EP2818059B1 - Manufacturing method for chewing tobacco material, and chewing tobacco material - Google Patents

Manufacturing method for chewing tobacco material, and chewing tobacco material Download PDF

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Publication number
EP2818059B1
EP2818059B1 EP13752001.1A EP13752001A EP2818059B1 EP 2818059 B1 EP2818059 B1 EP 2818059B1 EP 13752001 A EP13752001 A EP 13752001A EP 2818059 B1 EP2818059 B1 EP 2818059B1
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EP
European Patent Office
Prior art keywords
tobacco
tobacco material
oral
raw material
temperature
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Active
Application number
EP13752001.1A
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German (de)
French (fr)
Other versions
EP2818059A4 (en
EP2818059A1 (en
Inventor
Michinori Yokoi
Masashi FURUKOSHI
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Japan Tobacco Inc
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Japan Tobacco Inc
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Publication of EP2818059A4 publication Critical patent/EP2818059A4/en
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Classifications

    • 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
    • A24B15/183Treatment of tobacco products or tobacco substitutes sterilization, preservation or biological decontamination
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B13/00Tobacco for pipes, for cigars, e.g. cigar inserts, or for cigarettes; Chewing tobacco; Snuff
    • 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
    • A24B15/302Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by natural substances obtained from animals or plants

Definitions

  • the present invention relates to a method for producing an oral tobacco material, and an oral tobacco material. More specifically, the present invention relates to a method for producing an oral tobacco material having a reduced content of tobacco-specific nitrosamine, and an oral tobacco material obtained by that production method.
  • the oral tobacco product contains an oral tobacco material such as powdered tobacco in a water-permeable pouch. People insert such an oral tobacco product between a lip and a gum in a mouth, and enjoy the taste and flavor of the powdered tobacco (see, for example, Patent Document 1).
  • the oral tobacco material used in such an oral tobacco product contains various components such as nicotine, nitrosamines (including tobacco-specific nitrosamine), hydrocarbons, and proteins, similar to a general tobacco material for a cigarette.
  • these components there are some components which desirably are not removed or are increased in terms of smoking taste or other reasons; whereas, there are also some components whose amounts are desirably decreased. It is desired to decrease the amount of the tobacco-specific nitrosamine.
  • Patent Document 1 U.S. Patent Application Publication No. 2007/062549 US-A-2011048434 discloses a thermal treatment process for tobacco materials.
  • the tobacco materials are smokeless tobacco.
  • the thermal treatment is carried out at a temperature of above 80°C and preferably below 140°C and the pH is maintained below 8 during the heat treatment.
  • Additives are incorporated to the tobacco material before the heat treatment and include acidic compounds, citric acid, malic acid, glutaric acid, dicarboxylic acids, and the combination thereof.
  • the object of the present invention is to provide a method for producing an oral tobacco material having a reduced content of tobacco-specific nitrosamine (TSNA).
  • TSNA tobacco-specific nitrosamine
  • an oral tobacco material which is obtained by the method for producing an oral tobacco material according to the present invention.
  • the oral tobacco material produced according to the present invention shows a significantly reduced TSNA content.
  • a dry oral tobacco material having a pH of 8 or less is used as a raw material.
  • a dry oral tobacco material having a pH of 4 or more is usually used as the raw material.
  • the pH of a dry tobacco material refers to a value obtained by adding 20 to 100 g of distilled water (corresponding to 10 times the amount of the tobacco material) to 2 to 10 g of the tobacco material; shaking the mixture of the water and the tobacco material at 200 rpm at room temperature for 10 minutes; allowing the resulting mixture to stand for 5 minutes; and then measuring the pH of an extract obtained therefrom with a pH meter (IQ 240 manufactured by IQ Scientific Instruments Inc.).
  • the tobacco raw material includes a dry oral tobacco material which originally has a pH of 8 or less, and a material obtained by adding an acidic substance to a dry oral tobacco material having a pH of more than 8 to adjust the pH to 8 or less.
  • the former, the dry oral tobacco material which originally has a pH of 8 or less may include flue-cured tobacco, burley tobacco, dark air-cured tobacco, dark fire-cured tobacco, air-cured tobacco by early-dehydrating, sun-cured tobacco, oriental tobacco, and the like.
  • the dry oral tobacco material having a pH of more than 8 may include a part of burley tobacco, dark air-cured tobacco, air-cured tobacco, and the like.
  • an organic acid such as citric acid, ascorbic acid, acetic acid, lactic acid, malic acid, tartaric acid, or succinic acid may be used.
  • a dry oral tobacco material exhibiting acidity i.e., a pH of less than 7 (for example, flue-cured tobacco, burley tobacco, dark air-cured tobacco, dark fire-cured tobacco, air-cured tobacco by early-dehydrating, sun-cured tobacco or oriental tobacco) may also be used, instead of the organic acid.
  • the dry oral tobacco material exhibiting acidity is used as the acidic substance, the amount thereof is preferably 100% by weight or less with respect to the raw material.
  • TSNA typically includes N'-nitrosonornicotine (NNN), 4-(methylnitrosoamino)-1-(3-pyridyl)-1-butanone (NNK) and N'-nitrosoanatabine (NAT).
  • NNN N'-nitrosonornicotine
  • NNK 4-(methylnitrosoamino)-1-(3-pyridyl)-1-butanone
  • NAT N'-nitrosoanatabine
  • the antioxidant includes epigallocatechin gallate, ascorbic acid, green tea extract. Ascorbic acid is also the acidic substance for adjusting the pH, as described above; and it may be used as the antioxidant in combination with another acidic substance, or may be used alone to serve both as the antioxidant and the acidic substance.
  • the antioxidant is added preferably in an amount of 1 to 100 parts by weight based on 100 parts by weight of the tobacco raw material.
  • the tobacco raw material to which the antioxidant has been added is heated at a temperature of 80°C or higher.
  • the heating temperature is usually 130°C or lower.
  • the heating time is usually from 10 minutes to 30 minutes.
  • the tobacco raw material is put in a closed heating container (such as a cylindrical one) having a jacket at the outer side thereof and equipped with an introduction pipe and an exhaust pipe of heated steam, and heated steam is directly blown into the tobacco raw material through the introduction pipe, while the heated steam is circulated in the jacket, whereby the tobacco material can be heated at the same temperature as that of the heated steam.
  • a closed heating container such as a cylindrical one
  • heated steam is directly blown into the tobacco raw material through the introduction pipe, while the heated steam is circulated in the jacket, whereby the tobacco material can be heated at the same temperature as that of the heated steam.
  • Nitrite salts contained in the tobacco raw material become unstable when the tobacco raw material has a pH of 8 or less, and the nitrite salts can be decomposed and released as NO x gas by heating the tobacco raw material at 80°C or higher. Therefore, according to the method of the present invention, the amount of TSNA contained in the tobacco raw material can be decreased and the amount of the nitrate salt can also be decreased.
  • Nitrous acid contained in a sample is reacted with an aromatic primary amine (sulfanilamide) to form a diazonium salt.
  • An azo coupling reaction of the diazonium salt is caused with N-(1-naphthyl)-ehtylenediamine (NED) to form a purplish red azo compound.
  • a concentration of nitrite nitrogen (N) in the sample is measured by measurement of an absorbance (540 nm) of the colored part, and the obtained concentration is converted into a concentration of nitrous acid.
  • Example No. pH of tobacco material Acidic substance Antioxidant pH after adjustment Nitrous acid content after heat treatment ( ⁇ g/g) (dry basis) TSNA content after heat treatment ( ⁇ g/g) (dry basis)
  • Example 1 8.3 Citric acid Epigallocatechin gallate 6.1 0.2 2.3
  • Example 2 8.3 Citric acid Green tea extract 6.3 0.5 2.5
  • Example 3 8.3 Citric acid Ascorbic acid 5.6 1.6 2.0 Comparative example 1 8.3 Citric acid None 6.5 3.8 5.1 Comparative example 2 8.3 None None 8.3 180.2 3.6
  • the TSNA content in the tobacco raw material can be remarkably decreased.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Botany (AREA)
  • Toxicology (AREA)
  • Manufacture Of Tobacco Products (AREA)

Description

    Technical Field
  • The present invention relates to a method for producing an oral tobacco material, and an oral tobacco material. More specifically, the present invention relates to a method for producing an oral tobacco material having a reduced content of tobacco-specific nitrosamine, and an oral tobacco material obtained by that production method.
  • Background Art
  • Recently, oral tobacco products including snus have been drawing attention. The oral tobacco product contains an oral tobacco material such as powdered tobacco in a water-permeable pouch. People insert such an oral tobacco product between a lip and a gum in a mouth, and enjoy the taste and flavor of the powdered tobacco (see, for example, Patent Document 1).
  • The oral tobacco material used in such an oral tobacco product contains various components such as nicotine, nitrosamines (including tobacco-specific nitrosamine), hydrocarbons, and proteins, similar to a general tobacco material for a cigarette. In these components, there are some components which desirably are not removed or are increased in terms of smoking taste or other reasons; whereas, there are also some components whose amounts are desirably decreased. It is desired to decrease the amount of the tobacco-specific nitrosamine.
  • Prior Art Document Patent Document
  • Patent Document 1: U.S. Patent Application Publication No. 2007/062549 US-A-2011048434 discloses a thermal treatment process for tobacco materials. The tobacco materials are smokeless tobacco. The thermal treatment is carried out at a temperature of above 80°C and preferably below 140°C and the pH is maintained below 8 during the heat treatment. Additives are incorporated to the tobacco material before the heat treatment and include acidic compounds, citric acid, malic acid, glutaric acid, dicarboxylic acids, and the combination thereof.
  • Summary of Invention Problem to be solved by the Invention
  • The object of the present invention is to provide a method for producing an oral tobacco material having a reduced content of tobacco-specific nitrosamine (TSNA).
  • Means for solving the Problem
  • In order to solve the problem, according to the first aspect of the present invention, there is provided a method for producing an oral tobacco material, in accordance with claim 1.
  • Further, according to the second aspect of the present invention, there is provided an oral tobacco material which is obtained by the method for producing an oral tobacco material according to the present invention.
  • Effects of the Invention
  • The oral tobacco material produced according to the present invention shows a significantly reduced TSNA content.
  • Description of Embodiments
  • Various embodiments of the present invention will be explained in detail below.
  • In the method for producing an oral tobacco material according to the present invention, a dry oral tobacco material having a pH of 8 or less is used as a raw material. A dry oral tobacco material having a pH of 4 or more is usually used as the raw material. In the present specification, the pH of a dry tobacco material refers to a value obtained by adding 20 to 100 g of distilled water (corresponding to 10 times the amount of the tobacco material) to 2 to 10 g of the tobacco material; shaking the mixture of the water and the tobacco material at 200 rpm at room temperature for 10 minutes; allowing the resulting mixture to stand for 5 minutes; and then measuring the pH of an extract obtained therefrom with a pH meter (IQ 240 manufactured by IQ Scientific Instruments Inc.).
  • The tobacco raw material includes a dry oral tobacco material which originally has a pH of 8 or less, and a material obtained by adding an acidic substance to a dry oral tobacco material having a pH of more than 8 to adjust the pH to 8 or less.
  • The former, the dry oral tobacco material which originally has a pH of 8 or less may include flue-cured tobacco, burley tobacco, dark air-cured tobacco, dark fire-cured tobacco, air-cured tobacco by early-dehydrating, sun-cured tobacco, oriental tobacco, and the like.
  • The latter, the dry oral tobacco material having a pH of more than 8 may include a part of burley tobacco, dark air-cured tobacco, air-cured tobacco, and the like. As the acidic substance added to the above tobacco material, an organic acid such as citric acid, ascorbic acid, acetic acid, lactic acid, malic acid, tartaric acid, or succinic acid may be used. A dry oral tobacco material exhibiting acidity (i.e., a pH of less than 7) (for example, flue-cured tobacco, burley tobacco, dark air-cured tobacco, dark fire-cured tobacco, air-cured tobacco by early-dehydrating, sun-cured tobacco or oriental tobacco) may also be used, instead of the organic acid. When the dry oral tobacco material exhibiting acidity is used as the acidic substance, the amount thereof is preferably 100% by weight or less with respect to the raw material.
  • Next, an antioxidant is added to the tobacco raw material described above. The antioxidant significantly decreases the amount of TSNA contained in the tobacco raw material. TSNA typically includes N'-nitrosonornicotine (NNN), 4-(methylnitrosoamino)-1-(3-pyridyl)-1-butanone (NNK) and N'-nitrosoanatabine (NAT). The antioxidant includes epigallocatechin gallate, ascorbic acid, green tea extract. Ascorbic acid is also the acidic substance for adjusting the pH, as described above; and it may be used as the antioxidant in combination with another acidic substance, or may be used alone to serve both as the antioxidant and the acidic substance. The antioxidant is added preferably in an amount of 1 to 100 parts by weight based on 100 parts by weight of the tobacco raw material.
  • Next, the tobacco raw material to which the antioxidant has been added is heated at a temperature of 80°C or higher. The heating temperature is usually 130°C or lower. The heating time is usually from 10 minutes to 30 minutes.
  • In order to heat the tobacco raw material at a temperature of higher than 100°C, for example, the tobacco raw material is put in a closed heating container (such as a cylindrical one) having a jacket at the outer side thereof and equipped with an introduction pipe and an exhaust pipe of heated steam, and heated steam is directly blown into the tobacco raw material through the introduction pipe, while the heated steam is circulated in the jacket, whereby the tobacco material can be heated at the same temperature as that of the heated steam.
  • Nitrite salts contained in the tobacco raw material become unstable when the tobacco raw material has a pH of 8 or less, and the nitrite salts can be decomposed and released as NOx gas by heating the tobacco raw material at 80°C or higher. Therefore, according to the method of the present invention, the amount of TSNA contained in the tobacco raw material can be decreased and the amount of the nitrate salt can also be decreased.
  • Examples
  • The present invention will be explained by means of Examples, but the invention is not limited to those Examples.
  • Example 1
  • 5 kg of ground dry oral tobacco material (pH of 8.3) was put in a heating container, and 2% by weight of citric acid and 2% by weight of epigallocatechin gallate were added thereto, thereby adjusting the pH to 6.1. While the pH-adjusted tobacco material was stirred, heated steam having a temperature of 110°C was blown into the tobacco material and also the heated steam having a temperature of 110°C was circulated in a jacket provided at the outer side of the heating container, whereby the tobacco material was heated at 110°C for 30 minutes. After that, the heating container was cooled to room temperature, and the tobacco material was taken out from the container. A nitrous acid concentration and a TSNA concentration in the tobacco material were measured by the following methods. The results are shown in Table 1.
  • Example 2
  • 5 kg of ground dry oral tobacco material (pH of 8.3) was put in a heating container, and 2% by weight of citric acid and 2% by weight of a green tea extract were added thereto, thereby adjusting the pH to 6.3. While the pH-adjusted tobacco material was stirred, heated steam having a temperature of 110°C was blown into the tobacco material and also the heated steam having a temperature of 110°C was circulated in a jacket provided at the outer side of the heating container, whereby the tobacco material was heated at 110°C for 30 minutes. After that, the heating container was cooled to room temperature, and the tobacco material was taken out from the container. A nitrous acid concentration and a TSNA concentration in the tobacco material were measured. The results are shown in Table 1.
  • Example 3
  • 5 kg of ground dry oral tobacco material (pH of 8.3) was put in a heating container, and 2% by weight of citric acid and 2% by weight of ascorbic acid were added thereto, thereby adjusting the pH to 5.6. While the pH-adjusted tobacco material was stirred, heated steam having a temperature of 110°C was blown into the tobacco material and also the heated steam having a temperature of 110°C was circulated in a jacket provided at the outer side of the heating container, whereby the tobacco material was heated at 110°C for 30 minutes. After that, the heating container was cooled to room temperature, and the tobacco material was taken out from the container. A nitrous acid concentration and a TSNA concentration in the tobacco material were measured. The results are shown in Table 1.
  • Comparative Example 1
  • 5 kg of ground dry oral tobacco material (pH of 8.3) was put in a heating container, and 2% by weight of citric acid was added thereto, thereby adjusting the pH to 6.5. While the pH-adjusted tobacco material was stirred, heated steam having a temperature of 110°C was blown into the tobacco material and also the heated steam having a temperature of 110°C was circulated in a jacket provided at the outer side of the heating container, whereby the tobacco material was heated at 110°C for 30 minutes. After that, the heating container was cooled to room temperature, and the tobacco material was taken out from the container. A nitrous acid concentration and a TSNA concentration in the tobacco material were measured by the following methods. The results are shown in Table 1.
  • Comparative Example 2
  • 5 kg of ground dry oral tobacco material (pH of 8.3) was put in a heating container. While the tobacco material was stirred, heated steam having a temperature of 110°C was blown into the tobacco material and also the heated steam having a temperature of 110°C was circulated in a jacket provided at the outer side of the heating container, whereby the tobacco material was heated at 110°C for 30 minutes. After that, the heating container was cooled to room temperature, and the tobacco material was taken out from the container. A nitrous acid concentration and a TSNA concentration in the tobacco material were measured. The results are shown in Table 1.
  • <Measurement Method of TSNA Concentration>
  • In accordance with an official method (based on CORESTA METHOD CRM 72), a sample to which an internal standard fluid and 0.1 M ammonium acetate are added is shaken, diluted and filtered, and then the measurement is performed by UPLC/MS/MS.
  • <Measurement Method of Nitrous Acid Concentration>
  • Nitrous acid contained in a sample is reacted with an aromatic primary amine (sulfanilamide) to form a diazonium salt. An azo coupling reaction of the diazonium salt is caused with N-(1-naphthyl)-ehtylenediamine (NED) to form a purplish red azo compound. A concentration of nitrite nitrogen (N) in the sample is measured by measurement of an absorbance (540 nm) of the colored part, and the obtained concentration is converted into a concentration of nitrous acid.
  • [Table 1]
  • Table 1:
    Example No. pH of tobacco material Acidic substance Antioxidant pH after adjustment Nitrous acid content after heat treatment (µg/g) (dry basis) TSNA content after heat treatment (µg/g) (dry basis)
    Example 1 8.3 Citric acid Epigallocatechin gallate 6.1 0.2 2.3
    Example 2 8.3 Citric acid Green tea extract 6.3 0.5 2.5
    Example 3 8.3 Citric acid Ascorbic acid 5.6 1.6 2.0
    Comparative example 1 8.3 Citric acid None 6.5 3.8 5.1
    Comparative example 2 8.3 None None 8.3 180.2 3.6
  • As is apparent from the results shown in Table 1, according to the present invention, the TSNA content in the tobacco raw material can be remarkably decreased.

Claims (4)

  1. A method for producing an oral tobacco material, characterized by comprising the steps of:
    adding an antioxidant to a tobacco raw material consisting of a dry oral tobacco material having a pH of 8 or less; and
    heating the antioxidant-added tobacco raw material at a temperature of 80°C or higher, characterized in that the tobacco raw material is a material obtained by adding an organic acid or a dry oral tobacco material exhibiting acidity to a tobacco material having a pH of more than 8 to adjust the pH to 8 or less, and in that the antioxidant is selected from epigallocatechin gallate, ascorbic acid, and a green tea extract.
  2. The method according to claim 1, characterized in that the tobacco raw material is a material obtained by adding citric acid to a tobacco material having a pH of more than 8 to adjust the pH to 8 or less.
  3. The method according to claim 1 or 2, characterized in that the heating is performed at a temperature of 130°C or lower.
  4. An oral tobacco material which is obtained by the method according to any one of claims 1 to 3.
EP13752001.1A 2012-02-24 2013-02-20 Manufacturing method for chewing tobacco material, and chewing tobacco material Active EP2818059B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2012039028 2012-02-24
PCT/JP2013/054195 WO2013125586A1 (en) 2012-02-24 2013-02-20 Manufacturing method for chewing tobacco material, and chewing tobacco material

Publications (3)

Publication Number Publication Date
EP2818059A1 EP2818059A1 (en) 2014-12-31
EP2818059A4 EP2818059A4 (en) 2015-10-07
EP2818059B1 true EP2818059B1 (en) 2019-04-10

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EP13752001.1A Active EP2818059B1 (en) 2012-02-24 2013-02-20 Manufacturing method for chewing tobacco material, and chewing tobacco material

Country Status (5)

Country Link
EP (1) EP2818059B1 (en)
JP (1) JP5927288B2 (en)
DK (1) DK2818059T3 (en)
TW (1) TW201340889A (en)
WO (1) WO2013125586A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20121419A1 (en) * 2012-08-08 2014-02-09 Fattoria Autonoma Tabacchi S C A R L METHOD FOR THE PRODUCTION OF TOBACCO AIMED AT REDUCING THE NITROSAMINE CONTENT.
US11503853B2 (en) * 2013-09-09 2022-11-22 R.J. Reynolds Tobacco Company Smokeless tobacco composition incorporating a botanical material
CN104544549A (en) * 2014-12-31 2015-04-29 贵州中烟工业有限责任公司 Electronic cigarette smoke solution prepared through green tea leaf extract
EP3280278B1 (en) 2015-04-08 2019-05-29 Swedish Match North Europe AB Method for producing a pouched smokeless tobacco product comprising heat treatment

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007037962A1 (en) * 2005-09-22 2007-04-05 R.J. Reynolds Tobacco Company Smokeless tobacco composition
US20070062549A1 (en) 2005-09-22 2007-03-22 Holton Darrell E Jr Smokeless tobacco composition
US8944072B2 (en) * 2009-06-02 2015-02-03 R.J. Reynolds Tobacco Company Thermal treatment process for tobacco materials
US8434496B2 (en) * 2009-06-02 2013-05-07 R. J. Reynolds Tobacco Company Thermal treatment process for tobacco materials
DK2529634T3 (en) * 2010-01-28 2018-06-14 Japan Tobacco Inc Tobacco product with water repellent wrapping

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Also Published As

Publication number Publication date
EP2818059A4 (en) 2015-10-07
EP2818059A1 (en) 2014-12-31
TW201340889A (en) 2013-10-16
WO2013125586A1 (en) 2013-08-29
DK2818059T3 (en) 2019-05-13
JP5927288B2 (en) 2016-06-01
JPWO2013125586A1 (en) 2015-07-30

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