Cooling composition in the form of granules and oral preparation comprising this

Abstract

Cooling composition in the form of granules obtained by a process comprising the following steps: a) providing a cooling composition, wherein the cooling composition is a composition consisting of (A) 8 to 10 wt.% cooling agent (A) is selected from the group consisting of menthone glycerol acetal (FEMA GRAS 3807), menthone glycerol ketal (FEMA GRAS 3808), menthyl lactate (FEMA GRAS 3748), menthol ethylene glycol carbonate (FEMA GRAS 3805), menthol propylene glycol carbonate (FEMA GRAS 3806), menthyl N-ethyl oxamate, monomethyl succinate (FEMA GRAS 3810), monomenthyl glutamate (FEMA GRAS 4006), menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849) and the menthanecarboxylic acid esters and amides or acyclic carboxamides of the formula (I) where R' and R'' independently of one another are hydrogen, hydroxyl group or a branched, unbranched, cyclic alkyl radical having up to 25 C atoms, an aryl group having up to 10 C atoms, selected from substituted and unsubstituted phenyl, phenylalkyl, naphthyl and pyridyl radicals, or mixtures thereof, and (B) 15 to 35 wt.% alcohol selected from the group consisting of a C1 to C3 alcohol or mixtures thereof, and (C) 60 to 80 wt.% hydrophobic compound selected from the group consisting of essential oils, neutral oils, vegetable oils or mixtures thereof, b) Dissolving the cooling agent (A) in (B) and (C) completely to form a homogeneous mixture, keeping the temperature at 40 °C to 100 °C for complete dissolution of (A), c) spray granulating the homogeneous mixture obtained in step b) at a temperature of 35°C to 65°C to prevent recrystallization of (A), d) Obtaining a cooling composition in the form of granules, the particles having an average particle size of 0.3 mm to 0.9 mm.

Description

Field of the invention

[0001] The invention is in the field of food and relates to a composition that provides a physiologically cooling effect in the preparations to be used to impart a feeling of freshness, comprising 8 to 10% cooling agent (A), 15 to 35% alcohol (B), and 60 to 80% hydrophobic compound (C). Furthermore, the invention relates to the production and use of the cooling composition according to the invention in oral preparations, in particular in chewing gum and candies. State of the art

[0002] Chewing gums typically consist of a water-insoluble chewing mass that remains in the consumer's mouth even after prolonged and intensive chewing. In addition to this chewing mass, chewing gums contain, for example, flavorings, sweeteners, and substances with a physiological cooling effect, which are released during chewing and achieve a desired effect.

[0003] Especially when using cooling agents, one is faced with the challenge of creating not only the highest possible impact but also the longest-lasting cooling effect. However, with conventional formulations, it is often impossible or only very limited to create a particularly rapid and high impact and / or a particularly long-lasting cooling effect. Therefore, the cooling effect often takes a long time to set in and / or wears off very quickly.

[0004] It is already known in the art that the taste perception of chewing gum during chewing can be improved and prolonged by controlling and prolonging the release of sweeteners. Encapsulating agents are often used to delay the early and rapid release of sweeteners, thus controlling or slowing down the release of sweeteners. Suitable encapsulating materials include those suitable for food contact, such as food-grade shellac, which can be applied to the chewing gum in various ways, such as wet granulation, wax granulation, spray drying, spray chilling, fluidized-bed coating, coacervation, and the like.

[0005] EP 1 011 643 B1, for example, discloses the production of chewing gum. There, acyclic carboxamides are mixed as cooling agents, for example, with an encapsulating agent selected from maltodextrin and acacia to influence the cooling effect. This mixture is then added to a chewing gum formulation.

[0006] US 2007 / 0 098 842 A1 describes a process for producing chewing gum and the resulting chewing gum. Physiological cooling agents such as acyclic carboxamides or combinations of physiological cooling agents are used.

[0007] EP 0 413 539 A2 describes a flavor delivery system that provides improved flavor release, temperature stability, and taste and aroma masking.

[0008] EP 2 106 704 A1 discloses spray-dried particles with a high fragrance or flavor oil loading. A process for their production is also disclosed, as well as their use as fragrance and / or flavoring agents for products and products comprising such particles.

[0009] In general, encapsulants include a variety of different food-grade encapsulating materials, but these can be quite expensive and are not as effective in prolonging the release of flavors, sweeteners, and cooling agents to the desired extent.

[0010] There is therefore a need to maintain, prolong, improve, enhance and improve the impact of the sensory properties, such as the cooling effect or the feeling of freshness, in oral preparations, especially chewing gum and sweets, during consumption.

[0011] The object of the present invention was to provide a composition that exerts a long-lasting and / or rapidly acting cooling effect in oral preparations, particularly chewing gum and candy. Furthermore, the composition serves to enhance, prolong, and improve the cooling effect of specific cooling agents. Furthermore, the object of the invention was to incorporate this cooling composition into oral preparations, particularly chewing gum or other confectionery. The object of the invention was particularly to provide a process for stably incorporating the cooling composition into such oral preparations, particularly without the cooling effect being lost or destroyed. Description of the invention

[0012] A first aspect of the invention relates to a cooling composition in the form of granules obtained by a process comprising the following steps: a) providing a cooling composition, wherein the cooling composition is a composition consisting of (A) 8 to 10 wt.% cooling agent (A) is selected from the group consisting of menthone glycerol acetal (FEMA GRAS 3807), menthone glycerol ketal (FEMA GRAS 3808), menthyl lactate (FEMA GRAS 3748), menthol ethylene glycol carbonate (FEMA GRAS 3805), menthol propylene glycol carbonate (FEMA GRAS 3806), menthyl N-ethyl oxamate, monomethyl succinate (FEMA GRAS 3810), monomenthyl glutamate (FEMA GRAS 4006), menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849) and the menthanecarboxylic acid esters and amides or acyclic carboxamides of the formula (I)whereby R' and R'' independently of one another are hydrogen, hydroxyl group or a branched, unbranched, cyclic alkyl radical having up to 25 C atoms, an aryl group having up to 10 C atoms, selected from substituted and unsubstituted phenyl, phenylalkyl, naphthyl and pyridyl radicals, or mixtures thereof, and (B) 15 to 35 wt.% alcohol selected from the group consisting of a C1 to C3 alcohol or mixtures thereof, and (C) 60 to 80 wt.% hydrophobic compound selected from the group consisting of essential oils, neutral oils, vegetable oils or mixtures thereof, b) Dissolving the cooling agent (A) in (B) and (C) completely to form a homogeneous mixture, keeping the temperature at 40 °C to 100 °C for complete dissolution of (A), c) spray granulating the homogeneous mixture obtained in step b) at a temperature of 35°C to 65°C to prevent recrystallization of (A), d) Obtaining a cooling composition in the form of granules, the particles having an average particle size of 0.3 mm to 0.9 mm.

[0013] Furthermore, a composition with a cooling effect is described herein, comprising about 2 to about 15 wt.% cooling agent (A), 0 to about 35 wt.% alcohol (B), about 55 to about 95 wt.% hydrophobic compound (C), which in the oral preparations to be used causes a physiological cooling effect to impart a feeling of freshness.

[0014] The cooling agent in the cooling composition triggers a sensation of coolness on the skin and the (oral) mucosa. This sensation is created by an interaction of the cooling agents with thermoreceptors located in the skin or (oral) mucosa. The cooling agents bind to cold receptors in the skin or (oral) mucosa, thereby increasing the intracellular calcium concentration and triggering a nerve impulse that creates a sensation of cold in the body or is perceived as a feeling of cold. One such receptor is TRPM8, which belongs to the group of cold menthol receptors (also known as cold membrane receptor (CMR)1) or to the family of "transient receptor potential ion channels."This receptor is specifically expressed in a specific group of neurons and forms pores in the cell membrane (four units assemble to form a tetramer) that selectively allow Ca2+ ions to pass through. The protein has six transmembrane domains and a cytoplasmic C- and N-terminus. Low temperatures (preferably 10-25°C) stimulate this receptor, resulting in signal transduction that is interpreted by the nervous system as a sensation of cold. The receptor was first described as a cold receptor in several publications in 2002 (Peier AM et al., .A TRP Channel that senses cold Stimuli and menthol.Cell. 2002 Mar 8; 108(5):705-15; McKemy DD et al. Identification of a cold receptor reveals a general role for TRP Channels in thermosensation Nature 2002 Mar 7; 416 (6876): 52-8; Zuker CS. Neurobiology: A cool ion Channel Nature 2002 Mar 7; 416 (6876): 27-8).

[0015] In the present invention, it was surprisingly found that the addition of the above-mentioned composition not only has a cooling effect, but also, due to the method of preparation of the composition, the cooling effect sets in quickly and with a high impact, is intensified, improved, and / or long-lasting. Oral preparations containing such a cooling composition can also exhibit the aforementioned advantages of the above-mentioned composition according to the invention.

[0016] Accordingly, a process for producing the cooling composition is described herein, characterized in that the cooling composition is encapsulated in a spray granulation process, wherein the cooling agent (A) is dissolved in (B) and (C) in a preceding step to form a homogeneous mixture, and wherein the temperature is maintained at 40°C to 100°C, preferably at 45°C to 80°C, particularly preferably at 50°C to 70°C and most particularly preferably at 40°C to 50°C, for complete dissolution of (A). In the further spray granulation processing process, the temperature is maintained at 35°C to 65°C, preferably at 38°C to 60°C, particularly preferably at 39°C to 43°C, in order to prevent recrystallization of (A), wherein the granule particles obtained from the spray granulation have an average particle size of 0.3 mm to 0.9 mm, preferably of 0.4 mm to 0.8 mm, particularly preferably of 0.5 mm to 0.7 mm.

[0017] It has proven particularly advantageous if the ratio of cooling agent (A) : alcohol (B) : hydrophobic compound (C) is 1:1:8, preferably 1:1.5:7.5, particularly preferably 1:3:6.

[0018] A concentration of 5 to 10 wt.% cooling agent (A), 10 to 90 wt.% alcohol (B) and 55 to 90 wt.% hydrophobic compound (C), preferably a concentration of 8 to 10 wt.% cooling agent (A), 15 to 35 wt.% alcohol (B) and 60 to 80 wt.% hydrophobic compound (C), and very particularly of 9.5 to 10 wt.% cooling agent (A), 25 to 30 wt.% alcohol (B) and 60 to 75 wt.% hydrophobic compound (C) is particularly effective and can be prepared according to the above-mentioned method of preparation without the cooling effect subsequently being lost in oral preparations, in particular in chewing gum or sweets.

[0019] In a preferred embodiment, the concentration of the cooling agent is 10 wt.%, of the alcohol (B) is 30 wt.% and of the hydrophobic compound (C) is 60 wt.%.

[0020] The invention further provides an oral preparation comprising a cooling composition with components (A), (B), and (C) as described above, wherein the oral preparation is preferably a chewing gum or a candy. According to the invention, the term candy preferably refers to hard candies and chewy candies.

[0021] In a preferred embodiment, an oral preparation which is a chewing gum comprises a) 5-95 wt.% chewing gum base, b) 5-95 wt.% fillers and sweeteners, c) 0.1-15 wt.% flavorings, d) 0.4-2 wt.% of a cooling composition according to the present invention, which in the preparations to be used causes a physiological cooling effect and a long-lasting feeling of freshness.

[0022] When examining the sensory properties of oral preparations, in particular chewing gums, compared to conventional chewing gums, i.e. without the combination of cooling agent (A), alcohol (B) and hydrophobic compound (C), which are produced according to the described spray granulation process, no cooling effect is observed. Cooling agent A

[0023] Suitable cooling agents (A) are those compounds selected from the group consisting of acyclic carboxamide compounds and menthol compounds or mixtures thereof.

[0024] The combination of several active ingredients, such as mixtures of several cooling agents, has the advantage that they support each other synergistically. Menthol compounds

[0025] Menthol compounds that can be used according to the invention are, for example, selected from the group consisting of menthol methyl ether, menthone glycerol acetal (FEMA GRAS (FEMA stands for "Flavor and Extracts Manufacturers Association" and GRAS is defined as "Generally Regarded As Safe". A FEMA GRAS designation means that the substance labeled in this way has been tested according to a standard method and is considered toxicologically safe.) 3807), menthone glycerol ketal (FEMA GRAS 3808), menthyl lactate (FEMA GRAS 3748), menthol ethylene glycol carbonate (FEMA GRAS 3805), menthol propylene glycol carbonate (FEMA GRAS 3806), menthyl N-ethyl oxamate, monomethyl succinate (FEMA GRAS 3810), monomenthyl glutamate (FEMA GRAS 4006), Menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849) and the menthanecarboxylic acid esters and amides WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30 and mixtures thereof.

[0026] All of these substances are commercially available and can be obtained using standard organic chemistry methods.

[0027] A first important representative is monomenthyl succinate (FEMA GRAS 3810), which was patented as a substance by Brown & Williamson Tobacco Corp. in 1963 (US 3,111,127 A) and is protected as a cooling agent by US 5,725,865 A and US 5,843,466 A (V. Mane Fils). Both the succinate and the analogue monomenthyl glutarate (FEMA GRAS 4006) are important representatives of monomenthyl esters based on di- and polycarboxylic acids:

[0028] Examples of applications of these substances can be found in the publications WO 2003 / 043 431 A1 (Unilever) or EP 1 332 772 A2 (IFF).

[0029] The next important group of menthol compounds preferred in the context of the invention comprises carbonate esters of menthol and polyols, such as glycols, glycerol or carbohydrates, such as menthol ethylene glycol carbonate (FEMA GRAS 3805 = Frescolat ® MGC), menthol propylene glycol carbonate (FEMA GRAS 3784 = Frescolat ® MPC), Menthol 2-Methyl-1,2-propanediol Carbonate (FEMA GRAS 3849) or the corresponding sugar derivatives:

[0030] The use of such substances as a cooling agent for cigarettes is, for example, the subject of US 3 419 543 A (Mold et al.) from 1968; the use as a physiological cooling agent is claimed in DE 42 26 043 A1 (H&R).

[0031] For the purposes of the invention, the menthol compounds menthyl lactate (FEMA GRAS 3748 = Frescolat ®ML) and in particular the menthone glycerol acetal (FEMA GRAS 3807) or menthone glycerol ketal (FEMA GRAS 3808), which is sold under the name Frescolat ® MGA is marketed.

[0032] The former structure is obtained by esterification of lactic acid with menthol, the latter by acetalization of menthone with glycerol (cf. DE 26 08 226 A1, H&R). This group of compounds also includes 3-(L-menthoxy)-1,2-propanediol, also known as Cooling Agent 10 (FEMA GRAS 3784, cf. US 6 328 982 B1 TIC), as well as 3-(L-menthoxy)-2-methyl-1,2-propanediol.

[0033] (FEMA GRAS 3849), which has an additional methyl group.

[0034] The preparation of 3-(I-menthoxy)-1,2-propanediol, for example, starting from menthol is carried out according to the following scheme (cf. US 4 459 425 A, Takagaso).

[0035] Alternative routes, in which menthol is reacted with epichlorohydrin in the first step, are described in US Pat. Nos. 6,407,293 A and 6,515,188 A (Takagaso). The following is an overview of the preferred menthol compounds characterized by a CO bond:

[0036] Among these substances, menthone glycerol acetal / ketal, menthyl lactate, menthol ethylene glycol carbonate and menthol propylene glycol carbonate have proven particularly advantageous, which the applicant markets under the names Frescolat ® MGA, Frescolat ® ML, Frecolat ® MGC and Frescolat ® MPC distributes.

[0037] In the 1970s, menthol compounds were first developed that possess a CC bond in the 3-position, and several of these compounds can also be used in accordance with the invention. These substances are generally referred to as WS types. The basic structure is a menthol derivative in which the hydroxyl group is replaced by a carboxyl group (WS-1). All other WS types are derived from this structure, such as the species WS-3, WS-4, WS-5, WS-12, WS-14, and WS-30, which are also preferred in accordance with the invention. The two diagrams below show the synthesis routes:

[0038] The esters derived from WS-1 are described, for example, in US Pat. No. 4,157,384 A, and the corresponding N-substituted amides are described in J. Soc. Cosmet. Chem., pp. 185-200 (1978). Acyclic carboxamide compounds

[0039] Preferred acyclic carboxamides are derived from the following structure: where R' and R'' can independently be hydrogen, hydroxyl, or an alkyl radical with up to 25 carbon atoms, an aryl group with up to 10 carbon atoms, selected from substituted and unsubstituted phenyl, phenylalkyl, naphthyl, and pyridyl radicals. The alkyl radical can be branched, unbranched, or cyclic, thus encompassing alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, hydroxyalkyl, acyloxyalkyl, alkoxy, alkoxyalkyl, aminoalkyl, acylaminoalkyl, carboxyalkyl radicals, and similar combinations.

[0040] R' and R" are preferably methyl, ethyl, propyl, butyl, isobutyl, n-decyl, cyclopropyl, cyclohexyl, cyclopentyl, cycloheptylmethyl, 2-hydroxyethyl, 3-hydroxy-n-propyl, 6-hydroxy-n-hexyl, 2-aminoethyl, 2-acetoxyethyl, 2-Ethylcarboxyethyl, 4-Hydroxybut-2-ynyl, Carboxymethyl, Benzyl, Naphthyl, 4-Methoxyphenyl, 4-Hydroxyphenyl, 4-Methylphenyl, 3-Hydroxy-4-methylphenyl, 4-Fluorophenyl, 4-Nitrophenyl, 2-Hydroxynaphthyl, Pyridyl.

[0041] Most particularly preferred is the cooling agent A (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide (FEMA 4681), which has the following structure (II): Alcohol B

[0042] Suitable alcohols (B) are those compounds selected from the group consisting of C1 to C3 alcohols or mixtures thereof, such as methanol, ethanol, propanol, and 1,2-propanediol. Ethanol and 1,2-propanediol are particularly preferred. Hydrophobic compound C

[0043] Suitable hydrophobic compounds (C) are selected from the group consisting of essential oils (natural oils), neutral oil and vegetable oils (vegetable oils).

[0044] Preferred essential oils are selected from the group consisting of peppermint oil (menthol), carvone, eucalyptus oil, grapefruit, orange oil, lemon oil, turpentine oil, tea tree and clove oil, camphor, rose oil, lavender oil or methyl salicylate or mixtures thereof.

[0045] Preferred vegetable oils are fats and oils obtained from oilseeds and are selected from the group consisting of sunflower, olive, thistle, sesame and almond oil, algae oil, apricot kernel oil or apricot kernel oil, argan oil, avocado oil, borage oil or borage seed oil, cashew shell oil, rosehip seed oil, hazelnut oil, jojoba oil, coffee bean oil, camellia oil, macadamia oil, almond oil, papaya seed oil, pistachio oil, castor oil, sea buckthorn oil, sea buckthorn kernel oil, walnut oil or mixtures thereof.

[0046] Preferred neutral oils (MCT oil = medium chain triglycerides) are mixtures of medium-chain fatty acids (triglycerides), more precisely a mixture of capric acid and caprylic acid (CAS number 73398-61-5).

[0047] The starting point for the production of neutral oils is palm kernel or coconut oil. The fats are saponified (split by hydrolysis), undesirable fatty acids (including lauric acid and myristic acid) are separated, and the desired fatty acids are esterified with glycerol. MCT triglycerides, for example, are commercially available under the trade names Myglio1812° from Sasol, Myritol 312 ® the company Cognis and Tegosoft ®CT from Evonik. The various products differ in the percentage composition of the two fatty acids, capric acid and caprylic acid. All are lipids based on approximately 50-65% caprylic acid (C8:0) and approximately 30-45% capric acid (C10:0). Caproic acid (C6:0), lauric acid (C12:0), and myristic acid (C14:0) are present in very small amounts. Manufacturing process

[0048] The cooling composition is produced in a spray granulation process, in which the components cooling agent (A), alcohol (B), and hydrophobic compound (C) are encapsulated. It is important that the cooling agent (A) is completely dissolved in (B) and (C) in a preliminary step to form a homogeneous mixture. The temperature is maintained at 40°C to 100°C to ensure complete dissolution of (A). All components are then encapsulated in a spray granulation process. The temperature should then be maintained at 35°C to 65°C, preferably 38°C to 60°C, and particularly preferably 39°C to 43°C, to prevent recrystallization of the cooling agent (A). The granulate particles obtained from the spray granulation have an average particle size of 0.3 mm to 0.9 mm, preferably 0.4 mm to 0.8 mm, particularly preferably 0.5 mm to 0.6 mm.

[0049] When preparing the cooling composition, it is particularly important to ensure that the cooling agent (A) is completely dissolved. This is achieved partly by the temperature and partly by the specific combination of (A), (B), and (C). Dissolving (A) preferably takes place at 40°C to 100°C, preferably at 45°C to 80°C, particularly preferably at 50°C to 70°C, and most preferably at 40°C to 50°C.

[0050] It is also necessary that in the subsequent spray granulation process the temperature is maintained such that recrystallization of the cooling agent (A) is prevented, ie the temperature is maintained at 35°C to 65°C, preferably at 38°C to 60°C, particularly preferably at 40°C to 43°C.

[0051] In a preferred embodiment, the cooling agent (A) is (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane carboxamide (FEMA 4681), the alcohol (B) is ethanol and the hydrophobic compound (C) is neutral oil.

[0052] In a preferred embodiment, the cooling agent (A) is (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane carboxamide (FEMA 4681), the alcohol (B) is 1,2-propanediol and the hydrophobic compound (C) is neutral oil.

[0053] In a preferred embodiment, the cooling agent (A) is (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane carboxamide (FEMA 4681), the alcohol (B) is ethanol and the hydrophobic compound (C) is peppermint oil.

[0054] In these combinations, the cooling composition can be particularly well incorporated into chewing gum or candy, and the advantages of the invention described above are particularly evident. In particular, these special combinations make it possible to perceive a physiological cooling effect in chewing gum or candy upon consumption.

[0055] Fluidized bed spray granulation enables active ingredients to be encapsulated in compact, nearly spherical granules with excellent physical properties. The process is well known in the art and is described in detail, for example, in EP 1 139 791 A1. In fluidized bed spray granulation, liquids containing solids (e.g., suspensions or emulsions) are atomized in the fluidized bed and impinge on the granulation nuclei in droplet form. The liquid evaporates, and the solid is drawn onto the granulation nuclei, forming a solid shell. This process is repeated continuously in the fluidized bed, producing very compact, shell-like granules. Parameters such as particle size, residual moisture content, and solid content can be precisely adjusted in fluidized bed spray granulation, allowing a wide variety of substances to be processed into granules.Since the drying and shaping processes take place in parallel during granulation in the fluidized bed process, it is also referred to as continuous fluidized bed spray drying granulation (MJV Goldschmidt, GGC Weijersa, R. Boerefijn, JAM Kuipers: “Discrete element modelling of fluidised bed spray granulation”, Powder Technology 138 (2003) 39- 45; Maksym Dosta, Stefan Heinrich, Joachim Werther: Fluidized bed spray granulation: “Analysis of the system behaviour by means of dynamic flowsheet simulation”, Powder Technology 204 (2010) 71-82).

[0056] Accordingly, a further subject matter of the invention is a granulate containing cooling agent (A), alcohol (B) and hydrophobic compound (C), obtainable by the spray granulation process described above.

[0057] In a preferred embodiment, a granulate according to the invention is composed as follows: composition D E Mixture A Modified starch 45-60 45-60 Gum arabic (Senegal) 15-25 15-25 sugar alcohol 5-10 5-10 dye 0-2 0-2 Polysaccharides 0-2 0-2 Gelling agent* 0-2 0-2 Maltodextrin - 50-75 Mixture B Cooling composition according to the invention 10-30 10-30

[0058] In a preferred embodiment, a granulate according to the invention contains the composition: composition D E Mixture A Modified starch 50,0 50,0 Gum arabic (Senegal) 20,0 20,0 sugar alcohol 7,0 7,0 dye - 0,15 Polysaccharides - 1,5 Gelling agent* - 1,0 Maltodextrin - 68,0 Mixture B Cooling composition according to the invention 20,0 20,0 Commercial ApplicabilityChewing Gum

[0059] The preferred oral preparation incorporating the cooling composition is chewing gum.

[0060] The term “chewing gum” as used here includes in particular chewing gum tablets, chewing gum strips, chewing gum tablets, chewing gum pillows, chewing gum cubes and also bubble gums and the like.

[0061] The preferred oral preparation in which the cooling composition according to the invention is incorporated is chewing gum. Such a preparation preferably comprises a) 5-95% by weight of chewing gum base, b) 5-95% by weight of fillers and sweeteners, c) 0.1-15% by weight of flavorings, d) 0.4-2% by weight of the cooling composition according to the invention. The cooling composition produces a physiologically cooling effect in the oral preparations to be used, particularly in chewing gum or candy, so that the consumer is given the impression of a long-lasting feeling of freshness. Water-insoluble base

[0062] The water-insoluble base, also referred to as a "rubber base," typically comprises natural or synthetic elastomers, resins, fats and oils, plasticizers, fillers, dyes, and optionally waxes. The proportion of the base in the total composition typically amounts to 5 to 95, preferably 10 to 50, and in particular 20 to 35 wt.%. In a typical embodiment of the invention, the base is composed of 20 to 60 wt.% synthetic elastomers, 0 to 30 wt.% natural elastomers, 5 to 55 wt.% plasticizers, 4 to 35 wt.% fillers, and minor amounts of additives such as dyes, antioxidants, and the like, with the proviso that they are water-soluble at most in small amounts.

[0063] Suitable synthetic elastomers include, for example, polyisobutylenes with average molecular weights (according to GPC) of 10,000 to 100,000 and preferably 50,000 to 80,000, isobutylene-isoprene copolymers (“butyl elastomers”), styrene-butadiene copolymers (styrene:butadiene ratio e.g. 1: 3 to 3: 1), polyvinyl acetates with average molecular weights (according to GPC) of 2,000 to 90,000 and preferably 10,000 to 65,000, polyisoprenes, polyethylene, vinyl acetate-vinyl laurate copolymers and mixtures thereof. Examples of suitable natural elastomers are rubbers such as smoked or liquid latex or guayule, as well as natural gums such as jelutong, lechi caspi, perillo, sorva, massaranduba balata, massaranduba chocolate, nispero, rosindinba, chicle, gutta hang 1kang and mixtures thereof.The selection of synthetic and natural elastomers and their blending ratios depends primarily on whether the chewing gum is intended to produce bubbles ("bubble gum") or not. Elastomer blends containing jelutong, chicle, sorva, and massaranduba are preferred.

[0064] In most cases, the elastomers prove to be too hard or too malleable during processing, so it has proven advantageous to use special plasticizers, which, of course, must also meet all requirements for approval as food additives. In this regard, esters of resin acids are particularly suitable, for example, esters of lower aliphatic alcohols or polyols with fully or partially cured, monomeric, or oligomeric resin acids. Methyl, glycerol, or pentareythritol esters, as well as mixtures thereof, are particularly used for this purpose. Alternatively, terpene resins, which can be derived from alpha-pinene, beta-pinene, delta-limonene, or mixtures thereof, are also considered.

[0065] Fillers or texturizing agents include magnesium or calcium carbonate, ground pumice, silicates, especially magnesium or aluminum silicates, clays, aluminum oxides, talc, titanium dioxide, mono-, di-, and tricalcium phosphate, and cellulose polymers.

[0066] Suitable emulsifiers are tallow, hydrogenated tallow, hydrogenated or partially hydrogenated vegetable oils, cocoa butter, partial glycerides, lecithin, triacetin and saturated or unsaturated fatty acids having 6 to 22 and preferably 12 to 18 carbon atoms and mixtures thereof.

[0067] Examples of suitable dyes and whitening agents include FD and C types approved for coloring food, plant and fruit extracts, and titanium dioxide.

[0068] The base compositions may contain waxes or be wax-free; examples of wax-free compositions can be found, inter alia, in patent specification US 5,286,500 A, the contents of which are hereby expressly incorporated by reference. Water-soluble components

[0069] In addition to the water-insoluble gum base, chewing gum preparations regularly contain a water-soluble component, which may be formed, for example, by softeners, sweeteners, fillers, flavorings, flavor enhancers, emulsifiers, colorings, acidulants, antioxidants, and the like, provided that the components possess at least sufficient water solubility. Depending on the water solubility of the specific components, individual components can therefore belong to both the water-insoluble and the water-soluble phase. However, it is also possible to use combinations, for example, of a water-soluble and a water-insoluble emulsifier, with the individual components then being in different phases. The water-insoluble component typically makes up 5 to 95 and preferably 20 to 80% by weight of the preparation.

[0070] Water-soluble softeners or plasticizers are added to chewing gum compositions to improve chewability and chewing sensation and are typically present in the mixtures in amounts of 0.5 to 15% by weight. Typical examples are glycerin, lecithin, and aqueous solutions of sorbitol, hydrogenated starch hydrolysates, or corn syrup.

[0071] Both sugar-containing and sugar-free compounds can be used as sweeteners, used in amounts of 5 to 95, preferably 20 to 80, and especially 30 to 60 wt.% based on the chewing gum composition. Typical saccharide sweeteners are sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, galactose, corn syrup, and mixtures thereof. Suitable sugar substitutes include sorbitol, mannitol, xylitol, hydrogenated starch hydrolysates, maltitol, and mixtures thereof. Furthermore, so-called HIAS (“High Intensity Artificial Sweeteners”) can also be considered as additives, such as sucralose, aspartame, acesulfame salts, alitame, saccharin and saccharin salts, cyclamic acid and its salts, glycyrrhizins, dihydrochalcones, thaumatin, monellin and the like, alone or in mixtures.Also particularly effective are the hydrophobic HIAS, which are the subject of international patent application WO 2002 091849 A1 (Wrigley's), as well as stevia extracts and their active ingredients, particularly rebaudioside A. The amount of these substances used depends primarily on their performance and typically ranges from 0.02 to 8 wt.%.

[0072] Fillers such as polydextrose, raffinose, raffinyl, fructooligosaccharides (NutraFlora), palatinose oligosaccharides, guar gum hydrolysates (Sun Fiber) and dextrins (Fibersol) are particularly suitable for the production of low-calorie chewing gum.

[0073] The choice of additional flavorings is virtually unlimited and not critical to the essence of the invention. Typically, the total proportion of all flavorings is 0.1 to 15%, and preferably 0.2 to 5%, by weight of the chewing gum composition. Suitable additional flavorings include, for example, essential oils, aromas, and the like, such as mint oil, spearmint oil, anise oil, star anise oil, caraway oil, eucalyptus oil, fennel oil, lemon oil, wintergreen oil, clove oil, and the like, as are also used, for example, in oral and dental care products.

[0074] The chewing gum may also contain excipients and additives suitable for dental care, specifically for combating plaque and gingivitis, such as chlorhexidine, CPC, or trichlosan. They may also contain pH regulators (e.g., buffers or urea), anti-caries agents (e.g., phosphates or fluorides), and biogenic active ingredients (antibodies, enzymes, caffeine, plant extracts), as long as these substances are approved for use in food products and do not interact adversely with each other.

[0075] Accordingly, a process for producing a chewing gum with a longer lasting freshness feeling is also described herein, comprising: i) manufacturing a chewing gum composition containing 5-95% by weight of gum base, 5-95% by weight of fillers and sweeteners, 0.1-15% by weight of flavorings and ii) Addition of 0.2-3 wt.% of the cooling composition according to the invention, which produces a physiologically cooling effect in the preparations to be used, imparting a feeling of freshness. A concentration of 0.4-1 wt.% is particularly effective.

[0076] the cooling composition according to the invention. Candies

[0077] Another preferred oral preparation incorporating the cooling composition is in the form of candies.

[0078] Candies usually contain sugar compounds as a candy base, such as mono-, di-, and trisaccharides, oligosaccharides, or their derivatives, such as glucose, lactose, maltose, xylose, sucrose, and fruit oligosaccharides. A candy base contains 10 to 99 wt.%, preferably 15 to 95 wt.%, particularly preferably 15 to 95 wt.%, of sugar compounds.

[0079] Furthermore, sweets contain edible acids such as aliphatic, saturated and unsaturated mono-, di- and tricarboxylic acids, such as citric acid, fumaric acid, maleic acid, lactic acid, tartaric acid, adipic acid, succinic acid, ascorbic acid, glutaric acid, acetic acid, phosphoric acid, etc.

[0080] Candies (also called drops) come in almost every imaginable color, flavor, and shape. They are usually ellipsoidal or spherical. They typically have a particularly sweet, sour, or liquid filling. A distinction is made between hard candies, which have a glassy texture and a water content of up to 3%, and soft candies (toffee, toffee candy), which are chewy, have a chewy-gum consistency, and contain up to 8% water.

[0081] Candies of the present invention preferably have a filling comprising the cooling composition of the invention. These candies preferably have a candy base of 60-95 wt.%, particularly preferably 75 to 85 wt.%, and a filling of 5 to 40 wt.%, preferably 15 to 25 wt.%. In addition to the cooling composition, other ingredients are also present in the filling. The cooling composition is present in such a candy in an amount of 0.2 to 4 wt.%, preferably 0.5 to 2 wt.%.

[0082] The filling of such a candy can be solid, powdered, watery, pasty, gel-like, or gummy. A watery filling usually has a water content of less than 10%, preferably less than 8%, and particularly preferably less than 6%.

[0083] The filling may further contain edible ingredients approved for use in the food industry, such as alcohols and polyalcohols, such as glycerin, polyethylene glycol, or propylene glycols with low molecular weights (less than 1000 MW). These are present in the filling in a range of 30-95 wt.%, preferably 40 to 90 wt.%, particularly preferably 40 to 60 wt.%.

[0084] Furthermore, candy fillings can contain sweeteners in an amount of 5 to 80 wt.%, preferably 30 to 75 wt.%. The sweeteners used in candy can be found in the section on chewing gum, as they can be used analogously for candy.

[0085] Candy fillings also include thickeners approved for use in foodstuffs. These are, for example, xanthan gum, carrageenan and its derivatives, hydroxypropylmethylcellulose, sclerotium gum, pullulan, rhamsan gum, welan gum, konjac, kurdlan, carbomer, algin, alginic acid, alginates and their derivatives, hydroxyethylcellulose and its derivatives, hydroxypropylcellulose and its derivatives, phosphate starch derivatives, guar gum and its derivatives, starch and its derivatives, copolymers of maleic anhydride with alkenes and their derivatives, ethylene glycol / propylene glycol copolymers, long-chain alcohols such as behenyl alcohol, poloxamers and their derivatives, polyacyralet and their derivatives, methylcellulose and its derivatives, ethylcellulose and its derivatives, agar and its derivatives, pectin and its derivatives, chitosan and its derivatives, and higher molecular weight polyethylene glycols such as polyethylene glycols (with 10000 MW or more), Karaya gum,Copolymers of vinylpyrrolidone with alkenes, polyacrylamides, chitin derivatives, gelatin, beta-glucan, dextrin, dextran, cyclodextrin, methacrylates, microcrystalline cellulose, polyquats, furcellaren gum, ghatti gum, psyllium gum, quince gum, tamarind gum, larch gum, tara gum, tallow, kaolin clay, bentonite, cellulose, fumed silica and mixtures thereof.

[0086] Thickeners are preferably contained in sweets in an amount of 0.001 to 10 wt.%, particularly preferably 0.01 to 5 wt.%, very particularly preferably 0.01 to 2.5 wt.% and especially preferably 0.01 to 1 wt.%.

[0087] Flavorings can be aqueous or oil-based and derived from plant parts such as leaves, flowers, fruits, etc. Suitable flavorings include the oils of lemons, oranges, bananas, grapes, limes, apricots, grapefruit, apples, strawberries, cherries, oranges, pineapples, or coffee, cocoa, cola, peanuts, almonds, licorice root, or ginger root. Flavorings are used in candies in an amount preferably up to 4% by weight, particularly preferably from 0.1 to 1% by weight. Use of the preparations

[0088] Finally, the use of the cooling composition to provide a feeling of freshness through a physiologically cooling effect in oral preparations is further described herein. The oral preparation is preferably a chewing gum or a candy. Examples

[0089] Unless otherwise stated, all percentages are based on weight. I) Production of granulate particles with a cooling composition according to the invention

[0090] A mixture B is initially heated to 50°C and stirred until a homogeneous mixture is formed. A carrier component is then prepared from a homogeneous mixture A and also heated to 50°C. Mixture B is then dispersed into the carrier component mixture A, and the entire mixture is spray-granulated, maintaining the temperature between 39°C and 40°C during the process.

[0091] The granulate particles obtained from spray granulation can have an average particle size of 0.3 mm, 0.4 mm, 0.5 mm, 0.6 mm, 0.7 mm, 0.8 mm and 0.9 mm, depending on the process conditions.

[0092] The granulate particles from the production have the composition listed in Table 1. Table 1 Granules containing cooling composition composition D E Mixture A Modified starch 45-60 45-60 Gum arabic (Senegal) 15-25 15-25 sugar alcohol 5-10 5-10 dye 0-2 0-2 Polysaccharides 0-2 0-2 Gelling agent* 0-2 0-2 Maltodextrin - 50-75 Mixture B Cooling composition 10-30 10-30 *Pectin

[0093] Cooling compositions can be composed as follows (F1, F5 and F6 are not according to the invention): Table 2 Cooling composition composition F1 F2 F3 F4 i ) F5 F6 F7 F8 Cooling agent (A)* 10,0 10,0 10,0 10,0 10,0 15,0 10,0 10,0 Alcohol (B)** - 10,0 15,0 30,0 90,0 85,0 20,0 15,0 Hydrophobic compound (C)*** 90,0 80,0 75,0 60,0 - - 70,0 75,0 *Kühlwirkstoff A ausgewählt aus: Menthon-Glycerinacetal (FEMA GRAS i 3807), Menthon-Glycerinketal (FEMA GRAS 3808), Menthyllactat (FEMA GRAS 3748), Menthol-Ethylenglycol-Carbonat (FEMA GRAS 3805), Menthol-Propylenglycol-Carbonat (FEMA GRAS 3806), Menthoxy-1,2-Propandiol (FEMA GRAS 3784), Menthoxy-2-Methyl-1,2-Propandiol (FEMA GRAS 3849) oder (1R,2S,5R)-N-(4-Methoxyphenyl)-5-Methyl-2-(1-Methylethyl)-Cyclohexan-Carboxamid (FEMA 4681). **Alcohol B: Ethanol or 1,2-propanediol ***Hydrophobic compounds selected from: peppermint oil (menthol), carvone or neutral oils i) Cooling agent A: (1R,2S,5R)-N-(4-Methoxyphenyl)-5-Methyl-2-(1-Methylethyl)-Cyclohexane-Carboxamide (FEMA 4681), Alcohol B: Ethanol, Hydrophobic compound C: Peppermint oil II) Chewing gum mass

[0094] Chewing gums were produced from a granulate according to Table 1 and a chewing gum mass as indicated below in Table 3, and their cooling effect was sensorially evaluated. Table 3 Chewing gum masses composition K L M Polyisobutylene (MW 20,000) 20.0 25.0 30.0 Sorbitol 51,0 47,5 44,5 Mannitol 5,0 4,3 3,6 Glycerin 8,0 8,0 7,0 Lycasin:Glycerin (1:1) 8,2 8,0 7,0 Lecithin 0,2 0,2 0,2 Flavor blend 1,0 1,0 1,0 Water Ad 100 III) Sensory test

[0095] The cooling compositions according to the invention were incorporated into chewing gum masses. The cooling effect of the chewing gums was then sensorially evaluated by trained individuals. The sensory evaluation is summarized in Table 4, using the following scale: Rating range 0: nothing noticeable Rating range 1-3: weak cooling effect Rating range 4-6: medium cooling effect Rating range 7-8: strong cooling effect Rating range 9-10: strong cooling effect

[0096] Examples E1 to E4 are according to the invention, example V1 is for comparison. Table 4 Sensory evaluations of chewing gums with and without cooling composition Time [min] V1 E1 E2 E3 E4 1 1-3 1-3 4-6 4-6 4-6 2 4-6 4-6 7-8 3 4 7-8 9-10 9-10 5 7-8 6 9-10 7-8 7 8 9 10 4-6 15 4-6 4-6 20 25 4-6 1-3 30 1-3 1-3 35 40 45 1-3

[0097] V1 briefly explains how the table should be understood: In the first minute, a weak cooling effect is noticeable, which increases from the second to the third minute, reaching a medium cooling effect. From the fourth to the fifth minute, the product exhibits a strong cooling effect, which increases again in the sixth minute, producing a very strong organoleptic cooling effect, which decreases sharply in the 25th minute, reaching a medium cooling effect.

[0098] The control formulation V1 is a standard blend with Citrus Mint and was used as a benchmark. E1: 0.4% Granules D in a chewing gum mass according to Table 3 E2: 0.6% Granules D in a chewing gum mass according to Table 3 E3: 0.4% granules E in a chewing gum mass according to Table 3 E4: 0.6% granules E in a chewing gum mass according to Table 3

[0099] If the cooling agent (A) is incorporated only in sugar alcohol and not by spray granulation as in the invention, but is simply melted into it and then formulated into a chewing gum mass, no cooling effect is observed, as shown in Table 5: Table 5 Chewing gum mass with cooling composition incorporated without spray granulation Comparison test V1 V2 V3 Cooling agent in Isomalt 1% 10% 10% Isomalt with cooling agent in chewing gum 0,4% 0,2% 0,8% Addition of dummy* 1.2% 1.2% 1.2 Sensory test No cooling *1 part triacetin and 2 parts MCT vegetable oil

[0100] The following Table 6 shows an example formulation for a candy: Table 6 Candy containing cooling composition composition A Sucrose 59,8 Glucose (liquid) 43,7 Water 16,2 Citric anhydride 1,2 Cooling composition according to the invention 0,3 aroma 0,2

Claims

[1] Cooling composition in the form of granules obtained by a process comprising the following steps: a) Providing a cooling composition, wherein the cooling composition is a composition consisting of (A) 8 to 10 wt% cooling agent (A) selected from the group consisting of menthone glycerol acetal (FEMA GRAS 3807), menthone glycerol ketal (FEMA GRAS 3808), menthyl lactate (FEMA GRAS 3748), menthol ethylene glycol carbonate (FEMA GRAS 3805), menthol propylene glycol carbonate (FEMA GRAS 3806), menthyl N-ethyloxamate monomethyl succinate (FEMA GRAS 3810), monomenthyl glutamate (FEMA GRAS 4006), menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849) and the menthane carboxylic acid esters and amides or acyclic carboxamides of the formula (I) where R' and R'' independently of each other hydrogen, hydroxyl group or a branched, unbranched, cyclic alkyl group with up to 25 C atoms, an aryl group with up to 10 C atoms, selected from substituted and unsubstituted phenyl, phenylalkyl, naphthyl and pyridyl groups, or mixtures thereof, and (B) 15 to 35% by weight of alcohol selected from the group consisting of a C1 to C3 alcohol or mixtures thereof, and (C) 60 to 80 wt% hydrophobic compound selected from the group consisting of essential oils, neutral oils, vegetable oils or mixtures thereof, b) Dissolving the cooling agent (A) completely in (B) and (C) to form a homogeneous mixture, maintaining a temperature between 40 °C and 100 °C to ensure complete dissolution of (A), c) Spray granulation of the homogeneous mixture obtained in step b) at a temperature of 35°C to 65°C to prevent recrystallization of (A), d) Obtaining a cooling composition in the form of granules, wherein the particles have an average particle size of 0.3 mm to 0.9 mm. [2] Cooling composition in the form of granules according to claim 1, wherein the cooling agent (A) is (1R,2S,5R)-N-(4-Methoxyphenyl)-5-Methyl-2-(1-Methylethyl)-Cyclohexane-Carboxamide (FEMA 4681). [3] Cooling composition in the form of granules according to one of claims 1 or 2, wherein the hydrophobic compound (C) is selected from the group consisting of peppermint oil (menthol), carvone, eucalyptus oil, grapefruit, orange oil, lemon oil, turpentine oil, tea tree and clove oil, camphor, rose oil, lavender oil or methyl salicylate, sunflower, olive, safflower oil, sesame and almond oil, algae oil, apricot kernel oil or apricot kernel oil, argan oil, avocado oil, borage oil or borage seed oil, cashew shell oil, rosehip seed oil, hazelnut oil, jojoba oil, coffee bean oil, camellia oil, macadamia oil, almond oil, papaya seed oil, pistachio oil, castor oil, sea buckthorn oil, sea buckthorn kernel oil, walnut oil or neutral oils with a proportion of 50-65% caprylic acid. 30-45% capric acid and a small proportion of caproic acid, lauric acid and myristic acid or mixtures thereof. [4] Oral preparation comprising a cooling composition in the form of granules according to any one of claims 1 to 3. [5] Oral preparation according to claim 4, wherein the oral preparation is a chewing gum or a candy. [6] Oral preparation according to claim 5, wherein the oral preparation a) 5 to 95 wt.% chewing gum base, b) 5 to 95% by weight of fillers and sweeteners, c) 0.1 to 15% by weight flavorings, d) 0.4 to 2 wt.% cooling composition in the form of granules according to any one of claims 1 to 3, wherein the amounts are supplemented to 100 wt.%.