Sustained-release menthol and manufacturing method therefor

WO2025037740A1PCT designated stage expired Publication Date: 2025-02-20KT&G CO LTD
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Patent Information

Application Number
PCT/KR2024/008669
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2023-08-11
Filing Date
2024-06-24
Publication Date
2025-02-20

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Abstract

The present invention relates to a method for manufacturing sustained-release menthol, the method comprising the steps of: melting menthol (S1); preparing a mixed liquid by mixing molten menthol and glycerin (S2); and preparing a solid dispersion by stirring the mixed liquid (S3), wherein the weight of the melted menthol in the step S2 is greater than the weight of the glycerin.
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Description

Western-release menthol and its manufacturing method

[0001] The present invention relates to western-type menthol and a method for producing the same.

[0002] To satisfy smokers' preferences, smoking articles are flavored in a variety of ways. Typical examples of flavoring include adding flavoring directly to smoking materials such as cigarette butts or filter plugs (e.g., spraying).

[0003] However, since flavoring agents have volatile properties, there is a problem in that the flavor of the cigarette continuously deteriorates as the flavoring agent is lost during the distribution and consumption period of the smoking product.

[0004] The present invention aims to solve the above problems by providing a sustained-release menthol and a method for producing the same in a solid state, which can improve the retention and storability of a fragrance.

[0005]

[0006] However, the problems to be solved by the present invention are not limited to those mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the description below.

[0007] According to one embodiment of the present invention, there is provided a step (S1) of melting menthol;

[0008] Step (S2) of preparing a mixed liquid by mixing melted menthol and glycerin; and

[0009] A step (S3) of preparing a solid dispersion by stirring the above mixed liquid phase; including;

[0010] A method for producing sustained-release menthol is provided, wherein the weight of the menthol in the above step S2 is greater than the weight of the glycerin.

[0011]

[0012] According to another embodiment of the present invention, a solid dispersion comprising menthol and glycerin is provided,

[0013] The above solid dispersion is one in which the menthol is uniformly dispersed in the glycerin,

[0014] Provided is a sustained-release menthol wherein the weight of the menthol is greater than the weight of the glycerin.

[0015]

[0016] According to another embodiment of the present invention, in a smoking article including a medium portion, a filter portion, and a wrapper,

[0017] At least one selected from the group consisting of the above medium, filter, and wrapper comprises a western-type menthol,

[0018] The above-mentioned western menthol comprises a solid dispersion containing menthol and glycerin,

[0019] The above solid dispersion is one in which the menthol is uniformly dispersed in the glycerin,

[0020] A smoking article is provided wherein the weight of the menthol is greater than the weight of the glycerin.

[0021] By using the method for producing the western-type menthol of the present invention, menthol can be uniformly dispersed and can be easily applied to the composition of smoking articles.

[0022] The sustained-release menthol manufactured by the manufacturing method of the present invention has excellent fragrance retention and storability, and can continuously express fragrance without fragrance loss.

[0023] The smoking article including the western-type menthol of the present invention has excellent flavor retention, storability, and durability.

[0024]

[0025] The effects of the present invention are not limited to the effects described above, and should be understood to include all effects that can be inferred from the detailed description of the present invention or the composition of the invention described in the claims.

[0026] Figure 1 is a flow chart of a method for manufacturing western-type menthol according to one embodiment of the present invention.

[0027] Figure 2 is a drawing showing an image of a sustained-release menthol according to the weight ratio of menthol and glycerin.

[0028] Below, embodiments are described in detail with reference to the attached drawings. However, the embodiments may be modified in various ways, and the scope of the patent application is not limited or restricted by these embodiments. It should be understood that all modifications, equivalents, or alternatives to the embodiments are included within the scope of the patent application.

[0029] The terms used in the examples are for illustrative purposes only and should not be construed as limiting. Singular expressions include plural expressions unless the context clearly dictates otherwise. In this specification, terms such as "comprise" or "have" are intended to indicate the presence of a feature, number, step, operation, component, part, or combination thereof described in the specification, but should be understood to not preclude the possibility of the presence or addition of one or more other features, numbers, steps, operations, components, parts, or combinations thereof.

[0030] Unless otherwise defined, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by a person of ordinary skill in the art to which the embodiments pertain. Terms defined in commonly used dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the relevant technology, and shall not be interpreted in an idealized or overly formal sense unless explicitly defined herein.

[0031] In addition, when describing with reference to the attached drawings, identical components will be assigned the same reference numerals regardless of the drawing numbers, and redundant descriptions thereof will be omitted. When describing embodiments, if a detailed description of a related known technology is judged to unnecessarily obscure the gist of the embodiment, the detailed description will be omitted.

[0032] Additionally, in describing components of an embodiment, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms.

[0033] Components included in one embodiment and components with common functions will be described using the same names in other embodiments. Unless otherwise stated, the descriptions given in one embodiment can be applied to other embodiments, and detailed descriptions will be omitted to the extent of overlap.

[0034] Throughout the specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components.

[0035]

[0036] Throughout the specification, "smoking article" may refer to an article capable of generating an aerosol, such as a cigarette (cigarette), cigar, or the like. The smoking article may include an aerosol-generating material or an aerosol-forming substrate. Furthermore, the smoking article may include a solid material based on tobacco raw materials, such as tobacco leaf, tobacco ash, or reconstituted tobacco. The smoking material may include volatile compounds.

[0037] Throughout the specification, 'upstream' or 'upstream direction' means the direction away from the mouth of the user smoking the smoking article, and 'downstream' or 'downstream direction' means the direction toward the mouth of the user smoking the smoking article.

[0038] Throughout the specification, 'solid dispersion' may mean a system in which the active substance (menthol) is uniformly dispersed in solid glycerin and is in a solid state.

[0039]

[0040] According to one embodiment of the present invention, a method for producing sustained-release menthol may be provided. The method for producing sustained-release menthol may include a step (S1) of melting menthol; a step (S2) of producing a mixed liquid phase by mixing the melted menthol and glycerin; and a step (S3) of stirring the mixed liquid phase to produce a solid dispersion (Fig. 1). At this time, the weight of the melted menthol in step S2 may be greater than the weight of the glycerin.

[0041]

[0042] Below, each step is explained in detail.

[0043]

[0044] Step S1 is a step for melting menthol, and menthol can be melted at a temperature of 40°C to 50°C. Since the melting point of menthol is 42°C to 43°C, if step S1 is performed within the above temperature range, solid menthol can be changed into liquid menthol.

[0045]

[0046] Step S2 is the step of producing a mixed liquid by mixing melted menthol and glycerin.

[0047] When mixing powdered raw materials, or powdered and liquid raw materials, continuous review of the mixing amount and mixing method is necessary to ensure uniform mixing. For example, when dissolving powdered raw materials in liquid raw materials, if the solubility exceeds a certain level, the powdered raw materials will no longer dissolve, and a suspension or precipitation may occur. In the present invention, by mixing menthol dissolved in liquid form with glycerin to produce a solid dispersion, the menthol can be dispersed more uniformly than when using powdered raw materials.

[0048] The weight of menthol in the mixed liquid phase should be greater than the weight of glycerin. Preferably, the weight ratio of the melted menthol and glycerin in the mixed liquid phase in step S2 may be 6:4 to 9.9:0.1, more preferably 6:4 to 8:2. When the above weight ratio is satisfied, the solid dispersion in a solid state as desired by the present invention can be obtained.

[0049] The weight ratio of menthol and glycerin must satisfy the above-described range in order to produce sustained-release menthol that is in a solid state and has storability and flavor retention properties. Menthol is generally dissolved in glycerin, but if the menthol content in the mixed liquid is added below the lower limit of the weight ratio of menthol and glycerin, it may remain in a liquid state or may irreversibly change into a semi-solid state. On the other hand, if the menthol content in the mixed liquid is added exceeding the upper limit of the weight ratio, the storability and flavor retention properties may deteriorate due to the high sublimation property of menthol. Preferably, the content of menthol is 80 wt% or less based on the total content of menthol and glycerin.

[0050]

[0051] Step S3 is a step for preparing a solid dispersion, which can be prepared by stirring the previously prepared mixed liquid phase.

[0052] In step S3, the solid dispersion may be one in which the molten menthol is uniformly dispersed in the glycerin and solidified. Specifically, when the mixed liquid is stirred at high speed, the mixed liquid of the molten menthol and glycerin is uniformly mixed, thereby lowering the melting point of the mixed liquid and lowering the temperature of the mixed liquid. When the temperature of the mixed liquid is lowered, solid particles are generated, and when the temperature is further lowered with continued stirring, an irreversible change to a solid state occurs. As a result, a solid dispersion in which a large amount of menthol is uniformly dispersed in the glycerin and stably solidified can be manufactured.

[0053]

[0054] In a method for producing a western-type menthol according to one embodiment of the present invention, after step S3, a step of producing a form by adding an excipient to the solid dispersion may be further included.

[0055] The above excipient may include at least one selected from the group consisting of lactose, microcellulose, and a binder.

[0056] For example, when producing sustained-release menthol in the form of granules or cylindrical blocks of a certain size, lactose and microcellulose can act advantageously in forming and maintaining the shape. In particular, when producing sustained-release menthol in the form of cylindrical blocks, there may be an advantage in that it can be directly applied as a component (medium section, filter section, etc.) of smoking articles when manufacturing smoking articles.

[0057] The binder may serve to enhance cohesion. The binder may be at least one selected from the group consisting of water-soluble polymers and gums. The water-soluble polymer may include, for example, at least one selected from the group consisting of starch, gelatin, and polyvinyl alcohol. The gum may include, for example, at least one selected from the group consisting of guar gum and gum arabic.

[0058]

[0059] In one embodiment of the present invention, a sustained-release menthol can be provided, which comprises a solid dispersion comprising menthol and glycerin, wherein the solid dispersion is a solid dispersion in which the menthol is uniformly dispersed in the glycerin, and the weight of the menthol is greater than the weight of the glycerin. By including the solid dispersion, the sustained-release menthol can have improved flavor retention and storability.

[0060] The glycerin in slow-release menthol can act as a carrier for the menthol flavoring agent. For example, when heat is applied to slow-release menthol, the solidified menthol liquefies, breaking the bond between the menthol and glycerin, releasing the menthol.

[0061]

[0062] According to one embodiment of the present invention, the sustained-release menthol may have at least one form selected from the group consisting of powder, granules, and cylindrical blocks, preferably granules or cylindrical blocks. Since the sustained-release menthol has the above form, menthol can be administered in various dosages over a wider content range, and the dosage of menthol can be more easily set. The sustained-release menthol can be easily applied to smoking articles by being manufactured into a cylindrical block without a separate carrier and then inserted into a medium or filter portion.

[0063]

[0064] In one embodiment according to the present invention, a smoking article can be provided, which includes a medium portion, a filter portion, and a wrapper, wherein at least one selected from the group consisting of the medium portion, the filter portion, and the wrapper includes sustained-release menthol, and the sustained-release menthol includes a solid dispersion including menthol and glycerin, wherein the solid dispersion is a solid dispersion in which the menthol is uniformly dispersed in the glycerin, and the weight of the menthol is greater than the weight of the glycerin.

[0065] A smoking article containing sustained-release menthol can be heated to cause menthol to be released from the sustained-release menthol. For example, when the smoking article is heated, the heat applied to the smoking article (e.g., heat transferred from a heat source, heat transferred to the outer wrapper, heat accumulated inside, etc.) causes the solidified sustained-release menthol to liquefy, breaking the bond between menthol and glycerin. The molten menthol can be impregnated or permeated into the components of the smoking article (e.g., medium, filter, wrapper). At this time, the glycerin can be aerosolized and serve as a carrier for menthol when inhaled. This process allows for a uniform amount of menthol released during smoking, and therefore, the application of sustained-release menthol can provide a smoking article with excellent fragrance persistence. In addition, since the sustained-release menthol has an irreversibly stable solid form when heat is not applied to the smoking article, the menthol is not released, and the smoking article can also have excellent flavor retention and storability.

[0066]

[0067] The filter unit may be located at the downstream end of the smoking article and may be a mono-filter or a composite filter. The filter unit may include at least one fiber selected from the group consisting of cellulose acetate, lyocell, polypropylene, polyester, and polylactic acid, but is not limited to the examples described. Meanwhile, the filter unit may further include activated carbon and a plasticizer.

[0068] The wrapper may include filter paper and cigarette paper. The filter paper surrounds the filter portion and may have an oil-resistant function, while the cigarette paper surrounds the medium portion and is primarily made from materials such as flax or wood pulp. The cigarette paper may contain fillers as additives. The fillers can increase whiteness and opacity and control porosity.

[0069]

[0070] A smoking article according to one embodiment of the present invention may be a heat-not-burn smoking article. Non-combustion smoking articles include electric smoking articles that indirectly heat with electrical energy rather than directly combust.

[0071] In the case of an electric smoking device, it may include a non-combustible smoking device and an aerosol generating device into which the non-combustible smoking device can be inserted. The electric smoking device may be a device that uses electrical energy to heat the inserted smoking device, thereby generating an aerosol, and then allowing smoking to occur by having the aerosol be inhaled and then released by the user.

[0072] A non-combustible smoking article according to one embodiment of the present invention may have various structures.

[0073] For example, a smoking article according to one embodiment of the present invention may further include a support structure and a cooling structure between the medium portion and the filter portion.

[0074] The support structure may be a tubular structure that may be positioned downstream of the medium portion and may include a hollow space therein. The support structure may serve to support the medium portion so that it is not pushed when inserted into the aerosol generating device, and may serve to move the atomizer. The support structure may be manufactured using, for example, cellulose acetate, and the hardness of the support structure may be controlled by varying the content of a plasticizer added during the manufacture of the support structure. Alternatively, the support structure may be manufactured by inserting a structure such as a film or tube made of the same or different material into the hollow space.

[0075] The cooling structure may be positioned downstream of the support structure. When a smoker inhales an aerosol generated by heating the medium, a hot sensation may occur, particularly in the first puff, which may cause discomfort to the smoker. The cooling structure may function as a cooling member that cools the aerosol generated by heating the medium. Accordingly, the smoker can inhale an aerosol cooled to an appropriate temperature.

[0076] As another example, a smoking article according to one embodiment of the present invention may further include a shear filter segment and a support structure in addition to the medium portion and the filter portion.

[0077] A pre-filter segment may be positioned upstream of the media portion. The pre-filter segment may serve to identify a dedicated smoking article used in an aerosol generating device. The pre-filter segment may be made of, for example, cellulose acetate. The center of the pre-filter segment may be hollow, or may be formed with microchannels that are sufficient to prevent the tobacco medium within the media portion from falling out, while still allowing an airflow path.

[0078] However, the examples described above are only examples of non-combustible smoking articles in which the present invention can be used, and are not limited to the examples described.

[0079] An aerosol generating device may include some or all of a battery, a control unit, a vaporizer, and a heater. The arrangement of these components may vary depending on the design of the aerosol generating device. In addition to the configurations described above, the aerosol generating device may further include general-purpose components.

[0080]

[0081] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples.

[0082]

[0083] 1. Production of Western-type menthol

[0084] The western-type menthol of the examples and comparative examples was manufactured by the following method.

[0085]

[0086] Example 1

[0087] First, 10 g of crystalline menthol ((1R,2S,5R)-2-isopropyl-5-methylcyclohexanol, MW 156.27, melting point 42°C) was melted at 43°C (step S1). 10 g of the melted menthol was added to 6.6 g of glycerin (weight ratio of menthol and glycerin 6:4) and mixed (step S2). The mixed liquid was stirred at 40°C for 5 minutes at a speed of 300 to 600 rpm and cooled to room temperature to produce sustained-release menthol (step S3).

[0088]

[0089] Example 2

[0090] A sustained-release menthol was prepared in the same manner as in Example 1, except that the weight ratio of menthol and glycerin was mixed to be 6.3:3.7 in step S2.

[0091]

[0092] Example 3

[0093] A sustained-release menthol was prepared in the same manner as in Example 1, except that the weight ratio of menthol and glycerin was mixed to be 8:2 in step S2.

[0094]

[0095] Comparative Example 1

[0096] A sustained-release menthol was prepared in the same manner as in Example 1, except that the weight ratio of menthol and glycerin was mixed to be 5.5:4.5 in step S2.

[0097]

[0098] Comparative Example 2

[0099] A sustained-release menthol was prepared in the same manner as in Example 1, except that the weight ratio of menthol and glycerin was mixed to be 4.9:5.1 in step S2.

[0100]

[0101] Comparative Example 3

[0102] A sustained-release menthol was prepared in the same manner as in Example 1, except that the weight ratio of menthol and glycerin was mixed to be 4.2:5.8 in step S2.

[0103]

[0104] Comparative Example 4

[0105] A sustained-release menthol was prepared in the same manner as in Example 1, except that the weight ratio of menthol and glycerin was mixed to be 4:6 in step S2.

[0106]

[0107] Comparative Example 5

[0108] A sustained-release menthol was prepared in the same manner as in Example 1, except that the weight ratio of menthol and glycerin was mixed to be 3.6:6.4 in step S2.

[0109]

[0110] Comparative Example 6

[0111] A sustained-release menthol was prepared in the same manner as in Example 1, except that the weight ratio of menthol and glycerin was mixed to be 3:7 in step S2.

[0112]

[0113] Comparative Example 7

[0114] A sustained-release menthol was prepared in the same manner as in Example 1, except that the weight ratio of menthol and glycerin was mixed to be 1.5:8.5 in step S2.

[0115]

[0116] 2. Experimental Example 1: Comparison of images of sustained-release menthol according to the weight ratio of menthol and glycerin.

[0117] Images of the western-type menthol of Example 1 and Comparative Example 4 are shown in Fig. 2. As a result, it was confirmed that Example 1 was completely solidified into a solid state, whereas Comparative Example 4 was not completely solidified into a solid state.

[0118]

[0119] 3. Experimental Example 2: Comparison of the state of sustained-release menthol according to the weight ratio of menthol and glycerin

[0120] The state of the sustained-release menthol of Examples 1 to 3 and Comparative Examples 1 to 7 was observed. At this time, the state of the sustained-release menthol was observed when the mixed liquid of menthol and glycerin was stirred at high speed during the manufacturing process and left at room temperature, and the results are shown in Table 1 below. In order to compare the state of the sustained-release menthol of Examples 1 to 3 and Comparative Examples 1 to 7, a menthol-MCT mixture was also prepared by mixing menthol with medium chain triglycerides (MCT), which is an oil used in flavor capsules of smoking products, instead of glycerin.

[0121]

[0122]

[0123]

[0124] From Examples 1 to 3 and Comparative Examples 1 to 7, it was confirmed that the state of sustained-release menthol produced by varying the menthol content can be controlled. Specifically, glycerin is originally in a liquid state at room temperature (18 to 23°C). However, even when only a small amount of menthol is added to glycerin, sustained-release menthol in a semi-solid state is irreversibly produced (Comparative Examples 6 and 7), and it was confirmed that when the weight of menthol is 60 wt% or more, the solid-state sustained-release menthol desired in the present invention is produced (Examples 1 to 3).

[0125] Meanwhile, unlike Western menthol, when MCT was mixed with menthol, a rapid change in state occurred from a liquid state to a solid state as the weight of menthol became greater than the weight of MCT.

[0126] Solid, sustained-release menthol is a powder, and can be made into granules or cylindrical blocks by adding lactose and microcellulose. Additionally, a binder can be added to enhance the solid's cohesiveness. When heat is applied to sustained-release menthol, the glycerin melts, releasing the menthol.

[0127]

[0128] From the above Experimental Examples 1 and 2, it is predicted that by using the method for manufacturing sustained-release menthol described in the claims, sustained-release menthol can be easily applied to the composition of smoking articles, and sustained-release menthol manufactured by this manufacturing method has excellent flavor retention and storability, and a smoking article containing sustained-release menthol not only has excellent flavor retention and storability, but can also continuously express flavor without loss of menthol flavor.

[0129]

[0130] Although the embodiments described above have been described with limited drawings, those skilled in the art will appreciate that various technical modifications and variations can be applied based on the above. For example, appropriate results can still be achieved even if the described techniques are performed in a different order than described, and / or components of the described systems, structures, devices, circuits, etc. are combined or combined in a different manner than described, or are replaced or substituted with other components or equivalents.

[0131]

[0132] Therefore, other implementations, other embodiments, and equivalents to the claims also fall within the scope of the claims described below.

Claims

1. Step of melting menthol (S1); Step (S2) of preparing a mixed liquid by mixing melted menthol and glycerin; and A step (S3) of preparing a solid dispersion by stirring the above mixed liquid phase; including; A method for producing sustained-release menthol, wherein the weight of the melted menthol in the above step S2 is greater than the weight of the glycerin.

2. In paragraph 1, A method for producing a western-type menthol, wherein the above step S1 is performed at a temperature of 40°C to 50°C.

3. In paragraph 1, A method for producing sustained-release menthol, wherein the weight ratio of menthol and glycerin in the mixed liquid in the above step S2 is 6:4 to 9.9:0.

1.

4. In paragraph 1, A method for producing sustained-release menthol, wherein in the above step S3, the solid dispersion is solidified by uniformly dispersing the molten menthol in the glycerin.

5. In paragraph 1, A method for producing sustained-release menthol, which further comprises a step (S4) of adding an excipient to the solid dispersion to produce a form after the above step S3.

6. In paragraph 5, A method for producing sustained-release menthol, wherein in the above step S4, the excipient comprises at least one selected from the group consisting of lactose, microcellulose, and a binder.

7. Contains a solid dispersion containing menthol and glycerin, The above solid dispersion is one in which the menthol is uniformly dispersed in the glycerin, Sustained-release menthol, wherein the weight of the menthol is greater than the weight of the glycerin.

8. In paragraph 7, The above-mentioned sustained-release menthol further comprises an excipient.

9. In paragraph 7, Sustained-release menthol, wherein the form of the above-mentioned sustained-release menthol is at least one selected from the group consisting of powder, granules, and cylindrical blocks.

10. In a smoking article including a medium, a filter, and a wrapper, At least one selected from the group consisting of the above medium, filter, and wrapper comprises a western-type menthol, The above-mentioned western menthol comprises a solid dispersion containing menthol and glycerin, The above solid dispersion is one in which the menthol is uniformly dispersed in the glycerin, A smoking article wherein the weight of the menthol is greater than the weight of the glycerin.

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