WO2007032433A1 - Procédé destiné à la production d’un matériau recyclé à base de tabac - Google Patents

Procédé destiné à la production d’un matériau recyclé à base de tabac Download PDF

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Publication number
WO2007032433A1
WO2007032433A1 PCT/JP2006/318254 JP2006318254W WO2007032433A1 WO 2007032433 A1 WO2007032433 A1 WO 2007032433A1 JP 2006318254 W JP2006318254 W JP 2006318254W WO 2007032433 A1 WO2007032433 A1 WO 2007032433A1
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Prior art keywords
extract
adsorbent
amount
tobacco material
tobacco
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PCT/JP2006/318254
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English (en)
Japanese (ja)
Inventor
Shigenobu Tatsuoka
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Japan Tobacco Inc.
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Publication of WO2007032433A1 publication Critical patent/WO2007032433A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/12—Chemical features of tobacco products or tobacco substitutes of reconstituted tobacco
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts

Definitions

  • the present invention relates to a method for producing a recycled tobacco material.
  • Tobacco materials such as natural tobacco leaves, chopped bones, bones, stems and roots contain various components such as nicotine, nitrosamines, hydrocarbons and proteins.
  • these components extracted from natural tobacco materials are applied back to the recycled tobacco web made from the extracted residue.
  • Some components of these natural tobacco materials may be desirable to eliminate the power to reduce their amount for taste or other reasons, while others may not be desirable or increased.
  • U.S. Pat. No. 5810020 discloses the removal of trosamines by liquid-liquid extraction using a large amount of crown ether.
  • Trosamine, particularly TSNA, contained in natural tobacco materials is a desirable material to remove.
  • TSNA has a structure similar to that of nicotine, which is a useful component, and it is difficult to selectively remove TSNA without removing nicotine. Therefore, in the conventional method, a regenerated tobacco material that contains a significant amount of nicotine but is substantially free of TSNA is produced using an extract obtained from natural tobacco material and a fiber component that is an extraction residue. It was difficult.
  • the present invention is a comparatively simple operation, and the extract liquid power obtained from the natural tobacco material also reduces TSNA without significantly reducing the amount of cotin, and thus contains a significant amount of nicotine.
  • an object of the present invention is to provide a method for producing a recycled tobacco material from which TSNA is substantially removed.
  • the present invention (a) natural tobacco material is extracted with an aqueous extraction solvent to obtain an extract and an extraction residue containing the components of the natural tobacco material, and (b) the extract or its concentrated solution Subjecting to an adsorptive separation operation using an adsorbent exhibiting interpolarity-reducing trosamine; (c) preparing a regenerated tobacco web using the extraction residue; and (d) an extract with reduced trosamine.
  • the manufacturing method of the regenerated tobacco material which includes adding at least one part of a concentrate to the said regenerated tobacco web is provided.
  • the adsorbent is a porous adsorbent composed of an acrylic or methacrylic resin, a porous adsorbent composed of a hydrophobic resin having a hydrophilic functional group on the surface, and a hydrophilic adsorbent having a hydrophobic functional group on the surface.
  • Porous adsorbent power made of functional resin can be selected.
  • adsorption separation can be performed by tip chromatography separation using a column packed with an adsorbent.
  • the tobacco extract or its concentrate is passed through a column to obtain an effluent, and then the water eluate is combined with the effluent through three times or less of the volume of the adsorbent packed in the column. Can be added to the regenerated tobacco web.
  • FIG. 1 is a flow diagram for explaining a method of producing a regenerated tobacco material according to an embodiment of the present invention.
  • FIG. 2A is a graph showing the elution concentrations of nicotine and total TSNA in Example 66 described in detail below.
  • FIG. 2B is a graph showing the cumulative dissolution rate of nicotine and total TSNA in Example 66.
  • FIG. 3A is a graph showing the elution concentrations of total TSNA, sugar (glucose, fructose and sucrose) and amino acids in Example 67, which will be described in detail later.
  • FIG. 3B is a graph showing the cumulative elution rates of total TSNA, sugars (glucose, fructose and sucrose) and amino acids in Example 67.
  • the method of the present invention uses an adsorbent exhibiting an intermediate polarity, and the TSNA (N ′ -Nitrosonornicotine (NNN), 4- (Methylnitrosamino)-1-(3-Pyridyl)-1-Butanone (NNK), N'--Trosoanatabine (NAT))
  • TSNA N ′ -Nitrosonornicotine
  • NNK 4- (Methylnitrosamino)-1-(3-Pyridyl)-1-Butanone
  • NAT N'--Trosoanatabine
  • FIG. 1 shows a flow diagram for explaining a method of producing a recycled tobacco material according to one embodiment of the present invention.
  • the natural tobacco material 11 and the extraction solvent 12 are mixed and stirred to subject the natural tobacco material 11 to the extraction treatment S1.
  • the natural tobacco material 11 tobacco leaves, chopped, medium bones, stems, roots, and mixtures thereof can be used.
  • an aqueous solvent can be used.
  • the aqueous extraction solvent such as water may be alkaline or acidic.
  • a mixture of water and a water-miscible organic solvent can also be used. Examples of such organic solvents are alcohols such as ethanol.
  • inorganic salts such as sodium hydroxide can be dissolved.
  • the extraction treatment S1 is usually performed at a temperature of 50 to: LOO ° C for about 5 minutes to 6 hours.
  • the obtained extraction mixture is subjected to a separation operation S2 by, for example, filtration, and divided into an extraction liquid 13 and an extraction residue 14.
  • the extract 13 contains water-soluble components in the natural tobacco material, such as nicotine and TSNA.
  • the extraction residue 14 consists essentially of fibers.
  • a regenerated tobacco web 15 is produced by a conventional method.
  • the regenerated tobacco web 15 may be partially constituted by the extraction residue 14 or may be entirely constituted by the extraction residue 14.
  • the extract 13 obtained from the separation operation S2 is concentrated by an ordinary method such as a centrifugal thin film method, or the adsorption solution operation S4 using an adsorbent having intermediate polarity without being concentrated is used.
  • the adsorption separation operation S4 can be performed, for example, by bringing the extract 13 into contact with an adsorbent having intermediate polarity.
  • An adsorbent having an intermediate polarity is generally an adsorbent having an intermediate polarity between high polarity and low polarity, and is a highly porous resin based on acrylic or methacrylic resin, or styrene.
  • Hydrophobic rosin and other hydrophobic sorbents on the surface highly porous rosin having a hydrophilic functional group such as quaternary ammonium group, dalkamine group, iminodiacetic acid group, polyamine group and tertiary amine group, or silica
  • the highly porous resin having a hydrophobic functional group such as octadecyl group on the surface of hydrophilic resin such as fat.
  • the contact between the extract 13 and the adsorbent having intermediate polarity can be performed, for example, by adding particles of the adsorbent having intermediate polarity to the extract 13 and stirring (batch type).
  • the contact between the extract 13 and the adsorbent having an intermediate polarity can also be made by passing the extract through an adsorbent bed filled with particles of an adsorbent having an intermediate polarity.
  • a so-called advanced chromatography separation method can also be used.
  • tobacco extract or its concentrate is passed through a column packed with an adsorbent, and TSNA does not contain TSNA in the column effluent, but liquid containing nicotine begins to flow out. It is a technique to collect the fraction until the start.
  • the separation target liquid is adsorbed by an adsorbent in the column, and then a solvent (for example, water) different from the separation target liquid is used as a mobile phase to separate components during elution.
  • the liquid to be separated (in the present invention, the tobacco extract or its concentrated liquid) itself is used as the mobile phase, and the components can be separated from the time when the liquid to be separated is loaded onto the column. is there. Furthermore, in normal chromatography, the separation target When the liquid load is increased, the resolution decreases, but in the advanced chromatographic separation, since the separation target liquid itself is used as the mobile phase, the mobile phase is different from the case of elution with a mobile phase such as water. Since the hydrogen ion concentration (pH) of each column is different, the resolution is rarely reduced even when a large amount of separation target liquid is loaded onto the column.
  • the tobacco extract used for separation is concentrated by a conventional method such as a centrifugal thin film method so that the concentration of soluble components is about 10 to 20% by weight. It is preferable.
  • the amount of the intermediate polar adsorbent used is preferably an amount corresponding to 50% or more of the weight of the soluble component in the extract 13. If the amount of the intermediate polar adsorbent is less than 50%, it becomes difficult to sufficiently remove TSNA in the extract.
  • the amount of the tobacco extract or its concentrate to be subjected to the separation is about 20 times or less, preferably about 12 times or less the volume of the adsorbent packed in the column.
  • Nicotine can be recovered almost completely (over 90% in total) by passing the entire amount of tobacco extract or its concentrate through the column and then passing water through the column. In that case, it is desirable to use water in an amount of about 3 times or more, preferably about 5 times or more the volume of the adsorbent packed in the column.
  • the amount of the soluble component in the extract can be determined by a freeze-drying method.
  • the extract thus separated by adsorption is separated from the intermediate polar adsorbent (used adsorbent 17) (S5).
  • This separation can be performed by filtration when the contact between the extract and the intermediate polar adsorbent is carried out by adding the intermediate polar adsorbent to the extract and stirring.
  • the contact between the extract and the intermediate polar adsorbent is carried out by passing the extract through the intermediate polar adsorbent bed, or when using advanced chromatographic separation, the extract after the adsorption treatment is Needless to say, it flows out from the intermediate polar adsorbent bed in a state separated from the intermediate polar adsorbent.
  • an eluate from water can be used in combination.
  • the adsorption-treated extract 16 obtained in this way is concentrated by a conventional method, or a part or all of it is added to the regenerated tobacco web 15 without being concentrated (S5). Is obtained. Cigarettes made using the recycled tobacco material 18 thus obtained are TSNA in smoke generated during firing is significantly reduced.
  • the amount of TSNA is calculated according to Arista's time-lapse TSNA measurement method (Official Method T-309, Determination of Nitrosamines in Whole Tobacco, made by the Department or Health, dated December 31, 1999). Measured accordingly. That is, the sample solution (tobacco extract, adsorbent treatment solution, or column effluent) was subjected to LC MSZMS for measurement.
  • the amount of nicotine was measured by a method in accordance with DIN 10373, a German standardization organization. In other words, sodium hydroxide was added to the sample solution to make it alkaline, then hexane was added and mixed, nicotine was transferred to the hexane phase, and only the hexane phase was subjected to GCZFID for measurement.
  • the amount of sugar is measured by subjecting the sample solution to LC-RI.
  • Tobacco leaf was extracted by mixing tobacco leaf (X-KLl OOg with water lOOOOmL and stirring for 1 hour at a temperature of 25 ° C. The resulting extraction mixture was filtered, and the extract and the extraction residue were filtered. Paper from the extracted residue was obtained to obtain a regenerated tobacco web.
  • methacrylic resin in the extract in the amount (%) shown in Table 1 with respect to the weight of soluble components.
  • the total TSNA amount was significantly decreased by using an adsorbent in an amount of 50% or more of the amount of soluble components in the extract, while the decrease rate of the nicotine amount was It can be seen that even if the treatment time is increased, it can be suppressed to less than 25%. In particular, if the amount of adsorbent used is equivalent to 500% of the amount of soluble components in the extract, it is obvious that the total TSNA amount is reduced by more than 90%.
  • Table 2 shows acrylic resin (trade name XAD7H P, manufactured by Rohm and Haas; average particle size: 350 to 900 ⁇ m; specific surface area: 400 m 2 Zg or more, no functional group) as an intermediate polar adsorbent
  • acrylic resin trade name XAD7H P, manufactured by Rohm and Haas; average particle size: 350 to 900 ⁇ m; specific surface area: 400 m 2 Zg or more, no functional group
  • the total TSNA amount was significantly reduced by using an adsorbent in an amount of 50% or more of the amount of soluble components in the extract. It can be seen that even if the length is increased, it can be suppressed to less than 30%.
  • the amount of adsorbent used is the extract. The amount equivalent to 500% of the amount of soluble components in the mixture is said to reduce the total TSNA amount by more than 90%.
  • Each of the adsorption-treated extracts of Examples 12 to 20 was added to a regenerated tobacco web to prepare a regenerated tobacco material.
  • styrene-based resin having iminodiacetic acid type functional group (trade name Diaion CR11 manufactured by Mitsubishi Chemical Co., Ltd .: average particle size 355 to 1180 ⁇ m) is used in the amount shown in Table 3, and shown in Table 3 The same operation as in Examples 1 to 11 was performed except that the mixture was stirred with the time extract.
  • Table 3 shows the analysis results of the total TSNA and nicotine contained in the extract (filtrate) after the adsorption treatment.
  • results shown in Table 3 While using an adsorbent in an amount of 250% or more of the amount of soluble components in the extract, the total TSNA amount is significantly reduced, while the rate of decrease in the nicotine amount is less than the treatment time. It can be seen that even if it is made longer, it can be suppressed to 35% or less.
  • the amount of adsorbent used is extracted If the amount of soluble components in the liquid is equivalent to 500%, the total TSNA amount will decrease by up to 80%.
  • Each of the adsorption-treated extracts of Examples 21 to 29 was added to a regenerated tobacco web to prepare a regenerated tobacco material.
  • a styrene-based resin having a darucamine functional group (trade name Diaion CRB02 manufactured by Mitsubishi Chemical Co., Ltd .: average particle size of 300 m or more) is used in the amount shown in Table 4, and the time extract shown in Table 4 The same operation as in Examples 1 to 11 was performed except that stirring was performed.
  • the analysis results of the total TSNA and nicotine contained in the extract (filtrate) after the adsorption treatment are also shown in Table 4.
  • Each of the adsorption-treated extracts of Examples 30 to 38 was added to a regenerated tobacco web to prepare a regenerated tobacco material.
  • styrene resin having a quaternary ammonium functional group (trade name Diaion HPA25 manufactured by Mitsubishi Chemical Co., Ltd .: average particle size of 250 ⁇ m or more) is used in the amount shown in Table 5, and in Table 5 The same operations as in Examples 1 to 11 were carried out except that the extract was stirred for the indicated time.
  • Table 5 shows the results of analysis of total TSNA and nicotine contained in the extract (filtrate) after the adsorption treatment.
  • results shown in Table 5 The use of adsorbent in an amount of 250% or more of the amount of soluble components in the extract significantly decreases the total TSNA amount, while the decrease rate of the nicotine amount decreases the processing time. It can be seen that even if it is lengthened, it can be suppressed to about 10% or less.
  • the amount of adsorbent used is If the amount of soluble components in the extract is equivalent to 500%, the total TSNA amount will decrease by 70% or more.
  • Each of the adsorption-treated extracts of Examples 39 to 47 was added to a regenerated tobacco web to prepare a regenerated tobacco material.
  • silica-based rosin having a octadecyl group (trade name Bondpak C18 manufactured by Waters Co., Ltd .: average particle size: 37 to 55 / zm) is used in the amount shown in Table 6, and the time extract shown in Table 6 is used. The same operation as in Examples 1 to 11 was performed except that stirring was performed. Table 6 shows the results of analysis of total TSNA and nicotine contained in the extract (filtrate) after adsorption treatment.
  • Each of the adsorption-treated extracts of Examples 48 to 56 was added to a regenerated tobacco web to prepare a regenerated tobacco material.
  • Example 66 Tobacco leaf was extracted by mixing tobacco leaf (X-KLl OOg with water lOOOmL at a temperature of 25 ° C and stirring for 1 hour. The resulting extraction mixture was filtered, Paper from the extracted residue was obtained to obtain a regenerated tobacco web.
  • This concentrated solution (temperature 25 ° C) was subjected to advanced chromatographic separation under the following conditions.
  • Adsorbent Methacrylic resin (trade name Diaion HP2MG manufactured by Mitsubishi Chemical Corporation; average particle size: 250 ⁇ m or more; specific surface area: 470 m 2 Zg, no functional group)
  • the concentrated extract was first applied to the column in an amount of about 14 times or less the adsorbent packed volume. Subsequently, the cotin was completely eluted with about 5 times the volume of the adsorbent filling volume. Then, TSNA was eluted with 1% acetic acid aqueous solution.
  • FIGS. 2A and 2B show the elution patterns of nicotine and total TSNA.
  • Fig. 2A is a graph plotting the concentrations of nicotine and TSNA (stock standard values) in the eluate against the amount of liquid that passed through the force ram.
  • Fig. 2B is a graph plotting the cumulative elution rates of nicotine and total TSNA against the amount of liquid passed through the column.
  • V the drift dull
  • curve a is for nicotine
  • curve b is for total TSNA.
  • Table 8 shows the amounts of nicotine and total TSNA eluted by each elution treatment, and the total amount and recovery rate of each elution treatment.
  • Extraction was performed by mixing 30 kg of tobacco raw material (mixture of lamina and medium bone of yellow and burre each) with 150 L of water and stirring for 20 to 30 minutes at a temperature of about 60 ° C.
  • the obtained extraction mixture was filtered and divided into an extract and an extraction residue. Paper from the extraction residue was obtained to obtain recycled tapaco web.
  • Adsorbent Methacrylic resin (trade name Diaion HP2MG manufactured by Mitsubishi Chemical Corporation; average particle size: 250 ⁇ m or more; specific surface area: 470 m 2 Zg, no functional group)
  • the concentrated extract was applied to the column in an amount of about 14 times or less the adsorbent packed volume. Subsequently, the cotin was completely eluted with about 5 times the volume of the adsorbent filling volume. Then, TSNA was eluted with 1% acetic acid aqueous solution.
  • FIGS. 3A and 3B show the elution patterns of nicotine, total TSNA, sugars (glucose, fructose and sucrose) and total amino acids.
  • FIG. 3A is a graph plotting the concentrations of nicotine, total TSNA, sugar (glucose, fructose and sucrose) and total amino acids (stock solution standard values) in the eluate against the amount of liquid passed through the column.
  • Figure 3B is a graph that plots the cumulative elution rates of nicotine, total TSNA, sugars (glucose, fructose, and sucrose) and amino acids against the volume of fluid that passed through the column. In both graphs, curve a is for nicotine, curve b is for total TSNA, curve c is for sugar, and curve d is for total amino acids. Is.
  • Table 9 shows the total amount of nicotine, total TSNA, sugar (glucose, fructose and sucrose) and total amino acid eluted by each elution treatment, and the total amount and recovery rate of each elution treatment. Show.
  • TSNA can be separated without significantly reducing the amount of nicotine by a relatively simple method using the extractive force obtained from the natural tobacco material. Recycled tobacco material containing a significant amount of nicotine and substantially free of TSNA can be produced.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

La présente invention concerne un procédé destiné à la production d’un matériau à base de tabac recyclé qui comprend les étapes consistant à : extraire un matériau à base de tabac naturel à l’aide d’un solvant d’extraction aqueux afin d’obtenir un extrait contenant un composant provenant du matériau à base de tabac naturel et un résidu d’extraction ; soumettre l’extrait ou une solution concentrée de l’extrait à un procédé d’adsorption/séparation à l’aide d’un adsorbant possédant une polarité neutre afin de réduire la teneur en nitrosoamine présente dans l’extrait ou la solution concentrée ; préparer une bande de tabac recyclé en se servant du résidu d’extraction ; et ajouter au moins une partie de l’extrait ou de la solution concentrée possédant une teneur en nitrosoamine réduite à la bande de tabac recyclée.
PCT/JP2006/318254 2005-09-15 2006-09-14 Procédé destiné à la production d’un matériau recyclé à base de tabac WO2007032433A1 (fr)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008090477A2 (fr) * 2007-01-26 2008-07-31 Philip Morris Products S.A. Procédés et appareil pour l'élimination sélective de constituants d'extraits aqueux de tabac
WO2011013478A1 (fr) * 2009-07-27 2011-02-03 日本たばこ産業株式会社 Procédé de production de tabac reconstitué, procédé de production de cigarette contenant le tabac reconstitué, et cigarette
JP2014501104A (ja) * 2010-12-17 2014-01-20 アール・ジエイ・レイノルズ・タバコ・カンパニー タバコ由来シロップ組成物
CN103704872A (zh) * 2012-10-08 2014-04-09 朱大恒 一种具有甜香风格的再造烟草及其用途
JP2015512257A (ja) * 2012-03-28 2015-04-27 フィリップ・モーリス・プロダクツ・ソシエテ・アノニム 液体タバコ組成物
EP2769631A4 (fr) * 2012-12-20 2015-08-19 Shanghai Juhua Science And Technology Co Ltd Procédé d'amélioration de matériaux à base de tabac et dispositif à cet effet
JP2016511006A (ja) * 2013-03-14 2016-04-14 アール・ジエイ・レイノルズ・タバコ・カンパニー タバコ由来の糖濃縮抽出物
JPWO2017183589A1 (ja) * 2016-04-22 2018-12-06 日本たばこ産業株式会社 香味源の製造方法
CN109259292A (zh) * 2018-09-13 2019-01-25 云南中烟工业有限责任公司 一种烟草烘烤香型再造烟叶及其制备方法
CN113856639A (zh) * 2021-10-19 2021-12-31 湖北中烟工业有限责任公司 一种低次烟叶固相萃取吸附剂的制备方法及其应用

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Cited By (18)

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Publication number Priority date Publication date Assignee Title
WO2008090477A2 (fr) * 2007-01-26 2008-07-31 Philip Morris Products S.A. Procédés et appareil pour l'élimination sélective de constituants d'extraits aqueux de tabac
WO2008090477A3 (fr) * 2007-01-26 2009-09-17 Philip Morris Products S.A. Procédés et appareil pour l'élimination sélective de constituants d'extraits aqueux de tabac
EA018063B1 (ru) * 2007-01-26 2013-05-30 Филип Моррис Продактс С.А. Способ удаления ионов металла из водного табачного экстракта
US9049886B2 (en) 2007-01-26 2015-06-09 Philip Morris Usa Inc. Methods and apparatus for the selective removal of constituents from aqueous tobacco extracts
WO2011013478A1 (fr) * 2009-07-27 2011-02-03 日本たばこ産業株式会社 Procédé de production de tabac reconstitué, procédé de production de cigarette contenant le tabac reconstitué, et cigarette
JP5279098B2 (ja) * 2009-07-27 2013-09-04 日本たばこ産業株式会社 シガレットの製造方法及びこの製造方法にて得られたシガレット
US8839801B2 (en) 2009-07-27 2014-09-23 Japan Tobacco Inc. Method of manufacturing cigarettes
JP2014501104A (ja) * 2010-12-17 2014-01-20 アール・ジエイ・レイノルズ・タバコ・カンパニー タバコ由来シロップ組成物
JP2015512257A (ja) * 2012-03-28 2015-04-27 フィリップ・モーリス・プロダクツ・ソシエテ・アノニム 液体タバコ組成物
CN103704872A (zh) * 2012-10-08 2014-04-09 朱大恒 一种具有甜香风格的再造烟草及其用途
EP2769631A4 (fr) * 2012-12-20 2015-08-19 Shanghai Juhua Science And Technology Co Ltd Procédé d'amélioration de matériaux à base de tabac et dispositif à cet effet
US9480283B2 (en) 2012-12-20 2016-11-01 Shanghai Juhua Science And Technology Co., Ltd. Process and apparatus for improving raw tobacco
US10098377B2 (en) 2012-12-20 2018-10-16 Shanghai Juhua Science And Technology Co., Ltd. Process and apparatus for improving raw tobacco
JP2016511006A (ja) * 2013-03-14 2016-04-14 アール・ジエイ・レイノルズ・タバコ・カンパニー タバコ由来の糖濃縮抽出物
JPWO2017183589A1 (ja) * 2016-04-22 2018-12-06 日本たばこ産業株式会社 香味源の製造方法
CN109259292A (zh) * 2018-09-13 2019-01-25 云南中烟工业有限责任公司 一种烟草烘烤香型再造烟叶及其制备方法
CN109259292B (zh) * 2018-09-13 2022-02-01 云南中烟工业有限责任公司 一种烟草烘烤香型再造烟叶及其制备方法
CN113856639A (zh) * 2021-10-19 2021-12-31 湖北中烟工业有限责任公司 一种低次烟叶固相萃取吸附剂的制备方法及其应用

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