EP4725325A1 - Tobacco material containing specific amount of cbt, method for producing same, and smoking article containing same - Google Patents

Tobacco material containing specific amount of cbt, method for producing same, and smoking article containing same

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Publication number
EP4725325A1
EP4725325A1 EP23940748.9A EP23940748A EP4725325A1 EP 4725325 A1 EP4725325 A1 EP 4725325A1 EP 23940748 A EP23940748 A EP 23940748A EP 4725325 A1 EP4725325 A1 EP 4725325A1
Authority
EP
European Patent Office
Prior art keywords
tobacco
cbt
tobacco material
weight
smoking article
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP23940748.9A
Other languages
German (de)
French (fr)
Inventor
Atsushi Nagai
Masahiro Chida
Yoshinobu SHIRAHASHI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Japan Tobacco Inc
Original Assignee
Japan Tobacco Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Japan Tobacco Inc filed Critical Japan Tobacco Inc
Publication of EP4725325A1 publication Critical patent/EP4725325A1/en
Pending legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B3/00Preparing tobacco in the factory
    • A24B3/14Forming reconstituted tobacco products, e.g. wrapper materials, sheets, imitation leaves, rods, cakes; Forms of such products
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10Chemical features of tobacco products or tobacco substitutes
    • A24B15/12Chemical features of tobacco products or tobacco substitutes of reconstituted tobacco
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10Chemical features of tobacco products or tobacco substitutes
    • A24B15/16Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/24Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/24Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241Extraction of specific substances
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/24Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241Extraction of specific substances
    • A24B15/245Nitrosamines
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/28Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/28Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/32Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by acyclic compounds
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24FSMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F40/00Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24FSMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F40/00Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
    • A24F40/20Devices using solid inhalable precursors

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Manufacture Of Tobacco Products (AREA)

Abstract

A tobacco material in which the cembratrienediol (CBT)/total nitrogen content is 0.16 or more. The tobacco material preferably comprises the CBT in an amount of 0.6% by weight or more.

Description

    TECHNICAL FIELD
  • The present invention relates to a tobacco material containing a specific amount of CBT, a method for producing the same, and a smoking article comprising the same.
  • BACKGROUND ART
  • Cembranoids are a group of natural diterpenoid compounds characterized by a 14-membered ring structure, and are widely distributed throughout the natural world. Many cembranoids from plants (coniferous trees and tobacco), insects, and marine life have been reported to date. Their bioactivity, including antimicrobial, anticancer, and anti-inflammatory effects, and their appealing structure have recently aroused considerable interest in researchers of natural products and pharmaceuticals. Nicotiana (tabacum) is a species of terrestrial plants containing the most abundant cembranoids contributing to the characteristic aroma of tobacco. The two major cembranoids of tobacco are 4S-cembranoid (1S,2E,4S,6R,7E,11E)-cembra-2,7,11-triene-4,6-diol (α-CBT) and its stereoisomer β-CBT. Interestingly, tobacco cembratrienediol is thought to have neuroprotective and anti-nicotine addiction effects by binding to nicotine acetylcholine receptors (nAChR), suggesting that tobacco has both nicotine-mediated addictive and anti-addictive physiologically active substances.
  • α- and β-CBT are the precursors of key flavor constituents in the Nicotiana genus (NPL 1 and 2). For example, α- and β-CBT are biochemically degraded and transformed into flavoring substances such as solanone and solandion (NPL 3 and 4). Solanone has garnered attention as a key constituent that imparts the flavors of carrot and licorice, and has a tea-like aroma (non-patent documents 5 through 7). The addition of solanone to tobacco is believed to enhance aroma, produce milder smoke, and significantly improve tobacco quality (NPL 8 through 10).
  • CITATION LIST NON-PATENT LITERATURE
    • NPL 1: https://www.chromatographyonline.com/view/py-gc-ms-investigation-of-pyrolysis-behaviours-and-decomposition-products-of---and--2-7-11-cembratriene-4-6-diols
    • NPL 2: AH. Martins, J. Hu, Z. Xu, C. Mu, P. Alvarez, B.D. Ford, et al., Neuroscience 291, 250-259 (2015).
    • NPL 3: K.W. Chang, W.W. Weeks, and J.A. Weybrew, Tobacco Sci. 29, 122-127 (1985).
    • NPL 4: I. Wahlberg, E. Olsson, and J.E. Berg, Progress in Flavour Precursor Studies: Analysis, Generation, Biotechnology: Proceedings of the International Conference, Würzburg, Germany, 30 September-2 October 1992 (Allured Publishing Corporation, Carol Stream, Illinois, USA, 1993), pp. 83-95.
    • NPL 5: A.W. Johnson, R.F. Severson, J. Hudson, G.R. Corner, and R.F. Arrendale, Tobacco Sci. 29, 67-72 (1985).
    • NPL 6: R.F. Severson, A.W. Johnson, and D.M. Jackson, Rec. Adv. Tobacco Sci. 11, 105-174 (1985).
    • NPL 7: R.L. Stedman, Chem. Rev. 68(2), 153-207 (1968).
    • NPL 8: M. Martens, G.A Dalen, and R. Helmut, Flavour Science and Technology (John Wiley and Sons Ltd, New York, NY, USA, 1987), pp. 101-106.
    • NPL 9: R.B. Griffith, R.R. Johnson, and A.D. Quinn. U.S. Patent, 3,174,485 (23 March, 1965 ).
    • NPL 10: K. Guanghui and Z. Hui, Chinese Agr. Sci. Bull. 12, 108-110 (2006).
    SUMMARY OF INVENTION TECHNICAL PROBLEM
  • As noted above, CBT is known to play a major role in the quality of tobacco. On the other hand, the CBT content in tobacco is usually, at most, around 6000 ppm, and attempts to use greater amounts of tobacco raw material in order to increase the CBT content in smoking articles inevitably result in a correspondingly greater content of nicotine-containing alkaloids. The inventors then came up with the idea that a high CBT/total nitrogen content ratio might enhance the distinctive flavor of tobacco while keeping alkaloid-related flavors under control. In view of the above circumstances, an object of the present invention is to provide a tobacco material in which the distinctive flavor of tobacco is enhanced while alkaloid-related flavors are kept under control.
  • SOLUTION TO PROBLEM
  • The inventors found that the above problem is solved by the following invention.
  • Aspect 1
  • A tobacco material in which the cembratrienediol (CBT)/total nitrogen content is 0.16 or more.
  • Aspect 2
  • The material according to Aspect 1, comprising said CBT in an amount of 0.6% by weight or more.
  • Aspect 3
  • The material according to Aspect 1 or 2, wherein the CBT is derived from a tobacco plant.
  • Aspect 4
  • A smoking article comprising the tobacco material according to any of Aspects 1 through 3.
  • Aspect 5
  • A method for producing the material according to any of Aspects 1 through 4, comprising:
    • a step for extracting the CBT from tobacco raw material; and
    • a step for adding the extracted CBT to a substrate
    Aspect 6
  • The method of production according to Aspect 5, wherein the substrate comprises leaf tobacco, a tobacco sheet, cut tobacco, tobacco strands, tobacco granules, or a combination thereof.
  • ADVANTAGEOUS EFFECTS OF INVENTION
  • The present invention makes it possible to provide a tobacco material in which the distinctive flavor of tobacco is enhanced while alkaloid-related flavors are kept under control.
  • BRIEF DESCRIPTION OF DRAWINGS
    • Fig. 1 shows an embodiment of a heat-not-burn smoking article.
    • Fig. 2 shows an embodiment of a heat-not-burn smoking system.
    DESCRIPTION OF EMBODIMENTS
  • As used in the present disclosure, the range "X-Y" includes X and Y as the end values.
  • 1. Tobacco material
  • The tobacco material is a material, such as a filler material or an additive, for a smoking article. A filler material is a material that can be used in tobacco filler. The filler material may be solid, such as cuttings, sheets, or strands. The additive may be a liquid that can be added to the substrate.
  • (1) CBT/total nitrogen content
  • In one embodiment, the cembratrienediol (CBT)/total nitrogen content ratio of the tobacco material is 0.16 or more. The tobacco material contains a high amount of CBT, thus enhancing the distinctive flavor of tobacco. The ratio (also referred to below as "C/N ratio") is preferably 0.19 or more, more preferably 0.20 or more, and even more preferably 1.0 or more. The upper limit of the C/N ratio is not limited but is preferably no more than 10.
  • The tobacco material preferably contains 0.6% by weight or more of CBT, and more preferably contains1.0% by weight or more of CBT, based on the weight of the material. The CBT is preferably derived from a natural material, and more preferably derived from a tobacco plant.
  • The CBT content can be determined by a known method. The content can be determined, for example, using gas chromatography. CBT is soluble in organic solvent, and samples are therefore preferably obtained via extraction using a non-polar organic solvent (such as hexane), and the organic phase is preferably analyzed by gas chromatography. The organic phase is preferably furthermore extracted using water to eliminate water-soluble components prior to analysis by gas chromatography. The conditions of gas chromatography analysis may also be based on known methods, but the analysis can be done under the following conditions, for example.
    • Column: HP-5MS (30 m×0.25 mm×0.25 µm)
    • Oven: Retention for 3 minutes at 40°C → heating at 4°C/min → retention for 20 minutes at 280°C
    • Detector: FID
    • Inlet: Split (10: 1), 270°C
    • Injection volume: 1 µL
    • Flow rate: 1 mL/minute (constant flow mode)
  • The total nitrogen content can be determined using a known method. For example, the content can be determined using the Keldahl method. For example, 0.2 g of tobacco material is weighed out, a digestion accelerator (KJELTAB) and 10 mL of concentrated sulfuric acid are then gradually added, and the contents are heated for 40 minutes to 400°C. After the reaction, the contents are diluted with water while cooled, and are rendered alkaline using sodium hydroxide. The solution is distilled using a Kjeldahl distillation device, and the distillate is trapped in a receiver and titrated with the addition of a pH indicator.
  • (2) Components [When in the form of a solid] 1) Tobacco material raw (Component (A))
  • In the present embodiment, the tobacco material preferably comprises tobacco raw material (also referred to as component (A)) and an aerosol source (also referred to as component (B)). Tobacco raw material is raw material derived from plants of the Nicotiana genus.Specific examples of component (A) include cut tobacco, tobacco fine powder, tobacco sheet, and strands, which are commonly used in this field. These may be used alone or in combination. Nicotiana tabacum is an example of leaf tobacco used in component (A). Examples of varieties that can be used include, but are not limited to, known varieties such as burley and flue-cured (yellow) varieties. One or more of these varieties of leaf tobacco can be mixed and used. A suitable blend of the above-mentioned varieties may be used in the form of a mixture to achieve the intended taste. In one embodiment, the tobacco material comprises a component (A) satisfying the C/N ratio noted above, and the tobacco material as a whole satisfies the C/N ratio noted above. In such cases, the tobacco material is composed of component (A) satisfying the C/N ratio, and a component that does not affect the C/N ratio. A method for preparing component (A) satisfying the C/N ratio is described below. In another embodiment, the tobacco material comprises a component (A), that does not satisfy the C/N ratio, and an externally added CBT, wherein the tobacco material as a whole satisfies the C/N ratio.
  • The content of component (A) in the tobacco material is preferably 70 to 95% by weight, and more preferably 85 to 95% by weight.
  • 2) Aerosol source (component (B))
  • An aerosol source (also referred to as a "component (B)") is a material that is heat-vaporized and cooled to produce an aerosol, or that is atomized to produce an aerosol. The inclusion of an aerosol source in the filler material will allow a sufficient amount of smoke to be achieved. Known aerosol sources can be used, examples of which include: polyhydric alcohols such as glycerol, vegetable glycerol, and propylene glycol (PG); and triethyl citrate (TEC) and triacetin. The amount of the aerosol source is preferably 3 to 30% by weight, and more preferably 5 to 15% by weight, in the tobacco material. An amount of aerosol source over the upper limit may result in tobacco segment staining, for example, and an amount under the lower limit may result in a loss of smoke intensity.
  • 3) Non-tobacco flavoring agent (component (C))
  • The tobacco material can furthermore comprise a non-tobacco flavoring agent (also referred to as "component (C)"). Non-tobacco flavoring agents are flavoring agents that are not derived from tobacco. Examples include flavoring, agents for providing a cooling sensation, and combinations thereof. Known flavoring and cooling agents can be used.
  • In particular, the following can be used, either alone or in combination, as flavoring: acetanisole, acetophenone, acetylpyrazine, 2-acetylthiazole, alfalfa extract, amyl alcohol, amyl butyrate, trans-anethole, star anise oil, apple juice, balsam of Peru oil, beeswax absolute, benzaldehyde, benzoin resinoid, benzyl alcohol, benzyl benzoate, benzyl phenylacetate, benzyl propionate, 2,3-butanedione, 2-butanol, butyl butyrate, butyric acid, caramel, cardamom oil, carob absolute, β-carotene, carrot juice, L-carvone, β-caryophyllene, cassia bark oil, cedarwood oil, celery seed oil, chamomile oil, cinnamaldehyde, cinnamic acid, cinnamyl alcohol, cinnamyl cinnamate, citronella oil, DL-citronellol, clary sage extract, cocoa, coffee, cognac oil, coriander oil, cuminaldehyde, davana oil, δ-decalactone, γ-decalactone, decanoic acid, dill herb oil, 3,4-dimethyl-1,2-cyclopentanedione, 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, 3,7-dimethyl-6-octenoic acid, 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, ethyl 2-methylbutyrate, ethyl acetate, ethyl butyrate, ethyl hexanoate, ethyl isovalerate, ethyl lactate, ethyl laurate, ethyl levulinate, ethyl maltol, ethyl octanoate, ethyl oleate, ethyl palmitate, ethyl phenylacetate, ethyl propionate, ethyl stearate, ethyl valerate, ethyl vanillin, ethyl vanillin glucoside, 2-ethyl-3,(5 or 6)-dimethylpyrazine, 5-ethyl-3-hydroxy-4-methyl-2-(5H)-furanone, 2-ethyl-3-methylpyrazine, eucalyptol, fenugreek absolute, genet absolute, gentian root infusion, geraniol, geranyl acetate, grape juice, guaiacol, guava extract, γ-heptalactone, γ-hexalactone, hexanoic acid, cis-3-hexen-1-ol, hexyl acetate, hexyl alcohol, hexyl phenylacetate, honey, 4-hydroxy-3-pentenoic acid lactone, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-2-cyclohexen-1-one, 4-(para-hydroxyphenyl)-2-butanone, sodium 4-hydroxyundecanoate, immortelle absolute, β-ionone, isoamyl acetate, isoamyl butyrate, isoamyl phenylacetate, isobutyl acetate, isobutyl phenylacetate, jasmine absolute, kola nut tincture, labdanum oil, lemon oil terpeneless, glycyrrhiza extract, linalool, linalyl acetate, lovage root oil, maltol, maple syrup, menthol, menthone, L-menthyl acetate, para-methoxy benzaldehyde, methyl-2-pyrrolyl ketone, methyl anthranilate, methyl phenylacetate, methyl salicylate, 4'-methylacetophenone, methylcyclopentenolone, 3-methylvaleric acid, mimosa absolute, molasses, myristic acid, nerol, nerolidol, γ-nonalactone, nutmeg oil, δ-octalactone, octanal, octanoic acid, orange flower oil, orange oil, orris root oil, palmitic acid, ω-pentadecalactone, peppermint oil, petitgrain Paraguay, phenethyl alcohol, phenethyl phenylacetate, phenylacetic acid, piperonal, plum extract, propenyl guaethol, propyl acetate, 3-propylidene phthalide, prune juice, pyruvic acid, raisin extract, rose oil, rum, sage oil, sandalwood oil, spearmint oil, styrax absolute, marigold oil, tea distillate, α-terpineol, terpinyl acetate, 5,6,7,8-tetrahydroquinoxaline, 1,5,5,9-tetramethyl-13-oxacyclo(8.3.0.0(4.9))tridecane, 2,3,5,6-tetramethylpyrazine, thyme oil, tomato extract, 2-tridecanone, triethyl citrate, 4-(2,6,6-trimethyl-1-cyclohexenyl)2-buten-4-one, 2,6,6-trimethyl-2-cyclohexene-1,4-dione, 4-(2,6,6-trimethyl-1,3-cyclohexadienyl)-2-buten-4-one, 2,3,5-trimethylpyrazine, γ-undecalactone, γ-valerolactone, vanilla extract, vanillin, veratric aldehyde, violet leaf absolute, N-ethyl-p-menthane-3-carboxamide (WS-3), and ethyl-2-(p-menthane-3-carboxamide) acetate (WS-5).
  • 4) Non-tobacco material (component (E))
  • The tobacco material may comprise a non-tobacco material (also referred to as "component (E)"). The non-tobacco material may be a cellulose derivative such as cellulose fiber or carboxymethylcellulose. The non-tobacco material is preferably used while mixed with component (A).
  • [When in the form of a liquid] 1) Solvent or dispersion medium (component (F))
  • In the present embodiment, the tobacco material preferably comprises a solvent or a dispersion medium (also referred to as "component (F)"). Alcohols such as ethanol are preferred as solvents. The amount can also be adjusted, as appropriate, to a suitable viscosity but, in one embodiment, can be 70 to 95% by weight in the tobacco material. In the present embodiment, the tobacco material may also include, as needed, components A through E noted above, and in particular components (B) or (C).
  • 2. Production Method
  • The tobacco material is preferably produced by the following methods.
  • (1) Method 1
  • The method comprises the following steps.
  • 1-1) CBT is prepared. 1-2) The CBT is added to a substrate.
  • Step 1-1 can be carried out by extracting tobacco raw material material (such as leaf tobacco) using an organic solvent. Specifically, tobacco plant-derived CBT can be prepared by this step. Examples of organic solvents include non-polar organic solvents; hexane can preferably be used. The extraction temperature is not limited but can be 20 to 50°C. The amount of organic solvent can be 5 to 20 times the weight of the tobacco raw material. The duration of extraction can be adjusted, as appropriate, but can be about 0.5 to 2 hours, for example. Components other than CBT are furthermore preferably removed from the organic phase that is obtained through the extraction. Specifically, the organic phase is preferably extracted using water. This step will allow nitrogen-containing compounds (alkaloids such as nicotine) to be removed.
  • Step 1-2 can be carried, for example, by adding the CBT-containing solution or dispersion that has been obtained in the above step to the substrate, or by impregnating the substrate with the CBT-containing solution or dispersion. The amount of CBT is adjusted, as appropriate, to the above C/N ratio. The substrate is preferably component (A) noted above. The form of the substrate may be, but is not limited to, leaf tobacco, tobacco sheets, cut tobacco, tobacco strands, or tobacco granules. The substrate may also be a mixture of tobacco raw material (component (A)) and a non-tobacco material. In such cases, a solid tobacco material can be prepared. The CBT-containing liquid obtained in step 1-1 can also used as such in the form of a liquid tobacco material when the C/N ratio is within the above range, or can be used in the form of a liquid tobacco material by adjusting the C/N ratio to within the above range.
  • (2) Method 2
  • The method comprises a step for removing nitrogen-containing compounds from the tobacco raw material. Specifically, the method comprises the following steps:
    • 2-1) The tobacco raw material is extracted using an organic solvent, and is separated into an organic phase 1 and residue 1.
    • 2-2) The organic solvent is removed from the organic phase 1 to obtain a concentrate 2.
    • 2-3) The residue 1 is extracted using water, and is separated into an aqueous phase 3 and residue 3.
    • 2-4) Nitrogen-containing compounds (such as alkaloids) are removed from the aqueous phase 3, and the water is then removed to obtain a concentrate 4.
    • 2-5) The concentrate 2 and concentrate 4 are added to the residue 3.
  • Steps 2-1 and 2-2 can be carried out in the same manner as Step 1-1. The concentrate 2 contains CBT-containing organic compounds.
  • In Step 2-3, water is preferably used in an amount 10 to 30 times the weight of the residue 1. The extraction temperature can be 20 to 40°C. The aqueous phase 3 contains nitrogen-containing compounds (alkaloids such as nicotine). The method for removing the nitrogen-containing compounds from the aqueous phase 3 is not limited, but a strongly acidic cation-exchange resin can be used, for example. As nitrogen-containing compounds are trapped by the strongly acidic cation exchange resin, the amount of nitrogen-containing compounds in the aqueous phase 3 is reduced, specifically, the total amount of nitrogen is reduced. The concentrate 4 (obtained upon the removal of water from the aqueous phase 3 from which nitrogen-containing compounds have been removed) includes active ingredients other than the nitrogen-containing compounds.
  • In Step 2-5, the concentrate 2 and concentrate 4 are added to the residue 3, making it possible to obtain tobacco raw material in which the CBT content is nearly the same as, but the total nitrogen content is lower than, in the raw material. The components noted above may be added, as needed, to the tobacco material.
  • 3. Application
  • The tobacco material is suitable for smoking articles. For example, the tobacco material, when in the form of cuttings, sheets, or strands is useful as tobacco filler for smoking articles. The tobacco material, when in the form of a liquid, is also useful as an additive for a member of a smoking article. Examples of members to which additives are added include non-tobacco cuttings, non-tobacco sheets, non-tobacco strands, wrappers, and filters. Examples of methods for the addition thereof include, but are not limited to, impregnation, spraying, and application. These members to which additives are added can also be a tobacco material of the present embodiment.
  • The tobacco material is particularly suitable for combusted smoking articles or heat-not-burn smoking articles, and is especially suitable for heat-not-burn smoking articles. A heat-not-burn smoking article is described below in typical typical applications.
  • Fig. 1 shows an embodiment of a heat-not-burn smoking article. As shown in drawing, the heat-not-burn smoking article 20 comprises: a tobacco segment 20A; a cylindrical cooling portion 20B having a perforation in the perimeter; and a filter portion 20C. The heat-not-burn smoking article 20 may comprise members other than these. The axial length of the heat-not-burn smoking article 20 is not particularly limited, but is preferably 40 mm to 90 mm, more preferably 50 mm to 75 mm, and even more preferably 50 mm to 60 mm. The circumferential length of the heat-not-burn smoking article 20 is also preferably 16 mm to 25 mm, more preferably 20 mm to 24 mm, and even more preferably 21 mm to 23 mm. In an exemplary mode that may be cited, the length of the tobacco segment 20A is 20 mm, the length of the cooling portion 20B is 20 mm, and the length of the filter portion 20C is 7 mm. The lengths of the individual members can be modified as appropriate, depending on manufacturability and required quality, etc. Fig. 1 shows an embodiment in which a first segment 25 is disposed, but a second segment 26 alone may be disposed, without a first segment being disposed, downstream of the cooling portion 20B.
  • 1) Tobacco segment 20A
  • The tobacco filler 21 in the tobacco segment 20A comprises a tobacco material having the predetermined C/N ratio. The method for packing the tobacco filler 21 inside the wrapper 22 is not particularly limited but, for example, the tobacco filler 21 may be enclosed inside the wrapper 22, or the tobacco filler 21 may be packed inside a cylindrically shaped wrapper 22. Rectangularly shaped tobacco filler (longer in the longitudinal direction) may be packed in such a way that the longitudinal direction of the tobacco filler is randomly oriented in any direction in the wrapper 22, or may be packed while oriented in the axial direction, or a direction perpendicular thereto, of the tobacco segment 20A. The tobacco segment 20A is heated, so that the tobacco component, aerosol source, and water that are included in the tobacco filler 21 are vaporized and are ready to be inhaled.
  • 2) Cooling portion 20B
  • The cooling portion 20B is preferably formed by a cylindrical member. The cylindrical member may be a paper tube 23 obtained by processing cardboard into a cylindrical shape, for example. Furthermore, the cooling portion 20B may also be formed by a sheet of a thin material that is creased and then pleated, gathered, or folded to form channels. Examples of such materials that can be used include sheet materials selected from the group consisting of polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, polylactic acid, cellulose acetate, and aluminum foil. The total surface area of the cooling portion 20B is prepared, as appropriate, taking cooling efficiency into account, and may for example be 300-1000 mm2/mm. The cooling portion 20B is preferably provided with a perforation 24. The perforation 24 allows external air to be introduced into the cooling portion 20B during drawing. As a result, the aerosol vaporized component generated by heating of the tobacco segment 20A is liquefied because it comes into contact with the external air so that the temperature thereof decreases, and an aerosol is formed. The diameter of the perforation 24 (length across) is not particularly limited, but may be 0.5 mm to 1.5 mm, for example. The number of perforations 24 is not particularly limited, and may be one or more. Multiple perforations 24 may be provided on the circumference of the cooling portion 20B, for example.
  • The cooling portion 20B may be formed into a rod shape having an axial length of 7-28 mm, for example. The axial length of the cooling portion 20B may be 18 mm, for example. The cooling portion 20B has a substantially circular axial cross-sectional shape, which can be 5 to 10 mm in diameter. The cooling portion can be approximately 7 mm in diameter, for example.
  • 3) Filter portion 20C
  • The configuration of the filter portion 20C is not particularly limited, but may be composed of one or more filling layers. The outside of the filling layer may be wrapped with a single or multiple wrapping papers. The airflow resistance of the filter portion 20C may be modified, as appropriate, depending on, for example, the amount and material of the filler with which the filter portion 20C is filled. For example, when the filter filling material is cellulose acetate fibers, an increase in the amount of cellulose acetate fibers with which the filter portion 20C is filled can cause increased airflow resistance. When the filter filler is cellulose acetate fibers, the packing density of cellulose acetate fibers may be 0.13 to 0.18 g/cm3. The airflow resistance is a value determined by means of an airflow resistance analyzer (trade name: SODIMAX, manufactured by SODIM).
  • There is no particular limitation as to the circumferential length of the filter portion 20C, but it is preferably 16-25 mm, more preferably 20-24 mm, and even more preferably 21-23 mm. The filter portion 20C can have an axial (horizontal direction in Fig. 1) length of 4 to 10 mm, which can be selected so as to result in an airflow resistance of 15 to 60 mmH2O per segment. The axial length of the filter portion 20C is preferably 5 to 9 mm, and more preferably 6 to 8 mm. The cross-sectional shape of the filter portion 20C is not particularly limited, but may be circular, elliptical, or polygonal, for example. Flavor-containing destructible capsules, flavor beads, and flavors can also be directly added to the filter portion 20C.
  • The filter portion 20C may comprise a center hole portion as the first segment 25. The center hole portion may comprise a first filling layer 25a having one or more hollow portions, and an inner plug wrapper (inside wrapping paper) 25b that covers said filling layer. The center hole portion has the function of strengthening a mouthpiece portion. The shape of the center hole portion may be retained by means of thermoforming, without an inner plug wrapper 25b being provided. The first filling layer 25a may be, for example, a rod having an inside diameter of φ5.0 mm to φ1.0 mm, in which cellulose acetate fibers have been packed to a high density, and to which a triacetin-containing plasticizer has been added, in an amount of 6 to 20% by weight relative to the weight of the cellulose acetate, and cured. Since the first filling layer 25a has a high fiber packing density, air or an aerosol will flow only through the hollow portion during inhalation, with virtually none flowing through the first filling layer 25a. The first filling layer 25a inside the center hole portion is a fiber filling layer, and the user will therefore experience little discomfort when touching the outside during use. The filter portion 20C may comprise a second segment 26. The second segment 26 comprises a second filling layer 26a and an inner plug wrapper (inside wrapping paper) 26b that covers said filling layer.
  • The first filling layer 25a and the second filling layer 26a are joined by an outer plug wrapper (outside wrapping paper) 27. The outer plug wrapper 27 may be cylindrical paper, for example. The tobacco segment 20A, cooling portion 20B, and the joined first filling layer 25 and second filling layer 26 can be joined by means of mouthpiece lining paper 28. These connections may be formed, for example, by coating an inside surface of the mouthpiece lining paper 28 with a glue such as a vinyl acetate-based glue, and wrapping the abovementioned three members. These members may also be connected by multiple separate connections with multiple lining papers.
  • The combination of a heat-not-burn smoking article and a heating device for generating an aerosol is, in particular, referred to as a heat-not-burn smoking system. An example of such a system is shown in Fig. 2. As shown in the figure, the heat-not-burn smoking system comprises a heat-not-burn smoking article 20 and a heating device 10 which heats the smoking segment 20A from the outside.
  • The heating device 10 comprises a body 11, a heater 12, a metal tube 13, a battery unit 14, and a control unit 15. The body 11 has a cylindrical recess 16, where the heater 12 and metal tube 13 are disposed at positions facing the smoking segment 20A which is inserted into the recess 16. The heater 12 can be a heater employing electrical resistance, where heating by the heater 12 is effected by the supply of electrical power from the battery unit 14 per commands from the control unit 15, which controls the temperature. Heat emitted from the heater 12 is transferred through the highly thermoconductive metal tube 13 to the tobacco segment 20A. The figure depicts an embodiment in which the heating device 10 heats the tobacco segment 20A from the outside, but the segment may also be heated from the inside. The heating temperature of the heating device 10 is not particularly limited, but is preferably 400°C or below, more preferably 150 to 400°C, and even more preferably 200 to 350°C. The heating temperature refers to the temperature of the heater of the heating device 10. A susceptor can also be disposed inside the tobacco segment 20A in order to heat the tobacco segment 20A by an IH method.
  • Modes of implementation are listed below.
  • Aspect 1
  • A tobacco material in which the cembratrienediol (CBT)/total nitrogen content is 0.16 or more.
  • Aspect 2
  • The material according to Aspect 1, comprising said CBT in an amount of 0.6% by weight or more.
  • Aspect 3
  • The material according to Aspect 1 or 2, wherein the CBT is derived from a tobacco plant.
  • Aspect 4
  • A smoking article comprising the tobacco material according to any of Aspects 1 through 3.
  • Aspect 5
  • A method for producing the material according to any of Aspects 1 through 4, comprising:
    • a step for extracting the CBT from tobacco raw material; and
    • a step for adding the extracted CBT to a substrate
    Aspect 6
  • The method of production according to Aspect 5, wherein the substrate comprises leaf tobacco, a tobacco sheet, cut tobacco, tobacco strands, tobacco granules, or a combination thereof.
  • EXAMPLES COMPARATIVE EXAMPLE 1
  • Varieties of leaf having a CBT content of 1000 to 4500 ppm and a total nitrogen content of 1.9 to 4.1% by weight were prepared. Glycerol was added to each to produce tobacco materials. The glycerol content in the tobacco materials was 10% by weight. The CBT/total nitrogen content in the tobacco materials was 0.048 to 0.136.
  • Example 1 (external addition of CBT)
  • Hexane was added, in an amount 10 times by weight, to dried burley variety tobacco powder, the contents were stirred for 1 hour at room temperature and were then allowed to stand at room temperature, and the solution and extract residue were separated. 0.1% by weight sulfuric acid and 10% by weight sodium chloride aqueous solutions were added to and mixed with the hexane solution, which was separated off. The amounts of the sulfuric acid and sodium chloride aqueous solutions were the same as that of the hexane solution. The hexane solution obtained via the above separation was dried over sodium sulfate, and was concentrated to dryness in a reduced pressure atmosphere. Ethanol was added to the dry material, the contents were ultrasonically dispersed, and the solids were separated from the liquid to obtain a concentrated ethanol solution of CBT. The solution was sprayed onto dried flue-cured (yellow) leaf tobacco, and glycerol was mixed therein to obtain tobacco material. In the tobacco material, the glycerol content was 10% by weight, the CBT content was 8519 ppm, and the total nitrogen content was 3.5% by weight. Specifically, the CBT/total nitrogen content was 0.244.
  • Example 2 (external addition of CBT)
  • Hexane was added, in an amount 10 times by weight, to dried burley variety tobacco powder, the contents were stirred for 1 hour at room temperature and were then allowed to stand at room temperature, and the solution and extract residue were separated. 0.1% by weight sulfuric acid and 10% by weight sodium chloride aqueous solutions were added to and mixed with the resulting solution, which was separated off. The amounts of the sulfuric acid and sodium chloride aqueous solutions were the same as that of the hexane solution. The hexane solution obtained via the above separation was dried over sodium sulfate, and was concentrated in a reduced pressure atmosphere. Crudely purified CBT was obtained via silica gel chromatography (developing solvent: methanol:ethyl acetate=3:1). An ethanol solution of the crudely purified CBT mixture was prepared, the solution was sprayed onto dried burley variety leaf tobacco, and glycerol was mixed therein to obtain tobacco material. In the tobacco material, the glycerol content was 10% by weight, the CBT content was 9112 ppm, and the total nitrogen content was 4.7% by weight. Specifically, the CBT/total nitrogen content was 0.194.
  • Example 3 (no CBT added, reduced N content)
  • Hexane was used, in an amount of 10 times by weight, to impregnate dried flue-cured (yellow) leaf tobacco, and the solution and residue X were separated. 0.1% sulfuric acid and 10% sodium chloride aqueous solutions were added to and mixed with the resulting solution, which was separated off. The amounts of the sulfuric acid and sodium chloride aqueous solutions were the same as that of the hexane solution. The hexane solution obtained via the above separation was dried over sodium sulfate, and was concentrated in a reduced pressure atmosphere to obtain concentrate H of the hexane solution.
  • The residue X was dried to remove the hexane, and was extracted using water in an amount 20 times the weight thereof. The resulting aqueous extract and the residue Y were separated. Strongly acidic cation exchange resin (degree of cross-linking: 8%; mesh: 200 to 400) was added to the aqueous extract, the contents were stirred, the resin was then removed, and the aqueous extract was concentrated in a reduced pressure atmosphere to obtain the concentrate W.
  • The concentrate H and concentrate W were each sprayed back onto the residue X, and glycerol was furthermore mixed therein to obtain tobacco material. In the tobacco material, the glycerol content was 10% by weight, the CBT content was 1084 ppm, and the total nitrogen content was 0.6% by weight. Specifically, the CBT/total nitrogen content was 0.168.
  • Example 4 (no CBT added, reduced N content)
  • Tobacco material was prepared in the same manner as Example 3, except that dried burley variety leaf tobacco was used. In the tobacco material, the glycerol content was 10% by weight, the CBT content was 1505 ppm, and the total nitrogen content was 0.6% by weight. Specifically, the CBT/total nitrogen content was 0.245.
  • Example 5 (external addition of CBT, reduced N content)
  • Water was added, in an amount 20 times by weight, to dried burley variety leaf tobacco, and the contents were gently stirred and extracted at room temperature. The liquid extract and residue were separated, strongly acidic cation exchange resin (degree of cross-linking: 8%; mesh: 200 to 400) was added to the liquid extract, the contents were stirred, the resin was then removed, and the liquid extract was concentrated in a reduced pressure atmosphere. The liquid concentrate was added back to the extract residue.
  • A solution containing purified CBT was separately prepared. The solution, in an amount corresponding to a CBT content of 6000 ppm, was added to the extract residue to obtain tobacco material. In the tobacco material, the CBT content was 7800 ppm, and the total nitrogen content was 0.6% by weight. Specifically, the CBT/total nitrogen content was 1.25.
  • Example 6 (non-tobacco material mixed in)
  • A concentrated ethanol solution of CBT was obtained in the same manner as Example 1.
  • Tobacco powder consisting of flue-dried (yellow) and burley varieties was mixed with cellulose fibers, carboxymethylcellulose, glycerol, and the concentrated ethanol solution of CBT, and water was furthermore added and kneaded therein. The kneaded product was laminated to obtain tobacco material in the form of a sheet. In the tobacco material, the CBT content was 8519 ppm, and the total nitrogen content was 3.5% by weight. Specifically, the CBT/total nitrogen content was 1.31.
  • Example 7
  • The tobacco segment shown in Fig. 1 was prepared from the tobacco materials obtained in the comparative example and Examples 1 through 6. Heat-not-burn smoking articles comprising the tobacco segment were then produced, and were assessed via a smoking test by a panel of four experts. Smoking volume and mouth feel during the smoking tests were assessed as assessment factors on a 7-point scale. The higher the smoke volume score/mouth feel score, the more desirable the organoleptic characteristics. [Table 1]
    CBT (ppm) (A) Total nitrogen (%) (B) (A)/(B) Smoke volume (J) Mouth feel (K) (J)/(K)
    Comparative Example 1 2517 4.1% 0.061 2.75 4.25 0.65
    Comparative Example 2 1112 2.1% 0.052 2.75 3.25 0.85
    Comparative Example 3 1529 3.2% 0.048 2.75 3.25 0.85
    Comparative Example 4 1911 3.3% 0.058 2.50 3.75 0.67
    Comparative Example 5 4505 3.3% 0.136 3.50 4.00 0.88
    Comparative Example 6 1084 1.9% 0.056 1.75 2.00 0.88
    Comparative Example 7 3033 2.9% 0.104 3.50 3.50 1.00
    Example 1 8519 3.5% 0.244 5.75 2.50 2.30
    Example 2 9112 4.7% 0.194 5.75 2.50 2.30
    Example 3 1084 0.6% 0.168 4.00 2.25 1.78
    Example 4 1505 0.6% 0.245 4.25 2.50 1.70
    Example 5 7033 0.6% 1.246 5.00 2.25 2.22
    Example 6 8033 0.6% 1.310 4.25 1.75 2.43
  • It is evident that Examples 1 through 6 resulted in tobacco materials in which the distinctive flavor of tobacco was enhanced while alkaloid-related flavors were kept under control.
  • REFERENCE SIGNS LIST
    • 10 Heating device
    • 11 Body
    • 12 Heater
    • 13 Metal tube
    • 14 Battery unit
    • 15 Control unit
    • 16 Recess
    • 17 Ventilation hole
    • 20 Heat-not-burn smoking article
    • 20A Tobacco segment
    • 20B Cooling portion
    • 20C Filter portion
    • 21 Tobacco filler
    • 22 Wrapping paper
    • 23 Paper tube
    • 24 Perforation
    • 25 First segment
    • 25a First filling layer
    • 25b Inner plug wrapper
    • 26 Second segment
    • 26a Second filling layer
    • 26b Inner plug wrapper
    • 27 Outer plug wrapper
    • 28 Lining paper

Claims (6)

  1. A tobacco material in which the cembratrienediol (CBT)/total nitrogen content is 0.16 or more.
  2. The material according to Claim 1, comprising said CBT in an amount of 0.6% by weight or more.
  3. The material according to Claim 1 or 2, wherein the CBT is derived from a tobacco plant.
  4. A smoking article comprising the tobacco material according to any of Claims 1 through 3.
  5. A method for producing the material according to any of Claims 1 through 4, comprising:
    a step for extracting the CBT from tobacco raw material; and
    a step for adding the extracted CBT to a substrate.
  6. The method of production according to Claim 5, wherein the substrate comprises leaf tobacco, a tobacco sheet, cut tobacco, tobacco strands, tobacco granules, or a combination thereof.
EP23940748.9A 2023-06-09 2023-06-09 Tobacco material containing specific amount of cbt, method for producing same, and smoking article containing same Pending EP4725325A1 (en)

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US3174485A (en) 1963-05-23 1965-03-23 Brown & Williamson Tobacco Corp Organoleptically improved tobacco product
US6508254B1 (en) * 2000-07-07 2003-01-21 Brown & Williamson Tobacco Corporation Reduced protein reconstituted tobacco and method of making same
EP4268619A4 (en) * 2020-12-24 2024-12-18 Japan Tobacco Inc. Tobacco composition, tobacco-containing segment, non-combustion heating-type flavor inhaler, and non-combustion heating-type flavor inhalation system

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