is insoluble in medium-chain triglycerides even at 60°C. Comparison example 3:

[0088] Example 1 was repeated, but instead of 2-hydroxypropyl(2-isopropyl-5-methylcyclohexyl)carbonate, N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide was used as solvent, 1 g of (1R,2S,5R)- N -(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide was dissolved, and the mixture was heated until both substances melted. Both substances crystallized upon cooling.

Claims

1. A cooling composition for producing cooling particles consisting of or comprising (A) a solvent component consisting of or comprising i) 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate and / or ii) (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate and dissolved therein (B) 0.5 to 12 wt.-% of (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane carboxamide (CAS number 68489-09-8; FEMA number 4681), based on the total weight of the composition, as cooling agent.

2. The composition according to claim 1, wherein the composition A) comprises 0.5 to 6 wt.-%, preferably 1 to 4 wt.-%, more preferably 1.5 to 3 wt.-%, of (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide (FEMA 4681) as cooling agent or B) comprises 6 to 12 wt.-%, preferably 6.5 to 10 wt.-%, more preferably 7 to 9 wt.-% of (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide (FEMA 4681) as cooling agent based on the total weight of the composition, respectively.

3. The composition according to claim 1 or 2, wherein the composition additionally comprises N-ethyl-2-isopropyl-5-methyl-cyclohexane carboxamide.

4. The composition according to any of the preceding claims, wherein 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate is 2-hydroxypropyl [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] carbonate (CAS number 260781-16-6), and / or wherein N-ethyl-2-isopropyl-5-methyl-cyclohexane carboxamide is (1R,2S,5R)-N-ethyl-2-isopropyl-5-methyl-cyclohexane carboxamide (CAS number 68489-00-9), and / or wherein (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate is [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl]-(2S)-2-hydroxypropanoate (CAS number 61597-98-6).

5. The composition according to any of the preceding claims, wherein the solvent component comprises 2 to 20 wt.-%, preferably 4 to 15 wt.-%, more preferably 6.4 to 11.8 wt.-%, based on the total weight of the solvent component, of 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate and / or wherein the solvent component comprises 15 to 35 wt.-%, preferably 20 to 30 wt.-%, more preferably 23 to 27 wt.-%, based on the total weight of the solvent component, of N-ethyl-2-isopropyl-5-methyl-cyclohexane carboxamide.

6. The composition according to any of the preceding claims, wherein the solvent component comprises 55 to 75 wt.-%, preferably 60 to 70 wt.-%, more preferably 63 to 67 wt.-%, based on the total weight of the solvent component, of (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate.

7. The composition according to any of the preceding claims, wherein the composition comprises 88 to 99.5 wt.-%, preferably 90 to 94 wt.-% ,based on the total weight of the composition, of the solvent component (A).

8. The composition according to any of claims 1 to 5, wherein the composition additionally comprises 0.5 to 8 wt.-%, preferably 4 to 7.5 wt.-%, more preferably 5 to 7 wt.-%, based on the total weight of the composition, of medium-chain triglycerides, preferably wherein the composition comprises 80 to 99 wt.-%, preferably 80.5 to 95.5 wt.-%, more preferably 81 to 94.5 wt.-%, based on the total weight of the composition, of the solvent component (A).

9. The composition according to any of the preceding claims, wherein the composition comprises more than 50 wt.-%, preferably more than 65 wt.-%, more preferably more than 80 wt.-%, based on the total weight of the composition, of the solvent component (A).

10. Cooling particles comprising a composition according to any of claims 1 to 9, preferably wherein the particles have a mean particle diameter D50 in the range of 10 µm to 2000 µm as determined by laser light diffraction according to ISO ISO13320:2009-10.

11. An oral preparation, comprising the cooling particles according to claim 10 or a composition according to any of claims 1 to 9, preferably wherein the oral preparation is a beverage, a chewing gum, a mouthwash, a toothpaste, a lip balm or a candy.

12. The oral preparation according to claim 11, comprising a) 5 to 95 wt.-% of a chewing gum base, b) 5 to 95 wt.-% of filling agents and sweeteners, c) 0.1 to 15 wt.-% of flavourings, d) 0.2 to 4 wt.-% of cooling particles according to claim 10.

13. Use of cooling particles according to claim 10 or a composition according to any of claims 1 to 9, to impart a feeling of freshness in oral preparations through a physiologically cooling effect.

14. Use of a composition according to any of claims 1 to 9, in an encapsulation process, preferably spray-drying or spray granulation.

15. A process for preparing cooling particles comprising the following steps: - Producing or providing a composition according to any of claims 1 to 9, - storing the produced or provided composition, - producing or providing matrix materials, - optionally, mixing the produced or provided composition with the produced or provided matrix materials, - carrying out an encapsulation process such that cooling particles are obtained, in which the composition is enclosed by the matrix material.

16. The process according to claim 15, wherein the encapsulation process is spray-drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion process, coating or other suitable encapsulation processes, preferably is spray-drying or spray granulation, and / or wherein the matrix material is starch, starch derivatives (e.g., modified starch), cellulose or cellulose derivatives (e.g., hydroxypropyl cellulose), other polysaccharides (e.g., pectin, dextrin, alginate, curdlan, carrageenan, chitin, chitosan, pullulan, gum arabic), natural fats, natural waxes (e.g. beeswax, carnauba wax), proteins, e.g., gelatin and / or other natural products (e.g., shellac), and / or wherein the storing of the produced or provided composition is performed at a temperature between 15°C and 65°C, preferably between 18°C and 35°C, more preferably between 20°C and 25°C, and / or wherein the storing of the produced or provided composition is performed without applying heat energy, and / or wherein the particles have a mean particle diameter D50 in the range of 10 to 2000 µm as determined by laser light diffraction according to ISO ISO13320:2009-10.

17. Use of a solvent component consisting of or comprising i) 2-hydroxypropyl (2-isopropyl-5-methylcyclohexyl) carbonate and / or ii) (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate to dissolve cooling agents, wherein the cooling agent, at least one of the multiple cooling agents, or all of the multiple cooling agents is / are cooling agents selected from the group comprising (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamide (FEMA GRAS 4681), menthol methyl ether (FEMA GRAS 4054), menthoxyethanol (FEMA GRAS 4154), menthone glyceryl acetal (FEMA GRAS 3807 and 3808), menthol ethylenglycolcarbonate (FEMA GRAS 3805), menthyl-N-ethylox-amate, monomethyl succinate (FEMA GRAS 3810), monomenthyl glutarate (FEMA GRAS 4006), menthoxy-1,2-propane diol (FEMA GRAS 3784), -menthoxy-2-methyl-1,2-propane diol (FEMA GRAS 3849), isopropyl trimethyl butyramide (WS-23, FEMA GRAS 3804), N-((ethoxycarbonyl)methyl)-p-menthane-3-carboxamide (WS-5, FEMA GRAS 4309), diethylhydroxydimethylethylbutanamide (WS-116, FEMA GRAS 4603), ethyldiisopropylbutanamide (WS-27, FEMA GRAS 4557), cyclopropylmenthylcarboxamide (FEMA GRAS 4693), mentholethylen glycol carbonate (FEMA GRAS 3805), menthanediol (FEMA GRAS 4053), menthyl pyrrolidone carboxylate (FEMA GRAS 4155), dimethyl menthyl succinamide (FEMA GRAS 4230), 3,9-dimethyl-6-(1-methylethyl)-1,4-dioxaspiro[4.5]decan-2-one (FEMA GRAS 4285), menthyl hydroxybutyrate (FEMA GRAS 4308), menthyl acetoacetate (FEMA GRAS 4327), N-(4-cyanomethylphenyl)-p-menthylcarboxamide (FEMA GRAS 4496), N-(2-(pyridin-2-yl)ethyl)menthylcarboxamide (FEMA GRAS 4549), N-hydroxyethyldimethylisopropylbutanamide (FEMA GRAS 4602), dimenthyl glutarate (FEMA GRAS 4604), N-[4-(2-amino-2-oxoethyl)phenyl]-p-menthylcarboxamide, (FEMA GRAS 4684), menthoxyethoxyethanol (FEMA GRAS 4718), hydroxymethylcyclohexylethanone (FEMA GRAS 4742), 2-(4-Methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide (FEMA GRAS 4809), 2-(4-Ethylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide (FEMA GRAS 4880), N-(3-Hydroxy-4-methoxyphenyl)-2-isopropyl-5,5-dimethylcyclohexanecarboxamide (FEMA GRAS 4881), N-(4-(cyanomethyl)phenyl)-2-isopropyl-5,5-dimethylcyclohexanecarboxamide (FEMA GRAS 4882) and N-(2-hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide (FEMA GRAS 4896).